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Sample records for acid vinyl ester

  1. Ester Sensing with Poly (Aniline-co-m-aminobenzoic Acid Deposited on Poly (Vinyl Alcohol

    Directory of Open Access Journals (Sweden)

    S. ADHIKARI

    2011-02-01

    Full Text Available Poly (aniline-co-m-aminobenzoic acid was deposited on poly (vinyl alcohol film by in situ oxidative polymerization of the monomers aniline and m-aminobenzoic acid. Sensing experiments were performed on the composite film with the injection of various concentrations of hexenyl acetate and hexenyl butyrate at room temperature. The sensor responded rapidly and reversibly in the presence of hexenyl acetate and hexenyl butyrate vapors which was detected by resistance change of the composite film upon exposure to the vapor. Selectivity tests revealed that the sensor selectively responded to hexenyl butyrate compared to hexenyl acetate. The sensing response has been explained on the basis of FT-IR spectroscopic analysis of the polymer film before and after exposure to the ester vapor.

  2. Gamma radiolysis and vinyl esters

    International Nuclear Information System (INIS)

    De Bruyn, H.; Balic, R.; Gilbert, R.G.

    1998-01-01

    The principle behind γ relaxation of free-radical polymerizations is that the source of initiating radicals can be switched off 'instantaneously'. In the absence of initiating radicals the only kinetic events remaining are propagation, transfer and termination. For monomers whose propagation rate coefficients have been determined, relaxation behaviour can be interpreted to determine radical-loss rate coefficients and test models of loss mechanisms. This technique has been employed successfully on styrene and MMA emulsion polymerizations. In the present study, vinyl acetate and vinyl neo-decanoate (a ten-carbon-branched homologue of vinyl acetate) were studied, with the propagation rate coefficients for both monomers being established by pulsed-laser polymerization. Both were found to exhibit rapid γ relaxation rates in emulsion polymerization. This is a surprising result because mechanisms for rapid relaxation in emulsion polymerizations require that chain transfer to monomer (which is rapid for both monomers) is followed by exit from the particle into the aqueous phase with subsequent re-entry into a radical-containing particle leading to bimolecular termination. It is not unreasonable to suppose that this may be possible for vinyl acetate which is fairly water soluble (∼0.3 M). However, vinyl neo-decanoate is virtually insoluble (∼0.00004 M) and hence desorption is extremely unlikely. The most likely explanation for the observed rapid relaxations is that some of the radicals produced by γ radiolysis are slow to initiate vinyl esters and hence act as radical traps. As vinyl esters are known to be particularly unreactive monomers. it is feasible that this experimental artifact affects them to a much greater extent than some of the monomers studied successfully with this technique in the past

  3. On the complexing of phosphoric acid vinyl esters with praseodymium (3) and europium (3) nitrates in acetonitrile

    International Nuclear Information System (INIS)

    Goryushko, A.G.; Gololobov, Yu.G.; Boldeskul, A.E.; Oganesyan, A.S.; Yartsev, V.G.

    1990-01-01

    By the methods of electron, IR and PMR spectroscopy interaction of vinyl esters of phosphoric acid with praseodymium (3) and europium (3) nitrates in acetonitrile solutions has been studied. It is shown that the character of metal-ligand interaction is determined by chemical nature of the ligands: for a compound of ionic structure partially covalent bond is formed, and for a compound of betaine structure the interaction has mainly dipole character. Addition of molecule with betaine structure to praseodymium nitrate causes a change in geometry of Pr 3+ close surrounding and increase in its coordination number. The possibility of formation of the complex with metal-ligand ratio equal to 1:3 is shown

  4. Emission and Mechanical Evaluations of Vinyl-Ester Resin Systems

    National Research Council Canada - National Science Library

    Sands, James

    2003-01-01

    Vinyl-ester resins (VE) are frequently used in liquid molding of composite materials for several applications including naval and army structures, commercial boat manufacturing, and building construction...

  5. Vinyl ester resin and process for curing same with ionizing radiation in the presence of amines

    International Nuclear Information System (INIS)

    Mani, I.

    1975-01-01

    The addition of about 2 to 5 weight percent of certain amines to a thermosettable mixture of certain vinyl monomers and a polymerizable vinyl ester resin reduces the dosage level of ionizing radiation required to cure the mixture. (U.S.)

  6. ANALYSIS OF ADIPATE ESTER CONTENTS IN POLY(VINYL CHLORIDE) PLASTICS

    DEFF Research Database (Denmark)

    Berg, Rolf W.; Otero, Amalia Dopazo

    2006-01-01

    Fourier transform (FT-) Raman spectroscopy excited with a 1064 nm laser can be used to determine the content of plasticizers in commercial flexible poly vinyl chloride (PVC) products. Our previous study [T. Nørbygaard, R.W. Berg, Analysis of phthalate ester content in PVC plastics by means of FT......-Raman Spectroscopy, Appl. Spectrosc. 58 (4) (2004) 410–413]—on detection of the presence of phthalate esters in PVC by FT-Raman spectroscopy — is here extended to the similar case of adipate esters (AEs) in samples of soft poly vinyl chloride plastics. Spectra of a range of adipate ester plasticizers (11 AEs......) in pure form are reported. We studied if qualitative and quantitative determination of the adipate ester content would be possible based on the use of proper reference samples. It was found that AEs as a group cannot be definitively identified by their characteristic Raman bands because other aliphatic...

  7. Biocatalytic Asymmetric Synthesis of (1R, 2S)-N-Boc-vinyl-ACCA Ethyl Ester with a Newly Isolated Sphingomonas aquatilis.

    Science.gov (United States)

    Zhu, Shaozhou; Shi, Ying; Zhang, Xinyu; Zheng, Guojun

    2018-02-01

    1-amino cyclopropane-1-carboxylic acid (ACCA) and its derivatives are essential pharmacophoric unit that widely used in drug research and development. Specifically, (1R, 2S)-N-Boc-vinyl-ACCA ethyl ester (vinyl-ACCA) is a key chiral intermediate in the synthesis of highly potent hepatitis C virus (HCV) NS3/4A protease inhibitors such as asunaprevir and simeprevir. Developing strategies for the asymmetric synthesis of vinyl-ACCA is thus extremely high demand. In this study, 378 bacterial strains were isolated from soil samples using N-Boc-vinyl-ACCA ethyl ester as the sole carbon source and were screened for esterase activity. Fourteen of which worked effectively for the asymmetric synthesis of (1R, 2S)-N-Boc-1-vinyl ACCA ethyl ester. The strain CY-2, identified as Sphingomonas aquatilis, which showed the highest stability and enantioselectivity was selected as whole cell biocatalyst for further study. A systematic study of all factors influencing the enzymatic hydrolysis was performed. Under optimized conditions, resolution of rac-vinyl-ACCA to (1R, 2S)-N-Boc-1-vinyl ACCA ethyl ester with 88.2% ee and 62.4% conversion (E = 9) was achieved. Besides, S. aquatilis was also used to transform other 10 different substrates. Notably, it was found that 7 of them could be stereoselectively hydrolyzed, especially for (1R,2S)-1-amino-vinyl-ACCA ethyl ester hydrochloride (99.6% ee, E>200). Our investigations provide a new efficient whole cell biocatalyst for resolution of ACCA and might be developed for industry application.

  8. Nanoscale Characterization of Glass Flake Filled Vinyl Ester Anti-Corrosion Coatings

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    Salim Barbhuiya

    2017-08-01

    Full Text Available Vinyl ester is a thermoset matrix resin that is widely used in the coating industry. The presence of glass flakes further enhances the anti-corrosion performance of this coating. This paper reports the nanoscaled characterization of glass flake filled vinyl ester anti-corrosion coatings on mild steel. Bond strength properties of one uncoated and four coated samples with different thicknesses (300, 600, 900 and 1200 μm were studied using nanoscratch technique and ASTM Standard Test. It was found that the bond strength of coating with thickness 900 μm was the highest. The frequency distributions of elastic modulus on coating with 900 μm thickness determined using nanoindentation indicated that only 20–25% of the coating is composed of glass flakes and the balance is vinyl ester matrix. The critical depth at which the material is subject to failure due to external load and abrasion, was found to be around 100 nm.

  9. Enzymatic synthesis of arbutin undecylenic acid ester and its inhibitory effect on melanin synthesis.

    Science.gov (United States)

    Tokiwa, Yutaka; Kitagawa, Masaru; Raku, Takao; Yanagitani, Shusaku; Yoshino, Kenji

    2007-06-01

    Transesterification of arbutin and undecylenic acid vinyl ester was catalyzed by alkaline protease, Bioprase, in dimethylformamide to get arbutin derivative having undecylenic acid at 6-position of glucose moiety, 6-O-undecylenoyl p-hydroxyphenyl beta-D-glucopyranoside. The reaction rate increased with increase of arbutin concentration, and when its concentration was 0.9 M, the conversion rate was more than 90% under addition of 2 M undecylenic acid vinyl ester. The obtained arbutin ester significantly suppressed melanin production in murine B16 melanoma cells.

  10. Vinyl ester resin and process for curing same with ionizing radiation in the presence of amines

    International Nuclear Information System (INIS)

    Mani, I.

    1975-01-01

    The addition of about 1.5 to 5 weight percent of certain amines to a thermosettable mixture of an alkenyl aromatic monomer and a polymerizable vinyl ester resin reduces the dosage level of ionizing radiation required to cure the mixture. (U.S.)

  11. Strain Rate Dependent Ductile-to-Brittle Transition of Graphite Platelet Reinforced Vinyl Ester Nanocomposites

    Directory of Open Access Journals (Sweden)

    Brahmananda Pramanik

    2014-01-01

    Full Text Available In previous research, the fractal dimensions of fractured surfaces of vinyl ester based nanocomposites were estimated applying classical method on 3D digital microscopic images. The fracture energy and fracture toughness were obtained from fractal dimensions. A noteworthy observation, the strain rate dependent ductile-to-brittle transition of vinyl ester based nanocomposites, is reinvestigated in the current study. The candidate materials of xGnP (exfoliated graphite nanoplatelets reinforced and with additional CTBN (Carboxyl Terminated Butadiene Nitrile toughened vinyl ester based nanocomposites that are subjected to both quasi-static and high strain rate indirect tensile load using the traditional Brazilian test method. High-strain rate indirect tensile testing is performed with a modified Split-Hopkinson Pressure Bar (SHPB. Pristine vinyl ester shows ductile deformation under quasi-static loading and brittle failure when subjected to high-strain rate loading. This observation reconfirms the previous research findings on strain rate dependent ductile-to-brittle transition of this material system. Investigation of both quasi-static and dynamic indirect tensile test responses show the strain rate effect on the tensile strength and energy absorbing capacity of the candidate materials. Contribution of nanoreinforcement to the tensile properties is reported in this paper.

  12. Preparation of Thermoplastic Poly (vinyl Alcohol), Ethylene Vinyl Acetate and Vinyl Acetate Versatic Ester Blends for Exterior Masonry Coating

    International Nuclear Information System (INIS)

    EL-Nahas, H.H.; Gad, Y.H.; Magida, M.M.

    2013-01-01

    Blend systems including ethylene vinyl acetate (EVA), poly (vinyl alcohol) (PVA) and vinyl acetate versatic copolymer latex (VAcVe) were prepared and used as exterior coatings. Mechanical and thermal properties of the blends were investigated using a testo meter, shore hardness tester, thermogravimetric analysis (TGA) and scanning electron microscopy (SEM). The water resistance of the samples was measured. Effect of ionizing irradiation on gel content, tensile strength and surface hardness were also followed. The blend offers binder base for exterior masonry coating systems having superior water resistant and mechanical properties

  13. An Evaluation of Fracture Toughness of Vinyl Ester Composites Cured under Microwave Conditions

    Science.gov (United States)

    Ku, H.; Chan, W. L.; Trada, M.; Baddeley, D.

    2007-12-01

    The shrinkage of vinyl ester particulate composites has been reduced by curing the resins under microwave conditions. The reduction in the shrinkage of the resins by microwaves will enable the manufacture of large vinyl ester composite items possible (H.S. Ku, G. Van Erp, J.A.R. Ball, and S. Ayers, Shrinkage Reduction of Thermoset Fibre Composites during Hardening using Microwaves Irradiation for Curing, Proceedings, Second World Engineering Congress, Kuching, Malaysia, 2002a, 22-25 July, p 177-182; H.S. Ku, Risks Involved in Curing Vinyl Ester Resins Using Microwaves Irradiation. J. Mater. Synth. Proces. 2002b, 10(2), p 97-106; S.H. Ku, Curing Vinyl Ester Particle Reinforced Composites Using Microwaves. J. Comp. Mater., (2003a), 37(22), p 2027-2042; S.H. Ku and E. Siores, Shrinkage Reduction of Thermoset Matrix Particle Reinforced Composites During Hardening Using Microwaves Irradiation, Trans. Hong Kong Inst. Eng., 2004, 11(3), p 29-34). In tensile tests, the yield strengths of samples cured under microwave conditions obtained are within 5% of those obtained by ambient curing; it is also found that with 180 W microwave power, the tensile strengths obtained for all duration of exposure to microwaves are also within the 5% of those obtained by ambient curing. While, with 360 W microwave power, the tensile strengths obtained for all duration of exposure to microwaves are 5% higher than those obtained by ambient curing. Whereas, with 540 W microwave power, the tensile strengths obtained for most samples are 5% below those obtained by ambient curing (H. Ku, V.C. Puttgunta, and M. Trada, Young’s Modulus of Vinyl Ester Composites Cured by Microwave Irradiation: Preliminary Results, J. Electromagnet. Waves Appl., 2007, 20(14), p. 1911-1924). This project, using 33% by weight fly ash reinforced vinyl ester composite [VE/FLYSH (33%)], is to further investigate the difference in fracture toughness between microwave cured vinyl ester particulate composites and those cured

  14. Preparation of Macroporous Poly (vinyl alcohol-co-triallyl isocyanurate) Beads Bearing Aminocarboxylic Acid as Functional Groups by Suspension Polymerization

    Institute of Scientific and Technical Information of China (English)

    2003-01-01

    Macroporous poly (vinyl acetate-co-triallyl isocyanurate) beads were prepared with suspension polymerization method. The copolymer beads were then transformed into poly (vinyl alcohol-co-triallyl isocyanurate) by ester exchange reaction. Aminocarboxylic acids were immobilized on the copolymer beads by the esterification of hydroxyl groups with diethyl-lenetriaminepentaacetic bisanhydride. The weak acid exchange capacities, specific surface areas and mean pore diameters of the resultant resin beads were measured.

  15. Thermal and mechanical properties of fatty acid starch esters.

    Science.gov (United States)

    Winkler, H; Vorwerg, W; Rihm, R

    2014-02-15

    The current study examined thermal and mechanical properties of fatty acid starch esters (FASEs). All highly soluble esters were obtained by the sustainable, homogeneous transesterification of fatty acid vinyl esters in dimethylsulfoxide (DMSO). Casted films of products with a degree of substitution (DS) of 1.40-1.73 were compared with highly substituted ones (DS 2.20-2.63). All films were free of any plasticizer additives. Hydrophobic surfaces were characterized by contact angle measurements. Dynamic scanning calorimetry (DSC) and dynamic mechanical thermal analysis (DMTA) revealed thermal transitions (T(g), T(m)) which were influenced by the internal plasticizing effect of the ester groups. Thermal gravimetric analysis (TGA) measurements showed the increased thermal stability toward native starch. Tensile tests revealed the decreasing strength and stiffness of the products with increasing ester-group chain length while the elongation increased up to the ester group laurate and after that decreased. Esters of the longest fatty acids, palmitate and stearate turned out to be brittle materials due to super molecular structures of the ester chains such as confirmed by X-ray. Summarized products with a DS 1.40-1.73 featured more "starch-like" properties with tensile strength up to outstanding 43 MPa, while products with a DS >2 behaved more "oil-like". Both classes of esters should be tested as a serious alternative to commercial starch blends and petrol-based plastics. The term Cnumber is attributed to the number of total C-Atoms of the fatty acid (e.g. C6=Hexanoate). Copyright © 2013 Elsevier Ltd. All rights reserved.

  16. Production of methyl-vinyl ketone from levulinic acid

    Energy Technology Data Exchange (ETDEWEB)

    Dumesic, James A [Verona, WI; West,; Ryan, M [Madison, WI

    2011-06-14

    A method for converting levulinic acid to methyl vinyl ketone is described. The method includes the steps of reacting an aqueous solution of levulinic acid, over an acid catalyst, at a temperature of from room temperature to about 1100 K. Methyl vinyl ketone is thereby formed.

  17. Analysis of phthalate ester content in poly(vinyl chloride) plastics by means of Fourier transform Raman spectroscopy

    DEFF Research Database (Denmark)

    Nørbygaard, Thomas; Berg, Rolf W.

    2004-01-01

    Fourier transform (FT) Raman spectroscopy is applied to a range of phthalate ester plasticizers in pure form as well as in poly(vinyl chloride) (PVC) samples. It is found that phthalate esters as a group can be identified by a set of six characteristic Raman bands. FT-Raman spectra of 22 phthalate...

  18. Preparation of poly (vinyl alcohol) membranes grafted with n-vinyl pyridine/ acrylic acid binary monomers

    International Nuclear Information System (INIS)

    Ajji, A.; Ali, A.

    2014-03-01

    Poly(vinyl alcohol) films were grafted with two monomers using gamma radiation, acrylic acid and N-vinyl pyridine. The influence of different parameters on the grafting yield was investigated as: the comonomer concentration and composition, and irradiation dose. The suitable conditions of the process had been determined to prepare PVA membranes have both properties of the two monomers, acrylic acid and vinyl pyridine as comonomer concentration and composition, and irradiation dose. Some properties of the membranes had been investigated as maximum swelling and grafting. Also the ability of the grafted films to adsorb some heavy metals and dyes was elaborated and discussed.(author)

  19. Investigations on mechanical and two-body abrasive wear behaviour of glass/carbon fabric reinforced vinyl ester composites

    International Nuclear Information System (INIS)

    Suresha, B.; Kumar, Kunigal N. Shiva

    2009-01-01

    The aim of the research article is to study the mechanical and two-body abrasive wear behaviour of glass/carbon fabric reinforced vinyl ester composites. The measured wear volume loss increases with increase in abrading distance/abrasive particle size. However, the specific wear rate decreases with increase in abrading distance and decrease in abrasive particle size. The results showed that the highest specific wear rate is for glass fabric reinforced vinyl ester composite with a value of 10.89 x 10 -11 m 3 /Nm and the lowest wear rate is for carbon fabric reinforced vinyl ester composite with a value of 4.02 x 10 -11 m 3 /Nm. Mechanical properties were evaluated and obtained values are compared with the wear behaviour. The worn surface features have been examined using scanning electron microscope (SEM). Photomicrographs of the worn surfaces revealed higher percentage of broken glass fiber as compared to carbon fiber. Also better interfacial adhesion between carbon and vinyl ester in carbon reinforced vinyl ester composite was observed.

  20. Using the Maturity Method in Predicting the Compressive Strength of Vinyl Ester Polymer Concrete at an Early Age

    Directory of Open Access Journals (Sweden)

    Nan Ji Jin

    2017-01-01

    Full Text Available The compressive strength of vinyl ester polymer concrete is predicted using the maturity method. The compressive strength rapidly increased until the curing age of 24 hrs and thereafter slowly increased until the curing age of 72 hrs. As the MMA content increased, the compressive strength decreased. Furthermore, as the curing temperature decreased, compressive strength decreased. For vinyl ester polymer concrete, datum temperature, ranging from −22.5 to −24.6°C, decreased as the MMA content increased. The maturity index equation for cement concrete cannot be applied to polymer concrete and the maturity of vinyl ester polymer concrete can only be estimated through control of the time interval Δt. Thus, this study introduced a suitable scaled-down factor (n for the determination of polymer concrete’s maturity, and a factor of 0.3 was the most suitable. Also, the DR-HILL compressive strength prediction model was determined as applicable to vinyl ester polymer concrete among the dose-response models. For the parameters of the prediction model, applying the parameters by combining all data obtained from the three different amounts of MMA content was deemed acceptable. The study results could be useful for the quality control of vinyl ester polymer concrete and nondestructive prediction of early age strength.

  1. The elastoplastic response of and moisture diffusion through a vinyl ester resin-clay nanocomposite

    DEFF Research Database (Denmark)

    Drozdov, Aleksey D.; Christiansen, Jesper de Claville; Gupta, R.K.

    2002-01-01

    Experimental data are reported on the elastoplastic response of and moisture diffusion through a vinyl ester resin–montmorillonite clay nanocomposite with various amounts of filler. Two simple models are developed for the elastoplastic behavior of a nanocomposite and for the anomalous diffusion...... of penetrant molecules. Adjustable parameters in the constitutive equations are found by fitting the observations. It is revealed that some critical concentration of filler exists (about 1 wt.-%): in the sub-critical region of concentrations, molecular mobility of the host polymer strongly decreases...

  2. Anticholinesterase activity of fluorochloronitroacetic acid esters

    Energy Technology Data Exchange (ETDEWEB)

    Ivanov, Yu.Ya.; Brel, V.K. Martynov, I.V.

    1984-11-01

    Results are presented from pharmacologic and biochemical experiments leading to the conclusion that fluorochloronitroacetic acid esters have anticholinesterase activity. Since the esters caused muscular weakness in mice, experiments were performed on isolated tissue preparation. The biochemical experiments consisted of finding the biomolecular constants of irreversible inhibition of acetylcholinesterase by the esters, using acetylcholinesterase from human erythrocytes, as well as horse serum cholinesterase. The ethyl and n-propyl esters of halogen nitroacetic acid were used in all experiments. It was found that the propyl ester caused an increase in the force of individual contractions in the isolated muscle specimens, plus an inability of the muscle to retain tetanus. The substances were determined to have an anticholinesterase effect. The mechanism of cholinesterase inhibition is not yet known. It is probable that the substances acylate the serine hydroxyl of the esterase center of the cholinestersase. 7 references, 1 figure.

  3. Incorporation of coconut shell based nanoparticles in kenaf/coconut fibres reinforced vinyl ester composites

    Science.gov (United States)

    S, Abdul Khalil H. P.; Masri, M.; Saurabh, Chaturbhuj K.; Fazita, M. R. N.; Azniwati, A. A.; Sri Aprilia, N. A.; Rosamah, E.; Dungani, Rudi

    2017-03-01

    In the present study, a successful attempt has been made on enhancing the properties of hybrid kenaf/coconut fibers reinforced vinyl ester composites by incorporating nanofillers obtained from coconut shell. Coconut shells were grinded followed by 30 h of high energy ball milling for the production of nanoparticles. Particle size analyzer demonstrated that the size of 90% of obtained nanoparticles ranged between 15-140 nm. Furthermore, it was observed that the incorporation of coconut shell nanofillers into hybrid composite increased water absorption capacity. Moreover, tensile, flexural, and impact strength increased with the filler loading up to 3 wt.% and thereafter decrease was observed at higher filler concentration. However, elongation at break decreased and thermal stability increased in nanoparticles concentration dependent manner. Morphological analysis of composite with 3% of filler loading showed minimum voids and fiber pull outs and this indicated that the stress was successfully absorbed by the fiber.

  4. Toward reliable morphology assessment of thermosets via physical etching: Vinyl ester resin as an example

    Directory of Open Access Journals (Sweden)

    J. Karger-Kocsis

    2013-05-01

    Full Text Available The morphology of peroxide-cured, styrene crosslinked, bisphenol A-based vinyl ester (VE resin was investigated by atomic force microscopy (AFM after ‘physical’ etching with different methods. Etching was achieved by laser ablation, atmospheric plasma treatment and argon ion bombardment. Parameters of the etching were varied to get AFM scans of high topography resolution. VE exhibited a nanoscaled nodular structure the formation of which was ascribed to complex intra- and intermolecular reactions during crosslinking. The microstructure resolved after all the above physical etching techniques was similar provided that optimized etching and suitable AFM scanning conditions were selected. Nevertheless, with respect to the ‘morphology visualization’ these methods follow the power ranking: argon bombardment > plasma treatment > laser ablation.

  5. The effects of water absorption on an ester vinyl resin system

    Directory of Open Access Journals (Sweden)

    Ledjane Lima Sobrinho

    2009-09-01

    Full Text Available Derakene is a vinyl ester resin largely employed as matrix for polymeric based composite systems. In this work, the performance of such polymeric system was evaluated considering the effect of hygrothermal aging. The mechanical and thermal properties were examined for the processed material before and after ageing in water at 60 ºC for a maximum period of 64 days. Both analyses indicated the occurrence of post cure of the system after 16 days due to exposition at 60 ºC in water, which was also confirmed by analyses in samples with post cure treatment. Moreover, it was observed plasticizing of resin after 36 and 64 days of ageing. Micro structural and fracture surface analyses were carried out in order to characterize the samples. The appearance of surface voids was also observed.

  6. 21 CFR 172.854 - Polyglycerol esters of fatty acids.

    Science.gov (United States)

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Polyglycerol esters of fatty acids. 172.854 Section... HUMAN CONSUMPTION Multipurpose Additives § 172.854 Polyglycerol esters of fatty acids. Polyglycerol esters of fatty acids, up to and including the decaglycerol esters, may be safely used in food in...

  7. 21 CFR 172.848 - Lactylic esters of fatty acids.

    Science.gov (United States)

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Lactylic esters of fatty acids. 172.848 Section 172... CONSUMPTION Multipurpose Additives § 172.848 Lactylic esters of fatty acids. Lactylic esters of fatty acids... prepared from lactic acid and fatty acids meeting the requirements of § 172.860(b) and/or oleic acid...

  8. Thermal stabilization and plasticization of poly(vinyl chloride) by ester thiols: Update and current status

    International Nuclear Information System (INIS)

    Starnes, William H.; Du, Bin; Kim, Soungkyoo; Zaikov, Vadim G.; Ge, Xianlong; Culyba, Elizabeth K.

    2006-01-01

    Poly(vinyl chloride) (PVC) is one of the most important medical plastics. Recently, however, the safety of flexible PVC containing the common plasticizer, di(2-ethylhexyl) phthalate, has been called into question. Widely used heat stabilizers for PVC that incorporate toxic heavy metals also have fallen into disfavor. In order to address these problems, we have synthesized and tested, as potential replacements, several organic thiols that contain one or more carboxylate ester functions and thus are highly compatible with the polymer. When introduced into PVC at high loading levels (e.g., 30-35 parts by weight), the ester thiols are extremely effective as heat stabilizers and also useful as primary plasticizers. When used at a low loading level (e.g., 3 parts by weight), they still are excellent heat stabilizers for both plasticized and rigid PVC. Importantly, their high potency is achieved in the absence of any costabilizers that incorporate heavy metals. Their syntheses are simple and straightforward, and their odors are not offensive, because their volatilities are low. Described here are some typical results obtained with this new additive technology, which was licensed for commercialization in 2005

  9. Biotransformation of ferulic acid to 4-vinyl guaiacol by Lactobacillus ...

    African Journals Online (AJOL)

    Continuously growing demand for natural flavors has led to a tremendous increase in biotransformation process employing microorganisms of different genera using ferulic acid (FA) as the precursor. In this study, potential of Lactobacillus farciminis (ATCC 29644) for biotransformation of FA to 4-vinyl guaiacol (4VG) was ...

  10. Naturally Occurring Cinnamic Acid Sugar Ester Derivatives

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    Yuxin Tian

    2016-10-01

    Full Text Available Cinnamic acid sugar ester derivatives (CASEDs are a class of natural product with one or several phenylacrylic moieties linked with the non-anomeric carbon of a glycosyl skeleton part through ester bonds. Their notable anti-depressant and brains protective activities have made them a topic of great interest over the past several decades. In particular the compound 3′,6-disinapoylsucrose, the index component of Yuanzhi (a well-known Traditional Chinese Medicine or TCM, presents antidepressant effects at a molecular level, and has become a hotspot of research on new lead drug compounds. Several other similar cinnamic acid sugar ester derivatives are reported in traditional medicine as compounds to calm the nerves and display anti-depression and neuroprotective activity. Interestingly, more than one third of CASEDs are distributed in the family Polygalaceae. This overview discusses the isolation of cinnamic acid sugar ester derivatives from plants, together with a systematic discussion of their distribution, chemical structures and properties and pharmacological activities, with the hope of providing references for natural product researchers and draw attention to these interesting compounds.

  11. Hybrid thermosets from vinyl ester resin and acrylated epoxidized soybean oil (AESO

    Directory of Open Access Journals (Sweden)

    2011-01-01

    Full Text Available A series of hybrids composed of styrene crosslinkable vinyl ester (VE and acrylated epoxidized soybean oil (AESO were produced via free radical-induced crosslinking. The VE/AESO ratio was changed between 75/25 and 25/75 wt%. Moreover, to support phase grafting the VE/AESO = 50/50 wt% hybrid was modified with phthalic anhydride in various amounts (1, 5 and 10 wt%. The structure of the hybrid systems was investigated by dynamic mechanical thermal analysis (DMTA, differential scanning calorimetry (DSC, and atomic force microscopy (AFM. The properties of the systems were assessed by static flexural and fracture mechanical tests. The resistance to thermal degradation was inspected by thermogravimetric analysis (TGA. The results suggested that the hybrids have an interpenetrating network (IPN structure. With increasing AESO content the stiffness (modulus, strength and glass transition temperature (Tg of the hybrids decreased, whereas their ductility increased. Phthalic anhydride caused an adverse trend. Both the fracture toughness and fracture energy increased with increasing AESO content. They were less affected by adding phthalic anhydride phase couplant. Interestingly, the hybrids outperformed the parent VE and AESO in respect to resistance to thermal degradation.

  12. Effect of maleic anhydride treatment on the mechanical properties of sansevieria fiber/vinyl ester composites

    Science.gov (United States)

    Pradipta, Rangga; Mardiyati, Steven, Purnomo, Ikhsan

    2017-03-01

    Sanseviera trifasciata commonly called mother-in-law tongue also known as snake plant is native to Indonesia, India and Africa. Sansevieria is a new fiber in composite research and has showed promising properties as reinforcement material in polymer matrix composites. Chemical treatment on reinforcing fiber is crucial to reduce hydrophilic tendency and thus improve compatibility with the matrix. In this study, effect of maleic anhydride as chemical treatment on the mechanical properties of Sansevieria fiber/vinyl ester composite was investigated. Sansevieria fibers were immersed by using NaOH 3% for two hours at 100°C and then treated by using maleic anhydrate for two hours at 120°C. Composites were prepared by solution casting with various volume fractions of fiber; 0%, 2.5%, 5%, 7.5% and 10%. Actual density, volume fraction of void and mechanical properties of composite were conducted according to ASTM standard testing methods D792, D3171 and D3039. It was found that mechanical properties of composites increased as volume fractions of fiber was increased. The highest tensile strength and modulus of elasticity of composites were 57.45 MPa and 3.47 GPa respectively, obtained from composites with volume fraction of fiber 10%.

  13. Dispersant optimization using design of experiments for SiC/vinyl ester nanocomposites

    Science.gov (United States)

    Yong, Virginia; Hahn, H. Thomas

    2005-04-01

    The effect of dispersants on particle dispersion and flexural properties of SiC/vinyl ester nanocomposites was studied by factorial and response surface designs. The results show that the coupling agent 'gamma-methacryloxy propyl trimethoxy silane (MPS)' has no adverse side effect on the flexural properties as illustrated by the good correlation between maximizing the flexural strength and minimizing the agglomerates. However, the dispersant 'BYK-W 966' has a slight adverse side effect on the flexural properties although it improves dispersion at higher dosage. With an optimal dosage of MPS and W966, a small amount of SiC in 0.5 wt% results in 8% increase in strength and 14% increase in modulus. The flushing operation using the dispersant '1-octanol/decane' achieves an excellent SiC dispersion but it does not result in improved flexural properties. This confirmed that a better state of nanoparticle dispersion does not necessarily lead to improved flexural properties. A good dispersion coupling with a strong filler/matrix interfacial bonding is the key to obtain enhanced flexural properties.

  14. Synthesis and properties of fatty acid starch esters.

    Science.gov (United States)

    Winkler, Henning; Vorwerg, Waltraud; Wetzel, Hendrik

    2013-10-15

    Being completely bio-based, fatty acid starch esters (FASEs) are attractive materials that represent an alternative to crude oil-based plastics. In this study, two synthesis methods were compared in terms of their efficiency, toxicity and, especially, product solubility with starch laurate (C12) as model compound. Laurates (DS>2) were obtained through transesterification of fatty acid vinylesters in DMSO or reaction with fatty acid chlorides in pyridine. The latter lead to higher DS-values in a shorter reaction time. But due to the much better solubility of the products compared to lauroyl chloride esterified ones, vinylester-transesterification was preferred to optimize reaction parameters, where reaction time could be shortened to 2h. FASEs C6-C18 were also successfully prepared via transesterification. To determine the DS of the resulting starch laurates, the efficient ATR-IR method was compared with common methods (elementary analysis, (1)H NMR). Molar masses (Mw) of the highly soluble starch laurates were analyzed using SEC-MALLS (THF). High recovery rates (>80%) attest to the outstanding solubility of products obtained through transesterification, caused by a slight disintegration during synthesis. Particle size distributions (DLS) demonstrated stable dissolutions in CHCl3 of vinyl laurate esterified - contrary to lauroyl chloride esterified starch. For all highly soluble FASEs (C6-C18), formation of concentrated solutions (10 wt%) is feasible. Copyright © 2013 Elsevier Ltd. All rights reserved.

  15. Enzymatic synthesis of hydrophilic undecylenic acid sugar esters and their biodegradability.

    Science.gov (United States)

    Raku, Takao; Kitagawa, Masaru; Shimakawa, Hiromi; Tokiwa, Yutaka

    2003-01-01

    To enhance water solubility of 10-undecylenic acid, which has anti-fungus, anti-bacterial and anti-virus activity, D-glucose, trehalose and sucrose were regioselectively esterified with vinyl 10-undecylenic acid ester in dimethyl formamide by a commercial protease, Bioprase conc., from Bacillus subtilis. 6-O-(10-Undecylenoyl) D-glucose, 6-O-(10-undecylenoyl) trehalose and 1'-O-(10-undecylenoyl) sucrose were obtained. The influence of structural variation by changing the sugar moiety was analyzed the surface tension and biodegradability.

  16. Effect of Reinforced Hybrid Palm Shells on Mechanical Properties of Polyurethane-Jute Woven/ Vinyl Ester Sandwich Board

    International Nuclear Information System (INIS)

    Cheng, T.S.; Nurul Ain Nanyan; Lan, D.N.U.; Leng, T.P.

    2014-01-01

    A natural fiber sandwich was constructed from palm shells/polyurethane core and jute woven/vinyl ester face sheets by the in-situ sandwich process (core and panel prepared simultaneously). The polyurethane sandwich core was reinforced by hybrid shell systems of dried palm shell (DPS) and palm kernel shell (PKS) (50P-50D, 25P-75D), and single shell system of PKS (100P) as well as 20 phr empty fruit bunch (EFB) based on hundred part of polyurethane. The sandwich face sheets are prepared by using two jute woven layers and impregnated by vinyl ester. Interlocking between DPS and polyurethane matrix was formed, which hence enhanced the mechanical properties. The interfacial adhesion between DPS, PKS, and EFB with the polyurethane binder played the important role to achieve high mechanical properties. It was found that hybrid shells exhibited high reinforcement for sandwich's performance resulting better compression (50P-50D) and flexural (25P-75D) properties. The single shell 100P showed only improvement on flexural modulus.The fracture surface morphology of sandwich under mechanical test was performed by using optical microscopy. (author)

  17. Preparation of poly(vinyl alcohol) membranes grafted with N-vinyl imidazole/acrylic acid binary monomers

    International Nuclear Information System (INIS)

    Ajji, Zaki; Ali, Ali

    2006-01-01

    Poly(vinyl alcohol) films were grafted with two monomers using gamma radiation, acrylic acid and N-vinyl imidazole. The influence of different parameters on the grafting yield was investigated as: type of solvent and solvent composition, comonomer concentration and composition, addition of mineral acids, and irradiation dose. Water uptake in respect to the grafting yield was also evaluated. The ability of the grafted films to adsorb copper ions was elaborated and discussed for different grafting yields and ph values of the solution. (authors)

  18. Lipase-Catalyzed Production of 6-O-cinnamoyl-sorbitol from D-sorbitol and Cinnamic Acid Esters.

    Science.gov (United States)

    Kim, Jung-Ho; Bhatia, Shashi Kant; Yoo, Dongwon; Seo, Hyung Min; Yi, Da-Hye; Kim, Hyun Joong; Lee, Ju Hee; Choi, Kwon-Young; Kim, Kwang Jin; Lee, Yoo Kyung; Yang, Yung-Hun

    2015-05-01

    To overcome the poor properties of solubility and stability of cinnamic acid, cinnamate derivatives with sugar alcohols were produced using the immobilized Candida antarctica lipase with vinyl cinnamate and D-sorbitol as substrate at 45 °C. Immobilized C. antarctica lipase was found to synthesize 6-O-cinnamoyl-sorbitol and confirmed by HPLC and (1)H-NMR and had a preference for vinyl cinnamate over other esters such as allyl-, ethyl-, and isobutyl cinnamate as co-substrate with D-sorbitol. Contrary to D-sorbitol, vinyl cinnamate, and cinnamic acid, the final product 6-O-cinnamoyl-sorbitol was found to have radical scavenging activity. This would be the first report on the biosynthesis of 6-O-cinnamoyl-sorbitol with immobilized enzyme from C. antarctica.

  19. Interpolymer complexses of vinyl ether copolymer with polyacrylic and polymethacrylic acids

    Directory of Open Access Journals (Sweden)

    E. Shaikhutdinov

    2012-03-01

    Full Text Available The interactions between macromolecules of copolymers based on vinyl ethers (vinyl ether of monoethanolamine and vinyl buthyl ether and 2-acryloilamido-2-methylpropanesulphonic acid with polyacrylic and polymethacrylic acid and, as well as study the effect of interpolymer interactions in the adsorption of polymers at the aqueous solution-air interface were investigated. The observed synergistic increase in surface activity of macromolecules into polyelectrolyte mixtures explained by the formation of interpolymer complexes polyacid - copolymer.

  20. Synthesis and Antiradical Activity of Isoquercitrin Esters with Aromatic Acids and Their Homologues

    Directory of Open Access Journals (Sweden)

    Eva Heřmánková-Vavříková

    2017-05-01

    Full Text Available Isoquercitrin, (IQ, quercetin-3-O-β-d-glucopyranoside is known for strong chemoprotectant activities. Acylation of flavonoid glucosides with carboxylic acids containing an aromatic ring brings entirely new properties to these compounds. Here, we describe the chemical and enzymatic synthesis of a series of IQ derivatives at the C-6″. IQ benzoate, phenylacetate, phenylpropanoate and cinnamate were prepared from respective vinyl esters using Novozym 435 (Lipase B from Candida antarctica immobilized on acrylic resin. The enzymatic procedure gave no products with “hydroxyaromatic” acids, their vinyl esters nor with their benzyl-protected forms. A chemical protection/deprotection method using Steglich reaction yielded IQ 4-hydroxybenzoate, vanillate and gallate. In case of p-coumaric, caffeic, and ferulic acid, the deprotection lead to the saturation of the double bonds at the phenylpropanoic moiety and yielded 4-hydroxy-, 3,4-dihydroxy- and 3-methoxy-4-hydroxy-phenylpropanoates. Reducing capacity of the cinnamate, gallate and 4-hydroxyphenylpropanoate towards Folin-Ciocalteau reagent was significantly lower than that of IQ, while other derivatives displayed slightly better or comparable capacity. Compared to isoquercitrin, most derivatives were less active in 1,1-diphenyl-2-picrylhydrazyl (DPPH radical scavenging, but they showed significantly better 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid, ABTS scavenging activity and were substantially more active in the inhibition of tert-butylhydroperoxide induced lipid peroxidation of rat liver microsomes. The most active compounds were the hydroxyphenylpropanoates.

  1. Alternative Production of Fatty Acid Methyl Esters from Triglycerides ...

    African Journals Online (AJOL)

    The catalysts activity was tested in thermocatalytic cracking of triglyceride; a direct conversion process for fatty acid methyl esters (biodiesel). The SZ1 not only exhibited higher conversion of triglycerides but higher fatty acid methyl esters (FAMEs) yields of approximately 59% after 3h as compared to SZ2 (32%). In addition ...

  2. SYNTHESIS OF FATTY ACID ETHYL ESTER FROM CHICKEN FAT ...

    African Journals Online (AJOL)

    eobe

    synthesis of fatty acid ethyl ester from chicken fat waste using ZnO/SiO fatty acid ethyl ester ... obtained in the range of 56−88%and a second order quadratic polynomial regression model that established the ... Transesterification is a chemical.

  3. Synthesis and application of a novel environmental C26 diglycidyl ester plasticizer based on castor oil for poly(vinyl chloride)

    Science.gov (United States)

    In this work, for the first time, a castor oil derived diglycidyl ester plasticizer (C26-DGE) was prepared and incorporated into poly(vinyl chloride) (PVC). The chemical structure of the product was characterized by Fourier transform infrared spectroscopy (FT-IR), proton nuclear magnetic resonance (...

  4. Palladium-catalysed arylation of acetoacetate esters to yield 2-arylacetic acid esters

    CSIR Research Space (South Africa)

    Zeevaart, JG

    2004-05-24

    Full Text Available , was developed simultaneously by Hart- wig and Buchwald.5 Typically the tert-butyl ester of propionic acid is treated with an aryl halide (bromide or chloride) in the presence of a strong base, palladium and a bulky phosphine ligand or a bulky imidazolinium CO2t... novel palladium- catalysed conditions for the arylation of acetoacetate esters resulting in the formation of 2-arylacetic acid esters. When we attempted the arylation of tert-butyl aceto- acetate 1a with bromobenzene 2a using mild reaction conditions (K3...

  5. Preparation of carbon fiber unsaturated sizing agent for enhancing interfacial strength of carbon fiber/vinyl ester resin composite

    Science.gov (United States)

    Jiao, Weiwei; Cai, Yemeng; Liu, Wenbo; Yang, Fan; Jiang, Long; Jiao, Weicheng; Wang, Rongguo

    2018-05-01

    The practical application of carbon fiber (CF) reinforced vinyl ester resin (VE) composite was hampered seriously by the poor interfacial adhesion property. In this work, a novel unsaturated sizing agent was designed and prepared to improve the interfacial strength by covalently bonding CF with VE matrix. The main component of the sizing agent, N-(4‧4-diaminodiphenyl methane)-2-hydroxypropyl methacrylate (DMHM), was synthesized and confirmed by FTIR and NMR. XPS results of sized carbon fiber (SCF) showed that DMHM has adhered to desized fiber surface and reacted with some active functional groups on the surface. The SCF was characterized by high surface roughness and surface energy (especially the polar component), which means better wettability by VE. As a result, the interface shear strength and interlaminar shear strength of SCF/VE composite were enhanced by 96.56% and 66.07% respectively compared with CF/VE composite, benefited mainly from the strong and tough interphase.

  6. Preparation of esters of gallic acid with higher primary alcohols

    NARCIS (Netherlands)

    Kerk, G.J.M. van der; Verbeek, J.H.; Cleton, J.C.F.

    1951-01-01

    The esters of gallic acid and higher primary alcohols, especially fatty alcohols, have recently gained considerable interest as possible antioxidants for fats. Two independent methods for the preparation of these esters are described. In the first method the hitherto unknown compound galloyl

  7. 21 CFR 172.852 - Glyceryl-lacto esters of fatty acids.

    Science.gov (United States)

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Glyceryl-lacto esters of fatty acids. 172.852... HUMAN CONSUMPTION Multipurpose Additives § 172.852 Glyceryl-lacto esters of fatty acids. Glyceryl-lacto esters of fatty acids (the lactic acid esters of mono- and diglycerides) may be safely used in food in...

  8. Effect of side chain length and degree of polymerization on the decomposition and crystallization behaviour of chlorinated poly(vinyl ester) oligomers

    International Nuclear Information System (INIS)

    Heinze, D.; Mang, Th.; Popescu, C.; Weichold, O.

    2016-01-01

    Highlights: • Thermal behaviour of telomerized polyvinyl esters is investigated. • Thermal stability relies mainly on the contribution of side chains. • At equal molecular weights thermal stability is dictated by length of side chain. • Increasing the length of side chains improves also the packing degree of polymer. - Abstract: Four members of a homologous series of chlorinated poly(vinyl ester) oligomers CCl_3–(CH_2CH (OCO(CH_2)_mCH_3))_n–Cl with degrees of polymerization of 10 and 20 were prepared by telomerisation using carbon tetrachloride. The number of side chain carbon atoms ranges from 2 (poly(vinyl acetate) to 18 (poly(vinyl stearate)). The effect of the n-alkyl side chain length and of the degree of polymerization on the thermal stability and crystallization behaviour of the synthesized compounds was investigated. All oligomers degrade in two major steps by first losing HCl and side chains with subsequent breakdown of the backbone. The members with short side chains, up to poly(vinyl octanoate), are amorphous and show internal plasticization, whereas those with high number of side chain carbon atoms are semi-crystalline due to side-chain crystallization. A better packing for poly(vinyl stearate) is also noticeable. The glass transition and melting temperatures as well as the onset temperature of decomposition are influenced to a larger extent by the side chain length than by the degree of polymerization. Thermal stability is improved if both the size and number of side chains increase, but only a long side chain causes a significant increase of the resistance to degradation. This results in a stabilization of PVAc so that oligomers from poly(vinyl octanoate) on are stable under atmospheric conditions. Thus, the way to design stable, chlorinated PVEs oligomers is to use a long n-alkyl side chain.

  9. Effect of side chain length and degree of polymerization on the decomposition and crystallization behaviour of chlorinated poly(vinyl ester) oligomers

    Energy Technology Data Exchange (ETDEWEB)

    Heinze, D.; Mang, Th. [Aachen University of Applied Sciences, Heinrich-Mussmann-Str. 1, 52428 Jülich (Germany); Popescu, C., E-mail: crisan.popescu@kao.com [KAO Germany GmbH, Pfungstädterstr. 98-100, 64297 Darmstadt (Germany); Weichold, O., E-mail: weichold@ibac.rwth-aachen.de [Institute of Building Materials Research, Schinkelstr. 3, 52062 Aachen (Germany)

    2016-08-10

    Highlights: • Thermal behaviour of telomerized polyvinyl esters is investigated. • Thermal stability relies mainly on the contribution of side chains. • At equal molecular weights thermal stability is dictated by length of side chain. • Increasing the length of side chains improves also the packing degree of polymer. - Abstract: Four members of a homologous series of chlorinated poly(vinyl ester) oligomers CCl{sub 3}–(CH{sub 2}CH (OCO(CH{sub 2}){sub m}CH{sub 3})){sub n}–Cl with degrees of polymerization of 10 and 20 were prepared by telomerisation using carbon tetrachloride. The number of side chain carbon atoms ranges from 2 (poly(vinyl acetate) to 18 (poly(vinyl stearate)). The effect of the n-alkyl side chain length and of the degree of polymerization on the thermal stability and crystallization behaviour of the synthesized compounds was investigated. All oligomers degrade in two major steps by first losing HCl and side chains with subsequent breakdown of the backbone. The members with short side chains, up to poly(vinyl octanoate), are amorphous and show internal plasticization, whereas those with high number of side chain carbon atoms are semi-crystalline due to side-chain crystallization. A better packing for poly(vinyl stearate) is also noticeable. The glass transition and melting temperatures as well as the onset temperature of decomposition are influenced to a larger extent by the side chain length than by the degree of polymerization. Thermal stability is improved if both the size and number of side chains increase, but only a long side chain causes a significant increase of the resistance to degradation. This results in a stabilization of PVAc so that oligomers from poly(vinyl octanoate) on are stable under atmospheric conditions. Thus, the way to design stable, chlorinated PVEs oligomers is to use a long n-alkyl side chain.

  10. Characterization of Functionalized Acrylic acid /4- Vinyl Pyridine Graft Copolymers

    International Nuclear Information System (INIS)

    Kamal, H.; Mahmoud, Gh.A.; Hegazy, D.E.

    2009-01-01

    Properties and characterization of the membranes prepared by radiation grafting of acrylic acid (AAc) or/ and 4-vinyl pyridine (4VP) onto low density polyethylene (LDPE) and polypropylene (PP) films were carried out. The FTIR spectra for the grafted membranes were studied to evaluate the structure change as a result of grafting. The swelling behaviour of the graft copolymer in methanol was studied. It was found that the grafting of AAc and/ or 4- VP onto LDPE and PP resulted in introducing good hydrophilic properties to such polymer substrates. The hydrophilic properties were directly proportional to the amount of functional groups. The mechanical properties (Young's modulus, elongation percent and tensile strength) of the grafted membranes also, have been investigated. As the grafting degree increases, the modulus also increases. Increasing the hydrophilicity of the membranes by chemical treatment enhances its mechanical properties. The thermal parameters of the grafted membranes such as δH m1 . δH m2 , and T rc have been also studied by using DSC

  11. Three new fatty acid esters from the mushroom Boletus pseudocalopus.

    Science.gov (United States)

    Kim, Ki Hyun; Choi, Sang Un; Lee, Kang Ro

    2012-06-01

    A bioassay-guided fractionation and chemical investigation of a MeOH extract of the Korean wild mushroom Boletus pseudocalopus resulted in the identification of three new fatty acid esters, named calopusins A-C (1-3), along with two known fatty acid methyl esters (4-5). These new compounds are structurally unique fatty acid esters with a 2,3-butanediol moiety. Their structures were elucidated through 1D- and 2D-NMR spectroscopic data and GC-MS analysis as well as a modified Mosher's method. The new compounds 1-3 showed significant inhibitory activity against the proliferation of the tested cancer cell lines with IC(50) values in the range 2.77-12.51 μM.

  12. A monolithic lipase reactor for biodiesel production by transesterification of triacylglycerides into fatty acid methyl esters

    KAUST Repository

    Urban, Jiří T.; Švec, František; Frechet, Jean

    2011-01-01

    An enzymatic reactor with lipase immobilized on a monolithic polymer support has been prepared and used to catalyze the transesterification of triacylglycerides into the fatty acid methyl esters commonly used for biodiesel. A design of experiments procedure was used to optimize the monolithic reactor with variables including control of the surface polarity of the monolith via variations in the length of the hydrocarbon chain in alkyl methacrylate monomer, time of grafting of 1-vinyl-4,4-dimethylazlactone used to activate the monolith, and time used for the immobilization of porcine lipase. Optimal conditions involved the use of a poly(stearyl methacrylate-co-ethylene dimethacrylate) monolith, grafted first with vinylazlactone, then treated with lipase for 2h to carry out the immobilization of the enzyme. Best conditions for the transesterification of glyceryl tributyrate included a temperature of 37°C and a 10min residence time of the substrate in the bioreactor. The reactor did not lose its activity even after pumping through it a solution of substrate equaling 1,000 reactor volumes. This enzymatic reactor was also used for the transesterification of triacylglycerides from soybean oil to fatty acid methyl esters thus demonstrating the ability of the reactor to produce biodiesel. © 2011 Wiley Periodicals, Inc.

  13. A monolithic lipase reactor for biodiesel production by transesterification of triacylglycerides into fatty acid methyl esters

    KAUST Repository

    Urban, Jiří T.

    2011-09-26

    An enzymatic reactor with lipase immobilized on a monolithic polymer support has been prepared and used to catalyze the transesterification of triacylglycerides into the fatty acid methyl esters commonly used for biodiesel. A design of experiments procedure was used to optimize the monolithic reactor with variables including control of the surface polarity of the monolith via variations in the length of the hydrocarbon chain in alkyl methacrylate monomer, time of grafting of 1-vinyl-4,4-dimethylazlactone used to activate the monolith, and time used for the immobilization of porcine lipase. Optimal conditions involved the use of a poly(stearyl methacrylate-co-ethylene dimethacrylate) monolith, grafted first with vinylazlactone, then treated with lipase for 2h to carry out the immobilization of the enzyme. Best conditions for the transesterification of glyceryl tributyrate included a temperature of 37°C and a 10min residence time of the substrate in the bioreactor. The reactor did not lose its activity even after pumping through it a solution of substrate equaling 1,000 reactor volumes. This enzymatic reactor was also used for the transesterification of triacylglycerides from soybean oil to fatty acid methyl esters thus demonstrating the ability of the reactor to produce biodiesel. © 2011 Wiley Periodicals, Inc.

  14. A monolithic lipase reactor for biodiesel production by transesterification of triacylglycerides into fatty acid methyl esters.

    Science.gov (United States)

    Urban, Jiri; Svec, Frantisek; Fréchet, Jean M J

    2012-02-01

    An enzymatic reactor with lipase immobilized on a monolithic polymer support has been prepared and used to catalyze the transesterification of triacylglycerides into the fatty acid methyl esters commonly used for biodiesel. A design of experiments procedure was used to optimize the monolithic reactor with variables including control of the surface polarity of the monolith via variations in the length of the hydrocarbon chain in alkyl methacrylate monomer, time of grafting of 1-vinyl-4,4-dimethylazlactone used to activate the monolith, and time used for the immobilization of porcine lipase. Optimal conditions involved the use of a poly(stearyl methacrylate-co-ethylene dimethacrylate) monolith, grafted first with vinylazlactone, then treated with lipase for 2 h to carry out the immobilization of the enzyme. Best conditions for the transesterification of glyceryl tributyrate included a temperature of 37°C and a 10 min residence time of the substrate in the bioreactor. The reactor did not lose its activity even after pumping through it a solution of substrate equaling 1,000 reactor volumes. This enzymatic reactor was also used for the transesterification of triacylglycerides from soybean oil to fatty acid methyl esters thus demonstrating the ability of the reactor to produce biodiesel. Copyright © 2011 Wiley Periodicals, Inc.

  15. In vitro pharmacokinetics of anti-psoriatic fumaric acid esters

    NARCIS (Netherlands)

    N.H.R. Litjens (Nicolle); E. van Strijen (Elizabeth); C. van Gulpen (Co); H. Mattie (Herman); J.T. van Dissel (Jaap); H.B. Thio (Bing); P.H. Nibbering (Peter)

    2004-01-01

    textabstractBackground: Psoriasis is a chronic inflammatory skin disease that can be successfully treated with a mixture of fumaric acid esters (FAE) formulated as enteric-coated tablets for oral use. These tablets consist of dimethylfumarate (DMF) and salts of monoethylfumarate (MEF) and its main

  16. Effect of a novel insulinotropic agent, succinic acid monoethyl ester ...

    Indian Academy of Sciences (India)

    Madhu

    index (AAI) (ratio of HDL-C to total cholesterol) were studied. ... ester; FFA, free falty acids; HDL-C, high density lipoprotein-cholesterol; LDL-C, low density lipoprotein-cholesterol; ..... and impaired catabolism of triglyceride-rich particles. The.

  17. Fatty acid methyl esters production: chemical process variables

    Directory of Open Access Journals (Sweden)

    Paulo César Narváez Rincón

    2004-05-01

    Full Text Available The advantages of fatty acid methyl esters as basic oleochemicals over fatty acids, the seventies world energy crisis and the use of those oleochemicals as fuels, have increased research interest on fats and oils trans-esterification. In this document, a review about basic aspects, uses, process variables and problems associated to the production process of fatty acid methyl esters is presented. A global view of recent researches, most of them focused in finding a new catalyst with same activity as the alcohol-soluble hydroxides (NaOH, KOH, and suitable to be used in transforming fats and oils with high levels of free fatty acids and water avoiding separation problems and reducing process costs, is also discussed.

  18. Transformation of Unsaturated Fatty Acids/Esters to Corresponding Keto Fatty Acids/Esters by Aerobic Oxidation with Pd(II)/Lewis Acid Catalyst.

    Science.gov (United States)

    Senan, Ahmed M; Zhang, Sicheng; Zeng, Miao; Chen, Zhuqi; Yin, Guochuan

    2017-08-16

    Utilization of renewable biomass to partly replace the fossil resources in industrial applications has attracted attention due to the limited fossil feedstock with the increased environmental concerns. This work introduced a modified Wacker-type oxidation for transformation of unsaturated fatty acids/esters to the corresponding keto fatty acids/esters, in which Cu 2+ cation was replaced with common nonredox metal ions, that is, a novel Pd(II)/Lewis acid (LA) catalyst. It was found that adding nonredox metal ions can effectively promote Pd(II)-catalyzed oxidation of unsaturated fatty acids/esters to the corresponding keto fatty acids/esters, even much better than Cu 2+ , and the promotional effect is highly dependent on the Lewis acidity of added nonredox metal ions. The improved catalytic efficiency is attributed to the formation of heterobimetallic Pd(II)/LA species, and the oxidation mechanism of this Pd(II)/LA catalyst is also briefly discussed.

  19. Encapsulating fatty acid esters of bioactive compounds in starch

    Science.gov (United States)

    Lay Ma, Ursula Vanesa

    Interest in the use of many bioactive compounds in foods is growing in large part because of the apparent health benefits of these molecules. However, many of these compounds can be easily degraded during processing, storage, or their passage through the gastrointestinal tract before reaching the target site. In addition, they can be bitter, acrid, or astringent, which may negatively affect the sensory properties of the product. Encapsulation of these molecules may increase their stability during processing, storage, and in the gastrointestinal tract, while providing controlled release properties. The ability of amylose to form inclusion complexes and spherulites while entrapping certain compounds has been suggested as a potential method for encapsulation of certain molecules. However, complex formation and spherulitic crystallization are greatly affected by the type of inclusion molecules, type of starch, and processing conditions. The objectives of the present investigation were to: (a) study the effect of amylose, amylopectin, and intermediate material on spherulite formation and its microstructure; (b) investigate the formation of amylose and high amylose starch inclusion complexes with ascorbyl palmitate, retinyl palmitate, and phytosterol esters; (c) evaluate the ability of spherulites to form in the presence of fatty acid esters and to entrap ascorbyl palmitate, retinyl palmitate, and phytosterol esters; and (d) evaluate the effect of processing conditions on spherulite formation and fatty acid ester entrapment. Higher ratios of linear to branched molecules resulted in the formation of more and rounder spherulites with higher heat stability. In addition to the presence of branches, it appears that spherulitic crystallization is also affected by other factors, such as degree of branching, chain length, and chain length distribution. Amylose and Hylon VII starch formed inclusion complexes with fatty acid esters of ascorbic acid, retinol, or phytosterols

  20. PROCESS FOR HYDROGENOLYSIS OF ALPHA-HYDROXY ESTERS OR ACIDS USING A HETEROGENEOUS CATALYST

    DEFF Research Database (Denmark)

    2017-01-01

    The present invention relates to a method for hydrogenolysis of alpha-hydroxy esters or acids, comprising reacting the alpha-hydroxy ester or acid in the presence of a heterogeneous catalyst. The present invention also relates to a method for producing propionic acid ester, and the use of any...

  1. 21 CFR 573.640 - Methyl esters of higher fatty acids.

    Science.gov (United States)

    2010-04-01

    ... 21 Food and Drugs 6 2010-04-01 2010-04-01 false Methyl esters of higher fatty acids. 573.640... ANIMALS Food Additive Listing § 573.640 Methyl esters of higher fatty acids. The food additive methyl esters of higher fatty acids may be safely used in animal feeds in accordance with the following...

  2. 40 CFR 721.3800 - Formaldehyde, condensated polyoxyethylene fatty acid, ester with styrenated phenol, ethylene...

    Science.gov (United States)

    2010-07-01

    ... polyoxyethylene fatty acid, ester with styrenated phenol, ethylene oxide adduct. 721.3800 Section 721.3800... Formaldehyde, condensated polyoxyethylene fatty acid, ester with styrenated phenol, ethylene oxide adduct. (a... generically as formaldehyde, condensated polyoxyethylene fatty acid, ester with styrenated phenol, ethylene...

  3. Oil recovery with vinyl sulfonic acid-acrylamide copolymers

    Energy Technology Data Exchange (ETDEWEB)

    Norton, C.J.; Falk, D.O.

    1973-12-18

    An aqueous polymer flood containing sulfomethylated alkali metal vinyl sulfonate-acrylamide copolymers was proposed for use in secondary or tertiary enhanced oil recovery. The sulfonate groups on the copolymers sustain the viscosity of the flood in the presence of brine and lime. Injection of the copolymer solution into a waterflooded Berea core, produced 30.5 percent of the residual oil. It is preferred that the copolymers are partially hydrolyzed.

  4. Green Synthesis of Acid Esters from Furfural via Stobbe Condensation

    Directory of Open Access Journals (Sweden)

    Shubhra Banerjee

    2013-01-01

    Full Text Available Solvent-free Stobbe condensation of furfural 1 with dimethyl succinate 2 under anhydrous conditions at room temperature using dry-solid potassium tertiary butoxide gave 3-carbomethoxy, 4-furyl-3-butenoic acid 3, which upon methylation followed by Stobbe condensation reaction with different aldehydes and/or ketones under anhydrous conditions at room temperature afforded substituted carbomethoxy acids 5a–f. These acid ester products were saponified to the corresponding dicarboxylic acids 6a–f which are useful in the synthesis of photochromic fulgides.

  5. Neutral Lipid Biosynthesis in Engineered Escherichia coli: Jojoba Oil-Like Wax Esters and Fatty Acid Butyl Esters

    OpenAIRE

    Kalscheuer, Rainer; Stöveken, Tim; Luftmann, Heinrich; Malkus, Ursula; Reichelt, Rudolf; Steinbüchel, Alexander

    2006-01-01

    Wax esters are esters of long-chain fatty acids and long-chain fatty alcohols which are of considerable commercial importance and are produced on a scale of 3 million tons per year. The oil from the jojoba plant (Simmondsia chinensis) is the main biological source of wax esters. Although it has a multitude of potential applications, the use of jojoba oil is restricted, due to its high price. In this study, we describe the establishment of heterologous wax ester biosynthesis in a recombinant E...

  6. Conversion of carbohydrates to levulinic acid esters

    DEFF Research Database (Denmark)

    2014-01-01

    The present invention relates to the field of converting carbohydrates into levulinic acid, a platform chemical for many chemical end products. More specifically the invention relates to a method for converting carbohydrates such as mono-, di- or polysaccharides, obtained from for example biomass...

  7. Synthesis and emulsifying properties of carbohydrate fatty acid esters produced from Agave tequilana fructans by enzymatic acylation.

    Science.gov (United States)

    Casas-Godoy, Leticia; Arrizon, Javier; Arrieta-Baez, Daniel; Plou, Francisco J; Sandoval, Georgina

    2016-08-01

    Carbohydrate fatty acid esters are non-ionic surfactants with a broad spectrum of applications. These molecules are generally synthesized using short carbohydrates or linear fructans; however in this research carbohydrate fatty acid esters were produced for the first time with branched fructans from Agave tequilana. Using immobilized lipases we successfully acylated A. tequilana fructans with vinyl laurate, obtaining products with different degrees of polymerization (DP). Lipozyme 435 was the most efficient lipase to catalyze the transesterification reaction. HPLC and ESI-MS analysis proved the presence of a mixture of acylated products as a result of the chemical complexity of fructans in the A. tequilana. The ESI-MS spectra showed a molecular mass shift between 183 and 366g/mol for fructooligosaccharides with a DP lower than 6, which indicated the presence of Agave fructans that had been mono- and diacylated with lauric acid. The carbohydrate fatty acid esters (CFAE) obtained showed good emulsifying properties in W/O emulsions. Copyright © 2016 Elsevier Ltd. All rights reserved.

  8. Organising pneumonia associated with fumaric acid ester treatment for psoriasis.

    Science.gov (United States)

    Deegan, Alexander Paul; Kirby, Brian; Rogers, Sarah; Crotty, Tom Bernard; McDonnell, Timonthy John

    2010-10-01

      We present the case of a 49-year old male who presented with dyspnoea, cough, weight loss, night sweats and general malaise. He had been on treatment with oral fumaric acid esters (FAE, Fumaderm®; Biogen Idec GmbH, Ismaning, Germany) for 6 months.   Report of a case.   His chest X-ray showed patchy infiltrates in the left upper lobe which failed to resolve under empiric antibiotic therapy. A computed tomography of thorax revealed bilateral, mostly peripheral foci of consolidation with air bronchograms. Transbronchial biopsies showed a pattern of organising pneumonia (OP).   Therapy with oral prednisolone (40 mg/day) resulted in a rapid clinical and radiological improvement. An association of FAE and OP has not previously been reported. Please cite this paper as: Deegan AP, Kirby B, Rogers S, Crotty TB and McDonnell TJ. Organising pneumonia associated with fumaric acid ester treatment for psoriasis. © 2010 Blackwell Publishing Ltd.

  9. Organising pneumonia associated with fumaric acid ester treatment for psoriasis.

    LENUS (Irish Health Repository)

    Deegan, Alexander Paul

    2012-02-01

    INTRODUCTION: We present the case of a 49-year old male who presented with dyspnoea, cough, weight loss, night sweats and general malaise. He had been on treatment with oral fumaric acid esters (FAE, Fumaderm(R); Biogen Idec GmbH, Ismaning, Germany) for 6 months. METHODS: Report of a case. RESULTS: His chest X-ray showed patchy infiltrates in the left upper lobe which failed to resolve under empiric antibiotic therapy. A computed tomography of thorax revealed bilateral, mostly peripheral foci of consolidation with air bronchograms. Transbronchial biopsies showed a pattern of organising pneumonia (OP). CONCLUSIONS: Therapy with oral prednisolone (40 mg\\/day) resulted in a rapid clinical and radiological improvement. An association of FAE and OP has not previously been reported. Please cite this paper as: Deegan AP, Kirby B, Rogers S, Crotty TB and McDonnell TJ. Organising pneumonia associated with fumaric acid ester treatment for psoriasis.

  10. 40 CFR 721.6200 - Fatty acid polyamine condensate, phosphoric acid ester salts.

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Fatty acid polyamine condensate... New Uses for Specific Chemical Substances § 721.6200 Fatty acid polyamine condensate, phosphoric acid... substances identified as fatty acid polyamine condensate, phosphate ester salts (PMNs P-90-1984 and P-90-1985...

  11. Poly(aniline-co-m-aminobenzoic acid) deposited on poly(vinyl ...

    Indian Academy of Sciences (India)

    Abstract. In this work, we have deposited poly(aniline-co-m-aminobenzoic acid) on poly(vinyl alcohol) (PVA) by in situ ... along the polyaniline (PANI) chain results in self dop- ing of PANI and ..... The value of electrical conductivity is found to be ...

  12. Fracture behavior of highly toughened poly(lactic acid)/ethylene-co-vinyl acetate blends

    NARCIS (Netherlands)

    Zeng, Q.; Feng, Y.; Wang, R.; Ma, P.

    2018-01-01

    Poly(lactic acid) (PLA) is brittle which restricts the range of its applications. The toughness of PLA was effectively improved in this work by incorporation of rubber grade ethylene-co-vinyl acetate (EVM). For example, the elongation at break of PLA increased by about 50 times after the addition of

  13. Fatty acid methyl ester profiles of bat wing surface lipids.

    Science.gov (United States)

    Pannkuk, Evan L; Fuller, Nathan W; Moore, Patrick R; Gilmore, David F; Savary, Brett J; Risch, Thomas S

    2014-11-01

    Sebocytes are specialized epithelial cells that rupture to secrete sebaceous lipids (sebum) across the mammalian integument. Sebum protects the integument from UV radiation, and maintains host microbial communities among other functions. Native glandular sebum is composed primarily of triacylglycerides (TAG) and wax esters (WE). Upon secretion (mature sebum), these lipids combine with minor cellular membrane components comprising total surface lipids. TAG and WE are further cleaved to smaller molecules through oxidation or host enzymatic digestion, resulting in a complex mixture of glycerolipids (e.g., TAG), sterols, unesterified fatty acids (FFA), WE, cholesteryl esters, and squalene comprising surface lipid. We are interested if fatty acid methyl ester (FAME) profiling of bat surface lipid could predict species specificity to the cutaneous fungal disease, white nose syndrome (WNS). We collected sebaceous secretions from 13 bat spp. using Sebutape(®) and converted them to FAME with an acid catalyzed transesterification. We found that Sebutape(®) adhesive patches removed ~6× more total lipid than Sebutape(®) indicator strips. Juvenile eastern red bats (Lasiurus borealis) had significantly higher 18:1 than adults, but 14:0, 16:1, and 20:0 were higher in adults. FAME profiles among several bat species were similar. We concluded that bat surface lipid FAME profiling does not provide a robust model predicting species susceptibility to WNS. However, these results provide baseline data that can be used for lipid roles in future ecological studies, such as life history, diet, or migration.

  14. Unsaturated Fatty Acid Esters Metathesis Catalyzed by Silica Supported WMe5

    KAUST Repository

    Riache, Nassima; Callens, Emmanuel; Talbi, Karima; Basset, Jean-Marie

    2015-01-01

    Metathesis of unsaturated fatty acid esters (FAEs) by silica supported multifunctional W-based catalyst is disclosed. This transformation represents a novel route towards unsaturated di-esters. Especially, the self-metathesis of ethyl undecylenate

  15. Inclusion polymerization of vinyl chloride monomer in deoxycholic acid host via γ-ray irradiation

    International Nuclear Information System (INIS)

    Chirachanchai, S.; Kumkrong, A.; Ishida, Hatsuo

    2000-01-01

    Inclusion polymerization of vinyl chloride monomer (VCM) was studied in the system of 3α, 12α -dihydroxy-5β-cholan-24-oic acid (deoxycholic acid, DCA). DCA-VCM inclusion compound system was originally prepared by guest intercalation technique in DCA guest free crystal. The inclusion polymerization of DCA-VCM by γ-irradiation at total dose 2 Mrad, gives a syndiotactic rich polyvinyl chloride (PVC) as can be confirmed by FT-IR and FT-NMR. (author)

  16. Inclusion polymerization of vinyl chloride monomer in deoxycholic acid host via {gamma}-ray irradiation

    Energy Technology Data Exchange (ETDEWEB)

    Chirachanchai, S.; Kumkrong, A. [The Petroleum and Petrochemical College, Chulalongkorn University, Bangkok (Thailand); Ishida, Hatsuo [Department of Macromolecular Science, Case Western Reserve University, Cleveland, OH (United States)

    2000-03-01

    Inclusion polymerization of vinyl chloride monomer (VCM) was studied in the system of 3{alpha}, 12{alpha} -dihydroxy-5{beta}-cholan-24-oic acid (deoxycholic acid, DCA). DCA-VCM inclusion compound system was originally prepared by guest intercalation technique in DCA guest free crystal. The inclusion polymerization of DCA-VCM by {gamma}-irradiation at total dose 2 Mrad, gives a syndiotactic rich polyvinyl chloride (PVC) as can be confirmed by FT-IR and FT-NMR. (author)

  17. Origin of estradiol fatty acid esters in human ovarian follicular fluid.

    Science.gov (United States)

    Pahuja, S L; Kim, A H; Lee, G; Hochberg, R B

    1995-03-01

    The estradiol fatty acid esters are the most potent of the naturally occurring steroidal estrogens. These esters are present predominantly in fat, where they are sequestered until they are hydrolyzed by esterases. Thus they act as a preformed reservoir of estradiol. We have previously shown that ovarian follicular fluid from patients undergoing gonadotropin stimulation contains very high amounts of estradiol fatty acid esters (approximately 10(-7) M). The source of these esters is unknown. They can be formed by esterification of estradiol in the follicular fluid by lecithin:cholesterol acyltransferase (LCAT), or in the ovary by an acyl coenzyme A:acyltransferase. In order to determine which of these enzymatic processes is the source of the estradiol esters in the follicular fluid, we incubated [3H]estradiol with follicular fluid and cells isolated from human ovarian follicular fluid and characterized the fatty acid composition of the [3H]estradiol esters biosynthesized in each. In addition, we characterized the endogenous estradiol fatty acid esters in the follicular fluid and compared them to the biosynthetic esters. The fatty acid composition of the endogenous esters was different than those synthesized by the cellular acyl coenzyme A:acyltransferase, and the same as the esters synthesized by LCAT, demonstrating that the esters are produced in situ in the follicular fluid. Although the role of these estradiol esters in the ovary is not known, given their remarkable estrogenic potency it is highly probable that they have an important physiological role.

  18. Synthesis of new fatty acids amides from aminolysis of fatty acid methyl esters (FAMEs)

    International Nuclear Information System (INIS)

    Lopes, Carolina R.; Montes D'Oca, Caroline da Ros; Duarte, Rodrigo da C.; Kurz, Marcia H.S.; Primel, Ednei G.; Clementin, Rosilene M.; Villarreyes, Joaquin Ariel M.; Montes D'Oca, Marcelo G.

    2010-01-01

    Recent biochemical and pharmacological studies have led to the characterization of different fatty acid amides as a new family of biologically active lipids. Here, we describe the synthesis of new amides from C16:0, 18:0, 18:1 and 18:1, OH fatty acids (FFA) families with cyclic and acyclic amines and demonstrate for the first time that these compounds produce cytotoxic effects. Application of this method to the synthesis of fatty acid amides was performed using the esters aminolysis as a key step and various carboxylic amides were prepared in good yield from fatty acid methyl esters (FAMEs). (author)

  19. Inactivation of γ-aminobutyric acid aminotransferase by γ-ethynyl- and γ-vinyl GABA

    International Nuclear Information System (INIS)

    Silverman, R.B.; Burke, J.R.; Nanavati, S.M.

    1989-01-01

    γ-Ethynyl- and γ-vinyl GABA (vigabatrin) are anticonvulsant agents that have been shown to be mechanism-based inactivators of γ-aminobutyric acid aminotransferase (GABA-T). The inactivation mechanisms of these compounds have been investigated. Inactivation of GABA-T by [ 3 H]γ-ethynyl GABA led to the incorporation of 1.0 equiv of 3 H into the enzyme which is not released by enzyme denaturation. Inactivation by γ-ethynyl GABA of GABA-T reconstituted with [ 3 H]PLP followed by denaturation resulted in release of 3 H as PLP. Eight different possible adducts are consistent with that result. Experiments have been carried out to differentiate these possibilities. Similar studies have been carried out with γ-vinyl GABA. Inactivation by [ 14 C]γ-vinyl GABA resulted in the incorporation of 1.0 equiv of 14 C per active site. Unlike the case with γ-ethynyl GABA, γ-vinyl GABA inactivation of GABA-T reconstituted with [ 3 H]PLP followed by denaturation resulted in release of 3 H as PMP

  20. Coating of Carbon Fiber with Polyhedral Oligomeric Silsesquioxane (POSS to Enhance Mechanical Properties and Durability of Carbon/Vinyl Ester Composites

    Directory of Open Access Journals (Sweden)

    Mujib Khan

    2011-09-01

    Full Text Available Our continuing quest to improve the performance of polymer composites under moist and saltwater environments has gained momentum in recent years with the reinforcement of inorganic nanoparticles into the polymer. The key to mitigate degradation of composites under such environments is to maintain the integrity of the fiber/matrix (F/M interface. In this study, the F/M interface of carbon/vinyl ester composites has been modified by coating the carbon fiber with polyhedral oligomeric silsesquioxane (POSS. POSS is a nanostructured inorganic-organic hybrid particle with a cubic structure having silicon atoms at the core and linked to oxygen atoms. The advantage of using POSS is that the silicon atoms can be linked to a substituent that can be almost any chemical group known in organic chemistry. Cubic silica cores are ‘hard particles’ and are about 0.53 nm in diameter. The peripheral organic unit is a sphere of about 1–3 nm in diameter. Further, cubic structure of POSS remains intact during the polymerization process and therefore with appropriate functional groups, if installed on the fiber surface, would provide a stable and strong F/M interface. Two POSS systems with two different functional groups; namely, octaisobutyl and trisilanolphenyl have been investigated. A set of chemical and mechanical procedures has been developed to coat carbon fibers with POSS, and to fabricate layered composites with vinyl ester resin. Interlaminar shear and low velocity impact tests have indicated around 17–38% improvement in mechanical properties with respect to control samples made without the POSS coating. Saltwater and hygrothermal tests at various environmental conditions have revealed that coating with POSS reduces water absorption by 20–30% and retains the composite properties.

