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Sample records for acid allyl ester

  1. Catalytic Oxidation of Allylic Alcohols to Methyl Esters

    DEFF Research Database (Denmark)

    Gallas-Hulin, Agata; Kotni, Rama Krishna; Nielsen, Martin

    2017-01-01

    parameters are studied to find the suitable reaction conditions. All catalysts are characterised by XRD, XRF and TEM. Among these catalysts, Au/TiO2 showed the most efficient catalytic activity towards the selective oxidation of allylic alcohols to the corresponding esters. Moreover, the same Au/TiO2...

  2. A convenient method for lactonization of α-allyl esters using iodine ...

    African Journals Online (AJOL)

    A simple method for the synthesis of α-γ-disubstituted-γ-butyrolactones by cyclization of α-allyl esters using iodine in dimethylsulphoxide is reported. This method is efficient and operationally simple in comparison to methods using transition metal complexes. KEY WORDS: γ-Butyrolactones, α-Allyl esters, Iodine, Dimethyl ...

  3. One-pot synthesis of optically active allyl esters via lipase-vanadium combo catalysis.

    Science.gov (United States)

    Akai, Shuji; Hanada, Ryosuke; Fujiwara, Noboru; Kita, Yasuyuki; Egi, Masahiro

    2010-11-05

    The combination of vanadium-oxo compounds (3 or 4) with a lipase produced the regio- and enantioconvergent transformation of racemic allyl alcohols (1 or 2) into optically active allyl esters. In this system, the vanadium compounds catalyzed the continuous racemization of the alcohols along with the transposition of the hydroxyl group, while the lipase effected the chemo- and enantioselective esterification to achieve the dynamic kinetic resolution.

  4. Petasis Borono-Mannich reaction and allylation of carbonyl compounds via transient allyl boronates generated by palladium-catalyzed substitution of allyl alcohols. an efficient one-pot route to stereodefined alpha-amino acids and homoallyl alcohols.

    Science.gov (United States)

    Selander, Nicklas; Kipke, Andreas; Sebelius, Sara; Szabó, Kalman J

    2007-11-07

    An efficient one-pot procedure was designed by integration of the pincer-complex-catalyzed borylation of allyl alcohols in the Petasis borono-Mannich reaction and in allylation of aldehydes and ketones. These procedures are suitable for one-pot synthesis of alpha-amino acids and homoallyl alcohols from easily available allyl alcohol, amine, aldehyde, or ketone substrates. In the presented transformations, the active allylating agents are in situ generated allyl boronic acid derivatives. These transient intermediates are proved to be reasonably acid-, base-, alcohol-, water-, and air-stable species, which allows a high level of compatibility with the reaction conditions of the allylation of various aldehyde/ketone and imine electrophiles. The boronate source of the reaction is diboronic acid or in situ hydrolyzed diboronate ester ensuring that the waste product of the reaction is nontoxic boric acid. The regio- and stereoselectivity of the reaction is excellent, as almost all products form as single regio- and stereoisomers. The described procedure is suitable to create quaternary carbon centers in branched allylic products without formation of the corresponding linear allylic isomers. Furthermore, products comprising three stereocenters were formed as single products without formation of other diastereomers. Because of the highly disciplined consecutive processes, up to four-step, four-component transformations could be performed selectively as a one-pot sequence. For example, stereodefined pyroglutamic acid could be prepared from a simple allyl alcohol, a commercially available amine, and glyoxylic acid in a one-step procedure. The presented method also grants an easy access to stereodefined 1,7-dienes that are useful substrates for Grubbs ring-closing metathesis.

  5. CATALYTIC ENANTIOSELECTIVE ALLYLIC OXIDATION

    NARCIS (Netherlands)

    Rispens, Minze T.; Zondervan, Charon; Feringa, Bernard

    Several chiral Cu(II)-complexes of cyclic amino acids catalyse the enantioselective allylic oxidation of cyclohexene to cyclohexenyl esters. Cyclohexenyl propionate was obtained in 86% yield with e.e.'s up to 61%.

  6. IBX mediated reaction of β-enamino esters with allylic alcohols: a one pot metal free domino approach to functionalized pyridines.

    Science.gov (United States)

    Gade, Narendar Reddy; Devendram, V; Pal, Manojit; Iqbal, Javed

    2013-09-18

    IBX facilitated the reaction of β-enamino esters with allylic alcohols affording a direct, one-pot and metal free synthesis of functionalized pyridines including 2-substituted nicotinic acids, densely substituted pyridines and precursors of azafluorenones. The methodology also afforded the racemic pyridine core of cyclothiazomycin.

  7. A convenient method for lactonization of α-allyl esters using iodine in dimethyl- sulphoxide

    Directory of Open Access Journals (Sweden)

    B. R. Nawghare

    2014-09-01

    Full Text Available A simple method for the synthesis of α-γ-disubstituted-γ-butyrolactones by cyclization of α-allyl esters using iodine in dimethylsulphoxide is reported. This method is efficient and operationally simple in comparison to methods using transition metal complexes. DOI: http://dx.doi.org/10.4314/bcse.v28i3.16

  8. One-pot synthesis of enantiomerically pure N-protected allylic amines from N-protected α-amino esters.

    Science.gov (United States)

    Silveira-Dorta, Gastón; Álvarez-Méndez, Sergio J; Martín, Víctor S; Padrón, José M

    2016-01-01

    An improved protocol for the synthesis of enantiomerically pure allylic amines is reported. N-Protected α-amino esters derived from natural amino acids were submitted to a one-pot tandem reduction-olefination process. The sequential reduction with DIBAL-H at -78 °C and subsequent in situ addition of organophosphorus reagents yielded the corresponding allylic amines without the need to isolate the intermediate aldehyde. This circumvents the problem of instability of the aldehydes. The method tolerates well both Wittig and Horner-Wadsworth-Emmons organophosphorus reagents. A better Z-(dia)stereoselectivity was observed when compared to the previous one-pot method. The (dia)stereoselectivity of the process was affected neither by the reaction solvent nor by the amount of DIBAL-H employed. The method is compatible with the presence of free hydroxy groups as shown with serine and threonine derivatives.

  9. Enantioselective Synthesis of Acyclic α-Quaternary Carboxylic Acid Derivatives through Iridium-Catalyzed Allylic Alkylation.

    Science.gov (United States)

    Shockley, Samantha E; Hethcox, J Caleb; Stoltz, Brian M

    2017-09-11

    The first highly enantioselective iridium-catalyzed allylic alkylation that provides access to products bearing an allylic all-carbon quaternary stereogenic center has been developed. The reaction utilizes a masked acyl cyanide (MAC) reagent, which enables the one-pot preparation of α-quaternary carboxylic acids, esters, and amides with a high degree of enantioselectivity. The utility of these products is further explored through a series of diverse product transformations. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  10. Palladium-catalyzed allylation of α-hydroxy acids

    NARCIS (Netherlands)

    Moorlag, Hendrik; Vries, de Johannes; KAPTEIN, B; Schoemaker, Hans E.; Kamphuis, Johan; KELLOGG, RM

    Mandelic and lactic acids are converted to the 1,3-dioxolan-4-ones by treatment with acetone dimethyl acetal. Deprotonation followed by treatment with an allyl acetate and a catalytic amount (1 mol%) of palladium catalyst afforded the allylated dioxolanones, which could be hydrolyzed to the

  11. Expedient iron-catalyzed coupling of alkyl, benzyl and allyl halides with arylboronic esters.

    Science.gov (United States)

    Bedford, Robin B; Brenner, Peter B; Carter, Emma; Carvell, Thomas W; Cogswell, Paul M; Gallagher, Timothy; Harvey, Jeremy N; Murphy, Damien M; Neeve, Emily C; Nunn, Joshua; Pye, Dominic R

    2014-06-23

    While attractive, the iron-catalyzed coupling of arylboron reagents with alkyl halides typically requires expensive or synthetically challenging diphosphine ligands. Herein, we show that primary and secondary alkyl bromides and chlorides, as well as benzyl and allyl halides, can be coupled with arylboronic esters, activated with alkyllithium reagents, by using very simple iron-based catalysts. The catalysts used were either adducts of inexpensive and widely available diphosphines or, in a large number of cases, simply [Fe(acac)3] with no added co-ligands. In the former case, preliminary mechanistic studies highlight the likely involvement of iron(I)-phosphine intermediates. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  12. Fumaric acid esters.

    Science.gov (United States)

    Rostami Yazdi, Martin; Mrowietz, Ulrich

    2008-01-01

    Several clinical studies have shown that systemic therapy with fumaric acid esters (FAEs) in patients with moderate to severe psoriasis is effective and has a good long-term safety profile. For therapeutic use, tablets with a defined mixture of FAEs (dimethylfumarate [DMF] and three different salts of monoethylfumarate) are registered in Germany. There is evidence that DMF is the most essential component in this formulation with an antipsoriatic effect. Currently, there are few data on the pharmacokinetics of fumarates in human beings. DMF seems to act as a prodrug for its main metabolite: monomethylfumarate. This hypothesis was supported by the observation that only monomethylfumarate was detected in the plasma of human beings after the oral administration of FAEs. FAEs have been tested in different biological assays, and effects such as inhibition of the nuclear factor kappa B pathway or induction of apoptosis by DMF have been described. For these data, the role of DMF as a modulator of intracellular glutathione plays an important role.

  13. Crystal structure of 4′-allyl-4,5,6,7,2′,7′-hexachlorofluorescein allyl ester unknown solvate

    Directory of Open Access Journals (Sweden)

    Lili Wang

    2018-01-01

    Full Text Available In the title compound, 4′-allyl-4,5,6,7,2′,7′-hexachlorofluorescein allyl ester {systematic name: prop-2-en-1-yl 2,3,4,5-tetrachloro-6-[2,7-dichloro-6-hydroxy-3-oxo-4-(prop-2-en-1-yl-3H-xanthen-9-yl]benzoate}, C26H14Cl6O5, accompanied by unknown solvate molecules, the dihedral angle between the xanthene ring system (r.m.s. deviation = 0.046 Å and the pentasubstituted benzene ring is 71.67 (9°. Both allyl groups are disordered over two sets of sites in statistical ratios. The scattering contributions of the disordered solvent molecules (both Ph2O and CHCl3, as identified by NMR were removed with the PLATON SQUEEZE algorithm [Spek (2015. Acta Cryst. C71, 9–18]. In the crystal, tetrameric supramolecular aggregates linked by O—H...O hydrogen bonds occur; these further interact with neighboring aggregates through C—Cl...π interactions arising from the benzene rings, forming infinite two-dimensional sheets. Each C6Cl4 ring shifts in the direction perpendicular to the two-dimensional sheet, exhibiting a helical chain in which every C6Cl4 ring is utilized as both a donor and an acceptor of Cl...π contacts. Thus, these two-dimensional sheets pack in a helical fashion, constructing a three-dimensional network.

  14. Synthesis and biological activities of 4-chloroindole-3-acetic acid and its esters.

    Science.gov (United States)

    Katayama, M

    2000-04-01

    4-Chloroindole-3-acetic acid (4-Cl-IAA) and its esters were synthesized from 2-chloro-6-nitrotoluene as the starting material. The biological activities of 4-CI-IAA and its esters were determined by four bioassays. Except for the tert-butyl ester, 4-Cl-IAA and its esters had stronger elongation activity toward Avena coleoptiles than had indole-3-acetic acid. The biological activities of the methyl, ethyl and allyl esters were as strong as the activity of the free acid. All the esters, except for the tert-butyl, inhibited Chinese cabbage hypocotyl growth more than the free acid did, and all the esters induced severe swelling and formation of numerous lateral roots in black gram seedlings even at a low concentration. Furthermore, adventitious root formation was strongly promoted in Serissa japonica cuttings by all the esters. The root formation-promoting activities of the ethyl and allyl esters were about three times the value for indole-3-butyric acid which is used to promote and accelerate root formation in plant cuttings.

  15. One-Pot Conversion of N-Allyl-α-cyano Esters to α-Allyl-α-cyano Lactams through a Hydrolysis/Ketene Formation/Cyclization/Claisen Rearrangement Sequence.

    Science.gov (United States)

    Shen, Mei-Hua; Han, Mei; Xu, Hua-Dong

    2016-03-04

    An intramolecular ketene aza-Claisen rearrangement is developed for the first time to enable the stereoselective synthesis of α-ally-α-cyano-lactams from N-allyl amino esters. This reaction also exhibits outstanding chemoselectivity when an unsymmetrical bis-N-allyl group is present in the starting molecule. The usefulness of this method is demonstrated by a short synthesis of optically active bicyclolactam from l-proline.

  16. Synthesis of Chiral, Enantiopure Allylic Amines by the Julia Olefination of α-Amino Esters

    Directory of Open Access Journals (Sweden)

    Fabio Benedetti

    2016-06-01

    Full Text Available The four-step conversion of a series of N-Boc-protected l-amino acid methyl esters into enantiopure N-Boc allylamines by a modified Julia olefination is described. Key steps include the reaction of a lithiated phenylalkylsulfone with amino esters, giving chiral β-ketosulfones, and the reductive elimination of related α-acetoxysulfones. The overall transformation takes place under mild conditions, with good yields, and without loss of stereochemical integrity, being in this respect superior to the conventional Julia reaction of α-amino aldehydes.

  17. Asymmetric allylation of α-ketoester-derived N-benzoylhydrazones promoted by chiral sulfoxides/N-oxides Lewis bases: highly enantioselective synthesis of quaternary α-substituted α-allyl-α-amino acids.

    Science.gov (United States)

    Reyes-Rangel, Gloria; Bandala, Yamir; García-Flores, Fred; Juaristi, Eusebio

    2013-09-01

    Chiral sulfoxides/N-oxides (R)-1 and (R,R)-2 are effective chiral promoters in the enantioselective allylation of α-keto ester N-benzoylhydrazone derivatives 3a-g to generate the corresponding N-benzoylhydrazine derivatives 4a-g, with enantiomeric excesses as high as 98%. Representative hydrazine derivatives 4a-b were subsequently treated with SmI2, and the resulting amino esters 5a-b with LiOH to obtain quaternary α-substituted α-allyl α-amino acids 6a-b, whose absolute configuration was assigned as (S), with fundament on chemical correlation and electronic circular dichroism (ECD) data. © 2013 Wiley Periodicals, Inc.

  18. Fumaric acid esters in dermatology

    OpenAIRE

    Uwe Wollina

    2011-01-01

    Fumaric acid esters (FAE) are substances of interest in dermatology. FAE exert various activities on cutaneous cells and cytokine networks. So far only a mixture of dimethylfumarate (DMF) and three salts of monoethylfumarate (MEF) have gained approval for the oral treatment of moderate-to-severe plaque-type psoriasis in Germany. DMF seems to be the major active component. There is evidence that FAE are not only effective and safe in psoriasis but granulomatous non-infectious diseases like gra...

  19. Fumaric acid esters in dermatology

    Directory of Open Access Journals (Sweden)

    Uwe Wollina

    2011-01-01

    Full Text Available Fumaric acid esters (FAE are substances of interest in dermatology. FAE exert various activities on cutaneous cells and cytokine networks. So far only a mixture of dimethylfumarate (DMF and three salts of monoethylfumarate (MEF have gained approval for the oral treatment of moderate-to-severe plaque-type psoriasis in Germany. DMF seems to be the major active component. There is evidence that FAE are not only effective and safe in psoriasis but granulomatous non-infectious diseases like granuloma annulare, necrobiosis lipoidica and sarcoidosis. In vitro and animal studies suggest some activity in malignant melanoma as well.

  20. Fumaric acid esters in dermatology.

    Science.gov (United States)

    Wollina, Uwe

    2011-07-01

    Fumaric acid esters (FAE) are substances of interest in dermatology. FAE exert various activities on cutaneous cells and cytokine networks. So far only a mixture of dimethylfumarate (DMF) and three salts of monoethylfumarate (MEF) have gained approval for the oral treatment of moderate-to-severe plaque-type psoriasis in Germany. DMF seems to be the major active component. There is evidence that FAE are not only effective and safe in psoriasis but granulomatous non-infectious diseases like granuloma annulare, necrobiosis lipoidica and sarcoidosis. In vitro and animal studies suggest some activity in malignant melanoma as well.

  1. Exciton Coupling in Circular Dichroic Spectroscopy as a Tool for Establishing the Absolute Configuration of alpha,beta-Unsaturated Esters of Allylic Alcohols

    DEFF Research Database (Denmark)

    Lauridsen, A.; Cornett, Claus; Christensen, S. B.

    1991-01-01

    alpha-beta-Unsaturated esters of allylic alcohols have been shown to exhibit exciton coupling by circular dichroic spectroscopy. This coupling permits the establishment of the absolute configuration. The method was used to prove the absolute configuration at C-2 of archangelolide. Detailed NMR...

  2. Bio-based acrylic acid from sugar via propylene glycol and allyl alcohol

    NARCIS (Netherlands)

    Pramod, C. V.; Fauziah, R.; Seshan, K.; Lange, J. P.

    2018-01-01

    A new route for producing bio-based acrylic acid is proposed. It starts with the conversion of carbohydrates to propylene glycol, being main or by-product, and proceeds via a subsequent dehydration to allyl alcohol under gas-phase conditions over K-modified ZrO2 and a final oxidation over MoWVOx

  3. A diastereoselective one-pot, three-step cascade toward α-substituted allylboronic esters.

    Science.gov (United States)

    Böse, Dietrich; Niesobski, Patrik; Lübcke, Marvin; Pietruszka, Jörg

    2014-05-16

    A new highly diastereoselective synthesis of chiral α-substituted allylboronic esters, based on a one-pot, three-step cascade, is presented. The palladium- and acid-cocatalyzed reaction cascade involves a desilylation of a TBS-protected allylic alcohol, borylation, and addition of an allyl group to an aldehyde. Herein we present the first application of a TBS-protected allylic alcohol in a palladium-catalyzed borylation/allylation reaction.

  4. Additive-free decarboxylative coupling of cinnamic acid derivatives in water: synthesis of allyl amines.

    Science.gov (United States)

    Park, Kyungho; Lee, Sunwoo

    2015-03-06

    The first example of an additive-free decarboxylative coupling of cinnamic acid derivatives with formaldehyde and amines to afford the corresponding allyl amines is reported. This reaction is highly environmentally friendly because it was conducted in H2O and without any additives, releasing only CO2 and H2O as byproducts. This reaction showed a broad substrate scope including cyclic and acyclic amines and high functional group tolerance. Moreover, phenyl dienoic acid participated in this type of decarboxylative coupling reaction.

  5. Use of fumaric acid esters in psoriasis

    OpenAIRE

    Roll Antonie; Reich Kristian; Boer Almut

    2007-01-01

    Fumaric acid esters (FAE) are chemical compounds derived from the unsaturated dicarbonic acid fumaric acid. The usage of FAEs in treatment of psoriasis was introduced in the late 1950′s. In the 1980s more standardized oral preparations of FAEs were developed containing dimethylfumarate(DMF) and salts of monoethylfumarate(MEF) as main compounds. In 1994, Fumaderm ® an enteric-coated tablet containing DMF and calcium, magnesium, and zinc salts of MEF was approved for the treatment...

  6. Naturally Occurring Cinnamic Acid Sugar Ester Derivatives

    Directory of Open Access Journals (Sweden)

    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.

  7. Microwave-assisted cleavage of Alloc and Allyl Ester protecting groups in solid phase peptide synthesis.

    Science.gov (United States)

    Wilson, Krista R; Sedberry, Seth; Pescatore, Robyn; Vinton, Daniel; Love, Brian; Ballard, Sarah; Wham, Bradley C; Hutchison, Stacy K; Williamson, Eric J

    2016-10-01

    Orthogonal protection of amino acid side chains in solid phase peptide synthesis allows for selective deprotection of side chains and the formation of cyclic peptides on resin. Cyclizations are useful as they may improve the activity of the peptide or improve the metabolic stability of peptides in vivo. One cyclization method often used is the formation of a lactam bridge between an amine and a carboxylic acid. It is desirable to perform the cyclization on resin as opposed to in solution to avoid unwanted side reactions; therefore, a common strategy is to use -Alloc and -OAllyl protecting groups as they are compatible with Fmoc solid phase peptide synthesis conditions. Alloc and -OAllyl may be removed using Pd(PPh3 )4 and phenylsilane in DMF. This method can be problematic as the reaction is most often performed at room temperature under argon gas. It is not usually done at higher temperatures because of the fear of poisoning the palladium catalyst. As a result, the reaction is long and reagent-intensive. Herein, we report the development of a method in which the -Alloc/-OAllyl groups are removed using a microwave synthesizer under atmospheric conditions. The reaction is much faster, allowing for the removal of the protecting groups before the catalyst is oxidized, as well as being less reagent-intensive. This method of deprotection was tested using a variety of amino acid sequences and side chain protecting groups, and it was found that after two 5-min deprotections at 38°C, all -Alloc and -OAllyl groups were removed with >98% purity. Copyright © 2016 European Peptide Society and John Wiley & Sons, Ltd. Copyright © 2016 European Peptide Society and John Wiley & Sons, Ltd.

  8. Organocopper reactions with allylic acrylates. The preparation of {gamma},{delta}-unsaturated acids and the subsequent transformation to {gamma}-lactones

    Energy Technology Data Exchange (ETDEWEB)

    Eriksson, M.; Nilsson, M.; Olsson, T. [Chalmers Univ. of Technology, Goeteborg (Sweden)

    1995-12-31

    The conjugate addition of organocopper reagents to {alpha},{beta}-unsaturated ketones and esters is a commonly used method for carbon-carbon bond formation. When this is applied on allylic enoates, the primary ester enolates/silyl ketene acetals from the addition undergo Claisen rearrangement at room temperature to afford diastereomeric mixtures of {gamma},{delta}-unsaturated acids after hydrolytic work-up. The E/Z ratio for the primary ester enolates/silyl ketene acetals controls the erythro:threo ratio for the {gamma},{delta}-unsaturated acids. The present work is an investigation of different organocopper reagents (e.g. RCu(LiI)-TMSI) in reactions with crotyl and cinnamyl acrylate. The diastereomeric ratio is strongly influenced by the organocopper reagent (RCu(LiI) vs R{sub 2}CuLi(LiI)) as well as the additive (TMSCl vs TMSI). Subsequent iodolactonization of the {gamma},{delta}-unsaturated acids followed by reduction give trisubstituted {gamma}-lactones in good overall yields.

  9. Methods of refining and producing isomerized fatty acid esters and fatty acids from natural oil feedstocks

    Energy Technology Data Exchange (ETDEWEB)

    Snead, Thomas E.; Cohen, Steven A.; Gildon, Demond L.; Beltran, Leslie V.; Kunz, Linda A.; Pals, Tessa M.; Quinn, Jordan R; Behrends, Jr., Raymond T.; Bernhardt, Randal J.

    2016-07-05

    Methods are provided for refining natural oil feedstocks and producing isomerized esters and acids. The methods comprise providing a C4-C18 unsaturated fatty ester or acid, and isomerizing the fatty acid ester or acid in the presence of heat or an isomerization catalyst to form an isomerized fatty ester or acid. In some embodiments, the methods comprise forming a dibasic ester or dibasic acid prior to the isomerizing step. In certain embodiments, the methods further comprise hydrolyzing the dibasic ester to form a dibasic acid. In certain embodiments, the olefin is formed by reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters, separating the olefins from the esters in the metathesized product, and transesterifying the esters in the presence of an alcohol to form a transesterified product having unsaturated esters.

  10. Mixed Allyl Rare-Earth Borohydride Complexes: Synthesis, Structure, and Application in (Co-)Polymerization Catalysis of Cyclic Esters.

    Science.gov (United States)

    Fadlallah, Sami; Jothieswaran, Jashvini; Capet, Frédéric; Bonnet, Fanny; Visseaux, Marc

    2017-11-07

    A series of new trivalent rare-earth allyl-borohydride complexes with the formula [RE(BH4 )2 (C3 H5 )(thf)x ] (RE=Sc (1), x=2; RE=Y (2) and La (3), x=3) were synthesized by reaction of the corresponding rare-earth trisborohydrides [RE(BH4 )3 (thf)x ] with half an equivalent of bis(allyl)magnesium. The complexes were fully characterized by determining their X-ray structure. Similar to their previously described Nd (4) and Sm (5) analogues, these complexes display a monomeric structure with two terminal trihapto BH4 groups, one π-η3 allyl ligand, three THF molecules for complexes 2 and 3, and two THF molecules for complex 1. The catalytic behavior of complexes 1-5 toward the ring-opening polymerization (ROP) of l-lactide (l-LA) and ϵ-caprolactone (ϵ-CL) was assessed. The Nd complex featured the best activity toward l-LA (turnover frequency (TOF)=1300 h-1 ) and the order was Nd>La>Sm>Y>Sc. Complexes 1-3 were found very active for the ROP of ϵ-CL (TOF=166 000 h-1 ), which is in line with the already established exceptionnally high performance of complexes 4 and 5. With both monomers, it was shown that the borohydride moiety was the preferentially initiating group, rather than the allyl one. The random copolymerization of l-LA and ϵ-CL was performed with complexes 1-5, in the absence or in the presence of benzyl alcohol as a chain-transfer agent, affording copolymers with ϵ-caprolactone up to 62 % inserted. The copolymers synthesized display a variety of microstructures, that is, blocky, random, or quasi-alternating. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  11. Use of fumaric acid esters in psoriasis.

    Science.gov (United States)

    Roll, Antonie; Reich, Kristian; Boer, Almut

    2007-01-01

    Fumaric acid esters (FAE) are chemical compounds derived from the unsaturated dicarbonic acid fumaric acid. The usage of FAEs in treatment of psoriasis was introduced in the late 1950's. In the 1980s more standardized oral preparations of FAEs were developed containing dimethylfumarate (DMF) and salts of monoethylfumarate (MEF) as main compounds. In 1994, Fumaderm an enteric-coated tablet containing DMF and calcium, magnesium and zinc salts of MEF was approved for the treatment of psoriasis in Germany and since then has become the most commonly used systemic therapy in this country. Fumaric acids have been proven to be an effective therapy in patients with psoriasis even though the mechanisms of action are not completely understood. About 50-70% of the patients achieve PASI 75 improvement within four months of treatment and without any long-term toxicity, immunosuppressive effects or increased risk of infection or malignancy. Tolerance is limited by gastrointestinal side effects and flushing of the skin. This article reviews pharmacokinetics, uses, contraindications, dosages and side effects of treatment with FAEs.

  12. Use of fumaric acid esters in psoriasis

    Directory of Open Access Journals (Sweden)

    Roll Antonie

    2007-01-01

    Full Text Available Fumaric acid esters (FAE are chemical compounds derived from the unsaturated dicarbonic acid fumaric acid. The usage of FAEs in treatment of psoriasis was introduced in the late 1950′s. In the 1980s more standardized oral preparations of FAEs were developed containing dimethylfumarate(DMF and salts of monoethylfumarate(MEF as main compounds. In 1994, Fumaderm ® an enteric-coated tablet containing DMF and calcium, magnesium, and zinc salts of MEF was approved for the treatment of psoriasis in Germany and since then has become the most commonly used systemic therapy in this country. Fumaric acids have been proven to be an effective therapy in patients with psoriasis even though the mechanisms of action are not completely understood. About 50-70% of the patients achieve PASI 75 improvement within four months of treatment and without any long-term toxicity, immunosuppressive effects, or increased risk of infection or malignancy. Tolerance is limited by gastrointestinal side effects and flushing of the skin. This article reviews pharmacokinetics, uses, contraindications, dosages, and side effects of treatment with FAEs.

  13. Adsorption and corrosion inhibition of mild steel in hydrochloric acid solution by S-allyl-O,O‧-dialkyldithiophosphates

    Science.gov (United States)

    Lai, Chuan; Xie, Bin; Zou, Like; Zheng, Xingwen; Ma, Xiao; Zhu, Shasha

    Here, S-allyl-O,O‧-diphenyldithiophosphate(SOD1), S-allyl-O,O‧-dibenzyldithiophosphate (SOD2) and S-allyl-O,O‧-di(2-phenylethyl)dithiophosphate(SOD3) were successful synthesized and characterized, which acting as the novel corrosion inhibitors for mild steel in hydrochloric acid (HCl) solution were evaluated by electrochemical measurements, weight loss measurement and scanning electron microscopy. Potentiodynamic polarization measurement indicates that the synthesized inhibitors are effective mixed-type inhibitors. The inhibition efficiency increases with inhibitor concentration increasing, decreases with HCl concentration and temperature increasing. The adsorption of SOD1, SOD2 and SOD3 on mild steel surface obeys Langmuir isotherm. The adsorption of SOD1 and SOD3 on mild steel surface is a mixed adsorption involving both physisorption and chemisorption, and that the adsorption of SOD2 on mild steel surface belongs to chemical adsorption.

  14. 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 ...

  15. Inactivation of Salmonella in tomato stem scars by organic acid wash and chitosan-allyl isothiocyanate coating

    Science.gov (United States)

    The objective of this study was to evaluate inactivation of inoculated Salmonella enterica on tomato stem scars exploiting integrated treatment of organic acid wash (AW) followed by chitosan-allyl isothiocyanate (CT-AIT) coating. The treatment effect on microbial loads and fruit quality during 21 d...

  16. Electron spin resonance study of oriented allyl-type free radicals of butene and butadienecarboxylic acids and derivatives

    Energy Technology Data Exchange (ETDEWEB)

    Muszkat, L.

    1981-10-01

    Single-crystal electron spin resonance studies of free radicals formed by ..gamma.. irradiation were performed on a series of unsaturated carboxylic acids and their derivatives. As a rule, allyl-type extended ..pi..-electron free radicals are the most persistent species observed in the butene series molecules (2- and 3-hexenedioic acids) and in the butadiene series molecules (sorbic acid, sorbamide, and dimethyl muconate).

  17. Inert Reassessment Document for PEG Fatty Acid Esters

    Science.gov (United States)

    The tolerance reassessment decision document and action memorandum for the PEG fatty acid ester date September 28, 2005, included two tolerance exemptions (under 40 CFR 180.910 and $) CFR 180.930, respectively)

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

    African Journals Online (AJOL)

    The synthesis of fatty acid ethyl ester from chicken fat waste using ZnO/SiO2 heterogeneous catalyst was carried out using two-step procedures of acid pretreatment by esterification and transesterification of the pretreated oil. The first step reduces the high free fatty acid in the oil to an acceptable level for transesterification ...

  19. Selective synthesis of thiodiglycol dicarboxylic acid esters via p ...

    Indian Academy of Sciences (India)

    The esterification of thiodiglycol and long alkyl-chain carboxylic acids is reported. Reaction of thiodiglycol with carboxylic acid via -TsOH/C-catalysed direct esterification afforded thiodiglycol dicarboxylic acid esters in good yields and chemoselectivity. The use of immobilized -TsOH on activated carbon as catalyst is ...

  20. A Convenient Synthesis of Amino Acid Methyl Esters

    Directory of Open Access Journals (Sweden)

    Yaowu Sha

    2008-05-01

    Full Text Available A series of amino acid methyl ester hydrochlorides were prepared in good toexcellent yields by the room temperature reaction of amino acids with methanol in thepresence of trimethylchlorosilane. This method is not only compatible with natural aminoacids, but also with other aromatic and aliphatic amino acids.

  1. Selective synthesis of thiodiglycol dicarboxylic acid esters via p ...

    Indian Academy of Sciences (India)

    Abstract. The esterification of thiodiglycol and long alkyl-chain carboxylic acids is reported. Reaction of thiodiglycol with carboxylic acid via p-TsOH/C-catalysed direct esterification afforded thiodiglycol dicar- boxylic acid esters in good yields and chemoselectivity. The use of immobilized p-TsOH on activated carbon.

  2. Microwave-assisted preparation of naphthenic acid esters

    Directory of Open Access Journals (Sweden)

    VERA CIRIN-NOVTA

    2006-12-01

    Full Text Available The synthesis of esters of natural petroleum acids of the naphthenic type assisted with microwave irradiation under the conditions of acid catalysis was carried out with various alcohols: methanol, ethanol, n-butanol and tert-butyl alcohol. Microwave dielectric heating of the reaction mixture in an unmodified microwave oven with activation of the naphthenic acids with sulfuric and p-toluenesulfonic acid afforded the esters of the naphthenic acids. Depending on the catalyst and the steric and nucleophilic properties of the alcohols, the yield of naphthenic esters ranged from 31.25 % to 88.90 %. As a consequence of microwave dielectric heating, the esterification time was reduced from 6–10 h to 5 min.

  3. Oral fumaric acid esters for psoriasis.

    Science.gov (United States)

    Atwan, Ausama; Ingram, John R; Abbott, Rachel; Kelson, Mark J; Pickles, Timothy; Bauer, Andrea; Piguet, Vincent

    2015-08-10

    Psoriasis is a chronic inflammatory skin condition that can markedly reduce life quality. Several systemic therapies exist for moderate to severe psoriasis, including oral fumaric acid esters (FAE). These contain dimethyl fumarate (DMF), the main active ingredient, and monoethyl fumarate. FAE are licensed for psoriasis in Germany but used off-licence in many countries. To assess the effects and safety of oral fumaric acid esters for psoriasis. We searched the following databases up to 7 May 2015: the Cochrane Skin Group Specialised Register, CENTRAL in the Cochrane Library (Issue 4, 2015), MEDLINE (from 1946), EMBASE (from 1974), and LILACS (from 1982). We searched five trials registers and checked the reference lists of included and excluded studies for further references to relevant randomised controlled trials. We handsearched six conference proceedings that were not already included in the Cochrane Skin Group Specialised Register. Randomised controlled trials (RCTs) of FAE, including DMF monotherapy, in individuals of any age and sex with a clinical diagnosis of psoriasis. Two review authors independently assessed trial quality and extracted data. Primary outcomes were improvement in Psoriasis Area and Severity Index (PASI) score and the proportion of participants discontinuing treatment due to adverse effects. We included 6 studies (2 full reports, 2 abstracts, 1 brief communication, and 1 letter), with a total of 544 participants. Risk of bias was unclear in several studies because of insufficient reporting. Five studies compared FAE with placebo, and one study compared FAE with methotrexate. All studies reported data at 12 to 16 weeks, and we identified no longer-term studies. When FAE were compared with placebo, we could not perform meta-analysis for the primary outcome of PASI score because the three studies that assessed this outcome reported the data differently, although all studies reported a significant reduction in PASI scores with FAE. Only 1 small

  4. Effects of high-melting methyl esters on crystallization properties of fatty acid methyl ester mixtures

    Science.gov (United States)

    Biodiesel is a renewable alternative diesel fuel made from vegetable oils and animal fats. The most common form of biodiesel in the United States are fatty acid methyl esters (FAME) from soybean, canola, and used cooking oils, waste greases, and tallow. Cold flow properties of biodiesel depend on th...

  5. Methods of refining and producing dibasic esters and acids from natural oil feedstocks

    Energy Technology Data Exchange (ETDEWEB)

    Snead, Thomas E.; Cohen, Steven A.; Gildon, Demond L.

    2016-06-14

    Methods and systems for making dibasic esters and/or dibasic acids using metathesis are generally disclosed. In some embodiments, the methods comprise reacting a terminal olefin ester with an internal olefin ester in the presence of a metathesis catalyst to form a dibasic ester and/or dibasic acid. In some embodiments, the terminal olefin ester or the internal olefin ester are derived from a renewable feedstock, such as a natural oil feedstock. In some such embodiments, the natural oil feedstock, or a transesterified derivative thereof, is metathesized to make the terminal olefin ester or the internal olefin ester.

  6. The synthesis of fatty acid ethyl ester by carboxylester lipase.

    Science.gov (United States)

    Tsujita, T; Okuda, H

    1994-08-15

    Carboxylester lipase obtained from pig pancreas is associated with fatty acid ethyl ester synthase as judged by their elution in the same fraction from a heparin-Sepharose column, coprecipitations by antibody against purified carboxylester lipase and identical profiles of inhibition by diisopropyl fluorophosphate. Only one polypeptide of molecular mass 74-kDa in purified carboxylester lipase was labeled by immunostaining and affinity labeling with [3H]diisopropyl fluorosphate. Bovine serum albumin decreased the fatty-acid-ethyl-ester-synthesizing activity in a concentration-dependent manner. On incubation of purified carboxylester lipase with trioleylglycerol in an ethanol/water mixture, fatty acid ethyl ester was formed in the presence of a high concentration of bovine serum albumin. The acyltransfer activities from trioleylglycerol to ethanol (ethanolysis) were approximately 25-30 times higher than the acyltransfer activities to water (hydrolysis). When cholesterol was used as an acceptor, acyltransfer activity from trioleylglycerol to cholesterol (cholesterolysis) was also observed. We propose the following mechanism of fatty acid ethyl ester formation from triacyl glycerol. The enzyme attacks triacyl glycerol forming an acyl-enzyme intermediate, and during the deacylation process, alcohol binds to fatty acid as an acceptor. These results suggest that during lipid (triacyl glycerol) degradation, carboxylester lipase contributes to non-oxidative ethanol metabolism in the intestinal lumen.

  7. Growth inhibitory properties of lactose fatty acid esters

    Directory of Open Access Journals (Sweden)

    Seung-Min Lee

    2017-11-01

    Full Text Available Sugar esters are biodegradable, nonionic surfactants which have microbial inhibitory properties. The influence of the fatty acid chain length on the microbial inhibitory properties of lactose esters was investigated in this study. Specifically, lactose monooctanoate (LMO, lactose monodecanoate (LMD, lactose monolaurate (LML and lactose monomyristate (LMM were synthesized and dissolved in both dimethyl sulfoxide (DMSO and ethanol. Minimum inhibitory concentrations (MIC and minimum bactericidal concentrations (MBC were determined in growth media. LML was the most effective ester, exhibiting MIC values of <0.05 to <5 mg/ml for each Gram-positive bacteria tested (Bacillus cereus, Mycobacterium KMS, Streptococcus suis, Listeria monocytogenes, Enterococcus faecalis, and Streptococcus mutans and MBC values of <3 to <5 mg/ml for B. cereus, M. KMS, S. suis, and L. monocytogenes. LMD showed MIC and MBC values of <1 to <5 mg/ml for B. cereus, M. KMS, S. suis, L. monocytogenes, and E. faecalis, with greater inhibition when dissolved in ethanol. LMM showed MIC and MBC values of <1 to <5 mg/ml for B. cereus, M. KMS, and S. suis. LMO was the least effective showing a MBC value of <5 mg/ml for only B. cereus, though MIC values for S. suis and L. monocytogenes were observed when dissolved in DMSO. B. cereus and S. suis were the most susceptible to the lactose esters tested, while S. mutans and E. faecalis were the most resilient and no esters were effective on Escherichia coli O157:H7. This research showed that lactose esters esterified with decanoic and lauric acids exhibited greater microbial inhibitory properties than lactose esters of octanoate and myristate against Gram-positive bacteria.

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

    Indian Academy of Sciences (India)

    Madhu

    artery disease such as hypertension, obesity and dyslipidemia. Effect of a novel insulinotropic agent, succinic acid monoethyl ester, on lipids and lipoproteins levels in rats with streptozotocin-nicotinamide- induced type 2 diabetes. RAMALINGAM SARAVANAN and LEELAVINOTHAN PARI*. Department of Biochemistry and ...

  9. 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

  10. Hydride as a leaving group in the reaction of pinacolborane with halides under ambient Grignard and Barbier conditions. One-pot synthesis of alkyl, aryl, heteroaryl, vinyl, and allyl pinacolboronic esters.

    Science.gov (United States)

    Clary, Jacob W; Rettenmaier, Terry J; Snelling, Rachel; Bryks, Whitney; Banwell, Jesse; Wipke, W Todd; Singaram, Bakthan

    2011-12-02

    Grignard reagents (aliphatic, aromatic, heteroaromatic, vinyl, or allylic) react with 1 equiv of 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (pinacolborane, PinBH) at ambient temperature in tetrahydrofuran (THF) to afford the corresponding pinacolboronates. The initially formed dialkoxy alkylborohydride intermediate quickly eliminates hydridomagnesium bromide (HMgBr) and affords the product boronic ester in very good yield. Hydridomagnesium bromide (HMgBr) in turn disproportionates to a 1:1 mixture of magnesium hydride (MgH(2)) and magnesium bromide (MgBr(2)) on addition of pentane to the reaction mixture. DFT calculations (Gaussian09) at the B3LYP/6-31G(d) level of theory show that disproportionation of HMgBr to MgH(2) and MgBr(2) is viable in the coordinating ethereal solvents. This reaction also can be carried out under Barbier conditions, where the neat PinBH is added to the flask prior to the in situ formation of Grignard reagent from the corresponding organic halide and magnesium metal. Pinacolboronic ester synthesis under Barbier conditions does not give Wurtz coupling side products from reactive halides, such as benzylic and allylic halides. The reaction between PinBH and various Grignard reagents is an efficient, mild, and general method for the synthesis of pinacolboronates. © 2011 American Chemical Society

  11. 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

  12. 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 Cu2+ 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 Cu2+, 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.

  13. Methods of refining and producing dibasic esters and acids from natural oil feedstocks

    Energy Technology Data Exchange (ETDEWEB)

    Snead, Thomas E.; Cohen, Steven A.; Gildon, Demond L.

    2016-03-15

    Methods are provided for refining natural oil feedstocks and producing dibasic esters and/or dibasic acids. The methods comprise reacting a terminal olefin with an internal olefin in the presence of a metathesis catalyst to form a dibasic ester and/or dibasic acid. In certain embodiments, the olefin esters are formed by reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters, separating the olefins from the esters in the metathesized product, and transesterifying the esters in the presence of an alcohol to form a transesterified product having olefin esters.

  14. Methods of refining and producing dibasic esters and acids from natural oil feedstocks

    Energy Technology Data Exchange (ETDEWEB)

    Snead, Thomas E; Cohen, Steven A; Gildon, Demond L

    2015-04-07

    Methods are provided for refining natural oil feedstocks and producing dibasic esters and/or dibasic acids. The methods comprise reacting a terminal olefin with an internal olefin in the presence of a metathesis catalyst to form a dibasic ester and/or dibasic acid. In certain embodiments, the olefin esters are formed by reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters, separating the olefins from the esters in the metathesized product, and transesterifying the esters in the presence of an alcohol to form a transesterified product having olefin esters.

  15. 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...

  16. 75 FR 52269 - Acetic Acid Ethenyl Ester, Polymer With Oxirane; Tolerance Exemption

    Science.gov (United States)

    2010-08-25

    ...-2010-0429; FRL-8841-2] Acetic Acid Ethenyl Ester, Polymer With Oxirane; Tolerance Exemption AGENCY... from the requirement of a tolerance for residues of acetic acid ethenyl ester, polymer with oxirane... permissible level for residues of acetic acid ethenyl ester, polymer with oxirane on food or feed commodities...

  17. 21 CFR 175.260 - Partial phosphoric acid esters of polyester resins.

    Science.gov (United States)

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Partial phosphoric acid esters of polyester resins... COMPONENTS OF COATINGS Substances for Use as Components of Coatings § 175.260 Partial phosphoric acid esters of polyester resins. Partial phosphoric acid esters of polyester resins identified in this section...

  18. 40 CFR 721.6110 - Alkyldi(alkyloxyhydroxypropyl) derivative, phosphoric acid esters, potassium salts.

    Science.gov (United States)

    2010-07-01

    ...) derivative, phosphoric acid esters, potassium salts. 721.6110 Section 721.6110 Protection of Environment...) derivative, phosphoric acid esters, potassium salts. (a) Chemical substance and significant new uses subject...) derivative, phosphoric acid esters, potassium salts (PMN P-91-818) is subject to reporting under this section...

  19. 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...

  20. 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...

  1. Substituted esters of stearic acid as potential lubricants

    Energy Technology Data Exchange (ETDEWEB)

    Kleinova, Andrea; Fodran, Peter; Brncalova, Lucia; Cvengros, Jan [Department of Physical Chemistry and Chemical Physics, Faculty of Chemical and Food Technology, Slovak University of Technology, Radlinskeho 9, SK-812 37 Bratislava (Slovakia)

    2008-04-15

    Preparation and properties of four triesters - derivatives of 9,10-dihydroxystearic acid after the epoxidation of methyl ester of the oleic acid, opening of the formed oxirane ring in suitable medium and esterification of free hydroxyl group is discussed in the paper. Removal of the double bond from acyl of the fatty acid, increase of the molar weight and change of molecular structure resulted in increase of viscosity and oxidation stability of prepared triesters. Lubrication tests performed on a four-ball machine showed better tribological characteristics of synthesized triesters when compared with mineral additive-free base oil. (author)

  2. 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.

  3. 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.

  4. Enzymatic synthesis and application of fatty acid ascorbyl esters

    Directory of Open Access Journals (Sweden)

    Stojanović Marija M.

    2013-01-01

    Full Text Available Fatty acid ascorbyl esters are liposoluble substances that possess good antioxidative properties. These compounds could be synthesized by using various acyl donors for acylation of vitamin C in reaction catalyzed by chemical means or lipases. Enzymatic process is preferred since it is regioselective, performed under mild reaction conditions, with the obtained product being environmentally friendly. Polar organic solvents, ionic liquids, and supercritical fluids has been successfully used as a reaction medium, since commonly used solvents with high Log P values are inapplicable due to ascorbic acid high polarity. Acylation of vitamin C using fatty acids, their methyl-, ethyl-, and vinyl esters, as well as triglycerides has been performed, whereas application of the activated acyl donors enabled higher molar conversions. In each case, majority of authors reported that using excessive amount of the acyl donor had positive effect on yield of product. Furthermore, several strategies have been employed for shifting the equilibrium towards the product by water content control. These include adjusting the initial water activity by pre-equilibration of reaction mixture, enzyme preparation with water vapor of saturated salt solutions, and the removal of formed water by the addition of molecular sieves or salt hydrate pairs. The aim of this article is to provide a brief overview of the procedures described so far for the lipase-catalyzed synthesis of fatty acid ascorbyl esters with emphasis on the potential application in food, cosmetics, and pharmaceutics. Furthermore, it has been pointed out that the main obstacles for process commercialization are long reaction times, lack of adequate purification methods, and high costs of lipases. Thus, future challenges in this area are testing new catalysts, developing continuous processes for esters production, finding cheaper acyl donors and reaction mediums, as well as identifying standard procedures for

  5. Fumaric acid esters in the management of psoriasis

    OpenAIRE

    Balak DMW

    2015-01-01

    Deepak MW Balak Department of Dermatology, Erasmus Medical Center, Rotterdam, the Netherlands Abstract: Fumaric acid esters (FAE) are small molecules with immunomodulating, anti-inflammatory, and anti-oxidative effects. FAE were introduced as a systemic psoriasis treatment in 1959 and empirically developed further between 1970 and 1990 in Germany, Switzerland, and the Netherlands. The development of FAE as psoriasis treatment did not follow the traditional drug development phases. Nonetheles...

  6. 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, phosphoric acid ester salts. 721.6200 Section 721.6200 Protection of Environment ENVIRONMENTAL PROTECTION... New Uses for Specific Chemical Substances § 721.6200 Fatty acid polyamine condensate, phosphoric acid...

  7. Unexpected ring-closure products derived from 3-(2-allylanilino)-3-phenylacrylate esters: crystal and molecular structures of 3-acetyl-8-allyl-6-methyl-2-phenylquinolin-4-yl acetate and (2RS)-2,8-dimethyl-4-phenyl-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinolin-6-one.

    Science.gov (United States)

    Luque, Adriana L; Sanabria, Carlos M; Palma, Alirio; Cobo, Justo; Glidewell, Christopher

    2016-08-01

    The reactions of two 3-(2-allylanilino)-3-phenylacrylate esters with acetic anhydride and with strong acids has revealed a richly diverse reactivity providing a number of unexpected products. Thus, acetylation of ethyl 3-(2-allylanilino)-3-phenylacrylate, (Ia), or ethyl 3-(2-allyl-4-methylanilino)-3-phenylacrylate, (Ib), with acetic anhydride yields not only the expected acetylated esters, (II), as the major products but also the unexpected polysubstituted quinolines 3-acetyl-8-allyl-2-phenylquinolin-4-yl acetate, (IIIa), and 3-acetyl-8-allyl-6-methyl-2-phenylquinolin-4-yl acetate, (IIIb), as minor products. Subsequent reaction of the major product ethyl 2-[(2-allyl-4-methylanilino)(phenyl)methylidene]-3-oxobutanoate, (IIb), with concentrated sulfuric acid did not provide the expected 3-acetylquinoline derivative, but instead two unexpected products, namely ethyl 4-ethyl-2-phenyl-1,4-dihydroquinoline-3-carboxylate, (IV), and ethyl 3-acetyl-4-ethyl-2-phenyl-3,4-dihydroquinoline-3-carboxylate, (V), in yields of 39 and 22%, respectively. The reaction of (Ib) with Eaton's reagent gave both the quinoline (Z)-6-methyl-2-phenyl-8-(prop-1-en-1-yl)quinolin-4(1H)-one, (VI), and the unexpected tricyclic product (2RS)-2,8-dimethyl-4-phenyl-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinolin-6-one, (VII), in yields of 71 and 12%, respectively. The products (II)-(VII) have all been fully characterized spectroscopically and the crystal structures of two of the unexpected products, i.e. (IIIb) (C23H21NO3) and (VII) (C19H17NO), are reported here. The formation of compounds (IV), (V) and (VII) all require an isomerization of the initial allyl substituent, with migration of the C=C double bond from the terminal site to the internal site. In (IIIb), the two acetyl substituents are oriented such that the intramolecular distance between the two carbonyl O atoms is only 3.243 (2) Å, and in (VII), the five-membered ring adopts a twisted half-chair conformation. The molecules of compound (IIIb

  8. 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.

  9. The Zinc Mediated Condensation of Amino Acid Esters with Imines to b-Lactams

    NARCIS (Netherlands)

    Koten, G. van; Jastrzebski, J.T.B.H.

    1993-01-01

    An experimentally attractive stereoselectie 'one pot' synthesis of beta-lactams is described. This route is based on the zinc mediated condensation of an alpha-amino acid ester with an imine via a zinc ester enolate. Making use of proper substituents in both the amino acid ester and the imine the

  10. Application of lipase technology for transesterification of fatty acid ester

    Directory of Open Access Journals (Sweden)

    JOKO SULISTYO

    2005-07-01

    Full Text Available We have reported the potency of microbial extracellular enzyme for synthesis of fatty acid ester. Further investigation was aimed to study capacity of the enzyme on bioprocess of crude palm oil by transesterification of saturated fatty acid to fatty acid ester. We have studied some lipases from culture filtrate of Candida rugosa FM-9301, Bacillus subtilis FM-9101 and Pseudomonas aerogenes FM-9201, which were preincubated in a medium containing olive oil as inducers, using a shaker under conditions that allowed for lipase production at pH 4.5-6.5 and room temperature for 5 days. Those strains shown different activities during the hydrolysis of substrates, which resulted in decreasing or increasing free fatty acids those, were liberated from media containing crude palm oil and organic solvents. The optimal transesterification condition was at temperature of 45-50C and at pH 4.5 for C. rugosa and pH 6.0 to 7.0 for P. aerogenes and B. subtilis. Under the enzyme concentration of 50% (v/v, the transesterification was rapidly occurred, while at the concentration of 20% (v/v the enzymatically biosynthesis required longer incubation period. The substrates incubated with C. rugosa lipase exhibited higher linoleic and linolenic acid (7.16 and 2.15%, respectively, than that of B. subtilis lipase (4.85% and 1.43%, respectively, while P. aerogenes lipase (3.73% and 1.11%, respectively.

