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Sample records for acid ethyl ester

  1. 40 CFR 721.4250 - Hexanoic acid, 2-ethyl-, ethenyl ester.

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Hexanoic acid, 2-ethyl-, ethenyl ester... Substances § 721.4250 Hexanoic acid, 2-ethyl-, ethenyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as hexanoic acid, 2-ethyl-, ethenyl ester...

  2. 40 CFR 721.10064 - 2-Propenoic acid, 2-[2-(ethenyloxy)ethoxy]ethyl ester.

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false 2-Propenoic acid, 2- ethyl ester. 721... Substances § 721.10064 2-Propenoic acid, 2- ethyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as 2-propenoic acid, 2- ethyl ester (PMN...

  3. 40 CFR 721.7290 - Propanoic acid, 2-(trimethoxysilyl)-, ethyl ester.

    Science.gov (United States)

    2010-07-01

    ...)-, ethyl ester. 721.7290 Section 721.7290 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.7290 Propanoic acid, 2-(trimethoxysilyl)-, ethyl ester. (a) Chemical... acid, 2-(trimethoxysilyl)-, ethyl ester (PMN P-01-22; CAS No. 137787-41-8) is subject to...

  4. 21 CFR 172.225 - Methyl and ethyl esters of fatty acids produced from edible fats and oils.

    Science.gov (United States)

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Methyl and ethyl esters of fatty acids produced... Methyl and ethyl esters of fatty acids produced from edible fats and oils. Methyl esters and ethyl esters... following prescribed conditions: (a) The additive consists of a mixture of either methyl or ethyl esters...

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

    Science.gov (United States)

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

    2015-11-25

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

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

    Science.gov (United States)

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

    2017-02-08

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

  7. 40 CFR 721.10074 - Acetic acid, 2-chloro-, 1-(3,3-dimethylcyclohexyl)ethyl ester.

    Science.gov (United States)

    2010-07-01

    ...-dimethylcyclohexyl)ethyl ester. 721.10074 Section 721.10074 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... 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)...

  8. 40 CFR 721.1950 - 2-Butenedioic acid (Z), mono(2-((1-oxopropenyloxy)ethyl) ester .

    Science.gov (United States)

    2010-07-01

    ...-oxopropenyloxy)ethyl) ester . 721.1950 Section 721.1950 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.1950 2-Butenedioic acid (Z), mono(2-((1-oxopropenyloxy)ethyl) ester . (a... 2-butenedioic acid (Z), mono(2-((1-oxopropenyloxy)ethyl) ester (PMN P-85-543) is subject...

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

    Directory of Open Access Journals (Sweden)

    Iurii S. Bodachivskyi

    2016-12-01

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

  10. Effects of switching from omega-3-acid ethyl esters to icosapent ethyl in a statin-treated patient with elevated triglycerides.

    Science.gov (United States)

    Kedia, Anurag W; Lynch, Erin

    2015-01-01

    In patients with dyslipidemia, elevated triglyceride (TG) levels, or TG-rich lipoproteins, and cardiovascular risk may remain despite statin therapy. Prescription omega-3 fatty acid formulations containing the ethyl esters of eicosapentaenoic acid (EPA) plus docosahexaenoic acid (DHA) (omega-3-acid ethyl esters; Lovaza®) or high-purity EPA ethyl ester (icosapent ethyl; Vascepa®) are TG-lowering treatments that may be administered in addition to statins. Here we describe the effects of switching from omega-3-acid ethyl esters to icosapent ethyl in a 44-year-old obese man with dyslipidemia, hypertension, and hypothyroidism. The patient was receiving stable treatment with medications, including atorvastatin 40 mg/day and extended-release niacin 1000 mg/day. Owing to persistently elevated TG levels and other cardiovascular risk factors, the patient was initiated on omega-3-acid ethyl esters 4 g/day. After approximately 2 years on omega-3-acid ethyl esters, his total cholesterol (TC) level was 184 mg/dL, low-density lipoprotein cholesterol (LDL-C) level was 81 mg/dL, TG level was elevated at 307 mg/dL despite statin therapy, and non-high-density lipoprotein cholesterol (non-HDL-C) level was 144 mg/dL. After the switch to icosapent ethyl, TC level decreased by 34% to 121 mg/dL, LDL-C level decreased by 28% to 58 mg/dL, TG level decreased by 41% to 180 mg/dL, and non-HDL-C level decreased by 44% to 81 mg/dL. Switching from omega-3-acid ethyl esters containing both EPA and DHA to icosapent ethyl containing high-purity EPA resulted in beneficial and substantial changes in the lipid profile with a notable reduction of TG levels along with additional reductions in LDL-C levels in a statin-treated obese patient with persistently high TG levels. Treatment with icosapent ethyl was well tolerated.

  11. 40 CFR 721.8450 - 2-Propenoic acid, 2-methyl-, 2-[3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl]ethyl ester.

    Science.gov (United States)

    2010-07-01

    ... ester. 721.8450 Section 721.8450 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED... Specific Chemical Substances § 721.8450 2-Propenoic acid, 2-methyl-, 2- ethyl ester. (a) Chemical substance... acid, 2-methyl-, 2- ethyl ester, (PMN P-90-333) is subject to reporting under this section for...

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

    DEFF Research Database (Denmark)

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

    2012-01-01

    Enzymatic conversion of fish oil free fatty acids (FFA) or fatty acid ethyl esters (FAE) into glycerides via esterification or transesterification was examined. The reactions catalyzed by Lipozyme™ 435, a Candida antarctica lipase, were optimized. Influence on conversion yields of fatty acid chain...

  13. 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.

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

    NARCIS (Netherlands)

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

    2001-01-01

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

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

    Directory of Open Access Journals (Sweden)

    Theresa W Gauthier

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

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

    Science.gov (United States)

    Gauthier, Theresa W; Mohan, Sowmya S; Gross, Teresa S; Harris, Frank L; Guidot, David M; Brown, Lou Ann S

    2015-01-01

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

  17. Usefulness of Icosapent Ethyl (Eicosapentaenoic Acid Ethyl Ester) in Women to Lower Triglyceride Levels (Results from the MARINE and ANCHOR Trials).

    Science.gov (United States)

    Mosca, Lori; Ballantyne, Christie M; Bays, Harold E; Guyton, John R; Philip, Sephy; Doyle, Ralph T; Juliano, Rebecca A

    2017-02-01

    There are limited data on the efficacy and safety of triglyceride (TG)-lowering agents in women. We conducted subgroup analyses of the effects of icosapent ethyl (a high-purity prescription form of the ethyl ester of the omega-3 fatty acid, eicosapentaenoic acid) on TG levels (primary efficacy variable) and other atherogenic and inflammatory parameters in a total of 215 women with a broad range of TG levels (200-2000 mg/dl) enrolled in two 12-week placebo-controlled trials: MARINE (n = 18; placebo, n = 18) and ANCHOR (n = 91; placebo, n = 88). Icosapent ethyl 4 g/day significantly reduced TG levels from baseline to week 12 versus placebo in both MARINE (-22.7%; p = 0.0327) and ANCHOR (-21.5%; p 500% in eicosapentaenoic acid levels in plasma and red blood cells (all p <0.001). Icosapent ethyl was well tolerated, with adverse-event profiles comparable with findings in the overall studies. In conclusion, icosapent ethyl 4 g/day significantly reduced TG levels and other atherogenic parameters in women without increasing low-density lipoprotein cholesterol levels compared with placebo; the clinical implications of these findings are being evaluated in the REDUCtion of Cardiovascular Events With Eicosapentaenoic Acid [EPA]-Intervention Trial (REDUCE-IT) cardiovascular outcomes study.

  18. 4-Hydroxy-3-methyl-6-phenylbenzofuran-2-carboxylic acid ethyl ester derivatives as potent anti-tumor agents.

    Science.gov (United States)

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

    2004-01-19

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

  19. In vivo tumor accumulation of nanoparticles formed by ionic interaction of glycol chitosan and fatty acid ethyl ester.

    Science.gov (United States)

    Kim, Jin; Lee, Chang-Moon; Jeong, Hwan-Jeong; Lee, Ki-Young

    2011-02-01

    In this study, novel fatty acid ethyl ester (FAEE)-based glycol chitosan (GC) nanoparticles were prepared through an electrostatic interaction. Additionally, the tumor accumulation of the FAEE-GC nanoparticles was evaluated in order to determine the enhanced permeability and retention (EPR) effect in a breast tumor model. FAEE, including eicosapentaenoic acid ethyl ester (EPAEE) and docosahexanoic acid ethyl ester (DHAEE), successfully formed ionic complexes with GC. The FAEE-GC complexes were self-aggregated with a spherical shape and a mean diameter of 110-333 nm in aqueous media. Cy7 was labeled to the FAEE-GC complexes for the in vivo optical imaging. A tumor animal model was developed by inoculating MDA-MB231 breast tumor cells into the right flanks of mice. The Cy7-labeled FAEE-GC nanoparticles were injected into the tail vein of the tumor-bearing mice. Fluorescence signals were strongly observed in the tumor because of the EPR effect. In the ex vivo imaging of the mice, the highest fluorescence intensity, except for the kidney, was observed in the tumor. Therefore, the FAEE-GC nanoparticles could be a useful vehicle for FAEE formulation as well as an in vivo tumor-selective drug delivery carrier.