  1. Neutral lipid biosynthesis in engineered Escherichia coli: jojoba oil-like wax esters and fatty acid butyl esters.

    Science.gov (United States)

    Kalscheuer, Rainer; Stöveken, Tim; Luftmann, Heinrich; Malkus, Ursula; Reichelt, Rudolf; Steinbüchel, Alexander

    2006-02-01

    Wax esters are esters of long-chain fatty acids and long-chain fatty alcohols which are of considerable commercial importance and are produced on a scale of 3 million tons per year. The oil from the jojoba plant (Simmondsia chinensis) is the main biological source of wax esters. Although it has a multitude of potential applications, the use of jojoba oil is restricted, due to its high price. In this study, we describe the establishment of heterologous wax ester biosynthesis in a recombinant Escherichia coli strain by coexpression of a fatty alcohol-producing bifunctional acyl-coenzyme A reductase from the jojoba plant and a bacterial wax ester synthase from Acinetobacter baylyi strain ADP1, catalyzing the esterification of fatty alcohols and coenzyme A thioesters of fatty acids. In the presence of oleate, jojoba oil-like wax esters such as palmityl oleate, palmityl palmitoleate, and oleyl oleate were produced, amounting to up to ca. 1% of the cellular dry weight. In addition to wax esters, fatty acid butyl esters were unexpectedly observed in the presence of oleate. The latter could be attributed to solvent residues of 1-butanol present in the medium component, Bacto tryptone. Neutral lipids produced in recombinant E. coli were accumulated as intracytoplasmic inclusions, demonstrating that the formation and structural integrity of bacterial lipid bodies do not require specific structural proteins. This is the first report on substantial biosynthesis and accumulation of neutral lipids in E. coli, which might open new perspectives for the biotechnological production of cheap jojoba oil equivalents from inexpensive resources employing recombinant microorganisms.

  2. 40 CFR 721.3680 - Ethylene oxide adduct of fatty acid ester with pentaerythritol.

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Ethylene oxide adduct of fatty acid... New Uses for Specific Chemical Substances § 721.3680 Ethylene oxide adduct of fatty acid ester with... identified generically as ethylene oxide adduct of fatty acid ester with pentaerythritol (PMN P-91-442) is...

  3. Preparation of Citric Acid Crosslinked Chitosan/Poly(Vinyl Alcohol Blend Membranes for Creatinine Transport

    Directory of Open Access Journals (Sweden)

    Retno Ariadi Lusiana

    2016-08-01

    Full Text Available Preparation of membrane using crosslinking reaction between chitosan and citric acid showed that functional group modification increased the number of active carrier groups which lead to better transport capacity of the membrane. In addition, the substitution of the carboxyl group increased creatinine permeation of chitosan membrane. The transport capacity of citric acid crosslinked chitosan membrane for creatinine was found to be 6.3 mg/L. The presence of cyanocobalamin slightly hindered the transport of creatinine although compounds did not able to pass through citric acid crosslinked chitosan/poly(vinyl alcohol blend membrane, as compounds no found in the acceptor phase.

  4. Novel fatty acid methyl esters from the actinomycete Micromonospora aurantiaca

    Science.gov (United States)

    Bruns, Hilke; Riclea, Ramona

    2011-01-01

    Summary The volatiles released by Micromonospora aurantiaca were collected by means of a closed-loop stripping apparatus (CLSA) and analysed by GC–MS. The headspace extracts contained more than 90 compounds from different classes. Fatty acid methyl esters (FAMEs) comprised the major compound class including saturated unbranched, monomethyl and dimethyl branched FAMEs in diverse structural variants: Unbranched, α-branched, γ-branched, (ω−1)-branched, (ω−2)-branched, α- and (ω−1)-branched, γ- and (ω−1)-branched, γ- and (ω−2)-branched, and γ- and (ω−3)-branched FAMEs. FAMEs of the last three types have not been described from natural sources before. The structures for all FAMEs have been suggested based on their mass spectra and on a retention index increment system and verified by the synthesis of key reference compounds. In addition, the structures of two FAMEs, methyl 4,8-dimethyldodecanoate and the ethyl-branched compound methyl 8-ethyl-4-methyldodecanoate were deduced from their mass spectra. Feeding experiments with isotopically labelled [2H10]leucine, [2H10]isoleucine, [2H8]valine, [2H5]sodium propionate, and [methyl-2H3]methionine demonstrated that the responsible fatty acid synthase (FAS) can use different branched and unbranched starter units and is able to incorporate methylmalonyl-CoA elongation units for internal methyl branches in various chain positions, while the methyl ester function is derived from S-adenosyl methionine (SAM). PMID:22238549

  5. Zeolite-catalysed preparation of alpha-hydroxy carboxylic acids and esters thereof

    DEFF Research Database (Denmark)

    2010-01-01

    A process for the production of lactic acid and 2-hydroxy-3-butenoic acid or esters thereof by conversion of glucose, fructose, sucrose, xylose and glycolaldehyde dissolved in a solvent in presence of a solid Lewis acidic catalyst.......A process for the production of lactic acid and 2-hydroxy-3-butenoic acid or esters thereof by conversion of glucose, fructose, sucrose, xylose and glycolaldehyde dissolved in a solvent in presence of a solid Lewis acidic catalyst....

  6. To immobilize polyethylene glycol-borate ester/lithium fluoride in graphene oxide/poly(vinyl alcohol for synthesizing new polymer electrolyte membrane of lithium-ion batteries

    Directory of Open Access Journals (Sweden)

    Y. F. Huang

    2017-01-01

    Full Text Available Polymer electrolyte membranes (PEMs are potentially applicable in lithium-ion batteries with high safety, low cost and good performance. Here, to take advantages of ionic conductivity and selectivity of borate ester-functionalized small molecules as well as structural properties of polymer nanocomposite, a strategy of immobilizing as-synthesized polyethylene glycol-borate ester/lithium fluoride (B-PEG/LiF in graphene oxide/poly(vinyl alcohol (GO/PVA to prepare a PEM is put forward. Chemical structure of the PEM is firstly characterized by 1H-, 11B- and 19F-nuclear magnetic resonance spectra, and Fourier transform infrared spectroscopy spectra, respectively, and then is further investigated under consideration of the interactions among PVA, B-PEG and LiF components. The immobilization of B-PEG/LiF in PVA-based structure is confirmed. As the interactions within electrolyte components can be further tuned by GO, ionic conductivity (~10–3 S·cm–1, lithium-ion transfer number (~0.49, and thermal (~273 °C/electrochemical (>4 V stabilities of the PEM can be obtained, and the feasibility of PEMs applied in a lithium-ion battery is also confirmed. It is believed that such PEM is a promising candidate as a new battery separator.

  7. Method for separating mono- and di-octylphenyl phosphoric acid esters

    International Nuclear Information System (INIS)

    Arnold, W.D. Jr.

    1977-01-01

    A method for separating mono-octylphenyl phosphoric acid ester and di-octylphenyl phosphoric acid ester from a mixture thereof comprises reacting the ester mixture with a source of lithium or sodium ions to form a mixture of the phosphate salts; contacting the salt mixture with an organic solvent which causes the dioctylphenyl phosphate salt to be dissolved in the organic solvent phase and the mono-octylphenyl phosphate salt to exist in a solid phase; separating the phases; recovering the phosphate salts from their respective phases; and acidifying the recovered salts to form the original phosphoric acid esters

  8. Chromatographic, Spectrometric and NMR Characterization of a New Set of Glucuronic Acid Esters Synthesized by Lipase

    Directory of Open Access Journals (Sweden)

    Michel Marlier

    2007-01-01

    Full Text Available An enzymatic synthesis was developed on a new set of D-glucuronic acid esters and particularly the tetradecyl-D-glucopyranosiduronate also named tetradecyl D-glucuronate. Chromatographic analyses revealed the presence of the ester as a mixture of anomeric forms for carbon chain lengths superior to 12. TOF/MS and MS/MS studies confirmed the synthesis of glucuronic acid ester. The NMR study also confirmed the structure of glucuronic acid esters and clearly revealed an anomeric (α/β ratio equivalent to 3/2

  9. Methyl esters from vegetable oils with hydroxy fatty acids: Comparison of lesquerella and castor methyl esters

    Science.gov (United States)

    The search for alternative feedstocks for biodiesel as partial replacement for petrodiesel has recently extended to castor oil. In this work, the castor oil methyl esters were prepared and their properties determined in comparison to the methyl esters of lesquerella oil, which in turn is seen as alt...

  10. Phthalic acid esters found in municipal organic waste

    DEFF Research Database (Denmark)

    Hartmann, Hinrich; Ahring, Birgitte Kiær

    2003-01-01

    Contamination of the organic fraction of municipal solid waste (OFMSW) with xenobiotic compounds and their fate during anaerobic digestion was investigated. The phthalic acid ester di-(2- ethylhexyl)phthalate (DEHP) was identified as the main contaminant in OFMSW in concentrations more than half.......41-0.79 d(-1), which is much higher than in previous investigations. It can be concluded that the higher removal rates are due to the higher temperature and higher initial concentrations per kg dry matter. These results suggest that the limiting factor for DEHP degradation is the bioavailability, which...... is enhanced at higher temperature and higher degradation of solid organic matter, to which the highly hydrophobic DEHP is adsorbed. The investigated reactor configuration with a thermophilic and a hyper-thermophilic treatment is, therefore, a good option for CD combining high rate degradation of organic...

  11. Effects of phthalic acid esters on the liver and thyroid

    International Nuclear Information System (INIS)

    Hinton, R.H.; Mitchell, F.E.; Mann, A.; Chescoe, D.; Price, S.C.; Nunn, A.; Grasso, P.; Bridges, J.W.

    1986-01-01

    The effects, over periods from 3 days to 9 months of administration, of diets containing di-2-ethylhexyl phthalate are very similar to those observed in rats administered diets containing hypolipidemic drugs such as clofibrate. Changes occur in a characteristic order commencing with alterations in the distribution of lipid within the liver, quickly followed by proliferation of hepatic peroxisomes and induction of the specialized P-450 isoenzyme(s) catalyzing omega oxidation of fatty acids. There follows a phase of mild liver damage indicated by changes in incorporation of 3 H-thymidine into DNA, by induction of glucose-6-phosphatase activity and a loss of glycogen, eventually leading to the formation of enlarged lysosomes through autophagy and the accumulation of lipofuscin. Associated changes are found in the kidney and thyroid. The renal changes are limited to the proximal convoluted tubules and are generally similar to changes found in the liver. The effects on the thyroid are more marked. Although the levels of thyroxine in plasma fall to about half normal values, serum triiodothyronine remains close to normal values while the appearance of the thyroid varies, very marked hyperactivity being noted 7 days after commencement of treatment, this is less marked at 14 days, but even after 9 months treatment there is clear cut evidence for hyperactivity with colloid changes which indicate this has persisted for some time. The short-term in vivo hepatic effects of the three phthalate esters can be reproduced in hepatocytes in tissue culture. All three phthalate esters, as well as clofibrate, have early marked effects on the metabolism of fatty acids in isolated hepatocytes. A hypothesis is presented to explain the progress from these initial metabolic effects to the final formation of liver tumors

  12. [Development of the determination methods of fatty acid esters of chloropropanediols in fat-rich foods].

    Science.gov (United States)

    Yan, Xiaobo; Wu, Shaoming; Li, Nan; Lü, Huadong; Fu, Wusheng

    2013-02-01

    Fatty acid esters of chloropropanediols are a kinds of newly emerged food contaminants, especially 3-monochloropropane-1,2-diol (3-MCPD) esters that have been detected in many foodstuffs such as infant formula and edible oils at relatively high levels. Based on the Tolerable Dose Intake (TDI) of 3-MCPD, the intake of 3-MCPD from 3-MCPD esters may cause the health risk to human beings. The researches for the analysis of 3-MCPD esters have been carried out in some institutes abroad, but there were only a few in China. This paper reviews the methods for the determination of 3-MCPD esters in fat-rich foods, including the extraction, hydrolysis, the derivatization of 3-MCPD esters, the total amount of 3-MCPD esters and the amounts of monoesters and diesters of 3-MCPD.

  13. Effect of gamma ray on poly(lactic acid)/poly(vinyl acetate-co-vinyl alcohol) blends as biodegradable food packaging films

    International Nuclear Information System (INIS)

    Razavi, Seyed Mohammad; Dadbin, Susan; Frounchi, Masoud

    2014-01-01

    Poly(lactic acid) (PLA)/poly(vinyl acetate-co-vinyl alcohol) [P(VAc-co-VA)] blends as new transparent film packaging materials were prepared at various blend compositions and different vinyl alcohol contents. The blends and pure PLA were irradiated by gamma rays to investigate the extent of changes in the packaging material during gamma ray sterilization process. The miscibility of the blends was dependent on the blend composition and vinyl alcohol content; gamma irradiation had little effect on the extent of miscibility. The glass transition temperature of pure PLA and PLA/P(VAc-co-VA) miscible blends reduced after irradiation. On the other hand in PLA/P(VAc-co-VA) immiscible blends, while the glass transition temperature of the PLA phase decreased; that of the copolymer phase slightly increased. The reduction in the glass transition was about 10 percent for samples irradiated with 50 kGy indicating dominance of chain scission of PLA molecules at high irradiation dose. The latter was verified by drop in mechanical properties of pure PLA after exposing to gamma irradiation at 50 kGy. Blending of PLA with the copolymer P(VAc-co-VA) compensated greatly the adverse effects of irradiation on PLA. The oxygen-barrier property of the blend was superior to the neat PLA and remained almost intact with irradiation. The un-irradiated and irradiated blends had excellent transparency. Gamma ray doses used for sterilization purposes are usually less than 20 kGy. It was shown that gamma irradiation at 20 kGy had no or little adverse effects on PLA/P(VAc-co-VA) blends mechanical and gas barrier properties. - Highlights: • Poly(lactic acid)/poly(vinyl acetate-co-vinyl alcohol) blends were prepared as new packaging film. • The blends are superior to PLA in oxygen gas barrier property. • The blends are suitable for gamma ray sterilization and maintain useful mechanical properties. • The blends are perfectly transparent

  14. 75 FR 20785 - Polyglyceryl Phthalate Ester of Coconut Oil Fatty Acids; Exemption from the Requirement of a...

    Science.gov (United States)

    2010-04-21

    ... Phthalate Ester of Coconut Oil Fatty Acids; Exemption from the Requirement of a Tolerance; Technical... ester of coconut oil fatty acids; exemption from the requirement of a tolerance. This document is being... requirement of a tolerance for ``polyglyceryl phthalate ester of coconut oil fatty acids'' pursuant to a...

  15. Intricate Conformational Tunneling in Carbonic Acid Monomethyl Ester.

    Science.gov (United States)

    Linden, Michael M; Wagner, J Philipp; Bernhardt, Bastian; Bartlett, Marcus A; Allen, Wesley D; Schreiner, Peter R

    2018-04-05

    Disentangling internal and external effects is a key requirement for understanding conformational tunneling processes. Here we report the s- trans/ s- cis tunneling rotamerization of carbonic acid monomethyl ester (1) under matrix isolation conditions and make comparisons to its parent carbonic acid (3). The observed tunneling rate of 1 is temperature-independent in the 3-20 K range and accelerates when using argon instead of neon as the matrix material. The methyl group increases the effective half life (τ eff ) of the energetically disfavored s- trans-conformer from 3-5 h for 3 to 11-13 h for 1. Methyl group deuteration slows the rotamerization further (τ eff ≈ 35 h). CCSD(T)/cc-pVQZ//MP2/aug-cc-pVTZ computations of the tunneling probability suggest that the rate should be almost unaffected by methyl substitution or its deuteration. Thus the observed relative rates are puzzling, and they disagree with previous explanations involving fast vibrational relaxation after the tunneling event facilitated by the alkyl rotor.

  16. Usage of methyl ester of tall oil fatty acids and resinic acids as alternative diesel fuel

    International Nuclear Information System (INIS)

    Keskin, Ali; Yasar, Abdulkadir; Guerue, Metin; Altiparmak, Duran

    2010-01-01

    In the experimental study, tall oil fatty and resinic acids were investigated as alternative diesel fuels. The fatty acids, obtained by distilling the crude tall oil, were esterified with methanol in order to obtain tall oil methyl ester (biodiesel). Blends of the methyl ester, resinic acids and diesel fuel were prepared for test fuels. Performance and emission tests of the test fuels were carried out in an unmodified direct injection diesel engine on full load conditions. The results showed that the specific fuel consumption (SFC) with the blend fuels did not show a significant change. CO emission and smoke level decreased up to 23.91% and 19.40%, respectively. In general, NO x emissions showed on trend of increasing with the blend fuels (up to 25.42%). CO 2 emissions did not vary with the blend fuels significantly.

  17. Usage of methyl ester of tall oil fatty acids and resinic acids as alternative diesel fuel

    Energy Technology Data Exchange (ETDEWEB)

    Keskin, Ali; Yasar, Abdulkadir [Tarsus Technical Education Faculty, Mersin University, 33500 Mersin (Turkey); Guerue, Metin [Engineering and Architectural Faculty, Gazi University, 06570 Maltepe, Ankara (Turkey); Altiparmak, Duran [Technical Education Faculty, Gazi University, 06500 Ankara (Turkey)

    2010-12-15

    In the experimental study, tall oil fatty and resinic acids were investigated as alternative diesel fuels. The fatty acids, obtained by distilling the crude tall oil, were esterified with methanol in order to obtain tall oil methyl ester (biodiesel). Blends of the methyl ester, resinic acids and diesel fuel were prepared for test fuels. Performance and emission tests of the test fuels were carried out in an unmodified direct injection diesel engine on full load conditions. The results showed that the specific fuel consumption (SFC) with the blend fuels did not show a significant change. CO emission and smoke level decreased up to 23.91% and 19.40%, respectively. In general, NO{sub x} emissions showed on trend of increasing with the blend fuels (up to 25.42%). CO{sub 2} emissions did not vary with the blend fuels significantly. (author)

  18. Synthesis of vinyl phosphites

    International Nuclear Information System (INIS)

    Kabachnik, M.M.; Novikova, Z.S.; Neganova, E.G.; Lutsenko, I.F.

    1986-01-01

    The authors investigated the reactions of phosphoriodidites and phosphinous iodides with a number of aldehydes and ketones in presence of tertiary amines (triethylamine, pyridine, N,N-diethylaniline), and they have shown that as a result of the reactions the corresponding vinyl esters of phosphorus acids are formed. The reactions of phosphoriodidites (and phosphorodiamidous iodides) with aliphatic aldehydes (acetaldehyde, propionaldehyde, butyraldehyde, and isobutyraldehyde) go at a molar reactant ratio of 1:1 in either at room temperature and are practically complete in 5-6 h. The yields of the alkenyl phosphites (phosphorodiamidites) were 45-70%. The compositions and structures of the compounds obtained were confirmed by elemental analysis and the IR and 1 H and 31 P NMR spectra

  19. Effect of gamma ray on poly(lactic acid)/poly(vinyl acetate-co-vinyl alcohol) blends as biodegradable food packaging films

    Science.gov (United States)

    Razavi, Seyed Mohammad; Dadbin, Susan; Frounchi, Masoud

    2014-03-01

    Poly(lactic acid) (PLA)/poly(vinyl acetate-co-vinyl alcohol) [P(VAc-co-VA)] blends as new transparent film packaging materials were prepared at various blend compositions and different vinyl alcohol contents. The blends and pure PLA were irradiated by gamma rays to investigate the extent of changes in the packaging material during gamma ray sterilization process. The miscibility of the blends was dependent on the blend composition and vinyl alcohol content; gamma irradiation had little effect on the extent of miscibility. The glass transition temperature of pure PLA and PLA/P(VAc-co-VA) miscible blends reduced after irradiation. On the other hand in PLA/P(VAc-co-VA) immiscible blends, while the glass transition temperature of the PLA phase decreased; that of the copolymer phase slightly increased. The reduction in the glass transition was about 10 percent for samples irradiated with 50 kGy indicating dominance of chain scission of PLA molecules at high irradiation dose. The latter was verified by drop in mechanical properties of pure PLA after exposing to gamma irradiation at 50 kGy. Blending of PLA with the copolymer P(VAc-co-VA) compensated greatly the adverse effects of irradiation on PLA. The oxygen-barrier property of the blend was superior to the neat PLA and remained almost intact with irradiation. The un-irradiated and irradiated blends had excellent transparency. Gamma ray doses used for sterilization purposes are usually less than 20 kGy. It was shown that gamma irradiation at 20 kGy had no or little adverse effects on PLA/P(VAc-co-VA) blends mechanical and gas barrier properties.

  20. Fatty acid sulphoalkyl amides and esters as cosmetic surfactants.

    Science.gov (United States)

    Petter, P J

    1984-10-01

    Synopsis A review is given of the manufacture, properties and applications of the anionic surfactants commonly known as taurates and isethionates (fatty acid sulphoalkyl amides and esters, respectively). Originally developed in the 1930s for textile processing, these surfactants are used increasingly in the cosmetic field, particularly those derived from coconut fatty acid. Both types are produced from sodium isethionate, HO degrees C(2)H(4)SO(3)Na. The acyl isethionate, R degrees COO degrees C(2)H(4)SO(3)Na, is obtained by reaction with a fatty acid ('direct process'). or fatty acid chloride ('indirect process'). The direct process is cheaper but requires extreme conditions which can lead to discoloration of the product and a loss of shorter chain fatty acid components. The N-methyl-N-acyltaurate, R degrees CON(R(1))C(2)H(4)SO(3)Na, is obtained by Schotten-Baumann reaction of a fatty acid chloride with N-methyltaurine, which is derived from sodium isethionate via methylamine. Taurates and isethionates retain the benefits of the soaps to which they are structurally similar, but chemical modifications have eliminated many undesirable features. Thus they combine good detergency and wetting with high foaming, and maintain their performance in hard or salt water. Taurates are stable to hydrolysis over the whole pH range. Isethionates are prone to hydrolysis at high (>8) or low (soap bars based on isethionate can be formulated at neutral pH ('Dove type'bars) instead of the alkaline pH of soap, and have been shown in various studies to be milder than soap and better tolerated by the young, the old and those with sensitive skins. Similarly, isethionates have been shown to be less irritating than other anionic or amphoteric surfactants used in cosmetics. The difference has been related to the negligible effect of isethionate on the water-binding capacity of stratum corneum. Other cosmetic applications besides toilet bars include shampoos (excellent cleaning, mild to scalp

  1. Impact of thermooxidation of phytosteryl and phytostanyl fatty acid esters on cholesterol micellarization in vitro.

    Science.gov (United States)

    Scholz, Birgit; Weiherer, Renate; Engel, Karl-Heinz

    2017-09-01

    The effects of thermooxidation of a phytosteryl/-stanyl and a phytostanyl fatty acid ester mixture on cholesterol micellarization were investigated using an in vitro digestion model simulating enzymatic hydrolysis by cholesterol esterase and subsequent competition of the liberated phytosterols/-stanols with cholesterol for incorporation into mixed micelles. As a first step, relationships between different doses of the ester mixtures and the resulting micellarized cholesterol were established. Subsequent subjection of the thermooxidized ester mixtures to the in vitro digestion model resulted in three principal observations: (i) thermal treatment of the ester mixtures led to substantial decreases of the intact esters, (ii) in vitro digestion of cholesterol in the presence of the thermooxidized ester mixtures resulted in significant increases of cholesterol micellarization, and (iii) the extents of the observed effects on cholesterol micellarization were strongly associated to the remaining contents of intact esters. The loss of efficacy to inhibit cholesterol micellarization due to thermally induced losses of intact esters corresponded to a loss of efficacy that would have been induced by an actual removal of these amounts of esters prior to the in vitro digestion. The obtained results suggest that in particular oxidative modifications of the fatty acid moieties might be responsible for the observed increases of cholesterol micellarization. Copyright © 2017 Elsevier Inc. All rights reserved.

  2. 21 CFR 172.225 - Methyl and ethyl esters of fatty acids produced from edible fats and oils.

    Science.gov (United States)

    2010-04-01

    ... from edible fats and oils. 172.225 Section 172.225 Food and Drugs FOOD AND DRUG ADMINISTRATION... Methyl and ethyl esters of fatty acids produced from edible fats and oils. Methyl esters and ethyl esters of fatty acids produced from edible fats and oils may be safely used in food, subject to the...

  3. Highly regioselective synthesis of undecylenic acid esters of purine nucleosides catalyzed by Candida antarctica lipase B.

    Science.gov (United States)

    Gao, Wen-Li; Li, Ning; Zong, Min-Hua

    2011-11-01

    Regioselective undecylenoylation of purine nucleosides as potential dual prodrugs was achieved by Candida antarctica lipase B using adenosine as a model reactant. The optimum organic solvent, molar ratio of vinyl ester to nucleoside, enzyme dosage, reaction temperature and molecular sieve amount were anhydrous THF, 5:1, 20 U/ml, 45°C and 75 mg/ml, respectively. Under the optimum conditions, the initial reaction rate, yield and 5'-regioselectivity were 1.1 mM/h, 90% and >99%, respectively. The enzymatic acylation of various nucleosides furnished the desired 5'-ester derivatives with the yields of 60-95% and 5'-regioselectivities of >99%. In addition, the lipase displayed excellent operational stability in THF, and retained 96% of its initial activity after reused for five batches.

  4. Influence of Fatty Acid Methyl Esters on Fuel properties of Biodiesel ...

    African Journals Online (AJOL)

    Influence of Fatty Acid Methyl Esters on Fuel properties of Biodiesel Produced from the. Seeds Oil of Curcubita ... Gas chromatograph coupled with mass spectrophotometer (GC-MS). The results indicate ..... Chemical and physical properties of ...

  5. Oxidative stability of fatty acid alkyl esters: a review.

    Directory of Open Access Journals (Sweden)

    Michal Angelovič

    2015-12-01

    Full Text Available The purpose of this study was to investigate and to process the current literary knowledge of the physico-chemical properties of vegetable oil raw used for biodiesel production in terms of its qualitative stability. An object of investigation was oxidative stability of biodiesel. In the study, we focused on the qualitative physico-chemical properties of vegetable oils used for biodiesel production, oxidative degradation and its mechanisms, oxidation of lipids, mechanisms of autooxidation, effectivennes of different synthetic antioxidants in relation to oxidative stability of biodiesel and methods of oxidative stability determination. Knowledge of the physical and chemical properties of vegetable oil as raw material and the factors affecting these properties is critical for the production of quality biodiesel and its sustainability. According to the source of oilseed, variations in the chemical composition of the vegetable oil are expressed by variations in the molar ratio among different fatty acids in the structure. The relative ratio of fatty acids present in the raw material is kept relatively constant after the transesterification reaction. The quality of biodiesel physico-chemical properties is influenced by the chain length and the level of unsaturation of the produced fatty acid alkyl esters. A biodiesel is thermodynamically stable. Its instability primarily occurs from contact of oxygen present in the ambient air that is referred to as oxidative instability. For biodiesel is oxidation stability a general term. It is necessary to distinguish ‘storage stability' and ‘thermal stability', in relation to oxidative degradation, which may occur during extended periods of storage, transportation and end use. Fuel instability problems can be of two related types, short-term oxidative instability and long-term storage instability. Storage instability is defined in terms of solid formation, which can plug nozzles, filters, and degrade engine

  6. Repellent activity of monoterpenoid esters with neurotransmitter amino acids against yellow fever mosquito, Aedes aegypti

    Directory of Open Access Journals (Sweden)

    Nesterkina Mariia

    2018-03-01

    Full Text Available Repellent activity of monoterpenoid esters (1-6 with neurotransmitter amino acids (GABA and glycine was investigated against Aedes aegypti by using a “cloth-patch” assay and compared to reference standard N,N-diethyl-3-methylbenzamide (DEET. Monoterpenoid esters showed repellent activity with minimum effective dosages (MED in the range of 0.031-0.469 mg/cm2. The carvacrol ester of GABA (2, MED of 0.031 ± 0.008 mg/cm2 exhibited the highest repellency of six monoterpenoid esters tested in comparison to the standard repellent DEET (MED of 0.009 ± 0.002 mg/cm2; however, the repellent activity of carvacrol-glycine ester (5 decreased 4-fold compared to the carvacrol-GABA derivative (2. The repellent activities of menthol GABA (1, MED= 0.375 ± 0.000 mg/cm2 and glycine ester (4, MED=0.312 ± 0.063 mg/cm2 were similar The guaiacol-glycine ester (6 was 3.75-fold more efficacious than the guaiacol ester of GABA (3. In the present study, we report repellent efficacy of prolonged exposure to GABA and glycine esters of menthol, carvacrol, guaiacol (1-6 as compared to the repellent activities of their monoterpene moieties alone.

  7. Reaction of acid esters of methylenebis(phosphonous acid) with carbonyl compounds

    International Nuclear Information System (INIS)

    Novikova, Z.S.; Odinets, I.L.; Lutsenko, I.F.

    1987-01-01

    The reaction of methylenebis(phosphonites) containing two hydrophosphoryl groupings with aliphatic and aromatic aldehydes and ketones in the presence of alkali metal fluorides leads to methylenebis(α-hydroxyalkylphosphinates). The reaction of methylenebis(phosphonites) containing one hydrophosphoryl groupings with carbonyl compounds in the presence of alkali metal fluorides proceeds with the formation of a new type of heterocyclic phosphorus compound, viz., 1,2λ 3 ,4λ 5 -oxadiphospholanes. The reaction of acid esters of methylenebis(phosphonous) acid with carbonyl compounds in the presence of alkali metal alkoxides or a tertiary amine is accompanied by phosphinate-phosphonate rearrangement of the intermediately formed α-hydroxylalkylphosphinates

  8. Pemisahan dan Pemurnian Phthalic Acid Ester dari Minyak Nyamplung

    Directory of Open Access Journals (Sweden)

    William Ekaputra Taifan

    2013-09-01

    Full Text Available Minyak nyamplung dikenal sebagai minyak yang tidak dapat dikonsumsi. Oleh sebab itu, penelitian tentang minyak ini hanya fokus pada konversi minyak menjadi biodiesel. Pada penelitian ini, kami berusaha untuk memisahkan resin beracun dari fraksi metanol menggunakan ekstraksi pelarut diikuti kolom kromatografi. Resin beracun ini diidentifikasi sebagai phthalic acid ester (PAE. PAE ini biasanya digunakan sebagai zat aditif di industri polimer. Minyak nyamplung mengandung 1,8% PAE, yang masih jauh melebihi nilai ambang batas. Isolasi PAE dari minyak ini diharapkan dapt mengubah minyak yang tidak dapat dikonsumsi menjadi suplemen makanan yang bernilai. Proses isolasi PAE dimulai dengan memisahkan senyawa yang diinginkan dari lipid menggunakan ekstraksi pelarut bertingkat dengan metanol dan n-heksan. Analisa mass spectra dari fraksi pertama dan fraksi kedua metanol menunjukkan kandungan PAE sebesar 60% dan 6% pada tiap fraksi. Fraksi heksan tidak mengandung PAE. PAE yang terkandung pada fraksi metanol diisolasi lebih lanjut dari asam lemak menggunakan liquid column chromatography dengan n-heksan – etil asetat sebagai mobile phase. Bis- 2ethylhexyl phthalate diidentifikasi pada ketiga fraksi sesuai dengan hasil analisa GC-MS. Fraksi pertama diambil pada kondisi mobile phase 5% etil asetat, sedangkan fraksi kedua merupakan campuran 5% etil asetat dan 10% etil asetat. Fraksi ketiga diambil pada kondisi mobile phase 10% etil asetat mengandung PAE sebesar 98%. Fraksi keempat merupakan campuran 10% dan 15% mobile phase dan mengandung PAE sebesar 97%. Akhirnya, kandungan PAE pada fraksi metanol sebesar 58%. Dari hasil analisa, dapat disimpulkan bahwa mobile phase yang optimum untuk kromatografi adalah 10- 15% etil asetat dalam n-heksan.

  9. Miscibility and specific interactions in blends of poly(n-vinyl-2-pyrrolidone) and acid functional polyester resins.

    NARCIS (Netherlands)

    Senatore, D.; Berix, M.J.A.; Laven, J.; Benthem, van R.A.T.M.; With, de G.; Mezari, B.; Magusin, P.C.M.M.

    2008-01-01

    Miscibility and intermol. interactions of novel blends of poly(N-vinyl-2-pyrrolidone) (PVP) and acid functional polyester resins (APE) were studied by use of Differential Scanning Calorimetry (DSC), Attenuated Total Reflectance Fourier Transform IR (ATR-FTIR), Cross-Polarization Magic Angle Spinning

  10. Pervaporation of alcohol-toluene mixtures through polymer blend membranes of poly(acrylic acid) and poly(vinyl alcohol)

    NARCIS (Netherlands)

    Park, H.C.; Park, H.; Meertens, R.M.; Meertens, R.M.; Mulder, M.H.V.; Smolders, C.A.; Smolders, C.A.

    1994-01-01

    Homogeneous membranes were prepared by blending poly(acrylic acid) with poly(vinyl alcohol). These blend membranes were evaluated for the selective separation of alcohols from toluene by pervaporation. The flux and selectivity of the membranes were determined both as a function of the blend

  11. Thermophysical properties of starch and whey protein composite prepared in presence of organic acid and esters

    Science.gov (United States)

    Previously, we prepared starch and protein composite by reactive mixing in presence of various organic acids and found that use of these acid esters resulted in composites with good mechanical properties. In this study, concentration (% w/w) of acid citrates in the starch-protein composites were var...

  12. Synthesis and antiproliferative properties of new hydrophilic esters of triterpenic acids.

    Science.gov (United States)

    Eignerova, Barbara; Tichy, Michal; Krasulova, Jana; Kvasnica, Miroslav; Rarova, Lucie; Christova, Romana; Urban, Milan; Bednarczyk-Cwynar, Barbara; Hajduch, Marian; Sarek, Jan

    2017-11-10

    To improve the properties of cytotoxic triterpenoid acids 1-5, a large set of hydrophilic esters was synthesized. We choose betulinic acid (1), dihydrobetulinic acid (2), 21-oxoacid 3 along with highly active des-E lupane acids 4 and 5 as a model set of compounds for esterification of which the properties needed to be improved. As ester moieties were used - methoxyethanol and 2-(2-methoxyethoxy)ethanol and glycolic unit (type a-d), pyrrolidinoethanol, piperidinoethanol and morpholinoethanol (type f-h), and monosaccharide groups (type i-l). As a result, 56 triterpenic esters (49 new compounds) were obtained and their cytotoxicity on four cancer cell lines and normal human fibroblasts was tested. All new compounds were fully soluble at all tested concentrations, which used to be a problem of the parent compounds 1 and 2. 16 compounds had IC 50  acids 1-5. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

  13. Microalgal fatty acid methyl ester a new source of bioactive compounds with antimicrobial activity

    Directory of Open Access Journals (Sweden)

    Arumugham Suresh

    2014-09-01

    Full Text Available Objective: To evaluate fatty acid composition and the antimicrobial activity of the major fraction of fatty acid methyl ester (FAME extracts from three microalgae collected from freshwater lakes in Theni District, Tamil Nadu, India. Methods: Antimicrobial study was carried out by well diffusion method against bacterial as well as fungal pathogens such as Escherichia coli, Staphylococcus aureus, Enterobacter sp., Klebsiella sp., Salmonella typhi, Fusarium sp., Cryptococcus sp., Candida sp., and Aspergillus niger and Aspergillus flavus. The FAME profiles were determined through gas chromatography with a flame ionization detector. Results: The FAME was found to be radial effective in inhibiting the radial growth of both bacterial and fungal pathogens. The FAME extracts exhibited the antibacterial activity against three clinical pathogens, namely, Escherichia coli, Salmonella typhi and Enterobacter sp. with the maximum zone of inhibition of 12.0 mm, 12.0 mm and 11.0 mm, respectively. The FAME showed moderate antifungal activity against Cryptococcus sp. (11.8 mm, Aspergillus niger (10.5 mm, Candida sp. (11.8 mm and Fusarium sp. (10.4 mm. Gas chromatography-flame ionization detector analysis revealed about 30 different FAMEs. Conclusions: We assume that the observed antimicrobial potency may be due to the abundance of erucic acid methyl ester (C22:0, arachidic acid methyl ester (C20:0, palmitic acid methyl ester (C16:0, cis-11-eicosenoicmethyl ester (C20:1, cis-11, 14-eicosadienoic acid methyl ester (C20:2 and linolenic acid methyl ester (C18:3 in FAMEs which appears to be promising to treat microbial diseases.

  14. Analysis of chemical signatures of alkaliphiles using fatty acid methyl ester analysis

    Directory of Open Access Journals (Sweden)

    Basha Sreenivasulu

    2017-01-01

    Full Text Available Background: Fatty acids occur in nearly all living organisms as the important predominant constituents of lipids. While all fatty acids have essentially the same chemical nature, they are an extremely diverse group of compounds. Materials and Methods: To test the hypothesis, fatty acids of alkaliphiles isolates, Bacillus subtilis SVUNM4, Bacillus licheniformis SVUNM8, Bacillus methylotrohicus SVUNM9, and Paenibacillus dendritiformis SVUNM11, were characterized compared using gas chromatography-mass spectrometry (GC-MS analysis. Results: The content of investigated ten fatty acids, 1, 2-benzenedicarboxylic acid butyl 2-methylpropyl ester, phthalic acid, isobutyl 2-pentyl ester, dibutyl phthalate, cyclotrisiloxane, hexamethyl, cyclotetrasiloxane, octamethyl, dodecamethyl, heptasiloxane 1,1,3,3,5,5,7,7,9,9,11,11,13,13-etradecamethyl, 7,15-dihydroxydehydroabietic acid, methyl ester, di (trimethylsilyl ether, hentriacontane, 2-thiopheneacetic acid, undec-2-enyl ester, obviously varied among four species, suggesting each species has its own fatty acid pattern. Conclusions: These findings demonstrated that GC-MS-based fatty acid profiling analysis provides the reliable platform to classify these four species, which is helpful for ensuring their biotechnological interest and novel chemotaxonomic.

  15. Tropanol esters of metallocene carboxylic acids. Syntheses, labelling with 103Ru and sup(103m)Rh and organ distribution

    International Nuclear Information System (INIS)

    Wenzel, M.; Wu, Y.

    1988-01-01

    The tropanol esters of the carboxylic acids of ferrocene, 103 Ru-ruthenocene and sup(103m)Rh-rhodocinium were synthezised. The organ distribution of the 103 Ru or sup(103m)Rh labelled tropanol-esters were investigated. Only the 103 Ru labelled ester showed a high heart/blood ratio. (author)

  16. Aspergillus niger whole-cell catalyzed synthesis of caffeic acid phenethyl ester in ionic liquids.

    Science.gov (United States)

    Rajapriya, Govindaraju; Morya, Vivek Kumar; Mai, Ngoc Lan; Koo, Yoon-Mo

    2018-04-01

    Synthesis of caffeic acid ester essentially requires an efficient esterification process to produce various kinds of medicinally important ester derivatives. In the present study, a comprehensive and comparative analysis of whole-cell catalyzed caffeic acid esters production in ionic liquids (ILs) media was performed. Olive oil induced mycelial mass of halotolerant Aspergillus niger (A.niger) EXF 4321 was freeze dried and used as a catalyst. To ensure maximum solubilization of caffeic acid for highest substrate loading several ILs were screened and 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([Emim][Tf 2 N]) was found to have the maximum solubility and favoured for enzymatic activity of freeze dried mycelia. The whole-cell catalyzed synthesis of caffeic acid phenethyl ester (CAPE) conditions were optimized and bioconversion up to 84% was achieved at a substrate molar ratio of 1:20 (caffeic acid:2-phenyl ethanol), 30°C for 12h. Results obtained during this study were encouraging and helpful to design a bioreactor system to produce caffeic acid derived esters. Copyright © 2017 Elsevier Inc. All rights reserved.

  17. Myo-inositol esters of indole-3-acetic acid are endogenous components of Zea mays L. shoot tissue

    Science.gov (United States)

    Chisnell, J. R.

    1984-01-01

    Indole-3-acetyl-myo-inositol esters have been demonstrated to be endogenous components of etiolated Zea mays shoots tissue. This was accomplished by comparison of the putative compounds with authentic, synthetic esters. The properties compared were liquid and gas-liquid chromatographic retention times and the 70-ev mass spectral fragmentation pattern of the pentaacetyl derivative. The amount of indole-3-acetyl-myo-inositol esters in the shoots was determined to be 74 nanomoles per kilogram fresh weight as measured by isotope dilution, accounting for 19% of the ester indole-3-acetic acid of the shoot. This work is the first characterization of an ester conjugate of indole-3-acetate acid from vegetative shoot tissue using multiple chromatographic properties and mass spectral identification. The kernel and the seedling shoot both contain indole-3-acetyl-myo-inositol esters, and these esters comprise approximately the same percentage of the total ester content of the kernel and of the shoot.

  18. Orally administered glycidol and its fatty acid esters as well as 3-MCPD fatty acid esters are metabolized to 3-MCPD in the F344 rat.

    Science.gov (United States)

    Onami, Saeko; Cho, Young-Man; Toyoda, Takeshi; Akagi, Jun-ichi; Fujiwara, Satoshi; Ochiai, Ryosuke; Tsujino, Kazushige; Nishikawa, Akiyoshi; Ogawa, Kumiko

    2015-12-01

    IARC has classified glycidol and 3-monochloropropane-1,2-diol (3-MCPD) as group 2A and 2B, respectively. Their esters are generated in foodstuffs during processing and there are concerns that they may be hydrolyzed to the carcinogenic forms in vivo. Thus, we conducted two studies. In the first, we administered glycidol and 3-MCPD and associated esters (glycidol oleate: GO, glycidol linoleate: GL, 3-MCPD dipalmitate: CDP, 3-MCPD monopalmitate: CMP, 3-MCPD dioleate: CDO) to male F344 rats by single oral gavage. After 30 min, 3-MCPD was detected in serum from all groups. Glycidol was detected in serum from the rats given glycidol or GL and CDP and CDO in serum from rats given these compounds. In the second, we examined if metabolism occurs on simple reaction with rat intestinal contents (gastric, duodenal and cecal contents) from male F344 gpt delta rats. Newly produced 3-MCPD was detected in all gut contents incubated with the three 3-MCPD fatty acid esters and in gastric and duodenal contents incubated with glycidol and in duodenal and cecal contents incubated with GO. Although our observation was performed at 1 time point, the results showed that not only 3-MCPD esters but also glycidol and glycidol esters are metabolized into 3-MCPD in the rat. Copyright © 2015 Elsevier Inc. All rights reserved.

  19. Gamma-aminobutyric acid esters. 1. Synthesis, brain uptake, and pharmacological studies of aliphatic and steroid esters of gamma-aminobutyric acid

    International Nuclear Information System (INIS)

    Shashoua, V.E.; Jacob, J.N.; Ridge, R.; Campbell, A.; Baldessarini, R.J.

    1984-01-01

    Labeled and unlabeled aliphatic and steroid esters of gamma-amino[U- 14 C]butyric acid (GABA) were synthesized and tested for their capacity to penetrate the blood-brain barrier and for evidence of central neuropharmacological activity in rodents. The uptake of the labeled 9,12,15-octadecatrienyl (linolenyl), 3-cholesteryl, 1-butyl, and the 9-fluoro-11 beta,17-dihydroxy-16 alpha-methyl-3,20-dioxopregna -1,4-dien-21-yl (dexamethasone) esters of GABA into mouse brain increased 2-, 25-, 74-, and 81-fold over GABA, respectively. The cholesteryl ester of GABA depressed the general motor activity of mice and rats in a dose-dependent manner, whereas the 1-butyl, linolenyl, and dexamethasone esters were inactive by this test. Studies of the rates of hydrolysis, GABA receptor binding capacity, and octanol/water partition coefficients indicated that pharmacological activity of the esters after entry into the central nervous system (CNS) was dependent on their capacity to release GABA by enzymatic hydrolysis and their lipid solubility

  20. Fatty Acid Methyl Esters and Solutol HS 15 Confer Neuroprotection After Focal and Global Cerebral Ischemia

    OpenAIRE

    Lin, Hung Wen; Saul, Isabel; Gresia, Victoria L.; Neumann, Jake T.; Dave, Kunjan R.; Perez-Pinzon, Miguel A.

    2013-01-01

    We previously showed that palmitic methyl ester (PAME) and stearic acid methyl ester (SAME) are simultaneously released from the sympathetic ganglion and PAME possesses potent vasodilatory properties which may be important in cerebral ischemia. Since PAME is a potent vasodilator simultaneously released with SAME, our hypothesis was that PAME/SAME confers neuroprotection in rat models of focal/global cerebral ischemia. We also examined the neuroprotective properties of Soluto...

  1. Crystal structures of hibiscus acid and hibiscus acid dimethyl ester isolated from Hibiscus sabdariffa (Malvaceae)

    OpenAIRE

    Zheoat, Ahmed M.; Gray, Alexander I.; Igoli, John O.; Kennedy, Alan R.; Ferro, Valerie A.

    2017-01-01

    The biologically active title compounds have been isolated from Hibiscus sabdariffa plants, hibiscus acid as a dimethyl sulfoxide monosolvate [systematic name: (2S,3R)-3-hy?droxy-5-oxo-2,3,4,5-tetra?hydro?furan-2,3-di?carb?oxy?lic acid dimethyl sulfoxide monosolvate], C6H6O7?C2H6OS, (I), and hibiscus acid dimethyl ester [systematic name: dimethyl (2S,3R)-3-hy?droxy-5-oxo-2,3,4,5-tetra?hydro?furan-2,3-di?carboxyl?ate], C8H10O7, (II). Compound (I) forms a layered structure with alternating laye...

  2. Process for preventing discoloration in hydrolyzed ethylene-vinyl acetate copolymers by exposure to radiation

    International Nuclear Information System (INIS)

    Hoyt, J.M.; Koch, K.; Williams, M. Jr.

    1975-01-01

    A process for the hydrolysis of a solid interpolymer of an ethylenically unsaturated hydrocarbon and a vinyl ester of a 2 to 6 carbon atom aliphatic carboxylic acid to products having a low yellowness index involves contacting of the solid interpolymer with a substantially anhydrous hydrolyzing agent and subjecting at least one of said interpolymer and said hydrolyzing agent to radiation. (U.S.)

  3. A microfluidic device for the automated derivatization of free fatty acids to fatty acid methyl esters.

    Science.gov (United States)

    Duong, Cindy T; Roper, Michael G

    2012-02-21

    Free fatty acid (FFA) compositions are examined in feedstock for biodiesel production, as source-specific markers in soil, and because of their role in cellular signaling. However, sample preparation of FFAs for gas chromatography-mass spectrometry (GC-MS) analysis can be time and labor intensive. Therefore, to increase sample preparation throughput, a glass microfluidic device was developed to automate derivatization of FFAs to fatty acid methyl esters (FAMEs). FFAs were delivered to one input of the device and methanolic-HCl was delivered to a second input. FAME products were produced as the reagents traversed a 29 μL reaction channel held at 55 °C. A Design of Experiment protocol was used to determine the combination of derivatization time (T(der)) and ratio of methanolic-HCl:FFA (R(der)) that maximized the derivatization efficiencies of tridecanoic acid and stearic acid to their methyl ester forms. The combination of T(der) = 0.8 min and R(der) = 4.9 that produced optimal derivatization conditions for both FFAs within a 5 min total sample preparation time was determined. This combination of T(der) and R(der) was used to derivatize 12 FFAs with a range of derivatization efficiencies from 18% to 93% with efficiencies of 61% for tridecanoic acid and 84% for stearic acid. As compared to a conventional macroscale derivatization of FFA to FAME, the microfluidic device decreased the volume of methanolic-HCl and FFA by 20- and 1300-fold, respectively. The developed microfluidic device can be used for automated preparation of FAMEs to analyze the FFA compositions of volume-limited samples.

  4. Convenient synthesis of 6-nor-9,10-dihydrolysergic acid methyl ester.

    Science.gov (United States)

    Crider, A M; Grubb, R; Bachmann, K A; Rawat, A K

    1981-12-01

    6-Nor-9,10-dihydrolysergic acid methyl ester (IV) was prepared by demethylation of 9,10-dihydrolysergic acid methyl ester (II) with 2,2,2-trichloroethyl chloroformate, followed by reduction of the intermediate carbamate (III) with zinc in acetic acid. The 6-ethyl-V and 6-n-propyl-VI derivatives were prepared by alkylation of IV with the appropriate halide. All of the ergoline derivatives were evaluated for stereotyped behavior in rats, with 6-nor-6-ethyl-9,10-dihydrolysergic acid methyl ester (V) being active but much less potent than apomorphine. Compound VI was evaluated for its effect on blood pressure; at a dose of 30 mg/kg ip, it significantly lowered, diastolic pressure in normotensive rats.

  5. Radiation curable coatings containing hydroxy functional polyethers and polyesters of monoethylenic acids or hydroxy esters thereof

    International Nuclear Information System (INIS)

    Kaufman, M.L.

    1978-01-01

    Relatively water insoluble hydroxy functional monoethylenic polyethers or polyesters of monoethylenic carboxylic acids or hydroxy alkyl esters thereof are formed by adducting the monoethylenic acid or its hydroxy ester with an anhydride selected from monoepoxides, lactones, or mixtures thereof in the presence of a Lewis acid catalyst, such as BF 3 etherate, at a temperature below that at which the unsaturation is consumed, typically about 30 to 70 0 C. These adducts are of low volatility and of low toxicity and can be radiation cured in admixture with polyacrylates to form coatings having improved resistance to elevated temperature exposure

  6. Determination of 4-Chloroindole-3-Acetic Acid Methyl Ester in Lathyrus Vicia and Pisum by Gas Chromatography - Mass Spectrometry

    DEFF Research Database (Denmark)

    Engvild, Kjeld Christensen; Egsgaard, Helge; Larsen, Elfinn

    1980-01-01

    4-Chloroindole-3-acetic acid methyl ester was identified unequivocally in Lathyrus latifolius L., Vicia faba L. and Pisum sativum L. by thin layer chromatography, gas chromatography and mass spectrometry. The gas chromatographic system was able to separate underivatized chloroindole-3-acetic acid...... methyl ester isomers. The quantitative determination of 4-chloroindole-3-acetic acid methyl ester in immature seeds of these three species was performed by gas chromatography – mass spectrometry using deuterium labelled 4-chloro-indole-3-acetic acid methyl ester as an internal standard. P. sativum...

  7. Alcohol consumption and synthesis of ethyl esters of fatty acids in adipose tissue

    NARCIS (Netherlands)

    Björntorp, P; Depergola, G; Sjöberg, C; Pettersson-Kymmer, U.; Hallgren, P; Boström, K; Helander, K G; Seidell, J

    1990-01-01

    Ethyl esters of fatty acids (EEFA) have been found to be formed during ethanol metabolism. Human adipose tissue contains high concentrations of free fatty acids, the substrate for EEFA synthesis, and might therefore be a tissue with great potential for EEFA formation. In order to explore their

  8. Asymmetric synthesis of α-amino acids by reduction of N-tert-butanesulfinyl ketimine esters.

    Science.gov (United States)

    Reddy, Leleti Rajender; Gupta, Aditya P; Liu, Yugang

    2011-05-06

    A highly regio- and diastereoselective reduction of various N-tert-butanesulfinyl ketimine esters with L-Selectride resulting in the formation of α-amino acids is reported. This method is quite general and also practical for the preparation of both enantiomers of aryl or aliphatic α-amino acids in high yields. © 2011 American Chemical Society

  9. Synthesis and antiproliferative properties of new hydrophilic esters of triterpenic acids

    Czech Academy of Sciences Publication Activity Database

    Eignerová, Barbara; Tichý, Michal; Krasulová, Jana; Kvasnica, Miroslav; Rárová, L.; Christová, R.; Urban, M.; Bednarczyk-Cwynar, B.; Hajdúch, M.; Šarek, J.

    2017-01-01

    Roč. 140, Nov 10 (2017), s. 403-420 ISSN 0223-5234 R&D Projects: GA MŠk(CZ) LO1304 Institutional support: RVO:61388963 ; RVO:61389030 Keywords : cytotoxicity * triterpenic acids * betulinic acid * hydrophilic ester * prodrug Subject RIV: CC - Organic Chemistry OBOR OECD: Organic chemistry Impact factor: 4.519, year: 2016

  10. The use of fatty acid esters to enhance free acid sophorolipid synthesis.

    Science.gov (United States)

    Ashby, Richard D; Solaiman, Daniel K Y; Foglia, Thomas A

    2006-02-01

    Fatty acid esters were prepared by transesterification of soy oil with methanol (methyl-soyate, Me-Soy), ethanol (ethyl-soyate, Et-Soy) and propanol (propyl-soyate, Pro-Soy) and used with glycerol as fermentation substrates to enhance production of free-acid sophorolipids (SLs). Fed-batch fermentations of Candida bombicola resulted in SL yields of 46 +/- 4 g/l, 42 +/- 7 g/l and 18 +/- 6 g/l from Me-Soy, Et-Soy, and Pro-Soy, respectively. Liquid chromatography with atmospheric pressure ionization mass spectrometry (LC/API-MS) showed that Me-Soy resulted in 71% open-chain SLs with 59% of those molecules remaining esterified at the carboxyl end of the fatty acids. Et-Soy and Pro-Soy resulted in 43% and 80% open-chain free-acid SLs, respectively (containing linoleic acid and oleic acid as the principal fatty acid species linked to the sophorose sugar at the omega-1 position), with no evidence of residual esterification.

  11. Role of dietary fatty acids in liver injury caused by vinyl chloride metabolites in mice

    Energy Technology Data Exchange (ETDEWEB)

    Anders, Lisanne C [Department of Pharmacology and Toxicology, University of Louisville Health Sciences Center, Louisville, KY 40292 (United States); Department of Medicine, University of Louisville Health Sciences Center, Louisville, KY 40292 (United States); Yeo, Heegook; Kaelin, Brenna R; Lang, Anna L; Bushau, Adrienne M; Douglas, Amanda N [Department of Pharmacology and Toxicology, University of Louisville Health Sciences Center, Louisville, KY 40292 (United States); Cave, Matt [Department of Pharmacology and Toxicology, University of Louisville Health Sciences Center, Louisville, KY 40292 (United States); Department of Medicine, University of Louisville Health Sciences Center, Louisville, KY 40292 (United States); Hepatobiology and Toxicology Program, University of Louisville Health Sciences Center, Louisville, KY 40292 (United States); Diabetes and Obesity Center, University of Louisville Health Sciences Center, Louisville, KY 40292 (United States); Robley Rex Louisville VAMC, Louisville, KY 40206 (United States); Arteel, Gavin E [Department of Pharmacology and Toxicology, University of Louisville Health Sciences Center, Louisville, KY 40292 (United States); Hepatobiology and Toxicology Program, University of Louisville Health Sciences Center, Louisville, KY 40292 (United States); McClain, Craig J [Department of Pharmacology and Toxicology, University of Louisville Health Sciences Center, Louisville, KY 40292 (United States); Department of Medicine, University of Louisville Health Sciences Center, Louisville, KY 40292 (United States); Hepatobiology and Toxicology Program, University of Louisville Health Sciences Center, Louisville, KY 40292 (United States); Diabetes and Obesity Center, University of Louisville Health Sciences Center, Louisville, KY 40292 (United States); Robley Rex Louisville VAMC, Louisville, KY 40206 (United States); and others

    2016-11-15

    Background: Vinyl chloride (VC) causes toxicant-associated steatohepatitis at high exposure levels. Recent work by this group suggests that underlying liver disease may predispose the liver to VC hepatotoxicity at lower exposure levels. The most common form of underlying liver disease in the developed world is non-alcoholic fatty liver disease (NAFLD). It is well-known that the type of dietary fat can play an important role in the pathogenesis of NAFLD. However, whether the combination of dietary fat and VC/metabolites promotes liver injury has not been studied. Methods: Mice were administered chloroethanol (CE - a VC metabolite) or vehicle once, 10 weeks after being fed diets rich in saturated fatty acids (HSFA), rich in poly-unsaturated fatty acids (HPUFA), or the respective low-fat control diets (LSFA; LPUFA). Results: In control mice, chloroethanol caused no detectable liver injury, as determined by plasma transaminases and histologic indices of damage. In HSFA-fed mice, chloroethanol increased HSFA-induced liver damage, steatosis, infiltrating inflammatory cells, hepatic expression of proinflammatory cytokines, and markers of endoplasmic reticulum (ER) stress. Moreover, markers of inflammasome activation were increased, while markers of inflammasome inhibition were downregulated. In mice fed HPUFA all of these effects were significantly attenuated. Conclusions: Chloroethanol promotes inflammatory liver injury caused by dietary fatty acids. This effect is far more exacerbated with saturated fat, versus poly-unsaturated fat; and strongly correlates with a robust activation of the NLRP3 inflammasome in the saturated fed animals only. Taken together these data support the hypothesis that environmental toxicant exposure can exacerbate the severity of NAFLD/NASH. - Highlights: • CE promotes inflammatory liver injury caused by dietary fatty acids. • This effect is stronger with saturated than with unsaturated fatty acids. • Damage caused by saturated fat and CE

  12. Role of dietary fatty acids in liver injury caused by vinyl chloride metabolites in mice

    International Nuclear Information System (INIS)

    Anders, Lisanne C; Yeo, Heegook; Kaelin, Brenna R; Lang, Anna L; Bushau, Adrienne M; Douglas, Amanda N; Cave, Matt; Arteel, Gavin E; McClain, Craig J

    2016-01-01

    Background: Vinyl chloride (VC) causes toxicant-associated steatohepatitis at high exposure levels. Recent work by this group suggests that underlying liver disease may predispose the liver to VC hepatotoxicity at lower exposure levels. The most common form of underlying liver disease in the developed world is non-alcoholic fatty liver disease (NAFLD). It is well-known that the type of dietary fat can play an important role in the pathogenesis of NAFLD. However, whether the combination of dietary fat and VC/metabolites promotes liver injury has not been studied. Methods: Mice were administered chloroethanol (CE - a VC metabolite) or vehicle once, 10 weeks after being fed diets rich in saturated fatty acids (HSFA), rich in poly-unsaturated fatty acids (HPUFA), or the respective low-fat control diets (LSFA; LPUFA). Results: In control mice, chloroethanol caused no detectable liver injury, as determined by plasma transaminases and histologic indices of damage. In HSFA-fed mice, chloroethanol increased HSFA-induced liver damage, steatosis, infiltrating inflammatory cells, hepatic expression of proinflammatory cytokines, and markers of endoplasmic reticulum (ER) stress. Moreover, markers of inflammasome activation were increased, while markers of inflammasome inhibition were downregulated. In mice fed HPUFA all of these effects were significantly attenuated. Conclusions: Chloroethanol promotes inflammatory liver injury caused by dietary fatty acids. This effect is far more exacerbated with saturated fat, versus poly-unsaturated fat; and strongly correlates with a robust activation of the NLRP3 inflammasome in the saturated fed animals only. Taken together these data support the hypothesis that environmental toxicant exposure can exacerbate the severity of NAFLD/NASH. - Highlights: • CE promotes inflammatory liver injury caused by dietary fatty acids. • This effect is stronger with saturated than with unsaturated fatty acids. • Damage caused by saturated fat and CE

  13. Synthesis of TMP-ester biolubricant basestock from palm stearin fatty acids

    Science.gov (United States)

    Fadzel, Fatimatuzzahraa Mohd; Salimon, Jumat; Derawi, Darfizzi

    2018-04-01

    A potential biolubricant; TMP-ester was produced via esterification of fatty acids (FA) from palm stearin (PS) with trimethylolpropane (TMP). The synthesis was conducted at four conditions; temperature, time, molar ratio of FA:TMP and H2SO4 as catalyst (by percent based on the weight of FA and TMP) that are 150 °C, 2 hours, 4:1 and 1% of H2SO4 respectively. The composition of ester produced was determined using gas chromatography (GC-FID). The presence of ester group was confirmed by the means of FTIR by the existence of strong carboxyl band of ester, v(C=O) at 1746cm-1 and 1H and 13C NMR spectroscopy shows the chemical shift, δ of ester, C=O at 2.27-2.31 ppm and 173.45 ppm accordingly. From the esterification reaction, 95% product of TMP-ester was formed. The thermal and oxidative stability of TMP-ester is 200°C.

  14. Synthesis of palm oil fatty acid and trimethylolpropane based ester for biolubricant base stocks

    Science.gov (United States)

    Nor, Nurazira Mohd; Derawi, Darfizzi; Salimon, Jumat

    2018-04-01

    RBD palm oil become one of the interesting renewable resources in biolubricant application. However, palm oil cannot be used directly as lubricant due to some performance limitations such as thermal and oxidative stability. This drawback can be overcome by chemical modification through esterification with polyhydric alcohol such as trimethylolpropane (TMP). The synthesis of ester was carried out via esterification of palm oil fatty acid (POFA) with TMP in the presence of 2% sulphuric acid as catalyst at 150 °C for 5 hours. Gas Chromatography equipped with a Flame Ionization Detector (GC-FID) was used to determine the percentage composition of POTMP ester. The structure confirmation of POTMP ester was proven by Fourier Transformation Infra-Red (FTIR), proton and carbon Nuclear Magnetic Resonance (1H-NMR and 13C-NMR) spectroscopy analysis. The result showed that POTMP ester has successfully synthesized with 97.7% composition of triesters (TE), proved by GC chromatogram. Presence of ester group also evidenced by 1H NMR at 2.27-2.30 ppm and 13C NMR at 173.52-173.54 ppm. The percentage yield of POTMP ester produced was 82% and exist in liquid form at room temperature.

  15. Rapid screening of fatty acid alkyl esters in olive oils by time domain reflectometry.

    Science.gov (United States)

    Berardinelli, Annachiara; Ragni, Luigi; Bendini, Alessandra; Valli, Enrico; Conte, Lanfranco; Guarnieri, Adriano; Toschi, Tullia Gallina

    2013-11-20

    The main aim of the present research is to assess the possibility of quickly screening fatty acid alkyl esters (FAAE) in olive oils using time domain reflectometry (TDR) and partial least-squares (PLS) multivariate statistical analysis. Eighteen virgin olive oil samples with fatty acid alkyl ester contents and fatty acid ethyl ester/methyl ester ratios (FAEE/FAME) ranging from 3 to 100 mg kg(-1) and from 0.3 to 2.6, respectively, were submitted to tests with time domain resolution of 1 ps. The results obtained in test set validation demonstrated that this new and fast analytical approach is able to predict FAME, FAEE, and FAME + FAEE contents with R(2) values of 0.905, 0.923, and 0.927, respectively. Further measurements on mixtures between olive oil and FAAE standards confirmed that the prediction is based on a direct influence of fatty acid alkyl esters on the TDR signal. The suggested technique appeared potentially suitable for monitoring one of the most important quality attribute of the olive oil in the extraction process.

  16. Biodegradation tests of mercaptocarboxylic acids, their esters, related divalent sulfur compounds and mercaptans.

    Science.gov (United States)

    Rücker, Christoph; Mahmoud, Waleed M M; Schwartz, Dirk; Kümmerer, Klaus

    2018-04-17

    Mercaptocarboxylic acids and their esters, a class of difunctional compounds bearing both a mercapto and a carboxylic acid or ester functional group, are industrial chemicals of potential environmental concern. Biodegradation of such compounds was systematically investigated here, both by literature search and by experiments (Closed Bottle Test OECD 301D and Manometric Respirometry Test OECD 301F). These compounds were found either readily biodegradable or at least biodegradable to a significant extent. Some related compounds of divalent sulfur were tested for comparison (mercaptans, sulfides, disulfides). For the two relevant monofunctional compound classes, carboxylic acids/esters and mercaptans, literature data were compiled, and by comparison with structurally similar compounds without these functional groups, the influence of COOH/COOR' and SH groups on biodegradability was evaluated. Thereby, an existing rule of thumb for biodegradation of carboxylic acids/esters was supported by experimental data, and a rule of thumb could be formulated for mercaptans. Concurrent to biodegradation, abiotic processes were observed in the experiments, rapid oxidative formation of disulfides (dimerisation of monomercaptans and cyclisation of dimercaptans) and hydrolysis of esters. Some problems that compromise the reproducibility of biodegradation test results were discussed.

  17. Thermodynamic analysis of fatty acid esterification for fatty acid alkyl esters production

    International Nuclear Information System (INIS)

    Voll, Fernando A.P.; Silva, Camila da; Rossi, Carla C.R.S.; Guirardello, Reginaldo; Castilhos, Fernanda de; Oliveira, J. Vladimir; Cardozo-Filho, Lucio

    2011-01-01

    The development of renewable energy source alternatives has become a planet need because of the unavoidable fossil fuel scarcity and for that reason biodiesel production has attracted growing interest over the last decade. The reaction yield for obtaining fatty acid alkyl esters varies significantly according to the operating conditions such as temperature and the feed reactants ratio and thus investigation of the thermodynamics involved in such reactional systems may afford important knowledge on the effects of process variables on biodiesel production. The present work reports a thermodynamic analysis of fatty acid esterification reaction at low pressure. For this purpose, Gibbs free energy minimization was employed with UNIFAC and modified Wilson thermodynamic models through a nonlinear programming model implementation. The methodology employed is shown to reproduce the most relevant investigations involving experimental studies and thermodynamic analysis.

  18. Alternative fuel properties of tall oil fatty acid methyl ester-diesel fuel blends

    Energy Technology Data Exchange (ETDEWEB)

    Altiparmak, D.; Keskin, A.; Koca, A. [Gazi University, Ankara (Turkey). Technical Education Faculty; Guru, M. [Gazi University, Ankara (Turkey). Engineering and Architectural Faculty

    2007-01-15

    In this experimental work, tall oil methyl ester-diesel fuel blends as alternative fuels for diesel engines were studied. Tall oil methyl ester was produced by reacting tall oil fatty acids with methyl alcohol under optimum conditions. The blends of tall oil methyl ester-diesel fuel were tested in a direct injection diesel engine at full load conditions. The effects of the new fuel blends on the engine performance and exhaust emission were tested. It was observed that the engine torque and power output with tall oil methyl ester-diesel fuel blends increased up to 6.1% and 5.9%, respectively. It was also seen that CO emissions decreased to 38.9% and NO{sub x} emissions increased up to 30% with the new fuel blends. The smoke capacity did not vary significantly. (author)

  19. Unsaturated Fatty Acid Esters Metathesis Catalyzed by Silica Supported WMe5

    KAUST Repository

    Riache, Nassima

    2015-11-14

    Metathesis of unsaturated fatty acid esters (FAEs) by silica supported multifunctional W-based catalyst is disclosed. This transformation represents a novel route towards unsaturated di-esters. Especially, the self-metathesis of ethyl undecylenate results almost exclusively on the homo-coupling product whereas with such catalyst, 1-decene gives ISOMET (isomerization and metathesis olefin) products. The olefin metathesis in the presence of esters is very selective without any secondary cross-metathesis products demonstrating that a high selective olefin metathesis could operate at 150 °C. Additionally, a cross-metathesis of unsaturated FAEs and α-olefins allowed the synthesis of the corresponding ester with longer hydrocarbon skeleton without isomerisation.

  20. Alternative fuel properties of tall oil fatty acid methyl ester-diesel fuel blends.

    Science.gov (United States)

    Altiparmak, Duran; Keskin, Ali; Koca, Atilla; Gürü, Metin

    2007-01-01

    In this experimental work, tall oil methyl ester-diesel fuel blends as alternative fuels for diesel engines were studied. Tall oil methyl ester was produced by reacting tall oil fatty acids with methyl alcohol under optimum conditions. The blends of tall oil methyl ester-diesel fuel were tested in a direct injection diesel engine at full load condition. The effects of the new fuel blends on the engine performance and exhaust emission were tested. It was observed that the engine torque and power output with tall oil methyl ester-diesel fuel blends increased up to 6.1% and 5.9%, respectively. It was also seen that CO emissions decreased to 38.9% and NO(x) emissions increased up to 30% with the new fuel blends. The smoke opacity did not vary significantly.

  1. FATTY ACID ETHYL ESTERS FROM MICROALGAE OF Scenedesmus ecornis BY ENZYMATIC AND ACID CATALYSIS

    Directory of Open Access Journals (Sweden)

    Gabryelle F. de Almeida

    Full Text Available Microalgae are an indispensable food source for the various growth stages of mollusks, crustaceans, and several fish species. Using a microalgae biomass present in the Amazonian ecosystem (Macapá-AP, we study extraction methods for fatty acid such as solvent extraction (magnetic stirring and/or Soxhlet and/or hydrolysis (acid and/or enzymatic catalysis followed by esterification and/or direct transesterification. Extraction of crude triacylglycerides by mechanical stirring at room temperature was more efficient than continuous reflux (Soxhlet. Subsequently, the lipid extract was subject to transesterification with ethanol and CAL-B as a biocatalyst, leading to production of fatty acid ethyl esters (FAEE. Additionally, FAEEs were prepared by hydrolysis of crude triacylglycerides followed by acid-mediated esterification or enzymatic catalysis (lipase. In this case, the type of catalyst did not significantly influence FAEE yields. In the lipid extract, we identified palmitic, linoleic, oleic, and stearic acids with palmitic acid being the most abundant. Our results suggest that enzymatic catalysis is a viable method for the extraction of lipids in the microalga, Scenedesmus ecornis.

  2. Fatty acid esters produced by Lasiodiplodia theobromae function as growth regulators in tobacco seedlings

    International Nuclear Information System (INIS)

    Uranga, Carla C.; Beld, Joris; Mrse, Anthony; Córdova-Guerrero, Iván; Burkart, Michael D.; Hernández-Martínez, Rufina

    2016-01-01

    The Botryosphaeriaceae are a family of trunk disease fungi that cause dieback and death of various plant hosts. This work sought to characterize fatty acid derivatives in a highly virulent member of this family, Lasiodiplodia theobromae. Nuclear magnetic resonance and gas chromatography-mass spectrometry of an isolated compound revealed (Z, Z)-9,12-ethyl octadecadienoate, (trivial name ethyl linoleate), as one of the most abundant fatty acid esters produced by L. theobromae. A variety of naturally produced esters of fatty acids were identified in Botryosphaeriaceae. In comparison, the production of fatty acid esters in the soil-borne tomato pathogen Fusarium oxysporum, and the non-phytopathogenic fungus Trichoderma asperellum was found to be limited. Ethyl linoleate, ethyl hexadecanoate (trivial name ethyl palmitate), and ethyl octadecanoate, (trivial name ethyl stearate), significantly inhibited tobacco seed germination and altered seedling leaf growth patterns and morphology at the highest concentration (0.2 mg/mL) tested, while ethyl linoleate and ethyl stearate significantly enhanced growth at low concentrations, with both still inducing growth at 98 ng/mL. This work provides new insights into the role of naturally esterified fatty acids from L. theobromae as plant growth regulators with similar activity to the well-known plant growth regulator gibberellic acid. - Highlights: • Lasiodiplodia theobromae produces a wide variety of fatty acid esters in natural substrates. • Ethyl stearate and ethyl linoleate inhibit tobacco germination at 0.2 mg/mL. • Ethyl stearate and ethyl linoleate induce tobacco germination at 98 ng/mL. • Tobacco growth increase in ethyl stearate and ethyl linoleate parallels gibberellic acid. • A role as plant growth regulators is proposed for fatty acid esters.

  3. Fatty acid esters produced by Lasiodiplodia theobromae function as growth regulators in tobacco seedlings

    Energy Technology Data Exchange (ETDEWEB)

    Uranga, Carla C., E-mail: curanga@cicese.edu.mx [Centro de Investigación Científica y de Educación Superior de Ensenada (CICESE), Carretera Ensenada-Tijuana 3918, Zona Playitas, 22860 Ensenada, B.C. (Mexico); Beld, Joris, E-mail: joris.beld@drexelmed.edu [University of California, San Diego, Department of Chemistry and Biochemistry, 9500 Gilman Dr., La Jolla, CA 92093-0358 (United States); Mrse, Anthony, E-mail: amrse@ucsd.edu [University of California, San Diego, Department of Chemistry and Biochemistry, 9500 Gilman Dr., La Jolla, CA 92093-0358 (United States); Córdova-Guerrero, Iván, E-mail: icordova@uabc.edu.mx [Universidad Autónoma de Baja California (UABC), Calzada Universidad 14418 Parque Industrial Internacional Tijuana, Tijuana, B.C. 22390 (Mexico); Burkart, Michael D., E-mail: mburkart@ucsd.edu [University of California, San Diego, Department of Chemistry and Biochemistry, 9500 Gilman Dr., La Jolla, CA 92093-0358 (United States); Hernández-Martínez, Rufina, E-mail: ruhernan@cicese.mx [Centro de Investigación Científica y de Educación Superior de Ensenada (CICESE), Carretera Ensenada-Tijuana 3918, Zona Playitas, 22860 Ensenada, B.C. (Mexico)

    2016-04-01

    The Botryosphaeriaceae are a family of trunk disease fungi that cause dieback and death of various plant hosts. This work sought to characterize fatty acid derivatives in a highly virulent member of this family, Lasiodiplodia theobromae. Nuclear magnetic resonance and gas chromatography-mass spectrometry of an isolated compound revealed (Z, Z)-9,12-ethyl octadecadienoate, (trivial name ethyl linoleate), as one of the most abundant fatty acid esters produced by L. theobromae. A variety of naturally produced esters of fatty acids were identified in Botryosphaeriaceae. In comparison, the production of fatty acid esters in the soil-borne tomato pathogen Fusarium oxysporum, and the non-phytopathogenic fungus Trichoderma asperellum was found to be limited. Ethyl linoleate, ethyl hexadecanoate (trivial name ethyl palmitate), and ethyl octadecanoate, (trivial name ethyl stearate), significantly inhibited tobacco seed germination and altered seedling leaf growth patterns and morphology at the highest concentration (0.2 mg/mL) tested, while ethyl linoleate and ethyl stearate significantly enhanced growth at low concentrations, with both still inducing growth at 98 ng/mL. This work provides new insights into the role of naturally esterified fatty acids from L. theobromae as plant growth regulators with similar activity to the well-known plant growth regulator gibberellic acid. - Highlights: • Lasiodiplodia theobromae produces a wide variety of fatty acid esters in natural substrates. • Ethyl stearate and ethyl linoleate inhibit tobacco germination at 0.2 mg/mL. • Ethyl stearate and ethyl linoleate induce tobacco germination at 98 ng/mL. • Tobacco growth increase in ethyl stearate and ethyl linoleate parallels gibberellic acid. • A role as plant growth regulators is proposed for fatty acid esters.