  11. Production of Oleic Acid Based Wax Ester Using Acidic Homogeneous Catalysts

    Directory of Open Access Journals (Sweden)

    Naowara Al-Arafi

    2012-01-01

    Full Text Available Four homogeneous acidic catalysts were tested for their ability to catalyze the esterification reaction of oleic acid and oleyl alcohol to produce oleyl oleate, a wax ester. Sulfuric acid showed relatively higher specific activity. Various reaction parameters were optimised to obtain high percentage yield of oleyl oleate. The optimum condition to produce oeyl oleate was reaction time; 5 h, temperture; 90°C, amount of sulforic acid 0.15 g and molar ratio of oleyl alcohol to oleic acid; 1:1. Percentage yield of wax ester obtained at these optimum reaction conditions was 93.88. Disappearance of carboxylic acid (C=O peak has confirmed by FTIR with appearance of ester (C=O peak at 1739 cm−1. 1H NMR spectra analyses confirmed the result of oleyl oleate with appearance of ester (-CH2OCOR at 4.02 ppm and also the 13C-NMR confirmed the result with appearance of ester (C=O peak at 173.2 ppm. The low-temperture behavior of compound synthesized was determined through its pour point (PP, viscosity index (VI and flash point (FP values. The results showed that oleyl oleate exhibited the most favorable low-temperture performance of PP, VI and FP with −31°C, 197.5 and 320°C respectively. This is due to increase of the molacular weight thus improve the low temperture property significantly.

  12. ESTIMATION OF HYDROLYSIS RATE CONSTANTS OF CARBOXYLIC ACID ESTER AND PHOSPHATE ESTER COMPOUNDS IN AQUEOUS SYSTEMS FROM MOLECULAR STRUCTURE BY SPARC

    Science.gov (United States)

    SPARC (SPARC Performs Automated Reasoning in Chemistry) chemical reactivity models were extended to calculate hydrolysis rate constants for carboxylic acid ester and phosphate ester compounds in aqueous non- aqueous and systems strictly from molecular structure. The energy diffe...

  13. gamma-Aminobutyric acid esters. 2. Synthesis, brain uptake, and pharmacological properties of lipid esters of gamma-aminobutyric acid.

    Science.gov (United States)

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

    1985-01-01

    Two lipid esters of U-14C-labeled and unlabeled gamma-aminobutyric acid (GABA) were synthesized to test the possibility that natural lipid analogues, which resemble normal components of lipid bilayer membranes, can penetrate the blood-brain barrier and transport exogenous GABA to the brain. The uptake of 1-linolenoyl-2,3-bis(4-aminobutyryl)propane-1,2,3-triol and 1,2-dilinolenoyl-3-(4-aminobutyryl)propane-1,2,3-triol into mouse brain relative to liver was found to be, respectively, 75- and 127-fold greater than that of free GABA. The results indicate that there is little or no blood-brain barrier for the GABA ester molecules at doses up to 0.36 mmol/kg. Both ester compounds, but neither free GABA nor the lipid components delivered systemically, demonstrated central nervous system depressant properties by inhibiting the general motor activity of mice. Brain tissue has esterase activity which can release GABA from these compounds. This suggests that these compounds function as "prodrugs" to release GABA in the CNS.

  14. A new sesquiterpene lactone glycoside and a new quinic acid methyl ester from Patrinia villosa.

    Science.gov (United States)

    Yang, Yong-Fen; Ma, Hong-Mei; Chen, Gang; Wang, Hai-Feng; Xiang, Zheng; Feng, Qing-Mei; Hua, Hui-Ming; Pei, Yue-Hu

    2016-10-01

    A new sesquiterpene lactone glycoside (1) and a new quinic acid methyl ester (2) were isolated from Patrinia villosa, together with another two known compounds chlorogenic acid n-butyl ester (3), 3, 4-di-O-caffeoylquinic acid methyl ester (4). Their structures were established using 1D/2D-NMR spectroscopy, mass spectrometry, and comparing with spectroscopic data reported in the literature.

  15. 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.

  16. 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...

  17. 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....

  18. A formal [3,3]-sigmatropic rearrangement route to quaternary alpha-vinyl amino acids: use of allylic N-PMP trifluoroacetimidates.

    Science.gov (United States)

    Berkowitz, David B; Wu, Bin; Li, Huijie

    2006-03-02

    Pd(II)-mediated rearrangement of allylic N-PMP (p-methoxyphenyl) trifluoroacetimidates provides the first formal sigmatropic route to quaternary, alpha-vinylic amino acids, potential suicide substrates for PLP enzymes. The amino acid side chains enter via transition-metal-mediated C-C bond constructions, including (i) Cu(I)-mediated conjugate addition (Ala); (ii) Pd(0)/AsPh3-mediated Stille coupling (allyl-Gly, Phe, DOPA, m-Tyr); and (iii) Pd(0)/Pt-Bu3-mediated Negishi coupling (Leu). In the synthesis of the DOPA decarboxylase inactivator, alpha-vinyl-m-tyrosine, the new N-PMP trifluoroacetimidate rearranges much more efficiently than the corresponding trichloroacetimidate.

  19. Impact of Association Colloids on Lipid Oxidation in Triacylglycerols and Fatty Acid Ethyl Esters.

    Science.gov (United States)

    Homma, Rika; Suzuki, Karin; Cui, Leqi; McClements, David Julian; Decker, Eric A

    2015-11-25

    The impact of association colloids on lipid oxidation in triacylglycerols and fatty acid ethyl esters was investigated. Association colloids did not affect lipid oxidation of high oleic safflower and high linoleic safflower triacylglycerols, but were prooxidative in fish triacylglycerols. Association colloids retarded aldehyde formation in stripped ethyl oleate, linoleate, and fish oil ethyl esters. Interfacial tension revealed that lipid hydroperoxides were surface active in the presence of the surfactants found in association colloids. The lipid hydroperoxides from ethyl esters were less surface active than triacylglycerol hydroperoxides. Stripping decreased iron and copper concentrations in all oils, but more so in fatty acid ethyl esters. The combination of lower hydroperoxide surface activity and low metal concentrations could explain why association colloids inhibited lipid oxidation in fatty acid ethyl esters. This research suggests that association colloids could be used as an antioxidant technology in fatty acid ethyl esters.

  20. 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

  1. Proteinuria with fumaric acid ester treatment for psoriasis.

    Science.gov (United States)

    Ogilvie, S; Lewis Jones, S; Dawe, R; Foerster, J

    2011-08-01

    Fumaric acid esters (FAE) have been used in the treatment of psoriasis for many years. In general, they are regarded as relatively safe compared with other antipsoriatic systemic treatments, with the most notable adverse effects being gastrointestinal upset, lymphopenia and transient flushing. Renal toxicity has only rarely been reported, and was not found in two independent prospective trials nor in a large retrospective evaluation of almost 1000 patients treated for a median of 44 months. We report three patients developing reversible proteinuria during FAE treatment. One of these displayed the same pattern upon repeated drug administration, thereby clearly indicating FAE treatment to be the causal trigger. The presented cases highlight proteinuria as a clinical concern in FAE treatment. Furthermore, as the novel FAE agent dimethylfumaric (DMF) ester (contained in BG00012/Panaclar) has previously been shown to be effective in psoriasis in a phase III trial and not shown renal toxicity in a large trial for multiple sclerosis, the current report suggests that market introduction of DMF for psoriasis should be pursued. © The Author(s). CED © 2011 British Association of Dermatologists.

  2. Depigmenting Effect of Kojic Acid Esters in Hyperpigmented B16F1 Melanoma Cells

    Directory of Open Access Journals (Sweden)

    Ahmad Firdaus B. Lajis

    2012-01-01

    Full Text Available The depigmenting effect of kojic acid esters synthesized by the esterification of kojic acid using Rhizomucor miehei immobilized lipase was investigated in B16F1 melanoma cells. The depigmenting effect of kojic acid and kojic acid esters was evaluated by the inhibitory effect of melanin formation and tyrosinase activity on alpha-stimulating hormone- (α-MSH- induced melanin synthesis in B16F1 melanoma cells. The cellular tyrosinase inhibitory effect of kojic acid monooleate, kojic acid monolaurate, and kojic acid monopalmitate was found similar to kojic acid at nontoxic doses ranging from 1.95 to 62.5 μg/mL. However, kojic acid monopalmitate gave slightly higher inhibition to melanin formation compared to other inhibitors at doses ranging from 15.63 to 62.5 μg/mL. Kojic acid and kojic acid esters also show antioxidant activity that will enhance the depigmenting effect. The cytotoxicity of kojic acid esters in B16F1 melanoma cells was significantly lower than kojic acid at high doses, ranging from 125 and 500 μg/mL. Since kojic acid esters have lower cytotoxic effect than kojic acid, it is suggested that kojic acid esters can be used as alternatives for a safe skin whitening agent and potential depigmenting agents to treat hyperpigmentation.

  3. Bioequivalence Demonstration for Ω-3 Acid Ethyl Ester Formulations: Rationale for Modification of Current Guidance.

    Science.gov (United States)

    Maki, Kevin C; Johns, Colleen; Harris, William S; Puder, Mark; Freedman, Steven D; Thorsteinsson, Thorsteinn; Daak, Ahmed; Rabinowicz, Adrian L; Sancilio, Frederick D

    2017-03-01

    The US Food and Drug Administration (FDA) draft guidance for establishing bioequivalence (BE) of ω-3 acid ethyl esters (containing both eicosapentaenoic acid [EPA] and docosahexaenoic acid [DHA] as ethyl esters), used to treat severe hypertriglyceridemia, recommends the conduct of 2 studies: one with participants in the fasting state and one with participants in the fed state. For the fasting study, the primary measures of BE are baseline-adjusted EPA and DHA levels in total plasma lipids. For the fed study, the primary measures of BE are EPA and DHA ethyl esters in plasma. This guidance differs from that established for icosapent ethyl (EPA ethyl esters) in which the primary measure of BE is baseline-adjusted total EPA in plasma lipids for both the fasting and fed states. The FDA guidance for ω-3 acid ethyl esters is not supported by their physiologic characteristics and triglyceride-lowering mechanisms because EPA and DHA ethyl esters are best characterized as pro-drugs. This article presents an argument for amending the FDA draft guidance for ω-3 acid ethyl esters to use baseline-adjusted EPA and DHA in total plasma lipids as the primary measures of BE for both fasting and fed conditions. This change would harmonize the approaches for demonstration of BE for ω-3 acid ethyl esters and icosapent ethyl (EPA ethyl esters) products for future development programs and is the most physiologically rational approach to BE testing. Copyright © 2017 Elsevier HS Journals, Inc. All rights reserved.

  4. 40 CFR 721.3800 - Formaldehyde, condensated polyoxyethylene fatty acid, ester with styrenated phenol, ethylene...

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Formaldehyde, condensated... 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...

  5. Ferulic acid esters of glucosylglucose from Allium macrostemon Bunge.

    Science.gov (United States)

    Usui, Ayaka; Matsuo, Yosuke; Tanaka, Takashi; Ohshima, Kazusato; Fukuda, Shinji; Mine, Takara; Yakashiro, Ichiro; Ishimaru, Kanji

    2017-03-01

    Three new ferulic acid esters of glucosylglucose, 1-O-(E)-feruloyl-β-d-glucopyranosyl (1-2)-[β- d-glucopyranosyl (1-6)]-β-d-glucopyranose (allimacronoid A, 1), 1-O-(E)-feruloyl-{β-d-glucopyranosyl (1-4)-[β-d-glucopyranosyl (1-2)]}-[β- d-glucopyranosyl (1-6)]-β-d-glucopyranose (allimacronoid B, 2), and 1-O-(E)-feruloyl-{β-d-glucopyranosyl (1-6)-[β-d-glucopyranosyl (1-2)]}-[β- d-glucopyranosyl (1-6)]-β-d-glucopyranose (allimacronoid C, 3) were isolated together with tuberonoid A (4), from the leaves of Allium macrostemon Bunge. The chemical structures were elucidated based on the analyses of the spectroscopic and chemical data.

  6. Fumaric acid esters in the management of severe psoriasis.

    Science.gov (United States)

    Brewer, L; Rogers, S

    2007-05-01

    Fumaric acid esters (FAEs) offer an effective alternative to patients with psoriasis in whom other systemic agents are contraindicated or have failed. We assessed the efficacy and side effect profile of FAEs in a group of patients with psoriasis. A retrospective study was carried out on patients treated with FAEs over 21 months. Information was gathered from patients' notes. Dosage, response and side effects were recorded. In total, 31 patients were included. The mean age was 46.8 years. All patients had been treated with other modalities and 61.5% had received previous systemic treatment. There was good to excellent response in 58.6% of patients. Subjective side-effects were common (87.1%), and lymphopenia occurred in 61.3%. The drug was not tolerated by one-fifth of patients. The relatively low toxicity and absence of hepatotoxicity makes FAEs a reasonable first-line systemic treatment in selected patients with difficult psoriasis.

  7. Fumaric acid esters in psoriasis and multiple sclerosis.

    Science.gov (United States)

    Zecca, C; Caporro, M; Adami, M; Mainetti, C; Gobbi, C

    2014-06-01

    Fumaric acid esters (FAEs) are effective in patients with moderate to severe psoriasis. Recent studies also report the efficacy of one FAE component, dimethylfumarate, in relapsing forms of multiple sclerosis (MS). We describe the case of a patient with MS who developed severe plaque psoriasis during interferon-β-1a treatment for MS. The psoriasis was unresponsive to usual topical treatments and phototherapy. The patient was started on FAE 720 mg daily, with complete remission of the psoriatic lesions and neurological stabilization at follow-up at 24 months. Our case suggests that FAEs could represent a therapeutic option for patients with MS who develop plaque psoriasis following exposure to immune-modulating agents. © 2014 British Association of Dermatologists.

  8. Fumaric acid esters in the management of psoriasis

    Directory of Open Access Journals (Sweden)

    Balak DMW

    2015-01-01

    Full Text Available Deepak MW Balak Department of Dermatology, Erasmus Medical Center, Rotterdam, the Netherlands Abstract: Fumaric acid esters (FAE are small molecules with immunomodulating, anti-inflammatory, and anti-oxidative effects. FAE were introduced as a systemic psoriasis treatment in 1959 and empirically developed further between 1970 and 1990 in Germany, Switzerland, and the Netherlands. The development of FAE as psoriasis treatment did not follow the traditional drug development phases. Nonetheless, in 1994 FAE were approved in Germany for the treatment of severe plaque psoriasis. FAE are currently one of the most commonly used treatments in Germany, and FAE are increasingly being used as an unlicensed treatment in several other European countries. To date, six randomized controlled trials and 29 observational studies have evaluated FAE in a combined total of 3,439 patients. The efficacy and safety profile of FAE is favorable. About 50%–70% of patients achieve at least 75% improvement in psoriasis severity after 16 weeks of treatment. Common adverse events of FAE include gastrointestinal complaints and flushing symptoms, which lead to treatment discontinuation in up to 40% of patients. Lymphocytopenia, eosinophilia, and proteinuria are commonly observed during FAE treatment, but rarely require treatment discontinuation. The long-term safety profile of continuous FAE treatment is favorable without an increased risk for infections, malignancies, or other serious adverse events. There are no known drug-interactions for FAE. The 2009 European evidence-based S3-guidelines on psoriasis treatment recommend FAE and suggest it as a first-line systemic treatment for moderate-to-severe plaque psoriasis. This review is aimed to give an overview of FAE treatment in the management of psoriasis. Keywords: fumaric acid esters, fumarates, dimethyl fumarate, Fumaderm, psoriasis, systemic treatment

  9. Thin film of Poly(acrylic acid-co-allyl acrylate as a Sacrificial Protective Layer for Hydrophilic Self Cleaning Glass

    Directory of Open Access Journals (Sweden)

    Jānis Lejnieks

    2010-05-01

    Full Text Available Poly(acrylic acid-co-allyl acrylate statistical copolymers were synthesized in a controlled manner in two steps: first tert.butyl acrylate and allyl acrylate were polymerized via atom transfer radical polymerization (ATRP and afterwords the tert.butyl protective groups were removed via hydrolysis. Samples of self cleaning glass (SCG were coated with thin films of poly(acrylic acid-co-allyl acrylate and cross-linked afterwards by UV irradiation (in the presence of a photoinitiator and an accelerator. Solution cast thin films were transparent and homogeneous before and after UV cross-linking. The irradiated samples were found to be hydrophilic (Θ < 20° and water insoluble. The coating prevented the spontaneous hydrophobization of the SCG by residual silicon exhaled from the sealing material. The TiO2 photocatalyst that covers the glass surface was found to strip the protective coating. The rate of the photooxidation process was measured by IR spectroscopy. The real field performance of the protective coating was also tested.

  10. Synthetic studies with Pinus elliottiis rosin derivatives. Oxidation of maleopimaric anhydride methyl ester and trimethyl fumaropimarate

    Directory of Open Access Journals (Sweden)

    Hess Sonia C.

    2000-01-01

    Full Text Available Ozonolysis of maleopimaric anhydride methyl ester in the presence of tetracyanoethylene led to an epoxide and an ozonide. Ozonolysis of the trimethyl fumaropimarate, followed by treatment with Me2S, led to an epoxide, a diene, a keto-acid and an allylic oxidation product. Some of the compounds obtained were active against Staphylococcus aureus, Bacillus subtilis and Micrococcus luteus.

  11. Characteristics of Palm Fatty Acid Ester (PFAE), a New Vegetable Based Insulating Oil for Transformers

    Science.gov (United States)

    Suzuki, Takashi; Kanoh, Takaaki; Koide, Hidenobu; Hikosaka, Tomoyuki

    We have developed new vegetable based insulating oil for transformers called PFAE (Palm Fatty Acid Ester). PFAE has 0.6 times less viscosity and 1.3 times higher dielectric constant compared to mineral oil. The oxidative stability, biodegradability and acute toxicity to fish of PFAE has also been determined to be superior to mineral oil. In this paper, in order to optimize the characteristics of fatty acid esters originating from palm oil, several kinds of fatty acid alkyl esters were first synthesized in the laboratory by the molecular design technique and the transesterification from fatty acid methyl esters and alkyl alcohols. Next the electro-chemical characteristics of the fatty acid alkyl esters as insulating oil were analyzed.

  12. Effect of variations in the fatty acid chain on functional properties of oligofructose fatty acid esters

    NARCIS (Netherlands)

    Kempen, van S.E.H.J.; Schols, H.A.; Linden, van der E.; Sagis, L.M.C.

    2014-01-01

    Oligofructose fatty acid esters are surfactants that considerably lower the surface tension of an air/water interface, provide the interface with a high dilatational modulus and lead to a high foam stability. In this study, we investigate the effect of the molecular structure of oligofructose fatty

  13. Energy-rich glyceric acid oxygen esters - Implications for the origin of glycolysis

    Science.gov (United States)

    Weber, Arthur L.; Hsu, Victor

    1990-01-01

    The apparent Gibbs free energy change (GFEC) of hydrolysis (pH 7) of the 2- and 3-O-glyceroyl esters of 2- and 3-O-L-glyceroyl-L-glyceric acid methyl ester were measured at 25 C. The 2- and 3-glyceroyl esters were found to be 'energy-rich' with GFEC values of -9.1 kcal/mol and -7.8 kcal/mol, respectively. This result indicates that the analogous 2- and 3-glyceroyl esters of polyglyceric acid are also energy-rich and, therefore, could have acted as an energy source for primitive phosphoanhydride synthesis.

  14. A New 31P NMR Method for the Enantiomeric Excess Determination of Alcohols, Amines and Amino Acid Esters.

    NARCIS (Netherlands)

    Hulst, Ron; Zijlstra, Robert W.J.; Vries, N. Koen de; Hoeve, Wolter ten; Wynberg, Hans; Feringa, Bernard

    1993-01-01

    Diastereoisomeric ester and amide derivatives of phosphoric acid chloride 2 show well separated signals in the 31P NMR spectra allowing accurate e.e. determination of chiral alcohols, esters of amino acids and amines.

  15. A NEW P-31 NMR METHOD FOR THE ENANTIOMERIC EXCESS DETERMINATION OF ALCOHOLS, AMINES AND AMINO-ACID ESTERS

    NARCIS (Netherlands)

    HULST, R; ZIJLSTRA, RWJ; FERINGA, BL; DEVRIES, NK; TENHOEVE, W; WYNBERG, H

    1993-01-01

    Diastereoisomeric ester and amide derivatives of phosphoric acid chloride 2 show well separated signals in the P-31 NMR spectra allowing accurate e.e. determination of chiral alcohols, esters of amino acids and amines.

  16. Synthesis of new fatty acids amides from aminolysis of fatty acid methyl esters (FAMEs); Sintese de novas amidas graxas a partir da aminolise de esteres metilicos

    Energy Technology Data Exchange (ETDEWEB)

    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., E-mail: dqmdoca@furg.b [Universidade Federal do Rio Grande, RS (Brazil). Escola de Quimica e Alimentos

    2010-07-01

    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)

  17. Predicting the Viscosity of Low VOC Vinyl Ester and Fatty Acid-Based Resins

    Science.gov (United States)

    2005-12-01

    1) (1). Epon 828 , 834, 836, 1001F, 1004F, 1007F, and 1009F (Miller- Stephenson, Danbury, CT) were used as the source of DGEBA. To determine the...Figure 1. The reaction of methacrylic acid with Epon to form vinyl-ester monomer. Pure vinyl ester was prepared via methacrylation of Epon 828 ...resins prepared. Bimodal blends of vinyl-ester monomers (BM-VE) were prepared by methacrylation of blends of Epon 828 , used as the low molecular weight

  18. Applications of Propargyl Esters of Amino Acids in Solution-Phase Peptide Synthesis

    OpenAIRE

    Ramesh Ramapanicker; Rohit Gupta; Rajendran Megha; Srinivasan Chandrasekaran

    2011-01-01

    Propargyl esters are employed as effective protecting groups for the carboxyl group during solution-phase peptide synthesis. The propargyl ester groups can be introduced onto free amino acids by treating them with propargyl alcohol saturated with HCl. The reaction between propargyl groups and tetrathiomolybdate is exploited to deblock the propargyl esters. The removal of the propargyl group with the neutral reagent tetrathiomolybdate ensures that most of the other protecting groups used in pe...

  19. 40 CFR 721.304 - Acetic acid, [(5-chloro-8-quinolinyl)oxy-], 1-methyl hexyl ester.

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Acetic acid, , 1-methyl hexyl ester... Substances § 721.304 Acetic acid, , 1-methyl hexyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as acetic acid, -, 1-methylhexyl ester (PMN P...

  20. 75 FR 20785 - Polyglyceryl Phthalate Ester of Coconut Oil Fatty Acids; Exemption from the Requirement of a...

    Science.gov (United States)

    2010-04-21

    ... AGENCY 40 CFR Part 180 Polyglyceryl Phthalate Ester of Coconut Oil Fatty Acids; Exemption from the..., concerning polyglyceryl phthalate ester of coconut oil fatty acids; exemption from the requirement of a... phthalate ester of coconut oil fatty acids'' pursuant to a petition by the Joint Inserts Task Force, Cluster...

  1. Applications of Propargyl Esters of Amino Acids in Solution-Phase Peptide Synthesis

    Science.gov (United States)

    Ramapanicker, Ramesh; Gupta, Rohit; Megha, Rajendran; Chandrasekaran, Srinivasan

    2011-01-01

    Propargyl esters are employed as effective protecting groups for the carboxyl group during solution-phase peptide synthesis. The propargyl ester groups can be introduced onto free amino acids by treating them with propargyl alcohol saturated with HCl. The reaction between propargyl groups and tetrathiomolybdate is exploited to deblock the propargyl esters. The removal of the propargyl group with the neutral reagent tetrathiomolybdate ensures that most of the other protecting groups used in peptide synthesis are untouched. Both acid labile and base labile protecting groups can be removed in the presence of a propargyl ester. Amino acids protected as propargyl esters are employed to synthesize di- to tetrapeptides in solution-phase demonstrating the possible synthetic utilities of the methodology. The methodology described here could be a valuable addition to currently available strategies for peptide synthesis. PMID:21760822

  2. Applications of propargyl esters of amino acids in solution-phase Peptide synthesis.

    Science.gov (United States)

    Ramapanicker, Ramesh; Gupta, Rohit; Megha, Rajendran; Chandrasekaran, Srinivasan

    2011-01-01

    Propargyl esters are employed as effective protecting groups for the carboxyl group during solution-phase peptide synthesis. The propargyl ester groups can be introduced onto free amino acids by treating them with propargyl alcohol saturated with HCl. The reaction between propargyl groups and tetrathiomolybdate is exploited to deblock the propargyl esters. The removal of the propargyl group with the neutral reagent tetrathiomolybdate ensures that most of the other protecting groups used in peptide synthesis are untouched. Both acid labile and base labile protecting groups can be removed in the presence of a propargyl ester. Amino acids protected as propargyl esters are employed to synthesize di- to tetrapeptides in solution-phase demonstrating the possible synthetic utilities of the methodology. The methodology described here could be a valuable addition to currently available strategies for peptide synthesis.

  3. Applications of Propargyl Esters of Amino Acids in Solution-Phase Peptide Synthesis

    Directory of Open Access Journals (Sweden)

    Ramesh Ramapanicker

    2011-01-01

    Full Text Available Propargyl esters are employed as effective protecting groups for the carboxyl group during solution-phase peptide synthesis. The propargyl ester groups can be introduced onto free amino acids by treating them with propargyl alcohol saturated with HCl. The reaction between propargyl groups and tetrathiomolybdate is exploited to deblock the propargyl esters. The removal of the propargyl group with the neutral reagent tetrathiomolybdate ensures that most of the other protecting groups used in peptide synthesis are untouched. Both acid labile and base labile protecting groups can be removed in the presence of a propargyl ester. Amino acids protected as propargyl esters are employed to synthesize di- to tetrapeptides in solution-phase demonstrating the possible synthetic utilities of the methodology. The methodology described here could be a valuable addition to currently available strategies for peptide synthesis.

  4. Inactivation of Salmonella in grape tomato stem scars by organic acid wash and chitosan-allyl isothiocyanate coating.

    Science.gov (United States)

    Mukhopadhyay, Sudarsan; Sokorai, Kimberly; Ukuku, Dike O; Jin, Tony; Fan, Xuetong; Olanya, Modesto; Juneja, Vijay

    2018-02-02

    The objective of this study was to evaluate inactivation of inoculated Salmonella enterica on grape tomato stem scars exploiting integrated treatment of organic acid wash (AW) followed by chitosan-allyl isothiocyanate (CT-AIT) coating. The treatment effect on microbial loads and fruit quality during 21days storage at 10°C was also determined. A bacterial cocktail containing three serotypes of Salmonella enterica was used for this study based on their association with produce-related outbreaks. Tomatoes were spot inoculated on stem scars and then immersed in an organic acid solution (700ml) containing 0.5% (v/v) each of acetic (AA) and formic acid (FA) to wash under mild agitation for 1min at ambient temperature (22°C) followed by 1min dipping in a coating solution containing 6mlAIT/g CT. AW in 0.5% organic acid (AA+FA) for 1min reduced Salmonella population by 2.7logCFU/g from an initial load of 7.8logCFU/g, while additional coating treatment of AW tomatoes reduced the pathogens on stem scars to undetectable levels (7logCFU/g reduction for the pathogen. Although the populations of Salmonella in the controls (approx. 7.8logCFU/g stem scar) did not change significantly during 21days of storage at 10°C, the populations were reduced to undetectable level in the integrated (AW plus CT-AIT) treated stem scars on day 1 and no regrowth was observed during storage. The treatment significantly (p<0.05) reduced background bacterial loads to approx. 1.3logCFU/g and the population remained unchanged through day 21 at 10°C. The treatment also completely inactivated mold and yeast on day 1 with no growth reoccurrence. These results indicate that the integrated treatment can provide a safe and effective intervention strategy for grape tomatoes. Published by Elsevier B.V.

  5. 21 CFR 172.850 - Lactylated fatty acid esters of glycerol and propylene glycol.

    Science.gov (United States)

    2010-04-01

    ... propylene glycol. 172.850 Section 172.850 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH... esters of glycerol and propylene glycol. The food additive lactylated fatty acid esters of glycerol and propylene glycol may be safely used in food in accordance with the following prescribed conditions: (a) The...

  6. 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.

  7. Sugar fatty acid esters inhibit biofilm formation by food-borne pathogenic bacteria

    Science.gov (United States)

    Furukawa, Soichi; Akiyoshi, Yuko; O’Toole, George A.; Ogihara, Hirokazu; Morinaga, Yasushi

    2010-01-01

    Effects of food additives on biofilm formation by food-borne pathogenic bacteria were investigated. Thirty-three potential food additives and 3 related compounds were added to the culture medium at concentrations from 0.001 to 0.1% (w/w), followed by inoculation and cultivation of five biofilm-forming bacterial strains for the evaluation of biofilm formation. Among the tested food additives, 21 showed inhibitory effects of biofilm formation by Staphylococcus aureus and Escherichia coli, and in particular, sugar fatty acid esters showed significant anti-biofilm activity. Sugar fatty acid esters with long chain fatty acid residues (C14-16) exerted their inhibitory effect at the concentration of 0.001%(w/w), but bacterial growth was not affected at this low concentration. Activities of the sugar fatty acid esters positively correlated with the increase of the chain length of the fatty acid residues. Sugar fatty acid esters inhibited the initial attachment of the Staphylococcus aureus cells to the abiotic surface. Sugar fatty acid esters with long chain fatty acid residues (C14-16) also inhibited biofilm formation by Streptococcus mutans and Listeria monocytogenes at 0.01%(w/w), while the inhibition of biofilm formation by Pseudomonas aeruginosa required the addition of a far higher concentration (0.1%(w/w)) of the sugar fatty acid esters. PMID:20089325

  8. Chemometric analysis of mass spectra of cis and trans fatty acid picolinyl esters

    DEFF Research Database (Denmark)

    Leth, Torben

    1997-01-01

    Capillary GC of fatty acid methyl esters with MS detection only yields information about the molecular weight of the compound. However, if picolinyl esters of fatty acids are analysed in this way it is possible to obtain more information about their structure, perhaps even the cis or trans...... with a quadropole MS-detector. The mass spectra clearly show the molecular weight and the position of double bonds in the fatty acids, but whether the configuration is cis or trans is impossible to discern visually. However, with the use of principal component analysis, it is possible to distinguish between cis...... configuration. Picolinyl esters of fatty acids are prepared by adding carbonyl-diimidazole, 3-hydroxy-methylpyridine and 4-pyrrolidin-o-pyridine to a solution of free fatty acids in dichloromethane. The picolinyl esters dissolved in heptane are then separated by capillary GC on a CP Sil 88 column equipped...

  9. Successful treatment of recalcitrant cutaneous sarcoidosis with fumaric acid esters

    Directory of Open Access Journals (Sweden)

    Hanefeld Christoph

    2002-12-01

    Full Text Available Abstract Background Sarcoidosis is a multisystem disease of unknown origin characterized by the formation of noncaseating granulomas, in particular in the lungs, lymph nodes, eyes, and skin. Systemic treatment for cutaneous sarcoidosis can be used for large disfiguring lesions, generalized involvement, or recalcitrant lesions that did not respond to topical therapy. Case presentations We report three patients with recalcitrant cutaneous sarcoidosis who were treated with oral fumaric acid esters (FAE. Three female patients presented with cutaneous sarcoidosis that have proved to be refractory to various therapies, including corticosteroids and chloroquine. We treated the patients with FAE in tablet form using two formulations differing in strength (Fumaderm® initial, Fumaderm®. Dosage of FAE was performed according to the standard therapy regimen for psoriasis patients. After treatment with FAE (4–12 months, a complete clearance of skin lesions was achieved in the three patients. The side effects observed in this trial correspond to the well-known spectrum of adverse effects of FAE (flush, minor gastrointestinal complaints, lymphopenia. Conclusions On the basis of our findings FAE therapy seems to be a safe and effective regimen for patients with recalcitrant cutaneous sarcoidosis. Nevertheless further investigations are necessary to confirm our preliminary results.

  10. Successful treatment of recalcitrant cutaneous sarcoidosis with fumaric acid esters

    Science.gov (United States)

    Nowack, Ute; Gambichler, Thilo; Hanefeld, Christoph; Kastner, Ulrike; Altmeyer, Peter

    2002-01-01

    Background Sarcoidosis is a multisystem disease of unknown origin characterized by the formation of noncaseating granulomas, in particular in the lungs, lymph nodes, eyes, and skin. Systemic treatment for cutaneous sarcoidosis can be used for large disfiguring lesions, generalized involvement, or recalcitrant lesions that did not respond to topical therapy. Case presentations We report three patients with recalcitrant cutaneous sarcoidosis who were treated with oral fumaric acid esters (FAE). Three female patients presented with cutaneous sarcoidosis that have proved to be refractory to various therapies, including corticosteroids and chloroquine. We treated the patients with FAE in tablet form using two formulations differing in strength (Fumaderm® initial, Fumaderm®). Dosage of FAE was performed according to the standard therapy regimen for psoriasis patients. After treatment with FAE (4–12 months), a complete clearance of skin lesions was achieved in the three patients. The side effects observed in this trial correspond to the well-known spectrum of adverse effects of FAE (flush, minor gastrointestinal complaints, lymphopenia). Conclusions On the basis of our findings FAE therapy seems to be a safe and effective regimen for patients with recalcitrant cutaneous sarcoidosis. Nevertheless further investigations are necessary to confirm our preliminary results. PMID:12498617

  11. 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 The coupling reaction between ethyl acetoacetate and a number of aryl halides in the presence of palladium acetate, a bulky and electron rich phosphine and K3PO4 is described. The arylated acetoacetate ester is de-acylated under the reaction...

  12. 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...

  13. A Convenient Synthesis and Antibacterial Activity of Novel α-Aminophosphonic Acid Esters from Amino Acids/Esters (Kabachnik-Fields Reaction

    Directory of Open Access Journals (Sweden)

    CH. Mohan

    2008-01-01

    Full Text Available Synthesis of novel α-aminophosphonic acid esters (5a-n were achieved with high yields through one-pot three component reaction process by Kabachnik-Fields reaction. It involves the reaction among amino acids/esters, substituted aromatic aldehydes and dialkyl phosphites in absolute ethanol at reflux temperature. Their structures were established by elemental analysis IR, ¹H, ¹³C, ³¹P NMR and mass spectral data. All the title compounds were screened for their antibacterial activity. Most of the compounds exhibited moderate antimicrobial activity.

  14. Synthesis of fatty acid sterol esters using cholesterol esterase from Trichoderma sp. AS59.

    Science.gov (United States)

    Morinaga, Naoya; Maeda, Atsushi; Mizuno, Takayuki; Bunya, Masanori; Sugihara, Shigeo; Sugihara, Akio

    2011-05-06

    We recently reported the characterization of novel cholesterol esterase (EC. 3.1.1.13) from Trichoderma sp. and preliminary work on sterol ester synthesis. In the present study, we further examined the enzyme ability to synthesize cholesterol esters from cholesterol and free fatty acids of various chain lengths, and compared the fatty acid specificity in synthesis with that in hydrolysis. The enzyme catalyzed the synthesis of medium- and long-chain fatty acid cholesterol esters, but failed to synthesize short-chain fatty acid esters. The fatty acid specificities in the synthesis and hydrolysis of cholesterol esters were entirely different from each other. Unlike other lipolytic enzymes, the enzyme was largely independent of water content in the synthesis of cholesterol oleate, and it achieved near-complete esterification in the presence of an equimolar excess of oleic acid. Of additional interest is the finding that the addition of n-hexane markedly enhanced the esterification activities on all the medium- and long-chain saturated fatty acids used. Based on these findings, we attempted to synthesize stigmasterol stearate as a food additive to lower cholesterol levels in blood plasma, and found that the enzyme catalyzed effective synthesis of the ester without the need of dehydration during the reaction, indicating the potential utility of the enzyme in the food industry. Copyright © 2011 Elsevier Inc. All rights reserved.

  15. 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

  16. 21 CFR 178.3780 - Polyhydric alcohol esters of long chain monobasic acids.

    Science.gov (United States)

    2010-04-01

    ... monobasic acids consist of polyhydric alcohol esters having number average molecular weights in the range of.../code_of_federal_regulations/ibr_locations.html. (4) Ultraviolet absorbance as specified in § 178.3770(a...

  17. Simple and Convenient Synthesis of Esters from Carboxylic Acids and Alkyl Halides Using Tetrabutylammonium Fluoride

    National Research Council Canada - National Science Library

    Matsumoto, Kouichi; Shimazaki, Hayato; Miyamoto, Yu; Shimada, Kazuaki; Haga, Fumi; Yamada, Yuki; Miyazawa, Hirotsugu; Nishiwaki, Keiji; Kashimura, Shigenori

    2014-01-01

    A simple and convenient method has been developed for the synthesis of esters from the corresponding carboxylic acids and alkyl halides by using a stoichiometric amount of tetrabutylammonium fluoride (Bu4NF) as the base...

  18. Enzymatic Synthesis of Hydroxycinnamic Acid Glycerol Esters Using Type A Feruloyl Esterase from Aspergillus niger

    National Research Council Canada - National Science Library

    TSUCHIYAMA, Moriyasu; SAKAMOTO, Tatsuji; TANIMORI, Shinji; MURATA, Shuichi; KAWASAKI, Haruhiko

    2007-01-01

    We found that hydroxycinnamic acid (HA) glycerol esters such as 1-sinapoyl glycerol and 1-p-coumaroyl glycerol can be synthesized through a direct esterification reaction using a type A feruloyl esterase from Aspergillus niger...

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

    National Research Council Canada - National Science Library

    Balak, Deepak; Bavinck, Jan Nico Bouwes; De Vries, A.P.J; Hartman, J; Martino Neumann, H.A; Zietse, Bob; 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...

  20. Enhancement of Emulsifying Properties of Cuttlefish Skin Gelatin by Modification with N-hydroxysuccinimide Esters of Fatty Acids

    NARCIS (Netherlands)

    Aewsiri, T.; Benjakul, S.; Visessanguan, W.; Encarnacion, A.B.; Wierenga, P.A.; Gruppen, H.

    2013-01-01

    Cuttlefish (Sepia pharaonis) skin gelatin modified with N-hydroxysuccinimide esters of various fatty acids including capric acid (C10:0), lauric acid (C12:0), and myristic acid (C14:0) at different molar ratios was characterized and determined for emulsifying property. Fatty acid esters were

  1. Immunogenicity of aryl esters of salicylic or acetylsalicylic acid in guinea pigs.

    Science.gov (United States)

    Schlumberger, H D

    1975-01-01

    A variety of derivatives of acetylsalicylic and salicylic acid have been investigated for their immunogenic properties in guinea pigs including salicylsalicylic acid (SSA), acetylsalicylsalicylic acid (ASSA), disalicylide (DI), trisalicylide (TRI), acetylsalicylic acid paracetamol ester (ASPE) and acetylsalicylic acid guajacol ester (ASGE). Contact sensitivity could be elicited by the sensitizing agent, however, with acetylsalicylic acid anhydride (ASAN) a more pronounced contact reaction could consistently be observed. Systemic anaphylactic reactions elicited by intravenous injection of N-salicyloyl bovine serum albumin could only be induced by ASAN, DI, TRI and ASSA, whereas SSA, ASPE and ASGE did not induce an anaphylactic state at a comparable dose level. From these results it is anticipated that all aryl esters of acetylsalicylic or salicylic acid are immunogenic when applied intradermally, leading to a N-salicyloyl specific immune response.

  2. Fumaric acid esters for psoriasis: a systematic review.

    Science.gov (United States)

    Smith, D

    2017-02-01

    Psoriasis is a chronic skin disease associated with increased morbidity and mortality. Effective and safe long term treatment options are required to manage the illness successfully. A number of systemic agents are available, however, each of them has potentially significant side effects. Fumaric acid esters (FAE) are used first line in Germany for the management of moderate to severe psoriasis, however, their use in Ireland is on an unlicensed basis (Clinical and Experimental Dermatology 37:786-801, 2012). The purpose of this literature review is to evaluate the efficacy and safety of FAEs in the management of moderate to severe psoriasis in adult patients. The reviewer intends to systematically review all available literature on the efficacy and/or safety of fumaric acid esters in the management of moderate to severe psoriasis in adult patients. A systematic review of the literature was performed by one reviewer. The PubMed, TRIP, Embase, and Cochrane Collaboration databases were systematically interrogated to include randomised controlled trials, cohort studies and case studies evaluating the efficacy and/or safety of FAEs in the management of moderate to severe psoriasis in adult patients. Inclusion criteria were studies which included adults over 18 years of age, with a diagnosis of moderate to severe chronic plaque psoriasis, who were treated with FAEs and no other systemic anti-psoriatic agents concurrently. Exclusion criteria were studies involving children, mild psoriasis, studies which did not include patients with chronic plaque psoriasis, the use of FAE for the management of illnesses other than psoriasis, and patients treated with more than one systemic anti-psoriatic agent concurrently. In total 19 articles were selected for review including 2 randomised placebo controlled trials, 1 non-randomised comparative study, 7 retrospective cohort studies, 2 prospective cohort studies and 7 case studies. The findings suggest that FAEs are a safe and effective

  3. 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.

  4. Fumaric Acid Esters Attenuate Secondary Degeneration after Spinal Cord Injury.

    Science.gov (United States)

    Cordaro, Marika; Casili, Giovanna; Paterniti, Irene; Cuzzocrea, Salvatore; Esposito, Emanuela

    2017-11-01

    Spinal cord injury (SCI) causes permanent changes in motor, sensory, and autonomic functions. Unfortunately, there are no stable cures and current treatments include surgical decompression, methylprednisolone, and hemodynamic control that lead to modest function recovery. Fumaric acid esters (FAEs) were firstly used in the management of an immunological skin disorder, such as psoriasis. Because of their potent anti-inflammatory effects, they have been introduced in multiple sclerosis (MS). Investigation has shown not only an anti-inflammatory, but also supposed neuroprotective mechanism of action. The goal of the present work was to evaluate the potential beneficial effects of dimethyl fumarate (DMF) and monomethyl fumarate (MMF) in a mouse model of traumatic SCI. SCI was produced by extradural compression for 1 min of the spinal cord at the T6-7 level using an aneurysm clip, and DMF and MMF (both at 30 mg/kg) were administered by oral gavage to the mice 1 and 6 h after SCI. For locomotor activity, study mice were treated with FAEs once daily for 10 days. We observed that mice treated with DMF exhibited a significant and sustained recovery of motor function. FAEs significantly reduced the severity of inflammation by a modulation of pro-inflammatory cytokines and apoptosis factors, and increased neutrophic factors such as anti-brain-derived neurotrophic factor (BDNF), anti-glial cell-derived neurotrophic factor (GDNF), and neurotrophin-3 (NT3). Our results showed important protective effects of DMF in an animal model of SCI, considerably improving recovery of motor function, possibly by reducing the secondary inflammation and tissue injury that characterize this model. DMF may constitute a promising target for future SCI therapies.

  5. Fluxional cyclic seleninate ester: NMR and computational studies, glutathione peroxidase-like behavior, and unexpected rearrangement.

    Science.gov (United States)

    McNeil, Nicole M R; Matz, Marie C; Back, Thomas G

    2013-10-18

    The oxidation of allyl selenide 12 with hydrogen peroxide produced the corresponding allyl selenurane 14, the cyclic seleninate ester 4, or the rearranged O-allyl seleninate ester 18, dependng on the conditions. Crossover experiments with selenide 12 and its deuterated crotyl analogue 27 indicated an intramolecular rearrangement that proceeds by an intramolecular pathway where the allyl or crotyl group is translocated via its distal carbon atom to the hydroxymethyl functionality. Variable-temperature NMR experiments with cyclic seleninate ester 4 revealed fluxional behavior at room temperature that was catalyzed by trifluoroacetic acid. Computational studies indicated an activation energy of 12.3 kcal mol(-1) for hydroxyl interchange at selenium, comparable to the value of 15.5 kcal mol(-1) derived from the NMR experiments. The glutathione peroxidase-like activity of 4 was measured in an assay where the catalysis of the reduction of hydrogen peroxide with benzyl thiol was monitored by the appearance of dibenzyl disulfide. The catalytic activity of 4 was double that observed with the unsubstituted seleninate ester 2 but was limited by the competing accumulation of the relatively inert selenenyl sulfide 32, resulting in a deactivation pathway that competes with the primary catalytic cycle.

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

    Science.gov (United States)

    Litjens, Nicolle HR; van Strijen, Elisabeth; van Gulpen, Co; Mattie, Herman; van Dissel, Jaap T; Thio, H Bing; Nibbering, Peter H

    2004-01-01

    Background 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 bioactive metabolite is monomethylfumarate (MMF). Little is known about the pharmacokinetics of these FAE. The aim of the present study was to investigate the hydrolysis of DMF to MMF and the stability of MMF, DMF and MEF at in vitro conditions representing different body compartments. Results DMF is hydrolyzed to MMF in an alkaline environment (pH 8), but not in an acidic environment (pH 1). In these conditions MMF and MEF remained intact during the period of analysis (6 h). Interestingly, DMF was hardly hydrolyzed to MMF in a buffer of pH 7.4, but was rapidly hydrolyzed in human serum having the same pH. Moreover, in whole blood the half-life of DMF was dramatically reduced as compared to serum. The concentrations of MMF and MEF in serum and whole blood decreased with increasing time. These data indicate that the majority of the FAE in the circulation are metabolized by one or more types of blood cells. Additional experiments with purified blood cell fractions resuspended in phosphate buffered saline (pH 7.4) revealed that at concentrations present in whole blood monocytes/lymphocytes, but not granulocytes and erythrocytes, effectively hydrolyzed DMF to MMF. Furthermore, in agreement with the data obtained with the pure components of the tablet, the enteric-coated tablet remained intact at pH 1, but rapidly dissolved at pH 8. Conclusion Together, these in vitro data indicate that hydrolysis of DMF to MMF rapidly occurs at pH 8, resembling that within the small intestines, but not at pH 1 resembling the pH in the stomach. At both pHs MMF and MEF remained intact. These data explain the observation that after oral FAE intake MMF and MEF, but not DMF, can be readily detected in the

  7. 40 CFR 721.1875 - Boric acid, alkyl and substituted alkyl esters (generic name).

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Boric acid, alkyl and substituted... Significant New Uses for Specific Chemical Substances § 721.1875 Boric acid, alkyl and substituted alkyl... chemical substance boric acid, alkyl and substituted alkyl esters (PMN P-86-1252) is subject to reporting...

  8. Selected Gamma Aminobutyric Acid (GABA Esters may Provide Analgesia for Some Central Pain Conditions

    Directory of Open Access Journals (Sweden)

    Joel S. Goldberg

    2010-08-01

    Full Text Available Central pain is an enigmatic, intractable condition, related to destruction of thalamic areas, resulting in likely loss of inhibitory synaptic transmission mediated by GABA. It is proposed that treatment of central pain, a localized process, may be treated by GABA supplementation, like Parkinson’s disease and depression. At physiologic pH, GABA exists as a zwitterion that is poorly permeable to the blood brain barrier (BBB. Because the pH of the cerebral spinal fluid (CSF is acidic relative to the plasma, ion trapping may allow a GABA ester prodrug to accumulate and be hydrolyzed within the CSF. Previous investigations with ester local anesthetics may be applicable to some GABA esters since they are weak bases, hydrolyzed by esterases and cross the BBB. Potential non-toxic GABA esters are discussed. Many GABA esters were investigated in the 1980s and it is hoped that this paper may spark renewed interest in their development.

  9. Polymers from amino acids: development of dual ester-urethane melt condensation approach and mechanistic aspects.

    Science.gov (United States)

    Anantharaj, S; Jayakannan, M

    2012-08-13

    A new dual ester-urethane melt condensation methodology for biological monomers-amino acids was developed to synthesize new classes of thermoplastic polymers under eco-friendly and solvent-free polymerization approach. Naturally abundant L-amino acids were converted into dual functional ester-urethane monomers by tailor-made synthetic approach. Direct polycondensation of these amino acid monomers with commercial diols under melt condition produced high molecular weight poly(ester-urethane)s. The occurrence of the dual ester-urethane process and the structure of the new poly(ester-urethane)s were confirmed by (1)H and (13)C NMR. The new dual ester-urethane condensation approach was demonstrated for variety of amino acids: glycine, β-alanine, L-alanine, L-leucine, L-valine, and L-phenylalanine. MALDI-TOF-MS end group analysis confirmed that the amino acid monomers were thermally stable under the melt polymerization condition. The mechanism of melt process and the kinetics of the polycondensation were studied by model reactions and it was found that the amino acid monomer was very special in the sense that their ester and urethane functionality could be selectively reacted by polymerization temperature or catalyst. The new polymers were self-organized as β-sheet in aqueous or organic solvents and their thermal properties such as glass transition temperature and crystallinity could be readily varied using different l-amino acid monomers or diols in the feed. Thus, the current investigation opens up new platform of research activates for making thermally stable and renewable engineering thermoplastics from natural resource amino acids.

  10. 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.

  11. 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.

  12. Analysis of Chemical Signatures of Alkaliphiles using Fatty Acid Methyl Ester Analysis.

    Science.gov (United States)

    Sreenivasulu, Basha; Paramageetham, Chinthala; Sreenivasulu, Dasari; Suman, Bukke; Umamahesh, Katike; Babu, Gundala Prasada

    2017-01-01

    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. 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. 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. 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.

  13. Enzymatic synthesis of oligo- and polysaccharide fatty acid esters

    NARCIS (Netherlands)

    Broek, van den L.A.M.; Boeriu, C.G.

    2013-01-01

    Amphiphilic oligo- and polysaccharides (e.g. polysaccharide alkyl or alkyl-aryl esters) form a new class of polymers with exceptional properties. They function as polymeric surfactants, whilst maintaining most of the properties of the starting polymeric material such as emulsifying, gelling, and

  14. Enantioconvergent synthesis by sequential asymmetric Horner-Wadsworth-Emmons and palladium-catalyzed allylic substitution reactions

    DEFF Research Database (Denmark)

    Pedersen, Torben Møller; Hansen, E. Louise; Kane, John

    2001-01-01

    A new method for enantioconvergent synthesis has been developed. The strategy relies on the combination of an asymmetric Horner-Wadsworth-Emmons (HWE) reaction and a palladium-catalyzed allylic substitution. Different $alpha@-oxygen-substituted, racemic aldehydes were initially transformed...... by asymmetric HWE reactions into mixtures of two major $alpha@,$beta@-unsaturated esters, possessing opposite configurations at their allylic stereocenters as well as opposite alkene geometry. Subsequently, these isomeric mixtures of alkenes could be subjected to palladium-catalyzed allylic substitution...

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

    Energy Technology Data Exchange (ETDEWEB)

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

    1984-05-01

    Labeled and unlabeled aliphatic and steroid esters of gamma-amino(U-/sup 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.

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

    Science.gov (United States)

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

    1984-05-01

    Labeled and unlabeled aliphatic and steroid esters of gamma-amino[U-14C]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.