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

    Science.gov (United States)

    Tatsuno, Ichiro

    2014-11-01

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

  1. 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.

  2. 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...

  3. 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

  4. 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%.

  5. Detecting alcohol abuse: traditional blood alcohol markers compared to ethyl glucuronide (EtG) and fatty acid ethyl esters (FAEEs) measurement in hair.

    Science.gov (United States)

    Hastedt, Martin; Büchner, Mara; Rothe, Michael; Gapert, René; Herre, Sieglinde; Krumbiegel, Franziska; Tsokos, Michael; Kienast, Thorsten; Heinz, Andreas; Hartwig, Sven

    2013-12-01

    Alcohol abuse is a common problem in society; however, the technical capabilities of evaluating individual alcohol consumption using objective biomarkers are rather limited at present. In recent years research has focused on alcohol markers using hair analysis but data on performance and reliable cut-off values are still lacking. In this study 169 candidates were tested to compare traditional biomarkers, such as carbohydrate-deficient-transferrin (CDT), gamma glutamyl transferase (GGT), aspartate amino transferase, alanine amino transferase and the mean corpuscular volume of the erythrocytes, with alcohol markers detectable in hair such as ethyl glucuronide (EtG) and fatty acid ethyl esters (FAEEs). This study revealed that EtG, GGT and CDT showed the best results, demonstrating areas under the curve calculated from receiver operating characteristics of 0.941, 0.943 and 0.899 respectively. The lowest false-negative and false-positive rates were obtained by using a combined interpretation system for hair EtG and FAEEs. All markers demonstrated only low to moderate correlations. Optimum cut-off values for differentiation between social and chronic excessive drinking calculated for hair EtG and FAEEs were 28 pg/mg and 0.675 ng/mg, respectively. The critical values published in the "Consensus on Alcohol Markers 2012" by the Society of Hair Testing were confirmed.

  6. 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%.

  7. 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.

  8. 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.

  9. 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.

  10. A library synthesis of 4-hydroxy-3-methyl-6-phenylbenzofuran-2-carboxylic acid ethyl ester derivatives as anti-tumor agents.

    Science.gov (United States)

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

    2004-09-06

    As a result of a hit-to-lead program using a technique of solution-phase parallel synthesis, a highly potent (2,4-dimethoxyphenyl)-[6-(3-fluorophenyl)-4-hydroxy-3-methylbenzofuran-2-yl]methanone (15b) was synthesized as an optimized derivative of 4-hydroxy-3-methyl-6-phenylbenzofuran-2-carboxylic acid ethyl ester (1), which was discovered as a screening hit from small-molecule libraries and exhibited selective cytotoxicity against a tumorigenic cell line.

  11. 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.

  12. Synthesis of sn-2 docosahexaenoyl monoacylglycerol by mild enzymatic transesterification of docosahexaenoic acid ethyl ester and glycerol in a solvent-free system

    Directory of Open Access Journals (Sweden)

    Sonia Moreno-Perez

    2016-12-01

    Full Text Available The enzymatic transesterification of docosahexaenoic acid (DHA ethyl ester with glycerol was performed with several lipases in a solvent-free system and it involves the initial formation of sn-2 docosahexaenyl monoacylglyceride. This DHA derivative is highly relevant for improving the bioavailability of DHA and it has received increasing interest in the field of nutrition. Three commercial lipases, from Rhizomucor miehei (RML, Alcaligenes sp (QL, and Candida antarctica-fraction B (CALB were tested. In certain cases (CALB, using an excess of DHA ethyl ester and high temperatures the transesterification reaction continues to the formation of triacylglycerides, but in other cases, sn-2 monoacylglyceride (2-MG is the unique synthetic product even in the presence of high concentrations of DHA ethyl ester. At low temperatures (e.g. 37°C, RML derivatives synthesize only 2-MG in 15 min. These very mild conditions are very interesting for the thermal oxidative stability of the omega-3 fatty acid and for the thermal stability of the biocatalyst. Using Normal Phase HPLC-ELSD and accurate markers, the formation of the 2-MG was confirmed.

  13. 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。

  14. Synthesis and characterization of 5-(4-hydroxy-3-methoxy-phenyl-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidine-2,6-dicarboxylic acid 2-ethyl ester 6-methyl ester and its 6-ethyl ester 5-naphthalene derivative

    Directory of Open Access Journals (Sweden)

    H. Nagarajaiah

    2015-11-01

    Full Text Available The compounds 5-(4-hydroxy-3-methoxy-phenyl-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidine-2,6-dicarboxylic acid 2-ethyl ester 6-methyl ester (2a and 3,7-dimethyl-5-naphthalen-1-yl-5H-thiazolo[3,2-a]pyrimidine-2,6-dicarboxylic acid diethyl ester (2b were synthesized by the base catalyzed cyclocondensation of 3,4-dihydropyrimidine-2-thione with ethylacetoacetate. IR, 1H NMR, 13C NMR spectra and elemental analysis were used to characterize these compounds. The structures were determined by single crystal X-ray diffraction. The crystal structure is stabilized by intermolecular O–H…N, C–H…O, C–H…π and π…π weak interactions.

  15. Synthesis, Purification, and Quantification of Fatty Acid Ethyl Esters After trans-Esterification of Large Batches of Tobacco Seed Oil

    Directory of Open Access Journals (Sweden)

    Ashraf-Khorassani Mehdi

    2015-03-01

    Full Text Available L'objectif de la présente étude était de quantifier les esters éthyliques d'acides gras (FAEE produits à partir de deux grands lots d'huile de graines de tabac soumis à une transéstérification éthanolique en présence d'un catalyseur d'acide sulfurique. La purification des produits combinés de la réaction des esters éthyliques visait la suppression, autant que faire se peut, de la couleur et de l'odeur du produit final et fut accomplie via une chromatographie sur colonne conventionnelle avec silice sublimée et une élution en tandem de l'hexane, dans un premier temps et de l'alcool éthylique, dans un deuxième temps, en guise de phase mobile. La chromatographie en phase gazeuse fut utilisée afin de quantifier les esters éthyliques des acides gras spécifiques dans la matière purifiée. Le pourcentage d'esters éthyliques d'acides gras purs récupérés dans le lot n°1 s'éleva à près de 87% tandis que le pourcentage d'esters éthyliques d'acides gras purs récupérés dans le lot n°2 fut supérieur à 89% avec des rendements à la préparation supérieurs à 400 g d'esters éthyliques par essai d'estérification. Les esters éthyliques d'acides gras ne possédaient pas d'arome détectable et ne présentaient qu'une légère coloration jaune à l'issue de ce traitement chromatographique. Pour caractériser la pureté de chaque lot d'esters éthyliques d'acides gras produits, une chromatographie en phase supercritique dont la phase mobile était un fluide composé de dioxyde de carbone modifié au méthanol/acétonitrile et une phase fixe composée d'une silice greffée avec groupement fonctionnel octadécyle furent utilisées. Aucune impureté liée au glycérol ou à des acides gras libres ne fut détectée dans le produit transestérifié purifié. Notre article est le premier rapport décrivant la transestérification optimisée de l'huile de graines de tabac à une échelle relativement grande, ladite transest

  16. Fatty acid ethyl esters induce intestinal epithelial barrier dysfunction via a reactive oxygen species-dependent mechanism in a three-dimensional cell culture model.

    Directory of Open Access Journals (Sweden)

    Elhaseen Elamin

    Full Text Available BACKGROUND & AIMS: Evidence is accumulating that ethanol and its oxidative metabolite, acetaldehyde, can disrupt intestinal epithelial integrity, an important factor contributing to ethanol-induced liver injury. However, ethanol can also be metabolized non-oxidatively generating phosphatidylethanol and fatty acid ethyl esters (FAEEs. This study aims to investigate the effects of FAEEs on barrier function, and to explore the role of oxidative stress as possible mechanism. METHODS: Epithelial permeability was assessed by paracellular flux of fluorescein isothiocyanate-conjugated dextran using live cell imaging. Cell integrity was evaluated by lactate dehydrogenase release. Localization and protein levels of ZO-1 and occludin were analyzed by immunofluorescence and cell-based ELISA, respectively. Intracellular oxidative stress and cellular ATP levels were measured by dichlorofluorescein and luciferase driven bioluminescence, respectively. RESULTS: In vitro, ethyl oleate and ethyl palmitate dose dependently increased permeability associated with disruption and decreased ZO-1 and occludin protein levels, respectively, and increased intracellular oxidative stress without compromising cell viability. These effects could partially be attenuated by pretreatment with the antioxidant, resveratrol, pointing to the role of oxidative stress in the FAEEs-induced intestinal barrier dysfunction. CONCLUSIONS: These findings show that FAEEs can induce intestinal barrier dysfunction by disrupting the tight junctions, most likely via reactive oxygen species-dependent mechanism.

