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Sample records for acid ethyl ester

  1. 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...

  2. Orthogonal Fatty Acid Biosynthetic Pathway Improves Fatty Acid Ethyl Ester Production in Saccharomyces cerevisiae.

    Science.gov (United States)

    Eriksen, Dawn T; HamediRad, Mohammad; Yuan, Yongbo; Zhao, Huimin

    2015-07-17

    Fatty acid ethyl esters (FAEEs) are a form of biodiesel that can be microbially produced via a transesterification reaction of fatty acids with ethanol. The titer of microbially produced FAEEs can be greatly reduced by unbalanced metabolism and an insufficient supply of fatty acids, resulting in a commercially inviable process. Here, we report on a pathway engineering strategy in Saccharomyces cerevisiae for enhancing the titer of microbially produced FAEEs by providing the cells with an orthogonal route for fatty acid synthesis. The fatty acids generated from this heterologous pathway would supply the FAEE production, safeguarding endogenous fatty acids for cellular metabolism and growth. We investigated the heterologous expression of a Type-I fatty acid synthase (FAS) from Brevibacterium ammoniagenes coupled with WS/DGAT, the wax ester synthase/acyl-coenzyme that catalyzes the transesterification reaction with ethanol. Strains harboring the orthologous fatty acid synthesis yielded a 6.3-fold increase in FAEE titer compared to strains without the heterologous FAS. Variations in fatty acid chain length and degree of saturation can affect the quality of the biodiesel; therefore, we also investigated the diversity of the fatty acid production profile of FAS enzymes from other Actinomyces organisms. PMID:25594225

  3. Circumvention of defective neutral amino acid transport in Hartnup disease using tryptophan ethyl ester.

    OpenAIRE

    Jonas, A J; Butler, I J

    1989-01-01

    Tryptophan ethyl ester, a lipid-soluble tryptophan derivative, was used to bypass defective gastrointestinal neutral amino acid transport in a child with Hartnup disease. The child's baseline tryptophan concentrations in serum (20 +/- 6 microM) and cerebrospinal fluid (1.0 +/- 0.2 microM) were persistently less than 50% of normal values. Cerebrospinal fluid 5-hydroxyindoleacetic acid (5-HIAA), a serotonin metabolite, was also less than 50% of normal (21 +/- 2 ng/ml). Serum tryptophan concentr...

  4. Circumvention of defective neutral amino acid transport in Hartnup disease using tryptophan ethyl ester.

    Science.gov (United States)

    Jonas, A J; Butler, I J

    1989-07-01

    Tryptophan ethyl ester, a lipid-soluble tryptophan derivative, was used to bypass defective gastrointestinal neutral amino acid transport in a child with Hartnup disease. The child's baseline tryptophan concentrations in serum (20 +/- 6 microM) and cerebrospinal fluid (1.0 +/- 0.2 microM) were persistently less than 50% of normal values. Cerebrospinal fluid 5-hydroxyindoleacetic acid (5-HIAA), a serotonin metabolite, was also less than 50% of normal (21 +/- 2 ng/ml). Serum tryptophan concentrations increased only modestly and briefly after an oral challenge with 200 mg/kg of oral L-tryptophan, reflecting the absorptive defect. An oral challenge with 200 mg/kg of tryptophan ethyl ester resulted in a prompt increase in serum tryptophan to a peak of 555 microM. Sustained treatment with 20 mg/kg q6h resulted in normalization of serum (66 +/- 15 microM) and cerebrospinal fluid tryptophan concentrations (mean = 2.3 microM). Cerebrospinal fluid 5-HIAA increased to more normal concentrations (mean = 33 ng/ml). No toxicity was observed over an 8-mo period of treatment, chronic diarrhea resolved, and body weight, which had remained unchanged for 7 mo before ester therapy, increased by approximately 26%. We concluded that tryptophan ethyl ester is effective at circumventing defective gastrointestinal neutral amino acid transport and may be useful in the treatment of Hartnup disease. PMID:2472426

  5. 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)...

  6. 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 chai...

  7. CHEMOTHERAPEUTIC POLYMERS ⅩⅩⅢ SYNTHESIS AND ANTITUMOR ACTIVITY OF POLYPHOSPHATES CONTAINING BOTH NUCLEIC ACID BASE AND PHOSPHONOACETIC ACID ETHYL ESTER

    Institute of Scientific and Technical Information of China (English)

    ZHUO Renxi; LIU Zhenghua; LI Li

    1989-01-01

    Eight new polyphosphates containing both nucleic acid base and phosphonoacetic acid ethyl ester were synthesized by the polycondensation of P, P- dichloride of phosphonoacetic acid ethyl ester with 1, 3-dihydroxyalkyl - 5 - fluorouracil, 1,3 - dihydroxyalkyl - uracil and 1, 3 - dihydroxyalkylthymine. These polyphosphates were tested against Ehrlich Ascites Carcinoma in mice. Polymer Ⅱa and Ⅱc exhibited excellent antitumor activity. Ⅱc also showed lower toxicity.

  8. Gas chromatography determination of fatty acid alkyl esters (methyl and ethyl in the presence of mono., di- and triglycerides

    Directory of Open Access Journals (Sweden)

    Paulo César Narváez Rincón

    2010-04-01

    Full Text Available Determining fatty acid methyl or ethyl esters, in the presence of mono-, di- and tri glycerides, is very important when studying fatty compounds' methanolysis or ethanolysis, as well as for controlling the quality of petrochemical products. This work presents a useful technique for determining fatty acids methyl or ethyl esters by high temperature gas chromastography in the presence of mono-, di- and triglycerides. Samples were silylated with N, O-bis (trimethylsilyl trifluroacetamide (BSTFA and then passed throught a 12m HT5 column coated with a phenyl-polysiloxane-carborane film. Standard methyl and ethyl palmitate, methyl and ethyl oleate, DL-palmitin, dipalmitin, tripalmitin and triolein solutions were used for calibrating the technique, using tricaprin as internal standard. Retention times and response factors were also determined. The results were employed in following-up palm oil methanolysis and ethanolysis reactions.

  9. Breast Cancer Genetic and Molecular Subtype Impacts Response to Omega-3 Fatty Acid Ethyl Esters.

    Science.gov (United States)

    Chen, Ching Hui; Fabian, Carol; Hursting, Stephen; deGraffenried, Linda A

    2016-01-01

    Epidemiological studies have correlated frequent omega-3 (n-3) fatty acid consumption with a lower risk for breast cancer; however, recent prospective studies have been less conclusive. Efforts in the preventive setting have focused on the use of n-3 fatty acids, and the pharmaceutical ethyl esters (EE) of these natural compounds, for high-risk patient populations. Limited understanding of specific mechanisms by which these agents function has hampered identification of the cancer subtype(s) that would gain the greatest therapeutic benefit. In this study, we investigated the in vitro effects of n-3 EEs in four distinct breast cancer subtypes and explored how they affect not only breast cancer cell survival but also modulate the nuclear factor kappa-light-chain enhancer of activated B cells (NF-κB) and peroxisome proliferator-activated receptor gamma signaling pathways. Similar to the high variance in response observed in human studies, we found that the effectiveness of n-3 EEs depends on the molecular characteristics of the MCF-7, CAMA-1, MDA-MB-231, and SKBR3 breast cancer cell lines and is closely associated with the suppression of NF-κB. These data strongly suggest that the use of n-3 fatty acids and their pharmaceutical ether esters in the prevention and therapeutic setting should be guided by specific tumor characteristics. PMID:27367296

  10. Combined use of fatty acid ethyl esters and ethyl glucuronide in hair for diagnosis of alcohol abuse: interpretation and advantages.

    Science.gov (United States)

    Pragst, F; Rothe, M; Moench, B; Hastedt, M; Herre, S; Simmert, D

    2010-03-20

    In this study the combined use of fatty acid ethyl esters (FAEE) and ethyl glucuronide (EtG) for diagnoses of chronically excessive alcohol abuse is investigated at 174 hair samples from driving ability examination, workplace testing and child custody cases for family courts and evaluated with respect to the basics of interpretation. Using the cut-off values of 0.50 ng/mg for FAEE and 25 pg/mg for EtG, both markers were in agreement in 75% of the cases with 103 negative and 28 positive results and there were 30 cases with FAEE positive and EtG negative and 13 cases with FAEE negative and EtG positive. As the theoretical basis of interpretation, the pharmacokinetics of FAEE and EtG is reviewed for all steps between drinking of ethanol to incorporation in hair with particular attention to relationships between alcohol dose and concentrations in hair. It is shown that the concentrations of both markers are essentially determined by the area under the ethanol concentration in blood vs. time curve AUC(EtOH), despite large inter-individual variations. It is demonstrated by calculation of AUC(EtOH) on monthly basis for moderate, risky and heavy drinking that AUC(EtOH) increases very strongly in the range between 60 and 120 g ethanol per day. This specific feature which is caused by the zero-order elimination of ethanol is a favorable prerequisite for a high discrimination power of the hair testing for alcohol abuse. From the consideration of the different profiles of FAEE and EtG along the hair and in agreement with the literature survey, a standardized hair segment 0-3 cm is proposed with cut-off values of 0.5 ng/mg for FAEE and 30 pg/mg for EtG. This improves also the agreement between FAEE and EtG results in the cases of the present study. A scheme for combined interpretation of FAEE and EtG is proposed which uses the levels of abstinence and the double of the cut-off values as criteria in addition to the cut-off's. Considering the large variations in the relationship

  11. Yarrowia lipolytica lipase Lip2: an efficient enzyme for the production of concentrates of docosahexaenoic acid ethyl ester.

    Science.gov (United States)

    Casas-Godoy, Leticia; Meunchan, Muchalin; Cot, Marlène; Duquesne, Sophie; Bordes, Florence; Marty, Alain

    2014-06-20

    The production of Omega-3 (ω-3) polyunsaturated fatty acids (PUFAs) rich in cis-4,7,10,13,16,19-docosahexaenoic acid (DHA) was studied using lipase-catalysed hydrolysis of a mixture of ethyl esters from tuna oil. Lipases from Yarrowia lipolytica (YLL2), Thermomyces lanuginosus (TLL) and Candida rugosa (CRL1, CRL3 and CRL4) were tested. C. rugosa lipases discriminated esters on the basis of their chain length, with less affinity for γ-linolenate, 11-eicosenoate, arachidonate, EPA, DPA and DHA ethyl esters. However, YLL2 and TLL improved discrimination towards DHA, as enzyme selectivity was shown to be mainly based on the position of the double bond closest to the carboxylic group. From the point of view of kinetics, purity and yield, YLL2 was the most effective lipase for DHA purification. Using this enzyme in an open reactor process resulted in the highest concentrations of DHA ethyl ester (77%) and ω-3 esters (81%) with a recovery of 94% and 77% respectively. PMID:24657346

  12. Engineering of chromosomal wax ester synthase integrated Saccharomyces cerevisiae mutants for improved biosynthesis of fatty acid ethyl esters.

    Science.gov (United States)

    Shi, Shuobo; Valle-Rodríguez, Juan Octavio; Siewers, Verena; Nielsen, Jens

    2014-09-01

    In recent years, significant advances have been made to engineer robust microbes for overproducing biochemical products from renewable resources. These accomplishments have to a large extend been based on plasmid based methods. However, plasmid maintenance may cause a metabolic burden on the host cell and plasmid-based overexpression of genes can result in genetically unstable strains, which contributes to loss in productivity. Here, a chromosome engineering method based on delta integration was applied in Saccharomyces cerevisiae for the production of fatty acid ethyl esters (FAEEs), which can be directly used as biodiesel and would be a possible substitute for conventional petroleum-based diesel. An integration construct was designed and integrated into chromosomal delta sequences by repetitive transformation, which resulted in 1-6 copies of the integration construct per genome. The corresponding FAEE production increased up to 34 mg/L, which is an about sixfold increase compared to the equivalent plasmid-based producer. The integrated cassette in the yeast genome was stably maintained in nonselective medium after deletion of RAD52 which is essential for efficient homologous recombination. To obtain a further increase of FAEE production, genes encoding endogenous acyl-CoA binding protein (ACB1) and a bacterial NADP(+)-dependent glyceraldehyde-3-phosphate dehydrogenase (gapN) were overexpressed in the final integration strain, which resulted in another 40% percent increase in FAEE production. Our integration strategy enables easy engineering of strains with adjustable gene copy numbers integrated into the genome and this allows for an easy evaluation of the effect of the gene copy number on pathway flux. It therefore represents a valuable tool for introducing and expressing a heterologous pathway in yeast. PMID:24752598

  13. 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 %.

  14. Ferulic acid ethyl ester diminished Complete Freund's Adjuvant-induced incapacitation through antioxidant and anti-inflammatory activity.

    Science.gov (United States)

    Cunha, Francisco Valmor Macedo; Gomes, Bruno de Sousa; Neto, Benedito de Sousa; Ferreira, Alana Rodrigues; de Sousa, Damião Pergentino; de Carvalho e Martins, Maria do Carmo; Oliveira, Francisco de Assis

    2016-01-01

    Ferulic acid ethyl ester (FAEE) is a derivate from ferulic acid which reportedly has antioxidant effect; however, its role on inflammation was unknown. In this study, we investigated the orally administered FAEE anti-inflammatory activity on experimental inflammation models and Complete Freund's Adjuvant (CFA)-induced arthritis in rats. CFA-induced arthritis has been evaluated by incapacitation model and radiographic knee joint records at different observation time. FAEE (po) reduced carrageenan-induced paw edema (p activities (p activity in radiographic records (p activity by inhibiting leukocyte migration, oxidative stress reduction, and pro-inflammatory cytokines.

  15. 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...

  16. 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

  17. Synthesis and Crystal Structure of 4-(4,6-Dimethoxylpyrimidin-2-yl)-3-thiourea Carboxylic Acid Ethyl Ester

    Institute of Scientific and Technical Information of China (English)

    ZHANG Yang; HUANG Jie; SONG Ji-Rong; REN Ying-Hui; XU Kang-Zhen

    2008-01-01

    4-(4,6-Dimethoxyl-pyrimidin-2-yl)-3-thiourea carboxylic acid ethyl ester was synthesized by the reaction of 2-amino-4,6-dimethoxyl pyrimidine,potassium thiocyanate and methyl chloroformate in ethyl acetate.Single crystals suitable for X-ray measurement were obtained by recrystallization with the solvent of dimethyl formamidc at room temperature.The crystal structure was determined by X-ray diffraction analysis.Crystallographic data:C10H14N4O4S,Mr=286.31,monoclinic,space group C2/c with a=2.5309(3),b=0.67682(6),c=1.74237(19)nm,β=114.744(3)°,V=2.7106(5)nm3,Dc=1.403 g/cm3,μ=0.225mm-1,F(000)=1200,Z=8,R=0.0514 and wR=0.1529.

  18. Environmental effect of rapeseed oil ethyl ester

    International Nuclear Information System (INIS)

    Exhaust emission tests were conducted on rapeseed oil methyl ester (RME), rapeseed oil ethyl ester (REE) and fossil diesel fuel as well as on their mixtures. Results showed that when considering emissions of nitrogen oxides (NOx), carbon monoxide (CO) and smoke density, rapeseed oil ethyl ester had less negative effect on the environment in comparison with that of rapeseed oil methyl ester. When fuelled with rapeseed oil ethyl ester, the emissions of NOx showed an increase of 8.3% over those of fossil diesel fuel. When operated on 25-50% bio-ester mixed with fossil diesel fuel, NOx emissions marginally decreased. When fuelled with pure rapeseed oil ethyl ester, HC emissions decreased by 53%, CO emissions by 7.2% and smoke density 72.6% when compared with emissions when fossil diesel fuel was used. Carbon dioxide (CO2) emissions, which cause greenhouse effect, decreased by 782.87 g/kWh when rapeseed oil ethyl ester was used and by 782.26 g/kWh when rapeseed oil methyl ester was used instead of fossil diesel fuel. Rapeseed oil ethyl ester was more rapidly biodegradable in aqua environment when compared with rapeseed oil methyl ester and especially with fossil diesel fuel. During a standard 21 day period, 97.7% of rapeseed oil methyl ester, 98% of rapeseed oil ethyl ester and only 61.3% of fossil diesel fuel were biologically decomposed. (author)

  19. 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. PMID:26620595

  20. 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%.

  1. Guiding optimal biofuels : a comparative analysis of the biochemical production of ethanol and fatty acid ethyl esters from switchgrass.

    Energy Technology Data Exchange (ETDEWEB)

    Paap, Scott M.; West, Todd H.; Manley, Dawn Kataoka; Dibble, Dean C.; Simmons, Blake Alexander; Steen, Eric J. [Joint BioEnergy Institute, Emeryville, CA; Beller, Harry R. [Lawrence Berkeley National Laboratory, Berkeley, CA; Keasling, Jay D. [Lawrence Berkeley National Laboratory, Berkeley, CA; Chang, Shiyan [Tsinghua University, Beijing, PR China

    2013-01-01

    In the current study, processes to produce either ethanol or a representative fatty acid ethyl ester (FAEE) via the fermentation of sugars liberated from lignocellulosic materials pretreated in acid or alkaline environments are analyzed in terms of economic and environmental metrics. Simplified process models are introduced and employed to estimate process performance, and Monte Carlo analyses were carried out to identify key sources of uncertainty and variability. We find that the near-term performance of processes to produce FAEE is significantly worse than that of ethanol production processes for all metrics considered, primarily due to poor fermentation yields and higher electricity demands for aerobic fermentation. In the longer term, the reduced cost and energy requirements of FAEE separation processes will be at least partially offset by inherent limitations in the relevant metabolic pathways that constrain the maximum yield potential of FAEE from biomass-derived sugars.

  2. Direct detection of fatty acid ethyl esters using low temperature plasma (LTP) ambient ionization mass spectrometry for rapid bacterial differentiation.

    Science.gov (United States)

    Zhang, J Isabella; Costa, Anthony B; Tao, W Andy; Cooks, R Graham

    2011-08-01

    Low temperature plasma mass spectrometry (LTP-MS) was employed to detect fatty acid ethyl esters (FAEE) from bacterial samples directly. Positive ion mode FAEE mass spectrometric profiles of sixteen different bacterial samples were obtained without extraction or other sample preparation. In the range m/z 200-300, LTP mass spectra show highly reproducible and characteristic patterns. To identify the FAEE's associated with the characteristic peaks, accurate masses were recorded in the full scan mode using an LTQ/Orbitrap instrument, and tandem mass spectrometry was performed. Data were examined by principal component analysis (PCA) to determine the degree of differentiation possible amongst different bacterial species. Gram-positive and gram-negative bacteria are readily distinguished, and 11 out of 13 Salmonella strains show distinctive patterns. Growth media effects are observed but do not interfere with species recognition based on the PCA results. PMID:21706093

  3. 2-吲哚乙酸乙酯的合成%Synthesis of 2-indoleacetic Acid Ethyl Ester

    Institute of Scientific and Technical Information of China (English)

    陈芬; 覃宇

    2015-01-01

    丙二酸二乙酯在醇溶液中,与氢氧化钾皂化得到丙二酸单乙酯钾盐,然后在N, N'-羰基二咪唑(CDI)作用下,与2-硝基苯乙酸进行亲核加成得到4-(2-硝基苯基)-乙酰乙酸乙酯,再经三氯化钛的催化还原环化制得医药中间体2-吲哚乙酸乙酯,收率达72.2%。%2- indole acetic acid ethyl ester, the important drug intermediate, was synthesized from diethyl malonate by saponification reaction with potassium hydroxide in the presence of alcohol solution to give ethyl malonate potassium salt and nucleophilic addition with 2-nitrophenyl acetic acid to give 4-(2-nitrophenyl)-ethylacetoacetate using N,N'-carbonyldiimidazole(CDI), and then reduct cyclization reaction upon the catalysis of titanium trichloride with an overall yield of about 72.2%.

  4. Antibacterial Activity of Protocatechuic Acid Ethyl Ester on Staphylococcus aureus Clinical Strains Alone and in Combination with Antistaphylococcal Drugs

    Directory of Open Access Journals (Sweden)

    Maria Miklasińska

    2015-07-01

    Full Text Available The aim of the presented study was to examine in vitro the antibacterial activity of protocatechuic acid ethyl ester (ethyl 3,4-dihydroxybenzoate, EDHB against Staphylococcus aureus clinical isolates alone and in the combination with four selected antibiotics. The EDHB antimicrobial activity was tested against twenty S. aureus strains isolated from the clinical samples, and three reference strains. The phenotypes and genotypes of resistance to methicillin for the tested strains were defined as well as the phenotypic resistance to macrolides, lincosamides and streptogramin B (MLSB. EDHB displayed diverse activity against examined S. aureus strains with the minimal inhibitory concentration (MIC within the range from 64 to 1024 µg/mL. Addition of ¼ MIC of EDHB into the Mueller-Hinton Agar (MHA resulted in augmented antibacterial effect in the presence of clindamycin. In the case of cefoxitin no synergistic effect with EDHB was noted. For erythromycin and vancomycin the decrease of mean MICs in the presence of EDHB was observed but did not reach statistical significance. The results of the present study showed that in vitro EDHB possesses antibacterial activity against S. aureus clinical strains and triggers a synergistic antimicrobial effect with clindamycin and to the lesser extent with erythromycin and vancomycin.

  5. 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.

  6. Ethyl ester production from (RBD palm oil

    Directory of Open Access Journals (Sweden)

    Oscar Mauricio Martínez Ávila

    2010-07-01

    Full Text Available This work develops a methodology for obtaining ethyl esters from RBD (refined, bleached and deodorised palm oil by evaluating the oil’s transesterification and separation. Two catalysts were first tested (KOH and NaOH by studying the effect of water presence on the reaction. The separation process was then evaluated by using water and water-salt and water-acid mixtures, establishing the agent offering the best results and carrying out the purification stage. Raw materials and products were characterised for comparing the latter with those obtained by traditional means and verifying the quality of the esters so produced; minimum differences were found bet-ween both. The proposed methodology thus allows esters to be used as raw material in petrochemical industry applications. A more profitable process can be obtained compared to those used today, given the amounts of separation agent so established (1% H3PO4 solution, in water. The overall process achieved 74.4% yield, based on the oil being used.

  7. Eicosapentaenoic and docosahexaenoic acid ethyl esters differentially enhance B-cell activity in murine obesity[S

    OpenAIRE

    Teague, Heather; Harris, Mitchel; Fenton, Jenifer; Lallemand, Perrine; Shewchuk, Brian M.; Shaikh, Saame Raza

    2014-01-01

    EPA and DHA are not biologically equivalent; however, their individual activity on B cells is unknown. We previously reported fish oil enhanced murine B-cell activity in obesity. To distinguish between the effects of EPA and DHA, we studied the ethyl esters of EPA and DHA on murine B-cell function as a function of time. We first demonstrate that EPA and DHA maintained the obese phenotype, with no improvements in fat mass, adipose inflammatory cytokines, fasting insulin, or glucose clearance. ...

  8. 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.

  9. Effect of omega-3 fatty acid ethyl esters on the oxylipin composition of lipoproteins in hypertriglyceridemic, statin-treated subjects.

    Directory of Open Access Journals (Sweden)

    John W Newman

    Full Text Available Oxylipins mediate inflammation, vascular tension, and more. Their presence in lipoproteins could explain why lipoproteins mediate nearly identical activities.To determine how oxylipins are distributed in the lipoproteins of hypertriglyceridemic subjects, and whether omega-3 fatty acids alter them in a manner consistent with improved cardiovascular health, we recruited 15 dyslipidemic subjects whose levels of low density lipoprotein cholesterol (LDL-C were at goal but who remained hypertriglyceridemic (200-499 mg/dL. They were treated them with the indicated dose of 4 g/d omega-3 acid ethyl esters (P-OM3 for 8 weeks. Measured oxylipins included mid-chain alcohols (HETEs, HEPEs and HDoHEs, ketones (KETEs, epoxides (as EpETrEs, EpETEs, and EpDPEs.At baseline, arachidonate-oxylipins (HETEs, KETEs, and EpETrEs were most abundant in plasma with the greatest fraction of total abundance (mean |95% CI| being carried in high density lipoproteins (HDL; 42% |31, 57| followed by very low density lipoproteins (VLDL; 27% |20, 36|; and LDL 21% |16, 28|. EPA- and DHA-derived oxylipins constituted less than 11% of total. HDL carried alcohols and epoxides but VLDL was also rich in ketones. Treatment decreased AA-derived oxylipins across lipoprotein classes (-23% |-33, -12|, p = 0.0003, and expanded EPA-(322% |241, 422|, p<0.0001 and DHA-derived oxylipins (123% |80, 176|, p<0.0001.Each lipoprotein class carries a unique oxylipin complement. P-OM3 treatment alters the oxylipin content of all classes, reducing pro-inflammatory and increasing anti-inflammatory species, consistent with the improved inflammatory and vascular status associated with the treatment.ClinicalTrials.gov NCT00959842.

  10. β-氨基酸乙酯盐酸盐的合成与表征%Synthesis and Characterization of β-Amino Acid Ethyl Ester Hydrochlorides

    Institute of Scientific and Technical Information of China (English)

    韩秋敏; 李登超

    2011-01-01

    β-Phenylalanine ethyl ester hydrochloride,2-F-β-phenylalanine ethyl ester hydrochloride and 3-F-β-phenylalanine ethyl ester hydrochloride were synthesized by reacting amino acids with ethanol in the presence of thionyl chloride,respectively.The structures of these compounds were characterized by melting point,1H-NMR,13C-NMR and mass spectrometry.This synthetic method was simple,with mild reaction conditions and the yields above 85%.%以三种β-苯丙氨酸、二氯亚砜、乙醇为原料分别合成了β-苯丙氨酸乙酯盐酸盐、2F-β-苯丙氨酸乙酯盐酸盐和3F-β-苯丙氨酸乙酯盐酸盐三种稳定的β-氨基酸乙酯盐酸盐,并通过熔点、核磁和质谱对化合物的结构进行了表征。该合成方法操作简单、反应条件温和,收率均在85%以上。

  11. [Allosteric regulation of glucosamine synthetase activity by naphthoquinone derivatives and ethyl ester of di-(4-oxycumarinyl-3)-acetic acid].

    Science.gov (United States)

    Sharaev, P N; Bogdanov, N G; Sarycheva, I K; Zhukova, E E

    1981-02-01

    The effects of derivatives of naphthoquinone, e.g. 2-methyl-3-phytyl-1,4-naphthoquinone (vitamin K1), 2-methyl-1,4-naphthoquinone (vitamin K3), 3-dihydro-2-methyl-1,4-naphthoquinone-2-sodium sulfonate (vicasol), derivatives of naphthohydroxyquinone, e.g. 2-methyl-1,4-naphthohydroxyquinone 1-monoacetate, 2-methyl-1,4-naphthohydroxyquinone 1,4-diacetate and the oxycumarine derivative di-(4-oxycumarinyl-3)-acetate ethyl ester (pelentan) on the activity of purified glutamine synthetase (EC 5.3.1.19) from rat liver were studied. The enzyme activity was increased under effects of vitamins K1 and K3 and was inhibited by pelentan. The data obtained are indicative of the allosteric effect of these compounds on the enzyme. PMID:7195738

  12. 3-Methylthiopropionic acid ethyl ester, isolated from Katsura-uri (Japanese pickling melon, Cucumis melo var. conomon), enhanced differentiation in human colon cancer cells.

    Science.gov (United States)

    Nakamura, Yasushi; Nakayama, Yuko; Ando, Hitomi; Tanaka, Atsuo; Matsuo, Tomoaki; Okamoto, Shigehisa; Upham, Brad L; Chang, Chia-Cheng; Trosko, James E; Park, Eun Young; Sato, Kenji

    2008-05-14

    The fully ripened fruit of Katsura-uri Japanese pickling melon ( Cucumis melo var. conomon) has rarely been used for food because the midripened fruit is utilized for making pickles, but the fully ripened fruit is no longer valuable for pickles due to the fruit body being too soft. We have considered the utilization of the fully ripened Katsura-uri fruit that may be used for nonpickling products, particularly if the fully ripened fruit demonstrated health benefits such as anticarcinogenic properties. The phytochemical extract from the fully ripened fruit of Katsura-uri Japanese pickling melon was purified via a bioassay-guided fractionation scheme, which was based on the induction of differentiation in a RCM-1 human colon cancer cell line. On the criteria of two differentiation markers (duct formation and alkaline phosphatase activity), the most potent fraction contained a compound identified as 3-methylthiopropionic acid ethyl ester, based on GC retention time, EI-MS, (1)H NMR, and (13)C NMR spectra. Previously, the role of 3-methylthiopropionic acid ethyl ester was considered as an odor producing compound in many fruits, but this study indicates potential medical benefits of this compound. PMID:18426216

  13. Production and Optimization of Oleic Acid Ethyl Ester Synthesis Using Lipase From Rice Bran (Oryza sativa L. and Germinated Jatropha Seeds (Jatropha curcas L. by Response Surface Methodology

    Directory of Open Access Journals (Sweden)

    Indro Prastowo

    2015-11-01

    Full Text Available Normal 0 false false false MicrosoftInternetExplorer4 Recently, the fatty acid ethyl ester has been synthesized in place of fatty acid methyl ester since ethanol has been more renewable. In this research, oleic acid ethyl ester (OAEE was synthesized using germinated jatropha seeds (Jatropha curcas.L and rice bran (Oryza sativa as source of lipase. The objective of the research was to optimize the synthesis conditions using Response Surface Methodology. Factors, such as crude enzyme concentration, molar ratio of oleic acid to ethanol, and the reaction time, were evaluated. The results show that lipase from germinated jatropha seeds had the hydrolitic and esterifi cation activity about 6.73 U/g and 298.07 U/g, respectively. Lipase from rice bran had the hydrolitic and esterifi cation activity about 10.57 U/g and 324.03 U/g, respectively. The optimum conditions of esterifi cation reaction using germinated jatropha seed lipase as biocatalyst were crude enzyme concentration of 0.31 g/ml, molar ratio of oleic acid to ethanol of 1 : 1.81, and reaction time of 50.9 min. The optimum conditions of esterifi cation reaction using rice bran lipase were crude enzyme concentration of 0.29 g/ml, molar ratio of oleic acid to ethanol of 1 : 2.05, and reaction time of 58.61 min. The obtained amounts of OAEE were 810.77 μmole and 626.92 μmole for lipases from rice bran and germinated jatropha seed, respectively. /* Style Definitions */ table.MsoNormalTable {mso-style-name:"Table Normal"; mso-tstyle-rowband-size:0; mso-tstyle-colband-size:0; mso-style-noshow:yes; mso-style-parent:""; mso-padding-alt:0cm 5.4pt 0cm 5.4pt; mso-para-margin:0cm; mso-para-margin-bottom:.0001pt; mso-pagination:widow-orphan; font-size:10.0pt; font-family:"Times New Roman"; mso-fareast-font-family:"Times New Roman"; mso-ansi-language:#0400; mso-fareast-language:#0400; mso-bidi-language:#0400;}

  14. 硬脂酸2-(4-苄氧基苯基)乙酯的结构表征%Structural Characterization of Stearic Acid, 2-[4-(Phenylmethoxy) phenyl]ethyl Ester

    Institute of Scientific and Technical Information of China (English)

    张国平; 李翔; 喻宗沅

    2012-01-01

    通过HPLC、DSC、FTIR、1 HNMR、13CNMR对硬脂酸2-(4-苄氧基苯基)乙酯的结构进行了表征.%The structure of stearic acid, 2-[4-(phenylmethoxy)phenyl] ethyl ester was characterized with HPLC,DSC,FTIR,1HNMR,13CNMR for the first time.

  15. Influences of process parameters on preparation of microparticle used as a carrier system for omega - 3 unsaturated fatty acid ethyl esters used in supplementary nutrition.

    Science.gov (United States)

    Lamprecht, A; Schäfer, U; Lehr, C M

    2001-01-01

    Microparticles were prepared by complex coacervation to encapsulate eicosapentaenoic acid ethyl ester (EPA-EE) for incorporation into foods as a nutrition supplement. Gelatin and acacia were used in the coacervation process. With an increasing oil/polymer ratio, both yield and encapsulation rate decreased; with an increasing homogenization time, the yield remained constant while the encapsulation rate slightly increased. Several particle hardening techniques were examined and their influence on particle structure, yield and encapsulation rate were examined. Ethanol hardening was compared to cross-linking with dehydroascrobic acid with respect to both yield and encapsulation rate. The particle diameters for both formulations were similar (ethanol: 38.4 +/- 4.1 microm; cross-linking: 41.8 +/- 3.0 microm). Spray-drying of the coacervates led to the smallest particles (5.2 +/- 1.1 microm), lowest yield and encapsulation rate. All microencapsulation products were assayed for their storage stability over 4 weeks with respect to the oxidation of the encapsulated omega - 3 unsaturated fatty acid ester inside the particles. Hardening with ethanol showed the lowest amount of peroxides: particle wall cross-linking by dehydroascorbic acid and spray-drying were observed to be less protective. All microparticles were characterized for their internal structure with confocal laser scanning microscopy (CLSM) after fluorescence labelling of the polymers, in order to localize the oil phase and visualize the distribution of the polymers in the coacervates. With increasing homogenization time, the internal structure changed stepwise from a capsule structure (core/wall) towards a matrix structure. For all experiments, a homogeneous distribution for both polymers, gelatin and acacia was observed inside the particle wall. No influence of the different particle hardening procedures on the polymer distribution was found.

  16. Catalytic Synthesis of Ethyl Ester of Acetyl Ferulic Acid with DCC/DMAP%DCC/DMAP 催化制备乙酰阿魏酸乙酯

    Institute of Scientific and Technical Information of China (English)

    石翛然

    2014-01-01

    Intermediate 3-( 4-acetoxy-3-methoxyphenyl ) acrylic acid was synthesized by 4-hydroxy-3-methoxybenzaldehyde, with dicyclohexyl carbodiimide ( DCC) and 4-dime-thylamino pyridine ( DMAP) as catalyst. Ethyl ester of acetyl ferulic acid was synthesized by esterification reaction.Target product was characterized by IR, elemental analysis and MS.The experimental results showed at room temperature, the amount of catalyst accounts for 3%of the acetyl ferulic acid, and reaction 4 h was the best condition.%以4-羟基-3-甲氧基苯甲醛为起始原料,合成了中间产物乙酰阿魏酸,再以N,N-二环己基碳二亚胺( DCC)和4-二甲胺基吡啶( DMAP)为催化剂,通过酯化反应制备了乙酰阿魏酸乙酯,各步产物通过红外光谱、质谱和元素分析对其结构进行表征确认。实验结果表明:在室温下,催化剂用量为乙酰阿魏酸用量的3%,反应时间为4 h的条件下,产率达到75%,为最优条件。

  17. A newly discovered xenobiotic metabolic pathway: Ethyl ester formation

    Energy Technology Data Exchange (ETDEWEB)

    Chou, R.C.; Wyss, R.; Huselton, C.A.; Wiegand, U.W. (F. Hoffmann-La Roche Ltd., Basel (Switzerland))

    1991-01-01

    Formation of etretinate, ethyl ester of acitretin, can be confirmed in vitro and in vivo using acitretin as the substrate. Etretinate was identified by LC/MS. The in vitro incubation was performed using rat and human liver 12000 g supernatant, and the in vivo experiment was conducted in rats after oral dosing of acitretin. The ethyl ester formation was greatly enhanced by addition of or dosing with ethanol.

  18. 新型可逆热致变色油墨溶剂——癸酸2-(4-苄氧基苯基)乙酯和月桂酸2-(4-苄氧基苯基)乙酯的结构表征%Structural Characterization of Novel Reversible Thermochromic Ink Solvents Decanoic Acid, 2-[4-(Phenylmethoxy) phenyl]ethyl Ester and Dodecanoic Acid, 2-[4-(Phenylmethoxy) phenyl]ethyl Ester

    Institute of Scientific and Technical Information of China (English)

    张国平; 李翔; 喻宗沅

    2012-01-01

    This thesis conducts the structural characterization of the two reversible thermochromic ink solvents decanoic acid,2-[4-(phenylmethoxy)phenyl]ethyl ester and dodecanoic acid,2-[4-(phenylmethoxy)phen-yl]ethyl ester based on HPLCDSCFTIR,1 HNMR,13CNMR and reports the characterization results for the first time.%通过HPLC、DSC、FTIR、1 HNMR、13CNMR对自制的两种可逆热致变色油墨溶剂癸酸2-(4-苄氧基苯基)乙酯和月桂酸2-(4-苄氧基苯基)乙酯进行了表征,并首次予以报道.

  19. Biocatalytic ammonolysis of (5S)-4,5-dihydro-1H-pyrrole-1,5-dicarboxylic acid, 1-(1,1-dimethylethyl)-5-ethyl ester: preparation of an intermediate to the dipeptidyl peptidase IV inhibitor Saxagliptin.

    Science.gov (United States)

    Gill, Iqbal; Patel, Ramesh

    2006-02-01

    An efficient biocatalytic method has been developed for the conversion of (5S)-4,5-dihydro-1H-pyrrole-1,5-dicarboxylic acid, 1-(1,1-dimethylethyl)-5-ethyl ester (1) into the corresponding amide (5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid, 1-(1,1-dimethylethyl)ester (2), which is a critical intermediate in the synthesis of the dipeptidyl peptidase IV (DPP4) inhibitor Saxagliptin (3). Candida antartica lipase B mediates ammonolysis of the ester with ammonium carbamate as ammonia donor to yield up to 71% of the amide. The inclusion of Ascarite and calcium chloride as adsorbents for carbon dioxide and ethanol byproducts, respectively, increases the yield to 98%, thereby offering an efficient and practical alternative to chemical routes which yield 57-64%.

  20. 一锅法合成4-甲基-5-咪唑甲酸乙酯工艺%The Preparation of 4-Methyl-5-imidazole-carboxylic Acid Ethyl Ester by One-pot Reaction

    Institute of Scientific and Technical Information of China (English)

    朱驯; 魏运洋

    2012-01-01

    [Aims] The aim is to look for a new preparation method of 4-methyl-5-imidazole-carboxylic acid ethyl ester. [Methods] 4-Methyl-5-imidazole-carboxylic acid ethyl ester with versatility was prepared from 3-oxo-butyric acid ethyl ester, sulfuryl chloride and formamide by one-pot reaction. [Results] The effect on yield of the mole ratio of materials, reaction temperature, different solvent were discussed by experiments. We could receive the optimal reaction condition, the mole ratio of 3-oxo-butyric acid ethyl ester, sulfuryl chloride and formamide is 1:1:2 (in mol), the reaction temperature is 120 ℃, the solvent is dioxane. And the syntheses yield of 4-methyl-5-imidazole-carboxylic acid ethyl ester is 70% under this condition. [Conclusions] The new route is simple and the raw materials are easily obtained, which is suitable for industrial production.%[目的]寻找一条合成4-甲基-5-咪唑甲酸乙酯的新工艺路线。[方法]以乙酰乙酸乙酯、磺酰氯与甲酰胺为原料,采用一锅法合成一种用途广泛的多功能单体4-甲基-5-咪唑甲酸乙酯。[结果]通过实验,确定了一条合成4-甲基-5-咪唑甲酸乙酯的新工艺:以二氧六环为溶剂,环化时反应温度为120℃,反应时间为4 h,n(乙酰乙酸乙酯)∶n(磺酰氯)∶n(甲酰胺)为1∶1∶2,在该条件下,4-甲基-5-眯唑甲酸乙酯的产率为70%。[结论]该方法路线简单,原料易得,适合工业化生产。

  1. 鱼油中二十碳五烯酸乙酯和二十二碳六烯酸乙酯的超临界流体色谱分离技术%Supercritical Fluid Chromatographic Separation of Eicosapentaenoic Acid Ethyl Ester and Docosahexaenoic Acid Ethyl Ester from Fish Oil

    Institute of Scientific and Technical Information of China (English)

    陈伟珠; 洪专; 赵敏; 张怡评; 谢全灵; 易瑞灶

    2012-01-01

    A supercritical fluid chromatographic method to separate eicosapentaenoic acid ethyl ester (EPA-EE) and docosahexaenoic acid ethyl ester (DHA-EE) from fish oil was established. Hedera ODS-BP was found to be the most effective column for separating EPA-EE and DHA-EE from fish oil as demonstrated by a comparison with Luna 5u Silica, Hypersil ODS2, ZORBAX SB-C8, and Hypersil C8. The effects of mobile phase modifier type, methanol percentage in mobile phase, back pressure and column temperature for the separation of both esters by Hedera ODS-BP on capacity factor, diastereoselectivity and resolution were investigated. The optimum conditions forthese factors were found to be separation on Hedera ODS-BP column at a column temperature of 40 ℃ an a back pressure of 100 bar using a mobile phase containing 10% methanol as a modifier at a total flow rate of 2 mI./min. Under these conditions, baseline separation of EPA-EE and DHA-EE was achieved. The developed method was simple, rapid, highly reproducible and suitable for the separation of EPA-EE and DHA-EE from fish oil.%建立鱼油中二十碳五烯酸乙酯(EPA-EE)和二十二碳六烯酸乙酯(DHA-EE)的超临界流体色谱纯化方法。比较Luna5uSilica、HederaODS。BP、HypersilODS2、ZORBAXSB.CR和HypersilCR等色谱柱对EPA-EE和DHA.EE的分离效果,确定以HederaODS.BP作为优选色谱柱,进一步以容量因子、选择性和分离度为考核指标,考察改性剂、流动相比例、背压及温度对分离效果的影响。得到的优化分离条件为:以HederaODS.BP为色谱柱,10%甲醇为改性剂,总流速2mL/min、柱温40℃、背压100bar。在此条件下,鱼油中EPA-EE和IDHA.EE可以达到基线分离。结论:本法简便、快速、重现性好,可用于鱼油中EPA-EE和IDHA-EE的分离。

  2. Neurotoxic and teratogenic effects of an organophosphorus insecticide (phenyl phosphonothioic acid-O-ethyl -O-[4-nitrophenyl] ester) on mallard development

    Science.gov (United States)

    Hoffman, D.J.; Sileo, L.

    1984-01-01

    Phenyl phosphonothioic acid-O-ethyl-O-[4-nitrophenyl] ester (EPN) is one of the 10 most frequently used organophosphorus insecticides and causes delayed neurotoxicity in adult chickens and mallards. Small amounts of organophosphorus insecticides placed on birds' eggs are embryotoxic and teratogenic. For this reason, the effects of topical egg application on EPN were examined on mallard (Anas platyrhynchos) embryo development. Mallard eggs were treated topically at 72 hr of incubation with 25 microliter of a nontoxic oil vehicle or with EPN in the vehicle at concentrations of approximately 12, 36, or 108 micrograms/g egg, equivalent to one, three, and nine times the agricultural level of application used to spray crops. Treatment with EPN resulted in 22 to 44% mortality over this dose range by 18 days of development compared with 4 and 5% for untreated and vehicle-treated controls. EPN impaired embryonic growth and was highly teratogenic: 37-42% of the surviving embryos at 18 days were abnormal with cervical and axial scoliosis as well as severe edema. Brain weights were significantly lower in EPN-treated groups at different stages of development including hatchlings. Brain neurotoxic esterase (NTE) activity was inhibited by as much as 91% at 11 days, 81% at 18 days, and 79% in hatchlings. Examination of brain NTE activity during the course of normal development revealed an increase of nearly sixfold from Day 11 through hatching. The most rapid increase occurred between Day 20 and hatching. Brain acetylcholinesterase (AChE) activity was inhibited by as much as 41% at 11 days, 47% at 18 days, and 20% in hatchlings. Plasma cholinesterase and alkaline phosphatase activities were inhibited and plasma aspartate aminotransferase activity was increased at one or more stages of development. Hatchlings from EPN-treated eggs were weaker and slower to right themselves. Histopathological examination did not reveal demyelination and axonopathy of the spinal cord that was

  3. Effect of Omega-3 Fatty Acid Ethyl Esters on the Oxylipin Composition of Lipoproteins in Hypertriglyceridemic, Statin-Treated Subjects

    OpenAIRE

    NEWMAN, JOHN W.; Pedersen, Theresa L.; Brandenburg, Verdayne R.; Harris, William S.; Shearer, Gregory C.

    2014-01-01

    Background Oxylipins mediate inflammation, vascular tension, and more. Their presence in lipoproteins could explain why lipoproteins mediate nearly identical activities. Methods To determine how oxylipins are distributed in the lipoproteins of hypertriglyceridemic subjects, and whether omega-3 fatty acids alter them in a manner consistent with improved cardiovascular health, we recruited 15 dyslipidemic subjects whose levels of low density lipoprotein cholesterol (LDL-C) were at goal but who ...

  4. ENZYMATIC PRODUCTION OF ETHYL OLEATE ESTER USING A LIPASE FROM CANDIDA ANTARCTICA B

    Directory of Open Access Journals (Sweden)

    N. Sampaio Neta

    2012-05-01

    Full Text Available Lipases are biocatalysts of great importance in different areas, being able to catalyze reactions in aqueous or organic media. Furthermore, these enzymes are capable of using several substrates being stable in a wide range of pH and temperatures. Lipases promote the esterification between fatty acids and ethanol producing oleate esters. The aim of this work is to produce ethyl oleate ester by enzymatic esterification of oleic acid with ethanol. A lipase from Candida antarctica type B was used at a temperature of 55 °C. The reaction was conducted using oleic acid, sodium sulfate anhydrous, lipase and ethanol, with a ratio of oleic acid (0.03 mol or 10 ml, lipase (0.1 mol or 0.01 g, sodium sulfate anhydrous (5 g and ethanol 99 % (100 ml. Several reaction times were studied, namely 48, 72, 96 and 120 hours. Nuclear Magnetic Resonance (1H and 13C and Infrared spectra confirmed the production of ethyl oleate ester for the studied conditions. The highest ethyl oleate production yield was obtained for 96 hours reaction time. Ethyl oleate esters have been reported to possess interesting applications in several industrial fields, such as food, aromatics, cosmetics, detergents, flavors and pharmaceuticals.

  5. Synthesis of new radiotracers based of Ethyl Ester

    International Nuclear Information System (INIS)

    The in vivo study of a biochemical or physiological process requires the synthesis of specific radiotracers but also the targeting of these compounds so that they can reach their target tissue. Methodologies original synthesis associated with radioisotopes used, the quantities and chemical forms often have to be available developed. The chemistry of metal complexes booming, we were able to use the ethyl ester combined with technetium, forming a stable radiotracer. Finally, a counting of radioactivity in different rat's organs completed our study. (Author)

  6. Deptermination of Partial Molar Volumes of EPA and DHA Ethyl Esters in Supercritical Carbon Dioxide

    Institute of Scientific and Technical Information of China (English)

    MeiHUANG; XianDaWANG; 等

    2002-01-01

    The use of supercritical-fluid shromatogrphy for determining partial molar volumes of ethyl esters of cis-5,8,11,14,17-eicosapentaenoic acid (EPA) and cis-4,7,10,13,16,19-docosa-hexaenoic acid(DHA) in supercritical carbon dioxide is presented and discussed. Partial molar volumes of EPA and DHA esters are obtained from the variation of the retention properties with the density of mobile phase at 313.15K,323.15K,333.15K and in the pressure range from 9 MPa to 21 MPa.

  7. Determination of Partial Molar Volumes of EPA and DHA Ethyl Esters in Supercritical Carbon Dioxide

    Institute of Scientific and Technical Information of China (English)

    2002-01-01

    The use of supercritical-fluid chromatography for determining partial molar volumes of ethyl esters of cis-5,8,11,14,17-eicosapentaenoic acid (EPA) and cis -4,7,10,13,16,19- docosa-hexaenoic acid (DHA) in supercritical carbon dioxide is presented and discussed. Partial molar volumes of EPA and DHA esters are obtained from the variation of the retention properties with the density of mobile phase at 313.15 K, 323.15 K, 333.15 K and in the pressure range from 9 MPa to 21 MPa.

  8. Tropane ethyl esters in illicit cocaine: isolation, detection, and determination of new manufacturing by-products from the clandestine purification of crude cocaine base with ethanol.

    Science.gov (United States)

    Casale, John F; Boudreau, Danielle K; Jones, Laura M

    2008-05-01

    Seven ethyl homologues of known tropane esters have recently been detected as impurities in the gas chromatographic signature profiles of authentic Peruvian illicit cocaine base and hydrochloride exhibits. Peruvian cocaine base processors are now known to use ethanol for the purification of crude cocaine base. This process is referred to as the "base lavada" or "washed base" process and is a recent substitute method for the potassium permanganate oxidation purification methodology. Seven ethyl ester homologues were formed in illicit cocaine from the transesterification of known tropane methyl esters or possibly ethyl esterification of their respective tropane C-2 carboxylic acids in the presence of ethanol. Exhibits containing these compounds were subjected to gas chromatographic-mass spectrometric analyses to determine their identity and were subsequently synthesized to verify their structures. Quantitative determinations were obtained from ion-pair chromatography isolation followed by gas chromatography with flame ionization detection. Specifically, hexanoylecgonine ethyl ester, cocaethylene, cis-cinnamoylecgonine ethyl ester, trans-cinnamoylecgonine ethyl ester, 3',4',5'-trimethoxybenzoylecgonine ethyl ester, cis-3',4',5'-trimethoxycinnamoylecgonine ethyl ester, and trans-3',4',5'-trimethoxycinnamoylecgonine ethyl ester were detected and characterized. When present, these compounds were detected at levels ranging from 8.6 x 10(-4) to 9.3 x 10(-1)% relative to cocaine. PMID:18471211

  9. Application of substituted 2-(trimethylsilyl)ethyl esters to suppress diketopiperazine formation

    NARCIS (Netherlands)

    Borsuk, K.; Delft, F.L. van; Eggen, I.F.; Kortenaar, P.B.W. ten; Petersen, A.; Rutjes, F.P.J.T.

    2004-01-01

    The use of differently substituted 2-(trimethylsilyl)ethyl esters for C-terminal protection in peptide synthesis has been investigated. While the use of the unsubstituted 2-(trimethylsilyl)ethyl ester resulted in a substantial amount of diketopiperazine at the dipeptide stage, use of the correspondi

  10. Amidation reaction of eugenyl oxyacetate ethyl ester with 1,3 diaminopropane

    Science.gov (United States)

    Suryanti, V.; Wibowo, F. R.; Kusumaningsih, T.; Wibowo, A. H.; Khumaidah, S. A.; Wijayanti, L. A.

    2016-04-01

    Eugenol having various substituents on the aromatic ring (hydroxy, methoxy and allyl) are useful for starting material in synthesizing of its derivatives. Eugenol derivatives have shown wide future potential applications in many areas, especially as future drugs against many diseases. The aim of this work was to synthesize an amide of eugenol derivative. The starting material used was eugenol from clove oil and the reaction was conducted in 3 step reactions to give the final product. Firstly, eugenol was converted into eugenyl oxyacetate [2-(4-allyl-2-methoxyphenoxy) acetic acid] as a white crystal with 70.5% yield, which was then esterified with ethanol to have eugenyl oxyacetate ethyl ester [ethyl 2-(4-allyl-2-methoxyphenoxy) acetate] as brown liquid in 75.7%. The last step was the reaction between eugenyl oxyacetate ethyl ester and 1,3 diaminopropane to give 2-(4-allyl-2-methoxyphenoxy)-N-(3-aminopropyl) acetamide as a brown powder with 71.6% yield, where the amidation reaction was occurred.

  11. Determination of 13C isotopic enrichment of valine and threonine by GC-C-IRMS after formation of the N(O,S)-ethoxycarbonyl ethyl ester derivatives of the amino acids.

    Science.gov (United States)

    Godin, Jean-Philippe; Faure, Magali; Breuille, Denis; Hopfgartner, Gérard; Fay, Laurent-Bernard

    2007-06-01

    We describe a new method of assessing, in a single run, (13)C isotopic enrichment of both Val and Thr by gas chromatography-combustion-isotope-ratio mass spectrometry (GC-C-IRMS). This method characterised by a rapid one-step derivatisation procedure performed at room temperature to form the N(O,S)-ethoxycarbonyl ethyl ester derivatives, and a polar column for GC. The suitability of this method for Val and Thr in in-vivo samples (mucosal hydrolysate) was demonstrated by studying protein metabolism with two tracers ((13)C-valine or (13)C-threonine). The intra-day and inter-day repeatability were both assessed either with standards or with in-vivo samples at natural abundance and at low (13)C isotopic enrichment. For inter-day repeatability CVs were between 0.8 and 1.5% at natural abundance and lower than 5.5% at 0.112 and 0.190 atom% enrichment for Val and Thr, respectively. Overall isotopic precision was studied for eleven standard amino acid derivatives (those of Val, Ala, Leu, Iso, Gly, Pro, Asp, Thr, Ser, Met, and Phe) and was assessed at 0.32 per thousand. The (13)C isotopic measurement was then extended to the other amino acids (Ala, Val, Leu, Iso, Gly, Pro, Thr, and Phe) at natural abundance for in-vivo samples. The isotopic precision was better than 0.002 atom% per amino acid (for n = 4 rats). This analytical method was finally applied to an animal study to measure Thr utilization in protein synthesis. PMID:17468859

  12. Uses and benefits of omega-3 ethyl esters in patients with cardiovascular disease

    Directory of Open Access Journals (Sweden)

    Giacomo Levantesi

    2010-07-01

    Full Text Available Giacomo Levantesi, Maria Giuseppina Silletta, Roberto MarchioliLaboratory of Clinical Epidemiology of Cardiovascular Disease, Consorzio Mario Negri Sud, Chieti, ItalyAbstract: Much evidence on the favorable effects of omega-3 ethyl esters on cardiovascular morbidity and mortality has been obtained in studies performed in healthy subjects and in different clinical settings. Here the clinical effects of omega-3 ethyl ester administration in patients with previous myocardial infarction or heart failure are reviewed, together with a discussion of underlying mechanisms of action. The pharmacokinetic and pharmacodynamic properties of omega-3 ethyl esters, as well as evidence concerning their safety and tolerability, are also reported.Keywords: omega-3 ethyl esters, myocardial infarction, heart failure

  13. 超声提取-毛细管气相色谱法检测酱腌菜中对羟基苯甲酸酯%Determination of p-Hydroxy Benzoic Acid Ethyl Ester in Pickles by Ultrasonic Extracting-Gas Chromatography

    Institute of Scientific and Technical Information of China (English)

    张全美; 黄锦燕; 王守卿

    2012-01-01

    采用超声提取法提取酱腌菜中的对羟基苯甲酸甲酯、对羟基苯甲酸乙酯及对羟基苯甲酸丙酯,在SE30毛细管柱(33 m×0.53 mm,2.65 μm)上得到了良好分离.对羟基苯甲酸甲酯、对羟基苯甲酸乙酯及对羟基苯甲酸丙酯在0~750 μg/mL浓度范围内与色谱峰面积呈良好的线性关系,相关系数为0.9999.对羟基苯甲酸甲酯、对羟基苯甲酸乙酯、对羟基苯甲酸丙酯的检出限分别为0.1,0.1,0.2 μg/mL,测定结果的相对标准偏差小于3.6%(n=11),平均回收率为84.5%~97.1%.%Ultrasonic extraction method was used to extract p-hydroxy benzoic acid methyl ester, ethyl ester and acrylic ester, which were separated in SE30 column(33 m×0.53 mm,2.65 μm). The content of p-hydroxy benzoic acid methyl ester, ethyl ester and acrylic ester had a linear relationship with the chromatographpeak area in the range of 0-750 μg / mL, and results correlation coefficient was 0.9999. The detection limits of p-hydroxy benzoic acid methyl ester, p-hydroxy benzoic acid ethyl ester and p-hydroxy benzoic acid acrylic ester were 0.1, 0.1,0.2 μg/mL, repectively, the RSD of determination results was less than 3.6%(n=ll). The average recoveries were 84.5%-97.1%.