  4. Effect of sugar fatty acid esters on rumen fermentation in vitro

    OpenAIRE

    Wakita, M.; Hoshino, S.

    1987-01-01

    1.The effect of sugar fatty acid esters (SFEs; currently used as food additives for human consumption) on rumen volatile fatty acids (VFA) and gas production was studied with sheep rumen contents in vitro.2. Some SFEs having monoester contents of more than 70% increased the molar proportion of propionate in conjunction with reduction in the acetate: propionate ratio when the individual SFE was added to rumen contents in a final concentration of 4 g/l. Laurate sugar ester was the most potent p...

  5. The occurrence of 2-hydroxy-6-methoxybenzoic acid methyl ester in Securidaca longepedunculata Fresen root bark

    Directory of Open Access Journals (Sweden)

    Lognay G.

    2000-01-01

    Full Text Available As part of our ongoing search for natural fumigants from Senegalese plants, we have investigated Securicicidaca longepedunculata root barks and demonstrated that 2-hydroxy-benzoic acid methyl ester (methyl salicylate, I is responsible of their biocide effect against stored grain insects. A second unknown apparented product, II has been systematically observed in all analyzed samples. The present paper describes the identification of this molecule. The analytical investigations including GCMS, GLC and 1H-NMR. spectrometry led to the conclusion that II corresponds to the 2-hydroxy-6-methoxybenzoic acid methyl ester.

  6. Effect of sugar fatty acid esters on rumen fermentation in vitro.

    Science.gov (United States)

    Wakita, M; Hoshino, S

    1987-11-01

    1. The effect of sugar fatty acid esters (SFEs; currently used as food additives for human consumption) on rumen volatile fatty acids (VFA) and gas production was studied with sheep rumen contents in vitro. 2. Some SFEs having monoester contents of more than 70% increased the molar proportion of propionate in conjunction with reduction in the acetate:propionate ratio when the individual SFE was added to rumen contents in a final concentration of 4 g/l. Laurate sugar ester was the most potent propionate enhancer and rumen gas depressor, the effective dose being as low as 1 g/l in a final concentration. Fatty acid esters other than SFEs had little, if any, effect on rumen VFA production and their molar proportions. 3. Approximately 50% of laurate sugar ester was hydrolysed by in vitro incubation with rumen fluid for 2 h. The addition of fatty acids and sucrose was also effective in the alterations of rumen VFA and gas production. However, the effect of SFEs on in vitro rumen fermentation was significantly greater than that of their constituent fatty acids or sucrose, or both. Accordingly, the effect appeared to be ascribed to the complex action of SFE itself and to its constituents, free fatty acids and sucrose. 4. SFEs, at the level of 4 g/l, reduced substantially the froth formation (ingesta volume increase) and seemed to be effective for the prevention of bloat.

  7. Palladium-Catalyzed Decarboxylative γ-Olefination of 2,5-Cyclohexadiene-1-carboxylic Acid Derivatives with Vinyl Halides.

    Science.gov (United States)

    Chang, Chi-Hao; Chou, Chih-Ming

    2018-04-06

    This study explores a Pd-catalyzed decarboxylative Heck-type Csp 3 -Csp 2 coupling reaction of 2,5-cyclohexadiene-1-carboxylic acid derivatives with vinyl halides to provide γ-olefination products. The olefinated 1,3-cyclohexadienes can be further oxidized to produce meta-alkylated stilbene derivatives. Additionally, the conjugated diene products can also undergo a Diels-Alder reaction to produce a bicyclo[2.2.2]octadiene framework.

  8. Synthesis of sulfur-containing lubricant additives on the basis of fatty acid ethyl esters

    Directory of Open Access Journals (Sweden)

    Iurii S. Bodachivskyi

    2016-12-01

    Full Text Available The study reveals an energy-, resource- and eco-friendly method for preparation of sulfur-containing lubricant additives via interaction of fatty acid ethyl esters of rapeseed oil with elemental sulfur. The structure of synthesized compounds under various reactants ratio (5–50 wt.% of sulfur, duration (30–240 min and temperature of the process (160–215°С was investigated using various analytical techniques. According to the established data, aside from addition to double bonds, the side reaction of hydrogen substitution at α-methylene groups near these bonds occurs and induces the formation of conjugated systems and chromophoric sulfur-rich derivatives. Also, we found that increase of process duration evokes growth of polysulfane chains, in contrast to the raise of temperature, which leads to the formation of sulfur-containing heterocycles and hydrogen sulfide, as a result of elimination. Influence of accelerators on sulfurization of fatty acid ethyl esters was also examined. The most effective among them are mixtures of zinc dibutyldithiocarbamate with zinc oxide or stearic acid, which soften synthesis conditions and doubly decrease duration of the high-temperature stage. In addition, sulfur-containing compositions of ethyl esters and α-olefins, vulcanized esters by benzoyl peroxide, nonylphenols and zinc dinonylphenyldithiophosphate were designed. The study identified that lithium lubricant with sulfurized vulcanized esters provides improved tribological properties, in comparison with base lubricant or lubricant with the non-modified product.

  9. Poly(vinyl alcohol)-Tannic Acid Hydrogels with Excellent Mechanical Properties and Shape Memory Behaviors.

    Science.gov (United States)

    Chen, Ya-Nan; Peng, Lufang; Liu, Tianqi; Wang, Yaxin; Shi, Shengjie; Wang, Huiliang

    2016-10-12

    Shape memory hydrogels have promising applications in a wide variety of fields. Here we report the facile fabrication of a novel type of shape memory hydrogels physically cross-linked with both stronger and weaker hydrogen bonding (H-bonding). Strong multiple H-bonding formed between poly(vinyl alcohol) (PVA) and tannic acid (TA) leads to their coagulation when they are physically mixed at an elevated temperature and easy gelation at room temperature. The amorphous structure and strong H-bonding endow the PVA-TA hydrogels with excellent mechanical properties, as indicated by their high tensile strengths (up to 2.88 MPa) and high elongations (up to 1100%). The stronger H-bonding between PVA and TA functions as the "permanent" cross-link and the weaker H-bonding between PVA chains as the "temporary" cross-link. The reversible breakage and formation of the weaker H-bonding imparts the PVA-TA hydrogels with excellent temperature-responsive shape memory. Wet and dried hydrogel samples with a deformed or elongated shape can recover to their original shapes when immersed in 60 °C water in a few seconds or at 125 °C in about 2.5 min, respectively.

  10. Adsorption of {alpha}-amylase onto poly(N-vinyl 2-pyrrolidone/itaconic acid) hydrogels

    Energy Technology Data Exchange (ETDEWEB)

    Tuemtuerk, Hayrettin; Caykara, Tuncer; Kantoglu, Oemer; Gueven, Olgun

    1999-05-02

    {alpha}-Amylase enzyme was adsorbed on poly(N-vinyl 2-pyrrolidone/itaconic acid) (P(VP/IA)) hydrogels prepared by irradiating the ternary mixtures of VP/IA/water by {gamma}-rays at ambient temperature. The adsorption capacity of the hydrogels was determined to increase from 2.30 to 3.40 mg {alpha}-amylase/g dry gel with increasing amount of IA in gel system. Kinetic parameters were calculated as 2.51 g/dm{sup 3} for K{sub m} and 1.67x10{sup -3} g/dm{sup 3} min for V{sub max} for free enzyme and in the range of 3.88-5.02 g/dm{sup 3} for K{sub m} and 1.62x10{sup -3}-2.27 x 10{sup -3} g/dm{sup 3} min for V{sub max} depending on the amount of IA in the hydrogel. Enzyme activities were found to increase from 49.9% to 77.4% with increasing amount of IA in the gel system and retained their activities for one month storage. On the other hand, the free enzyme loses its activity completely after 20 days.

  11. Removal of some basic dyes by poly (Vinyl Alcohol/ acrylic acid)Hydrogel

    International Nuclear Information System (INIS)

    Hegazy, S.A.; Abdel-AAl, S.E.; Abdel-Rehim, H.A.; Khalifa, N.A.; El-Hosseiny, E.M.

    2000-01-01

    A study has made on the preparation and properties of poly (vinyl alcohol/ acrylic acid) hydrogel for the purpose of removal of cationic dyes from aqueous solutions. The effect of dose and monomer concentration on the uptake property of the hydrogel toward dye was studied. The uptake of basic methylene blue-9 dye with PVA/AAc was studied by the batch adsorption technique. The effect of pH on the dye uptake was demonstrated to find out that the suitable pH for maximum uptake occurred at pH 5. It was observed that as the concentration of dye is increased the dye uptake decreased. Furthermore, the uptake of dye by hydrogels increased as the temperature was elevated. The recovery of dye adsorbed is possible by treating the hydrogel with 5% HCl. The results obtained suggested this hydrogel possessed good removal properties towards basic methylene blue-9 dye, and this suggests that such hydrogels could be acceptable for practical uses

  12. Lipase catalyzed epoxidation of fatty acid methyl esters derived from unsaturated vegetable oils in absence of carboxylic acid.

    Science.gov (United States)

    Sustaita-Rodríguez, Alejandro; Ramos-Sánchez, Víctor H; Camacho-Dávila, Alejandro A; Zaragoza-Galán, Gerardo; Espinoza-Hicks, José C; Chávez-Flores, David

    2018-04-11

    Nowadays the industrial chemistry reactions rely on green technologies. Enzymes as lipases are increasing its use in diverse chemical processes. Epoxidized fatty acid methyl esters obtained from transesterification of vegetable oils have recently found applications as polymer plasticizer, agrochemical, cosmetics, pharmaceuticals and food additives. In this research article, grapeseed, avocado and olive oils naturally containing high percents of mono and poly unsaturations were used as starting materials for the production of unsaturated fatty acid methyl esters. The effect of lauric acid as an active oxygen carrier was studied on epoxidation reactions where unsaturated fatty acid methyl esters were converted to epoxy fatty acid methyl esters using immobilized Candida antarctica Lipase type B as catalyst and hydrogen peroxide as oxygen donor at mild temperature and pressure conditions. After this study it was confirmed by 1 H NMR, 13 C NMR and GC-MS that the addition of lauric acid to the enzymatic reaction is unnecessary to transform the alkenes in to epoxides. It was found that quantitative conversions were possible in despite of a carboxylic acid absence.

  13. α,β-Unsaturated monoterpene acid glucose esters: structural diversity, bioactivities and functional roles.

    Science.gov (United States)

    Goodger, Jason Q D; Woodrow, Ian E

    2011-12-01

    The glycosylation of lipophilic small molecules produces many important plant secondary metabolites. The majority of these are O-glycosides with relatively fewer occurring as glucose esters of aromatic or aliphatic acids. In particular, monoterpene acid glucose esters have much lower structural diversity and distribution compared to monoterpene glycosides. Nevertheless, there have been over 20 monoterpene acid glucose esters described from trees in the genus Eucalyptus (Myrtaceae) in recent years, all based on oleuropeic acid, menthiafolic acid or both. Here we review all of the glucose esters containing these monoterpenoids identified in plants to date. Many of the compounds contain phenolic aglycones and all contain at least one α,β-unsaturated carbonyl, affording a number of important potential therapeutic reactivities such as anti-tumor promotion, carcinogenesis suppression, and anti-oxidant and anti-inflammatory activities. Additional properties such as cytotoxicity, bitterness, and repellency are suggestive of a role in plant defence, but we also discuss their localization to the exterior of foliar secretory cavity lumina, and suggest they may also protect secretory cells from toxic terpenes housed within these structures. Finally we discuss how the use of a recently developed protocol to isolate secretory cavities in a functional state could be used in conjunction with systems biology approaches to help characterize their biosynthesis and roles in plants. Copyright © 2011 Elsevier Ltd. All rights reserved.

  14. Molecular Basis of Prodrug Activation by Human Valacyclovirase, an [alpha]-Amino Acid Ester Hydrolase

    Energy Technology Data Exchange (ETDEWEB)

    Lai, Longsheng; Xu, Zhaohui; Zhou, Jiahai; Lee, Kyung-Dall; Amidon, Gordon L. (Michigan)

    2008-07-08

    Chemical modification to improve biopharmaceutical properties, especially oral absorption and bioavailability, is a common strategy employed by pharmaceutical chemists. The approach often employs a simple structural modification and utilizes ubiquitous endogenous esterases as activation enzymes, although such enzymes are often unidentified. This report describes the crystal structure and specificity of a novel activating enzyme for valacyclovir and valganciclovir. Our structural insights show that human valacyclovirase has a unique binding mode and specificity for amino acid esters. Biochemical data demonstrate that the enzyme hydrolyzes esters of {alpha}-amino acids exclusively and displays a broad specificity spectrum for the aminoacyl moiety similar to tricorn-interacting aminopeptidase F1. Crystal structures of the enzyme, two mechanistic mutants, and a complex with a product analogue, when combined with biochemical analysis, reveal the key determinants for substrate recognition; that is, a flexible and mostly hydrophobic acyl pocket, a localized negative electrostatic potential, a large open leaving group-accommodating groove, and a pivotal acidic residue, Asp-123, after the nucleophile Ser-122. This is the first time that a residue immediately after the nucleophile has been found to have its side chain directed into the substrate binding pocket and play an essential role in substrate discrimination in serine hydrolases. These results as well as a phylogenetic analysis establish that the enzyme functions as a specific {alpha}-amino acid ester hydrolase. Valacyclovirase is a valuable target for amino acid ester prodrug-based oral drug delivery enhancement strategies.

  15. Synthesis and Structural Characterization of 1- and 2-Substituted Indazoles: Ester and Carboxylic Acid Derivatives

    Directory of Open Access Journals (Sweden)

    Isabel Bento

    2006-11-01

    Full Text Available A series of indazoles substituted at the N-1 and N-2 positions with ester-containing side chains -(CH2nCO2R of different lengths (n = 0-6, 9, 10 are described.Nucleophilic substitution reactions on halo esters (X(CH2nCO2R by 1H-indazole inalkaline solution lead to mixtures of N-1 and N-2 isomers, in which the N-1 isomerpredominates. Basic hydrolysis of the ester derivatives allowed the synthesis of thecorresponding indazole carboxylic acids. All compounds were fully characterised bymultinuclear NMR and IR spectroscopies, MS spectrometry and elemental analysis; theNMR spectroscopic data were used for structural assignment of the N-1 and N-2 isomers.The molecular structure of indazol-2-yl-acetic acid (5b was determined by X-raydiffraction, which shows a supramolecular architecture involving O2-H...N1intermolecular hydrogen bonds.

  16. 40 CFR 721.3100 - Oligomeric silicic acid ester compound with a hy-droxyl-al-kyla-mine.

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Oligomeric silicic acid ester compound with a hy-droxyl-al-kyla-mine. 721.3100 Section 721.3100 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.3100 Oligomeric silicic acid ester compound with a...

  17. The Inhibition of Aluminum Corrosion in Sulfuric Acid by Poly(1-vinyl-3-alkyl-imidazolium Hexafluorophosphate

    Directory of Open Access Journals (Sweden)

    Paulina Arellanes-Lozada

    2014-08-01

    Full Text Available Compounds of poly(ionic liquids (PILs, derived from imidazole with different alkylic chain lengths located in the third position of the imidazolium ring (poly(1-vinyl-3-dodecyl-imidazolium (PImC12, poly(1-vinyl-3-octylimidazolium (PImC8 and poly(1-vinyl-3-butylimidazolium (PImC4 hexafluorophosphate were synthesized. These compounds were tested as corrosion inhibitors on aluminum alloy AA6061 in diluted sulfuric acid (0.1–1 M H2SO4 by weight loss tests, polarization resistance measurements and inductively coupled plasma optical emission spectroscopy. Langmuir’s isotherms suggested film formation on bare alloy while standard free energy indicated inhibition by a physisorption process. However, compound efficiencies as inhibitors ranked low (PImC12 > PImC8 > PImC4 to reach 61% for PImC12 in highly diluted acidic solution. Apparently, the high mobility of sulfates favored their adsorption in comparison to PILs. The surface film displayed general corrosion, and pitting occurred as a consequence of PILs’ partial inhibition along with a continuous dissolution of defective patchy film on formation. A slight improvement in efficiency was displayed by compounds having high molecular weight and a long alkyl chain, as a consequence of steric hindrance and PIL interactions.

  18. The Inhibition of Aluminum Corrosion in Sulfuric Acid by Poly(1-vinyl-3-alkyl-imidazolium Hexafluorophosphate).

    Science.gov (United States)

    Arellanes-Lozada, Paulina; Olivares-Xometl, Octavio; Guzmán-Lucero, Diego; Likhanova, Natalya V; Domínguez-Aguilar, Marco A; Lijanova, Irina V; Arce-Estrada, Elsa

    2014-08-07

    Compounds of poly(ionic liquid)s (PILs), derived from imidazole with different alkylic chain lengths located in the third position of the imidazolium ring (poly(1-vinyl-3-dodecyl-imidazolium) (PImC 12 ), poly(1-vinyl-3-octylimidazolium) (PImC₈) and poly(1-vinyl-3-butylimidazolium) (PImC₄) hexafluorophosphate) were synthesized. These compounds were tested as corrosion inhibitors on aluminum alloy AA6061 in diluted sulfuric acid (0.1-1 M H₂SO₄) by weight loss tests, polarization resistance measurements and inductively coupled plasma optical emission spectroscopy. Langmuir's isotherms suggested film formation on bare alloy while standard free energy indicated inhibition by a physisorption process. However, compound efficiencies as inhibitors ranked low (PImC 12 > PImC₈ > PImC₄) to reach 61% for PImC 12 in highly diluted acidic solution. Apparently, the high mobility of sulfates favored their adsorption in comparison to PILs. The surface film displayed general corrosion, and pitting occurred as a consequence of PILs' partial inhibition along with a continuous dissolution of defective patchy film on formation. A slight improvement in efficiency was displayed by compounds having high molecular weight and a long alkyl chain, as a consequence of steric hindrance and PIL interactions.

  19. Metabolism of dietary fatty alcohol, fatty acid, and wax ester in carp

    International Nuclear Information System (INIS)

    Mankura, Mitsumasa; Kayama, Mitsu; Iijima, Noriaki.

    1987-01-01

    Lipids in various tissues of the carp, Cyprinus carpio were analyzed. The fates of force-fed [1- 14 C]palmitic acids, [1- 14 C]cetyl alcohol, and oleyl[1- 14 C]linoleate, were compared with those given in vitro experiments. Major lipid classes in all except adipose tissue were found to be polar lipids (phospholipids) and triacylglycerols. The major fatty acids in nearly all the tissues were 16 : 0, 18 : 1, 18 : 2, and 22 : 6. Although the radioactivity incorporation into wax esters from [1- 14 C]palmitic acid and [1- 14 C]cetyl alcohol for various tissue homogenates was quite high, in vivo incorporation of these labelled compounds into wax esters was very low and radioactivity was distributed mainly in the lipids of muscle, skin, hepatopancreas, intestine, and gill. Almost all the radioactivity in various tissues was present in phospatidylcholine and triacylglycerols. Most of the oleyl[1- 14 C]linoleate was easily hydrolyzed by various tissue homogenates. Force-fed oleyl[1- 14 C]linoleate was hydrolyzed in the intestine and then transported to other tissues, such as muscle, kin, gill, and hepatopancreas. Moreover, released radioactivity from oleyl[1- 14 C]linoleate was present in mainly phosphatidylcholine and triacylglycerols. Radioactivity was also detected in wax esters in plasma. Certain amounts for fatty acids released from [1- 14 C]triolein in the hepatopancreas homogenates were incorporated into wax esters; this was stimulated by the addition of oleyl alcohol. The present results indicate extensive hydrolysis of wax ester to possibly occur in the intestine and certain portions of the fatty alcohol moiety to be resterfied. The portions may be oxidized to fatty acids and which subsequently behave as dietary fatty acids. (author) 50 ref

  20. Theoretical Studies Of Molecular Structure And Vibrational Spectra Of 5-Aminolevulinic Acid Hexyl Ester

    International Nuclear Information System (INIS)

    Comert, H.

    2010-01-01

    The molecular geometry and vibrational frequencies of The 5-Aminolevulinic acid's hexyl ester (ALA-H) in the ground state have been calculated using Hartree-Fock (HF) and Density functional method (B3LYP) with 6-31++G(d) basis set. The calculated vibrational spectra and geometric parameters of title compound were compered with experimental ones.

  1. 40 CFR 721.3700 - Fatty acid, ester with styrenated phenol, ethylene oxide adduct.

    Science.gov (United States)

    2010-07-01

    ... phenol, ethylene oxide adduct. 721.3700 Section 721.3700 Protection of Environment ENVIRONMENTAL..., ethylene oxide adduct. (a) Chemical substances and significant new uses subject to reporting. (1) The chemical substance identified generically as fatty acid, ester with styrenated phenol, ethylene oxide...

  2. 4-[(2-Hydroxy-4-pentadecyl-benzylidene-amino]-benzoic Acid Methyl Ester

    Directory of Open Access Journals (Sweden)

    Gadada Naganagowda

    2013-11-01

    Full Text Available A new Schiff base, 4-[(2-hydroxy-4-pentadecyl-benzylidene-amino]-benzoic acid methyl ester was synthesized and its UV, IR, 1H-NMR, 13C-NMR and ESI-MS spectroscopic data are presented.

  3. CFD simulation of fatty acid methyl ester production in bubble column reactor

    Science.gov (United States)

    Salleh, N. S. Mohd; Nasir, N. F.

    2017-09-01

    Non-catalytic transesterification is one of the method that was used to produce the fatty acid methyl ester (FAME) by blowing superheated methanol bubbles continuously into the vegetable oil without using any catalyst. This research aimed to simulate the production of FAME from palm oil in a bubble column reactor. Computational Fluid Dynamic (CFD) simulation was used to predict the distribution of fatty acid methyl ester and other product in the reactor. The fluid flow and component of concentration along the reaction time was investigated and the effects of reaction temperature (523 K and 563 K) on the non-catalytic transesterification process has been examined. The study was carried out using ANSYS CFX 17.1. The finding from the study shows that increasing the temperature leads to higher amount of fatty acid methyl ester can be produced in shorter time. On the other hand, concentration of the component such as triglyceride (TG), glycerol (GL) and fatty acid methyl ester (FAME) can be known when reaching the optimum condition.

  4. Structural study of bis(triorganotin(IV)) esters of 4-ketopimelic acid

    Czech Academy of Sciences Publication Activity Database

    Chalupa, J.; Handlíř, K.; Císařová, I.; Jirásko, R.; Brus, Jiří; Lyčka, A.; Růžička, A.; Holeček, J.

    2006-01-01

    Roč. 691, č. 12 (2006), s. 2631-2640 ISSN 0022-328X R&D Projects: GA ČR GA203/03/1118 Institutional research plan: CEZ:AV0Z40500505 Keywords : triorganotin(IV) esters * ketopimelic acid * NMR Subject RIV: CD - Macromolecular Chemistry Impact factor: 2.332, year: 2006

  5. Low-temperature side-chain cleavage and decarboxylation of polythiophene esters by acid catalysis

    DEFF Research Database (Denmark)

    Søndergaard, Roar; Norrman, Kion; Krebs, Frederik C

    2012-01-01

    Solubility switching of polymers is very useful in thin layer processing of conjugated polymers, as it allows for multilayer processing and increases the stability of the polymer. Acid catalyzed thermocleavage of ester groups from thiophene polymers carrying primary, secondary, and tertiary subst...

  6. Chemical modification of nanocellulose with canola oil fatty acid methyl ester

    Science.gov (United States)

    Liqing Wei; Umesh P. Agarwal; Kolby C. Hirth; Laurent M. Matuana; Ronald C. Sabo; Nicole M. Stark

    2017-01-01

    Cellulose nanocrystals (CNCs), produced from dissolving wood pulp, were chemically functionalized by transesterification with canola oil fatty acid methyl ester (CME). CME performs as both the reaction reagent and solvent. Transesterified CNC (CNCFE) was characterized for their chemical structure, morphology, crystalline structure, thermal stability, and hydrophobicity...

  7. Carbohydrate fatty acid monosulphate esters are safe and effective adjuvants for humoral responses

    NARCIS (Netherlands)

    Hilgers, L.A.T.; Platenburg, P.; Bajramovic, J.; Veth, J.; Sauerwein, R.; Roeffen, W.; Pohl, M.; Amerongen, G. van; Stittelaar, K.J.; Bosch, J.F. van den

    2017-01-01

    Carbohydrate fatty acid sulphate esters (CFASEs) formulated in a squalane-in-water emulsion are effective adjuvants for humoral responses to a wide range of antigens in various animal species but rise in body temperature and local reactions albeit mild or minimal hampers application in humans. In

  8. SEPARATION OF T-MAZ ETHOXYLATED SORBITAN FATTY ACID ESTERS BY SUPERCRITICAL FLUID CHROMATOGRAPHY

    Science.gov (United States)

    The application of supercritical fluid chromatography (SFC) to the analysis of T-MAZ ethoxylated sorbitan fatty acid esters is described. FC separation methods utilize a density programming technique and a 50 um I.D. capillary column. his work demonstrates that capillary column S...

  9. Process Intensification of Enzymatic Fatty Acid Butyl Ester Synthesis Using a Continuous Centrifugal Contactor Separator

    NARCIS (Netherlands)

    Ilmi, Miftahul; Abduh, Muhammad Yusuf; Hommes, Arne; Winkelman, Jozef; Hidayat, C.; Heeres, Hero

    2018-01-01

    Fatty acid butyl esters were synthesized from sunflower oil with 1-butanol using a homogeneous Rhizomucor miehei lipase in a biphasic organic (triglyceride, 1-butanol, hexane)– water (with enzyme) system in a continuous setup consisting of a cascade of a stirred tank reactor and a continuous

  10. Drug-induced Fanconi syndrome associated with fumaric acid esters treatment for psoriasis: A case series

    NARCIS (Netherlands)

    D.M.W. Balak (Deepak); J.N.B. Bavinck (Jan Nico Bouwes); De Vries, A.P.J. (Aiko P. J.); Hartman, J. (Jenny); Martino Neumann, H.A. (Hendrik A.); R. Zietse (Bob); H.B. Thio (Bing)

    2016-01-01

    textabstractBackground: Fumaric acid esters (FAEs), an oral immunomodulating treatment for psoriasis and multiple sclerosis, have been anecdotally associated with proximal renal tubular dysfunction due to a drug-induced Fanconi syndrome. Few data are available on clinical outcomes of FAE-induced

  11. Amino acids and glycine ethyl ester as new crystallization reagents for lysozyme

    International Nuclear Information System (INIS)

    Ito, Len; Shiraki, Kentaro; Yamaguchi, Hiroshi

    2010-01-01

    During the past two decades, amino acids and amino-acid derivatives have been applied in various fields of protein chemistry. The potential use of amino acids and their derivatives as new precipitating agents is described. Several amino acids and their derivatives are prominent additives in the field of protein chemistry. This study reports the use of charged amino acids and glycine ethyl ester as precipitants in protein crystallization, using hen egg-white lysozyme (HEWL) as a model. A discussion of the crystallization of HEWL using these reagents as precipitating agents is given

  12. Potentiation of insulin release in response to amino acid methyl esters correlates to activation of islet glutamate dehydrogenase activity

    DEFF Research Database (Denmark)

    Kofod, Hans; Lernmark, A; Hedeskov, C J

    1986-01-01

    Column perifusion of mouse pancreatic islets was used to study the ability of amino acids and their methyl esters to influence insulin release and activate islet glutamate dehydrogenase activity. In the absence of L-glutamine, L-serine and the methyl ester of L-phenylalanine, but neither L...... glutamate dehydrogenase activity showed that only the two methyl esters of L-phenylalanine and L-serine activated the enzyme. It is concluded that the mechanism by which methyl esters of amino acids potentiate insulin release is most likely to be mediated by the activation of pancreatic beta-cell glutamate...

  13. Crystal structures of hibiscus acid and hibiscus acid dimethyl ester isolated from Hibiscus sabdariffa (Malvaceae).

    Science.gov (United States)

    Zheoat, Ahmed M; Gray, Alexander I; Igoli, John O; Kennedy, Alan R; Ferro, Valerie A

    2017-09-01

    The biologically active title compounds have been isolated from Hibiscus sabdariffa plants, hibiscus acid as a dimethyl sulfoxide monosolvate [systematic name: (2 S ,3 R )-3-hy-droxy-5-oxo-2,3,4,5-tetra-hydro-furan-2,3-di-carb-oxy-lic acid dimethyl sulfoxide monosolvate], C 6 H 6 O 7 ·C 2 H 6 OS, (I), and hibiscus acid dimethyl ester [systematic name: dimethyl (2 S ,3 R )-3-hy-droxy-5-oxo-2,3,4,5-tetra-hydro-furan-2,3-di-carboxyl-ate], C 8 H 10 O 7 , (II). Compound (I) forms a layered structure with alternating layers of lactone and solvent mol-ecules, that include a two-dimensional hydrogen-bonding construct. Compound (II) has two crystallographically independent and conformationally similar mol-ecules per asymmetric unit and forms a one-dimensional hydrogen-bonding construct. The known absolute configuration for both compounds has been confirmed.

  14. Synthesis of All-Z-1,6,9,12,15-Octadecapenten-3-one, A Vinyl Ketone Polyunsaturated Marine Natural Product Isolated from Callysponga sp.

    Directory of Open Access Journals (Sweden)

    Anne Marie Langseter

    2014-03-01

    Full Text Available The synthesis of the marine natural product 1,6Z,9Z,12Z,15Z-octadecapentaen-3-one (1 has been achieved by two different routes starting from the ethyl esters of eicosapentaenoic acid (EPA and docosahexaenoic acid (DHA, respectively. Using EPA ethyl ester as starting material the polyunsaturated vinyl ketone lipid 1 was obtained in 17% overall yield.

  15. Synthesis of esters of morpholino-4-carbothionothiolic acid as compounds of potential radioprotective action

    Energy Technology Data Exchange (ETDEWEB)

    Strzelczyk, M.; Kucharski, A. (Wojskowa Akademia Medyczna, Lodz (Poland))

    1979-01-01

    The compounds of the group of dithiocarbaminianes as complexing compounds are of importance in radioprotection. Present paper concerns the synthesis of 19, as yet undescribed dithiocarbaminianes esters of morpholino-4-carbothionothiolic acid. They were obtained in the reaction of the potassium salt of the mentioned acid with adequate alkyl or alkyloaryl halogenatas. Potassium salt of the morpholino-4-carbothionothiolic acid was obtained in the reaction of morpholine with carbon disulphite in the presence of potassium hydroxide. Obtaining of the pure potassium salt of the mentioned acid enabled the accurate calculation of the used substarate in further reactions and conduction of reaction in different solvents. Phenyloalkyl, phenacyl and morpholino-4-carbonyloalkyl esters were obtained. Their chemical structure was confirmed by elementary and spectral infrared analysis.

  16. Asymmetric Meerwein–Ponndorf–Verley reduction of long chain keto alkanoic acid methyl esters

    Directory of Open Access Journals (Sweden)

    AYE YUSUFOGLU

    2007-05-01

    Full Text Available 3-, 7- and 13-Monoketo tetradecanoic acid methyl esters carrying a ketogroup at the ends and at the middle of the chain with 14 carbon atoms were reduced by a Meerwein–Ponndorf–Verley reaction in the presence of R-(+-1,1'-binaphthalene-2,2'-diol, 1,2:5,6-D-di-O-isopropylidene-D-mannitol and L-(–-menthol. The highest enantiomeric purity of 65% ee was found for 13-hydroxy ester isomer. The enantiomeric excess was determined by 1H-NMR shift with Eu(tfc3 and by optical rotation.

  17. Changes of lipid and fatty acid absorption induced by high dose of citric acid ester and lecithin emulsifiers.

    Science.gov (United States)

    Sadouki, Mohamed; Bouchoucha, Michel

    2014-09-01

    To describe the effect of two food emulsifiers, lecithin (E322) and citric acid esters of mono-and diglycerides of fatty acids (E472c), on the intestinal absorption of lipids. The experiment was conducted on 24 male Wistar rats randomly assigned in three groups. For two groups of six rats, 30% of the lipid intake was replaced with lecithin (L) or citric acid ester of mono and diglycerides, (E); the remaining 12 rats were the control group (C). Diet and fecal fat analysis was used to determine the apparent lipid absorption (ALA) and fatty acids. ALA was significantly lower in the group E than in the groups C and L (p acids decreased while the length of the carbon chains increased, and this decrease was higher in the group E. E472c emulsifier decreased the intestinal absorption of lipids.

  18. Microalgal fatty acid methyl ester a new source of bioactive compounds with antimicrobial activity

    OpenAIRE

    Arumugham Suresh; Ramasamy Praveenkumar; Ramasamy Thangaraj; Felix Lewis Oscar; Edachery Baldev; Dharumadurai Dhanasekaran; Nooruddin Thajuddin

    2014-01-01

    Objective: To evaluate fatty acid composition and the antimicrobial activity of the major fraction of fatty acid methyl ester (FAME) extracts from three microalgae collected from freshwater lakes in Theni District, Tamil Nadu, India. Methods: Antimicrobial study was carried out by well diffusion method against bacterial as well as fungal pathogens such as Escherichia coli, Staphylococcus aureus, Enterobacter sp., Klebsiella sp., Salmonella typhi, Fusarium sp., Cryptococcus sp.,...

  19. GC-MS ANALYSIS OF THE FATTY ACID METHYL ESTER IN JAPANESE QUAIL FAT

    Directory of Open Access Journals (Sweden)

    Ion Dragalin

    2015-12-01

    Full Text Available The accumulated as production waste fat from Faraon quail breeds has been investigated for the first time by using GC-MS technique, preventively converting it via methanolysis to fatty acid methyl esters. The test results, regarding the content of unsaturated fatty acids having a favorable to human body cis-configuration (77.8%, confirm their nutritional value and the possibility of using this fat in cosmetic, pharmaceutical and food industries.

  20. Tribological study of a highly hydrolytically stable phenylboronic acid ester containing benzothiazolyl in mineral oil

    International Nuclear Information System (INIS)

    Li, Zhipeng; Li, Xiufeng; Zhang, Yawen; Ren, Tianhui; Zhao, Yidong; Zeng, Xiangqiong; Heide, E. van der

    2014-01-01

    A novel long chain alkyl phenylboronic acid ester containing heterocyclic compound, bis (1-(benzothiazol-2-ylthio) propan-2-yl)-4-dodecylphenylboronic acid ester (DBBMT), was synthesized and characterized. The hydrolytic stability of the DBBMT was evaluated and the results show that DBBMT is of outstanding hydrolytic stability compared with normal borate esters, which indicates that the designed molecular structure, by introducing benzene ring to conjugate with the electron-deficient boron and the benzothiazole as a hinder group, is effective on obtaining a hydrolytically stable long chain alkyl phenylboronic acid ester. The tribological properties of DBBMT and ZDDP in mineral base oil were evaluated using a four-ball tribometer, which suggests that the DBBMT possesses comprehensive tribological properties and could be a potential candidate for the replacement of ZDDP. Furthermore, in order to understand the tribological behaviors, the worn surface was analyzed by X-ray photoelectron spectroscopy (XPS) and X-ray absorption near edge structure (XANES) spectroscopy. The results indicate that the elements S, B, O and Fe perform complicated tribochemical reactions to form the compact tribological film composed of B 2 O 3 , FeS, Fe 3 O 4 and FeSO 4 .

  1. Effects of partial hydrogenation, epoxidation, and hydroxylation on the fuel properties of fatty acid methyl esters

    Energy Technology Data Exchange (ETDEWEB)

    Wadumesthrige, Kapila; Salley, Steven O.; Ng, K.Y. Simon [Department of Chemical Engineering and Materials Science, Wayne State University, 5050 Anthony Wayne Drive, Detroit, MI 48202 (United States)

    2009-10-15

    The properties of biodiesel depend on the chemical structure of individual fatty acid methyl esters (FAME). In this work the chemical structure of fatty acid chains was modified by catalytic hydrogenation, epoxidation and hydroxylation under controlled conditions. Hydrolysis of ester functionality or oxidation of fatty acid chain was not observed during these reactions. The properties of hydrogenated FAME strongly depend on the hydrogenation time. The total saturated fatty acid (SFA) percentage increased from 29.3% to 76.2% after 2 h of hydrogenation. This hydrogenated FAME showed higher oxidation stability and higher cetane number but poor cold flow properties. Formation of trans FAME was observed during hydrogenation. Both hydroxylation and epoxidation resulted in a decrease of unsaturated fatty acid methyl ester (UFA) fraction. The percentages of total unsaturated FAME decreased 39% in the epoxidation reaction and 44% in the hydroxylation reaction. The addition of hydroxyl groups to the unsaturated regions of the fatty acid chain yields biodiesel with better cold flow properties, increased lubricity and slightly increased oxidative stability. However, epoxy FAME shows some interesting properties such as higher oxidation stability, higher cetane number and acceptable cold flow properties, which met the limits of ASTM D6751 biodiesel specifications. (author)

  2. Enzymatic synthesis of arbutin undecylenic acid ester and its inhibitory effect on mushroom tyrosinase.

    Science.gov (United States)

    Tokiwa, Y; Kitagawa, M; Raku, T

    2007-03-01

    A novel tyrosinase inhibitor, an arbutin derivative having undecylenic acid at the 6-position of its glucose moiety, was enzymatically synthesized. Its inhibitory activity was studied in vitro by using catechol and phenol as substrates. The IC(50) value of the arbutin ester on tyrosinase using catechol (4 x 10(-4) M) was 1% of that when arbutin (4 x 10(-2) M) was used. Using phenol, IC(50) of the arbutin ester (3 x 10(-4) M) as substrate was 10% of that of arbutin (3 x 10(-3) M). These results suggest that the arbutin ester inhibits the latter part of the tyrosinase reaction, which consists of hydroxylation and oxidation.

  3. Permeability of solutes through cellophanes grafted with vinyl monomers. I. Diffusion of potassium chloride, urea, and uric acid

    International Nuclear Information System (INIS)

    Takigami, S.; Maeda, Y.; Nakamura, Y.

    1979-01-01

    The diffusive permeability of potassium chloride, urea, and uric acid through cellophanes grafted with acrylamide, acrylic acid, styrene, and N-vinyl-2-pyrrolidone by γ-ray irradiation was studied. The diffusive permeability coefficients of the permeants through the grafted cellophanes were increased with increase in hydration of the grafted membranes, except for the permeation of potassium chloride through cellophanes grafted with acrylic acid. The permeation of potassium chloride, urea, and uric acid through the various grafted cellophanes is explained by the free volume concept of homogeneously water-swollen membranes. However, the behavior of the permeation of potassium chloride through cellophane grafted with acrylic acid deviated from that of nonionic membranes because of the contribution of the electrical interaction between electrolyte and charge of the membrane. 4 figures, 3 tables

  4. Toxicological assessment of 3-chloropropane-1,2-diol and glycidol fatty acid esters in food.

    Science.gov (United States)

    Bakhiya, Nadiya; Abraham, Klaus; Gürtler, Rainer; Appel, Klaus Erich; Lampen, Alfonso

    2011-04-01

    Fatty acid esters of 3-chloropropane-1,2-diol (3-MCPD) and glycidol are a newly identified class of food process contaminants. They are widespread in refined vegetable oils and fats and have been detected in vegetable fat-containing products, including infant formulas. There are no toxicological data available yet on the 3-MCPD and glycidol esters, and the primary toxicological concern is based on the potential release of 3-MCPD or glycidol from the parent esters by lipase-catalyzed hydrolysis in the gastrointestinal tract. Although 3-MCPD is assessed as a nongenotoxic carcinogen with a tolerable daily intake (TDI) of 2 μg/kg body weight (bw), glycidol is a known genotoxic carcinogen, which induces tumors in numerous organs of rodents. The initial exposure estimates, conducted by Federal Institute for Risk Assessment (BfR) under the assumption that 100% of the 3-MPCD and glycidol are released from their esters, revealed especially that infants being fed commercial infant formula could ingest harmful amounts of 3-MCPD and glycidol. However, the real oral bioavailability may be lower. As this gives rise for toxicological concern, the currently available toxicological data of 3-MCPD and glycidol and their esters are summarized in this review and discussed with regard to data gaps and further research needs. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  5. A new, direct analytical method using LC-MS/MS for fatty acid esters of 3-chloro-1,2-propanediol (3-MCPD esters) in edible oils.

    Science.gov (United States)

    Yamazaki, K; Ogiso, M; Isagawa, S; Urushiyama, T; Ukena, T; Kibune, N

    2013-01-01

    A new, direct analytical method for the determination of 3-chloro-1,2-propanediol fatty acid esters (3-MCPD esters) was developed. The targeted 3-MCPD esters included five types of monoester and 25 [corrected] types of diester. Samples (oils and fats) were dissolved in a mixture of tert-butyl methyl ether and ethyl acetate (4:1), purified using two solid-phase extraction (SPE) cartridges (C(18) and silica), then analysed by liquid chromatography-tandem mass spectrometry (LC-MS/MS). Five monoesters and five diesters with the same fatty acid group could be separated and quantified. Pairs of 3-MCPD diesters carrying the same two different fatty acid groups, but at reversed positions (sn-1 and sn-2), could not be separated and so were expressed as a sum of both compounds. The limits of quantification (LOQs) were estimated to be between 0.02 to 0.08 mg kg(-1), depending on the types of 3-MCPD ester. Repeatability expressed as relative standard deviation (RSD(r)%) varied from 5.5% to 25.5%. The new method was shown to be applicable to various commercial edible oils and showed levels of 3-MCPD esters varying from 0.58 to 25.35 mg kg(-1). The levels of mono- and diesters ranged from 0.10 to 0.69 mg kg(-1) and from 0.06 to 16 mg kg(-1), respectively.

  6. Docosahexaenoic Acid-Derived Fatty Acid Esters of Hydroxy Fatty Acids (FAHFAs) With Anti-inflammatory Properties.

    Science.gov (United States)

    Kuda, Ondrej; Brezinova, Marie; Rombaldova, Martina; Slavikova, Barbora; Posta, Martin; Beier, Petr; Janovska, Petra; Veleba, Jiri; Kopecky, Jan; Kudova, Eva; Pelikanova, Terezie; Kopecky, Jan

    2016-09-01

    White adipose tissue (WAT) is a complex organ with both metabolic and endocrine functions. Dysregulation of all of these functions of WAT, together with low-grade inflammation of the tissue in obese individuals, contributes to the development of insulin resistance and type 2 diabetes. n-3 polyunsaturated fatty acids (PUFAs) of marine origin play an important role in the resolution of inflammation and exert beneficial metabolic effects. Using experiments in mice and overweight/obese patients with type 2 diabetes, we elucidated the structures of novel members of fatty acid esters of hydroxy fatty acids-lipokines derived from docosahexaenoic acid (DHA) and linoleic acid, which were present in serum and WAT after n-3 PUFA supplementation. These compounds contained DHA esterified to 9- and 13-hydroxyoctadecadienoic acid (HLA) or 14-hydroxydocosahexaenoic acid (HDHA), termed 9-DHAHLA, 13-DHAHLA, and 14-DHAHDHA, and were synthesized by adipocytes at concentrations comparable to those of protectins and resolvins derived from DHA in WAT. 13-DHAHLA exerted anti-inflammatory and proresolving properties while reducing macrophage activation by lipopolysaccharides and enhancing the phagocytosis of zymosan particles. Our results document the existence of novel lipid mediators, which are involved in the beneficial anti-inflammatory effects attributed to n-3 PUFAs, in both mice and humans. © 2016 by the American Diabetes Association.

  7. [Preparation and physicochemical property of carboxymethyl-chitosan/hyaluronic acid poly(vinyl alcohol) blend membrane].

    Science.gov (United States)

    Liu, Wen; Li, Shuning; Chang, Jing; Han, Baoqin; Liu, Wanshun

    2009-08-01

    To prepare carboxymethyl-chitosan/hyaluronic acid/poly(vinyl alcohol) (CHP) blend membrane, evaluate its physicochemical properties and intraocular biocompatibility and to investigate its feasibility to be applied to glaucoma filtering surgery. CHP blend membrane was prepared using solution casting method after blending carboxymethyl-chitosan, HA and poly(vinyl alcohol) in a proportion of 5 : 4 : 1 (M/M). Its water absorption rate, swelling rate, permeability, and mechanical properties were detected. Subconjunctival fibroblasts separated from subconjunctival tissue of New Zealand white rabbits were cultured, and the cells at passage 4 were cultured on cell culture plate with or without the CHP blend membrane, serving as the experimental group and the control group, respectively. Effect of the CHP blend membrane on the subconjunctival fibroblasts was tested by MTT method 24, 48, and 72 hours after culture. Six New Zealand white rabbits were randomly divided into two groups (n = 3 rabbits per group), and the CHP blend membrane and SK gel were implanted into the rabbits' subconjunctival space and anterior chamber in the experimental group and the control group, respectively. Slit lamp observation and binocular reaction record were conducted 1, 3, 5, 9, 11, 20, 30, 45, and 60 days after operation. Corneal tissue harvested from the experimental group was observed using scanning electron microscope 15 days after operation to study ophthalmic biocompatibility and biodegradability. The water absorption rate and the swelling rate of the CHP blend membrane was 83.8% +/- 1.3% and 3.59 +/- 0.50, respectively. The tensile strength of the dry and the wet CHP blend membrane was (20.59 +/- 1.73) and (0.51 +/- 0.13) MPa, respectively. The breaking elongation rate of the dry and the wet CHP blend membrane was 10.69% +/- 1.16% and 53.15% +/- 2.46%, respectively. The CHP blend membrane had good permeability to NaCl and L-tyrosine. Absorbance (A) value of the experimental group 24, 48

  8. Gas chromatography-vacuum ultraviolet spectroscopy for analysis of fatty acid methyl esters.

    Science.gov (United States)

    Fan, Hui; Smuts, Jonathan; Bai, Ling; Walsh, Phillip; Armstrong, Daniel W; Schug, Kevin A

    2016-03-01

    A new vacuum ultraviolet (VUV) detector for gas chromatography was recently developed and applied to fatty acid methyl ester (FAME) analysis. VUV detection features full spectral acquisition in a wavelength range of 115-240nm, where virtually all chemical species absorb. VUV absorption spectra of 37 FAMEs, including saturated, monounsaturated, and polyunsaturated types were recorded. Unsaturated FAMEs show significantly different gas phase absorption profiles than saturated ones, and these classes can be easily distinguished with the VUV detector. Another advantage includes differentiating cis/trans-isomeric FAMEs (e.g. oleic acid methyl ester and linoleic acid methyl ester isomers) and the ability to use VUV data analysis software for deconvolution of co-eluting signals. As a universal detector, VUV also provides high specificity, sensitivity, and a fast data acquisition rate, making it a powerful tool for fatty acid screening when combined with gas chromatography. The fatty acid profile of several food oil samples (olive, canola, vegetable, corn, sunflower and peanut oils) were analyzed in this study to demonstrate applicability to real world samples. Copyright © 2015 Elsevier Ltd. All rights reserved.

  9. Mucoadhesive hydrogel microparticles based on poly (methacrylic acid-vinyl pyrrolidone)-chitosan for oral drug delivery.

    Science.gov (United States)

    Sajeesh, S; Sharma, Chandra P

    2011-05-01

    The study was aimed at the evaluation of N-vinyl pyrrolidone (NVP) incorporated polymethacrylic acid-chitosan microparticles for oral drug delivery applications. Poly (methacrylic acid)-chitosan (PMC) and poly(methacrylic acid-vinyl pyrrolidone)-chitosan (PMVC) microparticles were prepared by an ionic-gelation method. Mucoadhesion behaviour of these particles was evaluated by ex-vivo adhesion method using freshly excised rat intestinal tissue. Cytotoxicity and absorption enhancing property of PMC and PMVC particles were evaluated on Caco 2 cell monolayers. Protease enzyme inhibition capability and insulin loading/release properties of these hydrogel particles was evaluated under in vitro experimental conditions. Addition of NVP units enhanced the mucoadhesion behavior of PMC particles on isolated rat intestinal tissue. Both PMC and PMVC particles were found non-toxic on Caco 2 cell monolayers and PMC particles was more effective in improving paracellular transport of fluorescent dextran across Caco 2 cell monolayers as compared to PMVC particles. However, protease inhibition efficacy of PMC particles was not significantly affected with NVP addition. NVP incorporation improved the insulin release properties of PMC microparticles at acidic pH. Hydrophilic modification seems to be an interesting approach in improving mucoadhesion capability of PMC microparticles.

  10. Actinic-radiation curable polymers prepared from a reactive polymer, halogenated cyclic anhydride and glycidyl ester

    International Nuclear Information System (INIS)

    Pastor, S.D.

    1979-01-01

    A novel class of photosensitive polymers are disclosed which are prepared by the reaction, preferably in the presence of a catalyst, of a reactive polymer, a halogenated cyclic anhydride and glycidyl ester of an alpha, beta-unsaturated carboxylic acid. These polymers are capable of undergoing vinyl-type polymerization when exposed to actinic radiation

  11. Preparation and characterization of acrylic acid-grafted poly (vinyl alcohol) hydrogel actuators using γ-ray irradiation

    International Nuclear Information System (INIS)

    An, Sung Jun; Lim, Youn Mook; Gwon, Hui Jeong; Kim, Yun Hye; Youn, Min Ho; Nho, Young Chang; Han, Dong Hyun; Kim, Chong Yeal

    2008-01-01

    Active polymer gels expand and contract in response to certain environmental stimuli, such as the application of an electric field or a change in the pH level of the surroundings. This ability to achieve large, reversible deformations with no external mechanical loading has generated much interest in the use of these gels as biomimetic actuators and artificial muscles. In this study, poly (vinyl alcohol)(PVA) grafted acrylic acid monomer (PVA-g-AAc) hydrogels were prepared by 60 Co γ-ray irradiation and their properties such as degree of grafting and weight swelling in electrostimulation as an artificial muscle and actuator were investigated

  12. Synthesis and Antiradical/Antioxidant Activities of Caffeic Acid Phenethyl Ester and Its Related Propionic, Acetic, and Benzoic Acid Analoguesc

    Directory of Open Access Journals (Sweden)

    Mohamed Touaibia

    2012-12-01

    Full Text Available Caffeic acid phenethyl ester (CAPE is a bioactive component isolated from propolis. A series of CAPE analogues was synthesized and their antiradical/antioxidant effects analyzed. The effect of the presence of the double bond and of the conjugated system on the antioxidant effect is evaluated with the analogues obtained from 3-(3,4-dihydroxyphenyl propanoic acid. Those obtained from 2-(3,4-dihydroxyphenyl acetic acid and 3,4-dihydroxybenzoic acid allow the evaluation of the effect of the presence of two carbons between the carbonyl and aromatic system.

  13. Occurrence of fatty acid short-chain-alkyl esters in fruits of Celastraceae plants.

    Science.gov (United States)

    Sidorov, Roman A; Zhukov, Anatoly V; Pchelkin, Vasily P; Vereshchagin, Andrei G; Tsydendambaev, Vladimir D

    2013-06-01

    Small amounts of a mixture of fatty acid short-chain-alkyl esters (FASCAEs) were obtained from the fruits of twelve plant species of Celastraceae family, and in five of them the FASCAEs were present not only in the arils but also in the seeds. These mixtures contained 32 individual FASCAE species, which formed four separate fractions, viz. FA methyl, ethyl, isopropyl, and butyl esters (FAMEs, FAEEs, FAIPEs, and FABEs, resp.). The FASCAE acyl components included the residues of 16 individual C₁₄-C₂₄ saturated, mono-, di-, and trienoic FAs. Linoleic, oleic, and palmitic acids, and, in some cases, also α-linolenic acid predominated in FAMEs and FAEEs, while myristic acid was predominant in FAIPEs. It can be suggested that, in the fruit arils of some plant species, FAMEs and FAEEs were formed at the expense of a same FA pool characteristic of a given species and were strongly different from FAIPEs and FABEs esters regarding the mechanism of their biosynthesis. However, as a whole, the qualitative and quantitative composition of various FASCAE fractions, as well as their FA composition, varied considerably depending on various factors. Therefore, separate FASCAE fractions seem to be synthesized from different FA pools other than those used for triacylglycerol formation. Copyright © 2013 Verlag Helvetica Chimica Acta AG, Zürich.

  14. Isoquercitrin Esters with Mono- or Dicarboxylic Acids: Enzymatic Preparation and Properties.

    Science.gov (United States)

    Vavříková, Eva; Langschwager, Fanny; Jezova-Kalachova, Lubica; Křenková, Alena; Mikulová, Barbora; Kuzma, Marek; Křen, Vladimír; Valentová, Kateřina

    2016-06-07

    A series of isoquercitrin (quercetin-3-O-β-d-glucopyranoside) esters with mono- or dicarboxylic acids was designed to modulate hydro- and lipophilicity and biological properties. Esterification of isoquercitrin was accomplished by direct chemoenzymatic reaction using Novozym 435 (lipase from Candida antarctica), which accepted C₅- to C12-dicarboxylic acids; the shorter ones, such as oxalic (C₂), malonic (C₃), succinic (C₄) and maleic (C₄) acids were not substrates of the lipase. Lipophilicity of monocarboxylic acid derivatives, measured as log P, increased with the chain length. Esters with glutaric and adipic acids exhibited hydrophilicity, and the dodecanedioic acid hemiester was more lipophilic. All derivatives were less able to reduce Folin-Ciocalteau reagent (FCR) and scavenge DPPH (1,1-diphenyl-2-picrylhydrazyl) than isoquercitrin; ABTS (2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid)) radical-scavenging activity was comparable. Dodecanoate and palmitate were the least active in FCR and ABTS scavenging; dodecanoate and hemiglutarate were the strongest DPPH scavengers. In contrast, most derivatives were much better inhibitors of microsomal lipoperoxidation than isoquercitrin; butyrate and hexanoate were the most efficient. Anti-lipoperoxidant activity of monocarboxylic derivatives, except acetates, decreased with increasing aliphatic chain. The opposite trend was noted for dicarboxylic acid hemiesters, isoquercitrin hemidodecanedioate being the most active. Overall, IQ butyrate, hexanoate and hemidodecanedioate are the most promising candidates for further studies.

  15. Coriander seed oil methyl esters as biodiesel fuel: Unique fatty acid composition and excellent oxidative stability

    International Nuclear Information System (INIS)

    Moser, Bryan R.; Vaughn, Steven F.

    2010-01-01

    Coriander (Coriandrum sativum L.) seed oil methyl esters were prepared and evaluated as an alternative biodiesel fuel and contained an unusual fatty acid hitherto unreported as the principle component in biodiesel fuels: petroselinic (6Z-octadecenoic; 68.5 wt%) acid. Most of the remaining fatty acid profile consisted of common 18 carbon constituents such as linoleic (9Z,12Z-octadeca-dienoic; 13.0 wt%), oleic (9Z-octadecenoic; 7.6 wt%) and stearic (octadecanoic; 3.1 wt%) acids. A standard transesterification procedure with methanol and sodium methoxide catalyst was used to provide C. sativum oil methyl esters (CSME). Acid-catalyzed pretreatment was necessary beforehand to reduce the acid value of the oil from 2.66 to 0.47 mg g -1 . The derived cetane number, kinematic viscosity, and oxidative stability (Rancimat method) of CSME was 53.3, 4.21 mm 2 s -1 (40 o C), and 14.6 h (110 o C). The cold filter plugging and pour points were -15 o C and -19 o C, respectively. Other properties such as acid value, free and total glycerol content, iodine value, as well as sulfur and phosphorous contents were acceptable according to the biodiesel standards ASTM D6751 and EN 14214. Also reported are lubricity, heat of combustion, and Gardner color, along with a comparison of CSME to soybean oil methyl esters (SME). CSME exhibited higher oxidative stability, superior low temperature properties, and lower iodine value than SME. In summary, CSME has excellent fuel properties as a result of its unique fatty acid composition.

  16. Measurement uncertainty of ester number, acid number and patchouli alcohol of patchouli oil produced in Yogyakarta

    Science.gov (United States)

    Istiningrum, Reni Banowati; Saepuloh, Azis; Jannah, Wirdatul; Aji, Didit Waskito

    2017-03-01

    Yogyakarta is one of patchouli oil distillation center in Indonesia. The quality of patchouli oil greatly affect its market price. Therefore, testing quality of patchouli oil parameters is an important concern, one through determination of the measurement uncertainty. This study will determine the measurement uncertainty of ester number, acid number and content of patchouli alcohol through a bottom up approach. Source contributor to measurement uncertainty of ester number is a mass of the sample, a blank and sample titration volume, the molar mass of KOH, HCl normality, and replication. While the source contributor of the measurement uncertainty of acid number is the mass of the sample, the sample titration volume, the relative mass and normality of KOH, and repetition. Determination of patchouli alcohol by Gas Chromatography considers the sources of measurement uncertainty only from repeatability because reference materials are not available.

  17. Evaluating the Intoxicating Degree of Liquor Products with Combinations of Fusel Alcohols, Acids, and Esters

    Directory of Open Access Journals (Sweden)

    Jia Xie

    2018-05-01

    Full Text Available To investigate the effects of fusel alcohols on the intoxicating degree of liquor products, formulated liquors (FLs were prepared by blending 1-propanol, isobutanol, and isoamyl alcohol with ethanol, organic acids, and corresponding ethyl esters to simulate the formula of traditional Chinese liquors. The prepared FLs were submitted for evaluation of their intoxicating degree (ID. The results showed that the fusel alcohols had a biphasic effect on the IDs of the FLs, depending on the comprehensive coordination of the characteristic minor components. The importance of the suitable ratio of alcohols/acids/esters (RAAE on the IDs was also revealed. Under an optimal ratio level, the fusel alcohols exhibited negligible effects on the IDs of the FLs. Moreover, the ratio of isoamyl alcohol to isobutanol (IA/IB showed a strong positive correlation to the IDs of the FLs. This study lays a foundation for the potential application in producing low-ID liquor.

  18. Evaluating the Intoxicating Degree of Liquor Products with Combinations of Fusel Alcohols, Acids, and Esters.

    Science.gov (United States)

    Xie, Jia; Tian, Xiao-Fei; He, Song-Gui; Wei, Yun-Lu; Peng, Bin; Wu, Zhen-Qiang

    2018-05-23

    To investigate the effects of fusel alcohols on the intoxicating degree of liquor products, formulated liquors (FLs) were prepared by blending 1-propanol, isobutanol, and isoamyl alcohol with ethanol, organic acids, and corresponding ethyl esters to simulate the formula of traditional Chinese liquors. The prepared FLs were submitted for evaluation of their intoxicating degree (ID). The results showed that the fusel alcohols had a biphasic effect on the IDs of the FLs, depending on the comprehensive coordination of the characteristic minor components. The importance of the suitable ratio of alcohols/acids/esters (RAAE) on the IDs was also revealed. Under an optimal ratio level, the fusel alcohols exhibited negligible effects on the IDs of the FLs. Moreover, the ratio of isoamyl alcohol to isobutanol (IA/IB) showed a strong positive correlation to the IDs of the FLs. This study lays a foundation for the potential application in producing low-ID liquor.

  19. Simultaneous determination of oxalic, citric, nitrilotriacetic and ethylenediamenetetraacetic acids by gas liquid chromatography of their methyl esters

    International Nuclear Information System (INIS)

    Eskell, C.J.; Pick, M.E.

    1980-04-01

    A procedure for simultaneous determination of ethylenediaminetetraacetic acid (EDTA), nitrilotriacetic acid (NTA), citric acid and oxalic acid by gas liquid chromatography is described. The involatile acids are first concerted to their volatile methyl ester derivatives by reaction with boron trifluoride in methanol. Transition metal ions (Fe 3+ , Cr 3+ and Ni 2+ ) which will be present in decontamination liquors from nuclear reactors, and form strong chelates with the acids, have been shown to cause no interference to the esterification reaction. The esters were separated by temperature programming on a 3.5 metre capillary column packed with 3% OV1 on Diatomite CQ and were detected by flame ionisation. (author)

  20. Hydroxycinnamic acids are ester-linked directly to glucosyl moieties within the lignan macromolecule from flaxseed hulls

    NARCIS (Netherlands)

    Struijs, K.; Vincken, J.P.; Verhoef, R.P.; Voragen, A.G.J.; Gruppen, H.

    2008-01-01

    In flaxseed hulls, lignans are present in an oligomeric structure. Secoisolariciresinol diglucoside (SDG), ester-linked to hydroxy-methyl-glutaric acid (HMGA), forms the backbone of this lignan macromolecule. The hydroxycinnamic acids p-coumaric acid glucoside (CouAG) and ferulic acid glucoside

  1. Amide and Ester-Functionalized Humic Acid for Fuel Combustion Enhancement

    Science.gov (United States)

    Riggs, Mark

    Humic acid is a class of naturally occurring molecules composed of large sheet-like regions of cyclic aromatic hydrocarbon networks with surface and edge functional groups including phenols, carboxylic acids, and epoxides. These naturally occurring molecules are found in brown coal deposits near lignite formations. Humic acid has gained attention from the scientific community as a precursor for graphene. Graphene is a 2-dimensional honeycomb structure of fully unsaturated carbon atoms that has exceptional material properties and inherent aromaticity. Graphene's incredible properties are matched by the difficulty associated with reproducibly manufacturing it on a large scale. This issue has limited the use of graphene for commercial applications. The polar functional groups of humic acid contribute to the hydrophilic nature of the molecule, limiting its miscibility in any alkyl-based solvent. Surfactants containing long alkyl chains can affect the miscibility of the molecule in an organic solvent. Surfactants are often difficult to remove from the system. It is theorized that alkylation of the functional sites of humic acid can affect the hydrophilic nature of the molecule, and effectively enable its dispersion into organic solvents without simultaneous incorporation of surfactants. This dissertation investigated the amidation and esterification of humic acid molecules extracted from leonardite. The resulting change in the modified humic acid dispersibility in organic solvents and its potential usage as a fuel additive were evaluated. Butyl, hexyl, octyl, and decyl amide-modified and ester-modified humic acids were synthesized. These products were characterized to confirm successful chemical reaction through thermogravimetric analysis, Fourier-transform infrared spectroscopy, and scanning electron microscopy. The decyl-modified humic acids remained suspended in kerosene mixtures for longer than 1 week. Other organo-humic acids showed varying degrees of flocculation

  2. Synthesis of 2-(6-Acetamidobenzothiazolethioacetic Acid Esters as Photosynthesis Inhibitors

    Directory of Open Access Journals (Sweden)

    Dusan Loos

    1998-04-01

    Full Text Available The synthesis and photosynthesis-inhibiting activity of 13 new 2-(6-acetamidobenzothiazolethioacetic acid esters are reported. The new compounds were prepared by acetylation of 2-(alkoxycarbonylmethylthio-6-aminobenzothiazoles with acetic anhydride. The structure of the compounds was verified by 1H NMR spectra. The compounds inhibit photosynthetic electron transfer in spinach chloroplasts. The structure - activity relation was studied. Lipophilicity was found to influence substantially photosynthetic electron transfer.

  3. Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters

    Directory of Open Access Journals (Sweden)

    Yoshinori Yamamoto

    2011-05-01

    Full Text Available Unprecedented alkylation of silyl enol ethers has been developed by the use of ortho-alkynylbenzoic acid alkyl esters as alkylating agents in the presence of a gold catalyst. The reaction probably proceeds through the gold-induced in situ construction of leaving groups and subsequent nucleophilic attack on the silyl enol ethers. The generated leaving compound abstracts a proton to regenerate the silyl enol ether structure.

  4. Palmitic Acid Curcumin Ester Facilitates Protection of Neuroblastoma against Oligomeric Aβ40 Insult

    OpenAIRE

    Zhangyang Qi; Meihao Wu; Yun Fu; Tengfei Huang; Tingting Wang; Yanjie Sun; Zhibo Feng; Changzheng Li

    2017-01-01

    Background/Aims: The generation of reactive oxygen species (ROS) caused by amyloid-β (Aβ) is considered to be one of mechanisms underlying the development of Alzheimer’s disease. Curcumin can attenuate Aβ-induced neurotoxicity through ROS scavenging, but the protective effect of intracellular curcumin on neurocyte membranes against extracellular Aβ may be compromised. To address this issue, we synthesized a palmitic acid curcumin ester (P-curcumin) which can be cultivated on the cell membrane...

  5. Use of citric acid esters as alternative fuel for diesel engines

    Energy Technology Data Exchange (ETDEWEB)

    Huber, Georg; Thuneke, Klaus; Remmele, Edgar [Technologie- und Foerderzentrum, Straubing (Germany); Schieder, Doris [Technische Univ. Muenchen, Straubing (Germany). Lehrstuhl fuer Chemie Biogener Rohstoffe

    2013-06-01

    Common fuels for (adapted) diesel engines are fossil diesel fuel, fatty acid methyl ester (FAME or biodiesel) or vegetable oils. Furthermore the citric acid esters tributylcitrate (TBC) and triethylcitrate (TEC) are expected to be a possible diesel substitute. Their use as fuel was applied for a patent in Germany in 2010. According to the patent applicant the advantages are low soot combustion, independence of energy imports due to the possibility of local production and a broad raw material base. Their fuel properties have been analysed in the laboratory and compared with the relevant fuel standards. Only some of the determined values are meeting the specifications, but on the other hand few rapeseed oil characteristics (e. g. oxidation stability and viscosity) can be improved if the citric acid esters are used as a blend component. The operating and emission behaviour of a vegetable oil compatible CHP unit fuelled with various rapeseed oil and TBC blends were investigated and a trouble free and soot emission reduced engine operation due to the high molecularly bound oxygen content was observed. Long term test runs are necessary for an entire technical validation. (orig.)

  6. Chromatographic analyses of fatty acid methyl esters by HPLC-UV and GC-FID

    Energy Technology Data Exchange (ETDEWEB)

    Carvalho, Myller S.; Pinho, David M.M.; Suarez, Paulo A.Z., E-mail: psuarez@unb.br [Laboratorio de Materiais e Combustiveis, Instituto de Quimica, Universidade de Brasilia, DF (Brazil); Mendonca, Marcio A. [Faculdade de Agronomia e Medicina Veterinaria, Universidade de Brasilia, DF (Brazil); Resck, Ines S. [Laboratorio de Ressonancia Magnetica Nuclear, Universidade de Brasilia, DF (Brazil)

    2012-04-15

    An analytical method using high performance liquid chromatography with UV detection (HPLC-UV) (method A) was used for simultaneous determination of total amounts of triacylglycerides, diacylglycerides, monoacylglycerides and fatty acid methyl esters in alcoholysis of different oil (cotton, canola, sunflower, corn and soybean) samples. Analyses were carried out at 40 deg C for 20 min using a gradient of methanol (MeOH) and 2-propanol-hexane 5:4 (v/v) (PrHex): 100% of MeOH in 0 min, 50% of MeOH and 50% of PrHex in 10 min maintained with isocratic elution for 10 min. Another HPLC-UV method (method B) with acetonitrile isocratic elution for 34 min was used to determine the fatty acid composition of oils analyzing their methyl ester derivatives. Contents were determined with satisfactory repeatability (relative standard deviation, RSD < 3%), linearity (r{sup 2} > 0.99) and sensitivity (limit of quantification). Method B was compared with an official gas chromatographic method with flame ionization detection (GC-FID) from American Oil Chemists' Society (AOCS) in the determination of fatty acid methyl esters (FAME) in biodiesel real samples. (author)

  7. Chromium–tungsten–titanium mixed oxides solid catalyst for fatty acid methyl ester synthesis from palm fatty acid distillate

    International Nuclear Information System (INIS)

    Wan, Zuraida; Hameed, B.H.

    2014-01-01

    Highlights: • Chromium–tungsten–titanium mixed oxides as solid catalyst. • Catalyst used for esterification of palm fatty acid distillate to methyl esters. • The maximum methyl ester content is 83%. • Catalyst has shown good activity and can be recycled for 4 times. - Abstract: Chromium–tungsten–titanium mixed oxides solid catalysts were prepared and evaluated in the esterification of palm fatty acid distillate (PFAD) to produce fatty acid methyl ester (FAME). Esterification was conducted in a batch reactor at 110–200 °C temperature ranges. The catalysts were characterized by several techniques such as BET, TEM, FTIR, TGA, XRD, EDX and SEM. The treatment conditions during catalyst preparation, effect of reaction parameters, leaching of the active species and the recycled use of the catalyst were investigated. The catalyst with formula CrWTiO 2 was found to be the most active with maximum FAME content of 83% obtained at best reaction conditions of 170 °C for 3 h, 2:1 (methanol to oil molar ratio) and 2 wt.% catalyst dosage. The catalyst can be recycled for 4 times. The results revealed CrWTiO 2 good potentials for use in esterification of high acid value oil

  8. Lipase immobilization and production of fatty acid methyl esters from canola oil using immobilized lipase

    International Nuclear Information System (INIS)

    Yuecel, Yasin; Demir, Cevdet; Dizge, Nadir; Keskinler, Buelent

    2011-01-01

    Lipase enzyme from Aspergillus oryzae (EC 3.1.1.3) was immobilized onto a micro porous polymeric matrix which contains aldehyde functional groups and methyl esters of long chain fatty acids (biodiesel) were synthesized by transesterification of crude canola oil using immobilized lipase. Micro porous polymeric matrix was synthesized from styrene-divinylbenzene (STY-DVB) copolymers by using high internal phase emulsion technique and two different lipases, Lipozyme TL-100L ® and Novozym 388 ® , were used for immobilization by both physical adsorption and covalent attachment. Biodiesel production was carried out with semi-continuous operation. Methanol was added into the reactor by three successive additions of 1:4 M equivalent of methanol to avoid enzyme inhibition. The transesterification reaction conditions were as follows: oil/alcohol molar ratio 1:4; temperature 40 o C and total reaction time 6 h. Lipozyme TL-100L ® lipase provided the highest yield of fatty acid methyl esters as 92%. Operational stability was determined with immobilized lipase and it indicated that a small enzyme deactivation occurred after used repeatedly for 10 consecutive batches with each of 24 h. Since the process is yet effective and enzyme does not leak out from the polymer, the method can be proposed for industrial applications. -- Research highlights: → Lipozyme TL-100L and Novozym 388 were immobilized onto micro porous polymeric matrix by both physical adsorption and covalent linking. → Immobilized enzymes were used for synthesis of fatty acid methyl esters by transesterification of canola oil and methanol using semi-continuous operation system. → According to chromatographic analysis, Lipase Lipozyme TL-100L resulted in the highest yield of methyl ester as 92%.

  9. Development of Manufacturing Method of Highly Functional Material Gallic acid-CLA Ester Using Irradiation

    International Nuclear Information System (INIS)

    Cho, C. H.; Byun, M. W.; Jeong, I. Y.; Kim, D. H.

    2006-01-01

    Increasing interest and current trends for natural materials with various health beneficial functions by radiation (RT)-biotechnology (BT) fusion by developed countries. However, the information and development of new functional materials using the RT-BT fusion technology is still limited. The target material developed and manufactured by RT-BT fusion technology may have a multi-functional effect on human health and it can be applied for pharmaceutical materials as well as functional food ingredient. The market of functional new materials has been grown dramatically and a multi-functional material manufactured by RT-BT fusion technology may have a great economic impact for both the domestic and overseas market. Development of GA-CLA ester by chemical synthetic method. Transformation of linoleic acid to conjugated linoleic acid by irradiation. Identification and confirmation of the biological functions including antioxidative, cancer cell proliferation inhibition, anti-microbial, enhancement of immune response and lipid metabolism of GA-CLA ester. Increase industrial applicability of the new materials. Development of GA-CLA ester by chemical synthetic method(2 patents submitted). Development of the optimum methodology of GA-CLA and its derivative, octadeca-9,12-dienyl-3,4,5-trihydroxy benzoate). Identification and confirmation of biological activities of GA-CLA. Extramural funding from the Ministry of Commerce, Industry, and Energy subjected by gallic acid-fatty acid derivatives (205,000,000 Won). Provides the basic data for successful project 'Development of cosmeceutical and cosmetics using gallic acid fatty acid derivatives' funded by Ministry of Commerce, Industry, and Energy and collaboration with the Technology-invested venture company, SunBiotech, Co. and problem-solving for industrial application. Complete the patent procedure and publish the results to international or domestic peer-reviewed journals

  10. Scalable preparation of high purity rutin fatty acid esters following enzymatic synthesis

    DEFF Research Database (Denmark)

    Lue, Bena-Marie; Guo, Zheng; Xu, Xuebing

    2010-01-01

    Investigations into expanded uses of modified flavonoids are often limited by the availability of these high purity compounds. As such, a simple, effective and relatively fast method for isolation of gram quantities of both long and medium chain fatty acid esters of rutin following scaled......-up biosynthesis reactions was established. Acylation reactions of rutin and palmitic or lauric acids were efficient in systems containing dried acetone and molecular sieves, yielding from 70–77% bioconversion after 96 h. Thereafter, high purity isolates (>97%) were easily obtained in significant quantities...

  11. [Chloroquine analogues from benzofuro- and benzothieno[3,2-b]-4-pyridone-2-carboxylic acid esters].

    Science.gov (United States)

    Gölitzer, K; Meyer, H; Jomaa, H; Wiesner, J

    2004-08-01

    The amides 7 were synthesized from the annulated methyl 4-pyridone-2-carboxylates 4 via the carboxylic acids 5 and their acid chlorides by reacting with the novaldiamine base 6. The alcohol 8b, obtained from DIBAH reduction of the ester 4b, was transformed to the chloromethyl derivative 9 which reacted with 6 and 18-crown-6 leading to the 2-novaldiaminomethyl-4-pyridone 10. Compound 10 was obtained with higher yield from DIBAH reduction of the amide 7b. The substances 7 and 10 were inactive when tested against the chloroquine resistant Plasmodium falciparum strain Dd2.