  17. 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;}

  18. Methyl and ethyl soybean esters production

    Energy Technology Data Exchange (ETDEWEB)

    Pighinelli, Anna Leticia Montenegro Turtelli; Park, Kil Jin; Zorzeto, Thais Queiroz [Universidade Estadual de Campinas (FEAGRI/UNICAMP), SP (Brazil). Fac. de Engenharia Agricola], E-mail: annalets@feagri.unicamp.br; Bevilaqua, Gabriela [Universidade Estadual de Campinas (IQ/UNICAMP), SP (Brazil). Inst. de Quimica

    2008-07-01

    Biodiesel is a fuel obtained from triglycerides found in nature, like vegetable oils and animal fats. Nowadays it has been the subject of many researches impulses by the creation of the Brazilian law that determined the blend of 2% of biodiesel with petrodiesel. Basically, there are no limitations on the oilseed type for chemical reaction, but due to high cost of this major feedstock, it is important to use the grain that is available in the region of production. Soybean is the oilseed mostly produced in Brazil and its oil is the only one that is available in enough quantity to supply the current biodiesel demand. The objective of this work was to study the effects of reaction time and temperature on soybean oil transesterification reaction with ethanol and methanol. A central composite experimental design with five variation levels was used and response surface methodology applied for the data analysis. The statistical analysis of the results showed that none of the factors affected the ethyl esters production. However, the methyl esters production suffered the influence of temperature (linear effect), reaction time (linear and quadratic) and interaction of these two variables. None of the generated models showed significant regression consequently it was not possible to build the response surface. The experiments demonstrated that methanol is the best alcohol for transesterification reactions and the ester yield was up to 85%. (author)

  19. 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.

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

    Energy Technology Data Exchange (ETDEWEB)

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

    2005-06-01

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

  1. 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。

  2. Ethanolysis of rapeseed oil - distribution of ethyl esters, glycerides and glycerol between ester and glycerol phases.

    Science.gov (United States)

    Cernoch, Michal; Hájek, Martin; Skopal, Frantisek

    2010-04-01

    The distribution of ethyl esters, triglycerides, diglycerides, monoglycerides, and glycerol between the ester and glycerol phase was investigated after the ethanolysis of rapeseed oil at various reaction conditions. The determination of these substances in the ester and glycerol phases was carried out by the GC method. The amount of ethyl esters in the glycerol phase was unexpectedly high and therefore the possibility of the reduction of this amount was investigated. The distribution coefficients and the weight distributions of each investigated substance were calculated and compared mutually. The distribution coefficients between the ester and glycerol phase increase in this sequence: glycerol, monoglycerides, diglycerides, ethyl esters, and triglycerides. Soaps and monoglycerides in the reaction mixture cause a worse separation of ethyl esters from the reaction mixture. The existence of a non-separable reaction mixture was observed also, and its composition was determined.

  3. Spectroscopy reveals that ethyl esters interact with proteins in wine.

    Science.gov (United States)

    Di Gaspero, Mattia; Ruzza, Paolo; Hussain, Rohanah; Vincenzi, Simone; Biondi, Barbara; Gazzola, Diana; Siligardi, Giuliano; Curioni, Andrea

    2017-02-15

    Impairment of wine aroma after vinification is frequently associated to bentonite treatments and this can be the result of protein removal, as recently demonstrated for ethyl esters. To evaluate the existence of an interaction between wine proteins and ethyl esters, the effects induced by these fermentative aroma compounds on the secondary structure and stability of VVTL1, a Thaumatin-like protein purified from wine, was analyzed by Synchrotron Radiation Circular Dichroism (SRCD) spectroscopy. The secondary structure of wine VVTL1 was not strongly affected by the presence of selected ethyl esters. In contrast, VVTL1 stability was slightly increased by the addition of ethyl-octanoate, -decanoate and -dodecanoate, but decreased by ethyl-hexanoate. This indicates the existence of an interaction between VVTL1 and at least some aroma compounds produced during fermentation. The data suggest that proteins removal from wine by bentonite can result in indirect removal of at least some aroma compounds associated with them.

  4. Analysis of the herbicidal mechanism of 4-hydroxy-3-methoxy cinnamic acid ethyl ester using iTRAQ and real-time PCR.

    Science.gov (United States)

    Zhang, Mingyue; Liu, Ce; Yang, Juan; Yang, Peng; Zhang, Lihui; Dong, Jingao

    2017-02-24

    Absolute quantitation (iTRAQ) is the latest development in the new quantitative proteomics technology for high-throughput identification and quantitation of proteins. The mechanisms underlying the 4-hydroxy-3-methoxy cinnamic acid ethyl ester treatment in Arabidopsis thaliana was investigated. Deficiency-induced changes in the protein profile of A. thaliana caused by this compound were analyzed using iTRAQ and quantitative real-time PCR. A total of 2909 proteins were quantified, of which 49 and 34 proteins were upregulated and downregulated, respectively, in the experimental plants compared with the controls. Treatment results showed that numerous proteins were involved in photosystemII, energy metabolism, and cell structure formation. Based on the upregulated and downregulated proteins, high amount of AT4G21280 protein acted on the oxygen-evolving enhancer protein 3-1, while low amount of AT1G10340 protein affected the catabolic process of the photosystemII-associated light-harvesting complex II. We selected these proteins to preliminarily verify the expression of proteins using quantitative real-time PCR to provide a reliable basis for further studies after proteomics analysis. Results show that the combined use of iTRAQ and quantitative real-time PCR provides an effective method to study proteins, leading to the determination of a new herbicide mechanism.

  5. Production of Omega-3 Fatty Acid Ethyl Esters from Menhaden Oil Using Proteus vulgaris Lipase-Mediated One-Step Transesterification and Urea Complexation.

    Science.gov (United States)

    Kim, Soo-Jin; Kim, Hyung Kwoun

    2016-05-01

    An organic solvent-stable lipase from Proteus vulgaris K80 was used to produce the omega-3 polyunsaturated fatty acid ethyl esters (ω-3 PUFA EEs). First, the lyophilized recombinant lipase K80 (LyoK80) was used to perform the transesterification reaction of menhaden oil and ethanol. LyoK80 produced the ω-3 PUFA EEs with a conversion yield of 82 % in the presence of 20 % water content via a three-step ethanol-feeding process; however, in a non-aqueous condition, LyoK80 produced only a slight amount of the ω-3 PUFA EEs. To enhance its reaction properties, the lipase K80 was immobilized on a hydrophobic bead to derive ImmK80; the biochemical properties and substrate specificity of ImmK80 are similar to those of LyoK80. ImmK80 was then used to produce ω-3 PUFA EEs in accordance with the same transesterification reaction. Unlike LyoK80, ImmK80 achieved a high ω-3 PUFA EE conversion yield of 86 % under a non-aqueous system via a one-step ethanol-feeding reaction. The ω-3 PUFA EEs were purified up to 92 % using a urea complexation method.

  6. Synthesis, screening for antiacetylcholinesterase activity and binding mode prediction of a new series of [3-(disubstituted-phosphate)-4,4,4-trifluoro-butyl]-carbamic acid ethyl esters

    Energy Technology Data Exchange (ETDEWEB)

    Zanatta, Nilo; Marchi, Tiago M.; Bonacorso, Helio G.; Martins, Marcos A.P.; Flores, Alex F.C. [Universidade Federal de Santa Maria, RS (Brazil). Dept. de Quimica. Nucleo de Quimica de Heterociclos]. E-mail: zanatta@base.ufsm.br; Borchhardt, Deise M.; Andricopulo, Adriano D.; Salum, Livia B. [Universidade de Sao Paulo (USP), Sao Carlos, SP (Brazil). Centro de Biotecnologia Molecular Estrutural. Lab. de Quimica Medicinal e Computacional; Carpes, Adriana D.; Schetinger, Maria R.C. [Universidade Federal de Santa Maria, RS (Brazil). Dept. de Quimica. Lab. de Enzimologia Toxicologica

    2008-07-01

    A series of nine new [3-(disubstituted-phosphate)-4,4,4-trifluoro-butyl]-carbamic acid ethyl esters (phosphate-carbamate compounds) was obtained through the reaction of (4,4,4-trifluoro-3-hydroxybut-1-yl)-carbamic acid ethyl esters with phosphorus oxychloride followed by the addition of alcohols. The products were characterized by {sup 1}H, {sup 13}C, {sup 31}P, and {sup 19}F NMR spectroscopy, GC-MS, and elemental analysis. All the synthesized compounds were screened for acetylcholinesterase (AChE) inhibitory activity using the Ellman method. All compounds containing phosphate and carbamate pharmacophores in their structures showed enzyme inhibition, being the compound bearing the diethoxy phosphate group (2b) the most active compound. Molecular modeling studies were performed to investigate the detailed interactions between AChE active site and small-molecule inhibitor candidates, providing valuable structural insights into AChE inhibition. (author)

  7. Development of continuous deglycerolisation reactor for ethyl ester production

    Directory of Open Access Journals (Sweden)

    Ruamporn Nikhom

    2014-12-01

    Full Text Available In this work, the development of continuous deglycerolisation (CD reactor for ethyl ester production was investigated to improve the ethyl ester conversion. The device to assist separation of glycerol, in the CD unit, integrates transesterification (mixing zone and separation (settling zone into one unit. For reversible transesterification, removing glycerol during reaction can drive the equilibrium to the product side in order to achieve high conversion. Two models of device to assist separation of glycerol have been carried out to investigate the suitable conditions for ethyl ester production. Results showed that the fin-type model could separate higher amount of glycerol from the reaction system in order to achieve high transesterification conversion. The suitable conditions found in this study were: molar ratio of oil to ethanol of 1:5, KOCH3 concentration of 1.6 %wt. retention time of 15 min and reaction temperature of 70°C. At these conditions, ethyl ester’s purity and yield were 97.3%wt. and 92.0%wt., respectively. In addition, the fuel properties of the final ethyl ester product met the biodiesel standard for methyl ester which specified by Department of Energy Business.