  17. Novel Approach: Tungsten Oxide Nanoparticle as a Catalyst for Malonic Acid Ester Synthesis via Ozonolysis

    Directory of Open Access Journals (Sweden)

    Bilal A. Wasmi

    2014-01-01

    Full Text Available Malonic acid ester was synthesized via the one-step ozonolysis of palm olein. Malonic acid ester was spectroscopically characterized using gas chromatography mass spectroscopy (GC-MS. Tungsten oxide nanoparticles were used as the catalyst, which was characterized via X-ray powder diffraction (XRD and field emission scanning electron microscopy (FE-SEM. Tungsten oxide provided several advantages as a catalyst for the esterification malonic acid such as simple operation for a precise ozonation method, an excellent yield of approximately 10%, short reaction times of 2 h, and reusability due to its recyclability.

  18. Inhibitory effects of caffeic acid phenethyl ester derivatives on replication of hepatitis C virus.

    Directory of Open Access Journals (Sweden)

    Hui Shen

    Full Text Available Caffeic acid phenethyl ester (CAPE has been reported as a multifunctional compound. In this report, we tested the effect of CAPE and its derivatives on hepatitis C virus (HCV replication in order to develop an effective anti-HCV compound. CAPE and CAPE derivatives exhibited anti-HCV activity against an HCV replicon cell line of genotype 1b with EC50 values in a range from 1.0 to 109.6 µM. Analyses of chemical structure and antiviral activity suggested that the length of the n-alkyl side chain and catechol moiety are responsible for the anti-HCV activity of these compounds. Caffeic acid n-octyl ester exhibited the highest anti-HCV activity among the tested derivatives with an EC50 value of 1.0 µM and an SI value of 63.1 by using the replicon cell line derived from genotype 1b strain Con1. Treatment with caffeic acid n-octyl ester inhibited HCV replication of genotype 2a at a similar level to that of genotype 1b irrespectively of interferon signaling. Caffeic acid n-octyl ester could synergistically enhance the anti-HCV activities of interferon-alpha 2b, daclatasvir, and VX-222, but neither telaprevir nor danoprevir. These results suggest that caffeic acid n-octyl ester is a potential candidate for novel anti-HCV chemotherapy drugs.

  19. 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 Impact factor: 4.519, year: 2016

  20. 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

  1. 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...

  2. Selective Cross-Coupling of Organic Halides with Allylic Acetates

    Science.gov (United States)

    Anka-Lufford, Lukiana L.; Prinsell, Michael R.

    2012-01-01

    A general protocol for the coupling of haloarenes with a variety of allylic acetates is presented. Strengths of the method are a tolerance for electrophilic (ketone, aldehyde) and acidic (sulfonamide, trifluoroacetamide) substrates and the ability to couple with a variety of substituted allylic acetates. Secondary alkyl bromides can also be allylated under slightly modified conditions, demonstrating the generality of the approach. Finally, the coupling of a reactive vinyl halide could be achieved by the use of a very hindered ligand and more reactive, branched allylic acetates. PMID:23095043

  3. 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.

  4. A Lewis Base Catalysis Approach for the Photoredox Activation of Boronic Acids and Esters.

    Science.gov (United States)

    Lima, Fabio; Sharma, Upendra K; Grunenberg, Lars; Saha, Debasmita; Johannsen, Sandra; Sedelmeier, Joerg; Van der Eycken, Erik V; Ley, Steven V

    2017-11-20

    We report herein the use of a dual catalytic system comprising a Lewis base catalyst such as quinuclidin-3-ol or 4-dimethylaminopyridine and a photoredox catalyst to generate carbon radicals from either boronic acids or esters. This system enabled a wide range of alkyl boronic esters and aryl or alkyl boronic acids to react with electron-deficient olefins via radical addition to efficiently form C-C coupled products in a redox-neutral fashion. The Lewis base catalyst was shown to form a redox-active complex with either the boronic esters or the trimeric form of the boronic acids (boroxines) in solution. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  5. Esterification Reaction of Glycerol and Palm Oil Oleic Acid Using Methyl Ester Sulfonate Acid Catalyst as Drilling Fluid Formulation

    Science.gov (United States)

    Sari, V. I.; Hambali, E.; Suryani, A.; Permadi, P.

    2017-02-01

    Esterification reaction between glycerol with palm oil oleic acid to produce glycerol ester and one of the utilization of glycerol esters is as ingredients of drilling fluids formula for oil drilling needs. The purpose of this research is to get the best conditions of the esterification process. The esterification reaction does with the reactants is glycerol with purity of 97.6%, palm oil oleic acid with the molar ratio is 1:1, Methyl Ester Sulfonate Acid (MESA) catalyst 0.5%, and stirring speed 400 rpm. The temperature range of 180°C to 240°C and the processing time between 120 to 180 minutes. The results showed that the best conditions of the esterification reaction at the temperature 240°C and time process are 180 minute. The increasing temperature resulted that the acid number decreases and causing the conversion increased. The maximum conversion is 99.24%, density 0.93 g/cm3, flash point 241°C, pour point -3°C, the boiling point of 244 °C, the acid value of 1.90 mg KOH/g sample, kinematic viscosity 31.51 cSt (40°C), surface tension 37.0526 dyne/cm and GCMS identification, glycerol ester at 22,256 retention time (minutes) and wide area 73.75 (%). From the research results obtained glycerol ester with characteristics suitable for drilling fluid formulations.

  6. 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.

  7. Quantification of primary fatty acid amides in commercial tallow and tallow fatty acid methyl esters by HPLC-APCI-MS.

    Science.gov (United States)

    Madl, Tobias; Mittelbach, Martin

    2005-04-01

    Primary fatty acid amides are a group of biologically highly active compounds which were already identified in nature. Here, these substances were determined in tallow and tallow fatty acid methyl esters for the first time. As tallow is growing in importance as an oleochemical feedstock for the soap manufacturing, the surfactant as well as the biodiesel industry, the amounts of primary fatty acid amides have to be considered. As these compounds are insoluble in tallow as well as in the corresponding product e.g. tallow fatty acid methyl esters, filter plugging can occur. For the quantification in these matrices a purification step and a LC-APCI-MS method were developed. Although quantification of these compounds can be performed by GC-MS, the presented approach omitted any derivatization and increased the sensitivity by two orders of magnitude. Internal standard calibration using heptadecanoic acid amide and validation of the method yielded a limit of detection of 18.5 fmol and recoveries for the tallow and fatty acid methyl ester matrices of 93% and 95%, respectively. A group of commercially available samples were investigated for their content of fatty acid amides resulting in an amount of up to 0.54%m/m (g per 100 g) in tallow and up to 0.16%m/m (g per 100 g) in fatty acid methyl esters.

  8. 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 bios...... following a two-step solvent purification procedure whereby excess fatty acid substrate was first removed in a heptane/water (4:1, v/v) system, followed by selective ester extraction using an ethyl acetate/water system (1:6, v/v) at elevated temperature....

  9. Urinary excretion of N-acetyl-S-allyl-L-cystein upon garlic consumption by human volunteers.

    NARCIS (Netherlands)

    de Rooij, B.M.; Boogaard, P.J.; Rijksen, D.A.; Commandeur, J.N.M.; Vermeulen, N.P.E.

    1996-01-01

    N-Acetyl-S-allyl-L-cysteine (allylmercapturic acid, ALMA) was previously detected in urine from humans consuming garlic. Exposure of rats to allyl halides is also known to lead to excretion of ALMA in urine. ALMA is a potential biomarker for exposure assessment of workers exposed to allyl halides.

  10. 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.

  11. Synthesis of some monocyclic analogues of mycophenolic acid via the Johnson ortho ester Claisen rearrangement.

    Science.gov (United States)

    Meza-Aviña, Ma Elena; Ordoñez, Mario; Fernández-Zertuche, Mario; Rodríguez-Fragoso, Lourdes; Reyes-Esparza, Jorge; de Los Ríos-Corsino, Abril A Martínez

    2005-12-01

    The synthesis of some monocyclic analogues of mycophenolic acid in which the lactone ring has been eliminated, leaving the aromatic ring intact and the same oxygenated substituents flanking the hexenoic acid side chain with an (E)-geometry at the double bond, has been accomplished via the Johnson ortho ester Claisen rearrangement. The synthetic methodology reported here allows the preparation of mycophenolic acid analogues bearing alkyl substituents at the alpha- and beta-positions on the side chain.

  12. Fumaric Acid and its Esters: An Emerging Treatment for Multiple Sclerosis

    OpenAIRE

    Moharregh-Khiabani, D.; Linker, R. A.; Gold, R.; Stangel, M.

    2009-01-01

    Fumaric acid is an intermediate product of the citric acid cycle that is a source of intracellular energy in the form of adenosine triphosphate (ATP). It is generated by oxidation of adenylsuccinate by the enzyme succinate dehydrogenase and is then converted to maleate by the enzyme fumarase. At present, fumaric acid esters (FAE) are licensed for the treatment of psoriasis. Several lines of evidence have demonstrated immunomodulatory effects for FAE. Clinical studies in psoriasis showed a red...

  13. Preparation of 9-hydroxynonanoic acid methyl ester by ozonolysis of vegetable oils and its polycondensation

    Directory of Open Access Journals (Sweden)

    Cvetković Ivana

    2008-01-01

    Full Text Available Vegetable oil-based and potentially biodegradable polyesters were prepared from 9-hydroxynonanoic acid methyl ester. This paper describes ozonolysis of vegetable oils and the method for preparation of useful monomers and in particular 9-hydroxynonanoic acid methyl ester. Ozonolysis of soybean oil and castor oil in methanol and methylene chloride solution, followed by reduction with sodium borohydride was used to obtain a mixture of triols, diols and monols. Triglyceride triols were separated from the rest of the mixture and transesterified with methanol to obtain methyl esters of fatty acids and glycerin. The main component of fatty acids was 9-hydroxynonanoic acid methyl ester, which was characterized and used for polycondensation by transesterification. High molecular weight polyhydroxy alcanoate was a solid having a melting point of 75°C. The molecular weight of the resulting polyester was affected by the purity of the monomer and side reactions such as cyclization. The polymer was characterized by chromatographic, thermal and analytical methods.

  14. Enantiomeric Excess Determination without Chiral Auxiliary Compounds. A New 31P NMR Method for Amino Acid Esters and Primary Amines

    NARCIS (Netherlands)

    Strijtveen, Bert; Kellogg, Richard M.; Feringa, Bernard

    1986-01-01

    Amino acid esters and primary amines yield diastereoisomeric methylphosphonic diamides 5 upon reaction with MePSCl2. The enantiomeric excess of amino acid esters and amines is easily determined by measurement of the ratio of diastereoisomers of 5 by 31P NMR spectroscopy.

  15. Synthesis and evaluation of odour-active methionyl esters of fatty acids via esterification and transesterification of butter oil.

    Science.gov (United States)

    Li, Cheng; Sun, Jingcan; Fu, Caili; Yu, Bin; Liu, Shao Quan; Li, Tianhu; Huang, Dejian

    2014-02-15

    Methionol-derived fatty acid esters were synthesised by both chemical and lipase catalysed esterification between fatty acids and methionol. Beneficial effects of both methods were compared qualitatively and quantitatively by GC-MS/GC-FID results. And the high acid and heat stability of our designed methionyl esters meet the requirement of the food industry. Most importantly, the sensory test showed that fatty acid carbon-chain length had an important effect on the flavour attributes of methionyl esters. Moreover, through Lipozyme TL IM-mediated transesterification, valuable methionol-derived esters were synthesised from the readily available natural material butter oil as the fatty acid source. The conversion of methionol and yield of each methionyl ester were also elucidated by GC-MS-FID. Copyright © 2013 Elsevier Ltd. All rights reserved.

  16. N-Cholyl Amino Acid Alkyl Esters - A Novel Class of Organogelators

    NARCIS (Netherlands)

    Willemen, H.M.; Vermonden, T.; Marcelis, A.T.M.; Sudhölter, E.J.R.

    2001-01-01

    Several N-cholyl amino acid alkyl esters were found to act as novel, potent organogelators for aromatic solvents and cyclohexene. These novel organogelators afford stable, transparent, and thermoreversible gels. Modification of the molecular structure and IR measurements show that gelation takes

  17. 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

    substituents have been examined by TGA‐MS using different sulphonic acids. A substantial lowering of the cleavage temperature is observed, and the ester cleavage can even be performed in situ on roll‐to‐roll‐coated films on polyethylene terephthalate (PET). © 2011 Wiley Periodicals, Inc. J Polym Sci Part A...

  18. Developmental toxicity study of vegetable oil-derived stanol fatty acid esters

    NARCIS (Netherlands)

    Slesinski, R.S.; Turnbull, D.; Frankos, V.H.; Wolterbeek, A.P.M.; Waalkens-Berendsen, D.H.

    1999-01-01

    In a standard developmental toxicity study, a mixture of vegetable oil- derived stanol fatty acid esters was administered in the diet to groups of 28 mated female HsdCpb:WU Wistar rats at concentrations that provided 0, 1, 2.5, and 5% total stanols (equivalent to 0, 1.75, 4.38, and 8.76% plant

  19. 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

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

    African Journals Online (AJOL)

    Oil extracted from the seeds of Curcubita pepo was transesterified using potassium hydroxide in methanol. Fatty acid methyl esters (FAME) profile of the produced diesel was analyzed using Gas chromatograph coupled with mass spectrophotometer (GC-MS). The results indicate the presence of methyl ...

  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. 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.

  3. 40 CFR 721.6475 - Alkyl polycarboxylic acids, esters with ethoxylated fatty alcohols.

    Science.gov (United States)

    2010-07-01

    ... PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES... chemical substances identified generically as alkyl polycarboxylic acids, esters with ethoxylated fatty... requirements. The provisions of subpart A of this part apply to this section except as modified by this...

  4. 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.

  5. 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

  6. 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

  7. Fumaric acid esters in recalcitrant pediatric psoriasis: A prospective, daily clinical practice case series

    NARCIS (Netherlands)

    Geel, M.J. van; Kerkhof, P.C. van de; Oostveen, A.M.; Jong, E.M. de; Seyger, M.M.

    2016-01-01

    BACKGROUND: Evidence on fumaric acid esters (FAE) in the treatment of pediatric psoriasis is scarce. OBJECTIVE: Describe the effectiveness, influence on the quality of life (QoL) and safety of FAE in children with recalcitrant psoriasis in daily clinical practice. METHODS: A prospective case series.

  8. Regulated genes in psoriatic skin during treatment with fumaric acid esters

    NARCIS (Netherlands)

    Onderdijk, A. J.; Balak, D. M. W.; Baerveldt, E. M.; Florencia, E. F.; Kant, M.; Laman, J. D.; van IJcken, W. F. . J.; Racz, E.; de Ridder, D.; Thio, H. B.; Prens, E. P.

    2014-01-01

    BackgroundFumaric acid esters (FAEs) are widely used in Europe for the treatment of psoriasis because of their clinical efficacy and favourable safety profile. However, the mechanisms of action by which FAEs improve psoriasis remain largely unknown. ObjectivesTo identify pathways and mechanisms

  9. 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...

  10. 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: (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 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.

  11. 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...

  12. Synthesis and transdermal properties of acetylsalicylic acid and selected esters

    OpenAIRE

    Gerber, Minja; Breytenbach, Jaco C.; Hadgraft, Jonathan; du Plessis, Jeanetta

    2006-01-01

    The primary aim of this study was to determine the transdermal penetration of acetylsalicylic acid and some of its derivatives, to establish a correlation, if any, with selected physicochemical properties and to determine if transdermal application of acetylsalicylic acid and its derivatives will give therapeutic drug concentrations with respect to transdermal flux. Ten derivatives of acetylsalicylic acid were prepared by esterification of acetylsalicyloyl chloride with ten different alcohols...

  13. 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.

  14. 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.

  15. Secreted 3-isopropylmalate methyl ester signals invasive growth during amino acid starvation in Saccharomyces cerevisiae.

    Science.gov (United States)

    Dumlao, Darren S; Hertz, Nicholas; Clarke, Steven

    2008-01-15

    The Saccharomyces cerevisiae methyltransferase encoded by TMT1 catalyzes the AdoMet-dependent monomethylation of 3-isopropylmalate, an intermediate of the leucine biosynthetic pathway. The biological significance of methylating 3-isopropylmalate and the relationship between Tmt1 and the leucine biosynthetic pathway is not yet established. We present evidence here showing that methylation of 3-isopropylmalate functions to extracellularly signal yeast to grow invasively. We show that methyl esterification generates 3-isopropylmalate-1-methyl ester. We find that the Tmt1 methyltransferase functions independently of the biosynthetic pathway but is induced when cells are starved for amino acids; the largest induction is observed with the removal of leucine from the media. This amino acid starvation stress response is controlled by the transcriptional activator Gcn4. After methylation, 3-isopropylmalate methyl ester is secreted into the media within 3 h. Thin layer chromatography and gas chromatography mass spectroscopy confirm that the intact molecule is secreted. Finally, we show that purified 3-isopropylmalate methyl ester can enhance the ability of the haploid yeast strain 10560-23C to grow invasively. Our data identifies 3-isopropylmalate methyl ester as an autoinductive molecule that provides a signal to yeast to switch from vegetative to invasive growth in response to amino acid starvation.

  16. Biosynthesis of the fatty acid isopropyl esters by engineered Escherichia coli.

    Science.gov (United States)

    Pan, Hong; Zhang, Lihua; Li, Xun; Guo, Daoyi

    2017-07-01

    The fatty acid methyl esters and fatty acid ethyl esters are known as biodiesels which are considered to be renewable, nontoxic and biodegradable biofuels. However, the conventional biodiesels show a high crystallization temperature which is one of the most critical obstacles against the widespread biodiesel usage. The high crystallization temperature of biodiesel can be reduced by replacing the methyl or ethyl ester with an isopropyl moiety. Here we report on a strategy to establish biosynthesis of the fatty acid isopropyl esters(FAIPEs) from the simple substrate glucose in Escherichia coli with heterologous coexpression of atoB encoded acetyl-CoA acetyltransferase and atoAD encode acetoacetyl-CoA transferase from E. coli, ADC encode acetoacetate decarboxylase from Clostridium acetobutylicum, ADH encoded NADP-dependent alcohol dehydrogenase from Clostridium beijerinckii, 'TesA encoded a truncated fatty acyl-ACP thioesterase and FadD encoded fatty acyl-CoA synthetase from E. coli, and the WS/DGAT encoded acyltransferase from Acinetobacter baylyi strain ADP1. It was found that the yield of FAIPEs was up to 203.4mg/L and accounted for around 6.4% (wt/wt) of the dry cell weight. Our results indicates that it is a feasible strategy to improve the yield of FAIPEs by increasing fatty acyl-CoA availability in biosynthetic pathway and exhibit a promising method for production of biodiesels with good low-temperature flow properties. Copyright © 2017 Elsevier Inc. All rights reserved.

  17. Synthesis and transdermal properties of acetylsalicylic acid and selected esters.

    Science.gov (United States)

    Gerber, Minja; Breytenbach, Jaco C; Hadgraft, Jonathan; du Plessis, Jeanetta

    2006-03-09

    The primary aim of this study was to determine the transdermal penetration of acetylsalicylic acid and some of its derivatives, to establish a correlation, if any, with selected physicochemical properties and to determine if transdermal application of acetylsalicylic acid and its derivatives will give therapeutic drug concentrations with respect to transdermal flux. Ten derivatives of acetylsalicylic acid were prepared by esterification of acetylsalicyloyl chloride with ten different alcohols. The experimental aqueous solubility, logD and transdermal flux values were determined for acetylsalicylic acid and its derivatives at pH 4.5. In vitro penetration was measured through excised female human abdominal skin in diffusion cells. The experimental aqueous solubility of acetylsalicylic acid (6.56 mg/ml) was higher than that of the synthesised acetylsalicylate derivatives (ranging from 1.76 x 10(-3) to 3.32 mg/ml), and the logD of acetylsalicylic acid (-0.85) was lower than that of its derivatives (ranging from -0.25 to 1.95). There was thus an inverse correlation between the aqueous solubility data and the logD values. The experimental transdermal flux of acetylsalicylic acid (263.83 nmol/cm(2)h) was much higher than that of its derivatives (ranging from 0.12 to 136.02 nmol/cm(2)h).

  18. Uptake in brain and neurophysiological activity of two lipid esters of gamma-aminobutyric acid.

    Science.gov (United States)

    Hesse, G W; Jacob, J N; Shashoua, V E

    1988-06-01

    Two lipid esters of gamma-aminobutyric acid (GABA), 1-linolenoyl-2,3-bis(4-aminobutyryl)propane-1,2,3-triol and 1,2-dilinolenoyl-3-(4-aminobutyryl)propane-1,2,3-triol, were found to have brain uptake indices of greater than 30% using the single-pass carotid artery injection technique. Both compounds produced dose-dependent inhibition of the evoked population spike in slices of rat hippocampus maintained in vitro. This effect was blocked reversibly by picrotoxin. The magnitude of the inhibition produced by the lipid esters of GABA was comparable to that of similar doses of GABA, but for both compounds the duration of the effect was at least 10 times longer than that produced by GABA. These data are consistent with the idea that the lipid esters of GABA can effectively penetrate the blood-brain barrier and act as prodrugs for the delivery of GABA to the central nervous system.

  19. 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.

  20. Physiological and transcriptional characterization of Saccharomyces cerevisiae engineered for production of fatty acid ethyl esters

    DEFF Research Database (Denmark)

    de Jong, Bouke Wim; Siewers, Verena; Nielsen, Jens

    2016-01-01

    Saccharomyces cerevisiae has previously been engineered to become a cell factory for the production of fatty acid ethyl esters (FAEEs), molecules suitable for crude diesel replacement. To find new metabolic engineering targets for the improvement of FAEE cell factories, three different FAEE......-producing strains of S. cerevisiae, constructed previously, were compared and characterized by quantification of key fluxes and genome-wide transcription analysis. From both the physiological and the transcriptional data, it was indicated that strain CB2I20, with high expression of a heterologous wax ester synthase...... gene (ws2) and strain BdJ15, containing disruptions of genes DGA1, LRO1, ARE1, ARE2 and POX1, which prevent the conversion of acyl-CoA to sterol esters, triacylglycerides and the degradation to acetyl-CoA, triggered oxidative stress that consequently influenced cellular growth. In the latter strain...

  1. Hydroxycinnamic acid ethyl esters as precursors to ethylphenols in wine.

    Science.gov (United States)

    Hixson, Josh L; Sleep, Nicola R; Capone, Dimitra L; Elsey, Gordon M; Curtin, Christopher D; Sefton, Mark A; Taylor, Dennis K

    2012-03-07

    A method for determining ethyl coumarate and ethyl ferulate in wine using GC-MS with deuterium-labeled analogues has been developed and used to measure the evolution of these two esters during the production of two commercial monovarietal red wines, cv. Grenache and Shiraz. During fermentation, the concentration of ethyl coumarate rose from low levels to 0.4 mg/L in Grenache and 1.6 mg/L in Shiraz wines. These concentrations then increased further during barrel aging to 1.4 and 3.6 mg/L, respectively. The concentration of ethyl ferulate was much lower, reaching a maximum of only 0.09 mg/L. Conversion of ethyl coumarate and ethyl ferulate to their corresponding ethylphenols was observed during fermentations of a synthetic medium with two strains of Dekkera bruxellensis (AWRI 1499 and AWRI 1608), while a third (strain AWRI 1613) produced no ethylphenols at all from these precursors. Strains AWRI 1499 and 1608 produced 4-ethylphenol from ethyl coumarate in 68% and 57% yields, respectively. The corresponding yields of 4-ethylguaiacol from ethyl ferulate were much lower, 7% and 3%. Monitoring of ethyl coumarate and ethyl ferulate concentration during the Dekkera fermentations showed that the selectivity for ethylphenol production according to yeast strain and the precursor was principally a result of variation in esterase activity. Consequently, ethyl coumarate can be considered to be a significant precursor to 4-ethylphenol in wines affected by these two strains of Brettanomyces/Dekkera yeast, while ethyl ferulate is not an important precursor to 4-ethylguaiacol.

  2. Parallel Synthesis of an Imidazole-4,5-dicarboxamide Library Bearing Amino Acid Esters and Alkanamines

    Directory of Open Access Journals (Sweden)

    Rosanna Solinas

    2008-12-01

    Full Text Available The imidazole-4,5-dicarboxylic acid scaffold is readily derivatized with amino acid esters and alkanamines to afford compounds with intramolecularly hydrogen bonded conformations that mimic substituted purines and therefore are hypothesized to be potential inhibitors of kinases through competitive binding to the ATP site. In this work, a total of 126 dissymmetrically disubstituted imidazole-4,5-dicarboxamides with amino acid ester and alkanamide substituents 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.

  3. Synthesis, molecular modeling and biological evaluation of novel 2-allyl amino 4-methyl sulfanyl butyric acid as α-amylase and α-glucosidase inhibitor

    Science.gov (United States)

    Balan, Kannan; Perumal, Perumal; Sundarabaalaji, Narayanan; Palvannan, Thayumanavan

    2015-02-01

    In the present study 2-allyl amino 4-methyl sulfanyl butyric acid (AMSB) was synthesized in good yield. AMSB was characterized by Fourier transforms infrared spectroscopy (FTIR), Nuclear magnetic resonance (NMR) (1H and 13C) and Liquid chromatography mass spectrometry (LCMS). The radical scavenging activity and reducing power assay of AMSB was assessed using 1-1-diphenyl 2-picryl hydrazyl (DPPH), 2,2‧-azino-bis (3-ethyl benzothiazoline-6-sulfonic acid) (ABTS) and ferric ion reducing antioxidant power assay (FRAP) and was found to be 44.1, 34.71 and 41.7 μg/ml respectively. The compound showed effective inhibition against α-amylase and α-glucosidase. AMSB was identified to be a reversible mixed noncompetitive inhibitor of α-amylase and α-glucosidase. The molecular docking study was carried out to evaluate the specific groove binding properties and affords valuable information of AMSB binding mode in the active site of α-glucosidase the study may lead to the which leads to the rational design of new class of antidiabetic drugs targeting α-glucosidase based on AMSB in near future.

  4. Treatment of psoriasis with non-registered fumaric acid esters in The Netherlands: a nationwide survey among Dutch dermatologists.

    Science.gov (United States)

    Fallah Arani, S; Balak, D M W; Neumann, H A M; Kuipers, M V; Thio, H B

    2014-07-01

    Psoriasis vulgaris is a T-cell mediated disease that affects 2-3% of the worldwide white-skinned population. Fumaric acid esters are mentioned as an effective therapy for moderate-to-severe psoriasis vulgaris in adult patients in the new guidelines for psoriasis treatment. To obtain an insight into the use of fumaric acid esters by Dutch dermatologists in the Netherlands. This was a cross-sectional postal survey. An anonymous survey was posted to all Dutch dermatologists. In this survey, data were collected on the extent of fumaric acid esters use, the reasons for use, the reasons for non- or limited use of fumaric acid esters, the perception of fumaric acid esters as a mono-therapy with regards to the effectiveness, the safety, the adverse events and the overall satisfaction of fumaric acid esters as a mono-therapy. Sixty-three per cent of the 300 responders indicated to prescribe fumaric acid esters for the treatment of psoriasis. About 37% of the dermatologists indicated (almost) never to prescribe it. Biologicals were considered as the most effective therapy. Fumaric acid esters were regarded as the safest therapy. They were generally well-tolerated by the patients similar to that for methotrexate according to the respondents. A large proportion of the dermatologists in our survey indicated to prescribe fumaric acid esters. It is considered to be effective, safe and without adverse events profile that is favourable in the practice, also as compared with other systemic therapies such as methotrexate and biologicals. © 2013 European Academy of Dermatology and Venereology.

  5. The Synthesis and Evaluation of Arctigenin Amino Acid Ester Derivatives.

    Science.gov (United States)

    Cai, En-Bo; Yang, Li-Min; Jia, Cai-Xia; Zhang, Wei-Yuan; Zhao, Yan; Li, Wei; Song, Xing-Zhuo; Zheng, Man-Ling

    2016-10-01

    The use of arctigenin (ARG), a traditional medicine with many pharmacological activities, has been restricted due to its poor solubility in water. Five amino acid derivatives of ARG have been synthesized using glycine, o-alanine, valine, leucine, and isoleucine, which have t-butyloxy carbonyl (BOC) as a protective group. In this study, we examined the effects of removing these protective groups. The results showed that the amino acid derivatives have better solubility and nitrite-clearing ability than ARG. Among the compounds tested, the amino acid derivatives without protective group were the best. Based on these results, ARG and its two amino acid derivatives without protective group (ARG8, ARG10) were selected to evaluate their anti-tumor activity in vivo at a dosage of 40 mg/kg. The results indicated that ARG8 and ARG10 both exhibit more anti-tumor activity than ARG in H22 tumor-bearing mice. The tumor inhibition rates of ARG8 and ARG10 were 69.27 and 43.58%, which was much higher than ARG. Furthermore, the mice treated with these compounds exhibited less damage to the liver, kidney and immune organs compared with the positive group. Furthermore, ARG8 and ARG10 improved the serum cytokine levels significantly compared to ARG. In brief, this study provides a method to improve the water solubility of drugs, and we also provide a reference basis for new drug development.

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

    African Journals Online (AJOL)

    eobe

    where R is a mixture of various fatty acid chains. Generally, transesterification is a reversible reaction, although in the production of biodiesel, the backward reaction does not occur or is negligible because the glycerol formed is not miscible with the product, leading to a two-phase system. Nevertheless, an excess of alcohol ...

  7. Chair interconversion and reactivity of mannuronic acid esters

    NARCIS (Netherlands)

    Ronnols, Jerk; Walvoort, Marthe T. C.; van der Marel, Gijsbert A.; Codee, Jeroen D. C.; Widmalm, Goran

    2013-01-01

    Mannopyranosyluronic acids display a very unusual conformation behavior in that they often prefer to adopt a C-1(4) chair conformation. They are endowed with a strikingly high reactivity when used in a glycosylation reaction as a glycosyl donor. To investigate the unusual conformational behavior a

  8. 40 CFR 721.10074 - Acetic acid, 2-chloro-, 1-(3,3-dimethylcyclohexyl)ethyl ester.

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Acetic acid, 2-chloro-, 1-(3,3... Specific Chemical Substances § 721.10074 Acetic acid, 2-chloro-, 1-(3,3-dimethylcyclohexyl)ethyl ester. (a... acetic acid, 2-chloro-, 1-(3,3-dimethylcyclohexyl)ethyl ester (PMN P-05-568; CAS No. 477218-59-0) is...

  9. Linear and cyclic ester Oligomers of succinic acid and 1,4-butanediol: Biocatalytic synthesis and characterization

    NARCIS (Netherlands)

    Habeych Narvaez, D.I.; Eggink, G.; Boeriu, C.G.

    2011-01-01

    The lipase-catalyzed synthesis of cyclic ester oligomers from non-activated succinic acid (A) and 1,4-butanediol (B) in the presence of immobilized Candida antarctica lipase B was investigated. Batch and pulse fed-batch systems were implemented to increase the formation of cyclic ester products. The

  10. 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.

  11. Fumaric Acid and its Esters: An Emerging Treatment for Multiple Sclerosis

    Science.gov (United States)

    Moharregh-Khiabani, D; Linker, R.A; Gold, R; Stangel, M

    2009-01-01

    Fumaric acid is an intermediate product of the citric acid cycle that is a source of intracellular energy in the form of adenosine triphosphate (ATP). It is generated by oxidation of adenylsuccinate by the enzyme succinate dehydrogenase and is then converted to maleate by the enzyme fumarase. At present, fumaric acid esters (FAE) are licensed for the treatment of psoriasis. Several lines of evidence have demonstrated immunomodulatory effects for FAE. Clinical studies in psoriasis showed a reduction of peripheral CD4+- and CD8+-T-lymphocytes due to the ability of FAE to induce apoptosis. In vitro studies with the ester dimethyl fumarate (DMF) described an inhibitory effect on nuclear factor kappa B (NF-κB)-dependent transcription of tumor necrosis factor-alpha (TNF-α) induced genes in human endothelial cells. Animal studies using a model of central nervous system demyelination, MOG-induced experimental autoimmune encephalomyelitis (EAE), revealed a reduction of microglia and macrophages in inflamed lesions. A phase II clinical study in relapsing-remitting multiple sclerosis (RRMS) patients with a modified fumaric acid ester, BG-12, showed as "proof of principle" a significant reduction in the number of gadolinium enhancing lesions after 24 weeks of treatment as compared to placebo. Further phase III studies have now started to explore the long-term efficacy of FAE. PMID:19721818

  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. Synthesis and antiradical/antioxidant activities of caffeic acid phenethyl ester and its related propionic, acetic, and benzoic acid analogues.

    Science.gov (United States)

    LeBlanc, Luc M; Paré, Aurélie F; Jean-François, Jacques; Hébert, Martin J G; Surette, Marc E; Touaibia, Mohamed

    2012-12-10

    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.

  14. Fatty acid esters of phloridzin induce apoptosis of human liver cancer cells through altered gene expression.

    Directory of Open Access Journals (Sweden)

    Sandhya V G Nair

    Full Text Available Phloridzin (phlorizin or phloretin 2'-O-glucoside is known for blocking intestinal glucose absorption. We have investigated the anticarcinogenic effect of phloridzin and its novel derivatives using human cancer cell lines. We have synthesised novel acylated derivatives of phloridzin with six different long chain fatty acids by regioselective enzymatic acylation using Candida Antarctica lipase B. The antiproliferative effects of the new compounds were investigated in comparison with the parent compounds, phloridzin, aglycone phloretin, the six free fatty acids and chemotherapeutic drugs (sorafenib, doxorubicin and daunorubicin using human hepatocellular carcinoma HepG2 cells, human breast adenocarcinoma MDA-MB-231 cells and acute monocytic leukemia THP-1 cells along with normal human and rat hepatocytes. The fatty acid esters of phloridzin inhibited significantly the growth of the two carcinoma and leukemia cells while similar treatment doses were not toxic to normal human or rat hepatocytes. The antiproliferative potency of fatty esters of phloridzin was comparable to the potency of the chemotherapeutic drugs. The fatty acid esters of phloridzin inhibited DNA topoisomerases IIα activity that might induce G0/G1 phase arrest, induced apoptosis via activation of caspase-3, and decreased ATP level and mitochondrial membrane potential in HepG2 cells. Based on the high selectivity on cancer cells, decosahexaenoic acid (DHA ester of phloridzin was selected for gene expression analysis using RT2PCR human cancer drug target array. Antiproliferative effect of DHA ester of phloridzin could be related to the down regulation of anti-apoptotic gene (BCL2, growth factor receptors (EBFR family, IGF1R/IGF2, PDGFR and its downstream signalling partners (PI3k/AKT/mTOR, Ras/Raf/MAPK, cell cycle machinery (CDKs, TERT, TOP2A, TOP2B as well as epigenetics regulators (HDACs. These results suggest that fatty esters of phloridzin have potential chemotherapeutic effects

  15. Production of alpha-hydroxy carboxylic acids and esters from higher sugars using tandem catalyst systems

    Energy Technology Data Exchange (ETDEWEB)

    Orazov, Marat; Davis, Mark E.

    2017-11-07

    The present disclosure is directed to methods and composition used in the preparation of alpha-hydroxy carboxylic acids and esters from higher sugars using a tandem catalyst system comprising retro-aldol catalysts and Lewis acid catalysts. In some embodiments, these alpha-hydroxy carboxylic acids may be prepared from pentoses and hexoses. The retro-aldol and Lewis catalysts may be characterized by their respective ability to catalyze a 1,2-carbon shift reaction and a 1,2-hydride shift reaction on an aldose or ketose substrate.

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

    Directory of Open Access Journals (Sweden)

    Eva Vavříková

    2016-06-01

    Full Text Available 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.

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

    Energy Technology Data Exchange (ETDEWEB)

    Moser, Bryan R.; Vaughn, Steven F. [United States Department of Agriculture, Agricultural Research Service, National Center for Agricultural Utilization Research, 1815 N. University St, Peoria, IL 61604 (United States)

    2010-04-15

    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{sup -1}. The derived cetane number, kinematic viscosity, and oxidative stability (Rancimat method) of CSME was 53.3, 4.21 mm{sup 2} s{sup -1} (40 C), and 14.6 h (110 C). The cold filter plugging and pour points were -15 C and -19 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. (author)

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

    Science.gov (United States)

    Ilmi, Miftahul; Abduh, Muhammad Y; Hommes, Arne; Winkelman, Jozef G M; Hidayat, Chusnul; Heeres, Hero J

    2018-01-17

    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 centrifugal contactor separator (CCCS), the latter being used for integrated reaction and liquid-liquid separation. A fatty acid butyl ester yield up to 93% was obtained in the cascade when operated in a once-through mode. The cascade was run for 8 h without operational issues. Enzyme recycling was studied by reintroduction of the water phase from the CCCS outlet to the stirred tank reactor. Product yield decreased over time to an average of 50% of the initial value, likely due to accumulation of 1-butanol in water phase, loss of enzyme due to agglomeration, and the formation of a separate enzyme layer.

  19. Sterol fatty acid esters from the mushroom Hericium erinaceum and their PPAR transactivational effects.

    Science.gov (United States)

    Li, Wei; Zhou, Wei; Song, Seok Bean; Shim, Sang Hee; Kim, Young Ho

    2014-12-26

    Six new (erinarols A-F, 1-6) and five known (7-11) ergostane-type sterol fatty acid esters were isolated from the methanol extract of the dried fruiting bodies of Hericium erinaceum. Their chemical structures were elucidated using chemical and physical methods as well as through comparison of NMR and mass spectral data with those reported previously. This is the first comprehensive investigation on ergostane-type sterol fatty acid esters from H. erinaceum. The isolated compounds were evaluated for their PPAR transactivational effects using a luciferase reporter system. Compounds 1 and 2 significantly activated the transcriptional activity of PPARs in a dose-dependent manner, with EC50 values of 8.2 and 6.4 μM, respectively. Moreover, compounds 1 and 2 also activated PPARα and PPARγ transcriptional activity, with stimulation from 1.3- to 3.9-fold at 20 μM concentrations.

  20. Possible molecular targets for therapeutic applications of caffeic acid phenethyl ester in inflammation and cancer

    Directory of Open Access Journals (Sweden)

    Ghulam Murtaza

    2015-03-01

    Full Text Available Of the various derivatives of caffeic acid, caffeic acid phenethyl ester (CAPE is a hydrophobic, bioactive polyphenolic ester obtained from propolis extract. The objective in writing this review article was to summarize all published studies on therapeutics of CAPE in inflammation and cancer to extract direction for future research. The possible molecular targets for the action of CAPE, include various transcription factors such as nuclear factor-κB, tissue necrosis factor-α, interleukin-6, cyclooxygenase-2, Nrf2, inducible nitric oxide synthase, nuclear factor of activated T cells, hypoxia-inducible factor-1α, and signal transducers and activators of transcription. Based on the valuable data on its therapeutics in inflammation and cancer, clinical studies of CAPE should also be conducted to explore its toxicities, if any.

  1. Headspace solid-phase microextraction of higher fatty acid ethyl esters in white rum aroma.

    Science.gov (United States)

    Pino, J; Martí, M P; Mestres, M; Pérez, J; Busto, O; Guasch, J

    2002-04-19

    Fatty acid ethyl esters are the main components of rum aroma and play an important sensorial impact in these distilled alcoholic beverages. Herein, a method for analysing these volatile compounds is described. It involves a separation and concentration step using headspace solid-phase microextraction and determination by capillary gas chromatography using flame ionisation detection. The influence of different parameters related to the isolation and concentration step, such as ethanol concentration, ionic strength, sample volume, time and temperature of extraction, was studied. The developed method enabled recoveries >91% for the analyzed compounds with limits of detection between 0.007 and 0.027 mg/l, all of them lower than the range of concentrations found in rum samples. The method was successfully applied to the analysis of fatty acid ethyl esters in different commercial white rums.

  2. Chemical Constituents from Flueggea virosa and the Structural Revision of Dehydrochebulic Acid Trimethyl Ester

    Directory of Open Access Journals (Sweden)

    Chih-Hua Chao

    2016-09-01

    Full Text Available In an attempt to study the chemical constituents from the twigs and leaves of Flueggea virosa, a new terpenoid, 9(10→20-abeo-ent-podocarpane, 3β,10α-dihydroxy-12-methoxy-13- methyl-9(10→20-abeo-ent-podocarpa-6,8,11,13-tetraene (1, as well as five known compounds were characterized. Their structures were elucidated on the basis of spectroscopic analysis. In addition, the structure of dehydrochebulic acid trimethyl ester was revised as (2S,3R-4E-dehydrochebulic acid trimethyl ester based on a single-crystal X-ray diffraction study. The in vitro anti-hepatitis C virus (anti-HCV activity and cytotoxicity against Huh7.5 cells for the isolated compounds were evaluated.

  3. 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.

  4. Condensation of anhydrides or dicarboxylic acids with compounds containing active methylene groups. Part 1: Condensation of phthalic anhydride with acetoacetic and malonic ester

    Science.gov (United States)

    Oshkaya, V. P.; Vanag, G. Y.

    1985-01-01

    Phthalic anhydride was condensed with acetoacetic ester in acetic anhydride and triethylamine solution, and when phthalyl chloride was reacted with sodium acetoacetic ester compounds were formed of the phthalide and indandione series: phthalylacetoacetic ester and a derivative of indan-1,3-dione which after boiling with hydrochloric acid yielded indan-1,3-dione. Phthalylmalonic ester was obtained from phthalic anhydride and malonic ester in the presence of triethylamine.

  5. Decomposition products of glycidyl esters of fatty acids by heating.

    Science.gov (United States)

    Kimura, Wataru; Endo, Yasushi

    2017-03-01

    In this study, decomposition products of glycidyl palmitate (GP) of fatty acids heated at high temperature such as deep frying were investigated. When GP and tripalmitin (TP) were heated at 180 and 200 °C, they were decreased with heating time. The weight of GP was less than that of TP, although both GP and TP were converted to polar compounds after heating. The decomposition rate of GP was higher than TP. Both GP and TP produced considerable amounts of hydrocarbons and aldehydes during heating. Aldehydes produced from GP and TP included saturated aldehydes with carbon chain length of 3-10, while hydrocarbons consisted of carbon chain length of 8-15. It was observed that major hydrocarbons produced from GP during heating were pentadecane. Moreover, the level of carbon dioxide (CO2) released from GP was higher than that of TP. It was suggested that fatty acids in GE might be susceptible to decarboxylation. From these results, GP might be quickly decomposed to hydrocarbons, aldehydes and CO2 besides polar compounds by heating, in comparison with TP.

  6. Influence of TNF-alpha inhibitors and fumaric acid esters on male fertility in psoriasis patients.

    Science.gov (United States)

    Heppt, F; Colsman, A; Maronna, A; Uslu, U; Heppt, M V; Kiesewetter, F; Sticherling, M

    2017-11-01

    Is there any influence of a therapy with TNF-alpha inhibitors or fumaric acid esters and of disease activity status on male fertility and sperm quality in patients with psoriasis? In this monocentric, open-label, prospective study, semen samples were collected from patients receiving either TNF-alpha inhibitors or fumaric acid esters for moderate-to-severe plaque psoriasis. Semen was analysed at baseline before onset of the systemic therapy and monitored every 3 months under therapy. Sperm parameters were assessed according to the current WHO definitions. In total, 101 semen specimens from 27 patients were obtained. Mean Psoriasis Area and Severity Index (PASI) score at baseline was 11.05. Only 14.8% of patients showed a normozoospermia without any other abnormal seminal values. 85.2% of patients had at least one sperm/seminal abnormality, including two patients showing an azoospermia. Interestingly, 48.1% showed sperm parameters indicative of genital tract inflammation. Therapy with TNF-alpha inhibitors or fumaric acid esters did not have any negative effects on relevant sperm parameters such as mean total sperm number, sperm concentration, total and progressive motility. No major gonadal dysfunction was observed in any patient. At baseline, many patients with psoriasis showed abnormal semen/sperm parameters and remarkably elevated leukocytes and values of seminal polymorphonuclear elastase, indicating a genital tract inflammation. Thus, genital tract inflammation may represent an important comorbidity of psoriasis, little attention paid to so far. Regarding treatment with TNF-alpha inhibitors or fumaric acid esters, no major negative (side-) effects on sperm quality were observed. © 2017 European Academy of Dermatology and Venereology.

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

    OpenAIRE

    Balak, Deepak; Bavinck, Jan Nico Bouwes; De Vries, A.P.J. (Aiko P. J.); Hartman, J.; Martino Neumann, H.A.; Zietse, Bob; 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 Fanconi syndrome. Methods: Descriptive case series with two cases of Fanconi syndrome associated with FAE treatment diagnosed at two Dutch university nephrology departments, three cases reported at th...

  8. Oral fumaric acid esters for psoriasis: abridged Cochrane systematic review including GRADE assessments

    OpenAIRE

    Atwan, A.; Ingram, John R.; Abbott, Rachel; Kelson, Mark James; Pickles, Timothy E.; Bauer, A.; Piguet, Vincent

    2016-01-01

    Summary Fumaric acid esters (FAEs) are licensed for the treatment of moderate?to?severe psoriasis in Germany but are also used off?label in many other countries. We conducted this systematic review to synthesize the highest?quality evidence for the benefits and risks of FAEs for psoriasis. Our primary outcomes were change in Psoriasis Area and Severity Index score and dropout rates due to adverse effects. Randomized controlled trials (RCTs) of FAEs or dimethylfumarate were included, with no r...

  9. Improvement of foaming properties of cuttlefish skin gelatin by modification with N-hydroxysuccinimide esters of fatty acid

    NARCIS (Netherlands)

    Aewsiri, T.; Benjakul, S.; Visessanguan, W.; Wierenga, P.A.; Gruppen, H.

    2011-01-01

    Conformation and foaming properties of cuttlefish skin gelatin modified by N-hydroxysuccinimide esters of different saturated fatty acids including capric acid (C10:0), lauric acid (C12:0) and myristic acid (C14:0) at different molar ratios (0.25, 0.50, 1.00 and 2.00) were investigated. Covalent

  10. 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)

  11. 40 CFR 721.1730 - Poly(oxy-1,2-ethanediyl), α-butyl-ω-hydroxy, ester with boric acid (H3BO3).

    Science.gov (United States)

    2010-07-01

    ...-hydroxy, ester with boric acid (H3BO3). 721.1730 Section 721.1730 Protection of Environment ENVIRONMENTAL..., ester with boric acid (H3BO3). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as poly(oxy-1,2-ethanediyl), α-butyl-ω-hydroxy, ester with boric...

  12. 40 CFR 721.1731 - Poly(oxy-1,2-ethanediyl), α-methyl-ω-hydroxy, ester with boric acid (H3BO3).

    Science.gov (United States)

    2010-07-01

    ...-hydroxy, ester with boric acid (H3BO3). 721.1731 Section 721.1731 Protection of Environment ENVIRONMENTAL..., ester with boric acid (H3BO3). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as poly(oxy-1,2-ethanediyl), α-methyl-ω-hydroxy, ester with boric...

  13. One-Pot Synthesis of Esters of Cyclopropane Carboxylic Acids via Tandem Vicarious Nucleophilic Substitution-Michael Addition Process.

    Science.gov (United States)

    Mąkosza, Mieczysław; Bester, Karol; Cmoch, Piotr

    2015-06-05

    α-Chlorocarbanions generated via base-induced vicarious nucleophilic substitution reaction of alkyl dichloroacetates with nitroarenes react with Michael acceptors to give esters of cyclopropane carboxylic acids substituted with p-nitroaromatic rings.

  14. Why are esters and amides weaker carbon acids than ketones and Acid fluorides? Contributions by resonance and inductive effects.

    Science.gov (United States)

    Fersner, Alexandra; Karty, Joel M; Mo, Yirong

    2009-10-02

    Two computational methodologies-a vinylogue extrapolation methodology and a block localized wave function (BLW) methodology-were employed to determine the contributions by resonance and inductive effects toward the gas-phase deprotonation enthalpies at the alpha carbons of acetone, acetamide, acetic acid, and acetyl fluoride, which were taken to be model compounds for ketones, amides, esters, and acid fluorides, respectively. Results from the vinylogue methodology suggest that resonance serves to enhance the gas-phase deprotonation enthalpy of a ketone by 34.3 kcal/mol, an amide by 26.2 kcal/mol, an ester by 30.5 kcal/mol, and an acid fluoride by 30.8 kcal/mol. Comparably, the BLW methodology suggests those numbers to be 42.3, 31.2, 36.1, and 39.7 kcal/mol, respectively. Results from the vinylogue methodology suggest that inductive effects serve to enhance the gas-phase deprotonation enthalpy of a ketone by 11.8 kcal/mol, an amide by 12.7 kcal/mol, an ester by 15.5 kcal/mol, and an acid fluoride by 26.0 kcal/mol, and in the same order, those numbers suggested by the BLW methodology are 3.0, 6.2, 8.5, and 16.3 kcal/mol.

  15. Isolation and Characterization of Esters of Indole-3-Acetic Acid from the Liquid Endosperm of the Horse Chestnut (Aesculus species) 1

    Science.gov (United States)

    Domagalski, Wojciech; Schulze, Aga; Bandurski, Robert S.

    1987-01-01

    Esters of indole-3-acetic acid were extracted and purified from the liquid endosperm of immature fruits of various species of the horse chestnut (Aesculus parviflora, A. baumanni, A.pavia rubra, and A. pavia humulis). The liquid endosperm contained, at least 12 chromatographically distinct esters. One of these compounds was purified and characterized as an ester of indole-3-acetic acid and myo-inositol. A second compound was found to be an ester of indole-3-acetic acid and the disaccharide rutinose (glucosyl-rhamnose). A third compound was partially characterized as an ester of indole-3-acetic acid and a desoxyaminohexose. PMID:11539676

  16. Integrated process of distillation with side reactors for synthesis of organic acid esters

    Science.gov (United States)

    Panchal, Chandrakant B; Prindle, John C; Kolah, Aspri; Miller, Dennis J; Lira, Carl T

    2015-11-04

    An integrated process and system for synthesis of organic-acid esters is provided. The method of synthesizing combines reaction and distillation where an organic acid and alcohol composition are passed through a distillation chamber having a plurality of zones. Side reactors are used for drawing off portions of the composition and then recycling them to the distillation column for further purification. Water is removed from a pre-reactor prior to insertion into the distillation column. An integrated heat integration system is contained within the distillation column for further purification and optimizing efficiency in the obtaining of the final product.