  14. Density functional study of electronic, charge density, and chemical bonding properties of 9-methyl-3-Thiophen-2-YI-Thieno [3,2-e] [1, 2, 4] Thriazolo [4,3-c] pyrimidine-8-Carboxylic acid ethyl ester crystals

    Energy Technology Data Exchange (ETDEWEB)

    Reshak, A.H., E-mail: maalidph@yahoo.co.uk [New Technologies – Research Center, University of West Bohemia, Univerzitni 8, 306 14 Pilsen (Czech Republic); Center of Excellence Geopolymer and Green Technology, School of Material Engineering, University Malaysia Perlis, 01007 Kangar, Perlis (Malaysia); Kamarudin, H. [Center of Excellence Geopolymer and Green Technology, School of Material Engineering, University Malaysia Perlis, 01007 Kangar, Perlis (Malaysia); Alahmed, Z.A. [Department of Physics and Astronomy, King Saud University, Riyadh 11451 (Saudi Arabia); Auluck, S. [CSIR-National Physical Laboratory, Dr. K S Krishnan Marg, New Delhi 110012 (India); Chyský, Jan [Department of Instrumentation and Control Engineering, Faculty of Mechanical Engineering, CTU in Prague, Technicka 4, 166 07 Prague 6 (Czech Republic)

    2014-06-01

    A comprehensive theoretical density functional investigation of the electronic crystal structure, chemical bonding, and the electron charge densities of 9-Methyl-3-Thiophen-2-YI-Thieno [3, 2-e] [1, 2, 4] Thriazolo [4,3-c] Pyrimidine-8-Carboxylic Acid Ethyl Ester (C{sub 15}H{sub 12}N{sub 4}O{sub 2}S{sub 2}) is performed. The density of states at Fermi level equal to 5.50 (3.45) states/Ry cell, and the calculated bare electronic specific heat coefficient is found to be 0.95 (0.59) mJ/mole-K{sup 2} for the local density approximation (Engel–Vosko generalized gradient approximation). The electronic charge density space distribution contours in (1 0 0) and (1 1 0) planes were calculated. We find that there are two independent molecules (A and B) in the asymmetric unit exhibit intramolecular C–H…O, C–H…N interactions. This intramolecular interaction is different in molecules A and B, where A molecule show C–H…O interaction while B molecule exhibit C–H…N interaction. We should emphasis that there is π–π interaction between the pyrimidine rings of the two neighbors B molecules gives extra strengths and stabilizations to the superamolecular structure. The calculated distance between the two neighbors pyrimidine rings found to be 3.345 Å, in good agreement with the measured one (3.424(1) Å). - Highlights: • Electronic structure, chemical bonding, and electron charge density were studied. • Density of states at Fermi level is 5.50 (3.45) states/Ry cell, for LDA (EVGGA). • Bare electronic specific heat coefficient is 0.95 (0.59) mJ/mole-K{sup 2} for LDA(EVGGA). • There are two independent molecules (A and B) in the asymmetric unit.

  15. Transesterification of vegetable oils with ethanol and characterization of the key fuel properties of ethyl esters

    Energy Technology Data Exchange (ETDEWEB)

    Anastopoulos, G.; Zannikou, Y.; Stournas, S. [National Technical University of Athens, School of Chemical Engineering, Laboratory of Fuels Technology and Lubricants, Iroon Polytechniou 9, Athens 15780 (Greece); Kalligeros, S. [Hellenic Organization for Standardization, Technical Committee 66, 67 Prevezis Street, Athens, 10444 (Greece)

    2009-07-01

    The transesterification reactions of four different vegetable oils (sunflower, rapeseed, olive oil and used frying oil) with ethanol, using sodium hydroxide as catalyst, were studied. The ester preparation involved a two-step transesterification reaction, followed by purification. The effects of the mass ratio of catalyst to oil (0.25 - 1.5%), the molar ratio of ethanol to oil (6:1 - 12:1), and the reaction temperature (35 - 90 {sup o}C) were studied for the conversion of sunflower oil to optimize the reaction conditions in both stages. The rest of the vegetable oils were converted to ethyl esters under optimum reaction parameters. The optimal conditions for first stage transesterification were an ethanol/oil molar ratio of 12:1, NaOH amount (1% wt/wt), and 80 {sup o}C temperature, whereas the maximum yield of ethyl esters reached 81.4% wt/wt. In the second stage, the yield of ethyl esters was improved by 16% in relation with the one-stage transesterification, which was obtained under the following optimal conditions: catalyst concentration 0.75% and ethanol/oil molar ratio 6:1. The fuel properties of the esters were measured according to EN test methods. Based on the experimental results one can see that the ethyl esters do not differ significantly from methyl esters. Moreover, the results showed that the values of density, viscosity, and higher heating value of ethyl esters were similar to those of automotive and heavy duty engine diesel fuel. However, the CFPP values were higher, which may contribute to potential difficulties in cold starts. On the other hand, the flash points, which were higher than those of diesel fuel constituted a safety guarantee from the point of view of handling and storage. (author)

  16. Transesterification of Vegetable Oils with Ethanol and Characterization of the Key Fuel Properties of Ethyl Esters

    Directory of Open Access Journals (Sweden)

    Stamoulis Stournas

    2009-06-01

    Full Text Available The transesterification reactions of four different vegetable oils (sunflower, rapeseed, olive oil and used frying oil with ethanol, using sodium hydroxide as catalyst, were studied. The ester preparation involved a two-step transesterification reaction, followed by purification. The effects of the mass ratio of catalyst to oil (0.25 – 1.5%, the molar ratio of ethanol to oil (6:1 – 12:1, and the reaction temperature (35 – 90 °C were studied for the conversion of sunflower oil to optimize the reaction conditions in both stages. The rest of the vegetable oils were converted to ethyl esters under optimum reaction parameters. The optimal conditions for first stage transesterification were an ethanol/oil molar ratio of 12:1, NaOH amount (1% wt/wt, and 80 °C temperature, whereas the maximum yield of ethyl esters reached 81.4% wt/wt. In the second stage, the yield of ethyl esters was improved by 16% in relation with the one-stage transesterification, which was obtained under the following optimal conditions: catalyst concentration 0.75% and ethanol/oil molar ratio 6:1. The fuel properties of the esters were measured according to EN test methods. Based on the experimental results one can see that the ethyl esters do not differ significantly from methyl esters. Moreover, the results showed that the values of density, viscosity, and higher heating value of ethyl esters were similar to those of automotive and heavy duty engine diesel fuel. However, the CFPP values were higher, which may contribute to potential difficulties in cold starts. On the other hand, the flash points, which were higher than those of diesel fuel constituted a safety guarantee from the point of view of handling and storage.

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

    Science.gov (United States)

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

    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. PMID:26926564

  18. Synergistic extraction of U(VI) with mixtures of 2-ethyl hexyl phosphonic acid-mono-2-ethyl hexyl ester (PC-88A) and TBP, TOPO or Cyanex 923

    International Nuclear Information System (INIS)

    The extraction of uranium (VI) from hydrochloric acid medium with PC-88A (H2A2 in dimeric form) and neutral organo phosphorous donors like TBP, TOPO and Cyanex 923 (S) in dodecane is reported. Experiments were performed with PC-88A, TOPO and Cyanex 923 alone and with the mixtures of PC-88A with TBP, TOPO or Cyanex 923. The presence of neutral donors in PC-88A solutions gave synergistic enhancement in the extraction of uranium (VI), the order being Cyanex 923 > TOPO > TBP. The species extracted with PC-88A alone is UO2(HA2)2, whereas with TOPO or Cyanex 923 alone, it is UO2Cl2.2S and with the synergistic mixtures it is UO2(HA2)2.S. The power dependencies of S and PC-88A under experimental conditions have also been evaluated using non-linear regression analysis. The equilibrium constants of synergistic extraction have been calculated and the mechanism of the extraction is discussed. The effect of different organic diluents on uranium (VI) extraction with PC-88A has also been examined. (orig.)

  19. Synergistic extraction of U(VI) with mixtures of 2-ethyl hexyl phosphonic acid-mono-2-ethyl hexyl ester (PC-88A) and TBP, TOPO or Cyanex 923

    Energy Technology Data Exchange (ETDEWEB)

    Singh, D.K.; Singh, H. [Rare Earth Development Section, Bhabha Atomic Research Centre, Trombay, Mumbai (India); Mathur, J.N. [Radiochemistry Div., Bhabha Atomic Research Centre, Trombay, Mumbai (India)

    2001-07-01

    The extraction of uranium (VI) from hydrochloric acid medium with PC-88A (H{sub 2}A{sub 2} in dimeric form) and neutral organo phosphorous donors like TBP, TOPO and Cyanex 923 (S) in dodecane is reported. Experiments were performed with PC-88A, TOPO and Cyanex 923 alone and with the mixtures of PC-88A with TBP, TOPO or Cyanex 923. The presence of neutral donors in PC-88A solutions gave synergistic enhancement in the extraction of uranium (VI), the order being Cyanex 923 > TOPO > TBP. The species extracted with PC-88A alone is UO{sub 2}(HA{sub 2}){sub 2}, whereas with TOPO or Cyanex 923 alone, it is UO{sub 2}Cl{sub 2}.2S and with the synergistic mixtures it is UO{sub 2}(HA{sub 2}){sub 2}.S. The power dependencies of S and PC-88A under experimental conditions have also been evaluated using non-linear regression analysis. The equilibrium constants of synergistic extraction have been calculated and the mechanism of the extraction is discussed. The effect of different organic diluents on uranium (VI) extraction with PC-88A has also been examined. (orig.)

  20. Optimization of the production of ethyl esters by ultrasound assisted reaction of soybean oil and ethanol

    Directory of Open Access Journals (Sweden)

    S. Rodrigues

    2009-06-01

    Full Text Available Biodiesel is a renewable liquid fuel that can be produced by a transesterification reaction between a vegetable oil and an alcohol. This paper evaluates and optimizes the production of ethyl esters (biodiesel from soybean oil and ethanol. The reaction was carried out by applying ultrasound under atmospheric pressure and ambient temperature. Response surface methodology was used to evaluate the influence of alcohol to oil molar ratio and catalyst concentration on the yield of conversion of soybean oil into ethyl esters. The process resulted in a maximum yield of 91.8% after 30 minutes of reaction. The process variables alcohol to oil ratio and catalyst to oil ratio were statistically significant regarding the yield of ethyl esters. The optimal operating condition was obtained applying an alcohol to oil molar ratio of 10.2 and a catalyst to oil weight ratio of 0.0035.

  1. Papain-Catalyzed Chemoenzymatic Synthesis of Telechelic Polypeptides Using Bis(Leucine Ethyl Ester) Initiator.

    Science.gov (United States)

    Tsuchiya, Kousuke; Numata, Keiji

    2016-07-01

    In order to construct unique polypeptide architectures, a novel telechelic-type initiator with two leucine ethyl ester units is designed for chemoenzymatic polymerization. Glycine or alanine ethyl ester is chemoenzymatically polymerized using papain in the presence of the initiator, and the propagation occurs at each leucine ethyl ester unit to produce the telechelic polypeptide. The formation of the telechelic polypeptides is confirmed by (1) H NMR and MALDI-TOF mass spectroscopies. It is revealed by AFM observation that long nanofibrils are formed from the telechelic polyalanine, whereas a conventional linear polyalanine with a similar degree of polymerization shows granule-like structures. The telechelic polyglycine and polyalanine show the crystalline structures of Polyglycine II and antiparallel β-sheet, respectively. It is demonstrated that this method to synthesize telechelic-type polypeptides potentially opens up a pathway to construct novel hierarchical structures by self-assembly. PMID:26947148

  2. Production of ethyl ester from crude palm oil by two-step reaction using continuous microwave system

    Directory of Open Access Journals (Sweden)

    Sukritthira Ratanawilai

    2011-02-01

    Full Text Available The esterification of free fatty acids (FFA in vegetable oils with alcohol using an acid catalyst is a promising methodto convert FFA into valuable ester and obtain a FFA-free oil that can be further transesterified using alkali bases. In thiswork, the direct esterification reaction of FFA in crude palm oil to ethyl ester by continuous microwave was studied and theeffects of the main variables involved in the process, amount of catalyst, reaction time and the molar ratio oil/ alcohol, wereanalyzed. The optimum condition for the continuous esterification process was carried out with a molar ratio of oil to ethanol1:6, using 1.25%wt of H2SO4/oil as a catalyst, microwave power of 78 W and a reaction time 90 min. This esterification processshows that the amount of FFA was reduced from 7.5%wt to values around 1.4 %wt. Similar results were obtained followingconventional heating at 70°C, but only after a reaction time of 240 min. The esterified crude palm oil is suitable to perform thetransesterification process. Transesterification of the esterified palm oil has been accomplished with a molar ratio of oil toethanol of 1:8.5, 2.5%wt of KOH as a catalyst, a microwave power of 78 W, and a reaction time of 7 min. In addition, theproblem of glycerin separation was solved by mixing 10%wt of pure glycerin into the ethyl ester to induce the glycerin fromthe reaction to separated. This two-step esterification and transesterification process provided a yield of 78%wt with anester content of 97.4%wt. The final ethyl ester product met with the specifications stipulated by ASTM D6751-02.

  3. A review of omega-3 ethyl esters for cardiovascular prevention and treatment of increased blood triglyceride levels

    Directory of Open Access Journals (Sweden)

    Clemens von Schacky

    2006-09-01

    Full Text Available Clemens von SchackyMedizinische Klinik and Poliklinik Innenstadt, University of Munich, Munich, GermanyAbstract: The two marine omega-3 fatty acids eicosapentaenoic acid (EPA and docosahexaenoic acid (DHA, prevalent in fish and fish oils, have been investigated as a strategy towards prophylaxis of atherosclerosis. While the results with fish and fish oils have been not as clear cut, the data generated with the purified ethyl ester forms of these two fatty acids are consistent. Although slight differences in biological activity exist between EPA and DHA, both exert a number of positive actions against atherosclerosis and its complications. EPA and DHA as ethyl esters inhibit platelet aggregability, and reduce serum triglycerides, while leaving other serum lipids essentially unaltered. Glucose metabolism has been studied extensively, and no adverse effects were seen. Pro-atherogenic cytokines are reduced, as are markers of endothelial activation. Endothelial function is improved, vascular occlusion is reduced, and the course of coronary atherosclerosis is mitigated. Heart rate is reduced, and heart rate variability is increased by EPA and DHA. An antiarrhythmic effect can be demonstrated on the supraventricular and the ventricular level. More importantly, two large studies showed reductions in clinical endpoints like sudden cardiac death or major adverse cardiac events. As a consequence, relevant cardiac societies recommend using 1 g/day of EPA and DHA for cardiovascular prevention, after a myocardial infarction and for prevention of sudden cardiac death.Keywords: sudden cardiac death, major adverse cardiac events, cardiovascular prevention, eicosapentaenoic acid, docosahexaenoic acid

  4. Elevated plasma creatinine due to creatine ethyl ester use.

    Science.gov (United States)

    Velema, M S; de Ronde, W

    2011-02-01

    Creatine is a nutritional supplement widely used in sport, physical fitness training and bodybuilding. It is claimed to enhance performance. We describe a case in which serum creatinine is elevated due to the use of creatine ethyl esther. One week after withdrawal, the plasma creatinine had normalised. There are two types of creatine products available: creatine ethyl esther (CEE) and creatine monohydrate (CM). Plasma creatinine is not elevated in all creatine-using subjects. CEE , but not CM, is converted into creatinine in the gastrointestinal tract. As a result the use of CEE may be associated with elevated plasma creatinine levels. Since plasma creatinine is a widely used marker for renal function, the use of CEE may lead to a false assumption of renal failure.

  5. 21 CFR 172.859 - Sucrose fatty acid esters.

    Science.gov (United States)

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Sucrose fatty acid esters. 172.859 Section 172.859... CONSUMPTION Multipurpose Additives § 172.859 Sucrose fatty acid esters. Sucrose fatty acid esters identified...) Sucrose fatty acid esters are the mono-, di-, and tri-esters of sucrose with fatty acids and are...

  6. Studies on biodegradation and molecular characterization of 2,4-D Ethyl Ester and Pencycuron induced Cyanobacteria by using GC-MS and 16S rDNA sequencing

    Directory of Open Access Journals (Sweden)

    J. I. Nirmal Kumar

    2013-03-01

    Full Text Available GC-MS study and molecular characterization by 16S rDNA amplification were carried out to evaluate differential effects of 2,4-D ethyl ester and pencycuron on Anabaena fertilissima, Aulosira fertilissima and Westiellopsis prolifica. Each organism has its own capacity to degrade both pesticides into various subgroups depending largely upon the main functional group of each individual pesticide. Hence, different subgroups like 2,4-D methyl ester, 2,4-D isobutyl ester, Isobutyric acid allyl ester, 3-Bromobutyric acid, 2,4-D butyl ester, Hydroxyurea, Trifluroacetic acid, 2-Methyl propyl ester, Acetic acid 2-propenyl ester and Acetic acid (2,3-dichlorophenoxy were transformed from 2,4-D ethyl ester while Benzoxazole was the only compound generated from pencycuron treated W. prolifica. The results obtained by 16S rDNA sequencing confirmed that 16S rDNA region of Anabaena fertilissima was more affected by 2,4-D ethyl ester as there was no homology in the region of 39 basepairs, in addition, several mismatches and gaps were observed, whereas less difference in 16S rDNA was observed in case of Aulosira fertilissima and W. prolific on forth day. However, there was no significant change in the sequence of 16S rDNA pattern of all the three test organisms after 16-days of exposure to pencycuron treatment.

  7. Long-chain alkanoic acid esters of lupeol from Dorstenia harmsiana Engl. (Moraceae).

    Science.gov (United States)

    Poumale, Herve Martial P; Awoussong, Kenzo Patrice; Randrianasolo, Rivoarison; Simo, Christophe Colombe F; Ngadjui, Bonaventure Tchaleu; Shiono, Yoshihito

    2012-01-01

    In addition to lupeol (1a), three long-chain alkanoic acid esters of lupeol, in which two were new, were isolated from the hexane and ethyl acetate twigs extract of Dorstenia harmsiana Engl. (Moraceae). The structures of the new compounds were elucidated on the basis of 1D and 2D NMR experiments. Some isolated compounds were evaluated for their antimicrobial activities. The lupeol and its three long-chain alkanoic acid esters showed antifungal and antibacterial activities.

  8. Identification of rapeseed oil fatty acid esters in transesterification reactions by gas chromatography - mass spectrometry method

    International Nuclear Information System (INIS)

    Rapeseed oil transesterification with different alcohols - methyl, ethyl, n-propyl and isopropyl alcohol - has been carried out. Yields of fatty acid alkyl esters obtained from rapeseed oil were determined using the internal standard method. Results of interpretation of the obtained ester mass spectra are reported. The specimen of Latvian rape oil contains: 57.6% of oleic acid, 18.2% of linoleic acid, 8.2% linolenic acid, 3.3% palmitic acid, 2% of stearic acid and less than 1% of arachidic acid. Values of Kovats retention indices of the rapeseed oil fatty acid esters on the capillary columns DB-5 MS and DB-17 MS have been compared. More selective separation of fatty acid alkyl esters has been achieved on the stationary phase with higher content of phenyl groups (DB-17 MS). (authors)

  9. Experimental Autoignition of C4-C6 Saturated and Unsaturated Methyl and Ethyl Esters

    CERN Document Server

    Bennadji, Hayet; Coniglio-Jaubert, Lucie; Billaud, Francis; Glaude, Pierre-Alexandre; Battin-Leclerc, Frédérique

    2009-01-01

    Autoignition delay times, ?, of methyl crotonate, methyl acrylate, ethyl butanoate, ethyl crotonate, and ethyl acrylate were studied in shock tube experiments. A series of mixtures diluted with argon, of varying fuel/oxygen equivalence ratios (?=0.25, 0.4, 1.0, and 2.0), were measured behind reflected shock waves over the temperature range of 1280-1930 K, pressure range of 7-9.65 atm, during which the logarithm of ? varies linearly as a function of the inverse temperature for all equivalence ratios. The ignition delay time decreases as temperature rises. The dependence of ? on temperature, and reactant concentrations is given in an empirical correlation. The results provide a database for the validation of small saturated and unsaturated esters kinetic mechanisms at elevated temperatures and pressure combustion.

  10. Docosahexaenoic acid ethyl esther (DHAEE microcapsule production by spray-drying: optimization by experimental design

    Directory of Open Access Journals (Sweden)

    Rodney Alexandre Ferreira Rodrigues

    2011-09-01

    Full Text Available Docosahexaenoic acid is an essential polyunsaturated fatty acid with important metabolic activities. Its conjugated double bonds make it susceptible to decomposition. Its stability may be improved through fatty acid entrapment with a spray-drying technique; however, the many parameters involved in this technique must be considered to avoid affecting the final product quality. Therefore, this study aimed to evaluate the entrapment conditions and yields of fish oil enriched with docosahexaenoic acid ethyl ester. Microcapsules were obtained from Acacia gum using a spray-drying technique. The experimental samples were analyzed by chromatography and delineated by Statistica software, which found the following optimum entrapment conditions: an inlet temperature of 188 °C; 30% core material; an N2 flow rate of 55 mm; and a pump flow rate of 12.5 mL/minute. These conditions provided a 66% yield of docosahexaenoic acid ethyl ester in the oil, corresponding to 19.8% of entrapped docosahexaenoic acid ethyl ester (w/w. This result was considered significant since 30% corresponded to wall material.

  11. Antifungal activity of 4-substituted crotonic acid esters.

    Science.gov (United States)

    Gershon, H; Shanks, L; Gawiak, D E

    1976-08-01

    Twenty-three 4-substituted crotonic acid esters were tested for antifungal activity against Candida albicans, Aspergillus niger, Mucor mucedo, and Trichophyton mentagrophytes. For the analogues of the methyl ester containing substituents in the 4 position, the following order of fungitoxicity was observed: I greater than Br greater than Cl greater than CH3S greater than CH3O greater than F=H. Of the homologues of the esters of the 4-iodo and 4-bromo compounds which included methyl, ethyl, n-propyl, n-butyl, n-pentyl, and n-hexyl, ethyl 4-iodocrotonate was most toxic to the four fungi at pH 7.0 in the presence of 10% beef serum (C. albicans, 18mug/ml, A. niger, 40 mug/ml, M. mucedo, 5 mug/ml, T. mentagrophytes, 4 mug/ml). It is believed that the mechanism of fungitoxicity is due, in part, to a nucleophilic reaction involving SH-containing compounds. This is based on the correlation of fungitoxicity with the order of leaving groups in the nucleophilic reaction and the protection against the toxicity of the test compounds to the fungi by cysteine and glutathione.

  12. Acrylic Acid and Esters Will Be Oversupply

    Institute of Scientific and Technical Information of China (English)

    Zheng Chengwang

    2007-01-01

    @@ Drastic capacity growth The production capacity of acrylic acid in China has grown drastically in recent years. With the completion of the 80 thousand t/a acrylic acid and 130 thous and t/a acrylic ester project in Shenyang Paraffin Chemical Industrial Co., Ltd., (CCR2006,No. 31) the capacity of acrylic acid in China has reached 882 thousand t/a.

  13. Red blood cell oleic acid levels reflect olive oil intake while omega-3 levels reflect fish intake and the use of omega-3 acid ethyl esters: The Gruppo Italiano per lo Studio della Sopravvivenza nell'Infarto Miocardico-Heart Failure trial.

    Science.gov (United States)

    Harris, William S; Masson, Serge; Barlera, Simona; Milani, Valentina; Pileggi, Silvana; Franzosi, Maria Grazia; Marchioli, Roberto; Tognoni, Gianni; Tavazzi, Luigi; Latini, Roberto

    2016-09-01

    The Gruppo Italiano per lo Studio della Sopravvivenza nell'Infarto Miocardico-Heart Failure (GISSI-HF) study reported benefits of n-3 fatty acid (FA) treatment on cardiovascular (CV) events, but the effects of treatment on a putative CV disease risk factor, the red blood cell (RBC) n-3 FA level (the omega-3 index), have not been examined in this context. We hypothesized that treatment with prescription omega-3 acid ethyl esters (O3AEE) would increase the omega-3 index to the proposed cardioprotective value of 8%. RBCs were collected from a subset of patients participating in the GISSI-HF study (n=461 out of 6975 randomized), at baseline and after 3 months of treatment with either an olive oil placebo or O3AEE (1 g/d). RBC FA levels were expressed as a percentage of total FA. Patients also reported their typical olive oil and fish intakes. RBC oleic acid levels were directly correlated with reported frequency of olive oil consumption, and the omega-3 index was correlated with reported fish intake (P for trends <0.001 for both). After treatment, the omega-3 index increased from 4.8±1.7% to 6.7±1.9% but was unchanged in the placebo group (4.7±1.7 to 4.8±1.5%) (P<.0001 for changes between groups). At 3 months, more patients reached the proposed target omega-3 index level of 8%-12% in the treated vs placebo group (22.6% vs. 1.3%, P<.0001), however, what omega-3 index levels were ultimately achieved after four years in this trial are unknown. PMID:27632919

  14. Vapor-liquid equilibrium for the system ethyl alcohol + ester; Equilibrio liquido-vapor para o sistema alcool etilico+ester

    Energy Technology Data Exchange (ETDEWEB)

    Oliveira, Humberto Neves Maia de; Nascimento, Yuri Corsino do; Chiavone-Filho, Osvaldo [Universidade Federal do Rio Grande do Norte (UFRN), Natal, RN (Brazil)

    2004-07-01

    This work consists of the experimental determination of a series of vapor-liquid equilibrium (VLE) data, for mixtures of ethyl alcohol + ester (ethyl acetate), prepared synthetically, that may be present in the production of biodiesel. The separation of the ethyl alcohol from esters by distillation is an important stage of this process, and therefore it demands accurate data for an appropriate modelling, and later optimization via simulators. FISCHER'S ebulliometer, with digital control (Model 602), was used for measurement of VLE data for the system ethyl alcohol + ester. It consists of a recirculation cell of the both vapor and liquid phases, providing complete data, i.e., pressure, temperature and compositions of the liquid and vapor phases that were obtained by gaseous chromatography (PTxy). This apparatus is coupled to a thermostatic bath with cooling (TE-184 TECNAL) that aims to condense the coming steams of the ebullition in order to return to the mixture camera. The VLE data obtained experimentally were submitted to the test of thermodynamic consistence of the deviations, where the equation of Gibbs-Duhem is used, through the model UNIQUAC. The parameters obtained from the experimental data can be applied in the simulators of processes with the purpose of optimizing the separation of the ethyl alcohol of Ester. (author)

  15. Performance and emission study of Mahua oil (madhuca indica oil) ethyl ester in a 4-stroke natural aspirated direct injection diesel engine

    Energy Technology Data Exchange (ETDEWEB)

    Puhan, S.; Vedaraman, N.; Bharat Ram, B.V. [Central Leather Research Inst., Chennai (India). Chemical Engineering Division; Sankaranarayanan, G. [Central Leather Research Inst., Chennai (India). Chemical Engineering Division; Anna Univ., Chennai (India). Mechanical Engineering Division

    2005-07-01

    In this investigation, Mahua Oil Ethyl Ester was prepared by transesterification using sulfuric acid (H{sub 2}SO{sub 4}) as catalyst and tested in a 4-stroke direct injection natural aspirated diesel engine. Tests were carried out at constant speed of 1500 rev/min at different brake mean effective pressures. Results showed that brake thermal efficiency of Mahua Oil Ethyl Ester (MOEE) was comparable with diesel and it was observed that 26.36% for diesel whereas 26.42% for MOEE. Emissions of carbon monoxide, hydrocarbons, oxides of nitrogen and Bosch smoke number were reduced around 58, 63, 12 and 70%, respectively, in case of MOEE compared to diesel. Based on this study, MOEE can be used a substitute for diesel in diesel engine. (Author)

  16. Heat release and engine performance effects of soybean oil ethyl ester blending into diesel fuel

    International Nuclear Information System (INIS)

    The engine performance impact of soybean oil ethyl ester blending into diesel fuel was analyzed employing heat release analysis, in-cylinder exergy balances and dynamometric tests. Blends with concentrations of up to 30% of soybean oil ethyl ester in volume were used in steady-state experiments conducted in a high speed turbocharged direct injection engine. Modifications in fuel heat value, fuel-air equivalence ratio and combustion temperature were found to govern the impact resulting from the addition of biodiesel on engine performance. For the analyzed fuels, the 20% biodiesel blend presented the best results of brake thermal efficiency, while the 10% biodiesel blend presented the best results of brake power and sfc (specific fuel consumption). In relation to mineral diesel and in full load conditions, an average increase of 4.16% was observed in brake thermal efficiency with B20 blend. In the same conditions, an average gain of 1.15% in brake power and a reduction of 1.73% in sfc was observed with B10 blend.

  17. Solid acid catalysed formation of ethyl levulinate and ethyl glucopyranoside from mono- and disaccharides

    DEFF Research Database (Denmark)

    Shunmugavel, Saravanamurugan; Riisager, Anders

    2012-01-01

    Sulfonic acid functionalised SBA-15 (SO3H-SBA-15), sulfated zirconia and beta, Y, ZSM-5 and mordenite zeolite catalysts have been applied for the dehydration of sugars to ethyl levulinate and ethyl-D-glucopyranoside (EDGP) using ethanol as solvent and reactant. The SO3H-SBA-15 catalyst showed a...... high catalytic activity for the selective conversion of fructose to ethyl levulinate (57%) and glucose to EDGP (80%) at 140 °C, whereas the disaccharide sucrose yielded a significant amount of both products. The SO3H-SBA-15 catalysts were found to be highly active compared to the zeolites under...

  18. Tequila volatile characterization and ethyl ester determination by solid phase microextraction gas chromatography/mass spectrometry analysis.

    Science.gov (United States)

    Vallejo-Cordoba, Belinda; González-Córdova, Aarón Fernando; del Carmen Estrada-Montoya, María

    2004-09-01

    Solid phase microextraction (SPME) and gas chromatography were used for tequila volatile characterization and ethyl ester quantitation. Several factors determined the differences in tequila volatile profiles obtained by the SPME technique, namely, sampling mode, fiber coating, and fiber exposure time. Each of these factors determined the most suitable conditions for the analysis of volatile profiles in tequila. Volatile extraction consisted of placing 40 mL of tequila in a sealed vial kept at 40 degrees C. A poly(dimethylsiloxane) fiber was immersed in the liquid for 60 min and desorbed for 5 min into the gas chromatograph. The identified volatiles by mass spectrometry were mainly alcohols, esters, and ketones. The calibration curves for ethyl hexanoate, octanoate, and decanoate followed linear relationships with highly significant (p tequila samples. Quantitative differences in ethyl esters were found for the four most commonly known tequila types: silver, gold, aged, and extra-aged.

  19. 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

  20. Síntese, caracterização e análise térmica dos sais de lítio, sódio e potássio do ácido palmítico e do seu éster etílico Synthesis, characterization and thermal analysis of lithium, sodium and potassium salts of the palmitic acid and its ethyl ester

    Directory of Open Access Journals (Sweden)

    André Luis Castro de Sales

    2008-01-01

    Full Text Available Alkaline salts of the palmitic acid were synthesized and characterized from aqueous and ethanolic medium. The salts were characterized by elemental analysis (EA and infrared spectroscopy (IR. EA and IR, being its synthesis comproved, also characterized the ethyl palmitate. All the salts and the ester were submitted to thermal analysis using thermogravimetry (TG, and differential thermal analysis (DTA in the temperature ranging from room to 700 ºC under air dynamic atmosphere. Differential scanning calorimetry (DSC measurements were taken from -90 ºC up to temperatures close to the starting of the decomposition temperature, determined by thermogravimetry, using heating and cooling cycles.

  1. Lipid-lowering and anti-inflammatory effects of omega 3 ethyl esters and krill oil: a randomized, cross-over, clinical trial

    Science.gov (United States)

    Rosticci, Martina; Morbini, Martino; Cagnati, Marcella; Grandi, Elisa; Parini, Angelo; Borghi, Claudio

    2016-01-01

    Introduction Polyunsaturated fatty acids (PUFAs) derived from different sources could have different lipid-lowering effects in humans. The main aim of our study was to compare the short-term triglyceride-lowering efficacy of krill oil and purified omega 3 ethyl ester PUFAs in mildly overweight hypertriglyceridemic subjects. Material and methods This double-blind, randomized clinical trial was carried out in 25 moderately hypertriglyceridemic subjects (TG = 150–500 mg/dl). After a 4-week run-in, participants were allocated to treatment with similar pills containing omega 3 ethyl ester PUFAs 1000 mg twice a day vs. krill oil 500 mg twice a day. After 4 weeks of treatment, participants were asked to observe a 4-week wash-out period, and they were then assigned to the alternative treatment for a further period of 4 weeks. Results Although both PUFA sources were able to improve TG plasma levels, esterified omega 3 PUFAs were more efficacious than krill oil (p krill oil treatment was able to significantly improve high-density lipoprotein cholesterol and apolipoprotein AI levels, compared to both baseline (p krill oil improved it more efficaciously than esterified omega 3 PUFAs (p Krill oil has lipid-lowering effects comparable with those obtained through a 4-fold higher dose of purified omega 3 ethyl ester PUFAs in mildly overweight hypertriglyceridemic subjects, while more efficaciously reducing hs-CRP. PMID:27279841

  2. [Enantioseparation of 2-phenylcarboxylic acid esters by capillary gas chromatography].

    Science.gov (United States)

    Shi, Xueyan; Liu, Feipeng; Bian, Qinghua

    2016-01-01

    Chiral 2-arylcarboxylic acid derivatives are important intermediates for preparing 2-arylcarboxylic acids, which are non-steroidal anti-inflammatory drugs (NSAIDs). In order to separate 2-phenylcarboxylic acid ester enantiomers by capillary gas chromatography (CGC), 2, 6-di-O-pentyl-3-O-butyryl-β-cyclodextrin and 2,6-di-O-benzyl-3-O-heptanoyl-β-cyclodextrin were used as CGC chiral stationary phases, separately, and their enantioseparation abilities to enantiomers of methyl 2-phenylbutanoate, ethyl 2-phenylbutanoate, isopropyl 2-phenylbutanoate, methyl 2-phenylpropionate and cyclopentyl 2-phenylpropionate were examined. It was found that methyl 2-phenylbutanoate, methyl 2-phenylpropionate and cyclopentyl 2-phenylpropionate were successfully separated by using 2,6-di-O-pentyl-3-O-butyryl-β-cyclodextrin and 2,6-di-O-benzyl-3-O-heptanoyl-β-cyclodextrin as CGC chiral stationary phases, respectively. The enantiomer separation abilities of 2, 6-di-O-pentyl-3-O-butyryl-β-cyclodextrin to the three pairs of 2-phenylcarboxylic acid esters tested are superior to those of 2, 6-di-O-benzyl-3-O-heptanoyl-β-cyclodextrin. PMID:27319170

  3. Improved ethyl caproate production of Chinese liquor yeast by overexpressing fatty acid synthesis genes with OPI1 deletion.

    Science.gov (United States)

    Chen, Yefu; Luo, Weiwei; Gong, Rui; Xue, Xingxiang; Guan, Xiangyu; Song, Lulu; Guo, Xuewu; Xiao, Dongguang

    2016-09-01

    During yeast fermentation, ethyl esters play a key role in the development of the flavor profiles of Chinese liquor. Ethyl caproate, an ethyl ester eliciting apple-like flavor, is the characteristic flavor of strong aromatic liquor, which is the best selling liquor in China. In the traditional fermentation process, ethyl caproate is mainly produced at the later fermentation stage by aroma-producing yeast, bacteria, and mold in a mud pit instead of Saccharomyces cerevisiae at the expense of grains and fermentation time. To improve the production of ethyl caproate by Chinese liquor yeast (S. cerevisiae) with less food consumption and shorter fermentation time, we constructed three recombinant strains, namely, α5-ACC1ΔOPI1, α5-FAS1ΔOPI1, and α5-FAS2ΔOPI1 by overexpressing acetyl-CoA carboxylase (ACC1), fatty acid synthase 1 (FAS1), and fatty acid synthase 2 (FAS2) with OPI1 (an inositol/choline-mediated negative regulatory gene) deletion, respectively. In the liquid fermentation of corn hydrolysate, the contents of ethyl caproate produced by α5-ACC1ΔOPI1, α5-FAS1ΔOPI1, and α5-FAS2ΔOPI1 increased by 0.40-, 1.75-, and 0.31-fold, correspondingly, compared with the initial strain α5. The contents of other fatty acid ethyl esters (FAEEs) (C8:0, C10:0, C12:0) also increased. In comparison, the content of FAEEs produced by α5-FAS1ΔOPI1 significantly improved. Meanwhile, the contents of acetyl-CoA and ethyl acetate were enhanced by α5-FAS1ΔOPI1. Overall, this study offers a promising platform for the development of pure yeast culture fermentation of Chinese strong aromatic liquor without the use of a mud pit. PMID:27344573

  4. Ethyl ester purpurine-18 from Gossypium mustelinum (Malvaceae);Feoforbideo (etoxi-purpurina-18) isolado de Gossypium mustelinum (Malvaceae)

    Energy Technology Data Exchange (ETDEWEB)

    Silva, Tania Maria Sarmento; Camara, Celso Amorim, E-mail: taniasarmento@dq.ufrpe.b [Universidade Federal de Pernambuco (UFPE), Recife, PE (Brazil). Dept. de Quimica; Barbosa-Filho, Jose Maria [Universidade Federal da Paraiba (UFPB), Joao Pessoa, PB (Brazil). Lab. de Tecnologia Farmaceutica; Giulietti, Ana Maria [Universidade Estadual de Feira de Santana, BA (Brazil). Dept. de Ciencias Biologicas

    2010-07-01

    The phaeophorbide ethyl ester named Purpurine-18 and the flavonoids quercetin and kaempferol were obtained by chromatographic procedures from the chloroform fraction of aerial parts of Gossypium mustelinum. The structure of these compound was determined by NMR, IR and mass spectra data analysis. This is the first occurrence of this compound in Angiosperm. (author)

  5. 27 CFR 21.107 - Ethyl acetate.

    Science.gov (United States)

    2010-04-01

    ... 27 Alcohol, Tobacco Products and Firearms 1 2010-04-01 2010-04-01 false Ethyl acetate. 21.107....107 Ethyl acetate. (a) 85 percent ester: (1) Acidity (as acetic acid). Not more than 0.015 percent by...); for incorporation by reference, see § 21.6(b).) When 100 ml of ethyl acetate are distilled by...

  6. Kinetics of Ethyl Acetate Synthesis Catalyzed by Acidic Resins

    Science.gov (United States)

    Antunes, Bruno M.; Cardoso, Simao P.; Silva, Carlos M.; Portugal, Ines

    2011-01-01

    A low-cost experiment to carry out the second-order reversible reaction of acetic acid esterification with ethanol to produce ethyl acetate is presented to illustrate concepts of kinetics and reactor modeling. The reaction is performed in a batch reactor, and the acetic acid concentration is measured by acid-base titration versus time. The…

  7. Fatty acid ethyl esters production using a non-commercial lipase in pressurized propane medium Produção de ésteres etílicos de ácidos graxos utilizando uma lipase não comercial em propano pressurizado

    Directory of Open Access Journals (Sweden)

    Cristiane Hildebrand

    2009-09-01

    Full Text Available The objective of this work is to investigate the production of fatty acid ethyl esters from soybean oil in compressed propane using a non-commercial lipase from Yarrowia lipolytica and two commercial ones as catalysts, Amano PS and Amano AY30. The experiments were performed in the temperature range of 35-65 °C. at 50 bar, enzyme concentration of 5 wt%, oil to ethanol molar ratio of 1:6 and 1:9, and solvent to substrates mass ratio of 2:1 and 4:1. The results indicated that low reaction conversions were generally obtained with the use of commercial and non-commercial lipases in pressurized propane medium. On the other hand, the aspects of low solvent to substrates mass ratio and mild temperature and pressure operating conditions used to produce ethyl esters justify further investigations to improve reaction yields.O principal objetivo deste trabalho foi investigar a produção de ésteres etílicos de ácidos graxos a partir de óleo de soja em propano pressurizado, utilizando uma lipase não comercial (obtida por fermentação submersa de Yarrowia lipolytica e duas comerciais, Amano PS e Amano AY30. Os experimentos foram conduzidos no intervalo de temperatura de 35-65 °C, em pressão de 50 bar, concentração de enzima de 5 m/v%, razão molar óleo etanol de 1:6 e 1:9 e razão molar substratos solvente de 2:1 e 4:1. Os resultados obtidos indicaram que baixas conversões foram geralmente obtidas com o emprego das lipases testadas em propano pressurizado. Por outro lado, os aspectos de baixas razões molares entre o solvente e os substratos (óleo e etanol e condições amenas de temperatura e pressão usadas na produção dos ésteres etílicos possam justificar investigações futuras no sentido de aumentar a conversão do processo.

  8. Influence of poly(2-methoxy-5-(2’-ethyl)-hexyloxy-p-phenylene vinylene):(6,6)-phenyl C61 butyric acid methyl ester blend ratio on the performance of inverted type organic solar cells based on Eosin-Y-coated ZnO nanorod arrays

    Energy Technology Data Exchange (ETDEWEB)

    Ginting, Riski Titian [School of Applied Physics, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor (Malaysia); Yap, Chi Chin, E-mail: ccyap@ukm.my [School of Applied Physics, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor (Malaysia); Yahaya, Muhammad [School of Applied Physics, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor (Malaysia); Salleh, Muhamad Mat [Institute of Microengineering and Nanoelectronics (IMEN), Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor (Malaysia)

    2013-06-01

    The influence of poly(2-methoxy-5-(2’-ethyl)-hexyloxy-p-phenylene vinylene) (MEH-PPV) and (6,6)-phenyl C61 butyric acid methyl ester (PCBM) weight ratio on the photovoltaic performance of inverted type organic solar cell based on Eosin-Y-coated ZnO nanorods has been investigated. Experimental results showed that the photovoltaic performance improved with weight ratio of MEH-PPV:PCBM from 1:1 to 1:3 due to better percolation pathway for electron transport and enhanced infiltration of polymer blend into interspace of Eosin-Y-coated ZnO nanorods. However, the overall performance started to decrease at weight ratio of 1:4 due to the aggregation of PCBM clusters which results in poor polymer blend infiltration. The optimum device at weight ratio of 1:3 exhibited short circuit current density of 3.95 ± 0.10 mA cm{sup −2}, open circuit voltage of 0.53 ± 0.03 V, fill factor of 0.50 ± 0.03, and power conversion efficiency of 1.02 ± 0.07 %. - Highlights: • The device performance increased with donor:acceptor weight ratio up to 1:3. • Aggregation of fullerene-derivative led to poor infiltration at weight ratio of 1:4. • The optimum weight ratio was different from that of conventional device.

  9. Affinity labelling enzymes with esters of aromatic sulfonic acids

    Science.gov (United States)

    Wong, Show-Chu; Shaw, Elliott

    1977-01-01

    Novel esters of aromatic sulfonic acids are disclosed. The specific esters are nitrophenyl p- and m-amidinophenylmethanesulfonate. Also disclosed is a method for specific inactivation of the enzyme, thrombin, employing nitrophenyl p-amidinophenylmethanesulfonate.

  10. Synthesis and Antitumor Activity of Amino Acid Ester Derivatives Containing 5-Fluorouracil

    Directory of Open Access Journals (Sweden)

    Jing Xiong

    2009-08-01

    Full Text Available A series of amino acid ester derivatives containing 5-fluorouracil were synthesized using 1-ethyl-3-(3-dimethylaminopropylcarbodiimide hydrochloride (EDC•HCl and N-hydroxybenzotriazole (HOBt as a coupling agent. The structures of the products were assigned by NMR, MS, IR etc. The in vitro antitumor activity tests against leukaemia HL-60 and liver cancer BEL-7402 indicated that (R-ethyl 2-(2-(5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H-ylacetamido-3-(4-hydroxyphenyl propanoate showed more inhibitory effect against BEL-7402 than 5-FU.

  11. Effects of ethanol and long-chain ethyl ester concentrations on volatile partitioning in a whisky model system.

    Science.gov (United States)

    Boothroyd, Emily L; Linforth, Robert S T; Cook, David J

    2012-10-10

    Ethanolic atmospheric pressure chemical ionization mass spectrometry (APCI-MS) was used to analyze the headspace concentrations of a test set of 14 whisky volatile compounds above a series of aqueous ethanolic solutions differing in alcohol content (5-40% ABV) and with regard to concentration of ethyl hexadecanoate (0-500 mg/L). The latter was selected to represent the long-chain ethyl esters found at various concentrations in new-make spirit. Headspace ion intensities were modeled against ethanol and ethyl hexadecanoate concentrations as factors. A separate model was prepared for each compound. Not surprisingly, ethanol content in the range of 5-40% ABV had a significant effect (P 2.5). This finding is discussed in terms of the "structuring" effects of ethyl hexadecanoate when present above critical micelle concentration, leading to the selective incorporation of hydrophobic volatile compounds into the interior of micelle-like structures. Data presented illustrate that dilution of whiskies to 23% ABV for "nosing" in the presence of long-chain ethyl esters is likely to change the balance of volatile compounds in the headspace and thus the perceived aroma character.

  12. 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.

  13. Synthesis of stearic acid triethanolamine ester over solid acid catalysts

    Institute of Scientific and Technical Information of China (English)

    Tao Geng; Qiu Xiao Li; Ya Jie Jiang; Wei Wang

    2010-01-01

    The synthesis of stearic acid triethanolamine ester over solid acid catalysts was investigated.The results showed that the catalytic activity and selectivity of zirconium sulfate supported on SBA-15(6)(pore diameter 6 nm)is better than that of commonly used hypophosphorous acid,zirconium sulfate supported on MCM-41 and zirconium sulfate supported on SBA-15(9)(pore diameter 9 nm).

  14. Transesterification of mustard (Brassica nigra) seed oil with ethanol: Purification of the crude ethyl ester with activated carbon produced from de-oiled cake

    International Nuclear Information System (INIS)

    Highlights: • Biodiesel ethyl ester has been developed from mustard seed oil. • Variables affect the transesterification were investigated. • Dry washing using the activated carbon produced from the extraction remaining was applied to purify the ethyl esters. • Properties of the produced fuels were measured. • Blending of the produced ethyl ester with petro diesel was also investigated. - Abstract: The present study reports the production of mustard seed oil ethyl esters (MSOEE) through alkali-catalyzed transesterification with ethanol using potassium hydroxide as a catalyst. The influence of the process parameters such as catalyst concentration, ethanol to oil molar ratio, reaction temperature, reaction duration and the catalyst type was investigated so as to find out the optimal conditions for the transesterification process. As a result, optimum conditions for production of MSOEE were found to be: 0.90% KOH wt/wt of oil, 8:1 ethanol to oil molar ratio, a reaction temperature of 60 °C, and a reaction time of 60 min. Dry washing method with (2.50% wt.) of the activated carbon that was produced from the de-oiled cake was used to purify the crude ethyl ester from the residual catalyst and glycerol. The transesterification process provided a yield of 94% w/w of ethyl esters with an ester content of 98.22% wt. under the optimum conditions. Properties of the produced ethyl esters satisfied the specifications prescribed by the ASTM standards. Blending MSOEE with petro diesel was also investigated. The results showed that the ethyl esters had a slight influence on the properties of petro diesel

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

    Science.gov (United States)

    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.

  16. 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.

  17. NF EN 14103. July 2003. Fatty compounds derived products. Fatty acids methylic esters (FAME). Determination of the ester and methylic ester content of linoleic acid; NF EN 14103. Juillet 2003. Produits derives des corps gras. Esters methyliques d'acides gras (EMAG). Determination de la teneur en ester et en ester methylique de l'acide linolenique

    Energy Technology Data Exchange (ETDEWEB)

    NONE

    2003-07-01

    This European standard aims at determining the ester and methylic ester content of fatty acids methylic esters (FAME) used as pure bio-fuels or as constituent of a heating or diesel fuel. This method allows also to determine the methylic ester content of linoleic acid. It allows to verify that the ester content of FAMEs is greater than 90% (m/m) and that the linoleic acid content is comprised between 1% (m/m) and 15% (m/m). The method is applicable to FAMEs with methylic ester contents comprised between C14 and C24. (J.S.)

  18. Antifungal properties of 2-bromo-3-fluorosuccinic acid esters and related compounds.

    Science.gov (United States)

    Gershon, H; Shanks, L

    1977-04-01

    Twelve esters (C1-C6) of erythro- and threo-2-bromo-3-fluorosuccinic acid and related compounds were tested for antifungal activity against Candida albicans, Aspergillus niger, Mucor mucedo, and Trichophyton mentagrophytes at pH 5.7 and 7.0 in the absence and presence of 10% beef serum in Sabouraud dextrose agar. At pH 7.0 in the presence of 10% beef serum, no consistent pattern in the fungitoxicity of the erythro- and threo-2-bromo-3-fluorosuccinate esters was seen. Increasing the length of the ester function affects fungitoxicity as follows: C2 greater than C1 greater than C3 greater than C4 greater than C5 greater than C6. The most fungitoxic compound in this study was threo-ethyl 2-bromo-3-fluorosuccinate (C. albicans, 14 mug/ml; A. niger, 30 mug/ml; M. mucedo, 9 mug/ml; T. mentagrophytes, 5 mug/ml). Due to the ease of dehydrohalogenation, the fungitoxicity of 2-bromo-3-fluorosuccinic acid esters may be the result of a mixture composed of the parent compound, the bromo- and fluorofumaric acid esters, and HF and HBr of which part may be formed extracellularly and part within the cell.

  19. NMR Studies of a New Binding Mode of the Amino Acid Esters by Porphyrinatozinc(Ⅱ)

    Institute of Scientific and Technical Information of China (English)

    2001-01-01

    The binding mode of the amino acid ethyl esters(guest) by 5-(2-carboxylphenyl)-10,15,20-triphenylporphyrinatozinc(Ⅱ)(host 1) was studied by means of 1H NMR spectra. The binding mode is the hydrogen-bonding between the amino group of the guest and the carboxyl group of host 1 plus the coordination between the zinc atom of porphyrinatozinc(Ⅱ) and the carbonyl group of the guest. This is a novel binding mode of the metalloporphyrin to amino acid derivatives.

  20. Expanding the modular ester fermentative pathways for combinatorial biosynthesis of esters from volatile organic acids.

    Science.gov (United States)

    Layton, Donovan S; Trinh, Cong T

    2016-08-01

    Volatile organic acids are byproducts of fermentative metabolism, for example, anaerobic digestion of lignocellulosic biomass or organic wastes, and are often times undesired inhibiting cell growth and reducing directed formation of the desired products. Here, we devised a general framework for upgrading these volatile organic acids to high-value esters that can be used as flavors, fragrances, solvents, and biofuels. This framework employs the acid-to-ester modules, consisting of an AAT (alcohol acyltransferase) plus ACT (acyl CoA transferase) submodule and an alcohol submodule, for co-fermentation of sugars and organic acids to acyl CoAs and alcohols to form a combinatorial library of esters. By assembling these modules with the engineered Escherichia coli modular chassis cell, we developed microbial manufacturing platforms to perform the following functions: (i) rapid in vivo screening of novel AATs for their catalytic activities; (ii) expanding combinatorial biosynthesis of unique fermentative esters; and (iii) upgrading volatile organic acids to esters using single or mixed cell cultures. To demonstrate this framework, we screened for a set of five unique and divergent AATs from multiple species, and were able to determine their novel activities as well as produce a library of 12 out of the 13 expected esters from co-fermentation of sugars and (C2-C6) volatile organic acids. We envision the developed framework to be valuable for in vivo characterization of a repertoire of not-well-characterized natural AATs, expanding the combinatorial biosynthesis of fermentative esters, and upgrading volatile organic acids to high-value esters. Biotechnol. Bioeng. 2016;113: 1764-1776. © 2016 Wiley Periodicals, Inc. PMID:26853081

  1. Synthesis and characterization of biodegradable polyurethane based on poly(ε-caprolactone) and L-lysine ethyl ester diisocyanate

    Institute of Scientific and Technical Information of China (English)

    Jian HAN; Bing CHEN; Lin YE; Ai-ying ZHANG; Jian ZHANG; Zeng-guo FENG

    2009-01-01

    A biocompatible diisocyanate, lysine ethyl ester diisocyanate, was prepared. Afterwards, biodegra-dable polyurethane (PU) was synthesized by the step-growth polymerization of this diisocyanate with hydroxyl terminated poly(ε-caprolactone) in the presence of 1,4-butanediol as a chain-extender. The resulting PU was characterized by GPC, IR and DSC measurements. Its mechanical strength was found to increase with increasing the hard segment content. The PU microfiber meshes with high porosity were obtained by solution electrospinning technique. Their degradation behavior in the PBS and enzymatic solution was also investigated.

  2. A critical comparison of methyl and ethyl esters production from soybean and rice bran oil in the presence of microwaves.

    Science.gov (United States)

    Kanitkar, Akanksha; Balasubramanian, Sundar; Lima, Marybeth; Boldor, Dorin

    2011-09-01

    Transesterification of vegetable oils (from soybeans and rice bran) into methyl and ethyl esters using a batch microwave system was investigated in this study. A critical comparison between the two alcohols was performed in terms of yields, quality, and reaction kinetics. Parameters tested were temperature (60, 70 and 80°C) and time (5, 10, 15 and 20 min). At all tested conditions, more than 96% conversion rates were obtained for both ethanol and methanol. Use of microwave technology to assist the transesterification process resulted in faster reaction times and reduced catalyst requirement (about ten-fold decrease). Methanol required lower alcohol:oil ratios than normally used in conventional heating, whereas ethanol required higher molar ratios. All esters produced using this method met ASTM biodiesel quality specifications. Methanol performed better in terms of performance and costs, while ethanol may have some environmental and safety benefits.

  3. The CGC enantiomer separation of 2-arylcarboxylic acid esters by using β-cyclodextrin derivatives as chiral stationary phases.