  8. 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

  9. 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.

  10. Anticholinesterase activity of fluorochloronitroacetic acid esters

    Energy Technology Data Exchange (ETDEWEB)

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

    1984-11-01

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

  11. 催化合成脂肪族二元酸烷氧基酯的反应动力学研究%Kinetics for catalytic synthesis of aliphatic dicarboxylic acid alkoxy ethyl ester

    Institute of Scientific and Technical Information of China (English)

    陈慕华; 方亮; 刘准; 曹惠庆; 朱新宝

    2012-01-01

    Aliphatic dicarboxylic acid alkoxy ethyl ester is synthesized from aliphatic dicarboxylic acid and ethyle glycol monobutyl ether by using sulfuric acid as catalyst. Apparent rate constants for those acid-catalyzed homogeneous esterification reactions are obtained, and apparent kinetics models are established. The results show that the synthesis of aliphatic dicarboxylic acid alkoxy ethyl ester under the temperature from 453. 15 to 473. 15 K is the third order irreversible reaction. According to the kinetic data of those experiments using different aliphatic dicarboxylic acid (C5-C8), activation energy values (Ea) are all in the range from 220 to 250 kj/mol.%脂肪族二元酸烷氧基酯是一类性能优良的耐寒性增塑剂产品.以二元羧酸及乙二醇丁醚为原料,在硫酸催化下合成烷氧基酯,测定了表观速率常数,并建立了反应体系的酯化反应动力学模型.实验结果表明,在453.15~473.15 K,合成脂肪族二元酸烷氧基酯的宏观动力学符合三级不可逆反应特征,以C5至C8的二元羧酸为原料的酯化过程其反应表观活化能在220~250 kJ/mol内.

  12. 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.

  13. 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.

  14. 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.

  15. Optimization of lipase-catalyzed synthesis of fatty acid ethyl ester from corn oil%脂肪酶催化玉米油合成脂肪酸乙酯工艺研究

    Institute of Scientific and Technical Information of China (English)

    康建波; 胡士恒; 王亚男; 周亚军

    2012-01-01

    为研制食药两用的功能性原料亚油酸乙酯,以玉米油和乙醇为原料,经固定化脂肪酶催化合成脂肪酸乙酯.通过单因素试验和响应面分析法(RSM)研究醇油摩尔比、脂肪酶用量、反应温度、反应时间对玉米油脂肪酸乙酯合成的影响.研究结果表明,玉米油脂肪酸乙酯合成的最佳工艺条件为醇油摩尔比为4∶1,脂肪酶质量分数为30.82%,反应温度为50.39℃,反应时间为24.15 h,在此工艺条件下脂肪酸乙酯转化率为90.20%.%In order to develop the functional raw material linoleic acid ethylester which can be used as both food and medicine, the fatty acid ethyl esters are synthesized by immobilized lipase-catalyzed reaction with corn oil and alcohol as raw material in this study. Based on the single factor experiments and response surface methodology ( RSM ) , the influences of molar ratio ethanol and corn oil, the amount of enzyme, the reaction temperature and reaction time on the synthesis of fatty acid ethyl ester from corn oil are investigated. The obtained optimal parameters are shown as follows -A-1 molar ratio of ethanol to oil,30 % of amount of enzyme,50. 39℃ of reaction temperature and 24 hours of reaction time. The rate of conversion of corn oil can reach 90. 20% .

  16. Growth of glycine ethyl ester hydrochloride and its characterizations

    Science.gov (United States)

    Venkatesan, G.; Pari, S.

    2016-11-01

    Single crystal of glycine ethyl ester hydrochloride by slow evaporation method is reported. The grown crystal characterized by single crystal X-ray diffraction, FT-IR, UV-Vis-NIR and fluorescence spectroscopy. It is established that the crystal falls under the monoclinic system and space group P21/c with the cell parameters as: a=8.565 Å, b=12.943 Å, c=6.272 Å, α=γ=90°, β=103.630º. UV-Vis-NIR spectrum shows indirect allowed transition with a band gap of 5.21 eV and other optical properties are measured. The crystal is also shown to have a high transmittance in the visible region. The third order nonlinear property and optical limiting have been investigated using Z-Scan technique. Complex impedance spectrum measured at the dc conductivity. Dependence of dielectric constant, dielectric loss and ac conductivity on frequency at different temperature of applied ac field is analyzed. The mechanical behavior has been assessed by Vickers microhardness indenter. The thermal behavior of glycine ethyl ester hydrochloride was analyzed using TG/DTA thermal curves. From the thermal study, the material was found to possess thermal stability up to 174 °C. The predicted NLO properties, UV-Vis transmittance and Z-scan studies indicate that is an attractive material for photonics optical limiting applications.

  17. 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

  18. ω-3多烯酸乙酯对肿瘤恶病质的影响及其机制%Effect of ω-3 Acid Ethyl Ester on Cancer Cachexia and Its Mechanism

    Institute of Scientific and Technical Information of China (English)

    郭丹; 柳欣欣; 刘玉琴; 顾蓓; 徐锡霞

    2012-01-01

    目的 临床上肿瘤恶病质的治疗十分棘手,初步的研究提示ω-3多不饱和脂肪酸本身作为免疫营养素具有改善肿瘤恶病质的功能.本研究应用在心血管疾病中广泛使用的ω-3多烯酸乙酯口服制剂来干预荷瘤小白鼠,探讨其对肿瘤恶病质的改善作用及机制.方法 使用小白鼠结肠癌细胞株C-26皮下注射Balb/c小白鼠,构建荷瘤小白鼠肿瘤恶病质模型,将小白鼠分为3组:对照组(无荷瘤小白鼠组)、荷瘤无干预组和荷瘤ω-3多烯酸乙酯干预组,荷瘤ω-3多烯酸乙酯干预组小白鼠给予ω-3多烯酸乙酯(DHA、EPA>80%)灌胃(2 g·kg-1·d-1,体积<0.1 ml).连续2周记录小白鼠饮食量、体质量及腓肠肌重量等指标,并比较各组肿瘤组织炎性因子IL-1β、IL-6的mRNA表达差异.结果 ω-3多烯酸乙酯干预组相对于荷瘤无干预组可显著改善荷瘤小白鼠的体质量减轻程度,减少瘦肉体(腓肠肌)的丢失,并降低肿瘤组织的炎性因子IL-1β、IL-6 的mRNA表达水平.结论 口服ω-3多烯酸乙酯可以降低组织炎性因子表达,达到改善肿瘤恶病质的作用.%Objective Treatment of cancer cachexia is difficult, and some studies have suggested that as a kind of immune nutrient, to -3 polyunsaturated fatty acids can improve cancer cachexia and is likely to be a very promising treatment of cancer cachexia. In this study, we used ω -3 acid ethyl ester, which is widely used in cardiovascular diseases, to intervene in the tumor - bearing mice to investigate its effect on cancer cachexia as well as its mechanism. Methods Subcutaneous injection of colon cancer cell line ( C - 26 ) was given to Balb/c mice to build tumor cachexia model. Then the mice were divided into three groups: normal control group ( no tumor - bearing mice ), tumor - bearing mice without intervention group and tumor - bearing mice intervened with oral to -3 acid ethyl ester group. The intervened group was fed with ω -3 acid

  19. Functional group induced excited state intramolecular proton transfer process in 4-amino-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester: a combined spectroscopic and density functional theory study.

    Science.gov (United States)

    Jana, Sankar; Dalapati, Sasanka; Guchhait, Nikhil

    2013-09-01

    The molecule methyl-2-aminonicotinate (2-MAN) does not exhibit excited state intramolecular proton transfer (ESIPT), but its derivative 4-amino-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (AMPCE), widely used in the preparation of pyrimidopyrimidines as a protein kinase inhibitor, does exhibit ESIPT. Increasing acidic and basic character at the proton donor and proton acceptor sites by adding functional groups is found to be responsible for the large Stokes shifted ESIPT emission (Δν = 12,706 cm(-1)) in AMPCE. The photophysics of AMPCE have been explored on the basis of steady state and time resolved spectral measurements, quantum yield calculation with variation of polarity, as well as hydrogen bonding ability of solvents. Experimental findings have been correlated with the calculated structure and potential energy surfaces based on the intramolecular proton transfer model obtained by density functional theory (DFT). Properties based on the calculated excited state surfaces generated in vacuo and methanol solvent using time dependent density functional theory (TDDFT) and time dependent density functional theory polarized continuum model (TDDFT-PCM), respectively, show good agreement with the experimental findings. HOMO and LUMO diagrams also support the favorable ESIPT process in the first excited state potential energy surface.