  12. Final safety assessment of thiodipropionic acid and its dialkyl esters as used in cosmetics.

    Science.gov (United States)

    Diamante, Catherine; Fiume, Monice Zondlo; Bergfeld, Wilma F; Belsito, Donald V; Hill, Ronald A; Klaassen, Curtis D; Liebler, Daniel C; Marks, James G; Shank, Ronald C; Slaga, Thomas J; Snyder, Paul W; Alan Andersen, F

    2010-07-01

    Dilauryl thiodipropionate (DLTDP), dicetyl thiodipropionate, dimyristyl thiodipropionate, distearyl thiodipropionate, and ditridecyl thiodipropionate are dialkyl esters of their respective alcohols and thiodipropionic acid (TDPA) used in cosmetics. Ingested DLTDP was excreted in the urine as TDPA. Single-dose acute oral and parenteral studies and subchronic and chronic repeated dose oral studies did not suggest significant toxicity. Neither DLTDP nor TDPA was irritating to animal skin or eyes and they were not sensitizers. TDPA was neither a teratogen nor a reproductive toxicant. Genotoxicity studies were negative for TDPA and DLTDP. Clinical testing demonstrated some evidence of irritation but no sensitization or photosensitization. The Cosmetic Ingredient Review Expert Panel considered that the data from DLTDP reasonably may be extrapolated to the other dialkyl esters and concluded that these ingredients were safe for use in cosmetic products that are formulated to be nonirritating.

  13. One-pot conversion of biomass-derived xylose and furfural into levulinate esters via acid catalysis.

    Science.gov (United States)

    Hu, Xun; Jiang, Shengjuan; Wu, Liping; Wang, Shuai; Li, Chun-Zhu

    2017-03-07

    Direct conversion of biomass-derived xylose and furfural into levulinic acid, a platform molecule, via acid-catalysis has been accomplished for the first time in dimethoxymethane/methanol. Dimethoxymethane acted as an electrophile to transform furfural into 5-hydroxymethylfurfural (HMF). Methanol suppressed both the polymerisation of the sugars/furans and the Aldol condensation of levulinic acid/ester.

  14. Sucrose fatty esters from underutilized seed oil of Terminalia catappa as potential steel corrosion inhibitor in acidic medium

    Directory of Open Access Journals (Sweden)

    Adewale Adewuyi

    2016-12-01

    Full Text Available Corrosion of metals is a common problem which requires definite attention. In response to this, the oil was extracted from the seed of Terminalia catappa and used to synthesize sucrose fatty esters via simple reaction mechanism which was considered eco-friendly and sustainable. The corrosion inhibition capacity of sucrose fatty esters for mild steel in 1 M HCl was studied using the weight loss method. It was shown that sucrose fatty ester inhibited corrosion process of mild steel and obeyed Langmuir isotherm. Corrosion rate and inhibition efficiency of sucrose fatty esters were found to reduce with increase of immersion time. The study presented sucrose fatty ester as a promising inhibitor of mild steel corrosion in acidic medium.

  15. Effects of supplementation with 2-hydroxy-4-(methylthio)-butanoic acid isopropyl ester on splanchnic amino acid metabolism and essential amino acid mobilization in postpartum transition Holstein cows

    DEFF Research Database (Denmark)

    Dalbach, Kristine Foged; Larsen, Mogens; Raun, Birgitte Marie Løvendahl

    2011-01-01

    The present study aimed to investigate the effects of 2-hydroxy-4-(methylthio)-butanoic acid isopropyl ester (HMBi) supplementation on splanchnic AA metabolism, essential AA (EAA) mobilization, and plasma AA status in postpartum transition dairy cows. The EAA mobilization was calculated by differ......The present study aimed to investigate the effects of 2-hydroxy-4-(methylthio)-butanoic acid isopropyl ester (HMBi) supplementation on splanchnic AA metabolism, essential AA (EAA) mobilization, and plasma AA status in postpartum transition dairy cows. The EAA mobilization was calculated...

  16. 21 CFR 582.4101 - Diacetyl tartaric acid esters of mono- and diglycerides of edible fats or oils, or edible fat...

    Science.gov (United States)

    2010-04-01

    ... diglycerides of edible fats or oils, or edible fat-forming fatty acids. 582.4101 Section 582.4101 Food and... Diacetyl tartaric acid esters of mono- and diglycerides of edible fats or oils, or edible fat-forming fatty acids. (a) Product. Diacetyl tartaric acid esters of mono- and diglycerides of edible fats or oils, or...

  17. Vinyl ether hydrolysis. VII. Isotope effects on catalysis by aqueous hydrofluoric acid

    International Nuclear Information System (INIS)

    Kresge, A.J.; Chen, H.J.; Chiang, Y.

    1977-01-01

    Comparison of rates of hydrolysis of three vinyl ethers catalyzed by HF in H 2 O and DF in D 2 O at 25 0 C gives primary isotope effects in the range k/sub H//k/sub D/ = 3.3 to 3.5. The unexpectedly small size of these effects may be attributed to strong, ω = 1325 to 1450 cm -1 , hydrogenic bending vibrations in the proton transfer transition states of these reactions along with the lack of compensatory bending vibrations in the diatomic proton donor

  18. Antibacterial and antifungal efficacy of fatty acid methyl esters from the leaves of Sesuvium portulacastrum L.

    Science.gov (United States)

    Chandrasekaran, M; Senthilkumar, A; Venkatesalu, V

    2011-07-01

    The fatty acid methyl esters (FAME extract) from Sesuvium (S.) portulacastrum was studied for its fatty acid composition and antimicrobial activity against human pathogenic microorganisms. The gas chromatographic analysis of FAME extract revealed the presence of palmitic acid with the highest relative percentage (31.18%), followed by oleic acid (21.15%), linolenic acid (14.18%) linoleic acid (10.63%), myristic acid (6.91%) and behenic acid (2.42%). The saturated fatty acids were higher than the unsaturated fatty acids. FAME extract showed the highest antibacterial and anticandidal activities and moderate antifungal activity against the tested microorganisms. The highest mean zone of inhibition (16.3 mm) and the lowest MIC (0.25 mg/ml) and MBC (0.5 mg/ml) values were recorded against Bacillus subtilis. The lowest mean zone of inhibition (8.8 mm) and the highest MIC (8 mg/ml) and MFC (16 mg/ml) values were recorded against Aspergillus fumigatus and Aspergillus niger. The results of the present study justify the use of S. portulacastrum in traditional medicine and the FAME extract can be used as a potential antimicrobial agent against the tested human pathogenic microorganisms.

  19. Occurrence of 3-MCPD fatty acid esters in human breast milk.

    Science.gov (United States)

    Zelinková, Z; Novotný, O; Schůrek, J; Velísek, J; Hajslová, J; Dolezal, M

    2008-06-01

    A series of twelve breast milk samples were analysed by gas chromatography-mass spectrometry (GC/MS) operated in selected ion monitoring mode for 3-chloropropane-1,2-diol (3-MCPD). Whilst none of the samples contained 3-MCPD above the limit of detection of 3 microg kg(-1) milk, all contained high amounts of 3-MCPD esterified with higher fatty acids. The levels of 3-MCPD released by hydrolysis of these esters (bound 3-MCPD) ranged from the limit of detection (300 microg kg(-1), expressed on a fat basis) to 2195 microg kg(-1); with a mean level of bound 3-MCPD of 1014 microg kg(-1), which corresponded to 35.5 microg kg(-1) milk. The presence of bound 3-MCPD was confirmed using orthogonal gas chromatography coupled with high-speed time-of-flight mass spectrometry analysis for four randomly selected breast milk samples. Six breast milks collected from one of the nursing mothers 14-76 days after childbirth contained bound 3-MCPD within the range of 328-2078 microg kg(-1) fat (mean 930 microg kg(-1) fat). The calculated bound 3-MCPD content of these samples was within the range of 6 and 19 microg kg(-1) milk (mean of 12 microg kg(-1) milk). The major types of 3-MCPD esters were the symmetric diesters with lauric, palmitic, and oleic acids, and asymmetric diesters with palmitic acid/oleic acid among which 3-chloro-1,2-propanediol 1,2-dioleate prevailed.

  20. α-Imino Esters in Organic Synthesis: Recent Advances.

    Science.gov (United States)

    Eftekhari-Sis, Bagher; Zirak, Maryam

    2017-06-28

    α-Imino esters are useful precursors for the synthesis of a variety of types of natural and unnatural α-amino acid derivatives, with a wide range of biological activities. Due to the adjacent ester group, α-imino esters are more reactive relative to other types of imines and undergo different kinds of reactions, including organometallics addition, metal catalyzed vinylation and alkynylation, aza-Henry, aza-Morita-Baylis-Hillman, imino-ene, Mannich-type, and cycloaddition reactions, as well as hydrogenation and reduction. This review discusses the mechanism, scope, and applications of the reactions of α-imino esters and related compounds in organic synthesis, covering the literature from the last 12 years.

  1. Tailoring the morphology and properties of poly(lactic acid)/poly(ethylene-co-vinyl acetate)/starch blends via reactive compatibilization

    NARCIS (Netherlands)

    Ma, P.; Hristova - Bogaerds, D.G.; Schmit, P.; Goossens, J.G.P.; Lemstra, P.J.

    2012-01-01

    Poly(lactic acid)/poly(ethylene-co-vinyl acetate)/starch (PLA/EVA/starch) ternary blends were prepared by multi-step melt processing (reactive extrusion) in the presence of maleic anhydride (MA), benzoyl peroxide and glycerol. The effects of MA and glycerol concentration on the morphology and

  2. Chemically imaging the effects of the addition of nanofibrillated cellulose on the distribution of poly(acrylic acid) in poly(vinyl alcohol)

    Science.gov (United States)

    Craig Clemons; Julia Sedlmair; Barbara Illman; Rebecca Ibach; Carol Hirschmugl

    2013-01-01

    The distribution of poly(acrylic acid) (PAA) in model laminates of nanocellulose and poly(vinyl alcohol) (PVOH) was investigated by FTIR chemical imaging. The method was effective in spatially discerning the three components of the composite. PAA can potentially improve the performance of nanocellulose reinforced PVOH by not only crosslinking the PVOH matrix but also...

  3. Study of the Transformation of the Oil of Used Soya in Fatty Acid Ethyl Ester

    Directory of Open Access Journals (Sweden)

    Anabel Sarracent-López

    2016-07-01

    Full Text Available The reuse of vegetable oils in food processing brings harmful health effects and on the other hand needs a complex treatment to discard without affecting the environment. Transformed into methyl or ethyl esters of fatty acids and glycerin by transesterification with the corresponding alcohol, can be a suitable method for treatment. It was investigated residual soybean oil from a producer of fried foods and ethanol. It is known that with this spirit the transformation process presents difficulties not listed with methanol, but at the same time does not bring the drawbacks of the latter, for toxicity and acquisition, and that since it is a derivative of the domestic sugar industry does not constitute a raw material import. We experimented with ethanol 80 %, 85 % and 90 % purity and worked 35 ºC and 50 ºC. Final yields of ethyl esters, are low compared with those obtained for similar processes with methanol, 85 % being the highest yield obtained under the conditions of the process. An assessment of costs was conducted to produce 1L of ethyl esters in the laboratory, the expenses of 0,56 pesos/L.

  4. QTL for phytosterol and sinapate ester content in Brassica napus L. collocate with the two erucic acid genes

    Science.gov (United States)

    Amar, Samija; Ecke, Wolfgang; Becker, Heiko C.

    2008-01-01

    Improving oil and protein quality for food and feed purposes is an important goal in rapeseed (Brassica napus L.) breeding programs. Rapeseed contains phytosterols, used to enrich food products, and sinapate esters, which are limiting the utilization of rapeseed proteins in the feed industry. Increasing the phytosterol content of oil and lowering sinapate ester content of meal could increase the value of the oilseed rape crop. The objective of the present study was to identify quantitative trait loci (QTL) for phytosterol and sinapate ester content in a winter rapeseed population of 148 doubled haploid lines, previously found to have a large variation for these two traits. This population also segregated for the two erucic acid genes. A close negative correlation was found between erucic acid and phytosterol content (Spearman’s rank correlation, rs = −0.80**). For total phytosterol content, three QTL were detected, explaining 60% of the genetic variance. The two QTL with the strongest additive effects were mapped on linkage groups N8 and N13 within the confidence intervals of the two erucic acid genes. For sinapate ester content four QTL were detected, explaining 53% of the genetic variance. Again, a close negative correlation was found between erucic acid and sinapate ester content (rs = −0.66**) and the QTL with the strongest additive effects mapped on linkage groups N8 and N13 within the confidence intervals of the two erucic acid genes. The results suggests, that there is a pleiotropic effect of the two erucic acid genes on phytosterol and sinapate ester content; the effect of the alleles for low erucic acid content is to increase phytosterol and sinapate ester content. Possible reasons for this are discussed based on known biosynthetic pathways. Electronic supplementary material The online version of this article (doi:10.1007/s00122-008-0734-2) contains supplementary material, which is available to authorized users. PMID:18335203

  5. Chemo-enzymatic epoxidation of olefins by carboxylic acid esters and hydrogen peroxide

    Energy Technology Data Exchange (ETDEWEB)

    Ruesch gen. Klaas, M.; Warwel, S. [Inst. for Biochemistry and Technology of Lipids, H.P. Kaufmanm-Inst., Federal Centre for Cereal, Potato and Lipid Research, Muenster (Germany)

    1998-12-31

    Ethylen and, recently, butadiene can be epoxidized directly with oxygen and for the epoxidation of propylene, the use of heterogeneous transition metals and organic peroxides (Halcon-Process) is the major player. But, beside from those notable exceptions, all other epoxidations, including large ones like the epoxidation of plant oils as PVC-stabilizers (about 200.000 t/year), are carried out with peroxy acids. Because mcpba is far to expensive for most applications, short chain peracids like peracetic acid are used. Being much less stable than mcpba and thus risky handled in large amounts and high concentrations, these peroxy acids were preferably prepared in-situ. However, conventional in-situ formation of peracids has the serious drawback, that a strong acid is necessary to catalyze peroxy acid formation from the carboxylic acid and hydrogen peroxide. The presence of a strong acid in the reaction mixture often results in decreased selectivity because of the formation of undesired by-products by opening of the oxirane ring. Therefore, we propose a new method for epoxidation based on the in-situ preparation of percarboxylic acids from carboxylic acid esters and hydrogen peroxide catalyzed by a commercial, immobilized lipase. (orig.)

  6. Synthesis and Suzuki Cross-Coupling Reactions of 2,6-Bis(trifluoromethyl)pyridine-4-boronic Acid Pinacol Ester

    KAUST Repository

    Batool, Farhat

    2016-11-18

    Iridium-catalyzed aromatic borylation provides quick one-step access to 2,6-bis(trifluoromethyl)pyridine-4-boronic acid pinacol ester. Suzuki couplings of this highly electron-deficient pyridine-4-boronic ester with various (hetero)aryl bromides was successfully carried out and the coupled products were obtained in 46–95% isolated yields. Double and triple Suzuki couplings, with dibromo- and tribromoarenes, respectively, were also achieved. Thus demonstrating that this pyridine-4-boronic ester can be a useful source for the installation of one of the strongest electron-withdrawing aromatic group in organic compounds. Copyright © 2016, Georg Thieme Verlag. All rights reserved.

  7. Synthesis and Suzuki Cross-Coupling Reactions of 2,6-Bis(trifluoromethyl)pyridine-4-boronic Acid Pinacol Ester

    KAUST Repository

    Batool, Farhat; Emwas, Abdul-Hamid M.; Gao, Xin; Munawar, Munawar A.; Chotana, Ghayoor A.

    2016-01-01

    Iridium-catalyzed aromatic borylation provides quick one-step access to 2,6-bis(trifluoromethyl)pyridine-4-boronic acid pinacol ester. Suzuki couplings of this highly electron-deficient pyridine-4-boronic ester with various (hetero)aryl bromides was successfully carried out and the coupled products were obtained in 46–95% isolated yields. Double and triple Suzuki couplings, with dibromo- and tribromoarenes, respectively, were also achieved. Thus demonstrating that this pyridine-4-boronic ester can be a useful source for the installation of one of the strongest electron-withdrawing aromatic group in organic compounds. Copyright © 2016, Georg Thieme Verlag. All rights reserved.

  8. Docosahexaenoic acid ester of phloridzin inhibit lipopolysaccharide-induced inflammation in THP-1 differentiated macrophages.

    Science.gov (United States)

    Sekhon-Loodu, Satvir; Ziaullah; Rupasinghe, H P Vasantha

    2015-03-01

    Phloridzin or phlorizin (PZ) is a predominant phenolic compound found in apple and also used in various natural health products. Phloridzin shows poor absorption and cellular uptake due to its hydrophilic nature. The aim was to investigate and compare the effect of docosahexaenoic acid (DHA) ester of PZ (PZ-DHA) and its parent compounds (phloridzin and DHA), phloretin (the aglycone of PZ) and cyclooxygenase inhibitory drugs (diclofenac and nimesulide) on production of pro-inflammatory biomarkers in inflammation-induced macrophages by lipopolysaccharide (LPS)-stimulation. Human THP-1 monocytes were seeded in 24-well plates (5×10(5)/well) and treated with phorbol 12-myristate 13-acetate (PMA, 0.1μg/mL) for 48h to induce macrophage differentiation. After 48h, the differentiated macrophages were washed with Hank's buffer and treated with various concentrations of test compounds for 4h, followed by the LPS-stimulation (18h). Pre-exposure of PZ-DHA ester was more effective in reducing tumor necrosis factor-alpha (TNF-α), interleukin-6 (IL-6) and cyclooxygenase-2 (COX-2) protein levels compared to DHA and nimesulide. However, diclofenac was the most effective in reducing prostaglandin (PGE2) level by depicting a dose-dependent response. However, PZ-DHA ester and DHA were the most effective in inhibiting the activation of nuclear factor-kappa B (NF-κB) among other test compounds. Our results suggest that PZ-DHA ester might possess potential therapeutic activity to treat inflammation related disorders such as type 2 diabetes, asthma, atherosclerosis and inflammatory bowel disease. Copyright © 2015 Elsevier B.V. All rights reserved.

  9. Radiation sensitivity and EPR dosimetric potential of gallic acid and its esters

    International Nuclear Information System (INIS)

    Tuner, Hasan; Oktay Bal, M.; Polat, Mustafa

    2015-01-01

    In the preset work the radiation sensitivities of Gallic Acid anhydrous and monohydrate, Octyl, Lauryl, and Ethyl Gallate (GA, GAm, OG, LG, and EG) were investigated in the intermediate (0.5–20 kGy) and low radiation (<10 Gy) dose range using Electron Paramagnetic Resonance (EPR) spectroscopy. While OG, LG, and EG are presented a singlet EPR spectra, their radiation sensitivity found to be very different in the intermediate dose range. At low radiation dose range (<10 Gy) only LG is found to be present a signal that easily distinguished from the noise signals. The intermediate and low dose range radiation sensitivities are compared using well known EPR dosimeter alanine. The radiation yields (G) of the interested material were found to be 1.34×10 −2 , 1.48×10 −2 , 4.14×10 −2 , and 6.03×10 −2 , 9.44×10 −2 for EG, GA, GAm, OG, and LG, respectively at the intermediate dose range. It is found that the simple EPR spectra and the noticeable EPR signal of LG make it a promising dosimetric material to be used below 10 Gy of radiation dose. - Highlights: • Radiation sensitivity of gallic acid and its esters were studied in intermediate and low radiation dose range using EPR. • While the irradiated samples of GA were presented complex EPR spectra the esters presented singlet ESR spectra. • Samples were compared to alanine in terms of the dosimetric point of view. • The radiation sensitivities of the investigated materials were very low at intermediate doses. • Lauryl ester of gallic acid was found to present a good sensitivity below 10 Gy

  10. Branched-chain dicationic ionic liquids for fatty acid methyl ester assessment by gas chromatography.

    Science.gov (United States)

    Talebi, Mohsen; Patil, Rahul A; Sidisky, Leonard M; Berthod, Alain; Armstrong, Daniel W

    2017-12-06

    Twelve bis- or dicationic ionic liquids (ILs) including eight based on imidazolium, a single one based on phosphonium, and three based on pyrrolidinium cationic units were prepared with the bis(trifluoromethyl sulfonyl) imide anion. The two identical cationic moieties were attached by different alkyl spacers having three or five carbons and differing alkyl substituents attached to the spacer. The SLB-IL111 column, as the most polar commercial stationary phase known, was included in the study for comparison. Isothermal separations of a rapeseed oil fatty acid methyl ester (FAME) sample were used to study and compare the 12 IL-based column performances and selectivities. The retention times of the most retained methyl esters of lignoceric (C24:0) and erucic (C22:1) acids were used to estimate the IL polarity. The phosphonium dicationic IL column was, by far, the least polar. Imidazolium-based dicationic IL columns were the most polar. Polarity and selectivity for the FAME separation were somewhat related. The separation of a 37-FAME standard mixture allowed the investigation of selectivity variations observed on the 12 IL-based columns under temperature gradients up to 230 °C. The remarkable selectivity of the IL-based columns is demonstrated by the detailed analysis of the cis/trans C18:1 isomers of a partially hydrogenated vegetable oil sample on 30-m columns, separations competing with that done following an "official method" performed on a 100-m column. Graphical abstract Separation of fatty acid methyl esters on a 30-m 3m 2 C 5 (mpy) 2 . 2NTf 2 branched-chain dicationic IL-based column. Branched chain dicationic ILs show great selectivity for separation of cis/trans, ω-3/ω-6, and detailed analysis of cis/trans fats.

  11. Vinyl Record

    DEFF Research Database (Denmark)

    Bartmanski, Dominik; Woodward, Ian

    2018-01-01

    . This relational process means that both the material affordances and entanglements of vinyl allow us to feel, handle, experience, project, and share its iconicity. The materially mediated meanings of vinyl enabled it to retain currency in independent and collector’s markets and thus resist the planned......In this paper, we use the case of the vinyl record to show that iconic objects become meaningful via a dual process. First, they offer immersive engagements which structure user interpretations through various material experiences of handling, use, and extension. Second, they always work via...

  12. Radiation preparation of drug carriers based polyacrylic acid (PAAc) using poly(vinyl pyrrolidone) (PVP) as a template polymer

    Science.gov (United States)

    Abd El-Rehim, H. A.; Hegazy, E. A.; Khalil, F. H.; Hamed, N. A.

    2007-01-01

    The present study deals with the radiation synthesis of stimuli response hydrophilic polymers from polyacrylic acid (PAAc). To maintain the property of PAAc and control the water swellibility for its application as a drug delivery system, radiation polymerization of AAc in the presence of poly(vinyl pyrrolidone) (PVP) as a template polymer was carried out. Characterization of the prepared PAA/PVP inter-polymer complex was investigated by determining gel content, swelling property, hydrogel microstructure and the release rate of caffeine as a model drug. The release rate of caffeine from the PAA/PVP inter-polymer complexes showed pH-dependency, and seemed to be mainly controlled by the dissolution rate of the complex above a p Ka of PAAc. The prepared inter-polymer complex could be used for application as drug carriers.

  13. Synthesis of water-soluble poly [acrylic acid-co-vinyl butyl ether] and its applications in cement admixtures

    International Nuclear Information System (INIS)

    Negim, S.M.; Mun, G.A.; Nurkeeva, Z.S.; Danveesh, H.H.M.

    2005-01-01

    Three composition ratios of poly[acrylic acid (AA)-co-vinyl butyl ether)] were prepared in alcoholic solution using azo-bis-isobutyro-nitrile as initiator (ABIN). The water-soluble copolymers were characterized through FT-IR, 1 H NMR, Mass spectra, ESEM as well as viscosity. The effect of water-soluble copolymers and their sodium salts on the physico-mechanical properties of Ordaniary Portland Cement (O.P.C) pastes was investigated. The results showed that the addition of aqueous solutions from the prepared copolymers and their sodium salts to the cement improve most of the specific characteristics of (O.P.C). As the concentration of the water-soluble copolymer increases, the setting time increases. The combined water content enhances the addition of copolymer to the mixing water. The compressive strength was she increased at all any hydration. The results of the solution of the prepared sodium salt copolymers are better than its copolymers. (author)

  14. A Spectroscopic Method for Determining Free Iodine in Iodinated Fatty-Acid Esters

    Science.gov (United States)

    Klyubin, V. V.; Klyubina, K. A.; Makovetskaya, K. N.

    2018-01-01

    It is shown that the concentration of free iodine in samples of iodinated fatty-acid esters can be measured using the electronic absorption spectra of their solutions in ethanol. The method proposed is rather simple in use and highly sensitive, allowing detection of presence of less than 10 ppm of free iodine in iodinated compounds. It is shown using the example of Lipiodol that this makes it possible to easily detect small amounts of free iodine in samples containing bound iodine in concentrations down to 40 wt %.

  15. Conducting polymers of octanoic acid 2-thiophen-3-yl-ethyl ester and their electrochromic properties

    International Nuclear Information System (INIS)

    Camurlu, Pinar; Cirpan, Ali; Toppare, Levent

    2005-01-01

    Octanoic acid 2-thiophen-3-yl-ethyl ester was synthesized via the reaction of 3-thiophene ethanol with octanoyl chloride. The resulting monomer was electrochemically homopolymerized in the presence of tetrabutylammonium tetrafluoroborate as the supporting electrolyte, in the acetonitrile/borontrifluoride ethyl ether solvent system. The resulting polymer was characterized using various experimental techniques. Spectroelectrochemistry analysis of the homopolymer reflects electronic transitions at 434, ∼800 and ∼1100 nm, revealing π-π* transition, polaron and bipolaron band formation, respectively, leading to esthetically pleasing color changes between transmissive yellow and blue, with reasonable switching times

  16. Conducting polymers of decanedioic acid bis-(4-pyrrol-1-yl-phenyl) ester

    International Nuclear Information System (INIS)

    Cirpan, A.; Guner, Y.; Toppare, L.

    2004-01-01

    A dipyrrolyl monomer was synthesized via the reaction between 4-pyrrol-1-yl phenol and decanedioyl dichloride. The electrochemical behavior of this monomer was studied. Polymerization of decanedioic acid bis-(4-pyrrol-1-yl-phenyl) ester (DAPE) was achieved by chemical and constant current electrolyses methods. Copolymerization of DAPE with thiophene was performed by constant potential electrolysis in acetonitrile-tetrabutylammonium tetrafluoroborate (TBAFB), dichloromethane-TBAFB, solvent-electrolyte couples. The chemical structures and properties were investigated by Fourier transform infrared spectroscopy, nuclear magnetic resonance spectroscopy, differential scanning calorimetry and thermal gravimetry analysis. The conductivities of the samples were measured by a four-probe technique

  17. Conducting polymers of decanedioic acid bis-(4-pyrrol-1-yl-phenyl) ester

    Energy Technology Data Exchange (ETDEWEB)

    Cirpan, A.; Guner, Y.; Toppare, L

    2004-05-15

    A dipyrrolyl monomer was synthesized via the reaction between 4-pyrrol-1-yl phenol and decanedioyl dichloride. The electrochemical behavior of this monomer was studied. Polymerization of decanedioic acid bis-(4-pyrrol-1-yl-phenyl) ester (DAPE) was achieved by chemical and constant current electrolyses methods. Copolymerization of DAPE with thiophene was performed by constant potential electrolysis in acetonitrile-tetrabutylammonium tetrafluoroborate (TBAFB), dichloromethane-TBAFB, solvent-electrolyte couples. The chemical structures and properties were investigated by Fourier transform infrared spectroscopy, nuclear magnetic resonance spectroscopy, differential scanning calorimetry and thermal gravimetry analysis. The conductivities of the samples were measured by a four-probe technique.

  18. Synthesis, Crystal Structure and Biological Activities of Novel Anthranilic(Isophthalic) Acid Esters

    Institute of Scientific and Technical Information of China (English)

    YAN Tao; YU Guan-ping; LIU Peng-fei; XIONG Li-xia; YU Shu-jing; LI Zheng-ming

    2012-01-01

    In search of environmentally benign insecticides with high activity,low toxicity and low resistance,a series of novel anthranilic(isophthalic) acid esters was designed and synthesized based on the structure of ryanodine modulating agent.All the compounds were characterized by 1H NMR spectra,elemental analysis or high resolution mass spectrometry(HRMS).The preliminary results of biological activity assessment indicate that some of the title compounds exhibit certain but unremarkable insecticidal activity against Mythimna separata Walker at 200 mg/L and fungicidal activities against five funguses at 50 mg/L.

  19. AN ESTER OF 4-METHOXY CYNNAMIC ACID ISOLATED FROM Xylocarpus moluccencis (Lamk M. Roem (MELIACEAE

    Directory of Open Access Journals (Sweden)

    Tukiran Tukiran

    2012-06-01

    Full Text Available An ester derivative of 4-methoxycynnamic acid, i.e. 2-ethylhexyl 4-methoxy cynnamate was isolated for the first time from the chloroform extract of stem bark of Xylocarpus moluccencis (Lamk M. Roem (Meliaceae along with β-sitosterol and stigmasterol. The first structure was elucidated with the help of various spectroscopic techniques, including IR, GC-MS, and NMR spectra. Two last structures were determined by comparison with the reported compounds in literature. These compounds were also found in the hexane extract of the plant.

  20. Microbial dynamics in anaerobic enrichment cultures degrading di-n-butyl phthalic acid ester

    DEFF Research Database (Denmark)

    Trably, Eric; Batstone, Damien J.; Christensen, Nina

    2008-01-01

    losses were observed in the sterile controls (20-22%), substantial DBP biodegradation was found in the enrichment cultures (90-99%). In addition, significant population changes were observed. The dominant bacterial species in the DBP-degrading cultures was affiliated to Soehngenia saccharolytica...... in enrichment cultures degrading phthalic acid esters under methanogenic conditions. A selection pressure was applied by adding DBP at 10 and 200 mg L(-1) in semi-continuous anaerobic reactors. The microbial dynamics were monitored using single strand conformation polymorphism (SSCP). While only limited abiotic...

  1. Occurrence of 3-MCPD fatty acid esters in human breast milk

    OpenAIRE

    2008-01-01

    Abstract A series of twelve breast milks was analysed by GC/MS operated in SIM mode for 3-chloropropane-1,2-diol (3-MCPD). While none of samples contained free 3-MCPD at the level exceeding the method detection limit of (3 g/kg milk), all of them contained high amount of 3-MCPD esterified with higher fatty acids. The levels of 3-MCPD released by hydrolysis of these esters (bound 3-MCPD) ranged from the limit of detection (300 g/kg, expressed on fat basis) to 2195 &#...

  2. Lipases and whole cell biotransformations of 2-hydroxy-2-(ethoxyphenylphosphinyl)acetic acid and its ester.

    Science.gov (United States)

    Majewska, Paulina; Serafin, Monika; Klimek-Ochab, Magdalena; Brzezińska-Rodak, Małgorzata; Żymańczyk-Duda, Ewa

    2016-06-01

    A wide spectrum of commercially available lipases and microbial whole cells catalysts were tested for biotransformations of 2-hydroxy-2-(ethoxyphenylphosphinyl)acetic acid 1 and its butyryl ester. The best results were achieved for biocatalytic hydrolysis of ester: 2-butyryloxy-2-(ethoxyphenylphosphinyl)acetic acid 2 performed by lipase from Candida cylindracea, what gave optically active products with 85% enantiomeric excess, 50% conversion degree and enantioselectivity 32.9 for one pair of enantiomers. Also enzymatic systems of Penicillium minioluteum and Fusarium oxysporum were able to hydrolyze tested compound with high enantiomeric excess (68-93% ee), enantioselectivity (44 for one pair of enantiomers) and conversion degree about 50-55%. Enzymatic acylation of hydroxyphosphinate was successful in case when porcine pancreas lipase was used. After 4days of biotransformation the conversion reaches 45% but the enantiomeric enrichment of the isomers mixture do not exceed 43%. Obtained chiral compounds are valuable derivatizing agents for spectroscopic (NMR) evaluation of enantiomeric excess for particular compounds (e.g. amino acids). Copyright © 2016 The Authors. Published by Elsevier Inc. All rights reserved.

  3. Spectroscopic studies of the quality of WCO (Waste Cooking Oil fatty acid methyl esters

    Directory of Open Access Journals (Sweden)

    Matwijczuk Arkadiusz

    2018-01-01

    Full Text Available Different kinds of biodiesel fuels become more and more attractive form of fuel due to their unique characteristics such as: biodegradability, replenishability, and what is more a very low level of toxicity in terms of using them as a fuel. The test on the quality of diesel fuel is becoming a very important issue mainly due to the fact that its high quality may play an important role in the process of commercialization and admitting it on the market. The most popular techniques among the wellknown are: molecular spectroscopy and molecular chromatography (especially the spectroscopy of the electron absorption and primarily the infrared spectroscopy (FTIR.The issue presents a part of the results obtained with the use of spectroscopy of the electron absorption and in majority infrared spectroscopy FTIR selected for testing samples of the acid fats WCO (Waste Cooking Oil types. The samples were obtained using laboratory methods from sunflower oil and additionally from waste animal fats delivered from slaughterhouses. Acid methyl esters were selected as references to present the samples. In order to facilitate the spectroscopic analysis, free glycerol, methanol, esters and methyl linolenic acid were measured

  4. Equilibrium partitioning of drug molecules between aqueous and amino acid ester-based ionic liquids

    International Nuclear Information System (INIS)

    Jing, Jun; Li, Zhiyong; Pei, Yuanchao; Wang, Huiyong; Wang, Jianji

    2013-01-01

    Highlights: ► Partition coefficients of twelve drug molecules in ILs have been determined. ► The possible mechanism has been investigated from 13 C NMR measurements. ► Hydrophobic π–π interaction is the main driving force for the partitioning of drug molecules. -- Abstract: In this work, a series of novel room temperature ionic liquids (ILs) have been synthesized with cheap, naturally α-amino acid ester as cations and bis(trifluoromethylsulfonyl)imide as anion. The glass transition temperature and thermal decomposition temperature of these ILs, partition coefficients of some coumarins and purine alkaloids between water and the amino acid ester-based ILs at T = 298.15 K, and Gibbs energy, enthalpy and entropy changes for the transfer of caffeine and 6,7-dihydroxycoumarin from water to [LeuC 2 ][Tf 2 N] have been determined. It is shown that these ILs are highly effective materials for the extraction of drug compounds like coumarin, 4-hydroxycoumarin, 7-hydroxycoumarin, 3-aminocoumarin, coumarin-3-carboxylic acid, 6,7-dihydroxycoumarin, 6,7-dihydroxy-4-methylcoumarin, caffeine, theobromine, theophylline, inosine, and 2,6-diaminopurine. The partition process is driven by enthalpy term, and partition coefficients of the drug molecules increase with the increase of hydrophobicity of both the drug molecules and the ILs. Furthermore, the possible partition mechanism has been investigated from 13 C NMR measurements

  5. Wolman's disease and cholesteryl ester storage disorder: the phenotypic spectrum of lysosomal acid lipase deficiency.

    Science.gov (United States)

    Pericleous, Marinos; Kelly, Claire; Wang, Tim; Livingstone, Callum; Ala, Aftab

    2017-09-01

    Lysosomal acid lipase deficiency is a rare, autosomal recessive condition caused by mutations in the gene encoding lysosomal acid lipase (LIPA) that result in reduced or absent activity of this essential enzyme. The severity of the resulting disease depends on the nature of the underlying mutation and magnitude of its effect on enzymatic function. Wolman's disease is a severe disorder that presents during infancy, resulting in failure to thrive, hepatomegaly, and hepatic failure, and an average life expectancy of less than 4 months. Cholesteryl ester storage disorder arises later in life and is less severe, although the two diseases share many common features, including dyslipidaemia and transaminitis. The prevalence of these diseases has been estimated at one in 40 000 to 300 000, but many cases are undiagnosed and unreported, and awareness among clinicians is low. Lysosomal acid lipase deficiency-which can be diagnosed using dry blood spot testing-is often misdiagnosed as non-alcoholic fatty liver disease (NAFLD), non-alcoholic steatohepatitis (NASH), hereditary dyslipidaemia, or cryptogenic cirrhosis. There are no formal guidelines for treatment of these patients, and treatment options are limited. In this Review we appraise the existing literature on Wolman's disease and cholesteryl ester storage disease, and discuss available treatments, including enzyme replacement therapy, oral lipid-lowering therapy, stem-cell transplantation, and liver transplantation. Copyright © 2017 Elsevier Ltd. All rights reserved.

  6. Poly(vinyl alcohol)/poly(acrylic acid)/TiO2/graphene oxide nanocomposite hydrogels for pH-sensitive photocatalytic degradation of organic pollutants

    International Nuclear Information System (INIS)

    Moon, Young-E; Jung, Gowun; Yun, Jumi; Kim, Hyung-Il

    2013-01-01

    Graphical abstract: The photocatalytic removal of pollutants was improved by the two-step mechanism based on the adsorption of pollutants by hydrogel and the effective decomposition by combination of TiO 2 and graphene oxide. -- Highlights: • pH sensitive PVA/PAAc hydrogels were prepared by radical polymerization and condensation reaction. • PVA/PAAc/TiO 2 /graphene oxide nanocomposite hydrogels were used for treatment of basic waste water. • Photocatalytic acitivity of TiO 2 was improved by incorporation of graphene oxide. • Photocatalytic decomposition by nanocomposite hydrogel was improved by increasing pH. -- Abstract: Poly(vinyl alcohol)/poly(acrylic acid)/TiO 2 /graphene oxide nanocomposite hydrogels were prepared using radical polymerization and condensation reaction for the photocatalytic treatment of waste water. Graphene oxide was used as an additive to improve the photocatalytic activity of poly(vinyl alcohol)/poly(acrylic acid)/TiO 2 nanocomposite hydrogels. Both TiO 2 and graphene oxide were immobilized in poly(vinyl alcohol)/poly(acrylic acid) hydrogel matrix for an easier recovery after the waste water treatment. The photocatalytic activity of poly(vinyl alcohol)/poly(acrylic acid)/TiO 2 /graphene oxide nanocomposite hydrogels was evaluated on the base of the degradation of pollutants by using UV spectrometer. The improved removal of pollutants was due to the two-step mechanism based on the adsorption of pollutants by nanocomposite hydrogel and the effective decomposition of pollutants by TiO 2 and graphene oxide. The highest swelling of nanocomposite hydrogel was observed at pH 10 indicating that poly(vinyl alcohol)/poly(acrylic acid)/TiO 2 /graphene oxide nanocomposite hydrogels were suitable as a promising system for the treatment of basic waste water

  7. Stereochemistry of Endogenous Palmitic Acid Ester of 9-Hydroxystearic Acid and Relevance of Absolute Configuration to Regulation.

    Science.gov (United States)

    Nelson, Andrew T; Kolar, Matthew J; Chu, Qian; Syed, Ismail; Kahn, Barbara B; Saghatelian, Alan; Siegel, Dionicio

    2017-04-05

    Lipids have fundamental roles in the structure, energetics, and signaling of cells and organisms. The recent discovery of fatty acid esters of hydroxy fatty acids (FAHFAs), lipids with potent antidiabetic and anti-inflammatory activities, indicates that our understanding of the composition of lipidome and the function of lipids is incomplete. The ability to synthesize and test FAHFAs was critical in elucidating the roles of these lipids, but these studies were performed with racemic mixtures, and the role of stereochemistry remains unexplored. Here, we synthesized the R- and S- palmitic acid ester of 9-hydroxystearic acid (R-9-PAHSA, S-9-PAHSA). Access to highly enantioenriched PAHSAs enabled the development of a liquid chromatography-mass spectrometry (LC-MS) method to separate and quantify R- and S-9-PAHSA, and this approach identified R-9-PAHSA as the predominant stereoisomer that accumulates in adipose tissues from transgenic mice where FAHFAs were first discovered. Furthermore, biochemical analysis of 9-PAHSA biosynthesis and degradation indicate that the enzymes and pathways for PAHSA production are stereospecific, with cell lines favoring the production of R-9-PAHSA and carboxyl ester lipase (CEL), a PAHSA degradative enzyme, selectively hydrolyzing S-9-PAHSA. These studies highlight the role of stereochemistry in the production and degradation of PAHSAs and define the endogenous stereochemistry of 9-PAHSA in adipose tissue. This information will be useful in the identification and characterization of the pathway responsible for PAHSA biosynthesis, and access to enantiopure PAHSAs will elucidate the role of stereochemistry in PAHSA activity and metabolism in vivo.

  8. Isolation and characterization of fatty acid methyl ester (FAME)-producing Streptomyces sp. S161 from sheep (Ovis aries) faeces.

    Science.gov (United States)

    Lu, Y; Wang, J; Deng, Z; Wu, H; Deng, Q; Tan, H; Cao, L

    2013-09-01

    An actinomycete producing oil-like mixtures was isolated and characterized. The strain was isolated from sheep faeces and identified as Streptomyces sp. S161 based on 16S rRNA gene sequence analysis. The strain showed cellulase and xylanase activities. The (1) H nuclear magnetic resonance (NMR) spectra of the mixtures showed that the mixtures were composed of fatty acid methyl esters (52·5), triglycerides (13·7) and monoglycerides (9·1) (mol.%). Based on the gas chromatography-mass spectrometry (GC-MS) analysis, the fatty acid methyl esters were mainly composed of C14-C16 long-chain fatty acids. The results indicated that Streptomyces sp. S161 could produce fatty acid methyl esters (FAME) directly from starch. To our knowledge, this is the first isolated strain that can produce biodiesel (FAME) directly from starch. © 2013 The Society for Applied Microbiology.

  9. Bioreversible Derivatives of Phenol. 2. Reactivity of Carbonate Esters with Fatty Acid-like Structures Towards Hydrolysis in Aqueous Solutions

    Directory of Open Access Journals (Sweden)

    Claus Larsen

    2007-10-01

    Full Text Available A series of model phenol carbonate ester prodrugs encompassing derivatives with fatty acid-like structures were synthesized and their stability as a function of pH (range 0.4 – 12.5 at 37°C in aqueous buffer solutions investigated. The hydrolysis rates in aqueous solutions differed widely, depending on the selected pro-moieties (alkyl and aryl substituents. The observed reactivity differences could be rationalized by the inductive and steric properties of the substituent groups when taking into account that the mechanism of hydrolysis may change when the type of pro-moiety is altered, e.g. n-alkyl vs. t-butyl. Hydrolysis of the phenolic carbonate ester 2-(phenoxycarbonyloxy-acetic acid was increased due to intramolecular catalysis, as compared to the derivatives synthesized from ω-hydroxy carboxylic acids with longer alkyl chains. The carbonate esters appear to be less reactive towards specific acid and base catalyzed hydrolysis than phenyl acetate. The results underline that it is unrealistic to expect that phenolic carbonate ester prodrugs can be utilized in ready to use aqueous formulations. The stability of the carbonate ester derivatives with fatty acid-like structures, expected to interact with the plasma protein human serum albumin, proved sufficient for further in vitro and in vivo evaluation of the potential of utilizing HSA binding in combination with the prodrug approach for optimization of drug pharmacokinetics.

  10. Scientific opinion: Risks for human health related to the presence of 3- and 2-monochloropropanediol (MCPD), and their fatty acid esters, and glycidyl fatty acid esters in food

    NARCIS (Netherlands)

    Hoogenboom, L.A.P.

    2016-01-01

    EFSA was asked to deliver a scientific opinion on free and esterified 3- and 2-monochloropropane-1,2-diol (MCPD) and glycidyl esters in food. Esters of 3- and 2-MCPD and glycidol are contaminants of processed vegetable oils; free MCPDs are formed in some processed foods. The Panel on Contaminants in

  11. Improving the Performances of Poly(vinylphosphonic acid) by Compositing or Copolymerization with Poly(4-(α-methyl)vinyl-1H-1,2,3-triazole)

    International Nuclear Information System (INIS)

    Han, Shuaiyuan; Yue, Baohua; Yan, Liuming

    2014-01-01

    Graphical abstract: - Highlights: • Poly(4-(α-methyl)vinyl-1H-1,2,3-triazole) is synthesized • PVPA/PMVTri polymeric composite proton conducting membranes are prepared • The proton conductivity of PVPA is improved by compositing with PMVTri • The water resistance of PVPA is improved by compositing with PMVTri • The oxidative stability is greatly improved - Abstract: The poly(vinylphosphonic acid) (PVPA), poly(4-(α-methyl)vinyl-1H-1,2,3-triazole) (PMVTri), and poly(VPA-co-MVTri) were synthesized, and proton exchange membranes were prepared based on the acid-base polymeric composite of PVPA and PMVTri, and acid-base amphoteric copolymer of poly(VPA-co-MVTri). The overall performances of PVPA, proton conductivity, thermal and oxidative stability, and water resistance, are greatly improved by compositing of PMVTri or copolymerization with 4-(α-methyl)vinyl-1H-1,2,3-triazole (MVTri). About four or eight folds improvement in maximum proton conductivity was observed in the polymeric composite of PVPA/PMVTri or acid-base amphoteric copolymer poly(VPA-co-MVTri) because of the redistribution of ions in the heterostructures of PVPA and PMVTri, respectively, compared with the pristine PVPA. At the same time, the oxidative stability and the water resistance of PVPA were also greatly improved attributing to the absent of α-H in the main chain of PMVTri and the acid-base interaction between the phosphonic acid groups and the triazolyl groups, respectively

  12. In vitro assessment of phthalate acid esters-trypsin complex formation.

    Science.gov (United States)

    Chi, Zhenxing; Zhao, Jing; Li, Weiguo; Araghi, Arash; Tan, Songwen

    2017-10-01

    In this work, interactions of three phthalate acid esters (PAEs), including dimethyl phthalate (DMP), diethyl phthalate (DEP) and dibutyl phthalate (DBP), with trypsin have been studied in vitro, under simulated physiological conditions using multi-spectroscopic techniques and molecular modeling. The results show that these PAEs can bind to the trypsin, forming trypsin-PAEs complexes, mainly via hydrophobic interactions, with the affinity order of DMP > DEP > DBP. Binding to the PAEs is found to result in molecular deformation of trypsin. The modeling results suggest that only DBP can bind with the amino acid residues of the catalytic triad and S1 binding pocket of trypsin, leading to potential competitive enzyme inhibition. Copyright © 2017 Elsevier Ltd. All rights reserved.

  13. Thermodynamic study of phase transitions in methyl esters of ortho- meta- and para-aminobenzoic acids

    International Nuclear Information System (INIS)

    Almeida, Ana R.R.P.; Monte, Manuel J.S.

    2012-01-01

    Highlights: ► Vapor pressures of liquid and crystalline phases of methyl esters of the aminobenzoic acids were measured. ► Accurate values of enthalpies of sublimation, vaporization, and fusion were derived. ► The enthalpy of intermolecular NH–O hydrogen bonds in methyl p-aminobenzoate was determined. ► The volatility of the methyl benzoates was compared with the volatility of the parent acids. - Abstract: A static method based on capacitance gauges was used to measure the vapor pressures of the condensed phases of the methyl esters of the three aminobenzoic acids. For methyl o-aminobenzoate the vapor pressures of the liquid phase were measured in the range (285.4 to 369.5) K. For the meta and para isomers vapor pressures of both crystalline and liquid phases were measured in the ranges (308.9 to 376.6) K, and (332.9 to 428.0) K, respectively. Vapor pressures of the latter compound were also measured using the Knudsen effusion method in the temperature range (319.1 to 341.2) K. From the dependence of the vapor pressures on the temperature, the standard molar enthalpies and entropies of sublimation and of vaporization were derived. Differential scanning calorimetry was used to measure the temperatures and molar enthalpies of fusion of the three isomers. The results enabled the estimation of the enthalpy of the intermolecular (N−H … O) hydrogen bond in the crystalline methyl p-aminobenzoate. A correlation relating the temperature of fusion and the enthalpy and Gibbs energy of sublimation of benzene, methyl benzoates and benzoic acids was derived.

  14. Supported phosphate and carbonate salts for heterogeneous catalysis of triglycerides to fatty acid methyl esters

    Science.gov (United States)

    Britton, Stephanie Lynne

    Fatty acid methyl esters made from vegetable oil, or biodiesel, have been identified as a substitute for diesel derived from crude oil. Biodiesel is currently made using a homogeneous base catalyst to perform the transesterification of triglycerides with methanol to generate fatty acid methyl esters (FAME). The use of a homogeneous catalyst necessitates additional purification of the product and byproducts before sale, and the catalyst is consumed and discarded. The development of a heterogeneous basic catalyst for the production of FAME is desirable. Tribasic phosphate salts and dibasic carbonate salts are active for the production of FAME but generally operate as homogeneous catalysts. Supporting these phosphate and carbonate salts on mesoporous MCM-41, microporous silica gel, and nonporous a-alumina proved successful to greater or lesser degrees depending on the identity of the support and pretreatment of the support. Although these salts were supported and were active for the production of FAME from canola oil, they proved to be operating as homogeneous catalysts due to leaching of the active species off the surface of the support. Further investigation of the active species present in the tribasic phosphate catalysts identified the active support as orthophosphate, and NMR studies revealed the phosphorus to be present as orthophosphate and diphosphate in varying proportions in each catalyst. Evaluation of the acid-washing support pretreatment process revealed that the exposure of the support to acid plays a large role in the development of activity on the surface of the catalyst, but manipulation of these parameters did not prevent leaching of the active site off the surface of the catalyst. Alternate methods of support pretreatment were no more effective in preventing leaching. Tribasic phosphate supported on silica gel is not effective as a heterogeneous catalyst for FAME production from triglycerides because of the lack of stability of the phosphate on the

  15. Conversion of beet molasses and cheese whey into fatty acid methyl esters by the yeast Cryptococcus curvatus.

    Science.gov (United States)

    Takakuwa, Naoya; Saito, Katsuichi

    2010-01-01

    Eighty-one yeast isolates from raw milk were surveyed for the production of fatty acid methyl esters (FAME). Only one species, identified as Cryptococcus curvatus, produced FAME at a detectable level. Cr. curvatus TYC-19 produced more FAME from beet molasses and cheese whey medium than other strains of the same species. In both media, the major FAME produced were linoleic and oleic acid methyl esters. Sequence analysis of the internal transcribed spacer region of ribosomal DNA indicated that TYC-19 diverged from the same species.

  16. Evaluation of the influence of base and alkyl bromide on synthesis of pyrazinoic acid esters through factorial design

    International Nuclear Information System (INIS)

    Fernandes, Joao Paulo dos Santos; Felli, Veni Maria Andres

    2009-01-01

    Pyrazinoic acid esters have been synthesized as prodrugs of pyrazinoic acid. In the literature, its preparation is reported through the reaction of pyrazinoyl chloride with alcohols and the reaction with DCC/DMAP. In this work, it is reported a 22 factorial design to evaluate the preparation of these esters through the substitution of alkyl bromides with carboxylate anion. The controlled factors were alkyl chain length of bromides (ethyl and hexyl) and the used base (triethylamine and DBU). Results revealed that the used base used has significant effect on yield, and alkyl bromide used has neither significant influence, nor its interaction effect with base. (author)

  17. Saponification of esters of chiral alpha-amino acids anchored through their amine function on solid support.

    Science.gov (United States)

    Cantel, Sonia; Desgranges, Stéphane; Martinez, Jean; Fehrentz, Jean-Alain

    2004-06-01

    Anchoring an alpha-amino acid residue by its amine function onto a solid support is an alternative to develop chemistry on its carboxylic function. This strategy can involve the use of amino-acid esters as precursors of the carboxylic function. A complete study on the Wang-resin was performed to determine the non racemizing saponification conditions of anchored alpha-amino esters. The use of LiOH, NaOH, NaOSi(Me)3, various solvents and temperatures were tested for this reaction. After saponification and cleavage from the support, samples were examined through their Marfey's derivatives by reversed phase HPLC to evaluate the percentage of racemization.

  18. Autoxidation of conjugated linoleic acid methyl ester in the presence of α-tocopherol: the hydroperoxide pathway

    OpenAIRE

    Pajunen, Taina

    2009-01-01

    The autoxidation of conjugated linoleic acid (CLA) is poorly understood in spite of increasing interest in the beneficial biological properties of CLA and growing consumption of CLA-rich foods. In this thesis, the autoxidation reactions of the two major CLA isomers, 9-cis,11-trans-octadecadienoic acid and 10-trans,12-cis-octadecadienoic acid, are investigated. The results contribute to an understanding of the early stages of the autoxidation of CLA methyl ester, and provide for the first time...

  19. Fatty acid methyl esters and Solutol HS 15 confer neuroprotection after focal and global cerebral ischemia.

    Science.gov (United States)

    Lin, Hung Wen; Saul, Isabel; Gresia, Victoria L; Neumann, Jake T; Dave, Kunjan R; Perez-Pinzon, Miguel A

    2014-02-01

    We previously showed that palmitic acid methyl ester (PAME) and stearic acid methyl ester (SAME) are simultaneously released from the sympathetic ganglion and PAME possesses potent vasodilatory properties which may be important in cerebral ischemia. Since PAME is a potent vasodilator simultaneously released with SAME, our hypothesis was that PAME/SAME confers neuroprotection in rat models of focal/global cerebral ischemia. We also examined the neuroprotective properties of Solutol HS15, a clinically approved excipient because it possesses similar fatty acid compositions as PAME/SAME. Asphyxial cardiac arrest (ACA, 6 min) was performed 30 min after PAME/SAME treatment (0.02 mg/kg, IV). Solutol HS15 (2 ml/kg, IP) was injected chronically for 14 days (once daily). Histopathology of hippocampal CA1 neurons was assessed 7 days after ACA. For focal ischemia experiments, PAME, SAME, or Solutol HS15 was administered following reperfusion after 2 h of middle cerebral artery occlusion (MCAO). 2,3,5-Triphenyltetrazolium staining of the brain was performed 24 h after MCAO and the infarct volume was quantified. Following ACA, the number of surviving hippocampal neurons was enhanced by PAME-treated (68%), SAME-treated (69%), and Solutol-treated HS15 (68%) rats as compared to ACA only-treated groups. Infarct volume was decreased by PAME (83%), SAME (68%), and Solutol HS15 (78%) as compared to saline (vehicle) in MCAO-treated animals. PAME, SAME, and Solutol HS15 provide robust neuroprotection in both paradigms of ischemia. This may prove therapeutically beneficial since Solutol HS15 is already administered as a solublizing agent to patients. With proper timing and dosage, administration of Solutol HS15 and PAME/SAME can be an effective therapy against cerebral ischemia.

  20. Lasiojasmonates A-C, three jasmonic acid esters produced by Lasiodiplodia sp., a grapevine pathogen.

    Science.gov (United States)

    Andolfi, Anna; Maddau, Lucia; Cimmino, Alessio; Linaldeddu, Benedetto T; Basso, Sara; Deidda, Antonio; Serra, Salvatorica; Evidente, Antonio

    2014-07-01

    In this study, a strain (BL 101) of a species of Lasiodiplodia, not yet formally described, which was isolated from declining grapevine plants showing wedge-shaped cankers, was investigated for its ability to produce in vitro bioactive secondary metabolites. From culture filtrates of this strain three jasmonic acid esters, named lasiojasmonates A-C and 16-O-acetylbotryosphaerilactones A and C were isolated together with (1R,2R)-jasmonic acid, its methyl ester, botryosphaerilactone A, (3S,4R,5R)-4-hydroxymethyl-3,5-dimethyldihydro-2-furanone and (3R,4S)-botryodiplodin. The structures of lasiojasmonates A-C were established by spectroscopic methods as (1R*,2R*,3'S*,4'R*,5'R*)-4-hydroxymethyl-3,5-dimethyldihydro-2-furanone, (1R*,2R*,3'S*,4'R*,5'R*,10'R*,12'R*,13'R*,14'S*) and (1R*,2R*,3'S*,4'R*,5'R*,10'S*,12'R*,13'R*,14'S*)-4-(4-hydroxymethyl-3,5-dimethyltetrahydro-furan-2-yloxymethyl)-3,5-dimethyldihydro-2-furanones jasmonates (1, 4 and 5). The structures of 16-O-acetylbotryosphaerilactones A and C were determined by comparison of their spectral data with those of the corresponding acetyl derivatives obtained by acetylation of botryosphaerilactone A. The metabolites isolated, except 4 and 5, were tested at 1mg/mL on leaves of grapevine cv. Cannonau and cork oak using the leaf puncture assay. They were also tested on detached grapevine leaves at 0.5mg/mL and tomato cuttings at 0.1mg/mL. In all phytotoxic assays only jasmonic acid was found to be active. All metabolites were inactive in the zootoxic assay at 50 μg/mL. Copyright © 2014. Published by Elsevier Ltd.

  1. Recognition/removal of phloretic acid on molecularly imprinted poly(n-vinyl imidazole) based polymers grafted onto nonwoven fabrics

    International Nuclear Information System (INIS)

    Ranada, Ma. Llorina; Abad, Lucille; Akbulut, Meshude; Guven, Olgun

    2013-01-01

    Molecular imprinting is the process of developing polymeric matrices for recognizing a target molecule in the presence of chemically similar structures. These matrices can be tailored using one or more functional monomers with a cross linker in the presence of a molecule behaving as the template. Phloretic acid is one of the members of dietary phenolic group which may have physiological antioxidant properties, potentially modifying pathological mechanisms relevant to some health problems such as cardiovascular diseases and cancer. The content of these compounds is generally very low in plants to be detected by traditional instruments. Thus, the development of an easy, cheap and reliable method is an important issue. In this study, a solution of n-vinyl imidazole was grafted onto polypropylene/polyethylene (PP/PE) films through gamma irradiation to create a film-based polymer matrix for phloretic acid. These films are assessed in terms of structural and binding capacity. The maximum free-volume ratio was obtained at 5 kGy using positron annihilation lifetime spectroscopy (PALS). The imprinting capacity of the matrix system is 2.41 between the molecularly-imprinted and the non-imprinted films. Scanning electron microscopy and Fourier-Transform Infrared Spectroscopy complemented the PALS data in elucidating the structure of the grafted films. (author)

  2. Sugar-Responsive Layer-by-Layer Film Composed of Phenylboronic Acid-Appended Insulin and Poly(vinyl alcohol).

    Science.gov (United States)

    Takei, Chihiro; Ohno, Yui; Seki, Tomohiro; Miki, Ryotaro; Seki, Toshinobu; Egawa, Yuya

    2018-01-01

    Previous studies have shown that reversible chemical bond formation between phenylboronic acid (PBA) and 1,3-diol can be utilized as the driving force for the preparation of layer-by-layer (LbL) films. The LbL films composed of a PBA-appended polymer and poly(vinyl alcohol) (PVA) disintegrated in the presence of sugar. This type of LbL films has been recognized as a promising approach for sugar-responsive drug release systems, but an issue preventing the practical application of LbL films is combining them with insulin. In this report, we have proposed a solution for this issue by using PBA-appended insulin as a component of the LbL film. We prepared two kinds of PBA-appended insulin derivatives and confirmed that they retained their hypoglycemic activity. The LbL films composed of PBA-appended insulin and PVA were successfully prepared through reversible chemical bond formation between the boronic acid moiety and the 1,3-diol of PVA. The LbL film disintegrated upon treatment with sugars. Based on the results presented herein, we discuss the suitability of the PBA moiety with respect to hypoglycemic activity, binding ability, and selectivity for D-glucose.

  3. Poly(vinyl chloride) catheters modified with pH-responsive poly(methacrylic acid) with affinity for antimicrobial agents

    Science.gov (United States)

    Zuñiga-Zamorano, Ivette; Meléndez-Ortiz, H. Iván; Costoya, Alejandro; Alvarez-Lorenzo, Carmen; Concheiro, Angel; Bucio, Emilio

    2018-01-01

    Radiation-grafting of pH-responsive methacrylic acid (MAA) onto poly(vinyl chloride) (PVC) was carried out by the pre-irradiation method using gamma rays, which demonstrated to be an efficient and fast procedure for obtaining PVC-g-MAA copolymers. The influence of preparation conditions, such as absorbed dose, monomer concentration, reaction time, and reaction temperature on the grafting yield was studied. The grafting of MAA onto PVC catheters was confirmed by means of Fourier transform infrared spectroscopy (FT-IR), thermogravimetry analysis (TGA), and differential scanning calorimetry (DSC). The pH-responsiveness of the grafted copolymers (critical point 8.5) was measured by swelling under cyclic changes in the pH of the medium. Interestingly, PVC-g-MAA showed enhanced capability to immobilize benzalkonium chloride and, particularly, ciprofloxacin and to sustain the release this antimicrobial agent at both acid and alkaline pH. Tests carried out with Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus point out that the developed functionalized catheters may play a role in the prevention/management of urinary tract infections.

  4. Antinociceptive esters of N-methylanthranilic acid: Mechanism of action in heat-mediated pain.

    Science.gov (United States)

    Pinheiro, Mariana Martins Gomes; Radulović, Niko S; Miltojević, Ana B; Boylan, Fabio; Dias Fernandes, Patrícia

    2014-03-15

    Recently, we identified a new natural antinociceptive alkaloid ternanthranin, isopropyl N-methylanthranilate (ISOAN), from the plant species Choisya ternata Kunth (Rutaceae). In this work we concentrated on the elucidation of its mechanism of action in comparison with two other esters of this acid (methyl (MAN) and propyl (PAN)). Mice orally pre-treated with ISOAN, MAN or PAN (at 0.3, 1 and 3mg/kg) were less sensitive to chemical or thermal stimuli in different nociception models (formalin-, capsaicin- and glutamate-induced licking response, tail flick and hot plate). All compounds (1 and 3mg/kg) showed significant activity in the peripheral nociception models, as well as a dose-dependent spinal antinociceptive effect in the tail flick model. We observed that glibenclamide was able to reverse the antinociceptive effect of ISOAN in the hot plate model suggesting the involvement of K(+)ATP channels. The antinociceptive effect of MAN and PAN may be related to adrenergic, nitrergic and serotoninergic pathways. In addition, the antinociception of PAN was reverted by naloxone implying that the opioid pathway participates in its activity. The cholinergic and cannabinoid systems were found not be involved in the onset of the antinociceptive effects of any of the esters. In conclusion, isopropyl, methyl and propyl N-methylanthranilates produced significant peripheral and central antinociception at doses lower than that of morphine, the classical opioid analgesic drug, without causing toxicity. Copyright © 2014 Elsevier B.V. All rights reserved.

  5. Lipid profiling of the soybean pathogen Phytophthora sojae using Fatty Acid Methyl Esters (FAMEs).

    Science.gov (United States)

    Yousef, Lina Fayez; Wojno, Michal; Dick, Warren A; Dick, Richard P

    2012-05-01

    Phytophthora sojae is a destructive soilborne pathogen of soybean, but currently there is no rapid or commercially available testing for its infestation level in soil. For growers, such information would greatly improve their ability to make management decisions to minimize disease damage to soybean crops. Fatty acid profiling of P. sojae holds potential for determining the prevalence of this pathogen in soil. In this study, the Fatty Acid Methyl Ester (FAME) profile of P. sojae was determined in pure culture, and the profile was subsequently evaluated for its potential use in detecting the pathogen in soil. The predominant fatty acids in the FAME profile of P. sojae are the unsaturated 18C fatty acids (18:1ω9 and 18:2ω6) followed by the saturated and unsaturated 16C fatty acids (16:0 and 16:1ω7). FAME analysis of P. sojae zoospores showed two additional long-chain saturated fatty acids (20:0 and 22:0) that were not detected in the mycelium of this organism. Addition of a known number of zoospores of P. sojae to soil demonstrated that fatty acids such as 18:1ω9, 18:2ω6, 20:1ω9, 20:4ω6, and 22:1ω9 could be detected and quantified against the background levels of fatty acids present in soil. These results show the potential for using selected FAMEs of P. sojae as a marker for detecting this pathogen in soybean fields. Copyright © 2012 British Mycological Society. Published by Elsevier Ltd. All rights reserved.

  6. Synthesis, characterization and application of lipase-conjugated citric acid-coated magnetic nanoparticles for ester synthesis using waste frying oil.

    Science.gov (United States)

    Patel, Unisha; Chauhan, Kishor; Gupte, Shilpa

    2018-04-01

    In the present work, magnetic nanoparticles (MNPs) were prepared by chemical precipitation of trivalent and divalent iron ions which were functionalized using citric acid. The bacterial isolate Staphylococcus epidermidis KX781317 was isolated from oil-contaminated site. The isolate produced lipase, which was purified and immobilized on magnetic nanoparticles (MNPs) for ester synthesis from waste frying oil (WFO). The characterization of MNPs employed conventional TEM, XRD and FTIR techniques. TEM analysis of MNPs showed the particle size in the range of 20-50 nm. FTIR spectra revealed the binding of citric acid to Fe 3 O 4 and lipase on citric acid-coated MNPs. The citric acid-coated MNPs and lipase-conjugated citric acid-coated MNPs had similar XRD patterns which indicate MNPs could preserve their magnetic properties. The maximum immobilization efficiency 98.21% of lipase-containing citric acid-coated MNPs was observed at ratio 10:1 of Cit-MNPs:lipase. The pH and temperature optima for lipase conjugated with Cit-MNPs were 7 and 35 °C, respectively. Isobutanol was found to be an effective solvent for ester synthesis and 1:2 ratio of oil:alcohol observed significant for ester formation. The ester formation was determined using TLC and the % yield of ester conversion was calculated. The rate of ester formation is directly proportional to the enzyme load. Formed esters were identified as isobutyl laurate ester and isobutyl myristate ester through GC-MS analysis.

  7. Studies on the Simultaneous Formation of Aroma-Active and Toxicologically Relevant Vinyl Aromatics from Free Phenolic Acids during Wheat Beer Brewing.

    Science.gov (United States)

    Langos, Daniel; Granvogl, Michael

    2016-03-23

    During the brewing process of wheat beer, the desired aroma-active vinyl aromatics 2-methoxy-4-vinylphenol and 4-vinylphenol as well as the undesired and toxicologically relevant styrene are formed from their respective precursors, free ferulic acid, p-coumaric acid, and cinnamic acid, deriving from the malts. Analysis of eight commercial wheat beers revealed high concentrations of 2-methoxy-4-vinylphenol and 4-vinylphenol always in parallel with high concentrations of styrene or low concentrations of the odorants in parallel with low styrene concentrations, suggesting a similar pathway. To better understand the formation of these vinyl aromatics, each process step of wheat beer brewing and the use of different strains of Saccharomyces cerevisiae were evaluated. During wort boiling, only a moderate decarboxylation of free phenolic acids and formation of desired and undesired vinyl aromatics were monitored due to the thermal treatment. In contrast, this reaction mainly occurred enzymatically catalyzed during fermentation with S. cerevisiae strain W68 with normal Pof(+) activity (phenolic off-flavor) resulting in a wheat beer eliciting the typical aroma requested by consumers due to high concentrations of 2-methoxy-4-vinylphenol (1790 μg/L) and 4-vinylphenol (937 μg/L). Unfortunately, also a high concentration of undesired styrene (28.3 μg/L) was observed. Using a special S. cerevisiae strain without Pof(+) activity resulted in a significant styrene reduction (beer aroma.

  8. Radiolysis of fatty acid esters in n-hexane solution in an atmosphere of nitrogen

    International Nuclear Information System (INIS)

    Kimura, Kazuo; Shirai, Kazuo

    1975-01-01

    There have been several problems in food preservation by irradiation. Deterioration of food components by irradiation is one of the most substantial subjects. This investigation was undertaken as a basic experiment to discuss the radiolysis of lipids in food irradiation. In the previous paper, radiolytic examination on six of methyl esters of fatty acids in n-hexane solution in the presence of air was reported. In the present work the same samples-methyl stearate (C sub(18:0)), methyl oleate (C sub(18:1)), methyl linoleate (C sub(18:2)), methyl linolenate (C sub(18:3)), methyl arachidate (C sub(20:0)) and methyl arachidonate (C sub(20:4)) were examined in an atmosphere of nitrogen. Samples in n-hexane solution were sealed in glass ampules after substituted with nitrogen. Preparations were treated with 60 Co-gamma-radiation at dose from 1.8 x 10 6 to 7.1 x 10 6 rads. These preparations were analyzed by gas chromatography, infrared spectrophotometry and iodine value determination. The results were as follows: 1. Generally speaking saturated acids were stable and unsaturated were unstable. 2. In unsaturated series, the high unsaturated fatty acids were more labile to gamma-irradiation and the more increased doses induced the more drastic decompositions. 3. It was observed by infrared spectra that some isomerization from cis to trans configuration occured at double bond systems in unsaturated fatty acids. (auth.)

  9. Studies of reaction difference between γ-ray and glow discharge on hydrogenation of unsaturated fatty acid esters

    International Nuclear Information System (INIS)

    Sakoda, Tatsuya; Nieda, Hiroshi; Kitahara, Kazuta; Ando, Kiyomi

    2000-01-01

    Hydrogenation of unsaturated fatty acid esters using an inductively coupled plasma at low pressure was performed, and electron temperature and density were measured using a double-probe in order to investigate the reaction difference between γ-ray and glow discharge on hydrogenation. In this experiment, unsaturated fatty acid esters were partly hydrogenated by the hydrogen plasma that had electron temperature of 3.5 eV, which was more efficient than γ-ray irradiation method. As a result, it was found that the plasma can effectively supply electrons that had the optimum energy for hydrogenation at the interface of fatty acids as well as excited atoms and ions. Also, the plasma generated at low pressure would be possible to convert unsaturated fatty acids into saturated fatty acids without breaking the starting monomer. (author)

  10. Increased production of wax esters in transgenic tobacco plants by expression of a fatty acid reductase:wax synthase gene fusion.

    Science.gov (United States)

    Aslan, Selcuk; Hofvander, Per; Dutta, Paresh; Sun, Chuanxin; Sitbon, Folke

    2015-12-01

    Wax esters are hydrophobic lipids consisting of a fatty acid moiety linked to a fatty alcohol with an ester bond. Plant-derived wax esters are today of particular concern for their potential as cost-effective and sustainable sources of lubricants. However, this aspect is hampered by the fact that the level of wax esters in plants generally is too low to allow commercial exploitation. To investigate whether wax ester biosynthesis can be increased in plants using transgenic approaches, we have here exploited a fusion between two bacterial genes together encoding a single wax ester-forming enzyme, and targeted the resulting protein to chloroplasts in stably transformed tobacco (Nicotiana benthamiana) plants. Compared to wild-type controls, transgenic plants showed both in leaves and stems a significant increase in the total level of wax esters, being eight-fold at the whole plant level. The profiles of fatty acid methyl ester and fatty alcohol in wax esters were related, and C16 and C18 molecules constituted predominant forms. Strong transformants displayed certain developmental aberrations, such as stunted growth and chlorotic leaves and stems. These negative effects were associated with an accumulation of fatty alcohols, suggesting that an adequate balance between formation and esterification of fatty alcohols is crucial for a high wax ester production. The results show that wax ester engineering in transgenic plants is feasible, and suggest that higher yields may become achieved in the near future.

  11. Process for the conversion of sugars to lactic acid and 2-hydroxy-3-butenoic acid or esters thereof comprising a metallo-silicate material and a metal ion

    DEFF Research Database (Denmark)

    2015-01-01

    A process for the preparation of lactic acid and 2-hydroxy- 3-butenoic acid or esters thereof from a sugar in the presence of a metallo-silicate material, a metal ion and a solvent, wherein the metal ion is selected from one or more of the group consisting of potassium ions, sodium ions, lithium...

  12. Antiviral Properties of Caffeic Acid Phenethyl Ester and Its Potential Application

    Directory of Open Access Journals (Sweden)

    Haci Kemal Erdemli

    2015-12-01

    Full Text Available Caffeic acid phenethyl ester (CAPE is found in variety of plants and well known active ingredient of the honeybee propolis. CAPE showed anti-inflammatory, anticarcinogenic, antimitogenic, antiviral and immunomodulatory properties in several studies. The beneficial effects of CAPE on different health issues attracted scientists to make more studies on CAPE. Specifically, the anti-viral effects of CAPE and its molecular mechanisms may reveal the important properties of virus-induced diseases. CAPE and its targets may have important roles to design new therapeutics and understand the molecular mechanisms of virus related diseases. In this mini-review, we summarize the antiviral effects of CAPE under the light of medical and chemical literature. [J Intercult Ethnopharmacol 2015; 4(4.000: 344-347

  13. Solubility Testing of Sucrose Esters of Fatty Acids in International Food Additive Specifications.

    Science.gov (United States)

    Nagai, Yukino; Kawano, Satoko; Motoda, Kenichiro; Tomida, Masaaki; Tatebe, Chiye; Sato, Kyoko; Akiyama, Hiroshi

    2017-03-01

    We investigated the solubility of 10 samples of sucrose esters of fatty acids (SEFA) products that are commercially available worldwide as food additives (emulsifiers). Although one sample dissolved transparently in both water and ethanol, other samples produced white turbidity and/or precipitates and did not meet the solubility criterion established by the Joint Food and Agriculture Organization of the United Nations (FAO)/WHO Expert Committee on Food Additives (JECFA). When the sample solutions were heated, the solubility in both water and ethanol increased. All of the samples dissolved transparently in ethanol, and dispersed and became white without producing precipitates in water. The present study suggests that the current solubility criterion of the JECFA SEFA specifications needs to be revised.

  14. Comparison of GC stationary phases for the separation of fatty acid methyl esters in biodiesel fuels.

    Science.gov (United States)

    Goding, Julian C; Ragon, Dorisanne Y; O'Connor, Jack B; Boehm, Sarah J; Hupp, Amber M

    2013-07-01

    The fatty acid methyl ester (FAME) content of biodiesel fuels has traditionally been determined using gas chromatography with a polar stationary phase. In this study, a direct comparison of the separation of FAMEs present in various biodiesel samples on three polar stationary phases and one moderately polar stationary phase (with comparable column dimensions) was performed. Retention on each column was based on solubility in and polarity of the phase. Quantitative metrics describing the resolution of important FAME pairs indicate high resolution on all polar columns, yet the best resolution, particularly of geometric isomers, is achieved on the cyanopropyl column. In addition, the separation of four C18 monounsaturated isomers was optimized and the elution order determined on each column. FAME composition of various biodiesel fuel types was determined on each column to illustrate (1) chemical differences in biodiesels produced from different feedstocks and (2) chemical similarities in biodiesels of the same feedstock type produced in different locations and harvest seasons.

  15. Study on the concentration of unsaturated fatty acid methyl esters by urea complexation

    International Nuclear Information System (INIS)

    Jiang, B.; Liu, Y.