    Science.gov (United States)

    Shi, Xueyan; Liu, Feipeng; Mao, Jianyou

    2016-03-17

    Chiral 2-arylcarboxylic acid esters are important intermediates in preparation of enantioenriched 2-arylpropionic acids type Non-steroidal anti-inflammatory drugs (NSAIDs). Enantiomer separation of 2-arylcarboxylic acid esters is crucial for evaluation of the asymmetric synthesis efficiency and the enantiomer excess of chiral 2-arylcarboxylic acid derivatives. The capillary gas chromatography (CGC) enantiomer separation of 17 pairs of 2-arylcarboxylic acid esters enantiomers was conducted by using seven different β-cyclodextrin derivatives (CDs) as chiral stationary phases. It was found that for the 7 pairs of 2-phenylpropionates enantiomers, CDs with both alkyl and acyl substituents especially 2,6-di-O-pentyl-3-O-butyryl-β-cyclodextrin exhibited better enantiomer separation abilities than the other CDs examined. For the 7 pairs of 2-(4-substituted phenyl)propionates enantiomers, 2,3,6-tri-O-methyl-β-cyclodextrin possessed better enantiomer separation abilities than the other CDs. Among the 3 pairs of 2-phenylbutyrates enantiomers examined, only methyl 2-phenylbutyrate enantiomers could be separated by three CDs among the 7 CDs tested, while enantiomers of ethyl 2-phenylbutyrate and isopropyl 2-phenylbutyrate couldn't be separated by any of the 7 CDs tested. Besides the structures of CDs, the structures of 2-arylcarboxylic acid esters including different ester moieties, substituents of phenyl, and different carboxylic acids moieties in 2-arylcarboxylic acid esters also affected the enantiomer separation results greatly. The CGC enantiomer separation results of 2-arylcarboxylic acid esters on different CDs are useful for solving the enantiomer separation problem of 2-arylcarboxylic acid esters. PMID:26920785

  4. Rare linking hydrogels based on acrylic acid and carbohydrate esters

    Directory of Open Access Journals (Sweden)

    U. Akhmedov

    2012-09-01

    Full Text Available The process of copolymerization of acrylic acid and esters poliallil sucrose; pentaerythritol and sorbitol, some of its laws are identified. The kinetic regularities of copolymerization and the optimum conditions of synthesis was established.

  5. SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF OXIME ESTERS FROM DIHYDROCUMIC ACID

    Directory of Open Access Journals (Sweden)

    Yanqing Gao,

    2012-07-01

    Full Text Available Dihydrocumic acid was prepared from β-pinene through oxidation and dehydration. Then, ten oxime esters from dihydrocumic acid were synthesized. Reaction conditions of the oxime esters were adjusted and their structures were characterized by IR, 1H-NMR, MS, and elemental analysis. The antibacterial activity of these newly synthesized oxime esters against Gram-negative bacteria and Gram-positive bacteria was also investigated using the inhibition zone method. The preliminary results indicated that seven compounds displayed better antibacterial activity against Gram-negative bacteria compared with bromogeramine, a commercially available antibacterial agent.

  6. The oxidative stability of rapeseed oil methyl and ethyl esters - environment friendly alternative fuel

    International Nuclear Information System (INIS)

    The oxidative stability of rapeseed oil and bio diesel fuel RME and REE, produced from it, has been determined. The addition of antioxidant BHT essentially prolongs the utility term of oil and its esters. (authors)

  7. Lanthionine ketimine ethyl ester partially rescues neurodevelopmental defects in unc-33 (DPYSL2/CRMP2) mutants.

    Science.gov (United States)

    Hubbard, Caleb; Benda, Erica; Hardin, Tyler; Baxter, Taylor; St John, Elizabeth; O'Brien, Sean; Hensley, Kenneth; Holgado, Andrea M

    2013-09-01

    Lanthionine ketimine (LK) is a natural sulfur amino acid metabolite with potent neurotrophic activity. Proteomics indicate that LK interacts with collapsin response mediator protein-2 (CRMP2/DPYSL2/UNC-33), a brain-enriched protein that was shown to regulate cytoskeletal remodeling, neuronal morphology, and synaptic function. To elucidate further the molecular interplay and biological action of LK and UNC-33, we began examining the nervous system of Caenorhabditis elegans nematodes in which both LK concentrations and UNC-33 protein were manipulated. To this end, a cell-permeable LK-ester (LKE) was administered to developing C. elegans engineered to express yellow fluorescent protein (YFP) in cholinergic neurons (strain RM3128) or green fluorescent protein (GFP) in GABAergic neurons (strain CZ1200), and neural morphology was assessed. Fluorescent imaging analyses show that LKE exposure to wild-type animals induced neural commissure outgrowth, crossing over, and bundling in both neurites from GABAergic and cholinergic motor neurons. Additionally, when unc-33(e204) hypomorph mutant nematodes (D389N substitution mutants) were exposed to LKE, both the neuroanatomical defects of incomplete dorsoventral neural commissures and the ventral nerve cord gaps were partially rescued. In contrast, LKE did not rescue ventral nerve cord gaps found in unc-33(mn407) null mutant. Together these data suggest possible functions for LK as a regulator of neuritic elongation, corroborate roles for UNC-33/CRMP2 in the mechanism of LKE activity, and suggest the potential of LKE as a therapeutic molecule for neurological diseases involving CRMP2 dysfunction. PMID:23825043

  8. 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.

  9. Direct Asymmetric Aldol Type Reaction with Ethyl Diazoacetate: Stereoselective Synthesis of α, β-Dihydroxy Esters

    Institute of Scientific and Technical Information of China (English)

    LIAO Ming-Yi; YAO Wen-Gang; FENG Hai-Tao; WANG Jian-Bo

    2003-01-01

    @@ Enantioselective aldol condensation under catalytic condition remains a challenging task in modern organic synthesis, and numerous efforts have been directed to this area. In particular, the direct catalytic asymmetric aldol reaction is very attractive considering the requirement of atom efficiency. This has been studied only recently, and several very practical processes have been developed. We have recently initiated a study on the direct asymmetric aldol type reaction with ethyl diazoacetate as nucleophile. Moderate enantioselectivities (65% ~91% ee ) were achieved in the condensation of aldehydes with ethyl diazoacetate catalyzed by the chiral complex of BINOL derivatives-Zr (OBu- t )4. [1

  10. 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.

  11. Energetic balance of castor oil methyl and ethyl esters; Balanco energetico de esteres metilicos e etilicos de oleo de mamona

    Energy Technology Data Exchange (ETDEWEB)

    Almeida Neto, Jose Adolfo de; Cruz, Rosenira Serpa da; Alves, Jaenes Miranda; Pires, Monica de Moura; Robra, Sabine [Universidade Estadual de Santa Cruz, Ilheus BA (Brazil). Grupo Bioenergia e Meio Ambiente]. E-mails: jalmeida@uesc.br; Parente Junior, Expedito [Tecnologias Bioenergeticas Ltda. (TECBIO), Fortaleza, CE (Brazil); Fundacao Nucleo de Tecnologia Industrial (NUTEC), Fortaleza, CE (Brazil)]. E-mail: expeditojr@tecbio.com.br

    2004-07-01

    Castor oil (Ricinus communis L.) is one of the cultures chosen by the biodiesel federal and state programs to supply raw material for biodiesel production - a biofuel indicated as renewable and less pollutant than its fossil competitor. An energetic balance was performed based on LCA - Life Cycle Analysis principles and Input-Output Analysis, comparing the castor oil energy performance with others traditional cultures: colza (Brassica napus) in Europe and soybean (Glycine max) in the United States. Energy balance (O-I) was positive in both production ways (methyl and ethyl) independent of coproduct use allocation alternative. The relation Output-Input (O-I) calculated for castor oil biodiesel [1.3-2.9] was higher than the colza (1.2-1.9) and lower than the soybean (3.2--3.4), independent of the way and allocation of the used byproduct. Both indicators suggest the energy and environmental viability of the castor oil biodiesel, provided that high agricultural productivity (higher than 1.500 kg/ha year) can be guaranteed. The potentialization of the positive energetic and environmental effects depends on the adequate utilization of the coproducts and process residues, the improvement of the energy efficiency in the the castor oil and biodiesel processing and the implementation of efficient management in the use of the chemical inputs (specially the N), responsible for up 5% of the total energy input.

  12. Synthesis, characterization and superoxide dismutase activity of bi-copper(II)-bisacetato-−phthalicacid[bis(benzyloxy)ethyl]ester

    Indian Academy of Sciences (India)

    Babita Sarma; Pradip K Bhattacharyya; Diganta Kumar Das

    2015-03-01

    A new binuclear copper(II) complex, bridged by the ligand phthalicacid[bis(benzyloxy)ethyl]ester, where each copper(II) is coordinated to one carboxylate (from ligand) and one acetate in square planar mode is reported. The ligand synthesized by the reaction of phthalic anhydride and ethylene glycol, has been characterized by FT-IR, 1HNMR and LCMS. The binuclear Copper(II) complex has been characterized by UV/visible spectra, FTIR spectra, EPR spectra, ESI-MS spectra, magnetic moment measurement and thermogravimetric analysis. DFT calculation has shown a Z type structure for the complex. Excellent superoxide dismutase activity with IC50 value 8.6 × 10−6 M for the complex has been observed.

  13. Sodium borohydride reduction of aromatic carboxylic acids via methyl esters

    Indian Academy of Sciences (India)

    Aamer Saeed; Zaman Ashraf

    2006-09-01

    A number of important aromatic carboxylic acids precursors, or intermediates in the syntheses of natural products, are converted into methyl esters and reduced to the corresponding primary alcohols using a sodium borohydride-THF-methanol system. The alcohols are obtained in 70-92% yields in 2-5 hours, in a pure state. This two-step procedure not only provides a better alternative to aluminum hydride reduction of acids but also allows the selective reduction of esters in presence of acids, amides, nitriles or nitro functions which are not affected under these conditions.

  14. 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...

  15. Stereo Selective Synthesis and Absolute Configuration Determination of (2E,4S)-4-(t-butoxycarbonylamino)-5-[ (3S)-2'-oxo-3'-pyrrolidinyl]-2-pentenoic Acid Ethyl Ester%(2E,4S)-4-叔丁氧羰基氨基-5-[(3S)-2'-氧代-3'-吡咯烷基]-2-戊烯酸乙酯的立体选择性合成及绝对构型

    Institute of Scientific and Technical Information of China (English)

    张永坡; 张洋; 孙怀林

    2014-01-01

    (2E,4S)-4-(t-Butoxycarbonylamino)-5-[(3S)-2’-oxo-3’-pyrrolidinyl]-2-pentenoic acid ethyl ester(1) is a key intermediate widely used in drug candidate synthesis, such as the human rhinovious 3C pro-tease inhibitor AG7088 and its related substances which are currently being developed for treatment of common cold, severe acute respiratory syndromes( SARS) and hand, foot, mouth disease( HFMD) . Based on existing synthetic routes using L-glutamic acid as starting material, the optical purities of each intermediate product was rigorously examined, and the effects of reaction conditions on the optical purities of the products were studied in details. Meanwhile, racemic samples of each product were prepared from D, L-glutamic acids using the same procedures and used for comparison in high performance liquid chromatography( HPLC) analyses. Thus, new factors that could influence the optical purities of the final products were discovered, and methods for sol-ving the problems were provided. The molecular structure of intermediate product (2S)-2-( t-butoxycarbonyl-amino)-3-[(3S)-2’-oxo-3’-pyrrolidinyl]propanol(5) was determined by the X-ray diffraction method, which provides direct evidence for the absolute configuration of these products.%在(2E,4S)-4-叔丁氧羰基氨基-5-[(3S)-2'-氧代-3'-吡咯烷基]-2-戊烯酸乙酯(1)已有立体选择性合成路线的基础上,对各步产物的光学纯度进行了严格的检验,研究了反应条件对这些产物光学纯度的影响,并利用单晶X射线衍射方法确定了该类化合物的绝对构型。

  16. 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.

  17. Synergistic cosolubilization of omega-3 fatty acid esters and CoQ10 in dilutable microemulsions.

    Science.gov (United States)

    Deutch-Kolevzon, Rivka; Aserin, Abraham; Garti, Nissim

    2011-10-01

    Water-dilutable microemulsions were prepared and loaded with two types of omega-3 fatty acid esters (omega-3 ethyl esters, OEE; and omega-3 triacylglycerides, OTG), each separately and together with ubiquinone (CoQ(10)). The microemulsions showed high and synergistic loading capabilities. The linear fatty acid ester (OEE) solubilization capacity was greater than that of the bulky and robust OTG. The location of the guest molecules within the microemulsions at any dilution point were determined by electrical conductivity, viscosity, DSC, SAXS, cryo-TEM, SD-NMR, and DLS. We found that OEE molecules pack well within the surfactant tails to form reverse micelles that gradually, upon water dilution, invert into bicontinuous phase and finally into O/W droplets. The CoQ(10) increases the stabilization and solubilization of the omega-3 fatty acid esters because it functions as a kosmotropic agent in the micellar system. The hydrophobic and bulky OTG molecule strongly interferes with the tail packing and spaces them significantly - mainly in the low and medium range water dilutions. When added to the micellar system, CoQ(10) forms some reverse hexagonal mesophases. The inversion into direct micelles is more difficult in comparison to the OEE system and requires additional water dilution. The OTG with or without CoQ(10) destabilizes the structures and decreases the solubilization capacity since it acts as a chaotropic agent to the micellar system and as a kosmotropic agent to hexagonal packing. These results explain the differences in the behavior of these molecules with vehicles that solubilize them in aqueous phases. Temperature disorders the bicontinuous structures and reduces the supersaturation of the system containing OEE with CoQ(10); as a result CoQ(10) crystallization is retarded. PMID:21723268

  18. 21 CFR 172.848 - Lactylic esters of fatty acids.

    Science.gov (United States)

    2010-04-01

    ... fruits and vegetables Dehydrated fruit and vegetable juices Edible vegetable fat-water emulsions As... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Lactylic esters of fatty acids. 172.848 Section 172.848 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES...

  19. Synthesis and insecticidal activities of new pyrethroid acid oxime ester derivatives

    Institute of Scientific and Technical Information of China (English)

    2002-01-01

    A series of compounds containing oxime-ester linkage in place of the ester linkage in pyrethroid ester are designed and prepared. Bioassay data of insecticidal activities of these compounds on Ostrinia nubilalis (H.) and Culex pipines (L.) are presented. Among them 4-dimethyaminobenzaldehyde oxime ester of 2,2,3,3-tetramethylcyclopropanecarboxylic acid and 4-dimethyamino benzaldehyde oxime ester of cyclopropanecarboxylic acid are found to be potent insecticide against Ostrinia nubilalis (H.). Structure-activity relationship of the compounds is discussed.

  20. Fatty acid methyl esters production: chemical process variables

    Directory of Open Access Journals (Sweden)

    Paulo César Narváez Rincón

    2010-06-01

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

  1. 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

  2. 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.

  3. 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.

  4. 75 FR 52269 - Acetic Acid Ethenyl Ester, Polymer With Oxirane; Tolerance Exemption

    Science.gov (United States)

    2010-08-25

    ... AGENCY 40 CFR Part 180 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...

  5. 40 CFR 721.3800 - Formaldehyde, condensated polyoxyethylene fatty acid, ester with styrenated phenol, ethylene...

    Science.gov (United States)

    2010-07-01

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

  6. 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... of polyester resins. Partial phosphoric acid esters of polyester resins identified in this section... prescribed conditions: (a) For the purpose of this section, partial phosphoric acid esters of...

  7. Synthesis, Crystal Structure and Inhibition of N-2-Thiophenesulfonyl-α-L-phenylalanine Ethyl Ester on K562 Cell Proliferation

    Institute of Scientific and Technical Information of China (English)

    2007-01-01

    The title compound N-2-thiophenesulfonyl-α-L-phenylalanine ethyl ester has been synthesized. Complete assignments were achieved by IR, MS, 1H NMR and single-crystal X-ray diffraction analyses. Using MTT assay, the inhibitory rate of the title compound on K562 cells (chronic myeloid 1eukemic cells) was measured and the result of preliminary bioassay showed that the title compound possesses antiproliferation effects on K562 cells. In order to investigate the relationship between structure and activity of the target compound, we report its crystal structure and biological behavior in the present paper. Crystallographic data: C15H17NO4S2, Mr = 339.42, monoclinic, space group P21, flack = -0.15(12), a = 5.7916(10), b = 11.5078(19), c = 12.924(2) (A), β = 97.781(3)°, Z = 2, V = 853.4(2) (A)3, Dc = 1.321 g/cm3, F(000) = 356, -7≤h≤7, -10≤k≤14, -15≤l≤15, R = 0.0628, wR = 0.1540 and μ(MoKα) = 0.327 mm-1. The molecule comprises a benzene and a thiofuran rings, and the intramolecular N(1)-H(1A)…O(1) makes a five-membered ring of O(1)-C(6)-C(5)-N(1)-H(1A).

  8. Elevation of brain glutathione by gamma-glutamylcysteine ethyl ester protects against peroxynitrite-induced oxidative stress.

    Science.gov (United States)

    Drake, Jennifer; Kanski, Jaroslaw; Varadarajan, Sridhar; Tsoras, Maria; Butterfield, D Allan

    2002-06-15

    Elevation of glutathione (GSH) has been recognized as an important method for modulating levels of reactive oxygen species (ROS) in the brain. We investigated the antioxidant properties of gamma-glu-cys-ethyl ester (GCEE) in vitro and its ability to increase GSH levels upon in vivo i.p. injection. GCEE displays antioxidant activity similar to GSH as assessed by various in vitro indices such as hydroxyl radical scavenging, dichlorofluorescein fluorescence (DCF), protein specific spin labeling, glutamine synthetase (GS) activity, and protein carbonyls. Intraperitoneal injection of GCEE to gerbils resulted in a 41% increase in brain total GSH levels in vivo as determined by the DTNB-GSH reductase recycling method. Gerbils injected with buthionine sulfoximine (BSO), an inhibitor of gamma-glutamylcysteine synthetase, had 40% less total brain glutathione. Gerbils injected with BSO followed by a GCEE injection had GSH levels similar to vehicle-injected controls, suggesting that GCEE upregulates GSH biosynthesis by providing gamma-glutamylcysteine and not cysteine. Cortical synaptosomes from GCEE-injected animals were less susceptible to peroxynitrite-induced oxidative damage as assessed by DCF fluorescence, protein-specific spin labeling, and GS activity. These experiments suggest that GCEE is effective in increasing brain GSH levels and may potentially play an important therapeutic role in attenuating oxidative stress in neurodegenerative diseases associated with oxidative stress such as Alzheimer disease.

  9. Comparative behavioral pharmacology and toxicology of cocaine and its ethanol-derived metabolite, cocaine ethyl-ester (cocaethylene)

    Energy Technology Data Exchange (ETDEWEB)

    Katz, J.L.; Terry, P.; Witkin, J.M. (NIDA Addiction Research Center, Baltimore, MD (United States))

    1992-01-01

    The present study compared the behavioral and toxic effects of cocaine and its ethanol derived metabolite, cocaine ethyl-ester (cocaethylene). Both drugs produced qualitatively similar psychomoter stimulant effects. Cocaine and cocaethylene increased locomotor activity in mice, with cocaine approximately four times more potent than cocaethylene. The durations of action of ED{sub 75} doses of each of the drugs were comparable. Each of the drugs also produced stimulation of operant responding in rats. In rats and squirrel monkeys trained to discriminate cocaine injections from saline, cocaine was approximately three to five times more potent than cocaethylene in producing these cocaine-like interoceptive effects. In contrast to the behavioral effects, cocaine and cocaethylene were equipotent in producing convulsions, and cocaethylene was more potent than cocaine in producing lethality. These results suggest that the conversion of cocaine to cocaethylene with simultaneous cocaine and alcohol use may produce an increased risk of toxicity due to a decrease in the potency of cocaethylene in producing psychomotor stimulant effects, and its increased potency in producing toxicity.

  10. Combustion performance and emissions of ethyl ester of a waste vegetable oil in a water-cooled furnace

    International Nuclear Information System (INIS)

    Food consumption around the world produces large amounts of waste vegetable oils and fats that, in many world regions, are disposed of in harmful ways. Consequently, this study intended to investigate the feasibility of utilizing this renewable and low cost fuel raw material as a diesel fuel replacement in small-scale applications such as in residential heating boilers. Specifically, the study examined the aspects of combustion performance and emissions of the ethyl ester of used palm oil (biodiesel) relative to the baseline diesel fuel in a water-cooled furnace. The combustion efficiency, ηc and exhaust temperature, T exh as well as the common pollutants and emissions were tested over a wide range of air/fuel ratio ranging from very lean to very rich (10:1-20:1). All tests were conducted at two different energy inputs for both fuels. The findings showed that, at the lower energy rate used, biodiesel burned more efficiently with higher combustion efficiency and exhaust temperature of, respectively, 66% and 600 deg C compared to 56% and 560 deg C for the diesel fuel. At the higher energy input, biodiesel combustion performance deteriorated and was inferior to diesel fuel due to its high viscosity, density and low volatility. As for emissions, biodiesel emitted less pollutants at both energy levels over the whole range of A/F ratio considered. (Author)

  11. 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...

  12. 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.

  13. Enzymatic synthesis and application of fatty acid ascorbyl esters

    OpenAIRE

    Stojanović Marija M.; Carević Milica B.; Mihailović Mladen D.; Knežević-Jugović Zorica D.; Petrović Slobodan D.; Bezbradica Dejan I.

    2013-01-01

    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 use...

  14. Evaluation of salicylic acid fatty ester prodrugs for UV protection.

    Science.gov (United States)

    Im, Jong Seob; Balakrishnan, Prabagar; Oh, Dong Hoon; Kim, Jung Sun; Jeon, Eun-Mi; Kim, Dae-Duk; Yong, Chul Soon; Choi, Han-Gon

    2011-07-01

    The purpose of this study was to investigate the physicochemical properties and in vitro evaluation of fatty ester prodrugs of salicylic acid for ultraviolet (UV) protection. The physicochemical properties such as lipophilicity, chemical stability and enzymatic hydrolysis were investigated with the following fatty ester prodrugs of salicylic acid: octanoyl (C8SA), nonanoyl (C9SA), decanoyl (C10SA), lauroyl (C12SA), myristoyl (C14SA) and palmitoyl oxysalicylate (C16SA). Furthermore, their skin permeation and accumulation were evaluated using a combination of common permeation enhancing techniques such as the use of a lipophilic receptor solution, removal of stratum corneum and delipidization of skin. Their k' values were proportional to the degree of carbon-carbon saturation in the side chain. All these fatty esters were highly stable in 2-propanol, acetonitrile and glycerin, but unstable in methanol and ethanol. They were relatively unstable in liver and skin homogenates. In particular, C16SA was mostly hydrolyzed to its parent compound in hairless mouse liver and skin homogenates, suggesting that it might be converted to salicylic acid after its topical administration. In the skin permeation and accumulation study, C16SA showed the poorest permeation in all skins, suggesting that it could not be permeated in the skin. Furthermore, C14SA and C16SA were less accumulated in delipidized skin compared with normal skin or stripped skin, suggesting that these esters had relatively strong affinities for lipids compared with the other prodrugs in the skin. C16SA showed significantly higher dermal accumulation in all skins compared with its parent salicylic acid. Thus, the palmitoyl oxysalicylate (C16SA) might be a potential candidate for UV protection due to its absence of skin permeation, smaller uptake in the lipid phase and relatively lower skin accumulation.

  15. 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.

  16. 杂环氨基酸酯的合成与表征%Synthesis and characterization of heterocyclic amino acid esters

    Institute of Scientific and Technical Information of China (English)

    马养民; 刘斌

    2011-01-01

    L-trytophan methyl/ethyl ester hydrochloride, L-histidine methyl ester hydrochloride and L-proline methyl/ethyl ester hydrochloride were synthesized by reacting with three kinds of heterocyclic amino acids in a methanol/alcohol in the presence of thionyl chloride,and high yield product was produced. The structures of these compounds were characterized by NMR spectroscopy, IR spectroscopy and elemental analysis. Three types of heterocuclic amino acid esters were prepared by amino acid ester hydrochiloride in saturatede sodium carbonate,and extracted by methylene chloride.%以三种杂环结构的氡基酸、二氯亚砜、甲醇/乙醇为原料,合成L-色氨酸甲/乙酯盐酸盐、L-组氨酸甲酯盐酸盐以及L-脯氨酸甲/乙酯盐酸盐.产率较高,并通过核磁共振谱、红外光谱、元素分析对其盐酸盐进行了结构表征,所得到的氨基酸酯盐酸盐分别用饱和碳酸钠溶液中和、二氯甲烷萃取,最终得到了三类杂环氨基酸酯.

  17. Metabolism of hydroxycinnamic acids and their tartaric acid esters by Brettanomyces and Pediococcus in red wines.

    Science.gov (United States)

    Caffeic, p-coumaric, and ferulic acids and their corresponding tartaric acid esters (caftaric, coutaric, and fertaric, respectively) are found in wines in varying concentrations. While Brettanomyces and Pediococcus can utilize the free acids, it is not known whether they can metabolize the correspon...

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

    International Nuclear Information System (INIS)

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

  19. The effects of creatine ethyl ester supplementation combined with heavy resistance training on body composition, muscle performance, and serum and muscle creatine levels

    Directory of Open Access Journals (Sweden)

    Greenwood Mike

    2009-02-01

    Full Text Available Abstract Numerous creatine formulations have been developed primarily to maximize creatine absorption. Creatine ethyl ester is alleged to increase creatine bio-availability. This study examined how a seven-week supplementation regimen combined with resistance training affected body composition, muscle mass, muscle strength and power, serum and muscle creatine levels, and serum creatinine levels in 30 non-resistance-trained males. In a double-blind manner, participants were randomly assigned to a maltodextrose placebo (PLA, creatine monohydrate (CRT, or creatine ethyl ester (CEE group. The supplements were orally ingested at a dose of 0.30 g/kg fat-free body mass (approximately 20 g/day for five days followed by ingestion at 0.075 g/kg fat free mass (approximately 5 g/day for 42 days. Results showed significantly higher serum creatine concentrations in PLA (p = 0.007 and CRT (p = 0.005 compared to CEE. Serum creatinine was greater in CEE compared to the PLA (p = 0.001 and CRT (p = 0.001 and increased at days 6, 27, and 48. Total muscle creatine content was significantly higher in CRT (p = 0.026 and CEE (p = 0.041 compared to PLA, with no differences between CRT and CEE. Significant changes over time were observed for body composition, body water, muscle strength and power variables, but no significant differences were observed between groups. In conclusion, when compared to creatine monohydrate, creatine ethyl ester was not as effective at increasing serum and muscle creatine levels or in improving body composition, muscle mass, strength, and power. Therefore, the improvements in these variables can most likely be attributed to the training protocol itself, rather than the supplementation regimen.

  20. Synthesis of N-(methoxycarbonyl or isopropylcarbamoyl- methoxyphosphonyl)-α-amino acid ester and their stereomers

    Institute of Scientific and Technical Information of China (English)

    陈茹玉; 李慧英

    1996-01-01

    N-(methoxycarbonyl-methoxyphosphonyl)-α-amino add esters (I) were synthesized via the reaction of the corresponding phosphonyl chloride with amino acid ester hydrochlorides in the presence of a base. Compound I was aminated to yield N-(isopropylcarbainoyl-methoxyphosphonyl)-α-amino acid esters (II). With l-amino acids as starting materials, the isomers of products I and II were separated and their configurations were confirmed by the single crystal X-ray diffraction of II.

  1. A Convenient, General Synthesis of 1,1-Dimethylallyl Esters as Protecting Groups for Carboxylic Acids

    Science.gov (United States)

    Sedighi, Minoo; Lipton, Mark A.

    2006-01-01

    Carboxylic acids were converted in high yield to their 1,1-dimethylallyl (DMA) esters in two steps. Palladium-catalyzed deprotection of DMA esters was shown to be compatible with tert-butyl, benzyl and Fmoc protecting groups, and Fmoc deprotection could be carried out selectively in the presence of DMA esters. DMA esters were also shown to be resistant to nucleophilic attack, suggesting that they will serve as alternatives to tert-butyl esters when acidic deprotection conditions need to be avoided. PMID:15816730

  2. A convenient, general synthesis of 1,1-dimethylallyl esters as protecting groups for carboxylic acids.

    Science.gov (United States)

    Sedighi, Minoo; Lipton, Mark A

    2005-04-14

    [reaction: see text] Carboxylic acids were converted in high yield to their 1,1-dimethylallyl (DMA) esters in two steps. Palladium-catalyzed deprotection of DMA esters was shown to be compatible with tert-butyl, benzyl, and Fmoc protecting groups, and Fmoc deprotection could be carried out selectively in the presence of DMA esters. DMA esters were also shown to be resistant to nucleophilic attack, suggesting that they will serve as alternatives to tert-butyl esters when acidic deprotection conditions need to be avoided.

  3. Data from mass spectrometry, NMR spectra, GC-MS of fatty acid esters produced by Lasiodiplodia theobromae.

    Science.gov (United States)

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

    2016-09-01

    The data described herein is related to the article with the title "Fatty acid esters produced by Lasiodiplodia theobromae function as growth regulators in tobacco seedlings" C.C. Uranga, J. Beld, A. Mrse, I. Cordova-Guerrero, M.D. Burkart, R. Hernandez-Martinez (2016) [1]. Data includes nuclear magnetic resonance spectroscopy and GC-MS data used for the identification and characterization of fatty acid esters produced by L. theobromae. GC-MS traces are also shown for incubations in defined substrate, consisting in Vogel׳s salts supplemented with either 5% grapeseed oil or 5% glucose, the two combined, or 5% fructose. Traces for incubations in the combination of 5% grapeseed oil and 5% glucose for different fungal species are also included. Images of mycelium morphology when grown in 5% glucose with or without 5% grapeseed oil are shown due to the stark difference in mycelial pigmentation in the presence of triglycerides. High concentration gradient data for the plant model Nicotiana tabacum germinated in ethyl stearate (SAEE) and ethyl linoleate (LAEE) is included to show the transition between growth inhibition and growth induction in N. tabacum by these compounds. PMID:27274528

  4. Data from mass spectrometry, NMR spectra, GC–MS of fatty acid esters produced by Lasiodiplodia theobromae

    Directory of Open Access Journals (Sweden)

    Carla C. Uranga

    2016-09-01

    Full Text Available The data described herein is related to the article with the title “Fatty acid esters produced by Lasiodiplodia theobromae function as growth regulators in tobacco seedlings” C.C. Uranga, J. Beld, A. Mrse, I. Cordova-Guerrero, M.D. Burkart, R. Hernandez-Martinez (2016 [1]. Data includes nuclear magnetic resonance spectroscopy and GC–MS data used for the identification and characterization of fatty acid esters produced by L. theobromae. GC–MS traces are also shown for incubations in defined substrate, consisting in Vogel׳s salts supplemented with either 5% grapeseed oil or 5% glucose, the two combined, or 5% fructose. Traces for incubations in the combination of 5% grapeseed oil and 5% glucose for different fungal species are also included. Images of mycelium morphology when grown in 5% glucose with or without 5% grapeseed oil are shown due to the stark difference in mycelial pigmentation in the presence of triglycerides. High concentration gradient data for the plant model Nicotiana tabacum germinated in ethyl stearate (SAEE and ethyl linoleate (LAEE is included to show the transition between growth inhibition and growth induction in N. tabacum by these compounds.

  5. 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.

  6. Scientific Opinion on the safety and efficacy of straight-chain primary aliphatic alcohols/aldehydes/acids, acetals and esters with esters containing saturated alcohols and acetals containing saturated aldehydes (chemical group 1 when used as flavourings for all animal species

    Directory of Open Access Journals (Sweden)

    EFSA Panel on Additives and Products or Substances used in Animal Feed (FEEDAP

    2013-04-01

    Full Text Available Chemical group 1 (CG 1 consists of straight-chain primary aliphatic alcohols/aldehydes/acids, acetals and esters with esters containing saturated alcohols and acetals containing saturated aldehydes of which 86 are currently authorised for use as flavours in food. The FEEDAP Panel was unable to perform an assessment of ethyl oleate because of its insufficient purity. The following compounds are considered to be safe for all animal species at the use level proposed for feed flavourings: formic acid, acetic acid, propionic acid, octanoic acid, decanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid, oleic acid, decanol, dodecanol, decyl acetate and dodecyl acetate. The remaining substances are considered safe for all animal species at 5 mg/kg complete feed (with a margin of safety between 1 and 120 and at 25 mg/kg complete feed (ethyl acetate and hexyl acetate, with a margin of safety between 2 and 6; and at 1 mg/kg complete feed for pigs and poultry and 1.5 mg/kg complete feed for all other species (ethylacrylate, ethyl hex-3-enoate, ethyl trans-2-butenoate, ethyl isobutyrate, ethyl isovalerate, butyl isovalerate, methyl isovalerate, hexyl isobutyrate, methyl 2-methyl butyrate, pentyl isovalerate, butyl 2-methyl butyrate, hexyl isovalerate, ethyl 2-methyl butyrate, hexyl 2-methyl butyrate and methyl 2-methylvalerate. No safety concern would arise for the consumer from the use of compounds belonging to CG 1 up to the highest safe level in feedingstuffs for all animal species. The FEEDAP Panel considers it prudent to treat all compounds under assessment as irritants to skin, eyes and respiratory tract and as skin sensitizers. No risk for the safety for the environment is foreseen. Since all 85 compounds are used in food as flavourings, no further demonstration of efficacy is necessary.

  7. GROUP TRANSFER POLYMERIZATION OF ETHYL ACRYLATE WITH LEWIS ACID CATALYST

    Institute of Scientific and Technical Information of China (English)

    XU Linyun; Wang Lei

    1989-01-01

    This paper reports the kinetics of group transfer polymerization (GTP) of ethyl acrylate (EA) with zinc iodide catalyst in 1,2- dichloroethane using dimethyl ketene methyl trimethylsilyl acetal ( MTS ) as initiator at 0 ℃ and above 0 ℃ . The amount of catalyst used was studied. When zinc iodide catalyst used is more than 10mol% relative to monomer, the rate of polymerization is proportional to the concentration of monomer, whereas zinc iodide catalyst used is less than 10 mol% of the monomer, the rate of polymerization is independent of the monomer concentration. In the GTP of EA an induction period was observed when the zinc iodide contents are less than 10 mol%. If the reaction temperature is over 0 ℃ , living species become unstable and diminish, leading to incomplete monomer conversion. The reaction curves equations are obtained. The polymers have narrow molecular weight distributions which are not changed as decreasing zinc iodide contents. The polydispersity is about 1.2.

  8. Performance of an enzymatic packed bed reactor running on babassu oil to yield fatty ethyl esters (FAEE in a solvent-free system

    Directory of Open Access Journals (Sweden)

    Aline Simões

    2015-06-01

    Full Text Available The transesterification reaction of babassu oil with ethanol mediated by Burkholderia cepacia lipase immobilized on SiO2-PVA composite was assessed in a packed bed reactor running in the continuous mode. Experiments were performed in a solvent-free system at 50 °C. The performance of the reactor (14 mm ×210 mm was evaluated using babassu oil and ethanol at two molar ratios of 1:7 and 1:12, respectively, and operational limits in terms of substrate flow rate were determined. The system’s performance was quantified for different flow rates corresponding to space times between 7 and 13 h. Under each condition, the impact of the space time on the ethyl esters formation, the transesterification yield and productivity were determined. The oil to ethanol molar ratio was found as a critical parameter in the conversion of babassu oil into the correspondent ethyl esters. The highest transesterification yield of 96.0 ± 0.9% and productivity of 41.1 ± 1.6 mgester gcatalyst-1h-1 were achieved at the oil to ethanol molar ratio of 1:12 and for space times equal or higher than 11 h. Moreover, the immobilized lipase was found stable with respect to its catalytic characteristics, exhibiting a half-life of 32 d.

  9. On the chemical ladder of esters. Detection and formation of ethyl formate in the W51 e2 hot molecular core

    CERN Document Server

    Rivilla, V M; Martín-Pintado, J; Fontani, F; Caselli, P; Cesaroni, R

    2016-01-01

    The detection of organic molecules with increasing complexity and potential biological relevance is opening the possibility to understand the formation of the building blocks of life in the interstellar medium. One of the families of molecules with astrobiological interest are the esters, whose simplest member, methyl formate, is rather abundant in star-forming regions. The next step in the chemical complexity of esters is ethyl formate, C$_2$H$_5$OCHO. Only two detections of this species have been reported so far, which strongly limits our understanding of how complex molecules are formed in the interstellar medium. We have searched for ethyl formate towards the W51 e2 hot molecular core, one of the most chemically rich sources in the Galaxy and one of the most promising regions to study prebiotic chemistry, especially after the recent discovery of the P$-$O bond, key in the formation of DNA. We have analyzed a spectral line survey towards the W51 e2 hot molecular core, which covers 44 GHz in the 1, 2 and 3 ...

  10. 邻苯二甲酸酯类增塑剂的生产工艺%Production Processes of Phthalic acid ester Plasticizers

    Institute of Scientific and Technical Information of China (English)

    吴国华

    2012-01-01

    Phthalic acid ester plasticizers include di-n-butyl phthalate (DOP), diisobutyl phthalate (DOP) and di ( 2- ethyl hexyl) phthalate (DIBP). To review the process of non acid method of DOP and process of acid method of DBP and DIBP.%邻苯二甲苯酸酯类增塑剂主要包括邻苯二甲酸二辛酯(DOP)、邻苯二甲酸二丁酯(DBP)和邻苯二甲酸二异丁酯(DIBP)3种。综述了非酸法DOP生产工艺以及酸法DBP和DIBP生产工艺。

  11. 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

  12. [Anaerobic biodegradation of phthalic acid esters (Paes) in municipal sludge].

    Science.gov (United States)

    Liang, Zhi-Feng; Zhou, Wen; Lin, Qing-Qi; Yang, Xiu-Hong; Wang, Shi-Zhong; Cai, Xin-De; Qiu, Rong-Liang

    2014-04-01

    Phthalic acid esters (PAEs), a class of organic pollutants with potent endocrine-disrupting properties, are widely present in municipal sludge. Study of PAEs biodegradation under different anaerobic biological treatment processes of sludge is, therefore, essential for a safe use of sludge in agricultural practice. In this study, we selected two major sludge PAEs, i.e. di-n-butyl phthalate (DBP) and di-(2-enthylhexyl) phthalate (DEHP), to investigate their biodegradation behaviors in an anaerobic sludge digestion system and a fermentative hydrogen production system. The possible factors influencing PAEs biodegradation in relation to changes of sludge properties were also discussed. The results showed that the biodegradation of DBP reached 99.6% within 6 days, while that of DEHP was 46.1% during a 14-day incubation period in the anaerobic digestion system. By comparison, only 19.5% of DBP was degraded within 14 days in the fermentative hydrogen production system, while no degradation was detected for DEHP. The strong inhibition of the degradation of both PAEs in the fermentative hydrogen production system was ascribed to the decreases in microbial biomass and ratios of gram-positive bacteria/gram-negative bacteria and fungi/ bacteria, and the increase of concentrations of volatile fatty acids (e. g. acetic acid, propionic acid and butyric acid) during the fermentative hydrogen-producing process.

  13. Design, Synthesis and Biological Evaluation of 2-(2-Aryl- morpholino-4-yl)ethyl Esters of Indomethacin as Potential Cyclooxygenase-2 (COX-2) Inhibitors

    Institute of Scientific and Technical Information of China (English)

    石磊; 胡艾希; 徐江平; 蒋毅萍

    2012-01-01

    A number of novel 2-(2-arylmorpholino-4-yl)ethyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-lH-indol-3- acetate hydrochlorides were synthesized and tested for their cyclooxygenase (COX-1 and COX-2) inhibition prop- erties in vitro. Many of these compounds exhibited moderate to good selective COX-2 inhibition, and subtle struc- tural changes in the substituents on the side chain of the ester moiety altered the inhibitory properties significantly. 2-[2-(4-Butoxyphenyl)morpholino-4-yl]ethyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-IH-indol-3-acetate hydro- chloride (If), showed good selective COX-2 inhibitory activity (Selective index (SI) 182), which is comparative with celecoxib (SI 214), a COX-2 inhibitor of diarylpyrazoles. While 2-[2-(2,4-dichloro-5-fluorophenyl)mor- pholino-4-yl]ethyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-IH-indol-3-acetate hydrochloride (lg), showed greater selective COX-2 inhibitory activity (SI 358) than celecoxib. Both compounds were identified as compromising de- rivatives in this class to reduce the side effects generated by nonsteroidal anti-inflammatory drugs (NSAIDs) indo- methacin.

  14. 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.

  15. Determining Phthalic Acid Esters Using Terahertz Time Domain Spectroscopy

    Science.gov (United States)

    Liu, L.; Shen, L.; Yang, F.; Han, F.; Hu, P.; Song, M.

    2016-09-01

    In this report terahertz time domain spectroscopy (THz-TDS) is applied for determining phthalic acid esters (PAEs) in standard materials. We reported the THz transmission spectrum in the frequency range of 0.2 to 2.0 THz for three PAEs: di-n-butyl phthalate (DBP), di-isononyl phthalate (DINP), and di-2-ethylhexyl phthalate ester (DEHP). The study provided the refractive indices and absorption features of these materials. The absorption spectra of three PAEs were simulated by using Gaussian software with Density Functional Theory (DFT) methods. For pure standard PAEs, the values of the refractive indices changed between 1.50 and 1.60. At 1.0 THz, the refractive indices were 1.524, 1.535, and 1.563 for DINP, DEHP, and DBP, respectively. In this experiment different concentrations of DBP were investigated using THz-TDS. Changes were measured in the low THz frequency range for refractive indices and characteristic absorption. The results indicated that THz-TDS is promising as a new method in determining PAEs in many materials. The results of this study could be used to support the practical application of THz-TDS in quality detection and food monitoring. In particular, this new technique could be used in detecting hazardous materials and other substances present in wine or foods.

  16. 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... Significant New Uses for Specific Chemical Substances § 721.3700 Fatty acid, ester with styrenated phenol... chemical substance identified generically as fatty acid, ester with styrenated phenol, ethylene...

  17. Synthesis and Characteristics of an Aspartame Analogue, L-Asparaginyl L-3-Phenyllactic Acid Methyl Ester

    Institute of Scientific and Technical Information of China (English)

    Hu TAO; Da-Fu CUI; You-Shang ZHANG

    2004-01-01

    An aspartame analogue,L-asparaginyl L-3-phenyllactic acid methyl ester was synthesized with aspartic acid replaced by asparagine and peptide bond replaced by ester bond.The aspartic acid of aspartame could be replaced by asparagine as reported in the literature.In this analogue,the hydrogen ofamide group could still form a hydrogen bond with the oxygen of ester bond and the ester bond was isosteric with peptide bond.However,the product was not sweet,showing that the peptide bond could not be replaced by ester bond.The peptide C-N bond behaves as a double bond that is not free to rotate and the C,O,N and H atoms are in the same plane.The replacement of peptide bond by ester bond destroyed the unique conformation of peptide bond,resulting in the loss of sweet taste.

  18. Synthesis and characteristics of an aspartame analogue, L-asparaginyl L-3-phenyllactic acid methyl ester.

    Science.gov (United States)

    Tao, Hu; Cui, Da-Fu; Zhang, You-Shang

    2004-06-01

    An aspartame analogue, L-asparaginyl L-3-phenyllactic acid methyl ester was synthesized with aspartic acid replaced by asparagine and peptide bond replaced by ester bond. The aspartic acid of aspartame could be replaced by asparagine as reported in the literature. In this analogue, the hydrogen of amide group could still form a hydrogen bond with the oxygen of ester bond and the ester bond was isosteric with peptide bond. However, the product was not sweet, showing that the peptide bond could not be replaced by ester bond. The peptide C-N bond behaves as a double bond that is not free to rotate and the C, O, N and H atoms are in the same plane. The replacement of peptide bond by ester bond destroyed the unique conformation of peptide bond, resulting in the loss of sweet taste.

  19. Phthalic acid esters found in municipal organic waste

    DEFF Research Database (Denmark)

    Hartmann, Hinrich; Ahring, Birgitte Kiær

    2003-01-01

    Contamination of the organic fraction of municipal solid waste (OFMSW) with xenobiotic compounds and their fate during anaerobic digestion was investigated. The phthalic acid ester di-(2- ethylhexyl)phthalate (DEHP) was identified as the main contaminant in OFMSW in concentrations more than half...... was observed. However, after treatment of the effluent from the thermophilic reactor in a hyper-thermophilic digester (HRT: 5 days) 0 CO 34-53% of the DEHP content was removed and the DBP removal was increased to further 62-74%. Removal rates (k(h)) of DEHP and DBP were found to be 0.11-0.32 d(-1) and 0...... is enhanced at higher temperature and higher degradation of solid organic matter, to which the highly hydrophobic DEHP is adsorbed. The investigated reactor configuration with a thermophilic and a hyper-thermophilic treatment is, therefore, a good option for CD combining high rate degradation of organic...

  20. Omega-3 free fatty acids for the treatment of severe hypertriglyceridemia

    DEFF Research Database (Denmark)

    Kastelein, John J P; Maki, Kevin C; Susekov, Andrey;

    2014-01-01

    Omega-3 fatty acids in free fatty acid form have enhanced bioavailability, and plasma levels are less influenced by food than for ethyl ester forms.......Omega-3 fatty acids in free fatty acid form have enhanced bioavailability, and plasma levels are less influenced by food than for ethyl ester forms....

  1. Layered metal laurates as active catalysts in the methyl/ethyl esterification reactions of lauric acid

    Energy Technology Data Exchange (ETDEWEB)

    Lisboa, Fabio da Silva; Cordeiro, Claudiney S.; Wypych, Fernando, E-mail: wypych@ufpr.br [Centro de Pesquisas em Quimica Aplicada (CEPESQ), Departamento de Quimica, Universidade Federal do Parana, Curitiba, PR (Brazil); Gardolinski, Jose Eduardo F. da Costa [Laboratorio de Analise de Minerais e Rochas (LAMIR), Departamento de Geologia, Universidade Federal do Parana, Curitiba, PR (Brazil)

    2012-07-01

    In this work we report the synthesis, characterization and investigation of the catalytic activity of layered copper(II), manganese(II), lanthanum(III) and nickel(II) laurates in the methyl and ethyl esterification reactions of lauric acid. In the methyl esterification, conversions between 80 and 90% were observed for all catalysts, while for the ethyl esterification only manganese laurate showed reasonable catalytic activity, with conversions close to 75%. Reuse of copper and lanthanum laurates in three cycles of reaction was also investigated and both catalysts preserved the structure and retained catalytic activity close to that observed for the first reaction cycle. (author)

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

    Science.gov (United States)

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

    2015-05-01

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

  3. KINETIC OF ESTERIFICATION OF ETHYL ALCOHOL BY ACETIC ACID ON A CATALYTIC RESIN

    Directory of Open Access Journals (Sweden)

    Erol İNCE

    2002-01-01

    Full Text Available The conversion kinetics of diluted acetic acid to ethyl acetate by ethanol esterification in a batch reactor in liquid phase with an acidic polymer catalyst (lewatit series was studied. The intrinsic rate constants have been correlated with the reaction temperature, concentration of catalyst, initial ratios of reactants and initial water concentrations. The kinetic analysis was restricted to the system at hand in which a liquid and vapor phase are at equilibrium.

  4. Process intensification for the ethyl lactate synthesis : integrated pervaporation reactor

    OpenAIRE

    Pereira, C.S.M.; Silva, V.M.T.M.; Pinho, Simão; A. E. Rodrigues

    2011-01-01

    Ethyl lactate is an important organic ester, which is biodegradable, produced by renewable resources and can be used as food additive, perfumery, flavor chemicals, solvent and pharmaceutical preparations[1]. It is a green solvent and could replace a range of environment-damaging halogenated and toxic solvents (for example: Nmethylpyrrolidone, toluene)[2]. The conventional way to produce ethyl lactate is the esterification of lactic acid with ethanol in the presence of an acid cata...

  5. 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)

  6. Potential grape-derived contributions to volatile ester concentrations in wine.

    Science.gov (United States)

    Boss, Paul K; Pearce, Anthony D; Zhao, Yanjia; Nicholson, Emily L; Dennis, Eric G; Jeffery, David W

    2015-01-01

    Grape composition affects wine flavour and aroma not only through varietal compounds, but also by influencing the production of volatile compounds by yeast. C9 and C12 compounds that potentially influence ethyl ester synthesis during fermentation were studied using a model grape juice medium. It was shown that the addition of free fatty acids, their methyl esters or acyl-carnitine and acyl-amino acid conjugates can increase ethyl ester production in fermentations. The stimulation of ethyl ester production above that of the control was apparent when lower concentrations of the C9 compounds were added to the model musts compared to the C12 compounds. Four amino acids, which are involved in CoA biosynthesis, were also added to model grape juice medium in the absence of pantothenate to test their ability to influence ethyl and acetate ester production. β-Alanine was the only one shown to increase the production of ethyl esters, free fatty acids and acetate esters. The addition of 1 mg∙L(-1) β-alanine was enough to stimulate production of these compounds and addition of up to 100 mg∙L(-1) β-alanine had no greater effect. The endogenous concentrations of β-alanine in fifty Cabernet Sauvignon grape samples exceeded the 1 mg∙L(-1) required for the stimulatory effect on ethyl and acetate ester production observed in this study. PMID:25939071

  7. Lewis acid promoted ruthenium(II)-catalyzed etherifications by selective hydrogenation of carboxylic acids/esters.

    Science.gov (United States)

    Li, Yuehui; Topf, Christoph; Cui, Xinjiang; Junge, Kathrin; Beller, Matthias

    2015-04-20

    Ethers are of fundamental importance in organic chemistry and they are an integral part of valuable flavors, fragrances, and numerous bioactive compounds. In general, the reduction of esters constitutes the most straightforward preparation of ethers. Unfortunately, this transformation requires large amounts of metal hydrides. Presented herein is a bifunctional catalyst system, consisting of Ru/phosphine complex and aluminum triflate, which allows selective synthesis of ethers by hydrogenation of esters or carboxylic acids. Different lactones were reduced in good yields to the desired products. Even challenging aromatic and aliphatic esters were reduced to the desired products. Notably, the in situ formed catalyst can be reused several times without any significant loss of activity. PMID:25728921

  8. 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...

  9. 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,...

  10. Pseudo catalytic transformation of volatile fatty acids into fatty acid methyl esters.

    Science.gov (United States)

    Jung, Jong-Min; Cho, Jinwoo; Kim, Ki-Hyun; Kwon, Eilhann E

    2016-03-01

    Instead of anaerobic digestion of biodegradable wastes for producing methane, this work introduced the transformation of acidogenesis products (VFAs) into fatty acid methyl esters (FAMEs) to validate the feasible production of short-chained fatty alcohols via hydrogenation of FAMEs. In particular, among VFAs, this work mainly described the mechanistic explanations for transforming butyric acid into butyric acid methyl ester as a case study. Unlike the conventional esterification process (conversion efficiency of ∼94%), the newly introduced esterification under the presence of porous materials via the thermo-chemical process reached up to ∼99.5%. Furthermore, the newly introduced esterification via the thermo-chemical pathway in this work showed extremely high tolerance of impurities: the conversion efficiency under the presence of impurities reached up to ∼99±0.3%; thus, the inhibition behaviors attributed from the impurities used for the experimental work were negligible. PMID:26720136

  11. Short-range order and fractal cluster structure of aggregates of barium titanate microparticles in a composite based on cyano-ethyl ester of polyvinyl alcohol

    Science.gov (United States)

    Krasovskii, A. N.; Novikov, D. V.; Vasina, E. S.; Matveichikova, P. V.; Sychev, M. M.; Rozhkova, N. N.

    2015-12-01

    The distribution of barium titanate (BaTiO3) microparticles in the matrix of cyano-ethyl ester of polyvinyl alcohol and the change in the surface energy upon introduction of shungite carbon nanoclusters into the dielectric composite have been investigated using the methods of scanning electron microscopy and contact angles. The computer processing of the electron microscopy data has demonstrated that the introduction of 0.04% shungite carbon nanoparticles into the composite leads to a decrease in the spatial homogeneity of the quasi-lattice and to an increase in the local density distribution of BaTiO3 microparticles, as well as in the correlation length corresponding to the formation of an infinite cluster of BaTiO3 particles. It has been found that, in this case, the surface energy and dielectric permittivity of the composite extremely increase.

  12. Metabolism of hydroxycinnamic acids and esters by Brettanomyces in different red wines

    Science.gov (United States)

    Depending on the cultivars and other factors, differing concentrations of hydroxycinnamic acids (caffeic, p-coumaric, and ferulic acids) and their corresponding tartaric acid esters (caftaric, coutaric, and fertaric acid, respectively) are found in red wines. Hydroxycinnamic acids are metabolized by...

  13. Synthesis of some glucose-fatty acid esters by lipase from Candida antarctica and their emulsion functions.

    Science.gov (United States)

    Ren, Kangzi; Lamsal, Buddhi P

    2017-01-01

    The synthesis of glucose esters with palmitic acid, lauric acid and hexanoic acid using lipase enzyme was studied and their emulsion functionality in oil-in-water system were compared. Reactions at 3:1M ratio of fatty acids-to-glucose had the highest conversion percentages (over 90% for each of the fatty acid). Initial conversion rate increased as substrate solubility increased. Ester bond formation was confirmed by nuclear magnetic resonance technique that the chemical shifts of glucose H-6 and α-carbon protons of fatty acids in the ester molecules shifted to the higher fields. Contact angle of water on esters' pelleted surface increased as the hydrophobicity increased. Glucose esters' and commercial sucrose esters' functionality as emulsifiers were compared. Glucose esters delayed, but did not prevent coalescence, because the oil droplets diameter doubled during 7days. Sucrose esters prevented coalescence during 7days since the droplets diameter did not have significant change. PMID:27507510

  14. Oxidative decarboxylation of mandelic acid derivative by recombinant Escherichia coli: a novel method of ethyl vanillin synthesis.

    Science.gov (United States)

    Pan, Xiao-Xia; Li, Jing-Jing; Wang, Mei-Gui; He, Wen-Sen; Jia, Cheng-Sheng; Zhang, Xiao-Ming; Feng, Biao; Li, Da-Li; Zeng, Zeng

    2013-06-01

    The benzoylformate decarboxylase gene (mdlC) from Pseudomonas putida was expressed in Escherichia coli BL21(DE3). The recombinant strain together with E. coli/pET30a-mdlB converted (S)-3-ethoxy-4-hydroxymandelic acid (S-EMA) into ethyl vanillin without ethyl vanillin degradation. 4 g ethyl vanillin/l was obtained from 10 g EMA/l within 12 h at 30 °C. This is the first report on the biotransformation of (S)-EMA to ethyl vanillin.

  15. Determination of a peroxisome proliferator-activated receptor γ agonist, 1-(trans-methylimino-N-oxy)-6-(2-morpholinoethoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (KR-62980) in rat plasma by liquid chromatography-tandem mass spectrometry.