  20. 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.

  1. 栀子油制备脂肪酸乙酯工艺的优化%Optimization of the Preparation Process of Fatty Acid Ethyl Ester from Gardenia Oil

    Institute of Scientific and Technical Information of China (English)

    孟陆丽; 程谦伟; 秦利平

    2012-01-01

    Using gardenia oil as raw material, fatty acid ethyl ester was prepared by NaOH catalyzed transesterification. The effects of molar ratio of alcohol to oil, catalyst dosage, reaction temperature, reaction time on the ethyl esterification were e-valuated through single factor tests, based on which response surface method was adopted to optimize the preparation conditions. The results showed that the optimum conditions for the esterification process were as follows, molar ratio of alcohol to oil, 6.7:1; catalyst dosage, 1.65% of the mass of gardenia oil; reaction temperature, 75℃; reaction time, 2.5 h. Under the optimal conditions, the hydroxyl value of the preduct was 146.62 mg(KOH)/g.%以栀子油为原料,采用碱催化法进行乙酯化反应,采用单因素试验考察醇油摩尔比、催化剂用量、反应温度、反应时间对乙酯化反应产物羟基值的影响,并进一步设计响应面试验优化反应条件.结果表明,栀子油乙酯化的最佳工艺条件为醇油摩尔比6.7∶1,催化剂用量为栀子油质量的1.65%,反应温度75℃,反应时间2.5 h,在此工艺条件下乙酯化反应产物的羟基值为146.62 mg(KOH)/g.

  2. Synthesis, spectroscopic and structural studies of 4-Amino-3-(ethyl)-5-(4-chlorophenyl)-4H-1,2,4-triazole and 4-Amino-3-cyclopropyl-5-oxo-4,5-dihydro-1,2,4-triazole-1-yl-acetic acid ethyl ester

    Science.gov (United States)

    Şahin, Onur; Kantar, Cihan; Şaşmaz, Selami; Gümrükçüoğlu, Nurhan; Büyükgüngör, Orhan

    2014-06-01

    The title compounds of 4-Amino-3-(ethyl)-5-(4-chlorophenyl)-4H-1,2,4-triazole (I, C10H11ClN4) and 4-Amino-3-cyclopropyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl-acetic acid ethyl ester (II, C9H14N4O3), have been determined using X-ray diffraction techniques and characterized by IR, 1H NMR and 13C NMR. X-ray study shows that the title compounds both have strong intermolecular Nsbnd H⋯N hydrogen bonds. The molecules of I are linked into a two-dimensional framework structure by Nsbnd H⋯N and Csbnd H⋯N hydrogen bonds which produce R22(8)R44(14)R44(15) chain of rings, while in II, the combination of Nsbnd H⋯N, Nsbnd H⋯O and Csbnd H⋯O hydrogen bonds along [1 0 0] generates a chain of edge-fused R22(10)R22(16)R42(14) R44(14) rings.

  3. 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

  4. 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%.

  5. A novel alkenoic acid ester and a new benzophenone from Ranunculus ternatus

    Institute of Scientific and Technical Information of China (English)

    2007-01-01

    A novel alkenoic acid ester, (E)-4-hydroxy-dodec-2-enedioic acid-12-O-methyl ester and a new benzophenone, ethyl (S)-3-[2-(3,4-dihydroxybenzoyl)-4,5-dihydroxyphenyl]-2-hydroxypropanoate, together with a known compound, (E)-4-hydroxy-dodec-2-enedioic acids were isolated from the roots of Ranunculus ternatus. Their structures were elucidated by spectroscopic methods.

  6. 78 FR 53051 - Ethyl-2E,4Z-Decadienoate (Pear Ester); Exemption From the Requirement of a Tolerance

    Science.gov (United States)

    2013-08-28

    ... AGENCY 40 CFR Part 180 Ethyl-2E,4Z-Decadienoate (Pear Ester); Exemption From the Requirement of a...-2E,4Z- decadienoate (pear ester) in or on all food commodities. This regulation eliminates the need to establish a maximum permissible level for residues of ethyl-2E,4Z-decadienoate (pear ester)....

  7. 75 FR 17769 - In the Matter of Certain Products Advertised as Containing Creatine Ethyl Ester; Notice of...

    Science.gov (United States)

    2010-04-07

    ... COMMISSION In the Matter of Certain Products Advertised as Containing Creatine Ethyl Ester; Notice of... Ester of Respondents Found in Default; Issuance of Cease and Desist Orders AGENCY: U.S. International... ethyl ester by reason of false advertising in violation of Section 43(a) of the Lanham Act, 15...

  8. 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.

  9. 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.

  10. 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.)

  11. Fumaric acid esters in dermatology

    Directory of Open Access Journals (Sweden)

    Uwe Wollina

    2011-01-01

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

  12. 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

  13. 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.

  14. Transferable force field for carboxylate esters: application to fatty acid methylic ester phase equilibria prediction.

    Science.gov (United States)

    Ferrando, Nicolas; Lachet, Véronique; Boutin, Anne

    2012-03-15

    In this work, a new transferable united-atoms force field for carboxylate esters is proposed. All Lennard-Jones parameters are reused from previous parametrizations of the AUA4 force field, and only a unique set of partial electrostatic charges is introduced for the ester chemical function. Various short alkyl-chain esters (methyl acetate, ethyl acetate, methyl propionate, ethyl propionate) and two fatty acid methylic esters (methyl oleate and methyl palmitate) are studied. Using this new force field in Monte Carlo simulations, we show that various pure compound properties are accurately predicted: saturated liquid densities, vapor pressures, vaporization enthalpies, critical properties, liquid-vapor surface tensions. Furthermore, a good accuracy is also obtained in the prediction of binary mixture pressure-composition diagrams, without introducing empirical binary interaction parameters. This highlights the transferability of the proposed force field and gives the opportunity to simulate mixtures of industrial interest: a demonstration is performed through the simulation of the methyl oleate + methanol mixture involved in the purification sections of biodiesel production processes.

  15. 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...

  16. Antiviral and Virucidal Activities of N-Cocoyl-L-Arginine Ethyl Ester

    Directory of Open Access Journals (Sweden)

    Hisashi Yamasaki

    2011-01-01

    Full Text Available Various amino acid-derived compounds, for example, Nα-Cocoyl-L-arginine ethyl ester (CAE, alkyloxyhydroxylpropylarginine, arginine cocoate, and cocoyl glycine potassium salt (Amilite, were examined for their virucidal activities against herpes simplex virus type 1 and 2 (HSV-1 and HSV-2, influenza A virus (IAV, and poliovirus type 1 (PV-1 in comparison to benzalkonium chloride (BKC and sodium dodecylsulfate (SDS as a cationic and anionic control detergent and also to other commercially available disinfectants. While these amino acid-derived compounds were all effective against HSV-1 and HSV-2, CAE and Amilite were the most effective. These two compounds were, however, not as effective against IAV, another enveloped virus, as against HSV. Cytotoxicity of CAE was weak; at 0.012%, only 5% of the cells were killed under the conditions, in which 100% cells were killed by either SDS or BKC. In addition to these direct virucidal effects, CAE inhibited the virus growth in the HSV-1- or PV-1-infected cells even at 0.01%. These results suggest a potential application of CAE as a therapeutic or preventive medicine against HSV superficial infection at body surface.

  17. 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.

  18. 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.

  19. Conversion of carbohydrates to levulinic acid esters

    DEFF Research Database (Denmark)

    2014-01-01

    The present invention relates to the field of converting carbohydrates into levulinic acid, a platform chemical for many chemical end products. More specifically the invention relates to a method for converting carbohydrates such as mono-, di- or polysaccharides, obtained from for example biomass...... production into a suitable levulinic acid ester in the presence of a zeolite or zeotype catalyst and a suitable alcohol, and the ester may be further converted into levulinic acid if desired....

  20. 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.

  1. The synthesis of 5-(1- sup 11 C)ethyl barbiturates from labelled malonic esters

    Energy Technology Data Exchange (ETDEWEB)

    Gee, A.; Laangstroem, B. (Uppsala Univ. (Sweden). Dept. of Organic Chemistry)

    1991-01-01

    The synthesis of ({sup 11}C)phenobarbital, ({sup 11}C)pentobarbital and({sup 11}C)amobarbital labelled in the 5-(1-{sup 11}C)ethyl position is reported. The malonic esters R- CH(CO{sub 2}Et){sub 2} R phenyl-, 1-methylbutyl-, and 3- methylbutyl- were alkylated with (1-{sup 11}C)ethyl iodide prepared from ({sup 11}C)carbon dioxide. Ring closure of the 2-(1-{sup 11}C)ethyl-labelled malonic esters with urea afforded 5-(1-{sup 11}C)ethyl-phenobarbital,-phenobarbital, -pentobarbital and -amobarbital synthesis times of 42-47 min, counted from ({sup 11}C) carbon dioxide. In typical syntheses starting with 3 GBq pentobarbitol and (81 mCi) ({sup 11}C)carbon dioxide, 150-215 MBq (4-6 mCi) were produced in 25-30% decay corrected -amobarbital radiochemical yields with radiochemical purities greater than 98%. (author).