  17. Phenolic Acid-based Poly(anhydride-esters) as Antioxidant Biomaterials.

    Science.gov (United States)

    Prudencio, Almudena; Faig, Jonathan J; Song, MinJung; Uhrich, Kathryn E

    2016-02-01

    Poly(anhydride-esters) comprised of naturally occurring, non-toxic phenolic acids, namely syringic and vanillic acid, with antioxidant properties were prepared via solution polymerization methods. Polymer and polymer precursor physiochemical properties were characterized, including polymer molecular weight and thermal properties. In vitro release studies illustrated that polymer hydrolytic degradation was influenced by relative hydrophobicity and degree of methoxy substitution of the phenolic acids. Further, the released phenolic acids were found to maintain antioxidant potency relative to free phenolic acid controls as determined by a 2,2-diphenyl-1-picrylhydrazyl assay. Polymer cytotoxicity was assessed with L929 fibroblasts in polymer-containing media; appropriate cell morphology and high fibroblast proliferation were obtained for the polymers at the lower concentrations. These polymers deliver non-cytotoxic levels of naturally occurring antioxidants, which could be efficacious in topical delivery of antioxidant therapies. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  18. Enantioselective Iridium Catalyzed Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level via Transfer Hydrogenative Coupling of Allyl Acetate: Departure from Chirally Modified Allyl Metal Reagents in Carbonyl Addition

    OpenAIRE

    Kim, In Su; Ngai, Ming-Yu; Krische, Michael J.

    2008-01-01

    Under the conditions of transfer hydrogenation employing an iridium catalyst generated in situ from [Ir(cod)Cl]2, the chiral phosphine ligands (R)-BINAP or (R)-Cl,MeO-BIPHEP and m-nitrobenzoic acid, allyl acetate couples to allylic alcohols 1a-1c, aliphatic alcohols 1d-1l and benzylic alcohols 1m-1u to furnish products of carbonyl allylation 3a-3u with exceptional levels of asymmetric induction. The very same set of optically enriched carbonyl allylation products 3a-3u are accessible from ena...

  19. Treatment of severe psoriasis with fumaric acid esters: scientific background and guidelines for therapeutic use. The German Fumaric Acid Ester Consensus Conference.

    Science.gov (United States)

    Mrowietz, U; Christophers, E; Altmeyer, P

    1999-09-01

    Fumaric acid ester (FAE) therapy has proved to be safe and effective in patients with severe psoriasis vulgaris. This treatment was introduced nearly 30 years ago, but is only now gaining renewed interest among dermatologists. FAE therapy is licensed in Germany and registration is pending in many European countries. Multicentre trials have confirmed the beneficial effect of FAE in psoriasis and have defined the spectrum of its adverse effects. Although the mode of action of FAEs in the treatment of psoriasis is not fully understood, recent experimental data point towards a skewing of the Th1-dominated T-cell response in psoriasis to a Th2-like pattern, and inhibition of proliferation of keratinocytes. This article reviews the experimental and clinical information on FAEs in psoriasis and provides guidelines for the clinical use of FAEs derived from a consensus meeting of leading experts.

  20. Direct synthesis of esters and amides from unprotected hydroxyaromatic and -aliphatic carboxylic acids.

    Science.gov (United States)

    Katritzky, Alan R; Singh, Sanjay K; Cai, Chunming; Bobrov, Sergey

    2006-04-28

    A facile method for the activation of hydroxy-substituted carboxylic acids using benzotriazole chemistry without prior protection of the hydroxy substituents is presented. The N-acylbenzotriazole intermediates 2a-g, 6a-d, and 9a-c have been used for high-yielding synthesis of both aliphatic (3a-l) and aromatic (7a-h, 10a-f) hydroxy carboxamides. High yields of aromatic hydroxy esters 12a-h and 13a-i were obtained using either neat alcohols in neutral microwave conditions or nucleophilic alkoxides and the intermediate N-(arylacyl)benzotriazoles. Moderate yields were obtained in the case of aliphatic hydroxy esters 11a,b and thiolesters 11e-g from the intermediates 2a-c.

  1. Synthesis and immunomodulatory activites of new 5-hydrazino-3-methyl-4-isothiazolecarboxylic acid ethyl esters.

    Science.gov (United States)

    Lipnicka, Urszula; Maczyński, Marcin; Artym, Jolanta; Zimecki, Michał

    2009-01-01

    Several new derivatives of 5-hydrazino-3-methyl-4-isothiazolecarboxylic ethyl esters were synthesized. Using 4-aminoacetophenone, the hydrazine group was transformed in position 5 in the hydrazone which reacted with the isocyanates, aldehydes and sugars. Thirteen newly synthesized compounds were tested for their ability to affects the immunological response in vitro in several rodent models. The immunoregulatory properties of the compounds were differential and dose-dependent. The strongest activity was exhibited by 5-{N'-[1-4{-4-[3-(-methoxyphenyl)-ureidol]-phenylethylidene]-hydrazino}-3-methyl-4-isothiazolecarboxylic acid ethyl ester (compound 3a). The compound strongly inhibited the secondary, humoral immune response to sheep erythrocytes and the proliferative response of mouse splenocytes to concanavalin A and pokeweed mitogen. The immunotropic activities of the new isothiazole derivatives and potential application of the compounds in therapy are discussed.

  2. Aspects of the Influence of Light on the Adsorption and Electrooxidation of Allyl Alcohol on Pt/Pt Electrodes in Perchloric Acid Solutions

    Directory of Open Access Journals (Sweden)

    Barin Claudia Smaniotto

    1998-01-01

    Full Text Available The electrooxidation of the adsorbed species produced by allyl alcohol adsorption on platinized platinum electrode has been studied in 1.0 M HClO4 medium. The maximum amount of adsorbed intermediates formed during allyl alcohol adsorption on the electrode surface, was observed at the adsorption potential, Eads = 0.00 V (SCE. Chronoamperometric studies at this potential confirm that the current associated with the hydrogen adsorption process decreases in the presence of the organic compound. Allyl alcohol displaces adsorbed hydrogen at the active sites. The incidence of polychromatic light on the electrode improves this effect as shown by comparison with the same experiments in the darkness. However, the electrooxidation of the adsorbed species comprise a monoelectronic charge transfer step. The anodic current associated with this process was higher under illumination than in the dark. This difference was attributed to a light-induced effect: either on the adsorption process of allyl alcohol on Pt/Pt, or on the electrooxidation of the adsorbed species. The electrooxidation of the adsorbed species formed during allyl alcohol adsorption demands apparent activation energies equivalent to 33.3 kJ mol-1 and 24.9 kJ mol-1 in the dark and under illumination, respectively.

  3. Sintesis Metil Ester Sulfonat Dari Asam Stearat Dan Metil Ester Sulfonat Dari Asam Oleat

    OpenAIRE

    Samosir, Yustina

    2011-01-01

    The Synthesis of Methyl Ester Sulfonate (MES) from stearic acid and from oleic acid through the stages of esterification reaction, that are esterification from stearic acid and oleic acid that forms methyl ester stearic acid and methyl ester oleic acid next stage was sulfonating the two of methyl esters to form a methyl ester sulfonate stearic acid and methyl ester oleic acid sulfonate. Furthermore, both fatty acid methyl ester sulfonate is neutralized with NaOH to obtain sulfonate salt. ...

  4. GESTATIONAL-AGE DEPENDENCY OF ESSENTIAL FATTY-ACIDS IN CORD PLASMA-CHOLESTEROL ESTERS AND TRIGLYCERIDES

    NARCIS (Netherlands)

    HOVING, EB; VANBEUSEKOM, CM; NIJEBOER, HJ; MUSKIET, FAJ

    Plasma cholesterol ester and triglyceride fatty acid compositions of 38 singleton deliveries (23-42 wk), three twins (32, 39, and 40 wk), and their mothers were investigated. No gestational age-dependent changes occurred in maternal fatty acid compositions. Long-chain polyunsaturated fatty acids in

  5. 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.

  6. Temperature dependence of the dielectric permittivity of acetic acid, propionic acid and their methyl esters: a molecular dynamics simulation study.

    Science.gov (United States)

    Riniker, Sereina; Horta, Bruno A C; Thijssen, Bram; Gupta, Saumya; van Gunsteren, Wilfred F; Hünenberger, Philippe H

    2012-04-10

    For most liquids, the static relative dielectric permittivity is a decreasing function of temperature, because enhanced thermal motion reduces the ability of the molecular dipoles to orient under the effect of an external electric field. Monocarboxylic fatty acids ranging from acetic to octanoic acid represent an exception to this general rule. Close to room temperature, their dielectric permittivity increases slightly with increasing temperature. Herein, the causes for this anomaly are investigated based on molecular dynamics simulations of acetic and propionic acids at different temperatures in the interval 283-363 K, using the GROMOS 53A6(OXY) force field. The corresponding methyl esters are also considered for comparison. The dielectric permittivity is calculated using either the box-dipole fluctuation (BDF) or the external electric field (EEF) methods. The normal and anomalous temperature dependences of the permittivity for the esters and acids, respectively, are reproduced. Furthermore, in the EEF approach, the response of the acids to an applied field of increasing strength is found to present two successive linear regimes before reaching saturation. The low-field permittivity ε, comparable to that obtained using the BDF approach, increases with increasing temperature. The higher-field permittivity ε' is slightly larger, and decreases with increasing temperature. Further analyses of the simulations in terms of radial distribution functions, hydrogen-bonded structures, and diffusion properties suggest that increasing the temperature or the applied field strength both promote a relative population shift from cyclic (mainly dimeric) to extended (chain-like) hydrogen-bonded structures. The lower effective dipole moment associated with the former structures compared to the latter ones provides an explanation for the peculiar dielectric properties of the two acids compared to their methyl esters. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  7. Study of UltraHigh Performance Supercritical Fluid Chromatography to measure free fatty acids with out fatty acid ester preparation.

    Science.gov (United States)

    Ashraf-Khorassani, M; Isaac, G; Rainville, P; Fountain, K; Taylor, L T

    2015-08-01

    Most lipids are best characterized by their fatty acids which may differ in (a) chain length, (b) degree of unsaturation, (c) configuration and position of the double bonds, and (d) the presence of other functionalities. Thus, a fast, simple, and quantitative analytical technique to determine naturally occurring free fatty acids (FFA) in different samples is very important. Just as for saponified acylglycerols, the determination of FFA's has generally been carried out by high resolution gas chromatography (HRGC). The use of an open tubular capillary column coupled with a flame ionization or mass spectrometric detector provides for both high resolution and quantification of FFA's but only after conversion of all free fatty acids to fatty acid methyl esters (FAME) or pentafluorobenzyl esters. Unfortunately, volatilization of labile ester derivatives of mono- and poly-unsaturated FFA's can cause both thermal degradation and isomerization of the fatty acid during HRGC. The employment of a second generation instrument (here referred to as UltraHigh Performance Supercritical Fluid Chromatograph, UHPSFC) with high precision for modified flow and repeated back pressure adjustment in conjunction with sub-2μm various bonded silica particles (coupled with evaporative light scattering, ELSD, and mass spectrometric, MS, detection) for separation and detection of the following mixtures is described: (a) 31 free fatty acids, (b) isomeric FFA's, and (c) lipophilic materials in two real world fish oil samples. Limits of detection for FFA's via UHPSFC/MS and UHPSFC/ELSD versus detection of FAME's via HRGC/MS are quantitatively compared. Copyright © 2015 Elsevier B.V. All rights reserved.

  8. Allyl 4-hydroxyphenyl carbonate

    Directory of Open Access Journals (Sweden)

    Víctor Hugo Flores Ahuactzin

    2009-07-01

    Full Text Available The title molecule, C10H10O4, is a functionalized carbonate used in the synthetic route to organic glasses. The central CH fragment of the allyl group is disordered over two positions, with occupancies in a 0.758 (10:0.242 (10ratio. This disorder reflects the torsional flexibility of the oxygen–allyl group, although both disordered parts present the expected anticlinal conformation, with O—CH2—CH=CH2 torsion angles of −111 (2 and 119.1 (4°. The crystal structure is based on chains parallel to [010], formed by O...H—O hydrogen bonds involving hydroxyl and carbonyl groups as donors and acceptors, respectively. The molecular packing is further stabilized by two weak C—H...π contacts from the benzene ring of the asymmetric unit with two benzene rings of neighboring molecules.

  9. Enhancing the Acylation Activity of Acetic Acid by Formation of an Intermediate Aromatic Ester.

    Science.gov (United States)

    Duong, Nhung N; Wang, Bin; Sooknoi, Tawan; Crossley, Steven P; Resasco, Daniel E

    2017-07-10

    Acylation is an effective C-C bond-forming reaction to condense acetic acid and lignin-derived aromatic compounds into acetophenones, valuable precursors to fuels and chemicals. However, acetic acid is intrinsically an ineffective acylating agent. Here, we report that its acylation activity can be greatly enhanced by forming intermediate aromatic esters directly derived from acetic acid and phenolic compounds. Additionally, the acylation reaction was studied in the liquid phase over acid zeolites and was found to happen in two steps: 1) formation of an acylium ion and 2) C-C bond formation between the acylium ion and the aromatic substrate. Each of these steps may be rate-limiting, depending on the type of acylating agent and the aromatic substrate. Oxygen-containing substituents, such as -OH and -OCH3 , can activate aromatic substrates for step 2, with -OH> -OCH3 , whereas alkyl substituent -R cannot. At the same time, aromatic esters can rearrange to acetophenones by both an intramolecular pathway and, preferentially, an intermolecular one. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  10. Metal-Free Domino One-Pot Decarboxylative Cyclization of Cinnamic Acid Esters: Synthesis of Functionalized Indanes.

    Science.gov (United States)

    Gopi Krishna Reddy, Alavala; Satyanarayana, Gedu

    2016-12-16

    Trifluoroacetic acid promoted unprecedented domino reaction for the synthesis of diverse indanes starting from simple cinnamic acid esters is described. Their formation can be explained via acid triggered decarboxylation of cinnamic acid esters and subsequent inter/intramolecular cyclization. Overall process involves in the intramolecular cleavage of two σ-bonds (C-O and C-C) and inter/intramolecular construction of two/one C-C σ-bond(s). Significantly, this protocol was successful without the aid of any metal salts.

  11. 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...

  12. 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.

  13. Enantioselective Hydrolysis of Amino Acid Esters Promoted by Bis(β-cyclodextrin) Copper Complexes

    Science.gov (United States)

    Xue, Shan-Shan; Zhao, Meng; Ke, Zhuo-Feng; Cheng, Bei-Chen; Su, Hua; Cao, Qian; Cao, Zhen-Kun; Wang, Jun; Ji, Liang-Nian; Mao, Zong-Wan

    2016-02-01

    It is challenging to create artificial catalysts that approach enzymes with regard to catalytic efficiency and selectivity. The enantioselective catalysis ranks the privileged characteristic of enzymatic transformations. Here, we report two pyridine-linked bis(β-cyclodextrin) (bisCD) copper(II) complexes that enantioselectively hydrolyse chiral esters. Hydrolytic kinetic resolution of three pairs of amino acid ester enantiomers (S1-S3) at neutral pH indicated that the “back-to-back” bisCD complex CuL1 favoured higher catalytic efficiency and more pronounced enantioselectivity than the “face-to-face” complex CuL2. The best enantioselectivity was observed for N-Boc-phenylalanine 4-nitrophenyl ester (S2) enantiomers promoted by CuL1, which exhibited an enantiomer selectivity of 15.7. We observed preferential hydrolysis of L-S2 by CuL1, even in racemic S2, through chiral high-performance liquid chromatography (HPLC). We demonstrated that the enantioselective hydrolysis was related to the cooperative roles of the intramolecular flanking chiral CD cavities with the coordinated copper ion, according to the results of electrospray ionization mass spectrometry (ESI-MS), inhibition experiments, rotating-frame nuclear Overhauser effect spectroscopy (ROESY), and theoretical calculations. Although the catalytic parameters lag behind the level of enzymatic transformation, this study confirms the cooperative effect of the first and second coordination spheres of artificial catalysts in enantioselectivity and provides hints that may guide future explorations of enzyme mimics.

  14. Methyl Ester Production via Heterogeneous Acid-Catalyzed Simultaneous Transesterification and Esterification Reactions

    Science.gov (United States)

    Indrayanah, S.; Erwin; Marsih, I. N.; Suprapto; Murwani, I. K.

    2017-05-01

    The heterogeneous acid catalysts (MgF2 and ZnF2) have been used to catalyze the simultaneous transesterification and esterification reactions of crude palm oil (CPO) with methanol. Catalysts were synthesized by sol-gel method (combination of fluorolysis and hydrolysis). The physicochemical, structural, textural, thermal stability of the prepared catalysts was investigated by N2 adsorption-desorption, XRD, FT-IR, SEM and TG/DTG. Both MgF2 and ZnF2 have rutile structures with a different phase. The surface area of ZnF2 is smaller than that of MgF2, but the pore size and volume of ZnF2 are larger than those of MgF2. However, these materials are thermally stable. The performance of the catalysts is determined from the yield of catalysts toward the formation of methyl ester determined based on the product of methyl ester obtained from the reaction. The catalytic activity of ZnF2 is higher than MgF2 amounted to 85.21% and 26.82% with the optimum condition. The high activity of ZnF2 could be attributed to its pore diameter and pore volume but was not correlated with its surface area. The yield of methyl ester decreased along with the increase in molar ratio of methanol/CPO from 85.21 to 80.99 for ZnF2, respectively.

  15. 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.)

  16. 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.

  17. Development of biodegradable flexible films of starch and poly(lactic acid) plasticized with adipate or citrate esters.

    Science.gov (United States)

    Shirai, M A; Grossmann, M V E; Mali, S; Yamashita, F; Garcia, P S; Müller, C M O

    2013-01-30

    Biodegradable films were produced from blends contained a high amount of thermoplastic starch (TPS) and poly(lactic acid) (PLA) plasticized with different adipate or citrate esters. It was not possible to obtain pellets for the production of films using only glycerol as a plasticizer. The plasticization of the PLA with the esters and mixture stages added through extrusion was critical to achieve a blend capable of producing films by blow extrusion. Adipate esters were the most effective plasticizers because they interacted best with the PLA and yielded films with appropriate mechanical properties. Copyright © 2012 Elsevier Ltd. All rights reserved.

  18. Electronically Rich N-Substituted Tetrahydroisoquinoline 3-Carboxylic Acid Esters: Concise Synthesis and Conformational Studies.

    Science.gov (United States)

    Al-Horani, Rami A; Desai, Umesh R

    2012-02-25

    Recent work in our laboratory has shown that the highly substituted, electronically rich 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (THIQ3CA) scaffold is a key building block for a novel class of promising anticoagulants (Al-Horani et al. J. Med. Chem.2011, 54, 6125-6138). The synthesis of THIQ3CA analogs, especially containing specific, electronically rich substituents, has been a challenge and essentially no efficient methods have been reported in the literature. We describe three complementary, glycine donor-based strategies for high yielding synthesis of highly substituted, electronically rich THIQ3CA esters. Three glycine donors studied herein include hydantoin 1, (±)-Boc-α-phosphonoglycine trimethyl ester 2 and (±)-Z-α-phosphonoglycine trimethyl ester 3. Although the synthesis of THIQ3CA analogs could be achieved using either of the three, an optimal, high yielding approach for the desired THIQ3CA esters was best achieved using 3 in three mild, efficient steps. Using this approach, a focused library of advanced N-arylacyl, N-arylalkyl, and bis-THIQ3CA analogs was synthesized. Variable temperature and solvent-dependent NMR chemical shift studies indicated the presence of two major conformational rotamers in 3:1 proportion for N-arylacyl-THIQ3CA analogs, which were separated by a high kinetic barrier of ~17 kcal/mol. In contrast, N-arylalkyl and bis-THIQ3CA variants displayed no rotamerism, which implicates restricted rotation around the amide bond as the origin for high-barrier conformational interconversion. This phenomenon is of major significance because structure-based drug design typically utilizes only one conformation. Overall, the work presents fundamental studies on the synthesis and conformational properties of highly substituted, electronically rich THIQ3CA analogs.

  19. Effects of fatty acid glycerol esters on intestinal absorptive and secretory transport of ceftibuten.

    Science.gov (United States)

    Koga, K; Murakami, M; Kawashima, S

    1999-04-01

    The effects of fatty acid glycerol esters and Tweens on the intestinal transport of ceftibuten were studied using a diffusion chamber system. The apparent permeation coefficient (P(app)) was used as an index of the mucosal permeability to ceftibuten. The P(app) markedly increased by the addition of hexaglycerol monostearate (HGMS) or hexaglycerol sesquistearate (HGSS) under an H+-gradient condition, while hexaglycerol tristearate (HGTS) and Tweens showed no effect on the absorptive ceftibuten permeability. These results are in agreement with those obtained in the previous study in the brush-border membrane vesicles. On the other hand, in the absence of an H+-gradient, the S-to-M transport of ceftibuten was proven to be significantly higher than the M-to-S one. In addition, either ATP-depletion of the mucosa or the addition of probenecid proved to enhance significantly the permeability of ceftibuten. These findings suggest the existence of an active secretory transport system for ceftibuten in the jejunal mucosa. To estimate potential effects of glycerol esters on efflux pumps as well as peptide transporters, the mucosal-to-serosal (M-to-S) and serosal-to-mucosal (S-to-M) permeability in the presence of the esters was further examined. HGMS, HGSS and HGTS markedly enhanced the M-to-S but not the S-to-M transport in the ATP-depleted jejunum without an H+-gradient, in which conditions contributions of both peptide transporter and efflux pump should be substantially small. HGMS and HGSS significantly enhanced the M-to-S ceftibuten transport in the ATP-depleted jejunum with an H+-gradient (pceftibuten due to the glycerol esters may be based on their effects on peptide transporters but neither on efflux pumps nor on the passive permeation routes.

  20. Synthesis and characterization of phosphonate ester and phosphonic acid containing polymers and blends

    Science.gov (United States)

    Tamber, Harinder Singh

    1997-12-01

    Vinylbenzylphosphonate ester (VBP) was homopolymerized and copolymerized with methyl methacrylate and the reactivity ratio of this pair of monomers was calculated from Finneman-Ross and Kelen-Tudos methods. These methods provided identical values, which are rsb1 (VBP) = 1.23 and rsb2(MMA) = 0.43. The phosphonate ester group, -P = O(OEt)sb2; in VBP and poly(VBP-MMA) copolymers was hydrolysed to phosphonic acid, -P = O(OH)sb2; at room temperature to obtain vinylbenzylphosphonic acid (VBPa) and poly(VBPa-MMA) copolymers. sp1H, sp{13}C & sp{31}P NMR spectroscopy, DSC and FTIR were used to monitor the hydrolysis of these phosphorylated monomers and polymers. The glass transition temperature of PVBP was 13sp°C as compared to 198sp°C of PVBPa. The phosphoryl group in the parent polymers acts as a self plasticizing agent resulting in lower glass transition temperature, on the other hand inter and intra hydrogen bonding results in broad and high Tsbg in these hydrolysed polymers. VBP was also polymerized with BisGMA or TEGDM to low conversions. These oligomers were tested in vitro as potential adhesive materials for dental/enamel and composite resins. The phosphonate esters containing polymers show substantial capacity to dissolve the heavy metal salts, e.g., UOsb2(NO)sb3.6Hsb2O and thus provides radiopaque polymers. Excessive sorption of water lead to phase separation and, hence, loss of radiopacity. Thus, an alternate method of synthesis of radiopaque polymers is also described in which radiopacifying agent is covalently linked to polymer backbone. Styryldiphenylbismuth was prepared by the reaction of diphenylbismuthchloride and Grignard of p-bromostyrene, but some other by-products such as triphenylbismuth, distyrylphenyl bismoth were also obtained as revealed by reverse phase HPLC and the yield of the reaction was low. Iodinated monomers VBTIsb3 and IEMIsb3 were prepared by reacting VBC or IEM to triiodophenol in high yields. Decomposition kinetic analysis was done by

  1. Development of a New Environment-conscious Transformer Impregnated with Palm Fatty Acid Ester (PFAE)

    Science.gov (United States)

    Hikosaka, Tomoyuki; Yamazaki, Akina; Hatta, Yasunori; Koide, Hidenobu; Kanoh, Takaaki; Suzuki, Takashi; Yamada, Junichi; Uemura, Shingo

    We have developed a new environment-conscious transformer impregnated with vegetable based insulating oil which called PFAE (Palm Fatty Acid Ester). PFAE has 0.6 times less viscosity and 1.3 times higher dielectric constant compared to mineral oil. This means that a PFAE immersed transformer has better cooling efficiency and better insulating performance in paper-and-oil composite insulation systems, resulting in size reduction in comparison to conventional mineral oil immersed transformers. In this paper, insulating performance of lead to plane electrode models, cooling performance of a PFAE immersed transformer, and the result of analytical study of dissolved gas for abnormal diagnosis are described.

  2. Protective Effects of Caffeic Acid Phenethyl Ester on Cyclophosphamide-Induced Hemorrhagic Cystitis in Rats.

    Science.gov (United States)

    Uysal, Ersin; Yılmaz, H Ramazan; Ugan, Yunus; Altuntas, Atila; Dogru, Atalay; Kutlucan, Ali; Tunc, Sevket Ercan

    2015-12-01

    We investigated the protective effect of caffeic acid phenethyl ester (CAPE) on cyclophosphamide-induced hemorrhagic cystitis in rats in comparison with 2-mercaptoethane sulfonate (MESNA). Forty male rats were randomized into four groups: group 1 (control), group 2 (cyclophosphamide), group 3 (cyclophosphamide + MESNA), group 4 (cyclophosphamide + CAPE). Cyclophosphamide injection increased malondialdehyde levels indicating oxidative stress, whereas CAPE and MESNA ameliorated malondialdehyde levels in the bladder (p hemorrhagic cystitis, we suggest that it would be more beneficial to use MESNA with CAPE to prevent histological damage. © 2015 Wiley Periodicals, Inc.

  3. 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 Intercult Ethnopharmacol 2016; 5(1.000: 105-107

  4. Synthesis and Biological Activity of Arylspiroborate Salts Derived from Caffeic Acid Phenethyl Ester

    Directory of Open Access Journals (Sweden)

    Martin J. G. Hébert

    2015-01-01

    Full Text Available Two novel boron compounds containing caffeic acid phenethyl ester (CAPE derivatives have been prepared and characterized fully. These new compounds and CAPE have been investigated for potential antioxidant and antimicrobial properties and their ability to inhibit 5-lipoxygenase and whether chelation to boron improves their biological activity. Sodium salt 4 was generally more active than ammonium salt 5 in the biological assays and surpassed the radical scavenging ability of CAPE. Compounds 4 and 5 were more active than CAPE and Zileuton in human polymorphonuclear leukocytes. These results clearly show the effectiveness of the synthesized salts as transporter of CAPE.

  5. Nail psoriasis improvement in a patient treated with fumaric acid esters.

    Science.gov (United States)

    Vlachou, Christina; Berth-Jones, John

    2007-01-01

    Nail psoriasis is common in adult psoriatic patients and it causes serious psychological and physical distress. Topical treatments such as corticosteroids, calcipotriol, retinoids, and 5-fluorouracil have limited efficacy and are not without side effects. Relative effective systemic treatments are ciclosporin, methotrexate and acitretin, all of which have a serious toxicity potential. Biologics in the treatment of nail psoriasis have been the subject of recent research, but their cost-effectiveness is questionable. We present a case of psoriatic nail disease which improved greatly on treatment with fumaric acid esters (FAE).

  6. Radioimmunoassay for anileridine, meperidine, and other N-substituted phenylpiperidine carboxylic acid esters

    Energy Technology Data Exchange (ETDEWEB)

    Van Vunakis, H.; Freeman, D.S.; Gjika, H.B.

    1975-10-01

    Antibodies that bind an /sup 125/I-tyramyl derivative of N-succinylanileridine have been produced in animals immunized with N-succinylanileridine-hemocyanin conjugate. Several congeners and metabolites have been tested as competitors of this antigen-antibody reaction. The concentrations (in picomoles) required for 50 percent inhibition have been found to be: anileridine (0.2), meperidine (3.5), piminodine (3.8), diphenoxylate (20.5), normeperidine (20.0), meperidine acid (45,000) and anileridine acid (3,400). Although ester hydrolysis results in changes in inhibiting capacities on the order of 10/sup 4/, major structural changes in the substituent on the nitrogen of the piperidine ring are not readily recognized by the antibody. This radioimmunoassay can be used to study a variety of N-substituted phenylpiperidine carboxylic acid esters by relating the results to the standard curve obtained for the drug under investigation. For all practical purposes, alphaprodine, morphine and methadone do not interfere with the assay.

  7. One-Pot Synthesis of Highly Substituted Nicotinic Acid Derivatives Based on a Formylation Strategy of Enamino Keto Esters.

    Science.gov (United States)

    Kumar, Sukeerthi; Sawant, Aarti A; Chikhale, Rajendra P; Karanjai, Keya; Thomas, Abraham

    2016-02-19

    A facile one-pot synthesis of 4-chloro or 4-bromonicotinic acid esters with optional 2- and 2,5-disubstitution on the pyridine ring has been developed from easily accessible enamino keto esters by a formylation followed by in situ intramolecular cyclization strategy under optimized Vilsmeier reaction conditions. The effect of the substituents on the β-carbon and the nature of the keto functionality were explored in detail to understand the mechanism of pyridine ring formation under the described conditions.

  8. Phosphoric acid esters cannot replace polyvinylphosphonic acid as phosphoprotein analogs in biomimetic remineralization of resin-bonded dentin.

    Science.gov (United States)

    Mai, Sui; Kim, Young Kyung; Toledano, Manuel; Breschi, Lorenzo; Ling, Jun Qi; Pashley, David H; Tay, Franklin R

    2009-10-01

    Polyvinylphosphonic acid (PVPA), a biomimetic analog of phosphoproteins, is crucial for recruiting polyacrylic acid (PAA)-stabilized amorphous calcium phosphate nanoprecursors during biomimetic remineralization of dentin collagen matrices. This study tested the null hypothesis that phosphoric acid esters of methacrylates in dentin adhesives cannot replace PVPA during bimimetic remineralization of resin-dentin interfaces. Human dentin specimens were bonded with: (I) XP Bond, an etch-and-rinse adhesive using moist bonding; (II) XP Bond using dry bonding; (III) Adper Prompt L-Pop, a self-etching adhesive. The control medium contained only set Portland cement and a simulated body fluid (SBF) without any biomimetic analog. Two experimental Portland cement/SBF remineralization media were evaluated: the first contained PAA as the sole biomimetic analog, the second contained PAA and PVPA as dual biomimetic analogs. No remineralization of the resin-dentin interfaces could be identified from specimens immersed in the control medium. After 2-4 months in the first experimental medium, specimens exhibited either no remineralization or large crystal formation within hybrid layers. Only specimens immersed in the second remineralization medium produced nanocrystals that accounted for intrafibrillar remineralization within hybrid layers. The null hypothesis could not be rejected; phosphoric acid esters in dentin adhesives cannot replace PVPA during biomimetic remineralization of adhesive-bonded dentin.

  9. One-Pot, Three-Step Synthesis of Cyclopropylboronic Acid Pinacol Esters from Synthetically Tractable Propargylic Silyl Ethers.

    Science.gov (United States)

    Spencer, Jonathan A; Jamieson, Craig; Talbot, Eric P A

    2017-07-21

    Simple propargylic silyl ethers can be converted to complex cyclopropylboronic acid pinacol esters in an efficient one-pot procedure. Terminal acetylenes undergo a Schwartz's reagent catalyzed hydroboration; subsequent addition of further Schwartz's reagent and Lewis acid-mediated activation of neighboring silyl ether allows cyclization to access a range of cyclopropylboronic acid pinacol esters. The scope includes aromatic, aliphatic, quaternary, and spiro substituted cyclopropyl rings, which can be transformed via Suzuki coupling into a range of lead-like substituted cyclopropyl aryl products.

  10. 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

    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....

  11. Cloning, Sequence Analysis, and Expression in Escherichia coli of the Gene Encoding an α-Amino Acid Ester Hydrolase from Acetobacter turbidans

    NARCIS (Netherlands)

    Polderman-Tijmes, Jolanda J.; Jekel, P; de Vries, Erik; van Merode, Annet; Floris, René; Laan, Jan-Metske van der; Sonke, Theo; Janssen, Dick B.

    The α-amino acid ester hydrolase from Acetobacter turbidans ATCC 9325 is capable of hydrolyzing and synthesizing β-lactam antibiotics, such as cephalexin and ampicillin. N-terminal amino acid sequencing of the purified α-amino acid ester hydrolase allowed cloning and genetic characterization of the

  12. Cloning, sequence analysis, and expression in Escherichia coli of the gene encoding an alpha-amino acid ester hydrolase from Acetobacter turbidans

    NARCIS (Netherlands)

    Polderman-Tijmes, JJ; Jekel, PA; de Vries, EJ; van Merode, Annet; Floris, R; van der Laan, JM; Sonke, T; Janssen, DB

    The alpha-amino acid ester hydrolase from Acetobacter turbidans ATCC 9325 is capable of hydrolyzing and synthesizing beta-lactam antibiotics, such as cephalexin and ampicillin. N-terminal amino acid sequencing of the purified alpha-amino acid ester hydrolase allowed cloning and genetic

  13. 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.

  14. Radio-Modulatory Potential ofCaffeic Acid Phenethyl Ester: A Therapeutic Perspective.

    Science.gov (United States)

    Anjaly, Km; Tiku, Ashu

    2017-11-13

    Use of natural agents is an upcoming area of research in cancer biology. Caffeic acid phenethyl ester has received great attention because of its therapeutic potential in various conditions including cancer. It is an active/abundant component of propolis. Propolis is a honey bee hive product produced by bees using their enzyme-rich digestive secretions on resinous mix, bee wax and pollen from plants. It is used to protect the beehive against bacteria and other infections.Although a lot of work has been done on chemotherapeutic aspects of CAPE, its role as a radiomodulator is yet to be delineated. It can act both as radioprotector and radiosensitizer. Depending on the tissue type it can modulate the radiation response by following different mechanisms. This review will focus on the differential radiomodulatory effects of Caffeic Acid Phenethyl Ester in normal and cancer cells.Besides chemistry and bioavailability,it's potential as a therapeutic agent against radiation induced damage will also be discussed. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

  15. 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.

  16. Alkyl esters of fatty acids a useful tool to detect soft deodorized olive oils.

    Science.gov (United States)

    Pérez-Camino, María del Carmen; Cert, Arturo; Romero-Segura, Ana; Cert-Trujillo, Rosa; Moreda, Wenceslao

    2008-08-13

    Fatty acid alkyl esters (FAAEs) are a family of natural neutral lipids present in olive oils and formed by esterification of free fatty acids (FFAs) with low molecular alcohols. Inappropriate practices during the olive oil extraction process and bad quality of the olive fruits promote their formation. Quantification can be done by isolation with a silica gel solid phase extraction cartridge followed by analysis on a gas chromatograph equipped with a programmed temperature vaporizer injector using a polar capillary column. The application of the method to more than 100 Spanish olive oils from different categories, varieties, and geographical origin allowed for establishing the average content of FAAEs and distinguishing the Spanish protected denomination of origin (PDO) and extra virgin olive oils from other categories of olive oils. Those other categories of oils can be subjected to a mild refining process, which leads to blending with extra virgin olive oils. Studies on low quality oils subjected to mild refining showed that FAAEs remain after that process. Thereby, blends of extra virgin olive and mildly refined low quality olive oils can be detected by their alkyl ester concentrations.

  17. Fatty acid ethyl ester synthesis in the preparation of scotch whiskey.

    Science.gov (United States)

    Goss, K A; Alharethi, R; Laposata, M

    1999-04-01

    Fatty acid ethyl esters (FAEE), nonoxidative ethanol metabolites present in human organs commonly damaged by ethanol abuse, have been implicated as mediators of organ damage. FAEE are additives in various foods and beverages to provide flavor or fragrance, and therefore are common dietary lipid constituents. We hypothesized that FAEE could be generated during alcoholic beverage production because fatty acids are present within microorganisms and ethanol is generated during the fermentation process. In this report, we demonstrate that FAEE are present in commercially available scotch beverages, and that in the preparation of scotch, FAEE can be produced during the fermentation reaction as a result of FAEE synthase activity in the yeast. Following ingestion of scotch, preformed FAEE are delivered to GI tract. The consequences of ingestion of FAEE in scotch, if any, remain to be determined.

  18. Preanalytical variables affecting the quantification of fatty acid ethyl esters in plasma and serum samples.

    Science.gov (United States)

    Soderberg, B L; Sicinska, E T; Blodget, E; Cluette-Brown, J E; Suter, P M; Schuppisser, T; Vetter, W; Laposata, M

    1999-12-01

    Fatty acid ethyl esters (FAEEs) are cytotoxic nonoxidative ethanol metabolites produced by esterification of fatty acids and ethanol. FAEEs are detectable in blood up to 24 h after ethanol consumption. The objective of this study was to assess the impact of gender, serum or plasma triglyceride concentration, time and temperature of specimen storage, type of alcoholic beverage ingested, and the rate of ethanol consumption on FAEE concentrations in plasma or serum. For some studies, subject were recruited volunteers; in others, residual blood samples after ethanol quantification were used. FAEEs were isolated by solid-phase extraction and quantified by gas chromatography-mass spectrometry. For weight-adjusted amounts of ethanol intake, FAEE concentrations were twofold greater for men than women (P /=24 h. The type of alcoholic beverage and rate of consumption did not affect FAEE concentrations. These studies advance plasma and serum FAEE measurements closer to implementation as a clinical test for ethanol intake.

  19. An Advanced TALSPEAK Concept Using 2-Ethylhexylphosphonic Acid Mono-2-Ethylhexyl Ester as the Extractant

    Energy Technology Data Exchange (ETDEWEB)

    Lumetta, Gregg J.; Casella, Amanda J.; Rapko, Brian M.; Levitskaia, Tatiana G.; Pence, Natasha K.; Carter, Jennifer C.; Niver, Cynthia M.; Smoot, Margaret R.

    2014-12-21

    A method for separating the trivalent actinides and lanthanides is being developed using 2-ethylhexylphosphonic acid mono-2-ethylhexyl ester (HEH[EHP]) as the extractant. The method is based on the preferential binding of the actinides in the aqueous phase by N-(2-hydroxyethyl)ethylenediamine-N,N',N'-triacetic acid (HEDTA), which serves to keep the actinides in the aqueous phase while the lanthanides are extracted into an organic phase containing HEH[EHP]. The process is very robust, showing little dependence upon the pH or the HEH[EHP], HEDTA, and citrate concentrations over the ranges that might be expected in a nuclear fuel recycling plant. Single-stage runs with a 2-cm centrifugal contactor indicate that modifications to the process chemistry may be needed to increase the extraction rate for Sm, Eu, and Gd. The hydraulic properties of the system are favorable to application in centrifugal contactors.

  20. Effects of fatty acid sucrose esters on ceftibuten transport by rat intestinal brush-border membrane vesicles.

    Science.gov (United States)

    Koga, K; Murakami, M; Kawashima, S

    1998-07-01

    The effects of fatty acid sucrose esters on membrane lipid dynamics and ceftibuten transport by rat intestinal brush-border membrane vesicles (BBMV) were examined to clarify the differences in the action of mono- and poly-acyl sucrose esters on the drug transport. Fatty acid sucrose mono-acyl ester (SS) inhibited ceftibuten transport by BBMV similar to the action of polyoxyethylene sorbitans (Tweens), while fatty acid sucrose polyacyl ester mixtures (F-160 and F-140) did not affect the drug transport by BBMV. SS but not F-160 and F-140 caused an increase in the anisotropy of 1,6-diphenyl-1,3,5-hexatriene (DPH)- and 1-(4-trimethylammoniumphenyl)-6-phenyl-1,3,5-hexatriene iodide (TMA-DPH)-labeled BBMV in a concentration-dependent manner. Thus, the uptake of ceftibuten by BBMV was strongly correlated with the lipid fluidity of BBMV, in the outer layer and in the inner hydrophobic regions; however, there was no strong correlation between the membrane lipid fluidity and the drug uptake by BBMV. The micelle size and the size distribution of F-160 and F-140 were larger and more widely dispersed, respectively, compared to those of SS and Tweens. These results suggest that the effects of fatty acid sucrose esters on ceftibuten transport by BBMV are related to the dispersion parameter of these pharmaceutical adjuvants.

  1. Highly functionalized 1,2-diamino compounds through reductive amination of amino acid-derived β-keto esters.

    Directory of Open Access Journals (Sweden)

    Paula Pérez-Faginas

    Full Text Available 1,2-Diamine derivatives are valuable building blocks to heterocyclic compounds and important precursors of biologically relevant compounds. In this respect, amino acid-derived β-keto esters are a suitable starting point for the synthesis of β,γ-diamino ester derivatives through a two-step reductive amination procedure with either simple amines or α-amino esters. AcOH and NaBH(3CN are the additive and reducing agents of choice. The stereoselectivity of the reaction is still an issue, due to the slow imine-enamine equilibria through which the reaction occurs, affording mixtures of diastereoisomers that can be chromatographically separated. Transformation of the β,γ-diamino esters into pyrrolidinone derivatives allows the configuration assignment of the linear compounds, and constitutes an example of their potential application in the generation of molecular diversity.

  2. Selective syntheses of Δ(α,β) and Δ(β,γ) butenolides from allylic cyclopropenecarboxylates via tandem ring expansion/[3,3]-sigmatropic rearrangements.

    Science.gov (United States)

    Xie, Xiaocong; Li, Yi; Fox, Joseph M

    2013-04-05

    Allylic cyclopropenecarboxylates undergo ring expansion reactions to give 2-allyloxyfuran intermediates, which subsequently rearrange to Δ(β,γ) butenolides via a Claisen rearrangement or to the corresponding Δ(α,β) butenolides via further Cope rearrangement. Also described are methods for chirality transfer in the rearrangement of nonracemic allylic esters.

  3. 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

  4. 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.

  5. Modification of ceftibuten transport by changes in lipid fluidity caused by fatty acid glycerol esters.

    Science.gov (United States)

    Koga, K; Murakami, M; Kawashima, S

    1999-01-01

    The effects of various fatty acid glycerol esters (FAGE) on the transport of ceftibuten in rat intestinal brush-border membrane vesicles (BBMV) were investigated. The HLB numbers of FAGE used were in the range of 6.5 to 15.7. The ceftibuten uptake by BBMV was examined by a rapid filtration method in the presence or absence of FAGE of a non-solubilizing concentration (0.03%, w/v). Tetraglycerol monostearate, hexaglycerol monostearate, hexaglycerol sesquistearate, hexaglycerol tristearate and decaglycerol tristearate were found significantly to enhance the ceftibuten uptake under an inward H+-gradient condition, while FAGE with oleate or laurate did not affect it. The extent of ceftibuten uptake with FAGE correlated with the HLB of the esters (r= -0.90, pceftibuten uptake induced by FAGE proved to correlate with an increase in fluidity of the outer lipid layer (r= -0.83, pceftibuten transport in the presence of the H+-gradient should, at least in part, be explained by the interaction with the outer lipid regions of BBMV.

  6. Separation and purification of the antioxidant compounds, caffeic acid phenethyl ester and caffeic acid from mushrooms by molecularly imprinted polymer.

    Science.gov (United States)

    Li, Ning; Ng, Tzi Bun; Wong, Jack Ho; Qiao, Ji Xuan; Zhang, Ye Ni; Zhou, Rong; Chen, Rong Rong; Liu, Fang

    2013-08-15

    Caffeic acid phenethyl ester (CAPE) and caffeic acid (CA), two naturally occurring phenolic antioxidants, have been reported to have a diversity of biological activities. In this investigation, a novel approach to separate and enrich CAPE and CA from 25 species of mushrooms using molecularly imprinted polymers (MIPs) as the sorbent material is reported. The MIPs were synthesized using CAPE as the template, and its adsorption behavior was investigated in detail. In comparison with C18-solid phase extraction (SPE), MIP-SPE displayed high selectivity and good affinity for CAPE and CA. The antioxidant potential of the mushroom extracts, before and after preconcentration using MIPs, was assayed by inhibition of erythrocyte hemolysis and lipid peroxidation. Application of MIPs with a high affinity toward CAPE and CA provides a novel method for obtaining active compounds from natural products. Copyright © 2013 Elsevier Ltd. All rights reserved.

  7. Melanogenesis-inhibitory saccharide fatty acid esters and other constituents of the fruits of Morinda citrifolia (noni).

    Science.gov (United States)

    Akihisa, Toshihiro; Tochizawa, Shun; Takahashi, Nami; Yamamoto, Ayako; Zhang, Jie; Kikuchi, Takashi; Fukatsu, Makoto; Tokuda, Harukuni; Suzuki, Nobutaka

    2012-06-01

    Five new saccharide fatty acid esters, named nonioside P (3), nonioside Q (4), nonioside R (8), nonioside S (10), and nonioside T (14), and one new succinic acid ester, butyl 2-hydroxysuccinate (=4-butoxy-3-hydroxy-4-oxobutanoic acid) (31), were isolated, along with 26 known compounds, including eight saccharide fatty acid esters, 1, 2, 5, 6, 7, 9, 12, and 13, three hemiterpene glycosides, 15, 17, and 18, six iridoid glycosides, 21-25, and 27, and nine other compounds, 20, 28, 29, and 32-37, from a MeOH extract of the fruit of Morinda citrifolia (noni). Upon evaluation of these and five other glycosidic compounds, 11, 16, 19, 26, and 30, from M. citrifolia fruit extract for their inhibitory activities against melanogenesis in B16 melanoma cells induced with α-melanocyte-stimulating hormone (α-MSH), most of the saccharide fatty acid esters, hemiterpene glycosides, and iridoid glycosides showed inhibitory effects with no or almost no toxicity to the cells. These compounds were further evaluated with respect to their cytotoxic activities against two human cancer cell lines (HL-60 and AZ521) and their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced with 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells. Copyright © 2012 Verlag Helvetica Chimica Acta AG, Zürich.

  8. Analysis of testosterone fatty acid esters in the digestive gland of mussels by liquid chromatography-high resolution mass spectrometry.

    Science.gov (United States)

    Guercia, Cesare; Cianciullo, Piergiorgio; Porte, Cinta

    2017-07-01

    Several studies have indicated that up to 70% of the total steroids detected in molluscs are in the esterified form and that pollutants, by modifying the esterification of steroids with fatty acids, might act as endocrine disrupters. However, despite the strong physiological significance of this process, there is almost no information on which fatty acids form the steroid esters and how this process is modulated. This study (a) investigates the formation of fatty acid esters of testosterone in digestive gland microsomal fractions of the mussel Mytilus galloprovincialis incubated with either palmitoly-CoA or CoA and ATP, and (b) assesses whether the endocrine disruptor tributyltin (TBT) interferes with the esterification of testosterone. Analysis of testosterone esters was performed by liquid chromatography-high resolution mass spectrometry (UPLC-HRMS). When microsomal fractions were incubated with testosterone and palmitoly-CoA, the formation of testosterone palmitate was detected. However, when microsomes were incubated with CoA and ATP, and no exogenous activated fatty acid was added, the synthesis of 16:0, 16:1, 20:5 and 22:6 testosterone esters was observed. The presence of 100µM TBT in the incubation mixture did not significantly alter the esterification of testosterone. These results evidence the conjugation of testosterone with the most abundant fatty acids in the digestive gland microsomal fraction of mussels. Copyright © 2017 Elsevier Inc. All rights reserved.

  9. Tsuji-Trost N-allylation with allylic acetates using cellulose-Pd catalyst

    Science.gov (United States)

    Allylic amines are synthesized using heterogeneous cellulose-Pd catalyst via N-allylation of amines; aliphatic and benzyl amines undergo facile reaction with substituted and unsubstituted allyl acetates in high yields.

  10. Soybean biodiesel methyl esters, free glycerin and acid number quantification by 1H nuclear magnetic resonance spectroscopy.

    Science.gov (United States)

    Coral, Natasha; Rodrigues, Elizabeth; Rumjanek, Victor; Zamian, José Roberto; da Rocha Filho, Geraldo Narciso; da Costa, Carlos Emmerson Ferreira

    2013-02-01

    Production of alternative fuels, such as biodiesel, from transesterification of vegetable oil driven by heterogeneous catalysts is a promising alternative to fossil diesel. However, achieving a successful substitution for a new renewable fuel depends on several quality parameters. (1)H NMR spectroscopy was used to determine the amount of methyl esters, free glycerin and acid number in the transesterification of soybean oil with methanol in the presence of hydrotalcite-type catalyst to produce biodiesel. Reaction parameters, such as temperature and time, were used to evaluate soybean oil methyl esters rate conversion. Temperatures of 100 to 180 °C and times of 20 to 240 min were tested on a 1 : 12 molar ratio soybean oil/methanol reaction. At 180 °C/240 min conditions, a rate of 94.5 wt% of methyl esters was obtained, where free glycerin and free fatty acids were not detected. Copyright © 2012 John Wiley & Sons, Ltd.

  11. Process for the conversion of C-terminal peptide esters or acids to amides employing subtilisin in the presence of ammonium salts

    NARCIS (Netherlands)

    Eggen, I.F.; Boeriu, C.G.

    2008-01-01

    The present invention relates to a process for the amidation of C-terminal esters or acids of peptide substrates in solution-phase synthesis of peptides, comprising amidating one or more peptide substrates comprising C-terminal esters or acids using the protease subtilisin in any suitable form in

  12. 40 CFR 721.1729 - Boric acid (H3BO3), mixed esters with polyethylene glycol mono-Bu ether and polyethylene glycol...

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Boric acid (H3BO3), mixed esters with... identified as boric acid (H3BO3), mixed esters with polyethylene glycol mono-Bu ether and polyethylene glycol... NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.1729 Boric...

  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. Efficient Synthesis and Anti-Fungal Activity of Oleanolic Acid Oxime Esters

    Directory of Open Access Journals (Sweden)

    Xiaomei Liang

    2013-03-01

    Full Text Available In order to develop potential glucosamine-6-phosphate synthase inhibitors and anti-fungal agents, twenty five oleanolic acid oxime esters were synthesized in an efficient way. The structures of the new compounds were confirmed by MS, HRMS, 1H-NMR and 13C-NMR. Preliminary studies based on means of the Elson-Morgan method indicated that many compounds exhibited some inhibitory activity of glucosamine-6-phosphate synthase (GlmS, and the original fungicidal activities results showed that some of the compounds exhibited good fungicidal activities towards Sclerotinia sclerotiorum (Lib. de Bary, Rhizoctonia solani Kuhn and Botrytis cinerea Pers at the concentration of 50 µg/mL. These compounds would thus merit further study and development as antifungal agents.

  15. Synergetic deoxy reforming of cellulose and fatty acid esters for liquid hydrocarbon-rich oils.

    Science.gov (United States)

    Wang, Chao; Sui, Jingjing; Lu, Weipeng; Li, Baopeng; Li, Guoxing; Ding, Yihong; Huang, Yong; Geng, Jianxin

    2015-11-01

    A series of liquid hydrocarbons (alkylbenzenes, alkanes, and alkenes) were obtained by a synergetic deoxy reforming (SDR) process of cellulose and linoleic acid methyl ester (LAME) at 350°C and 4-6MPa in a closed system without external source of hydrogen. The liquid product was obtained with a yield of 15wt% at a LAME/cellulose ratio of 0.2. In contrast, the direct deoxy reforming of cellulose produces oil that contains plenty of phenols and oxygen-containing compounds. Due to the insufficiency of water employed (30wt%), a radical reaction pathway was proposed. Quantum chemical calculations indicate that the radicals from LAME interfere with the reactions of the intermediate products from cellulose, being responsible for the removal of phenols and the formation of hydrocarbons. The SDR process offers an embryonic insight in an alternative technique for preparation of hydrocarbon fuels. Copyright © 2015 Elsevier Ltd. All rights reserved.