    2014-01-01

    This study was done to obtain concentrated unsaturated fatty acid methyl esters (FAME) by urea complexation from soybean derived FAME. Effects of urea-to-FAME ratio, 95% ethanol-to-FAME ratio, crystallization temperature and time on the purification of unsaturated FAME were investigated through single factor experiments. Optimum conditions to obtain maximum FAME yield of NUCF with the purity of unsaturated FAME greater than 98% were established using Box-Behnken design (BBD) method and response surface methodology (RSM). Under optimal conditions, the FAME yield was 58.08%, and the purity of unsaturated FAME was 98% at a urea-to-FAME ratio of 1.23, 95% ethanol-to-FAME ratio of 7 and crystallization temperature of 0 degree C. Verification results revealed that the predicted values were reasonably close to experimentally observed values of 56.93% and 98.01%. (author)

  16. Can propolis and caffeic acid phenethyl ester (CAPE be promising agents against cyclophosphamide toxicity?

    Directory of Open Access Journals (Sweden)

    Sumeyya Akyol

    2016-03-01

    Full Text Available Propolis is a mixture having hundreds of polyphenols including caffeic acid phenethyl ester (CAPE. They have been using in several medical conditions/diseases in both in vitro and in vivo experimental setup. Cyclophosphamide has been used to treat a broad of malignancies including Hodgkin’s and non-Hodgking’s lymphoma, Burkitt’s lymphoma, chronic lymphocytic leukemia, Ewing’s sarcoma, breast cancer, testicular cancer, etc. It may cause several side effects after treatment. In this mini review, the protective effects of propolis and CAPE were compared each other in terms of effectiveness against cyclophosphamide-induced injuries. [J Complement Med Res 2016; 5(1.000: 105-107

  17. Microwave-assisted pyrolysis of methyl ricinoleate for continuous production of undecylenic acid methyl ester (UAME).

    Science.gov (United States)

    Nie, Yong; Duan, Ying; Gong, Ruchao; Yu, Shangzhi; Lu, Meizhen; Yu, Fengwen; Ji, Jianbing

    2015-06-01

    Undecylenic acid methyl ester (UAME) was continuously produced from methyl ricinoleate using a microwave-assisted pyrolysis system with atomization feeding. The UAME yield of 77 wt.% was obtained at 500°C using SiC as the microwave absorbent and heating medium. The methyl ricinoleate conversion and UAME yield from microwave-assisted pyrolysis process were higher than those from conventional pyrolysis. The effect of temperature on the pyrolysis process was also investigated. The methyl ricinoleate conversion increased but the cracking liquid yield decreased when the temperature increased from 460°C to 560°C. The maximum UAME yield was obtained at the temperature of 500°C. Copyright © 2015 Elsevier Ltd. All rights reserved.

  18. Drinking-water-criteria document for phthalic acid esters (PAES). Final report

    International Nuclear Information System (INIS)

    1991-08-01

    The document provides the health effects basis to be considered in establishing the MCLG. To achieve the objective, data on pharmacokinetics human exposure, acute and chronic toxicity to animals and humans, epidemiology and mechanisms of toxicity are evaluated for phthalic acid esters. Specific emphasis is placed on literature data providing dose-response information. Thus, while the literature search and evaluation performed in support of the document has been comprehensive, only the reports considered most pertinent in the derivation of the MCLG are cited in the document. The comprehensive literature data base in support of the document includes information published up to 1986; however, more recent data may have been added during the review process

  19. [Comparative assessment of Cladophora, Spirogyra and Oedogonium biomass for the production of fatty acid methyl esters].

    Science.gov (United States)

    Haq, I; Muhammad, A; Hameed, U

    2014-01-01

    The use of alternative fuels for the mitigation of ecological impacts by use of diesel has been focus of intensive research. In the present work, algal oils extracted from cultivated biomass of Cladophora sp., Spirogyra sp. and Oedogonium sp. were evaluated for the lipase-mediated synthesis of fatty acid monoalkyl esters (FAME, biodiesel). To optimize the transesterification of these oils, different parameters such as the alkyl group donor, reaction temperature, stirring time and oil to alcohol ratio were investigated. Four different alcohols i.e. methanol, ethanol, n-propanol and n-butanol were tested as alkyl group donor for the biosynthesis FAME and methanol was found to be the best. Similarly, temperature 50 C and stirring time of 6 h were optimized for the transesterification of oils with methanol. The maximum biodiesel conversions from Cladophora (75.0%), Spirogyra (87.5%) and Oedogonium (92.0%) were obtained when oil to alcohol ratio was 1 : 8.

  20. Selective rhodium-catalyzed reduction of tertiary amides in amino acid esters and peptides.

    Science.gov (United States)

    Das, Shoubhik; Li, Yuehui; Bornschein, Christoph; Pisiewicz, Sabine; Kiersch, Konstanze; Michalik, Dirk; Gallou, Fabrice; Junge, Kathrin; Beller, Matthias

    2015-10-12

    Efficient reduction of the tertiary amide bond in amino acid derivatives and peptides is described. Functional group selectivity has been achieved by applying a commercially available rhodium precursor and bis(diphenylphosphino)propane (dppp) ligand together with phenyl silane as a reductant. This methodology allows for specific reductive derivatization of biologically interesting peptides and offers straightforward access to a variety of novel peptide derivatives for chemical biology studies and potential pharmaceutical applications. The catalytic system tolerates a variety of functional groups including secondary amides, ester, nitrile, thiomethyl, and hydroxy groups. This convenient hydrosilylation reaction proceeds at ambient conditions and is operationally safe because no air-sensitive reagents or highly reactive metal hydrides are needed. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  1. Preparation and investigation of mefenamic acid - polyethylene glycol - sucrose ester solid dispersions.

    Science.gov (United States)

    Fülöp, Ibolya; Gyéresi, Árpád; Kiss, Lóránd; Deli, Mária A; Croitoru, Mircea Dumitru; Szabó-Révész, Piroska; Aigner, Zoltán

    2015-12-01

    Mefenamic acid (MA) is a widely used non-steroidal antiinflammatory (NSAID) drug. The adverse effects typical of NSAIDs are also present in the case of MA, partly due to its low water solubility. The aim of this study was to increase the water solubility of MA in order to influence its absorption and bioavailability. Solid dispersions of MA were prepared by the melting method using polyethylene glycol 6000 and different types (laurate, D-1216; palmitate, P-1670; stearate, S-1670) and amounts of sucrose esters as carriers. The X-ray diffraction results show that MA crystals were not present in the products. Dissolution tests carried out in artificial intestinal juice showed that the product containing 10 % D-1216 increased water solubility about 3 times. The apparent permeability coefficient of MA across human Caco-2 intestinal epithelial cell layers was high and, despite the difference in solubility, there was no further increase in drug penetration in the presence of the applied additives.

  2. Synthesis of carboxylic acids, esters, alcohols and ethers containing a tetrahydropyran ring derived from 6-methyl-5-hepten-2-one.

    Science.gov (United States)

    Hanzawa, Yohko; Hashimoto, Kahoko; Kasashima, Yoshio; Takahashi, Yoshiko; Mino, Takashi; Sakamoto, Masami; Fujita, Tsutomu

    2012-01-01

    3-hydroxy acids, 3-hydroxy-3,7-dimethyloct-6-enoic acid (1) and 3-hydroxy-2,2,3,7-tetramethyloct-6-enoic acid (2), were prepared from 6-methyl-5-hepten-2-one, and they were subsequently used to prepare (2,6,6-trimethyltetrahydropyran-2-yl)acetic acid (3) and 2-methyl-2-(2,6,6-trimethyltetrahydropyran-2-yl)propanoic acid (4), respectively, via cyclization with an acidic catalyst such as boron trifluoride diethyl etherate or iodine. The reaction of carboxylic acids 3 and 4 with alcohols, including methanol, ethanol, and 1-propanol, produced the corresponding methyl, ethyl, and propyl esters, which all contained a tetrahydropyran ring. Reduction of carboxylic acids 3 and 4 afforded the corresponding alcohols. Subsequent reactions of these alcohols with several acyl chlorides produced novel esters. The alcohols also reacted with methyl iodide and sodium hydride to provide novel ethers. A one-pot cyclization-esterification of 1 to produce esters containing a tetrahydropyran ring, using iodine as a catalyst, was also investigated.

  3. High-throughput and sensitive analysis of 3-monochloropropane-1,2-diol fatty acid esters in edible oils by supercritical fluid chromatography/tandem mass spectrometry.

    Science.gov (United States)

    Hori, Katsuhito; Matsubara, Atsuki; Uchikata, Takato; Tsumura, Kazunobu; Fukusaki, Eiichiro; Bamba, Takeshi

    2012-08-10

    We have established a high-throughput and sensitive analytical method based on supercritical fluid chromatography (SFC) coupled with triple quadrupole mass spectrometry (QqQ MS) for 3-monochloropropane-1,2-diol (3-MCPD) fatty acid esters in edible oils. All analytes were successfully separated within 9 min without sample purification. The system was precise and sensitive, with a limit of detection less than 0.063 mg/kg. The recovery rate of 3-MCPD fatty acid esters spiked into oil samples was in the range of 62.68-115.23%. Furthermore, several edible oils were tested for analyzing 3-MCPD fatty acid ester profiles. This is the first report on the analysis of 3-MCPD fatty acid esters by SFC/QqQ MS. The developed method will be a powerful tool for investigating 3-MCPD fatty acid esters in edible oils. Copyright © 2012 Elsevier B.V. All rights reserved.

  4. Effect of caffeic acid phenethyl ester on bone formation in the expanded inter-premaxillary suture

    Directory of Open Access Journals (Sweden)

    Kazancioglu HO

    2015-12-01

    Full Text Available Hakki Oguz Kazancioglu,1 Sertac Aksakalli,2 Seref Ezirganli,1 Muhammet Birlik,2 Mukaddes Esrefoglu,3 Ahmet Hüseyin Acar1 1Department of Oral and Maxillofacial Surgery, 2Department of Orthodontics, Faculty of Dentistry, 3Department of Histology, Faculty of Medicine, Bezmialem Vakif University, Istanbul, Turkey Background: Narrow maxilla is a common problem in orthodontics and dentofacial orthopedics. To solve this problem, a procedure called rapid maxillary expansion (RME has been used. However, relapse tendency is a major problem of RME. Although relapse tendency is not clearly understood, various treatment procedures and new application has been investigated. The present study aimed to investigate the possible effectiveness of caffeic acid phenethyl ester (CAPE on new bone formation in rat midpalatal suture after RME.Materials and methods: Twenty male Sprague Dawley rats were used in this study. The animals were randomly divided into two groups as control and CAPE group. In CAPE group, CAPE was administered systemically via intraperitoneal injection. RME procedure was performed on all animals. For this purpose, the springs were placed on the maxillary incisors of rats and activated for 5 days. After then, the springs were removed and replaced with short lengths of rectangular retaining wire for consolidation period of 15 days. At the end of the study, histomorphometric analysis was carried out to assess of new bone formation.Results: New bone formation was significantly greater in CAPE group than the control group (P<0.05. CAPE enhances new bone formation in midpalatal suture after RME.Conclusion: These results show that CAPE may decrease the time needed for retention. Keywords: rapid maxillary expansion, bone formation, caffeic acid phenethyl ester, midpalatal suture, histopathology

  5. Synthesis and Characterization of Fatty Acid Methyl Ester by In-Situ Transesterification in Capparis Deciduas Seed

    Directory of Open Access Journals (Sweden)

    Prasad E FUNDE

    2008-12-01

    Full Text Available (FAME Fatty acid methyl ester is made virgin or used vegetable oils (both edible and non-edible and animal fats. Fatty acid methyl ester operates in compression ignition engines like petro-diesel. Fatty acid methyl ester can be blended in any ratio with petroleum diesel fuels. It can be stored just like the petroleum diesel fuel. Petrodiesel can be replaced by biodiesel due to its superiority. It has various advantages. The seeds of Capparis deciduas are found to contain non-edible oil in the range of about 63.75 %. The percentage of biodiesel yield increases with concentration of KOH as a catalyst. The aim of this article is to demonstrate the cost effective new source of energy by single step reaction i.e. production of oil by combining extraction and reaction of extract with the mixture of alcohols. In this article the effect of catalyst concentration, time, water content and temperature on in-situ transesterification is studied to obtain optimum yield and Fatty acid methyl ester (Biodiesel Fuel characterization tests show the striking similarity of various physical & chemical properties and campers to ASTM standards.

  6. Effect of alkyl chain length in the terminal ester group on mesomorphic properties of new chiral lactic acid derivatives

    Czech Academy of Sciences Publication Activity Database

    Kohout, M.; Bubnov, Alexej; Šturala, J.; Novotná, Vladimíra; Svoboda, J.

    2016-01-01

    Roč. 43, č. 10 (2016), s. 1472-1485 ISSN 0267-8292 R&D Projects: GA MŠk(CZ) LD14007 Institutional support: RVO:68378271 Keywords : chiral liquid crystal * lactic acid derivative * terminal ester group * mesomorphic properties * dielectric spectroscopy * layer shrinkage Subject RIV: JJ - Other Materials Impact factor: 2.661, year: 2016

  7. Determination of Total Lipids as Fatty Acid Methyl Esters (FAME) by in situ Transesterification: Laboratory Analytical Procedure (LAP)

    Energy Technology Data Exchange (ETDEWEB)

    Van Wychen, Stefanie; Ramirez, Kelsey; Laurens, Lieve M. L.

    2016-01-13

    This procedure is based on a whole biomass transesterification of lipids to fatty acid methyl esters to represent an accurate reflection of the potential of microalgal biofuels. Lipids are present in many forms and play various roles within an algal cell, from cell membrane phospholipids to energy stored as triacylglycerols.

  8. Characterization of spirochetal isolates from arthropods collected in South Moravia, Czech Republic, using fatty acid methyl esters analysis

    Czech Academy of Sciences Publication Activity Database

    Čechová, L.; Durnová, E.; Šikutová, Silvie; Halouzka, Jiří; Němec, M.

    2004-01-01

    Roč. 808, č. 2 (2004), s. 249-254 ISSN 1570-0232 R&D Projects: GA ČR GA206/03/0726 Institutional research plan: CEZ:AV0Z6093917 Keywords : spirochetes * arthropods * fatty acid methyl esters Subject RIV: EE - Microbiology, Virology Impact factor: 2.176, year: 2004

  9. Glycidyl fatty acid esters in refined edible oils: A review on formation, occurrence, analysis, and elimination methods

    Science.gov (United States)

    Glycidyl fatty acid esters (GEs), one of the main contaminants in processed oil, are mainly formed during the deodorization step in the oil refining process of edible oils and therefore occur in almost all refined edible oils. GEs are potential carcinogens, due to the fact that they hydrolyze into t...

  10. Acetobacter turbidans α-Amino Acid Ester Hydrolase. How a Single Mutation Improves an Antibiotic-Producing Enzyme

    NARCIS (Netherlands)

    Barends, Thomas R.M.; Polderman-Tijmes, Jolanda J.; Jekel, Peter A.; Williams, Christopher; Wybenga, Gjalt; Janssen, Dick B.; Dijkstra, Bauke W.

    2006-01-01

    The α-amino acid ester hydrolase (AEH) from Acetobacter turbidans is a bacterial enzyme catalyzing the hydrolysis and synthesis of β-lactam antibiotics. The crystal structures of the native enzyme, both unliganded and in complex with the hydrolysis product D-phenylglycine are reported, as well as

  11. Improving the sustainability of fatty acid methyl esters (Fame – biodiesel) – assessment of options for industry and agriculture

    NARCIS (Netherlands)

    Jungmeier, G.; Pucker, J.; Ernst, M.; Haselbacher, P.; Lesschen, J.P.; Kraft, A.; Schulzke, T.; Loo, van E.N.

    2016-01-01

    The life cycle based greenhouse gas (GHG) balances of Fatty Acid Methyl Esters (FAME also called “Biodiesel”) from various resources have been set in the Renewable Energy Directive (RED). Due to technology and scientific progress there are various options to improve the GHG balances of FAME. In

  12. Dietary exposure of Hong Kong adults to fatty acid esters of 3-monochloropropane-1,2-diol.

    Science.gov (United States)

    Chung, H Y; Chung, Stephen W C; Chan, B T P; Ho, Yuk Yin; Xiao, Ying

    2013-01-01

    A total of 290 individual food samples were collected in Hong Kong, China, for 3-monochloropropane-1,2-diol (3-MCPD) fatty acid esters analysis. Most samples were processed food and in ready-to-eat form. The results show that the levels of 3-MCPD fatty acid esters were high in biscuits, fats and oils, snacks and Chinese pastry with mean bound 3-MCPD levels of 440, 390, 270 and 270 μg kg⁻¹, respectively. The dietary exposures to bound 3-MCPD of average and high adult consumers were estimated to be 0.20 and 0.53 μg kg bw⁻¹ day⁻¹, respectively. The primary toxicological concern of 3-MCPD fatty acid esters is its potential to release 3-MCPD in vivo during digestion in the gastrointestinal tract. 3-MCPD would affect the kidney, the central nervous system and the male reproductive system of rats. Assuming that 100% of the 3-MCPD was released from 3-MCPD fatty acid esters by hydrolysis in the digestive system, the dietary exposures to 3-MCPD for average and high adult consumers were only 10% and 26% of the provisional maximum tolerable daily intake (PMTDI) of 3-MCPD established by the Joint Food and Agriculture Organization/World Health Organization Expert Committee on Food Additives (JECFA) (2 μg kg bw⁻¹ day⁻¹), respectively. The results suggest that both average and high adult consumers are unlikely to experience major toxicological effects of 3-MCPD.

  13. 40 CFR 721.3130 - Sulfuric acid, mono-C9-11-alkyl esters, sodium salts.

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Sulfuric acid, mono-C9-11-alkyl esters, sodium salts. 721.3130 Section 721.3130 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... significant new uses are: (i) Industrial, commercial, and consumer activities. Requirements as specified in...

  14. The effects of egg and diacetyl tartaric acid esters of monoglycerides addition on gluten-free sorghum bread quality

    Science.gov (United States)

    The impact of whole egg addition (as is) at 20, 25, or 30% (flour basis) on sorghum bread quality was evaluated. The use of the antistaling agent diacetyl tartaric acid esters of monoglycerides (DATEM) at 0.5% (flour basis) at each of the egg addition levels was also studied. Evaluated quality facto...

  15. Free fatty acids and esters can be immobilized by receptor rich membranes from torpedo marmorata but not phospholipid acyl chains

    NARCIS (Netherlands)

    Rousselet, A.; Devaux, P.F.; Wirtz, K.W.A.

    1979-01-01

    A long chain spin labeled fatty acid and the corresponding ester have been introduced into receptor rich membranes from Torpedo Marmorata. Superimposed to a mobile component, typical of the lipid phase, a strongly immobilized component is seen on the ESR spectra, both at low temperature (−4°C) and

  16. Investigation of Complexation of Linear Poly(N-vinyl-2-pyrrolidone with Poly(methacrylic acid-co-methyl methacrylate Gel

    Directory of Open Access Journals (Sweden)

    Guoqin Liu

    2011-01-01

    Full Text Available The contraction of poly(methacrylic acid-co-methyl methacrylate (P(MAA-co-MMA gel induced by complexation with linear poly(N-vinyl-2-pyrrolidone (PVP is quite different from that of poly(acrylic acid (PAA or poly(methacrylic acid (PMAA gel. It was found that the concentration of PVP has a strong effect on the complexation with P(MAA-co-MMA gel. When PVP was introduced into the P(MAA-co-MMA network, its dynamic mechanic properties vary greatly between complexed and uncomplexed networks. It had the following results: (1 the higher modulus ratio; (2 a slight contraction of gel.

  17. Investigation of Complexation of Linear Poly(N-vinyl-2-pyrrolidone) with Poly(methacrylic acid-co-methyl methacrylate) Gel

    OpenAIRE

    Liu, Guoqin; Yan, Guojin; Zou, Wenjun; Li, Zhengxin

    2011-01-01

    The contraction of poly(methacrylic acid-co-methyl methacrylate) (P(MAA-co-MMA)) gel induced by complexation with linear poly(N-vinyl-2-pyrrolidone) (PVP) is quite different from that of poly(acrylic acid) (PAA) or poly(methacrylic acid) (PMAA) gel. It was found that the concentration of PVP has a strong effect on the complexation with P(MAA-co-MMA) gel. When PVP was introduced into the P(MAA-co-MMA) network, its dynamic mechanic properties vary greatly between complexed and uncomplexed netwo...

  18. Acute effects of sodium valproate and gamma-vinyl GABA on regional amino acid metabolism in the rat brain: incorporation of 2-[14C]glucose into amino acids.

    Science.gov (United States)

    Chapman, A G; Riley, K; Evans, M C; Meldrum, B S

    1982-09-01

    Amino acid concentrations have been determined in rat brain regions (cortex, striatum, cerebellum, and hippocampus) by HPLC after administration of acute anticonvulsant doses of sodium valproate (400 mg/kg, i.p.) and gamma-vinyl-GABA (1 g/kg, i.p.). After valproate administration the GABA level increases only in the cortex; aspartic acid concentration decreases in the cortex and hippocampus, and glutamic acid decreases in the hippocampus and striatum and increases in the cortex and cerebellum. There are no changes in the concentrations of glutamine, taurine, glycine, serine, and alanine following valproate administration. Only the GABA level increases in all the regions after gamma-vinyl-GABA administration. Cortical analyses 2, 4 and 10 minutes after pulse labeling with 2-[14C]glucose, i.v., show no change in the rate of cortical glucose utilization in the valproate treated group. The rate of labeling of glutamic acid is also unchanged, but the rate of labeling of GABA is reduced following valproate administration. After gamma-vinyl-GABA administration there is no change in the rate of labeling of GABA. These biochemical findings can be interpreted in terms of a primary anticonvulsant action of valproate on membrane receptors with secondary effects on the metabolism of amino acid neurotransmitters. This contrasts with the primary action of gamma-vinyl-GABA on GABA-transaminase activity.

  19. Preparation of Poly(Vinyl Alcohol) Grafted With Acrylic Acid/Styrene Binary Monomers For Selective Permeation of Heavy Metals

    International Nuclear Information System (INIS)

    Hegazy El-Sayed, A.; Abd El-Rehim, H.A.; Ali, A.M.; Aly, H.F.

    1999-01-01

    A study has been made to modify water-soluble poly(vinyl alcohol) (PVA), by grafting acrylic acid and styrene (AAc/Sty) binary monomers using gamma rays as initiator. The factors that affect the preparation process and grafting yield were studied and more economical grafts under the most favorable reaction conditions were obtained. It was found that the high degree of grafting of such system was obtained in presence of ethanol-water mixture in which water plays a significant role in enhancing the graft copolymerization. The critical amount of water to afford maximum grafting yield has been evaluated. The effect of comonomer composition on the grafting yield was also investigated and it was observed that using a mixture of AAc/Sty monomers influence the extent of grafting of each monomer onto the PVA substrate and the phenomenon of synergism occurs during such reaction. Also, degree of grafting increases as the content of the solvent decreases in the reaction medium. The permeation of heavy metals such as Ni and Co through the grafted membranes was investigated and efficiency of separation process is also determined

  20. Prolonged Hypocalcemic Effect by Pulmonary Delivery of Calcitonin Loaded Poly(Methyl Vinyl Ether Maleic Acid Bioadhesive Nanoparticles

    Directory of Open Access Journals (Sweden)

    J. Varshosaz

    2014-01-01

    Full Text Available The purpose of the present study was to design a pulmonary controlled release system of salmon calcitonin (sCT. Therefore, poly(methyl vinyl ether maleic acid [P(MVEMA] nanoparticles were prepared by ionic cross-linking method using Fe2+ and Zn2+ ions. Physicochemical properties of nanoparticles were studied in vitro. The stability of sCT in the optimized nanoparticles was studied by electrophoretic gel method. Plasma calcium levels until 48 h were determined in rats as pulmonary-free sCT solution or nanoparticles (25 μg·kg−1, iv solution of sCT (5 μg·kg−1, and pulmonary blank nanoparticles. The drug remained stable during fabrication and tests on nanoparticles. The optimized nanoparticles showed proper physicochemical properties. Normalized reduction of plasma calcium levels was at least 2.76 times higher in pulmonary sCT nanoparticles compared to free solution. The duration of hypocalcemic effect of pulmonary sCT nanoparticles was 24 h, while it was just 1 h for the iv solution. There was not any significant difference between normalized blood calcium levels reduction in pulmonary drug solution and iv injection. Pharmacological activity of nanoparticles after pulmonary delivery was 65% of the iv route. Pulmonary delivery of P(MVEMA nanoparticles of sCT enhanced and prolonged the hypocalcemic effect of the drug significantly.

  1. Radiation synthesis and characterization of pH-sensitive poly(acrylic acid-co-N-vinyl-2-pyrrolidone) hydrogels

    International Nuclear Information System (INIS)

    Yang Mingcheng; Zhu Jun; Song Weidong; Song Hongyan; Zhu Chengshen

    2006-01-01

    Hydrogels are crosslinked, three-dimensional hydrophilic polymer networks that swell but do not dissolve when brought into contact with water. These materials have been investigated extensively for potential applications in the biomedical field because of their similarities to soft tissues and their good tissue and blood compatibility. More specifically, pH-sensitive hydrogels are used for sustained gastro-intestinal drug delivery systems due to the intimacy and extended duration of contact. In this work, pH-sensitive copolymer hydrogels were prepared using acrylic acid and N-vinyl-2-pyrrolidone by γ-ray irradiation at ambient temperature. Effects of dose, monomer concentration, monomer composition, temperature and pH on the swelling ratio (SR) of the copolymer hydrogels were investigated in detail. The results show that SR of the copolymer hydrogels decreases with the monomer concentration and with the increase of absorbed dose. These copolymer hydrogels show good pH-sensitive behavior. These material shows no noticeable change in swelling at lower pH (pH<4) but an abrupt increase in swelling at higher pH (from pH7 to pH9.8). At pH 1.4, the SR of the copolymer hydrogels increases with the temperature. To the contrary, at pH 9.8, the SR of the copolymer hydrogels decreases with the temperature. (authors)

  2. Poly(methyl vinyl ether-alt-maleic acid)-functionalized porous silicon nanoparticles for enhanced stability and cellular internalization.

    Science.gov (United States)

    Shahbazi, Mohammad-Ali; Almeida, Patrick V; Mäkilä, Ermei; Correia, Alexandra; Ferreira, Mónica P A; Kaasalainen, Martti; Salonen, Jarno; Hirvonen, Jouni; Santos, Hélder A

    2014-03-01

    Currently, developing a stable nanocarrier with high cellular internalization and low toxicity is a key bottleneck in nanomedicine. Here, we have developed a successful method to covalently conjugate poly(methyl vinyl ether-co-maleic acid) (PMVE-MA) copolymer on the surface of (3-aminopropyl)triethoxysilane-functionalized thermally carbonized porous silicon nanoparticles (APSTCPSi NPs), forming a surface negatively charged nanovehicle with unique properties. This polymer conjugated NPs could modify surface smoothness, charge, and hydrophilicity of the developed NPs, leading to considerable improvement in the colloidal and plasma stabilities via enhanced suspensibility and charge repulsion. Furthermore, despite the surface negative charge of the polymer-conjugated NPs, the cellular internalization was increased in both MDA-MB-231 and MCF-7 breast cancer cells. These results provide a proof-of-concept evidence that such polymer-based PSi nanocomposite can be extensively used as a promising candidate for intracellular drug delivery. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  3. Amphoteric surfactants containing ?-hydroxy ester group and an amino acid residue

    Directory of Open Access Journals (Sweden)

    Eissa, A. M. F.

    2006-09-01

    Full Text Available A series of amphoteric surfactants containing α-hydroxy ester group and an amino acid residue were prepared with the addition of epoxy derivatives (which were prepared from epoxidation of alkyl methacrylate to different types of amino acids (glycine, alanine, valine, isoleucine, phenylalanine, tyrosine, serine, threonine, aspartic and anthranilic acid.The structures of the prepared compounds were confirmed by infrared spectra, proton magnetic resonance spectra, Mass spectra and elementary analysis. Surface tension, Kraft point, foaming power, critical micelle concentration emulsion and Ca++ stabilities were determined. Antimicrobial activity and biodegradability were also screened.Se prepararon una serie de tensioactivos anfóteros conteniendo un grupo alfa hidroxi éster y un residuo de aminoácido por adición de derivados epoxy (obtenidos mediante epoxidación de metacrilato de alquilo a diferentes tipos de aminoácidos (glicina, alanina, valina, isoleucina, fenilalanina, tirosina, serina, treonina y ácidos aspártico y antranílico. Las estructuras de los compuestos preparados se confirmaron por los espectros de infrarrojo, de masa, resonancia magnética nuclear de protones y análisis elemental. Se determinaron la tensión superficial, el punto de Kraft, el poder espumante, la concentración micelar crítica en emulsión y las estabilidades de Ca++. También se estudiaron la actividad antimicrobiana y la biodegradabilidad.

  4. Parallel Synthesis of a Library of Symmetrically- and Dissymmetrically-disubstituted Imidazole-4,5-dicarboxamides Bearing Amino Acid Esters

    Directory of Open Access Journals (Sweden)

    Rosanna Solinas

    2009-01-01

    Full Text Available The imidazole-4,5-dicarboxylic acid scaffold is readily derivatized with amino acid esters to afford symmetrically- and dissymmetrically-disubstituted imidazole-4,5-dicarboxamides with intramolecularly hydrogen bonded conformations that predispose the presentation of amino acid pharmacophores. In this work, a total of 45 imidazole-4,5-dicarboxamides bearing amino acid esters were prepared by parallel synthesis. The library members were purified by column chromatography on silica gel and the purified compounds characterized by LC-MS with LC detection at 214 nm. A selection of the final compounds was also analyzed by 1H-NMR spectroscopy. The analytically pure final products have been submitted to the Molecular Library Small Molecule Repository (MLSMR for screening in the Molecular Library Screening Center Network (MLSCN as part of the NIH Roadmap.

  5. Quantiifcation of methyl esters of fatty acids in the oil of Physalis minima by GC-MS

    Institute of Scientific and Technical Information of China (English)

    Muhammad Nasimullah Qureshi; Fazal Wajid; Inayat-ur-Rahman

    2015-01-01

    Objective:To investigate quantification of methyl esters of fatty acids in the oil extracted from Physalis minima (P. minima) using gas chromatography-mass spectrometer. Methods: Oil was extracted from the shade dried plant with n-hexane through Soxhlet extraction. Fatty acids that present in the oil were derivatized to fatty acid methyl esters and analysed through gas chromatography-mass spectrometer. Results:A total of nine fatty acids were detected in quantifiable amount in the oil. Both the saturated fatty acids and unsaturated fatty acids were identified. Palmitic acid was found in the highest concentration as 46.83%. Linoleic acid (ω-6) and linolenic acid (ω-3) were obtained in appreciable amount as 16.98%and 14.80%respectively among the unsaturated fatty acids in the oil under study. From the literature review, it appeared that fatty acids were determined for the first time in the oil of P. minima. Conclusions: Presence of these important fatty acids in high amount makes P. minima oil beneficial for health, which can be used in the preparation of phytopharmaceutical or pharmaceutical preparations. Moreover, the results of this study are useful for the phytopharmaceutical industries to establish their quality control profile.

  6. Quantification of methyl esters of fatty acids in the oil of Physalis minima by GC-MS

    Directory of Open Access Journals (Sweden)

    Muhammad Nasimullah Qureshi

    2015-02-01

    Full Text Available Objective: To investigate quantification of methyl esters of fatty acids in the oil extracted from Physalis minima (P. minima using gas chromatography-mass spectrometer. Methods: Oil was extracted from the shade dried plant with n-hexane through Soxhlet extraction. Fatty acids that present in the oil were derivatized to fatty acid methyl esters and analysed through gas chromatography-mass spectrometer. Results: A total of nine fatty acids were detected in quantifiable amount in the oil. Both the saturated fatty acids and unsaturated fatty acids were identified. Palmitic acid was found in the highest concentration as 46.83%. Linoleic acid (ω-6 and linolenic acid (ω-3 were obtained in appreciable amount as 16.98% and 14.80% respectively among the unsaturated fatty acids in the oil under study. From the literature review, it appeared that fatty acids were determined for the first time in the oil of P. minima. Conclusions: Presence of these important fatty acids in high amount makes P. minima oil beneficial for health, which can be used in the preparation of phytopharmaceutical or pharmaceutical preparations. Moreover, the results of this study are useful for the phytopharmaceutical industries to establish their quality control profile.

  7. 4-Hydroxy-3-methyl-6-phenylbenzofuran-2-carboxylic acid ethyl ester derivatives as potent anti-tumor agents.

    Science.gov (United States)

    Hayakawa, Ichiro; Shioya, Rieko; Agatsuma, Toshinori; Furukawa, Hidehiko; Naruto, Shunji; Sugano, Yuichi

    2004-01-19

    Based on the structure of 4-hydroxy-3-methyl-6-phenylbenzofuran-2-carboxylic acid ethyl ester (1), which exhibits selective cytotoxicity against a tumorigenic cell line, (2,4-dimethoxyphenyl)-(4-hydroxy-3-methyl-6-phenylbenzofuran-2-yl)-methanone (18m) was designed and synthesized as a biologically stable derivative containing no ester group. Although the potency of 18m was almost the same as our initial hit compound 1, 18m is expected to last longer in the human body as an anticancer agent.

  8. Microwave-assisted cyclizations promoted by polyphosphoric acid esters: a general method for 1-aryl-2-iminoazacycloalkanes

    Directory of Open Access Journals (Sweden)

    Jimena E. Díaz

    2016-09-01

    Full Text Available The first general procedure for the synthesis of 5 to 7-membered 1-aryl-2-iminoazacycloalkanes is presented, by microwave-assisted ring closure of ω-arylaminonitriles promoted by polyphosphoric acid (PPA esters. 1-Aryl-2-iminopyrrolidines were easily prepared from the acyclic precursors employing a chloroformic solution of ethyl polyphosphate (PPE. The use of trimethylsilyl polyphosphate (PPSE in solvent-free conditions allowed for the synthesis of 1-aryl-2-iminopiperidines and hitherto unreported 1-aryl-2-iminoazepanes. The cyclization reaction involves good to high yields and short reaction times, and represents a novel application of PPA esters in heterocyclic synthesis.

  9. Poly(acrylic acid)-block-poly(vinyl alcohol) anchored maghemite nanoparticles designed for multi-stimuli triggered drug release

    Science.gov (United States)

    Liu, Ji; Detrembleur, Christophe; Debuigne, Antoine; de Pauw-Gillet, Marie-Claire; Mornet, Stéphane; Vander Elst, Luce; Laurent, Sophie; Labrugère, Christine; Duguet, Etienne; Jérôme, Christine

    2013-11-01

    Original core/corona nanoparticles composed of a maghemite core and a stimuli-responsive polymer coating made of poly(acrylic acid)-block-poly(vinyl alcohol) macromolecules were fabricated for drug delivery system (DDS) application. This kind of DDS aims to combine the advantage of stimuli-responsive polymer coating, in order to regulate the drug release behaviours under different conditions and furthermore, improve the biocompatibility and in vivo circulation half-time of the maghemite nanoparticles. Drug loading capacity was evaluated with methylene blue (MB), a cationic model drug. The triggered release of MB was studied under various stimuli such as pH, ionic strength and temperature. Local heating generated under alternating magnetic field (AMF) application was studied, and remotely AMF-triggered release was also confirmed, while a mild heating-up of the release medium was observed. Furthermore, their potential application as magnetic resonance imaging (MRI) contrast agents was explored via relaxivity measurements and acquisition of T2-weighted images. Preliminary studies on the cytotoxicity against mouse fibroblast-like L929 cell line and also their cellular uptake within human melanoma MEL-5 cell line were carried out. In conclusion, this kind of stimuli-responsive nanoparticles appears to be promising carriers for delivering drugs to some tumour sites or into cellular compartments with an acidic environment.Original core/corona nanoparticles composed of a maghemite core and a stimuli-responsive polymer coating made of poly(acrylic acid)-block-poly(vinyl alcohol) macromolecules were fabricated for drug delivery system (DDS) application. This kind of DDS aims to combine the advantage of stimuli-responsive polymer coating, in order to regulate the drug release behaviours under different conditions and furthermore, improve the biocompatibility and in vivo circulation half-time of the maghemite nanoparticles. Drug loading capacity was evaluated with methylene

  10. The influence of surface oxygen and hydroxyl groups on the dehydrogenation of ethylene, acetic acid and hydrogenated vinyl acetate on pure Pd(1 0 0): A DFT study

    Energy Technology Data Exchange (ETDEWEB)

    Huang, Yanping [Key Laboratory for Green Chemical Technology of Ministry of Education, R& D Center for Petrochemical Technology, Tianjin University, Tianjin (China); Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300072 (China); Dong, Xiuqin [Key Laboratory for Green Chemical Technology of Ministry of Education, R& D Center for Petrochemical Technology, Tianjin University, Tianjin (China); Yu, Yingzhe, E-mail: yzhyu@tju.edu.cn [Key Laboratory for Green Chemical Technology of Ministry of Education, R& D Center for Petrochemical Technology, Tianjin University, Tianjin (China); Zhang, Minhua, E-mail: mhzhangtj@163.com [Key Laboratory for Green Chemical Technology of Ministry of Education, R& D Center for Petrochemical Technology, Tianjin University, Tianjin (China)

    2016-12-01

    Highlights: • All dehydrogenation reactions in vinyl acetate synthesis on Pd(1 0 0) were studied. • The energy barriers of the transition state of the three reactions were calculated. • The influence of surface Os and OHs on all dehydrogenation actions was discussed. - Abstract: On the basis of a Langmuir–Hinshelwood-type mechanism, the dehydrogenation of ethylene, acetic acid and hydrogenated vinyl acetate (VAH) on pure Pd(1 0 0) with surface oxygen atoms (Os) and hydroxyl groups (OHs) was studied with density functional theory (DFT) method. Our calculation results show that both Os and OHs can consistently reduce the activation energies of dehydrogenation of ethylene, acetic acid and VAH to some degree with only one exception that OHs somehow increase the activation energy of VAH. Based on Langmuir–Hinshelwood mechanism, the three dehydrogenation reactions in presence of surface Os and OHs are almost consistently favored, compared with the corresponding processes on clean Pd(1 0 0) surfaces, and thus a Langmuir–Hinshelwood-type mechanism may not be excluded beforehand when investigating the microscopic performance of the oxygen-assisted vinyl acetate synthesis on Pd(1 0 0) catalysts.

  11. Optimization of reaction parameters for enzymatic glyceride synthesis from fish oil: Ethyl esters versus free fatty acids

    DEFF Research Database (Denmark)

    Ravn, Helle Christine; Damstrup, Marianne L.; Meyer, Anne S.

    2012-01-01

    Enzymatic conversion of fish oil free fatty acids (FFA) or fatty acid ethyl esters (FAE) into glycerides via esterification or transesterification was examined. The reactions catalyzed by Lipozyme™ 435, a Candida antarctica lipase, were optimized. Influence on conversion yields of fatty acid chain...... length, saturation degree, temperature, enzyme dosage, molar ratio glycerol:fatty acids, acyl source composition (w/w ratio FFA:FAE), and reaction time was evaluated collectively by multiple linear regression. All reaction variables influenced the conversion into glycerides. Transesterification of FAE...

  12. Organogel polymers from 10-undecenoic acid and poly(vinyl acetate)

    Science.gov (United States)

    Organogels are used in a variety of high value applications including the removal of toxic solvents from aqueous environments and the time-controlled release of compounds. One of the most promising gelators is a polyvinyl polymer containing medium chain length carboxylic acids. The existing producti...

  13. Regulatory Effects of Caffeic Acid Phenethyl Ester on Neuroinflammation in Microglial Cells

    Directory of Open Access Journals (Sweden)

    Cheng-Fang Tsai

    2015-03-01

    Full Text Available Microglial activation has been widely demonstrated to mediate inflammatory processes that are crucial in several neurodegenerative disorders. Pharmaceuticals that can deliver direct inhibitory effects on microglia are therefore considered as a potential strategy to counter balance neurodegenerative progression. Caffeic acid phenethyl ester (CAPE, a natural phenol in honeybee propolis, is known to possess antioxidant, anti-inflammatory and anti-microbial properties. Accordingly, the current study intended to probe the effects of CAPE on microglia activation by using in vitro and in vivo models. Western blot and Griess reaction assay revealed CAPE significantly inhibited the expressions of inducible nitric oxide synthase (NOS, cyclooxygenase (COX-2 and the production of nitric oxide (NO. Administration of CAPE resulted in increased expressions of hemeoxygenase (HO-1and erythropoietin (EPO in microglia. The phosphorylated adenosine monophosphate-activated protein kinase (AMPK-α was further found to regulate the anti-inflammatory effects of caffeic acid. In vivo results from immunohistochemistry along with rotarod test also revealed the anti-neuroinflammatory effects of CAPE in microglia activation. The current study has evidenced several possible molecular determinants, AMPKα, EPO, and HO-1, in mediating anti-neuroinflammatory responses in microglial cells.

  14. Integrated multidimensional and comprehensive 2D GC analysis of fatty acid methyl esters.

    Science.gov (United States)

    Zeng, Annie Xu; Chin, Sung-Tong; Marriott, Philip J

    2013-03-01

    Fatty acid methyl ester (FAME) profiling in complex fish oil and milk fat samples was studied using integrated comprehensive 2D GC (GC × GC) and multidimensional GC (MDGC). Using GC × GC, FAME compounds--cis- and trans-isomers, and essential fatty acid isomers--ranging from C18 to C22 in fish oil and C18 in milk fat were clearly displayed in contour plot format according to structural properties and patterns, further identified based on authentic standards. Incompletely resolved regions were subjected to MDGC, with Cn (n = 18, 20) zones transferred to a (2)D column. Elution behavior of C18 FAME on various (2)D column phases (ionic liquids IL111, IL100, IL76, and modified PEG) was evaluated. Individual isolated Cn zones demonstrated about four-fold increased peak capacities. The IL100 provided superior separation, good peak shape, and utilization of elution space. For milk fat-derived FAME, the (2)D chromatogram revealed at least three peaks corresponding to C18:1, more than six peaks for cis/trans-C18:2 isomers, and two peaks for C18:3. More than 17 peaks were obtained for the C20 region of fish oil-derived FAMEs using MDGC, compared with ten peaks using GC × GC. The MDGC strategy is useful for improved FAME isomer separation and confirmation. © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  15. Characteristics of Oxidative Storage Stability of Canola Fatty Acid Methyl Ester Stabilised with Antioxidants

    Directory of Open Access Journals (Sweden)

    Tirto Prakoso

    2012-11-01

    Full Text Available The storage effects on the oxidation characteristics of fatty acid methyl ester of canola oil (CME were investigated in this study. CME stabilised with two antioxidants, i.e. 2,6-di-tert-bytyl-p-cresol (BHT and 6,6-di-tert-butyl-2, 2’-methylendi-p-cresol (BPH, was stored at 20, 40 and 60°C. The oxidation stability data were measured by the Rancimat test method and it was found that both BHT and BPH addition increased the oxidation resistance of the CME. The results showed that when BPH or BHT was added at a concentration of 100 ppm, the oxidation induction period of the neat CME samples increased from 5.53 h to 6.93 h and 6.14 h, respectively. Comparing both antioxidants, BPH proved to be more effective in increasing the oxidation resistance when both antioxidants were added at the same concentration. Furthermore, the oxidation induction time decreased linearly with the storage time. It was shown that the oxidation occurred rapidly in the first 8 weeks of storage. Later, a kinetic study was undertaken and first-order kinetics were applied to explain the oxidation characteristics of the CME added with antioxidants. This kinetic study focused on exploiting the activation energy values obtained from the Arrhenius equations. Also, the oxidation effects on other quality parameters, including acid value, peroxide value, kinematic viscosity, and water content, were examined.

  16. 3-Monochloropropane-1,2-diol fatty acid esters in commercial deep-fat fried foods.

    Science.gov (United States)

    Arisseto, Adriana Pavesi; Marcolino, Priscila Francisca Corrêa; Vicente, Eduardo

    2015-01-01

    Levels of 3-monochloropropane-1,2-diol (3-MCPD) fatty acid esters were evaluated in commercial deep-fat fried foods from the Brazilian market using a GC-MS method preceded by acid-catalysed methanolysis. A limit of detection of 0.04 mg kg(-1), a limit of quantitation of 0.08 mg kg(-1), mean recoveries varying from 82% to 92%, and coefficients of variation ranging from 2.5% to 5.0% for repeatability and from 3.6% to 6.5% for within-laboratory reproducibility were obtained during in-house validation. The levels of the compounds in the evaluated samples, expressed as free 3-MCPD equivalent, ranged from not detected to 0.99 mg kg(-)(1), and the highest concentrations were observed in samples of chopped onion and garlic. A preliminary estimation of 3-MCPD intake using these occurrence data suggested low risks to human health, but a potential concern may arise in particular cases of consumers of fried food.

  17. Relative oral bioavailability of 3-MCPD from 3-MCPD fatty acid esters in rats.

    Science.gov (United States)

    Abraham, Klaus; Appel, Klaus E; Berger-Preiss, Edith; Apel, Elisabeth; Gerling, Susanne; Mielke, Hans; Creutzenberg, Otto; Lampen, Alfonso

    2013-04-01

    In order to quantify the relative oral bioavailability of 3-chloropropane-1,2-diol (3-MCPD) from 3-MCPD fatty acid diesters in vivo, 1,2-dipalmitoyl-3-chloropropane-1,2-diol (3-MCPD diester) and 3-MCPD were orally applied to rats in equimolar doses. In both cases, the time courses of 3-MCPD concentrations were measured in blood, various organs, tissues and intestinal luminal contents. The results show that 3-MCPD is released by enzymatic hydrolysis from the 3-MCPD diester in the gastrointestinal tract and distributed to blood, organs and tissues. Based on the measurements in blood, the areas under the curve (AUC) for 3-MCPD were calculated. By comparing both AUC, the relative amount of 3-MCPD bioavailable from the 3-MCPD diester was calculated to be 86 % on average of the amount bioavailable following administration of 3-MCPD. In view of limited experimental data, it is justified for the purpose of risk assessment to assume complete hydrolysis of the diesters in the gastro-intestinal tract. Therefore, assessment of the extent of exposure to 3-MCPD released from its fatty acid esters should be performed in the same way as exposure to the same molar quantity of 3-MCPD.

  18. Recovery of slaughterhouse Animal Fatty Wastewater Sludge by conversion into Fatty Acid Butyl Esters by acid-catalyzed esterification.

    Science.gov (United States)

    Wallis, Christopher; Cerny, Muriel; Lacroux, Eric; Mouloungui, Zéphirin

    2017-02-01

    Two types of Animal Fatty Wastewater Sludges (AFWS 1 and 2) were analyzed and fully characterized to determine their suitability for conversion into biofuel. AFWS 1 was determined to be unsuitable as it contains 68.8wt.% water and only 32.3wt.% dry material, of which only around 80% is lipids to be converted. AFWS 2 has only 15.7wt.% water and 84.3wt.% dry material of which is assumed to 100% lipids as the protein and ash contents were determined to be negligible. The 4-dodecylbenzenesulfonic acid (DBSA) catalyzed esterification of AFWS with 1-butanol was performed in a novel batch reactor fitted with a drying chimney for the "in situ" removal of water and optimized using a non-conventional Doehlert surface response methodology. The optimized condition was found to be 1.66mol equivalent of 1-butanol (with respect to total fatty acid chains), 10wt.% of DBSA catalyst (with respect to AFWS) at 105°C for 3h. Fatty Acid Butyl Esters (FABEs) were isolated in good yields (95%+) as well as a blend of FABEs with 1-butanol (16%). The two potential biofuels were analyzed in comparison with current and analogous biofuels (FAME based biodiesel, and FABE products made from vegetable oils) and were found to exhibit high cetane numbers and flash point values. Copyright © 2016 Elsevier Ltd. All rights reserved.

  19. Production and Characterization of Ethyl Ester from Crude Jatropha curcas Oil having High Free Fatty Acid Content

    Science.gov (United States)

    Kumar, Rajneesh; Dixit, Anoop; Singh, Shashi Kumar; Singh, Gursahib; Sachdeva, Monica

    2015-09-01

    The two step process was carried out to produce biodiesel from crude Jatropha curcas oil. The pretreatment process was carried out to reduce the free fatty acid content by (≤2 %) acid catalyzed esterification. The optimum reaction conditions for esterification were reported to be 5 % H2SO4, 20 % ethanol and 1 h reaction time at temperature of 65 °C. The pretreatment process reduced the free fatty acid of oil from 7 to 1.85 %. In second process, alkali catalysed transesterification of pretreated oil was carried and the effects of the varying concentrations of KOH and ethanol: oil ratios on percent ester recovery were investigated. The optimum reaction conditions for transesterification were reported to be 3 % KOH (w/v of oil) and 30 % (v/v) ethanol: oil ratio and reaction time 2 h at 65 °C. The maximum percent recovery of ethyl ester was reported to be 60.33 %.

  20. Enhanced microemulsion formation in lipid-based drug delivery systems by combining mono-esters of mediumchain fatty acids with di- or tri-esters

    Directory of Open Access Journals (Sweden)

    Darshil P. Patel

    2012-06-01

    Full Text Available To develop strategies for selecting appropriate lipids from mono-, di- and tri-esters of medium-chain fatty acids for the development of lipid-based drug delivery systems, ternary phase diagrams of propylene glycol (PG monocaprylate (Capryol® 90; HLB~7, PG dicaprylocaprate (Labrafac™ PG; HLB~2 and glycerol tricaprylocaprate (Labrafac™ Lipophile WL1349; HLB~2 were determined in combination with a common surfactant, PEG-35 castor oil (Cremophor® EL, HLB~13, and water. Particle size and viscosity in different regions of the phase diagrams were measured, solubility of a model drug, danazol, in different lipid-surfactant mixtures was determined, and dispersion testing by diluting selected preconcentrates with 250 ml 0.01 NHCl was performed. Further, phase diagrams were constructed using binary mixtures of lipids (monoester with diester, or monoester with triester in place of single lipids. The phase diagrams of PG dicaprylocaprate and glycerol tricaprylocaprate were similar, while it was distinctly different for PG monocaprylate. The microemulsion regions in phase diagrams were rather limited for individual lipids, and additionally, the diand tri-esters showed pronounced gel regions in the phase diagrams, which could influence drug release from preconcentrates. The mixing of PG monocaprylate (monoester with PG dicaprylocaprate (diester or glycerol tricaprylocaprate (triester had dramatic effects on the performance of lipids as evidenced by the greatly reduced gel phases, much larger microemulsion regions, faster dispersion of the preconcentrates in an aqueous medium, and smaller particle size of the microemulsions subsequently formed.

  1. Prospects and potential of fatty acid methyl esters of some non-traditional seed oils for use as biodiesel in India

    Energy Technology Data Exchange (ETDEWEB)

    Mohibbe Azam, M.; Waris, Amtul; Nahar, N.M. [Central Arid Zone Research Institute, Jodhpur 342003 (India)

    2005-10-01

    Fatty acid profiles of seed oils of 75 plant species having 30% or more fixed oil in their seed/kernel were examined. Saponification number (SN), iodine value (IV) and cetane number (CN) of fatty acid methyl esters of oils were empirically determined and they varied from 169.2 to 312.5, 4.8 to 212 and 20.56 to 67.47, respectively. Fatty acid compositions, IV and CN were used to predict the quality of fatty acid methyl esters of oil for use as biodiesel. Fatty acid methyl ester of oils of 26 species including Azadirachta indica, Calophyllum inophyllum, Jatropha curcas and Pongamia pinnata were found most suitable for use as biodiesel and they meet the major specification of biodiesel standards of USA, Germany and European Standard Organization. The fatty acid methyl esters of another 11 species meet the specification of biodiesel standard of USA only. These selected plants have great potential for biodiesel. (author)

  2. Prospects and potential of fatty acid methyl esters of some non-traditional seed oils for use as biodiesel in India

    International Nuclear Information System (INIS)

    Mohibbe Azam, M.; Waris, Amtul; Nahar, N.M.

    2005-01-01

    Fatty acid profiles of seed oils of 75 plant species having 30% or more fixed oil in their seed/kernel were examined. Saponification number (SN), iodine value (IV) and cetane number (CN) of fatty acid methyl esters of oils were empirically determined and they varied from 169.2 to 312.5, 4.8 to 212 and 20.56 to 67.47, respectively. Fatty acid compositions, IV and CN were used to predict the quality of fatty acid methyl esters of oil for use as biodiesel. Fatty acid methyl ester of oils of 26 species including Azadirachta indica, Calophyllum inophyllum, Jatropha curcas and Pongamia pinnata were found most suitable for use as biodiesel and they meet the major specification of biodiesel standards of USA, Germany and European Standard Organization. The fatty acid methyl esters of another 11 species meet the specification of biodiesel standard of USA only. These selected plants have great potential for biodiesel

  3. Crystallisation of hydroxyapatite in phosphorylated poly(vinyl alcohol) as a synthetic route to tough mechanical hybrid materials

    Energy Technology Data Exchange (ETDEWEB)

    Kusakabe, Akane; Hirota, Ken; Mizutani, Tadashi, E-mail: tmizutan@mail.doshisha.ac.jp

    2017-01-01

    Partially phosphorylated poly(vinyl alcohol) was prepared by treating poly(vinyl alcohol) with 100% phosphoric acid, and 5, 10 and 20% of the hydroxyl groups were converted to phosphoric acid ester. Addition of Ca{sup 2+} to an aqueous solution of phosphorylated poly(vinyl alcohol) gave a transparent gel. Five cycles of alternate soaking of the gel in aqueous CaCl{sub 2} and aqueous (NH{sub 4}){sub 2}HPO{sub 4} were carried out to crystallise hydroxyapatite (HAP) in the phosphorylated poly(vinyl alcohol) matrix. The X-ray diffraction peaks of HAP formed in 5% phosphorylated PVA were sharp, while those of HAP formed in 20% phosphorylated PVA were broad. The contents of inorganic phase in the hybrid powder were increased from 58 to 76 wt% as the fraction of phosphate groups in the gel was decreased from 20% to 5%. The hybrid powder was first subjected to uniaxial pressing, followed by cold isostatic pressing (CIP) and warm isostatic pressing (WIP) at 120 °C at pressures of 300–980 MPa, to obtain the specimens for three-point bending test. These hybrid specimens showed bending strengths of 15–53 MPa. The hybrid compacts prepared from 10% phosphorylated poly(vinyl alcohol) showed the smallest Young's modulus, the largest displacement at break, and the largest fracture energy, showing that it has the highest toughness among the hybrid materials prepared from poly(vinyl alcohol) with varying degrees of phosphorylation. - Graphical abstract: Densification of hydroxyapatite crystallised in 10% phosphorylated poly(vinyl alcohol) gave the toughest compact. - Highlights: • Hydroxyapatite was crystallised in phosphorylated poly(vinyl alcohol) gels. • Crystallite size of hydroxyapatite decreased as phosphate density was increased. • The hybrid specimens prepared in 10% phosphorylated gel was the toughest. • Phosphate density in organic matrix regulated the mechanical properties of the hybrid.

  4. Crystallisation of hydroxyapatite in phosphorylated poly(vinyl alcohol) as a synthetic route to tough mechanical hybrid materials

    International Nuclear Information System (INIS)

    Kusakabe, Akane; Hirota, Ken; Mizutani, Tadashi

    2017-01-01

    Partially phosphorylated poly(vinyl alcohol) was prepared by treating poly(vinyl alcohol) with 100% phosphoric acid, and 5, 10 and 20% of the hydroxyl groups were converted to phosphoric acid ester. Addition of Ca 2+ to an aqueous solution of phosphorylated poly(vinyl alcohol) gave a transparent gel. Five cycles of alternate soaking of the gel in aqueous CaCl 2 and aqueous (NH 4 ) 2 HPO 4 were carried out to crystallise hydroxyapatite (HAP) in the phosphorylated poly(vinyl alcohol) matrix. The X-ray diffraction peaks of HAP formed in 5% phosphorylated PVA were sharp, while those of HAP formed in 20% phosphorylated PVA were broad. The contents of inorganic phase in the hybrid powder were increased from 58 to 76 wt% as the fraction of phosphate groups in the gel was decreased from 20% to 5%. The hybrid powder was first subjected to uniaxial pressing, followed by cold isostatic pressing (CIP) and warm isostatic pressing (WIP) at 120 °C at pressures of 300–980 MPa, to obtain the specimens for three-point bending test. These hybrid specimens showed bending strengths of 15–53 MPa. The hybrid compacts prepared from 10% phosphorylated poly(vinyl alcohol) showed the smallest Young's modulus, the largest displacement at break, and the largest fracture energy, showing that it has the highest toughness among the hybrid materials prepared from poly(vinyl alcohol) with varying degrees of phosphorylation. - Graphical abstract: Densification of hydroxyapatite crystallised in 10% phosphorylated poly(vinyl alcohol) gave the toughest compact. - Highlights: • Hydroxyapatite was crystallised in phosphorylated poly(vinyl alcohol) gels. • Crystallite size of hydroxyapatite decreased as phosphate density was increased. • The hybrid specimens prepared in 10% phosphorylated gel was the toughest. • Phosphate density in organic matrix regulated the mechanical properties of the hybrid.

  5. Synthesis, Purification, and Quantification of Fatty Acid Ethyl Esters After trans-Esterification of Large Batches of Tobacco Seed Oil

    Directory of Open Access Journals (Sweden)

    Ashraf-Khorassani Mehdi

    2015-03-01

    Full Text Available L'objectif de la présente étude était de quantifier les esters éthyliques d'acides gras (FAEE produits à partir de deux grands lots d'huile de graines de tabac soumis à une transéstérification éthanolique en présence d'un catalyseur d'acide sulfurique. La purification des produits combinés de la réaction des esters éthyliques visait la suppression, autant que faire se peut, de la couleur et de l'odeur du produit final et fut accomplie via une chromatographie sur colonne conventionnelle avec silice sublimée et une élution en tandem de l'hexane, dans un premier temps et de l'alcool éthylique, dans un deuxième temps, en guise de phase mobile. La chromatographie en phase gazeuse fut utilisée afin de quantifier les esters éthyliques des acides gras spécifiques dans la matière purifiée. Le pourcentage d'esters éthyliques d'acides gras purs récupérés dans le lot n°1 s'éleva à près de 87% tandis que le pourcentage d'esters éthyliques d'acides gras purs récupérés dans le lot n°2 fut supérieur à 89% avec des rendements à la préparation supérieurs à 400 g d'esters éthyliques par essai d'estérification. Les esters éthyliques d'acides gras ne possédaient pas d'arome détectable et ne présentaient qu'une légère coloration jaune à l'issue de ce traitement chromatographique. Pour caractériser la pureté de chaque lot d'esters éthyliques d'acides gras produits, une chromatographie en phase supercritique dont la phase mobile était un fluide composé de dioxyde de carbone modifié au méthanol/acétonitrile et une phase fixe composée d'une silice greffée avec groupement fonctionnel octadécyle furent utilisées. Aucune impureté liée au glycérol ou à des acides gras libres ne fut détectée dans le produit transestérifié purifié. Notre article est le premier rapport décrivant la transestérification optimisée de l'huile de graines de tabac à une échelle relativement grande, ladite transest

  6. Preparation of New 2,3-Diphenylpropenoic Acid Esters – Good Yields Even for the More Hindered Z Isomers

    Directory of Open Access Journals (Sweden)

    István Pálinkó

    2004-03-01

    Full Text Available The potassium salt of E- and Z-2,3-diphenylpropenoic acids prepared in situ could be esterified efficiently in DMSO with the appropriate alkyl halides at room temperature. In this way 10 previously undescribed esters of these acids were synthesised and characterised. Excellent yields were observed for most of the E isomers and the more hindered Z esters were also obtained in good yields, far better than those obtained applying the classical acid-catalysed esterification reaction.

  7. Fatty-acid alkyl esters in table olives in relation to abnormal fermentation and poorly conducted technological treatments

    Energy Technology Data Exchange (ETDEWEB)

    Lanza, B.; Serio, M.G. di; Giacinto, L. di

    2016-07-01

    There are several methods to prepare table olives, and each of the steps and conditions during this processing can affect the composition and nutritional value of the product. The influence of abnormal fermentation and poorly conducted technological treatments was examined here in terms of the lipid fraction of table olives. In ‘Greek style’ olives, a low concentration of brine can allow the growth of spontaneous microflora and consequent organoleptic defects (‘putrid/butyric fermentation’, ‘winey-vinegary’). Here, the ‘Kalamata’ and ‘Moresca’ cultivars can produce methyl esters (methyl oleate/ linoleate: 553 and 450 mg·kg−1 oil, respectively) and ethyl esters (ethyl oleate/ inoleate: 4764 and 4195; palmitate: 617 and 886 mg·kg −1 oil, respectively). In ‘Sevillan style’ olives, a high NaOH concentration influences the fatty-acid composition less, but is difficult to eliminate, for a ‘soapy’ defect. The ‘Giarraffa’ and ‘Nocellara del Belice’ cultivars produce only ethyl esters (ethyl oleate/ linoleate: 222 and 289 mg·kg−1 oil, respectively). With this production of ethyl and methyl esters from the principal fatty acids in the lipid fractions of table olives, methods that provide only biological treatments (i.e., Greek style) pose more risk than methods that provide only chemical treatments (i.e., Sevillan style). (Author)

  8. Preparation of sucrose fatty acid esters as food emulsifiers and evaluation of their surface active and emulsification properties.

    Directory of Open Access Journals (Sweden)

    Megahed, Mohamed G.

    1999-08-01

    Full Text Available A simple method for the preparation of sucrose esters, from fatty acids and the least expensive sucrose, has been conducted. Fatty acids namely lauric, palmitic and oleic were used in their preparation in the absence of any organic solvent. Reasonable yields amounting to 86.5%, 87.3% and 88.6% for sucrose esters of laurate, palmitate and oleate were obtained, respectively. The products were evaluated for their hydrophile-lipophile balance (HLB, surface and interfacial tension properties as well as emulsion stability. The results showed that these sucrose esters exhibit similar properties as those of the commercially prepared compounds.

    Se ha llevado a cabo un método simple para la preparación de ésteres de sacarosa a partir de ácidos grasos y sacarosa de bajo coste. Se han usado ácidos laurico, palmítico y oleico en su preparación, en ausencia de solventes orgánicos. Se obtuvieron rendimientos aceptables del 86.5%, 87.3% y 88.6% para los ásteres del láurico, palmítico y oleico respectivamente. En los productos se evaluaron sus balances hidrófilo-lipófilo (HLB, sus propiedades de tensión superficial e interfacial así como su estabilidad en emulsiones. Los resultados mostraron que estos esteres de sacarosa exhiben propiedades similares a las de los compuestos preparados comercialmente.

  9. Effects of caffeic acid phenethyl ester on palatal mucosal defects and tooth extraction sockets

    Directory of Open Access Journals (Sweden)

    Günay A

    2014-10-01

    Full Text Available Ahmet Günay,1 Osman Fatih Arpağ,2 Serhat Atilgan,3 Ferhan Yaman,3 Yusuf Atalay,4 İzzet Acikan3 1Department of Periodontology, Faculty of Dentistry, Dicle University, Diyarbakir, Turkey; 2Department of Periodontology, Faculty of Dentistry, Mustafa Kemal University, Hatay, Turkey; 3Department of Maxillofacial Surgery, Faculty of Dentistry, Dicle University, Diyarbakir, Turkey; 4Department of Maxillofacial Surgery, Faculty of Dentistry, Kocatepe University, Afyon, Turkey Aim: The purpose of this study was to evaluate the effects of caffeic acid phenethyl ester (CAPE on palatal mucosal defects and tooth extraction sockets in an experimental model.Materials and methods: Forty-two male Sprague-Dawley rats with a mean age of 7 weeks and weighing 280–490 g were used in this study. The rats were randomly divided into two groups: group A (the control group, n=21 and group B (the experimental group, n=21. Under anesthesia with ketamine (8 mg/100 g, intraperitoneally, palatal mucosal defects were created and tooth extraction was performed in the rats in groups A and B. Group A received no treatment, whereas group B received CAPE. CAPE was injected daily (10 µmol/kg, intraperitoneally. The rats were killed on days 7, 14, and 30 after the procedures. Palatal mucosa healing and changes in bone tissue and fibrous tissue were evaluated histopathologically.Result: Pairwise comparisons showed no statistically significant difference between days 7 and 14 in either group (P>0.05. At day 30, bone healing was significantly better in group B (CAPE than in group A (control (P<0.05. Fibrinogen levels at day 30 were significantly higher in group A (control than in group B (CAPE (P<0.05. Pairwise comparisons showed no statistically significant difference in palatal mucosa healing levels between days 7 and 14 in both groups (P>0.05.Conclusion: In conclusion, the findings of this study suggest that CAPE can significantly improve tooth socket healing. Keywords: caffeic

  10. Fatty acid esters-based composite phase change materials for thermal energy storage in buildings

    International Nuclear Information System (INIS)

    Sarı, Ahmet; Karaipekli, Ali

    2012-01-01

    In this study, fatty acid esters-based composite phase change materials (PCMs) for thermal energy storage were prepared by blending erythritol tetrapalmitate (ETP) and erythritol tetrastearate (ETS) with diatomite and expanded perlite (EP). The maximum incorporation percentage for ETP and ETS into diatomite and EP was found to be 57 wt% and 62 wt%, respectively without melted PCM seepage from the composites. The morphologies and compatibilities of the composite PCMs were structurally characterized using scanning electron microscope (SEM) and Fourier transformation infrared (FT–IR) analysis techniques. Thermal energy storage properties of the composite PCMs were determined by differential scanning calorimetry (DSC) analysis. The DSC analyses results indicated that the composite PCMs were good candidates for building applications in terms of their large latent heat values and suitable phase change temperatures. The thermal cycling test including 1000 melting and freezing cycling showed that composite PCMs had good thermal reliability and chemical stability. TG analysis revealed that the composite PCMs had good thermal durability above their working temperature ranges. Moreover, in order to improve the thermal conductivity of the composite PCMs, the expanded graphite (EG) was added to them at different mass fractions (2%, 5%, and 10%). The best results were obtained for the composite PCMs including 5wt% EG content in terms of the increase in thermal conductivity values and the decrease amount in latent heat capacity. The improvement in thermal conductivity values of ETP/Diatomite, ETS/Diatomite, ETP/EP and ETS/EP were found to be about 68%, 57%, 73% and 75%, respectively. Highlights: ► Fatty acid esters-based composite PCMs were prepared by blending ETP and ETS with diatomite and expanded perlite. ► The composite PCMs were characterized by using SEM, FT–IR, DSC and TG analysis methods. ► The DSC results indicated that the composites PCMs had good thermal

  11. Palmitic Acid Curcumin Ester Facilitates Protection of Neuroblastoma against Oligomeric Aβ40 Insult.

    Science.gov (United States)

    Qi, Zhangyang; Wu, Meihao; Fu, Yun; Huang, Tengfei; Wang, Tingting; Sun, Yanjie; Feng, Zhibo; Li, Changzheng

    2017-01-01

    The generation of reactive oxygen species (ROS) caused by amyloid-β (Aβ) is considered to be one of mechanisms underlying the development of Alzheimer's disease. Curcumin can attenuate Aβ-induced neurotoxicity through ROS scavenging, but the protective effect of intracellular curcumin on neurocyte membranes against extracellular Aβ may be compromised. To address this issue, we synthesized a palmitic acid curcumin ester (P-curcumin) which can be cultivated on the cell membrane and investigated the neuroprotective effect of P-curcumin and its interaction with Aβ. P-curcumin was prepared through chemical synthesis. Its structure was determined via nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS). An MTT assay was used to assess Aβ cytotoxicity and the protective effect of P-curcumin on SH-SY5Y cells. The effect of P-curcumin on Aβ-induced ROS production in vitro and in vivo were assessed based on changes in dichlorofluorescein (DCF) fluorescence. A spectrophotometric method was employed to detect lipid peroxidation. To mimic the interaction of P-curcumin on cell membranes with Aβ, liposomes were prepared by thin film method. Finally, the interactions between free P-curcumin and P-curcumin cultivated on liposomes and Aβ were determined via spectrophotometry. A novel derivative, palmitic acid curcumin ester was prepared and characterized. This curcumin, cultivated on the membranes of neurocytes, may prevent Aβ-mediated ROS production and may inhibit the direct interaction between Aβ and the cellular membrane. Furthermore, P-curcumin could scavenge Aβ-mediated ROS as curcumin in vitro and in vivo, and had the potential to prevent lipid peroxidation. Morphological analyses showed that P-curcumin was better than curcumin at protecting cell shape. To examine P-curcumin's ability to attenuate direct interaction between Aβ and cell membranes, the binding affinity of Aβ to curcumin and P-curcumin was determined. The association

  12. Palmitic Acid Curcumin Ester Facilitates Protection of Neuroblastoma against Oligomeric Aβ40 Insult

    Directory of Open Access Journals (Sweden)

    Zhangyang Qi

    2017-11-01

    Full Text Available Background/Aims: The generation of reactive oxygen species (ROS caused by amyloid-β (Aβ is considered to be one of mechanisms underlying the development of Alzheimer’s disease. Curcumin can attenuate Aβ-induced neurotoxicity through ROS scavenging, but the protective effect of intracellular curcumin on neurocyte membranes against extracellular Aβ may be compromised. To address this issue, we synthesized a palmitic acid curcumin ester (P-curcumin which can be cultivated on the cell membrane and investigated the neuroprotective effect of P-curcumin and its interaction with Aβ. Methods: P-curcumin was prepared through chemical synthesis. Its structure was determined via nuclear magnetic resonance (NMR and high-resolution mass spectrometry (HRMS. An MTT assay was used to assess Aβ cytotoxicity and the protective effect of P-curcumin on SH-SY5Y cells. The effect of P-curcumin on Aβ-induced ROS production in vitro and in vivo were assessed based on changes in dichlorofluorescein (DCF fluorescence. A spectrophotometric method was employed to detect lipid peroxidation. To mimic the interaction of P-curcumin on cell membranes with Aβ, liposomes were prepared by thin film method. Finally, the interactions between free P-curcumin and P-curcumin cultivated on liposomes and Aβ were determined via spectrophotometry. Results: A novel derivative, palmitic acid curcumin ester was prepared and characterized. This curcumin, cultivated on the membranes of neurocytes, may prevent Aβ-mediated ROS production and may inhibit the direct interaction between Aβ and the cellular membrane. Furthermore, P-curcumin could scavenge Aβ-mediated ROS as curcumin in vitro and in vivo, and had the potential to prevent lipid peroxidation. Morphological analyses showed that P-curcumin was better than curcumin at protecting cell shape. To examine P-curcumin’s ability to attenuate direct interaction between Aβ and cell membranes, the binding affinity of Aβ to curcumin

  13. Effect of 6 dietary fatty acids on the postprandial lipid profile, plasma fatty acids, lipoprotein lipase, and cholesterol ester transfer activities in healthy young men

    DEFF Research Database (Denmark)

    Tholstrup, T.; Sandstrøm, B.; Bysted, Anette

    2001-01-01

    , plasma fatty acids, and preheparin lipoprotein lipase and cholesterol ester transfer protein (CETP) activities. Design: Six test fats high (approximate to 43% by wt) in stearic acid, palmitic acid, palmitic + myristic acid, oleic acid, elaidic acid (trans 18:1), and linoleic acid were produced...... to the test-fat meals were observed for plasma lipoprotein triacylglycerol and cholesterol concentrations, plasma fatty acid concentrations, and lipoprotein lipase and CETP activities (diet x time interaction: 0.001 acids stearic and palmitic acids resulted......Background: There is increasing evidence that postprandial triacylglycerol-rich lipoproteins may be related to atherogenic risk. Objective: The objective was to investigate the effect of individual fatty acid intakes on postprandial plasma lipoprotein triacylglycerol and cholesterol concentrations...

  14. Thermal stability of homo- and copolymers of vinyl fluoride

    International Nuclear Information System (INIS)

    Raucher, D.; Levy, M.

    1979-01-01

    The thermal stability of poly(vinyl fluoride)(PVF) was studied by thermal gravimetry and mass spectrometry (TGA and TGA-MS). In low-molecular-weight polymers a two-step decomposition pattern was observed. It consisted of the dehydrofluorination to a polyene chain followed by decomposition of the resulting polyene at higher temperatures. Copolymers of vinyl fluoride-vinyl acetate (VF-VAc) and vinyl fluoride-vinyl chloride (VF-VCl) showed a simultaneous evolution of hydrofluoric acid and acetic acid and hydrofluoric acid and hydrochloric acid, respectively. This suggests that after the elimination of the weakest link a spontaneous elimination of neighboring HF molecules takes place

  15. Synthesis of Furandicarboxylic Acid Esters From Nonfood Feedstocks Without Concomitant Levulinic Acid Formation

    NARCIS (Netherlands)

    Klis, van der Frits; Haveren, van Jacco; Es, van Daan S.; Bitter, Harry

    2017-01-01

    5-Hydroxymethylfurfural (HMF) is a versatile intermediate in biomass conversion pathways. However, the notoriously unstable nature of HMF imposes challenges to design selective routes to chemicals such as furan-2,5-dicarboxylic acid (FDCA). Here, a new strategy for obtaining furans is presented,

  16. Improved separation of conjugated fatty acid methyl esters by silver ion-high-performance liquid chromatography.

    Science.gov (United States)

    Sehat, N; Rickert, R; Mossoba, M M; Kramer, J K; Yurawecz, M P; Roach, J A; Adlof, R O; Morehouse, K M; Fritsche, J; Eulitz, K D; Steinhart, H; Ku, Y

    1999-04-01

    Operating from one to six silver ion-high-performance liquid chromatography (Ag+-HPLC) columns in series progressively improved the resolution of the methyl esters of conjugated linoleic acid (CLA) isomeric mixtures from natural and commercial products. In natural products, the 8 trans, 10 cis-octadecadienoic (18:2) acid was resolved from the more abundant 7 trans, 9 cis-18:2, and the 10 trans, 12 cis-18:2 was separated from the major 9 cis, 11 trans-18:2 peak. In addition, both 11 trans, 13 cis-18:2 and 11 cis, 13 trans-18:2 isomers were found in natural products and were separated; the presence of the latter, 11 cis, 13 trans-18:2, was established in commercial CLA preparations. Three Ag+-HPLC columns in series appeared to be the best compromise to obtain satisfactory resolution of most CLA isomers found in natural products. A single Ag+-HPLC column in series with one of several normal-phase columns did not improve the resolution of CLA isomers as compared to that of the former alone. The 20:2 conjugated fatty acid isomers 11 cis, 13 trans-20:2 and 12 trans, 14 cis-20:2, which were synthesized by alkali isomerization from 11 cis, 14 cis-20:2, eluted in the same region of the Ag+-HPLC chromatogram just before the corresponding geometric CLA isomers. Therefore, CLA isomers will require isolation based on chain length prior to Ag+-HPLC separation. The positions of conjugated double bonds in 20:2 and 18:2 isomers were established by gas chromatography-electron ionization mass spectrometry as their 4,4-dimethyloxazoline derivatives. The double-bond geometry was determined by gas chromatography-direct deposition-Fourier transform infrared spectroscopy and by the Ag+-HPLC relative elution order.

  17. Simultaneous microwave extraction and synthesis of fatty acid methyl ester from the oleaginous yeast Rhodotorula glutinis

    International Nuclear Information System (INIS)

    Chuck, Christopher J.; Lou-Hing, Daniel; Dean, Rebecca; Sargeant, Lisa A.; Scott, Rod J.; Jenkins, Rhodri W.