  2. 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.

  3. Multicomponent Synthesis of a N-Protected Alpha-Amino Ester: Ethyl 2-((4-Methoxyphenyl)Amino)-3-Phenylpropanoate

    Science.gov (United States)

    Le Gall, Erwan; Pignon, Antoine

    2012-01-01

    This laboratory experiment describes the preparation of a N-protected phenylalanine ethyl ester by a zinc-mediated Mannich-like multicomponent reaction between benzyl bromide, "p"-anisidine, and ethyl glyoxylate. The one-step reaction involves the in situ metallation of benzyl bromide into a benzylzinc reagent and its addition onto imine (Barbier…

  4. 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.

  5. 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.

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

    Science.gov (United States)

    2010-04-01

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

  7. THE CLINICAL BENEFIT OF OMEGA-3 PUFA ETHYL ESTERS SUPPLEMENTATION IN PATIENTS WITH HEART FAILURE

    Directory of Open Access Journals (Sweden)

    Martin R Cowie

    2010-06-01

    Full Text Available Chronic heart failure, a syndrome of cardiac dysfunction associated with breathlessness, effort intolerance and fluid retention, affects 1-2% of the population. The most frequent cause is impairment of systolic function of the left ventricle, usually due to coronary artery disease. Hyper-tension or diabetes often co-exist. Treatment of heart failure (HF is centred on correction of any reversible pathology and antagonism of the intense neurohormonal activation triggered by the cardiac dysfunction. This is achieved by angiotensin converting enzyme inhibitors (or angiotensin receptor blockers, beta-blockers and in more severe cases, an aldosterone antagonist.The prognosis of HF remains poor – with a first year mortality of over 30%, reducing to 10% per annum thereafter. Death is usually due to either progressive pump failure or sudden death, which is presumably arrhythmic in origin. A randomised double-blind controlled trial of 1g daily of omega-3 polyunsaturated fatty acids (PUFA ethyl esters in almost 7000 patients with symptomatic chronic heart failure of any cause reported a 9% relative risk reduction in mortality (P=0.04 and 8% relative risk reduction in mortality or cardiovascular hospitalisation (P=0.009(GISSI-HF. In absolute terms, 56 patients need to be treated for 3.9 years to prevent one death. International guidelines recommend the prescription of 1g daily of n-3 PUFA as an adjuvant to secondary prevention in patients after myocardial infarction (based on the results of GISSI-Prevenzione, published in 1999 and for those with hypertriglyceridaemia, but are likely to be updated to recommend this therapy for patients with heart failure also.

  8. 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 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%) (Pomega-3 index level of 8%-12% in the treated vs placebo group (22.6% vs. 1.3%, Pomega-3 index levels were ultimately achieved after four years in this trial are unknown.

  9. Conditions of Using Mesoporous Molecular Sieves Al-MCM-41 as Catalyst to Synthesize Isoprene Ene Acid Ethyl Ester as Pesticide%利用中孔分子筛Al-MCM-41催化合成农药异戊烯酸乙酯的条件

    Institute of Scientific and Technical Information of China (English)

    唐晓红; 吴崇珍; 梁丽珍; 李成未; 李保军

    2012-01-01

    [方法]利用中孔分子筛A1-MCM-41作催化剂,直接用反应物乙醇作带水剂,以乙醇和异戊烯酸为原料,采用分批补充乙醇的工艺方法合成农药异戊烯酸乙酯.考察了催化剂用量、反应物物质的量比、反应温度和反应时间对反应转化率和选择性的影响.[结果]该反应最佳的合成条件:异戊烯酸和乙醇的物质的量比为1∶8,催化剂的量为异戊烯酸质量的1.8%,反应时间为6h,反应在剧烈回流温度下进行.在此条件下,异戊烯酸转化率可达89.9%,产品纯度大于99.7%.[结论]中孔分子筛Al-MCM-41可作为合成异戊烯酸乙酯高效而环保的固体酸催化剂.%[Methods] The isoprene ene acid ethyl ester was synthesized from isoprene ene acid and ethanol by using mesoporous molecular sieves AI-MCM-41 as catalyst and directly using reactant ethanol as dehydrant. The process methods of replenishing ethanol in batches was used. The factors such as catalyst amount, reactant ratio, reaction temperature and reaction time which affect the conversion and selectivity were investigated. [Results] The experimental result showed that the optimum conditions are as follows: the mole ratio of isoprene ene acid to ethanol is 1:8: the amount of catalyst is 1.8% to isoprene ene acid: the reaction time is 6 h at reflux temperature. The conversion is 89.9% and the purity of the product is above 99.7% under the optimum conditions. [Conclusions] The mesoporous molecular sieves AI-MCM-41 can be used as efficient and environmental solid acid catalyst on the catalytic synthesis of isoprene ene acid ethyl ester.

  10. 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)

  11. 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

  12. 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

    2004-09-08

    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.

  13. 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...

  14. 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

  15. Naturally Occurring Cinnamic Acid Sugar Ester Derivatives

    Directory of Open Access Journals (Sweden)

    Yuxin Tian

    2016-10-01

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

  16. Oxidative stability of biodiesel from soybean oil fatty acid ethyl esters Estabilidade oxidativa de biodiesel de ésteres etílicos de ácidos graxos de soja

    Directory of Open Access Journals (Sweden)

    Roseli Ap. Ferrari

    2005-06-01

    Full Text Available Biodiesel consists of long-chain fatty acid esters, derived from renewable sources such as vegetable oils, and its utilization is associated to the substitution of the diesel oil in engines. Depending on the raw material, biodiesel can contain more or less unsaturated fatty acids in its composition, which are susceptible to oxidation reactions accelerated by exposition to oxygen and high temperatures, being able to change into polymerized compounds. The objective of this work was to determine the oxidative stability of biodiesel produced by ethanolysis of neutralized, refined, soybean frying oil waste, and partially hydrogenated soybean frying oil waste. The evaluation was conducted by means of the Rancimat® equipment, at temperatures of 100 and 105ºC, with an air flow of 20 L h-1. The fatty acid composition was determined by GC and the iodine value was calculated. It was observed that even though the neutralized, refined and waste frying soybean oils presented close comparable iodine values, biodiesel presented different oxidative stabilities. The biodiesel from neutralized soybean oil presented greater stability, followed by the refined and the frying waste. Due to the natural antioxidants in its composition, the neutralized soybean oil promoted a larger oxidative stability of the produced biodiesel. During the deodorization process, the vegetable oils lose part of these antioxidants, therefore the biodiesel from refined soybean oil presented a reduced stability. The thermal process degrades the antioxidants, thus the biodiesel from frying waste oil resulted in lower stability, the same occuring with the biodiesel from partially hydrogenated waste oil, even though having lower iodine values than the other.Biodiesel consiste em ésteres de ácidos graxos de cadeia longa, proveniente de fontes renováveis como óleos vegetais, e sua utilização está associada à substituição do diesel em motores. Dependendo da matéria-prima, o biodiesel

  17. 75 FR 71556 - Polyoxyalkylated Glycerol Fatty Acid Esters; Tolerance Exemption

    Science.gov (United States)

    2010-11-24

    ... AGENCY 40 CFR Part 180 Polyoxyalkylated Glycerol Fatty Acid Esters; Tolerance Exemption AGENCY... from the requirement of a tolerance for residues of polyoxyalkylated glycerol fatty acid esters; the... ethylene oxide or propylene oxide, also known as polyoxyalkylated glycerol fatty acid esters, when used...

  18. 40 CFR 721.1732 - Nitrobenzoic acid octyl ester.

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Nitrobenzoic acid octyl ester. 721... Substances § 721.1732 Nitrobenzoic acid octyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as nitrobenzoic acid octyl ester (PMN...

  19. 40 CFR 721.5310 - Neononanoic acid, ethenyl ester.

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Neononanoic acid, ethenyl ester. 721... Substances § 721.5310 Neononanoic acid, ethenyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as neononanoic acid, ethenyl ester (PMN...

  20. 40 CFR 721.4158 - Hexadecanoic acid, ethenyl ester.

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Hexadecanoic acid, ethenyl ester. 721... Substances § 721.4158 Hexadecanoic acid, ethenyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as hexadecanoic acid, ethenyl ester (PMN...

  1. 40 CFR 721.4215 - Hexanedioic acid, diethenyl ester.

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Hexanedioic acid, diethenyl ester. 721... Substances § 721.4215 Hexanedioic acid, diethenyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as hexanedioic acid, diethenyl ester (PMN...

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

    DEFF Research Database (Denmark)

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

    2010-01-01

    Investigations into expanded uses of modified flavonoids are often limited by the availability of these high purity compounds. As such, a simple, effective and relatively fast method for isolation of gram quantities of both long and medium chain fatty acid esters of rutin following scaled-up bios...... following a two-step solvent purification procedure whereby excess fatty acid substrate was first removed in a heptane/water (4:1, v/v) system, followed by selective ester extraction using an ethyl acetate/water system (1:6, v/v) at elevated temperature....

  3. 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)

  4. 40 CFR 721.3152 - Ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl...

    Science.gov (United States)

    2010-07-01

    ...-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl sulfates (salts). 721.3152 Section 721... Ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl sulfates... ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl...