    Science.gov (United States)

    Kim, Min-Sun; Song, Jin Sook; Roh, Hyeongjin; Park, Jong-Shik; Ahn, Jin Hee; Ahn, Sung-Hoon; Bae, Myung Ae

    2011-01-01

    A novel peroxisome proliferator-activated receptor γ (PPARγ) agonist, KR-62980, was determined by liquid-liquid extraction with ethyl acetate and liquid chromatography-tandem mass spectrometry (LC/MS/MS) in rat plasma. In order to evaluate the pharmacokinetics of KR-62980, a reliable, selective and sensitive high-performance liquid chromatographic method with electrospray ionization tandem mass spectrometry was developed for the quantification of KR-62980 in rat plasma. KR-62980 and imipramine (IS) were separated on Hypersil GOLD C18 column with a mixture of acetonitrile-ammonium formate (10mM) (80:20, v/v) as mobile phase. The ion transitions monitored were m/z 437.2 → 114.2 for KR-62980, m/z 281.3 → 86.1 for imipramine in multiple reaction monitoring (MRM) mode. The percent recoveries of KR-62980 and imipramine were 90.1 and 98.4% from rat plasma, respectively. The linear dynamic range extended from 0.01 to 10 μg/ml with a correlation coefficient (R(2)) greater than 0.99 and the lower limit of quantification was 0.01 μg/ml. The mean of intra- and inter-assay precisions was 2.1 and 9.3%. The method was validated and successfully applied to the pharmacokinetic study of KR-62980 in rat.

  16. The assignment of the configuration for α-hydroxy acid esters using a CEC strategy.

    Science.gov (United States)

    Peng, Ruixue; Lin, Lili; Zhang, Yuheng; Wu, Wangbin; Lu, Yan; Liu, Xiaohua; Feng, Xiaoming

    2016-06-21

    A simple and efficient (1)H NMR method for determining the absolute configuration of chiral α-hydroxy acid esters using a competing enantioselective conversion (CEC) strategy was developed. The α-hydroxy acid esters were acylated in the presence of Feng's chiral N,N'-dioxide-scandium(iii) complex, and the faster reaction was identified when one enantiomer of the chiral α-hydroxy acid ester was treated with both enantiomers of the ligand by NMR analysis of the reaction mixture without further purification. A mnemonic is presented to aid the assignment of the absolute configuration of the substrates. PMID:27189590

  17. Synthesis and Crystal Structure of 4-(4,6-dimethoxyl -pyrimidin-2-yl)-3-thiourea Carboxylic Acid Methyl Ester

    Institute of Scientific and Technical Information of China (English)

    HUANG Jie; SONG Ji-Rong; REN Ying-Hui; XU Kang-Zhen; MA Hai-Xia

    2006-01-01

    The title compound 4-(4,6-dimethoxylpyrimidin-2-yl)-3-thiourea carboxylic acid methyl ester was synthesized by the reaction of 2-amino-4,6-dimethoxyl pyrimidine, potassium thiocyanate and methyl chloroformate in ethyl acetate. Single crystals suitable for X-ray measurement were obtained by recrystallization with the solvent of dimethyl formamide at the room temperature. The structure was characterized by elemental analysis and IR and determined by X-ray diffraction analysis. Crystallographic data: C9H12N4O4S, Mr = 272.29, monoclinic, space group C2/m with a = 1.6672(3), b = 0.66383(12), c = 1.1617(2) nm, β = 109.275(2)°, V = 1.2136(4) nm3, Dc = 1.490 g/cm3, μ = 0.281 mm-1, F(000) = 568, Z = 4, R1 = 0.0341and wR2 = 0.1042.

  18. [Phthalic acid esters (PAEs) pollution in farmland soils: a review].

    Science.gov (United States)

    Wang, Kai-Rong; Cui, Ming-Ming; Shi, Yan-Xi

    2013-09-01

    The environmental pollution and food safety problems caused by phthalic acid esters (PAEs) have been attracted 'extensive attention around the world. As a large PAEs producer and consumer, China is facing severe PAEs environmental pollution problems. This paper reviewed the present pollution status of six PAEs classified by the U.S. Environmental Protection Agency as the priority pollutants in China farmland soils, analyzed the sources of these six PAEs in this country, and discussed the absorption and accumulation characteristics of the PAEs in different crops as well as the bio-toxic effects of PAEs pollutants. The PAEs concentrations in China farmland soils are significantly higher those in the farmland soils of the United States and European countries. The main sources of PAEs in China farmland soils are atmospheric deposition, agricultural films, sewage sludge application, and wastewater irrigation. There exist significant differences in the characteristics of PAEs absorption, accumulation, and distribution among different crops. PAEs not only have negative effects on soil quality, crop growth, and crop physiological and biochemical properties, but also possess bio-accumulative characteristics. The weaknesses in current researches were pointed out, and the suggestions for the further researches were given, e. g., to expand the scope of PAEs pollution survey, to explore the toxic mechanisms of PAEs on crops, and to develop the techniques for in situ remediation of PAEs-polluted soils.

  19. Intrapulmonary Delivery of Ethyl Pyruvate Attenuates Lipopolysaccharide : and Lipoteichoic Acid-Induced Lung Inflammation in Vivo

    OpenAIRE

    van Zoelen, Marieke A.D.; de Vos, Alex F.; Larosa, Gregory J.; Draing, Christian; Aulock, Sonja von; van der Poll, Tom

    2007-01-01

    Ethyl pyruvate (EP) is a stable pyruvate derivative that has been shown to exert anti-inflammatory effects in various models of systemic inflammation including endotoxemia. We here sought to determine the local effects of EP, after intrapulmonary delivery, in models of lung inflammation induced by instillation via the airways of either lipopolysaccharide (LPS, a constituent of the gram-negative bacterial cell wall) or lipoteichoic acid (LTA, a component of the gram-positive bacterial cell wal...

  20. Gas chromatography-mass spectrometry of ethyl palmitate calibration and resolution with ethyl oleate as biomarker ethanol sub acute in urine application study

    Science.gov (United States)

    Suaniti, Ni Made; Manurung, Manuntun

    2016-03-01

    Gas Chromatography-Mass Spectrometry is used to separate two and more compounds and identify fragment ion specific of biomarker ethanol such as palmitic acid ethyl ester (PAEE), as one of the fatty acid ethyl esters as early detection through conyugated reaction. This study aims to calibrate ethyl palmitate and develop analysis with oleate acid. This methode can be used analysis ethanol and its chemistry biomarker in ethanol sub-acute consumption as analytical forensic toxicology. The result show that ethanol level in urine rats Wistar were 9.21 and decreased 6.59 ppm after 48 hours consumption. Calibration curve of ethyl palmitate was y = 0.2035 x + 1.0465 and R2 = 0.9886. Resolution between ethyl palmitate and oleate were >1.5 as good separation with fragment ion specific was 88 and the retention time was 18 minutes.

  1. 固体酸催化合成二氯乙酸乙酯%Synthesis of ethyl dichloroacetate catalyzed by solid acid

    Institute of Scientific and Technical Information of China (English)

    刘俊峰; 朱莹莹; 冯桂英; 王胜华; 何超

    2014-01-01

    One kind of method was introduled for the synthesis of dichloro -acetic acid ethyl ester. Dichloroacetic acid was used as staring material,the catalysis of the catalyst on dehydration of dichloroacetic acid and ethanol to produce the ether was discussed.At the same times,The effects of different water-carrying agent such as benzene,toluene,cyclohexane and their dosage on the reaction were investigated.Taking FeCl3·6H2O as catalyst,cyclohexane as dehydrant,ethanol as reaction solvent and raw materials,dichloro-acetic acid ethyl ester was product.The best reaction condition was as follows:12.9 g dichloroacetic acid,20 ml dehydrated alcohol,15 ml cyclohexane,0.5 g ferric trichloride,reaction temperature was reflux ,reaction time was 40 min. After the reaction was finished ,distilling and collecting 153 ~156 ℃ distillation to get dichloro -acetic acid ethyl ester of a colourless liquid.The yield was 85 .4% and the purity is greater than or equa 98%.After the solvent was distilled,the catalyst was reused total 240 mins.The dichloro-acetic acid ethyl ester productivities of four tests are as follows respectively:85.4%,77.1%,83.4%,78.3%.%介绍一种二氯乙酸乙酯的合成方法.以二氯乙酸为起始原料,研究了催化剂对二氯乙酸与乙醇脱水醚化反应的催化性能,同时讨论了不同带水剂苯、甲苯、环己烷及其用量对反应的影响,得到以FeCl3·6H2 O为催化剂,环己烷为带水剂,乙醇既作反应原料又为溶剂,制备二氯乙酸乙酯,最佳反应条件:二氯乙酸12.9 g,无水乙醇20 mL,环己烷15 mL,催化剂用量0.5 g,反应温度:回流,反应时间40 min.反应产物蒸馏收集153~156℃的馏分得到无色液体二氯乙酸乙酯,纯度大于98%,蒸干溶剂后,进行催化剂重复使用试验,其结果为:重复反应4次,累计反应时间为240 min,二氯乙酸乙酯产率分别为85.4%,77.1%,83.4%,78.3%.

  2. 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

  3. 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 incorpo

  4. Esterification of levulinic acid into ethyl levulinate catalysed by sulfonated hydrothermal carbons

    Institute of Scientific and Technical Information of China (English)

    Filoklis D. Pileidis; Maham Tabassum; Sam Coutts; Maria-Magdalena Ttitirici

    2014-01-01

    The synthesis of carbon-based, heterogeneous sulphonic catalysts for the production of levulinate esters. Hydrothermal treatment at moderated temperatures was employed to generate highly func-tional carbonaceous materials, referred to as hydrothermal carbons (HTCs), from both glucose, cellulose and rye straw. The products were sulfonated to generate solid acid-catalysts. Characterisa-tion of the as-synthesised materials as well as catalyst activity tests were performed. SEM images indicate the micrometre-sized particles present in both HTCs were largely unaffected by sulfona-tion, although cellulose-derived HTC displayed signs of inadequate hydrolysis. FT-IR spectroscopy and elemental analysis confirmed successful incorporation of sulphonic groups. 13C solid state NMR, in addition to TGA, elucidated the carbons’ structural composition and supported the common-ly-proposed hydrothermal carbonisation mechanism. Finally, the catalysts were tested via levulinic acid-ethanol esterification and gave high conversion and ester-selectivities (>90%).

  5. Phase diagram measurements by Heat-flux DSC and thermodynamic calculations of the mixture of the Esters Ethyl undecanoate (C13H26O2) and Ethyl tridecanoate (C15H30O2)

    NARCIS (Netherlands)

    Schaftenaar, H.P.C.

    2006-01-01

    In this report a phase diagram is determined by heat flux DSC of the binary mixture Ethyl undecanoate and Ethyl tridecanoate. Our hypothesis for equilibrium phase behaviour is that the components Ethyl undecanoate and Ethyl tridecanoate do have the same crystal form and they have restricted miscibil

  6. Synthesis and characterization of new biodegradable thermosensitive polyphosphazenes with lactic acid ester and methoxyethoxyethoxy side groups

    Institute of Scientific and Technical Information of China (English)

    2010-01-01

    Two novel biodegradable thermosensitive polyphosphazenes with lactic acid ester and methoxyethoxyethoxy side groups were synthesized via the macromolecular substitution reactions of poly(dichlorophosphazene) with the sodium salt of lactic acid ester and sodium methoxyethoxyethoxide.Their structures were confirmed by ~(31)p NMR,~1H NMR,~(13)C NMR,IR,DSC,and elemental analysis.The lower critical solution temperature(LCST) behavior in water and in vitro degradation property of the polymers was investigated....

  7. Effects of Processing Variables on the Morphology and Diameter of Electrospun Poly(amino acid ester)phosphazene Nanofibers

    Institute of Scientific and Technical Information of China (English)

    LIN Yijun; DENG Qinghua; JIN Riguang

    2012-01-01

    Poly[(alanino ethyl ester)0 67 (glycino ethyl ester)0 33 phosphazene] (PAGP) was synthesized,and morphology and diameter of the electrospun PAGP nanofibers were systematically evaluated by using a cool field emission scanning electron microscope (SEM) with changing the important processing variables such as applied voltage,polymeric concentration,and ambient temperature.The average diameter of PAGP nanofibers was inversely proportional to the applied voltage,but increased with the increase of solution concentration.Lower environmental temperature was unfavorable due to the nanofibers conglutination.

  8. Pemisahan dan Pemurnian Phthalic Acid Ester dari Minyak Nyamplung

    Directory of Open Access Journals (Sweden)

    William Ekaputra Taifan

    2013-09-01

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

  9. Spectroscopic and quantum chemical analysis of Isonicotinic acid methyl ester

    Science.gov (United States)

    Shoba, D.; Periandy, S.; Govindarajan, M.; Gayathri, P.

    2015-02-01

    In this present study, an organic compound Isonicotinic acid methyl ester (INAME) was structurally characterized by FTIR, FT-Raman, and NMR and UV spectroscopy. The optimized geometrical parameters and energies of all different and possible conformers of INAME are obtained from Density Functional Theory (DFT) by B3LYP/6-311++G(d,p) method. There are three conformers (SI, SII-1, and SII-2) for this molecule (ground state). The most stable conformer of INAME is SI conformer. The molecular geometry and vibrational frequencies of INAME in the ground state have been calculated by using HF and density functional method (B3LYP) 6-311++G (d,p) basis set. Detailed vibrational spectral analysis has been carried out and assignments of the observed fundamental bands have been proposed on the basis of peak positions and relative intensities. The computed vibrational frequencies were compared with the experimental frequencies, which yield good agreement between observed and calculated frequencies. A study on the electronic properties, such as HOMO and LUMO energies were performed by time independent DFT approach. Besides, molecular electrostatic potential (MEP) and thermodynamic properties were performed. The electric dipole moment (μ) and first hyper polarizability (β) values of the investigated molecule were computed using ab initio quantum mechanical calculations. The calculated results show that the INAME molecule may have microscopic nonlinear optical (NLO) behavior with non zero values. The 1H and 13C nuclear magnetic resonance (NMR) chemical shifts of the molecule were calculated by gauge independent atomic orbital (GIAO) method.

  10. Choline Chloride Catalyzed Amidation of Fatty Acid Ester to Monoethanolamide: A Green Approach.

    Science.gov (United States)

    Patil, Pramod; Pratap, Amit

    2016-01-01

    Choline chloride catalyzed efficient method for amidation of fatty acid methyl ester to monoethanolamide respectively. This is a solvent free, ecofriendly, 100% chemo selective and economically viable path for alkanolamide synthesis. The Kinetics of amidation of methyl ester were studied and found to be first order with respect to the concentration of ethanolamine. The activation energy (Ea) for the amidation of lauric acid methyl ester catalyzed by choline chloride was found to be 50.20 KJ mol(-1). The 98% conversion of lauric acid monoethanolamide was obtained at 110°C in 1 h with 6% weight of catalyst and 1:1.5 molar ratio of methyl ester to ethanolamine under nitrogen atmosphere. PMID:26666271

  11. Selective synthesis of thiodiglycol dicarboxylic acid esters via -TsOH/C-catalysed direct esterification

    Indian Academy of Sciences (India)

    Dahong Jiang; Min Huang

    2012-09-01

    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 crucial for the transformation.

  12. Preparation of fatty acid methyl esters from Osage orange (Maclura pomifera) oil and evaluation as biodiesel

    Science.gov (United States)

    Fatty acid methyl esters were prepared in high yield by transesterification of Osage orange (Maclura pomifera) oil. Extracted using supercritical CO2, the crude oil was initially treated with mineral acid and methanol to lower its content of free fatty acids, thus rendering it amenable to homogeneou...

  13. Antifungal properties of halofumarate esters.

    Science.gov (United States)

    Gershon, H; Shanks, L

    1978-04-01

    Alkyl esters (C1--C4) of the four halofumaric acids were tested for antifungal activity against Candida albicans, Aspergillus niger, Mucor mucedo, and Trichophyton mentagrophytes at pH 5.6 and 7.0 in the absence and presence of 10% beef serum in Sabouraud dextrose agar. The most toxic compound to each organism was: C. albicans, ethyl iodofumarate (0.054 mmole/liter); A. niger, methyl bromofumarate (0.090 mmole/liter); M. mucedo, methyl fluorofumarate (0.037 mmole/liter); and T. mentagrophytes, ethyl iodofumarate (0.020 mmole/liter). The order of overall activity of the six most toxic compounds was: ethyl iodofumarate greater than ethyl chlorofumarate greater than methyl iodofumarate = methyl bromofumarate greater than methyl chlorofumarate greater than bromofumarate.

  14. In vitro skin permeation and retention of 5-aminolevulinic acid ester derivatives for photodynamic therapy.

    Science.gov (United States)

    De Rosa, Fernanda Scarmato; Tedesco, Antônio Cláudio; Lopez, Renata Fonseca Vianna; Pierre, Maria Bernadete Riemma; Lange, Norbert; Marchetti, Juliana Maldonado; Rotta, Jeane Cristina Gomes; Bentley, Maria Vitória Lopes Badra

    2003-04-29

    In photodynamic therapy (PDT), 5-aminiolevulinic acid (5-ALA) applied topically is converted, via the heme cycle, into protoporphyrin IX (PpIX), a photosensitizing agent, which upon excitation with light can induce tumor destruction. Due to its hydrophilic and zwitterionic characteristics, 5-ALA has limited penetration into the skin. More lipophilic 5-ALA ester derivatives are expected to cross stratum corneum more easily than 5-ALA. According to the determination of the partition coefficients of 5-ALA methyl, n-butyl, n-hexyl and n-octyl esters, these compounds showed an increased affinity to the SC, with 5-ALA hexyl ester and 5-ALA-octyl ester having the highest partition coefficients. Our in vitro skin permeation studies demonstrated an increased permeated amount for hexyl-ALA after 6 h of incubation, compared to other esters and 5-ALA. After 6 h, more 5-ALA-hexyl ester and -octyl ester were retained at viable epidermis and dermis than 5-ALA. According to these results, and considering that the conversion of 5-ALA into PpIX occurs preferentially in epidermis, it can be supposed that topical use of ester derivatives with longer chains (C(6) or C(8)) is an interesting proposal to optimize topical 5-ALA-PDT

  15. Acetic acid removal from corn stover hydrolysate using ethyl acetate and the impact on Saccharomyces cerevisiae bioethanol fermentation.

    Science.gov (United States)

    Aghazadeh, Mahdieh; Ladisch, Michael R; Engelberth, Abigail S

    2016-07-01

    Acetic acid is introduced into cellulose conversion processes as a consequence of composition of lignocellulose feedstocks, causing significant inhibition of adapted, genetically modified and wild-type S. cerevisiae in bioethanol fermentation. While adaptation or modification of yeast may reduce inhibition, the most effective approach is to remove the acetic acid prior to fermentation. This work addresses liquid-liquid extraction of acetic acid from biomass hydrolysate through a pathway that mitigates acetic acid inhibition while avoiding the negative effects of the extractant, which itself may exhibit inhibition. Candidate solvents were selected using simulation results from Aspen Plus™, based on their ability to extract acetic acid which was confirmed by experimentation. All solvents showed varying degrees of toxicity toward yeast, but the relative volatility of ethyl acetate enabled its use as simple vacuum evaporation could reduce small concentrations of aqueous ethyl acetate to minimally inhibitory levels. The toxicity threshold of ethyl acetate, in the presence of acetic acid, was found to be 10 g L(-1) . The fermentation was enhanced by extracting 90% of the acetic acid using ethyl acetate, followed by vacuum evaporation to remove 88% removal of residual ethyl acetate along with 10% of the broth. NRRL Y-1546 yeast was used to demonstrate a 13% increase in concentration, 14% in ethanol specific production rate, and 11% ethanol yield. This study demonstrated that extraction of acetic acid with ethyl acetate followed by evaporative removal of ethyl acetate from the raffinate phase has potential to significantly enhance ethanol fermentation in a corn stover bioethanol facility. © 2016 American Institute of Chemical Engineers Biotechnol. Prog., 32:929-937, 2016.

  16. Acetic acid removal from corn stover hydrolysate using ethyl acetate and the impact on Saccharomyces cerevisiae bioethanol fermentation.

    Science.gov (United States)

    Aghazadeh, Mahdieh; Ladisch, Michael R; Engelberth, Abigail S

    2016-07-01

    Acetic acid is introduced into cellulose conversion processes as a consequence of composition of lignocellulose feedstocks, causing significant inhibition of adapted, genetically modified and wild-type S. cerevisiae in bioethanol fermentation. While adaptation or modification of yeast may reduce inhibition, the most effective approach is to remove the acetic acid prior to fermentation. This work addresses liquid-liquid extraction of acetic acid from biomass hydrolysate through a pathway that mitigates acetic acid inhibition while avoiding the negative effects of the extractant, which itself may exhibit inhibition. Candidate solvents were selected using simulation results from Aspen Plus™, based on their ability to extract acetic acid which was confirmed by experimentation. All solvents showed varying degrees of toxicity toward yeast, but the relative volatility of ethyl acetate enabled its use as simple vacuum evaporation could reduce small concentrations of aqueous ethyl acetate to minimally inhibitory levels. The toxicity threshold of ethyl acetate, in the presence of acetic acid, was found to be 10 g L(-1) . The fermentation was enhanced by extracting 90% of the acetic acid using ethyl acetate, followed by vacuum evaporation to remove 88% removal of residual ethyl acetate along with 10% of the broth. NRRL Y-1546 yeast was used to demonstrate a 13% increase in concentration, 14% in ethanol specific production rate, and 11% ethanol yield. This study demonstrated that extraction of acetic acid with ethyl acetate followed by evaporative removal of ethyl acetate from the raffinate phase has potential to significantly enhance ethanol fermentation in a corn stover bioethanol facility. © 2016 American Institute of Chemical Engineers Biotechnol. Prog., 32:929-937, 2016. PMID:27090191

  17. Strain Screening and Culture Condition Optimization for the Enantioselectively Hydrolysis of(3R) - 2-Carboxyethyl-3-Cyano-5-Methylhexanoic Acid Ethyl Ester%(3R)-2-羧乙基-3-氰基-5-甲基己酸乙酯水解酶产生菌的筛选与产酶条件优化

    Institute of Scientific and Technical Information of China (English)

    吴薇; 杨立荣; 徐刚; 吴坚平

    2011-01-01

    Using ( R, S)-2-carboxyethyl-3-cyano-5-methyl-hexanoic acid ethylester ( rac-CCMAE) as sole carbon source, Pseudomonas sp. CGMCC No. 4184 was isolated which can enantioselectively hydrolyze (R)-CCMAE to (3R) -2-carboxyethyl-3-cyano-5-methylhexanoic acid (3R-CCMA) with eep of over 90%. The optimal temperature and pH for the production of hydrolase by Pseudomonas CGMCC No. 4184 were 30℃ and 7.4. Single-factor experiment, Plackett-Burman design and response surface methodology were applied subsequently to optimize the fermentation medium. After optimization, the enzyme activity increased from 15. 92U/L to 33.43 U/L ( about 2. 1 fold). By using resting cell catalysis system, (S)-CCMAE were successfully prepared with the conversion of 56. 3% and ees of 98.3% after 48 h under the condition of 5g/L CCMAE, 8g/L (cell dry weight) resting cells,20ml 0.1mol/L phosphate buffer (pH 7.4) , 30℃ and 200r/min.%以2-羧乙基-3-氰基-5-甲基己酸乙酯为唯一碳源,采用手性气相法检测,筛选到一株能产对映选择性水解酶的假单胞菌Pseudomonas CGMCC No.4184.该菌产的水解酶能优先水解R型底物产生(3R)-2-羧乙基-3-氰基-5-甲基己酸,产物对映体过量值达到90%以上.对菌株Pseudomonas CGMCC No.4184的产酶条件进行了研究,结果表明该菌产酶最适温度为30℃,最适pH为7.4.通过单因素试验、PIackett-Burman试验和响应面法研究并优化了产酶培养基组成,使酶活提高到33.43 U/L,比初始酶活(15.92 U/L)提高了2.1倍.利用静息细胞催化水解底物,当底物浓度和静息细胞干重分别为5 g/L和8 g/L时,在pH 7.4的磷酸缓冲液中反应48 h(温度30℃,摇床转速200 r/min),转化率为56.3%,底物对映体过量值达到98.3%,较好地实现了拆分制备(3S)-2-羧乙基-3-氰基-5-甲基己酸乙酯的目标.

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

    OpenAIRE

    Isabel Bento; Teresa Duarte, M.; M. João M. Curto; Inês F. Antunes; Hélène Ramos; Fátima C. Teixeira

    2006-01-01

    A series of indazoles substituted at the N-1 and N-2 positions with ester-containing side chains -(CH2)nCO2R of different lengths (n = 0-6, 9, 10) are described.Nucleophilic substitution reactions on halo esters (X(CH2)nCO2R) by 1H-indazole inalkaline solution lead to mixtures of N-1 and N-2 isomers, in which the N-1 isomerpredominates. Basic hydrolysis of the ester derivatives allowed the synthesis of thecorresponding indazole carboxylic acids. All compounds were fully characterised bymultin...

  19. A Convenient Route to 4-Carboxy-4-Anilidopiperidine Esters and Acids

    Directory of Open Access Journals (Sweden)

    Gjermund Henriksen

    2012-03-01

    Full Text Available The route selection and development of a convenient synthesis of 4-carboxy-4-anilidopiperidines is described. Previous routes were hampered by the low yield of the target esters as well as the inability to convert the esters to the required free acids. Considerations for large-scale production led to a modified synthesis that utilised a tert-butyl ester of 4-carboxy-4-anilidopiperidines which resulted in a dramatic increase in the overall yield of the target N-propionylated- 4-anilidopiperidine-4-carboxylic acids and their corresponding methyl esters. These compounds are now available for use as precursors and reference standards, of particular value for the production of 11C and 18F-labelled 4-carboxy-4-anilidopiperidine radiotracers.

  20. Modified montmorillonite as a heterogeneous catalyst in (m)ethyl esterification reaction of lauric acid

    International Nuclear Information System (INIS)

    Montmorillonite was modified with zirconium polyoxycations in the presence of ammonium sulphate. The material was characterized and used as a catalyst in the esterification of lauric acid, the reactions being accompanied by 23 factorial design. Conversions of up to 95.33 and 83.35% were observed for the methyl and ethyl esterification reactions respectively, proving superior to results obtained by thermal conversion. The material was submitted to three reaction cycles and similar conversions were observed, indicating the catalyst is not significantly deactivated after reuse. The catalyst was also tested under reflux conditions, yielding a maximum conversion of 36.86%. (author)

  1. 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 fil

  2. High Dose Film Dosimeter Based on a Mixture of m-cresol Purple and Tetrabromo phenolphthalein Ethyl Ester Dyed Poly (vinyl alcohol)

    International Nuclear Information System (INIS)

    Gathering two ph indicator dyes m-cresol purple (MCP), tetrabromo phenolphthalein ethyl ester (TBPE), previously studied as individual dosimeter each at low dose application in the same polymer matrix (PVA) extends the application dose response to 60 kGy. This flexible plastic film changes its colour from green to red passing through yellow colour on exposure to γ-rays photons due to the consequent lowering of ph caused by HCl generated from the radiolysis of chloral hydrate. Effect of different concentrations of chloral hydrate on response of the film was investigated. The film shows excellent stability before and after irradiation. The film has excellent stability in 10% to 50% relative humidity range (RH). The overall combined uncertainty (at 2ϭ) associated with measurement of response (Ai/ A0) at 438 nm for dose range 5-60 kGy is 6.33 %. So this film has the ability to monitor the absorbed dose in low and moderate irradiation dose due to its excellent stability before and after irradiation with a significance confidence level.

  3. Natural antimicrobials subtilosin and lauramide arginine ethyl ester synergize with conventional antibiotics clindamycin and metronidazole against biofilms of Gardnerella vaginalis but not against biofilms of healthy vaginal lactobacilli.

    Science.gov (United States)

    Algburi, Ammar; Volski, Anna; Chikindas, Michael L

    2015-07-01

    The purpose of this study was to evaluate the ability of clindamycin and metronidazole to synergize with natural antimicrobials against biofilms of bacterial vaginosis (BV)-associated Gardnerella vaginalis. Minimum bactericidal concentrations for biofilm cells (MBCs-B) were determined for each antimicrobial. The MBCs-B of lauramide arginine ethyl ester (LAE), subtilosin, clindamycin and metronidazole were 50, 69.5, 20 and 500 μg mL(-1), respectively. A checkerboard assay and isobologram were used to analyze the type of interactions between these antimicrobials. The combination of metronidazole with natural antimicrobials did not inhibit planktonic lactobacilli. Clindamycin with either LAE or with subtilosin was inhibitory for planktonic but not for biofilm-associated lactobacilli. All tested antimicrobial combinations were inhibitory for BV-associated Mobiluncus curtisii and Peptostreptococcus anaerobius. LAE and subtilosin synergized with clindamycin and metronidazole against biofilms of G. vaginalis but not biofilm-associated vaginal lactobacilli. The biofilms of BV-associated pathogens can be controlled by synergistically acting combinations of conventional antibiotics and natural antimicrobials which will help better management of current antibiotics, especially considering robust bacterial resistance. Our findings create a foundation for a new strategy in the effective control of vaginal infections.

  4. Bis(tetra-ethyl-ammonium) bis-(hydrogen l-tartrate) l-tartaric acid monohydrate.

    Science.gov (United States)

    Rajalakshmi, M; Indirajith, R; Gopalakrishnan, R; Ramamurthi, K; Stoeckli-Evans, Helen

    2011-06-01

    In the title compound, 2C(8)H(20)N(+)·2C(4)H(5)O(6) (-)·C(4)H(6)O(6)·H(2)O, the presence of the two tetra-ethyl-ammonium cations is balanced by two hydrogen l-tartrate anions. Also present in the asymmetric unit are a mol-ecule of l-tartaric acid and a water mol-ecule. The various components are linked by O-H⋯O hydrogen bonds. In the crystal, two-dimensional networks are formed via O-H⋯O hydrogen bonds and C-H⋯O inter-actions involving the water mol-ecule, the hydrogen l-tartrate anions and the l-tartaric acid mol-ecules. These layers, which stack along [001], are separated by tetra-ethyl-ammonium cations. The latter are also involved in C-H⋯O inter-actions with the anions and the l-tartaric acid and water mol-ecules participating in the two-dimensional network.

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

    Science.gov (United States)

    Chisnell, J. R.

    1984-01-01

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

  6. Fatty Acid Methyl Esters as Biosolvents of Epoxy Resins: A Physicochemical Study

    OpenAIRE

    Medina-González, Yaocihuatl; De Caro, Pascale; Thiebaud-Roux, Sophie; Lacaze-Dufaure, Corinne

    2007-01-01

    The C8 to C18 fatty acid methyl esters (FAME) have been compared as solvents for two epoxy resin pre-polymers, bisphenol A diglycidyl ether (DGEBA) and triglycidyl paminophenol ether (TGPA). It was found that the solubilization limits vary according to the ester and that methyl caprylate is the best solvent of both resins. To explain these solubility performances, physical and chemical properties of FAME were studied, such as the Hansen parameters, viscosity, binary diffusion coefficient and ...

  7. 白酒中乙酯类成分的气相色谱-质谱分析%Analysis of Ester in Some Spirit by Gas Chromatography-Mass Spectrometry

    Institute of Scientific and Technical Information of China (English)

    骆传环; 黄荣清; 肖炳坤; 梁乾德

    2004-01-01

    To determine fragrance character of Spirit “Bai” from Shandong. Spirit “Lu”was positive control, “Er”, egative control, three samples were extracted with either,then analyzed qualitatively and quantitatively with ISTD N-amyl acetate (EP) by gas chromatography-mass spectrometry (GC/MS). Fragranter components including ethyl acid ester(E),butanotic acid ester (B),lactic acid ester (L), pentoic acid ester(p), and hexanoic acid ester(H) were chosen. The result showed that the level of esters were higher in Bai close to “Lu”, so “Bai” can be called concentration fragrant type spirit.

  8. Solid Phase Synthesis of Ethyl β-Substituted Indolepropionates

    Institute of Scientific and Technical Information of China (English)

    刘占祥; 阮秀秀; 黄宪

    2003-01-01

    A facile solid phase synthesis of ethyl β-substituted indolepropionates is reported. Condensation between indole, polymer-supported cyclic malonic acid ester and aldehyde yielded the trimolecular adducts, which was cleaved by pyridine/EtOH to release the final products in good yield with high purity.

  9. Combustion and Emission Characteristics of Variable Compression Ignition Engine Fueled with Jatropha curcas Ethyl Ester Blends at Different Compression Ratio

    Directory of Open Access Journals (Sweden)

    Rajneesh Kumar

    2014-01-01

    Full Text Available Engine performance and emission characteristics of unmodified biodiesel fueled diesel engines are highly influenced by their ignition and combustion behavior. In this study, emission and combustion characteristics were studied when the engine operated using the different blends (B10, B20, B30, and B40 and normal diesel fuel (B0 as well as when varying the compression ratio from 16.5 : 1 to 17.5 : 1 to 18.5 : 1. The change of compression ratio from 16.5 : 1 to 18.5 : 1 resulted in 27.1%, 27.29%, 26.38%, 28.48%, and 34.68% increase in cylinder pressure for the blends B0, B10, B20, B30, and B40, respectively, at 75% of rated load conditions. Higher peak heat release rate increased by 23.19%, 14.03%, 26.32%, 21.87%, and 25.53% for the blends B0, B10, B20, B30, and B40, respectively, at 75% of rated load conditions, when compression ratio was increased from16.5 : 1 to 18.5 : 1. The delay period decreased by 21.26%, CO emission reduced by 14.28%, and NOx emission increased by 22.84% for B40 blends at 75% of rated load conditions, when compression ratio was increased from 16.5 : 1 to 18.5 : 1. It is concluded that Jatropha oil ester can be used as fuel in diesel engine by blending it with diesel fuel.

  10. 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.

  11. Cold Flow Properties of Fatty Esters

    Directory of Open Access Journals (Sweden)

    Andrea Kleinová

    2007-09-01

    Full Text Available The article is devoted to the study of cold fl ow properties of neat esters of branched chain alcohols with fatty acids and blends of these esters with fossil diesel fuel. According to the determined CFPP values, the influence of alcohol branching on the fuel filterability is negligible and was detected only in the case of 2-ethyl hexanol. Fossil fuel blending with fatty esters up to 10 % vol. does not substantially change the cold flow properties of fossil fuel. DSC cooling scan parameters should be employed to predict CFPP of blended diesel fuel.

  12. Concentration and stabilization of C₂₀-₂₂ n-3 polyunsaturated fatty acid esters from the oil of Sardinella longiceps.

    Science.gov (United States)

    Chakraborty, Kajal; Joseph, Deepu; Joseph, Dexy

    2016-05-15

    Methyl esters of C20-22n-3 polyunsaturated fatty acids derived from sardine oil triglycerides were concentrated to 86% purity with greater than 30% recovery by argentated chromatography. The synergistic effect of ethyl acetate fractions of seaweeds Kappaphycus alvarezii, Hypnea musciformis and Jania rubens used in 0.1:0.2:0.2 (%, w/w) ratio in arresting oxidative degradation of the n-3 PUFA methyl ester concentrate was demonstrated during accelerated storage. The induction time (6.8h) and antioxidant activity indices (>24) were greater for n-3 PUFA concentrates supplemented with seaweed extracts than antioxidants BHT and α-tocopherol (<5h and <17, respectively). Nuclear Magnetic Resonance spectroscopy was employed to study the oxidative changes of fatty acid signals of PUFA concentrate during accelerated storage. Potential of seaweeds to improve the storage stability of C20-22n-3 fatty acid methyl esters was studied. This study has applications in development of food and pharmaceutical products. PMID:26776041

  13. 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...

  14. Low-temperature phase behavior of fatty acid methyl esters by differential scanning calorimetry (DSC)

    Science.gov (United States)

    Fatty acid methyl ester (FAME) mixtures have many uses including biodiesel, lubricants, metal-working fluids, surfactants, polymers, coatings, green solvents and phase-change materials. The physical properties of a FAME mixture depends on the fatty acid concentration (FAC) profile. Some products hav...

  15. 40 CFR 721.10142 - Oxabicycloalkane carboxylic acid alkanediyl ester (generic).

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Oxabicycloalkane carboxylic acid alkanediyl ester (generic). 721.10142 Section 721.10142 Protection of Environment ENVIRONMENTAL PROTECTION... New Uses for Specific Chemical Substances § 721.10142 Oxabicycloalkane carboxylic acid...

  16. Plasma Cholesterol Ester Fatty Acids: A New Biochemical Abnormality in Obstructive Jaundice

    OpenAIRE

    Scriven, M. W.; Horrobin, D. F.; Puntis, M. C. A.

    1995-01-01

    Changes in fatty acid patterns may explain many of the observed abnormalities found in obstructive jaundice. This study looked at fatty acids in plasma cholesterol esters, in a group of patients with obstructive jaundice and a matched group of controls. Significant abnormalities were demonstrated, most importantly a fall in essential fatty acids, in the jaundiced group. Overall the saturation of this fraction, as assessed by double bond index, rose. The essential fatty acids ar...

  17. Aerobic oxidation of aqueous ethanol using heterogeneous gold catalysts: Efficient routes to acetic acid and ethyl acetate

    DEFF Research Database (Denmark)

    Jørgensen, Betina; Christiansen, Sofie Egholm; Thomsen, M.L.D.;

    2007-01-01

    The aerobic oxidation of aqueous ethanol to produce acetic acid and ethyl acetate was studied using heterogeneous gold catalysts. Comparing the performance of Au/MgAl2O4 and Au/TiO2 showed that these two catalysts exhibited similar performance in the reaction. By proper selection of the reaction...... conditions, yields of 90-95% of acetic acid could be achieved at moderate temperatures and pressures. Based on our findings, a reaction pathway for the catalytic oxidation of ethanol via acetaldehyde to acetic acid is proposed, and the rate-determining step (RDS) in the mechanism is found to be the (possibly......, the possibilities for producing ethyl acetate by the aerobic oxidation of ethanol is also studied. At low ethanol concentrations, the main product is acetic acid; at concentrations >60 wt%, it is ethyl acetate....

  18. Understanding hypertriglyceridemia in women: clinical impact and management with prescription omega-3-acid ethyl esters

    OpenAIRE

    Dayspring, Thomas D

    2011-01-01

    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 provi...

  19. Glucuronic acid and the ethanol metabolite ethyl-glucuronide cause toll-like receptor 4 activation and enhanced pain.

    Science.gov (United States)

    Lewis, Susannah S; Hutchinson, Mark R; Zhang, Yingning; Hund, Dana K; Maier, Steven F; Rice, Kenner C; Watkins, Linda R

    2013-05-01

    We have previously observed that the non-opioid morphine metabolite, morphine-3-glucuronide, enhances pain via a toll-like receptor 4 (TLR4) dependent mechanism. The present studies were undertaken to determine whether TLR4-dependent pain enhancement generalizes to other classes of glucuronide metabolites. In silico modeling predicted that glucuronic acid alone and ethyl glucuronide, a minor but long-lasting ethanol metabolite, would dock to the same MD-2 portion of the TLR4 receptor complex previously characterized as the docking site for morphine-3-glucuronide. Glucuronic acid, ethyl glucuronide and ethanol all caused an increase in TLR4-dependent reporter protein expression in a cell line transfected with TLR4 and associated co-signaling molecules. Glucuronic acid-, ethyl glucuronide-, and ethanol-induced increases in TLR4 signaling were blocked by the TLR4 antagonists LPS-RS and (+)-naloxone. Glucuronic acid and ethyl glucuronide both caused allodynia following intrathecal injection in rats, which was blocked by intrathecal co-administration of the TLR4 antagonist LPS-RS. The finding that ethyl glucuronide can cause TLR4-dependent pain could have implications for human conditions such as hangover headache and alcohol withdrawal hyperalgesia, as well as suggesting that other classes of glucuronide metabolites could have similar effects. PMID:23348028

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

    Directory of Open Access Journals (Sweden)

    Lognay G.

    2000-01-01

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

  1. Anticancer Activities of Substituted Cinnamic Acid Phenethyl Esters on Human Cancer Cell Lines

    Institute of Scientific and Technical Information of China (English)

    LIShu-chun; LIHui; ZHANGFa; LIZhong-jun; CUIJing-rong

    2003-01-01

    Caffeic acid phenethyl ester (CAPE) and sixteen substituted cinnamic acid phenethyl esters were prepared via conventional procedures in order to test their in vitro anticancer activities by either MTT assay or SRB assay on six different human cancer cell lines. The results indicated that in the concentration of 10μmol·L-1 the lead compmuM CAPE possessed anficancer activities against human HL-60, Bel-7402, and Hela cell lines, and two other compounds possessed potent anticancer activities against Bel-7402 and Hela cell lines.

  2. Improved stability and enhanced efficiency to degrade chlorimuron-ethyl by the entrapment of esterase SulE in cross-linked poly (γ-glutamic acid)/gelatin hydrogel

    International Nuclear Information System (INIS)

    Highlights: • Esterase SulE was entrapped in a three-dimensional network of CPE. • CPE-SulE obviously improved thermostability, pH stability and reusability. • CPE-SulE displayed obviously enhanced efficiency in degrading chlorimuron-ethyl. • The three-dimensional network and kinetic parameters of CPE-SulE were analysed. • CPE-SulE possesses the great potential to remediate chlorimuron-ethyl contaminated in situ. - Abstract: Free enzymes often undergo some problems such as easy deactivation, low stability, and less recycling in biodegradation processes, especially in soil condition. A novel esterase SulE, which is responsible for primary degradation of a wide range of sulfonylurea herbicides by methyl or ethyl ester de-esterification, was expressed by strain Hansschlegelia sp. CHL1 and entrapped for the first time in an environment-friendly, biocompatible and biodegradable cross-linked poly (γ-glutamic acid)/gelatin hydrogel (CPE). The activity and stability of CPE-SulE were compared with free SulE under varying pH and temperature condition by measuring chlorimuron-ethyl residue. Meanwhile, the three-dimensional network of CPE-SulE was verified by scanning electron microscopy (SEM). The results showed that CPE-SulE obviously improved thermostability, pH stability and reusability compared with free SulE. Furthermore, CPE-SulE enhanced degrading efficiency of chlorimuron-ethyl in both soil and water system, especially in acid environment. The characteristics of CPE-SulE suggested the great potential to remediate chlorimuron-ethyl contaminated soils in situ

  3. Improved stability and enhanced efficiency to degrade chlorimuron-ethyl by the entrapment of esterase SulE in cross-linked poly (γ-glutamic acid)/gelatin hydrogel

    Energy Technology Data Exchange (ETDEWEB)

    Yang, Liqiang [State Key Laboratory of Forest and Soil Ecology, Institute of Applied Ecology, Chinese Academy of Sciences, Shenyang (China); University of Chinese Academy of Sciences, Beijing (China); Li, Xinyu; Li, Xu; Su, Zhencheng; Zhang, Chenggang; Xu, MingKai [State Key Laboratory of Forest and Soil Ecology, Institute of Applied Ecology, Chinese Academy of Sciences, Shenyang (China); Zhang, Huiwen, E-mail: hwzhang@iae.ac.cn [State Key Laboratory of Forest and Soil Ecology, Institute of Applied Ecology, Chinese Academy of Sciences, Shenyang (China)

    2015-04-28

    Highlights: • Esterase SulE was entrapped in a three-dimensional network of CPE. • CPE-SulE obviously improved thermostability, pH stability and reusability. • CPE-SulE displayed obviously enhanced efficiency in degrading chlorimuron-ethyl. • The three-dimensional network and kinetic parameters of CPE-SulE were analysed. • CPE-SulE possesses the great potential to remediate chlorimuron-ethyl contaminated in situ. - Abstract: Free enzymes often undergo some problems such as easy deactivation, low stability, and less recycling in biodegradation processes, especially in soil condition. A novel esterase SulE, which is responsible for primary degradation of a wide range of sulfonylurea herbicides by methyl or ethyl ester de-esterification, was expressed by strain Hansschlegelia sp. CHL1 and entrapped for the first time in an environment-friendly, biocompatible and biodegradable cross-linked poly (γ-glutamic acid)/gelatin hydrogel (CPE). The activity and stability of CPE-SulE were compared with free SulE under varying pH and temperature condition by measuring chlorimuron-ethyl residue. Meanwhile, the three-dimensional network of CPE-SulE was verified by scanning electron microscopy (SEM). The results showed that CPE-SulE obviously improved thermostability, pH stability and reusability compared with free SulE. Furthermore, CPE-SulE enhanced degrading efficiency of chlorimuron-ethyl in both soil and water system, especially in acid environment. The characteristics of CPE-SulE suggested the great potential to remediate chlorimuron-ethyl contaminated soils in situ.

  4. [Degradation of urea and ethyl carbamate in Chinese Rice wine by recombinant acid urease].

    Science.gov (United States)

    Zhou, Jianli; Kang, Zhen; Liu, Qingtao; Du, Guocheng; Chen, Jian

    2016-01-01

    Ethyl carbamate (EC) as a potential carcinogen commonly exists in traditional fermented foods. It is important eliminate urea that is the precursors of EC in many fermented foods, including Chinese Rice wine. On the basis of achieving high-level overexpression of food-grade ethanol-resistant acid urease, we studied the hydrolysis of urea and EC with the recombinant acid urease. Recombinant acid urease showed degraded urea in both the simulated system with ethanol and Chinese Rice wine (60 mg/L of urea was completely degraded within 25 h), indicating that the recombinant enzyme is suitable for the elimination of urea in Chinese Rice wine. Although recombinant acid urease also has degradation catalytic activity on EC, no obvious degradation of EC was observed. Further investigation results showed that the Km value for urea and EC of the recombinant acid urease was 0.7147 mmol/L and 41.32 mmol/L, respectively. The results provided theoretical foundation for realizing simultaneous degradation of urea and EC.

  5. Ionic liquids as novel solvents for the synthesis of sugar fatty acid ester.

    Science.gov (United States)

    Mai, Ngoc Lan; Ahn, Kihun; Bae, Sang Woo; Shin, Dong Woo; Morya, Vivek Kumar; Koo, Yoon-Mo

    2014-12-01

    Sugar fatty acid esters are bio-surfactants known for their non-toxic, non-ionic, and high biodegradability . With great emulsifying and conditioning effects, sugar fatty acids are widely used in the food, pharmaceutical, and cosmetic industries. Biosynthesis of sugar fatty acid esters has attracted growing attention in recent decades. In this study, the enzymatic synthesis of sugar fatty acid esters in ionic liquids was developed, optimized, and scaled up. Reaction parameters affecting the conversion yield of lipase-catalyzed synthesis of glucose laurate from glucose and vinyl laurate (i.e. temperature, vinyl laurate/glucose molar ratio, and enzyme loads) were optimized by response surface methodology (RSM). In addition, production was scaled up to 2.5 L, and recycling of enzyme and ionic liquids was investigated. The results showed that under optimal reaction conditions (66.86 °C, vinyl laurate/glucose molar ratio of 7.63, enzyme load of 73.33 g/L), an experimental conversion yield of 96.4% was obtained which is close to the optimal value predicted by RSM (97.16%). A similar conversion yield was maintained when the reaction was carried out at 2.5 L. Moreover, the enzymes and ionic liquids could be recycled and reused effectively for up to 10 cycles. The results indicate the feasibility of ionic liquids as novel solvents for the biosynthesis of sugar fatty acid esters.

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

    Directory of Open Access Journals (Sweden)

    Isabel Bento

    2006-11-01

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

  7. Substituent effects and pH profiles for stability constants of arylboronic acid diol esters.

    Science.gov (United States)

    Martínez-Aguirre, Mayte A; Villamil-Ramos, Raul; Guerrero-Alvarez, Jorge A; Yatsimirsky, Anatoly K

    2013-05-17

    Stability constants of boronic acid diol esters in aqueous solution have been determined potentiometrically for a series of meta-, para-substituted phenylboronic acids and diols of variable acidity. The constants β(11-1) for reactions between neutral forms of reactants producing the anionic ester plus proton follow the Hammett equation with ρ depending on pKa of diol and varying from 2.0 for glucose to 1.29 for 4-nitrocatechol. Observed stability constants (K(obs)) measured by UV-vis and fluorometric titrations at variable pH for esters of 4,5-dihydroxy-1,3-benzenedisulfonate (Tiron) generally agree with those expected on the basis of β(11-1) values, but the direct fitting of K(obs) vs pH profiles gives shifted pKa values both for boronic acids and diol as a result of significant interdependence of fitting parameters. The subsituent effects on absorption and fluorescence spectra of Tiron arylboronate esters are characterized. The K(obs) for Tiron determined by (11)B NMR titrations are approximately 1 order of magnitude smaller than those determined by UV-vis titrations under identical conditions. A general equation, which makes possible an estimate of β(11-1) for any pair of boronic acid and diol from their pKa values, is proposed on the basis of established Brönsted-type correlation of Hammett parameters for β(11-1) with acidity of diols. The equation allows one to calculate stability constants expected only on basis of acid-base properties of the components, thus permitting more strict evaluation of contributions of additional factors such as steric or charge effects to the ester stability.

  8. [Primary research on anti-tumor activity of panaxadiol fatty acid esters].

    Science.gov (United States)

    Zhang, Chun-Hong; Zhang, Lian-Xue; Li, Xiang-Gao; Gao, Yu-Gang; Liu, Ya-Jing

    2006-11-01

    For making use of Ginseng resources and finding new anti-tumor drugs, the anti-tumor activity of three kinds of new panaxadiol fatty acid ester derivates: 3beta-acetoxy panaxadiol (I), 3beta-palmitic acid aceloxy panaxadiol (II), 3beta-octadecanoic acid aceloxy panaxadiol (Ill) and panaxaiol were compared through the method of cell stain and counting. Tumor cell was Vero cell line. Positive control was 5-FU. Blank was RPM11640 culture medium. Negative control was RPM11640 culture medium and the solvent for subjected drugs. The result showed that compound I had the strongest anti-tumor activity, second was panaxadiol, II and III had the same and the weakest antitumor activity. Furthermore, the anti-tumor activities of panaxadiol fatty acid ester derivates showed positive correlation with subjects' concentrations, but no relationship with molecular weight of fatty acid. PMID:17228662

  9. Dielectric properties of solution-grown-undoped and acrylic-acid-doped ethyl cellulose

    Indian Academy of Sciences (India)

    P K Khare; Sandeep K Jain

    2000-02-01

    Dielectric capacities and losses were measured, in the temperature (50–170°C) and frequency (01–100 kHz range), for undoped and acrylic acid (AA) doped ethyl cellulose (EC) films (thickness about 20 m) with progressive increase in the concentration of dopant in the polymer matrix. The variation of capacity with temperature is attributed to thermal expansion in the lower temperature region to the orientation of dipolar molecules in the neighbourhood of glass transition temperature () and random thermal motion of molecules above . The dielectric losses exhibit a broad peak. Doping with AA is found to affect the magnitude and position of the peak. AA is found to have a two-fold action. Firstly, it enhances the chain mobility and secondly, it increases the dielectric loss by forming charge transfer complexes.

  10. Preparation of sphingolipid fatty acid methyl esters for determination by gas-liquid chromatography.

    Science.gov (United States)

    MacGee, J; Williams, M G

    1981-01-30

    Sphingolipid fatty acids are first converted to a mixture of free acids and their n-butyl esters by heating the specimen at 85 degree C in aqueous butanolic hydrogen chloride; the butyl esters are then saponified with methanolic potassium hydroxide. After acidification and extraction into hexane, the fatty acids are extracted into a very small volume of aqueous trimethyl(m-trifluorotolyl)ammonium hydroxide (TMTFTH), injection of an aliquot of the TMTFTH extract into the gas chromatograph yields the fatty acid methyl esters by pyrolytic methylation of the quaternary ammonium salts of the fatty acids. The preparation of a specimen ready for the gas--liquid chromatographic (GLC) analysis with quantitative recovery of the sphingolipid fatty acids can be accomplished in less than 2 h. By comparison, none of a number of well-accepted techniques for the release of sphingomyelin fatty acids by hydrolysis or methanolysis released the fatty acids quantitatively in less than 3 h, and all required additional manipulations before GLC analysis. PMID:7217267

  11. Encapsulation of ployunsaturated fatty acid esters with solid lipid particles

    Science.gov (United States)

    Polyunsaturated fatty acids (PUFA) such as a-linolenic acid (ALA) and docosahexaenoic acid (DHA) are known to improve cardiovascular and nervous system health. These compounds are increasingly used in food and animal feed formulations. However, the high degree of unsaturation in these structures can...

  12. 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.

  13. Synthesis and characterization of biodegradable polymer: Poly (ethene maleic acid ester-co-D,L-lactide acid)

    Institute of Scientific and Technical Information of China (English)

    Mei Na Huang; Yan Feng Luo; Jia Chen; Yong Gang Li; Chun Hua Fu; Yuan Liang Wang

    2007-01-01

    A novel biodegradable polymer-poly (ethene maleic acid ester-co-D,L-lactide acid) was synthesized by copolymerizing lactide and prepolymer, which was prepared by the condensation of maleic anhydride and glycol, using p-toluene sulphonic acid as a catalyst, attempting to improve the hydrophilicity, increase flexibility and modulate the degradation rate. FTIR, 1H NMR, MALLS and DSC were employed to characterize these polymers.

  14. Enzymatic Synthesis of l-Ascorbyl Fatty Acid Esters Under Ultrasonic Irradiation and Comparison of Their Antioxidant Activity and Stability.

    Science.gov (United States)

    Jiang, Chen; Lu, Yuyun; Li, Zhuo; Li, Cunzhi; Yan, Rian

    2016-06-01

    A series of novel l-ascorbyl fatty acid esters were synthesized by catalization of Novozym(®) 435 under ultrasonic irradiation and characterized by infrared spectroscopy, electrospray ionization mass spectra, and nuclear magnetic resonance. Their properties especially antioxidant activity and stability were investigated. The results showed that the reducing power, the scavenging activity of hydroxyl radical and 2,2-diphenyl-1-picrylhydrazyl radical were decreased with the increase of the number of carbon atoms in fatty acid. The hydroxyl radical scavenging activity and reducing power of l-ascorbyl saturated fatty acid esters were better than that of tert-butylhydroquinone. The induction period in lipid oxidation of l-ascorbyl saturated fatty acid esters and tert-butylhydroquinone were longer than that of l-ascorbyl unsaturated fatty acid esters and l-ascorbic acid both in soybean oil and lard. Besides, the l-ascorbyl fatty acid esters showed different stabilities in different conditions by comparing with l-ascorbic acid, and the l-ascorbyl saturated fatty acid esters were more stable than l-ascorbyl unsaturated fatty acid esters in ethanol solution. PMID:27100741

  15. Beyond fatty acid methyl esters: Expanding the renewable carbon profile with alkenones from Isochrysis sp.

    Science.gov (United States)

    In addition to characteristic fatty acid methyl esters (FAMEs), biodiesel produced from Isochrysis sp. contains a significant amount (14% dry weight) of predominantly C37 and C38 longchain alkenones. These compounds are members of a class of lipids known collectively as polyunsaturated long-chain al...