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

    Science.gov (United States)

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

    2017-08-01

    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. Analysis by Fourier transform infrared (FTIR) and FT-Raman spectroscopies showed that the long chain hydrocarbon structure was successfully grafted onto CNC surfaces. After transesterification the crystal size and crystallinity of nanocrystals were not changed as determined by Raman spectroscopy and wide angle X-ray diffraction (XRD). CNCFE showed higher thermal stability and smaller particle size than unmodified CNCs. Water contact angle measurement indicated the CNCFE surface has significantly higher hydrophobicity than unmodified CNCs. The transesterified CNCs could be potentially used as hydrophobic coatings and reinforcing agents to hydrophobic polymer for nanocomposites. Published by Elsevier Ltd.

  17. 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

  18. Caffeic acid phenethyl ester attenuates IgE-induced immediate allergic reaction.

    Science.gov (United States)

    Nader, Manar A

    2013-04-01

    Caffeic acid phenethyl ester (CAPE) is the active component of honey bee propolis extracts. The results of the current study demonstrate that CAPE attenuated immunoglobulin (Ig)E-mediated allergic response in mast cells. Oral administration of CAPE inhibited IgE-mediated passive cutaneous anaphylaxis. CAPE effectively reduced both histamine and serotonin (5-HT)-induced vascular permeability in rats. CAPE also reduced histamine and leukotrienes (LTs) release from isolated rat peritoneal mast cells. Moreover, CAPE suppressed contraction induced by histamine (3 × 10(-8)-3 × 10(-5) M), 5-HT (3 × 10(-9)-10(-6) M) and adenosine (3 × 10(-8)-10(-5) M) in guinea pig tracheal zigzag. These findings provide evidence that CAPE may serve as an effective therapeutic agent for allergic diseases.

  19. 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

    Although anaerobic biodegradation of di-n-butyl phthalic acid ester (DBP) has been studied over the past decade, only little is known about the microorganisms involved in the biological anaerobic degradation pathways. The aim of this work is to characterize the microbial community dynamics...... 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......, a microorganism described previously as an anaerobic benzaldehyde degrader. Within the archaeal community, there was a shift between two different species of the genus Methanosaeta sp., indicating a highly specific impact of DBP or degradation products on archaeal species. RNA-directed probes were designed from...

  20. The Implications of Recent Recommendations for Managing Patients with Psoriasis Treated with Fumaric Acid Esters.

    Science.gov (United States)

    Foley, Catherine C; Molloy, Oonagh E; Lally, Aoife; Kirby, Brian

    2017-01-01

    Fumaric acid esters (FAEs) are a well-established efficacious systemic treatment for psoriasis. Recent recommendations from the European Medicines Agency suggest monitoring of full blood count every 4 weeks for the duration of therapy for psoriasis. The aim of our study was to assess the incidence of lymphopenia in patients taking FAEs and the impact of recent recommendations for our practice. We reviewed 151 patients treated with FAEs for psoriasis between December 2013 and 2015. Lymphopenia <700 × 109/L was detected within the last 12 months in 36/151 (24%) and lymphopenia <500 × 109/L in 10/151 (7%). Of 39 patients no longer on treatment, 7 (18%) stopped because of persistent lymphopenia. The implementation of these recommendations would have significant resource implications and also likely influence the acceptability of FAEs to patients. Cessation of FAEs necessitates the need for alternative therapy, commonly biologic therapy. © 2017 S. Karger AG, Basel.

  1. Systemic treatment with fumaric acid esters in six paediatric patients with psoriasis in a psoriasis centre.

    Science.gov (United States)

    Steinz, Kirsten; Gerdes, Sascha; Domm, Silja; Mrowietz, Ulrich

    2014-01-01

    Psoriasis is one of the most common inflammatory skin disorders. There are only limited data on systemic treatment in children. To assess the safety and clinical efficacy of the treatment of six paediatric patients with fumaric acid esters (FAE, Fumaderm) for psoriasis. Six patients aged 6-17 years were treated with FAE. Patients underwent regular assessment. Treatment efficacy was evaluated using the Psoriasis Area and Severity Index (PASI) and body surface area (BSA). The mean duration of treatment was 17.8 months. PASI and BSA were determined after 12 weeks. All patients showed improvement in their skin condition, two achieving PASI75, one PASI90 and three PASI100 response. Proteinuria was encountered in one patient and two patients suffered from gastrointestinal discomfort. Treatment was discontinued due to remission in two patients. Treatment with FAE in paediatric patients is a valuable alternative option when systemic treatment is needed.

  2. 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...... ions, rubidium ions and caesium ions....

  3. 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

  4. Fatty acid methyl esters are detectable in the plasma and their presence correlates with liver dysfunction.

    Science.gov (United States)

    Aleryani, Samir Lutf; Cluette-Brown, Joanne E; Khan, Zia A; Hasaba, Hasan; Lopez de Heredia, Luis; Laposata, Michael

    2005-09-01

    Methanol is a component of certain alcoholic beverages and is also an endogenously formed product. On this basis, we have proposed that methanol may promote synthesis of fatty acid methyl esters (FAMEs) in the same way that ethanol promotes fatty acid ethyl ester (FAEE) synthesis. We tested the hypothesis that FAMEs appear in the blood after ethanol intake. Patient plasma samples obtained from our laboratory (n=78) were grouped according to blood ethanol concentrations (intoxicated, blood ethanol >800 mg/l) and non-intoxicated. These samples were further subdivided into groups based on whether the patient had normal or abnormal liver function tests (abnormal, defined as > or =1 abnormality of plasma alanine and aspartate aminotransferase, albumin, total bilirubin, and alkaline phosphatase). A separate set of plasma samples were also divided into normal and abnormal groups based on pancreatic function tests (amylase and lipase). There were no patients with detectable ethanol in this group. Patients with abnormalities in pancreatic function tests were included upon recognition of endogenously produced FAMEs by patients with liver function test abnormalities. FAMEs were extracted from plasma and individual species of FAMEs quantified by gas chromatography-mass spectrometry (GC/MS). Increased concentrations of FAME were found in patient samples with evidence of liver dysfunction, regardless of whether or not they were intoxicated (n=21, p=0.01). No significant differences in plasma FAME concentrations were found between patients with normal (n=15) versus abnormal pancreatic function tests (n=22, p=0.72). The presence of FAMEs in human plasma may be related to the existence of liver disease, and not to blood ethanol concentrations or pancreatic dysfunction. The metabolic pathways associated with FAME production in patients with impaired liver function remain to be identified.

  5. Drug survival of fumaric acid esters for psoriasis: a retrospective study.

    Science.gov (United States)

    Ismail, N; Collins, P; Rogers, S; Kirby, B; Lally, A

    2014-08-01

    Fumaric acid esters (FAEs) have been used for over 30 years in the management of psoriasis. To determine drug survival of FAEs in patients with psoriasis, treatment-limiting adverse drug events and the range of effective drug doses. A retrospective, single-centre study assessing all patients commenced on FAEs between October 2003 and July 2012. Demographic data, length of treatment, reasons for discontinuation of FAEs, side-effects and range of doses were recorded. Two hundred and forty-nine patients [160 (64%) male] were included. The mean age at which FAEs were commenced was 44·5 years (range 17-82 years). The mean length of treatment was 28 months (range 1 week to 106 months). In patients who were commenced on FAEs ≥ 4 years before inclusion in this study, the 4-year drug survival was 60% (64/107). FAEs were discontinued in 146/249 patients (59%); this was due to lack of efficacy in 59/146 (40%) and gastrointestinal upset in 39/146 (27%). A very low dose of FAEs (psoriasis in 26 (10%) patients. The mean treatment duration of these patients was 64 months (range 32-106 months). Fumaric acid esters have a 4-year drug survival rate of 60%, which compares favourably with reported 4-year survival rates of 40% for etanercept and adalimumab and 70% for infliximab. Longer drug survival is more likely in the significant subgroup of patients in whom a very low dose of FAEs is sufficient to control disease. The reasons for this are unclear. © 2014 British Association of Dermatologists.

  6. Renal dysfunction in patients taking fumaric acid esters - a retrospective cross-sectional study.

    Science.gov (United States)

    Menzies, S; Ismail, N; Abdalla, A; Collins, P; Kirby, B; Holian, J; Lally, A

    2017-04-01

    Fumaric acid esters (FAE) have been used for over 30 years in the management of psoriasis. There have been a number of case reports linking the use of FAE with nephrotoxicity, including acute renal injury and Fanconi syndrome. However, one large multicentre retrospective trial showed no evidence of renal dysfunction with FAE. The aim of this study was to determine the number of patients in our institution being treated with FAE who developed significant proteinuria or renal dysfunction. This was a single-centre retrospective study assessing all patients on FAE who attended for follow-up during an 18-week period between February and June 2015. Demographics, comorbidities, duration and dose of treatment with FAE, proteinuria, renal function and other biochemical serum abnormalities were recorded. One hundred and twenty-seven patients were included in the study. Eighty-two patients had proteinuria detected at some stage during treatment with FAE, and 18 of these had persistent proteinuria (positive in at least three consecutive specimens, 12 weeks apart). Six patients (five female) developed proximal tubular dysfunction (PTD). The risk factors for the development of PTD appear to be lower bodyweight (P = 0.03), higher dose per weight (P = 0.03) and longer duration of treatment (P = 0.03). Renal dysfunction improved on discontinuation or dose reduction in FAE. Fumaric acid esters are frequently associated with transient or persistent proteinuria. Significant renal dysfunction is rare and usually reversible on dose reduction or discontinuation of FAE. This study highlights the importance of screening for proteinuria. Higher doses per weight of treatment and longer duration of FAE therapy are likely risk factors for PTD. © 2016 European Academy of Dermatology and Venereology.

  7. 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.

  8. 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

  9. Photo-Crosslinked Biodegradable Hydrogels Prepared From Fumaric Acid Monoethyl Ester-Functionalized Oligomers for Protein Delivery

    NARCIS (Netherlands)

    Jansen, Janine; Mihov, George; Feijen, Jan; Grijpma, Dirk W.

    Photo-crosslinkable, fumaric acid monoethyl ester-functionalized triblock oligomers are synthesized and copolymerized with N-vinyl-2-pyrrolidone to form biodegradable photo-crosslinked hydrogels. Poly(ethylene glycol) is used as the middle hydrophilic segment and the hydrophobic segments are based

  10. 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

  11. Environmental exposure to the plasticizer 1,2-cyclohexane dicarboxylic acid, diisononyl ester (DINCH) in US adults (2000—2012)

    Science.gov (United States)

    Silva, Manori J.; Jia, Tao; Samandar, Ella; Preau, James L.; Calafat, Antonia M.

    2015-01-01

    1,2-Cyclohexane dicarboxylic acid, diisononyl ester (DINCH) is a complex mixture of nine carbon branched-chain isomers. It has been used in Europe since 2002 as a plasticizer to replace phthalates such as di(2-ethylhexyl)phthalate (DEHP) and diisononyl phthalate (DINP). Urinary concentrations of the oxidative metabolites of DINCH, namely cyclohexane-1,2-dicarboxylic acid-monocarboxy isooctyl ester (MCOCH); cyclohexane-1,2-dicarboxylic acid-mono(oxo-isononyl) ester (MONCH); and cyclohexane-1,2-dicarboxylic acid-mono(hydroxy-isononyl) ester (MHNCH), can potentially be used as DINCH exposure biomarkers. The concentrations of MCOCH, MONCH and MHNCH were measured by online solid phase extraction-high performance liquid chromatography-tandem mass spectrometry in urine collected in 2000 (n=114), 2001 (n=57), 2007 (n=23), 2009 (n=118), 2011 (n=94) and 2012 (n=121) from convenience groups of anonymous U.S. adult volunteers with no known DINCH exposure. None of the DINCH metabolites were detected in samples collected in 2000 and 2001. Only one sample collected in 2007 had measureable concentrations of DINCH metabolites. The detection rate for all three metabolites increased from 2007 to 2012. The presence of oxidative metabolites of DINCH in urine suggests that these oxidative metabolites can be used as DINCH biomarkers for exposure assessment even at environmental exposure levels. PMID:23777640

  12. 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.

  13. 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.

  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. Peak alignment and robust principal component analysis of gas chromatograms of fatty acid methyl esters and volatiles

    DEFF Research Database (Denmark)

    Frosch, Stina; Jørgensen, Bo

    2007-01-01

    Gas chromatograms of fatty acid methyl esters and of volatile lipid oxidation products from fish lipid extracts are analyzed by multivariate data analysis [principal component analysis (PCA)]. Peak alignment is necessary in order to include all sampled points of the chromatograms in the data set....

  16. Early detection of renal damage caused by fumaric acid ester therapy by determination of urinary β2-microglobulin.

    Science.gov (United States)

    Häring, N; Mähr, H Sprenger; Mündle, M; Strohal, R; Lhotta, K

    2011-03-01

    Fumaric acid esters are considered efficacious and safe drugs for the treatment of psoriasis. Renal damage, caused either by acute renal injury or Fanconi syndrome, is a recognized side-effect of this therapy. To investigate whether the measurement of urinary excretion of β2-microglobulin, a marker of renal proximal tubular dysfunction, allows early detection of kidney damage before an increase in serum creatinine or significant proteinuria occurs. Urinary β2-microglobulin excretion was measured regularly in 23 patients undergoing fumaric acid ester therapy. Urinary β2-microglobulin remained normal in all 10 male patients. Three (23%) out of 13 female patients experienced an increase in urinary β2-microglobulin excretion. In two of these patients a sharp increase was observed in association with high doses. One further patient had moderately elevated levels on rather low doses of fumaric acid esters. After discontinuing treatment, urinary β2-microglobulin levels returned to normal within a few weeks. Determination of urinary β2-microglobulin possibly allows early detection of renal damage by fumaric acid esters. Female patients seem to be prone to this side-effect, especially when taking high doses. © 2011 The Authors. BJD © 2011 British Association of Dermatologists.

  17. Effectiveness and safety of fumaric acid esters in children with psoriasis: a retrospective analysis of 14 patients from The Netherlands

    NARCIS (Netherlands)

    Balak, D.M.; Oostveen, A.M.; Bousema, M.T.; Venema, A.W.; Arnold, W.P.; Seyger, M.M.B.; Thio, H.B.

    2013-01-01

    BACKGROUND: Fumaric acid esters (FAE) are used as an effective and safe oral treatment for plaque psoriasis in adult patients, but little is known about their efficacy and safety in children with psoriasis. OBJECTIVES: To assess the effectiveness and safety of FAE in the treatment of paediatric

  18. gamma-Aminobutyric acid esters. 3. Synthesis, brain uptake, and pharmacological properties of C-18 glyceryl lipid esters of GABA with varying degree of unsaturation.

    Science.gov (United States)

    Jacob, J N; Hesse, G W; Shashoua, V E

    1987-09-01

    A series of 14C-labeled and unlabeled di-gamma-aminobutyric acid esters of glyceryl lipids having zero to three double bonds (stearoyl, oleoyl, linoleoyl, and linolenoyl) were synthesized. Measurements of the octanol/water partition coefficients of the compounds showed an increase with decreasing number of double bonds (i.e., from linolenoyl to stearoyl). The brain-uptake index went up from 31.5 (linolenoyl) to 45.1 (stearoyl) and similarly the brain-penetration index went up from 15 (linolenoyl) to 28 (stearoyl). Intraperitoneal injections of these di-GABA lipid esters produced a substantial inhibition of the general motor activity in mice at a dose of 30 mg/kg; the most active molecules were those containing two and three double bonds, i.e., the linolenoyl and linolenoyl derivatives. This is in reverse order to that predicted by brain-uptake and lipid-solubility properties, suggesting that the structure of the fatty acid side chain may be an additional factor in influencing biological activity.

  19. On the formation of 4-[N,N-bis(2-chloroethyl)amino]phenyl acetic acid esters of hecogenin and aza-homo-hecogenin and their antileukemic activity.

    Science.gov (United States)

    Camoutsis, Charalambos; Trafalis, Dimitrios; Pairas, George; Papageorgiou, Athanasios

    2005-10-01

    The p-[N,N-bis(2-chloroethyl)amino]phenylacetic acid esters of hecogenin and aza-homo-hecogenin have been prepared and their antineoplastic activity was evaluated against two basic drug screening systems in rodents, P388 lymphocytic and L1210 lymphoid murine leukemias. Among the compounds tested, the p-[N,N-bis(2-chloroethyl)amino]phenylacetic acid ester of aza-homo-hecogenin was appeared to possess a significant higher antileukemic effect. These results support that the alkylating esters of hecogenin produce important antitumor activity as well as, indicate that the aza-homo-hecogenin ester exhibits significantly higher activity due to lactam group (-NHCO-) modification.

  20. 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.

  1. ω-3 Fatty Acid Ethyl Esters Diminish Postprandial Lipemia in Familial Hypercholesterolemia.

    Science.gov (United States)

    Chan, Dick C; Pang, Jing; Barrett, P Hugh R; Sullivan, David R; Burnett, John R; van Bockxmeer, Frank M; Watts, Gerald F

    2016-10-01

    Impaired postprandial chylomicron metabolism induces hypertriglyceridemia and may increase the risk of atherosclerotic cardiovascular disease. Omega-3 fatty acid ethyl ester (ω-3 FAEE) supplementation decreases plasma triglycerides. However, its effect on postprandial chylomicron metabolism in familial hypercholesterolemia (FH) has not yet been investigated. We aimed to examine the effect of ω-3 FAEE supplementation on postprandial responses in plasma triglycerides, very-low-density lipoprotein (VLDL) apolipoprotein B (apoB)-100, and apoB-48 in FH patients receiving standard cholesterol-lowering treatment. We carried out an 8-week open-label, randomized, crossover intervention trial to test the effect of oral supplementation with 4 g/d ω-3 FAEE (46% eicosapentaenoic acid and 38% docosahexaenoic acid) on postprandial triglyceride, VLDL-apoB-100, and apoB-48 responses in FH patients after ingestion of an oral fat load. Plasma total and incremental triglyceride, VLDL-apoB-100, and apoB-48 0- to 10-hour area under the curve (AUC). ω-3 FAEE supplementation significantly (P lipemia in FH patients receiving standard care; this may have implications for further reducing atherosclerotic cardiovascular disease in this high-risk patient group.

  2. 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.

  3. 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.

  4. 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.

  5. Organocatalytic synthesis of N-Phenylisoxazolidin-5-ones and a one-pot synthesis of beta-amino acid esters.

    Science.gov (United States)

    Seayad, Jayasree; Patra, Pranab Kumar; Zhang, Yugen; Ying, Jackie Y

    2008-03-06

    A novel N-heterocyclic carbene (NHC)-catalyzed C-N bond formation by the reaction of alpha,beta-unsaturated aldehydes and nitrosobenzene to N-phenylisoxazolidin-5-ones, followed by an acid-catalyzed esterification and Bamberger-like rearrangement in a mild one-pot protocol leads to N-p-methoxyphenyl (N-PMP) protected beta-amino acid esters.

  6. Nicotinic Acid Accelerates HDL Cholesteryl Ester Turnover in Obese Insulin-Resistant Dogs.

    Directory of Open Access Journals (Sweden)

    Jérôme Le Bloc'h

    Full Text Available Nicotinic acid (NA treatment decreases plasma triglycerides and increases HDL cholesterol, but the mechanisms involved in these change are not fully understood. A reduction in cholesteryl ester transfer protein (CETP activity has been advanced to explain most lipid-modulating effects of NA. However, due to the central role of CETP in reverse cholesterol transport in humans, other effects of NA may have been hidden. As dogs have no CETP activity, we conducted this study to examine the specific effects of extended-release niacin (NA on lipids and high-density lipoprotein (HDL cholesteryl ester (CE turnover in obese Insulin-Resistant dogs with increase plasma triglycerides.HDL kinetics were assessed in fasting dogs before and four weeks after NA treatment through endogenous labeling of cholesterol and apolipoprotein AI by simultaneous infusion of [1,2 13C2] acetate and [5,5,5 2H3] leucine for 8 h. Kinetic data were analyzed by compartmental modeling. In vitro cell cholesterol efflux of serum from NA-treated dogs was also measured.NA reduced plasma total cholesterol, low-density lipoprotein cholesterol, HDL cholesterol, triglycerides (TG, and very-low-density lipoprotein TG concentrations (p < 0.05. The kinetic study also showed a higher cholesterol esterification rate (p < 0.05. HDL-CE turnover was accelerated (p < 0.05 via HDL removal through endocytosis and selective CE uptake (p < 0.05. We measured an elevated in vitro cell cholesterol efflux (p < 0.05 with NA treatment in accordance with a higher cholesterol esterification.NA decreased HDL cholesterol but promoted cholesterol efflux and esterification, leading to improved reverse cholesterol transport. These results highlight the CETP-independent effects of NA in changes of plasma lipid profile.

  7. Omega-3 polyunsaturated fatty acids and cardiovascular disease: an emphasis on omega-3-acid ethyl esters 90 for the treatment of hypertriglyceridemia.

    Science.gov (United States)

    Tatsuno, Ichiro

    2014-11-01

    A number of epidemiological/observational studies, as well as large-scale randomized intervention studies, have been conducted to provide evidence for the efficacy of ω-3 fatty acids against atherosclerotic diseases. Currently, ω-3 fatty acids are commercially available in many parts of the world containing the same active ingredients as Lotriga(®) (ω-3-acid ethyl esters 90 [O3AE highly concentrated ω-3 fatty acid ethyl esters, consisting of eicosapentaenoic acid-ethyl ester and docosahexaenoic acid-ethyl ester [EPA-E/DHA-E]). A recent head-to-head comparative study of O3AEE90 versus EPA-E demonstrated that O3AEE90 4g/day led to a significantly greater reduction in triglycerides (TG) than EPA-E 1.8g/day and that O3AEE90 2g/day produced comparable effects on TG to those with EPA-E 1.8g/day. While both agents were shown to be useful in lowering TG, the hallmark feature of O3AEE90, that is, the presence of the DHA-E component versus its absence in EPA-E, needs to be further examined for its clinical implications.

  8. Condensation of anhydrides or dicarboxylic acids with compounds containing active methylene groups. Part 19: Condensation of phthalic and substituted phthalic anhydrides with benzoylacetic ester

    Science.gov (United States)

    Rotberg, Y. T.; Oshkaya, V. P.

    1985-01-01

    Phthalylbenzoylacetic ester and its nitro and halogen derivatives were prepared through condensation of phthalic anhydride, nitrophthalic anhydride, and phthalic halide anhydride with benzoylacetic ester in a solution of acetic anhydride and triethylamine. The condensation of hemipinic acid anhydride proceeds similarly, but under more drastic conditions. Derivatives of indan-1,3-dione are also formed, with a small yield, in the reaction of nitrophthalic anhydrides with benzoylacetic ester in the presence of increased quantities of triethylamine.

  9. 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...

  10. 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.

  11. In vitro enzymatic biodegradation of amino acid based poly(ester amide)s biomaterials.

    Science.gov (United States)

    Tsitlanadze, G; Kviria, T; Katsarava, R; Chu, C C

    2004-02-01

    A systematic in vitro biodegradation study of regular poly(ester amide)s (PEAs) composed of naturally occurring hydrophobic alpha-amino acids, fatty diols and dicarboxylic acids was carried out in the presence of hydrolases like trypsin, alpha-chymotrypsin, and lipase. An automatic potentiometric titration method was used to examine the biodegradation property of the PEAs. Spontaneous immobilization (absorption) of the enzymes onto the PEAs films surfaces was observed. The surface immobilized enzyme not only accelerated the erosion of the PEAs but also was able to catalyze the hydrolysis of both low-molecular-weight (ATEE) and high-molecular-weight (protein) external substrates. It was found that the enzyme surface absorption process is reversible by nature. A kinetic method for a quantitative determination of the enzyme desorbed from the film surface was developed. The enzymes could also be impregnated into the PEAs to make them "self-destructive" at a target rate. A comparison of the PEAs' in vitro biodegradation data with polylactide (PDLLA) showed that PEAs exhibited a far more tendency toward enzyme catalyzed biodegradation than PDLLA.

  12. Synthesis of trimethylolpropane esters of oleic acid by Lipoprime 50T.

    Science.gov (United States)

    Kiriliauskaitė, Vita; Bendikienė, Vida; Juodka, Benediktas

    2011-09-01

    The ability of the commercial lipolytic enzyme Lipoprime 50T to catalyze the biotechnologically important synthesis of the biodegradable and environmentally acceptable trimethylolpropane (2-ethyl-2-(hydroxymethyl)-1,3-propanediol) ester of oleic acid was investigated. Simple and accurate thin-layer chromatography and computer analysis methods were used that enable one to follow changes of all reaction mixture components simultaneously. The processes of transesterification and esterification were compared. The effects of the molar ratio of the substrates, reaction temperature, time, and medium on the composition of the reaction mixture were analyzed. Esterification was determined to be more preferable than transesterification in both studied solvents. Under the optimal conditions identified (15% w/w water, temperature 60°C, trimethylolpropane to oleic acid molar ratio 1:3.5, and reaction time 72 h), the highest trimethylolpropane trioleate yield of around 62% and trimethylolpropane mono-, di-, and trioleate overall yield of about 83% were obtained. Although the yields are not high enough for industrial application, the process shows the potential to be optimized for higher yields in the near future as the conversions were obtained at ambient pressure, whereas many other processes described in the literature are conducted under vacuum at a specific pressure.

  13. 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.

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

    Science.gov (United States)

    Balak, Deepak M W; Bouwes Bavinck, Jan Nico; de Vries, Aiko P J; Hartman, Jenny; Neumann, Hendrik A Martino; Zietse, Robert; Thio, Hok Bing

    2016-02-01

    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 Fanconi syndrome. Descriptive case series with two cases of Fanconi syndrome associated with FAE treatment diagnosed at two Dutch university nephrology departments, three cases reported at the Dutch and German national pharmacovigilance databases and six previously reported cases. All 11 cases involved female patients with psoriasis. The median age at the time of onset was 38 years [interquartile range (IQR) 37-46]. Patients received long-term FAEs treatment with a median treatment duration of 60 months (IQR 28-111). Laboratory tests were typically significant for low serum levels of phosphate and uric acid, while urinalysis showed glycosuria and proteinuria. Eight (73%) patients had developed a hypophosphataemic osteomalacia and three (27%) had pathological bone fractures. All patients discontinued FAEs, while four (36%) patients were treated with supplementation of phosphate and/or vitamin D. Five (45%) patients had persisting symptoms despite FAEs discontinuation. FAEs treatment can cause drug-induced Fanconi syndrome, but the association has been reported infrequently. Female patients with psoriasis treated long term with FAEs seem to be particularly at risk. Physicians treating patients with FAEs should be vigilant and monitor for the potential occurrence of Fanconi syndrome. Measurement of the urinary albumin:total protein ratio is a suggested screening tool for tubular proteinuria in Fanconi syndrome.

  15. Pharmacokinetics of anti-psoriatic fumaric acid esters in psoriasis patients.

    Science.gov (United States)

    Rostami-Yazdi, Martin; Clement, Bernd; Mrowietz, Ulrich

    2010-09-01

    The aim of this study was to evaluate pharmacokinetic parameters of fumaric acid esters (FAE) in psoriasis patients for the first time. For this prupose new HPLC assays were developed. Additionally, physicochemical parameters of FAE were determined, allowing a better interpretation of the in vivo data. In vivo, monomethylfumarate (MMF) and monoethylfumarate (MEF) were detected after t (lag) = 120 min. T (max) and c (max) of MMF were 210 min and 11.2 microM, respectively, 210 min and 5.2 microM for MEF. The half-life of MMF was 38.7 min, and 25.4 min of MEF. The AUC(0-infinity) of MMF was 172 min microg ml(-1) and 63.6 min microg ml(-1) of MEF. Data display median of three subjects. No plasma levels of dimethylfumarate (DMF) or fumaric acid (FA) were detected. The evaluation of physicochemical parameters of FAE showed that only DMF fulfils the criteria of Lipinski's rule of five. The pKa of MMF was determined as 3.63. The data of this study provide evidence that DMF is most likely absorbed out of the duodenum into the presystemic circulation and is not completely hydrolysed to MMF before uptake as assumed by others.

  16. Lupeol long-chain fatty acid esters with antimalarial activity from Holarrhena floribunda.

    Science.gov (United States)

    Fotie, Jean; Bohle, D Scott; Leimanis, Mara L; Georges, Elias; Rukunga, Geoffrey; Nkengfack, Augustin E

    2006-01-01

    An ethnopharmacological investigation was conducted among the Baka pygmies of Dja biosphere reserve (Cameroon) to collect information on the antimalarial plants used in their daily life. Holarrhena floribunda is one of those plants. Extracts of the stem barks of H. floribunda showed remarkable inhibitory activity against drug-resistant strains of Plasmodium falciparum at doses of 1.02-18.53 microg/mL when tested in vitro against two parasite clones designated as Indochina (W-2) and Sierra Leone (D-6). The aqueous extract was the most active against Indochina (W-2), with IC50 values of 1.02 microg/mL, while the ethanolic extract appeared to be the most active against Sierra Leone (D-6), with an IC50 of 4.33 microg/mL. The bioassay-guided fractionation of the neutral fraction of the crude extract led to the isolation of lupeol (1) and its three new long-chain fatty acid ester derivatives, namely, 3-O-(3'-hydroxyeicosanoyl)lupeol (2), 3-O-[(2'-(tetracosyloxy)acetyl]lupeol (3), and 3-O-[(1' '-hydroxyoctadecyloxy)-2'-hydroxypropanoyl]lupeol (4). These new compounds displayed some in vitro inhibition activity against the chloroquine-resistant strain FCR-3 isolated from Gambia and the chloroquine-sensitive standard strain 3D7. The hydroxy group of the fatty acid side chain appears to decrease the observed activity.

  17. 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.

  18. Role of HCA₂ (GPR109A) in nicotinic acid and fumaric acid ester-induced effects on the skin.

    Science.gov (United States)

    Hanson, Julien; Gille, Andreas; Offermanns, Stefan

    2012-10-01

    Nicotinic acid (NA) and fumaric acid esters (FAE) such as monomethyl fumarate or dimethyl fumarate are drugs that elicit a cutaneous reaction called flushing as a side effect. NA is used to reduce progression of atherosclerosis through its anti-dyslipidemic activity and lipid-independent mechanisms involving immune cells, whereas FAE are used to treat psoriasis via largely unknown mechanisms. Both, NA and FAE, induce flushing by the activation of the G-protein-coupled receptor (GPCR) Hydroxy-carboxylic acid receptor 2 (HCA₂, GPR109A) in cells of the epidermis. While the wanted effects of NA are at least in part also mediated by HCA₂, it is currently not clear whether this receptor is also involved in the anti-psoriatic effects of FAE. The HCA₂-mediated flushing response to these drugs involves the formation of prostaglandins D₂ and E₂ by Langerhans cells and keratinocytes via COX-1 in Langerhans cells and COX-2 in keratinocytes. This review summarizes recent progress in the understanding of the mechanisms underlying HCA₂-mediated flushing, describes strategies to mitigate it and discusses the potential link between flushing, HCA₂ and the anti-psoriatic effects of FAE. Copyright © 2012 Elsevier Inc. All rights reserved.

  19. Mobility-limited polyarylamine biscarbonate ester (PABC) /[6,6]-phenyl $C_{61}$ butyric acid methyl ester (PCBM) bulk heterojunction photovoltaic device

    CERN Document Server

    Lin, Liang-Bih; Preske, Amanda E; Mamiya, Arthur A; Filho, Demétrio A da Silva; Cardoso, George C

    2016-01-01

    Photovoltaic (PV) devices made from blends of a polyarylamine biscarbonate ester (PABC) and [6,6]-phenyl $C_{61}$ butyric acid methyl ester (PCBM) have been fabricated and characterized. PABC is a hole transporting co-polymer prepared from reacting N,N'diphenyl-N,N'bis(3-hydroxyphenyl)1,1;biphenyl(4,4'diamine), diethylene glycol bischloroformate, and triethylemine. By varying the polymer loading in the blend, optimal power conversion efficiency (PCE) of approximately 0.45\\% has been achieved for a blend consisting of 25 wt\\% PABC, which is an order of magnitude higher than the PCE for a 45 wt\\% blend. The optimal ratio is at about 0.44:0.56 molar ratio of the active hole transporting to electron transporting moieties. Results of mobility studies suggest that blends with higher PABC loading have efficiencies limited by 'hole' transport. Also responsible for the lower efficiency at higher PABC concentrations was optical filtering. The efficiency does not appear to be limited by deep charge trapping. Density fun...

  20. Reactivity of Elemental Tin and Zinc toward Organophosphonic Acid Dialkyl Esters: A New One-Pot Recipe for the Synthesis of Coordination Assemblies Derived from O-Alkylorganophosphonate Ligands.

    Science.gov (United States)

    Shankar, Ravi; Mendiratta, Swati; Singla, Nisha; Kociok-Köhn, Gabriele; Lutter, Michael; Jurkschat, Klaus

    2017-01-17

    A new recipe for the synthesis of diorganotin bis(O-alkylorganophosphonate)s, R12Sn{O(P)(O)(OR1)R}2 [R = R1 = methyl (1); R1 = ethyl and R = methyl (2), allyl (3), 2-thienyl (4), benzyl (5)], has been developed from the direct reaction of elemental tin (powder) with organophosphonic acid dialkyl esters, RP(O)(OR1)2, in the presence of a catalytic amount of potassium iodide under ambient conditions (130 °C, 18-20 h). The key steps in the proposed catalytic cycle involve the monodealkylation of phosphonate diester and in situ generation of a R1SnI or R12SnI2 intermediate via the oxidative addition of alkyl iodide on tin. Evidence in support of the formation of organotin species comes from the isolation of Me2Sn{O(P)(O)(OiPr)Me}2 (6) from the direct reaction of tin metal with MeP(O)(OiPr)2 in the presence of methyl iodide. The method has also been extended to isolate Zn{OP(O)(OMe)Me}2 (7) using metallic zinc as the precursor. All of the compounds have been characterized by IR and NMR studies as well as X-ray crystallography for 2, 4, 6, and 7.

  1. Enantioselective iridium-catalyzed carbonyl allylation from the alcohol or aldehyde oxidation level via transfer hydrogenative coupling of allyl acetate: departure from chirally modified allyl metal reagents in carbonyl addition.

    Science.gov (United States)

    Kim, In Su; Ngai, Ming-Yu; Krische, Michael J

    2008-11-05

    Under the conditions of transfer hydrogenation employing an iridium catalyst generated in situ from [Ir(cod)Cl]2, chiral phosphine ligand (R)-BINAP or (R)-Cl,MeO-BIPHEP, and m-nitrobenzoic acid, allyl acetate couples to allylic alcohols 1a-c, aliphatic alcohols 1d-l, and benzylic alcohols 1m-u to furnish products of carbonyl allylation 3a-u with exceptional levels of asymmetric induction. The very same set of optically enriched carbonyl allylation products 3a-u are accessible from enals 2a-c, aliphatic aldehydes 2d-l, and aryl aldehydes 2m-u, using iridium catalysts ligated by (-)-TMBTP or (R)-Cl,MeO-BIPHEP under identical conditions, but employing isopropanol as a hydrogen donor. A catalytically active cyclometallated complex V, which arises upon ortho-C-H insertion of iridium onto m-nitrobenzoic acid, was characterized by single-crystal X-ray diffraction. The results of isotopic labeling are consistent with intervention of symmetric iridium pi-allyl intermediates or rapid interconversion of sigma-allyl haptomers through the agency of a symmetric pi-allyl. Competition experiments demonstrate rapid and reversible hydrogenation-dehydrogenation of the carbonyl partner in advance of C-C coupling. However, the coupling products, which are homoallylic alcohols, experience very little erosion of optical purity by way of redox equilibration under the coupling conditions, although isopropanol, a secondary alcohol, may serve as terminal reductant. A plausible catalytic mechanism accounting for these observations is proposed, along with a stereochemical model that accounts for the observed sense of absolute stereoinduction. This protocol for asymmetric carbonyl allylation transcends the barriers imposed by oxidation level and the use of preformed allyl metal reagents.

  2. 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 %.

  3. Catalytic asymmetric generation of (Z)-disubstituted allylic alcohols.

    Science.gov (United States)

    Salvi, Luca; Jeon, Sang-Jin; Fisher, Ethan L; Carroll, Patrick J; Walsh, Patrick J

    2007-12-26

    A one-pot method for the direct preparation of enantioenriched (Z)-disubstituted allylic alcohols is introduced. Hydroboration of 1-halo-1-alkynes with dicyclohexylborane, reaction with t-BuLi, and transmetalation with dialkylzinc reagents generate (Z)-disubstituted vinylzinc intermediates. In situ reaction of these reagents with aldehydes in the presence of a catalyst derived from (-)-MIB generates (Z)-disubstituted allylic alcohols. It was found that the resulting allylic alcohols were racemic, most likely due to a rapid addition reaction promoted by LiX (X = Br and Cl). To suppress the LiX-promoted reaction, a series of inhibitors were screened. It was found that 20-30 mol % tetraethylethylenediamine inhibited LiCl without inhibiting the chiral zinc-based Lewis acid. In this fashion, (Z)-disubstituted allylic alcohols were obtained with up to 98% ee. The asymmetric (Z)-vinylation could be coupled with tandem diastereoselective epoxidation reactions to provide epoxy alcohols and allylic epoxy alcohols with up to three contiguous stereogenic centers, enabling the rapid construction of complex building blocks with high levels of enantio- and diastereoselectivity.

  4. 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)

  5. 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

  6. 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

  7. 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.

  8. Fatty-acid alkyl esters in table olives in relation to abnormal fermentation and poorly conducted technological treatments

    Directory of Open Access Journals (Sweden)

    Lanza, B.

    2016-06-01

    Full Text Available 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.H

  9. 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)

  10. 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,

  11. Reinvestigation of structures of robustasides B and C, and isolation of (E)-2,5-dihydroxycinnamic acid esters of arbutin and glucose from the leaves of Grevillea robusta.

    Science.gov (United States)

    Yamashita-Higuchi, Yukiko; Sugimoto, Sachiko; Matsunami, Katsuyoshi; Otsuka, Hideaki

    2012-01-01

    From the leaves of Grevillea robusta, compounds whose NMR data were superimposable on those of robustasides B and C were isolated along with two new compounds, (E)-2,5-dihydroxycinnamic acid esters of arbutin and D-glucose, and two known compounds, robustaside A and (E)-2,5-dihydroxycinnamic acid. The structures of robustasides B and C were not arbutin caffeates, being revised to arbutin (E)-2,5-dihydroxycinnamic acid esters.

  12. Fourier Transform Infrared (FTIR) Spectroscopy as a Utilitarian Tool for the Routine Determination of Acidity in Ester-Based Oils.

    Science.gov (United States)

    Meng, Xianghe; Li, Lei; Ye, Qin; van de Voort, Frederik

    2015-09-23

    A primary Fourier transform infrared (FTIR) method capable of determining acidity in ester-based oils is described and evaluated. Absolute free fatty acid (%FFA) and acid value (AV) calibrations were devised by spiking oleic acid into a refined, acid-free oil and measuring ν COO(-) at ∼ 1569 and ν phenolate(-) at ∼ 1588 cm(-1), respectively, in the second-derivative differential spectra. The FTIR acidity predictions were compared to the AOCS titrimetric method using acid mixtures as well as acid containing used vendor oils of undefined makeup and provenance, using two spectroscopically divergent reference oils as AC0. Relative to the AOCS reference method, the FTIR procedure was found to be both more accurate (± 0.107 vs ± 0.122) and reproducible (± 0.025 vs ± 0.077) in determining %FFA and similar in predicting AV. The FTIR phenolate method overcomes a variety of limitations of earlier FTIR-based methods, being particularly simple and well suited to routine, semiautomated acidity analysis of ester-based oils using a basic FTIR spectrometer.

  13. Alkyl protocatechuates as novel urinary biomarkers of exposure to p-hydroxybenzoic acid esters (parabens).

    Science.gov (United States)

    Wang, Lei; Kannan, Kurunthachalam

    2013-09-01

    Human exposure to p-hydroxybenzoic acid esters (parabens) is a concern, owing to adverse health effects of these compounds. Parabens are metabolized and eliminated from the human bodies within a few hours of exposure. In this study, for the first time, methyl- and ethyl-protocatechuates (OH-MeP and OH-EtP) and their parent compounds, methyl- (MeP) and ethyl-parabens (EtP), were determined in urine samples collected from U.S. children and adults. Alkyl protocatechuates were found in almost all urine samples, with median concentrations of 11.8 (OH-MeP) and 2.90ng/mL (OH-EtP) in adults, and 5.43 (OH-MeP) and 0.85ng/mL (OH-EtP) in children. In adults, the concentrations of urinary OH-MeP and OH-EtP were higher than the corresponding concentrations of MeP and EtP. Significant correlation between OH-MeP/OH-EtP and MeP/EtP was observed. This is the first report to document hydroxylation of parabens in humans, and to propose hydroxylated metabolites (i.e., alkyl protocatechuates) as alternative biomarkers of exposure to parabens in human biomonitoring studies. The rates of transformation of parabens between children and adults appeared to be different, as evidenced from the slopes of regression between alkyl protocatechuates and parabens. In addition to alkyl protocatechuates, hydroxybenzoic acid (4-HB) and 3,4-dihydroxybenzoic acid (3,4-DHB) were found at considerable levels in the urine samples. The occurrence of a significant proportion of alkyl protocatechuates and 3,4-DHB suggests the need for inclusion of these derivatives in accurate estimation of human exposure to parabens and in epidemiological studies that associate paraben exposure to health outcomes in populations. Copyright © 2013 Elsevier Ltd. All rights reserved.

  14. Activation of carboxylic acids by pyrocarbonates. Synthesis of symmetric anhydrides and esters of N-protected amino acids using dialkyl pyrocarbonates as condensing reagents.

    Science.gov (United States)

    Pozdnev, V F

    1992-11-01

    Activation of carboxylic acids was achieved via dialkyl pyrocarbonates (ROCO)2O, R = C2H5, i-C3H7, sec-C4H9, tert.-C4H9) in aprotic solvents in the presence tertiary amines. A convenient procedure for the preparation of carboxylic acid anhydrides from carboxylic acids and di-tert.-butyl pyrocarbonate in the presence of pyridine is reported. Analogously, di-isopropyl- or diethyl pyrocarbonate may be used in the presence of N-methylmorpholine (triethylamine). With pyridine, di-isopropyl- or diethyl pyrocarbonate carboxylic acids form isopropyl- or ethyl esters, respectively. A wide variety of esters were prepared in good yields in a one-pot procedure from carboxylic acids, including N-protected amino acids, and alcohols or from phenols by means of di-tert.-butyl pyrocarbonate in the presence of pyridine (Boc2O-pyridine system). t-Butyl esters of carboxylic acids were obtained by the same procedure with 4-dimethylaminopyridine. In the absence of carboxylic acid, with 4-dimethylaminopyridine Boc2O and alcohols generate alkyl tert.-butyl carbonates.

  15. Synthesis of Higher Fatty Acid Starch Esters using Vinyl Laurate and Stearate as Reactants

    NARCIS (Netherlands)

    Junistia, Laura; Sugih, Asaf K.; Manurung, Robert; Picchioni, Francesco; Janssen, Leon P. B. M.; Heeres, Hero J.

    2008-01-01

    This paper describes the synthesis of long-chain fatty esters of corn starch (starch laurate and starch stearate) with a broad range in degree of substitution (DS = 0.24-2.96). The fatty esters were prepared by reacting the starch with vinyl laurate or vinyl stearate in the presence of basic

  16. The sequence and crystal structure of the alpha-amino acid ester hydrolase from Xanthomonas citri define a new family of beta-lactam antibiotic acylases

    NARCIS (Netherlands)

    Barends, Thomas; Polderman - Tijmes, Jolanda; Jekel, PA; Hensgens, CMH; de Vries, Erik; Janssen, DB; Dijkstra, Bauke W.

    2003-01-01

    alpha-Amino acid ester hydrolases (AEHs) catalyze the hydrolysis and synthesis of esters and amides with an alpha-amino group. As such, they can synthesize beta-lactam antibiotics from acyl compounds and beta-lactam nuclei obtained from the hydrolysis of natural antibiotics. This article describes

  17. The effect of ethanol on the kinetics of lipase-mediated enantioselective esterification of 4-methyloctanoic acid and the hydrolysis of its ethyl ester

    NARCIS (Netherlands)

    Heinsman, N.W.J.T.; Valente, A.M.; Schmienk, H.G.F.; Padt, van der A.; Franssen, M.C.R.; Groot, de Æ.; Riet, van 't K.

    2001-01-01

    The Novozym 435? catalyzed esterification and hydrolysis reactions of 4-methyloctanoic acid (ethyl ester) were investigated. In both the hydrolysis and esterification reactions, the increase of ethanol concentration led to an increase in enantiomeric ratio (E). For hydrolysis of the ethyl ester, the

  18. The mechanism of oleic acid nitration by *NO(2).

    Science.gov (United States)

    Jain, Kavita; Siddam, Anjaiah; Marathi, Archana; Roy, Uzzal; Falck, J R; Balazy, Michael

    2008-08-01

    Fatty acid nitration is a recently discovered process that generates biologically active nitro lipids; however, its mechanism has not been fully characterized. For example, some structural details such as vinyl and allyl isomers of the nitro fatty acids have not been established. To characterize lipids that originated from a biomimetic reaction of *NO(2) with oleic acid, we synthesized several isomers of nitro oleic acids and studied their chromatography and mass spectra by various techniques of mass spectrometry. LC/MS analysis performed on a high resolution micro column detected molecular carboxylic anions of various oleic acid nitro isomers (NO(2)OA). Esterification of NO(2)OA with pentafluorobenzyl bromide and diisopropylethylamine as a catalyst produced a unique isoxazole ester derivative exclusively from allyl NO(2)OA isomers via dehydration of the nitro group at ambient temperatures. This new analytical procedure revealed that *NO(2) generated two vinyl and two allyl isomers of NO(2)OA. The vinyl isomers showed high regioselectivity with the 1.8:1 preference for the 10-NO(2)OA isomer that was absent among allylic isomers. The nitration also generated elaidic acid via cis-trans isomerization and diatereoisomers of vicinal nitro hydroxy, nitro keto and alpha-nitro epoxy stearic acids with high stereo and regioselectivity. Nitration of small unilamelar phospholipid vesicles resulted in several phospholipids containing nitro lipids and elaidic acid amenable to hydrolysis by phospholipase A(2).

  19. Separation and characterization of adjuvant oligosaccharide oleate ester derived from product mixture of mannitol-oleic acid esterification.

    Science.gov (United States)

    Oda, Kenji; Sato, Yukari; Katayama, Shigeji; Ito, Asao; Ohgitani, Toshiaki

    2004-07-29

    Nearly 30 years after intense investigations of mannide monooleates for use as vaccine adjuvants, a novel adjuvant-active saccharide oleate ester was isolated and identified from the product mixture synthesized from mannitol and oleic acid. The mixture, which contained many kinds of mannide mono- and dioleates and their derivatives, was fractionated by liquid chromatography (LC), and the fraction with the highest adjuvanticity was obtained. Gel permeation chromatography (GPC) showed that it consisted of one major compound with an average molecular weight (MW) 2850. Infrared (IR) absorption and proton nuclear magnetic resonance spectra suggested it had oligosaccharide moieties and oleate domains. These findings suggested that it was an oligosaccharide oleate ester of the average MW 2850. The molecular ratio of oleate chains per monosaccharide unit was approximately 0.8. The ester induced both IgG1 and IgG2a antibody responses in mice in a dispersed form without base oil. This ester thus appears to be one of the adjuvant-active compounds largely contributing to the excellent adjuvanticity of mannide oleate mixture broadly used as vaccine emulsifier. These results and previous findings suggest that the fundamental adjuvanticity of this 'oligo' saccharide acylate ester was in accord with the hydrophil-lipophil balance (HLB) theory, similarly to other saccharide acylate esters. It is now expected that this compound will be useful as novel vaccine adjuvant which may induce both Th1 and Th2 type immune responses with low or no toxicity, not only as an vaccine emulsifier but in an aqueous suspension form.

  20. Stereocomplexes of enantiomeric lactic acid and sebacic acid ester-anhydride triblock copolymers.

    Science.gov (United States)

    Slivniak, Raia; Domb, Abraham J

    2002-01-01

    A systematic study on the synthesis, characterization, degradation, and drug release of d-, l-, and dl-poly(lactic acid) (PLA)-terminated poly(sebacic acid) (PSA) and their stereocomplexes is reported. PLA-terminated sebacic acid polymers were synthesized by melt condensation of the acetate anhydride derivatives of PLA oligomers and sebacic anhydride oligomers to yield ABA triblock copolymers of molecular weights between 3000 and 9000 that melt at temperatures between 35 and 80 degrees C. Pairs of the corresponding enantiomeric ABA copolymers composed of l-PLA-PSA-l-PLA and d-PLA-PSA-d-PLA were solvent mixed to form stereocomplexes. The formed stereocomplexes exhibited higher crystalline melting temperature than the enantiomeric polymers, which indicate stereocomplex formulation. The PLA terminals had a significant effect on the polymer degradation and drug release rate. PSA with up to 20% w/w of PLA terminals degraded and released the incorporated drug for more than 3 weeks as compared with 10 days for PSA homopolymer.

  1. Simulated moving bed chromatography for the separation of ethyl esters of eicosapentaenoic acid and docosahexaenoic acid under nonlinear conditions.

    Science.gov (United States)

    Li, Min; Bao, Zongbi; Xing, Huabin; Yang, Qiwei; Yang, Yiwen; Ren, Qilong

    2015-12-18

    In this study, ethyl esters of eicosapentaenoic acid and docosahexaenoic acid were separated with simulated moving bed (SMB) chromatography, where the stationary phase was C18 silica gel with particle size of 10μm packed in eight columns, and the mobile phase was pure methanol. The Henry constants, transport parameters and total porosity were measured from pulse response chromatographic experiments using a single column. The Henry constants were obtained from the first moment analysis. The transport parameters including axial dispersion coefficients and effective mass transfer coefficients were obtained from the second moment analysis. Nonlinear adsorption equilibrium isotherms for the pure components and their mixture were determined from adsorption-desorption method. The Langmuir model was used to fit the experimental data, and the corresponding parameters were further used to predict the competitive adsorption equilibria of the mixture. The validity of mathematical model parameters was checked by a frontal chromatography experiment. The simulated results of the SMB process using these parameters agreed well with the experimental results. At the feed concentration of 100g/L, the SMB separation was able to produce both solutes with relative purity above 99%, productivity of 13.11g/L adsorbent/h, and solvent consumption of 0.46L/g. Copyright © 2015 Elsevier B.V. All rights reserved.

  2. Production of fatty acid butyl esters using the low cost naturally immobilized Carica papaya lipase.

    Science.gov (United States)

    Su, Erzheng; Wei, Dongzhi

    2014-07-09

    In this work, the low cost naturally immobilized Carica papaya lipase (CPL) was investigated for production of fatty acid butyl esters (FABE) to fulfill the aim of reducing the lipase cost in the enzymatic butyl-biodiesel process. The CPL showed specificities to different alcohol acyl acceptors. Alcohols with more than three carbon atoms did not have negative effects on the CPL activity. The CPL catalyzed butanolysis for FABE production was systematically investigated. The reaction solvent, alcohol/oil molar ratio, enzyme amount, reaction temperature, and water activity all affected the butanolysis process. Under the optimized conditions, the highest conversion of 96% could be attained in 24 h. These optimal conditions were further applied to CPL catalyzed butanolysis of other vegetable oils. All of them showed very high conversion. The CPL packed-bed reactor was further developed, and could be operated continuously for more than 150 h. All of these results showed that the low cost Carica papaya lipase can be used as a promising lipase for biodiesel production.