  5. 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.

  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. An overview of the properties of fatty acid alkyl esters

    Science.gov (United States)

    Fatty acid alkyl esters of plant oils, especially in the form of methyl esters, have numerous applications with fuel use having received the most attention in recent times due to the potential high volume. Various properties imparted by neat fatty acid alkyl esters have been shown to influence fuel ...

  8. 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.

  9. Incorportation of Ethyl Esters of EPA and DHA in Soybean Lecithin Using Rhizomucor miehei Lipase: Effect of Additives and Solvent-Free Conditions.

    Science.gov (United States)

    Marsaoui, Nabil; Naghmouchi, Karim; Baah, John; Raies, Aly; Laplante, Serge

    2015-06-01

    The transesterification of soybean lecithin with ethyl esters of polyunsaturated fatty acids (eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA)) using immobilized lipase from Rhizomucor miehei was tested in the presence or absence of organic solvent (hexane) and additives (urea with Ca(2+) or Mg(2+)). The reaction was carried out at a water concentration of 4 % and ethyl ester to phospholipid mass ratio of 3:1. After 24 h of reaction without solvent or additive, fatty acid incorporation reached 29.1 % and thereafter increased only slightly. After 48 h, incorporation was highest in the presence of Mg(2+), urea, and solvent. After 72 h, it was highest with Mg(2+) and urea in the presence or absence of solvent (56.8 and 45.7 %, respectively). Incorporation of EPA and DHA was thus initially fast without solvent and additive, but was increased after prolonged reaction in the presence of Mg(2+) and urea with or without solvent. These results are innovative and promising since they show that immobilized Rhizomucor miehei lipase has potential as a biocatalyst for interesterification reactions without solvent.

  10. Bioactive caffeic acid esters from Glycyrrhiza glabra.

    Science.gov (United States)

    Dey, Surajit; Deepak, Mundkinajeddu; Setty, Manjunath; D'Souza, Prashanth; Agarwal, Amit; Sangli, Gopal Krishna

    2009-01-01

    Thin layer chromatography bioautography (using DPPH spray reagent) guided fractionation of Glycyrrhiza glabra led to the isolation of two caffeic acid derivative esters, viz. eicosanyl caffeate (1) and docosyl caffeate (2). The two compounds exhibited potent elastase inhibitory activity, with IC(50) values of 0.99 microg mL(-1) and 1.4 microg mL(-1) for 1 and 2, respectively. The compounds also showed moderate antioxidant activity in DPPH and ABTS scavenging assays. The results indicate a possible role of caffeic acid derivatives, in addition to flavonoids in the anti-ulcer properties of G. glabra.

  11. 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.

  12. 尿素包合法富集鱼油乙酯中的EPA和DHA%Enrichment of EPA and DHA from Fish Oil Ethyl Ester by Urea Inclusion Method

    Institute of Scientific and Technical Information of China (English)

    单幸福; 李江; 郑晓林; 许媛; 刘发义

    2016-01-01

    采用尿素包合法富集鱼油乙酯中的二十碳五烯酸(EPA)和二十二碳六烯酸(DHA),通过单因素实验和正交实验确定最优富集工艺为:m(尿素)∶m(鱼油乙酯)为1.5∶1、V (乙醇)∶m(鱼油乙酯)为3∶1、包合时间1 h、包合温度75℃、结晶温度25℃,一次包合的 EPA+DHA含量可达85%以上,收率60%。%Eicosapentaenoic acid(EPA)and decosahexaenoic acid(DHA)from fish oil ethyl ester were en-riched by an urea inclusion method.The optimum enrichment process obtained by a single factor experiment and an orthogonal experiment were as follows:m(urea)∶m(fish oil ethyl ester)of 1 .5∶1 ,V(ethanol)∶m(fish oil ethyl ester)of 3∶1,inclusion time of 1 h,inclusion temperature of 75 ℃,crystallization temperature of 25 ℃. Under above conditions,the total content of EPA and DHA from fish oil ethyl ester reached 85%,and the yield was 6 0%.

  13. 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.

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

    Directory of Open Access Journals (Sweden)

    Lanza, B.

    2016-06-01

    Full Text Available There are several methods to prepare table olives, and each of the steps and conditions during this processing can affect the composition and nutritional value of the product. The influence of abnormal fermentation and poorly conducted technological treatments was examined here in terms of the lipid fraction of table olives. In ‘Greek style’ olives, a low concentration of brine can allow the growth of spontaneous microflora and consequent organoleptic defects (‘putrid/butyric fermentation’, ‘winey-vinegary’. Here, the ‘Kalamata’ and ‘Moresca’ cultivars can produce methyl esters (methyl oleate/ linoleate: 553 and 450 mg·kg-1 oil, respectively and ethyl esters (ethyl oleate/ inoleate: 4764 and 4195; palmitate: 617 and 886 mg·kg-1 oil, respectively. In ‘Sevillan style’ olives, a high NaOH concentration influences the fatty-acid composition less, but is difficult to eliminate, for a ‘soapy’ defect. The ‘Giarraffa’ and ‘Nocellara del Belice’ cultivars produce only ethyl esters (ethyl oleate/ linoleate: 222 and 289 mg·kg-1 oil, respectively. With this production of ethyl and methyl esters from the principal fatty acids in the lipid fractions of table olives, methods that provide only biological treatments (i.e., Greek style pose more risk than methods that provide only chemical treatments (i.e., Sevillan style.H

  15. High throughput, colorimetric screening of microbial ester biosynthesis reveals high ethyl acetate production from Kluyveromyces marxianus on C5, C6, and C12 carbon sources.

    Science.gov (United States)

    Löbs, Ann-Kathrin; Lin, Jyun-Liang; Cook, Megan; Wheeldon, Ian

    2016-10-01

    Advances in genome and metabolic pathway engineering have enabled large combinatorial libraries of mutant microbial hosts for chemical biosynthesis. Despite these advances, strain development is often limited by the lack of high throughput functional assays for effective library screening. Recent synthetic biology efforts have engineered microbes that synthesize acetyl and acyl esters and many yeasts naturally produce esters to significant titers. Short and medium chain volatile esters have value as fragrance and flavor compounds, while long chain acyl esters are potential replacements for diesel fuel. Here, we developed a biotechnology method for the rapid screening of microbial ester biosynthesis. Using a colorimetric reaction scheme, esters extracted from fermentation broth were quantitatively converted to a ferric hydroxamate complex with strong absorbance at 520 nm. The assay was validated for ethyl acetate, ethyl butyrate, isoamyl acetate, ethyl hexanoate, and ethyl octanoate, and achieved a z-factor of 0.77. Screening of ethyl acetate production from a combinatorial library of four Kluyveromyces marxianus strains on seven carbon sources revealed ethyl acetate biosynthesis from C5, C6, and C12 sugars. This newly adapted method rapidly identified novel properties of K. marxianus metabolism and promises to advance high throughput microbial strain engineering for ester biosynthesis.

  16. Yeast contribution to melatonin, melatonin isomers and tryptophan ethyl ester during alcoholic fermentation of grape musts.

    Science.gov (United States)

    Vigentini, Ileana; Gardana, Claudio; Fracassetti, Daniela; Gabrielli, Mario; Foschino, Roberto; Simonetti, Paolo; Tirelli, Antonio; Iriti, Marcello

    2015-05-01

    Melatonin (MEL) has been found in some medicinal and food plants, including grapevine, a commodity of particular interest for the production of wine, a beverage of economic relevance. It has also been suggested that MEL in wine may, at least in part, contribute to the health-promoting properties attributed to this beverage and, possibly, to other traditional Mediterranean foodstuffs. After a preliminary screening of 9 yeast strains in laboratory medium, three selected strains (Saccharomyces cerevisiae EC1118, Torulaspora delbrueckii CBS1146(T) and Zygosaccharomyces bailii ATCC36947(T) ) were inoculated in experimental musts obtained from 2 white (Moscato and Chardonnay) and 2 red (Croatina and Merlot) grape varieties. The production of MEL, melatonin isomers (MIs) and tryptophan ethyl ester (TEE) was monitored during the alcoholic fermentation. The screening showed that the three investigated strains produced the highest concentrations of MEL and two MIs in optimal growth conditions. However, MEL and MIs were not produced in oenological conditions, but the three strains synthesized high concentrations of a new MI and TEE in musts.

  17. Evaluation of cysteine ethyl ester as efficient inducer for glutathione overproduction in Saccharomyces spp.

    Science.gov (United States)

    Lorenz, Eric; Schmacht, Maximilian; Senz, Martin

    2016-11-01

    Economical yeast based glutathione (GSH) production is a process that is influenced by several factors like raw material and production costs, biomass production and efficient biotransformation of adequate precursors into the final product GSH. Nowadays the usage of cysteine for the microbial conversion into GSH is industrial state of practice. In the following study, the potential of different inducers to increase the GSH content was evaluated by means of design of experiments methodology. Investigations were executed in three natural Saccharomyces strains, S. cerevisiae, S. bayanus and S. boulardii, in a well suited 50ml shake tube system. Results of shake tube experiments were confirmed in traditional baffled shake flasks and finally via batch cultivation in lab-scale bioreactors under controlled conditions. Comprehensive studies showed that the usage of cysteine ethyl ester (CEE) for the batch-wise biotransformation into GSH led up to a more than 2.2 times higher yield compared to cysteine as inducer. Additionally, the intracellular GSH content could be significantly increased for all strains in terms of 2.29±0.29% for cysteine to 3.65±0.23% for CEE, respectively, in bioreactors. Thus, the usage of CEE provides a highly attractive inducing strategy for the GSH overproduction.