  16. Evaluation of Mosquito Repellent Activity of Isolated Oleic Acid, Eicosyl Ester from Thalictrum javanicum.

    Science.gov (United States)

    Gurunathan, Abinaya; Senguttuvan, Jamuna; Paulsamy, S

    2016-01-01

    To evaluate the traditional use, the mosquito repellent property of Thalictrum javanicum and to confirm the predicted larvicidal activity of the isolated compound, oleic acid, eicosyl ester from its aerial parts by PASS software, the present study was carried out using 4th instar stage larvae of the mosquitoes, Aedes aegypti (dengue vector) and Culex quinquefasciatus (filarial vector). Insecticidal susceptibility tests were conducted and the mortality rate was observed after 24 h exposure. The chitinase activity of isolated compound was assessed by using purified β-N-acetyl glucosaminidase (chitinase). Ecdysone 20-monooxygenase assay (radioimmuno assay) was made using the same larval stage of A. aegyptiand C. quinquefasciatus. The results were compared with the crude methanol extract of the whole plant. The isolated compound, oleic acid, eicosyl ester was found to be the most effective larvicide against A. aegypti (LC50/24 h -8.51 ppm) and C. quinquefasciatus (LC50/24 h - 12.5 ppm) than the crude methanol extract (LC50/24 h - 257.03 ppm and LC50/24 h - 281.83 ppm, respectively). The impact of oleic acid, eicosyl ester on reducing the activity of chitinase and ecdysone 20-monooxygenase was most prominent in both the target species, A. aegyptiand C. quinquefasciatus than the control. The results therefore suggest that the compound, oleic acid, eicosyl ester from Thalictrum javanicum may be considered as a potent source of mosquito larvicidal property. PMID:27168688

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

    Science.gov (United States)

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

  18. Evaluation of Mosquito Repellent Activity of Isolated Oleic Acid, Eicosyl Ester from Thalictrum javanicum.

    Science.gov (United States)

    Gurunathan, Abinaya; Senguttuvan, Jamuna; Paulsamy, S

    2016-01-01

    To evaluate the traditional use, the mosquito repellent property of Thalictrum javanicum and to confirm the predicted larvicidal activity of the isolated compound, oleic acid, eicosyl ester from its aerial parts by PASS software, the present study was carried out using 4th instar stage larvae of the mosquitoes, Aedes aegypti (dengue vector) and Culex quinquefasciatus (filarial vector). Insecticidal susceptibility tests were conducted and the mortality rate was observed after 24 h exposure. The chitinase activity of isolated compound was assessed by using purified β-N-acetyl glucosaminidase (chitinase). Ecdysone 20-monooxygenase assay (radioimmuno assay) was made using the same larval stage of A. aegyptiand C. quinquefasciatus. The results were compared with the crude methanol extract of the whole plant. The isolated compound, oleic acid, eicosyl ester was found to be the most effective larvicide against A. aegypti (LC50/24 h -8.51 ppm) and C. quinquefasciatus (LC50/24 h - 12.5 ppm) than the crude methanol extract (LC50/24 h - 257.03 ppm and LC50/24 h - 281.83 ppm, respectively). The impact of oleic acid, eicosyl ester on reducing the activity of chitinase and ecdysone 20-monooxygenase was most prominent in both the target species, A. aegyptiand C. quinquefasciatus than the control. The results therefore suggest that the compound, oleic acid, eicosyl ester from Thalictrum javanicum may be considered as a potent source of mosquito larvicidal property.

  19. Evaluation of mosquito repellent activity of isolated oleic acid, eicosyl ester from Thalictrum javanicum

    Directory of Open Access Journals (Sweden)

    Abinaya Gurunathan

    2016-01-01

    Full Text Available To evaluate the traditional use, the mosquito repellent property of Thalictrum javanicumand to confirm the predicted larvicidal activity of the isolated compound, oleic acid, eicosyl ester from its aerial parts by PASS software, the present study was carried out using 4th instar stage larvae of the mosquitoes, Aedes aegypti(dengue vector and Culex quinquefasciatus(filarial vector. Insecticidal susceptibility tests were conducted and the mortality rate was observed after 24 h exposure. The chitinase activity of isolated compound was assessed by using purified β-N-acetyl glucosaminidase (chitinase. Ecdysone 20-monooxygenase assay (radioimmuno assay was made using the same larval stage of A. aegyptiand C. quinquefasciatus. The results were compared with the crude methanol extract of the whole plant. The isolated compound, oleic acid, eicosyl ester was found to be the most effective larvicide against A. aegypti (LC50/24 h -8.51 ppm and C. quinquefasciatus (LC50/24 h - 12.5 ppm than the crude methanol extract (LC50/24 h - 257.03 ppm and LC50/24 h - 281.83 ppm, respectively. The impact of oleic acid, eicosyl ester on reducing the activity of chitinase and ecdysone 20-monooxygenase was most prominent in both the target species, A. aegyptiand C. quinquefasciatusthan the control. The results therefore suggest that the compound, oleic acid, eicosyl ester from Thalictrum javanicummay be considered as a potent source of mosquito larvicidal property.

  20. Evaluation of Mosquito Repellent Activity of Isolated Oleic Acid, Eicosyl Ester from Thalictrum javanicum

    Science.gov (United States)

    Gurunathan, Abinaya; Senguttuvan, Jamuna; Paulsamy, S.

    2016-01-01

    To evaluate the traditional use, the mosquito repellent property of Thalictrum javanicum and to confirm the predicted larvicidal activity of the isolated compound, oleic acid, eicosyl ester from its aerial parts by PASS software, the present study was carried out using 4th instar stage larvae of the mosquitoes, Aedes aegypti (dengue vector) and Culex quinquefasciatus (filarial vector). Insecticidal susceptibility tests were conducted and the mortality rate was observed after 24 h exposure. The chitinase activity of isolated compound was assessed by using purified β-N-acetyl glucosaminidase (chitinase). Ecdysone 20-monooxygenase assay (radioimmuno assay) was made using the same larval stage of A. aegyptiand C. quinquefasciatus. The results were compared with the crude methanol extract of the whole plant. The isolated compound, oleic acid, eicosyl ester was found to be the most effective larvicide against A. aegypti (LC50/24 h -8.51 ppm) and C. quinquefasciatus (LC50/24 h - 12.5 ppm) than the crude methanol extract (LC50/24 h - 257.03 ppm and LC50/24 h - 281.83 ppm, respectively). The impact of oleic acid, eicosyl ester on reducing the activity of chitinase and ecdysone 20-monooxygenase was most prominent in both the target species, A. aegyptiand C. quinquefasciatus than the control. The results therefore suggest that the compound, oleic acid, eicosyl ester from Thalictrum javanicum may be considered as a potent source of mosquito larvicidal property. PMID:27168688

  1. 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...

  2. Cold flow properties of fatty acid methyl esters: Additives versus diluents

    Science.gov (United States)

    Biodiesel is typically composed of fatty acid methyl esters (FAME) converted from agricultural lipids. Common feedstocks include soybean oil, canola oil, rapeseed oil, sunflower oil, and palm oil. Recent debate on the conversion of edible oils into non-food products has created opportunities to deve...

  3. 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.

  4. Synthesis of Versatile Building Blocks through Asymmetric Hydrogenation of Functionalized Itaconic Acid Mono-Esters

    NARCIS (Netherlands)

    Hekking, Koen F.W.; Lefort, Laurent; Vries, André H.M. de; Delft, Floris L. van; Schoemaker, Hans E.; Vries, Johannes G. de; Rutjes, Floris P.J.T.

    2008-01-01

    The rhodium-catalyzed asymmetric hydrogenation of several β-substituted itaconic acid mono-esters, using a library of monodentate phosphoramidite and phosphite ligands is described. Two β-alkyl-substituted substrates were readily hydrogenated by the rhodium complex Rh(COD)2BF4 in combination with (S

  5. Synthesis and antiproliferative activity of new bioconjugates of Salinomycin with amino acid esters.

    Science.gov (United States)

    Antoszczak, Michał; Sobusiak, Maria; Maj, Ewa; Wietrzyk, Joanna; Huczyński, Adam

    2015-09-01

    New Salinomycin (SAL) bioconjugates with amino acid methyl esters were obtained and their antiproliferative activity against cancer cell lines including drug-resistant ones was studied. New compounds exhibit antiproliferative activity towards leukemia and doxorubicin-resistant colon adenocarcinoma cell line and are more effective and less toxic than the commonly currently used anticancer drugs.

  6. Theoretical study of the decomposition of ethyl and ethyl 3-phenyl glycidate.

    Science.gov (United States)

    Josa, Daniela; Peña-Gallego, Angeles; Rodríguez-Otero, Jesús; Cabaleiro-Lago, Enrique M

    2013-01-01

    The mechanism of the decomposition of ethyl and ethyl 3-phenyl glycidate in gas phase was studied by density functional theory (DFT) and MP2 methods. A proposed mechanism for the reaction indicates that the ethyl side of the ester is eliminated as ethylene through a concerted six-membered cyclic transition state, and the unstable intermediate glycidic acid decarboxylates rapidly to give the corresponding aldehyde. Two possible pathways for glycidic acid decarboxylation were studied: one via a five-membered cyclic transition state, and the other via a four-membered cyclic transition state. The results of the calculations indicate that the decarboxylation reaction occurs via a mechanism with five-membered cyclic transition state.

  7. Preparation and Reactions of Amino Acid Ester Sulfones as New Remote Asymmetrical Induced Reagents

    Institute of Scientific and Technical Information of China (English)

    ZHOU,Cheng-He; BAI,Xue; LI,Tan-Qing; WU,Jun; Alfred Hassner

    2004-01-01

    @@ The development of chiral auxiliary-controlled asymmetric synthesis has been receiving increasing interest in recent yearsfi,2] Various chiral auxiliary reagents have been observed[3] and a lot of results showed that variation of the chiral auxiliary could influence asymmetric induction. Recently, it has been reported the reaction of the aminated sulfones as a remote chiral auxiliary with α,β-unsaturated carbonyl compounds.[4] Here we would like to report the preparation of amino acid ester sulfones as new remote asymmetrical induced reagents and their reactions with α,β-unsaturated esters.

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

    OpenAIRE

    Ion Dragalin; Olga Morarescu; Maria Sedcenco; Radu Marin Rosca

    2015-01-01

    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.

  9. 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.

  10. 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-phenylalanine...... nor L-serine methyl ester, stimulate insulin secretion. In the presence of L-glutamine, however, the effect of L-serine was additive, while the methyl esters of L-serine and L-phenylalanine as well as native L-phenylalanine, potentiated the glucose-stimulated release of insulin. Measurements of islet...... 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...

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

    Energy Technology Data Exchange (ETDEWEB)

    Li, Zhipeng [School of Chemistry and Chemical Engineering, Key Laboratory for Thin Film and Microfabrication of the Ministry of Education, Shanghai Jiao Tong University, 200240 (China); Laboratory of Solid Lubrication, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000 (China); Li, Xiufeng; Zhang, Yawen [School of Chemistry and Chemical Engineering, Key Laboratory for Thin Film and Microfabrication of the Ministry of Education, Shanghai Jiao Tong University, 200240 (China); Ren, Tianhui, E-mail: thren@sjtu.edu.cn [School of Chemistry and Chemical Engineering, Key Laboratory for Thin Film and Microfabrication of the Ministry of Education, Shanghai Jiao Tong University, 200240 (China); Zhao, Yidong [Beijing Synchrotron Radiation Facility, Institute of High Energy Physics, Chinese Academy of Sciences, Beijing 100039 (China); Zeng, Xiangqiong; Heide, E. van der [Laboratory for Surface Technology and Tribology, University of Twente, Drienerlolaan 5, 7522 NB Enschede (Netherlands)

    2014-07-01

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

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

    Science.gov (United States)

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

    2006-03-01

    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. 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).

  13. Efficient production of the Nylon 12 monomer ω-aminododecanoic acid methyl ester from renewable dodecanoic acid methyl ester with engineered Escherichia coli.

    Science.gov (United States)

    Ladkau, Nadine; Assmann, Miriam; Schrewe, Manfred; Julsing, Mattijs K; Schmid, Andreas; Bühler, Bruno

    2016-07-01

    The expansion of microbial substrate and product scopes will be an important brick promoting future bioeconomy. In this study, an orthogonal pathway running in parallel to native metabolism and converting renewable dodecanoic acid methyl ester (DAME) via terminal alcohol and aldehyde to 12-aminododecanoic acid methyl ester (ADAME), a building block for the high-performance polymer Nylon 12, was engineered in Escherichia coli and optimized regarding substrate uptake, substrate requirements, host strain choice, flux, and product yield. Efficient DAME uptake was achieved by means of the hydrophobic outer membrane porin AlkL increasing maximum oxygenation and transamination activities 8.3 and 7.6-fold, respectively. An optimized coupling to the pyruvate node via a heterologous alanine dehydrogenase enabled efficient intracellular L-alanine supply, a prerequisite for self-sufficient whole-cell transaminase catalysis. Finally, the introduction of a respiratory chain-linked alcohol dehydrogenase enabled an increase in pathway flux, the minimization of undesired overoxidation to the respective carboxylic acid, and thus the efficient formation of ADAME as main product. The completely synthetic orthogonal pathway presented in this study sets the stage for Nylon 12 production from renewables. Its effective operation achieved via fine tuning the connectivity to native cell functionalities emphasizes the potential of this concept to expand microbial substrate and product scopes. PMID:26969251

  14. PREPARATION AND PROPERTIES OF ETHYL-CYANOETHYL CELLULOSE/POLYACRYLIC ACID COMPOSITE FILMS WITH REFLECTION COLORS

    Institute of Scientific and Technical Information of China (English)

    Yong Huang

    2001-01-01

    Ethyl-cyanoethyl cellulose [(E-CE)C]/acrylic acid (AA) becomes a cholesteric liquid crystalline solution with vivid colors when the (E-CE)C concentration is 42 wt% ~52 wt%. (E-CE)C/polyacrylic acid (PAA) composites with cholesteric structure were prepared by polymerizing AA in (E-CE)C/AA liquid crystalline solutions. The layers of ordered polymer chains in the cholesteric phase were inclined during polymerization and the degree of the inclination depended on the polymerization temperature and the concentration of the solution before polymerization. The cholesteric structure in the composites could not be changed when temperature was lower than 100C. Cross-linking of the PAA in composites improved their water-resistance. The cholesteric order of the composites without cross-linking was destroyed when they where immersed in water. The color derived from the selective reflection of the cholesteric phase of the cross-linked composites turned from blue to red after the composites absorbed water. The color of the composites could be returned to the original one when the absorbed water was removed from the swollen composites.

  15. Isolation from Cussonia barteri of 1'-O-chlorogenoylchlorogenic acid and 1'-O-chlorogenoylneochlorogenic acid, a new type of quinic acid esters.

    Science.gov (United States)

    Papajewski, S; Vogler, B; Conrad, J; Klaiber, I; Roos, G; Walter, C U; Süssmuth, R; Kraus, W

    2001-11-01

    1'-O-Chlorogenoylchlorogenic acid and 1'-O-chlorogenoylneochlorogenic acid, a new type of quinic acid esters, have been isolated, in addition to six known quinic acid esters, rutin, and a mixture of saponins, from the methanol extract of Cussonia barteri Seemann (Araliaceae) leaves collected in Cameroon. Structure determination was achieved by NMR, mass, IR, and UV spectroscopy. All compounds were tested for inhibitory activity on 5-lipoxygenase and cyclooxygenase-1, for antimicrobial activity against Bacillus subtilis, Pseudomonas fluorescens, and Cladosporium cucumerinum, and for haemolytic activity. PMID:11731915

  16. Fatty Acid Methyl Esters of Melon Seed Oil: Characterisation for Potential Diesel Fuel Application

    Directory of Open Access Journals (Sweden)

    Paul M. EJIKEME

    2011-06-01

    Full Text Available Fatty acid methyl esters (FAME, biodiesel, are alternative diesel fuels usually obtained from renewable sources, mainly, vegetable and animal oils through transesterification among other processes. Melon seed oil was extracted from melon seeds bought from a local market, degummed and alkali refined using standard methods. FAME of the oil was produced using methanol in the molar ration of 1:6, 1% sodium hydroxide catalyst at the reaction temperature of 60 deg C for the duration of 1h. Results obtained showed that the fatty acid methyl esters had a specific gravity of 0.8786, viscosity of 6.24 centistokes, pH of 7.23, heating value of 36.34 J/g and flash point of 148 deg C. The FAME yield was 87.35% under the reaction conditions that applied. The infrared spectra of both the refined oil and the methyl esters from it, showed peaks at 1721.3cm-1 and 1167.8cm-1 (C=O and C-O stretches large and medium absorbance's for oils and methyl esters. Generally, the fuel properties of the FAME compared with values obtained under the same conditions for conventional petroleum diesel that was sourced from a retail outlet; suggesting that biodiesel from MSO could be used alone or in blends with petrodiesel to power compression ignition (diesel engines.

  17. Solid Phase Synthesis of 2-Substituted 1,3-Oxazin-6-ones Using Resin-bound Cyclic Malonic Acid Ester

    Institute of Scientific and Technical Information of China (English)

    LIU, Zhan-Xiang(刘占祥); RUAN, Xiu-Xiu(阮秀秀); HUANG, Xian(黄宪)

    2004-01-01

    A facile solid phase synthesis of 2-substituted 1,3-oxazin-6-ones using polymer-supported Meldrum's acid has been reported. Reaction of the resin-bound cyclic malonic acid ester with triethyl orthoformate and subsequent double substitution with amide, afforded the corresponding polymer-supported acylaminomethylene cyclic malonic acid ester, which upon thermal treatment led to 1, 3-oxazin-6-ones in good yields and with high purity.

  18. A convenient enantioselective decarboxylative aldol reaction to access chiral α-hydroxy esters using β-keto acids

    Directory of Open Access Journals (Sweden)

    Zhiqiang Duan

    2014-04-01

    Full Text Available We show a convenient decarboxylative aldol process using a scandium catalyst and a PYBOX ligand to generate a series of highly functionalized chiral α-hydroxy esters. The protocol tolerates a broad range of β-keto acids with inactivated aromatic and aliphatic α-keto esters. The possible mechanism is rationalized.

  19. Direct analysis of intact glycidyl fatty acid esters in edible oils using gas chromatography-mass spectrometry

    NARCIS (Netherlands)

    H. van Steenbergen; K. Hrnčiřík; A. Ermacora; S. de Koning; H.-G. Janssen

    2013-01-01

    Glycidyl esters (GE), fatty acid esters of glycidol, are process contaminants formed during edible oil processing. A novel direct method for the determination of intact GE in oils and fats based on gas chromatography-mass spectrometry (GC-MS) is presented. The method consists of a simple extraction

  20. 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

  1. 21 CFR 172.854 - Polyglycerol esters of fatty acids.

    Science.gov (United States)

    2010-04-01

    ..., lard, palm oil from fruit, peanut oil, safflower oil, sesame oil, soybean oil, and tallow and the fatty... acids are used as a cloud inhibitor in vegetable and salad oils when use is not precluded by standards... 172.854 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN...

  2. Synthesis of Free Amino Acid Esters Co-catalyzed by Ionic Liquid%离子液体协同催化合成游离氨基酸酯

    Institute of Scientific and Technical Information of China (English)

    尚岩; 贾俊英; 高海鹏; 裴蕾; 仲昭琪

    2011-01-01

    以L-氨基酸和醇为原料,酸性离子液体辅以少量强酸性阳离子交换树脂作催化剂,直接酯化合成了8种游离的L-氨基酸酯,并用1HNMR对产物进行了表征.通过L-苯丙氨酸正丁酯的合成对离子液体的活性进行了考察,结果表明,所选用的11种离子液体在反应过程中均起到了一定的催化作用和助溶作用.其中,[Hmim][HSO4]效果较好,在重复使用后,显示了较好的稳定性,是氨基酸酯化反应理想的催化剂和助溶剂.%Eight kinds of free L-amino acid esters including L-phenylalanine ethyl ester, L-phenylalanine n-butyl ester, L-phenylalanine i-butyl ester, L-tyrosine n-butyl ester, L-tyrosine i-butyl ester, L-tyrosine i-amyl ester, L-aspartic n-butyl diester and L-aspartic i-butyl diester were synthesized by direct esterification of L-amino acid and alcohol with acidic ionic liquid assisted by strong acidic cation resin as catalyst. The structures of free L-amino acid esters were characterized by 1HNMR.Optimal reaction conditions were obtained when synthesizing L-phenylalanine n-butyl ester. Among eleven kinds of the acidic ionic liquids used in this case, [Hmim] [ HSO4 ] indicated excellent activity and the catalyst is easily regenerated and reused. By this token, it exhibits its potential application as catalyst and co-solvent in the esterification of amino acid.

  3. Thermal tolerance and survival of Cronobacter sakazakii in powdered infant formula supplemented with vanillin, ethyl vanillin, and vanillic acid.

    Science.gov (United States)

    Yemiş, Gökçe Polat; Pagotto, Franco; Bach, Susan; Delaquis, Pascal

    2012-09-01

    The thermal tolerance Cronobacter sakazakii was examined in sterile powdered infant formula (PIF) rehydrated at 58 °C in water or apple juice supplemented with vanillin, ethyl vanillin, or vanillic acid. All three compounds decreased thermal tolerance during-rehydration and the lowest decimal reduction time (D-value, 0.19 ± 0.01 min) was measured in PIF rehydrated in apple juice supplemented with 20 mM vanillic acid. At this level of supplementation no C. sakazakii were detected in PIF stored for 48 h at 10 and 24 h at 21 °C subsequent to a sublethal heat treatment. Thermal tolerance during rehydration and survival in reconstituted PIF were influenced by compound type, concentration, and temperature. Supplementation of PIF with vanillin, ethyl vanillin, or vanillic acid could enhance the safety of PIF or other dehydrated foods contaminated with C. sakazakii.

  4. Gas chromatographic separation of fatty acid esters of cholesterol and phytosterols on an ionic liquid capillary column.

    Science.gov (United States)

    Hammann, Simon; Vetter, Walter

    2015-12-15

    Steryl esters are high molecular weight compounds (600-700g/mol) regularly present as a minor lipid class in animal and plant lipids. Different sterol backbones (e.g., cholesterol, β-sitosterol and brassicasterol) which can be esterified with various fatty acids can result in highly complex steryl ester patterns in food samples. The gas chromatographic (GC) analysis of intact steryl esters is challenging, since high elution temperatures are required for their elution. On nonpolar GC phases, steryl esters with fatty acids with differing degree of unsaturation (e.g., oleate and linoleate) cannot be separated and there are only few polar columns available with sufficient temperature stability. In this study, we used gas chromatography with mass spectrometry (GC/MS) and analyzed intact steryl esters on a commercial room temperature ionic liquid (RTIL) column which was shortened to a length of 12m. The column separated the steryl esters both by total carbon number and by degree of unsaturation of the fatty acid. For instance, cholesteryl esters with stearic acid (18:0), oleic acid (18:1n-9), linoleic acid (18:2n-6) and α-linolenic acid (18:3n-3) could be resolved (R≥1.3) from each other. By analysis of synthesized standard substances, the elution orders for different steryl backbones and different fatty acids on a given sterol backbone could be determined. Analysis of spreads and plant oils allowed to determine retention times for 37 steryl esters, although a few co-elutions were observed. The ionic liquid column proved to be well-suited for the analysis of intact steryl esters.

  5. Optimization of SPE for Analysis of Mandelic Acid as a Biomarker of Exposure to Ethyl Benzene

    Directory of Open Access Journals (Sweden)

    SJ Shahtaheri, M Abdollahi, F Golbabaei, A Rahimi-Froushani, F Ghamari

    2004-10-01

    Full Text Available Ethyl benzene is an important constituent of widely used solvents in industries and laboratories, causing widespread environmental and industrial pollutions. For evaluation of occupational exposure to such pollutants, biological monitoring is an essential process, in which, preparation of environmental and biological samples is one of the most time-consuming and error-prone aspects prior to chromatographic techniques. The use of solid-phase extraction (SPE has been grown and is a fertile technique of sample preparation as it provides better results than those of liquid-liquid extraction (LLE. In this study, SPE using bonded silica has been optimized with regard to sample pH, sample concentration, elution solvent, elution volume, sorbent type, and sorbent mass. Through experimental evaluation, a strong anion exchange silica cartridge (SAX has been found successful in simplifying sample preparation. The present approach proved that, mandelic acid could be retained on SAX sorbent based on specific interaction. Further study was employed using 10% acetic acid to extract the analyte from spiked urine and gave a clean sample for HPLC-UV system. In this study, a high performance liquid chromatography, using reverse-phase column was used. The isocratic run was done at a constant flow rate of 0.85 ml/min, the mobile phase was water/methanol/acetic acid and a UV detector was used, setting at 225 nm. At the developed conditions the extraction recovery was exceeded 98%. The factors were evaluated statically and also validated with three different pools of spiked urine samples and showed a good reproducibility over six consecutive days as well as six within-day experiments.

  6. Antifungal properties of alpha,omega-alkanedicarboxylic acids and their dimethyl esters.

    Science.gov (United States)

    Gershon, H; Shanks, L

    1976-08-01

    Thirteen alpha, omega-alkanedicarboxylic acids (C2-C12, C14, and C16) and their dimethyl esters were tested against Aspergillus niger, Trichoderma viride, and Myrothecium verrucaria in Sabourauc dextrose agar at pH 4.0 AND 5.6. Toxicity to Canadida albicans, Trichophyton mentagrophytes, and Mucor mucedo was determined in the same medium at pH 5.6 and 7.0 in the absence and presence of 10% beef serum. The dicarboxylic acids possessed very poor to no antifungal activity against all six fungi. The fungitoxicity of the dimethyl esters to A. niger, T. viride, and M. verrucaria was C8 = C9 greater than C7 greater than C6 = C5 greater than C10 greater than C4 greater than C11 and to C. albicans, T. mentagrophytes, and M. mucedo C9 greater than C10 greater than C11 greater than C12 = C8 greater than C7 greater than C6 greater than C5 greater than C4 greater than C3. The fungitoxicity of the esters of fatty acids and alpha-omega-alkanedicarboxylic acids was influenced by chain length and not by the pH of the medium or the absence or presence of beef serum.

  7. 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

  8. Nickel-Catalyzed Cross-Coupling of Redox-Active Esters with Boronic Acids.

    Science.gov (United States)

    Wang, Jie; Qin, Tian; Chen, Tie-Gen; Wimmer, Laurin; Edwards, Jacob T; Cornella, Josep; Vokits, Benjamin; Shaw, Scott A; Baran, Phil S

    2016-08-01

    A transformation analogous in simplicity and functional group tolerance to the venerable Suzuki cross-coupling between alkyl-carboxylic acids and boronic acids is described. This Ni-catalyzed reaction relies upon the activation of alkyl carboxylic acids as their redox-active ester derivatives, specifically N-hydroxy-tetrachlorophthalimide (TCNHPI), and proceeds in a practical and scalable fashion. The inexpensive nature of the reaction components (NiCl2 ⋅6 H2 O-$9.5 mol(-1) , Et3 N) coupled to the virtually unlimited commercial catalog of available starting materials bodes well for its rapid adoption. PMID:27380912

  9. 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.

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

    Science.gov (United States)

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

    2016-01-01

    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. PMID:27338349

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

    Science.gov (United States)

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

    2016-01-01

    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. PMID:27338349

  12. 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.

  13. Acid Corrosion Inhibition and Adsorption Behaviour of Ethyl Hydroxyethyl Cellulose on Mild Steel Corrosion

    Directory of Open Access Journals (Sweden)

    I. O. Arukalam

    2014-01-01

    Full Text Available The corrosion inhibition of mild steel in 1.0 M H2SO4 solution by ethyl hydroxyethyl cellulose has been studied in relation to the concentration of the additive using weight loss measurement, EIS, polarization, and quantum chemical calculation techniques. The results indicate that EHEC inhibited corrosion reaction in the acid medium and inhibition efficiency increased with EHEC concentration. Further increase in inhibition efficiency is observed in the presence of iodide ions, due to synergistic effect. Impedance results reveal that EHEC is adsorbed on the corroding metal surface. Adsorption followed a modified Langmuir isotherm, with very high negative values of the free energy of adsorption (ΔGads. The polarization data indicate that the inhibitor was of mixed type, with predominant effect on the cathodic partial reaction. The frontier molecular orbitals, HOMO (the highest occupied molecular orbital and LUMO (the lowest unoccupied molecular orbital as well as local reactivity of the EHEC molecule, were analyzed theoretically using the density functional theory to explain the adsorption characteristics at a molecular level. The theoretical predictions showed good agreement with experimental results.

  14. Labelling of 5-ethyl-5-phenylbarbituric acid with Technetium-99m: biodistribution study in Swiss mice

    International Nuclear Information System (INIS)

    The 5-ethyl-5-phenylbarbituric acid (phenobarbital) is used as a sedative, hypnotic and anticonvulsant drug. We decided to label it with technetium-99m. In order to determine the optimal conditions, different concentrations of this drug were incubated with various stannous chloride solutions. Then, 99mTc was added and chromatography was performed using 0.9% NaCl solution, acetone and n-butyl alcohol as the mobile phase. Using a solution of 0.01 mg/ml stannous chloride and 1.0 mg/ml phenobarbital over 92% of the radioactivity bound to phenobarbital 99mTc-phenobarbital. In the biodistribution study, 99mTc-phenobarbital was administered in mice intraperitoneal. The main uptake of the labeled drug was in the liver, blood, kidneys, spleen and stomach. The phenobarbital is also used as anesthetic drug in animals. Earlier studies confirm that this drug can dislocate the adult worms of Schistosoma mansoni to mesenteric vein towards the liver and portal vein, so that we used infected animals, radioactivity was not found in isolated worms and we can conclude that the phenobarbital has an indirect action in relation to the displacement of the worms. (author)

  15. Effect of addition of esters of fatty acids on the microstructure and properties of sintered Nd–Fe–B magnets produced by PLP

    Energy Technology Data Exchange (ETDEWEB)

    Popov, A.G., E-mail: apopov@imp.uran.ru [Institute of Metal Physics, Str. S. Kovalevskoy, 18, Ekaterinburg 620990 (Russian Federation); Gaviko, V.S.; Shchegoleva, N.N.; Golovnia, O.A. [Institute of Metal Physics, Str. S. Kovalevskoy, 18, Ekaterinburg 620990 (Russian Federation); Gorbunova, T.I. [Institute of Organic Synthesis of Ural Branch of Russian Academy of Sciences, Str. S. Kovalevskoy 20, Ekaterinburg 620990, Russia (Russian Federation); Hadjipanayis, G.C. [Department of Physics and Astronomy, University of Delaware, 217 Sharp Lab, Newark, DE 19716 (United States)

    2015-07-15

    High filling density of powders for production of sintered Nd–Fe–B magnets by the pressless process (PLP) impedes magnetic alignment. The latter can be enhanced by reduction of friction forces between powder particles. Thus, increase in the remanence and maximum energy product of the magnets by lubrication of powder particles is studied. Esters of fatty acids have been added in toluene or acetone in the course of grinding of Nd–Fe–B alloy in a vibratory mill. Coated by a thin layer of a lubricant powders have been aligned in pulsed magnetic field. It is shown that the remanence of sintered magnets has been increased by 5–7%. Lubricant concentration should not exceed critical values, which for the lubricants used varied between 2.0 wt% (ethyl butyrate) and 0.3 wt% (ethyl laurate). Otherwise, the complicated removal of lubricant residue leads to reaction of the latter with Nd-rich grain-boundary phase in the course of sintering and results in a sharp decrease in magnetic hysteresis properties. Addition of lubricating additives allows one to produce PLP-magnets with density exceeding 7.5 g/cm{sup 3}, B{sub r}≥14 kG, H{sub c}≥9 kOe and (BH){sub max}≥45 MG Oe. - Highlights: • Application of internal lubricants in the PLP-produced magnets is studied. • The alignment degree is enhanced by addition of esters of fatty acids. • Critical concentrations of lubricants are determined. • Exceeding the critical concentration decreases magnetic properties by increasing oxygen content.

  16. Antibacterial properties of soap containing some fatty acid esters.

    Science.gov (United States)

    Pandey, N K; Natraj, C V; Kalle, G P; Nambudiry, M E

    1985-02-01

    Synopsis Chemical microbial inhibitors compatible with formulations of soaps and deodorant perfumes are more effective if they are substantive to the skin. However, highly effective inhibitors are toxic and their substantivity on skin may accentuate the toxicity. Natural compounds such as short to medium chain fatty acids and their derivatives, which are known to be germicidal, offer a viable alternative to chemical inhibitors. We report here the synthesis of sodium 2-lauroyloxy propionate and an in vivo method to test its substantivity on skin following its incorporation in soaps. Among several compounds tested, sodium 2-lauroyloxy propionate was found to be highly substantive in soap formulation. PMID:19460009

  17. 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 att

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

    NARCIS (Netherlands)

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

    2008-01-01

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

  19. Evaluation of Mosquito Repellent Activity of Isolated Oleic Acid, Eicosyl Ester from Thalictrum javanicum

    OpenAIRE

    Abinaya Gurunathan; Jamuna Senguttuvan; S Paulsamy

    2016-01-01

    To evaluate the traditional use, the mosquito repellent property of Thalictrum javanicum and to confirm the predicted larvicidal activity of the isolated compound, oleic acid, eicosyl ester from its aerial parts by PASS software, the present study was carried out using 4th instar stage larvae of the mosquitoes, Aedes aegypti (dengue vector) and Culex quinquefasciatus (filarial vector). Insecticidal susceptibility tests were conducted and the mortality rate was observed after 24 h exposure. Th...

  20. Syntheses of Macrocyclic Amides from L-Amino Acid Esters by RCM

    Institute of Scientific and Technical Information of China (English)

    2007-01-01

    A series of succinate-derived macrocyclic amides( 1 ) was synthesized via ring-closing metathesis (RCM) as the key step. The substrate included 12 to 15 members. The metathesis precursors were obtained from the amide coupling of tert-butyl 3-carboxyhex-5-enoate(2) with numerous side-chain alkenylated amino acid esters of general type(3)derived from L-lysine and L-ornithine.

  1. Hydrolytic activity of -alkoxide/acetato-bridged binuclear Cu(II) complexes towards carboxylic acid ester

    Indian Academy of Sciences (India)

    Weidong Jiang; Bin Xu; Zhen Xiang; Shengtian Huang; Fuan Liu; Ying Wang

    2013-09-01

    Two -alkoxide/acetate-bridged small molecule binuclear copper(II) complexes were synthesized, and used to promote the hydrolysis of a classic carboxylic acid ester, -nitrophenyl picolinate (PNPP). Both binuclear complexes exhibited good hydrolytic reactivity, giving rise to . 15547- and 17462-fold acceleration over background value for PNPP hydrolysis at neutral conditions, respectively. For comparing, activities of the other two mononuclear analogues were evaluated, revealing that binuclear complexes show approximately 150- and 171-fold kinetic advantage over their mononuclear analogues.

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

    OpenAIRE

    Cheng-Fang Tsai; Yueh-Hsiung Kuo; Wei-Lan Yeh; Caren Yu-Ju Wu; Hsiao-Yun Lin; Sheng-Wei Lai; Yu-Shu Liu; Ling-Hsuan Wu; Jheng-Kun Lu; Dah-Yuu Lu

    2015-01-01

    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 ...

  3. Synthesis and Properties of Lactic Acid-based Cross-linked Poly(ester-amide)

    Institute of Scientific and Technical Information of China (English)

    Yue Ying HE; Cong Ming XIAO

    2006-01-01

    A novel lactic acid-based cross-linked poly(ester-amide) (LCPEA) was synthesized. The gel fraction of the LCPEA could be modulated by the reaction conditions and it affected the mechanical and thermal properties of the LCPEA. The tensile strength, elastic modulus and bend strength of the LCPEA of 65% gel fraction were 4.65, 136.55 and 39.63 MPa, respectively. The thermal decomposition temperature (50 wt%) of the LCPEA was around 410 ℃.

  4. New fatty acid, aromatic ester and monoterpenic benzyl glucoside from the fruits of Withania coagulans Dunal.

    Science.gov (United States)

    Ali, Abuzer; Jameel, Mohammad; Ali, Mohammed

    2015-01-01

    The fruits of Withania coagulans Dunal (family: Solanaceae) are sweet, sedative, emetic, alterative and diuretic; used to treat asthma, biliousness, strangury, wounds, dyspepsia, flatulent colic, liver complaints and intestinal infections in the indigenous system of medicine. Phytochemical investigation of the methanolic extract of W. coagulans fruits led to the isolation of a new fatty acid, an aromatic ester and a monoterpenic benzyl glucoside characterised as n-octatriacont-17-enoic acid (3), geranilan-10-olyl dihydrocinnamoate (4) and geranilan-8-oic acid-10-olyl salicyloxy-2-O-β-D-glucofuranosyl-(6″→1‴)-O-β-D-glucofuranosyl-6‴-n-octadec-9‴',11‴'-dienoate (5) along with two known fatty acids, n-dotriacont-21-enoic acid (1) and n-tetratriacontanoic acid (2). The structures of isolated phytoconstituents were established on the basis of 1D and 2D NMR, FT-IR, UV, and MS data and chemical means.

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

    Energy Technology Data Exchange (ETDEWEB)

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

    2013-06-01

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

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

    Energy Technology Data Exchange (ETDEWEB)

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

    2012-04-15

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

  7. Scientific Opinion on the re-evaluation of montan acid esters (E 912 as a food additive

    Directory of Open Access Journals (Sweden)

    EFSA Panel on Food Additives and Nutrient Sources added to Food (ANS

    2013-06-01

    Full Text Available Following a request from the European Commission, the EFSA Panel on Food Additives and Nutrient Sources added to Food (ANS was asked to deliver a scientific opinion re-evaluating the safety of montan acid esters (E 912 when used as a food additive. Montan acids are extracted from oxidised montan wax and esterified with ethylene glycol, 1,3-butanediol or triols, to form montan acid esters. Montan acid esters are authorised only for the surface treatment of fresh fruits. No data, specifically for montan acid esters, on toxicokinetics and reproductive and developmental toxicity were available. The available data on short-term and subchronic toxicity, genotoxicity and chronic toxicity and carcinogenicity were limited. Important deficiencies in the available studies on chronic toxicity and carcinogenicity were noticed. The data requested in the 1990s (i.e. chromosomal aberration in vitro, reproduction and teratogenicity studies, material characteristics, impurities, presence of PAHs were not submitted. Furthermore no data were submitted following an EFSA public call for data in 2012. The Panel identified some summary data in the European Chemicals Agency database (ECHA on registered substances that might have been relevant for the assessment of montan acid esters but the original study reports were not made available to EFSA. Based on these limitations in the toxicological database the Panel concluded that montan acid esters as a food additive could not be evaluated.

  8. Continuous production of palm biofuel under supercritical ethyl acetate

    International Nuclear Information System (INIS)

    Highlights: • Continuous synthesized biofuel from palm oil in supercritical ethyl acetate was examined. • Mass flow rate of palm oil and ethyl acetate mixture influent to biofuel production in continuous system. • Water addition to reacting mixture improves the production of fatty acid ethyl esters and triacetin. • The generated acetic acid from ETA hydrolysis can protect the products from thermal decomposition. - Abstract: The interesterification of palm oil in supercritical ethyl acetate (ETA) to produce fatty acid ethyl ester (FAEEs) or biofuel was conducted in a continuous tubular reactor. The density of the mixtures in the system was estimated using the Peng–Robinson equation of state process simulator, and the residence time was calculated. The effects of the reaction conditions, including the molar ratios of palm oil to ethyl acetate, the temperature, and the pressure, were investigated under various mass flow rates of the mixtures and optimized. The results showed that reaction temperatures above 653 K and long residence times affected the content of FAEEs and triacetin, a valuable by-product. The addition of water to the mixture in a 1:30:10 M ratio of palm oil to ethyl acetate to water at 653 K, 16 MPa, and a mixture mass flow rate of 1.5 g/min increased the total production of FAEEs and triacetin from 90.9 to 101.5 wt% in 42.4 min. The main finding of the present study is that triglyceride associated with ETA hydrolysis used to form acetic acid protected the products from decomposition at high temperatures and long residence times. The results will aid the selection of an efficient and economical process for alternative biofuel production from palm oil in supercritical ETA

  9. Pengaruh Katalis H2SO4 pada Reaksi Epoksidasi Metil Ester PFAD (Palm Fatty Acid Distillate)

    OpenAIRE

    Sinaga, Mersi Suriani

    2010-01-01

    Ester epoksi selain sebagai pelunak juga dapat memperbaiki ketahanan komponen polivinil klorida (PVC) terhadap panas dan cahaya. Penelitian ini dilakukan untuk merumuskan kondisi katalis yang sesuai bagi pembuatan senyawa epoksi metil ester PFAD dari senyawa metil ester PFAD. Metil ester PFAD terdiri dari ester lemak jenuh dan tidak jenuh., metode pemisahan kristalisasi dengan pelarut metanol untuk memisahkan ester lemak jenuh dari ester lemak tak jenuh, yang bertujuan meningkatkan kemamp...

  10. Caffeic acid phenethyl ester prevents apoptotic cell death in the developing rat brain after pentylenetetrazole-induced status epilepticus.

    Science.gov (United States)

    Yiş, Uluç; Topçu, Yasemin; Özbal, Seda; Tuğyan, Kazım; Bayram, Erhan; Karakaya, Pakize; Yilmaz, Osman; Kurul, Semra Hız

    2013-11-01

    Population-based studies suggest that seizure incidence is highest during the first year of life, and early-life seizures frequently result in the development of epilepsy and behavioral alterations later in life. The early-life insults like status epilepticus often lead to epileptogenesis, a process in which initial brain injury triggers cascades of molecular, cellular, and network changes and eventually spontaneous seizures. Caffeic acid phenethyl ester is an active component of propolis obtained from honeybees and has neuroprotective properties. The aim of this study was to investigate whether caffeic acid phenethyl ester exerts neuroprotective effects on the developing rat brain after status epilepticus. Twenty-one dams reared Wistar male rats, and 21-day-old rats were divided into three groups: control group, pentylenetetrazole-induced status epilepticus group, and caffeic acid phenethyl ester-treated group. Status epilepticus was induced on the first day of experiment. Caffeic acid phenethyl ester injections (30 mg/kg intraperitoneally) started 40 min after the tonic phase of status epilepticus was reached, and the injections of caffeic acid phenethyl ester were repeated over 5 days. Rats were sacrificed, and brain tissues were collected on the 5th day of experiment after the last injection of caffeic acid phenethyl ester. Apoptotic cell death was evaluated. Histopathological examination showed that caffeic acid phenethyl ester significantly preserved the number of neurons in the CA1, CA3, and dentate gyrus regions of the hippocampus and the prefrontal cortex. It also diminished apoptosis in the hippocampus and the prefrontal cortex. In conclusion, this experimental study suggests that caffeic acid phenethyl ester administration may be neuroprotective in status epilepticus in the developing rat brain.

  11. Synthesis, Resolution, and Enantiomeric Purity Assay of 2-n-Butylbutanedioic Acid 4-t-Butyl Esters

    Institute of Scientific and Technical Information of China (English)

    2006-01-01

    Racemic 2-n-butylbutanedioic acid 4-t-butyl esters were synthesized from methyl hexanoate and t-butyl α-iodoacetate via alkylation and subsequently selective hydrolyzation. The (R)-and (S)-2-n-butylbutanedioic acid 4-t-butyl esters were obtained by the resolution of the above-mentioned racemic compounds with(S)-( - ) or(R)-( + )-α-methylbenzylamine, respectively. The e.e. values of the two optical active products were determined to be above 99% by HPLC after the formation of two pairs of diastereoisomers with ( R)-( + )-α-methylbenzylamine and (S)-phenylalanine methyl ester.

  12. Glucuronic acid and the ethanol metabolite ethyl-glucuronide cause Toll-like receptor 4 activation and enhanced pain

    OpenAIRE

    Lewis, Susannah S.; Hutchinson, Mark R; Zhang, Yingning; Hund, Dana K.; Maier, Steven F.; Rice, Kenner C.; Watkins, Linda R

    2013-01-01

    We have previously observed that the non-opioid morphine metabolite, morphine-3-glucuronide, enhances pain via a toll-like receptor 4 (TLR4) dependent mechanism. The present studies were undertaken to determine whether TLR4-dependent pain enhancement generalizes to other classes of glucuronide metabolites. In silico modeling predicted that glucuronic acid alone and ethyl glucuronide, a minor but long-lasting ethanol metabolite, would dock to the same MD-2 portion of the TLR4 receptor complex ...

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

    International Nuclear Information System (INIS)

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

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

    Energy Technology Data Exchange (ETDEWEB)

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

    2006-01-15

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

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

    International Nuclear Information System (INIS)

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

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

    Energy Technology Data Exchange (ETDEWEB)

    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. Rapid ester biosynthesis screening reveals a high activity alcohol-O-acyltransferase (AATase) from tomato fruit.

    Science.gov (United States)

    Lin, Jyun-Liang; Zhu, Jie; Wheeldon, Ian

    2016-05-01

    Ethyl and acetate esters are naturally produced in various yeasts, plants, and bacteria. The biosynthetic pathways that produce these esters share a common reaction step, the condensation of acetyl/acyl-CoA with an alcohol by alcohol-O-acetyl/acyltransferase (AATase). Recent metabolic engineering efforts exploit AATase activity to produce fatty acid ethyl esters as potential diesel fuel replacements as well as short- and medium-chain volatile esters as fragrance and flavor compounds. These efforts have been limited by the lack of a rapid screen to quantify ester biosynthesis. Enzyme engineering efforts have also been limited by the lack of a high throughput screen for AATase activity. Here, we developed a high throughput assay for AATase activity and used this assay to discover a high activity AATase from tomato fruit, Solanum lycopersicum (Atf-S.l). Atf1-S.l exhibited broad specificity towards acyl-CoAs with chain length from C4 to C10 and was specific towards 1-pentanol. The AATase screen also revealed new acyl-CoA substrate specificities for Atf1, Atf2, Eht1, and Eeb1 from Saccharomyces cerevisiae, and Atf-C.m from melon fruit, Cucumis melo, thus increasing the pool of characterized AATases that can be used in ester biosynthesis of ester-based fragrance and flavor compounds as well as fatty acid ethyl ester biofuels. PMID:26814045

  18. 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...... and trans fatty acids of C16:1, C18:1,n-9, C18:1,n-12, C18:2 and C22:1 in two- and three-dimensional score plots. With Soft Independent Modelling of Class Analogy (SIMCA), it is possible to calculate models that can predict from the mass spectra of unknown fatty acids whether they are of the cis or trans...

  19. Effect of vanillin, ethyl vanillin, and vanillic acid on the growth and heat resistance of Cronobacter species.

    Science.gov (United States)

    Yemiş, Gökçe Polat; Pagotto, Franco; Bach, Susan; Delaquis, Pascal

    2011-12-01

    Preservatives could be part of an effective intervention strategy for the control of Cronobacter species in foods, but few compounds with the desired antimicrobial properties have been identified to date. We examined the antibacterial activity of vanillin, ethyl vanillin, and vanillic acid against seven Cronobacter spp. in quarter-strength tryptic soy broth with 5 g/liter yeast extract (TSBYE) adjusted to pH 5.0, 6.0, and 7.0 at 10, 21, and 37°C. All compounds exhibited pH- and temperature-dependant bacteriostatic and bactericidal activity. MICs of vanillin and ethyl vanillin consistently increased with decreasing pH and temperature, but vanillic acid had little activity at pH values of 6.0 and 7.0. The MICs for all temperatures, pH values, and bacterial strains tested were 2 mg/ml ethyl vanillin, 3 mg/ml vanillin, and >8 mg/ml vanillic acid. MBCs also were influenced by pH, although significantly higher concentrations were needed to inactivate the bacteria at 21°C than at 10 or 37°C. Survivor curves for Cronobacter sakazakii strains at the MBCs of each compound revealed that all treatments resulted in immediate loss of cell viability at 37°C. Measurements of propidium iodide uptake indicated that the cell membranes were damaged by exposure to all three compounds. The thermal resistance of C. sakazakii was examined at 58°C in TSBYE supplemented with MBCs of each compound at pH 5.0 and 6.0. D-values at pH 5.0 were reduced from 14.56 ± 0.60 min to 0.93 ± 0.01, 0.63 ± 0.01, and 0.98 ± 0.02 min for vanillin, ethyl vanillin, and vanillic acid, respectively. These results suggest that vanillin, ethyl vanillin, and vanillic acid may be useful for the control of Cronobacter spp. in food during preparation and storage.

  20. 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. ...

  1. 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,...

  2. Dehydrogenative Cross-Coupling Reaction between N-Aryl α-Amino Acid Esters and Phenols or Phenol Derivative for Synthesis of α-Aryl α-Amino Acid Esters.

    Science.gov (United States)

    Salman, Muhammad; Zhu, Zhi-Qiang; Huang, Zhi-Zhen

    2016-04-01

    A novel dehydrogenative cross-coupling (DCC) reaction between N-arylglycine esters and phenols or 1,3,5-trimethoxybenzene was developed by copper catalysis using di-tert-butyl peroxide (DTBP) as an oxidant. Under optimized conditions, a range of N-arylglycine esters 1 underwent the DCC reaction smoothly with various phenols 2 or 1,3,5-trimethoxybenzene 4 to give desired α-aryl α -amino acid esters 3 or 5, respectively, with high ortho regioselectivities in a moderate to excellent yield. A possible mechanism involving aromatic electrophilic substitution is proposed.

  3. Dehydrogenative Cross-Coupling Reaction between N-Aryl α-Amino Acid Esters and Phenols or Phenol Derivative for Synthesis of α-Aryl α-Amino Acid Esters.

    Science.gov (United States)

    Salman, Muhammad; Zhu, Zhi-Qiang; Huang, Zhi-Zhen

    2016-04-01

    A novel dehydrogenative cross-coupling (DCC) reaction between N-arylglycine esters and phenols or 1,3,5-trimethoxybenzene was developed by copper catalysis using di-tert-butyl peroxide (DTBP) as an oxidant. Under optimized conditions, a range of N-arylglycine esters 1 underwent the DCC reaction smoothly with various phenols 2 or 1,3,5-trimethoxybenzene 4 to give desired α-aryl α -amino acid esters 3 or 5, respectively, with high ortho regioselectivities in a moderate to excellent yield. A possible mechanism involving aromatic electrophilic substitution is proposed. PMID:26984111

  4. The Effect of Caffeic Acid Phenethyl Ester (CAPE) Fortification on the Liver Element Distribution that Occurs After Exercise.

    Science.gov (United States)

    Akil, Mustafa; Coban, Funda Karabag; Yalcinkaya, Ozcan

    2016-08-01

    The purpose of this study is to examine the effect of the caffeic acid phenethyl ester (CAPE) fortification applied to the rats, which were made to exercise, on the liver elements. The study was conducted on 32 Sprague-Dawley male rats. The experimental animals were divided into 4 groups in equal numbers. Group 1 is the group which was applied 10 μmol/kg/day CAPE as intraperitoneal (IP) for 4 weeks, and they were not made to exercise at the end of the application. Group 2 is the group which was applied 10 μmol/kg/day CAPE as IP for 4 weeks, and they were made to exercise at the end of the 4th week. Group 3 is the general control group. Group 4 is the swimming control group. A 10 mmol/kg CAPE application dissolved in ethyl alcohol of 10 % was applied to the CAPE group. Sodium (Na), zinc (Zn), calcium (Ca), iron (Fe), chrome (Cr), magnesium (Mg), potassium (K), copper (Cu) and cadmium (Cd) levels were identified in the liver samples at the end of the application. The results of the study suggest that exercise and CAPE fortification in rats cause changes in the Na, Zn, Ca, Fe and Cr parameters in liver tissues, and it does not affect Cd, Cu, Mg and K element distribution. It is thought that CAPE fortification would be helpful for preserving those parameters whose levels are known to be changing with exercise. PMID:26743862

  5. Influence of fatty acid on lipase-catalyzed synthesis of ascorbyl esters and their free radical scavenging capacity.

    Science.gov (United States)

    Stojanović, Marija; Carević, Milica; Mihailović, Mladen; Veličković, Dušan; Dimitrijević, Aleksandra; Milosavić, Nenad; Bezbradica, Dejan

    2015-01-01

    Fatty acid (FA) ascorbyl esters are recently emerging food, cosmetic, and pharmaceutical additives, which can be prepared in an eco-friendly way by using lipases as catalysts. Because they are amphiphilic molecules, which possess high free radical scavenging capacity, they can be applied as liposoluble antioxidants as well as emulsifiers and biosurfactants. In this study, the influence of a wide range of acyl donors on ester yield in lipase-catalyzed synthesis and ester antioxidant activity was examined. Among saturated acyl donors, higher yields and antioxidant activities of esters were achieved when short-chain FAs were used. Oleic acid gave the highest yield overall and its ester exhibited a high antioxidant activity. Optimization of experimental factors showed that the highest conversion (60.5%) in acetone was achieved with 5 g L(-1) of lipase, 50 mM of vitamin C, 10-fold molar excess of oleic acid, and 0.7 mL L(-1) of initial water. Obtained results showed that even short- and medium-chain ascorbyl esters could be synthesized with high yields and retained (or even exceeded) free radical scavenging capacity of l-ascorbic acid, indicating prospects of broadening their application in emulsions and liposomes. PMID:25224149

  6. Widespread occurrence of bisphenol A diglycidyl ethers, p-hydroxybenzoic acid esters (parabens), benzophenone type-UV filters, triclosan, and triclocarban in human urine from Athens, Greece.

    Science.gov (United States)

    Asimakopoulos, Alexandros G; Thomaidis, Nikolaos S; Kannan, Kurunthachalam

    2014-02-01

    Biomonitoring of human exposure to bisphenol A diglycidyl ethers (BADGEs; resin coating for food cans), p-hydroxybenzoic acid esters (parabens; preservatives), benzophenone-type UV filters (BP-UV filters; sunscreen agents), triclosan (TCS; antimicrobials), and triclocarban (TCC; antimicrobials) has been investigated in western European countries and North America. Nevertheless, little is known about the exposure of Greek populations to these environmental chemicals. In this study, 100 urine samples collected from Athens, Greece, were analyzed by liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) for the determination of total concentrations of five derivatives of BADGEs, six parabens and their metabolite (ethyl-protocatechuate), five derivatives of BP-UV filters, TCS, and TCC. Urinary concentrations of BADGEs, parabens, ethyl-protocatechuate, BP-UV filters, TCS and TCC (on a volume basis) ranged 0.3-20.9 (geometric mean: 0.9), 1.6-1010 (24.2), <2-71.0 (2.1), 0.5-1120 (4.4), <0.5-2580 (8.0) and <0.5-1.9 (0.6) ng/mL, respectively. All 19 target chemicals were found in urine, and the highest detection rates were observed for methyl paraben (100%), bisphenol A bis (2,3-dihydroxypropyl) ether (90%), ethyl paraben (87%), 2,4-dihydroxybenzophenone (78%), propyl paraben (72%), and TCS (71%). Estimated daily intakes (EDIurine), calculated on the basis of the measured urinary concentrations, ranged from 0.023 μg/kg bw/day for Σ5BADGEs to 31.4 μg/kg bw/day for Σ6Parabens. PMID:24246946

  7. 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.