  3. [Determination of phthalic acid esters in imitation jewellery and investigation of their migration risk].

    Science.gov (United States)

    Lai, Ying; Huang, Zongping; Ge, Xiuxiu; Lin, Rui; Chen, Hexiu

    2012-07-01

    A reliable gas chromatography-mass spectrometry (GC-MS) method was developed for the determination of 14 phthalic acid esters (PAEs) in imitation jewellery. The influences of sample pretreatment methods including microwave extraction, ultrasonic extraction, accelerated solvent extraction (ASE) and Soxhlet extraction on the determination of PAEs were investigated. The migration risk of dibutyl phthalate (DBP), bis(2-ethyl hexyl) phthalate (DEHP) and dioctyl phthalate (DOP) in plastic imitation jewellery was investigated under the simulated body temperature and sweat environment within 0 h to 168 h. The results showed that the target compounds can be effectively extracted with hexane-acetone (1:1, v/v) under microwave extraction for 35 min. The limit of quantification (LOQ) of the method was 5 mg/kg for 12 PAEs (25 mg/kg for diisononyl phthalate (DINP) and diisodecyl phthalate (DIDP)). The calibration curves were linear within 0.1-50 mg/L (0.5-250 mg/L for DINP and DIDP) with the correlation coefficients above 0.99. The recoveries ranged from 90.95% to 98.67% at three spiked levels. The migration risk of DEHP was higher than DBP and DOP with 0.75% dissolved after soaking for 72 h under the simulated conditions. The sensitivity, recovery and selectivity of the method can meet the requirements of the practical work.

  4. High biobased content epoxy-anhydride thermosets from epoxidized sucrose esters of Fatty acids.

    Science.gov (United States)

    Pan, Xiao; Sengupta, Partha; Webster, Dean C

    2011-06-13

    Novel highly functional biobased epoxy compounds, epoxidized sucrose esters of fatty acids (ESEFAs), were cross-linked with a liquid cycloaliphatic anhydride to prepare polyester thermosets. The degree of cure or conversion was studied using differential scanning calorimetry (DSC), and the sol content of the thermosets was determined using solvent extraction. The mechanical properties were studied using tensile testing to determine Young's modulus, tensile stress, and elongation at break. Dynamic mechanical analysis (DMA) was used to determine glass-transition temperature, storage modulus, and cross-link density. The nanomechanical properties of the surfaces were studied using nanoindentation to determine reduced modulus and indentation hardness. The properties of coatings on steel substrates were studied to determine coating hardness, adhesion, solvent resistance, and mechanical durability. Compared with the control, epoxidized soybean oil, the anhydride-cured ESEFAs have high modulus and are hard and ductile, high-performance thermoset materials while maintaining a high biobased content (71-77% in theory). The exceptional performance of the ESEFAs is attributed to the unique structure of these macromolecules: well-defined compact structures with high epoxide functionality. These biobased thermosets have potential uses in applications such as composites, adhesives, and coatings.

  5. 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.

  6. 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.

  7. 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.

  8. 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.

  9. 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.

  10. Molecular Simulations of Fatty-Acid Methyl Esters and Representative Biodiesel Mixtures.

    Science.gov (United States)

    Bharadwaj, Vivek S; Eagan, Nathaniel M; Wang, Nicholas M; Liberatore, Matthew W; Maupin, C Mark

    2015-08-13

    Despite the importance of fatty-acid methyl esters (FAMEs) as key components of various green solvents, detergents, plasticizers, and biodiesels, our understanding of these systems at the molecular level is limited. An enhanced molecular-level perspective of FAMEs will enable a detailed analysis of the polymorph and crystallization phenomena that adversely impact flow properties at low temperatures. Presented here, is the parameterization and validation of a charge-modified generalized amber force field (GAFF) for eight common FAMEs and two representative biodiesel mixtures. Our simulations accurately reproduce available experimental data (e.g. densities and self-diffusivity coefficients) and their trends, with respect to temperature and degree of unsaturation. Structural analyses from our simulations provide a more detailed picture of liquid-phase molecular ordering in FAMEs and confirm recent experimental hypotheses. This study provides a firm foundation to initiate further studies into the mechanisms that drive crystallization phenomena at the molecular level. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  11. 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.

  12. Significance of the detection of esters of p-hydroxybenzoic acid (parabens) in human breast tumours.

    Science.gov (United States)

    Harvey, Philip W; Everett, David J

    2004-01-01

    This issue of Journal of Applied Toxicology publishes the paper Concentrations of Parabens in Human Breast Tumours by Darbre et al. (2004), which reports that esters of p-hydroxybenzoic acid (parabens) can be detected in samples of tissue from human breast tumours. Breast tumour samples were supplied from 20 patients, in collaboration with the Edinburgh Breast Unit Research Group, and analysed by high-pressure liquid chromatography and tandem mass spectrometry. The parabens are used as antimicrobial preservatives in underarm deodorants and antiperspirants and in a wide range of other consumer products. The parabens also have inherent oestrogenic and other hormone related activity (increased progesterone receptor gene expression). As oestrogen is a major aetiological factor in the growth and development of the majority of human breast cancers, it has been previously suggested by Darbre that parabens and other chemicals in underarm cosmetics may contribute to the rising incidence of breast cancer. The significance of the finding of parabens in tumour samples is discussed here in terms of 1). Darbre et al's study design, 2). what can be inferred from this type of data (and what can not, such as the cause of these tumours), 3). the toxicology of these compounds and 4). the limitations of the existing toxicology database and the need to consider data that is appropriate to human exposures. Copyright 2004 John Wiley & Sons, Ltd.

  13. Caffeic Acid Phenethyl Ester Regulates PPAR’s Levels in Stem Cells-Derived Adipocytes

    Directory of Open Access Journals (Sweden)

    Luca Vanella

    2016-01-01

    Full Text Available Hypertrophic obesity inhibits activation of peroxisome proliferators-activated receptor gamma (PPARγ, considered the key mediator of the fully differentiated and insulin sensitive adipocyte phenotype. We examined the effects of Caffeic Acid Phenethyl Ester (Cape, isolated from propolis, a honeybee hive product, on Adipose Stem Cells (ASCs differentiation to the adipocyte lineage. Finally we tested the effects of Cape on insulin-resistant adipocytes. Quantification of Oil Red O-stained cells showed that lipid droplets decreased following Cape treatment as well as radical oxygen species formation. Additionally, exposure of ASC to high glucose levels decreased adiponectin and increased proinflammatory cytokines mRNA levels, which were reversed by Cape-mediated increase of insulin sensitivity. Cape treatment resulted in decreased triglycerides synthesis and increased beta-oxidation. Exposure of ASCs to Lipopolysaccharide (LPS induced a reduction of PPARγ, an increase of IL-6 levels associated with a well-known stimulation of lipolysis; Cape partially attenuated the LPS-mediated effects. These observations reveal the main role of PPARγ in the adipocyte function and during ASC differentiation. As there is now substantial interest in functional food and nutraceutical products, the observed therapeutic value of Cape in insulin-resistance related diseases should be taken into consideration.

  14. Electronic Structures and Optical Properties of Phenyl C71 Butyric Acid Methyl Esters

    Directory of Open Access Journals (Sweden)

    Cai-Rong Zhang

    2013-01-01

    Full Text Available Phenyl C71 butyric acid methyl ester (PC71BM has been adopted as electron acceptor materials in bulk heterojunction solar cells with relatively higher power conversion efficiency. The understanding of the mechanism and performance for the devices based upon PC71BM requires the information of conformations, electronic structures, optical properties, and so forth. Here, the geometries, IR and Raman, electronic structures, polarizabilities, and hyperpolarizabilities of PC71BM isomers are studied by using density functional theory (DFT; the absorption and excitation properties are investigated via time-dependent DFT with B3LYP, PBE0, and CAM-B3LYP functionals. The calculated results show that [6,6]PC71BM is more stable than [5,6]PC71BM due to the lower total energy. The vibrational modes of the isomers at IR and Raman peaks are quite similar. As to absorption properties, CAM-B3LYP functional is the suitable functional for describing the excitations of PC71BM because the calculated results with CAM-B3LYP functional agree well with that of the experiment. The analysis of transition configurations and molecular orbitals demonstrated that the transitions at the absorption maxima in UV/Vis region are localized π-π* transitions in fullerenes cages. Furthermore, the larger isotropic polarizability of PC71BM indicates that the response of PC71BM to applied external electric field is stronger than that of PC61BM, and therefore resulting into better nonlinear optical properties.

  15. Enhancing fatty acid ethyl ester production in Saccharomyces cerevisiae through metabolic engineering and medium optimization.

    Science.gov (United States)

    Thompson, R Adam; Trinh, Cong T

    2014-11-01

    Biodiesels in the form of fatty acyl ethyl esters (FAEEs) are a promising next generation biofuel due to their chemical properties and compatibility with existing infrastructure. It has recently been shown that expression of a bacterial acyl-transferase in the established industrial workhorse Saccharomyces cerevisiae can lead to production of FAEEs by condensation of fatty acyl-CoAs and ethanol. In contrast to recent strategies to produce FAEEs in S. cerevisiae through manipulation of de novo fatty acid biosynthesis or a series of arduous genetic manipulations, we introduced a novel genetic background, which is comparable in titer to previous reports with a fraction of the genetic disruption by aiming at increasing the fatty acyl-CoA pools. In addition, we combined metabolic engineering with modification of culture conditions to produce a maximum titer of over 25 mg/L FAEEs, a 40% improvement over previous reports and a 17-fold improvement over our initial characterizations. Biotechnol. Bioeng. 2014;111: 2200-2208. © 2014 Wiley Periodicals, Inc. © 2014 Wiley Periodicals, Inc.

  16. Production of Hydroprocessed Esters and Fatty Acids (HEFA – Optimisation of Process Yield

    Directory of Open Access Journals (Sweden)

    Starck Laurie

    2016-01-01

    Full Text Available Both Fischer-Tropsch (FT and Hydroprocessed Esters and Fatty Acids (HEFA Synthetic Paraffinic Kerosine (SPK fuels are considered as leading alternative replacements for conventional jet fuel. To satisfy the requirements of Civil Aviation Authorities (CAA, their drop-in incorporations have been subjected to a rigorous certification process. To reach the ambitious incorporation targets, new routes for biofuels incorporation may need to emerge, involving optimizing the production processes and the blending strategies. This paper focuses on a new strategy for incorporating HEFA, allowing the process yield to be optimised. One of the major steps limiting the process yield for HEFA remains the isomerisation that allows production of a biofuel with very good cold flow properties. But this step introduces a substantial decrease of the overall yield (fuel component per kg of starting material due to the production of light compounds, unsuitable for conventional jet fuel. In this work relaxing the freezing point requirement for the neat HEFA component (by decreasing the severity of the isomerisation step is proposed in order to minimize the production of less valuable light compounds. This strategy could lead to a significant additional biofuel yield with respect to the oil compared to a process making a better freeze point component. This allows the land surface area necessary for HEFA feedstock cultivation to be reduced for a given amount of bio-jet fuel produced.

  17. Evaluation of Sucrose Fatty Acid Esters as Lubricants in Tablet Manufacturing.

    Science.gov (United States)

    Nakamura, Shohei; Ishii, Nozomi; Nakashima, Naoyuki; Sakamoto, Takatoshi; Yuasa, Hiroshi

    2017-01-01

    Lubricants are essential additives in tablet formulations. Magnesium stearate (Mg-St) is the most commonly used lubricant in tableting. Here, we used sucrose fatty acid ester (SE) as an additive to manufacture tablets by direct compression. We evaluated the effects of hydrophile-lipophile balance (HLB) and the amount of SE on the flowability of a pharmaceutical powder using angle of repose and practical angle of internal friction measurements. In addition, we investigated the effects of SE on tablet properties. When SEs with an HLB ≥3 were added, the angle of repose was approximately the same as that of a pharmaceutical powder containing Mg-St, with no major differences in flowability. However, the practical angle of internal friction became closer to pharmaceutical powder containing Mg-St as HLB decreased. As HLB increased, the practical angle of internal friction approached the value of additive-free pharmaceutical powder. Tablets containing 2.0% Mg-St had a mean hardness of 40 N and disintegrated in approximately 6 min, whereas tablets containing 2.0% SE (low HLB) had a mean hardness of approximately ≥80 N and disintegrated within 3 min. The results indicate that SEs can be used as lubricants in tablet production by direct compression and to reduce problems associated with the use of Mg-St. In particular, we suggest that SEs with low HLB values can be used as excipients to achieve high tablet hardness and short disintegration time.

  18. Lymphopenia and CD4+/CD8+ Cell Reduction under Fumaric Acid Esters.

    Science.gov (United States)

    Sondermann, Wiebke; Rompoti, Natalia; Leister, Larissa; Huptas, Lisa; Klode, Joachim; Dissemond, Joachim; Körber, Andreas

    2017-09-28

    Fumaric acid esters (FAEs) are a broadly used therapy option for patients suffering from moderate-to-severe plaque psoriasis. Various studies in psoriasis have already shown peripheral blood lymphopenia during oral FAE therapy. Smaller studies also documented a reduction of CD4+ and CD8+ cell counts. Up to now, there are few case reports on opportunistic infections under FAE therapy - all of them associated with lymphopenia. To examine the influence of FAEs on white blood cells with special regard to leukocytes, lymphocytes, and CD4+ and CD8+ cells during psoriasis therapy. A cohort of 105 patients with diagnosed moderate-to-severe chronic plaque psoriasis was enrolled in this single-centre observational trial. For a cohort of 36 patients, T-cell subset analyses were performed. Of the total, 65 patients were male (61.9%) and 40 (38.1%) female; the mean age was 43.3 years (range 16-73 years). The median lymphocyte count was significantly reduced by about 35.8% after the first 6 months of therapy. When assessing the lymphocyte count nadir over the whole period observed, 46.7% of the patients developed lymphopenia. Severe lymphopenia (psoriasis patients receiving FAEs. We suggest periodic monitoring of absolute lymphocyte counts as well as the establishment of the determination of T-cell subsets prior to and during therapy. © 2017 S. Karger AG, Basel.

  19. Severe recalcitrant cutaneous manifestations in systemic lupus erythematosus successfully treated with fumaric acid esters.

    Science.gov (United States)

    Saracino, A M; Orteu, C H

    2017-02-01

    Fumaric acid esters (FAEs) have proven efficacy in the treatment of psoriasis and have been in use for decades. More recently, as their mechanism of action and abundant immunomodulatory effects become clearer, the potential benefits of treating other inflammatory skin conditions using FAEs are increasingly being recognized. The use of FAEs as combination systemic therapy has not been well studied and data are lacking regarding the safety and efficacy of this type of therapy. In this case report, three patients with severe, extensive and recalcitrant cutaneous manifestations of systemic lupus erythematosus (SLE) (one case of disseminated discoid lesions and two with severe chilblain lesions) were treated with Fumaderm® (containing the FAE dimethylfumarate and monoethylhydrogen fumarate salts), after failing to respond to a multitude of other monotherapies and combination therapies. All patients showed a substantial clinical response when FAEs were added to their treatment, with concurrent improvements in quality-of-life instrument scores. The treatment was well tolerated in the context of systemic organ involvement and as combination therapy with other agents, such as hydroxychloroquine and mycophenolate mofetil. These cases of SLE illustrate the potential use of FAEs in severe, disfiguring and otherwise therapy-resistant skin lesions, including, to our knowledge, the first two reported cases of FAE-treated chilblain lupus erythematosus. © 2016 British Association of Dermatologists.

  20. Long-term safety aspects of systemic therapy with fumaric acid esters in severe psoriasis.

    Science.gov (United States)

    Hoefnagel, J J; Thio, H B; Willemze, R; Bouwes Bavinck, J N

    2003-08-01

    Therapy with fumaric acid esters (FAE) has been shown to be safe and effective in patients with severe psoriasis in several clinical studies with limited follow-up periods. In view of the chronic character of psoriasis, long-term safety aspects are of major importance in determining the suitability of a drug during prolonged periods of treatment. To investigate adverse events of therapy with systemic FAE with follow-up periods of up to 14 years, in order to determine safety aspects of their long-term use in patients with severe psoriasis. Current and/or past therapeutic use of FAE was reviewed in 66 patients with severe psoriasis. Forty-one of 66 patients had received FAE for at least 1 year, and 12 of these 41 patients had received FAE for between 10 and 14 years. Adverse events were reported in 73% of the patients. These were usually mild and mainly consisting of flushing (55%), diarrhoea (42%), nausea (14%), tiredness (14%) and stomach complaints (12%). A relative lymphocytopenia was observed in 76% of patients during therapy with FAE, resulting in a permanent discontinuation of therapy with FAE in four patients. A transient eosinophilia and moderate liver enzyme elevations were observed in 14% and 25% of patients, respectively. The present study indicates that FAE can be considered as a safe long-term treatment in patients with severe psoriasis.

  1. Progressive multifocal leukoencephalopathy in patients treated with fumaric acid esters: a review of 19 cases.

    Science.gov (United States)

    Gieselbach, Robbert-Jan; Muller-Hansma, Annemarie H; Wijburg, Martijn T; de Bruin-Weller, Marjolein S; van Oosten, Bob W; Nieuwkamp, Dennis J; Coenjaerts, Frank E; Wattjes, Mike P; Murk, Jean-Luc

    2017-06-01

    Progressive multifocal leukoencephalopathy (PML) is a rare and potentially fatal condition caused by a brain infection with JC polyomavirus (JCV). PML develops almost exclusively in immunocompromised patients and has recently been associated with use of fumaric acid esters (FAEs), or fumarates. We reviewed the literature and the Dutch and European pharmacovigilance databases in order to identify all available FAE-associated PML cases and distinguish possible common features among these patients. A total of 19 PML cases associated with FAE use were identified. Five cases were associated with FAE use for multiple sclerosis and 14 for psoriasis. Ten patients were male and nine were female. The median age at PML diagnosis was 59 years. The median duration of FAE therapy to PML symptom onset or appearance of first PML lesion on brain imaging was 31 months (range 6-110). In all cases a certain degree of lymphocytopenia was reported. The median duration of lymphocytopenia to PML symptom onset was 23 months (range 6-72). The median lymphocyte count at PML diagnosis was 414 cells/µL. CD4 and CD8 counts were reported in ten cases, with median cell count of 137 and 39 cells/µL, respectively. Three patients died (16% mortality). The association between occurrence of PML in patients with low CD4 and CD8 counts is reminiscent of PML cases in the HIV population and suggests that loss of T cells is the most important risk factor.

  2. Regulated genes in psoriatic skin during treatment with fumaric acid esters.

    Science.gov (United States)

    Onderdijk, A J; Balak, D M W; Baerveldt, E M; Florencia, E F; Kant, M; Laman, J D; van IJcken, W F J; Racz, E; de Ridder, D; Thio, H B; Prens, E P

    2014-10-01

    Fumaric acid esters (FAEs) are widely used in Europe for the treatment of psoriasis because of their clinical efficacy and favourable safety profile. However, the mechanisms of action by which FAEs improve psoriasis remain largely unknown. To identify pathways and mechanisms affected by FAE treatment and to compare these with pathways affected by treatment with the antitumour necrosis factor (anti-TNF)-α biologic etanercept. In a prospective cohort study, 50 patients with plaque psoriasis were treated with FAEs for 20 weeks. Nine patients were randomly selected for gene expression profiling of plaque biopsies from week 0 and week 12. The groups consisted of FAE responders [> Psoriasis Area and Severity Index (PASI)-75 improvement] and nonresponders (psoriasis pathway was most significantly activated. Glutathione and Nrf2 pathway molecules were specifically induced by FAE treatment and not by etanercept treatment, representing an FAE-specific effect in psoriatic skin. In addition, FAE treatment specifically induced the transcription factors PTTG1, NR3C1, GATA3 and NFκBIZ in responding patients. FAE treatment induces glutathione and Nrf2 pathway genes in lesional skin of patients with psoriasis. In responders, FAEs specifically regulate the transcription factors PTTG1, NR3C1, GATA3 and NFκBIZ, which are important in normal cutaneous development, and the T-helper (Th)2 and Th17 pathways, respectively. © 2014 British Association of Dermatologists.

  3. Fumaric acid esters in the treatment of psoriasis: an Italian experience.

    Science.gov (United States)

    Carboni, I; De Felice, C; De Simoni, I; Soda, R; Chimenti, S

    2004-01-01

    Psoriasis is a common, chronic, cell-mediated, inflammatory skin disease. Treatment limitations and a developing understanding of its pathogenesis on a molecular level have encouraged much interest in the field of immunomodulatory therapy. To evaluate the efficacy and safety of fumaric acid esters, in particular dimethylfumarate (DMF), in the treatment of moderate to severe plaque psoriasis intolerant and/or resistant to other conventional systemic therapies. A total of 40 patients were enrolled in this study. DMF was orally administered at the daily dose of 30 mg up to 360 mg for a minimum of 6 months treatment. Patients were followed-up with psoriasis area and severity index (PASI) score assessment, and clinical and photographic documentation. A total of 33 (82.5%) patients achieved complete clinical remission with DMF treatment: eight after 3 months and 25 after 6 months. Adverse events, such as intolerable abdominal cramps and incoercible diarrhoea, occurred in four patients who, for this reason, interrupted therapy. The findings suggest that DMF is a safe, effective and well-tolerated long-term oral treatment worthy of consideration for selective patients.

  4. Treatment of severe, recalcitrant, chronic plaque psoriasis with fumaric acid esters: a prospective study.

    Science.gov (United States)

    Wain, E M; Darling, M I; Pleass, R D; Barker, J N W N; Smith, C H

    2010-02-01

    Fumaric acid esters (FAE) are used in Germany as a first-line systemic treatment for chronic plaque psoriasis, with proven efficacy and low toxicity. Their use in the U.K. is variable, and they remain unlicensed. Consequently, efficacy and safety data from U.K. patients is limited and their place in the psoriasis treatment armamentarium is unclear. To examine the efficacy and safety of FAE in a prospective cohort of U.K. patients with severe, treatment-recalcitrant, chronic plaque psoriasis. A single-centre, open, nonrandomized, prospective study was performed in a regional referral centre for patients with severe psoriasis. Outcomes were measured by the Psoriasis Area and Severity Index (PASI), Dermatology Life Quality Index (DLQI), blood investigations and adverse events monitoring. Eighty patients were recruited. Fifty-nine per cent were taking a concomitant oral antipsoriatic agent; 20% achieved a PASI-50, 8% a PASI-75 and 4% a PASI-90 on intention-to-treat analysis at 3 months with an overall, statistically significant, reduction in PASI from 13.9 + or - 9.0 to 11.3 + or - 9.2 (P psoriasis and can allow dose reduction, and subsequent cessation, of other, potentially more toxic agents.

  5. Combination of ester biosynthesis and ω-oxidation for production of mono-ethyl dicarboxylic acids and di-ethyl esters in a whole-cell biocatalytic setup with Escherichia coli

    NARCIS (Netherlands)

    Nuland, van Youri M.; Eggink, Gerrit; Weusthuis, Ruud A.

    2017-01-01

    Background: Medium chain length (C6-C12) α,ω-dicarboxylic acids (DCAs) and corresponding esters are important building blocks for the polymer industry. For DCAs of 12 carbon atoms and longer, a sustainable process based on monooxygenase catalyzed ω-oxidation of fatty-acids has been realized. For

  6. GALLIUM-MEDIATED ALLYLATION OF CARBONYL COMPOUNDS IN WATER. (R828129)

    Science.gov (United States)

    Ga-mediated allylation of aldehydes or ketones in distilled or tap water generated the corresponding homoallyl alcohols in high yields without the assistance of either acidic media or sonication. Grap...

  7. Vanadium-Catalyzed Enantioselective Desymmetrization of meso-Secondary Allylic Alcohols and Homoallylic Alcohols

    OpenAIRE

    Li, Zhi; Zhang, Wei; Hisashi Yamamoto, H.

    2008-01-01

    Vanadium-catalyzed epoxidation has extended substrate scope. In addition to various bis-allylic alcohols, bis-homoallylic alcohols can also be desymmetrized using our Vanadium-Bis-hydroxamic acid complexes.

  8. Cu(II) /TEMPO-promoted one-pot synthesis of highly substituted pyrimidines from amino acid esters.

    Science.gov (United States)

    Zhou, Nini; Xie, Tao; Li, Zhongle; Xie, Zhixiang

    2014-12-22

    A novel, Cu(OAc)2/TEMPO promoted one-step approach for the preparation of fully substituted pyrimidines from readily available amino acid esters has been described. In this reaction, the amino acid esters act as the only N-C sources for the construction of corresponding pyrimidines. The mechanism of this process includes oxidative dehydrogenation, the generation of an imine radical, and a formal [3+3] cycloaddition. This methodology proves to be a high atom-economic and straightforward strategy for the synthesis of pyrimidines and diverse substrates which are substituted by various functional groups have been afforded in moderate to good yield. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  9. 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

  10. Copper(II) complex formation equilibria involving L-carnosine, the role in the catalysis of amino acid ester hydrolisis

    Energy Technology Data Exchange (ETDEWEB)

    Shoukry, E.M.; Shoukry, M.M.; Mahgoub, A.E.; Galal, H.M. [Cairo Univ., Cairo (Egypt). Faculty of Science

    2000-10-01

    The binary and ternary complexes of copper(II) involving carnosine (H{sub 3}L), amino acids and DNA constituents were examined. Copper(II) was found to form CuL and CuLH{sub 1} complexes with carnosine. The ternary complexes of Copper(II) with carnosine and DNA constituents are formed in a stepwise mechanism, whereby carnosine binds to copper(II), then followed by ligation of the DNA constituents. The concentration distribution of the various complex species has been evaluated. The hydrolysis of amino acid ester is catalysed by the Cu-carnosine complex. The rate enhancement compared with the fee ester hydrolysis is investigated in terms of the ester coordination mode. [Italian] Sono stati considerati i complessi binari e ternari del rame(II) con la carnosina (H{sub 3}L), amino acidi e constituenti del DNA. Si e' trovato che il rame(II) forma complessi CuL e CuLH{sub 1} con la carnosina. I complessi ternari di rame(II) con carnosina e constitutenti del DNA si formano con un meccanismo a stadi, prima la carnosina lega il rame e successivamente sono legati i constituenti del DNA. E' stata valutata la distribuzione della concentrazione delle varie specie complesse. Il complesso Cu-carnosina catalizza l'idrolisi degli esteri di aminoacidi. L'incremento di velocita', rispetto all'idrolisi dell'estere libero, e' stato studiato in termini di modo di coordinazione dell'estere.

  11. Physicochemical and structural properties of glycerin gel prepared using glycyrrhizic acid diethyl ester.

    Science.gov (United States)

    Koga, Kenjiro; Kimura, Toshiyuki; Sakai, Kenichi; Kushida, Hiroshi; Yoshikawa, Nobuji

    2014-01-01

    Glycyrrhizic acid diethyl ester (GZ-DE) was developed as a prodrug of glycyrrhizic acid (GZ), a hepatitis therapeutic drug. We fortuitously found that GZ-DE gels with glycerin selectively while searching for a safe solvent with which to dissolve GZ-DE. Based on this gelation, the aim of this study was to investigate the preparation of the gel and study the rheology, physicochemical and structural properties of the glycerin gel by differential scanning calorimeter (DSC), capillary electrophoresis (CEP), nuclear magnetic resonance (NMR), and small angle X-ray scattering (SAXS). The glycerin gel was prepared by the addition of at least 2.0% w/w GZ-DE. This gel did not flow at room temperature. After mixing glycerin and GZ-DE, a gel was formed after 2 days at 25°C or 3 h at 60°C. Glycerin gel containing 2.4% w/w GZ-DE provided the following results: 1) The glycerin gel exhibited creep at a constant stress of less than 10 Pa, but it is a fragile gel, showing Newtonian flow at 10 Pa stress. 2) Dynamic viscoelastic measurements showed that the elastic modulus (G') exceeds the viscous modulus (G''), indicating that glycerin gel has solid-like properties. 3) DSC showed a significant difference between the glass transition temperature of glycerin and glycerin gel. 4) CEP did not reveal a new compound in the glycerin gel. 5) NMR confirmed that glycerin gel is a physical gel. 6) SAXS measurements revealed that the glycerin gel has an oval-shaped basic frame (119 nm long and 65 nm wide).

  12. Anaerobic degradation of phthalic acid esters during digestion of municipal solid waste under landfilling conditions.

    Science.gov (United States)

    Ejlertsson, J; Meyerson, U; Svensson, B H

    1996-08-01

    Anaerobic microorganisms in municipal solid waste samples from laboratory-scale landfill reactors and a pilot-plant biogas digestor were investigated with the aim of assessing their ability to transform four commercially used phthalic acid esters (PAEs) and phthalic acid (PA). The PAEs studied were diethyl phthalate (DEP), butylbenzyl phthalate (BBP), dibutyl phthalate (DBP) and bis(2-ethylhexyl) phthalate (DEHP). No biological transformation of DEHP could be detected in any of the experiments. Together with waste samples from the simulated landfilling conditions, the PAEs (except DEHP) were hydrolytically transformed to their corresponding monoesters. These accumulated as end products, and in most cases they were not further degraded. During incubation with waste from the biogas digestor, the PAEs (except DEHP) were completely degraded to methane and carbon dioxide. The influence of the landfill development phase on the transformations was investigated utilizing PA and DEP as model substances. We found that during both the intense and stable methanogenic (but not the acidogenic) phases, the microorganisms in the samples had the potential to transform PA. A shorter lag phase was observed for the PA transformation in the samples from the stable methanogenic phase as compared with earlier phases. This indicates an increased capacity to degrade PA during the aging phases of the municipal solid waste in landfills. No enhancement of the DEP transformation could be observed as conditions in the methanogenic landfill model changed over a year's time. The results indicate that microorganisms developing in a methanogenic landfill environment have a substantially lower potential to degrade compared with those developing in a biogas reactor.

  13. 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)

  14. 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.

  15. Acidic 1,3-propanediaminetetraacetato lanthanides with luminescent and catalytic ester hydrolysis properties

    Science.gov (United States)

    Chen, Mao-Long; Shi, Yan-Ru; Yang, Yu-Chen; Zhou, Zhao-Hui

    2014-11-01

    In acidic solution, a serials of water-soluble coordination polymers (CPs) were isolated as zonal 1D-CPs 1,3-propanediaminetetraacetato lanthanides [Ln(1,3-H3pdta)(H2O)5]n·2Cln·3nH2O [Ln=La, 1; Ce, 2; Pr, 3; Nd, 4; Sm, 5] (1,3-H4pdta=1,3-propanediaminetetraacetic acid, C11H18N2O8) in high yields. When 1 eq. mol potassium hydroxide was added to the solutions of 1D-CPs, respectively, two 1D-CPs [Ln(1,3-H2pdta)(H2O)3]n·Cln·2nH2O [Ln=Sm, 6; Gd, 7] were isolated at room temperature and seven 2D-CPs [Ln(1,3-H2pdta)(H2O)2]n·Cln·2nH2O [Ln=La, 8; Ce, 9; Pr, 10; Nd, 11; Sm, 12; Eu, 13; Gd, 14] were isolated at 70 °C. When the crystals of 1-4 were hydrothermally heated at 180 °C with 1-2 eq. mol potassium hydroxide, four 3D-CPs [Ln(1,3-Hpdta)]n·nH2O [Ln=La, 15; Ce, 16; Pr, 17; Nd, 18] were obtained. The two 2D-CPs [Ln(1,3-Hpdta)(H2O)]n·4nH2O (Sm, 19; Eu, 20) were isolated in similar reaction conditions. With the increments of pH value in the solution and reaction temperature, the structure becomes more complicated. 1-5 are soluble in water and 1 was traced by solution 13C{1H} NMR technique, the water-soluble lanthanides 1 and 5 show catalytic activity to ester hydrolysis reaction respectively, which indicate their important roles in the hydrolytic reaction. The europium complexes 13 and 20 show visible fluorescence at an excitation of 394 nm. The structure diversity is mainly caused by the variation of coordinated ligand in different pH values and lanthanide contraction effect. Acidic conditions are favorable for the isolations of lanthanide complexes in different structures and this may helpful to separate different lanthanides. The thermal stability investigations reveal that acidic condition is favorable to obtain the oxides at a lower temperature.

  16. The preparation of poly(γ-glutamic acid)-NHS ester as a natural cross-linking agent of collagen.

    Science.gov (United States)

    Yang, Junhui; Ding, Cuicui; Huang, Liulian; Zhang, Min; Chen, Lihui

    2017-04-01

    γ-PGA-NHS ester, which was prepared using poly(γ-glutamic acid) (γ-PGA) and N-hydroxysuccinimide (NHS) as the raw materials, was synthesized to be a novel cross-linker of collagen. Fourier transform infrared spectra analysis suggested that the products displayed the characteristic absorption peak of ester. Results from nuclear magnetic resonance analysis indicated that the esterification degree of γ-PGA-NHS ester was increased with the increase of NHS. Modified collagen was prepared and characterized. The results of circular dichroism analysis indicated modified collagen retained the triple helix structure of natural collagen. Sodium dodecyl sulphate polyacrylamide gel electrophoresis revealed that the molecular weight of collagen was increased after cross-linking. Peptide mapping of collagen suggested that cross-linked collagen possessed an enhanced resistance to trypsin degradation. Differential scanning calorimeter results showed that the denaturation temperature of collagen was improved from 68.1±0.4 to 91.2±0.5°C (pcross-linked collagen retained porous structure and the pore size became larger as observed by scanning electron microscopy. The investigation results provided useful information to produce collagen with improved physicochemical properties, particularly the thermal stability via the use of γ-PGA-NHS ester as a biomacromolecule-based cross-linker. Copyright © 2016 Elsevier B.V. All rights reserved.

  17. Accumulation of short n-chain ethyl esters by esterases of lactic acid bacteria under conditions simulating ripening Parmesan cheese.

    Science.gov (United States)

    Fenster, K M; Rankin, S A; Steele, J L

    2003-09-01

    EstA from Lactobacillus helveticus CNRZ32 (Lbh-EstA), EstB, and EstC from Lactobacillus casei LILA, and EstA from Lactococcus lactis MG1363 (Lcl-EstA) were evaluated for their ability to accumulate esters in a model system simulating Parmesan cheese ripening conditions (10 degrees C, 2 to 3% NaCl, pH 5.4 to 5.5, aw = 0.850 to 0.925) using Capalase K from kid goat as a positive control. All of the LAB esterases and Capalase K mediated the accumulation of esters in the model system in an enzyme specific manner, which was influenced by a, and selectivity for fatty acid chain-length. In general, enzyme mediated accumulation of ethyl esters was higher at aw values of 0.850 and 0.900 than at aw of 0.925, demonstrating that aw is a critical parameter influencing ester accumulation. The substrate selectivity of esterases, aw, and enzyme type may be important factors in the development of fruity flavors, as evidenced by results in this model system simulating Parmesan cheese ripening conditions.

  18. 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.

  19. SYNTHESIS AND CHARACTERIZATION OF CELLULOSE STEARATE ESTER FROM BACTERIAL CELLULOSE AND STEARIC ACID ENZYMATICALLY USING IMMOBILIZED LIPASE

    Directory of Open Access Journals (Sweden)

    Suci Amaliyah

    2016-11-01

    Full Text Available The aims of this study were to determine the optimum conditions of enzymatic esterification between stearic acid with bacterial cellulose using immobilized lipase and to characterize the obtained ester. The optimum condition was observed by the effects of time and mass ratio of cellulose: stearic acid towards degree of esterification. The esterification reaction carried out in a heterogeneous system using n-butanol as solvent at 50 °C. The effect of reaction time on esterification degree is done by variating incubation time for 6, 12, 18, 24 and 30 hours. The influence of the mass ratio of cellulose: stearic acid to the esterification degree was carried out by variating 1: 1, 1: 2, 1: 3, 1: 4, 1: 5 and 1: 6. Products characterization consist of functional group analysis by Fourier Transform Infra Red (FTIR, determining degree of substitution (DS by saponification, swelling index by gravimetric method, and cristallinity by X-Ray Diffraction (XRD. The results showed that condition of esterification was optimum in 18 hours of reaction with mass ratio 1:5. The success of esterification was confirmed by FTIR spectrum that showed ester carbonyl peak at 1718.46 cm-1 . DS of  cellulose stearate ester was 0.35. The swelling and crystallinity index of cellulose stearate was smaller than bacterial cellulose.

  20. 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

    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......, 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

  1. Rapid synthesis of long chain fatty acid esters of steroids in ionic liquids with microwave irradiation: expedient one-pot procedure for estradiol monoesters.

    Science.gov (United States)

    Deb, Somdatta; Wähälä, Kristiina

    2010-10-01

    We report the rapid synthesis (1min) in high yield of fatty acid ester (FAE) derivatives of several steroids under microwave irradiation in an ionic liquid (IL). An expedient regioselective hydrolysis at C-3 of estradiol diesters is also reported.

  2. A Convenient Asymmetric Synthesis of a β-amino Ester with Additional Functionalization as a Precursor for Peptide Nucleic Acid (PNA Monomers

    Directory of Open Access Journals (Sweden)

    Julio G. Urones

    2006-06-01

    Full Text Available We report the asymmetric synthesis of di-3-pentyl (3S,αS,7E-3-N-benzyl-N- α-methylbenzylamino-dec-7-enedioate (9, which contains the correct functionalization to produce δ-amino acid derivatives to be used as monomers for Peptide Nucleic Acid (PNA formation With this aim, thymine-pentanoic acid 15 and some of its ester derivatives were obtained, their reactivity was studied and the noteworthy ethyl ester 12 was quantitatively produced by transesterification of methyl ester 11, thus paving the way for the synthesis of the thymine-containing amino ester IV, which has been designed as a building block for a Nucleic-Acid analog with a chiral, flexible peptide backbone

  3. Combination of ester biosynthesis and ω-oxidation for production of mono-ethyl dicarboxylic acids and di-ethyl esters in a whole-cell biocatalytic setup with Escherichia coli.

    Science.gov (United States)

    van Nuland, Youri M; Eggink, Gerrit; Weusthuis, Ruud A

    2017-11-02

    Medium chain length (C6-C12) α,ω-dicarboxylic acids (DCAs) and corresponding esters are important building blocks for the polymer industry. For DCAs of 12 carbon atoms and longer, a sustainable process based on monooxygenase catalyzed ω-oxidation of fatty-acids has been realized. For medium-chain DCAs with a shorter chain length however, such a process has not been developed yet, since monooxygenases poorly ω-oxidize medium-chain fatty acids (MCFAs). On the contrary, esterified MCFAs are ω-oxidized well by the AlkBGTHJ proteins from Pseudomonas putida GPo1. We show that MCFAs can be efficiently esterified and subsequently ω-oxidized in vivo. We combined ethyl ester synthesis and ω-oxidation in one-pot, whole-cell biocatalysis in Escherichia coli. Ethyl ester production was achieved by applying acyl-CoA ligase AlkK and an alcohol acyltransferase, either AtfA or Eeb1. E. coli expressing these proteins in combination with the ω-oxidation pathway consisting of AlkBGTHJ, produced mono-ethyl DCAs directly from C6, C8 and C9 fatty acids. The highest molar yield was 0.75, for mono-ethyl azelate production from nonanoic acid. Furthermore, di-ethyl esters were produced. Diethyl suberate was produced most among the di-ethyl esters, with a molar yield of 0.24 from octanoic acid. The results indicate that esterification of MCFAs and subsequent ω-oxidation to mono-ethyl DCAs via whole-cell biocatalysis is possible. This process could be the first step towards sustainable production of medium-chain DCAs and medium-chain di-ethyl esters.

  4. Toward Peptide Nucleic Acid (PNA) Directed Peptide Translation Using Ester Based Aminoacyl Transfer

    DEFF Research Database (Denmark)

    Singhal, Abhishek; Bagnacani, Valentina; Corradini, Roberto

    2014-01-01

    intermolecular aminoacyl transfer using simple ester aminolysis chemistry primitively analogous to the ribosomal peptidyl transferase reaction in the absence of anchimeric assistance from ribose and ribosome catalysis. These results help define the minimum chemical boundary conditions for the translation process...

  5. Simultaneous Disulfide and Boronic Acid Ester Exchange in Dynamic Combinatorial Libraries

    DEFF Research Database (Denmark)

    Diemer, Sanna L.; Kristensen, Morten; Rasmussen, Brian

    2015-01-01

    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...

  6. Return of the lysergamides. Part II: Analytical and behavioural characterization of N(6) -allyl-6-norlysergic acid diethylamide (AL-LAD) and (2'S,4'S)-lysergic acid 2,4-dimethylazetidide (LSZ).

    Science.gov (United States)

    Brandt, Simon D; Kavanagh, Pierce V; Westphal, Folker; Elliott, Simon P; Wallach, Jason; Colestock, Tristan; Burrow, Timothy E; Chapman, Stephen J; Stratford, Alexander; Nichols, David E; Halberstadt, Adam L

    2017-01-01

    Lysergic acid N,N-diethylamide (LSD) is perhaps one of the most intriguing psychoactive substances known and numerous analogs have been explored to varying extents in previous decades. In 2013, N(6) -allyl-6-norlysergic acid diethylamide (AL-LAD) and (2'S,4'S)-lysergic acid 2,4-dimethylazetidide (LSZ) appeared on the 'research chemicals'/new psychoactive substances (NPS) market in both powdered and blotter form. This study reports the analytical characterization of powdered AL-LAD and LSZ tartrate samples and their semi-quantitative determination on blotter paper. Included in this study was the use of nuclear magnetic resonance (NMR) spectroscopy, gas chromatography-mass spectrometry (GC-MS), low and high mass accuracy electrospray MS(/MS), high performance liquid chromatography diode array detection and GC solid-state infrared analysis. One feature shared by serotonergic psychedelics, such as LSD, is the ability to mediate behavioural responses via activation of 5-HT2A receptors. Both AL-LAD and LSZ displayed LSD-like responses in male C57BL/6 J mice when employing the head-twitch response (HTR) assay. AL-LAD and LSZ produced nearly identical inverted-U-shaped dose-dependent effects, with the maximal responses occurring at 200 µg/kg. Analysis of the dose responses by nonlinear regression confirmed that LSZ (ED50  = 114.2 nmol/kg) was equipotent to LSD (ED50  = 132.8 nmol/kg) in mice, whereas AL-LAD was slightly less potent (ED50  = 174.9 nmol/kg). The extent to which a comparison in potency can be translated directly to humans requires further investigation. Chemical and pharmacological data obtained from NPS may assist research communities that are interested in various aspects related to substance use and forensic identification. Copyright © 2016 John Wiley & Sons, Ltd. Copyright © 2016 John Wiley & Sons, Ltd.

  7. Photodynamic inactivation of Klebsiella pneumoniae biofilms and planktonic cells by 5-aminolevulinic acid and 5-aminolevulinic acid methyl ester.

    Science.gov (United States)

    Liu, Chengcheng; Zhou, Yingli; Wang, Li; Han, Lei; Lei, Jin'e; Ishaq, Hafiz Muhammad; Nair, Sean P; Xu, Jiru

    2016-04-01

    The treatment of Klebsiella pneumoniae, particularly extended-spectrum β-lactamase (ESBL)-producing K. pneumoniae, is currently a great challenge. Photodynamic antimicrobial chemotherapy is a promising approach for killing antibiotic-resistant bacteria. The aim of this study was to evaluate the capacity of 5-aminolevulinic acid (5-ALA) and its derivative 5-ALA methyl ester (MAL) in the presence of white light to cause photodynamic inactivation (PDI) of K. pneumoniae planktonic and biofilm cells. In the presence of white light, 5-ALA and MAL inactivated planktonic cells in a concentration-dependent manner. Biofilms were also sensitive to 5-ALA and MAL-mediated PDI. The mechanisms by which 5-ALA and MAL caused PDI of ESBL-producing K. pneumonia were also investigated. Exposure of K. pneumonia to light in the presence of either 5-ALA or MAL induced cleavage of genomic DNA and the rapid release of intracellular biopolymers. Intensely denatured cytoplasmic contents and aggregated ribosomes were also detected by transmission electron microscopy. Scanning electron microscopy showed that PDI of biofilms caused aggregated bacteria to detach and that the bacterial cell envelope was damaged. This study provides insights into 5-ALA and MAL-mediated PDI of ESBL-producing K. pneumoniae.

  8. 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.

  9. Enantioselective Iridium Catalyzed Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level via Transfer Hydrogenative Coupling of Allyl Acetate: Departure from Chirally Modified Allyl Metal Reagents in Carbonyl Addition

    Science.gov (United States)

    Kim, In Su; Ngai, Ming-Yu; Krische, Michael J.

    2010-01-01

    Under the conditions of transfer hydrogenation employing an iridium catalyst generated in situ from [Ir(cod)Cl]2, the chiral phosphine ligands (R)-BINAP or (R)-Cl,MeO-BIPHEP and m-nitrobenzoic acid, allyl acetate couples to allylic alcohols 1a-1c, aliphatic alcohols 1d-1l and benzylic alcohols 1m-1u to furnish products of carbonyl allylation 3a-3u with exceptional levels of asymmetric induction. The very same set of optically enriched carbonyl allylation products 3a-3u are accessible from enals 2a-2c, aliphatic aldehydes 2d-2l and aryl aldehydes 2m-2u, using iridium catalysts ligated by (-)-TMBTP or (R)-Cl,MeO-BIPHEP under identical conditions, but employing isopropanol as a hydrogen donor. As corroborated by single crystal X-ray diffraction, the active catalyst is the cyclometallated complex V, which arises upon ortho-C-H insertion of iridium onto m-nitrobenzoic acid. The results of isotopic labeling are consistent with intervention of symmetric iridium π-allylationl intermediates or rapid interconversion of σ-allyl haptomers through the agency of a symmetric π-allyl. Competition experiments demonstrate rapid and reversible hydrogenation-dehydrogenation of the carbonyl partner in advance of C-C coupling. The coupling products, which are homoallylic alcohols, experience very little erosion of optical purity by way of redox equilibration under the coupling conditions, although isopropanol, a secondary alcohol, may serve as terminal reductant. A plausible catalytic mechanism accounting for these observations is proposed, along with a stereochemical model that accounts for the observed sense of absolute stereoinduction. This protocol for asymmetric carbonyl allylation transcends the barriers imposed by oxidation level and the use of preformed allyl-metal reagents. PMID:18841896

  10. Phthalic acid esters in soils from vegetable greenhouses in Shandong Peninsula, East China.

    Science.gov (United States)

    Chai, Chao; Cheng, Hongzhen; Ge, Wei; Ma, Dong; Shi, Yanxi

    2014-01-01

    Soils at depths of 0 cm to 10 cm, 10 cm to 20 cm, and 20 cm to 40 cm from 37 vegetable greenhouses in Shandong Peninsula, East China, were collected, and 16 phthalic acid esters (PAEs) were detected using gas chromatography-mass spectrometry (GC-MS). All 16 PAEs could be detected in soils from vegetable greenhouses. The total of 16 PAEs (Σ16PAEs) ranged from 1.939 mg/kg to 35.442 mg/kg, with an average of 6.748 mg/kg. Among four areas, including Qingdao, Weihai, Weifang, and Yantai, the average and maximum concentrations of Σ16PAEs in soils at depths of 0 cm to 10 cm appeared in Weifang, which has a long history of vegetable production and is famous for extensive greenhouse cultivation. Despite the different concentrations of Σ16PAEs, the PAE compositions were comparable. Among the 16 PAEs, di(2-ethylhexyl) phthalate (DEHP), di-n-octyl phthalate (DnOP), di-n-butyl phthalate (DnBP), and diisobutyl phthalate (DiBP) were the most abundant. Compared with the results on agricultural soils in China, soils that are being used or were used for vegetable greenhouses had higher PAE concentrations. Among PAEs, dimethyl phthalate (DMP), diethyl phthalate (DEP) and DnBP exceeded soil allowable concentrations (in US) in more than 90% of the samples, and DnOP in more than 20%. Shandong Peninsula has the highest PAE contents, which suggests that this area is severely contaminated by PAEs.

  11. Labdanolic acid methyl ester (LAME) exerts anti-inflammatory effects through inhibition of TAK-1 activation.

    Science.gov (United States)

    Cuadrado, Irene; Cidre, Florencia; Herranz, Sandra; Estevez-Braun, Ana; de las Heras, Beatriz; Hortelano, Sonsoles

    2012-01-01

    Labdane derivatives obtained from the diterpenoid labdanediol suppressed NO and PGE(2) production in LPS-stimulated RAW 264.7 macrophages. However, mechanisms involved in these inhibitory effects are not elucidated. In this study, we investigated the signaling pathways involved in the anti-inflammatory effects of labdanolic acid methyl ester (LAME) in peritoneal macrophages and examined its therapeutic effect in a mouse endotoxic shock model. LAME reduced the production of NO and PGE(2) in LPS-activated macrophages. This effect involved the inhibition of NOS-2 and COX-2 gene expression, acting at the transcription level. Examination of the effects of the diterpene on NF-κB signaling showed that LAME inhibits the phosphorylation of IκBα and IκBβ, preventing their degradation and the nuclear translocation of the NF-κB p65 subunit. Moreover, inhibition of MAPK signaling was also observed. A further experiment revealed that LAME inhibited the phosphorylation of transforming growth factor-β (TGF-β)-activated kinase 1 (TAK1), an upstream signaling molecule required for IKK and mitogen-activated protein kinases (MAPKs) activation. Inflammatory cytokines such as IL-6, TNF-α and IP-10 were downregulated in the presence of this compound after stimulation with LPS. Additionally, LAME also improved survival in a mouse model of endotoxemia and reduced the circulatory levels of cytokines (IL-6, TNF-α). In conclusion, these results indicate that labdane diterpene LAME significantly attenuates the pro-inflammatory response induced by LPS both in vivo and in vitro. Copyright © 2011 Elsevier Inc. All rights reserved.