    2014-01-01

    Microbial lipids have the potential to substantially reduce the use of liquid fossil fuels, though one obstacle is the energy costs associated with the extraction and subsequent conversion into a biofuel. Here we report a one-step method to produce FAME (fatty acid methyl esters) from Rhodotorula glutinis by combining lipid extraction in a microwave reactor with acid-catalysed transesterification. The microwave did not alter the FAME profile and over 99% of the lipid was esterified when using 25 wt% H 2 SO 4 over 20 min at 120 °C. On using higher loadings of catalyst, similar yields were achieved over 30 s. Equivalent amounts of FAME were recovered in 30 s using this method as with a 4 h Soxhlet extraction, run with the same solvent system. When water was present at less than a 1:1 ratio with methanol, the main product was FAME, above this the major products were FFA (free fatty acids). Under the best conditions, the energy required for the microwave was less than 20% of the energy content of the biodiesel produced. Increasing the temperature did not change the EROI (energy return on investment) substantially; however, longer reaction times used an equivalent amount of energy to the total energy content of the biodiesel. - Highlights: • The extraction and transesterification of yeast lipid were achieved using a microwave reactor. • The lipid was extracted from Rhodotorula glutinis within 30 s under all conditions. • Addition of 25 wt% H 2 SO 4 catalyst converted 95% glycerides to FAME over 5 min. • Water could be tolerated up to 25 wt% without high FFA production. • The temperature of the microwave had less impact on EROI than the length of extraction

  18. [Development of gas chromatography-mass spectrometry for determination of fatty acid esters of chloropropanols in milk powder and the pollution level of infant formula].

    Science.gov (United States)

    Li, Shan; Miao, Hong; Cui, Xia; Zhao, Yunfeng; Wu, Yongning

    2015-06-01

    To establish a method for determination of fatty acid esters of chloropropanols (chloropropanols esters) in milk powder by isotope dilution-gas chromatography-mass spectrometry (GC-MS), and to acquire the pollution level of chloropropanols esters in infant formula and evaluate the dietary exposure risk of chloropropanols esters in infant formula for infants. A total of 111 infant formula samples were collected from supermarkets in Beijing, and the infant formula with no chloropropanols esters detected was served as the blank sample. The samples were ultrasonically extracted with hexane, followed by ester-bond cleavage reaction with sodium methylate-methanol and purification by matrix solid-supported liquid-liquid extraction, then being derivatived with heptafluoro butyrylimidazol. After extracted by sodium chloride solution, the derivatives were determined by GC-MS. The concentration of chloropropanols esters were quantified using the deuterium chloropropanols esters as the internal standards. The accuracy of the method was assessed by the recoveries of the blank spiked samples, and the relative standard deviations (RSD) of the recoveries represent the precision of the method. The contamination level of chloropropanols esters and the intake amount of the infant formula of the 6-month infant were used to estimate the dietary exposure assessment, and x (95% CI) and P97.5 of the contamination level of chloropropanols esters were used to represent the average dietary exposure and the high-end dietary exposure. The satisfied linear correlations in the range of 0.010-0.800 mg/L was acquired for 3-MCPD esters, 2-MCPD esters, 1,3-DCP esters and 2,3-DCP esters with coefficient correlations of 0.999 9, 0.999 8, 0.999 5 and 0.999 6, respectively. The limits of detection (LOD) and the limits of quantitation (LOQ) for 3-MCPD esters, 2-MCPD esters, 1,3-DCP esters and 2,3-DCP esters were 0.005, 0.005, 0.015, 0.015 mg/kg, and 0.015, 0.015, 0.045, 0.045 mg/kg. The average

  19. Synthesis of alkynes from vinyl triflates using tetrabutylammonium fluoride.

    Science.gov (United States)

    Okutani, Masaru; Mori, Yuji

    2015-01-01

    A convenient method for the preparation of alkynes and alkynyl esters from ketones and β-keto esters is described which involves the formation of vinyl triflates, followed by elimination with tetrabutylammonium fluoride trihydrate, to give alkynes. Unlike established elimination methods, the method requires neither a strong base nor anhydrous conditions.

  20. Microencapsulation of caffeic acid phenethyl ester and caffeic acid phenethyl amide by inclusion in hydroxypropyl-β-cyclodextrin.

    Science.gov (United States)

    Garrido, E Manuela P J; Cerqueira, Ana S; Chavarria, Daniel; Silva, Tiago; Borges, Fernanda; Garrido, Jorge M P J

    2018-07-15

    Caffeic acid phenethyl ester (CAPE) is a bioactive polyphenolic compound obtained from propolis extract. Although it has a broad therapeutic potential, the bioavailability of CAPE is limited, due to reduced solubility and poor plasmatic stability. Efforts to reduce these pharmacokinetic drawbacks resulted in the synthesis of caffeic acid phenethyl amide (CAPA). Cyclodextrins have been proved as promising excipients for the formulation of active ingredients. Herein, we report the inclusion complexation behavior and binding ability of CAPE and CAPA with hydroxypropyl-β-cyclodextrin (HP-β-CD). The supramolecular interactions were examined through UV and FTIR spectroscopy, DSC, 1 H NMR and 2D ROESY. The CAPE/HP-β-CD and CAPA/HP-β-CD inclusion complexes stability constants were determined to be, respectively, 2911.6 and 584.6 M -1 in water and 2866.2 and 700.1 M -1 at physiological pH. The aqueous solubility increased notably, proving that HP-β-CD can be potentially useful to improve the biological, chemical and physical properties of CAPE and CAPA. Copyright © 2018 Elsevier Ltd. All rights reserved.

  1. Saturated fatty acids and fatty acid esters promote the polymorphic transition of clarithromycin metastable form I crystal.

    Science.gov (United States)

    Watanabe, Miteki; Mizoguchi, Midori; Aoki, Hajime; Iwao, Yasunori; Noguchi, Shuji; Itai, Shigeru

    2016-10-15

    The phase transition of active pharmaceutical ingredients should be taken into account during manufacturing, processing- and storage, because different crystal forms lead to different physical properties of formulations. The phase transition of clarithromycin (CAM) metastable form I to stable form II was investigated on heating with additives such as fatty acids or fatty acid esters. Differential scanning calorimetry analyses revealed that when form I was heated with additives, the phase transition temperature of form I decreased close to the melting points of the additives. Powder X-ray diffraction analyses indicated the tentative presence of a non-crystalline component during the transition of form I to form II on heating with additives. These observations implied that CAM form I dissolved in the melted additives on heating and the dissolved CAM crystallized to form II. Reduction of transition temperatures in the presence of additives were also observed for the crystals of nifedipine form B and carbamazepine form III. These results suggested that the phenomena can be widely applicable for simultaneous crystalline phase transition and granulation using binder additives. Copyright © 2016 Elsevier B.V. All rights reserved.

  2. Levels of palmitic acid ester of hydroxystearic acid (PAHSA) are reduced in the breast milk of obese mothers.

    Science.gov (United States)

    Brezinova, Marie; Kuda, Ondrej; Hansikova, Jana; Rombaldova, Martina; Balas, Laurence; Bardova, Kristina; Durand, Thierry; Rossmeisl, Martin; Cerna, Marcela; Stranak, Zbynek; Kopecky, Jan

    2018-02-01

    To achieve optimal development of a newborn, breastfeeding is extensively recommended, but little is known about the role of non-nutritive bioactive milk components. We aimed to characterize the fatty acid esters of hydroxy fatty acids (FAHFAs), namely palmitic acid hydroxystearic acids (PAHSAs)-endogenous lipids with anti-inflammatory and anti-diabetic properties, in human breast milk. Breast milk samples from 30 lean (BMI=19-23) and 23 obese (BMI>30) women were collected 72h postpartum. Adipose tissue and milk samples were harvested from C57BL/6J mice. FAHFA lipid profiles were measured using reverse phase and chiral liquid chromatography-mass spectrometry method. PAHSA regioisomers as well as other FAHFAs were present in both human and murine milk. Unexpectedly, the levels of 5-PAHSA were higher relative to other regioisomers. The separation of both regioisomers and enantiomers of PAHSAs revealed that both R- and S-enantiomers were present in the biological samples, and that the majority of the 5-PAHSA signal is of R configuration. Total PAHSA levels were positively associated with weight gain during pregnancy, and 5-PAHSA as well as total PAHSA levels were significantly lower in the milk of the obese compared to the lean mothers. Our results document for the first time the presence of lipid mediators from the FAHFA family in breast milk, while giving an insight into the stereochemistry of PAHSAs. They also indicate the negative effect of obesity on 5-PAHSA levels. Future studies will be needed to explore the role and mechanism of action of FAHFAs in breast milk. Copyright © 2017 Elsevier B.V. All rights reserved.

  3. Cell killing and radiosensitization by caffeic acid phenethyl ester (CAPE) in lung cancer cells

    International Nuclear Information System (INIS)

    Chen, Miao-Fen; Chen, Wen-Cheng; Wu, Chun-Te; King, P.C.

    2004-01-01

    Caffeic acid phenethyl ester (CAPE) is a biologically active ingredient of honeybee propoplis. The cytotoxicity and radiation sensitization effects of CAPE were evaluated in human lung cancer A549 cells and normal lung fibroblast WI-38 cells. A549 cells treated with 6 μg/ml CAPE showed marked growth inhibition (60%) at 48 hr after treatments. During the same time, the number of viable cells decreased to 46% of the control value. In contrast, WI-38 cells showed 20% growth inhibition with no change in the number of viable cells under the same treatment conditions. At 72 hr after CAPE treatment (6 μg/ml), the percentage of apoptotic cells in A549 cultures increased significantly to 67% and an S/G2 arrest was also detected in the culture. Furthermore, there was a significant decrease in the level of intracellular glutathione and hydrogen peroxide contents within one hr after CAPE treatment, and the expression of cyclin B 1 was reduced 6 hr after treatment. The radiation sensitization effect of CAPE on A549 cells was determined from the clonogenic survival curves, and the results showed a small but significant difference in radiation survival between cells treated with or without CAPE. Taken together, our results suggest that the effects of CAPE on differential cytotoxicity, apoptosis, and radiosensitization are associated with glutathione depletion that occurred shortly after treatments. (author)

  4. Negative polarity of phenyl-C61 butyric acid methyl ester adjacent to donor macromolecule domains

    International Nuclear Information System (INIS)

    Alley, Olivia J.; Dawidczyk, Thomas J.; Hardigree, Josué F. Martínez; Katz, Howard E.; Wu, Meng-Yin; Johns, Gary L.; Markovic, Nina; Arnold, Michael S.

    2015-01-01

    Interfacial fields within organic photovoltaics influence the movement of free charge carriers, including exciton dissociation and recombination. Open circuit voltage (V oc ) can also be dependent on the interfacial fields, in the event that they modulate the energy gap between donor HOMO and acceptor LUMO. A rise in the vacuum level of the acceptor will increase the gap and the V oc , which can be beneficial for device efficiency. Here, we measure the interfacial potential differences at donor-acceptor junctions using Scanning Kelvin Probe Microscopy, and quantify how much of the potential difference originates from physical contact between the donor and acceptor. We see a statistically significant and pervasive negative polarity on the phenyl-C 61 butyric acid methyl ester (PCBM) side of PCBM/donor junctions, which should also be present at the complex interfaces in bulk heterojunctions. This potential difference may originate from molecular dipoles, interfacial interactions with donor materials, and/or equilibrium charge transfer due to the higher work function and electron affinity of PCBM. We show that the contact between PCBM and poly(3-hexylthiophene) doubles the interfacial potential difference, a statistically significant difference. Control experiments determined that this potential difference was not due to charges trapped in the underlying substrate. The direction of the observed potential difference would lead to increased V oc , but would also pose a barrier to electrons being injected into the PCBM and make recombination more favorable. Our method may allow unique information to be obtained in new donor-acceptor junctions

  5. Protective Effects of Intralipid and Caffeic Acid Phenethyl Ester on Nephrotoxicity Caused by Dichlorvos in Rats

    Directory of Open Access Journals (Sweden)

    Muhammet Murat Celik

    2015-01-01

    Full Text Available The protective effects of Caffeic Acid Phenethyl Ester (CAPE and intralipid (IL on nephrotoxicity caused by acute Dichlorvos (D toxicity were investigated in this study. Forty-eight Wistar Albino rats were divided into 7 groups as follows: Control, D, CAPE, intralipid, D + CAPE, D + IL, and D + CAPE + IL. When compared to D group, the oxidative stress index (OSI values were significantly lower in Control, CAPE, and D + IL + CAPE groups. When compared to D + IL + CAPE group, the TOS and OSI values were significantly higher in D group (P<0.05. When mitotic cell counts were assessed in the renal tissues, it was found that mitotic cell count was significantly higher in the D group while it was lower in the D + CAPE, D + IL, and D + IL + CAPE groups when compared to the control group (P<0.05. Also, immune reactivity showed increased apoptosis in D group and low profile of apoptosis in the D + CAPE group when compared to the Control group. The apoptosis level was significantly lower in D + IL + CAPE compared to D group (P<0.05 in the kidneys. As a result, we concluded that Dichlorvos can be used either alone or in combination with CAPE and IL as supportive therapy or as facilitator for the therapeutic effect of the routine treatment in the patients presenting with pesticide poisoning.

  6. Thermosetting gel for the delivery of 5-aminolevulinic acid esters to the cervix.

    Science.gov (United States)

    Collaud, Sabine; Peng, Qian; Gurny, Robert; Lange, Norbert

    2008-07-01

    5-Aminolevulinic acid (5-ALA)-mediated photodynamic therapy has been proposed as an alternative, cervix-sparing treatment for cervical intraepithelial neoplasia (CIN). In this context, topical application of 5-ALA to the cervix is beneficial due to the small necessary dose and its minimal side effects. Therefore, lipophilic 5-ALA esters, such as hexylaminolevulinate (HAL), have led to improved local bioavailability and therapeutic efficacy. Hydrogels have shown to be more appropriate for the local delivery of these derivatives, but due to the limited long-term stability of such formulations at 25 degrees C, the development of an extemporaneously prepared hydrogel targeting CIN can be advantageous. Therefore, a poloxamer 407 thermosetting gel, which is liquid at room temperature and becomes a semi-solid when in contact with the female genital tract, has been evaluated in vitro and in vivo. Rheological evaluation has shown that a 17.0% poloxamer 407 hydrogel with a sol-gel transition at 24.8 +/- 0.6 degrees C was the best formulation for easy application and optimal residence time. Furthermore, similarly to other hydrogels previously tested, such a formulation shows a more complete HAL release in vitro than conventional cream vehicles, and tends to increase porphyrin accumulation in nude mice skin. Finally, in vitro release profiles were correlated to the in vivo results.

  7. Effects of caffeic acid phenethyl ester on palatal mucosal defects and tooth extraction sockets

    Science.gov (United States)

    Günay, Ahmet; Arpağ, Osman Fatih; Atilgan, Serhat; Yaman, Ferhan; Atalay, Yusuf; Acikan, İzzet

    2014-01-01

    Aim The purpose of this study was to evaluate the effects of caffeic acid phenethyl ester (CAPE) on palatal mucosal defects and tooth extraction sockets in an experimental model. Materials and methods Forty-two male Sprague-Dawley rats with a mean age of 7 weeks and weighing 280–490 g were used in this study. The rats were randomly divided into two groups: group A (the control group, n=21) and group B (the experimental group, n=21). Under anesthesia with ketamine (8 mg/100 g, intraperitoneally), palatal mucosal defects were created and tooth extraction was performed in the rats in groups A and B. Group A received no treatment, whereas group B received CAPE. CAPE was injected daily (10 μmol/kg, intraperitoneally). The rats were killed on days 7, 14, and 30 after the procedures. Palatal mucosa healing and changes in bone tissue and fibrous tissue were evaluated histopathologically. Result Pairwise comparisons showed no statistically significant difference between days 7 and 14 in either group (P>0.05). At day 30, bone healing was significantly better in group B (CAPE) than in group A (control) (P0.05). Conclusion In conclusion, the findings of this study suggest that CAPE can significantly improve tooth socket healing. PMID:25364232

  8. Glucuronoyl Esterase Screening and Characterization Assays Utilizing Commercially Available Benzyl Glucuronic Acid Ester

    Directory of Open Access Journals (Sweden)

    Hampus Sunner

    2015-09-01

    Full Text Available Research on glucuronoyl esterases (GEs has been hampered by the lack of enzyme assays based on easily obtainable substrates. While benzyl d-glucuronic acid ester (BnGlcA is a commercially available substrate that can be used for GE assays, several considerations regarding substrate instability, limited solubility and low apparent affinities should be made. In this work we discuss the factors that are important when using BnGlcA for assaying GE activity and show how these can be applied when designing BnGlcA-based GE assays for different applications: a thin-layer chromatography assay for qualitative activity detection, a coupled-enzyme spectrophotometric assay that can be used for high-throughput screening or general activity determinations and a HPLC-based detection method allowing kinetic determinations. The three-level experimental procedure not merely facilitates routine, fast and simple biochemical characterizations but it can also give rise to the discovery of different GEs through an extensive screening of heterologous Genomic and Metagenomic expression libraries.

  9. Polycyclic aromatic hydrocarbon removal from contaminated soils using fatty acid methyl esters.

    Science.gov (United States)

    Gong, Zongqiang; Wang, Xiaoguang; Tu, Ying; Wu, Jinbao; Sun, Yifei; Li, Peng

    2010-03-01

    In this study, solubilization of PAHs from a manufactured gas plant (MGP) soil and two artificially spiked soils using fatty acid methyl esters (FAME) was investigated. PAH removals from both the MGP and the spiked soils by FAME, methanol, soybean oil, hydroxypropyl-beta-cyclodextrin, Triton X-100, and Tween 80 were compared. The effect of FAME:MGP soil ratios on PAH removals was also investigated. Results showed that the FAME mixture synthesized by our lab was more efficient than the cyclodextrin and the two surfactants used for PAH removal from the spiked soils with individual PAH concentrations of 200 and 400 mg kg(-1). However, the difference among three PAH removals by the FAME, soybean oil and methanol was not quite pronounced. The FAME synthesized and market biodiesel exhibited better performance for PAH removals (46% and 35% of total PAH) from the weathered contaminated MGP soil when compared with the other agents (0-31%). Individual PAH removals from the weathered MGP soil were much lower than those from the spiked soils. The percentages of total PAH removals from the MGP soil were 59%, 46%, and 51% for the FAME:MGP soil ratios of 1:2, 1:1, and 2:1, respectively. These results showed that the FAME could be a more attractive alternative to conventional surfactants in ex situ washing of PAH-contaminated soils. 2010 Elsevier Ltd. All rights reserved.

  10. Simultaneous production of fatty acid methyl esters and diglycerides by four recombinant Candida rugosa lipase's isozymes.

    Science.gov (United States)

    Chang, Shu-Wei; Huang, Myron; Hsieh, Yu-Hsun; Luo, Ying-Ting; Wu, Tsung-Ta; Tsai, Chia-Wen; Chen, Chin-Shuh; Shaw, Jei-Fu

    2014-07-15

    In this study, the catalytic efficiency of four recombinant CRL (Candida rugosa lipase) isozymes (LIP1-LIP4) towards the production of fatty acid methyl ester (FAME) was compared and evaluated as an alternative green method for industrial applications. The results indicated that the recombinant C. rugosa LIP1 enzyme exhibited the highest catalytic efficiency for FAME production compared to the recombinant C. rugosa LIP2-LIP4 enzymes. The optimal conditions were as follows: pH 7.0, methanol/soybean oil molar ratio: 3/1, enzyme amount: 2U (1.6 μL), reaction temperature: 20°C, 22 h of reaction time, and 3 times of methanol addition (1 mol/6h), and resulted in 61.5 ± 1.5 wt.% of FAME conversion. The reaction product contained also 10 wt.% of DAG with a ratio of 1,3-DAG to 1,2-DAG of approximately 4:6, and can be potentially used in industrial applications as a food emulsifier. Copyright © 2014 Elsevier Ltd. All rights reserved.

  11. Kinetics of enzymatic synthesis of liquid wax ester from oleic acid and oleyl alcohol.

    Science.gov (United States)

    Radzi, Salina Mat; Mohamad, Rosfarizan; Basri, Mahiran; Salleh, Abu Bakar; Ariff, Arbakariya; Rahman, Mohammad Basyaruddin Abdul; Rahman, Raja Noor Zaliha Raja Abdul

    2010-01-01

    The kinetics of wax ester synthesis from oleic acid and oleyl alcohol using immobilized lipase from Candida antartica as catalyst was studied with different types of impeller (Rushton turbine and AL-hydrofoil) to create different mixing conditions in 2l stirred tank reactor. The effects of catalyst concentration, reaction temperature, and impeller tip speed on the synthesis were also evaluated. Rushton turbine impeller exhibited highest conversion rate at lower impeller tip speed as compared to AL-hydrofoil impeller. A second-order reversible kinetic model from single progress curve for the prediction of fractional conversion at given reaction time was proposed and the corresponding kinetic parameter values were calculated by non-linear regression method. The results from the simulation using the proposed model showed satisfactory agreement with the experimental data. Activation energy shows a value of 21.77 Kcal/mol. The thermodynamic parameters of the process, enthalpy and entropy, were 21.15 Kcal/mol and 52.07 cal/mol.K, respectively.

  12. Modulation of Tamoxifen Cytotoxicity by Caffeic Acid Phenethyl Ester in MCF-7 Breast Cancer Cells

    Directory of Open Access Journals (Sweden)

    Tarek K. Motawi

    2016-01-01

    Full Text Available Although Tamoxifen (TAM is one of the most widely used drugs in managing breast cancer, many women still relapse after long-term therapy. Caffeic acid phenethyl ester (CAPE is a polyphenolic compound present in many medicinal plants and in propolis. The present study examined the effect of CAPE on TAM cytotoxicity in MCF-7 cells. MCF-7 cells were treated with different concentrations of TAM and/or CAPE for 48 h. This novel combination exerted synergistic cytotoxic effects against MCF-7 cells via induction of apoptotic machinery with activation of caspases and DNA fragmentation, along with downregulation of Bcl-2 and Beclin 1 expression levels. However, the mammalian microtubule-associated protein light chain LC 3-II level was unchanged. Vascular endothelial growth factor level was also decreased, whereas levels of glutathione and nitric oxide were increased. In conclusion, CAPE augmented TAM cytotoxicity via multiple mechanisms, providing a novel therapeutic approach for breast cancer treatment that can overcome resistance and lower toxicity. This effect provides a rationale for further investigation of this combination.

  13. [Inhibition of oxidation of unsaturated fatty acid methyl esters by essential oils].

    Science.gov (United States)

    Misharina, T A; Alinkina, E S; Vorobjeva, A K; Terenina, M B; Krikunova, N I

    2016-01-01

    The essential oils from 16 various spice plants were studied as natural antioxidants for the inhibition of autooxidation of polyunsaturated fatty acids methyl esters isolated from linseed oil. The content of methyl oleate, methyl linoleate, and methyl linolenoate after 1, 2, and 4 months of autooxidation were used as criteria to estimate the antioxidant efficiencies of essential oils. In 4 months, 92% of the methyl linolenoate and 79% of the methyl linoleate were oxidized in a control sample of a model system. It was found that the most effective antioxidants were essential oils from clove bud, cinnamon leaves, and oregano. They inhibited autooxidation of methyl linolenoate by 76–85%. The antioxidant properties of these essential oils were due to phenols— eugenol, carvacrol, and thymol. Essential oil from coriander did not contain phenols, but it inhibited methyl linolenoate oxidation by 38%. Essential oils from thyme, savory, mace, lemon, and tea tree inhibited methyl linolenoate oxidation by 17–24%. The other essential oils had no antioxidant properties.

  14. Early Treatment of radiation-Induced Heart Damage in Rats by Caffeic acid phenethyl Ester

    International Nuclear Information System (INIS)

    Tawfik, S.S.; Mansour, H. H.

    2012-12-01

    The study designed to determine the therapeutic effect of caffeic acid phenethyl ester (CAPE) in minimising radiation-induced injuries in rats. Rats were exposed to 7 Gy γ-rays, 30 minutes later; rats were injected with CAPE (10μmol/ kg body, i.p.) for 7 consecutive days. Rats were sacrificed at 8 and 15 days after starting the experiment. Gamma-irradiation induced significant increase in malonaldehyde (MDA) level and xanthine oxidase (XO) and adenosine deaminase (ADA) activities, and significant decrease in total nitrate/nitrate (NO (x)) level and glutathione peroxidise (Gpx), superoxide dismutase (SOD)and catalase (CAT) activities in heart tissue and augmented activities of lactate dehydrogenase (LDH), creatine phosphokinase (CPK) and aspartate transaminase (AST) in serum. Irradiated rats early treated with CAPE showed significant decrease in MDA, XO and ADA and significant increase in group. Cardiac enzymes were restored. Conclusion, CAPE could exhibits curable effect on gamma irradiation-induced cardiac-oxidative impairment in rats. (Author)

  15. Antifungal and antioxidant activity of fatty acid methyl esters from vegetable oils

    Directory of Open Access Journals (Sweden)

    MARIA E.A. PINTO

    2017-08-01

    Full Text Available ABSTRACT Fatty acid methyl esters (FAMEs were obtained from vegetable oils of soybean, corn and sunflower. The current study was focused on evaluating the antifungal activity of FAMEs mainly against Paracoccidioides spp., as well as testing the interaction of these compounds with commercial antifungal drugs and also their antioxidant potential. FAMEs presented small IC50 values (1.86-9.42 μg/mL. All three FAMEs tested showed antifungal activity against isolates of Paracoccidioides spp. with MIC values ranging from 15.6-500 µg/mL. Sunflower FAMEs exhibited antifungal activity that extended also to other genera, with an MIC of 15.6 μg/mL against Candida glabrata and C. krusei and 31.2 μg/mL against C. parapsilosis. FAMEs exhibited a synergetic effect with itraconazole. The antifungal activity of the FAMEs against isolates of Paracoccidioides spp. is likely due to the presence of methyl linoleate, the major compound present in all three FAMEs. The results obtained indicate the potential of FAMEs as sources for antifungal and antioxidant activity.

  16. Experimental and numerical investigations on spray characteristics of fatty acid methyl esters

    Science.gov (United States)

    Lanjekar, R. D.; Deshmukh, D.

    2018-02-01

    A comparative experimental and numerical study is conducted to establish the significance of the use of single-component over multi-component representatives of biodiesel, diesel and their blend for predicting spray tip penetration. Methyl oleate and methyl laurate are used as single-component representative fuels for biodiesel. The pure components n-heptane, n-dodecane and n-tetradecane are used as single-component representative fuels for diesel. Methyl laurate is found to represent biodiesel of coconut, whereas methyl oleate is found to represent biodiesel having high percentage of long-chain fatty acid esters. The spray tip penetration of methyl oleate is found to be in good agreement with the measured spray tip penetration of karanja biodiesel. The spray tip penetration prediction of n-heptane fuel is closely following diesel spray tip penetration along with that of n-tetradecane and n-dodecane. The study suggests that the knowledge of the single-component representatives of biodiesel, diesel and their blend is sufficient to predict the spray tip penetration of the corresponding biodiesel, diesel and their blend under non-evaporating environment.

  17. Caffeic Acid Phenethyl Ester Is a Potential Therapeutic Agent for Oral Cancer

    Directory of Open Access Journals (Sweden)

    Ying-Yu Kuo

    2015-05-01

    Full Text Available Head and neck cancers, which affect 650,000 people and cause 350,000 deaths per year, is the sixth leading cancer by cancer incidence and eighth by cancer-related death worldwide. Oral cancer is the most common type of head and neck cancer. More than 90% of oral cancers are oral and oropharyngeal squamous cell carcinoma (OSCC. The overall five-year survival rate of OSCC patients is approximately 63%, which is due to the low response rate to current therapeutic drugs. In this review we discuss the possibility of using caffeic acid phenethyl ester (CAPE as an alternative treatment for oral cancer. CAPE is a strong antioxidant extracted from honeybee hive propolis. Recent studies indicate that CAPE treatment can effectively suppress the proliferation, survival, and metastasis of oral cancer cells. CAPE treatment inhibits Akt signaling, cell cycle regulatory proteins, NF-κB function, as well as activity of matrix metalloproteinase (MMPs, epidermal growth factor receptor (EGFR, and Cyclooxygenase-2 (COX-2. Therefore, CAPE treatment induces cell cycle arrest and apoptosis in oral cancer cells. According to the evidence that aberrations in the EGFR/phosphoinositide 3-kinase (PI3K/protein kinase B (Akt signaling, NF-κB function, COX-2 activity, and MMPs activity are frequently found in oral cancers, and that the phosphorylation of Akt, EGFR, and COX-2 correlates to oral cancer patient survival and clinical progression, we believe that CAPE treatment will be useful for treatment of advanced oral cancer patients.

  18. EFFECTS OF EXERCISE AND CAFFEIC ACID PHENETHYL ESTER AFTER CHRONIC EXERCISE RAT MODEL

    Directory of Open Access Journals (Sweden)

    Ayse Alp

    2011-01-01

    Full Text Available In order to understand whether exercise and caffeic acid phenethyl ester (CAPE has an effect on obesity and weight control, we investigated the effects of CAPE, and exercise on lipid parameters (triglyceride, total cholesterol, HDL-C, LDL-C, and adipokine substances such as leptin and resistin in rats. 40 male rat were randomly assigned into 4 groups. It was determined that CAPE does not have any significant effect on these parameters but that lipid parameters and leptin values in exercise groups decreased considerably, while no significant change occurred in resistin levels. In order to understand whether diet has an effect on exercise, body weights of all animal groups in pre and post-exercise were compared. A significant weight gain was observed (p = 0.005 in all groups. This study concluded that exercise has a considerable effect on leptin and lipid parameters; however, exercise alone was not sufficient for weight control and could be effective in weight control only when accompanied by a restricted diet.

  19. Experimental and numerical investigations on spray characteristics of fatty acid methyl esters.

    Science.gov (United States)

    Lanjekar, R D; Deshmukh, D

    2018-02-01

    A comparative experimental and numerical study is conducted to establish the significance of the use of single-component over multi-component representatives of biodiesel, diesel and their blend for predicting spray tip penetration. Methyl oleate and methyl laurate are used as single-component representative fuels for biodiesel. The pure components n -heptane, n -dodecane and n -tetradecane are used as single-component representative fuels for diesel. Methyl laurate is found to represent biodiesel of coconut, whereas methyl oleate is found to represent biodiesel having high percentage of long-chain fatty acid esters. The spray tip penetration of methyl oleate is found to be in good agreement with the measured spray tip penetration of karanja biodiesel. The spray tip penetration prediction of n -heptane fuel is closely following diesel spray tip penetration along with that of n -tetradecane and n -dodecane. The study suggests that the knowledge of the single-component representatives of biodiesel, diesel and their blend is sufficient to predict the spray tip penetration of the corresponding biodiesel, diesel and their blend under non-evaporating environment.

  20. Radiation-induced copolymerizations of perfluorovinyl acetic acid and its methyl ester with α-olefin

    International Nuclear Information System (INIS)

    Kawaguchi, M.; Watanabe, T.; Matsuda, O.; Tabata, Y.; Machi, S.

    1981-01-01

    Homopolymerizations and copolymerizations of perfluorovinyl acetic acid (FVA) and its methyl ester (MFVA) were carried out by γ radiation at a temperature of 25 0 C, a dose rate of 1 x 10 6 rad/hr, and FVA/α-olefin and MFVA/α-olefin ratios of 10/90-90/10 in the monomer mixture. FVA and MFVA gave small quantities of brown and greasy low-molecular-weight homopolymers. The polymerization rates of both FVA and MFVA were extremely small, as shown by the maximum G value of monomer consumption of 12. FVA and MFVA reacted with α-olefin to form waxlike copolymers. The copolymerization rates of both FVA and MFVA with α-olefin were remarkably larger than those of the homopolymerizations, particularly with ethylene. The polymer compositions of FVA/ethylene or MFVA/ethylene were nearly 1/2 over a wide range of the monomer compositions. The Mayo-Lewis method gave negative r 1 (FVA) and r 1 (MFVA). The polymer composition curves could be well interpreted by introducing the penultimate model

  1. Utilization of rapeseed pellet from fatty acid methyl esters production as an energy source.

    Science.gov (United States)

    Ciunel, Krzysztof; Klugmann-Radziemska, Ewa

    2014-01-01

    Rapeseed pellet - crushed seed residue from oil extraction is a by-product of fatty acid methyl esters production process. As other types of biomass, it can either be burned directly in furnaces or processed to increase its energetic value. Biomass is renewable, abundant and has domestic usage; the sources ofbiomass can help the world reduce its dependence on petroleum products, fossil coal and natural gas. Energetically effective utilization of rapeseed pellet could substantially improve the economic balance of an individual household in which biodiesel for fulfilling the producer's own energetic demand is obtained. In this article, the experimental results of combusting rapeseed pellet in a calorimeter, combustion in a boiler heater and the analysis of the emissions level of different pollutants in exhaust fumes during different stages of biomass boiler operation are presented. It has been proved that the pellet, a by-product of biodiesel production, is not only a valuable substitute of animal fodder, but also an excellent renewable and environmentally friendly energy source, viable for use in household tap water heating installations.

  2. Preparation and investigation of mefenamic acid – polyethylene glycol – sucrose ester solid dispersions

    Directory of Open Access Journals (Sweden)

    Fülöp Ibolya

    2015-12-01

    Full Text Available Mefenamic acid (MA is a widely used non-steroidal antiinflammatory (NSAID drug. The adverse effects typical of NSAIDs are also present in the case of MA, partly due to its low water solubility. The aim of this study was to increase the water solubility of MA in order to influence its absorption and bioavailability. Solid dispersions of MA were prepared by the melting method using polyethylene glycol 6000 and different types (laurate, D-1216; palmitate, P-1670; stearate, S-1670 and amounts of sucrose esters as carriers. The X-ray diffraction results show that MA crystals were not present in the products. Dissolution tests carried out in artificial intestinal juice showed that the product containing 10 % D-1216 increased water solubility about 3 times. The apparent permeability coefficient of MA across human Caco-2 intestinal epithelial cell layers was high and, despite the difference in solubility, there was no further increase in drug penetration in the presence of the applied additives.

  3. Multi-organ sarcoidosis treatment with fumaric acid esters: a case report and review of the literature.

    Science.gov (United States)

    Zouboulis, Christos C; Lippert, Undine; Karagiannidis, Ioannis

    2014-01-01

    Sarcoidosis is a rare, systemic disease that is characterized by the formation of granulomas in various organs, including the skin. As the etiology remains unknown, the treatment of sarcoidosis is challenging. We present a 47-year-old female patient with progressive, multi-organ sarcoidosis who had a complete clinical improvement of the skin lesions, a moderate reduction in pulmonary opacities on chest X-ray, a marked subjective improvement in general status and pulmonary efficiency and a marked reduction in serum angiotensin-converting enzyme and soluble interleukin-2 receptor after 6 months of therapy with fumaric acid esters. The present case and similar reports in the literature highlight the probable efficacy of fumaric acid esters in the treatment of sarcoidosis and other non-infectious, granulomatous diseases. © 2014 S. Karger AG, Basel.

  4. High-Throughput Analysis of Sucrose Fatty Acid Esters by Supercritical Fluid Chromatography/Tandem Mass Spectrometry

    Science.gov (United States)

    Hori, Katsuhito; Tsumura, Kazunobu; Fukusaki, Eiichiro; Bamba, Takeshi

    2014-01-01

    Supercritical fluid chromatography (SFC) coupled with triple quadrupole mass spectrometry was applied to the profiling of sucrose fatty acid esters (SEs). The SFC conditions (column and modifier gradient) were optimized for the effective separation of SEs. In the column test, a silica gel reversed-phase column was selected. Then, the method was used for the detailed characterization of commercial SEs and the successful analysis of SEs containing different fatty acids. The present method allowed for fast and high-resolution separation of monoesters to tetra-esters within a shorter time (15 min) as compared to the conventional high-performance liquid chromatography. The applicability of our method for the analysis of SEs was thus demonstrated. PMID:26819875

  5. Optimization of oligoglycerol fatty acid esters preparation catalyzed by Lipozyme 435

    Directory of Open Access Journals (Sweden)

    Wan, F. L.

    2015-09-01

    Full Text Available Oli goglycerol fatty acid esters (OGEs are an important kind of polyglycerol fatty acid esters (PGEs which have been widely used as emulsifiers in food, medicine and cosmetic industries. The aim of this study was to investigate the preparation of OGEs by the esterification of olig oglycerol with linoleic acid in a solvent- free system using Lipozyme 435 as the catalyst. The effects of substrate molar ratio, reaction time, reaction temperature, enzyme dosage, and water addition on the efficiency of esterification (EE were studied. Single factor experiments and response surface methodology (RSM were employed to optimize the reaction parameters. The optimum conditions were obtained as follows: reaction time 4.52 h, reaction temperature 90 °C, enzyme dosage 2 wt% (based on the total substrate mass, the molar ratio of oligoglycerol to linoleic acid 1.59:1 and no water addition. Under these conditions, the experimental EE (95.82±0.22% fitted well with that predicted by RSM (96.15%. Similar results were obtained when the process was scaled up to a production of 500 g in a pilot bubble column reactor (BCR. The enzyme maintained 98.2% of the relative activity after 10 batches of reaction in the BCR. Electro spray ionization mass spectrum was employed to rapidly analyze the esterification products, and most species of OGEs have been identified.Los ésteres grasos de oligoglicerol (OGEs son una clase importante de ésteres de ácidos grasos de poliglicerol (PGE que han sido ampliamente utilizados como emulsionantes en alimentación, medicina y en la industria cosmética. El objetivo de este estudio fue investigar la preparación de OGEs mediante la esterificación de oligoglicerol con ácido linoleico en un sistema libre de disolvente utilizando Lipozyme 435 como catalizador. Se estudiaron los efectos en la eficiencia de esterificación (EE de la relación molar de sustratos, de los tiempos de reacción, las temperaturas de reacción, la dosis de la

  6. Poly(ester amide)s based on (L)-lactic acid oligomers and α-amino acids: influence of the α-amino acid side chain in the poly(ester amide)s properties.

    Science.gov (United States)

    Fonseca, Ana C; Coelho, Jorge F J; Valente, Joana F A; Correia, Tiago R; Correia, Ilídio J; Gil, Maria H; Simões, Pedro N

    2013-01-01

    Novel biodegradable and low cytotoxic poly(ester amide)s (PEAs) based on α-amino acids and (L)-lactic acid (L-LA) oligomers were successfully synthesized by interfacial polymerization. The chemical structure of the new polymers was confirmed by spectroscopic analyses. Further characterization suggests that the α-amino acid plays a critical role on the final properties of the PEA. L-phenylalanine provides PEAs with higher glass transition temperature, whereas glycine enhances the crystallinity. The hydrolytic degradation in PBS (pH = 7.4) at 37 °C also depends on the α-amino acid, being faster for glycine-based PEAs. The cytotoxic profiles using fibroblast human cells indicate that the PEAs did not elicit an acute cytotoxic effect. The strategy presented in this work opens the possibility of synthesizing biodegradable PEAs with low citotoxicity by an easy and fast method. It is worth to mention also that the properties of these materials can be fine-tuned only by changing the α-amino acid.

  7. Temperature dependences of saturated vapor pressure and the enthalpy of vaporization of n-pentyl esters of dicarboxylic acids

    Science.gov (United States)

    Portnova, S. V.; Krasnykh, E. L.; Levanova, S. V.

    2016-05-01

    The saturated vapor pressures and enthalpies of vaporization of n-pentyl esters of linear C2-C6 dicarboxylic acids are determined by the transpiration method in the temperature range of 309.2-361.2 K. The dependences of enthalpies of vaporization on the number of carbon atoms in the molecule and on the retention indices have been determined. The predictive capabilities of the existing calculation schemes for estimation of enthalpy of vaporization of the studied compounds have been analyzed.

  8. Synthesis of 1-Methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic Acid Methyl Ester

    Directory of Open Access Journals (Sweden)

    Gil Valdo José da Silva

    2005-11-01

    Full Text Available A simple and efficient method for the preparation of 1-methyl-3-oxo-7- oxabicyclo[2.2.1]hept-5-en-2-carboxylic acid methyl ester (1 is described. The first step is a highly regioselective Diels-Alder reaction between 2-methylfuran and methyl-3-bromo- propiolate. A remarkably difficult ketal hydrolysis reaction was effected by treatment with HCl, a simple reagent that was shown to be more efficient, in this case, than commonly used more elaborate methods.

  9. Use of Fatty Acid Methyl Ester Profiles for Discrimination of Bacillus cereus T-Strain Spores Grown on Different Media▿

    OpenAIRE

    Ehrhardt, Christopher J.; Chu, Vivian; Brown, TeeCie; Simmons, Terrie L.; Swan, Brandon K.; Bannan, Jason; Robertson, James M.

    2010-01-01

    The goal of this study was to determine if cellular fatty acid methyl ester (FAME) profiling could be used to distinguish among spore samples from a single species (Bacillus cereus T strain) that were prepared on 10 different medium formulations. To analyze profile differences and identify FAME biomarkers diagnostic for the chemical constituents in each sporulation medium, a variety of statistical techniques were used, including nonmetric multidimensional scaling (nMDS), analysis of similarit...

  10. Effect of Caffeic Acid Phenethyl Ester on Vascular Damage Caused by Consumption of High Fructose Corn Syrup in Rats

    OpenAIRE

    Gun, Aburrahman; Ozer, Mehmet Kaya; Bilgic, Sedat; Kocaman, Nevin; Ozan, Gonca

    2016-01-01

    Fructose corn syrup is cheap sweetener and prolongs the shelf life of products, but fructose intake causes hyperinsulinemia, hypertriglyceridemia, and hypertension. All of them are referred to as metabolic syndrome and they are risk factors for cardiovascular diseases. Hence, the harmful effects of increased fructose intake on health and their prevention should take greater consideration. Caffeic Acid Phenethyl Ester (CAPE) has beneficial effects on metabolic syndrome and vascular function wh...

  11. Regiospecific synthesis of new fatty N-acyl trihalomethylated pyrazoline derivatives from fatty acid methyl esters (FAMEs)

    Energy Technology Data Exchange (ETDEWEB)

    Beck, Paulo; Santos, Juliane M. dos; D' Oca, Marcelo G. M.; Piovesan, Luciana A., E-mail: lpiovesan@gmail.com [Universidade Federal do Rio Grande (UFRS), RS (Brazil). Escola de Quimica e Alimentos; Kuhn, Bruna L.; Moreira, Dayse N.; Flores, Alex F.C.; Martins, Marcos A.P. [Universidade Federal de Santa Maria (UFSM), RS (Brazil). Dept. de Quimica

    2012-11-15

    A series of new fatty N-acyl trihalomethylated pyrazoline derivatives from fatty acid methyl esters was synthesized by the cyclo condensation of respective fatty hydrazides with 4-alkoxy- 1,1,1-trial omethyl-3-alquen-2-ones. Efficient and regiospecific cyclizations catalyzed by BF{sub 3}-MeOH gave the desired products in good to excellent yields and at high purity. (author)

  12. Longitudinal Associations of Phospholipid and Cholesteryl Ester Fatty Acids With Disorders Underlying Diabetes.

    Science.gov (United States)

    Johnston, Luke W; Harris, Stewart B; Retnakaran, Ravi; Zinman, Bernard; Giacca, Adria; Liu, Zhen; Bazinet, Richard P; Hanley, Anthony J

    2016-06-01

    Specific serum fatty acid (FA) profiles predict the development of incident type 2 diabetes; however, limited longitudinal data exist exploring their role in the progression of insulin sensitivity (IS) and β-cell function. To examine the longitudinal associations of the FA composition of serum phospholipid (PL) and cholesteryl ester (CE) fractions with IS and β-cell function over 6 years. The Prospective Metabolism and Islet Cell Evaluation (PROMISE) cohort is a longitudinal observational study, with clinic visits occurring every 3 years. Three visits have been completed, totaling 6 years of follow-up. Individuals (n = 477) at risk for diabetes recruited from the general population in London and Toronto, Canada. Values from an oral glucose tolerance test were used to compute 1/HOMA-IR and the Matsuda index for IS, the insulinogenic index over HOMA-IR, and the insulin secretion-sensitivity index-2 for β-cell function. Thin-layer chromatograph and gas chromatograph quantified FA. Generalized estimating equations were used for the analysis. IS and β-cell function declined by 8.3-19.4% over 6 years. In fully adjusted generalized estimating equation models, PL cis-vaccenate (18:1n-7) was positively associated with all outcomes, whereas γ-linolenate (GLA; 18:3n-6) and stearate (18:0) were negatively associated with IS. Tests for time interactions revealed that PL eicosadienoate (20:2n-6) and palmitate (16:0) and CE dihomo-γ-linolenate (20:3n-6), GLA, and palmitate had stronger associations with the outcomes after longer follow-up. In a Canadian population at risk for diabetes, we found that higher PL stearate and GLA and lower cis-vaccenic acid predicted consistently lower IS and β-cell function over 6 years.

  13. Ionic liquid phases with comprehensive two-dimensional gas chromatography of fatty acid methyl esters.

    Science.gov (United States)

    Pojjanapornpun, Siriluck; Nolvachai, Yada; Aryusuk, Kornkanok; Kulsing, Chadin; Krisnangkura, Kanit; Marriott, Philip J

    2018-02-17

    New generation inert ionic liquid (iIL) GC columns IL60i, IL76i and IL111i, comprising phosphonium or imidazolium cationic species, were investigated for separation of fatty acid methyl esters (FAME). In general, the iIL phases provide comparable retention times to their corresponding conventional columns, with only minor selectivity differences. The average tailing factors and peak widths were noticeably improved (reduced) for IL60i and IL76i, while they were slightly improved for IL111i. Inert IL phase columns were coupled with conventional IL columns in comprehensive two-dimensional GC (GC × GC) with a solid-state modulator which offers variable modulation temperature (T M ), programmable T M during analysis and trapping stationary phase material during the trap/release (modulation) process, independent of oven T and column sets. Although IL phases are classified as polar, relative polarity of the two phases comprising individual GC × GC column sets permits combination of less-polar IL/polar IL and polar IL/less-polar IL column sets; it was observed that a polar/less-polar column set provided better separation of FAME. A higher first dimension ( 1 D) phase polarity combined with a lower 2 D phase polarity, for instance 1 D IL111i with 2 D IL59 gave the best result; the greater difference in 1 D/ 2 D phase polarity results in increasing occupancy of peak area in the 2D space. The IL111i/IL59 column set was selected for analysis of fatty acids in fat and oil products (butter, margarine, fish oil and canola oil). Compared with the conventional IL111, IL111i showed reduced column bleed which makes this more suited to GC × GC analysis of FAME. The proposed method offers a fast profiling approach with good repeatability of analysis of FAME.

  14. Separation of fatty acid methyl esters by GC-online hydrogenation × GC.

    Science.gov (United States)

    Delmonte, Pierluigi; Fardin-Kia, Ali Reza; Rader, Jeanne I

    2013-02-05

    The separation of fatty acid methyl esters (FAME) provided by a 200 m × 0.25 mm SLB-IL111 capillary column is enhanced by adding a second dimension of separation ((2)D) in a GC × GC design. Rather than employing two GC columns of different polarities or using different elution temperatures, the separation in the two-dimensional space is achieved by altering the chemical structure of selected analytes between the two dimensions of separation. A capillary tube coated with palladium is added between the first dimension of separation ((1)D) column and the cryogenic modulator, providing the reduction of unsaturated FAMEs to their fully saturated forms. The (2)D separation is achieved using a 2.5 m × 0.10 mm SLB-IL111 capillary column and separates FAMEs based solely on their carbon skeleton. The two-dimensional separation can be easily interpreted based on the principle that all the saturated FAMEs lie on a straight diagonal line bisecting the separation plane, while the FAMEs with the same carbon skeleton but differing in the number, geometric configuration or position of double bonds lie on lines parallel to the (1)D time axis. This technique allows the separation of trans fatty acids (FAs) and polyunsaturated FAs (PUFAs) in a single experiment and eliminates the overlap between PUFAs with different chain lengths. To our knowledge, this the first example of GC × GC in which a chemical change is instituted between the two dimensions to alter the relative retentions of components and identify unsaturated FAMEs.

  15. Meso-ester and carboxylic acid substituted BODIPYs with far-red and near-infrared emission for bioimaging applications

    KAUST Repository

    Ni, Yong

    2014-01-21

    A series of meso-ester-substituted BODIPY derivatives 1-6 are synthesized and characterized. In particular, dyes functionalized with oligo(ethylene glycol) ether styryl or naphthalene vinylene groups at the α positions of the BODIPY core (3-6) become partially soluble in water, and their absorptions and emissions are located in the far-red or near-infrared region. Three synthetic approaches are attempted to access the meso-carboxylic acid (COOH)-substituted BODIPYs 7 and 8 from the meso-ester-substituted BODIPYs. Two feasible synthetic routes are developed successfully, including one short route with only three steps. The meso-COOH-substituted BODIPY 7 is completely soluble in pure water, and its fluorescence maximum reaches around 650 nm with a fluorescence quantum yield of up to 15 %. Time-dependent density functional theory calculations are conducted to understand the structure-optical properties relationship, and it is revealed that the Stokes shift is dependent mainly on the geometric change from the ground state to the first excited singlet state. Furthermore, cell staining tests demonstrate that the meso-ester-substituted BODIPYs (1 and 3-6) and one of the meso-COOH-substituted BODIPYs (8) are very membrane-permeable. These features make these meso-ester- and meso-COOH-substituted BODIPY dyes attractive for bioimaging and biolabeling applications in living cells. Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  16. Data from mass spectrometry, NMR spectra, GC–MS of fatty acid esters produced by Lasiodiplodia theobromae

    Directory of Open Access Journals (Sweden)

    Carla C. Uranga

    2016-09-01

    Full Text Available The data described herein is related to the article with the title “Fatty acid esters produced by Lasiodiplodia theobromae function as growth regulators in tobacco seedlings” C.C. Uranga, J. Beld, A. Mrse, I. Cordova-Guerrero, M.D. Burkart, R. Hernandez-Martinez (2016 [1]. Data includes nuclear magnetic resonance spectroscopy and GC–MS data used for the identification and characterization of fatty acid esters produced by L. theobromae. GC–MS traces are also shown for incubations in defined substrate, consisting in Vogel׳s salts supplemented with either 5% grapeseed oil or 5% glucose, the two combined, or 5% fructose. Traces for incubations in the combination of 5% grapeseed oil and 5% glucose for different fungal species are also included. Images of mycelium morphology when grown in 5% glucose with or without 5% grapeseed oil are shown due to the stark difference in mycelial pigmentation in the presence of triglycerides. High concentration gradient data for the plant model Nicotiana tabacum germinated in ethyl stearate (SAEE and ethyl linoleate (LAEE is included to show the transition between growth inhibition and growth induction in N. tabacum by these compounds. Keywords: NMR, GC–MS, Fatty acid esters, Ethyl stearate, Ethyl linoleate, Growth inhibition, Growth induction

  17. Intestinal absorption and biliary elimination of glycyrrhizic acid diethyl ester in rats

    Directory of Open Access Journals (Sweden)

    Koga K

    2013-10-01

    Full Text Available Kenjiro Koga,1 Mayuri Kawamura,1 Hiroshi Iwase,2 Nobuji Yoshikawa31Department of Clinical Pharmaceutics, Faculty of Pharmaceutical Sciences, Hokuriku University, Kanazawa, 2Research Division, 3Research and Development Division, Cokey Systems Co, Ltd, Matsusaka, JapanBackground: The purpose of this study was to evaluate absorption and elimination from the gastrointestinal tract of glycyrrhizic acid diethyl ester (GZ-DE which was prepared as a prodrug of glycyrrhizic acid (a poorly absorbed compound in rats.Methods: After the GZ-DE solution was administered via the intravenous, intraduodenal, intraileal, and stomach routes, GZ-DE and GZ concentrations in bile were determined by high-performance liquid chromatography. The stability of GZ-DE was estimated from residual GZ-DE and GZ produced in GZ-DE solutions prepared with distilled water, a pH 1.2 solution, 0.9% NaCl solution, and phosphate-buffered solution (pH 7.4 at 37°C.Results: GZ-DE was eliminated into bile by the pharmacokinetic parameters of apparent distribution rate constant (4.56 ± 0.36 per hour and apparent elimination rate constant (0.245 ± 0.042 per hour. After intravenous and intraduodenal administration of GZ-DE, the concentration ratio of GZ-DE to GZ in bile was approximately 4:1, and the bioavailability of GZ containing GZ-DE was three-fold higher compared with the bioavailability of GZ after intraduodenal administration. GZ-DE was immediately precipitated in pH 1.2 solution and was converted to GZ by hydrolysis in pH 7.4 solution.Conclusion: Improvement of intestinal absorption of GZ was made possible by administration of GZ-DE into the intestine where absorption of GZ is lower than in the strong acidic environment of the stomach. However, because the elimination rate in bile simulated from kinetic parameters of GZ-DE was higher than the conversion rate from GZ-DE to GZ by hydrolysis, it is thought that the availability of GZ as a revolutionary prodrug was not high from the

  18. Antiarrhythmogenic effect of omega-3 fatty acid ethyl esters in a patient treated with Omacor after a non-Q-wave myocardial infarction

    Directory of Open Access Journals (Sweden)

    Andrey Ardashev

    2014-02-01

    The patient agreed to add omega-3 fatty acid ethyl ester supplementation (1 g/day to his treatment regimen. Pacemaker analyses 3 months later demonstrated no NSVT and only 215 PVBs daily. In more than 1 year of follow-up, the patient has remained well and has had no further ventricular arrhythmias. We conclude that omega-3 fatty acid ethyl ester supplementation may be beneficial in post-MI patients with pacemakers who develop ventricular arrhythmias.

  19. Contribution to the analysis of the essential oil of Helichrysum italicum (Roth) G. Don. Determination of ester bonded acids and phenols.

    Science.gov (United States)

    Mastelić, Josip; Politeo, Olivera; Jerković, Igor

    2008-04-07

    The essential oil of Helichrysum italicum (Roth) G. Don (everlasting or Immortelle essential oil) was isolated by hydrodistillation and analysed by GC and GCMS. Forty four compounds were identified. The main components were alpha-pinene(12.8%), 2-methyl-cyclohexyl pentanoate (11.1 %), neryl acetate (10.4%), 1,7-di-epi-alpha-cedrene (6.8%) and other compounds. The oil was fractionated and ester-containing fraction was hydrolysed with KOH/H(2)SO(4). The liberated volatiles were analysed by GC and GC-MS: three phenols and twenty seven volatile carboxylic acids were identified[70% low fatty acids (C(2)-C(5)), 15% C(10)-C(12) acids and 15% other acids]. The main acids were acetic acid (24.3%) propanoic acid (17.2%), 2-methylpropanoic acid (11.4%),dodecanoic acid (8.7%), 2-methylbutanoic acid (8.3%), (Z)-2-methylbutenoic acid(5.1%) and decanoic acid (4.6%). With respect to the identified bonded carboxylic acids,the minimal number of esters in the oil was twenty seven, but their overall quantity was probably larger due to different possible combinations of alcohols with acids to form esters. On the other hand, only six main esters were identified in the oil before fractionation and hydrolysis.

  20. MILLIMETER WAVE SPECTRUM AND ASTRONOMICAL SEARCH FOR VINYL FORMATE

    Energy Technology Data Exchange (ETDEWEB)

    Alonso, E. R.; Kolesniková, L.; Cabezas, C.; Alonso, J. L. [Grupo de Espectroscopia Molecular (GEM), Edificio Quifima, Área de Química-Física, Laboratorios de Espectroscopia y Bioespectroscopia, Parque Científico UVa, Unidad Asociada CSIC, Universidad de Valladolid, E-47011 Valladolid (Spain); Tercero, B.; Cernicharo, J. [Grupo de Astrofísica Molecular, ICMM-CSIC, C/Sor Juana Inés de la Cruz 3, E-28049 Cantoblanco (Spain); Guillemin, J.-C. [Institut des Sciences Chimiques de Rennes, École Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, 11 Allée de Beaulieu, CS 50837, F-35708 Rennes Cedex 7 (France)

    2016-11-20

    Previous detections of methyl and ethyl formate make other small substituted formates potential candidates for observation in the interstellar medium. Among them, vinyl formate is one of the simplest unsaturated carboxylic ester. The aim of this work is to provide direct experimental frequencies of the ground vibrational state of vinyl formate in a large spectral range for astrophysical use. The room-temperature rotational spectrum of vinyl formate has been measured from 80 to 360 GHz and analyzed in terms of Watson’s semirigid rotor Hamiltonian. Two thousand six hundred transitions within J = 3–88 and K {sub a} = 0–28 were assigned to the most stable conformer of vinyl formate and a new set of spectroscopic constants was accurately determined. Spectral features of vinyl formate were then searched for in Orion KL, Sgr B2(N), B1-b, and TMC-1 molecular clouds. Upper limits to the column density of vinyl formate are provided.

  1. Chloroindolyl-3-acetic Acid and its Methyl Ester Incorporation of 36Cl in Immature Seeds of Pea and Barley

    DEFF Research Database (Denmark)

    Engvild, Kjeld Christensen

    1974-01-01

    Immature seeds of pea and barley were harvested on plants grown in solutions containing 36Cl−, but no other chlorides. Autoradiography of two-dimensional thin layer chromatograms (silicagel) of butanol extracts of freeze-dried seeds showed the presence in both species of several radioactive...... compounds besides Cl−. One compound, present in pea and probably in barley, cochromatographed with a mixture of 4- and 6-chloroindolyl-3-acetic acid methyl esters. Another, detected in pea, but probably not in barley, cochromatographed with a mixture of 4-and 6-chloroindolyl-3-acetic acids....

  2. Restorative Effects of Caffeic Acid Phenethyl Ester in Radiation-Induced Oxidative Hepatic Disorders

    International Nuclear Information System (INIS)

    El-Fatih, N.M.; EI-Tawil, G.A.

    2009-01-01

    The potential role of antioxidant natural phenolic compounds in the prevention of oxidative tissue-damage associated with ionizing-radiation has accumulated over the past decades. The possible restorative effect of caffeic acid phenethyl ester (CAPE) in minimizing radiation-induced hepatic injury in male albino rats was investigated. CAPE was given to rats via intraperitoneal (ip.) injection at a dose of (10μmol/ kg b.wt.) for 21 successive days throughout exposure to gamma radiation and continued for 15 successive days post gamma-radiation exposure. Whole body gamma-irradiation was delivered as fractionated doses (3 weeks) 2 Gy increment every week up to total cumulative dose of G Gy. Rats were sacrificed at either I, or 15 days after last dose of radiation. Malondialdehyde (MDA) content was determined in plasma and hepatic tissues. In addition, the activities of xanthine oxidase (XO), superoxide dismutase (SOD), catalase (CAT), glutathione peroxidase (GSH-Px) as well as the level of reduced glutathione (GSH) were determined to evaluate the changes of antioxidant-status in blood systems and hepatic tissues. Meantime, alanine aminotransferase (ALT), aspartate aminotransferase (AST), alkaline phosphatase (ALP) activities were estimated in rat serum. Results showed that exposure to gamma-radiation significantly increased the MDA levels and the activities of XO, ALT, AST and ALP. Moreover, SOD, CAT and GSH-Px activities as well GSH contents showed significant consumption in irradiated rats. Treatment with CAPE showed a significant decrease in MDA level and caused significant increases in all enzymes measured in hepatic tissues and blood systems when compared with irradiated group. Conclusion: radiation-exposure leads to a reduction in antioxidant enzymatic activities and causes lipid peroxidation in hepatic tissues and blood. Under experimental condition, CAPE exhibits restorative effects on gamma-rays-induced hepatic-oxidative impairment in rats

  3. Restorative Effects of Caffeic Acid Phenethyl Ester in Radiation-Induced Oxidative Hepatic Disorders

    International Nuclear Information System (INIS)

    El-Fatih, N.M.; EI-Tawil, G.A.

    2008-01-01

    The potential role of antioxidant natural phenolic compounds in the prevention of oxidative tissue-damage associated with ionizing-radiation has accumulated over the past decades. The possible restorative effect of caffeic acid phenethyl ester (CAPE) in minimizing radiation-induced hepatic injury in male albino rats was investigated. CAPE was given to rats via intraperitoneal (ip.) injection at a dose of (10μmol/ kg b.wt.) for 21 successive days throughout exposure to gamma radiation and continued for 15 successive days post gamma-radiation exposure. Whole body gamma-irradiation was delivered as fractionated doses (3 weeks) 2 Gy increment every week up to total cumulative dose of G Gy. Rats were sacrificed at either I, or 15 days after last dose of radiation. Malondialdehyde (MDA) content was determined in plasma and hepatic tissues. In addition, the activities of xanthine oxidase (XO), superoxide dismutase (SOD), catalase (CAT), glutathione peroxidase (GSH-Px) as well as the level of reduced glutathione (GSH) were determined to evaluate the changes of antioxidant-status in blood systems and hepatic tissues. Meantime, alanine aminotransferase (ALT), aspartate aminotransferase (AST), alkaline phosphatase (ALP) activities were estimated in rat serum. Results showed that exposure to gamma-radiation significantly increased the MDA levels and the activities of XO, ALT, AST and ALP. Moreover, SOD, CAT and GSH-Px activities as well GSH contents showed significant consumption in irradiated rats. Treatment with CAPE showed a significant decrease in MDA level and caused significant increases in all enzymes measured in hepatic tissues and blood systems when compared with irradiated group. Conclusion: radiation-exposure leads to a reduction in antioxidant enzymatic activities and causes lipid peroxidation in hepatic tissues and blood. Under experimental condition, CAPE exhibits restorative effects on gamma-rays-induced hepatic-oxidative impairment in rats

  4. Designing, synthesis, and antimicrobial action of oxazoline and thiazoline derivatives of fatty acid esters.

    Science.gov (United States)

    Ahmad, Anis; Ahmad, Aiman; Sudhakar, Raja; Varshney, Himani; Subbarao, Naidu; Ansari, Saba; Rauf, Abdul; Khan, Asad U

    2017-11-01

    In this study, a novel series of oxazoline and thiazoline were designed as inhibitors of cytochrome P450 14 alpha-sterol demethylase (CYP51) from Candida albicans and peptide deformylase (PDF) of Escherichia coli. The long chain dibromo derivative of fatty acid esters on reaction with urea and thiourea gave their corresponding oxazolines and thiazolines, respectively. All the compounds were characterized by their spectral data (IR, 1 H NMR, 13 C NMR and MS) and tested for antibacterial and antifungal activity by disk diffusion assay and minimum inhibitory concentration by the broth microdilution method against gram-positive and gram-negative strains of bacteria as well as fungus strains. The investigation into antimicrobial screening revealed that all the compounds were found to be potent antimicrobial agents. After calculating likeness drug properties of the compounds by Prediction of Activity Spectra for Substances software, ADMET-related descriptors were computed to predict the pharmacokinetic properties for the active and bioavailable compounds by discovery studio 2.5. Molecular docking studies have been performed on PDF of E. coli and CYP 450-14DM of C. albicans to understand the mode of binding of the molecules in the active site of the receptor. Compounds (2-amino-5-(carbomethoxyoctyl)-1,3-oxazoline, 2-amino-5-(carbomethoxyoctyl)-1,3-thiazoline and 2-amino-4-pentyl-5-[(8'R)-8' hydroxy (carbomethoxydecyl)-1,3-oxazoline) showed excellent antimicrobial activity nearly equivalent to the control compounds and compounds, 2-amino-4-octyl-5-(carbomethoxyheptyl)-1,3-oxazolin, 2-amino-4-(2'R)(2'-hydroxy octyl)-5-(carbomethoxyheptyl)-1,3-oxazoline and 2-amino-4-pentyl-5-[(8'R)-8'-hydroxy(carbomethoxy decyl)-1,3-oxazolineshowed vasodilation and antihypertensive properties. Furthermore, a computational analysis of physicochemical parameters revealed that the most of the compounds possessed drug-like attributes. Using Bioinformatics approach, we found a correlation

  5. Solutol HS 15, nontoxic polyoxyethylene esters of 12-hydroxystearic acid, reverses multidrug resistance.

    Science.gov (United States)

    Coon, J S; Knudson, W; Clodfelter, K; Lu, B; Weinstein, R S

    1991-02-01

    A recently developed non-ionic surfactant called Solutol HS 15 (poly-oxyethylene esters of 12-hydroxystearic acid), with low toxicity in vivo, was shown to reverse completely the multidrug resistance of KB 8-5 and KB 8-5-11 human epidermoid carcinoma cells in vitro but did not potentiate drug toxicity in drug-sensitive KB 3-1 cells. At a concentration of 10% of its own IC50 (mean concentration of drug that causes 50% inhibition of cell growth compared to controls), Solutol HS 15 produced a 35-, 28-, and 42-fold reduction in the resistance of KB 8-5-11 cells to colchicine, vinblastine, and doxorubicin, respectively. Solutol HS 15 was relatively much more potent than the prototypic reversing agent, verapamil, for reversing colchicine resistance, compared to the ability of each agent to reverse colchicine resistance, compared to the ability of each agent to reverse vinblastine resistance. Like verapamil, Solutol HS 15 promoted a 50-fold accumulation of rhodamine 123 in KB 8-5-11 cells, as measured by flow cytometry. Also, Solutol HS 15 and verapamil reduced the efflux of rhodamine 123 from KB 8-5-11 cells previously loaded with rhodamine 123 to a similar low rate. Solutol HS 15 did not affect the transport of alanine or glucose into KB 8-5-11 cells, indicating that its effect upon membrane active transport is not entirely nonspecific. Considering their different structure and different relative potency for reversing colchicine resistance, Solutol HS 15 and verapamil probably reverse multidrug resistance by different mechanisms. Solutol HS 15 merits consideration as a potential therapeutic agent because of its effectiveness for reversing multidrug resistance in vitro and its low toxicity in vivo.

  6. Sulfonated methyl esters of fatty acids in aqueous solutions: Interfacial and micellar properties.

    Science.gov (United States)

    Danov, Krassimir D; Stanimirova, Rumyana D; Kralchevsky, Peter A; Basheva, Elka S; Ivanova, Veronika I; Petkov, Jordan T

    2015-11-01

    The interest to sulfonated methyl esters of fatty acids (SME) has been growing during the last decade, because these surfactants are considered as an environmentally friendly and renewable alternative of the linear alkyl-benzene sulfonates (LAS). Here, we present a quantitative study on the properties of aqueous SME solutions, and especially on their surface tension isotherms, critical micelle concentration (CMC) and its dependence on the concentration of added NaCl. It is demonstrated that the CMC of an ionic surfactant determined by electrical conductivity is insensitive to the presence of a small nonionic admixture, so that the CMC values determined by conductivity represent the CMC of the pure surfactant. Using SME as an example, we have demonstrated the application of a new and powerful method for determining the physicochemical parameters of the pure ionic surfactant by theoretical data analysis ("computer purification") if the used surfactant sample contains nonionic admixtures, which are present as a rule. This method involves fits of the experimental data for surface tension and conductivity by a physicochemical model based on a system of mass-balance, chemical-equilibrium and electric-double-layer equations, which allows us to determine the adsorption and micellization parameters of C12-, C14-, C16- and C18-SME, as well the fraction of nonionic admixtures (if any). Having determined these parameters, we can further predict the interfacial and micellization properties of the surfactant solutions, such as surface tension, adsorption, degree of counterion binding, and surface electric potential at every surfactant, salt and co-surfactant concentrations. Copyright © 2015 Elsevier Inc. All rights reserved.

  7. Phenethyl ester and amide of Ferulic Acids: Synthesis and bioactivity against P388 Leukemia Murine Cells

    Science.gov (United States)

    Firdaus; Soekamto, N. H.; Seniwati; Islam, M. F.; Sultan

    2018-03-01

    Bioactivity of a compound is closely related to the molecular structure of the compound concerned, its strength being the quantitative relation of the strength of the activity of the group it possesses. The combining of moieties of the active compounds will produce more active compounds. Most phenolic compounds as well as compounds containing moiety phenethyl groups have potential activity as anticancer. Combining phenolic groups and phenethyl groups in a compound will result in compounds having strong anticancer bioactivity. This study aims to combine the feruloyl and phenethyl groups to form esters and amides by synthesize of phenethyl trans-3-(4-hydroxy-3-methoxyphenyl)acrylate (5) and trans-3-(4- hydroxy-3-methoxyphenyl)-N-phenethylacrylamide (6) from ferulic acid with phenethyl alcohol and phenethylamine, and to study their bioactivity as anticancer. The synthesis of both compounds was conducted via indirect reaction, including acetylation, chlorination, esterfication/amidation, and deacetylation. Structures of products were characterized by FTIR and NMR data, and their bioactivity assay of the compounds against P388 Leukemia Murine Cells was conducted by an MTT method. Results showed that the compound 5 was obtained as a yellow gel with the IC50 of 10.79 μg/mL (36.21 μΜ), and the compound 6 was a yellowish solid with a melting point of 118-120°C and the IC50 of 29.14 μg/mL (97.79 μΜ). These compounds were more active than the analog compounds.

  8. Carbohydrate fatty acid monosulphate esters are safe and effective adjuvants for humoral responses.

    Science.gov (United States)

    Hilgers, Luuk A Th; Platenburg, Peter Paul L I; Bajramovic, Jeffrey; Veth, Jennifer; Sauerwein, Robert; Roeffen, Will; Pohl, Marie; van Amerongen, Geert; Stittelaar, Koert J; van den Bosch, Johannes F

    2017-05-31

    Carbohydrate fatty acid sulphate esters (CFASEs) formulated in a squalane-in-water emulsion are effective adjuvants for humoral responses to a wide range of antigens in various animal species but rise in body temperature and local reactions albeit mild or minimal hampers application in humans. In rabbits, body temperature increased 1°C one day after intramuscular (IM) injection, which returned to normal during the next day. The effect increased with increasing dose of CFASE but not with the number of injections (up to 5). Antigen enhanced the rise in body temperature after booster immunization (P100-fold after the second immunization. In ferrets immunized with 7.5μg of inactivated influenza virus A/H7N9, CMS adjuvant gave 100-fold increase in HAI antibody titres after the first and 25-fold after the second immunisation, which were 10-20-fold higher than with the MF59-like AddaVax adjuvant. In both models, a single immunisation with CMS adjuvant revealed similar or higher titres than two immunisations with either benchmark, without detectable systemic and local adverse effects. Despite striking chemical similarities with monophospholipid A (MPL), CMS adjuvant did not activate human TLR4 expressed on HEK cells. We concluded that the synthetic CMS adjuvant is a promising candidate for poor immunogens and single-shot vaccines and that rise in body temperature, local reactions or activation of TLR4 is not a pre-requisite for high adjuvanticity. Copyright © 2017 The Author(s). Published by Elsevier Ltd.. All rights reserved.

  9. The Rheological Properties of Lipid Monolayers Modulate the Incorporation of l-Ascorbic Acid Alkyl Esters.

    Science.gov (United States)

    Díaz, Yenisleidy de Las Mercedes Zulueta; Mottola, Milagro; Vico, Raquel V; Wilke, Natalia; Fanani, María Laura

    2016-01-19

    In this work, we tested the hypothesis that the incorporation of amphiphilic drugs into lipid membranes may be regulated by their rheological properties. For this purpose, two members of the l-ascorbic acid alkyl esters family (ASCn) were selected, ASC16 and ASC14, which have different rheological properties when organized at the air/water interface. They are lipophilic forms of vitamin C used in topical pharmacological preparations. The effect of the phase state of the host lipid membranes on ASCn incorporation was explored using Langmuir monolayers. Films of pure lipids with known phase states have been selected, showing liquid-expanded, liquid-condensed, and solid phases as well as pure cholesterol films in liquid-ordered state. We also tested ternary and quaternary mixed films that mimic the properties of cholesterol containing membranes and of the stratum corneum. The compressibility and shear properties of those monolayers were assessed in order to define its phase character. We found that the length of the acyl chain of the ASCn compounds induces differential changes in the rheological properties of the host membrane and subtly regulates the kinetics and extent of the penetration process. The capacity for ASCn uptake was found to depend on the phase state of the host film. The increase in surface pressure resultant after amphiphile incorporation appears to be a function of the capacity of the host membrane to incorporate such amphiphile as well as the rheological response of the film. Hence, monolayers that show a solid phase state responded with a larger surface pressure increase to the incorporation of a comparable amount of amphiphile than liquid-expanded ones. The cholesterol-containing films, including the mixture that mimics stratum corneum, allowed a very scarce ASCn uptake independently of the membrane diffusional properties. This suggests an important contribution of Cho on the maintenance of the barrier function of stratum corneum.

  10. An evidence of C16 fatty acid methyl esters extracted from microalga for effective antimicrobial and antioxidant property.

    Science.gov (United States)

    Davoodbasha, MubarakAli; Edachery, Baldev; Nooruddin, Thajuddin; Lee, Sang-Yul; Kim, Jung-Wan

    2018-02-01

    Fatty acid methyl esters (FAME) derived from lipids of microalgae is known to have wide bio-functional materials including antimicrobials. FAME is an ideal super-curator and superior anti-pathogenic. The present study evaluated the efficiency of FAME extracted from microalgae Scenedesmus intermedius as an antimicrobial agent against Gram positive (Staphylococcus aureus, Streptococcus mutans, and Bacillus cereus) Gram negative (Escherichia coli and Pseudomonas aeruginosa) bacteria and Fungi (Aspergillus parasiticus and Candida albicans). The minimal inhibitory concentration (MIC) for the gram negative bacteria was determined as 12-24 μg mL -1 , whereas MIC for gram positive bacteria was 24-48 μg mL -1 . MIC for the fungi was as high as 60-192 μg mL -1 . The FAME profiles determined by gas chromatography showed 18 methyl esters. Among them, pharmacologically active FAME such as palmitic acid methyl ester (C16:0) was detected at high percentage (23.08%), which accounted for the bioactivity. FAME obtained in this study exhibited a strong antimicrobial activity at the lowest MIC than those of recent reports. This result clearly indicated that FAME of S. intermedius has a strong antimicrobial and antioxidant property and that could be used as an effective resource against microbial diseases. Copyright © 2017. Published by Elsevier Ltd.

  11. In vitro release studies of vitamin B12 from poly N-vinyl pyrrolidone /starch hydrogels grafted with acrylic acid synthesized by gamma radiation

    International Nuclear Information System (INIS)

    Eid, M.