  8. Lysosomal acid lipase deficiency: diagnosis and treatment of Wolman and Cholesteryl Ester Storage Diseases.

    Science.gov (United States)

    Porto, Anthony F

    2014-09-01

    Lysosomal acid lipase (LAL) is responsible for the hydrolysis of cholesterol esters and triglycerides. LAL is coded by the LIPA gene on chromosome 10q23.31. Its deficiency leads to two autosomal recessive disorders, Wolman disease (WD) and Cholesteryl Ester Storage Disease (CESD). WD has an estimated incidence of 1 in 500,000 live births and is the result of a complete loss of LAL and presents in infancy with vomiting, diarrhea, poor weight gain and hepatomegaly subsequently leading to death. CESD is the result of partial loss of LAL and its presentation is more variable. Patients may be asymptomatic or present with nonspecific gastrointestinal symptoms, hepatomegaly, elevated transaminases and dystipidemia which may be confused with the diagnosis of Non-alcoholic Fatty Liver Disease. CESD is currently underdiagnosed and has an estimated prevalence as high as I in 40,000 individuals. Radiologic findings in WD is calcification of the adrenal glands. Hepatomegaly is noted on CT scan in both WD and CESD. MRI may demonstrate accumulation of cholesterol esters and may be useful to study effects of potential medical therapies. The diagnosis of WD and CESD is based on LIPA gene sequencing and the measurement of LAL levels in peripheral blood leukocytes. Treatment of LAL deficiency is currently limited to control of cholesterol levels and to prevent premature atherosclerosis. Use of enzyme replacement therapy with recombinant human LAL in short-term studies has shown to be safe and effective. PMID:25345094

  9. 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

    2016-02-26

    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 CuL(1) favoured higher catalytic efficiency and more pronounced enantioselectivity than the "face-to-face" complex CuL(2). The best enantioselectivity was observed for N-Boc-phenylalanine 4-nitrophenyl ester (S2) enantiomers promoted by CuL(1), which exhibited an enantiomer selectivity of 15.7. We observed preferential hydrolysis of L-S2 by CuL(1), 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.

  10. 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.)

  11. Amino acid esters substituted phosphorylated emtricitabine and didanosine derivatives as antiviral and anticancer agents.

    Science.gov (United States)

    Sekhar, Kuruva Chandra; Janardhan, Avilala; Kumar, Yellapu Nanda; Narasimha, Golla; Raju, Chamarthi Naga; Ghosh, S K

    2014-07-01

    Owing to the promising antiviral activity of amino acid ester-substituted phosphorylated nucleosides in the present study, a series of phosphorylated derivatives of emtricitabine and didanosine substituted with bioactive amino acid esters at P-atom were synthesized. Initially, molecular docking studies were screened to predict their molecular interactions with hemagglutinin-neuraminidase protein of Newcastle disease virus and E2 protein of human papillomavirus. The title compounds were screened for their antiviral ability against Newcastle disease virus (NDV) by their in ovo study in embryonated chicken eggs. Compounds 5g and 9c exposed well mode of interactions with HN protein and also exhibited potential growth of NDV inhibition. The remaining compounds exhibited better growth of NDV inhibition than their parent molecules, i.e., emtricitabine (FTC) and didanosine (ddI). In addition, the in vitro anticancer activity of all the title compounds were screenedagainst HeLa cell lines at 10 and 100 μg/mL concentrations. The compounds 5g and 9c showed an effective anticancer activity than that of the remaining title compounds with IC50 values of 40 and 60 μg/mL, respectively. The present in silico and in ovo antiviral and in vitro anticancer results of the title compounds are suggesting that the amino acid ester-substituted phosphorylated FTC and ddI derivatives, especially 5g and 9c, can be used as NDV inhibitors and anticancer agents for the control and management of viral diseases with cancerous condition. PMID:24789416

  12. Caffeic Acid Phenethyl Ester as a Protective Agent against Nephrotoxicity and/or Oxidative Kidney Damage: A Detailed Systematic Review

    OpenAIRE

    Sumeyya Akyol; Veli Ugurcu; Aynur Altuntas; Rukiye Hasgul; Ozlem Cakmak; Omer Akyol

    2014-01-01

    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 ...

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

    Institute of Scientific and Technical Information of China (English)

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

    2012-01-01

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

  14. 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.

  15. Synthesis ,Structure and Biological Activities of Some Novel Anthranilic Acid Esters Containing N-Pyridyl-pyrazole

    Institute of Scientific and Technical Information of China (English)

    DONG,Weili; XU,Junying; XIONG,Lixia; LIU,Xinghai; LI,Zhengming

    2009-01-01

    In search of environmentally benign insecticides with high activity,low toxicity and low residue,a novel series of anthranilic acid esters containing N-pyridylpyrazole were designed and synthesized.All of the compounds were characterized and confirmed by IR,1H NMR,MS and elemental analysis.The single crystal structure of 14d was determined by X-ray diffraction.The bioassay tests showed that the synthesized compounds exhibited good insecti-tidal activities against Mythimna separata Walker and Culex pipiens pallens.

  16. 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.

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

    Science.gov (United States)

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

    2016-06-01

    A wide spectrum of commercially available lipases and microbial whole cells catalysts were tested for biotransformations of 2-hydroxy-2-(ethoxyphenylphosphinyl)acetic acid 1 and its butyryl ester. The best results were achieved for biocatalytic hydrolysis of ester: 2-butyryloxy-2-(ethoxyphenylphosphinyl)acetic acid 2 performed by lipase from Candida cylindracea, what gave optically active products with 85% enantiomeric excess, 50% conversion degree and enantioselectivity 32.9 for one pair of enantiomers. Also enzymatic systems of Penicillium minioluteum and Fusarium oxysporum were able to hydrolyze tested compound with high enantiomeric excess (68-93% ee), enantioselectivity (44 for one pair of enantiomers) and conversion degree about 50-55%. Enzymatic acylation of hydroxyphosphinate was successful in case when porcine pancreas lipase was used. After 4days of biotransformation the conversion reaches 45% but the enantiomeric enrichment of the isomers mixture do not exceed 43%. Obtained chiral compounds are valuable derivatizing agents for spectroscopic (NMR) evaluation of enantiomeric excess for particular compounds (e.g. amino acids). PMID:26989983

  18. 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.

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

    International Nuclear Information System (INIS)

    Antibodies that bind an 125I-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 104, 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

  20. A Robust, "One-Pot" Method for Acquiring Kinetic Data for Hammett Plots Used to Demonstrate Transmission of Substituent Effects in Reactions of Aromatic Ethyl Esters

    Science.gov (United States)

    Yau, Hon Man; Haines, Ronald S.; Harper, Jason B.

    2015-01-01

    A "one-pot" method for acquiring kinetic data for the reactions of a series of substituted aromatic esters with potassium hydroxide using [supserscript 13]C NMR spectroscopy is described, which provides an efficient way to obtain sufficient data to demonstrate the Hammett equation in undergraduate laboratories. The method is…

  1. Safety Assessment of Citric Acid, Inorganic Citrate Salts, and Alkyl Citrate Esters as Used in Cosmetics.

    Science.gov (United States)

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

    2014-05-26

    The CIR Expert Panel (Panel) assessed the safety of citric acid, 12 inorganic citrate salts, and 20 alkyl citrate esters as used in cosmetics, concluding that these ingredients are safe in the present practices of use and concentration. Citric acid is reported to function as a pH adjuster, chelating agent, or fragrance ingredient. Some of the salts are also reported to function as chelating agents, and a number of the citrates are reported to function as skin-conditioning agents but other functions are also reported. The Panel reviewed available animal and clinical data, but because citric acid, calcium citrate, ferric citrate, manganese citrate, potassium citrate, sodium citrate, diammonium citrate, isopropyl citrate, stearyl citrate, and triethyl citrate are generally recognized as safe direct food additives, dermal exposure was the focus for these ingredients in this cosmetic ingredient safety assessment.

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

    Science.gov (United States)

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

    2013-09-01

    An actinomycete producing oil-like mixtures was isolated and characterized. The strain was isolated from sheep faeces and identified as Streptomyces sp. S161 based on 16S rRNA gene sequence analysis. The strain showed cellulase and xylanase activities. The (1) H nuclear magnetic resonance (NMR) spectra of the mixtures showed that the mixtures were composed of fatty acid methyl esters (52·5), triglycerides (13·7) and monoglycerides (9·1) (mol.%). Based on the gas chromatography-mass spectrometry (GC-MS) analysis, the fatty acid methyl esters were mainly composed of C14-C16 long-chain fatty acids. The results indicated that Streptomyces sp. S161 could produce fatty acid methyl esters (FAME) directly from starch. To our knowledge, this is the first isolated strain that can produce biodiesel (FAME) directly from starch. PMID:23692633

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

    Directory of Open Access Journals (Sweden)

    Claus Larsen

    2007-10-01

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

  4. 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.

    2002-01-01

    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

  5. 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

    2002-01-01

    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 characterizat

  6. QSTR studies regarding the ECOSAR toxicity of benzene-carboxylic acid' esters to fathead minnow fish (Pimephales promelas).

    Science.gov (United States)

    Tarko, Laszlo; Putz, Mihai V; Ionascu, Cosmin; Putz, Ana-Maria

    2014-01-01

    The present work employs 152 benzene-carboxylic acid' esters having computed the toxicity within the range [2.251, 10.222] for fathead minnow fish (Pimephales promelas). Calibration set includes many pairs having very similar chemical structure, size, shape and hydrophilicity, but very different value of ECOSAR toxicity or vice versa. The QSTR study, which uses all esters as calibration set, emphasized a large percent (16.2%) of outliers. In this QSTR study most of the estimated values of toxicity for outliers are much lower than ECOSAR toxicity. The LogP and some aromaticity descriptors are predictors. The best QSTR for esters having low value (toxicity and the best QSTR for esters having high value (> 5.5) of ECOSAR toxicity are obtained when the number of outliers is very small. These QSTRs are different enough and highlight opposite influences of certain descriptors on toxicity. The results emphasize two possibilities: (a) the esters having low value of ECOSAR toxicity and the esters having high value of ECOSAR toxicity are included in two different classes from the point of view of structure-toxicity relationship and/or (b) many high values of ECOSAR toxicity are wrong. By comparison, a QSTR using experimental values of toxicity against rats for 37 benzene-carboxylic esters included in the same database gives good correlation experimental/computed values of toxicity, the number of outliers is null and the result of validation test is good. PMID:24724900

  7. Ultrasound assisted synthesis of isopropyl esters from palm fatty acid distillate.

    Science.gov (United States)

    Deshmane, Vishwanath G; Gogate, Parag R; Pandit, Aniruddha B

    2009-03-01

    Esterification is one of the most preferred synthesis routes for organic esters which are most frequently used as plasticizers, solvents and perfumery and flavour chemicals. The present work deals with acid catalyzed synthesis of isopropyl esters from palm fatty acid distillate (PFAD) in the presence of ultrasonic irradiations operating at 25kHz frequency and 1kW of supplied power. Effect of different operating parameters such as molar ratio of reactants, catalyst quantity and operating temperature has been studied with an aim of optimization. It has been observed that ultrasound enhances the rate of reaction and the extent of equilibrium conversion. The optimum parameters for this process have been found to be 1:5 molar ratio of PFAD to isopropanol, catalyst concentration of 5% of PFAD and 60 degrees C reaction temperature. Maximum conversion levels of about 80% have been obtained in 6h of reaction time under these optimized conditions. Analysis of the kinetic data indicates that the reaction follows first order reversible path. PMID:18977682

  8. The amphiphilic alkyl ester derivatives of l-ascorbic acid induce reorganization of phospholipid vesicles.

    Science.gov (United States)

    Giudice, Francesca; Ambroggio, Ernesto E; Mottola, Milagro; Fanani, Maria Laura

    2016-09-01

    l-ascorbic acid alkyl esters (ASCn) are lipophilic forms of vitamin C, which maintain some of its antioxidant power. Those properties make this drug family attractive to be used in pharmacological preparations protecting other redox-sensible drugs or designed to reduce possible toxic oxidative processes. In this work, we tested the ability of l-ascorbic acid alkyl esters (ASCn) to modulate the structure, permeability, and rheological properties of phospholipid bilayers. The ASCn studied here (ASC16, ASC14, and ASC12) alter the structural integrity as well as the rheological properties of phospholipid membranes without showing any evident detergent activity. ASC14 appeared as the most efficient drug in destabilize the membrane structure of nano- and micro-size phospholipid liposomes inducing vesicle content leakage and shape elongation on giant unilamellar vesicles. It also was the most potent enhancer of membrane microviscosity and surface water structuring. Only ASC16 induced the formation of drug-enriched condensed domains after its incorporation into the lipid bilayer, while ASC12 appeared as the less membrane-disturbing compound, likely because of its poor, and more superficial, partition into the membrane. We also found that incorporation of ASCn into the lipid bilayers enhanced the reduction of membrane components, compared with soluble vitamin C. Our study shows that ASCn compounds, which vary in the length of the acyl chain, show different effects on phospholipid vesicles used as biomembrane models. Those variances may account for subtly differences in the effectiveness on their pharmacological applications. PMID:27342371

  9. 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.

  10. N-( p-Ethynylbenzoyl) derivatives of amino acid and dipeptide methyl esters - Synthesis and structural study

    Science.gov (United States)

    Eißmann, Frank; Weber, Edwin

    2011-11-01

    A series of N-( p-ethynylbenzoyl) derivatives ( 1-4) of the amino acids glycine and L-alanine as well as the dipeptides glycylglycine and L-alanylglycine has been synthesized via a two-step reaction sequence including the reaction of an appropriate N-( p-bromobenzoyl) precursor with trimethylsilylacetylene followed by deprotection of the trimethylsilyl protecting group, respectively. X-ray crystal structures of the amino acid and dipeptide methyl esters 1-4 are reported. The amide and peptide bonds within each molecular structure are planar and adopt the trans-configuration. The packing structures are governed by N sbnd H⋯O interactions leading to the formation of characteristic strand motifs. Further stabilization results from weaker C sbnd H⋯O and C sbnd H⋯π contacts.

  11. Enzymatic Acylation of Anthocyanin Isolated from Black Rice with Methyl Aromatic Acid Ester as Donor: Stability of the Acylated Derivatives.

    Science.gov (United States)

    Yan, Zheng; Li, Chunyang; Zhang, Lixia; Liu, Qin; Ou, Shiyi; Zeng, Xiaoxiong

    2016-02-10

    The enzymatic acylation of anthocyanin from black rice with aromatic acid methyl esters as acyl donors and Candida antarctica lipase B was carried out under reduced pressure. The highest conversion of 91% was obtained with benzoic acid methyl ester as acyl donor; cyanidin 3-(6″-benzoyl)-glucoside, cyanidin 3-(6″-salicyloyl)-glucoside, and cyanidin 3-(6″-cinnamoyl)-glucoside were successfully synthesized. This is the first report on the enzymatic acylation of anthocyanin from black rice with methyl aromatic esters as acyl donors and lipase as biocatalyst. Furthermore, the acylation with aromatic carboxylic acids enhanced both the thermostability and light resistivity of anthocyanin. In particular, cyanidin 3-(6″-cinnamoyl)-glucoside was the most stable among the three acylated anthocyanins synthesized. PMID:26766135

  12. Accuracy, reproducibility, and interpretation of fatty acid methyl ester profiles of model bacterial communities

    Science.gov (United States)

    Kidd, Haack S.; Garchow, H.; Odelson, D.A.; Forney, L.J.; Klug, M.J.

    1994-01-01

    We determined the accuracy and reproducibility of whole-community fatty acid methyl ester (FAME) analysis with two model bacterial communities differing in composition by using the Microbial ID, Inc. (MIDI), system. The biomass, taxonomic structure, and expected MIDI-FAME profiles under a variety of environmental conditions were known for these model communities a priori. Not all members of each community could be detected in the composite profile because of lack of fatty acid 'signatures' in some isolates or because of variations (approximately fivefold) in fatty acid yield across taxa. MIDI- FAME profiles of replicate subsamples of a given community were similar in terms of fatty acid yield per unit of community dry weight and relative proportions of specific fatty acids. Principal-components analysis (PCA) of MIDI-FAME profiles resulted in a clear separation of the two different communities and a clustering of replicates of each community from two separate experiments on the first PCA axis. The first PCA axis accounted for 57.1% of the variance in the data and was correlated with fatty acids that varied significantly between communities and reflected the underlying community taxonomic structure. On the basis of our data, community fatty acid profiles can be used to assess the relative similarities and differences of microbial communities that differ in taxonomic composition. However, detailed interpretation of community fatty acid profiles in terms of biomass or community taxonomic composition must be viewed with caution until our knowledge of the quantitative and qualitative distribution of fatty acids over a wide variety of taxa and the effects of growth conditions on fatty acid profiles is more extensive.

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

    Science.gov (United States)

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

    2004-06-01

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

  14. 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. PMID:24768282

  15. RENEWABLE ENERGY CONTENT OF FATTY ACID METHYL ESTERS (FAME AND GLYCEROL

    Directory of Open Access Journals (Sweden)

    Giuseppe Toscano

    2009-12-01

    Full Text Available Fatty acid methyl esters (FAME and glycerol produced by transesterification reaction contain atoms that in the reagents belong to methanol and, therefore, are not renewable. A method to evaluate the content of the renewable and non-renewable energetic fraction, released during their combustion, was 52 Fig. 2 - Correlation between EFNR and NCM of FAME. Fig. 3 - Correlation between NCM and NS. Fig. 4 - Correlations between EFNR and NS. 07_Toscano(541_47 26-01-2010 9:35 Pagina 52 developed using a thermochemical criteria, based on bond dissociation energies and the knowledge of the molecular structure of the reagents and the products. Results show that the fraction of non-renewable energy in the most diffused FAME is lower than 1% depending on the lengths of the carbonaceous methyl esters. Meanwhile, the energetic supply for the GL of this fraction is about 1.6%. The data reported in this document can be used to develop a criteria that corrects the fiscal mechanism aspects of some renewable energy products.

  16. Catalysis of Heteropoly Acidic Salts for Synthesis of Diethylene Glycol Ethyl Ether with Diethylene Glycol and Ethanol

    Institute of Scientific and Technical Information of China (English)

    刘俊峰; 易平贵; 戚蕴石

    2001-01-01

    Ag3PW12O4o and Ag4 SiW12O40 showed high activity and stability in the synthesis of diethylene glycol ethyl ether with diethylene glycol and ethanol, on which the conversion is 80.2%and 78.4%, respectively, and the selectivity of diethylene glycol ether is 75.4% and 80.6%, respectively. After the third reaction cycle, Ag3PW12O40 and Ag4SiW12O4o still showed higher activity and selectivity, on which the conversion is 72.6% and 77.5% respectively. But the activity of Ag3PMo12O40is lower, the conversion is only 21.0%. IR, XRD, TG and n-lutylamine titrimetry showed that the catalysis may be conmected with two kinds of acidic centers owned by heteropoly acidic salt.

  17. 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.

  18. Enhanced microemulsion formation in lipid-based drug delivery systems by combining mono-esters of medium-chain fatty acids with di- or tri-esters

    OpenAIRE

    Darshil P Patel; Ping Li; Abu T. M. Serajuddin

    2012-01-01

    To develop strategies for selecting appropriate lipids from mono-, di- and tri-esters of medium-chain fatty acids for the development of lipid-based drug delivery systems, ternary phase diagrams of propylene glycol(PG) monocaprylate (Capryol® 90; HLB~7), PG dicaprylocaprate (Labrafac™PG; HLB~2) and glycerol tricaprylocaprate (Labrafac™Lipophile WL1349; HLB~2) were determined in combination with a commonsurfactant, PEG-35 castor oil (Cremophor®EL, HLB~13), and water. Particle size and v...

  19. Simultaneous determination of C2-C22 non-esterified fatty acids and other metabolically relevant carboxylic acids in biological material by gas chromatography of their benzyl esters.

    Science.gov (United States)

    Schatowitz, B; Gercken, G

    1988-03-18

    A method for the simultaneous determination of non-esterified short-, medium- and long-chain fatty acids and other types of metabolically relevant carboxylic acids such as hydroxy, keto, aromatic and dicarboxylic acids in biological material by capillary gas chromatography of benzyl ester derivatives is described. Sample preparation avoiding incomplete isolation of carboxylic acids consisted of deproteinization and extraction with ethanol, fixation of carboxylic acids as carboxylates, removal of interfering compounds such as neutral lipids by hexane extraction and amino acids, acyl carnitines and other cations by cation-exchange chromatography, derivatization of keto groups of ketocarboxylic acids into O-methyl oximes and benzyl ester formation by reaction of the potassium carboxylates with benzyl bromide via crown ether catalysis. The sample preparation conditions were investigated, showing the usefulness of this method for quantitative determinations. Chromatograms obtained from human serum, human urine and rat heart ventricle and concentrations of carboxylic acids in these specimens are presented. PMID:3372640

  20. NF EN 14213. - Heating fuels. - Fatty acid methyl esters (FAME) - Requirements and test methods; NF EN 14213. - Fioul domestique. - Esters methyliques d'acides gras (EMAG). - Exigences et methodes d'essais

    Energy Technology Data Exchange (ETDEWEB)

    NONE

    2004-04-01

    This standard specifies requirements and test methods for marketed and delivered fatty acid methyl ester (FAME) to be used as heating oil solely or as a blending component for the production of heating oil. At 100% concentration it is applicable to fuel for use in heating equipment designed or subsequently adapted to run on 100% FAME.

  1. Catalytic synthesis of butyric esters with TiSiW12O40/TiO2

    Institute of Scientific and Technical Information of China (English)

    2003-01-01

    The catalytic activities of TiSiW12O40/TiO2 in synthesizing ethyl ester, propyl ester, n-butyl ester, and amyl esterwere reported. It was demonstrated that TiSiW12O40/TiO2is an excellent catalyst. Various factors concemed with esterifica-tion were investigated. The optimum conditions were found: the mole ratio of alcohol to acid is 1.3:1, the mass ratio ofcatalyst to reactants is 1.5%, and the reaction time is 1.0 h. Under the optimum conditions, the yields are 88.0% for ethylester, 94.5% for propyl ester, 98.6% for n-butyl ester, 99.1% for n-amyl ester, and 96.7% for iso-amyl ester, respectively.

  2. Evaluation of the orofacial antinociceptive profile of the ethyl acetate fraction and its major constituent, rosmarinic acid, from the leaves of Hyptis pectinata on rodents

    Directory of Open Access Journals (Sweden)

    Rosângela E.A. Falcão

    2016-04-01

    Full Text Available ABSTRACT Hyptis pectinata (L. Poit., Lamiaceae, popularly known as "sambacaitá," is an aromatic shrub largely grown in the Brazilian northeastern. We investigated the antinociceptive effects of the ethyl acetate fraction obtained from the leaves of H. pectinata and of its main constituent rosmarinic acid, on formalin (2%-, glutamate (25 µM- and capsaicin (2.5 µg-induced orofacial nociception in rodents. Male mice were pretreated with ethyl acetate fraction (100, 200 or 400 mg/kg, p.o., rosmarinic acid (10 or 20 mg/kg, p.o., morphine (5 mg/kg, i.p., or vehicle (distilled water + 0.2% Tween 80. Ethyl acetate fraction reduced the nociceptive face-rubbing behavior during the two phase of the formalin test, whereas pretreatment with rosmarinic acid decreased the pain behavior in the second phase. Ethyl acetate fraction produced significant antinociceptive effects in the capsaicin and glutamate tests. This study showed that oral administration of ethyl acetate fraction produced potent antinociceptive effects compared to treatment with rosmarinic acid.

  3. Highly Lewis Acidic Arylboronate Esters Capable of Colorimetric Turn-On Response.

    Science.gov (United States)

    Oehlke, Alexander; Auer, Alexander A; Schreiter, Katja; Friebe, Nadine; Spange, Stefan

    2015-12-01

    A series of boronate-π-acceptor compounds containing different types of π bridges (1,4-phenylen or thien-2,5-diyl or furan-2,5-diyl) that link the switchable boronate ester group with the efficient TCF acceptor group (TCF=2-dicyanomethylen-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran) has been synthesized. A TCF chromophore of this type undergoes transition to a donor-π-acceptor compound upon coordination of Lewis bases at the Lewis acidic boron center, which is accompanied by an enhanced intramolecular charge-transfer interaction. The Lewis acid character has been investigated by spectroscopic measurements (UV/Vis, NMR spectroscopies) as well as DFT and ab initio-based calculations. It is shown that the TCF acceptor group and thiophene or furan π-bridges directly bound to the boron atom cooperatively increase the Lewis acidity. UV/Vis titration experiments confirm fluoride binding constants in the range of up to 10(8)  M(-1) in CH2 Cl2 . In addition to the strong boron fluoride binding motif, Lewis interactions also occur with weaker Lewis bases, such as pyridine or aliphatic alcohols. The unique combination of chromophoric and Lewis acidic properties is responsible for the intense colorimetric turn-on response detectable after complex formation. PMID:26489784

  4. Heteropoly Acid/Nitrogen Functionalized Onion-like Carbon Hybrid Catalyst for Ester Hydrolysis Reactions.

    Science.gov (United States)

    Liu, Wei; Qi, Wei; Guo, Xiaoling; Su, Dangsheng

    2016-02-18

    A novel heteropoly acid (HPA)/nitrogen functionalized onion-like carbon (NOLC) hybrid catalyst was synthesized through supramolecular (electrostatic and hydrogen bond) interactions between the two components. The chemical structure and acid strength of the HPA/NOLC hybrid have been fully characterized by thermogravimetric analysis, IR spectroscopy, X-ray photoelectron spectroscopy, NH3 temperature-programmed desorption and acid-base titration measurements. The proposed method for the fabrication of the HPA/NOLC hybrid catalyst is a universal strategy for different types of HPAs to meet various requirements of acidic or redox catalysis. The hydrophobic environment of NOLC effectively prevents the deactivation of HPA in an aqueous system, and the combination of uniformly dispersed HPA clusters and the synergistic effect between NOLC and HPA significantly promotes its activity in ester hydrolysis reactions, which is higher than that of bare PWA as homogeneous catalyst. The kinetics of the hydrolysis reactions indicate that the aggregation status of the catalyst particles has great influence on the apparent activity. PMID:26606266

  5. Insights into the formation mechanism of chloropropanol fatty acid esters under laboratory-scale deodorization conditions.

    Science.gov (United States)

    Hori, Katsuhito; Hori-Koriyama, Natsuko; Tsumura, Kazunobu; Fukusaki, Eiichiro; Bamba, Takeshi

    2016-08-01

    Chloropropanol fatty acid esters (CPFAEs) are well-known contaminants in refined oils and fats, and several research groups have studied their formation. However, the results obtained in these studies were not satisfactory because the CPFAEs were not analyzed comprehensively. Thus, in the present study, a comprehensive analysis was performed to obtain new details about CPFAE formation. Each lipid (monopalmitin, dipalmitin, tripalmitin, monoolein, diolein, triolein, and crude palm oil) was heated at 250°C for 90 min, and the CPFAEs were analyzed using supercritical fluid chromatography/tandem mass spectrometry. It was found that CP fatty acid monoesters were formed from monoacylglycerols and diacylglycerols after heating in the presence of a chlorine compound. In addition, CP fatty acid diesters were formed from diacylglycerols and triacylglycerols under the same conditions. In the case of crude palm oil, only CP fatty acid diesters were formed. Therefore, these results indicated that CPFAEs in refined palm oil were formed mainly from triacylglycerols. PMID:26822095

  6. 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....

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

    Science.gov (United States)

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

    2015-12-01

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

  8. Antifeedant activity of fatty acid esters and phytosterols from Echium wildpretii.

    Science.gov (United States)

    Santana, Omar; Reina, Matias; Fraga, Braulio M; Sanz, Jesús; González-Coloma, Azucena

    2012-03-01

    Crude extracts and fractions from Echium wildpretii H. Pearson ex Hook. f. subsp. wildpretii (Boraginaceae) have been tested against insect species Spodoptera littoralis, Leptinotarsa decemlineata, and the aphids Myzus persicae, Diuraphis noxia, Metopolophium dirhodum, Rhopalosiphum maidis, and Rhopalosiphum padi. The EtOH extract and the lipid and steroidal fractions of E. wildpretii exhibited significant antifeedant activities against the aphids and L. decemlineata. Two bioactive mixtures composed of fatty acid esters and n-alkanes were obtained from the lipid fraction. The bioguided fractionation of the steroidal fraction resulted in the isolation of glutinol, β-sitosterol, (3β,7α)-stigmast-5-ene-3,7-diol, and (3β,7α)-7-methoxystigmast-5-en-3-ol. The latter two compounds exhibited potent antifeedant activities against L. decemlineata indicating that the presence of an O-bearing C(7) was responsible for the activities of these molecules.

  9. 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

  10. Interfacial properties of air/water interfaces stabilized by oligofructose palmitic acid esters in the presence of whey protein isolate

    NARCIS (Netherlands)

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

    2013-01-01

    To study the applicability of oligofructose palmitic acid esters (OF-C16) as novel surfactants in food systems, the functional properties of OF-C16 were studied in the presence of whey protein isolate (WPI). Surface tension measurements, surface dilatational rheology, foam stability tests and Brewst

  11. Preparation of fatty acid methyl esters from hazelnut, high-oleic peanut and walnut oils and evaluation as biodiesel

    Science.gov (United States)

    Hazelnut, walnut and high-oleic peanut oils were converted into fatty acid methyl esters using catalytic sodium methoxide and evaluated as potential biodiesel fuels. These feedstocks were of interest due to their adaptability to marginal lands and their lipid production potentials (780-1780 L ha-1 y...

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

    Science.gov (United States)

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

    2013-01-01

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

  13. A Comprehensive Evaluation of the Melting Points of Fatty Acids and Esters Determined by Differential Scanning Calorimetry

    Science.gov (United States)

    The melting point is one of the most important physical properties of a chemical compound and plays a significant role in determining possible applications. For fatty acid esters the melting point is essential for a variety of food and non-food applications, the latter including biodiesel and its c...

  14. 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, S.; Laurens, L. M. L.

    2013-12-01

    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.

  15. Colour indicator for enantiomeric excess and assignment of the configuration of the major enantiomer of an amino acid ester

    NARCIS (Netherlands)

    Delden, R.A.van; Feringa, B.L.

    2002-01-01

    A colour indicator for the full range of enantiomeric excess (-100% --> 100% ee) is presented which is based on visual colour inspection of a liquid crystal doped with the analyte, i.e. the methyl ester of amino acid phenylglycine, providing the enantiomeric excess and allowing the assignment of the

  16. Separation of middle rare earths by solvent extraction using 2-ethylhexylphosphonic acid mono-2-ethylhexyl ester as an extractant

    Institute of Scientific and Technical Information of China (English)

    Danilo; Fontana; Loris; Pietrelli

    2009-01-01

    The extraction of the trivalent middle rare earths from chloride media by kerosene solutions of 2-ethylhexylphosphonic acid mono-2-ethylhexyl ester as an extractant was studied. The separation factors between the elements using solution simulating wastes from NiMH spent batteries have been evaluated: the order of the extractive ability of extractant can be confirmed in ThGdEuSm.

  17. 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.

    2012-01-01

    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 o

  18. 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.

  19. 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.

  20. Versatile Biodegradable Poly(ester amides Derived from α-Amino Acids for Vascular Tissue Engineering

    Directory of Open Access Journals (Sweden)

    Pooneh Karimi

    2010-03-01

    Full Text Available Biodegradable poly(ester amide (PEA biomaterials derived from α-amino acids, diols, and diacids are promising materials for biomedical applications such as tissue engineering and drug delivery because of their optimized properties and susceptibility for either hydrolytic or enzymatic degradation. The objective of this work was to synthesize and characterize biodegradable PEAs based on the α-amino acids L-phenylalanine and L-methionine. Four different PEAs were prepared using 1,4-butanediol, 1,6-hexanediol, and sebacic acid by interfacial polymerization. High molecular weight PEAs with narrow polydispersity indices and excellent film-forming properties were obtained. The incubation of these PEAs in PBS and chymotrypsin indicated that the polymers are biodegradable. Human coronary artery smooth muscle cells were cultured on PEA films for 48 h and the results showed a well-spread morphology. Porous 3D scaffolds fabricated from these PEAs were found to have excellent porosities indicating the utility of these polymers for vascular tissue engineering.

  1. 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.

  2. 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.

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

    Institute of Scientific and Technical Information of China (English)

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

    2015-01-01

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

  4. Catalyst-free ethyl biodiesel production from rice bran under subcritical condition

    Science.gov (United States)

    Zullaikah, Siti; Afifudin, Riza; Amalia, Rizky

    2015-12-01

    In-situ ethyl biodiesel production from rice bran under subcritical water and ethanol with no catalyst was employed. This process is environmentally friendly and is very flexible in term of feedstock utilization since it can handle relatively high moisture and free fatty acids (FFAs) contents. In addition, the alcohol, i.e. bioethanol, is a non-toxic, biodegradable, and green raw material when produced from non-edible biomass residues, leading to a 100% renewable biodiesel. The fatty acid ethyl esters (FAEEs, ethyl biodiesel) are better than fatty acid methyl esters (FAMEs, methyl biodiesel) in terms of fuel properties, including cetane number, oxidation stability and cold flow properties. The influences of the operating variables such as reaction time (1 - 10 h), ethanol concentration (12.5 - 87.5%), and pressurizing gas (N2 and CO2) on the ethyl biodiesel yield and purity have been investigated systematically while the temperature and pressure were kept constant at 200 °C and 40 bar. The optimum results were obtained at 5 h reaction time and 75% ethanol concentration using CO2 as compressing gas. Ethyl biodiesel yield and purity of 58.78% and 61.35%, respectively, were obtained using rice bran with initial FFAs content of 37.64%. FFAs level was reduced to 14.22% with crude ethyl biodiesel recovery of 95.98%. Increasing the reaction time up to 10 h only increased the yield and purity by only about 3%. Under N2 atmosphere and at the same operating conditions (5h and 75% ethanol), ethyl biodiesel yield and purity decreased to 54.63% and 58.07%, respectively, while FFAs level was increased to 17.93% and crude ethyl biodiesel recovery decreased to 87.32%.

  5. Synthesis of alkyl esters by cutinase in miniemulsion and organic solvent media.

    Science.gov (United States)

    de Barros, Dragana P C; Fonseca, Luís P; Cabral, Joaquim M S; Weiss, Clemens K; Landfester, Katharina

    2009-05-01

    The main objective of this work was studying and testing the nature and influence of reaction media (organic solvent vs. miniemulsion system) on the synthesis of alkyl esters catalyzed by Fusarium solani pisi cutinase. Ester synthesis and cutinase selectivity for different chain length of acids and alcohols (ethyl and hexyl) were evaluated. In iso-octane, after 1 h of reaction, cutinase exhibits rates of esterification between 0.24 micromol x mg(-)1 x min(-1) for ethyl oleate and 1.15 micromol x mg(-)1 x min(-1) for ethyl butyrate, while in a miniemulsion system the rates were from 0.05 for ethyl heptanoate to 0.76 micromol x mg(-1) x min(-1) for ethyl decanoate. The reaction rate for the synthesis of hexyl esters in a miniemulsion system was from 0.19 for hexyl heptanoate to 1.07 micromol x mg(-)1 x min(-1) for hexyl decanoate. High conversion yields of 95% at equilibrium after 8 h of reaction in iso-octane for pentanoic acid (C(5)) with ethanol at equimolar concentration (0.1 M) was achieved. Additionally, this work showed that a significant and unexpected shift in cutinase selectivity occurred towards longer chain length carboxylic acids (C(8)-C(10)) in miniemulsion system as compared to organic solvent (iso-octane) and previous studies in reverse micellar systems. The possibility of working with higher concentration of substrates, without inhibitory effect on the enzyme, was another advantage of the miniemulsion system.

  6. Alanine Esters of Enterococcal Lipoteichoic Acid Play a Role in Biofilm Formation and Resistance to Antimicrobial Peptides

    OpenAIRE

    Fabretti, Francesca; Theilacker, Christian; Baldassarri, Lucilla; Kaczynski, Zbigniew; Kropec, Andrea; Holst, Otto; Huebner, Johannes

    2006-01-01

    Enterococcus faecalis is among the predominant causes of nosocomial infections. Surface molecules like d-alanine lipoteichoic acid (LTA) perform several functions in gram-positive bacteria, such as maintenance of cationic homeostasis and modulation of autolytic activities. The aim of the present study was to evaluate the effect of d-alanine esters of teichoic acids on biofilm production and adhesion, autolysis, antimicrobial peptide sensitivity, and opsonic killing. A deletion mutant of the d...

  7. Esters of o- and m-carborane-C-carboxylic acids with o- and m-C-carborane alcohols

    International Nuclear Information System (INIS)

    Acid chlorides of o- and m-carborane-C-carboxylic acids reacted with primary o- and m-C-carborane alcohols in anhydrous benzene to form in a high yield (81-86%) previously unknown corresponding o- and m-carborane-containing two- and three-nuclear esters. The composition and structure of the compounds prepared have been characterized by elementary analysis, 1H and 11B NMR, IR and UV spectroscopy, by measuring their molecular weights and melting points

  8. Synthesis of monoketo and monohydroxy eicosanoic acids and esters with substituents at odd–numbered (3-13 carbons

    Directory of Open Access Journals (Sweden)

    HULYA CELIK

    2002-07-01

    Full Text Available In this study, monoketo and monohydroxy eicosanoic acids and their methyl esters with the position of the substituent on odd numbered carbon atoms from 3 to 13 were synthesized with high purity. Furthermore, the semicarbazone and anilide derivatives of the obtained keto acids were prepared. They were characterized by TLC, IR and 1H-NMR spectroscopy and their physical and chemical properties were established.

  9. Lipoprotein composition and serum cholesterol ester fatty acids in nonwesternized Melanesians.

    Science.gov (United States)

    Lindeberg, S; Nilsson-Ehle, P; Vessby, B

    1996-02-01

    In this study, the relationships between dietary fat [as measured by serum cholesterol ester fatty acids (CE-FA)], age, smoking, body mass index, and serum lipids were analyzed in 151 subsistence horticulturalists, aged 20-86 yr, from Kitava, Trobriand Islands, Papua New Guinea. Their diet consists of tubers, fruit, coconut, fish, and vegetables with a negligible influence of western food and alcohol. Total fat intake is low [21% of energy (en%)], while saturated fat intake from coconuts is high (17 en%, mainly lauric and myristic acid). In multivariate analysis, 11-43% of the variation of the serum lipoprotein composition was explained by CE-FA, age, and smoking habits. The proportion of CE20:5n-3 explained much of the variation of triglycerides (TG, negative relation) and high density lipoprotein-cholesterol (HDL-C, positive) in both sexes and serum apolipoprotein A1 (ApoA1, positive) in the males. CE16:0 was positively related to TG and negatively related to HDL-C and ApoA1 in both sexes, and in males it related negatively to total cholesterol (TC) and low density lipoprotein-cholesterol (LDL-C). In males, negative relationships were present between CE18:2n-6 and TC and between CE14:0 and serum lipoprotein(a). Smoking was independently associated with lower ApoA1 in both sexes and with lower HDL-C and higher TG, TC, LDL-C, and apolipoprotein B in males. In conclusion, marine n-3 fatty acids and linoleic acid showed the same potentially beneficial relationships with lipoproteins and apolipoproteins as in western populations. The relations of palmitic acid to serum lipids may be explained in terms of endogenous fat synthesis at a low-fat intake, rather than reflecting its relative intake.

  10. Patient with Hypertriglyceridemia, Type 2 Diabetes, and Chronic Kidney Disease Treated with Atorvastatin and Omega-3 Fatty Acid Ethyl Esters

    OpenAIRE

    Athyros, Vasilios G.; Mikhailidis, Dimitri P

    2012-01-01

    This is a case report that describes a 67-year-old woman with mixed hyperlipidemia and diabetic nephropathy. She was initially prescribed a combination of simvastatin plus gemfibrozil by her general practitioner (GP). When referred to our cardiovascular unit, we further diagnosed the patient to have mixed hyperlipidemia and rhabdomyolysis. Because of concerns with her chronic kidney disease (CKD), we temporarily stopped all her drug treatments and started insulin treatment for her type 2 diab...

  11. Benzyl esters of C2-C20 fatty acids and metabolically relevant carboxylic acids. Preparation and gas chromatography-mass spectrometry.

    Science.gov (United States)

    Schatowitz, B; Gercken, G

    1987-11-13

    Short-, medium- and long-chain fatty acids, and other types of metabolically relevant carboxylic acids like hydroxy-, keto-, aromatic and dicarboxylic acids, were analyzed by capillary gas chromatography. For separation, benzyl ester derivatives were used, prepared by reaction of the potassium carboxylates with benzyl bromide in acetonitrile catalyzed by a crown ether. The reaction conditions for quantitative benzylation were studied. Keto groups of ketocarboxylic acids were stabilized prior to benzylation by formation of O-methyl oximes using methoxyamine hydrochloride in aqueous-ethanolic solution. The separation of more than 45 carboxylic acids was achieved on a CP-Sil 5 CB fused-silica capillary column in less than 70 min. The electron impact mass spectra of ketocarboxylic acid O-methyl oxime benzyl esters PMID:3693495

  12. Determination of P-hydroxy Benzoic Acid EthyI ester in Fresh Bamboo Liquid Compound by HPLC%HPLC法测定复方鲜竹沥液中对羟基苯甲酸乙酯的含量

    Institute of Scientific and Technical Information of China (English)

    金卓

    2015-01-01

    OBJECTIVE Establish a determination method of p-hydroxy benzoic acid ethyl ester in fresh bam-boo liquid.METHODS Lichrospher C18 column(4.6 ×250mm,including 5μm) for the chromatographic column;In A:0.025 mol・ L-1 sodium dihydrogen phosphate solution ( adjustable pH 3.7 phosphate )-B:methanol as the gra-dient elution;Detection wavelength:258 nm;Flow rate:1.0 mL・ min -1;Column temperature 35℃.RESULTS P-hydroxy benzoic acid ethyl ester had a good linear and linear correlation in the range of 0.6915~55.32μg・ mL-1 ( r=0.9999 ) ,the average recovery was 96.31%,RSD was 1.17%( n=6 ) .CONCLUSION This method is simple and feasible ,and reproducible ,and Can be used to compound in fresh bamboo liquid content determination of hydrox -yl benzoic acid ethyl ester .%目的:建立复方鲜竹沥液中对羟基苯甲酸乙酯的含量测定方法。方法以 Lichrospher C18柱(4.6×250mm,5μm)为色谱柱;以 A:0.025mol・ L -1磷酸二氢钠溶液(磷酸调pH 3.7)-B:甲醇为梯度洗脱;检测波长:258nm;流速:1.0mL・ min -1;柱温:35℃。结果对羟基苯甲酸乙酯在0.6915~55.32μg・ mL -1范围内呈良好的线性关系(r=0.9999),平均回收率为96.31%,RSD为1.17%(n=6)。结论本方法简便可行,重现性好,可用于复方鲜竹沥液中对羟基苯甲酸乙酯的含量测定。

  13. Attraction of the Parasitic Mite Varroa to the Drone Larvae of Honey Bees by Simple Aliphatic Esters

    Science.gov (United States)

    Le Conte, Yves; Arnold, Gerard; Trouiller, Jerome; Masson, Claudine; Chappe, Bertrand; Ourisson, Guy

    1989-08-01

    An important parasitic threat to honey bees, the mite Varroa jacobsoni, is attracted to its major prey, drone larvae, by methyl and ethyl esters of straight-chain fatty acids, in particular methyl palmitate. These esters were extracted from drone larvae with n-hexane and were identified by gas chromatography-mass spectrometry. Their behavioral effect was evaluated with the use of a four-arm airflow olfactometer.

  14. Synthesis and Characterization of Fatty Acid/Amino Acid Self-Assemblies

    OpenAIRE

    Gajowy, Joanna; Bolikal, Durgadas; Kohn, Joachim; El Fray, Miroslawa

    2014-01-01

    In this paper, we discuss the synthesis and self-assembling behavior of new copolymers derived from fatty acid/amino acid components, namely dimers of linoleic acid (DLA) and tyrosine derived diphenols containing alkyl ester pendent chains, designated as “R” (DTR). Specific pendent chains were ethyl (E) and hexyl (H). These poly(aliphatic/aromatic-ester-amide)s were further reacted with poly(ethylene glycol) (PEG) and poly(ethylene glycol methyl ether) of different molecular masses, thus resu...

  15. NF EN 14104. July 2003. Fatty compounds derived products. Fatty acids methylic esters (FAME). Determination of the acid index; NF EN 14104. Juillet 2003. Produits derives des corps gras. Esters methyliques d'acides gras (EMAG). Determination de l'indice d'acide

    Energy Technology Data Exchange (ETDEWEB)

    NONE

    2003-07-01

    This European standard describes a titration method for the determination of the acid index of slightly colored fatty acids methylic esters (FAME). This method allows the determination of the acid index over a concentration range comprised between 0.10 mg of KOH/g and 1 mg of KOH/g. (J.S.)

  16. Sonolytic and Silent Polymerization of Methacrlyic Acid Butyl Ester Catalyzed by a New Onium Salt with bis-Active Sites in a Biphasic System — A Comparative Investigation

    Directory of Open Access Journals (Sweden)

    Perumberkandgai A. Vivekanand

    2013-02-01

    Full Text Available Currently, ingenious new analytical and process experimental techniques which are environmentally benign techniques, viz., ultrasound irradiation, have become immensely popular in promoting various reactions. In this work, a novel soluble multi-site phase transfer catalyst (PTC viz., 1,4-bis-(propylmethyleneammounium chloridebenzene (BPMACB was synthesized and its catalytic efficiency was assessed by observing the kinetics of sonolytic polymerization of methacrylic acid butyl ester (MABE using potassium persulphate (PPS as an initiator. The ultrasound–multi-site phase transfer catalysis (US-MPTC-assisted polymerization reaction was compared with the silent (non-ultrasonic polymerization reaction. The effects of the catalyst and various reaction parameters on the catalytic performance were in detail investigated by following the kinetics of polymerization of MABE in an ethyl acetate-water biphasic system. From the detailed kinetic investigation we propose a plausible mechanism. Further the kinetic results demonstrate clearly that ultrasound-assisted phase-transfer catalysis significantly increased the reaction rate when compared to silent reactions. Notably, this environmentally benign and cost-effective process has great potential to be applied in various polymer industries.

  17. 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.

  18. Molecular Characterization and Enhancement of Anticancer Activity of Caffeic Acid Phenethyl Ester by γ Cyclodextrin

    Science.gov (United States)

    Wadhwa, Renu; Nigam, Nupur; Bhargava, Priyanshu; Dhanjal, Jaspreet Kaur; Goyal, Sukriti; Grover, Abhinav; Sundar, Durai; Ishida, Yoshiyuki; Terao, Keiji; Kaul, Sunil C

    2016-01-01

    Caffeic Acid Phenethyl Ester (CAPE) is a key component in New Zealand propolis, known for a variety of health promoting and therapeutic potentials. We investigated the molecular mechanism of anticancer and anti-metastasis activities of CAPE. cDNA array performed on the control and CAPE-treated breast cancer cells revealed activation of DNA damage signaling involving upregulation of GADD45α and p53 tumor suppressor proteins. Molecular docking analysis revealed that CAPE is capable of disrupting mortalin-p53 complexes. We provide experimental evidence and demonstrate that CAPE induced disruption of mortalin-p53 complexes led to nuclear translocation and activation of p53 resulting in growth arrest in cancer cells. Furthermore, CAPE-treated cells exhibited downregulation of mortalin and several other key regulators of cell migration accountable for its anti-metastasis activity. Of note, we found that whereas CAPE was unstable in the culture medium (as it gets degraded into caffeic acid by secreted esterases), its complex with gamma cyclodextrin (γCD) showed high efficacy in anti-tumor and anti-metastasis assays in vitro and in vivo (when administered through either intraperitoneal or oral route). The data proposes that CAPE-γCD complex is a potent anti-cancer and anti-metastasis reagent. PMID:27698914

  19. Antioxidant Properties of Caffeic acid Phenethyl Ester and 4-Vinylcatechol in Stripped Soybean Oil.

    Science.gov (United States)

    Jia, Cai-Hua; Wang, Xiang-Yu; Qi, Jin-Feng; Hong, Soon-Taek; Lee, Ki-Teak

    2016-01-01

    Caffeic acid was used to synthesize 4-vinylcatechol (4-VC) by thermal decarboxylation and to prepare caffeic acid phenethyl ester (CAPE) by esterification reaction. The identities of synthesized products were confirmed by (1)H NMR. Antioxidative activities of 4-VC and CAPE were compared with α-tocopherol and BHT in stripped soybean oil at 60 °C under the dark. To evaluate the degrees of oxidation at different concentrations and combinations, peroxide value (PV) and (1)H NMR were performed. From the results of PV, the formation of primary oxidation products (i.e., hydroperoxides) in stripped soybean oil containing 200 ppm CAPE was the slowest. The relative oxidation degree of 200 ppm CAPE (9.5%) was lower than other samples on 9 d. Similar results were obtained by (1)H NMR analysis. After 15 d of storage, levels of conjugated diene forms and aldehydes of 200 ppm CAPE sample (57.3 and 0.9 mmol/mol oil) were also lower than other treatments. In addition, 4-VC and α-tocopherol were found to have a synergistic antioxidant effect. PMID:26641978

  20. Regulatory effects of caffeic acid phenethyl ester on neuroinflammation in microglial cells.

    Science.gov (United States)

    Tsai, Cheng-Fang; Kuo, Yueh-Hsiung; Yeh, Wei-Lan; Wu, Caren Yu-Ju; Lin, Hsiao-Yun; Lai, Sheng-Wei; Liu, Yu-Shu; Wu, Ling-Hsuan; Lu, Jheng-Kun; Lu, Dah-Yuu

    2015-01-01

    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. PMID:25768341

  1. Molecular Characterization and Enhancement of Anticancer Activity of Caffeic Acid Phenethyl Ester by γ Cyclodextrin

    Science.gov (United States)

    Wadhwa, Renu; Nigam, Nupur; Bhargava, Priyanshu; Dhanjal, Jaspreet Kaur; Goyal, Sukriti; Grover, Abhinav; Sundar, Durai; Ishida, Yoshiyuki; Terao, Keiji; Kaul, Sunil C

    2016-01-01

    Caffeic Acid Phenethyl Ester (CAPE) is a key component in New Zealand propolis, known for a variety of health promoting and therapeutic potentials. We investigated the molecular mechanism of anticancer and anti-metastasis activities of CAPE. cDNA array performed on the control and CAPE-treated breast cancer cells revealed activation of DNA damage signaling involving upregulation of GADD45α and p53 tumor suppressor proteins. Molecular docking analysis revealed that CAPE is capable of disrupting mortalin-p53 complexes. We provide experimental evidence and demonstrate that CAPE induced disruption of mortalin-p53 complexes led to nuclear translocation and activation of p53 resulting in growth arrest in cancer cells. Furthermore, CAPE-treated cells exhibited downregulation of mortalin and several other key regulators of cell migration accountable for its anti-metastasis activity. Of note, we found that whereas CAPE was unstable in the culture medium (as it gets degraded into caffeic acid by secreted esterases), its complex with gamma cyclodextrin (γCD) showed high efficacy in anti-tumor and anti-metastasis assays in vitro and in vivo (when administered through either intraperitoneal or oral route). The data proposes that CAPE-γCD complex is a potent anti-cancer and anti-metastasis reagent.

  2. 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.

  3. Antioxidant Properties of Caffeic acid Phenethyl Ester and 4-Vinylcatechol in Stripped Soybean Oil.

    Science.gov (United States)

    Jia, Cai-Hua; Wang, Xiang-Yu; Qi, Jin-Feng; Hong, Soon-Taek; Lee, Ki-Teak

    2016-01-01

    Caffeic acid was used to synthesize 4-vinylcatechol (4-VC) by thermal decarboxylation and to prepare caffeic acid phenethyl ester (CAPE) by esterification reaction. The identities of synthesized products were confirmed by (1)H NMR. Antioxidative activities of 4-VC and CAPE were compared with α-tocopherol and BHT in stripped soybean oil at 60 °C under the dark. To evaluate the degrees of oxidation at different concentrations and combinations, peroxide value (PV) and (1)H NMR were performed. From the results of PV, the formation of primary oxidation products (i.e., hydroperoxides) in stripped soybean oil containing 200 ppm CAPE was the slowest. The relative oxidation degree of 200 ppm CAPE (9.5%) was lower than other samples on 9 d. Similar results were obtained by (1)H NMR analysis. After 15 d of storage, levels of conjugated diene forms and aldehydes of 200 ppm CAPE sample (57.3 and 0.9 mmol/mol oil) were also lower than other treatments. In addition, 4-VC and α-tocopherol were found to have a synergistic antioxidant effect.

  4. Locally delivered salicylic acid from a poly(anhydride-ester): impact on diabetic bone regeneration.

    Science.gov (United States)

    Wada, Keisuke; Yu, Weiling; Elazizi, Mohamad; Barakat, Sandrine; Ouimet, Michelle A; Rosario-Meléndez, Roselin; Fiorellini, Joseph P; Graves, Dana T; Uhrich, Kathryn E

    2013-10-10

    Diabetes mellitus (DM) involves metabolic changes that can impair bone repair, including a prolonged inflammatory response. A salicylic acid-based poly(anhydride-ester) (SA-PAE) provides controlled and sustained release of salicylic acid (SA) that locally resolves inflammation. This study investigates the effect of polymer-controlled SA release on bone regeneration in diabetic rats where enhanced inflammation is expected. Fifty-six Sprague-Dawley rats were randomly assigned to two groups: diabetic group induced by streptozotocin (STZ) injection or normoglycemic controls injected with citrate buffer alone. Three weeks after hyperglycemia development or vehicle injection, 5mm critical sized defects were created at the rat mandibular angle and treated with SA-PAE/bone graft mixture or bone graft alone. Rats were euthanized 4 and 12weeks after surgery, then bone fill percentage in the defect region was assessed by micro-computed tomography (CT) and histomorphometry. It was observed that bone fill increased significantly at 4 and 12weeks in SA-PAE/bone graft-treated diabetic rats compared to diabetic rats receiving bone graft alone. Accelerated bone formation in normoglycemic rats caused by SA-PAE/bone graft treatment was observed at 4weeks but not at 12weeks. This study shows that treatment with SA-PAE enhances bone regeneration in diabetic rats and accelerates bone regeneration in normoglycemic animals.