  12. Caffeic Acid Phenethyl Ester Protects against Amphotericin B Induced Nephrotoxicity in Rat Model

    Science.gov (United States)

    Altuntaş, Atila; Yılmaz, H. Ramazan; Altuntaş, Ayşegül; Uz, Efkan; Demir, Murat; Gökçimen, Alparslan; Aksu, Oğuzhan; Bayram, Dilek Şenol; Sezer, Mehmet Tuğrul

    2014-01-01

    The present study was conducted to investigate whether caffeic acid phenethyl ester (CAPE), an active component of propolis extract, has a protective effect on amphotericin B induced nephrotoxicity in rat models. Male Wistar-Albino rats were randomly divided into four groups: (I) control group (n = 10), (II) CAPE group (n = 9) which received 10 μmol/kg CAPE intraperitoneally (i.p.), (III) amphotericin B group (n = 7) which received one dose of 50 mg/kg amphotericin B, and (IV) amphotericin B plus CAPE group (n = 7) which received 10 μmol/kg CAPE i.p. and one dose of 50 mg/kg amphotericin B. The left kidney was evaluated histopathologically for nephrotoxicity. Levels of malondialdehyde (MDA), nitric oxide (NO), enzyme activities including catalase (CAT), and superoxide dismutase (SOD) were measured in the right kidney. Histopathological damage was prominent in the amphotericin B group compared to controls, and the severity of damage was lowered by CAPE administration. The activity of SOD, MDA, and NO levels increased and catalase activity decreased in the amphotericin B group compared to the control group (P = 0.0001, P = 0.003, P = 0.0001, and P = 0.0001, resp.). Amphotericin B plus CAPE treatment caused a significant decrease in MDA, NO levels, and SOD activity (P = 0.04, P = 0.02, and P = 0.0001, resp.) and caused an increase in CAT activity compared with amphotericin B treatment alone (P = 0.005). CAPE treatment seems to be an effective adjuvant agent for the prevention of amphotericin B nephrotoxicity in rat models. PMID:25032223

  13. Effect of icosapent ethyl (eicosapentaenoic acid ethyl ester) on omeprazole plasma pharmacokinetics in healthy adults.

    Science.gov (United States)

    Braeckman, Rene A; Stirtan, William G; Soni, Paresh N

    2014-09-01

    Icosapent ethyl (IPE) is a high-purity prescription form of eicosapentaenoic acid ethyl ester approved by the US Food and Drug Administration as an adjunct to diet to reduce triglyceride levels in adult patients with severe hypertriglyceridemia. Patients with high serum triglycerides may be taking concurrent medications for associated conditions such as obesity and/or diabetes mellitus. To evaluate the effect of IPE on the plasma pharmacokinetics (PK) of omeprazole, a commonly used proton pump inhibitor and a substrate of cytochrome P450 (CYP) 2C19. Omeprazole (40 mg/day for 7 days) was administered orally without and with 4 g/day IPE at steady state. The primary PK endpoint was area under the concentration-time curve from time 0 to 24 h (AUC0-24); secondary endpoints included maximum observed plasma concentration (C max). Safety was monitored in all subjects who received one or more dose(s) of the study drug. Thirty healthy adult subjects were enrolled and 28 completed the study. IPE 4 g/day at steady state did not significantly change the AUC0-24 or C max of omeprazole when co-administered at 40 mg/day to steady state. The ratios of least squares geometric means (90 % confidence interval) for AUC0-24 and C max (omeprazole with IPE vs. omeprazole alone) were 0.84 (76.0-91.9) and 1.01 (87.4-116.3), respectively. There were no clinically significant findings from laboratory tests, vital signs, or physical examinations. At steady-state concentrations, IPE 4 g/day did not inhibit the AUC0-24 or C max of omeprazole 40 mg/day, a CYP2C19 substrate. Co-administration of IPE with omeprazole was safe and well tolerated.

  14. Placental Fatty Acid ethyl esters are elevated with maternal alcohol use in pregnancies complicated by prematurity.

    Directory of Open Access Journals (Sweden)

    Theresa W Gauthier

    Full Text Available The accumulation of fatty acid ethyl esters (FAEEs in meconium of term newborns has been described as one potential biomarker of maternal alcohol use during pregnancy. FAEEs accumulate in multiple alcohol-exposed fetal tissues and in the placenta. Limited research has focused on the identification of the premature newborn exposed to alcohol in utero. We hypothesized that maternal alcohol use occurs in a significant proportion of premature deliveries and that this exposure can be detected as elevated placental FAEEs. The goals of this study were to 1 determine the prevalence of maternal alcohol use in the premature newborn and 2 investigate whether placental FAEEs could identify those newborns with fetal alcohol exposure. This prospective observational study evaluated 80 placentas from 80 women after premature delivery. Subjects were interviewed for alcohol intake and placental FAEEs were quantified via GC/MS. Receiver Operator Characteristic (ROC Curves were generated to evaluate the ability of placental FAEEs to predict maternal drinking during pregnancy. Adjusted ROC curves were generated to adjust for gestational age, maternal smoking, and illicit drug use. 30% of the subjects admitted to drinking alcohol during pregnancy and approximately 14% answered questions indicative of problem drinking (designated AUDIT+. The specific FAEEs ethyl stearate and linoleate, as well as combinations of oleate + linoleate + linolenate (OLL and of OLL + stearate, were significantly (p<0.05 elevated in placentas from AUDIT+ pregnancies. Adjusted ROC Curves generated areas under the curve ranging from 88-93% with negative predictive values of 97% for AUDIT+ pregnancies. We conclude that nearly one third of premature pregnancies were alcohol-exposed, and that elevated placental FAEEs hold great promise to accurately determine maternal alcohol use, particularly heavy use, in pregnancies complicated by premature delivery.

  15. The protective effects of caffeic acid phenethyl ester against toluene-induced nephrotoxicity in rats.

    Science.gov (United States)

    Meydan, Sedat; Nacar, Ahmet; Oztürk, Hasan Oktay; Tas, Ufuk; Köse, Evren; Zararsiz, Ismail; Yılmaz, Nigar; Kus, Ilter

    2016-01-01

    Caffeic acid phenethyl ester (CAPE) has antioxidant and anti-inflammatory properties. The aim of this study is to examine the negative effects of toluene on kidney tissues and functions and to investigate the protective effects of CAPE against toluene-induced nephrotoxicity in rats. A total of 21 male Wistar rats were divided into three groups of equal number in each. The rats in group I were the controls. Toluene was intraperitoneally injected into the rats in group II with a dose of 500 mg/kg. Rats in group III received CAPE daily while exposed to toluene. After 14 days of experimental period, all rats were killed by decapitation. Enzymatic activities of superoxide dismutase (SOD), glutathione peroxidase (GSH-Px), and catalase (CAT) and malondialdehyde (MDA) levels were studied in the rat kidneys. Blood urea nitrogen (BUN) and serum creatinine levels were measured for renal function. The CAT and SOD enzyme activities and serum creatinine levels were significantly increased in rats treated with toluene when compared with the controls. But GSH-Px activity, MDA, and BUN levels showed statistically nonsignificant changes. However, increased CAT and SOD enzyme activities and decreased serum creatinine levels were detected in the rats that received CAPE while exposed to toluene. The GSH-Px activity and MDA and BUN levels in the same group did not show statistically significant changes. The results of our study demonstrated that toluene damages kidney tissue and is a nephrotoxic substance. CAPE was able to prevent the renal damage as antioxidant, antitoxic, and nephroprotective agent. © The Author(s) 2013.

  16. Mechanisms of Oxidative Damage in Multiple Sclerosis and Neurodegenerative Diseases: Therapeutic Modulation via Fumaric Acid Esters

    Directory of Open Access Journals (Sweden)

    Ralf Gold

    2012-09-01

    Full Text Available Oxidative stress plays a crucial role in many neurodegenerative conditions such as Alzheimer’s disease, amyotrophic lateral sclerosis and Parkinson’s as well as Huntington’s disease. Inflammation and oxidative stress are also thought to promote tissue damage in multiple sclerosis (MS. Recent data point at an important role of anti-oxidative pathways for tissue protection in chronic-progressive MS, particularly involving the transcription factor nuclear factor (erythroid-derived 2-related factor 2 (Nrf2. Thus, novel therapeutics enhancing cellular resistance to free radicals could prove useful for MS treatment. Here, fumaric acid esters (FAE are a new, orally available treatment option which had already been tested in phase II/III MS trials demonstrating beneficial effects on relapse rates and magnetic resonance imaging markers. In vitro, application of dimethylfumarate (DMF leads to stabilization of Nrf2, activation of Nrf2-dependent transcriptional activity and abundant synthesis of detoxifying proteins. Furthermore, application of FAE involves direct modification of the inhibitor of Nrf2, Kelch-like ECH-associated protein 1. On cellular levels, the application of FAE enhances neuronal survival and protects astrocytes against oxidative stress. Increased levels of Nrf2 are detected in the central nervous system of DMF treated mice suffering from experimental autoimmune encephalomyelitis (EAE, an animal model of MS. In EAE, DMF ameliorates the disease course and improves preservation of myelin, axons and neurons. Finally, Nrf2 is also up-regulated in the spinal cord of autopsy specimens from untreated patients with MS, probably as part of a naturally occurring anti-oxidative response. In summary, oxidative stress and anti-oxidative pathways are important players in MS pathophysiology and constitute a promising target for future MS therapies like FAE.

  17. 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 (Psqualane in-water emulsion and investigated. In contrast to CFASE, CMS adjuvant did not generate rise in body temperature or local reactions in rabbits immunized with a purified, recombinant malaria chimeric antigen R0.10C. In comparison to alum, CMS adjuvant revealed approximately 30-fold higher antibody titres after the first and >100-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.

  18. Progressive multifocal leukoencephalopathy associated with fumaric acid esters treatment in psoriasis patients.

    Science.gov (United States)

    Balak, D M W; Hajdarbegovic, E; Bramer, W M; Neumann, H A M; Thio, H B

    2017-09-01

    Fumaric acid esters (FAEs) are a systemic treatment for psoriasis considered to have a favourable long-term safety profile without an increased risk for immunosuppression. However, progressive multifocal leukoencephalopathy (PML), a rare, opportunistic viral infection of the central nervous system, has been linked anecdotally to FAE treatment. To assess clinical features and outcomes of FAE-associated PML cases. Systematic literature search in multiple databases up to 25th February 2016 for reports of PML in psoriasis patients treated with FAEs. Eight cases (four male, four female) of FAE-associated PML were identified. Median age was 64 years (range 42-74 years); median FAE treatment duration was 3 years (range 1.5-5 years). Six patients were treated with a formulation containing dimethyl fumarate (DMF) and monoethyl fumarates, and two patients with a DMF formulation. Patients exhibited neurological symptoms, such as aphasia, hemiparesis and dysarthria. PML diagnosis was based on MRI findings and presence of JC virus in cerebrospinal fluid and/or brain tissue. All cases were linked to moderate-to-severe reductions in absolute lymphocyte counts, with nadirs ranging from 200 to 792 cells per mm3 . Median exposure to lymphocytopenia was 2 years (range 1-5 years). In all cases, FAE treatment was discontinued; PML was treated with mefloquine plus mirtazapine. Three patients improved, two had stable disease, two had residual symptoms, and one patient died to an immune reconstitution inflammatory syndrome. Progressive multifocal leukoencephalopathy is infrequently linked to FAE treatment, but underreporting cannot be excluded. Physicians treating patients with FAEs should be vigilant for the occurrence of PML, and both clinicians and patients should be alert for onset of new neurological symptoms. Periodic monitoring of lymphocyte counts and FAE discontinuation in case of moderate-to-severe lymphocytopenia is recommended to minimize the risk for PML. © 2017 European

  19. Fumaric acid esters for severe psoriasis: a retrospective review of 58 cases.

    Science.gov (United States)

    Harries, M J; Chalmers, R J G; Griffiths, C E M

    2005-09-01

    Fumaric acid esters (FAE) have been used to treat severe psoriasis in northern Europe for over 20 years. A recent systematic review has shown FAE to be an effective systemic treatment for severe psoriasis. However, FAE remain unlicensed in the U.K. To present data relating to the efficacy and tolerability of FAE in severe psoriasis and report our experiences of FAE therapy at one U.K. centre. Patients who had received FAE for severe psoriasis at one U.K. regional referral centre between June 1999 and October 2003 were identified from pharmacy records. Their records were analysed retrospectively. Fifty-eight patients (25 women, 33 men) were identified. Fifty-five (95%) of the 58 patients had previously used other systemic antipsoriatic therapies with over 70% previously using two or more agents. Thirty-two patients (55%) showed improvement in their psoriasis with 10 (17%) being rated as 'clear' or 'virtually clear' by the attending physician. No improvement was seen in 28% patients and 16% showed worsening of their disease. Adverse events were common and were reported in 66% patients. These mainly consisted of abdominal pain (61%), diarrhoea (55%), flushing (45%), nausea (21%) and malaise (15%). They led to discontinuation of treatment in 15 patients after a mean period of 4.7 months. Lymphocytopenia developed during treatment in 57% of patients, all of whom had had a baseline value within the normal range. In only one patient was this considered severe enough to warrant withdrawal of treatment. Our study has shown that FAE are an effective therapy in selected patients with severe psoriasis, even in those who have previously been intolerant of systemic therapy or where it has failed.

  20. Fumaric acid esters in recalcitrant pediatric psoriasis: A prospective, daily clinical practice case series.

    Science.gov (United States)

    van Geel, M J; van de Kerkhof, P C M; Oostveen, A M; de Jong, E M G J; Seyger, M M B

    2016-01-01

    Evidence on fumaric acid esters (FAE) in the treatment of pediatric psoriasis is scarce. Describe the effectiveness, influence on the quality of life (QoL) and safety of FAE in children with recalcitrant psoriasis in daily clinical practice. A prospective case series. Fourteen patients with recalcitrant plaque-type psoriasis were described (mean age 13.7, range 8-17 years). Mean treatment duration was 48.6 weeks (range 12-124). Maximum daily dose varied between 180 and 1200 mg with a mean of 564 mg per day. Mean Psoriasis Area and Severity Index (PASI) (±SEM) at baseline was 10.5 (1.0) compared to 8.6 (1.1), 6.2 (1.6) and 4.9 (1.5) at week 12, 24 and 36, respectively. An improvement in PASI was observed in nine patients (64.3%). Mean CDLQI (±SEM) at week 0, 12, 24 and 36 was 8.9 (1.4), 6.8 (1.2), 3.7 (1.4) and 3.1 (2.0), respectively. Most common adverse events (AEs) were gastrointestinal complaints (n = 13, 92.9%) and flushes (n = 10, 71.4%). Lymphocytopenia (n = 5, 45.5%) and eosinophilia (n = 4, 36.4%) were frequently observed laboratory abnormalities. AEs were usually mild and transient. One serious adverse event, unrelated to FAE, was reported. FAE showed improvement of disease severity and QoL in the majority of children. Side-effects occurred frequently, but were usually mild and transient. FAE may be an alternative systemic treatment option for pediatric psoriasis, provided that also the long-term safety data are closely monitored, in particular lymphocytopenia.

  1. Fumaric acid esters in severe psoriasis, including experience of use in combination with other systemic modalities.

    Science.gov (United States)

    Balasubramaniam, P; Stevenson, O; Berth-Jones, J

    2004-04-01

    Fumaric acid esters (FAE) are used as a systemic treatment for severe psoriasis in Germany but there has been only very little published experience from the U.K. The potential for use in combination with other systemic drugs has not been explored. To present data relating to the efficacy of FAE in severe psoriasis and to examine the potential dose-sparing effect and safety issues when FAE are combined with other systemic agents. We retrospectively analysed the records of patients who had received FAE for severe psoriasis either alone (in two cases) or along with other systemic medications (in 10 cases). We reviewed the efficacy of FAE and assessed whether dose reductions were achieved for other systemic drugs. Patients were monitored carefully for possible adverse effects. Of 12 patients treated with FAE one discontinued the drug very early, due to flushing, while on a very low dose. The other 11 patients all demonstrated an improvement in psoriasis after starting FAE. Nine patients received FAE in combination with other systemic therapies including ciclosporin, acitretin, hydroxyurea and methotrexate. Seven achieved useful overall reductions in the dose of the other drugs. In two patients severe psoriasis was controlled using FAE alone. The side-effect profile of FAE was similar to that previously reported. There was no evidence of drug interactions. FAE appear effective and less toxic than other systemic treatments for psoriasis. FAE were used successfully in combination with other systemic agents and generally enabled the doses of the more hazardous drugs to be reduced. Extremely careful monitoring is required when using FAE in such combined regimens as experience is currently very limited.

  2. The Hypoxia Mimetic Protocatechuic Acid Ethyl Ester Inhibits Synaptic Signaling and Plasticity in the Rat Hippocampus.

    Science.gov (United States)

    Lanigan, Sinead M; O'Connor, John J

    2018-01-15

    During hypoxia a number of physiological changes occur within neurons including the stabilization of hypoxia-inducible factors (HIFs). The activity of these proteins is regulated by O 2 , Fe 2+ , 2-OG and ascorbate-dependant hydroxylases which contain prolyl-4-hydroxylase domains (PHDs). PHD inhibitors have been widely used and have been shown to have a preconditioning and protective effect against a later and more severe hypoxic insult. In this study we have investigated the neuroprotective effects of the PHD inhibitor, protocatechuic acid ethyl ester (ethyl 3,4, dihydroxybenzoate: EDHB), as well as its effects on synaptic transmission and plasticity in the rat hippocampus using electrophysiological techniques. We report for the first time, an acute concentration-dependent and reversible inhibitory effect of EDHB (10-100 μM) on synaptic transmission in the dentate gyrus but not Cornu Ammonis 1 (CA1) region which does not affect cell viability. This effect was attenuated through the application of the NMDA or GABA A receptor antagonists, AP-5 and picrotoxin in the dentate gyrus. There were no changes in the ratio of paired responses after EDHB application suggesting a post-synaptic mechanism of action. EDHB (100 μM), was found to inhibit synaptic plasticity in both the dentate gyrus and CA1 regions. Application of exogenous Fe 2+ (100 μM) or digoxin (100 nM) did not reverse EDHB's inhibitory effect on synaptic transmission or plasticity in both regions, suggesting that its effects may be HIF-independent. These results highlight a novel modulatory role for the PHD inhibitor EDHB in hippocampal synaptic transmission and plasticity. A novel post-synaptic mechanism of action may be involved, possibly involving NMDA and GABA A receptor activation. Copyright © 2017 IBRO. Published by Elsevier Ltd. All rights reserved.

  3. Hollow fiber stir bar sorptive extraction for determination of phthalic acid esters in environmental and biological matrices.

    Science.gov (United States)

    Li, Jia; Wang, Yan-Bin; Su, Qiong; Wu, Shang; Wu, Lan

    2017-02-01

    The purpose of this paper is to introduce a novel hollow fiber stir bar sorptive extraction for collecting and determining of phthalic acid esters in environmental and biological matrices. Shell-core ZrO2 /SiO2 composite microspheres and porous C18 silica microspheres were compared as the sorbents, which were loaded in the lumen of a microporous hollow fiber membrane. A thin stainless-steel wire was also inside of the hollow fiber membrane acting as the magnetic stirrer, thus affording the procedures like stir bar sorptive extraction to perform the active trapping of the analytes. Variables affecting the extraction (salt addition and pH of samples, extraction temperature, and time) and desorption (microwave time and eluted solvents) have been optimized. Under the optimal conditions, good linearity (r > 0.9968) of all calibration curves was obtained in validation experiments. And the limits of quantification ranged from 0.01 to 1000 ng/mL. The recoveries in different matrices were in the range of 64.90-112.60% with relative standard deviations less than 8.60%. The present work demonstrated the applicability of the developed method for the determination of phthalic acid esters in environmental and biological sample, allowing the selective extraction of phthalate esters in complex samples with low consumption of organic solvents and no sample clean-up. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  4. Synthesis of alkynyl ethers and low-temperature sigmatropic rearrangement of allyl and benzyl alkynyl ethers.

    Science.gov (United States)

    Sosa, Juan R; Tudjarian, Armen A; Minehan, Thomas G

    2008-11-06

    Alpha-alkoxy ketones 3 can be transformed into 1-alkynyl ethers 5 by a two-step procedure involving formation of the enol triflate or phosphate and base-induced elimination. Performing the same reaction sequence with allylic alcohols (R2OH, R2 = allyl) furnishes instead gamma,delta-unsaturated carboxylic acid derivatives 6, derived from [3,3]-sigmatropic rearrangement of the intermediate allyl alkynyl ethers at -78 degrees C and trapping of the subsequently formed ketene with nucleophiles (Nu-H). Benzyl alkynyl ether 5 (R2 = benzyl) rearranges to indanone 7 upon heating to 60 degrees C.

  5. Synthesis of Alkynyl Ethers and Low Temperature Sigmatropic Rearrangement of Allyl and Benzyl Alkynyl Ethers

    Science.gov (United States)

    Sosa, Juan R.; Tudjarian, Armen A.; Minehan, Thomas G.

    2009-01-01

    α–Alkoxy ketones 3 can be transformed into 1-alkynyl ethers 5 by a two-step procedure involving formation of the enol triflate or phosphate and base-induced elimination. Performing the same reaction sequence with allylic alcohols (R2OH, R2 = allyl) furnishes instead γ,δ-unsaturated carboxylic acid derivatives 6, derived from [3,3]-sigmatropic rearrangement of the intermediate allyl alkynyl ethers at −78 °C and trapping of the subsequently formed ketene with nucleophiles (Nu-H). Benzyl alkynyl ether 5 (R2 = benzyl) rearranges to indanone 7 upon heating to 60 °C. PMID:18847213

  6. 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.

  7. Effects of propolis, caffeic acid phenethyl ester, and pollen on renal injury in hypertensive rat: An experimental and theoretical approach.

    Science.gov (United States)

    Salmas, Ramin Ekhteiari; Gulhan, Mehmet Fuat; Durdagi, Serdar; Sahna, Engin; Abdullah, Huda I; Selamoglu, Zeliha

    2017-08-01

    The objective of this study was to evaluate the antioxidant effects of propolis, caffeic acid phenethyl ester (CAPE; active compound in propolis), and pollen on biochemical oxidative stress biomarkers in rat kidney tissue inhibited by Nω -nitro-L-arginine methyl ester (L-NAME). The biomarkers evaluated were paraoxonase (PON1), oxidative stress index (OSI), total antioxidant status (TAS), total oxidant status (TOS), asymmetric dimethylarginine (ADMA), and nuclear factor kappa B (NF-κB). TAS levels and PON1 activity were significantly decreased in kidney tissue samples in the L-NAME-treated group (P propolis, CAPE, and pollen groups compared with the L-NAME-treated group. TOS, ADMA, and NF-κB levels were significantly increased in the kidney tissue samples of the L-NAME-treated group (P propolis, CAPE, and pollen groups (P propolis, CAPE administration. Copyright © 2017 John Wiley & Sons, Ltd.

  8. Oxidative stability of biodiesel from soybean oil fatty acid ethyl esters; Estabilidade oxidativa de biodiesel de esteres etilicos de acidos graxos de soja

    Energy Technology Data Exchange (ETDEWEB)

    Ferrari, Roseli Ap.; Oliveira, Vanessa da Silva; Scabio, Ardalla [Universidade Estadual de Ponta Grossa (UEPG), PR (Brazil). Dept. de Engenharia de Alimentos]. E-mail: ferrarir@uepg

    2005-06-01

    Biodiesel consists of long-chain fatty acid esters, derived from renewable sources such as vegetable oils, and its utilization is associated to the substitution of the diesel oil in engines. Depending on the raw material, bio diesel can contain more or less unsaturated fatty acids in its composition, which are susceptible to oxidation reactions accelerated by exposition to oxygen and high temperatures, being able to change into polymerized compounds. The objective of this work was to determine the oxidative stability of bio diesel produced by ethanolysis of neutralized, refined, soybean frying oil waste, and partially hydrogenated soybean frying oil waste. The evaluation was conducted by means of the Rancimat equipment, at temperatures of 100 and 105 deg C, with an air flow of 20 L h{sup -1}. The fatty acid composition was determined by GC and the iodine value was calculated. It was observed that even though the neutralized, refined and waste frying soybean oils presented close comparable iodine values, bio diesel presented different oxidative stabilities. The bio diesel from neutralized soybean oil presented greater stability, followed by the refined and the frying waste. Due to the natural antioxidants in its composition, the neutralized soybean oil promoted a larger oxidative stability of the produced bio diesel. During the deodorization process, the vegetable oils lose part of these antioxidants, therefore the bio diesel from refined soybean oil presented a reduced stability. The thermal process degrades the antioxidants, thus the bio diesel from frying waste oil resulted in lower stability, the same occurring with the bio diesel from partially hydrogenated waste oil, even though having lower iodine values than the other. (author)

  9. 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.

  10. Synthesis, Properties and Applications of Biodegradable Polymers Derived from Diols and Dicarboxylic Acids: From Polyesters to Poly(ester amides

    Directory of Open Access Journals (Sweden)

    Angélica Díaz

    2014-04-01

    Full Text Available Poly(alkylene dicarboxylates constitute a family of biodegradable polymers with increasing interest for both commodity and speciality applications. Most of these polymers can be prepared from biobased diols and dicarboxylic acids such as 1,4-butanediol, succinic acid and carbohydrates. This review provides a current status report concerning synthesis, biodegradation and applications of a series of polymers that cover a wide range of properties, namely, materials from elastomeric to rigid characteristics that are suitable for applications such as hydrogels, soft tissue engineering, drug delivery systems and liquid crystals. Finally, the incorporation of aromatic units and α-amino acids is considered since stiffness of molecular chains and intermolecular interactions can be drastically changed. In fact, poly(ester amides derived from naturally occurring amino acids offer great possibilities as biodegradable materials for biomedical applications which are also extensively discussed.

  11. 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.

  12. 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.

  13. Enzymatic Synthesis of Glucose-Based Fatty Acid Esters in Bisolvent Systems Containing Ionic Liquids or Deep Eutectic Solvents

    Directory of Open Access Journals (Sweden)

    Kai-Hua Zhao

    2016-09-01

    Full Text Available Sugar fatty acid esters (SFAEs are biocompatible nonionic surfactants with broad applications in food, cosmetic, and pharmaceutical industries. They can be synthesized enzymatically with many advantages over their chemical synthesis. In this study, SFAE synthesis was investigated by using two reactions: (1 transesterification of glucose with fatty acid vinyl esters and (2 esterification of methyl glucoside with fatty acids, catalyzed by Lipozyme TLIM and Novozym 435 respectively. Fourteen ionic liquids (ILs and 14 deep eutectic solvents (DESs were screened as solvents, and the bisolvent system composed of 1-hexyl-3-methylimidazolium trifluoromethylsulfonate ([HMIm][TfO] and 2-methyl-2-butanol (2M2B was the best for both reactions, yielding optimal productivities (769.6 and 397.5 µmol/h/g, respectively which are superior to those reported in the literature. Impacts of different reaction conditions were studied for both reactions. Response surface methodology (RSM was employed to optimize the transesterification reaction. Results also demonstrated that as co-substrate, methyl glucoside yielded higher conversions than glucose, and that conversions increased with an increase in the chain length of the fatty acid moieties. DESs were poor solvents for the above reactions presumably due to their high viscosity and high polarity.

  14. Reversible formation of fatty acid esters of budesonide, an antiasthma glucocorticoid, in human lung and liver microsomes.

    Science.gov (United States)

    Tunek, A; Sjödin, K; Hallström, G

    1997-11-01

    Microsomes from human lung and liver catalyze the formation of fatty acid esters of budesonide, a glucocorticoid used for inhalation treatment of asthma. The conjugation was dependent on coenzyme A and ATP. Addition of free fatty acids to the incubations affected the pattern of metabolites, but ester formation was observed also without such addition. Budesonide oleate, palmitate, linoleate, palmitoleate, and arachidonate were identified as metabolites. The fatty acid conjugates of budesonide were shown to be substrates for lipase in vitro, thus budesonide is regainable from the conjugates. The data suggest that an equilibrium between budesonide and these pharmacologically inactive lipoidal conjugates will be established in tissues at repeated exposure to budesonide. Since the fatty acid conjugates most likely will be retained intracellularly for a longer time than unchanged budesonide, the duration of tissue exposure to budesonide will depend partly on the rate of lipase-catalyzed hydrolysis of the conjugates. The findings in this study provide a possible explanation for the efficacy of budesonide in mild asthmatics also when inhaled once daily.

  15. 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

    The aim of this paper is to screen suitable reaction systems for the modification of antioxidants through enzy-matic synthesis. Enzymatic esterification of ascorbic acid with conjugated linoleic acid (CLA) was investigated as a mod-el. Four organic solvents and five different enzymes were evaluated....... 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...... 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...

  16. PENGGUNAAN GETAH PEPAYA DALAM SINTESIS ESTER XILITOL ASAM LEMAK (EXAL [The Use of Papaya Exudates for Fatty Acid Xilitol Synthesis

    Directory of Open Access Journals (Sweden)

    Suhardi

    2003-12-01

    Full Text Available Fatty acid xylitol-ester (FAXILE are xylitol esters of fatty acids with one to five DE (degree of esterification value. FAXILE with DE value of 3 or higher can be used as low calorie fat replacer since they have low digestive property; while the xylitol ester with DE of less than 3 can be used as emulsifier. The FAXILE synthesis experiments were carried out by esterification of xylitol with palm oil¡¦s fatty acid (POFA using papaya exudates as a lipase source. The objective of this experiment was to evaluate the potential of papaya exuadates for the synthesis of FAXILE. In this first experiment, test were carried out to determine hydrolytic activity of lipases obtained from different part of papaya plant. The test, were performed with the presence of CaO and under different pH value. The papaya exudates were used for FAXILE synthesis under an optimum condition obtained from the first experiment. Samples were drawn during incubation at 40„aC for 1,2,3, and 4 days and hydroxyl number was analyzed to confirm the ester formation. The results showed that the most active exudate was from papaya leaves, followed by exudates from fruit with hydrolytic activity of 653 and 296 ƒÝmol/g. minutes, respectively. The hydrolytic activity of the fruit exudate was optimum at pH 6.0, at 45-50„aC, with the addition of CaO 4% dry exudates. The FAXILE synthesis with acid of papaya exudates was optimum at pH 6.0, at 45„aC with molar ratio of xylitol: fatty acids was 1 to 6,3 days incubation. At this condition the conversion rate xylitol to FAXILE was 79%.

  17. In vivo analgesic and anti-inflammatory activities of Rosmarinus officinalis aqueous extracts, rosmarinic acid and its acetyl ester derivative.

    Science.gov (United States)

    Lucarini, Rodrigo; Bernardes, Wagner A; Ferreira, Daniele S; Tozatti, Marcos G; Furtado, Ricardo; Bastos, Jairo K; Pauletti, Patrícia M; Januário, Ana H; Silva, Márcio L Andrade E; Cunha, Wilson R

    2013-09-01

    Despite several pharmacological applications of Rosmarinus officinalis L. (Lamiaceae), studies on its analgesic and anti-inflammatory properties have been scarce. The aim of this work was to use in vivo models to evaluate the analgesic and anti-inflammatory activities of the aqueous extracts obtained from leaves (AEL) and stems (AES) of Rosmarinus officinalis, as well as its isolated compound--rosmarinic acid (RA). We also prepared and assessed the acetyl ester derivative of RA. The analgesic activity was evaluated using abdominal constriction and formalin tests. For the evaluation of the anti-inflammatory effects, carrageenin-induced paw edema in rats were used. The extracts were used at doses of 100, 200 and 400 mg kg⁻¹ compounds were tested at 10, 20 and 40 mg kg⁻¹. Orally administered AEL, AES and RA were not significantly active at any of the doses tested during the abdominal constriction test; the acetyl ester derivative of RA displayed significant analgesic activity. In the carrageenin-induced paw edema assay, the acetyl derivative of RA at all the tested doses produced significant anti-inflammatory effects and reduced the number of paw licks in the second phase of the formalin test. The results suggest that the analgesic effects of the acetyl derivative of RA operate via a peripheral-mediated mechanism. The acetyl ester derivative of RA is potentially applicable as a new lead compound for the management of pain and inflammation.

  18. Labdanolic acid methyl ester (LAME) exerts anti-inflammatory effects through inhibition of TAK-1 activation

    Energy Technology Data Exchange (ETDEWEB)

    Cuadrado, Irene [Departamento de Farmacología, Facultad de Farmacia, Universidad Complutense, Plaza Ramón y Cajal s/n, 28040 Madrid (Spain); Cidre, Florencia; Herranz, Sandra [Unidad de Inflamación y Cáncer. Área de Biología Celular y Desarrollo. Centro Nacional de Microbiología, Instituto de Salud Carlos III, Madrid (Spain); Estevez-Braun, Ana [Instituto Universitario de Bio-Orgánica “Antonio González”. Universidad de La Laguna. Avda. Astrofísico Fco. Sánchez 2. 38206. La Laguna, Tenerife (Spain); Instituto Canario de Investigaciones del Cáncer (ICIC) (Spain); Heras, Beatriz de las, E-mail: lasheras@farm.ucm.es [Departamento de Farmacología, Facultad de Farmacia, Universidad Complutense, Plaza Ramón y Cajal s/n, 28040 Madrid (Spain); Hortelano, Sonsoles, E-mail: shortelano@isciii.es [Unidad de Inflamación y Cáncer. Área de Biología Celular y Desarrollo. Centro Nacional de Microbiología, Instituto de Salud Carlos III, Madrid (Spain)

    2012-01-01

    Labdane derivatives obtained from the diterpenoid labdanediol suppressed NO and PGE{sub 2} production in LPS-stimulated RAW 264.7 macrophages. However, mechanisms involved in these inhibitory effects are not elucidated. In this study, we investigated the signaling pathways involved in the anti-inflammatory effects of labdanolic acid methyl ester (LAME) in peritoneal macrophages and examined its therapeutic effect in a mouse endotoxic shock model. LAME reduced the production of NO and PGE{sub 2} in LPS-activated macrophages. This effect involved the inhibition of NOS-2 and COX-2 gene expression, acting at the transcription level. Examination of the effects of the diterpene on NF-κB signaling showed that LAME inhibits the phosphorylation of IκBα and IκBβ, preventing their degradation and the nuclear translocation of the NF-κB p65 subunit. Moreover, inhibition of MAPK signaling was also observed. A further experiment revealed that LAME inhibited the phosphorylation of transforming growth factor-β (TGF-β)-activated kinase 1 (TAK1), an upstream signaling molecule required for IKK and mitogen-activated protein kinases (MAPKs) activation. Inflammatory cytokines such as IL-6, TNF-α and IP-10 were downregulated in the presence of this compound after stimulation with LPS. Additionally, LAME also improved survival in a mouse model of endotoxemia and reduced the circulatory levels of cytokines (IL-6, TNF-α). In conclusion, these results indicate that labdane diterpene LAME significantly attenuates the pro-inflammatory response induced by LPS both in vivo and in vitro. Highlights: ► LAME reduced the production of NO and PGE{sub 2} in LPS-activated macrophages. ► IL-6, TNF-α and IP-10 were also inhibited by LAME. ► Inhibition of TAK-1 activation is the mechanism involved in this process. ► LAME improved survival in a mouse model of endotoxemia. ► LAME reduced the circulatory levels of cytokines (IL-6, TNF-α).

  19. 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

  20. Elimination and ecotoxicity evaluation of phthalic acid esters from textile-dyeing wastewater.

    Science.gov (United States)

    Liang, Jieying; Ning, Xun-An; Kong, Minyi; Liu, Daohua; Wang, Guangwen; Cai, Haili; Sun, Jian; Zhang, Yaping; Lu, Xingwen; Yuan, Yong

    2017-12-01

    Phthalic acid esters (PAEs), presented in fabrics, surfactants and detergents, were discharged into the ecosystem during textile-dyeing wastewater treatment and might have adverse effects on water ecosystems. In this study, comprehensive investigations of the content and component distributions of 12 PAEs across different units of four textile-dyeing wastewater plants were carried out in Guangdong Province, China. Ecotoxicity assessments were also conducted based on risk quotients (RQs). On average, 93.54% TOC and 80.14% COD Cr were removed following treatment at the four plants. The average concentration of Σ 12 PAEs in effluent was 11.78 μg/L. PAEs with highest concentrations were dimethylphthalate (6.58 μg/L), bis(2-ethylhexyl)phthalate (2.23 μg/L), and dibutylphthalate (1.98 μg/L). The concentrations of the main toxic PAEs were 2.23 μg/L (bis(2-ethylhexyl)phthalate), 0.19 μg/L (diisononylphthalate) and 0.67 μg/L (dinoctylphthalate); corresponding RQs were 1.4, 0.55, and 0.54 for green algae, respectively. The RQs of Σ 12 PAEs in effluent of the four plants were >0.1, indicating that Σ 12 PAEs posed medium or higher ecological risk to fish, Daphnia and green algae. Physicochemical-biochemical system was found to be more effective than biochemical-physicochemical system for TOC and COD Cr removal, because pre-physicochemical treatment helped to remove macromolecular organic substances, and reduced the competition with other pollutants during biochemical treatment. However, biochemical-physicochemical system was more effective than physicochemical-biochemical system for elimination of PAEs and for detoxification, since the biochemical treatment might produce the toxic PAEs that could helpfully be settled by post-physicochemical treatment. Moreover, ecotoxicity evaluation was recommended for current textile-dyeing wastewater treatment plants. Copyright © 2017. Published by Elsevier Ltd.

  1. Lithium-induced renal toxicity in rats: protection by a novel antioxidant caffeic acid phenethyl ester.

    Science.gov (United States)

    Oktem, Faruk; Ozguner, Fehmi; Sulak, Osman; Olgar, Seref; Akturk, Onur; Yilmaz, H Ramazan; Altuntas, Irfan

    2005-09-01

    Lithium carbonate used in the long-term treatment of manic-depressive illness has been reported to lead to progressive renal impairment in rats and humans. Caffeic acid phenethyl ester (CAPE), a component of honeybee propolis, protects tissues from reactive oxygene species mediated oxidative stress in ischemia-reperfusion and toxic injuries. The beneficial effect CAPE on lithium-induced nephrotoxicity has not been reported yet. The purpose of this study was to examine a possible renoprotective effect of CAPE against lithium-induced nephrotoxicity in a rat model. Twenty-two adult male rats were randomly divided into three experimental groups, as follows: control group, lithium-treated group (Li), and lithium plus CAPE-treated group (Li+CAPE). Li were treated intraperitoneally (i.p.) with 25 mg/kg Li2CO3 solution in 0.9% NaCl twice daily for 4 weeks. CAPE was co-administered i.p. with a dose of 10 microM/kg/day for 4 weeks. Serum Li, blood urea nitrogen and plasma creatinine, urinary N-acetyl-beta-D-glucosaminidase (NAG, a marker of renal tubular injury), and malondialdehyde (MDA, an index of lipid peroxidation), were used as markers of oxidative stress-induced renal impairment in Li-treated rats. Superoxide dismutase (SOD), catalase (CAT), and glutathione peroxidase (GSH-Px) activities were studied to evaluate the changes of antioxidant status in renal tissue. Serum Li levels were found high in the Li and Li+CAPE groups. In Li-administrated rats, urinary NAG and renal MDA levels were increased according to control and Li+CAPE groups (p < 0.05). CAPE caused a significant reduction in the levels of these parameters. Likewise, renal SOD, CAT and GSH-Px activities were decreased in Li-administrated animals; CAPE caused a significant increase in the activities of these antioxidant enzymes. In conclusion, CAPE treatment has a protective effect against Li-induced renal tubular damage and oxidative stress in a rat model.

  2. Oral fumaric acid esters for psoriasis: abridged Cochrane systematic review including GRADE assessments.

    Science.gov (United States)

    Atwan, A; Ingram, J R; Abbott, R; Kelson, M J; Pickles, T; Bauer, A; Piguet, V

    2016-11-01

    Fumaric acid esters (FAEs) are licensed for the treatment of moderate-to-severe psoriasis in Germany but are also used off-label in many other countries. We conducted this systematic review to synthesize the highest-quality evidence for the benefits and risks of FAEs for psoriasis. Our primary outcomes were change in Psoriasis Area and Severity Index score and dropout rates due to adverse effects. Randomized controlled trials (RCTs) of FAEs or dimethylfumarate were included, with no restriction on age or psoriasis subtype. We searched the Cochrane Skin Group Specialised Register, CENTRAL in the Cochrane Library, Medline, Embase, LILACS and five trials registers, and hand searched six conference proceedings. Six RCTs with a total of 544 participants were included, four of which were published only as abstracts or brief reports, limiting study reporting. Five RCTs compared FAEs with placebo, and all demonstrated benefit in favour of FAEs. However, meta-analysis was possible only for PASI 50 response after 12-16 weeks, which was achieved by 64% of participants on FAEs compared with 14% on placebo: risk ratio (RR) 4·55, 95% confidence interval (CI) 2·80-7·40; two studies; 247 participants; low-quality evidence). There was no difference in dropout rates due to adverse effects (RR 5·36, 95% CI 0·28-102·12; one study; 27 participants; very low-quality evidence and wide CI). More participants experienced nuisance adverse effects with FAEs (76%) than with placebo (16%) (RR 4·72, 95% CI 2·45-9·08; one study; 99 participants; moderate-quality evidence), mainly abdominal pain, diarrhoea and flushing. One head-to-head study of very low-quality evidence comparing FAEs with methotrexate reported comparable efficacy and dropout rates, although FAEs caused more flushing. The evidence in this review was limited and must be interpreted with caution; studies with better design and outcome reporting are needed. © 2016 The Authors. British Journal of Dermatology published by

  3. 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.

  4. The allylic chalcogen effect in olefin metathesis

    Directory of Open Access Journals (Sweden)

    Yuya A. Lin

    2010-12-01

    Full Text Available Olefin metathesis has emerged as a powerful tool in organic synthesis. The activating effect of an allylic hydroxy group in metathesis has been known for more than 10 years, and many organic chemists have taken advantage of this positive influence for efficient synthesis of natural products. Recently, the discovery of the rate enhancement by allyl sulfides in aqueous cross-metathesis has allowed the first examples of such a reaction on proteins. This led to a new benchmark in substrate complexity for cross-metathesis and expanded the potential of olefin metathesis for other applications in chemical biology. The enhanced reactivity of allyl sulfide, along with earlier reports of a similar effect by allylic hydroxy groups, suggests that allyl chalcogens generally play an important role in modulating the rate of olefin metathesis. In this review, we discuss the effect of allylic chalcogens in olefin metathesis and highlight its most recent applications in synthetic chemistry and protein modifications.

  5. The allylic chalcogen effect in olefin metathesis.

    Science.gov (United States)

    Lin, Yuya A; Davis, Benjamin G

    2010-12-23

    Olefin metathesis has emerged as a powerful tool in organic synthesis. The activating effect of an allylic hydroxy group in metathesis has been known for more than 10 years, and many organic chemists have taken advantage of this positive influence for efficient synthesis of natural products. Recently, the discovery of the rate enhancement by allyl sulfides in aqueous cross-metathesis has allowed the first examples of such a reaction on proteins. This led to a new benchmark in substrate complexity for cross-metathesis and expanded the potential of olefin metathesis for other applications in chemical biology. The enhanced reactivity of allyl sulfide, along with earlier reports of a similar effect by allylic hydroxy groups, suggests that allyl chalcogens generally play an important role in modulating the rate of olefin metathesis. In this review, we discuss the effect of allylic chalcogens in olefin metathesis and highlight its most recent applications in synthetic chemistry and protein modifications.

  6. 40 CFR 721.987 - Dialkylaminophenyl imino pyrazole acid ester (generic).

    Science.gov (United States)

    2010-07-01

    ... ester (generic). 721.987 Section 721.987 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... substance and significant new uses subject to reporting. (1) The chemical substance identified generically... as modified by this paragraph. (1) Recordkeeping. Recordkeeping requirements as specified in § 721...

  7. 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...

  8. 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.

  9. Interplay of metal-allyl and metal-metal bonding in dimolybdenum allyl complexes

    Energy Technology Data Exchange (ETDEWEB)

    John, Kevin D [Los Alamos National Laboratory; Martin, Richard L [Los Alamos National Laboratory; Obrey, Steven J [Los Alamos National Laboratory; Scott, Brian L [Los Alamos National Laboratory

    2008-01-01

    Addition of PMe{sub 3} to Mo{sub 2}(allyl){sub 4} afforded Mo{sub 2}(allyl){sub 4}(PMe{sub 3}){sub 2}, in which two of the allyl groups adopt an unprecedented {mu}{sub 2{sup -}}{eta}{sup 1}, {eta}{sup 3} bonding mode; theoretical studies elucidate the role sof the {sigma}- and {pi}-donor ligands in the interplay of metal-allyl and metal-metal bonding.

  10. 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.

  11. 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.

  12. Electronic properties of electron-doped [6,6]-phenyl-C61-butyric acid methyl ester and silylmethylfullerene

    Science.gov (United States)

    Furutani, Sho; Okada, Susumu

    2017-06-01

    Electronic properties of electron-doped chemically decorated C60 fullerenes, [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) and silylmethylfullerene (SIMEF), by a planar electrode were studied using density functional theory combined with the effective screening medium method to simulate the heterointerface between the chemically decorated C60 and cationic counter materials. We find that the distribution of accumulated electrons and induced electric field depend on the molecular arrangement with respect to the external electric field of the electrode. We also show that the quantum capacitance of the molecule is sensitive to molecular arrangement owing to the asymmetric distribution of the accumulated electrons.

  13. Long-term treatment with fumaric acid esters in an 11-year-old male child with psoriasis.

    Science.gov (United States)

    Gerdes, S; Domm, S; Mrowietz, U

    2011-01-01

    Moderate to severe psoriasis is common in childhood and adolescence and is often a challenge for the treating dermatologist. In most cases, systemic therapies in children are only available 'off-label'. Fumaric acid esters (FAEs) have been used successfully in the treatment of moderate to severe psoriasis in adults and are recommended for long-term treatment in the German S3 guideline. In childhood psoriasis, FAEs may be a treatment alternative if a systemic therapy is indicated. Here, we report about the successful long-term treatment with FAEs in a male child with severe psoriasis. Copyright © 2011 S. Karger AG, Basel.

  14. Raman Spectroscopy of Fish Oil Capsules: Polyunsaturated Fatty Acid Quantitation Plus Detection of Ethyl Esters and Oxidation.

    Science.gov (United States)

    Killeen, Daniel P; Marshall, Susan N; Burgess, Elaine J; Gordon, Keith C; Perry, Nigel B

    2017-05-03

    Fish oils are the primary dietary source of ω-3 polyunsaturated fatty acids (PUFA), but these compounds are prone to oxidation, and commercial fish oil supplements sometimes contain less PUFA than claimed. These supplements are predominantly sold in softgel capsules. In this work, we show that Fourier transform (FT)-Raman spectra of fish oils (n = 5) and ω-3 PUFA concentrates (n = 6) can be acquired directly through intact softgel (gelatin) capsules. These spectra could be used to rapidly distinguish supplements containing ethyl esters from those containing triacylglyceride oils. Raman spectroscopy calibrated with partial least-squares regression against traditional fatty acid methyl ester analyses by gas chromatography-mass spectrometry could be used to rapidly and nondestructively quantitate PUFA and other fatty acid classes directly though capsules. We also show that FT-Raman spectroscopy can noninvasively detect oxidation with high sensitivity. Oils with peroxide values of as low as 10 mequiv kg -1 , which are on the cusp of falling outside of specification, could be readily distinguished from oils that were within specification (7 mequiv kg -1 ).

  15. Two New Saccharide Fatty Acid Esters from the Fruit of Morinda citrifolia L. and Their ABTS Radical Scavenging Activities

    Directory of Open Access Journals (Sweden)

    Hong-Cai Zhang

    2014-01-01

    Full Text Available Two n ew saccharide fatty acid esters (1 and (2, and six other compounds were isolated from the fruit of Morinda citrifolia L. (Rubiaceae The structures were established as (2E-oct-2-enoate-2-O-β-D - glucopyranosyl-β-D-glucopyranoside(1, (2E-2,6-dimethyl -6-hydroxyl-oct-2,7-dienoate-2-O-β-D-glucopyranosyl-β-D-glucopyranoside(2, saccharumoside C(3, O-β-D-apiofuranosyl-(1→6-O-β-D-glucopyranosides of 3-methyl-2-butenol(4, 3-methyl-but-2-en-1-yl β-D-glucopyranosyl (1→6-β-D-glucopyranoside(5, benzyl - glucopyranoside(6, Hexyl-O-β-D-glucopyranoside(7, and caproic acid(8. Compound 1 and 2 showed moderate activity against ABTS (2,2’-azino-bis(3-ethylbenzothiazoline-6-sulphonate radical in concentration of 0.1-3.2 mg/mL. Morinda citrifolia L., saccharide fatty acid ester, ABTS radical scavenging activity

  16. 40 CFR 721.6120 - Phosphoric acid, 1,2-eth-a-ne-diyl tet-ra-kis(2-chloro-1-meth-yl-ethyl) ester.

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Phosphoric acid, 1,2-eth-a-ne-diyl tet-ra-kis(2-chloro-1-meth-yl-ethyl) ester. 721.6120 Section 721.6120 Protection of Environment...-diyl tet-ra-kis(2-chloro-1-meth-yl-ethyl) ester. (a) Chemical substances and significant new uses...

  17. Electrospun fibers of acid-labile biodegradable polymers containing ortho ester groups for controlled release of paracetamol.

    Science.gov (United States)

    Qi, Mingbo; Li, Xiaohong; Yang, Ye; Zhou, Shaobing

    2008-10-01

    The local delivery and controllable release profiles make electrospun ultrafine fibers as potential implantable drug carriers and functional coatings of medical devices. There are few attempts to form acid-labile electrospun fibers, whose release behaviors respond to the local environment and fiber characteristics. In the current study a novel strategy was presented to synthesize biodegradable pH-sensitive polymers containing ortho ester groups. The acid-labile segments were synthesized through reacting 3,9-dimethylene-2,4,8,10-tetraoxaspiro [5.5] undecane with 1,10-decanediol or poly(ethylene glycol), which were further copolymerized with D,L-lactide to obtain triblock copolymers. Biodegradable acid-labile polymers were electrospun with the encapsulation of paracetamol as a model drug. In vitro release study showed that the total amount of drug released from acid-labile polymeric fibers was accelerated after incubation into acid buffer solutions, and the amount of initial burst release and sustained release rate were significantly higher for matrix polymers with hydrophilic acid-labile segments. In vitro degradation study indicated that the electrospun fibers containing acid-labile segments were stable in neutral buffer solution, but the molecular weight reduction of matrix polymers, the morphological changes and mass loss of fibrous mats were significantly enhanced under acid circumstances.

  18. Development of a new Lewis acid-catalyzed [3,3]-sigmatropic rearrangement: the allenoate-Claisen rearrangement.

    Science.gov (United States)

    Lambert, Tristan H; MacMillan, David W C

    2002-11-20

    A new Lewis acid-catalyzed Claisen rearrangement has been developed that allows the stereoselective construction of beta-amino-alpha,beta,epsilon,zeta-unsaturated-gamma,delta-disubstituted esters from simple allylic amines and allenoate esters. This reaction, which is contingent upon the use of Lewis acid, can be conducted with a range of metal salts (Yb(OTf)3, AlCl3, Sn(OTf)2, Cu(OTf)2, MgBr2.Et2O, FeCl3, Zn(OTf)2) with catalyst loadings as low as 5 mol %. This catalytic process provides access to a diverse range of beta-amino-alpha,beta,epsilon,zeta-unsaturated-gamma,delta-disubstituted esters in high yield and with excellent levels of diastereoselectivity for a series of allyl pyrrolidines (R1 = H, Me, i-Pr, Ph, NR2 = pyrrolidine, piperidine, NMe2; >/=81% yield, >/=94:6 syn:anti) and allenoate esters (R2 = H, Me, i-Pr, Ph, allyl, NPht, Cl; >/=75% yield, >/=91:9 syn:anti). The capacity of this new Claisen rearrangement to provide catalytic access to elusive structural motifs has also been demonstrated in the stereospecific formation of quaternary carbon bearing frameworks arising from geranyl- and neryl pyrrolidine (>/=93% yield, >98:2 dr).