    2008-01-01

    Co-polymeric hydrogels containing N-vinyl pyrrolidone and starch grafted with acrylic acid were synthesized by gamma radiation. Their gel contents, grafting process and swelling were evaluated. The gels were also characterized by thermal gravimetric analysis. The gel content found to be increase with increasing the irradiation dose up to 50 kGy then decrease. The grafting percent increase by increasing the percentage of acrylic acid in the grafted hydrogels. The thermal stability and the rate of the thermal decomposition showed to be changed according to the different composition of the hydrogels. It also showed a decrease in the maximum rate of the thermal decomposition by the increasing of the irradiation dose from 20 to 30 kGy and increases by increasing the irradiation dose from 30 to 70 kGy. The hydrogels loaded with vitamin B 12 as drug model, demonstrated a decrease release in acidic medium than the neutral one

  12. Caffeic Acid Phenethyl Ester as a Protective Agent against Nephrotoxicity and/or Oxidative Kidney Damage: A Detailed Systematic Review

    Directory of Open Access Journals (Sweden)

    Sumeyya Akyol

    2014-01-01

    Full Text Available Caffeic acid phenethyl ester (CAPE, an active component of propolis, has been attracting the attention of different medical and pharmaceutical disciplines in recent years because of its antioxidant, anti-inflammatory, antiproliferative, cytotoxic, antiviral, antifungal, and antineoplastic properties. One of the most studied organs for the effects of CAPE is the kidney, particularly in the capacity of this ester to decrease the nephrotoxicity induced by several drugs and the oxidative injury after ischemia/reperfusion (I/R. In this review, we summarized and critically evaluated the current knowledge regarding the protective effect of CAPE in nephrotoxicity induced by several special medicines such as cisplatin, doxorubicin, cyclosporine, gentamycin, methotrexate, and other causes leading to oxidative renal injury, namely, I/R models and senility.

  13. Cytotoxicity of Endoperoxides from the Caribbean Sponge Plakortis halichondrioides towards Sensitive and Multidrug-Resistant Leukemia Cells: Acids vs. Esters Activity Evaluation

    Directory of Open Access Journals (Sweden)

    Tanja Schirmeister

    2017-03-01

    Full Text Available The 6-epimer of the plakortide H acid (1, along with the endoperoxides plakortide E (2, plakortin (3, and dihydroplakortin (4 have been isolated from a sample of the Caribbean sponge Plakortis halichondrioides. To perform a comparative study on the cytotoxicity towards the drug-sensitive leukemia CCRF-CEM cell line and its multi-drug resistant subline CEM/ADR5000, the acid of plakortin, namely plakortic acid (5, as well as the esters plakortide E methyl ester (6 and 6-epi-plakortide H (7 were synthesized by hydrolysis and Steglich esterification, respectively. The data obtained showed that the acids (1, 2, 5 exhibited potent cytotoxicity towards both cell lines, whereas the esters showed no activity (6, 7 or weaker activity (3, 4 compared to their corresponding acids. Plakortic acid (5 was the most promising derivative with half maximal inhibitory concentration (IC50 values of ca. 0.20 µM for both cell lines.

  14. 2-Chloro-1,3-propanediol (2-MCPD) and its fatty acid esters: cytotoxicity, metabolism, and transport by human intestinal Caco-2 cells.

    Science.gov (United States)

    Buhrke, Thorsten; Frenzel, Falko; Kuhlmann, Jan; Lampen, Alfonso

    2015-12-01

    The food contaminants 3-chloro-1,2-propanediol (3-MCPD) and 3-MCPD fatty acid esters have attracted considerable attention in the past few years due to their toxic properties and their occurrence in numerous foods. Recently, significant amounts of the isomeric compounds 2-chloro-1,3-propanediol (2-MCPD) fatty acid esters have been detected in refined oils. Beside the interrogation which toxic effects might be related to the core compound 2-MCPD, the key question from the risk assessment perspective is again-as it was discussed for 3-MCPD fatty acid esters before-to which degree these esters are hydrolyzed in the gut, thereby releasing free 2-MCPD. Here, we show that free 2-MCPD but not 2-MCPD fatty acid esters were able to cross a monolayer of differentiated Caco-2 cells as an in vitro model for the human intestinal barrier. Instead, the esters were hydrolyzed by the cells, thereby releasing free 2-MCPD which was neither absorbed nor metabolized by the cells. Cytotoxicity assays revealed that free 2-MCPD as well as free 3-MCPD was not toxic to Caco-2 cells up to a level of 1 mM, whereas cellular viability was slightly decreased in the presence of a few 2-MCPD and 3-MCPD fatty acid esters at concentrations above 10 µM. The observed cytotoxic effects correlated well with the induction of caspase activity and might be attributed to the induction of apoptosis by free fatty acids which were released from the esters in the presence of Caco-2 cells.

  15. Synthesis, Anti-HCV, Antioxidant and Reduction of Intracellular Reactive Oxygen Species Generation of a Chlorogenic Acid Analogue with an Amide Bond Replacing the Ester Bond.

    Science.gov (United States)

    Wang, Ling-Na; Wang, Wei; Hattori, Masao; Daneshtalab, Mohsen; Ma, Chao-Mei

    2016-06-08

    Chlorogenic acid is a well known natural product with important bioactivities. It contains an ester bond formed between the COOH of caffeic acid and the 3-OH of quinic acid. We synthesized a chlorogenic acid analogue, 3α-caffeoylquinic acid amide, using caffeic and quinic acids as starting materials. The caffeoylquinc acid amide was found to be much more stable than chlorogenic acid and showed anti-Hepatitis C virus (anti-HCV) activity with a potency similar to chlorogenic acid. The caffeoylquinc acid amide potently protected HepG2 cells against oxidative stress induced by tert-butyl hydroperoxide.

  16. Esterification of oil adsorbed on palm decanter cake into methyl ester using sulfonated rice husk ash as heterogeneous acid catalyst

    Science.gov (United States)

    Hindryawati, Noor; Erwin, Maniam, Gaanty Pragas

    2017-02-01

    Palm Decanter cake (PDC) which is categorized as the waste from palm oil mill has been found to contain residual crude palm oil. The oil adsorbed on the PDC (PDC-oil) can be extracted and potentially used as feedstock for biodiesel production. Feedstock from waste like PDC-oil is burdened with high free fatty acids (FFAs) which make the feedstock difficult to be converted into biodiesel using basic catalyst. Therefore, in this study, a solid acid, RHA-SO3H catalyst was synthesized by sulfonating rice husk ash (RHA) with concentrated sulfuric acid. The RHA-SO3H prepared was characterized with TGA, FTIR, BET, XRD, FE-SEM, and Hammett indicators (methyl red, bromophenol blue, and crystal violet). PDC was found to have about 11.3 wt. % oil recovered after 1 hour extraction using ultrasound method. The presence of sulfonate group was observed in IR spectrum, and the surface area of RHA-SO3H was reduced to 37 m2.g-1 after impregnation of sulfonate group. The RHA-SO3H catalyst showed that it can work for both esterification of free fatty acid which is present in PDC-oil, and transesterification of triglycerides into methyl ester. The results showed highest methyl ester content of 70.2 wt.% at optimal conditions, which was 6 wt.% catalyst amount, methanol to oil molar ratio of 17:1 for 5 hours at 120 °C.

  17. Production of oleic acid ethyl ester catalyzed by crude rice bran (Oryza sativa lipase in a modified fed-batch system: problem and its solution

    Directory of Open Access Journals (Sweden)

    Indro Prastowo

    2015-01-01

    Full Text Available A fed-batch system was modified for the enzymatic production of Oleic Acid Ethyl Ester (OAEE using rice bran (Oryza sativa lipase by retaining the substrate molar ratio (ethanol/oleic acid at 2.05: 1 during the reaction. It resulted in an increase in the ester conversion up to 76.8% in the first 6 h of the reaction, and then followed by a decrease from 76.8% to 22.9% in 6 h later. Meanwhile, the production of water in the reaction system also showed a similar trend to the trend of ester production. The water was hypothesized to lead lipase to reverse the reaction which resulted in a decrease in both (water and esters in the last 6 h of the reaction. In order to overcome the problem, zeolite powders (25 and 50 mg/ml were added into the reaction system at 5 h of the reaction. As the result, final ester conversions increased drastically up to 90 - 95.7% (1.17 – 1.24 times. The addition also proved a hypothesis that the water was involved in reducing the ester conversion in the last 6 h of the reaction. Thus, the combination was effective to produce the high final ester conversion.

  18. [Determination of fatty acid esters of chloropropanediols in diet samples by gas chromatography-mass spectrometry coupled with solid-supported liquid-liquid extraction].

    Science.gov (United States)

    Gao, Jie; Liu, Qing; Han, Feng; Miao, Hong; Zhao, Yunfeng; Wu, Yongning

    2014-05-01

    To establish a method for the determination of fatty acid esters of 3-monochloropropane-1, 2-diol (3-MCPD) and 2-monochloropropane-1, 3-diol (2-MCPD) in diet samples by gas chromatography-mass spectrometry (GC-MS) with solid-supported liquid-liquid extraction (SLE). Diet samples were ultrasonically extracted by hexane, followed by ester cleavage reaction with sodium methylate in methanol, and then purified by solid-supported liquid-liquid extraction. (SLE) using diatomaceous earth as the sorbent. After derivatization with heptafluorobutyrylimidazole, the analytes were detected by GC-MS and quantified by the deuterated internal standards. The limits of detection (LODs) of 3-MCPD esters and 2-MCPD esters in different diet samples were 0.002 - 0.005 mg/kg and 0.002 - 0.006 mg/kg. The average recoveries of 3-MCPD esters and 2-MCPD esters at the spiking levels of 0.05 and 0.1 mg/kg in the diet samples were in the range of 65.9% - 104.2% and 75.4% - 118.0%, respectively, with the relative standard deviations in the range of 2.2% - 14.2% and 0.8% - .13.9%. The method is simple, accurate and rugged for the determination of fatty acid esters of 3-MCPD and 2-MCPD in diet samples.

  19. A kinetic study on the Novozyme 435-catalyzed esterification of free fatty acids with octanol to produce octyl esters.

    Science.gov (United States)

    Chowdhury, Avisha; Mitra, Debarati

    2015-01-01

    Octyl esters can serve as an important class of biolubricant components replacing their mineral oil counterparts. The purpose of the current work was to investigate the enzymatic esterification reaction of free fatty acids (FFA, from waste cooking oil) with octanol in a solvent-free system using a commercial lipase Novozyme 435. It was found that the esterificaton reaction followed the Ping-pong bi-bi kinetics with no inhibition by substrates or products within the studied concentration range. The maximum reaction rate was estimated to be 0.041 mol L(-1) g(-1) h(-1) . Additionally, the stability of Novozyme 435 in the current reaction system was studied by determining its activity and final conversion of FFA to esters after 12 successive utilizations. Novozyme 435 exhibited almost 100% enzyme activity up to 7 cycles of reaction and gradually decreased (by 5%) thereafter. The kinetic parameters evaluated from the study shall assist in the design of reactors for large-scale production of octyl esters from a cheap biomass source. The enzyme reusability data can further facilitate mass production by curtailing the cost of expensive enzyme consumption. © 2015 American Institute of Chemical Engineers.

  20. Moderate intake of myristic acid in sn-2 position has beneficial lipidic effects and enhances DHA of cholesteryl esters in an interventional study.

    Science.gov (United States)

    Dabadie, Henry; Peuchant, Evelyne; Bernard, Mireille; LeRuyet, Pascale; Mendy, François

    2005-06-01

    Among the saturated fatty acids (SFA), myristic acid is known to be one of the most atherogenic when consumed at high levels. Our purpose was to compare the effects of two moderate intakes of myristic acid on plasma lipids in an interventional study. Twenty-five male monks without dyslipidemia were given two isocaloric diets for 5 weeks each. In diet 1, 30% of the calories came from fat (8% SFA, 0.6% myristic acid) and provided 200 mg cholesterol/day. Calories of diet 2 were 34% fat (11% SFA, 1.2% myristic acid) with the same levels of oleate, linoleate, alpha-linolenate and cholesterol. A baseline diet was provided before each diet. In comparison with baseline, diets 1 and 2 induced a decrease in total cholesterol, LDL-cholesterol and triglycerides (Pdiet 2 than after diet 1 whereas HDL-cholesterol was higher (Pdiet 2 vs. baseline (Pdiet 1 (Pdiets were associated with an increase in alpha-linolenate of cholesteryl esters (Pdiet 2 was associated with an increase in DHA of cholesteryl esters (Pdiet 2, myristic acid intake was positively correlated with myristic acid of phospholipids, and alpha-linolenic acid intake was correlated with alpha-linolenic acid of cholesteryl esters. Moderate intake (1.2% of total calories) of myristic acid has beneficial lipidic effects and enhances DHA of cholesteryl esters.

  1. A simple synthesis of 2-keto-3-deoxy-D-erythro-hexonic acid isopropyl ester, a key sugar for the bacterial population living under metallic stress.

    Science.gov (United States)

    Grison, Claire M; Renard, Brice-Loïc; Grison, Claude

    2014-02-01

    2-Keto-3-deoxy-D-erythro-hexonic acid (KDG) is the key intermediate metabolite of the Entner Doudoroff (ED) pathway. A simple, efficient and stereoselective synthesis of KDG isopropyl ester is described in five steps from 2,3-O-isopropylidene-D-threitol with an overall yield of 47%. KDG isopropyl ester is studied as an attractive marker of a functional Entner Doudoroff pathway. KDG isopropyl ester is used to promote growth of ammonium producing bacterial strains, showing interesting features in the remediation of heavy-metal polluted soils. Copyright © 2013 Elsevier Inc. All rights reserved.

  2. The 4-pyridylmethyl ester as a protecting group for glutamic and aspartic acids: 'flipping' peptide charge states for characterization by positive ion mode ESI-MS.

    Science.gov (United States)

    Garapati, Sriramya; Burns, Colin S

    2014-03-01

    Use of the 4-pyridylmethyl ester group for side-chain protection of glutamic acid residues in solid-phase peptide synthesis enables switching of the charge state of a peptide from negative to positive, thus making detection by positive ion mode ESI-MS possible. The pyridylmethyl ester moiety is readily removed from peptides in high yield by hydrogenation. Combining the 4-pyridylmethyl ester protecting group with benzyl ester protection reduces the number of the former needed to produce a net positive charge and allows for purification by RP HPLC. This protecting group is useful in the synthesis of highly acidic peptide sequences, which are often beset by problems with purification by standard RP HPLC and characterization by ESI-MS. Copyright © 2014 European Peptide Society and John Wiley & Sons, Ltd.

  3. Caffeic acid phenethyl ester prevents cadmium-induced cardiac impairment in rat

    International Nuclear Information System (INIS)

    Mollaoglu, Hakan; Gokcimen, Alpaslan; Ozguner, Fehmi; Oktem, Faruk; Koyu, Ahmet; Kocak, Ahmet; Demirin, Hilmi; Gokalp, Osman; Cicek, Ekrem

    2006-01-01

    Caffeic acid phenethyl ester (CAPE), a flavonoid like compound, is one of the major components of honeybee propolis. It was found to be a potent free radical scavenger and antioxidant recently. The aim of this study was to examine the effect of CAPE on cadmium (Cd)-induced hypertension and cardiomyopathy in rats. In particular, nitric oxide (NO) may contribute to the pathophysiology of Cd induced cardiac impairment. Malondialdehyde (MDA, an index of lipid peroxidation) levels and nitric oxide (NO, a vasodilator) levels were used as markers Cd-induced cardiac impairment and the success of CAPE treatment. Also, the findings have been supported by the histopathologic evidences. The rats were randomly divided into three experimental groups each (12), as follows: the control group, Cd-treated group (Cd) and Cd plus CAPE-treated group (Cd + CAPE). CdCl 2 in 0.9% NaCl was administrated intraperitoneally (i.p.) with a dose of 1 mg/kg/day. CAPE was co-administered i.p. a dose of 10 μM/kg for 15 days. Hypertension was found to be induced by intraperitoneal administration of Cd in a dose of 1 mg/kg/day on the measurements taken 15 days later. MDA levels were increased (p < 0.001) in cardiac tissue and NO levels were decreased (p < 0.05) in serum in the Cd group than those of the control group had. On the other hand, there was a slight difference (increase) in MDA levels in the Cd + CAPE group than the ones in the control group (p < 0.003). In addition, MDA levels were decreased and NO levels were increased in the Cd + CAPE group compared with the Cd group (p < 0.001, p < 0.0001, respectively). As a result, treatment with CAPE significantly reversed the increased lipid peroxidation (LPO) product, MDA, and decreased NO levels in Cd treated animals. In the histopathologic examination, a significant hypertrophy in atrial and ventricular myofibrils was observed in only Cd administered group, in comparison with the control group. There was no statistically significant difference

  4. Understanding hypertriglyceridemia in women: clinical impact and management with prescription omega-3-acid ethyl esters

    Directory of Open Access Journals (Sweden)

    Thomas D Dayspring

    2011-03-01

    Full Text Available Thomas D DayspringNorth Jersey Institute of Menopausal Lipidology, Wayne, NJ, USABackground: Elevated triglycerides (TGs are a common lipid disorder in the US and are associated with comorbidities such as pancreatitis, obesity, type 2 diabetes, and metabolic syndrome. TGs are generally elevated in postmenopausal women compared with premenopausal women. Meta-analysis has shown that elevated TGs are associated with an increased risk of coronary heart disease (CHD.Objective: This article provides a general overview of TG metabolism and reviews data on the epidemiology and risk of elevated TGs in women, as pregnancy and menopause, in particular, have been associated with unfavorable changes in the lipoprotein profile, including elevations in TGs. In addition, this review seeks to explain the recommended TG goals and treatment options for hypertriglyceridemia with an emphasis on severe hypertriglyceridemia (TGs ≥ 500 mg/dL and its respective treatment with prescription omega-3-acid ethyl esters (P-OM3.Methods: MedLine was searched for articles published through August 2009 using the terms “hypertriglyceridemia” and “dyslipidemia”, with subheadings for “prevalence”, “women”, “treatment”, “guidelines”, “risk”, and “omega-3 fatty acids”. Publications discussing the epidemiology of hypertriglyceridemia, CHD risk, treatment guidelines for lipid management, or clinical trials involving P-OM3 were selected for review. The reference lists of relevant articles were also examined for additional citations.Results: Hypertriglyceridemia is associated with increased CHD risk. Women, especially those with polycystic ovarian syndrome, type 2 diabetes, or who are postmenopausal, should be monitored regularly for the impact of hypertriglyceridemia on their lipid profile. Cardiovascular risk of TGs can be indirectly assessed by monitoring non-high-density lipoprotein cholesterol (non-HDL-C levels. There are multiple sets of guidelines

  5. Is caffeic acid phenethyl ester more protective than doxycycline in experimental periodontitis?

    Science.gov (United States)

    Yiğit, Umut; Kırzıoğlu, Fatma Yeşim; Uğuz, Abdülhadi Cihangir; Nazıroğlu, Mustafa; Özmen, Özlem

    2017-09-01

    Host modulation therapies (anti-inflammatory drugs, bone-stimulating agents, anti-proteinase etc.) target the inhibition or stabilization of tissue breakdown. The aim of the present study was to evaluate the effects of caffeic acid phenethyl ester (CAPE) and/or low dose doxycycline (LDD) administrations on alveolar bone loss (ABL), serum cytokines and gingival apoptosis, as well as the levels of oxidants and anti-oxidants in rats with ligature-induced periodontitis. The animals were randomly divided into five groups: Group C (periodontally healthy), Group PC (Periodontitis+CAPE), Group PD (Periodontitis+LDD), Group PCD (Periodontitis+CAPE+LDD), Group P (Periodontitis). Experimental periodontitis was induced for 14days. Levels of ABL, and the serum cytokines, interleukin (IL)-1 β, IL-6, tumor necrosis factor-α (TNF-α) and IL-10 were assessed as were the levels of the oxidants and anti-oxidants, malondialdehyde (MDA), glutathione (GSH) and glutathione peroxidase (GSH-Px), and levels of gingival apoptosis. The lowest ABL levels was evident in the PC group, among the experimental groups. There was also less inflammatory infiltration in the PC group than the PD group. IL-1β, IL-6, and IL-10 were lower in the PC group and higher in the P group in comparison to the levels in the other experiment groups. TNF-α levels in the PD group were higher than levels in the PC and PCD groups. The PC and PCD groups did not differ from the C group in regard to MDA levels. The highest GSH-Px level was found in the PC group. Gingival apoptosis in the PC group was not only lower than the PD and PCD groups, but also lower than in the C group. The present study suggests that CAPE has more anti-inflammatory, anti-oxidant and anti-apoptotic effects than LDD, with no additive benefits of a CAPE+LDD combination being evident in rats with periodontitis. Copyright © 2017 Elsevier Ltd. All rights reserved.

  6. Structural characterization of saturated branched chain fatty acid methyl esters by collisional dissociation of molecular ions generated by electron ionization.

    Science.gov (United States)

    Ran-Ressler, Rinat R; Lawrence, Peter; Brenna, J Thomas

    2012-01-01

    Saturated branched chain fatty acids (BCFA) are present as complex mixtures in numerous biological samples. The traditional method for structure elucidation, electron ionization (EI) mass spectrometry, sometimes does not unambiguously enable assignment of branching in isomeric BCFA. Zirrolli and Murphy (Zirrolli , J. A. , and R. A. Murphy. 1993. Low-energy tandem mass spectrometry of the molecular ion derived from fatty acid methyl esters: a novel method for analysis of branched-chain fatty acids. J. Am. Soc. Mass Spectrom. 4: 223-229.) showed that the molecular ions of four BCFA methyl ester (BCFAME) yield highly characteristic fragments upon collisional dissociation using a triple quadrupole instrument. Here, we confirm and extend these results by analysis using a tabletop 3-D ion trap for activated molecular ion EI-MS/MS to 30 BCFAME. iso-BCFAME produces a prominent ion (30-100% of base peak) for [M-43] (M-C₃H₇), corresponding to the terminal isopropyl moiety in the original iso-BCFAME. Anteiso-FAME yield prominent ions (20-100% of base peak) corresponding to losses on both side of the methyl branch, [M-29] and [M-57], and tend to produce more prominent m/z 115 peaks corresponding to a cyclization product around the ester. Dimethyl and tetramethyl FAME, with branches separated by at least one methylene group, yield fragment on both sides of the sites of methyl branches that are more than 6 C away from the carboxyl carbon. EI-MS/MS yields uniquely specific ions that enable highly confident structural identification and quantification of BCFAME.

  7. Synthesis of Amide and Ester Derivatives of Cinnamic Acid and Its Analogs: Evaluation of Their Free Radical Scavenging and Monoamine Oxidase and Cholinesterase Inhibitory Activities.

    Science.gov (United States)

    Takao, Koichi; Toda, Kazuhiro; Saito, Takayuki; Sugita, Yoshiaki

    2017-01-01

    A series of cinnamic acid derivatives, amides (1-12) and esters (13-22), were synthesized, and structure-activity relationships for antioxidant activity, and monoamine oxidases (MAO) A and B, acetylcholinesterase, and butyrylcholinesterase (BChE) inhibitory activities were analyzed. Among the synthesized compounds, compounds 1-10, 12-18, and rosmarinic acid (23), which contained catechol, o-methoxyphenol or 5-hydroxyindole moieties, showed potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity. Compounds 9-11, 15, 17-22 showed potent and selective MAO-B inhibitory activity. Compound 20 was the most potent inhibitor of MAO-B. Compounds 18 and 21 showed moderate BChE inhibitory activity. In addition, compound 18 showed potent antioxidant activity and MAO-B inhibitory activity. In a comparison of the cinnamic acid amides and esters, the amides exhibited more potent DPPH free radical scavenging activity, while the esters showed stronger inhibitory activities against MAO-B and BChE. These results suggested that cinnamic acid derivatives such as compound 18, p-coumaric acid 3,4-dihydroxyphenethyl ester, and compound 20, p-coumaric acid phenethyl ester, may serve as lead compounds for the development of novel MAO-B inhibitors and candidate lead compounds for the prevention or treatment of Alzheimer's disease.

  8. Methyl esters (biodiesel) from and fatty acid profile of Gliricidia sepium seed oil

    Science.gov (United States)

    Increasing the supply of biodiesel by defining and developing additional feedstocks is important to overcome the still limited amounts available of this alternative fuel. In this connection, the methyl esters of the seed oil of Gliricidia sepium were synthesized and the significant fuel-related prop...

  9. Differential alterations of phospholipid metabolism in cultured cells of neural origin by phorbol esters, fatty acids, diacylglycerols and related compounds

    International Nuclear Information System (INIS)

    Cook, H.W.; Spence, M.W.

    1986-01-01

    The uptake and metabolism of [ 3 H]methylcholine, [1,2- 14 C]-ethanolamine, [1- 14 C]fatty acids and [ 32 P] were studied in glioma (C6), neuroblastoma (N1E-115) and neuroblastoma-glioma hybrid (NG108-15) cells in culture in the presence of tetradecanoylphorbolacetate (TPA) and related analogues, fatty acids and diacylglycerol (DAG) to assess mechanisms of stimulation of phospholipid synthesis. Choline incorporation into phosphatidylcholine (PC) was stimulated 1.5-3 fold by phorbol esters and 3-10 fold by 18:1(n-9) in C6 cultures; these agents were without effect on N1E-115 and had intermediate effects on NG108-15 cells. Stimulation of [ 32 P] incorporation was predominantly into PC, ethanolamine incorporation into phosphatidylethanolamine (PE) was less stimulated ( 3 H]choline and its incorporation via intracellular phosphocholine into PC whereas exogenous 18:1(n-9) stimulated only utilization of intracellular P-choline in C6 cells. Choline incorporation into PC and relative stimulation by TPA or 18:1 was influenced by medium glucose and choline. Thus, metabolism of phospholipids and their precursors in neural cells can be markedly influenced by phorbol esters and fatty acids but this stimulation is dependent on cell type, growth medium, phospholipid class and nature of the stimulator

  10. Linoleic acid-menthyl ester reduces the secretion of apolipoprotein B100 in HepG2 cells.

    Science.gov (United States)

    Inoue, Nao; Yamano, Naomi; Sakata, Kotaro; Arao, Keisuke; Kobayashi, Takashi; Nagao, Toshihiro; Shimada, Yuji; Nagao, Koji; Yanagita, Teruyoshi

    2009-01-01

    The effect of linoleic acid-menthyl ester (LAME) on lipid metabolism were assessed in HepG2 cells. It is well known that high level of apolipoprotein (apo) B100 in the serum is risk for atherosclerosis. Although linoleic acid (LA) treatment and LA plus L-mentol treatment increased apo B100 secretion, LAME treatment significantly decreased apo B100 secretion in HepG2 cells compared with control medium. The hypolipidemic effect of LAME was attributable to the suppression of triglyceride synthesis in HepG2 cells. It is also known that the risk of coronary heart disease is negatively related to the concentration of serum apo A-1. In the present study, LAME treatment increased apo A-1 secretion as compared with LA treatment in HepG2 cells. These results suggest that mentyl-esterification of fatty acids may be beneficial in anti-atherogenic dietary therapy.

  11. In-situ formation of silver nanoparticles on poly (lactic acid) film by γ-radiation induced grafting of N-vinyl pyrrolidone

    Energy Technology Data Exchange (ETDEWEB)

    Wang, Jingxia; Chen, Hao; Chen, Zhuping; Chen, Yuheng; Guo, Dan; Ni, Maojun; Liu, Siyang; Peng, Chaorong, E-mail: pengchaorong_siae@163.com

    2016-06-01

    A fast, easy and novel method for preparing biodegradable polymer films with silver nanoparticles was investigated to endow the material with excellent biocompatibility and antibacterial property. Silver nanoparticles (Ag NPs) were immobilized on the surface of polylactic acid (PLA) film by gamma radiation induced grafting of N-vinyl pyrrolidone (NVP). In this method, poly (N-vinyl pyrrolidone) (PVP) was produced and grafted onto the surface of PLA film by gamma radiation polymerization of NVP. PVP acted as both a bridge to connect the Ag NPs with the PLA film, and a stabilizer to protect the Ag NPs from agglomeration. The effect of various reaction parameters, including NVP/Ag mole ratio and radiation dose, on the fabrication of PLA-g-NVP/Ag film was demonstrated. Moreover, the interaction between PVP and Ag NPs was studied by X-ray photoelectron spectroscopy and Fourier-transform infrared spectroscopy, that revealed the Ag NPs coordinated through the oxygen atom on the carbonyl group of PVP at 15 kGy radiation dose, but through the nitrogen atom and the oxygen atom of the amide group of PVP at 1 kGy dose. - Highlights: • PLA-graft-NVP/Ag film was produced by a simple one-step method. • Ag nanoparticles were immobilized on PLA film by gamma radiation grafting technology. • PVP acted as a bridge to connect Ag nanoparticles and PLA film. • Different content and size of Ag NPs can be reached by varying radiation dose.

  12. In-situ formation of silver nanoparticles on poly (lactic acid) film by γ-radiation induced grafting of N-vinyl pyrrolidone

    International Nuclear Information System (INIS)

    Wang, Jingxia; Chen, Hao; Chen, Zhuping; Chen, Yuheng; Guo, Dan; Ni, Maojun; Liu, Siyang; Peng, Chaorong

    2016-01-01

    A fast, easy and novel method for preparing biodegradable polymer films with silver nanoparticles was investigated to endow the material with excellent biocompatibility and antibacterial property. Silver nanoparticles (Ag NPs) were immobilized on the surface of polylactic acid (PLA) film by gamma radiation induced grafting of N-vinyl pyrrolidone (NVP). In this method, poly (N-vinyl pyrrolidone) (PVP) was produced and grafted onto the surface of PLA film by gamma radiation polymerization of NVP. PVP acted as both a bridge to connect the Ag NPs with the PLA film, and a stabilizer to protect the Ag NPs from agglomeration. The effect of various reaction parameters, including NVP/Ag mole ratio and radiation dose, on the fabrication of PLA-g-NVP/Ag film was demonstrated. Moreover, the interaction between PVP and Ag NPs was studied by X-ray photoelectron spectroscopy and Fourier-transform infrared spectroscopy, that revealed the Ag NPs coordinated through the oxygen atom on the carbonyl group of PVP at 15 kGy radiation dose, but through the nitrogen atom and the oxygen atom of the amide group of PVP at 1 kGy dose. - Highlights: • PLA-graft-NVP/Ag film was produced by a simple one-step method. • Ag nanoparticles were immobilized on PLA film by gamma radiation grafting technology. • PVP acted as a bridge to connect Ag nanoparticles and PLA film. • Different content and size of Ag NPs can be reached by varying radiation dose.

  13. Study of Substituted Ester Formation in Red Wine by the Development of a New Method for Quantitative Determination and Enantiomeric Separation of Their Corresponding Acids.

    Science.gov (United States)

    Lytra, Georgia; Franc, Celine; Cameleyre, Margaux; Barbe, Jean-Christophe

    2017-06-21

    A new method was developed for quantifying substituted acids including, where applicable, their various unexplored enantiomeric forms. A new step was added to acids' usual quantification methods, consisting of extraction, derivatization to methyl esters, and gas chromatography analysis: preliminary extraction was performed at basic pH to eliminate ethyl esters, thus avoiding their transesterification during derivatization. Quantitation and enantiomeric distribution of some substituted esters and their corresponding acids were established in 31 commercial Bordeaux red wines from 0 to 20 years old. A strong positive correlation was observed between the age of wine and levels of ethyl 2-methylpropanoate, ethyl 3-methylbutanoate, ethyl 2-methylbutanoate, ethyl (3R)-3-hydroxybutanoate, both enantiomeric forms of ethyl 2-hydroxy-3-methylbutanoate, and ethyl (2S)-2-hydroxy-4-methylpentanoate, but not ethyl (3S)-3-hydroxybutanoate. However, the standard deviations of average concentrations for the corresponding substituted acids were so large that only few correlations between concentrations and age were observed. Concentrations of (2S)-2-hydroxy-3-methylbutanoic acid and (2S)-2-hydroxy-4-methylpentanoic acid increased slightly over time, while (2R)-2-hydroxy-4-methylpentanoic acid levels decreased slightly with the age. Variations in the ratio of substituted ethyl esters to their corresponding acids over time detected thanks to these analytical advances suggested that, in general, acids were continuously esterified during aging.

  14. Syntheses of protoporphyrin-IX regioselectivity carbon-13 labelled at the alpha-vinyl carbons

    International Nuclear Information System (INIS)

    Smith, K.M.; Fujinari, E.M.

    1986-01-01

    A method for transformation of readily available beta-vinyl 99% carbon-13 enriched derivatives of protoporphyrin-IX dimethyl ester into the less accessible alpha-vinyl labelled isomers is described. The procedure involves thallium(III) promoted vinyl carbon rearrangement, and proceeds through 2,2-dimethoxyethyl, formylmethyl, 2-hydroxyethyl and 2-chloroethyl porphyrins; the rearranged vinyl groups are regenerated from 2-chloroethyl in the last step by treatment with base. No evidence of vinyl carbon scrambling in the sequence is observed, and spectroscopic data of the products are given. (author)

  15. Lipase-Catalyzed Synthesis of Sugar Esters in Honey and Agave Syrup

    Directory of Open Access Journals (Sweden)

    Sascha Siebenhaller

    2018-02-01

    Full Text Available Honey and agave syrup are high quality natural products and consist of more than 80% sugars. They are used as sweeteners, and are ingredients of cosmetics or medical ointments. Furthermore, both have low water content, are often liquid at room temperature and resemble some known sugar-based deep eutectic solvents (DES. Since it has been shown that it is possible to synthesize sugar esters in these DESs, in the current work honey or, as vegan alternative, agave syrup are used simultaneously as solvent and substrate for the enzymatic sugar ester production. For this purpose, important characteristics of the herein used honey and agave syrup were determined and compared with other available types. Subsequently, an enzymatic transesterification of four fatty acid vinyl esters was accomplished in ordinary honey and agave syrup. Notwithstanding of the high water content for transesterification reactions of the solvent, the successful sugar ester formation was proved by thin-layer chromatography (TLC and compared to a sugar ester which was synthesized in a conventional DES. For a clear verification of the sugar esters, mass determinations by ESI-Q-ToF experiments and a NMR analysis were done. These environmentally friendly produced sugar esters have the potential to be used in cosmetics or pharmaceuticals, or to enhance their effectiveness.

  16. Lipase-Catalyzed Synthesis of Sugar Esters in Honey and Agave Syrup

    Science.gov (United States)

    Siebenhaller, Sascha; Gentes, Julian; Infantes, Alba; Muhle-Goll, Claudia; Kirschhöfer, Frank; Brenner-Weiß, Gerald; Ochsenreither, Katrin; Syldatk, Christoph

    2018-02-01

    Honey and agave syrup are high quality natural products and consist of more than 80% sugars. They are used as sweeteners, and are ingredients of cosmetics or medical ointments. Furthermore, both have low water content, are often liquid at room temperature and resemble some known sugar-based deep eutectic solvents. Since it has been shown that it is possible to synthesize sugar esters in these deep eutectic solvents, in the current work honey or, as vegan alternative, agave syrup are used simultaneously as solvent and substrate for the enzymatic sugar ester production. For this purpose, important characteristics of the herein used honey and agave syrup were determined and compared with other available types. Subsequently, an enzymatic transesterification of four fatty acid vinyl esters was accomplished in ordinary honey and agave syrup. Notwithstanding of the high water content for transesterification reactions of the solvent, the successful sugar ester formation was proved by thin-layer chromatography and compared to a sugar ester which was synthesized in a conventional deep eutectic solvent. For a clear verification of the sugar esters, mass determinations by ESI-Q-ToF experiments and a NMR analysis were done. These environmentally friendly produced sugar esters have the potential to be used in cosmetics or pharmaceuticals, or to enhance their effectiveness.

  17. A 13-week repeated dose study of three 3-monochloropropane-1,2-diol fatty acid esters in F344 rats.

    Science.gov (United States)

    Onami, Saeko; Cho, Young-Man; Toyoda, Takeshi; Mizuta, Yasuko; Yoshida, Midori; Nishikawa, Akiyoshi; Ogawa, Kumiko

    2014-04-01

    3-monochloropropane-1,2-diol (3-MCPD), a rat renal and testicular carcinogen, has been reported to occur in various foods and food ingredients as free or esterified forms. Since reports about toxicity of 3-MCPD esters are limited, we conducted a 13-week rat subchronic toxicity study of 3-MCPD esters (palmitate diester: CDP, palmitate monoester: CMP, oleate diester: CDO). We administered a carcinogenic dose (3.6 × 10(-4) mol/kg B.W./day) of 3-MCPD or these esters at equimolar concentrations and two 1/4 lower doses by gavage with olive oil as a vehicle five times a week for 13 weeks to F344 male and female rats. As a result, five out of ten 3-MCPD-treated females died from acute renal tubular necrosis, but none of the ester-treated rats. Decreased HGB was observed in all high-dose 3-MCPD fatty acid ester-treated rats, except CDO-treated males. The absolute and relative kidney weights were significantly increased in the ester-treated rats at medium and high doses. Relative liver weights were significantly increased in the esters-treated rat at high dose, except for CMP females. Significant increase in apoptotic epithelial cells in the initial segment of the epididymis of high-dose ester-treated males was also observed. The results suggested that although acute renal toxicity was lower than 3-MCPD, these three 3-MCPD fatty acid esters have the potential to exert subchronic toxicity to the rat kidneys and epididymis, to a similar degree as 3-MCPD under the present conditions. NOAELs (no-observed-adverse-effect levels) of CDP, CMP and CDO were suggested to be 14, 8 and 15 mg/kg B.W./day, respectively.

  18. The effect of sorbic acid and esters of p-hydroxybenzoic acid on the protonmotive force in Escherichia coli membrane vesicles.

    Science.gov (United States)

    Eklund, T

    1985-01-01

    The effect of three food preservatives, sorbic acid and methyl and butyl esters of p-hydroxybenzoic acid, on the protonmotive force in Escherichia coli membrane vesicles was investigated. Radioactive chemical probes were used to determine the two components of the protonmotive force: delta pH (pH difference) and delta psi (membrane potential). Both types of compound selectively eliminated delta pH across the membrane, while leaving delta psi much less disturbed indicating that transport inhibition by neutralization of the protonmotive force cannot be the only mechanism of action for the food preservatives tested.

  19. Absolute configuration and enantiomeric composition of partially resolved mandelic, atrolactic and lactic acids by {sup 1}H NMR of their (S)-2-methylbutyl esters

    Energy Technology Data Exchange (ETDEWEB)

    Andrade, Francisco A. da C.; Mendes, Maricleide P. de L.; Fonseca, Neuracy C. da, E-mail: fandrade@ufba.br [Universidade Federal da Bahia (UFBA), Salvador, BA (Brazil). Instituto de Quimica. Departamento de Quimica Organica

    2013-06-15

    The mandelic, atrolactic and lactic acid esters of the (S)-2-methyl-1-butanol were examined as diastereomeric derivatives for the stereochemical analysis of the mentioned acids by {sup 1}H nuclear magnetic resonance (NMR) at 300 MHz. The diastereomeric esters showed distinctive signals in the methylenic absorption range (O-CH{sub 2}-CH) of the alcoholic moieties. By spectral analysis at this region, absolute configurations were attributed, chemical shifts of the correspondent pro-(R) and pro-(S) hydrogens from the methylene group of the alcohol moiety were assigned and enantiomeric compositions were determined for the original partially resolved acids. (author)

  20. Highly efficient high-performance liquid chromatographic separation of xylene isomers and phthalate acid esters on a homemade DUT-67(Zr) packed column.

    Science.gov (United States)

    Chen, Sha; Li, Xiao-Xin; Feng, Fan; Li, Sumei; Han, Jia-Hui; Jia, Zi-Yi; Shu, Lun; Somsundaran, P; Li, Jian-Rong

    2018-04-16

    In this study, the baseline separations of xylene isomers and phthalate acid esters on a homemade DUT-67(Zr) packed column were achieved, respectively. The high selectivity for xylene isomers and phthalate acid esters was obtained with the increase of temperature and decrease of the retention time. The hydrophobicity of xylene isomers and phthalate acid esters caused the different separation time on the DUT-67(Zr) packed column. The relative standard deviation values of retention time, peak area, peak height and half peak width for five repeat separation of the xylene isomers were 0.26-0.35, 2.11-2.26, 1.51-2.03, and 0.29-0.77%, and the values of the phthalate acid esters on DUT-67(Zr) column were 0.1-0.4, 4.4-5.2, 3.9-6.3, and 0.6-2.1%, respectively. The thermodynamic properties indicated that the separation of xylene isomers was controlled by ΔH and ΔS, but the separation of phthalate acid esters was mainly controlled by ΔS. This article is protected by copyright. All rights reserved. This article is protected by copyright. All rights reserved.

  1. Randomised clinical study: inulin short-chain fatty acid esters for targeted delivery of short-chain fatty acids to the human colon.

    Science.gov (United States)

    Polyviou, T; MacDougall, K; Chambers, E S; Viardot, A; Psichas, A; Jawaid, S; Harris, H C; Edwards, C A; Simpson, L; Murphy, K G; Zac-Varghese, S E K; Blundell, J E; Dhillo, W S; Bloom, S R; Frost, G S; Preston, T; Tedford, M C; Morrison, D J

    2016-10-01

    Short-chain fatty acids (SCFA) produced through fermentation of nondigestible carbohydrates by the gut microbiota are associated with positive metabolic effects. However, well-controlled trials are limited in humans. To develop a methodology to deliver SCFA directly to the colon, and to optimise colonic propionate delivery in humans, to determine its role in appetite regulation and food intake. Inulin SCFA esters were developed and tested as site-specific delivery vehicles for SCFA to the proximal colon. Inulin propionate esters containing 0-61 wt% (IPE-0-IPE-61) propionate were assessed in vitro using batch faecal fermentations. In a randomised, controlled, crossover study, with inulin as control, ad libitum food intake (kcal) was compared after 7 days on IPE-27 or IPE-54 (10 g/day all treatments). Propionate release was determined using (13) C-labelled IPE variants. In vitro, IPE-27-IPE-54 wt% propionate resulted in a sevenfold increase in propionate production compared with inulin (P inulin (439.5 vs. 703.9 kcal, P = 0.025) and IPE-54 (439.5 vs. 659.3 kcal, P = 0.025), whereas IPE-54 was not significantly different from inulin control. IPE-27 significantly reduced food intake suggesting colonic propionate plays a role in appetite regulation. Inulin short-chain fatty acid esters provide a novel tool for probing the diet-gut microbiome-host metabolism axis in humans. © 2016 The Authors. Alimentary Pharmacology & Therapeutics Published by John Wiley & Sons Ltd.

  2. Contribution to the Analysis of the Essential Oil of Helichrysum italicum (Roth G. Don. – Determination of Ester Bonded Acids and Phenols

    Directory of Open Access Journals (Sweden)

    Igor Jerković

    2008-04-01

    Full Text Available The essential oil of Helichrysum italicum (Roth G. Don (everlasting orImmortelle essential oil was isolated by hydrodistillation and analysed by GC and GCMS.Forty four compounds were identified. The main components were α-pinene(12.8%, 2-methyl-cyclohexyl pentanoate (11.1 %, neryl acetate (10.4%, 1,7-di-epi-α-cedrene (6.8% and other compounds. The oil was fractionated and ester-containingfraction was hydrolysed with KOH/H2SO4. The liberated volatiles were analysed by GCand GC-MS: three phenols and twenty seven volatile carboxylic acids were identified[70% low fatty acids (C2-C5, 15% C10-C12 acids and 15% other acids]. The main acidswere acetic acid (24.3% propanoic acid (17.2%, 2-methylpropanoic acid (11.4%,dodecanoic acid (8.7%, 2-methylbutanoic acid (8.3%, (Z-2-methylbutenoic acid(5.1% and decanoic acid (4.6%. With respect to the identified bonded carboxylic acids,the minimal number of esters in the oil was twenty seven, but their overall quantity wasprobably larger due to different possible combinations of alcohols with acids to formesters. On the other hand, only six main esters were identified in the oil beforefractionation and hydrolysis.

  3. Constituents of Mediterranean Spices Counteracting Vascular Smooth Muscle Cell Proliferation: Identification and Characterization of Rosmarinic Acid Methyl Ester as a Novel Inhibitor

    Czech Academy of Sciences Publication Activity Database

    Liu, R.; Heiss, E.H.; Waltenberger, B.; Blažević, T.; Schachner, B.; Jiang, B.; Kryštof, Vladimír; Liu, W.; Schwaiger, S.; Peña-Rodríguez, L. M.; Breuss, J.; Stuppner, H.; Dirsch, V.M.; Atanasov, A. G.

    2018-01-01

    Roč. 62, č. 7 (2018), č. článku 1700860. ISSN 1613-4125 Institutional support: RVO:61389030 Keywords : Mediterranean spices * neointima formation * rosmarinic acid * rosmarinic acid methyl ester * vascular smooth muscle cells Subject RIV: CE - Biochemistry OBOR OECD: Biochemical research methods Impact factor: 4.323, year: 2016

  4. Enzymatically and reductively degradable α-amino acid-based poly(ester amide)s: Synthesis, cell compatibility, and intracellular anticancer drug delivery

    NARCIS (Netherlands)

    Sun, H.; Cheng, Ru; Deng, Chao; Meng, Fenghua; Dias, Aylvin A.; Hendriks, Marc; Feijen, Jan; Zhong, Zhiyuan

    2015-01-01

    A novel and versatile family of enzymatically and reductively degradable α-amino acid-based poly(ester amide)s (SS-PEAs) were developed from solution polycondensation of disulfide-containing di-p-toluenesulfonic acid salts of bis-l-phenylalanine diesters (SS-Phe-2TsOH) with di-p-nitrophenyl adipate

  5. Fatty acid methyl esters, carbon nanotubes and carbon nanowalls coatings such as lubricity improvers of low sulfur diesel fuels

    Energy Technology Data Exchange (ETDEWEB)

    Cursaru, Diana Luciana; Tanasescu, Constantin [Petroleum-Gas Univ. of Ploiesti (Romania); Vizireanu, Sorin [National Institute for Laser, Plasma and Radiation Physics (Romania)

    2013-06-01

    In this study the lubricity of diesel fuel was restored by different methods, firstly by classic addition of fatty acid methyl esters or by dispersing carbon nanotubes into diesel fuels and secondly, by protecting the metallic surfaces which are in the direct contact to the low sulfur diesel fuel, by application of solid carbon nanowalls coatings synthesized by radiofrequency plasma beam deposition. The fatty acid methyl esters were prepared by transesterification of the sun flower oil in the presence of methanol. The carbon nanotubes were synthesized by CO disproportionation method and were characterized by RAMAN spectroscopy and high resolution transmission electron microscopy (TEM). The CNWs layers, before the friction tests, were examined by scanning electron microscopy (SEM), atomic force microscopy (AFM) and Raman spectroscopy, while the wear on the steel balls was investigated by optical microscopy of the HRRT apparatus and the wear track on the steel disk was investigated by SEM, AFM and profilometry. The lubricity was measured using the High Frequency Reciprocating Rig (HFRR) method. It has been found that CNWs layers exhibit a lubricating potential for the rubbed surfaces in the presence of low sulfur diesel fuels. Tribological analyses of various carbon materials revealed that the friction coefficient of carbon nanowalls is close to the values obtained for graphite. (orig.)

  6. Fatty acid methyl ester from Neurospora intermedia N-1 isolated from Indonesian red peanut cake (oncom merah).

    Science.gov (United States)

    Priatni, S; Hartati, S; Dewi, P; Kardono, L B S; Singgih, M; Gusdinar, T

    2010-08-01

    The objective of this study was to identify the Fatty Acid Methyl Ester (FAME) from Neurospora intermedia N-1 that isolated from Indonesian red peanut cake (oncom). FAME profiles have been used as biochemical characters to study many different groups of organisms, such as bacteria and yeasts. FAME from N. intermedia N-1 was obtained by some stages of extraction the orange spores and fractination using a chromatotron. The pure compound (1) was characterized by 500 mHz NMR (1H and 13C), FTIR and LC-MS. Summarized data's of 1H and 13C NMR spectra of compound 1 contained 19 Carbon, 34 Hydrogen and 2 Oxygen (C19H34O2). The position of the double bonds at carbon number 8 and 12 were indicated in the HMBC spectrum (2D-NMR). LC-MS spectrum indicates molecular weight of the compound 1 as 294 which is visible by the presence of protonated molecular ion [M+H] at m/z 295. Methyl esters of long chain fatty acids was presented by a 3 band pattern of IR spectrum with bands near 1249, 1199 and 1172 cm(-1). We suggested that the structure of the pure compound 1 is methyl octadeca-8,12-dienoate. The presence methyl octadeca-8,12-dienoate in N. intermedia is the first report.

  7. Heat-shrink tubing as a solid-phase microextraction coating for the enrichment and determination of phthalic acid esters.

    Science.gov (United States)

    Luo, Xi; He, Chengxia; Zhang, Feifang; Wang, Hailong; Yang, Bingcheng; Liang, Xinmiao

    2014-12-01

    Heat-shrink tubing, which shrinks in one plane only (its diameter) when heated, commonly used for sealing protection in electrical engineering, was found to be able to function as a solid-phase microextraction coating. Its utility was demonstrated for the determination of phthalic acid esters in an aqueous solution combined with high-performance liquid chromatography equipped with a UV absorbance detector. The preparation procedure was rather simple and only ∼10 min was needed. The fiber cost is extremely low (∼10 cent each). The parameters affecting the extraction were optimized. Heat-shrink tubing fiber exhibited a significant enrichment effect for the three examined phthalic acid esters and up to 931-fold enrichment factor was obtained. The limit of detection was <10 μg/L for all analytes. The operation repeatability and fiber-to-fiber reproducibility were 1.2-8.3 and 5.4-9.1%, respectively. It was successfully applied for the analysis of bottled drinking water with recoveries ranging from 90.1-100.5%. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  8. System Development from Organic Solvents to Ionic Liquids for Synthesiz-ing Ascorbyl Esters with Conjugated Linoleic Acids

    DEFF Research Database (Denmark)

    Yang, Zhiyong; Schultz, Lise; Guo, Zheng

    2012-01-01

    . Results show that only Novozym® 435 turned out to be a useful enzymatic preparation for the production of ascorbyl-CLA ester. The optimum reaction conditions in the or-ganic solvent system were 4 h at 55°C and at a molar ratio of 5 (CLA/ascorbic acid). The esterification reaction was trans......-ferred to an ionic liquid system for the purpose of improving solubility of the polar substrate and avoiding the application of organic solvents. From screening experiments, it was evident that only methyltrioctylammonium triflouroacetate (tO-MA·TFA) could provide a proper reaction environment for production...... of ascorbyl-CLA ester when using Novozym® 435 as biocatalyst. It was possible to significantly increase the productivity (150 g/l) through the increase of ascorbic acid sol-ubility in ionic liquids by super saturation together with the increase of reaction temperature to 70°C, far beyond than that in organic...

  9. Comparison of Antioxidant Evaluation Assays for Investigating Antioxidative Activity of Gallic Acid and Its Alkyl Esters in Different Food Matrices.

    Science.gov (United States)

    Phonsatta, Natthaporn; Deetae, Pawinee; Luangpituksa, Pairoj; Grajeda-Iglesias, Claudia; Figueroa-Espinoza, Maria Cruz; Le Comte, Jérôme; Villeneuve, Pierre; Decker, Eric A; Visessanguan, Wonnop; Panya, Atikorn

    2017-08-30

    The addition of antioxidants is one of the strategies to inhibit lipid oxidation, a major cause of lipid deterioration in foods leading to rancidity development and nutritional losses. However, several studies have been reported that conventional antioxidant assays, e.g., TPC, ABTS, FRAP, and ORAC could not predict antioxidant performance in several foods. This study aimed to investigate the performance of two recently developed assays, e.g., the conjugated autoxidizable triene (CAT) and the apolar radical-initiated conjugated autoxidizable triene (ApoCAT) assays to predict the antioxidant effectiveness of gallic acid and its esters in selected food models in comparison with the conventional antioxidant assays. The results indicated that the polarities of the antioxidants have a strong impact on antioxidant activities. In addition, different oxidant locations demonstrated by the CAT and ApoCAT assays influenced the overall antioxidant performances of the antioxidants with different polarities. To validate the predictability of the assays, the antioxidative performance of gallic acid and its alkyl esters was investigated in oil-in-water (O/W) emulsions, bulk soybean oils, and roasted peanuts as the lipid food models. The results showed that only the ApoCAT assay could be able to predict the antioxidative performances in O/W emulsions regardless of the antioxidant polarities. This study demonstrated that the relevance of antioxidant assays to food models was strongly dependent on physical similarities between the tested assays and the food structure matrices.

  10. Heterogeneous ozonation reactions of PAHs and fatty acid methyl esters in biodiesel particulate matter

    Science.gov (United States)

    Kasumba, John; Holmén, Britt A.

    2018-02-01

    Numerous studies have examined the oxidation of PAHs found in diesel particulate matter (PM) by ozone, but no studies have investigated the ozone oxidation of biodiesel exhaust PM. Fatty acid methyl esters (FAMEs), found in high abundance in biodiesel PM, can potentially alter the kinetics of the reactions between atmospheric oxidants such as ozone and particle-phase PAHs. In this study, the heterogeneous reactivity of 16 EPA PAHs upon 24 h exposure to 0.4 ppm ozone in the presence (PAH + FAMES) and absence (PAH-only) of FAMEs was investigated at room temperature and 50% relative humidity. The ozone-reactivity of the PAHs detected in 20% biodiesel (B20) exhaust PM was also investigated. In the absence of FAMEs, the pseudo-first order ozone reaction rate constant, kO 3 , of PAHs varied from 0.086 ± 0.030 hr-1 (chrysene) to 0.184 ± 0.078 hr-1 (anthracene). In the presence of FAMEs, kO 3 of the PAHs varied between 0.013 ± 0.012 hr-1 (benzo[b]fluoranthene) and 0.168 ± 0.028 hr-1 (benzo[a]pyrene), and with the exception of benzo[a]pyrene, the kO 3 of PAHs were 1.2-8 times lower compared to those obtained during the PAH-only ozone exposure. Only one PAH, benzo[a]pyrene (BaP), did not show a significant change in kO3 with addition of FAMEs. Phenanthrene, fluoranthene, and pyrene, the only PAHs detected in the B20 PM, had kO 3 values about 4 times lower in B20 PM than those obtained when spiked PAHs-only were exposed to ozone. The kO 3 values of phenanthrene and fluoranthene in the B20 PM were 2 times higher than rates obtained when the PAH mix was exposed to ozone in the presence of the FAMEs. In contrast, pyrene's kO 3 in the B20 PM was about 2 times lower than that obtained for the PAH + FAMEs exposure. Observed differences in PAH behavior demonstrate individual PAH heterogeneous reactivity with gas-phase ozone is sensitive to PAH (vapor pressure, solubility/sorption to matrix components, chemical reactivity) as well as substrate properties (PAH and O3 diffusivity

  11. Enzymatic Synthesis of Glyserol-Coconut Oil Fatty Acid and Glycerol-Decanoic Acis Ester as Emulsifier and Antimicrobial Agents Using Candida rugosa Lipase EC 3.1.1.3

    Science.gov (United States)

    Handayani, Sri; Putri, Ayu Tanissa Tamara; Setiasih, Siswati; Hudiyono, Sumi

    2018-01-01

    In this research, enzymatic esterification was carried out between glycerol and fatty acid from coconut oil and decanoic acid using n-hexane as solvent. In this reaction Candida rugosa lipase was used as biocatalyst. Optimization esterification reaction was carried out for parameter of the substrate ratio. The mmol ratio between fatty acid and glycerol were used are 1:1, 1:2, 1:3, and 1: 4. The highest conversion percentage obtained at the mole ratio of 1: 4 with the value of 78.5% for the glycerol-decanoic acid ester and 55.4% for the glycerol coconut oil fatty acid ester. Esterification products were characterized by FT-IR. The FT-IR spectrum showed that the ester bond was formed as indicated by the wave number 1750-1739 cm-1. The esterification products were then examined by simple emulsion test and was proved to be an emulsifier. The glycerol-coconut oil fatty acid ester produced higher stability emulsion compare with glycerol decanoic ester. The antimicrobial activity assay using disc diffusion method showed that both glycerol-coconut oil fatty acid ester and glycerol-decanoic ester had the ability inhibiting the growth of Propionibacterium acnes and Staphylococcus epidermidis. Glycerol-decanoic ester shows higher antimicrobial activity than glycerol-coconut oil fatty acid ester.

  12. Investigation of nanocomposites made with poly(methacrylic acid-co-methyl methacrylate)/poly(N-vinyl-2-pyrrolidone)/multi-walled carbon nanotubes

    Energy Technology Data Exchange (ETDEWEB)

    Guoqin, Liu; Wei, Miao [College of Material Science and Engineering, Henan University of Technology (China); Lin-Jian, Shangguan, E-mail: mikepolymer@126.com [School of Mechanical Engineering, North China University of Water Conservancy and Electric Power (China)

    2014-06-01

    Poly(methacrylic acid-co-methyl methacrylate) (P(MAA-co-MMA)) was prepared in the presence of poly(N-vinyl-2-pyrrolidone) (PVP) and multi-walled carbon nanotubes (MWNTs) via ultrasonic assisted solution free radical polymerization, i.e., P(MAA-co-MMA)/PVP/MWNTs nanocomposites. The morphology, glassy-state storage modulus, thermal behavior and swelling characteristics of P(MAA-co-MMA)/PVP/MWNTs nanocomposites were investigated. Scanning electron micrographs (SEM) revealed that MWNTs at low concentration could be uniformly dispersed into P(MAA-co-MMA)/PVP blends. With increasing MWNTs weight fraction, the average glassy-state modulus, glass transition temperatures and decomposition temperature of the nanocomposites increased, but their swelling characteristics decreased. (author)

  13. Investigation of nanocomposites made with poly(methacrylic acid-co-methyl methacrylate/poly(N-vinyl-2-pyrrolidone/multi-walled carbon nanotubes

    Directory of Open Access Journals (Sweden)

    Liu Guoqin

    2014-01-01

    Full Text Available Poly(methacrylic acid-co-methyl methacrylate (P(MAA-co-MMA was prepared in the presence of poly(N-vinyl-2-pyrrolidone (PVP and multiwalled carbon nanotubes (MWNTs via ultrasonic assisted solution free radical polymerization, i.e., P(MAA-co-MMA/PVP/MWNTs nanocomposites. The morphology, glassy-state storage modulus, thermal behavior and swelling characteristics of P(MAA-co-MMA/PVP/MWNTs nanocomposites were investigated. Scanning electron micrographs (SEM revealed that MWNTs at low concentration could be uniformly dispersed into P(MAA-co-MMA/PVP blends. With increasing MWNTs weight fraction, the average glassy-state modulus, glass transition temperatures and decomposition temperature of the nanocomposites increased, but their swelling characteristics decreased.

  14. Preparation and characterization of reactive blends of poly(lactic acid), poly(ethylene-co-vinyl alcohol), and poly(ethylene-co-glycidyl methacrylate)

    International Nuclear Information System (INIS)

    Warangkhana, Phromma; Rathanawan, Magaraphan; Jana Sadhan, C.

    2015-01-01

    The ternary blends of poly(lactic acid) (PLA), poly(ethylene-co-vinyl alcohol) (EVOH), and poly(ethylene-co-glycidyl methacrylate) (EGMA) were prepared. The role of EGMA as a compatibilizer was evaluated. The weight ratio of PLA:EVOH was 80:20 and the EGMA loadings were varied from 5-20 phr. The blends were characterized as follows: thermal properties by differential scanning calorimetry, morphology by scanning electron microscopy, and mechanical properties by pendulum impact tester, and universal testing machine. The glass transition temperature of PLA blends did not change much when compared with that of PLA. The blends of PLA/EGMA and EVOH/EGMA showed EGMA dispersed droplets where the latter led to poor impact properties. However, the tensile elongation at break and tensile toughness substantially increased upon addition of EGMA to blends of PLA and EVOH. It was noted in tensile test samples that both PLA and EVOH domains fibrillated significantly to produce toughness

  15. Preparation and characterization of reactive blends of poly(lactic acid), poly(ethylene-co-vinyl alcohol), and poly(ethylene-co-glycidyl methacrylate)

    Energy Technology Data Exchange (ETDEWEB)

    Warangkhana, Phromma; Rathanawan, Magaraphan, E-mail: rathanawan.k@chula.ac.th [Chulalongkorn University, Petroleum and Petrochemical College - Bangkok (Thailand); Jana Sadhan, C., E-mail: janas@uakron.edu [The University of Akron, Department of Polymer Engineering, Ohio (United States)

    2015-05-22

    The ternary blends of poly(lactic acid) (PLA), poly(ethylene-co-vinyl alcohol) (EVOH), and poly(ethylene-co-glycidyl methacrylate) (EGMA) were prepared. The role of EGMA as a compatibilizer was evaluated. The weight ratio of PLA:EVOH was 80:20 and the EGMA loadings were varied from 5-20 phr. The blends were characterized as follows: thermal properties by differential scanning calorimetry, morphology by scanning electron microscopy, and mechanical properties by pendulum impact tester, and universal testing machine. The glass transition temperature of PLA blends did not change much when compared with that of PLA. The blends of PLA/EGMA and EVOH/EGMA showed EGMA dispersed droplets where the latter led to poor impact properties. However, the tensile elongation at break and tensile toughness substantially increased upon addition of EGMA to blends of PLA and EVOH. It was noted in tensile test samples that both PLA and EVOH domains fibrillated significantly to produce toughness.

  16. Synthesis and Characterization of Waterborne Fluoropolymers Prepared by the One-Step Semi-Continuous Emulsion Polymerization of Chlorotrifluoroethylene, Vinyl Acetate, Butyl Acrylate, Veova 10 and Acrylic Acid

    Directory of Open Access Journals (Sweden)

    Hongzhu Liu

    2017-01-01

    Full Text Available Waterborne fluoropolymer emulsions were synthesized using the one-step semi-continuous seed emulsion polymerization of chlorotrifluoroethylene (CTFE, vinyl acetate (VAc, n-butyl acrylate (BA, Veova 10, and acrylic acid (AA. The main physical parameters of the polymer emulsions were tested and analyzed. Characteristics of the polymer films such as thermal stability, glass transition temperature, film-forming properties, and IR spectrum were studied. Meanwhile, the weatherability of fluoride coatings formulated by the waterborne fluoropolymer and other coatings were evaluated by the quick ultraviolet (QUV accelerated weathering test, and the results showed that the fluoropolymer with more than 12% fluoride content possessed outstanding weather resistance. Moreover, scale-up and industrial-scale experiments of waterborne fluoropolymer emulsions were also performed and investigated.

  17. Effect of homopolymer poly(vinyl acetate on compatibility and mechanical properties of poly(propylene carbonate/poly(lactic acid blends

    Directory of Open Access Journals (Sweden)

    J. Gao

    2012-11-01

    Full Text Available A small amount of homopolymer poly(vinyl acetate (PVAc is used to compatibilize the biodegradable blends of poly(propylene carbonate (PPC and poly(lactic acid (PLA. Scanning electron microscopy (SEM and differential scanning calorimetry (DSC results show that PVAc is selectively localized in the PLA phase and at the interface between PPC and PLA phases. As a result, these interface-localized PVAc layers act as not only a compatibilizer to improve the phase dispersion significantly but also a bridge to increase the interfacial adhesion between PPC and PLA phases dramatically. Both of them are believed to be responsible for the enhancement in mechanical properties. This work provides a simple avenue to fabricate eco-friendly PPC/PLA blends with high performance, and in some cases, reducing the demand for petroleumbased plastics such as polypropylene.

  18. Synthesis and Characterization of Modified Epoxy Resins by Silicic Acid Tetraethyl Ester and Nano-SiO2

    Institute of Scientific and Technical Information of China (English)

    李海燕; 张之圣

    2004-01-01

    A kind of modified epoxy resins was obtained by condensation of epoxy resin with silicic acid tetraethyl ester(TEOS) and nano-SiO2. The reactions were performed with hydrochloric acid as a catalyst at 63 °C.The structure, thermal stability and morphological characteristics of the modified epoxy resins were studied through infrared spectra(FT-IR) analysis, thermogravimetric (TG) analysis and scanning electron microscopy respectively. It has been found from the IR and TG study that modified epoxy resins have greater thermal stability than epoxy resins, and its thermal stability has been improved by the formation of inter-crosslinked network structure. The modified epoxy resins exhibit heterogeneous morphology and heterogeneity increases with more TEOS feeding, which in turn confirms the formation of inter-crosslinked network structure in modified epoxy resins.

  19. Continuous production of fatty acid ethyl esters from soybean oil at supercritical conditions - doi: 10.4025/actascitechnol.v34i2.11255

    Directory of Open Access Journals (Sweden)

    Camila da Silva

    2012-03-01

    Full Text Available This work reports the production of fatty acid ethyl esters (FAEE from the transesterification of soybean oil in supercritical ethanol in a continuous catalyst-free process using different reactor configurations. Experiments were performed in a tubular reactor in one-step reaction and experimentally simulating two reactors, one operated in series and the other a recycle reactor. The reaction products were analyzed for their content of residual triglycerides, glycerol, monoglycerides, diglycerides, ethyl esters and decomposition. Results show that the configurations studied with intermediate separation of glycerol afford higher conversions of vegetable oil to their fatty acid ethyl esters derivatives when compared to the one-step reaction, with relatively low decomposition of fatty acids (< 5.0 wt%.

  20. Direct methylation procedure for converting fatty amides to fatty acid methyl esters in feed and digesta samples.

    Science.gov (United States)

    Jenkins, T C; Thies, E J; Mosley, E E

    2001-05-01

    Two direct methylation procedures often used for the analysis of total fatty acids in biological samples were evaluated for their application to samples containing fatty amides. Methylation of 5 mg of oleamide (cis-9-octadecenamide) in a one-step (methanolic HCl for 2 h at 70 degrees C) or a two-step (sodium methoxide for 10 min at 50 degrees C followed by methanolic HCl for 10 min at 80 degrees C) procedure gave 59 and 16% conversions of oleamide to oleic acid, respectively. Oleic acid recovery from oleamide was increased to 100% when the incubation in methanolic HCl was lengthened to 16 h and increased to 103% when the incubation in methoxide was modified to 24 h at 100 degrees C. However, conversion of oleamide to oleic acid in an animal feed sample was incomplete for the modified (24 h) two-step procedure but complete for the modified (16 h) one-step procedure. Unsaturated fatty amides in feed and digesta samples can be converted to fatty acid methyl esters by incubation in methanolic HCl if the time of exposure to the acid catalyst is extended from 2 to 16 h.

  1. Surface characterization of poly(vinyl chloride) urinary catheters functionalized with acrylic acid and poly(ethylene glycol) methacrylate using gamma-radiation

    Energy Technology Data Exchange (ETDEWEB)

    Islas, Luisa [Departamento de Química de Radiaciones y Radioquímica, Instituto de Ciencias Nucleares, Universidad Nacional Autónoma de México, Ciudad Universitaria, Mexico D.F. 04510 (Mexico); Ruiz, Juan-Carlos [División de Ciencias Básicas e Ingeniería, Depto. de Ingeniería de Procesos e Hidráulica, Universidad Autónoma Metropolitana-Iztapalapa, Av. San Rafael Atlixco No. 186, 09340 México D.F. (Mexico); Muñoz-Muñoz, Franklin [Facultad de Ingeniería, Arquitectura y Diseño, Universidad Autónoma de Baja California, Carretera Transpeninsular Ensenada-Tijuana 3917, Ensenada, B.C. C.P 22860 (Mexico); Isoshima, Takashi [Nano Medical Engineering Laboratory, RIKEN, 2-1Hirosawa, Wako, Saitama 351-0198 (Japan); Burillo, Guillermina, E-mail: burillo@nucleares.unam.mx [Departamento de Química de Radiaciones y Radioquímica, Instituto de Ciencias Nucleares, Universidad Nacional Autónoma de México, Ciudad Universitaria, Mexico D.F. 04510 (Mexico)

    2016-10-30

    Highlights: • Polymer grafting using gamma-radiation allowed for acrylic acid and poly(ethylene glycol) methacrylate to graft on the inner and outer surface of poly(vinyl chloride) urinary catheters. • HR-XPS revealed the different compositional percentages of the compounds present on the surface of the catheter. • Catheters that were grafted with PEGMA had the roughest surface as observed using scanning electron microscopy (SEM) and confocal laser microscopy (CLM). - Abstract: Poly(vinyl chloride) (PVC) urinary catheters were modified with either a single or binary graft of acrylic acid (AAc) and/or poly(ethylene glycol) methacrylate (PEGMA) using gamma-radiation from {sup 60}Co to obtain PVC-g-AAc, PVC-g-PEGMA, [PVC-g-AAc]-g-PEGMA, and [PVC-g-PEGMA]-g-AAc copolymers. The outer and inner surfaces of the modified catheters were characterized using scanning electron microscopy (SEM), confocal laser microscopy (CLM) and X-ray photoelectron spectroscopy (XPS). The XPS analyses, by examining the correlation between the variation of the C{sub 1s} and O{sub 1s} content at the catheter’s surface, revealed that the catheter’s surfaces were successfully grafted with the chosen compounds, with those that were binary grafted showing a slightly more covered surface as was evidenced by the disappearance of PVC’s Cl peak. The SEM and CLM analyses revealed that catheters that had been grafted with PEGMA had a rougher outer surface as compared to those that had only been grafted with AAc. In addition, these imaging techniques showed that the inner surface of the singly grafted catheters, whether they had been grafted with AAc or PEGMA, retained some smoothness at the analyzed grafting percentages, while the binary grafted catheters showed many protuberances and greater roughness on both outer and inner surfaces.

  2. Thermal energy storage properties of mannitol–fatty acid esters as novel organic solid–liquid phase change materials

    International Nuclear Information System (INIS)

    Sari, Ahmet

    2012-01-01

    Highlights: ► Four kinds of mannitol–fatty acid esters were synthesized as novel organic PCMs for thermal energy storage applications. ► The synthesized PCMs were characterized using FT-IR, 1 H NMR, 13 C NMR, DSC and TGA methods and thermal cycling test. ► The melting temperatures and latent heat values of the PCMs were in the range of 42–65 °C and 145–202 J/g, respectively. ► Thermal conductivity of the PCMs was increased significantly by addition of EG with especially 10 wt%. ► The synthesized PCMs are promising organic PCMs for solar heating applications. - Abstract: In this study, four kinds of mannitol–fatty acid esters were synthesized as novel organic phase change materials (PCMs) for thermal energy storage applications. The structural characterization of synthesized mannitol hexastearate (MHS), mannitol hexapalmitate (MHP), mannitol hexamyristate (MHM) and mannitol hexalaurate (MHL) were carried out using Fourier Transform Infrared (FT-IR), Proton Nuclear Magnetic Resonance ( 1 H NMR), and 13 C NMR spectroscopy methods. Thermal energy storage properties and thermal reliability of the synthesized PCMs were determined using differential scanning calorimetry (DSC) method at a heating rate of 1 °C/min. DSC results showed that the melting temperatures of the PCMs were in the temperature range of 42–65 °C and their latent heat values spanned between 145 and 202 J/g. The latent heats of these PCMs are low compared to mannitol but they fall into the same range as fatty acids. The synthesized PCMs have much lower phase change temperatures and supercooling degree (about 1–8 °C) and compared to the mannitol. They have also better odor, noncorrosivity and thermal durability properties as compared to the fatty acids. Thermal cycling test consisted of repeated 1000 melting/solidification cycles also revealed that the synthesized PCMs have good thermal reliability. In addition, thermal conductivity of the PCMs was increased significantly by

  3. Effects of fatty acid methyl esters proportion on combustion and emission characteristics of a biodiesel fueled diesel engine

    International Nuclear Information System (INIS)

    E, Jiaqiang; Liu, Teng; Yang, W.M.; Li, Jing; Gong, Jinke; Deng, Yuanwang

    2016-01-01

    Highlights: • The effects of FAMEs proportion on combustion and emission were numerically studied. • The impact of the saturation level on combustion characteristic is not straightforward. • The NO_x emission is mainly related to the fuel kinetic viscosity. - Abstract: With the growing energy problems, scholars has focused on utilizing renewable biodiesel as a fossil fuel alternative. Four different typical biodiesels were employed to investigate the effects of fatty acid methyl esters proportion on combustion and emission characteristics of a biodiesel fueled diesel engine in terms of heat release rate, cylinder pressure, indicated power and formation of NO_x emission. The corresponding computational fluid dynamic modeling was performed by KIVA4 coupled CHEMKIN II code, and a special chemical kinetics mechanism consisting of 106 species and 263 reactions was developed to simulate the combustion process since it contained methyl linoleate, a majority component in most biodiesel, thereby improved the accuracy of simulation. The simulation results indicated that chemical ignition delay time and kinetic viscosity of biodiesel played very important roles in combustion process. Higher saturation level could shorten chemical ignition delay time, but the higher saturation contents like C16:0 and C18:0 together with C18:1 (a single double bond methyl ester) would increase the kinetic viscosity, resulting in poor fuel–air mixing and evaporation process. Lower kinetic viscosity methyl esters like C18:2 and C18:3 was favorable for better fuel–air mixing and subsequent combustion, however, a higher NO_x emission was discovered. Therefore, the relationship between saturation levels and combustion and emission characteristics of biodiesels is not simple and straightforward, the balance of five majority components is very important.

  4. Bias voltage dependence of molecular orientation of dialkyl ketone and fatty acid alkyl ester at the liquid–graphite interface

    Energy Technology Data Exchange (ETDEWEB)

    Hibino, Masahiro, E-mail: hibino@mmm.muroran-it.ac.jp [Department of Applied Sciences, Muroran Institute of Technology, 27-1 Mizumoto-cho, Muroran 050-8585 (Japan); Tsuchiya, Hiroshi [Department of Applied Physics, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8601 (Japan)

    2014-10-30

    Graphical abstract: - Highlights: • Self-assembled monolayers (SAMs) of 18-pentatriacontanone (as ketone) and stearyl stearate (as ester) were formed on a graphite surface at the liquid–solid interface. • Orientations of the molecules in SAMs on the substrate were studied by scanning tunneling microscopy. • A perpendicular carbon skeleton-plane orientation with the CO pointing up on the surface is favorable for a substrate with negative charge and vice versa. - Abstract: Molecular orientations of self-assembled 18-pentatriacontanone (as ketone) and stearyl stearate (as ester) monolayers adsorbed on a graphite surface were studied by scanning tunneling microscopy (STM) at the liquid–solid interface. At a positive sample bias, the central areas of the dialkyl ketone and fatty acid alkyl ester molecules in the STM images appeared as two bright regions on both sides of a dim spot and a bright region on one side of a dim spot, whereas at a negative sample bias, the areas appeared dim. This contrast variation indicates that a perpendicular carbon skeleton-plane orientation with the CO pointing down on the surface is favorable for a substrate with positive charge and vice versa because of the greater electronegativity of the oxygen atom. Upon the bias voltage reversal, the delay time for the STM image contrast change in the region was observed on a time scale of minutes. The difference between the delay time lengths for the direction of bias polarity change indicates that the perpendicular configuration with CO pointing up is more stable than that with CO pointing down. These results indicate that the use of an electric field along a direction vertical to the monolayer on the substrate provides control over the orientations of the molecules between two stable states at the liquid–solid interface.