  5. Ethyl pyruvate regulates the levels of leptin, lactin acid-pyruvic, ALT and UA in mice sepsis model

    International Nuclear Information System (INIS)

    To explore the effect of ethyl pyruvate (EP) on the serum levels of leptin, lactin acid to pyruvic acid ratio, ALT and UA in sepsis mice. The mice sepsis model of cecum ligation and perforation was established. The 90 male mice were divided randomly into sham-operation ( Sham), injury (RLS) and EP(REPS)-intervened groups, the latter two groups were further divided into 15 min, 1 h, 3 h and 6 h subgroups, each of them had 10 mice. The serum lactin acid to pyruvic acid ratio, ALT and UA were detected by autonomous biochemical analyzer, and the serum leptin were detected by RIA. The results showed that the serum leptin level in REPS group was significantly higher than that of in RLS group at the later phase (P<0.05). The ratio of lactin acid to pyruvic acid in RLS and REPS groups were significantly higher that of in sham group, but there is no significant different between REPS group and RLS group at same time points. The serum levels of ALT in RLS and REPS groups were significantly higher than that of in Sham group, and the serum level of ALT in REPS group at later time points was significantly higher than that of RLS group. Compared with Sham group, the serum UA in RLS group was increased significantly at first time points (P<0.05) and then decreased at later time points; the serum UA in REPS group was significantly lower than that of RLS group (P<0.05). The results indicated that EP may protect renal function, worsen hepatic injury at the early phase and up-regulate the serum leptin level. (authors)

  6. 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)

  7. Enhanced microemulsion formation in lipid-based drug delivery systems by combining mono-esters of medium-chain fatty acids with di- or tri-esters

    Directory of Open Access Journals (Sweden)

    Darshil P Patel

    2012-06-01

    Full Text Available To develop strategies for selecting appropriate lipids from mono-, di- and tri-esters of medium-chain fatty acids for the development of lipid-based drug delivery systems, ternary phase diagrams of propylene glycol(PG monocaprylate (Capryol® 90; HLB~7, PG dicaprylocaprate (Labrafac™PG; HLB~2 and glycerol tricaprylocaprate (Labrafac™Lipophile WL1349; HLB~2 were determined in combination with a commonsurfactant, PEG-35 castor oil (Cremophor®EL, HLB~13, and water. Particle size and viscosity in different regions of the phase diagrams were measured, solubility of a model drug, danazol, in different lipid-surfactant mixtures was determined, and dispersion testing by diluting selected preconcentrates with 250 ml 0.01 NHCl was performed. Further, phase diagrams were constructed using binary mixtures of lipids (monoester with diester, or monoester with triester in place of single lipids. The phase diagrams of PG dicaprylocaprate andglycerol tricaprylocaprate were similar, while it was distinctly different for PG monocaprylate. The microemulsion regions in phase diagrams were rather limited for individual lipids, and additionally, the diand tri-esters showed pronounced gel regions in the phase diagrams, which could influence drug release from preconcentrates. The mixing of PG monocaprylate (monoester with PG dicaprylocaprate (diester or glycerol tricaprylocaprate (triester had dramatic effects on the performance of lipids as evidenced by thegreatly reduced gel phases, much larger microemulsion regions, faster dispersion of the preconcentrates in an aqueous medium, and smaller particle size of the microemulsions subsequently formed.

  8. 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...

  9. The effects of a single oral dose of ethyl linoleate on urinary prostaglandin E excretion in essential fatty acid-deficient rats

    DEFF Research Database (Denmark)

    Hansen, Harald S.; Jensen, B.

    1985-01-01

    The effects of a single oral dose of ethyl linoleate on urinary prostaaglandin E (PGE) excretion and urine output were investigated in essential fatty acid (EFA)-deficient rats. Weanling male rats were fed a fat-free diet. After 13 wk of feeding, eight rats received an oral dose of 400 mg of ethy...

  10. 2-(Sulfooxy)propane-1,2,3-tricarboxylic acid as novel and versatile catalyst for the formylation of alcohols and amines using ethyl formate under neat conditions

    Institute of Scientific and Technical Information of China (English)

    Arash Ghorbani-Choghamarani; Ziba Akbaripanah

    2012-01-01

    2-(Sulfooxy)propane-1,2,3-tricarboxylic acid (supported on silica gel) has been introduced as novel and green catalyst for the formylation of alcohols and amines with ethyl formate,as mild formylation agent,under neat conditions at room temperature.

  11. 新型Lewis酸铁钾矾催化合成己酸乙酯%Catalytic Synthesis of Ethyl Caproate over New Lewis Acid Ferric Potassium Alum

    Institute of Scientific and Technical Information of China (English)

    郭小丹; 张福捐

    2012-01-01

    新型Lewis酸铁钾矾催化己酸和乙醇合成反应生成己酸乙酯,其性能优于硫酸,并且是一种绿色催化剂.研究了催化剂的用量、酸醇摩尔比、反应时间对酯化反应的影响.实验结果表明,较佳的反应条件为:催化剂用量1.0 g/0.05 mol己酸,酸醇物质的量比为1∶2.4,反应时间为100 min,此条件下己酸转化率为94.3%.%Ethyl caproate was synthesized from hexanoic acid and ethyl alcohol with new Lewis acid ferric potassium alum as catalyst.The factors of influencing esterification rate were investigated.The results showed that ferric potassium alum was a good green catalyst for synthesis of ethyl caproate.The optimum conditions were:molar ratio of hexanoic acid to ethyl alcohol was 1∶ 2.4,amount of catalyst was 1.0 g /0.05 mol hexanoic acid,the water-carrying toluene was 10 mL,and the reaction time was 100 min.The highest esterification rate was 94.3%,and the catalyst can be recycled for many times.

  12. Effects of caffeic acid phenethyl ester on palatal mucosal defects and tooth extraction sockets

    Directory of Open Access Journals (Sweden)

    Günay A

    2014-10-01

    Full Text Available Ahmet Günay,1 Osman Fatih Arpağ,2 Serhat Atilgan,3 Ferhan Yaman,3 Yusuf Atalay,4 İzzet Acikan3 1Department of Periodontology, Faculty of Dentistry, Dicle University, Diyarbakir, Turkey; 2Department of Periodontology, Faculty of Dentistry, Mustafa Kemal University, Hatay, Turkey; 3Department of Maxillofacial Surgery, Faculty of Dentistry, Dicle University, Diyarbakir, Turkey; 4Department of Maxillofacial Surgery, Faculty of Dentistry, Kocatepe University, Afyon, Turkey Aim: The purpose of this study was to evaluate the effects of caffeic acid phenethyl ester (CAPE on palatal mucosal defects and tooth extraction sockets in an experimental model.Materials and methods: Forty-two male Sprague-Dawley rats with a mean age of 7 weeks and weighing 280–490 g were used in this study. The rats were randomly divided into two groups: group A (the control group, n=21 and group B (the experimental group, n=21. Under anesthesia with ketamine (8 mg/100 g, intraperitoneally, palatal mucosal defects were created and tooth extraction was performed in the rats in groups A and B. Group A received no treatment, whereas group B received CAPE. CAPE was injected daily (10 µmol/kg, intraperitoneally. The rats were killed on days 7, 14, and 30 after the procedures. Palatal mucosa healing and changes in bone tissue and fibrous tissue were evaluated histopathologically.Result: Pairwise comparisons showed no statistically significant difference between days 7 and 14 in either group (P>0.05. At day 30, bone healing was significantly better in group B (CAPE than in group A (control (P<0.05. Fibrinogen levels at day 30 were significantly higher in group A (control than in group B (CAPE (P<0.05. Pairwise comparisons showed no statistically significant difference in palatal mucosa healing levels between days 7 and 14 in both groups (P>0.05.Conclusion: In conclusion, the findings of this study suggest that CAPE can significantly improve tooth socket healing. Keywords: caffeic

  13. 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. PMID:26321291

  14. Simultaneous microwave extraction and synthesis of fatty acid methyl ester from the oleaginous yeast Rhodotorula glutinis

    International Nuclear Information System (INIS)

    Microbial lipids have the potential to substantially reduce the use of liquid fossil fuels, though one obstacle is the energy costs associated with the extraction and subsequent conversion into a biofuel. Here we report a one-step method to produce FAME (fatty acid methyl esters) from Rhodotorula glutinis by combining lipid extraction in a microwave reactor with acid-catalysed transesterification. The microwave did not alter the FAME profile and over 99% of the lipid was esterified when using 25 wt% H2SO4 over 20 min at 120 °C. On using higher loadings of catalyst, similar yields were achieved over 30 s. Equivalent amounts of FAME were recovered in 30 s using this method as with a 4 h Soxhlet extraction, run with the same solvent system. When water was present at less than a 1:1 ratio with methanol, the main product was FAME, above this the major products were FFA (free fatty acids). Under the best conditions, the energy required for the microwave was less than 20% of the energy content of the biodiesel produced. Increasing the temperature did not change the EROI (energy return on investment) substantially; however, longer reaction times used an equivalent amount of energy to the total energy content of the biodiesel. - Highlights: • The extraction and transesterification of yeast lipid were achieved using a microwave reactor. • The lipid was extracted from Rhodotorula glutinis within 30 s under all conditions. • Addition of 25 wt% H2SO4 catalyst converted 95% glycerides to FAME over 5 min. • Water could be tolerated up to 25 wt% without high FFA production. • The temperature of the microwave had less impact on EROI than the length of extraction

  15. Abiotic degradation of four phthalic acid esters in aqueous phase under natural sunlight irradiation

    Institute of Scientific and Technical Information of China (English)

    Ruttapol Lertsirisopon; Satoshi Soda; Kazunari Sei; Michihiko Ike

    2009-01-01

    Abiotic degradability of four phthalic acid esters (PAEs) in the aquatic phase was evaluated over the wide pH range (5-9). The PAE solutions in glass test tubes were placed in the dark and under natural sunlight irradiation for evaluating the degradation rate via hydrolysis and photolysis plus hydrolysis, respectively, at ambient temperature for 140 d from autumn to winter in Osaka, Japan. The efficiency of abiotic degradation of the PAEs with relatively short alkyl chain, butylbenzyl phthalate (BBP) and di-n-butyl phthalate (DBP) at neutral pH was significant less than that in the acidic or alkaline condition. Photolysis was considered to mainly contribute to total abiotic degradation at any pH. Neither hydrolysis nor photolysis of di-ethylhexyl phthalate (DEHP) proceeded significantly at any pH, especially hydrolysis at neutral pH was negligible. On the other hand, the degradation rate of di-isononyl phthalate (DINP) mainly catalyzed by photolysis was much higher compared with that of the other PAEs, and almost complete removal was observed during the experimental period at pH 5.0 and 9.0. As a whole, according to the half-life (t1/2) obtained in the experiments, the abiotic degradability of the PAEs was in the sequence, DINP (32-140 d) > DBP (50-360 d), BBP (58-480 d) > DEHP (390-1600 d) under sunlight irradiation (via photolysis plus hydrolysis). Although the abiotic degradation rate for BBP, DBP, and DEHP are much lower than their biodegradation rate reported, the photolysis rate for DINP is comparable to its biodegradation rate in the acidic or alkaline condition.

  16. 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 catalys

  17. 21 CFR 178.3780 - Polyhydric alcohol esters of long chain monobasic acids.

    Science.gov (United States)

    2010-04-01

    ...) Saponification value 120-160 for the ethylene glycol ester and 90-130 for the glycerol ester as determined the A.O.C.S. method Trla-64T “Saponification Value,” which is incorporated by reference. Copies...

  18. Characterization of Mycolic Acids in Total Fatty Acid Methyl Ester Fractions from Mycobacterium Species by High Resolution MALDI-TOFMS.

    Science.gov (United States)

    Teramoto, Kanae; Suga, Mitsuo; Sato, Takafumi; Wada, Takayuki; Yamamoto, Atsushi; Fujiwara, Nagatoshi

    2015-01-01

    Mycolic acids (MAs) are characteristic components of bacteria in the suborder Corynebacterineae, such as Mycobacterium. MAs are categorized into subclasses based on their functional bases (cyclopropane ring, methoxy, keto, and epoxy group). Since MAs have heterogeneity among bacterial species, analyzing of MAs are required in the chemotaxonomic field. However, their structural analysis is not easy because of their long carbon-chain lengths and several functional groups. In this study, total fatty acid (FA) methyl ester (ME) fraction of M. tuberculosis H37Rv was analyzed by matrix-assisted laser desorption/ionization (MALDI) time-of-flight mass spectrometry (TOFMS) with a spiral ion trajectory (MALDI spiral-TOFMS). The distributions of carbon-chain length and their relative peak intensities were confirmed with those obtained by analysis of each subclass fraction which was separated from total FA ME fraction using thin-layer chromatography (TLC). The observed major peaks were reliably assigned as MAs owing to the high mass accuracy (errorodd-numbered carbon-chain MAs for the total FA ME fraction were consistent with those of MA subclass fractions. To visualize whole MAs, contour maps of relative peak intensities for whole MAs were created. The contour maps indicated the MA subclasses and their distributions of carbon-chains with relative peak intensities at a glance. Our proposed method allows simple characterization in a short time and thus enables the analysis of large numbers of samples, and it would contribute to the chemotaxonomy. PMID:26819906

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

    Science.gov (United States)

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

    2016-08-01

    Carbohydrate fatty acid esters are non-ionic surfactants with a broad spectrum of applications. These molecules are generally synthesized using short carbohydrates or linear fructans; however in this research carbohydrate fatty acid esters were produced for the first time with branched fructans from Agave tequilana. Using immobilized lipases we successfully acylated A. tequilana fructans with vinyl laurate, obtaining products with different degrees of polymerization (DP). Lipozyme 435 was the most efficient lipase to catalyze the transesterification reaction. HPLC and ESI-MS analysis proved the presence of a mixture of acylated products as a result of the chemical complexity of fructans in the A. tequilana. The ESI-MS spectra showed a molecular mass shift between 183 and 366g/mol for fructooligosaccharides with a DP lower than 6, which indicated the presence of Agave fructans that had been mono- and diacylated with lauric acid. The carbohydrate fatty acid esters (CFAE) obtained showed good emulsifying properties in W/O emulsions. PMID:26988522

  20. Fatty acid steryl, stanyl, and steroid esters by esterification and transesterification in vacuo using Candida rugosa lipase as catalyst.

    Science.gov (United States)

    Weber, N; Weitkamp, P; Mukherjee, K D

    2001-01-01

    Sterols (sitosterol, cholesterol, stigmasterol, ergosterol, and 7-dehydrocholesterol) and sitostanol have been converted in high to near-quantitative yields to the corresponding long-chain acyl esters via esterification with fatty acids or transesterification with methyl esters of fatty acids or triacylglycerols using lipase from Candida rugosa as biocatalyst in vacuo (20-40 mbar) at 40 degrees C. Neither organic solvent nor water is added in these reactions. Under similar conditions, cholesterol has been converted to cholesteryl butyrate and steroids (5alpha-pregnan-3beta-ol-20-one or 5-pregnen-3beta-ol-20-one) have been converted to their propionic acid esters, both in moderate to high yields, via transesterification with tributyrin and tripropionin, respectively. Reaction parameters studied in esterification include the temperature and the molar ratio of the substrates as well as the amount and reuse properties of the C. rugosa lipase. Lipases from porcine pancreas, Rhizopus arrhizus, and Chromobacterium viscosum are quite ineffective as biocatalysts for the esterification of cholesterol with oleic acid under the above conditions.

  1. Unequivocal NMR assignments: O-methoxy-methyl esters derivatives of acid chromanones from Calophyllum brasiliense CAMB. (Guanandi).

    Science.gov (United States)

    Caneppele, D; Vieira, P C; Dall'Oglio, E L; da Silva, L E; Sousa, P T

    2008-01-01

    The present work describes the fractionation of the crude hexane extract (EBHEX) from Calophyllum brasiliense (Clusiaceae) stem bark. Derivatization of DCM(2-9) fraction with diazomethane afforded the chromanones inophylloidic acid, isobrasiliensic acid, as well as, a mixture containing isobrasiliensic and brasiliensic acids, in the form of their more stable O-methoxy-methyl esters derivatives 1, 2, and 3, respectively. The isolation of 1 from C. brasiliense is described for the first time herein. The use of two-dimensional NMR methods ((1)H-COSY, HMQC, and HMBC) allowed the precise determination of (13)C and (1)H chemical shifts of compounds 1, 2, and 3. PMID:18626818

  2. A database of chromatographic properties and mass spectra of fatty acid methyl esters from omega-3 products.

    Science.gov (United States)

    Wasta, Ziar; Mjøs, Svein A

    2013-07-19

    Fatty acids in products claimed to contain oils with the omega-3 fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) were analyzed as fatty acid methyl esters by gas chromatography-mass spectrometry using electron impact ionization. To cover the variation in products on the market, the 20 products that were studied in detail were selected from a larger sample set by statistical methodology. The samples were analyzed on two different stationary phases (polyethylene glycol and cyanopropyl) and the fatty acid methyl esters were identified by methodology that combines the mass spectra and retention indices into a single score value. More that 100 fatty acids had a chromatographic area above 0.1% of the total, in at least one product. Retention indices are reported as equivalent chain lengths, and overlap patterns on the two columns are discussed. Both columns were found suitable for analysis of major and nutritionally important fatty acids, but the large number of minor compounds that may act as interferents will be problematic if low limits of quantification are required in analyses of similar sample types. A database of mass spectral libraries and equivalent chain lengths of the detected compounds has been compiled and is available online. PMID:23773584

  3. Study on the Mechanism of Interaction between Phthalate Acid Esters and Bovine Hemoglobin.

    Science.gov (United States)

    Chi, Zhenxing; Zhao, Jing; You, Hong; Wang, Mingjing

    2016-08-01

    Phthalate acid esters (PAEs) are widely used in plastic products as a series of chemical softeners. However, PAEs, which now exist in many environmental media such as the atmosphere, water, and soil, have been shown to be environmental endocrine disruptors. Hemoglobin is a functional protein that carries oxygen in the red blood cells of animals. This study aims at revealing the interactions between bovine hemoglobin (BHb) and PAEs using spectroscopic and molecular modeling methods. The results indicate that the selected representative PAEs-dimethyl phthalate (DMP), diethyl phthalate (DEP), and dibutyl phthalate (DBP)-can interact with BHb to form BHb-PAE complexes with one binding site, mainly relying on hydrophobic forces, with the affinity order DMP > DEP > DBP, opposite to the order of side-chain length. The binding of PAEs can cause conformational and micro-environmental changes in BHb, which may affect the physiological functions of Hb. Furthermore, molecular docking was applied to define the specific binding sites, the results of which show that all the three PAEs can bind into the central cavity of BHb. The study contributes to expound the toxic mechanism of PAEs in vivo from the point of hematological toxicology. PMID:27379662

  4. 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.

  5. Effects of caffeic acid phenethyl ester on proliferation of vascular smooth muscle cells in rats

    Institute of Scientific and Technical Information of China (English)

    Gang Yang; Chao Chang; YuQing Wang; Yibo Feng; ShuLing Rong

    2006-01-01

    Objective: To investigate the inhibitory effect of caffeic acid phenethyl ester(CAPE) on the proliferation of vascular smooth muscle cells (VSMC) activated by lipopolysaccharide (LPS) and to clarify its mechanism. Methods: VSMC activated by LPS (1 mg·L-1) were treated with CAPE at different concentrations. The inhibitory effects of CAPE on the proliferation of VSMC were determined by methabenzthiazuron(MTT) colorimetry. The effects of CAPE on the expression of proliferating cell nuclear antigen (PCNA) and Survivin protein in VSMC were evaluated by immunocytochemistry staining technique (SABC method). Cell cycle was analyzed by flow cytometry(FCM) with propidium iodide (PI) labeling method. The relative expression level of Survivin mRNA was measured with real-time quantified RT-PCR technique. Results: CAPE exerted significant inhibitory effects on. proliferation of VSMC at concentrations ranging from 5 mg·L-1 to 80 mg·L-1, decreased the rate of cells positive for PCNA and Survivin protein and repressed the expression of Survivin mRNA in a dose- and time-dependent manner (P < 0.05).FCM analysis displayed that CAPE up-regulated the ratio of G0/G1 stages and reduced the percentage of VSMC in S stage (P <0.05). Conclusion: CAPE can significantly inhibit the proliferation of VSMC activated by LPS in a dose- and time-dependent manner, which may be carried out through regulating cell cycle and repressing the expression of PCNA and Survivin.

  6. 脂肪酸甲酯磺酸盐%Fatty acid methyl ester sulfonate

    Institute of Scientific and Technical Information of China (English)

    韩建英

    2012-01-01

    Fatty acid methyl ester sulfonate(MES) is an anionic surfactant based on natural oils generated from plant and animal as raw materials. MES has good detergency, lime soap dispersing ability, hard water-resistance, emulsibility, water-solubility and biodegradability; besides, it can improve the solubility of soap in water. Because of the good performance of MES, it can be used in synthetic powder detergent, compound soap powder, composite soap, shampoo and personal care products. The present production situation, product forms, properties as well as applications of MES were related.%脂肪酸甲酯磺酸盐简称(MES)是以天然动植物油脂为原料制得的脂肪酸系阴离子表面活性剂。它具有良好的去污性、钙皂分散性、抗硬水性、乳化性、增溶性和生物降解性,并能改进肥皂的溶解性。由于MES性能优良,主要用于合成洗衣粉、复合皂粉、复合肥皂、香波以及个人清洁用品中。对MES的生产现状、产品形式、性能以及应用进行了概述。

  7. Negative polarity of phenyl-C61 butyric acid methyl ester adjacent to donor macromolecule domains

    International Nuclear Information System (INIS)

    Interfacial fields within organic photovoltaics influence the movement of free charge carriers, including exciton dissociation and recombination. Open circuit voltage (Voc) can also be dependent on the interfacial fields, in the event that they modulate the energy gap between donor HOMO and acceptor LUMO. A rise in the vacuum level of the acceptor will increase the gap and the Voc, which can be beneficial for device efficiency. Here, we measure the interfacial potential differences at donor-acceptor junctions using Scanning Kelvin Probe Microscopy, and quantify how much of the potential difference originates from physical contact between the donor and acceptor. We see a statistically significant and pervasive negative polarity on the phenyl-C61 butyric acid methyl ester (PCBM) side of PCBM/donor junctions, which should also be present at the complex interfaces in bulk heterojunctions. This potential difference may originate from molecular dipoles, interfacial interactions with donor materials, and/or equilibrium charge transfer due to the higher work function and electron affinity of PCBM. We show that the contact between PCBM and poly(3-hexylthiophene) doubles the interfacial potential difference, a statistically significant difference. Control experiments determined that this potential difference was not due to charges trapped in the underlying substrate. The direction of the observed potential difference would lead to increased Voc, but would also pose a barrier to electrons being injected into the PCBM and make recombination more favorable. Our method may allow unique information to be obtained in new donor-acceptor junctions

  8. Combustion characteristics of fatty acid methyl esters derived from recycled cooking oil

    Energy Technology Data Exchange (ETDEWEB)

    Yo-ping Greg Wu; Ya-fen Lin; Chang-Tang Chang [National Ilan University, Ilan (Taiwan). Department of Chemical and Materials Engineering

    2007-12-15

    The goal of this study is to find out the exhaust emissions differences produced by different kinds of fatty acid methyl esters (FAME) derived from used cooking oils and animal fats, as well as the importance of the purification step in exhaust emissions production. A total of 120 L of waste vegetable oil and 30 L of waste frying oil were collected and converted into three batches of FAME. There were two batches of FAME produced from waste vegetable oil (B01 and B02), and one batch of FAME produced by mixing 2% of waste frying oil with waste vegetable oil (B03). The FAMEs used in this study had higher density, kinematic viscosity, and flash point, but a lower gross heating value, when compared to the premium diesel. The B01 engine produced higher CO formation and the diesel-fuelled engine produced higher CO than the B02 and B03 did for engine speeds higher than 1400 rpm. Most of the FAME fuels produced higher CO{sub 2} than the diesel fuel did. The FAME fuels emitted higher NOx and PM, but lower SO{sub 2}, than the diesel fuel. C{sub n}H{sub 2n+2}, diphenyl sulfone (C{sub 12}H{sub 10}O{sub 2}S), and diethyl phthalate (C{sub 12}H{sub 14}O{sub 4}) can be selected as the character index for the combustion of FAME. 26 refs., 8 figs., 1 tab.

  9. EFFECTS OF EXERCISE AND CAFFEIC ACID PHENETHYL ESTER AFTER CHRONIC EXERCISE RAT MODEL

    Directory of Open Access Journals (Sweden)

    Ayse Alp

    2011-01-01

    Full Text Available In order to understand whether exercise and caffeic acid phenethyl ester (CAPE has an effect on obesity and weight control, we investigated the effects of CAPE, and exercise on lipid parameters (triglyceride, total cholesterol, HDL-C, LDL-C, and adipokine substances such as leptin and resistin in rats. 40 male rat were randomly assigned into 4 groups. It was determined that CAPE does not have any significant effect on these parameters but that lipid parameters and leptin values in exercise groups decreased considerably, while no significant change occurred in resistin levels. In order to understand whether diet has an effect on exercise, body weights of all animal groups in pre and post-exercise were compared. A significant weight gain was observed (p = 0.005 in all groups. This study concluded that exercise has a considerable effect on leptin and lipid parameters; however, exercise alone was not sufficient for weight control and could be effective in weight control only when accompanied by a restricted diet.

  10. 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.

  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. 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.

  13. Biodegradability of four phthalic acid esters under anaerobic condition assessed using natural sediment

    Institute of Scientific and Technical Information of China (English)

    Ruttapol Lertsirisopon; Satoshi Soda; Kazunari Sei; Michihiko Ike; Masanori Fujita

    2006-01-01

    Biodegradability of di-n-butyl phthalate (DBP), butylbenzyl phthalate (BBP), di-ethylhexyl phthalate (DEHP), and di-isononyl phthalate (DINP) under an anaerobic condition was evaluated using three natural sediment microcosms obtained from ponds in Osaka, which had not been significantly polluted by the chemicals. The degradabilities of the four phthalic acid esters(PAEs)were analyzed by a first-order kinetic model with a lag phase and ranked as DBP>BBP>>DEHP>DINP. The PAEs with shorter alkyl-chains, DBP and BBP, were degraded with quite short lag phases near to zero and short half-lives of a few days. The PAEs with longer alkyl-chains, DEHP and DINP, were degraded with lag phases of 5-30 d and the quite long half-lives of a couple of hundred days. Although no data was available on the anaerobic biodegradability of DINP before this study, it was clarified that DINP can be degraded with slow degradation rates. The fact that all the three intact sediments were capable of biodegradation of the PAEs suggests that potential of anaerobic biodegradation of PAEs is widespread in the aquatic environment.

  14. 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.

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

    Science.gov (United States)

    Su, Erzheng; Wei, Dongzhi

    2014-07-01

    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.

  16. Kinetics of enzymatic synthesis of liquid wax ester from oleic acid and oleyl alcohol.

    Science.gov (United States)

    Radzi, Salina Mat; Mohamad, Rosfarizan; Basri, Mahiran; Salleh, Abu Bakar; Ariff, Arbakariya; Rahman, Mohammad Basyaruddin Abdul; Rahman, Raja Noor Zaliha Raja Abdul

    2010-01-01

    The kinetics of wax ester synthesis from oleic acid and oleyl alcohol using immobilized lipase from Candida antartica as catalyst was studied with different types of impeller (Rushton turbine and AL-hydrofoil) to create different mixing conditions in 2l stirred tank reactor. The effects of catalyst concentration, reaction temperature, and impeller tip speed on the synthesis were also evaluated. Rushton turbine impeller exhibited highest conversion rate at lower impeller tip speed as compared to AL-hydrofoil impeller. A second-order reversible kinetic model from single progress curve for the prediction of fractional conversion at given reaction time was proposed and the corresponding kinetic parameter values were calculated by non-linear regression method. The results from the simulation using the proposed model showed satisfactory agreement with the experimental data. Activation energy shows a value of 21.77 Kcal/mol. The thermodynamic parameters of the process, enthalpy and entropy, were 21.15 Kcal/mol and 52.07 cal/mol.K, respectively.

  17. Kinetics of phenolic and phthalic acid esters biodegradation in membrane bioreactor (MBR) treating municipal landfill leachate.

    Science.gov (United States)

    Boonnorat, Jarungwit; Chiemchaisri, Chart; Chiemchaisri, Wilai; Yamamoto, Kazuo

    2016-05-01

    The kinetic of phenolic and phthalic acid esters (PAEs) biodegradation in membrane bioreactor (MBR) treating municipal landfill leachate was investigated. Laboratory-scale MBR was fed with mixture of fresh and stabilized landfill leachate containing carbon to nitrogen (C/N) ratio of 10, 6, 3 and operated under different solid retention time (SRT) of 90, 15 and 5 d. Batch experiments using MBR sludge obtained from each steady-state operating condition revealed highest biodegradation rate constant (k) of 0.059-0.092 h(-1) of the phenolic and PAEs compounds at C/N of 6. Heterotrophic bacteria were the major group responsible for biodegradation of compounds whereas the presence of ammonia-oxidizing bacteria (AOB) helped accelerating their removals. Heterotrophic nitrifying bacteria found under high ammonia condition had an important role in enhancing the biodegradation of phenols and PAEs by releasing phenol hydroxylase (PH), esterase (EST) and phthalate dioxygenase (PDO) enzymes and the presence of AOB helped improving biodegradation of phenolic and PAEs compounds through their co-metabolism. PMID:26908045

  18. Early Treatment of radiation-Induced Heart Damage in Rats by Caffeic acid phenethyl Ester

    International Nuclear Information System (INIS)

    The study designed to determine the therapeutic effect of caffeic acid phenethyl ester (CAPE) in minimising radiation-induced injuries in rats. Rats were exposed to 7 Gy γ-rays, 30 minutes later; rats were injected with CAPE (10μmol/ kg body, i.p.) for 7 consecutive days. Rats were sacrificed at 8 and 15 days after starting the experiment. Gamma-irradiation induced significant increase in malonaldehyde (MDA) level and xanthine oxidase (XO) and adenosine deaminase (ADA) activities, and significant decrease in total nitrate/nitrate (NO (x)) level and glutathione peroxidise (Gpx), superoxide dismutase (SOD)and catalase (CAT) activities in heart tissue and augmented activities of lactate dehydrogenase (LDH), creatine phosphokinase (CPK) and aspartate transaminase (AST) in serum. Irradiated rats early treated with CAPE showed significant decrease in MDA, XO and ADA and significant increase in group. Cardiac enzymes were restored. Conclusion, CAPE could exhibits curable effect on gamma irradiation-induced cardiac-oxidative impairment in rats. (Author)

  19. In vitro antifungal potentials of bioactive compound oleic acid, 3-(octadecyloxy) propyl ester isolated from Lepidagathis cristata Willd. (Acanthaceae) inflorescence

    Institute of Scientific and Technical Information of China (English)

    Maghdu Nainamohamed Abubacker; Palaniyappan Kamala Devi

    2014-01-01

    Objective: To identify bioactive compound oleic acid, 3-(octadecyloxy) propyl ester from Lepidagathis cristata Willd. (L. cristata) and to assess antifungal potentials of the isolated compound. Methods: Aqueous extracts of L. cristata inflorescence were used for this study. The major bioactive compound isolated was tested for antifungal activities. Results: The major bioactive compound oleic acid, 3-(octadecyloxy) propyl ester was isolated from the inflorescence of L. cristata. The bioactive compound was tested for antifungal potentials and found to be highly effective to plant pathogenic fungi Colletotrichum fulcatum NCBT 146, Fusarium oxysporum NCBT 156 and Rhizoctonia solani NCBT 196 as well as for the human pathogenic fungi Curvularia lunata MTCC 2030 and Microsporum canis MTCC 2820. Conclusions: The results justify the antifungal potentials of both plant and human pathogenic fungi. The plant bioactive compound will be helpful in herbal antifungal formulations.

  20. Synthesis and Antioxidant Evaluation of Enantiomerically Pure Bis-(1,2,3-triazolylmethylamino Esters from Modified α-Amino Acids

    Directory of Open Access Journals (Sweden)

    Juan I. Sarmiento-Sánchez

    2014-01-01

    Full Text Available The efforts for synthesis of enantiomerically pure bis-(1,2,3-triazolylmethylamino esters 6 are reported in good yields from an in situ generated α-azidomethyl ketone. Optimum experimental conditions were established for preparation of α-halomethyl ketones 10 and α-N,N-dipropargylamino esters 11, all derived from α-amino acids. The starting materials reacted under conventional click chemistry conditions, revealing a specific reactivity of bromomethyl ketones over chloromethyl ketones. The antioxidant activity of compounds 6 was assayed by DPPH method. The compound 6c with an IC50 of 75.57 ± 1.74 μg mL−1 was the most active. Technically, this methodology allows the preparation of a combinatorial library of analogues with different structural characteristics depending on the nature of the modified α-amino acids employed in the synthesis.

  1. Self-assembled structure of alkyloxy substituted benzoic acid methyl ester on HOPG:An STM study

    Institute of Scientific and Technical Information of China (English)

    YUAN Qunhui; LU Jun; WAN Lijun; BAI Chunli

    2004-01-01

    Self-assembled structures of 3,4,5-tris-dodecy- loxy benzoic acid methyl ester (E12), 3,4,5-tris-tetradecy- loxy-benzoic acid methyl ester (E14) and their mixture (E12/E14) have been studied on HOPG by scanning tunneling microscopy (STM). Dimer-like patterns induced by dipole-dipole interaction are observed in E12 and E14 monolayers. The molecules form close-packed rows and interdigitate with the alkyl chains in adjacent molecules. The structural differences are proposed to be from the different length of substituted alkyl chains. Owing to similar adsorption energy, phase separation is observed in the E12 and E14 mixed adlayer with different domains.

  2. Poly(ester amide)s based on (L)-lactic acid oligomers and α-amino acids: influence of the α-amino acid side chain in the poly(ester amide)s properties.

    Science.gov (United States)

    Fonseca, Ana C; Coelho, Jorge F J; Valente, Joana F A; Correia, Tiago R; Correia, Ilídio J; Gil, Maria H; Simões, Pedro N

    2013-01-01

    Novel biodegradable and low cytotoxic poly(ester amide)s (PEAs) based on α-amino acids and (L)-lactic acid (L-LA) oligomers were successfully synthesized by interfacial polymerization. The chemical structure of the new polymers was confirmed by spectroscopic analyses. Further characterization suggests that the α-amino acid plays a critical role on the final properties of the PEA. L-phenylalanine provides PEAs with higher glass transition temperature, whereas glycine enhances the crystallinity. The hydrolytic degradation in PBS (pH = 7.4) at 37 °C also depends on the α-amino acid, being faster for glycine-based PEAs. The cytotoxic profiles using fibroblast human cells indicate that the PEAs did not elicit an acute cytotoxic effect. The strategy presented in this work opens the possibility of synthesizing biodegradable PEAs with low citotoxicity by an easy and fast method. It is worth to mention also that the properties of these materials can be fine-tuned only by changing the α-amino acid.

  3. 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.

  4. Electrospun Scaffolds from Low Molecular Weight Poly(ester amide)s Based on Glycolic Acid, Adipic Acid and Odd or Even Diamines

    OpenAIRE

    Sara Keiko Murase; Luís Javier del Valle; Jordi Puiggalí

    2015-01-01

    Electrospinning of regular poly(ester amide)s (PEAs) constituted by glycolic acid, adipic acid and diamines with five and six carbon atoms has been carried out. Selected PEAs were constituted by natural origin products and could be easily prepared by a polycondensation method that avoids tedious protection and deprotection steps usually required for obtaining polymers with a regular sequence. Nevertheless, the synthesis had some limitations that mainly concerned the final low/moderate molecul...

  5. S-(−)-10,11-Dihydroxyfarnesoic Acid Methyl Ester Inhibits Melanin Synthesis in Murine Melanocyte Cells

    OpenAIRE

    Seung-Hwa Baek; Jun-Won Ahn; Sung-Hee Nam; Cheol-Sik Yoon; Jae-Cheon Shin; Sang-Han Lee

    2014-01-01

    The development of antimelanogenic agents is important for the prevention of serious aesthetic problems such as melasmas, freckles, age spots, and chloasmas. In the course of screening for melanin synthesis inhibitors, we found that the culture broth from an insect morphopathogenic fungus, Beauveria bassiana CS1029, exhibits potent antimelanogenic activity. We isolated and purified an active metabolite and identified it as S-(−)-10,11-dihydroxyfarnesoic acid methyl ester (dhFAME), an insect j...

  6. Analysis of. gamma. -radiolysis products of aqueous solutions of esters of aliphatic amino acids by the PMR method

    Energy Technology Data Exchange (ETDEWEB)

    Panin, V.I.; Sidorov, P.S.; Usatyi, A.F.

    1987-09-01

    The ..gamma..-radiolysis of aqueous solutions of methyl esters of aliphatic amino acids and peptides was investigated by the method of nuclear (proton) magnetic resonance (PMR). The resonance lines appearing in the PMR spectra of the irradiated systems were identified, and a conclusion was drawn about the molecular structure of the radiolysis products. The kinetics of the accumulation of radiolysis products was studied, and the values of their radiation yields were estimated.

  7. 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)

  8. Synthesis of insecticidal sucrose esters

    Institute of Scientific and Technical Information of China (English)

    Song Zi-juan; Li Shu-jun; Chen Xi; Liu Li-mei; Song Zhan-qian

    2006-01-01

    Some synthetic sucrose esters (SE) are a relatively new class of insecticidal compounds produced by reacting sugars with fatty acids, which are safe for the environment. Especially, sucrose esters composed of C6-C12 fatty acids have desirable insecticidal properties against many soft-bodied arthropod pests. In our study, sucrose octanoate which has the highest activity against a range of arthropod species was synthesized by a trans-esterification method and proved its insecticidal property. Under the condition of a homogeneous liquid, sucrose octanoate was prepared by reacting ethyl octanoate with sucrose at reduced pressure; the yield was 79.11%. Sucrose octanoate synthesized was identified and its property analyzed by IR, TLC and spectrophotometric analysis. It was shown that the ratio of monoester to polyester in sucrose octanoate was 1.48:1. The insecticidal activity of the synthetic sucrose octanoate was evaluated at a concentration of 4 and 8 mg·mL-1. The mortality of first-instar larvae ofLymantria dispar from its contact toxicity was 72.5% after 36 hours, the revision insect reduced rate of Aphis glycines reached above 80% at 4 and 8 mg·mL-1 after being treated for 5 days. Since the SE products are nontoxic to humans and higher animals, fully biodegradable and hydrolyzed to readily metabolizable sucrose and fatty acid, they are not harmful to crops and appear to be good insecticide candidates.

  9. Catalytic Synthesis of Hexanoic Acid 2-(Diethylamino) Ethyl Este with Copper Sulfate%硫酸铜催化合成己酸二乙氨基乙醇酯的研究

    Institute of Scientific and Technical Information of China (English)

    张豫黎; 代本才; 霍萃萌; 朱向珺; 李岩

    2011-01-01

    Copper sulfate was used as catalyst in the synthesis of hexanoic acid 2-(diethylamino) ethyl este. The optimized condition was obtained: the mole ratio of hexanoic acid, N,N-diethyl ethanolamine and copper sulfate is l:l.3:0.02,reaction tempreture is 155~160 ℃,reaction time is 2 h, the yielding of the ester could reach 95.2 %.Copper suffate can be reused for times without any less of catalytic activity.%在硫酸铜催化剂存在下,由己酸和二乙氨基乙醇合成了己酸二乙氨基乙醇酯,当己酸、二乙氨基乙醇和硫酸铜的物质的量之比为1∶1.3∶0.02,在155~160℃条件下回流2 h,酯的收率达95.2%.硫酸铜重可复使用多次,催化活性没有明显下降.

  10. 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.

  11. Synthesis and Biological Activity of New Pyrethroid Acid Oxime-esters Containing Pyrazole Ring

    Institute of Scientific and Technical Information of China (English)

    MA Jun-an; HUANG Run-qiu; FENG Lei; SONG Jian; QIU De-wen

    2003-01-01

    A series of compounds containing oxime-ester linkage and pyrazole ring(in place of the ester linkage and the alcohol moiety in pyrethroid ester) was designed and synthesized. The structures of all the compounds prepared were confirmed by 1H NMR and MS spectroscopy as well as elemental analyses. The bioassay data of those compounds against tobacco mosaic virus(TMV), cucumber mosaic virus(CMV), potato virus X(PVX) and potato virus Y(PVY) were presented. Among them compound 6i was found to possess significant plant antiviral activities. But all the compounds showed low insecticidal and acaricidal activities.

  12. 微波催化合成三乙醇胺双硬脂酸酯季铵盐%Study on microwave catalysis in preparation of quaternized triethanolamine double stearic acid ester

    Institute of Scientific and Technical Information of China (English)

    郑革

    2013-01-01

    Using microwave catalysis, the triethanolamine stearic acid ester was synthesized by the stea-ric acid and triethanolamine, and the optimum conditions of the esterification were determined by the orthogonal experimental design. The influences of reaction time, microwave power, ratio of stearic acid to triethanolamine on the esterization yield were discussed. The esterification products were separated by column chro-matogram, and the eluent was methanol and chloroform with 1:4 of volume ratio. The contents percent of the stearic acid monoesteramine, diesteramine and triesteramine were 30.3%, 65.1%, 4.6%. Quaternized triethanolamine double stearic acid ester was synthesized by the triethanolamine double stearic acid ester and di-ethyl sulphate. The relative performance of the product was determined.%以硬脂酸和三乙醇胺为原料,微波催化下合成了三乙醇胺硬脂酸酯,利用正交试验优化了酯化的反应条件,考察了酯化反应时间、微波功率、n(硬脂酸)∶n(三乙醇胺)等因素对酯化率的影响.采用色谱柱对酯化产品进行分离,洗脱液为甲醇和氯仿[V(甲醇):V(氯仿)=1∶4],三乙醇胺单硬脂酸酯、三乙醇胺双硬脂酸酯和三乙醇胺三硬脂酸酯的含量分别为30.3%、65.1%、4.6%.以硫酸二乙酯为季铵化试剂,与三乙醇胺双硬脂酸酯合成了季铵盐,并对产品的相关性能进行了测定.

  13. High sensitive extraction-spectrophotometric determination of ruthenium(II) with 3-(2-pyridy1)-5,6-dipheny1-1,2,4-triazine and tetrabromophenolphthalein ethyl ester

    International Nuclear Information System (INIS)

    A sensitive method for the spectrophotometric determination of ruthenium(II) has been developed. Ru(II) reacts with 3-(2-pyridyl)-5,6-diphenyl-1,2,4-triazine (PDT) in aqueous solution by heating at 850C and pH 4--5 for 1 h, to form a 1 : 2 complex cation which can be extracted into 1,2-dichloroethane (DCE) as an ion associate with tetrabromophenolphthalein ethyl ester (TBPE). The recommended procedure is as follows; transfer the sample solution (up to 25μg), 2 ml of buffer solution (pH 4.5), 1.5 ml of 5 x 10-3 M PDT solution and water to a 50 ml volumetric flask. Heat it in a water bath at 850C for 1 h. After cooling, add 10 ml of buffer solution (pH 4.5) and 1.5 ml of 3 x 10-3 M TBPE solution, and dilute to 50 ml with water. And shake the solution for 5 min with 10 ml of DCE in a 100 ml separatory funnel. After phase separation, centrifuge the organic phase to remove droplets of water. Measure the absorbance of the extracts at 610 nm against water or reagent blank as a reference. Calibration graphs are linear over the range 0--0.1 ppm of Ru(II) and the apparent molar absorptivity of the ion associate is 1.25 x 105 l mol-1 cm-1. The extracted associate has a molar ratio of Ru : PDT : TBPE=1 : 2 : 1. The tolerance of coexisting transition metal ions which cause enormous positive errors can be increased by adding masking reagents such as EDTA. Ruthenium in the prepared samples and ruthenium catalysts was determined sensitively and selectively by this method. (author)

  14. 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...

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

    DEFF Research Database (Denmark)

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

    2011-01-01

    The present study aimed to investigate the effects of 2-hydroxy-4-(methylthio)-butanoic acid isopropyl ester (HMBi) supplementation on splanchnic AA metabolism, essential AA (EAA) mobilization, and plasma AA status in postpartum transition dairy cows. The EAA mobilization was calculated by differ...... the first 29 DIM. Extra-splanchnic EAA mobilization can be crucial to sustain milk protein yield in the postpartum transition period and HMBi is a fast-working Met source that can improve Met status of postpartum transition cows.......The present study aimed to investigate the effects of 2-hydroxy-4-(methylthio)-butanoic acid isopropyl ester (HMBi) supplementation on splanchnic AA metabolism, essential AA (EAA) mobilization, and plasma AA status in postpartum transition dairy cows. The EAA mobilization was calculated...... by difference: EAA excretion in milk protein − net portal absorption of EAA or net splanchnic release of EAA. Eight Holstein cows fitted with permanent indwelling catheters in the hepatic portal vein, hepatic vein, mesenteric vein, and an artery in the dry period preceding second parturition were used...

  16. Very-long-chain 3-hydroxy fatty acids, 3-hydroxy fatty acid methyl esters and 2-alkanols from cuticular waxes of Aloe arborescens leaves.

    Science.gov (United States)

    Racovita, Radu C; Peng, Chen; Awakawa, Takayoshi; Abe, Ikuro; Jetter, Reinhard

    2015-05-01

    The present work aimed at a comprehensive chemical characterization of the cuticular wax mixtures covering leaves of the monocot species Aloe arborescens. The wax mixtures were found to contain typical aliphatic compound classes in characteristic chain length distributions, including alkanes (predominantly C31), primary alcohols (predominantly C28), aldehydes (predominantly C32), fatty acid methyl esters (predominantly C28) and fatty acids (bimodal distribution around C32 and C28). Alkyl esters ranging from C42 to C52 were identified, and found to mainly contain C28 alcohol linked to C16-C20 acids. Three other homologous series were identified as 3-hydroxy fatty acids (predominantly C28), their methyl esters (predominantly C28), and 2-alkanols (predominantly C31). Based on structural similarities and homolog distributions, the biosynthetic pathways leading to these novel wax constituents can be hypothesized. Further detailed analyses showed that the A. arborescens leaf was covered with 15 μg/cm(2) wax on its adaxial side and 36 μg/cm(2) on the abaxial side, with 3:2 and 1:1 ratios between epicuticular and intracuticular wax layers on each side, respectively. Terpenoids were found mainly in the intracuticular waxes, whereas very-long-chain alkanes and fatty acids accumulated to relatively high concentrations in the epicuticular wax, hence near the true surface of the leaf. PMID:25200334

  17. Synthesis of bio-additives: transesterification of ethyl acetate with glycerol using homogeneous or heterogeneous acid catalysts

    Energy Technology Data Exchange (ETDEWEB)

    Meireles, Bruno A.; Pereira, Vera Lucia P., E-mail: patrocinio@nppn.ufrj.br [Universidade Federal do Rio de Janeiro (UFRJ), RJ (Brazil). Centro de Ciencias da Saude. Nucleo de Pesquisas de Produtos Naturais

    2013-01-15

    A new catalytic route with potential practical interest to sustainable production of bioadditives from glycerol is described. Ethyl acetate was transesterified with glycerol, in the ratio glycerol:EtOAc 1:10, at 25 or 90 deg C using 0.1 equiv.of H{sub 2}SO{sub 4} or TsOH, as homogeneous catalysts. H{sub 2}SO{sub 4} led to the total glycerol consumption in 2 h. In the equilibrium, attained in 9 h, 100% yield of a diacetin:triacetin (55:45) mixture was formed. Using Amberlyst Registered-Sign 15 dry and Amberlyst Registered-Sign 16 wet in 1:30 glycerol:EtOAc ratio and reflux at 90 Degree-Sign C the total glycerol consumption was achieved in 2 and 10h, respectively. The lower reactivity of Amberlyst-16 wet was explained in terms of deactivation of acid sites and decrease in glycerol diffusion to the inner resin pores, both factors caused by adsorbed water. The kinetics of glycerol transformation and product distribution in the equilibrium in relation to the H{sub 2}SO{sub 4}, Amberlyst-15 (dry) and Amberlyst-16 (wet) catalyzed reactions were measured. (author)

  18. Corrosion Mitigation of Copper in Acidic Chloride Pickling Solutions by 2-Amino-5-ethyl-1,3,4-thiadiazole

    Science.gov (United States)

    Sherif, El-Sayed M.

    2010-08-01

    Corrosion of copper in acidic chloride pickling solutions of 0.5 M HCl and its mitigation by 2-amino-5-ethyl-1,3,4-thiadiazole (AETDA) have been investigated using potentiodynamic polarization, chronoamperometry, electrochemical impedance spectroscopy (EIS), and weight-loss measurements. The study was also complemented by scanning electron microscopy (SEM), energy dispersive x-ray (EDX), and UV-Visible absorption spectroscopy investigations. The presence of AETDA and the increase of its concentration in the chloride solutions greatly decreased the corrosion rate and increased the surface and polarization resistances of copper as indicated by the electrochemical measurements. Weight-loss data also indicated that AETDA decreases the dissolution of copper coupons in the studied chloride solution. SEM/EDX investigations showed that AETDA molecules are strongly adsorbed onto copper surface. The UV-Visible absorption spectra confirmed that AETDA molecules suppress the corrosion of copper via their interactions with the copper surface via their adsorption then formation of AETDA-Cu complex.

  19. Synthesis and structure of a new 1D infinite neutral chain based on organotin and selenious acid monoethyl ester

    Institute of Scientific and Technical Information of China (English)

    Long Shen; Yu Cao; Chang Wen Hu

    2009-01-01

    A new ID infinite neutral chain (Ph3SnO2SeOCH2CH3)n (1) based on organotin and selenious acid monoethyl ester has been synthesized successfully and characterized by IR, elemental analysis, and X-ray single-crystal diffraction. In the compound 1, the Sn atom exists in slightly distorted trigonal bipyramidal geometry and the Se center is tri-coordinated with a distorted pyramidal arrangement. It is noted that the synthesis is facile and selenium oxide is directly introduced into synthesis route replacing organoseleninic acid under room temperature.

  20. Fumaric acid esters stimulate astrocytic VEGF expression through HIF-1α and Nrf2.

    Directory of Open Access Journals (Sweden)

    Diana Wiesner

    Full Text Available Fumaric acid esters (FAE are oral analogs of fumarate that have recently been shown to decrease relapse rate and disease progression in multiple sclerosis (MS, prompting to investigate their protective potential in other neurological diseases such as amyotrophic lateral sclerosis (ALS. Despite efficacy in MS, mechanisms of action of FAEs are still largely unknown. FAEs are known to activate the transcription factor Nrf2 and downstream anti-oxidant responses through the succination of Nrf2 inhibitor KEAP1. However, fumarate is also a known inhibitor of prolyl-hydroxylases domain enzymes (PhD, and PhD inhibition might lead to stabilization of the HIF-1α transcription factor under normoxic conditions and subsequent activation of a pseudo hypoxic response. Whether Nrf2 activation is associated with HIF-1α stabilization in response to FAEs in cell types relevant to MS or ALS remains unknown. Here, we show that FAEs elicit HIF-1α accumulation, and VEGF release as its expected consequence, in astrocytes but not in other cell types of the central nervous system. Reporter assays demonstrated that increased astrocytic VEGF release in response to FAEs was dependent upon both HIF-1α and Nrf2 activation. Last, astrocytes of transgenic mice expressing SOD1(G93A, an animal model of ALS, displayed reduced VEGF release in response to FAEs. These studies show that FAEs elicit different signaling pathways in cell types from the central nervous system, in particular a pseudo-hypoxic response in astrocytes. Disease relevant mutations might affect this response.

  1. Fumaric acid esters stimulate astrocytic VEGF expression through HIF-1α and Nrf2.

    Science.gov (United States)

    Wiesner, Diana; Merdian, Irma; Lewerenz, Jan; Ludolph, Albert C; Dupuis, Luc; Witting, Anke

    2013-01-01

    Fumaric acid esters (FAE) are oral analogs of fumarate that have recently been shown to decrease relapse rate and disease progression in multiple sclerosis (MS), prompting to investigate their protective potential in other neurological diseases such as amyotrophic lateral sclerosis (ALS). Despite efficacy in MS, mechanisms of action of FAEs are still largely unknown. FAEs are known to activate the transcription factor Nrf2 and downstream anti-oxidant responses through the succination of Nrf2 inhibitor KEAP1. However, fumarate is also a known inhibitor of prolyl-hydroxylases domain enzymes (PhD), and PhD inhibition might lead to stabilization of the HIF-1α transcription factor under normoxic conditions and subsequent activation of a pseudo hypoxic response. Whether Nrf2 activation is associated with HIF-1α stabilization in response to FAEs in cell types relevant to MS or ALS remains unknown. Here, we show that FAEs elicit HIF-1α accumulation, and VEGF release as its expected consequence, in astrocytes but not in other cell types of the central nervous system. Reporter assays demonstrated that increased astrocytic VEGF release in response to FAEs was dependent upon both HIF-1α and Nrf2 activation. Last, astrocytes of transgenic mice expressing SOD1(G93A), an animal model of ALS, displayed reduced VEGF release in response to FAEs. These studies show that FAEs elicit different signaling pathways in cell types from the central nervous system, in particular a pseudo-hypoxic response in astrocytes. Disease relevant mutations might affect this response. PMID:24098549

  2. Effects of novel hybrids of caffeic acid phenethyl ester and NSAIDs on experimental ocular inflammation.

    Science.gov (United States)

    Pittalà, Valeria; Salerno, Loredana; Romeo, Giuseppe; Siracusa, Maria Angela; Modica, Maria Nunziata; Romano, Giovanni Luca; Salomone, Salvatore; Drago, Filippo; Bucolo, Claudio

    2015-04-01

    In this study, we report the design and synthesis of novel hybrids of caffeic acid phenetyl ester (CAPE) and non-steroidal anti-inflammatory drugs (NSAIDs). We assessed their effects on an experimental ocular inflammation in New Zealand rabbits. The formulations of CAPE-aspirin and CAPE-indomethacin hybrids were topical instilled in the rabbit׳s eye. Afterwards, the anti-inflammatory activity was evaluated by grading the clinical signs and by assessing the inflammatory cell count, protein, PGE2 and TNFα levels in the aqueous humor. Furthermore, ocular tolerability of hybrids formulations was evaluated in a separate set of animals by using a modified Draize test. The ocular inflammation in the control group was significantly higher than in both the hybrid-treated groups, as indicated by clinical grading and biomarkers assessment. However, only the CAPE-aspirin hybrid reduced, in a significant dose-dependent manner, the ocular inflammation elicited by paracentesis. CAPE-indomethacin hybrid was able to significantly attenuate the clinical grading and the PGE2 aqueous levels only at the highest dose (0.1%). CAPE-aspirin significantly reduced PGE2 and TNFα levels in the aqueous humor as well as proteins and PMNs. Finally, all formulations showed no ocular irritation compared with vehicle-treated group. In conclusion, CAPE-aspirin shows full anti-inflammatory efficacy in experimental model of ocular inflammation demonstrating an optimal pharmacological and safety profile. Taken together these data indicate that CAPE-aspirin hybrid represents a valid and safe new chemical entity potentially useful for the treatment of ocular inflammation. PMID:25704612

  3. Toxicological review and oral risk assessment of terephthalic acid (TPA) and its esters: A category approach.

    Science.gov (United States)

    Ball, Gwendolyn L; McLellan, Clifton J; Bhat, Virunya S

    2012-01-01

    Polyethylene terephthalate, a copolymer of terephthalic acid (TPA) or dimethyl terephthalate (DMT) with ethylene glycol, has food, beverage, and drinking water contact applications. Di-2-ethylhexyl terephthalate (DEHT) is a plasticizer in food and drinking water contact materials. Oral reference doses (RfDs) and total allowable concentrations (TACs) in drinking water were derived for TPA, DMT, and DEHT. Category RfD and TAC levels were also established for nine C(1)-C(8) terephthalate esters. The mode of action of TPA, and of DMT, which is metabolized to TPA, involves urinary acidosis, altered electrolyte elimination and hypercalciuria, urinary supersaturation with calcium terephthalate or calcium hydrogen terephthalate, and crystallization into bladder calculi. Weanling rats were more sensitive to calculus formation than dams. Calculi-induced irritation led to bladder hyperplasia and tumors in rats fed 1000 mg/kg-day TPA. The lack of effects at 142 mg/kg-day supports a threshold for urine saturation with calcium terephthalate, a key event for calculus formation. Chronic dietary DMT exposure in rodents caused kidney inflammation, but not calculi. Chronic dietary DEHT exposure caused general toxicity unrelated to calculi, although urine pH was reduced suggesting the TPA metabolite was biologically-active, but of insufficient concentration to induce calculi. Respective oral reference doses of 0.5, 0.5, and 0.2 mg/kg-day and total allowable drinking water concentrations of 3, 3, and 1 mg/L were derived for TPA, DMT, and DEHT. An oral RfD of 0.2 mg/kg-day for the terephthalate category chemicals corresponded to a drinking water TAC of 1 mg/L.