  19. L-Lactate-mediated Dynamic Kinetic Resolution of α-Bromo Esters for Asymmetric Syntheses of α-Amino Acid Derivatives

    Energy Technology Data Exchange (ETDEWEB)

    Kim, Yelim; Park, Kon Ji; Choi, Yun Soo; Lee, Myungsu; Park, Yong Sun [Konkuk Univ., Seoul (Korea, Republic of)

    2013-08-15

    We conclude that ethyl L-lactate is an effective and convenient chiral auxiliary for dynamic kinetic resolution of α-bromo esters in nucleophilic substitution with various amine nucleophiles. The methodology can provide a general procedure for asymmetric syntheses of dihydroquinoxalinones, dihydrobenzoxazinones and 1,1'-iminodicarboxylic acid derivatives. Simple and easy procedure in obtaining highly enantioenriched α-amino acid derivatives suggests that the dynamic kinetic resolution approach should be further developed. For asymmetric synthesis of α-substituted carboxylic acid derivatives, a variety of chiral auxiliaries have been used for the dynamic resolution of α-halo esters in nucleophilic substitution.1 For example, L-lactamide-mediated dynamic kinetic resolution of α-bromo esters was successfully used for the asymmetric preparation of α-aryloxy carboxylic acids and oxazin-2-ones.

  20. 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)

  1. The influence of the substrate structure in the telluro-cyclo-functionalization reaction of {gamma}, {delta}-unsaturated carboxylic acids and their corresponding benzyl esters

    Energy Technology Data Exchange (ETDEWEB)

    Moraes, Denilson N.; Santos, Rute A.; Comasseto, Joao V. [Sao Paulo Univ., SP (Brazil). Inst. de Quimica

    1998-07-01

    {gamma},{delta}-Unsaturated carboxylic acids containing mono substituted double bonds react with aryl tellurium trichlorides to give the expected telluro lactone. Reaction of the corresponding benzyl esters gives the addition product of the aryl tellurium trichlorides to the double bond {gamma}, {delta}-Unsaturated carboxylic acids containing 1,1-disubstituted double bonds lead to a mixture of the expected telluro lactone and the product of hydrochloric acid addition to the double bond; the corresponding benzyl ester gives the telluro lactone as the only product. The stereoselectivity of the reaction is low; mixtures of the two possible diastereomeric lactones are formed in approximately 1:1 ratios. (author)

  2. 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.

  3. Dietary taurine reduces hepatic secretion of cholesteryl ester and enhances fatty acid oxidation in rats fed a high-cholesterol diet.

    Science.gov (United States)

    Fukuda, Nobuhiro; Yoshitama, Ayako; Sugita, Satomi; Fujita, Michiko; Murakami, Shigeru

    2011-01-01

    We investigated the fate of exogenous fatty acid in connection with decreased hepatic accumulation and secretion of cholesteryl esters in rats fed diets containing taurine. Providing taurine as 5% of the diet for 14 d significantly decreased concentrations of cholesterol, especially cholesteryl esters in both serum and liver. Ketone body production and incorporation of exogenous [1-(14)C]oleate into ketone bodies in liver perfusate were consistently higher during a 4-h perfusion period in taurine-fed rats than in control rats. The elevation was accompanied by increased activity of liver mitochondrial carnitine palmitoyltransferase, a rate-limiting enzyme for fatty acid oxidation. Dietary taurine significantly reduced hepatic secretion of cholesteryl ester and decreased incorporation of exogenous oleic acid substrate into this lipid molecule. Further, the extent of reduction in hepatic secretion of cholesteryl ester was closely related to its diminished accumulation in the liver. The conversion pattern of exogenous [1-(14)C]oleic acid substrate suggested a decreased esterification-to-oxidation ratio in the taurine group compared with the control. These results suggest that taurine-induced reduction in hepatic accumulation of cholesteryl ester was associated with reduced hepatic secretion of this lipid molecule, and was inversely related to enhanced ketone body production and fatty acid oxidation.

  4. High Performance Fatty Acid-Based Vinyl Ester Resin for Liquid Molding

    Science.gov (United States)

    2007-07-01

    novolac epoxy, and Epon 828 , a diglycidyl ether of bisphenol A (DGEBA), were purchased from Hexion Specialty Chemicals and was used to synthesize vinyl...with Epon 160 (n=0.5) and Epon 828 (n=0.098) to produce VE 160 and VE 828 , respectively (Figure 1). The reaction was catalyzed by 1 wt% AMC-2...PROCEDURE 2.1 Materials Derakane 470HT-400 vinyl ester resin was obtained from Ashland and was used without modification. Epon Resin 160, a

  5. Synthesis of alkenyl boronates from allyl-substituted aromatics using an olefin cross-metathesis protocol.

    Science.gov (United States)

    Hemelaere, Rémy; Carreaux, François; Carboni, Bertrand

    2013-07-05

    An efficient synthesis of 3-aryl-1-propenyl boronates from pinacol vinyl boronic ester and allyl-substituted aromatics by cross metathesis is reported. Although the allylbenzene derivatives are prone to isomerization reaction under metathesis conditions, we found that some ruthenium catalysts are effective for this methodology. This strategy thus provides an interesting alternative approach to alkyne hydroboration, leading to the preparation of unknown compounds. Moreover, the boron substituent can be replaced by various functional groups in good yields.

  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. Bioactivity and structure-activity relationship of cinnamic acid esters and their derivatives as potential antifungal agents for plant protection.

    Science.gov (United States)

    Zhou, Kun; Chen, Dongdong; Li, Bin; Zhang, Bingyu; Miao, Fang; Zhou, Le

    2017-01-01

    A series of cinnamic acid esters and their derivatives were synthesized and evaluated for antifungal activities in vitro against four plant pathogenic fungi by using the mycelium growth rate method. Structure-activity relationship was derived also. Almost all of the compounds showed some inhibition activity on each of the fungi at 0.5 mM. Eight compounds showed the higher average activity with average EC50 values of 17.4-28.6 μg/mL for the fungi than kresoxim-methyl, a commercial fungicide standard, and ten compounds were much more active than commercial fungicide standards carbendazim against P. grisea or kresoxim-methyl against both P. grisea and Valsa mali. Compounds C1 and C2 showed the higher activity with average EC50 values of 17.4 and 18.5 μg/mL and great potential for development of new plant antifungal agents. The structure-activity relationship analysis showed that both the substitution pattern of the phenyl ring and the alkyl group in the alcohol moiety significantly influences the activity. There exists complexly comprehensive effect between the substituents on the phenyl ring and the alkyl group in the alcohol moiety on the activity. Thus, cinnamic acid esters showed great potential the development of new antifungal agents for plant protection due to high activity, natural compounds or natural compound framework, simple structure, easy preparation, low-cost and environmentally friendly.

  8. Bioactivity and structure-activity relationship of cinnamic acid esters and their derivatives as potential antifungal agents for plant protection.

    Directory of Open Access Journals (Sweden)

    Kun Zhou

    Full Text Available A series of cinnamic acid esters and their derivatives were synthesized and evaluated for antifungal activities in vitro against four plant pathogenic fungi by using the mycelium growth rate method. Structure-activity relationship was derived also. Almost all of the compounds showed some inhibition activity on each of the fungi at 0.5 mM. Eight compounds showed the higher average activity with average EC50 values of 17.4-28.6 μg/mL for the fungi than kresoxim-methyl, a commercial fungicide standard, and ten compounds were much more active than commercial fungicide standards carbendazim against P. grisea or kresoxim-methyl against both P. grisea and Valsa mali. Compounds C1 and C2 showed the higher activity with average EC50 values of 17.4 and 18.5 μg/mL and great potential for development of new plant antifungal agents. The structure-activity relationship analysis showed that both the substitution pattern of the phenyl ring and the alkyl group in the alcohol moiety significantly influences the activity. There exists complexly comprehensive effect between the substituents on the phenyl ring and the alkyl group in the alcohol moiety on the activity. Thus, cinnamic acid esters showed great potential the development of new antifungal agents for plant protection due to high activity, natural compounds or natural compound framework, simple structure, easy preparation, low-cost and environmentally friendly.

  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. Mono- and tri-ester hydrogenolysis using tandem catalysis. Scope and mechanism.

    Energy Technology Data Exchange (ETDEWEB)

    Lohr, Tracy L.; Li, Zhi; Assary, Rajeev S.; Curtiss, Larry A.; Marks, Tobin J.

    2016-01-01

    The scope and mechanism of thermodynamically leveraged ester RC(O)O-R' bond hydrogenolysis by tandem metal triflate + supported Pd catalysts are investigated both experimentally and theoretically by DFT and energy span analysis. This catalytic system has a broad scope, with relative cleavage rates scaling as, tertiary 4 secondary 4 primary ester at 1 bar H-2, yielding alkanes and carboxylic acids with high conversion and selectivity. Benzylic and allylic esters display the highest activity. The rate law is nu = k[M(OTf )(n)](1)[ester](0)[H-2](0) with an H/D kinetic isotope effect = 6.5 +/- 0.5, implying turnover-limiting C-H scission following C-O cleavage, in agreement with theory. Intermediate alkene products are then rapidly hydrogenated. Applying this approach with the very active Hf(OTf)(4) catalyst to bio-derived triglycerides affords near-quantitative yields of C-3 hydrocarbons rather than glycerol. From model substrates, it is found that RC(O)O-R' cleavage rates are very sensitive to steric congestion and metal triflate identity. For triglycerides, primary/external glyceryl CH2-O cleavage predominates over secondary/internal CH-O cleavage, with the latter favored by less acidic or smaller ionic radius metal triflates, raising the diester selectivity to as high as 48% with Ce(OTf)(3).

  12. Adhesion properties of catechol-based biodegradable amino acid-based poly(ester urea) copolymers inspired from mussel proteins.

    Science.gov (United States)

    Zhou, Jinjun; Defante, Adrian P; Lin, Fei; Xu, Ying; Yu, Jiayi; Gao, Yaohua; Childers, Erin; Dhinojwala, Ali; Becker, Matthew L

    2015-01-12

    Amino acid-based poly(ester urea) (PEU) copolymers functionalized with pendant catechol groups that address the need for strongly adhesive yet degradable biomaterials have been developed. Lap-shear tests with aluminum adherends demonstrated that these polymers have lap-shear adhesion strengths near 1 MPa. An increase in lap-shear adhesive strength to 2.4 MPa was achieved upon the addition of an oxidative cross-linker. The adhesive strength on porcine skin adherends was comparable with commercial fibrin glue. Interfacial energies of the polymeric materials were investigated via contact angle measurements and Johnson-Kendall-Roberts (JKR) technique. The JKR work of adhesion was consistent with contact angle measurements. The chemical and physical properties of PEUs can be controlled using different diols and amino acids, making the polymers candidates for the development of biological glues for use in clinical applications.

  13. Caffeic Acid Phenethyl Ester from the Twigs of Cinnamomum cassia Inhibits Malignant Cell Transformation by Inducing c-Fos Degradation.

    Science.gov (United States)

    Shin, Seung Ho; Lee, Seoung Rak; Lee, Eunjung; Kim, Ki Hyun; Byun, Sanguine

    2017-07-28

    The twigs of Cinnamomum cassia, commonly referred to as Cinnamomi Ramulus, are widely used as one of the primary ingredients in Chinese/Korean traditional medicines that have anticancer effects. However, the active constituents responsible for its anticancer effects and their molecular mechanisms still remain to be elucidated. Caffeic acid phenethyl ester (CAPE) and caffeic acid (CA) were isolated for the first time from C. cassia using LC-MS-guided phytochemical isolation methods. CAPE significantly suppressed EGF- and TPA-induced cell transformation of JB6 P+ cells at sub-micromolar concentrations, whereas CA, a structurally similar compound to CAPE, had no such effect. The antiproliferative and chemopreventive activity of CAPE was found to arise through the inhibition of AP-1 transcriptional activity via the promotion of c-Fos degradation. These findings demonstrate that CAPE may contribute to the chemopreventive/chemotherapeutic effects of C. cassia through downregulating c-Fos.

  14. Gas chromatography/mass spectrometric analysis of methyl esters of N,N-dialkylaminoethane-2-sulfonic acids for verification of the Chemical Weapons Convention.

    Science.gov (United States)

    Pardasani, Deepak; Gupta, Arvinda K; Palit, Meehir; Shakya, Purushottam; Kanaujia, Pankaj K; Sekhar, K; Dubey, Devendra K

    2005-01-01

    This paper describes the synthesis and gas chromatography/electron ionization mass spectrometric (GC/EI-MS) analysis of methyl esters of N,N-dialkylaminoethane-2-sulfonic acids (DAESAs). These sulfonic acids are important environmental signatures of nerve agent VX and its toxic analogues, hence GC/EI-MS analysis of their methyl esters is of paramount importance for verification of the Chemical Weapons Convention. DAESAs were prepared by condensation of 2-bromoethane sulfonic acid with dialkylamines, and by condensation of dialkylaminoethyl chloride with sodium bisulfite. GC/EI-MS analysis of methyl esters of DAESAs yielded mass spectra; based on these spectra, generalized fragmentation routes are proposed that rationalize most of the characteristic ions. (c) 2005 John Wiley & Sons, Ltd.

  15. 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%.

  16. Bioequivalence of two omega-3 fatty acid ethyl ester formulations: a case of clinical pharmacology of dietary supplements

    Science.gov (United States)

    Galli, Claudio; Maggi, Franco M; Risé, Patrizia; Sirtori, Cesare R

    2012-01-01

    AIM To evaluate the bioequivalence of two omega-3 long chain polyunsaturated fatty acid (n-3 LC-PUFA) ethyl ester preparations, previously shown not to be bioequivalent in healthy subjects, with the objective of providing a guideline for future work in this area. METHOD A randomized double-blind crossover protocol was chosen. Volunteers with the lowest blood concentrations of n-3 LC-PUFA were selected. They received the ethyl esters in a single high dose (12 g) and eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) blood concentrations were analyzed after fingerprick collection at intervals up to 24 h. RESULTS Differently from a prior study, the pharmacokinetic analysis indicated a satisfactory bioequivalence: for the AUC(0,24 h) 90% CI of the ratio between the two formulations were in the range for bioequivalence (for EPA 0.98, 1.04 and for DHA 0.99, 1.04) and the same was true for Cmax and tmax (90% CI were 0.95, 1.14 and 1.10, 1.25 for EPA and 0.88, 1.02 and 0.84, 1.24 for DHA). CONCLUSION This study shows that, in order to obtain reliable bioequivalence data of products present in the daily diet, certain conditions should be met. Subjects should have low, homogeneous baseline concentrations and not be exposed to food items containing the product under evaluation, e.g. fish. Finally, as in the case of omega-3 fatty acids, selected doses should be high, eventually with appropriate conditions of intake. PMID:22242645

  17. The Saccharomyces cerevisiae EHT1 and EEB1 genes encode novel enzymes with medium-chain fatty acid ethyl ester synthesis and hydrolysis capacity.

    Science.gov (United States)

    Saerens, Sofie M G; Verstrepen, Kevin J; Van Laere, Stijn D M; Voet, Arnout R D; Van Dijck, Patrick; Delvaux, Freddy R; Thevelein, Johan M

    2006-02-17

    Fatty acid ethyl esters are secondary metabolites produced by Saccharomyces cerevisiae and many other fungi. Their natural physiological role is not known but in fermentations of alcoholic beverages and other food products they play a key role as flavor compounds. Information about the metabolic pathways and enzymology of fatty acid ethyl ester biosynthesis, however, is very limited. In this work, we have investigated the role of a three-member S. cerevisiae gene family with moderately divergent sequences (YBR177c/EHT1, YPL095c/EEB1, and YMR210w). We demonstrate that two family members encode an acyl-coenzymeA:ethanol O-acyltransferase, an enzyme required for the synthesis of medium-chain fatty acid ethyl esters. Deletion of either one or both of these genes resulted in severely reduced medium-chain fatty acid ethyl ester production. Purified glutathione S-transferase-tagged Eht1 and Eeb1 proteins both exhibited acyl-coenzymeA:ethanol O-acyltransferase activity in vitro, as well as esterase activity. Overexpression of Eht1 and Eeb1 did not enhance medium-chain fatty acid ethyl ester content, which is probably due to the bifunctional synthesis and hydrolysis activity. Molecular modeling of Eht1 and Eeb1 revealed the presence of a alpha/beta-hydrolase fold, which is generally present in the substrate-binding site of esterase enzymes. Hence, our results identify Eht1 and Eeb1 as novel acyl-coenzymeA:ethanol O-acyltransferases/esterases, whereas the third family member, Ymr210w, does not seem to play an important role in medium-chain fatty acid ethyl ester formation.

  18. Characterization of Armillaria spp. from peach orchards in the southeastern United States using fatty acid methyl ester profiling.

    Science.gov (United States)

    Cox, K D; Scherm, H; Riley, M B

    2006-04-01

    Limited information is available regarding the composition of cellular fatty acids in Armillaria and the extent to which fatty acid profiles can be used to characterize species in this genus. Fatty acid methyl ester (FAME) profiles generated from cultures of A. tabescens, A. mellea, and A. gallica consisted of 16-18 fatty acids ranging from 12-24 carbons in length, although some of these were present only in trace amounts. Across the three species, 9-cis,12-cis-octadecadienoic acid (9,12-C18:2), hexadecanoic acid (16:0), heneicosanoic acid (21:0), 9-cis-octadecenoic acid (9-C18:1), and 2-hydroxy-docosanoic acid (OH-22:0) were the most abundant fatty acids. FAME profiles from different thallus morphologies (mycelium, sclerotial crust, or rhizomorphs) displayed by cultures of A. gallica showed that thallus type had no significant effect on cellular fatty acid composition (P > 0.05), suggesting that FAME profiling is sufficiently robust for species differentiation despite potential differences in thallus morphology within and among species. The three Armillaria species included in this study could be distinguished from other lignicolous basidiomycete species commonly occurring on peach (Schizophyllum commune, Ganoderma lucidum, Stereum hirsutum, and Trametes versicolor) on the basis of FAME profiles using stepwise discriminant analysis (average squared canonical correlation = 0.953), whereby 9-C18:1, 9,12-C18:2, and 10-cis-hexadecenoic acid (10-C16:1) were the three strongest contributors. In a separate stepwise discriminant analysis, A. tabescens, A. mellea, and A. gallica were separated from one another based on their fatty acid profiles (average squared canonical correlation = 0.924), with 11-cis-octadecenoic acid (11-C18:1), 9-C18:1, and 2-hydroxy-hexadecanoic acid (OH-16:0) being most important for species separation. When fatty acids were extracted directly from mycelium dissected from naturally infected host tissue, the FAME-based discriminant functions

  19. Toward Peptide Nucleic Acid (PNA) Directed Peptide Translation Using Ester Based Aminoacyl Transfer

    DEFF Research Database (Denmark)

    Singhal, Abhishek; Bagnacani, Valentina; Corradini, Roberto

    2014-01-01

    Peptide synthesis is a fundamental feature of life. However, it still remains unclear how the contemporary translation apparatus evolved from primitive prebiotic systems and at which stage of the evolution peptide synthesis emerged. Using simple molecular architectures, in which aminoacyl transfer...... intermolecular aminoacyl transfer using simple ester aminolysis chemistry primitively analogous to the ribosomal peptidyl transferase reaction in the absence of anchimeric assistance from ribose and ribosome catalysis. These results help define the minimum chemical boundary conditions for the translation process...... and also give insight into the possibilities for the prebiotic emergence of RNA-independent translation....

  20. SO2 F2 -Mediated One-Pot Synthesis of Aryl Carboxylic Acids and Esters from Phenols through a Pd-Catalyzed Insertion of Carbon Monoxide.

    Science.gov (United States)

    Fang, Wan-Yin; Leng, Jing; Qin, Hua-Li

    2017-09-05

    A one-pot Pd-catalyzed carbonylation of phenols into their corresponding aryl carboxylic acids and esters through the insertion of carbon monoxide has been developed. This procedure offers a direct synthesis of aryl carboxylic acids and esters from inexpensive and abundant starting materials (phenols, SO2 F2 and CO) under mild conditions. This method tolerates a broad range of functional groups and is also applicable for the modification of complicated natural products. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  1. Synthesis, characterisation and antimicrobial activity of (5-bromo-5-nitro-2-oxido-1,3,2-dioxaphosphinan-2-yl amino acid esters

    Directory of Open Access Journals (Sweden)

    CIRANDUR SURESH REDDY

    2011-05-01

    Full Text Available Synthesis of a new series of (5-bromo-5-nitro-2-oxido-1,3,2-dioxaphosphinan-2-ylamino acid esters (3a–l was accomplished via a two step process, which involves the prior preparation of the monochloride intermediate (2 and its subsequent reaction with the amino acid esters in dry tetrahydrofuran in the presence of triethylamine at reflux temperature. The title compounds (3a–l structures were established by analytical, IR, 1H-, 13C- and 31P-NMR, and mass spectral data. They exhibited significant antibacterial and antifungal activity.

  2. 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.

  3. Recent advances in the biomedical applications of fumaric acid and its ester derivatives: The multifaceted alternative therapeutics.

    Science.gov (United States)

    Das, Ratul Kumar; Brar, Satinder Kaur; Verma, Mausam

    2016-04-01

    Several lines of evidence have demonstrated the potential biomedical applications of fumaric acid (FA) and its ester derivatives against many human disease conditions. Fumaric acid esters (FAEs) have been licensed for the systemic treatment of the immune-mediated disease psoriasis. Biogen Idec Inc. announced about the safety and efficacy of the formulation FAE (BG-12) for treating RRMS (relapsing-remitting multiple sclerosis). Another FAE formulation DMF (dimethyl fumarate) was found to be capable of reduction in inflammatory cardiac conditions, such as autoimmune myocarditis and ischemia and reperfusion. DMF has also been reported to be effective as a potential neuroprotectant against the HIV-associated neurocognitive disorders (HAND). Many in vivo studies carried out on rat and mice models indicated inhibitory effects of fumaric acid on carcinogenesis of different origins. Moreover, FAEs has emerged as an important matrix ingredient in the fabrication of biodegradable scaffolds for tissue engineering applications. Drug delivery vehicles composed of FAEs have shown promising results in delivering some leading drug molecules. Apart from these specific applications and findings, many more studies on FAEs have revealed new therapeutic potentials with the scope of clinical applications. However, until now, this scattered vital information has not been written into a collective account and analyzed for minute details. The aim of this paper is to review the advancement made in the biomedical application of FA and FAEs and to focus on the clinical investigation and molecular interpretation of the beneficial effects of FA and FAEs. Copyright © 2015 Institute of Pharmacology, Polish Academy of Sciences. Published by Elsevier Urban & Partner Sp. z o.o. All rights reserved.

  4. Biosynthesis of D-alanyl-lipoteichoic acid by Lactobacillus casei: interchain transacylation of D-alanyl ester residues

    Energy Technology Data Exchange (ETDEWEB)

    Childs, W.C. 3d.; Taron, D.J.; Neuhaus, F.C.

    1985-06-01

    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-(/sup 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.

  5. Biocatalytic potential of lipase from Staphylococcus sp. MS1 for transesterification of jatropha oil into fatty acid methyl esters.

    Science.gov (United States)

    Sharma, Monika; Singh, Shelley Sardul; Maan, Pratibha; Sharma, Rohit

    2014-11-01

    An extracellular lipase producing isolate Staphylococcus sp. MS1 was optimized for lipase production and its biocatalytic potential was assessed. Medium with tributyrin (0.25 %) and without any exogenous inorganic nitrogen source was found to be optimum for lipase production from Staphylococcus sp. MS1. The optimum pH and temperature for lipase production were found to be pH 7 and 37 °C respectively, showing lipase activity of 37.91 U. It showed good lipase production at pH 6-8. The lipase was found to be stable in organic solvents like hexane and petroleum ether, showing 98 and 88 % residual activity respectively. The biotransformation using the concentrated enzyme in petroleum ether resulted in the synthesis of fatty acid methyl esters like methyl oleate, methyl palmitate and methyl stearate. Thus, the lipase under study has got the potential to bring about transesterification of oils into methyl esters which can be exploited for various biotechnological applications.

  6. Development and characterisation of chondroitin sulfate- and hyaluronic acid-incorporated sorbitan ester nanoparticles as gene delivery systems.

    Science.gov (United States)

    Fernandez-Piñeiro, I; Pensado, A; Badiola, I; Sanchez, A

    2018-01-17

    Glycosaminoglycans (GAGs) are natural polymers that are broadly used in gene delivery systems to increase stability as well as decrease toxicity and nonspecific interactions, thereby increasing transfection efficiency. In this work, we propose sorbitan ester-based lipid nanoparticles (SENS) functionalised with the GAGs chondroitin sulfate (CS) and hyaluronic acid (HA) as gene delivery systems. For this purpose, we describe the design and evaluation of these nanosystems loaded with plasmid DNA, including an evaluation of their physicochemical characteristics, stability properties, ability to protect and efficiently transfect cells with Enhanced Green Fluorescent Protein plasmid (pEGFP) in vitro, and biocompatibility both in vitro and in vivo. We confirm that molecules with high biological value and targeting potential, such as HA and CS, can be successfully incorporated into our recently developed sorbitan ester-based nanoparticles (SENS) and that this incorporation leads to effective stabilisation of both nanosystems as well as protects plasmid DNA. We demonstrated that the aforementioned incorporation of HA and CS enables long-term stability of the nanosystems in both liquid and lyophilised states, which is a remarkable property that can aid in their transfer to industry. The ability of these functionalised nanosystems to transfect the A549 cell line without compromising cell viability was also shown, as well as their innocuous safety profile in vivo. Thus, we provide valuable evidence of the suitable properties and potential of these hybrid nanoparticles as gene delivery systems. Copyright © 2018. Published by Elsevier B.V.

  7. Ether- and Ester-Bound iso-Diabolic Acid and Other Lipids in Members of Acidobacteria Subdivision 4

    Science.gov (United States)

    Rijpstra, W. Irene C.; Hopmans, Ellen C.; Foesel, Bärbel U.; Wüst, Pia K.; Overmann, Jörg; Tank, Marcus; Bryant, Donald A.; Dunfield, Peter F.; Houghton, Karen; Stott, Matthew B.

    2014-01-01

    Recently, iso-diabolic acid (13,16-dimethyl octacosanedioic acid) has been identified as a major membrane-spanning lipid of subdivisions 1 and 3 of the Acidobacteria, a highly diverse phylum within the Bacteria. This finding pointed to the Acidobacteria as a potential source for the bacterial glycerol dialkyl glycerol tetraethers that occur ubiquitously in peat, soil, lakes, and hot springs. Here, we examined the lipid composition of seven phylogenetically divergent strains of subdivision 4 of the Acidobacteria, a bacterial group that is commonly encountered in soil. Acid hydrolysis of total cell material released iso-diabolic acid derivatives in substantial quantities (11 to 48% of all fatty acids). In contrast to subdivisions 1 and 3 of the Acidobacteria, 6 out of the 7 species of subdivision 4 (excepting “Candidatus Chloracidobacterium thermophilum”) contained iso-diabolic acid ether bound to a glycerol in larger fractional abundance than iso-diabolic acid itself. This is in agreement with the analysis of intact polar lipids (IPLs) by high-performance liquid chromatography-mass spectrometry (HPLC-MS), which showed the dominance of mixed ether-ester glycerides. iso-Diabolic acid-containing IPLs were not identified, because these IPLs are not released with a Bligh-Dyer extraction, as observed before when studying lipid compositions of subdivisions 1 and 3 of the Acidobacteria. The presence of ether bonds in the membrane lipids does not seem to be an adaptation to temperature, because the five mesophilic isolates contained a larger amount of ether lipids than the thermophile “Ca. Chloracidobacterium thermophilum.” Furthermore, experiments with Pyrinomonas methylaliphatogenes did not reveal a major influence of growth temperature over the 50 to 69°C range. PMID:24928878

  8. Fumaric acid esters in combination with a 6-week course of narrow-band UVB provides for an accelerated response as compared to fumaric acid esters monotherapy in patients with moderate to severe plaque psoriasis: A randomized prospective clinical study.

    Science.gov (United States)

    Tzaneva, S; Geroldinger, A; Trattner, H; Tanew, A

    2017-11-08

    Fumaric acid esters are (FAE) safe and effective in patients with moderate to severe psoriasis but have a slow onset of action. A short-term combination with narrow-band UVB (NB UVB) may substantially accelerate the therapeutic response in the induction phase of treatment. To assess the synergistic effect of a 6-week course of NB UVB phototherapy in addition to fumaric acid esters in adult patients with moderate to severe plaque psoriasis. In this randomized, assessor-blinded trial patients with a Psoriasis Area and Severity Index (PASI) of ≥10 and a body surface area (BSA) of ≥10 were randomized to either monotherapy with FAE (n=16) or a combination of FAE with NB UVB (n=14). The primary outcome parameter of the study was the mean PASI reduction after 6 weeks of treatment. In addition, the PASI 75 response, the psoriasis log-based area and severity index (PLASI) and the dermatology life quality index (DLQI) were assessed as secondary outcome measures. Thirty patients (19 males, 11 females; median age 52 years, IQR 36;56) were analysed. The mean reduction in PASI after 6 weeks was significantly greater with the combination treatment as compared to FAE monotherapy (p=0.016). This was paralleled by a much faster improvement in DLQI in the combination group than in the FAE monotherapy group. Adding a 6-week course of narrow-band UVB to FAE both accelerates and augments the therapeutic response during the early phase of treatment and increases quality of life in patients with moderate-to-severe plaque psoriasis. This article is protected by copyright. All rights reserved. This article is protected by copyright. All rights reserved.

  9. 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.

  10. 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.

  11. 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.

  12. Improvement of glucoamylase production for raw-starch digestion in Aspergillus niger F-01 by maltose stearic acid ester.

    Science.gov (United States)

    Sun, Haiyan; Peng, Ming

    2017-04-01

    To investigate the role of maltose stearic acid ester (MSAE) for improving raw-starch-digesting glucoamylase (RSDG) production by Aspergillus niger F-01 and its regulatory mechanism. RSDG activity was enhanced 8.3-fold by adding 5 g MSAE to 1 l basal medium at the beginning of the culture. RSDG biosynthesis nearly ceased by adding 100 μg actinomycin D/ml or 50 μg cycloheximide/ml in a 48 h culture in the basal medium. RSDG biosynthesis was restarted by adding MSAE in the culture repressed by actinomycin D. No revival of RSDG synthesis was observed by adding MSAE in the culture repressed by cycloheximide. MSAE improved RSDG production in A. niger by inducing the transcription of RSDG.

  13. Synergistic Effects of Copper and Butylic Ester of 2,4-Dichlorophenoxyacetic Acid (Esternon Ultra on Amphibian Embryos

    Directory of Open Access Journals (Sweden)

    Jorge Herkovits

    2006-12-01

    Full Text Available Cu2+ and butylic ester of 2,4-Dichlorophenoxyacetic acid as Esternon Ultra (2,4-D toxicity on Bufo arenarum embryos were evaluated by means of a short-term chronic toxicity test (AMPHITOX. The NOEC values for Cu and 2,4-D were 0.02 mg/L and 2 mg/L respectively. The toxicity profile curves for Cu and 2,4-D were reported. The interactions of the metal and the herbicide were evaluated by combined treatments with different concentrations of Cu and 2,4-D. Although in all cases, a synergistic effect between these chemicals was observed, the combination of concentrations exerting low level effects in isolated treatments resulted in more adverse embryonic survival. Considering that both products are extensively used in agroecosystems, this fact could be of concern for non target species like amphibians.

  14. Adsorption of phthalic acid esters (PAEs) by amphiphilic polypropylene nonwoven from aqueous solution: the study of hydrophilic and hydrophobic microdomain.

    Science.gov (United States)

    Zhou, Xiangyu; Wei, Junfu; Zhang, Huan; Liu, Kai; Wang, Han

    2014-05-30

    A kind of amphiphilic polypropylene nonwoven with hydrophilic and hydrophobic microdomain was prepared through electron beam induced graft polymerization and subsequent ring opening reaction and then utilized in the adsorption of phthalic acid esters (PAEs). To elucidate the superiority of such amphiphilic microdomain, a unique structure without hydrophilic part was constructed as comparison. In addition, the adsorption behaviors including adsorption kinetics, isotherms and pH effect were systematically investigated. The result indicated that the amphiphilic structure and the synergy between hydrophilic and hydrophobic microdomain could considerably improve the adsorption capacities, rate and affinity. Particularly the existence of hydrophilic microdomain could reduce the diffusion resistance and energy barrier in the adsorption process. These adsorption results showed that the amphiphilic PP nonwoven have the potential to be used in environmental application. Copyright © 2014 Elsevier B.V. All rights reserved.

  15. Biocatalytic Resolution of Rac-α-Ethyl-2-Oxo-Pyrrolidineacetic Acid Methyl Ester by Immobilized Recombinant Bacillus cereus Esterase.

    Science.gov (United States)

    Zheng, Jian-Yong; Liu, Yin-Yan; Luo, Wei-Feng; Zheng, Ren-Chao; Ying, Xiang-Xian; Wang, Zhao

    2016-04-01

    A new esterase-producing strain (Bacillus cereus WZZ001) which exhibiting high hydrolytic activity and excellent enantioselectivity on rac-α-ethyl-2-oxo-pyrrolidineacetic acid methyl ester (R, S-1) has been isolated from soil sample by our laboratory. In this study, the stereoselective hydrolysis of (R, S-1) was performed using the recombinant Bacillus cereus esterase which expressed in Escherichia coli BL21 (DE3). Under the optimized conditions of pH 8.0, 35 °C, and concentration of substrate 400 mM, a successful enzymatic resolution was achieved with an e.e. s of 99.5 % and conversion of 49 %. Immobilization considerably increased the reusability of the recombinant esterase; the immobilized enzyme showed excellent reusability during 6 cycles of repeated 2 h reactions at 35 °C. Thereby, it makes the recombinant B. cereus esterase a usable biocatalyst for industrial application.

  16. Systemic antipsoriatic combination therapy with fumaric acid esters for plaque-type psoriasis: report on 17 cases.

    Science.gov (United States)

    Wilsmann-Theis, Dagmar; Frambach, Yvonne; Philipp, Sandra; Weyergraf, Ansgar J; Jacobi, Arnd; Mössner, Rotraut; Gerdes, Sascha

    2015-01-01

    In the literature as well as in existing psoriasis guidelines, only little evidence is available on combination regimens with systemic antipsoriatic agents. However, if systemic monotherapy is not efficacious enough to control the disease, a combination therapy might be necessary. To evaluate the use of fumaric acid esters (FAEs) in combination with other antipsoriatic agents in 6 specialized dermatological departments in Germany. A systematic retrospective chart review of patients receiving FAEs was performed. A total of 17 cases of patients receiving FAEs combined with at least one other systemic therapy (methotrexate, acitretin, etanercept, cyclosporine, leflunomide and infliximab) to treat psoriasis or psoriatic arthritis were identified. FAEs can be combined in an off-label setting with conventional as well as biological agents to treat recalcitrant psoriasis or psoriatic arthritis. Safety monitoring should be taken seriously as no controlled data for these combination regimens exist. © 2015 S. Karger AG, Basel.

  17. Synthesis and photopolymerization kinetics of a novel oxime ester sulfonic acid photoacid generator

    Science.gov (United States)

    Pang, Yu-Lian; Zou, Ying-Quan

    2012-03-01

    On the basis of the chemical structure of (5-Hydroxyimino-5H-thiophen-2-ylidene)-phenylacetonitrile, we synthesized a novel sulfonic oxime ester photoacid generator named (5-Ptoluenesulfonyloxyimino- 5H-thiophen-2-ylidene)-phenyl-acetonitrile (TTPA),which was an efficient Photoacid generator (PAG) for 405nm violet laser imaging system.It was synthesized from 2- Nitrothiophen ,Phenylqceto-nitrile and P-toluenesulfonyl chloride.TTPA was characterized by FTIR1HNMR and UV absorption spectra. Real time infrared spectroscopy(RTIR) was used to investigate the effect of different monomers system and different concentrations of TTPA on the polymerization kinetics. The results showed that with the concentration of TTPA increase, with limits, the rate of photopolymerization(Rp) and final double bond conversion increased and the induction period shortened.

  18. Copolymerization of Ethylene and Vinyl Amino Acidic Ester Catalyzed by Titanium and Zirconium Complexes

    Directory of Open Access Journals (Sweden)

    Jing Wang

    2015-10-01

    Full Text Available A series of titanium and zirconium complexes with ligands based on di-isopropyl phosphorus-phenylamine and their derivatives were synthesized and characterized. These catalysts were utilized to catalyze the copolymerization of ethylene with N-acetyl-O-(dec-9-enyl-L-tyrosine ethyl ester with high catalytic activity of 6.63 × 104 g P (mol Ti−1 h−1 after activation by methylaluminoxane (MAO. The effects of ligand structure, metal atoms (Ti, Zr and polymerization conditions were investigated in detail. The obtained polymers were characterized by 13C-NMR, DSC, FT-IR, and GPC. The results showed that the obtained copolymer had a high comonomer incorporation rate of 2.56 mol % within the copolymer chain. The melting temperature of the copolymer was up to 138.9 °C, higher than that of the obtained homopolyethylene.

  19. 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.

  20. 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.

  1. 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.

  2. Palladium-catalyzed allylic transposition of (allyloxy) iminodiazaphospholidines: a formal [3,3]-aza-phospha-oxa-Cope sigmatropic rearrangement for the stereoselective synthesis of allylic amines.

    Science.gov (United States)

    Lee, Ernest E; Batey, Robert A

    2005-10-26

    The synthesis of N-protected allylic amines has been achieved utilizing a palladium(II)-catalyzed, [3,3]-rearrangement of (allyloxy) iminodiazaphospholidines. This [3,3]-aza-phospha-oxa-Cope sigmatropic rearrangement reaction is thermodynamically driven by a P=N to P=O interconversion and is an alternative to the Overman rearrangement. The overall process involves the nucleophilic displacement of an allylic alcohol onto a P(III) precursor, followed by a Staudinger reaction to generate the (allyloxy) iminodiazaphospholidine precursors. Pd(II)-catalyzed [3,3]-aza-phospha-oxa-Cope rearrangement then gives a phosphoramide, which is readily hydrolyzed under acidic conditions to yield allylic amine derivatives. Pd(II) catalysis is believed to occur in a fashion analogous to that of the rearrangement of allylic imidates. The scope of racemic, diastereoselective, and enantioselective variants of this rearrangement is described. The use of chiral diamine auxiliaries in diastereoselective rearrangements is reported. Rearrangement of chiral N,N'-dimethyl cyclohexanediamine derived diazaphospholidines gives rise to phosphoramides with moderate diastereoselectivities (up to 3.5:1 dr). The same major diastereomeric product in these rearrangements was prepared irrespective of the starting allylic alcohol geometry. An enantioselective variant of the reaction was demonstrated for the rearrangement of cis-(allyloxy) iminodiazaphospholidines with cobalt oxazoline palladacycle (COP-X) catalysts (5 mol %) in high yield and enantioselectivity (up to 96% ee).

  3. Highly enantio- and diastereoselective allylic alkylation of Morita-Baylis-Hillman carbonates with allyl ketones

    KAUST Repository

    Tong, Guanghu

    2013-05-17

    The asymmetric allylic alkylation of Morita-Baylis-Hillman (MBH) carbonates with allyl ketones has been developed. The α-regioselective alkylation adducts, containing a hexa-1,5-diene framework with important synthetic value, were achieved in up to 83% yield, >99% ee, and 50:1 dr by using a commercially available Cinchona alkaloid as the catalyst. From the allylic alkylation adduct, a cyclohexene bearing two adjacent chiral centers was readily prepared. © 2013 American Chemical Society.

  4. Identification of the catalytic residues of alpha-amino acid ester hydrolase from Acetobacter turbidans by labeling and site-directed mutagenesis

    NARCIS (Netherlands)

    Polderman - Tijmes, Jolanda j.; Jekel, Peter A.; Jeronimus-Stratingh, CM; Bruins, Andries P.; van der Laan, Jan-Metske; Sonke, Theo; Janssen, Dick B.

    2002-01-01

    The alpha-amino acid ester hydrolase from Acetobacter turbidans ATCC 9325 is capable of hydrolyzing and synthesizing the side chain peptide bond in beta-lactam antibiotics. Data base searches revealed that the enzyme contains an active site serine consensus sequence Gly-X-Ser-Tyr-X-Gly that is also

  5. Environmental exposure to the plasticizer 1,2-cyclohexane dicarboxylic acid, diisononyl ester (DINCH) in U.S. adults (2000-2012).

    Science.gov (United States)

    Silva, Manori J; Jia, Tao; Samandar, Ella; Preau, James L; Calafat, Antonia M

    2013-10-01

    1,2-Cyclohexane dicarboxylic acid, diisononyl ester (DINCH) is a complex mixture of nine carbon branched-chain isomers. It has been used in Europe since 2002 as a plasticizer to replace phthalates such as di(2-ethylhexyl)phthalate (DEHP) and diisononyl phthalate (DINP). Urinary concentrations of the oxidative metabolites of DINCH, namely cyclohexane-1,2-dicarboxylic acid-monocarboxy isooctyl ester (MCOCH); cyclohexane-1,2-dicarboxylic acid-mono(oxo-isononyl) ester (MONCH); and cyclohexane-1,2-dicarboxylic acid-mono(hydroxy-isononyl) ester (MHNCH), can potentially be used as DINCH exposure biomarkers. The concentrations of MCOCH, MONCH and MHNCH were measured by online solid phase extraction-high performance liquid chromatography-tandem mass spectrometry in urine collected in 2000 (n=114), 2001 (n=57), 2007 (n=23), 2009 (n=118), 2011 (n=94) and 2012 (n=121) from convenience groups of anonymous U.S. adult volunteers with no known DINCH exposure. None of the DINCH metabolites were detected in samples collected in 2000 and 2001. Only one sample collected in 2007 had measureable concentrations of DINCH metabolites. The detection rate for all three metabolites increased from 2007 to 2012. The presence of oxidative metabolites of DINCH in urine suggests that these oxidative metabolites can be used as DINCH biomarkers for exposure assessment even at environmental exposure levels. Published by Elsevier Inc.

  6. Plasma Cholesteryl Ester Fatty Acids do not Mediate the Association of Ethnicity with Type 2 Diabetes: Results From the HELIUS Study

    NARCIS (Netherlands)

    Muilwijk, Mirthe; Celis-Morales, Carlos; Nicolaou, Mary; Snijder, Marieke B.; Gill, Jason M. R.; van Valkengoed, Irene G. M.

    2018-01-01

    Scope: Ethnic minority groups have a higher risk of type 2 diabetes (T2D) than the host population. Our aim is to identify whether plasma cholesteryl ester fatty acids (CEFA) mediate the ethnic differences in type 2 diabetes. Methods and results: We included 202 Dutch, 206 South-Asian Surinamese,

  7. Water-triggered self-assembly polycondensation for the one-pot synthesis of cyclomatrix polyphosphazene nanoparticles from amino acid ester.

    Science.gov (United States)

    Huang, Zhangjun; Chen, Shuangshuang; Lu, Xuemin; Lu, Qinghua

    2015-05-14

    Water-triggered self-assembly polycondensation was proposed for preparation of cyclomatrix polyphosphazene nanoparticles from amino acid esters, and a critical solubility parameter was found to determine whether the nanoparticles were formed. Based on this rule, we also investigated the control of the size of its nanoparticles.

  8. Asymmetric construction of binaphthyl by the chiral diether-mediated conjugate addition of naphthyllithium to naphthalenecarboxylic acid 2,6-di-t-butyl-4-methoxyphenyl ester.

    Science.gov (United States)

    Shindo, Mitsuru; Yamamoto, Yasutomo; Yamada, Ken-Ichi; Tomioka, Kiyoshi

    2009-07-01

    Two ways for the synthesis of binaphthyl were examined based on a chiral ligand-mediated asymmetric conjugate addition of 1-naphthyllithium to naththalene-2-carboxylic acid 2,6-di-t-butyl-4-methoxyphenyl esters. The one pot method by conjugate addition-elimination gave a relatively higher enantioselectivity than the two step synthesis based on addition and subsequent oxidative aromatization.

  9. A Green Solventless Protocol for the Synthesis of β-Enaminones and β-Enamino Esters Using Silica Sulfuric Acid as a Highly Efficient, Heterogeneous and Reusable Catalyst

    Directory of Open Access Journals (Sweden)

    Alireza Hasaninejad

    2010-01-01

    Full Text Available Silica sulfuric acid is utilized as a green, highly efficient, heterogeneous and recyclable catalyst for the preparation of β-enaminones and β-enamino esters from amines and β-dicarbonyl compounds under solvent-free conditions at 80 °C. Using this method, the title compounds are produced in high to excellent yields and in short reaction times.

  10. Characteristics of retention and enthalpies of sorption from the gas phase of esters of trimethylolpropane and C2-C5 acids on DB-1 stationary phase

    Science.gov (United States)

    Krasnykh, E. L.; Aleksandrov, A. Yu.; Sokolova, A. A.; Levanova, S. V.

    2017-02-01

    Characteristics of retention and their temperature dependences, along with the thermodynamic characteristics of sorption on DB-1 nonpolar phase, are determined in the temperature range of 220-280°C for 21 mono-, di-, and trisubstituted esters of trimethylolpropane and monobasic acids with a variety of structures containing from 2 to 6 carbon atoms.

  11. 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.

  12. Optimization of enzymatic synthesis of palm-based kojic acid ester using response surface methodology.

    Science.gov (United States)

    Ashari, Siti Efliza; Mohamad, Rosfarizan; Ariff, Arbakariya; Basri, Mahiran; Salleh, Abu Bakar

    2009-01-01

    Kojic acid monooleate is a fatty acid derivative of kojic acid which can be widely used as a skin whitening agent in a cosmetic applications. In avoiding any possible harmful effects from chemically synthesized product, the enzymatic synthesis appears to be the best way to satisfy the consumer demand nowadays. The ability of immobilized lipase from Rhizomucor meihei (lipozyme RMIM) to catalyze the direct esterification of kojic acid and oleic acid was investigated. Response Surface Methodology (RSM) and 5-level-4-factor central composite rotatable were employed to evaluate the effects of synthesis parameters such as enzyme amount (0.1-0.4 g), temperature (30-60 degrees C), substrate molar ratio (1-4 mmol, kojic acid:oleic acid) and reaction time (24-48 h) on percentage molar conversion to kojic acid monooleate. Analysis of the product using TLC, GC and FTIR showed the presence of kojic acid monooleate. The optimal conditions for the enzymatic reaction were obtained after analysis with backward elimination using 0.17 g of enzyme and 4 mmol of substrate at 52.50 degrees C for 42 h. Under these conditions the esterification percentage was 37.21%. The results demonstrated that response surface methodology can be applied effectively to optimize the lipase-catalysed synthesis of kojic acid monooleate. The optimum conditions can be used to scale up the process.

  13. Two-step synthesis of fatty acid ethyl ester from soybean oil catalyzed by Yarrowia lipolytica lipase

    Directory of Open Access Journals (Sweden)

    Chen Jinnan

    2011-03-01

    Full Text Available Abstract Background Enzymatic biodiesel production by transesterification in solvent media has been investigated intensively, but glycerol, as a by-product, could block the immobilized enzyme and excess n-hexane, as a solution aid, would reduce the productivity of the enzyme. Esterification, a solvent-free and no-glycerol-release system for biodiesel production, has been developed, and two-step catalysis of soybean oil, hydrolysis followed by esterification, with Yarrowia lipolytica lipase is reported in this paper. Results First, soybean oil was hydrolyzed at 40°C by 100 U of lipase broth per 1 g of oil with approximately 30% to 60% (vol/vol water. The free fatty acid (FFA distilled from this hydrolysis mixture was used for the esterification of FFA to fatty acid ethyl ester by immobilized lipase. A mixture of 2.82 g of FFA and equimolar ethanol (addition in three steps were shaken at 30°C with 18 U of lipase per 1 gram of FFA. The degree of esterification reached 85% after 3 hours. The lipase membranes were taken out, dehydrated and subjected to fresh esterification so that over 82% of esterification was maintained, even though the esterification was repeated every 3 hours for 25 batches. Conclusion The two-step enzymatic process without glycerol released and solvent-free demonstrated higher efficiency and safety than enzymatic transesterification, which seems very promising for lipase-catalyzed, large-scale production of biodiesel, especially from high acid value waste oil.

  14. Enhancement of the lipid productivity and fatty acid methyl ester profile of Chlorella vulgaris by two rounds of mutagenesis.

    Science.gov (United States)

    Sarayloo, Ehsan; Simsek, Salim; Unlu, Yigit Sabri; Cevahir, Gul; Erkey, Can; Kavakli, Ibrahim Halil

    2017-12-02

    In this study, we applied a second round of random mutagenesis using ethyl methanesulfonate to further increase the lipid productivity of a Chlorella vulgaris mutant strain. We generated a mutant (UV715-EMS25) with a lipid content and biomass that were respectively 67% and 35% higher than those of the wild type (WT). The highest achieved lipid productivity in UV715-EMS25 was 91 mg L-1 day-1. Gas chromatography-mass spectrophotometric analysis revealed that the fatty acid methyl ester content of the mutant was 3.9-fold higher compared with that of WT cells. Amounts of saturated and monounsaturated fatty acids were also higher in the mutant, while the total amounts of polyunsaturated fatty acids were lower. Finally, the mutant displayed superior lipid productivity compared with the WT during pilot-scale cultivation in a flat panel photobioreactor. All these results demonstrate that UV715-EMS25 is highly suitable for biodiesel production. Copyright © 2017 Elsevier Ltd. All rights reserved.

  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...... 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...... 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...

  16. 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......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...

  17. 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

  18. Optical measurements of the phase diagrams of Langmuir monolayers of fatty acid, ester, and alcohol mixtures by Brewster-angle microscopy

    Science.gov (United States)

    Teer, Ellis; Knobler, Charles M.; Lautz, Carsten; Wurlitzer, Stefan; Kildae, John; Fischer, Thomas M.

    1997-02-01

    Surface pressure-temperature phase diagrams have been determined by Brewster-angle microscopy for Langmuir monolayers of heneicosanoic acid with the esters methyl and ethyl heneicosanoate and octadecanoic acid with methyl, ethyl, and propyl octadecanoate. The behavior is similar to that found previously in mixtures of an acid and an alcohol. In each case with increasing ester concentration the L2/L2' phase boundary moves toward lower pressure and higher temperature while the L2/Ov boundary moves toward lower pressure and lower temperature. The L2' and Ov phases eventually merge and the boundary with the L2 phase moves to zero pressure. The phase diagram of eicosyl acetate is similar to that of the fatty acids. We attribute the variations in the diagrams to the extent of hydrogen bonding between the head group and the subphase.

  19. 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.)

  20. Accurate and Reliable Quantification of Total Microalgal Fuel Potential as Fatty Acid Methyl Esters by in situ Transesterfication

    Energy Technology Data Exchange (ETDEWEB)

    Laurens, L. M. L.; Quinn, M.; Van Wychen, S.; Templeton, D. W.; Wolfrum, E. J.

    2012-04-01

    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.