  5. Enantioselective Synthesis of α-Mercapto-β-amino Esters via Rh(II)/Chiral Phosphoric Acid-Cocatalyzed Three-Component Reaction of Diazo Compounds, Thiols, and Imines.

    Science.gov (United States)

    Xiao, Guolan; Ma, Chaoqun; Xing, Dong; Hu, Wenhao

    2016-12-02

    An enantioselective method for the synthesis of α-mercapto-β-amino esters has been developed via a rhodium(II)/chiral phosphoric acid-cocatalyzed three-component reaction of diazo compounds, thiols, and imines. This transformation is proposed to proceed through enantioselective trapping of the sulfonium ylide intermediate generated in situ from the diazo compound and thiol by the phosphoric acid-activated imine. With this method, a series of α-mercapto-β-amino esters were obtained in good yields with moderate to good stereoselectivities.

  6. Larvicidal activity of oils, fatty acids, and methyl esters from ripe and unripe fruit of Solanum lycocarpum (Solanaceae against the vector Culex quinquefasciatus (Diptera: Culicidae

    Directory of Open Access Journals (Sweden)

    Viviane de Cássia Bicalho Silva

    2015-10-01

    Full Text Available ABSTRACTINTRODUCTION:The larvicidal activity of oils, fatty acids, and methyl esters of Solanum lycocarpum fruit against Culex quinquefasciatus is unknown.METHODS:The larvicidal activity of samples of ripe and unripe fruit from S. lycocarpum was evaluated against third and fourth instar larvae of C. quinquefasciatus .RESULTS:The oils, fatty acids, and methyl esters of S. lycocarpum showed the greatest larvicidal effect (57.1-95.0% at a concentration of 100mg/L (LC 50values between 0.70 and 27.54mg/L.CONCLUSIONS:Solanum lycocarpum fruit may be a good source of new natural products with larvicidal activity.

  7. The Effect of Storage Time, Temperature and Type of Packaging on the Release of Phthalate Esters into Packed Acidic Liquids

    Directory of Open Access Journals (Sweden)

    Noushin Rastkari

    2017-01-01

    Full Text Available Acidic liquids such as verjuice, lemon juice and vinegar are frequently consumed in Iran. Different kinds of acidic liquids are packaged in polyethylene terephthalate (PET and high-density polyethylene (HDPE bottles. There is evidence indicating that phthalates can leach from PET and HDPE bottles into their contents. In this work the effect of storage time, temperature and bottle type on the migration of phthalates from packaging materials into acidic liquids is studied by analyzing the samples stored under different conditions, before storage and after 2, 4 and 6 months of storage. The determined mean phthalate concentrations in μg/L were: <0.04 to 0.501 in verjuice, <0.04 to 0.231 in lemon juice and <0.04 to 0.586 in vinegar. The highest concentrations of diethyl phthalate (DEP and diethyl hexyl phthalate (DEHP were found in PET and HDPE bottles, respectively. Results of analyses before and after storage indicate that under some storage conditions, the concentrations of DEP, DEHP and dibutyl phthalate (DBP increased in acidic liquids. The possible migration of phthalic acid esters from plastic packaging materials into the contents was indicated by the results of the present study.

  8. Identification of tocopherols, tocotrienols, and their fatty acid esters in residues and distillates of structured lipids purified by short-path distillation.

    Science.gov (United States)

    Zou, Long; Akoh, Casimir C

    2013-01-09

    The fate of endogenous vitamin E isomers during production and purification of structured lipids (SLs) was investigated. Two SLs involving tripalmitin, stearidonic acid soybean oil, and docosahexaenoic acid were synthesized by transesterification catalyzed by Novozym 435 (NSL) and acidolysis by Lipozyme TL IM (LDHA) and purified by short-path distillation (SPD). The electron impact and chemical ionization mass spectra of tocopheryl and tocotrienyl fatty acid esters in the distillates measured by GC-MS in synchronous scan/SIM mode demonstrated that these esters were formed during acidolysis as well as transesterification. The predominant esters were tocopheryl palmitate, tocopheryl oleate, and tocopheryl linoleate homologues, and no tocopheryl or tocotrienyl linolenate, stearidonate, or docosahexaenoate was found. Meanwhile, none of these esters were detected in the residues for either NSL or LDHA. Less than 50% of vitamin E isomers were present in residues after SPD. This loss played a major role in the rapid oxidative deterioration of SLs from previous studies with less contribution from the formation of tocopheryl and tocotrienyl esters. The lost tocopherols and tocotrienols present at high concentration in the distillates may be recovered and used to improve the oxidative stability of SLs.

  9. Absorption and metabolism of the food contaminant 3-chloro-1,2-propanediol (3-MCPD) and its fatty acid esters by human intestinal Caco-2 cells.

    Science.gov (United States)

    Buhrke, Thorsten; Weisshaar, Rüdiger; Lampen, Alfonso

    2011-10-01

    3-Chloro-1,2-propanediol (3-MCPD) fatty acid esters are formed upon thermal processing of fat-containing foods in the presence of chloride ions. Upon hydrolytic cleavage, these substances could release free 3-MCPD. This compound is toxicologically well characterised and displayed cancerogenic potential in rodent models. Recently, serious contaminations of different food products with 3-MCPD fatty acid esters have been reported. In regard to a risk assessment, the key question is to which degree these 3-MCPD fatty acid esters are hydrolysed in the human gut. Therefore, the aim of the present project was to examine the hydrolysis of 3-MCPD fatty acid esters and the resulting release of free 3-MCPD by using differentiated Caco-2 cells, a cellular in vitro model for the human intestinal barrier. Here, we show that 3-MCPD fatty acid esters at a concentration of 100 μM were neither absorbed by the cells nor the esters were transported via a Caco-2 monolayer. 3-MCPD-1-monoesters were hydrolysed in the presence of Caco-2 cells. In contrast, a 3-MCPD-1,2-diester used in this study was obviously absorbed and metabolised by the cells. Free 3-MCPD was not absorbed by the cells, but the substance migrated through a Caco-2 monolayer by paracellular diffusion. From these in vitro studies, we conclude that 3-MCPD-1-monoesters are likely to be hydrolysed in the human intestine, thereby increasing the burden with free 3-MCPD. In contrast, intestinal cells seem to have the capacity to metabolise 3-MCPD diesters, thereby detoxifying the 3-MCPD moiety.

  10. Cu2+ Montmorillonite K10 Clay Catalyst as a Green Catalyst for Production of Stearic Acid Methyl Ester: Optimization Using Response Surface Methodology (RSM)

    OpenAIRE

    Enas A. Almadani; Farah W. Harun; Salina M. Radzi; Syamsul K. Muhamad

    2018-01-01

    Clay catalyst has received much attention to replace the homogeneous catalysts in the esterification reaction to produce fatty acid methyl ester as the source of biodiesel as it is low cost, easily available, as well as environmental friendly. However, the use of unmodified clay, in particular montmorillonite K10 (MMT K10), for the esterification of fatty acids showed that the acid conversion was less than 60% and this is not preferable to the production of biodiesel. In this study, synthesis...

  11. Used frying oils and fats and their utilization in the production of methyl esters of higher fatty acids

    Energy Technology Data Exchange (ETDEWEB)

    Cvengros, J. Jan; Cvengrosova, Zuzana [Slovak Univ. of Technology, Faculty of Chemical and Food Technology, Bratislava (Slovakia)

    2004-08-01

    From the point of view price and available capacity used frying oils or fats (UFO) represent an attractive raw material for the production of methyl esters (ME) of higher fatty acids as alternative fuels for diesel engines. If they are treated such that the required quality, with an acidity number up to 3.0 mg KOH/g and a water content up to 0.1 wt%, is achieved they can be processed to ME using standard techniques of alkali-catalysed transesterification with methanol which are utilized for production of the ME from new oils/fats. The problematic waste can thus be converted to an ecologically friendly fuel. Vacuum distillation of free fatty acids in a film evaporator is an effective method for simultaneously decreasing the content of FFA and water in UFO. Final distillation of raw ME in a film vacuum evaporator results in practically all parameters required by the standard, in the final ME being achieved. Undesirable low-temperature properties of ME derived from UFO, due to higher fraction of saturated acyls, can be adjusted by the addition of depressants-flow improvers for winterization. Some simplified methods for the quality control of UFO and ME are discussed. The conversion of acylglycerols to ME is monitored by GLC with a packed column, where the peak areas of ME in the sample before and after the reaction with an effective methylation agent are compared. The method for the determination of the water content in esters utilizes the reaction of calcium carbide with water, the volume of acetylene being measured. (Author)

  12. Biodegradable Nanoparticles Made of Amino-Acid-Based Ester Polymers: Preparation, Characterization, and In Vitro Biocompatibility Study

    Directory of Open Access Journals (Sweden)

    Temur Kantaria

    2016-12-01

    Full Text Available A systematic study of fabricating nanoparticles (NPs by cost-effective polymer deposition/solvent displacement (nanoprecipitation method has been carried out. Five amino acid based biodegradable (AABB ester polymers (four neutral and one cationic, four organic solvents miscible with water, and eight surfactants were tested for the fabrication of the goal NPs. Depending on the nature of the AABB polymers, organic solvents and surfactants, as well as on the fabrication conditions, the size (Mean Particle Diameter of the NPs could be tuned within 42 ÷ 398 nm, the zeta-potential within 12.5 ÷ +28 mV. The stability (resuspendability of the NPs upon storage (at room temperature and refrigerated was tested as well. In Vitro biocompatibility study of the NPs was performed with four different stable cell lines: A549, HeLa (human; RAW264.7, Hepa 1-6 (murine. Comparing the NPs parameters, their stability upon storage, and the data of biological examinations the best were found: As the AABB polymer, a poly(ester amide composed of l-leucine, 1,6-hexanediol and sebacic acid–8L6, as a solvent (organic phase—DMSO, and as a surfactant, Tween 20.

  13. Biosynthesis of D-alanyl-lipoteichoic acid by Lactobacillus casei: interchain transacylation of D-alanyl ester residues

    International Nuclear Information System (INIS)

    Childs, W.C. III; Taron, D.J.; Neuhaus, F.C.

    1985-01-01

    Lipoteichoic acid (LTA) from Lactobacillus casei contains poly(glycerophosphate) substituted with D-alanyl ester residues. The distribution of these residues in the in vitro-synthesized polymer is uniform. Esterification of LTA with D-alanine may occur in one of two modes: (i) addition at random or (ii) addition at a defined locus in the poly(glycerophosphate) chain followed by redistribution of the ester residues. A time-dependent transacylation of these residues from D-[ 14 C]alanyl-lipophilic LTA to hydrophilic acceptor was observed. The hydrophilic acceptor was characterized as D-alanyl-hydrophilic LTA. This transacylation requires neither ATP nor the D-alanine incorporation system, i.e., the D-alanine activating enzyme and D-alanine:membrane acceptor ligase. No evidence for an enzyme-catalyzed transacylation reaction was observed. The authors propose that this process of transacylation may be responsible for the redistribution of D-alanyl residues after esterification to the poly(glycerophosphate). As a result, it is difficult to distinguish between these proposed modes of addition

  14. Safety of docosahexaenoic acid (DHA) administered as DHA ethyl ester in a 9-month toxicity study in dogs.

    Science.gov (United States)

    Dahms, Irina; Beilstein, Paul; Bonnette, Kimberly; Salem, Norman

    2016-06-01

    DHA Ethyl Ester (DHA-EE) is a 90% concentrated ethyl ester of docosahexaenoic acid manufactured from the microalgal oil. The objective of the 9-month study was to evaluate safety of DHA-EE administered to beagle dogs at dose levels 150, 1000 and 2000 mg/kg bw/day by oral gavage and to determine reversibility of any findings after a 2-month recovery period. DHA-EE was well tolerated at all doses. There were observations of dry flaky skin with occasional reddened areas at doses ≥1000 mg/kg bw/day. These findings lacked any microscopic correlate and were no longer present after the recovery period. There were no toxicologically relevant findings in body weights, body weight gains, food consumption, ophthalmological examinations, and ECG measurements. Test article-related changes in hematology parameters were limited to decreases in reticulocyte count in the high-dose males and considered non-adverse. In clinical chemistry parameters, dose-related decreases in cholesterol and triglycerides levels were observed at all doses in males and females and attributed to the known lipid-lowering effects of DHA. There were no effects on other clinical chemistry, urinalysis or coagulation parameters. There were no abnormal histopathology findings attributed to test article. The No-Observable-Adverse-Effect Level of DHA-EE was established at 2000 mg/kg bw/day for both genders. Copyright © 2016 Elsevier Ltd. All rights reserved.

  15. Substituted thiobenzoic acid S-benzyl esters as potential inhibitors of a snake venom phospholipase A2: Synthesis, spectroscopic and computational studies

    Science.gov (United States)

    Henao Castañeda, I. C.; Pereañez, J. A.; Jios, J. L.

    2012-11-01

    4-Chlorothiobenzoic acid S-benzyl ester (I), 3-nitrothiobenzoic acid S-benzyl ester (II), 4-nitrothiobenzoic acid S-benzyl ester (III) and 4-methylthiobenzoic acid S-benzyl ester (IV) were prepared and characterized by 1H and 13C NMR, Mass spectrometry and IR spectroscopy. Quantum chemical calculations were performed with Gaussian 09 to calculate the geometric parameters and vibrational spectra. Phospholipase A2 (PLA2) was purified from Crotalus durissus cumanensis venom by molecular exclusion chromatography, followed by reverse phase-high performance liquid chromatography. Two studies of the inhibition of phospholipase A2 activity were performed using phosphatidilcholine and 4-nitro-3-octanoyloxybenzoic acid as substrates, in both cases compound II showed the best inhibitory ability, with 74.89% and 69.91% of inhibition, respectively. Average percentage of inhibition was 52.49%. Molecular docking was carried out with Autodock Vina using as ligands the minimized structures of compounds (I-IV) and as protein PLA2 (PDB code 2QOG). The results suggest that compounds I-IV could interact with His48 at the active site of PLA2. In addition, all compounds showed Van der Waals interactions with residues from hydrophobic channel of the enzyme. This interaction would impede normal catalysis cycle of the PLA2.

  16. Cavitation assisted synthesis of fatty acid methyl esters from sustainable feedstock in presence of heterogeneous catalyst using two step process.

    Science.gov (United States)

    Dubey, Sumit M; Gole, Vitthal L; Gogate, Parag R

    2015-03-01

    The present work reports the intensification aspects for the synthesis of fatty acid methyl esters (FAME) from a non-edible high acid value Nagchampa oil (31 mg of KOH/g of oil) using two stage acid esterification (catalyzed by H₂SO₄) followed by transesterification in the presence of heterogeneous catalyst (CaO). Intensification aspects of both stages have been investigated using sonochemical reactors and the obtained degree of intensification has been established by comparison with the conventional approach based on mechanical agitation. It has been observed that reaction temperature for esterification reduced from 65 to 40 °C for the ultrasonic approach whereas there was a significant reduction in the optimum reaction time for transesterification from 4h for the conventional approach to 2.5h for the ultrasound assisted approach. Also the reaction temperature reduced marginally from 65 to 60 °C and yield increased from 76% to 79% for the ultrasound assisted approach. Energy requirement and activation energy for both esterification and transesterification was lower for the ultrasound based approach as compared to the conventional approach. The present work has clearly established the intensification obtained due to the use of ultrasound and also illustrated the two step approach for the synthesis of FAME from high acid value feedstock based on the use of heterogeneous catalyst for the transesterification step. Copyright © 2014 Elsevier B.V. All rights reserved.

  17. Fast and accurate preparation fatty acid methyl esters by microwave-assisted derivatization in the yeast Saccharomyces cerevisiae.

    Science.gov (United States)

    Khoomrung, Sakda; Chumnanpuen, Pramote; Jansa-ard, Suwanee; Nookaew, Intawat; Nielsen, Jens

    2012-06-01

    We present a fast and accurate method for preparation of fatty acid methyl esters (FAMEs) using microwave-assisted derivatization of fatty acids present in yeast samples. The esterification of free/bound fatty acids to FAMEs was completed within 5 min, which is 24 times faster than with conventional heating methods. The developed method was validated in two ways: (1) through comparison with a conventional method (hot plate) and (2) through validation with the standard reference material (SRM) 3275-2 omega-3 and omega-6 fatty acids in fish oil (from the Nation Institute of Standards and Technology, USA). There were no significant differences (P>0.05) in yields of FAMEs with both validations. By performing a simple modification of closed-vessel microwave heating, it was possible to carry out the esterification in Pyrex glass tubes kept inside the closed vessel. Hereby, we are able to increase the number of sample preparations to several hundred samples per day as the time for preparation of reused vessels was eliminated. Pretreated cell disruption steps are not required, since the direct FAME preparation provides equally quantitative results. The new microwave-assisted derivatization method facilitates the preparation of FAMEs directly from yeast cells, but the method is likely to also be applicable for other biological samples.

  18. Cellulose-polyhydroxylated fatty acid ester-based bioplastics with tuning properties: Acylation via a mixed anhydride system.

    Science.gov (United States)

    Heredia-Guerrero, José A; Goldoni, Luca; Benítez, José J; Davis, Alexander; Ceseracciu, Luca; Cingolani, Roberto; Bayer, Ilker S; Heinze, Thomas; Koschella, Andreas; Heredia, Antonio; Athanassiou, Athanassia

    2017-10-01

    The synthesis of microcrystalline cellulose (MCC) and 9,10,16-hydroxyhexadecanoic (aleuritic) acid ester-based bioplastics was investigated through acylation in a mixed anhydride (trifluoroacetic acid (TFA)/trifluoroacetic acid anhydride (TFAA)), chloroform co-solvent system. The effects of chemical interactions and the molar ratio of aleuritic acid to the anhydroglucose unit (AGU) of cellulose were investigated. The degree of substitution (DS) of new polymers were characterized by two-dimensional solution-state NMR and ranged from 0.51 to 2.60. The chemical analysis by attenuated total reflection-Fourier transform infrared spectroscopy (ATR-FTIR) confirmed the presence of aleuritate groups in the structure induces the formation of new H-bond networks. The tensile analysis and the contact angle measurement confirmed the ductile behavior and the hydrophobicity of the prepared bioplastics. By increasing the aleuritate amounts, the glass transition temperature decreased and the solubility of bioplastic films in most common solvents was improved. Furthermore, this new polymer exhibits similar properties compared to commercial cellulose derivatives. Copyright © 2017 Elsevier Ltd. All rights reserved.

  19. Biomimetic L-aspartic acid-derived functional poly(ester amide)s for vascular tissue engineering.

    Science.gov (United States)

    Knight, Darryl K; Gillies, Elizabeth R; Mequanint, Kibret

    2014-08-01

    Functionalization of polymeric biomaterials permits the conjugation of cell signaling molecules capable of directing cell function. In this study, l-phenylalanine and l-aspartic acid were used to synthesize poly(ester amide)s (PEAs) with pendant carboxylic acid groups through an interfacial polycondensation approach. Human coronary artery smooth muscle cell (HCASMC) attachment, spreading and proliferation was observed on all PEA films. Vinculin expression at the cell periphery suggested that HCASMCs formed focal adhesions on the functional PEAs, while the absence of smooth muscle α-actin (SMαA) expression implied the cells adopted a proliferative phenotype. The PEAs were also electrospun to yield nanoscale three-dimensional (3-D) scaffolds with average fiber diameters ranging from 130 to 294nm. Immunoblotting studies suggested a potential increase in SMαA and calponin expression from HCASMCs cultured on 3-D fibrous scaffolds when compared to 2-D films. X-ray photoelectron spectroscopy and immunofluorescence demonstrated the conjugation of transforming growth factor-β1 to the surface of the functional PEA through the pendant carboxylic acid groups. Taken together, this study demonstrates that PEAs containing aspartic acid are viable biomaterials for further investigation in vascular tissue engineering. Copyright © 2014 Acta Materialia Inc. Published by Elsevier Ltd. All rights reserved.

  20. Synthesis, Formulation, and Adjuvanticity of Monodesmosidic Saponins with Olenanolic Acid, Hederagenin and Gypsogenin Aglycones, and some C-28 Ester Derivatives

    DEFF Research Database (Denmark)

    Greatrex, Ben W.; Daines, Alison M.; Hook, Sarah

    2015-01-01

    In an attempt to discover a new synthetic vaccine adjuvant, the glycosylation of hederagenin, gypsogenin, and oleanolic acid acceptors with di- and trisaccharide donors to generate a range of mimics of natural product QS-21 was carried out. The saponins were formulated with phosphatidylcholine...... of cholesterol and phospholipid, the choline ester derivatives produced nanocrystalline rods or helical micelles. The effects of modifying sugar stereochemistry and the aglycone on the immunostimulatory effects of the saponins was then evaluated using the activation markers MHC class II and CD86 in murine bone...... marrow dendritic cells. The most active saponin, 3-O-(Manp(13)Glcp)hederagenin, was stimulatory at high concentrations in cell culture, but this did not translate to strong responses in vivo....

  1. Caffeic acid phenethyl ester as a remedial agent for reproductive functions and oxidative stress-based pathologies of gonads.

    Science.gov (United States)

    Akyol, Sumeyya; Akbas, Ali; Butun, Ilknur; Toktas, Muhsin; Ozyurt, Huseyin; Sahin, Semsettin; Akyol, Omer

    2015-01-01

    In recent years, the studies on the roles of caffeic acid phenethyl ester (CAPE) in several disease models and cell cultures are tremendously growing. It is such a great molecule that was used by ancient times to ameliorate some diseases and nowadays, it is used by modern medicine to test the effectiveness. In this mini-review article, the protection capability of CAPE, as a liposoluble antioxidant and a potent nuclear factor kappa B inhibitor, on oxidative and non-oxidative ovary, and testis damages has been summarized. In view of our laboratory findings/experience and those reported in the hitherto literature, we suggest that CAPE possesses protective effects for pathologies of the reproductive organs induced by untoward effects of harmful molecules such as free oxygen radicals, pesticides, methotrexate, and MK-801 (dizocilpine).

  2. Determination of Chlorophenoxy Acid Methyl Esters and Other Chlorinated Herbicides by GC High-resolution QTOFMS and Soft lonization

    Directory of Open Access Journals (Sweden)

    Viorica Lopez-Avila

    2015-01-01

    Full Text Available Gas chromatography with quadrupole time-of-flight mass spectrometry (GC-QTOFMS and soft ionization generated by a rare-gas plasma is described here for the determination of various chlorophenoxy acid methyl esters and a few chlorinated herbicides. This plasma-based, wavelength-selectable ionization source, which can use Xe, Kr, Ar, Ne, or He as the plasma gas, enables ionization of GC-amenable compounds with ionization energies below 8.4, 10, 11.6, 16.5, or 22.4 eV, respectively. The advantages of soft ionization include enhanced molecular ions, reduced fragmentation, and reduced background noise as compared to electron ionization. In the study presented here for two plasma gases, we demonstrate that Kr plasma, which is softer than Ar plasma, yields molecular ions with a relative intensity >60% for 11 of the 16 test compounds. When using this “tunable” plasma to ionize the analytes, there is the possibility for selective ionization and less fragmentation, which may lead to increased sensitivity and may help structure elucidation, especially when using high-resolution mass spectrometry that generates accurate masses within a few parts per million (ppm mass errors. Data generated with the Ar plasma and real matrices such as a peppermint extract, a plum extract, and an orange peel extract, spiked with 16 test compounds, indicate that the test compounds can be detected at 1-10 pg/µL of extract, and compounds such as menthone, limonene, eucalyptol, pinene, caryophylene, and other C 15 H 24 isomers, which are present in the peppermint and the orange peel extracts at ppm to percent levels, do not appear to interfere with the determination of the chlorophenoxy acid methyl esters or the chlorinated herbicides, although there were matrix effects when the test compounds were spiked at 1-10 pg/µL of extract.

  3. Fatty acid methyl esters synthesis from non-edible vegetable oils using supercritical methanol and methyl tert-butyl ether

    International Nuclear Information System (INIS)

    Lamba, Neha; Modak, Jayant M.; Madras, Giridhar

    2017-01-01

    Highlights: • FAMEs were synthesized from non-edible oils using supercritical MeOH and MTBE. • Effect of time, temperature, pressure and molar ratio on conversions was studied. • Rate constants of reaction with methanol and MTBE differ by an order of magnitude. • Non-catalytic supercritical reactions are one order faster than acid catalyzed synthesis. - Abstract: Fatty acid methyl esters (FAMEs) are useful as biodiesel and have environmental benefits compared to conventional diesel. In this study, these esters were synthesized non-catalytically from non-edible vegetable oils: neem oil and mahua oil with two different methylating agents: methanol and methyl tert-butyl ether (MTBE). The effects of temperature, pressure, time and molar ratio on the conversion of triglycerides were studied. The temperature was varied in the range of 523–723 K with molar ratios upto 50:1 and a reaction time of upto 150 min. Conversion of neem and mahua oil to FAMEs with supercritical methanol was found to be 83% in 15 min and 99% in 10 min, respectively at 698 K. Further, a conversion of 46% of mahua oil and 59% of neem oil was obtained in 15 min at 723 K using supercritical MTBE. The rate constants evaluated using pseudo first order reaction kinetics were in the range of 4.7 × 10"−"6 to 1.0 × 10"−"3 s"−"1 for the investigated range of temperatures. The activation energies obtained were in the range of 62–113 kJ/mol for the reaction systems investigated. The supercritical synthesis was found to be superior to the catalytic synthesis of the corresponding FAMEs.

  4. Fatty Acid Methyl Ester (FAME) Succession in Different Substrates as Affected by the Co-Application of Three Pesticides.

    Science.gov (United States)

    Cardinali, Alessandra; Pizzeghello, Diego; Zanin, Giuseppe

    2015-01-01

    In intensive agriculture areas the use of pesticides can alter soil properties and microbial community structure with the risk of reducing soil quality. In this study the fatty acid methyl esters (FAMEs) evolution has been studied in a factorial lab experiment combining five substrates (a soil, two aged composts and their mixtures) treated with a co-application of three pesticides (azoxystrobin, chlorotoluron and epoxiconazole), with two extraction methods, and two incubation times (0 and 58 days). FAMEs extraction followed the microbial identification system (MIDI) and ester-linked method (EL). The pesticides showed high persistence, as revealed by half-life (t1/2) values ranging from 168 to 298 days, which confirms their recalcitrance to degradation. However, t1/2 values were affected by substrate and compost age down to 8 days for chlorotoluron in S and up to 453 days for epoxiconazole in 12M. Fifty-six FAMEs were detected. Analysis of variance (ANOVA) showed that the EL method detected a higher number of FAMEs and unique FAMEs than the MIDI one, whereas principal component analysis (PCA) highlighted that the monosaturated 18:1ω9c and cyclopropane 19:0ω10c/19ω6 were the most significant FAMEs grouping by extraction method. The cyclopropyl to monoenoic acids ratio evidenced higher stress conditions when pesticides were applied to compost and compost+soil than solely soil, as well as with final time. Overall, FAMEs profiles showed the importance of the extraction method for both substrate and incubation time, the t1/2 values highlighted the effectiveness of solely soil and the less mature compost in reducing the persistence of pesticides.

  5. Fatty Acid Methyl Ester (FAME Succession in Different Substrates as Affected by the Co-Application of Three Pesticides.

    Directory of Open Access Journals (Sweden)

    Alessandra Cardinali

    Full Text Available In intensive agriculture areas the use of pesticides can alter soil properties and microbial community structure with the risk of reducing soil quality.In this study the fatty acid methyl esters (FAMEs evolution has been studied in a factorial lab experiment combining five substrates (a soil, two aged composts and their mixtures treated with a co-application of three pesticides (azoxystrobin, chlorotoluron and epoxiconazole, with two extraction methods, and two incubation times (0 and 58 days. FAMEs extraction followed the microbial identification system (MIDI and ester-linked method (EL.The pesticides showed high persistence, as revealed by half-life (t1/2 values ranging from 168 to 298 days, which confirms their recalcitrance to degradation. However, t1/2 values were affected by substrate and compost age down to 8 days for chlorotoluron in S and up to 453 days for epoxiconazole in 12M. Fifty-six FAMEs were detected. Analysis of variance (ANOVA showed that the EL method detected a higher number of FAMEs and unique FAMEs than the MIDI one, whereas principal component analysis (PCA highlighted that the monosaturated 18:1ω9c and cyclopropane 19:0ω10c/19ω6 were the most significant FAMEs grouping by extraction method. The cyclopropyl to monoenoic acids ratio evidenced higher stress conditions when pesticides were applied to compost and compost+soil than solely soil, as well as with final time.Overall, FAMEs profiles showed the importance of the extraction method for both substrate and incubation time, the t1/2 values highlighted the effectiveness of solely soil and the less mature compost in reducing the persistence of pesticides.

  6. Identification of hydroxylcinnamoyl tartaric acid esters in Bidens pilosa by UPLC-tandem mass spectrometry

    CSIR Research Space (South Africa)

    Khoza, BS

    2016-03-01

    Full Text Available of these extracts using UPLC-qTOF-MS/MS revealed the presence of several hydoxylcinnamoyl tartaric acids. Here, different isomers of coutaric-, caftaric-, fertaric-, chicoric acid and caftaric acid glycosides were detected. The contribution of mass spectrometry...

  7. Simultaneous Disulfide and Boronic Acid Ester Exchange in Dynamic Combinatorial Libraries

    Directory of Open Access Journals (Sweden)

    Sanna L. Diemer

    2015-09-01

    Full Text Available Dynamic combinatorial chemistry has emerged as a promising tool for the discovery of complex receptors in supramolecular chemistry. At the heart of dynamic combinatorial chemistry are the reversible reactions that enable the exchange of building blocks between library members in dynamic combinatorial libraries (DCLs ensuring thermodynamic control over the system. If more than one reversible reaction operates in a single dynamic combinatorial library, the complexity of the system increases dramatically, and so does its possible applications. One can imagine two reversible reactions that operate simultaneously or two reversible reactions that operate independently. Both these scenarios have advantages and disadvantages. In this contribution, we show how disulfide exchange and boronic ester transesterification can function simultaneous in dynamic combinatorial libraries under appropriate conditions. We describe the detailed studies necessary to establish suitable reaction conditions and highlight the analytical techniques appropriate to study this type of system.

  8. Preparation of five 3-MCPD fatty acid esters, and the effects of their chemical structures on acute oral toxicity in Swiss mice.

    Science.gov (United States)

    Liu, Man; Liu, Jie; Wu, Yizhen; Gao, Boyan; Wu, Pingping; Shi, Haiming; Sun, Xiangjun; Huang, Haiqiu; Wang, Thomas Ty; Yu, Liangli Lucy

    2017-02-01

    3-monochloro-1, 2-propanediol fatty acid esters (3-MCPDEs) comprise a group of food toxicants formed during food processing. 3-MCPDEs have received increasing attention concerning their potential negative effects on human health. However, reports on the toxicity of 3-MCPD esters are still limited. To determine the effects of fatty acid substitutions on the toxicity of their esters, 1-stearic, 1-oleic, 1-linoleic, 1-linoleic-2-palmitic and 1-palmitic-2-linoleic acid esters of 3-MCPD were synthesized and evaluated with respect to their acute oral toxicities in Swiss mice. 3-MCPDEs were obtained through the reaction of 3-MCPD and fatty acid chlorides, and their purities and structures were characterized by ultraperformance liquid chromatography-quadrupole-time of flight-mass spectrometry (UPLC-Q-TOF-MS), infrared, 1 H and 13 C spectroscopic analyses. Medial lethal doses of 1-stearic, 1-oleic, 1-linoleic, 1-linoleic-2-palmitic and 1-palmitic-2-linoleic acid esters were 2973.8, 2081.4, 2016.3, 5000 and > 5000 mg kg -1 body weight. For the first time, 3-MCPDEs were observed for their toxic effects in the thymus and lung. In addition, major histopathological changes, as well as blood urea nitrogen and creatinine, were examined for mice fed the five 3-MCPDEs. The results from the present study suggest that the degree of unsaturation, chain length, number of substitution and relative substitution locations of fatty acids might alter the toxicity of 3-MCPDEs. © 2016 Society of Chemical Industry. © 2016 Society of Chemical Industry.

  9. Determining the fatty acid composition in plasma and tissues as fatty acid methyl esters using gas chromatography – a comparison of different derivatization and extraction procedures.

    Science.gov (United States)

    Ostermann, Annika I; Müller, Maike; Willenberg, Ina; Schebb, Nils Helge

    2014-12-01

    Analysis of the fatty acid (FA) composition in biological samples is commonly carried out using gas liquid chromatography (GC) after transesterification to volatile FA methyl esters (FAME). We compared the efficacy of six frequently used protocols for derivatization of different lipid classes as well as for plasma and tissue samples. Transesterification with trimethylsulfonium hydroxide (TMSH) led to insufficient derivatization efficacies for polyunsaturated FAs (PUFA, ester (CE) as well as triacylglycerols (TGs). In contrast, methanolic hydrochloric acid (HCl) as well as a combination of BF3 with methanolic sodium hydroxide (NaOH+BF3) were suitable for the derivatization of FFAs, polar lipids, TGs, and CEs (derivatization rate >80% for all tested lipids). Regarding plasma samples, all methods led to an overall similar relative FA pattern. However, significant differences were observed, for example, for the relative amount of EPA+DHA (n3-index). Absolute FA plasma concentrations differed considerably among the methods, with low yields for KOH and BF3. We also demonstrate that lipid extraction with tert-butyl methyl ether/methanol (MTBE/MeOH) is as efficient as the classical method according to Bligh and Dyer, making it possible to replace (environmentally) toxic chloroform.We conclude that HCl-catalyzed derivatization in combination with MeOH/MTBE extraction is the most appropriate among the methods tested for the analysis of FA concentrations and FA pattern in small biological samples. A detailed protocol for the analysis of plasma and tissues is included in this article.

  10. Origin of the enhanced performance in poly(3-hexylthiophene) : [6,6]-phenyl C-61-butyric acid methyl ester solar cells upon slow drying of the active layer

    NARCIS (Netherlands)

    Mihailetchi, Valentin D.; Xie, Hangxing; Boer, Bert de; Popescu, Lacramioara M.; Hummelen, Jan C.; Blom, Paul W.M.; Koster, L. Jan Anton

    2006-01-01

    The origin of the enhanced performance of bulk heterojunction solar cells based on slowly dried films of poly(3-hexylthiophene) (P3HT) and [6,6]-phenyl C-61-butyric acid methyl ester is investigated, combining charge transport measurements with numerical device simulations. Slow drying leads to a

  11. Minimal food effect for eicosapentaenoic acid and docosahexaenoic acid bioavailability from omega-3-acid ethyl esters with an Advanced Lipid TechnologiesTM (ALT®)-based formulation.

    Science.gov (United States)

    Lopez-Toledano, Miguel A; Thorsteinsson, Thorsteinn; Daak, Ahmed A; Maki, Kevin C; Johns, Colleen; Rabinowicz, Adrian L; Sancilio, Frederick D

    The absorption of eicosapentaenoic acid (EPA; 20:5n-3) and docosahexaenoic acid (DHA; 22:6n-3) omega-3-acid ethyl esters (EEs) is influenced by food. There is a need for a formulation of EE that is less impacted by food effect. SC401 is a novel Advanced Lipid Technologies-based formulation of EPA-EE and DHA-EE. In the presence of an aqueous medium, Advanced Lipid Technologies forms stable micelles in situ independent of bile salt secretion. This effect is hypothesized to improve EPA-EE and DHA-EE bioavailability while it helps mitigate the food effect associated with their consumption. The aim of the article was to assess the effect of food on the bioavailability of DHA and EPA after a single oral dose of 1530 mg omega-3 fatty acids EE (SC401) in 24 healthy subjects under fasted and low-fat (9% of total calories from fat) and high-fat (50% of total calories from fat) meal conditions. This was a randomized, open-label, single-dose, 3-period, 3-way crossover study. Blood samples for pharmacokinetic analyses were taken at predose and at 0.5, 1, 2, 3, 3.5, 4, 4.5, 5, 5.5, 6, 6.5, 7, 8, 10, 12 and 24 hours postdose. To assess the safety of the intervention, active monitoring of adverse events, physical examinations, vital signs, clinical laboratory assessments (chemistry, hematology, and urinalysis), and 12-lead electrocardiograms were conducted. SC401 showed high bioavailability of both EPA and DHA in fasted, low-fat meal, and high-fat meal conditions. No differences were found in SC401 DHA AUC 0-t (t = 24 hours) among the 3 conditions (91.69% high-fat/fasted, 97.12% low-fat/fasted, and 105.92% low-fat/high-fat; P > .05 in all cases). In contrast, SC401 EPA AUC 0-t was affected by food intake (179.06% high-fat/fasted, P food effect for DHA and partially ameliorated it for EPA. SC401 represents a convenient option for treatment of severe hypertriglyceridemia, especially for patients under a restricted intake of dietary fat. Copyright © 2017 National Lipid

  12. Effects of MAT9001 containing eicosapentaenoic acid and docosapentaenoic acid, compared to eicosapentaenoic acid ethyl esters, on triglycerides, lipoprotein cholesterol, and related variables.

    Science.gov (United States)

    Maki, Kevin C; Bobotas, George; Dicklin, Mary R; Huebner, Margie; Keane, William F

    Long-chain omega-3 fatty acid concentrate pharmaceuticals are used in the United States for treatment of severe hypertriglyceridemia (≥500 mg/dL) and are under investigation as adjuncts to statins for lowering cardiovascular risk in patients with high triglycerides (TGs; 200-499 mg/dL). To evaluate MAT9001, an investigational prescription-only omega-3 fatty acid agent containing predominantly eicosapentaenoic acid (EPA) and docosapentaenoic acid, in 42 men and women with fasting TG 200 to 400 mg/dL. In this open-label, crossover trial, subjects received MAT9001 and EPA ethyl esters (EPA-EE) in random order. They were housed in a clinical research unit for 2 14-day treatment periods, separated by a ≥35-day washout. Lipoprotein lipids, apolipoproteins (Apos) and proprotein convertase subtilisin kexin type 9 levels were measured before and at the end of each treatment period. MAT9001, compared with EPA-EE, resulted in significantly (P < .05) larger reductions from pretreatment levels for TG (-33.2% vs -10.5%), total cholesterol (-9.0% vs -6.2%), non-high-density lipoprotein cholesterol (-8.8% vs -4.6%), very low-density lipoprotein cholesterol (-32.5% vs -8.1%), Apo C3 (-25.5% vs -5.0%), and proprotein convertase subtilisin kexin type 9 (-12.3% vs +8.8%). MAT9001 also produced a significantly (P = .003) larger reduction in Apo A1 (-15.3% vs -10.2%), but responses for high-density lipoprotein cholesterol (-11.3% vs -11.1%), low-density lipoprotein cholesterol (-2.4% vs -4.3%), and Apo B (-3.8% vs -0.7%), respectively, were not significantly different relative to EPA-EE. MAT9001 produced significantly larger reductions than EPA-EE in several lipoprotein-related variables that would be expected to favorably alter cardiovascular disease risk in men and women with hypertriglyceridemia. Copyright © 2016 National Lipid Association. Published by Elsevier Inc. All rights reserved.

  13. Synthesis, characterization and fuel cell performance tests of boric acid and boron phosphate doped, sulphonated and phosphonated poly(vinyl alcohol) based composite membranes

    Science.gov (United States)

    Şahin, Alpay; Ar, İrfan

    2015-08-01

    The aim of this study is to synthesize a composite membrane having high proton conductivity, ion exchange capacity and chemical stability. In order to achieve this aim, poly(vinyl alcohol) (PVA) based composite membranes are synthesized by using classic sol-gel method. Boric acid (H3BO3) and boron phosphate (BPO4) are added to the membrane matrix in different ratios in order to enhance the membrane properties. Characterization tests, i.e; FT-IR analysis, mechanical strength tests, water hold-up capacities, swelling properties, ion exchange capacities, proton conductivities and fuel cell performance tests of synthesized membranes are carried out. As a result of performance experiments highest performance values are obtained for the membrane containing 15% boron phosphate at 0.6 V and 750 mA/cm2. Water hold-up capacity, swelling ratio, ion exchange capacity and proton conductivity of this membrane are found as 56%, 8%, 1.36 meq/g and 0.37 S/cm, respectively. These values are close to the values obtained ones for perfluorosulphonic acid membranes. Therefore this membrane can be regarded as a promising candidate for usage in fuel cells.

  14. Fatty acid methyl ester (FAME) technology for monitoring biological foaming in activated sludge: full scale plant verification.

    Science.gov (United States)

    Lee, J W; Cha, D K; Kim, I; Son, A; Ahn, K H

    2008-02-01

    Fatty acid methyl ester (FAME) technology was evaluated as a monitoring tool for quantification of Gordonia amarae in activated sludge systems. The fatty acid, 19:1 alcohol, which was identified as a unique fatty acid in G. amarae was not only confirmed to be present in foaming plant samples, but the quantity of the signature peak correlated closely with the degree of foaming. Foaming potential experiment provided a range of critical foaming levels that corresponded to G. amarae population. This range of critical Gordonia levels was correlated to the threshold signature FAME amount. Six full-scale wastewater treatment plants were selected based on a survey to participate in our full-scale study to evaluate the potential application of the FAME technique as the Gordonia monitoring tool. Greater amounts of signature FAME were extracted from the mixed liquor samples obtained from treatment plants experiencing Gordonia foaming problems. The amounts of signature FAME correlated well with the conventional filamentous counting technique. These results demonstrated that the relative abundance of the signature FAMEs can be used to quantitatively monitor the abundance of foam-causing microorganism in activated sludge.

  15. Efficient Enzymatic Synthesis of Phenolic Ester by Increasing Solubility of Phenolic Acids in Ionic Liquids

    DEFF Research Database (Denmark)

    Yang, Zhiyong; Guo, Zheng; Xu, Xuebing

    Compounds from phenolic acid family are well known natural antioxidants, but the application of phenolic acids as antioxidants in industry is limited due to the relatively low solubility in oil-based media. The properties of phenolic acids can be modified through enzymatic lipophilization...... and modified phenolic acids will have amphiphilic property, therefore they can be localized at oil-water or water-oil phase where oxidation is considered to occur frequently. It had been reported that immobilized Candida Antarctica lipase B was the most effective biocatalyst for the various esterification...... reactions, and it had been widely used for esterification of various phenolic acids with fatty alcohol or triglycerides. However, the conversion of phenolic acids is low due to low solubility in hydrophobic solvents and hindrance effect of unsaturated side chain towards the enzyme. Our studies show...

  16. Use of Fatty Acid Methyl Ester Profiles to Compare Copper-Tolerant and Copper-Sensitive Strains of Pantoea ananatis.

    Science.gov (United States)

    Nischwitz, C; Gitaitis, R; Sanders, H; Langston, D; Mullinix, B; Torrance, R; Boyhan, G; Zolobowska, L

    2007-10-01

    ABSTRACT A survey was conducted to evaluate differences in fatty acid methyl ester (FAME) profiles among strains of Pantoea ananatis, causal agent of center rot of onion (Allium cepa), isolated from 15 different onion cultivars in three different sites in Georgia. Differences in FAME composition were determined by plotting principal components (PCs) in two-dimensional plots. Euclidean distance squared (ED(2)) values indicated a high degree of similarity among strains. Plotting of PCs calculated from P. ananatis strains capable of growing on media amended with copper sulfate pentahydrate (200 mug/ml) indicated that copper-tolerant strains grouped into tight clusters separate from clusters formed by wild-type strains. However, unlike copper-sensitive strains, the copper-tolerant strains tended to cluster by location. A total of 80, 60, and 73% of the strains from Tift1, Tift2, and Tattnall, respectively, exhibited either confluent growth or partial growth on copper-amended medium. However, all strains were sensitive to a mixture of copper sulfate pentahydrate (200 mug/ml) and maneb (40 mug/ml). When copper-tolerant clones were analyzed and compared with their wild-type parents, in all cases the plotting of PCs developed from copper-tolerant clones formed tight clusters separate from clusters formed by the parents. Eigenvalues generated from these tests indicated that two components provided a good summary of the data, accounting for 98, 98, and 96% of the standardized variance for strains Pna 1-15B, Pna 1-12B, and Pna 2-5A, respectively. Furthermore, feature 4 (cis-9-hexadecenoic acid/2-hydroxy-13-methyltetradecanoic acid) and feature 7 (cis-9/trans-12/cis-7-octadecenoic acid) were the highest or second highest absolute values for PC1 in all three strains of the parents versus copper-tolerant clones, and hexadecanoic acid was the highest absolute value for PC2 in all three strains. Along with those fatty acids, dodecanoic acid and feature 3 (3-hydroxytetradecanoic

  17. A chiral Brønsted acid-catalyzed highly enantioselective Mannich-type reaction of α-diazo esters with in situ generated N-acyl ketimines.

    Science.gov (United States)

    Unhale, Rajshekhar A; Sadhu, Milon M; Ray, Sumit K; Biswas, Rayhan G; Singh, Vinod K

    2018-04-03

    A chiral phosphoric acid-catalyzed asymmetric Mannich-type reaction of α-diazo esters with in situ generated N-acyl ketimines, derived from 3-hydroxyisoindolinones has been demonstrated in this communication. A variety of isoindolinone-based α-amino diazo esters bearing a quaternary stereogenic center were afforded in high yields (up to 99%) with excellent enantioselectivities (up to 99% ee). Furthermore, the synthetic utility of the products has been depicted by the hydrogenation of the diazo moiety of adducts.

  18. New entry for synthesis of N-acylhydrazones, pyridazinones, and 1,3,4-oxadiazin-6-ones from alpha-amino acid esters.

    Science.gov (United States)

    Yasui, Eiko; Wada, Masao; Takamura, Norio

    2007-11-01

    Versatile electrophiles N-acylhydrazones are synthesized via diazotization, reduction, and acylation of alpha-amino acid esters. Reduction of diazo esters with L-selectride or tributylphosphine affords the corresponding hydrazones in good yields. Both reducing agents give anti-hydrazones as the major product although the reactivity of each reductant is slightly different. The resulting hydrazones are acylated to give N-acylhydrazones, which are subjected to further reactions to give 1,3,4-oxadiazin-6-ones that serve as useful synthetic intermediates for the Diels-Alder reaction.

  19. Antioxidant activity of phenolic acids and esters present in red wine on human Low-Density Lipoproteins

    Science.gov (United States)

    Urizzi, P.; Monje, M.-C.; Souchard, J.-P.; Abella, A.; Chalas, J.; Lindenbaum, A.; Vergnes, L.; Labidalle, S.; Nepveu, F.

    1999-01-01

    To evaluate the antioxidant activity of different phenolic acids and their esters, three types of experiments have been used. Electron paramagnetic resonance (EPR) quantitative analysis was carried out using the acetaldehyde/xanthine oxidase system and Fenton's reaction to generate superoxide and hydroxyl radicals, respectively. In a second test, hydroperoxides generated by Cu2+-catalysed oxidation of low density lipoproteins (LDL) were quantified by a modified iodometric method. In a third assay, LDL were oxidized with Esterbauer's method and modified LDL species were quantified by HPLC. The results show that the esterified phenolic derivatives present a better antioxidant activity, on the lipoperoxidation of LDL, than the corresponding phenolic acids. Trois expériences ont été menées afin d'évaluer l'activité antioxydante de différents acides et de leurs esters. Une analyse quantitative par résonance paramagnétique électronique (RPE) a été réalisée en utilisant le système acétaldéhyde/xanthine oxydase et la réaction de Fenton générant, respectivement, les radicaux superoxyde et hydroxyle. Dans un second test, les hydroperoxydes générés par une réaction d'oxydation des lipoprotéines de basse densité (LDL) catalysée par Cu2+ ont été quantifiés par une méthode iodométrique modifiée. Dans une troisième étude, les LDL ont été oxydées par la méthode d'Esterbauer et les espèces oxydées ont été quantifiées par HPLC. Les résultats montrent que les dérivés estérifiés présentent une activité antioxydante contre la lipoperoxydation des LDL bien plus importante que celle des acides phénoliques correspondants.

  20. Microwave Energy Increases Fatty Acid Methyl Ester Yield in Human Whole Blood Due to Increased Sphingomyelin Transesterification.

    Science.gov (United States)

    Metherel, Adam H; Aristizabal Henao, Juan J; Ciobanu, Flaviu; Taha, Ameer Y; Stark, Ken D

    2015-09-01

    Dried blood spots (DBS) by fingertip prick collection for fatty acid profiling are becoming increasingly popular due to ease of collection, minimal invasiveness and its amenability to high-throughput analyses. Herein, we assess a microwave-assisted direct transesterification method for the production of fatty acid methyl esters (FAME) from DBS. Technical replicates of human whole blood were collected and 25-μL aliquots were applied to chromatography strips prior to analysis by a standard 3-h transesterification method or microwave-assisted direct transesterification method under various power (variable vs constant), time (1-5 min) and reagent (1-10% H2SO4 in methanol) conditions. In addition, a standard method was compared to a 5-min, 30-W power microwave in 1% H2SO4 method for FAME yield from whole blood sphingomyelin, and sphingomyelin standards alone and spiked in whole blood. Microwave-assisted direct transesterification yielded no significant differences in both quantitative (nmol/100 µL) and qualitative (mol%) fatty acid assessments after as little as 1.5- and 1-min reaction times, respectively, using the variable power method and 5% H2SO4 in methanol. However, 30-W power for 5 min increased total FAME yield of the technical replicates by 14%. This increase appears largely due to higher sphingomyelin-derived FAME yield of up to 109 and 399% compared to the standard method when determined from whole blood or pure standards, respectively. In conclusion, microwave-assisted direct transesterification of DBS achieved in as little as 1-min, and 5-min reaction times increase total fatty acids primarily by significantly improving sphingomyelin-derived fatty acid yield.

  1. Accurate and reliable quantification of total microalgal fuel potential as fatty acid methyl esters by in situ transesterification

    Energy Technology Data Exchange (ETDEWEB)

    Laurens, Lieve M.L.; Quinn, Matthew; Wychen, Stefanie van; Templeton, David W.; Wolfrum, Edward J. [National Bioenergy Center, National Renewable Energy Laboratory, Golden, CO (United States)

    2012-04-15

    In the context of algal biofuels, lipids, or better aliphatic chains of the fatty acids, are perhaps the most important constituents of algal biomass. Accurate quantification of lipids and their respective fuel yield is crucial for comparison of algal strains and growth conditions and for process monitoring. As an alternative to traditional solvent-based lipid extraction procedures, we have developed a robust whole-biomass in situ transesterification procedure for quantification of algal lipids (as fatty acid methyl esters, FAMEs) that (a) can be carried out on a small scale (using 4-7 mg of biomass), (b) is applicable to a range of different species, (c) consists of a single-step reaction, (d) is robust over a range of different temperature and time combinations, and (e) tolerant to at least 50% water in the biomass. Unlike gravimetric lipid quantification, which can over- or underestimate the lipid content, whole biomass transesterification reflects the true potential fuel yield of algal biomass. We report here on the comparison of the yield of FAMEs by using different catalysts and catalyst combinations, with the acid catalyst HCl providing a consistently high level of conversion of fatty acids with a precision of 1.9% relative standard deviation. We investigate the influence of reaction time, temperature, and biomass water content on the measured FAME content and profile for 4 different samples of algae (replete and deplete Chlorella vulgaris, replete Phaeodactylum tricornutum, and replete Nannochloropsis sp.). We conclude by demonstrating a full mass balance closure of all fatty acids around a traditional lipid extraction process. (orig.)

  2. Graft polymerization of vinyl acetate onto starch. Saponification to starch-g-poly(vinyl alcohol)

    International Nuclear Information System (INIS)

    Fanta, G.F.; Burr, R.C.; Doane, W.M.; Russell, C.R.

    1979-01-01

    Graft polymerizations of vinyl acetate onto granular cornstarch were initiated by cobalt-60 irradiation of starch-monomer-water mixtures, and ungrafted poly(vinyl acetate) was separated from the graft copolymer by benzene extraction. Conversions of monomer to polymer were quantitative at a radiation dose of 1.0 Mrad. Over half of the polymer was present as ungrafted poly(vinyl acetate) (grafting efficiency less than 50%), and the graft copolymer contained only 34% grafted synthetic polymer (34% add-on). Lower irradiation doses produced lower conversions of monomer to polymer and gave graft copolymers with lower % add-on. Addition of minor amounts of acrylamide, methyl acrylate, and methacrylic acid as comonomers produced only small increases in % add-on and grafting efficency. Grafting efficiency was increased to 70% when a monomer mixture containing about 10% methyl methacrylate was used. Grafting efficiency could be increased to over 90% if the graft polymerization of vinyl acetate--methyl methacrylate was carried out near 0 0 C; although conversion of monomers to polymer was low and grafted polymer contained 40 to 50% poly(methyl methacrylate). Selected graft copolymers were treated with methanolic sodium hydroxide to convert starch-g-poly(vinyl acetate) to starch-g-poly(vinyl alcohol). The molecular weight of the poly(vinyl alcohol) moiety was about 30,000. The solubility of starch-g-poly(vinyl alcohol) in hot water was less than 50; however, solubility could be increased by substituting either acid-modified or hypochlorite-oxidized for unmodified starch in the graft polymerization reaction. Vinyl acetate was also graft polymerized onto acid-modified starch which had been dispersed and partially solubilized by heating in water. A total irradiation dose of either 1.0 or 0.5 Mrad gave starch-g-poly

  3. Unsaturated fatty acids lactose esters: cytotoxicity, permeability enhancement and antimicrobial activity

    OpenAIRE

    Lucarini, Simone; Fagioli, Laura; Campana, Raffaella; Cole, Hannah; Duranti, Andrea; Baffone, Wally; Vllasaliu, Driton; Casettari, Luca

    2016-01-01

    Sugar based surfactants conjugated with fatty acid chains are an emerging broad group of highly biocompatible and biodegradable compounds with established and potential future applications in the pharmaceutical, cosmetic and food industries. In this work, we investigated absorption enhancing and antimicrobial properties of disaccharide lactose, mono-esterified with unsaturated fatty acids through an enzymatic synthetic approach. After chemical and cytotoxicity characterizations, their permeab...

  4. Synthesis of Poly(vinyl ether) Thermoplastic Elastomers Having Functional Soft Segments

    OpenAIRE

    今枝, 嗣人; 漆崎, 美智遠; 阪口, 壽一; 橋本, 保; Tsuguto, IMAEDA; Michio, URUSHISAKI; Toshikazu, SAKAGUCHI; Tamotsu, HASHIMOTO

    2013-01-01

    The ABA-type triblock copolymers consisting of poly(2-adarnantyl vinyl ether) [poly(2-AdVE) as outer hard segments and poly(6-acetoxyhexyl vinyl ether) [poly(AcHVE)] poly(6-hydroxyhexyl vinyl ether) [poly(H HVE)], or poly(2-(2-methoxyethoxy)ethyl vinyl ether [poly(MOEOVE)] as inner soft segments were synthesized by sequential living cationic polymerization. Despite the presence of polar functional groups such as ester, hydroxy, and oxyethylene units in their soft segments, the two polymer seg...

  5. Direct quantification of fatty acids in wet microalgal and yeast biomass via a rapid in situ fatty acid methyl ester derivatization approach.

    Science.gov (United States)

    Dong, Tao; Yu, Liang; Gao, Difeng; Yu, Xiaochen; Miao, Chao; Zheng, Yubin; Lian, Jieni; Li, Tingting; Chen, Shulin

    2015-12-01

    Accurate determination of fatty acid contents is routinely required in microalgal and yeast biofuel studies. A method of rapid in situ fatty acid methyl ester (FAME) derivatization directly from wet fresh microalgal and yeast biomass was developed in this study. This method does not require prior solvent extraction or dehydration. FAMEs were prepared with a sequential alkaline hydrolysis (15 min at 85 °C) and acidic esterification (15 min at 85 °C) process. The resulting FAMEs were extracted into n-hexane and analyzed using gas chromatography. The effects of each processing parameter (temperature, reaction time, and water content) upon the lipids quantification in the alkaline hydrolysis step were evaluated with a full factorial design. This method could tolerate water content up to 20% (v/v) in total reaction volume, which equaled up to 1.2 mL of water in biomass slurry (with 0.05-25 mg of fatty acid). There were no significant differences in FAME quantification (p>0.05) between the standard AOAC 991.39 method and the proposed wet in situ FAME preparation method. This fatty acid quantification method is applicable to fresh wet biomass of a wide range of microalgae and yeast species.

  6. Chlorzoxazone esters of some non-steroidal anti-inflammatory (NSAI) carboxylic acids as mutual prodrugs: design, synthesis, pharmacological investigations and docking studies.

    Science.gov (United States)

    Abdel-Azeem, Ahmed Z; Abdel-Hafez, Atef A; El-Karamany, Gamal S; Farag, Hassan H

    2009-05-15

    The discovery of the inducible isoform of cyclooxygenase enzyme (COX-2) spurred the search for anti-inflammatory agents devoid of the undesirable effects associated with classical NSAIDs. New chlorzoxazone ester prodrugs (6-8) of some acidic NSAIDs (1-3) were designed, synthesized and evaluated as mutual prodrugs with the aim of improving the therapeutic potency and retard the adverse effects of gastrointestinal origin. The structure of the synthesized mutual ester prodrugs (6-8) were confirmed by IR, (1)H NMR, mass spectroscopy (MS) and their purity was ascertained by TLC and elemental analyses. In vitro chemical stability revealed that the synthesized ester prodrugs (6-8) are chemically stable in hydrochloric acid buffer pH 1.2 as a non-enzymatic simulated gastric fluid (SGF) and in phosphate buffer pH 7.4 as non-enzymatic simulated intestinal fluid (SIF). In 80% human plasma, the mutual prodrugs were found to be susceptible to enzymatic hydrolysis at relatively faster rate (t(1/2) approximately 37 and 34 min for prodrugs 6 and 7, respectively). Mutual ester prodrugs (6-8) were evaluated for their anti-inflammatory and muscle relaxation activities. Scanning electromicrographs of the stomach showed that the ester prodrugs induced very little irritancy in the gastric mucosa of rats after oral administration for 4days. In addition, docking of the mutual ester prodrugs (6-8) into COX-2 active site was conducted in order to predict the affinity and orientation of these prodrugs at the enzyme active site.

  7. Improvement of epoxy resin properties by incorporation of TiO2 nanoparticles surface modified with gallic acid esters

    International Nuclear Information System (INIS)

    Radoman, Tijana S.; Džunuzović, Jasna V.; Jeremić, Katarina B.; Grgur, Branimir N.; Miličević, Dejan S.; Popović, Ivanka G.; Džunuzović, Enis S.

    2014-01-01

    Highlights: • Nanocomposites of epoxy resin and TiO 2 nanoparticles surface modified with gallates. • The T g of epoxy resin was increased by incorporation of surface modified TiO 2 . • WVTR of epoxy resin decreased in the presence of surface modified TiO 2 nanoparticles. • WVTR of nanocomposites was reduced with increasing gallates hydrophobic chain length. • Modified TiO 2 nanoparticles react as oxygen scavengers, inhibiting steel corrosion. - Abstract: Epoxy resin/titanium dioxide (epoxy/TiO 2 ) nanocomposites were obtained by incorporation of TiO 2 nanoparticles surface modified with gallic acid esters in epoxy resin. TiO 2 nanoparticles were obtained by acid catalyzed hydrolysis of titanium isopropoxide and their structural characterization was performed by X-ray diffraction and transmission electron microscopy. Three gallic acid esters, having different hydrophobic part, were used for surface modification of the synthesized TiO 2 nanoparticles: propyl, hexyl and lauryl gallate. The gallate chemisorption onto surface of TiO 2 nanoparticles was confirmed by Fourier transform infrared and ultraviolet–visible spectroscopy, while the amount of surface-bonded gallates was determined using thermogravimetric analysis. The influence of the surface modified TiO 2 nanoparticles, as well as the length of hydrophobic part of the gallate used for surface modification of TiO 2 nanoparticles, on glass transition temperature, barrier, dielectric and anticorrosive properties of epoxy resin was investigated by differential scanning calorimetry, water vapor transmission test, dielectric spectroscopy, electrochemical impedance spectroscopy and polarization measurements. Incorporation of surface modified TiO 2 nanoparticles in epoxy resin caused increase of glass transition temperature and decrease of the water vapor permeability of epoxy resin. The water vapor transmission rate of epoxy/TiO 2 nanocomposites was reduced with increasing hydrophobic part chain length of

  8. Higher value films prepared from poly(vinyl alcohol) and amylose-fatty acid derivatives inclusion complexes

    Science.gov (United States)

    Water soluble amylose fatty acid and fatty ammonium salt inclusion complexes (AIC) were prepared by jet cooked high amylose corn starch with water soluble salts of long chain fatty acids or fatty amines. The formation of AIC was confirmed by X-ray diffraction of freeze-dried samples. After dissoluti...

  9. High-level accumulation of oleyl oleate in plant seed oil by abundant supply of oleic acid substrates to efficient wax ester synthesis enzymes.

    Science.gov (United States)

    Yu, Dan; Hornung, Ellen; Iven, Tim; Feussner, Ivo

    2018-01-01

    overall yields and the compositions of wax esters can be strongly affected by the availability of acyl-CoA substrates and to a lesser extent, by the characteristics of wax ester synthesis enzymes. For synthesis of oleyl oleate in plant seed oil, appropriate wax ester synthesis enzymes with high catalytic efficiency and desired substrate specificity should be expressed in plant cells; meanwhile, high levels of oleic acid-derived substrates need to be supplied to these enzymes by modifying the fatty acid profile of developing seeds.

  10. Suppression of skin inflammation in keratinocytes and acute/chronic disease models by caffeic acid phenethyl ester.

    Science.gov (United States)

    Lim, Kyung-Min; Bae, SeungJin; Koo, Jung Eun; Kim, Eun-Sun; Bae, Ok-Nam; Lee, Joo Young

    2015-04-01

    Skin inflammation plays a central role in the pathophysiology and symptoms of diverse chronic skin diseases including atopic dermatitis (AD). In this study, we examined if caffeic acid phenethyl ester (CAPE), a skin-permeable bioactive compound from propolis, was protective against skin inflammation using in vitro cell system and in vivo animal disease models. CAPE suppressed TNF-α-induced NF-κB activation and expression of inflammatory cytokines in human keratinocytes (HaCaT). The potency and efficacy of CAPE were superior to those of a non-phenethyl derivative, caffeic acid. Consistently, topical treatment of CAPE (0.5 %) attenuated 12-O-tetradecanoylphorbol-13-acetate(TPA)-induced skin inflammation on mouse ear as CAPE reduced ear swelling and histologic inflammation scores. CAPE suppressed increased expression of pro-inflammatory molecules such as TNF-α, cyclooxygenase-2 and inducible NO synthase in TPA-stimulated skin. TPA-induced phosphorylation of IκB and ERK was blocked by CAPE suggesting that protective effects of CAPE on skin inflammation is attributed to inhibition of NF-κB activation. Most importantly, in an oxazolone-induced chronic dermatitis model, topical application of CAPE (0.5 and 1 %) was effective in alleviating AD-like symptoms such as increases of trans-epidermal water loss, skin thickening and serum IgE as well as histologic inflammation assessment. Collectively, our results propose CAPE as a promising candidate for a novel topical drug for skin inflammatory diseases.

  11. Improving fatty acid methyl ester production yield in a lipase-catalyzed process using waste frying oils as feedstock.

    Science.gov (United States)

    Azócar, Laura; Ciudad, Gustavo; Heipieper, Hermann J; Muñoz, Robinson; Navia, Rodrigo

    2010-06-01

    The application of waste frying oil (WFO) mixed with rapeseed oil as a feedstock for the effective production of fatty acid methyl esters (FAME) in a lipase-catalyzed process was investigated. The response surface methodology (RSM) was used to optimize the interaction of four variables: the percentage of WFO in the mixed feedstock, the methanol-to-oil ratio, the dosage of Novozym 435 as a catalyst and the temperature. Furthermore, the addition of methanol to the reaction mixture in a second step after 8 h was shown to effectively diminish enzyme inhibition. Using this technique, the model predicted the optimal conditions that would reach 100% FAME, including a methanol-to-oil molar ratio of 3.8:1, 100% (wt) WFO, 15% (wt) Novozym 435 and incubation at 44.5 degrees C for 12 h with agitation at 200 rpm, and verification experiments confirmed the validity of the model. According to the model, the addition of WFO increased FAME production yield, which is largely due to its higher contents of monoacylglycerols, diacylglycerols and free fatty acids (in comparison to rapeseed oil), which are more available substrates for the enzymatic catalysis. Therefore, the replacement of rapeseed oil with WFO in Novozym 435-catalyzed processes could diminish biodiesel production costs since it is a less expensive feedstock that increases the production yield and could be a potential alternative for FAME production on an industrial scale. (c) 2009 The Society for Biotechnology, Japan. Published by Elsevier B.V. All rights reserved.

  12. Caffeic acid phenethyl ester downregulates phospholipase D1 via direct binding and inhibition of NFκB transactivation

    Energy Technology Data Exchange (ETDEWEB)

    Park, Mi Hee; Kang, Dong Woo [Department of Molecular Biology, Pusan National University, Busan 609-735 (Korea, Republic of); Jung, Yunjin [College of Pharmacy, Pusan National University, Busan 609-735 (Korea, Republic of); Choi, Kang-Yell [Translational Research Center for Protein Function Control, Department of Biotechnology, College of Life Science and Biotechnology, Yonsei University, Seoul (Korea, Republic of); Min, Do Sik, E-mail: minds@pusan.ac.kr [Department of Molecular Biology, Pusan National University, Busan 609-735 (Korea, Republic of)

    2013-12-06

    Highlights: •We found CAFÉ, a natural product that suppresses expression and activity of PLD1. •CAPE decreased PLD1 expression by inhibiting NFκB transactivation. •CAPE rapidly inhibited PLD activity via its binding to a Cys837 of PLD1. •PLD1 downregulation by CAPE inhibited invasion and proliferation of glioma cells. -- Abstract: Upregulation of phospholipase D (PLD) is functionally linked with oncogenic signals and tumorigenesis. Caffeic acid phenethyl ester (CAPE) is an active compound of propolis extract that exhibits anti-proliferative, anti-inflammatory, anti-oxidant, and antineoplastic properties. In this study, we demonstrated that CAPE suppressed the expression of PLD1 at the transcriptional level via inhibition of binding of NFκB to PLD1 promoter. Moreover, CAPE, but not its analogs, bound to a Cys837 residue of PLD1 and inhibited enzymatic activity of PLD. CAPE also decreased activation of matrix metalloproteinases-2 induced by phosphatidic acid, a product of PLD activity. Ultimately, CAPE-induced downregulation of PLD1 suppressed invasion and proliferation of glioma cells. Taken together, the results of this study indicate that CAPE might contribute to anti-neoplastic effect by targeting PLD1.

  13. Poly(glycerol adipate)-fatty acid esters as versatile nanocarriers

    DEFF Research Database (Denmark)

    Weiss, Verena M; Naolou, Toufik; Hause, Gerd

    2012-01-01

    Poly(glycerol adipate) (PGA) is a biodegradable polymer with promising features for nanoparticulate drug carrier systems. By acylation of PGA with fatty acids, composite systems with amphiphilic properties can be obtained. Variation of the fatty acid (laurate, stearate and behenate) and their sub...... and the nanoparticles. With their diverse particle shapes and internal structures as well as their different thermal behavior, aggregate states and polarities, the systems offer promising possibilities as delivery systems for lipophilic, amphiphilic and water soluble drugs.......Poly(glycerol adipate) (PGA) is a biodegradable polymer with promising features for nanoparticulate drug carrier systems. By acylation of PGA with fatty acids, composite systems with amphiphilic properties can be obtained. Variation of the fatty acid (laurate, stearate and behenate...

  14. Synthesis and Antiradical Activity of Isoquercitrin Esters with Aromatic Acids and Their Homologues

    Czech Academy of Sciences Publication Activity Database

    Heřmánková-Vavříková, Eva; Křenková, Alena; Petrásková, Lucie; Chambers, Christopher S.; Zápal, Jakub; Kuzma, Marek; Valentová, Kateřina; Křen, Vladimír

    2017-01-01

    Roč. 18, č. 5 (2017), s. 1-14, č. článku 1074. E-ISSN 1422-0067 R&D Projects: GA ČR(CZ) GP14-14373P; GA MŠk(CZ) LD15082 Institutional support: RVO:61388971 Keywords : isoquercitrin * aromatic acid * gallic acid Subject RIV: CE - Biochemistry OBOR OECD: Microbiology Impact factor: 3.226, year: 2016

  15. N-(Fluoren-9-ylmethoxycarbonyl-l-aspartic acid 4-tert-butyl ester

    Directory of Open Access Journals (Sweden)

    Kazuhiko Yamada

    2009-11-01

    Full Text Available The bond distances and bond angles of the title compound, C23H25NO6, are consistent with values typically found for fluoren-9-ylmethoxycarbonyl-protected amino acids. The conformations of the backbone and the side chain are slightly different from those of l-aspartic acid. The crystal structure exhibits two intermolecular hydrogen bonds, forming a two-dimensional sheet structure parallel to the ab plane.

  16. Non-catalytic production of fatty acid ethyl esters from soybean oil with supercritical ethanol in a two-step process using a microtube reactor

    International Nuclear Information System (INIS)

    Silva, Camila da; Lima, Ana Paula de; Castilhos, Fernanda de; Cardozo Filho, Lucio; Oliveira, J. Vladimir

    2011-01-01

    This work reports the production of fatty acid ethyl esters (FAEE) from the transesterification of soybean oil in supercritical ethanol in a continuous catalyst-free process using different reactor configurations. Experiments were performed in a microtube reactor with experimental simulation of two reactors operated in series and a reactor with recycle, both configurations at a constant temperature of 573 K, pressure of 20 MPa and oil to ethanol mass ratio of 1:1. Results show that the configurations studied with intermediate separation of glycerol afford higher conversions of vegetable oil to its fatty acid ethyl ester derivatives when compared to the one-step reaction, with relatively low decomposition of fatty acids (<3.0 wt%).

  17. Scientific opinion on the risks for human health related to the presence of 3-and 2-monochloropropanediol (MCPD), and their fatty acid esters, and glycidyl fatty acid esters in food

    DEFF Research Database (Denmark)

    Petersen, Annette

    EFSA was asked to deliver a scientific opinion on free and esterified 3- and 2-monochloropropane-1, 2-diol (MCPD) and glycidyl esters in food. Esters of 3- and 2-MCPD and glycidol are contaminants of processed vegetable oils; free MCPDs are formed in some processed foods. The Panel on Contaminant...

  18. Preparation of nanogels by radiation-induced cross-linking of interpolymer complexes of poly (acrylic acid) with poly (vinyl pyrrolidone) in aqueous medium

    Science.gov (United States)

    Ghaffarlou, Mohammadreza; Sütekin, S. Duygu; Güven, Olgun

    2018-01-01

    Functional nanogels were prepared from interpolymer complexes (IPC) of poly (vinyl pyrrolidone) and poly (acrylic acid) by gamma irradiation of their aqueous solutions. The coil size of IPCs prepared under different experimental conditions (polymer molecular weight, concentration, mixing ratios, pH and temperature) were measured by Dynamic Light Scattering (DLS) technique prior to irradiation. At relatively low absorbed doses of 5 and 10 kGy, IPC nanogels with a range of 30-250 nm diameters, -12 to -28 mV zeta potentials and polydispersities lower than 0.17 were obtained. The sizes of the nanogels were found to be smaller than the size of the precursor IPC coil sizes (40-300 nm) due to the formation of intra-chain crosslinks. Thus a recipe of preparing multifunctional nanogels with double amphiphilic properties carrying polyacidic and nonionic polymer structures with the range of above listed properties has been developed. These nanogels show narrow size distribution and high colloidal stability increasing their potential to be used as biocompatible drug carriers with controlled-release properties. PVP-PAA IPC nanogels were characterized by dynamic light scattering (DLS), atomic force microscopy (AFM) and scanning electron microscopy (SEM) techniques.

  19. Radiation grafting of pH-sensitive acrylic acid and 4-vinyl pyridine onto nylon-6 using one- and two-step methods

    International Nuclear Information System (INIS)

    Ortega, Alejandra; Alarcón, Darío; Muñoz-Muñoz, Franklin; Garzón-Fontecha, Angélica; Burillo, Guillermina

    2015-01-01

    Acrylic acid (AAc) and 4-vinyl pyridine (4VP) were γ-ray grafted onto nylon-6 (Ny 6 ) films via pre-irradiation oxidative method. These monomers were grafted using a one-step method to render Ny 6 -g–(AAc/4VP). A two-step or sequential method was used to render (Ny 6 -g–AAc)-g–4VP. Random copolymer branches were obtained when the grafting was carried out via one-step method using the two monomers together. The two-step method was applied to graft chains of 4VP on both Ny 6 substrate and previously grafted AAc chains (Ny 6 -g–AAc). The two types of binary copolymers synthesized were characterized to determine the amount of grafted polymers, the thermal behavior (DSC and TGA), the surface composition (XPS), and the pH responsiveness. In the two-step process, it is possible to achieve a higher graft yield, better control of the amount of each monomer, good reversibility in the swelling/deswelling process and shorter time to achieve equilibrium swelling. - Highlights: • A new binary graft of 4VP and AAc onto Ny 6 films was synthesized by γ-radiation. • The binary grafted material has potential application for heavy ion retention. • The two-step method shows better conditions in swelling and reversibility properties. • Surface distribution of monomers was evaluate by XPS characterization

  20. Synthesis of fatty acid methyl ester from crude jatropha (Jatropha curcas Linnaeus) oil using aluminium oxide modified Mg-Zn heterogeneous catalyst.

    Science.gov (United States)

    Olutoye, M A; Hameed, B H

    2011-06-01

    The synthesis of fatty acid methyl esters (FAME) as a substitute to petroleum diesel was investigated in this study from crude jatropha oil (CJO), a non-edible, low-cost alternative feedstock, using aluminium modified heterogeneous basic oxide (Mg-Zn) catalyst. The transesterification reaction with methanol to methyl esters yielded 94% in 6h with methanol-oil ratio of 11:1, catalyst loading of 8.68 wt.% at 182°C and the properties of CJO fuel produced were determine and found to be comparable to the standards according to ASTM. In the range of experimental parameters investigated, it showed that the catalyst is selective to production of methyl esters from oil with high free fatty acid (FFA) and water content of 7.23% and 3.28%, respectively in a single stage process. Thus, jatropha oil is a promising feedstock for methyl ester production and large scale cultivation will help to reduce the product cost. Copyright © 2011 Elsevier Ltd. All rights reserved.