  4. Pharmacokinetics of amino acid ester prodrugs of acyclovir after oral administration: interaction with the transporters on Caco-2 cells.

    Science.gov (United States)

    Katragadda, Suresh; Jain, Ritesh; Kwatra, Deep; Hariharan, Sudharshan; Mitra, Ashim K

    2008-10-01

    In vivo systemic absorption of the amino acid prodrugs of acyclovir (ACV) after oral administration was evaluated in rats. Stability of the prodrugs, L-alanine-ACV (AACV), L-serine-ACV (SACV), L-isoleucine-ACV (IACV), gamma-glutamate-ACV (EACV) and L-valine-ACV (VACV) was evaluated in various tissues. Interaction of these prodrugs with the transporters on Caco-2 cells was studied. In vivo systemic bioavailability of these prodrugs upon oral administration was evaluated in jugular vein cannulated rats. The amino acid ester prodrugs showed affinity towards various amino acid transporters as well as the peptide transporter on the Caco-2 cells. In terms of stability, EACV was most enzymatically stable compared to other prodrugs especially in liver homogenate. In oral absorption studies, ACV and AACV showed high terminal elimination rate constants (lambda(z)). SACV and VACV exhibited approximately five-fold increase in area under the curve (AUC) values relative to ACV (pACV. C(last(T)) (concentration at the last time point) of SACV was observed to be 0.18+/-0.06 microM in plasma which is two times better than VACV and three times better than ACV. Amino acid ester prodrugs of ACV were absorbed at varying amounts (C(max)) and eliminated at varying rates (lambda(z)) thereby leading to varying extents (AUC). The amino acid ester prodrug SACV owing to its enhanced stability, higher AUC and better concentration at last time point seems to be a promising candidate for the oral treatment of herpes infections.

  5. 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.

  6. Radiation Crosslinking of a Mixture of Poly vinyle Alcohol Methacrylic acid and 2-Hydroxy ethyle Methacrylate to Removal of Pollutant Dyes from its Aqueous Solution

    International Nuclear Information System (INIS)

    Hydrogels based on poly vinyle alcohol methacrylic acid/ 2-hydroxy ethyle methacrylate [P(PVA-MAAc/HEMA)] were synthesized by gamma-radiation. The prepared hydrogels were characterized by infrared spectroscopy (FT-IR), scanning electron microscopy (SEM) and thermal gravimetric analysis (TGA). The results of the adsorption studies reveals the higher adsorption capacity of P(PVA-MAAc/ HEMA), hydrogel for the removal of methylene blue and xylenol orange dyes from aqueous solution.

  7. 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

    Directory of Open Access Journals (Sweden)

    Ling-Na Wang

    2016-06-01

    Full Text Available 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.

  8. 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.

  9. 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.

  10. Ethyl diazoacetate synthesis in flow

    Directory of Open Access Journals (Sweden)

    Mariëlle M. E. Delville

    2013-09-01

    Full Text Available Ethyl diazoacetate is a versatile compound in organic chemistry and frequently used on lab scale. Its highly explosive nature, however, severely limits its use in industrial processes. The in-line coupling of microreactor synthesis and separation technology enables the synthesis of this compound in an inherently safe manner, thereby making it available on demand in sufficient quantities. Ethyl diazoacetate was prepared in a biphasic mixture comprising an aqueous solution of glycine ethyl ester, sodium nitrite and dichloromethane. Optimization of the reaction was focused on decreasing the residence time with the smallest amount of sodium nitrite possible. With these boundary conditions, a production yield of 20 g EDA day−1 was achieved using a microreactor with an internal volume of 100 μL. Straightforward scale-up or scale-out of microreactor technology renders this method viable for industrial application.

  11. 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%.

  12. [Research of imidazo[1,2-a]benzimidazole derivatives. XXX. Synthesis and properties of (imidazo[1,2-a]benzimidazolyl-2)acetic acid derivatives].

    Science.gov (United States)

    Anisimova, V A; Tolpygin, I E; Spasov, A A; Serdiuk, T S; Sukhov, A G

    2011-01-01

    Ethyl esters of (9-subtituted-imidazo[1,2-a]benzimidazolyl-2)acetic acids were synthesized. The chemical properties of these esters (hydrolysis, decarboxylation, hydrazinolysis) and biological activity (fungicidal, antimicrobial, antiarrhythmic activity, and also affects on the brain rhythmogenesis) of the prepared compounds were studied.

  13. Synthesis, thermal energy storage properties and thermal reliability of some fatty acid esters with glycerol as novel solid-liquid phase change materials

    Energy Technology Data Exchange (ETDEWEB)

    Sari, Ahmet; Bicer, Alper; Karaipekli, Ali; Alkan, Cemil; Karadag, Ahmet [Gaziosmanpasa University, Department of Chemistry, 60240 Tokat (Turkey)

    2010-10-15

    The synthesis, thermal energy storage properties and thermal reliability of some fatty acid esters with glycerol as novel solid-liquid phase change energy storage materials were investigated. The esters were synthesized by means of the Fischer esterification reaction of the glycerol with myristic, palmitic and stearic acids. The chemical structures of esters were proven by FT-IR and {sup 1}H NMR techniques. The melting temperatures and latent heats of the synthesized esters were found in the range of 31-63 C and 149-185 J/g, by DSC method. The results showed that the esters as phase change materials (PCMs) had good thermal reliability with respect to the 1000 thermal cycles. TGA analysis was performed to determine thermal stability of the esters. The thermal conductivity of the PCMs was also improved significantly by adding 5 wt% expanded graphite. Based on all results it can also be concluded that the synthesized esters can be considered as potential PCMs for thermal energy storage. (author)

  14. Dietary ethyl-eicosapentaenoic acid but not soybean oil reverses central interleukin-1-induced changes in behavior, corticosterone and immune response in rats.

    Science.gov (United States)

    Song, Cai; Leonard, Brian E; Horrobin, David F

    2004-03-01

    Omega (n)-3 and n-6 fatty acids are important membrane components of neurons and immune cells, and related to psychiatric and inflammatory diseases. Increased ratio of n-6/n-3 in the blood has been reported in depressed patients and in students following stress exposure. The n-3 fatty acid, eicosapentaenoic acid (ethyl-EPA) suppresses inflammation and has antidepressant properties. Interleukin (IL)-1beta can stimulate corticosterone secretion, induce anxiety and stress-like behavior and inflammatory responses. This study was to evaluate the effect of diets enriched with coconut oil, ethyl-EPA and soybean oil on central IL-1beta induced stress and anxiety-like behavior, induced changes in the concentration of prostaglandin (PG) E2 and corticosterone and the release of IL-10. Groups of rats were fed with either 5% coconut oil (as control diet), 0.2% EPA with 4.8% coconut oil or 1% EPA with 4% coconut oil and 5% soybean oil for 7 weeks. The central administration of IL-1beta induced sickness, stress and anxiety-like behavior as indicated by a reduction in body weight, decreased time spent, and the number of entries, into the open arms of the elevated plus maze and decreased exploration and entry into the central zone of the "open field" apparatus. IL-1beta also increased PGE2 and corticosterone concentrations and decreased the release of IL-10 from leucocytes. Food enriched with ethyl-EPA but not soybean oil, significantly attenuated most of these changes. These results demonstrate that ethyl-EPA has anti-inflammatory, anti-stress and anti-anxiety effects in rats.

  15. Amino Acid and Peptide Immobilization on Oxidized Nanocellulose: Spectroscopic Characterization

    OpenAIRE

    Claude Daneault; Saïd Barazzouk

    2012-01-01

    In this work, oxidized nanocellulose (ONC) was synthesized and chemically coupled with amino acids and peptides using a two step coupling method at room temperature. First, ONC was activated by N-ethyl-N’-(3-dimethylaminopropyl) carbodiimide hydrochloride, forming a stable active ester in the presence of N-hydroxysuccinimide. Second, the active ester was reacted with the amino group of the amino acid or peptide, forming an amide bond between ONC and the grafted molecule. Using this method, th...

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

    International Nuclear Information System (INIS)

    Labdane derivatives obtained from the diterpenoid labdanediol suppressed NO and PGE2 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 PGE2 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 PGE2 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).

  17. Protective Effect of Caffeic Acid Phenethyl Ester in Rat Cerebral Ischemia/Reperfusion Damage

    Directory of Open Access Journals (Sweden)

    Ertuğrul Uzar

    2011-09-01

    Full Text Available OBJECTIVE: Because oxidative stress is related to cerebral ischemia/reperfusion (I/R injury, modulation of oxygen free radical production may represent a new approach to the management of cerebral I/R. Caffeic acid phenethyl ester (CAPE has been determined to have neuroprotective, antioxidant, anti-inflammatory, and anti-apoptotic activities. The aim of this study was to investigate whether CAPE has a protective effect on cerebral I/R damage, and to determine the possible effects of CAPE on total antioxidant/oxidant status. METHODS: A total of 30 rats were randomly divided into three groups as control group, I/R group, and I/R + CAPE. Total oxidant status (TOS, total antioxidant status (TAS and oxidative stress index (OSI levels and histopathological cellular structures were evaluated in cerebral tissues obtained after the experiment procedure in all groups. RESULTS: In the brain tissue, TOS and OSI levels were found to be significantly increased in the I/R group compared to the controls (p= 0.023, p= 0.001, respectively. Significantly decreased TAS levels were found in the I/R group compared to the controls (p= 0.001. CAPE treatment prevented the increase in TOS and OSI that is produced by cerebral I/R (p= 0.041, p= 0.001, respectively. TAS was found to be increased in the CAPE + I/R group compared with the I/R group (p= 0.002. In the I/R group, the brain sections showed findings of cerebral I/R damage including inflammation, vascular congestion and necrosis (for both variables, p= 0.001. These histopathological cerebral damage findings were found to be significantly reduced in the CAPE + I/R group compared to the I/R group (for both parameters, p< 0.05. CONCLUSION: In this study, it was found that oxidative stress had an important role in the pathogenesis of cerebral I/R damage, and histopathological and biochemical evaluations showed significantly decreased I/R damage following CAPE treatment in rats.

  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. Separation of uranium and ruthenium mixture by liquid surfactant membrane extraction using span 80 and DI-(2-ethyl hexyl) phosphoric acid

    International Nuclear Information System (INIS)

    Separation of uranium and ruthenium mixture in a nitric acid solution using liquid surfactant membrane consisting of the Span 80 as surfactant, mixture of di-(2-ethyl hexyl) phosphoric acid (D2EHPA) in kerosene as extractant and phosphoric acid as internal phase had been done. This technique is the combination of extraction and stripping processes designed to working simultaneously. The parameters studied included the molarity of phosphoric acid (H3PO4) as the internal phase, the molarity of nitric acid (HNO3) in the feed, concentration of di-(2-ethyl hexyl) phosphoric acid in kerosene as extractant, and time of extraction. the result for the experimental separation of 20,000 ppm of uranium in 500 ppm of ruthenium mixture showed that total recovery efficiency for uranium was 87.62% at the optimum conditions, i.e. 1.5 M molarity of H3PO4 3 M of HNO3, 1 % of D2EHPA in kerosene, and 10 minutes extraction time. at such conditions a 100% uranium can be separated from ruthenium

  20. Redox intermediates of flavonoids and caffeic acid esters from propolis: an EPR spectroscopy and cyclic voltammetry study.

    Science.gov (United States)

    Rapta, P; Misík, V; Stasko, A; Vrábel, I

    1995-05-01

    The redox properties of flavonoids: chrysin (1), tectochrysin (2), galangin (3), isalpinin (4), pinostrobin (5), pinobanksin (6), pinobanksin-3-acetate (7), and of caffeic acid ester (8) and diacetylcaffeic acid ester (9), all isolated from propolis, were investigated by cyclic voltammetry in acetonitrile. The choice of aprotic solvent lowered the reactivity of the radical intermediates and made possible to identify redox steps and intermediates not detected so far. The oxidation potentials (vs. saturated calomel electrode) of the investigated compounds were in the region of 1.5 V for 3 and 4; 1.9 V for 1, 2, and 5; 2.0 V for 6 and 7; 1.29 V for 8; and 2.3 V for 9. These oxidation potentials were mainly influenced by the presence of a double bond in 2,3-position and substituent R1 in position 3. Comparison with our earlier data revealed that flavonoids, 1-4, and caffeic acid ester 8 with lower oxidation potentials showed the maximal lipid antioxidant activity, whereas those with higher potentials (5, 6, 7, and 9) are less active. On reduction of 1-9 several one-electron-steps were typically observed in the potential regions: -1.5 V, -1.8 V, and -2 V. where in simultaneous EPR experiments anion radicals of 1 and 3 were observed with the center of unpaired spin density on ring A. Upon oxidation of flavonoids 1-4 carbonyl carbon-centered radicals, .C(O)R, were identified as consecutive products using the EPR spin trapping technique. PMID:7797098

  1. Kinematic viscosity of biodiesel components (fatty acid alkyl esters) and related compounds at low temperatures

    Science.gov (United States)

    Biodiesel, defined as the mono-alkyl esters of vegetable oils and animal fats, has undergone rapid development and acceptance recently. Kinematic viscosity is one of the fuel properties specified in biodiesel standards, with 40 deg C being the temperature at which this property is to be determined ...

  2. Fuel properties of highly polyunsaturated fatty acid methyl esters: Prediction of fuel properties of algal biodiesel

    Science.gov (United States)

    Biodiesel, defined as the mono-alkyl esters of vegetable oils and animal fats, can be derived from other triacylglycerol-containing feedstocks. Especially algae are being considered for this purpose due to their claimed high production potential. However, there are no comprehensive reports regarding...

  3. 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...

  4. Method of making alkyl esters

    Science.gov (United States)

    Elliott, Brian

    2010-09-14

    Methods of making alkyl esters are described herein. The methods are capable of using raw, unprocessed, low-cost feedstocks and waste grease. Generally, the method involves converting a glyceride source to a fatty acid composition and esterifying the fatty acid composition to make alkyl esters. In an embodiment, a method of making alkyl esters comprises providing a glyceride source. The method further comprises converting the glyceride source to a fatty acid composition comprising free fatty acids and less than about 1% glyceride by mass. Moreover, the method comprises esterifying the fatty acid composition in the presence of a solid acid catalyst at a temperature ranging firm about 70.degree. C. to about 120.degree. C. to produce alkyl esters, such that at least 85% of the free fatty acids are converted to alkyl esters. The method also incorporates the use of packed bed reactors for glyceride conversion and/or fatty acid esterification to make alkyl esters.

  5. 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...... that the usage of ROPCA is advantageous, compared with traditional PCA, when analysing the entire profile of chromatographic data in cases of sub-optimally aligned data. It also demonstrates how choosing the most robust PCA (sample or element-wise) depends on the type of outliers present in the data set....

  6. 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

    -ferred to an ionic liquid system for the purpose of improving solubility of the polar substrate and avoiding the application of organic solvents. From screening experiments, it was evident that only methyltrioctylammonium triflouroacetate (tO-MA·TFA) could provide a proper reaction environment for production...... of ascorbyl-CLA ester when using Novozym® 435 as biocatalyst. It was possible to significantly increase the productivity (150 g/l) through the increase of ascorbic acid sol-ubility in ionic liquids by super saturation together with the increase of reaction temperature to 70°C, far beyond than that in organic...

  7. Noncytotoxic and Antitumour-Promoting Activities of Garcinia Acid Esters from Garcinia atroviridis Griff. ex T. Anders (Guttiferae)

    OpenAIRE

    Abdul M. Ali; Nashriyah Mat; Lajis, Nordin H.; Mooi, Lim Y.; Mohidin Amran; Mackeen, Mukram M.

    2012-01-01

    The in vitro antitumour-promoting, cytotoxic, and antioxidant activities of two ester derivatives of garcinia acid, that is, 2-(butoxycarbonylmethyl)-3-butoxycarbonyl-2-hydroxy-3-propanolide (1) and 1′,1′′-dibutyl methyl hydroxycitrate (2), that had been previously isolated from the fruits of Garcinia atroviridis Griff. ex T. Anders (Guttiferae), were examined. Based on the inhibition of Epstein-Barr virus early antigen (EBV-EA) activation, compound 1 (IC50: 70  μ M) showed much higher (8-fol...

  8. Anticonvulsant and behavioral effects observed in mice following treatment with an ester derivative of ferulic acid: Isopentyl ferulate.

    Science.gov (United States)

    Machado, Keylla C; Oliveira, George Laylson S; Machado, Kátia C; Islam, Md Torequl; Junior, Antonio Luiz G; De Sousa, Damião P; Freitas, Rivelilson M

    2015-12-01

    The objective of this study was to evaluate the potential anticonvulsant effect of isopentyl ferulate, a new ester derived from ferulic acid in mice (Mus musculus) subjected to two models of induced seizures. According to the results obtained, the IF at doses of 25, 50 and 75 mg/kg (i.p.) showed protective effect against induced seizures by pilocarpine (400 mg/kg, i.p.) and pentylenetetrazole (70 mg/kg, i.p.). In the two animal models of seizures, the pretreatment of the IF (25, 50 and 75 mg/kg) with flumazenil blocked the anticonvulsant effect, suggesting that the mechanism of action of this ester derived of ferulic acid may be related to activity in the benzodiazepine-binding site of the GABAA receptor (γ-aminobutyric acid, type A). In addition to the anticonvulsant effect, behavioral changes as neurotoxicity indication were assessed by using the rota rod and open field tests. The results obtained showed that the IF (25, 50 and 75 mg/kg) does not induce significant changes in locomotor activity and motor coordination when compared with the control group, unlike the results presented by diazepam. Thus, these results demonstrate a new pharmacological knowledge of IF with potential application against epileptic seizures. However, further studies are needed to elucidate other neurobiological mechanisms underlying epilepsy.

  9. Common and distinct gene expression patterns induced by the herbicides 2,4-dichlorophenoxyacetic acid, cinidon-ethyl and tribenuron-methyl in wheat.

    Science.gov (United States)

    Pasquer, Frédérique; Ochsner, Urs; Zarn, Jürg; Keller, Beat

    2006-12-01

    In wheat, herbicides are used to control weeds. Little is known about the changes induced in the metabolism of tolerant plants after herbicide treatment. The impact of three herbicides [2,4-dichlorophenoxyacetic acid (2,4-D), cinidon-ethyl and tribenuron-methyl] on the wheat transcriptome was studied using cDNA microarrays. Gene expression of plants grown in a controlled environment or in the field was studied between 24 h and 2 weeks after treatment. Under controlled conditions, 2,4-D induced genes of the phenylpropanoid pathway soon after treatment. Cinidon-ethyl triggered peroxidase and defence-related gene expression under controlled conditions, probably because reactive oxygen species are released by photo-oxidation of protoporphyrin-IX. The same genes were upregulated in the field as under controlled conditions, albeit at a weaker level. These results show that cinidon-ethyl specifically induces genes involved in plant defence. Under controlled conditions, tribenuron-methyl did not change the expression profile immediately after treatment, but defence-related genes were upregulated after 1 week. Sulfonylurea compounds such as tribenuron-methyl specifically inhibit acetolactate synthase and are rapidly detoxified, but the activity of some of the resulting metabolites could explain later changes in gene expression. Finally, overexpression of the isopropylmalate synthase gene, involved in branched-chain amino acid synthesis, and of defence-related genes was observed in the field after sulfonylurea treatment. PMID:17054088

  10. 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)

  11. Using glucaminium-based ionic liquids for improving the separation of 2-aminopyrimidine-5-ylboronic acid and its pinacol ester by high performance liquid chromatography.

    Science.gov (United States)

    Joshi, Manishkumar D; Li, Tianhao; Zhong, Qiqing; Anderson, Jared L

    2013-09-20

    A reversed-phase high performance liquid chromatography (HPLC) method is described for the determination of boronic acids that are commonly present as impurities in pinacolboronate ester reagents. Boronic acids and their pinacolboronate esters are key reagents in the Suzuki-Miyaura coupling reaction. The retention of hydrophilic boronic acids in reversed-phase chromatography is often a challenge, especially in very high pH mobile phases, which are needed to mitigate the on-column degradation of pinacolboronate esters. In this study, a hydrophilic boronic acid, 2-aminopyrimidine-5-ylboronic acid, was complexed with specifically functionalized glucaminium-based ionic liquids that were added to the diluent. The two glucaminium-based ILs possess cis-diol moieties that are capable of forming complexes with boronic acids. In addition, aromatic functional groups within the glucaminium cation allow strong π-π interactions with the polymeric stationary phase. Using this approach, the limit of detection for 2-aminopyrimidine-5-ylboronic acid was found to be 3-4μM. The quantification of 2-aminopyrimidine-5-ylboronic acid within a 2-aminopyrimidine-5-pinacolboronate ester sample was successfully achieved using this method. PMID:23958694

  12. Scientific Opinion on the safety evaluation of the active substance, acrylic acid, sodium salt, co-polymer with acrylic acid, methyl ester, methacrylic acid, 2 hydroxypropylester, and acrylic acid cross-linked for use in active food contact materials

    Directory of Open Access Journals (Sweden)

    EFSA Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids (CEF

    2013-04-01

    Full Text Available This scientific opinion of the EFSA Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids deals with the safety evaluation of the acrylic acid, sodium salt, co-polymer with acrylic acid, methyl ester, methacrylic acid, 2 hydroxypropylester, and acrylic acid cross-linked (CAS No. 117675-55-5, FCM Substance No 1022, to be used as liquid absorber in the form of fibres in absorbent pads for the packaging of fresh or frozen meat, poultry, and fish as well as fresh fruits and vegetables. The Panel considered that migration is not expected when the absorption capacity of the pads is not exceeded. Therefore no exposure from the consumption of the packed food is expected. The Panel also considered that none of these starting substances and the cross-linked polymer gives rise to concern for genotoxicity. Therefore the CEF Panel concluded that the use of the substance acrylic acid, sodium salt, co-polymer with acrylic acid, methyl ester, methacrylic acid, 2 hydroxypropylester, and acrylic acid cross-linked does not raise a safety concern when used as fibres in absorber pads for the packaging of fresh or frozen meat, poultry, fish, fruits and vegetables under conditions under which the absorption capacity of the pads is not exceeded and mechanical release of the fibres from the pads is excluded.

  13. Comparison of removal of endodontic smear layer using ethylene glycol bis (beta-amino ethyl ether)-N, N, N', N'-tetraacetic acid and citric acid in primary teeth: A scanning electron microscopic study

    OpenAIRE

    Hegde, Rahul J.; Kavita Bapna

    2016-01-01

    Background: Root canal irrigants are considered momentous in their tissue dissolving property, eliminating microorganisms, and removing smear layer. The present study was aimed to compare the removal of endodontic smear layer using ethylene glycol bis (beta-amino ethyl ether)-N, N, N', N'-tetraacetic acid (EGTA) and citric acid solutions with saline as a control in primary anterior teeth. Materials and Methods: Thirty primary anterior teeth were chosen for the study. The teeth were distribute...

  14. Antibacterial mono- and sesquiterpene esters of benzoic acids from Iranian propolis

    OpenAIRE

    Daneshmand Ali; Najdenski Hristo; Ninova Mariana; Todorov Ivelin; Trusheva Boryana; Bankova Vassya

    2010-01-01

    Abstract Background Propolis (bee glue) has been used as a remedy since ancient times. Propolis from unexplored regions attracts the attention of scientists in the search for new bioactive molecules. Results From Iranian propolis from the Isfahan province, five individual components were isolated: the prenylated coumarin suberosin 1, and four terpene esters: tschimgin (bornyl p-hydroxybenzoate) 2, tschimganin (bornyl vanillate) 3, ferutinin (ferutinol p-hydroxybenzoate) 4, and tefernin (ferut...

  15. Anti-tyrosinase kinetics and antibacterial process of caffeic acid N-nonyl ester in Chinese Olive (Canarium album) postharvest.

    Science.gov (United States)

    Jia, Yu-Long; Zheng, Jing; Yu, Feng; Cai, Yi-Xiang; Zhan, Xi-Lan; Wang, Hui-Fang; Chen, Qing-Xi

    2016-10-01

    Enzymatic browning and bacterial putrefaction are mainly responsible for quality losses of Chinese Olive (Canarium album) postharvest and lead to very short shelf life on average. Screening anti-browning and anti-bacterial agents is important for preservation of Chinese Olive. Caffeic acid N-nonyl ester (C-9) and caffeic acid N- Heptyl ester (C-7) was synthesized as inhibitors of tyrosinase, which is a key enzyme in browning process. The compound of C-9 could inhibit the activity of tyrosinase strongly and its IC50 value was determined to be 37.5μM, while the compound of C-7 had no inhibitory ability. Kinetic analyses showed that compound of C-9 has been a reversible inhibitory mechanism below 50μM and been irreversible mechanisms above 50μM. For the reversible inhibitory mechanism, the values of inhibitory constants (KI and KIS) were determined to be 24.6 and 37.4μM, respectively. The results of Chinese Olive fruit postharvest showed that the compound of C-9 could effectively anti-browning and anti-bacterial putrefaction. In addition, this compound had strong antibacterial activities against Staphylococcus aureus, Escherichia coli, Bacillus subtilis and Salmonella. Therefore, C-9 could be a potential anti-browning and anti-bacterial reagent. PMID:27246378

  16. Analysis of fatty acid steryl esters in tetraploid and hexaploid wheats: identification and comparison between chromatographic methods.

    Science.gov (United States)

    Caboni, Maria Fiorenza; Iafelice, Giovanna; Pelillo, Marco; Marconi, Emanuele

    2005-09-21

    Fatty acid steryl esters (FASE) in whole meal of 14 genotypes of tetraploid wheats (Triticum dicocconand T. durum) and 17 genotypes of hexaploid wheats (T. spelta and T. aestivum) were analyzed using different chromatographic strategies. By both GC-FID and HPLC-ELSD, tetraploid wheats are lacking two major peaks. The amounts of FASE, calculated on the basis of the GC-FID analysis, were double in hexaploid species as compared to tetraploids (40 and 20 mg/100 g db, respectively). HPLC with ESI-MS detection enabled the identification of FASE by the characteristic fragmentations and ion-adducts of each molecule. The distribution of steryl residues was not different between the wheat species: the main class of steryl derivatives found was the beta-sitosteryl derivatives, followed by campesteryl derivatives with small amounts of stigmasteryl esters. The esterified fatty acids explain the difference between the hexaploid and tetraploid wheats. In particular, small amounts of campesteryl and beta-sitosteryl, while no trace of stigmasteryl palmitates, were found in T. durum or its hulled ancestor T. dicoccon. Steryl oleates were not detectable in T. aestivum or its hulled ancestor T. spelta, which is consistent with the filogenesis of tetraploid and hexaploid species. Both chromatographic techniques (GC and HPLC) showed that FASE are useful to discriminate between hexaploid and tetraploid wheats from both qualitative and quantitative points of view.

  17. Real-time in vitro dissolution of 5-aminosalicylic acid from single ethyl cellulose coated extrudates studied by UV imaging

    DEFF Research Database (Denmark)

    Gaunø, Mette Høg; Vilhelmsen, Thomas; Larsen, Crilles Casper;

    2013-01-01

    extrudates were film coated with ethyl cellulose in a typical lab system coater equipped with one Wurster partition. Dissolution testing was performed first in a conventional paddle dissolution apparatus and second, in a flow through geometry equipped with a UV imaging system. Selected film coated extrudates...

  18. An approach based on ultrahigh performance liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry allowing the quantification of both individual phytosteryl and phytostanyl fatty acid esters in complex mixtures.

    Science.gov (United States)

    Scholz, Birgit; Menzel, Nicole; Lander, Vera; Engel, Karl-Heinz

    2016-01-15

    A method for the analysis of both individual phytosteryl and phytostanyl fatty acid esters in complex mixtures was established. The approach was based on a previously not described combination of three elements: (i) the formation of [M-FA+H](+) fragment ions via APCI (atmospheric pressure chemical ionization), (ii) a highly efficient UHPLC-based separation on a 1.7 μ C8 column, previously established for phytostanyl fatty acid esters, allowing the distinction of individual fatty acid esters sharing the same sterol/stanol nucleus and of isotope peaks of phytosteryl fatty acid esters and corresponding phytostanyl fatty acid esters based on these [M-FA+H](+) fragment ions, and (iii) the adjustment of the APCI conditions allowing the differential APCI-MS-SIM (single ion monitoring) detection of phytostanyl esters of linoleic and linolenic acid based on their distinct formation of a [M+H](+) ion. The usefulness of the methodology was demonstrated by the analysis of a commercially available enriched margarine. Two runs per sample allowed the quantification of 35 target analytes; the total amounts of esters were between 124.7 and 125.3g/kg, being in good agreement with the labelled 125 g/kg. Validation data were elaborated for 35 individual fatty acid esters of sitosterol, campesterol, brassicasterol, stigmasterol, sitostanol and campestanol. Recovery rates ranged from 95 to 106%; the coefficients of variation were consistently fatty acid esters and thus closes an analytical gap related to this class of health-relevant food constituents.

  19. 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

    2013-11-01

    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.

  20. Synthesis and Characterization of Modified Epoxy Resins by Silicic Acid Tetraethyl Ester and Nano-SiO2

    Institute of Scientific and Technical Information of China (English)

    李海燕; 张之圣

    2004-01-01

    A kind of modified epoxy resins was obtained by condensation of epoxy resin with silicic acid tetraethyl ester(TEOS) and nano-SiO2. The reactions were performed with hydrochloric acid as a catalyst at 63 °C.The structure, thermal stability and morphological characteristics of the modified epoxy resins were studied through infrared spectra(FT-IR) analysis, thermogravimetric (TG) analysis and scanning electron microscopy respectively. It has been found from the IR and TG study that modified epoxy resins have greater thermal stability than epoxy resins, and its thermal stability has been improved by the formation of inter-crosslinked network structure. The modified epoxy resins exhibit heterogeneous morphology and heterogeneity increases with more TEOS feeding, which in turn confirms the formation of inter-crosslinked network structure in modified epoxy resins.

  1. Adsorption of acetanilide herbicides on soil and its components II. Adsorption and catalytic hydrolysis of diethatyl-ethyl on saturated Na+-, K+-, Ca2+-, and Mg2+-montmorillonite

    Institute of Scientific and Technical Information of China (English)

    2001-01-01

    Adsorption and catalytic hydrolysis of the herbicidediethatyl-ethyl [N-chloroacetyl-N-(2,6-diethylphenyl)glycine ethyl ester] on homoionic Na+-, K+-, Ca2+-, and Mg2+-montmorillonite clays were investigated in water solution. The Freundlich adsorption coefficient, Kf, got from isotherms on clay followed the order of Na+ K+ > Mg2+ Ca2+. Analysis of FT-IR spectra of diethatyl-ethyl adsorbed on clay suggests probable bonding at the carboxyl and amide carbonyl groups of the herbicide. The rate of herbicide hydrolysis in homoionic clay suspensions followed the same order as that for adsorption, indicating that adsorption may have preceded and thus caused hydrolysis. Preliminary product identification showed that hydrolysis occurred via nucleophilic substitution at the carboxyl carbon, causing the cleavage of the ester bond and formation of diethatyl and its dechlorinated derivative, and at the amide carbon, yielding an ethyl ester derivative and its acid.These pathways also suggest that hydrolysis of diethatyl-ethyl was catalyzed by adsorption on the clay surface.

  2. Quantification of fatty acids as methyl esters and phospholipids in cheese samples after separation of triacylglycerides and phospholipids

    Energy Technology Data Exchange (ETDEWEB)

    Hauff, Simone [University of Hohenheim, Institute of Food Chemistry, Garbenstrasse 28, D-70599 Stuttgart (Germany); Vetter, Walter [University of Hohenheim, Institute of Food Chemistry, Garbenstrasse 28, D-70599 Stuttgart (Germany)], E-mail: w-vetter@uni-hohenheim.de

    2009-03-23

    Determination of the individual fatty acid composition of neutral- and phospholipids as well as the phospholipid content of dairy food and other foodstuffs are important tasks in life sciences. For these purposes, a method was developed for the separation of lipids (standards of triolein and diacylphosphatidylcholines as well as three cheese samples) by solid-phase extraction using a self-packed column filled with partly deactivated silica. Non-halogenated solvents were used for the elution of the lipid classes. Cyclohexane/ethyl acetate (1:1, v/v) served for the elution of neutral lipids, while polar lipids were eluted with three solvents (ethyl acetate/methanol, methanol, and methanol/water) into one fraction. The separated lipid fractions were transesterified and the individual fatty acids were quantified by using gas chromatography coupled to electron ionization mass spectrometry (GC/EI-MS) in the selected ion monitoring (SIM) mode. The recovery rate for standard phosphatidylcholines was {approx}90% and cross-contamination from neutral lipids was negligible. The method was applied to cheese samples. Quantitative amounts of individual fatty acids in the phospholipid fraction were <0.002-0.29% of total lipids from camembert, <0.002-0.12% of total lipids from mozzarella, and <0.002-0.18% of total lipids in a goat cream cheese. Differences in the fatty acid pattern of neutral and polar lipids were detected. The quantity of the fatty acids determined in the phospholipid fraction was divided by the factor 0.7 in order to convert the fatty acid content into the phospholipid content of the cheese samples. This factor is based on the contribution of 16:0 to dipalmitoylphosphatidylcholine (DPPC). The resulting DPPC equivalents (DPPC{sub eq}) were found to be representative for the average contribution of fatty acids to all classes of phospholipids in dairy products. Using this approach, the phospholipid content of lipids from mozzarella, camembert, and goat cream cheese

  3. Bias voltage dependence of molecular orientation of dialkyl ketone and fatty acid alkyl ester at the liquid–graphite interface

    International Nuclear Information System (INIS)

    Graphical abstract: - Highlights: • Self-assembled monolayers (SAMs) of 18-pentatriacontanone (as ketone) and stearyl stearate (as ester) were formed on a graphite surface at the liquid–solid interface. • Orientations of the molecules in SAMs on the substrate were studied by scanning tunneling microscopy. • A perpendicular carbon skeleton-plane orientation with the CO pointing up on the surface is favorable for a substrate with negative charge and vice versa. - Abstract: Molecular orientations of self-assembled 18-pentatriacontanone (as ketone) and stearyl stearate (as ester) monolayers adsorbed on a graphite surface were studied by scanning tunneling microscopy (STM) at the liquid–solid interface. At a positive sample bias, the central areas of the dialkyl ketone and fatty acid alkyl ester molecules in the STM images appeared as two bright regions on both sides of a dim spot and a bright region on one side of a dim spot, whereas at a negative sample bias, the areas appeared dim. This contrast variation indicates that a perpendicular carbon skeleton-plane orientation with the CO pointing down on the surface is favorable for a substrate with positive charge and vice versa because of the greater electronegativity of the oxygen atom. Upon the bias voltage reversal, the delay time for the STM image contrast change in the region was observed on a time scale of minutes. The difference between the delay time lengths for the direction of bias polarity change indicates that the perpendicular configuration with CO pointing up is more stable than that with CO pointing down. These results indicate that the use of an electric field along a direction vertical to the monolayer on the substrate provides control over the orientations of the molecules between two stable states at the liquid–solid interface

  4. 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.

  5. Studies of a pyridino-crown ether-based chiral stationary phase on the enantioseparation of biogenic chiral aralkylamines and α-amino acid esters by high-performance liquid chromatography.

    Science.gov (United States)

    Lévai, Sándor; Németh, Tamás; Fődi, Tamás; Kupai, József; Tóth, Tünde; Huszthy, Péter; Balogh, György Tibor

    2015-11-10

    This paper reports the enantioseparation ability of a pyridino-18-crown-6 ether-based chiral stationary phase [(S,S)-CSP-1]. The enantiomeric discrimination of chiral stationary phase (S,S)-CSP-1 was evaluated by HPLC using the mixtures of enantiomers of various protonated primary aralkylamines [1-phenylethylamine hydrogen perchlorate (PEA), 2,3-dihydro-1H-inden-1-amine (1-aminoindan), 2,2'-(1,2-diaminoethane-1,2-diyl) diphenol (HPEN)] and perchlorate salts of α-amino acid esters [alanine benzyl ester (Ala-OBn), phenylalanine benzyl ester (Phe-OBn), phenylalanine methyl ester (Phe-OMe), phenylglycine methyl ester (PhGly-OMe), glutamic acid dibenzyl ester (Glu-diOBn), and valine benzyl ester (Val-OBn)]. The best enantioseparation was achieved in the case of PEA. The high enantioselectivity was rationalized by the strong π-π interaction of the extended π system of the aryl-substituted pyridine unit. PMID:26218505

  6. Carboxylesterase activities toward pesticide esters in crops and weeds.

    Science.gov (United States)

    Gershater, Markus; Sharples, Kate; Edwards, Robert

    2006-12-01

    Proteins were extracted from maize, rice, sorghum, soybean, flax and lucerne; the weeds Abutilon theophrasti, Echinochloa crus-galli, Phalaris canariensis, Setaria faberii, Setaria viridis, Sorghum halepense and the model plant Arabidopsis thaliana and assayed for carboxylesterase activity toward a range of xenobiotics. These included the pro-herbicidal esters clodinafop-propargyl, fenoxaprop-ethyl, fenthioprop-ethyl, methyl-2,4-dichlorophenoxyacetic acid (2,4-d-methyl), bromoxynil-octanoate, the herbicide-safener cloquintocet-mexyl and the pyrethroid insecticide permethrin. Highest activities were recorded with alpha-naphthyl acetate and methylumbelliferyl acetate. Esters of p-nitrophenol were also readily hydrolysed, with turnover declining as the chain length of the acyl component increased. Activities determined with model substrates were much higher than those observed with pesticide esters and were of limited value in predicting the relative rates of hydrolysis of the crop protection agents. Substrate preferences with the herbicides were typically 2,4-d-methyl>clodinafop-propargyl>fenthioprop-ethyl, fenoxaprop-ethyl and bromoxynil-octanoate. Isoelectric focussing in conjunction with staining for esterase activity using alpha-naphthyl acetate as substrate confirmed the presence of multiple carboxylesterase isoenzymes in each plant, with major qualitative differences observed between species. The presence of serine hydrolases among the resolved isoenzymes was confirmed through their selective inhibition by the organophosphate insecticide paraoxon. Our studies identify potentially exploitable differences between crops and weeds in their ability to bioactivate herbicides by enzymic hydrolysis and also highlight the usefulness of Arabidopsis as a plant model to study xenobiotic biotransformation.

  7. Study of Lewis Acid Promoting KBH_4 Reduce Carboxylic Acid Ester%Lewis酸促进KBH_4还原某些羧酸酯的研究

    Institute of Scientific and Technical Information of China (English)

    汪一波; 金召磊; 唐守万; 孙佰申; 潘富友; 高建荣

    2011-01-01

    Potassium borohydride reduction of some carboxylic esters into the corresponding alcohols by the Lewis acid was introduced.The structures were confirmed by 1HNMR,MS and IR,consistent with its structure and the target,and the yield of 37.5~68.5.%在Lewis酸的作用下,研究硼氢化钾将某些羧酸酯还原成相应的醇。其产物经1HNMR、MS和IR表征,其结构与目标物一致,收率在37.5~68.5之间。

  8. Used frying oils and fats and their utilization in the production of methyl esters of higher fatty acids

    Energy Technology Data Exchange (ETDEWEB)

    Cvengros, J. Jan; Cvengrosova, Zuzana [Slovak Univ. of Technology, Faculty of Chemical and Food Technology, Bratislava (Slovakia)

    2004-08-01

    From the point of view price and available capacity used frying oils or fats (UFO) represent an attractive raw material for the production of methyl esters (ME) of higher fatty acids as alternative fuels for diesel engines. If they are treated such that the required quality, with an acidity number up to 3.0 mg KOH/g and a water content up to 0.1 wt%, is achieved they can be processed to ME using standard techniques of alkali-catalysed transesterification with methanol which are utilized for production of the ME from new oils/fats. The problematic waste can thus be converted to an ecologically friendly fuel. Vacuum distillation of free fatty acids in a film evaporator is an effective method for simultaneously decreasing the content of FFA and water in UFO. Final distillation of raw ME in a film vacuum evaporator results in practically all parameters required by the standard, in the final ME being achieved. Undesirable low-temperature properties of ME derived from UFO, due to higher fraction of saturated acyls, can be adjusted by the addition of depressants-flow improvers for winterization. Some simplified methods for the quality control of UFO and ME are discussed. The conversion of acylglycerols to ME is monitored by GLC with a packed column, where the peak areas of ME in the sample before and after the reaction with an effective methylation agent are compared. The method for the determination of the water content in esters utilizes the reaction of calcium carbide with water, the volume of acetylene being measured. (Author)

  9. Synthesis and Crystal Structure of 2-[(4-Methoxy- 6-methylthio-2-pyrimidinyl)aminocarbonyl-aminosulfonyl] Benzoic Acid Methyl Ester

    Institute of Scientific and Technical Information of China (English)

    黄明智; 王晓光; 毛春晖; 黄路; 宋海斌

    2004-01-01

    The title compound 2-[(4-methoxy-6-methylthio-2-pyrimidinyl)aminocarbonyl-aminosulfonyl]benzoic acid methyl ester (C15H16N4O6S2,Mr = 412.44) was obtained by the reaction of (4-methoxy-6-methylthio-2-pyrimidinyl)amine with 2-methoxylcarbonylbenzene-sulfonylisocya-nate.The crystal is of monoclinic,space group P21/c with a =11.169(3),b = 9.508(3),c = 17.690(5)(A),β = 91.593(5)o,Z = 4,V = 1877.9(10)(A)3,Dc = 1.459 g/cm3,F(000) = 856,μ(MoKα) = 0.324 mm-1,R = 0.0690 and Wr = 0.1368 for 3301 observed reflections (I > 2((I)).The N(1)-H…N(3) and N(2)-H…O(4) hydrogen bonds can be observed.In the molecule the phenyl plane(I),pyrimi-din-2-yl-urea bridge plane(Ⅱ) and ester plane(Ⅲ) form three conjugated systems.

  10. Cavitation assisted synthesis of fatty acid methyl esters from sustainable feedstock in presence of heterogeneous catalyst using two step process.

    Science.gov (United States)

    Dubey, Sumit M; Gole, Vitthal L; Gogate, Parag R

    2015-03-01

    The present work reports the intensification aspects for the synthesis of fatty acid methyl esters (FAME) from a non-edible high acid value Nagchampa oil (31 mg of KOH/g of oil) using two stage acid esterification (catalyzed by H₂SO₄) followed by transesterification in the presence of heterogeneous catalyst (CaO). Intensification aspects of both stages have been investigated using sonochemical reactors and the obtained degree of intensification has been established by comparison with the conventional approach based on mechanical agitation. It has been observed that reaction temperature for esterification reduced from 65 to 40 °C for the ultrasonic approach whereas there was a significant reduction in the optimum reaction time for transesterification from 4h for the conventional approach to 2.5h for the ultrasound assisted approach. Also the reaction temperature reduced marginally from 65 to 60 °C and yield increased from 76% to 79% for the ultrasound assisted approach. Energy requirement and activation energy for both esterification and transesterification was lower for the ultrasound based approach as compared to the conventional approach. The present work has clearly established the intensification obtained due to the use of ultrasound and also illustrated the two step approach for the synthesis of FAME from high acid value feedstock based on the use of heterogeneous catalyst for the transesterification step.

  11. Caffeic Acid Phenethyl Ester: Consequences of Its Hydrophobicity in the Oxidative Functions and Cytokine Release by Leukocytes

    Directory of Open Access Journals (Sweden)

    Luana Chiquetto Paracatu

    2014-01-01

    Full Text Available Numerous anti-inflammatory properties have been attributed to caffeic acid phenethyl ester (CAPE, an active component of propolis. NADPH oxidases are multienzymatic complexes involved in many inflammatory diseases. Here, we studied the importance of the CAPE hydrophobicity on cell-free antioxidant capacity, inhibition of the NADPH oxidase and hypochlorous acid production, and release of TNF-α and IL-10 by activated leukocytes. The comparison was made with the related, but less hydrophobic, caffeic and chlorogenic acids. Cell-free studies such as superoxide anion scavenging assay, triene degradation, and anodic peak potential (Epa measurements showed that the alterations in the hydrophobicity did not provoke significant changes in the oxidation potential and antiradical potency of the tested compounds. However, only CAPE was able to inhibit the production of superoxide anion by activated leukocytes. The inhibition of the NADPH oxidase resulted in the blockage of production of hypochlorous acid. Similarly, CAPE was the more effective inhibitor of the release of TNF-α and IL-10 by Staphylococcus aureus stimulated cells. In conclusion, the presence of the catechol moiety and the higher hydrophobicity were essential for the biological effects. Considering the involvement of NADPH oxidases in the genesis and progression of inflammatory diseases, CAPE should be considered as a promising anti-inflammatory drug.

  12. 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.

  13. Structural and electronic properties of single-walled carbon nanotubes adsorbed with 1-pyrenebutanoic acid, succinimidyl ester

    Institute of Scientific and Technical Information of China (English)

    FAN WenJie; ZHANG RuiQin

    2008-01-01

    The adsorption of a 1-pyrenebutanoic acid, succinimidyl ester (PSE) interacting with metallic armchair (n, n) carbon nanotubes (CNTs) (n=3-13)was investigated by using a density-functional tight-binding method with an empirical van der Waals force correction. In this study of large systems involving weak interactions, our calculations showed that the pyrene ring of PSE could be spontaneously absorbed onto the CNTs surface through π-π stacking at the physisorption distances. Increasing of the CNTs diameter leads to a higher adsorption energy. After adsorption of PSE on its sidewall, the geometric and electronic structures of CNTs are basically undamaged. CNTs contribute to the main peak of the elec-tron excitation procedure in the UV/vis spectrum, with a slight red shift after adsorption of PSE.

  14. Synthesis, Formulation, and Adjuvanticity of Monodesmosidic Saponins with Olenanolic Acid, Hederagenin and Gypsogenin Aglycones, and some C-28 Ester Derivatives

    DEFF Research Database (Denmark)

    Greatrex, Ben W.; Daines, Alison M.; Hook, Sarah;

    2015-01-01

    cholesterol and phospholipid, the choline ester derivatives produced nanocrystalline rods or helical micelles. The effects of modifying sugar stereochemistry and the aglycone on the immunostimulatory effects of the saponins was then evaluated using the activation markers MHC class II and CD86 in murine bone......In an attempt to discover a new synthetic vaccine adjuvant, the glycosylation of hederagenin, gypsogenin, and oleanolic acid acceptors with di- and trisaccharide donors to generate a range of mimics of natural product QS-21 was carried out. The saponins were formulated with phosphatidylcholine and...... marrow dendritic cells. The most active saponin, 3-O-(Manp(13)Glcp)hederagenin, was stimulatory at high concentrations in cell culture, but this did not translate to strong responses in vivo....

  15. Distribution of polychlorinated biphenyls, phthalic acid esters, polycyclic aromatic hydrocarbons and organochlorine substances in the Moscow River, Russia.

    Science.gov (United States)

    Eremina, Natalia; Paschke, Albrecht; Mazlova, Elena A; Schüürmann, Gerrit

    2016-03-01

    The purpose of this study was to investigate the levels of polychlorinated biphenyl (PCB), phthalic acid esters (PAE), polycyclic aromatic hydrocarbons (PAH) and organochlorine substances (OCP) in the Moscow River water. Some studies have reported the occurrence of these substances in the soil of the Moscow region; however, no study has yet established an overview for these compounds in the Moscow River water. In this study the Moscow River water contamination with PAEs, PAHs and OCPs was determined. Obtained results were associated with the resident area located on the river bank, and the possible contamination sources were considered. The obtained data were compared with the data on the contamination of the different world-wide rivers. This research indicates the further study necessity of the Moscow region to cover more contaminated sites and environmental compartments. PMID:26807987

  16. Spectroscopic studies on 9H-carbazole-9-(4-phenyl) boronic acid pinacol ester by DFT method

    Science.gov (United States)

    Sas, E. B.; Kurt, M.; Can, M.; Horzum, N.; Atac, A.

    2016-08-01

    9H-Carbazole-9-(4-phenyl) boronic acid pinacol ester (9-CPBAPE) molecule was investigated by FT-IR, Raman, UV-vis, 1H and 13C NMR spectra. FT-IR, FT-Raman and dispersive Raman spectra were recorded in the solid phase. 1H, 13C NMR and UV-vis spectra were recorded in dimethyl sulfoxide (DMSO) solution. The results of theoretical calculations for the spectra of the title molecule were compared with the experimental spectra. The highest occupied molecular orbital (HOMO) the lowest unoccupied molecular orbital (LUMO) and molecular electrostatic potential (MEP) analyses were performed. The theoretical calculations for the molecular structure and spectroscopic studies were performed with DFT (B3LYP) and 6-311G (d,p) basis set calculations using the Gaussian 09 program. The total (TDOS), partial (PDOS) density of state and overlap population density of state (OPDOS) diagrams analyses were performed using GaussSum 2.2 program.

  17. Widespread occurrence of phthalic acid esters in raw oilseeds in China used for edible vegetable oil production.

    Science.gov (United States)

    Hu, Ai-Peng; Liu, Yu-Lan; Shi, Long-Kai

    2016-09-01

    Seven different phthalic acid esters (PAEs) were quantified in 124 samples of 16 types of oilseeds from China using a simplified GC-MS method. Di-2-ethylhexyl phthalate and di-n-butyl phthalate were found in all tested oilseed samples. Each made a high contribution to the summed total PAEs. Total PAE concentrations in 124 oilseeds ranged from 0.14 to 3.05 mg kg(-1), and the mean was 0.99 mg kg(-1). Mandulapalka (Cyperus esculentus) samples were the most severely contaminated among all the tested specimens; maize germ samples were least contaminated. Di-n-octyl phthalate and butylbenzyl phthalate were not detected in 12 and five types of oilseeds, respectively. Only eight samples contained all seven analytes. No difference was observed between woody oil-bearing plant and herbaceous oil-bearing plant in terms of PAEs content. PMID:27603777

  18. Structural and electronic properties of single-walled carbon nanotubes adsorbed with 1-pyrenebutanoic acid,succinimidyl ester

    Institute of Scientific and Technical Information of China (English)

    2008-01-01

    The adsorption of a 1-pyrenebutanoic acid, succinimidyl ester (PSE) interacting with metallic armchair (n, n) carbon nanotubes (CNTs) (n= 3-13) was investigated by using a density-functional tight-binding method with an empirical van der Waals force correction. In this study of large systems involving weak interactions, our calculations showed that the pyrene ring of PSE could be spontaneously absorbed onto the CNTs surface through π-π stacking at the physisorption distances. Increasing of the CNTs diameter leads to a higher adsorption energy. After adsorption of PSE on its sidewall, the geometric and electronic structures of CNTs are basically undamaged. CNTs contribute to the main peak of the electron excitation procedure in the UV/vis spectrum, with a slight red shift after adsorption of PSE.

  19. Widespread occurrence of phthalic acid esters in raw oilseeds in China used for edible vegetable oil production.

    Science.gov (United States)

    Hu, Ai-Peng; Liu, Yu-Lan; Shi, Long-Kai

    2016-09-01

    Seven different phthalic acid esters (PAEs) were quantified in 124 samples of 16 types of oilseeds from China using a simplified GC-MS method. Di-2-ethylhexyl phthalate and di-n-butyl phthalate were found in all tested oilseed samples. Each made a high contribution to the summed total PAEs. Total PAE concentrations in 124 oilseeds ranged from 0.14 to 3.05 mg kg(-1), and the mean was 0.99 mg kg(-1). Mandulapalka (Cyperus esculentus) samples were the most severely contaminated among all the tested specimens; maize germ samples were least contaminated. Di-n-octyl phthalate and butylbenzyl phthalate were not detected in 12 and five types of oilseeds, respectively. Only eight samples contained all seven analytes. No difference was observed between woody oil-bearing plant and herbaceous oil-bearing plant in terms of PAEs content.

  20. Cytotoxicity of copper(II)-complexes with some S-alkyl derivatives of thiosalicylic acid. Crystal structure of the binuclear copper(II)-complex with S-ethyl derivative of thiosalicylic acid

    Science.gov (United States)

    Nikolić, Miloš V.; Mijajlović, Marina Ž.; Jevtić, Verica V.; Ratković, Zoran R.; Novaković, Slađana B.; Bogdanović, Goran A.; Milovanović, Jelena; Arsenijević, Aleksandar; Stojanović, Bojana; Trifunović, Srećko R.; Radić, Gordana P.

    2016-07-01

    The spectroscopically predicted structure of the obtained copper(II)-complex with S-ethyl derivative of thiosalicylic acid was confirmed by X-ray structural study and compared to previously reported crystal structure of the Cu complex with S-methyl derivative. Single crystals suitable for X-ray measurements were obtained by slow crystallization from a water solution. Cytotoxic effects of S-alkyl (R = benzyl (L1), methyl (L2), ethyl (L3), propyl (L4) and butyl (L5)) derivatives of thiosalicylic acid and the corresponding binuclear copper(II)-complexes on murine colon carcinoma cell lines, CT26 and CT26.CL25 and human colon carcinoma cell line HCT-116 were reported here. The analysis of cancer cell viability showed that all the tested complexes had low cytotoxic effect on murine colon carcinoma cell lines, but several times higher cytotoxicity on normal human colon carcinoma cells.