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

    Energy Technology Data Exchange (ETDEWEB)

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

    2016-07-05

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

  19. 40 CFR 721.2950 - Carboxylic acid glycidyl esters.

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Carboxylic acid glycidyl esters. 721... Substances § 721.2950 Carboxylic acid glycidyl esters. (a) Chemical substances and significant new uses subject to reporting. (1) The chemical substance identified generically as carboxylic acid glycidyl...

  20. 40 CFR 721.3110 - Polycarboxylic acid ester (generic).

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Polycarboxylic acid ester (generic... Substances § 721.3110 Polycarboxylic acid ester (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as a polycarboxylic acid...

  1. 40 CFR 721.8660 - Propionic acid methyl ester (generic).

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Propionic acid methyl ester (generic... Substances § 721.8660 Propionic acid methyl ester (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as a propionic acid methyl...

  2. Crystal structure and characterization of esterase Est25 mutants reveal improved enantioselectivity toward (S)-ketoprofen ethyl ester.

    Science.gov (United States)

    Kim, Jinyeong; Seok, Seung-Hyeon; Hong, Eunsoo; Yoo, Tae Hyeon; Seo, Min-Duk; Ryu, Yeonwoo

    2017-03-01

    Esterases comprise a group of enzymes that catalyze the cleavage and synthesis of ester bonds. They are important in biotechnological applications owing to their enantioselectivity, regioselectivity, broad substrate specificity, and the fact that they do not require cofactors. In a previous study, we isolated the esterase Est25 from a metagenomic library. Est25 showed catalytic activity toward the (R,S)-ketoprofen ethyl ester but had low enantioselectivity toward the (S)-ketoprofen ethyl ester. Because (S)-ketoprofen has stronger anti-inflammatory effects and fewer side effects than (R)-ketoprofen, enantioselectivity of this esterase is important. In this study, we generated Est25 mutants with improved enantioselectivity toward the (S)-ketoprofen ethyl ester; improved enantioselectivity of mutants was established by analysis of their crystal structures. The enantioselectivity of mutants was influenced by substitution of Phe72 and Leu255. Substituting these residues changed the size of the binding pocket and the entrance hole that leads to the active site. The enantioselectivity of Est25 (E = 1.1 ± 0.0) was improved in the mutants F72G (E = 1.9 ± 0.2), L255W (E = 16.1 ± 1.1), and F72G/L255W (E = 60.1 ± 0.5). Finally, characterization of Est25 mutants was performed by determining the optimum reaction conditions, thermostability, effect of additives, and substrate specificity after substituting Phe72 and Leu255.

  3. Phenylpropanoid acid esters from Korean propolis and their antioxidant activities.

    Science.gov (United States)

    Lee, In-Kyoung; Han, Myung-Suk; Kim, Dae-Won; Yun, Bong-Sik

    2014-08-01

    Ten phenylpropanoic acid esters were isolated from an ethanolic extract of Korean propolis. Their structures were elucidated by spectroscopic methods including NMR and ESI-MS. Caffeic acid esters with catechol moiety exhibited significant ABTS and DPPH radical scavenging activity and protective effect against DNA damage by a Fenton reaction.

  4. 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...... matter with high biogas yields and efficient reduction of the phthalic acid ester contamination....

  5. 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.

  6. 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.

  7. Thermolytic reactions of esters. Part IV. The methyl esters of cyanoacetic, acetoacetic and malonic acid

    NARCIS (Netherlands)

    Tonkelaar, W.A.M. den; Louw, R.; Kooyman, E.C.

    1968-01-01

    The compounds on the title proved to be more stable than their ethyl analogues, 1,2-acid elimination being impossible. Acetic acid causes a pronounced rate enhancement. Kinetic as well as product data - including the effect of added water and/or alcohols - are interpreted on the basis of acetic acid

  8. 40 CFR 721.10125 - Alkenedioic acid, dialkyl ester, reaction products with polyaminocarbomonocycle and alkenoic acid...

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Alkenedioic acid, dialkyl ester, reaction products with polyaminocarbomonocycle and alkenoic acid alkyl ester (generic). 721.10125 Section... Substances § 721.10125 Alkenedioic acid, dialkyl ester, reaction products with polyaminocarbomonocycle...

  9. Improved enantioselectivity of thermostable esterase from Archaeoglobus fulgidus toward (S)-ketoprofen ethyl ester by directed evolution and characterization of mutant esterases.

    Science.gov (United States)

    Kim, Jinyeong; Kim, Seungbum; Yoon, Sangyoung; Hong, Eunsoo; Ryu, Yeonwoo

    2015-08-01

    Thermostable esterases have potential applications in various biotechnology industries because of their resistance to high temperature and organic solvents. In a previous study, we isolated an esterase from Archaeoglobus fulgidus DSM 4304 (Est-AF), which showed high thermostability but low enantioselectivity toward (S)-ketoprofen ethyl ester. (R)-ketoprofenor (S)-ketoprofenis produced by esterase hydrolysis of the ester bond of (R,S)-ketoprofen ethyl ester and (S)-ketoprofen has better pharmaceutical activity and lower side effects than (R)-ketoprofen. Therefore, we have generated mutants of Est-AF that retained high thermostability whilst improving enantioselectivity. A library of Est-AF mutants was created by error-prone polymerase chain reaction, and mutants with improved enantioselectivity were isolated by site-saturation mutagenesis. The regions of Est-AF containing amino acid mutations were analyzed by homology modeling of its three-dimensional structure, and structure-based explanations for the changes in enantioselectivity are proposed. Finally, we isolated two mutants showing improved enantioselectivity over Est-AF (ee% = -16.2 ± 0.2 and E = 0.7 ± 0.0): V138G (ee% = 35.9 ± 1.0 and E = 3.0 ± 0.1) and V138G/L200R (ee% = 89.2 ± 0.2 and E = 19.5 ± 0.5). We also investigated various characteristics of these mutants and found that the mutants showed similar thermostability and resistance to additives or organic solvents to Est-AF, without a significant trade-off between activity and stability.

  10. 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.

  11. 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.

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

    NARCIS (Netherlands)

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

    1951-01-01

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

  13. 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.

  14. 40 CFR 721.6200 - Fatty acid polyamine condensate, phosphoric acid ester salts.

    Science.gov (United States)

    2010-07-01

    ..., phosphoric acid ester salts. 721.6200 Section 721.6200 Protection of Environment ENVIRONMENTAL PROTECTION... ester salts. (a) Chemical substances and significant new uses subject to reporting. (1) The chemical substances identified as fatty acid polyamine condensate, phosphate ester salts (PMNs P-90-1984 and...

  15. 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.

  16. Triterpene hexahydroxydiphenoyl esters and a quinic acid purpurogallin carbonyl ester from the leaves of Castanopsis fissa.

    Science.gov (United States)

    Huang, Yong-Lin; Tsujita, Takaaki; Tanaka, Takashi; Matsuo, Yosuke; Kouno, Isao; Li, Dian-Peng; Nonaka, Gen-ichiro

    2011-11-01

    Triterpene hexahydroxydiphenoyl (HHDP) esters have only been isolated from Castanopsis species, and the distribution of these esters in nature is of chemotaxonomical interest. In this study, the chemical constituents of the leaves of Castanopsis fissa were examined in detail to identify and isolate potential HHDP esters. Together with 53 known compounds, 3,4-di-O-galloyl-1-O-purpurogallin carbonyl quinic acid (1) and 3,24-(S)-HHDP-2α,3β,23,24-tetrahydroxytaraxastan-28,20β-olide (2) were isolated and their structures were elucidated by spectroscopic and chemical methods. The polyphenols of the leaves were mainly composed of galloyl quinic acids, triterpenes HHDP esters, ellagitannins and flavonol glycosides. In particular, the isolation yields of 1,3,4-trigalloyl quinic acid and compound 2 were 1.53% and 0.27%, respectively, from the fresh leaves. The presence of lipid soluble HHDP esters of oleanane-type triterpenes as one of the major metabolites is an important chemotaxonomical discovery. Lipase inhibition activities and ORAC values of the major constituents were compared. The triterpene HHDP ester showed moderate lipase inhibition activity and myricitrin gave the largest ORAC value.

  17. 21 CFR 172.852 - Glyceryl-lacto esters of fatty acids.

    Science.gov (United States)

    2010-04-01

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

  18. Fatty acid phytyl ester synthesis in chloroplasts of Arabidopsis.

    Science.gov (United States)

    Lippold, Felix; vom Dorp, Katharina; Abraham, Marion; Hölzl, Georg; Wewer, Vera; Yilmaz, Jenny Lindberg; Lager, Ida; Montandon, Cyrille; Besagni, Céline; Kessler, Felix; Stymne, Sten; Dörmann, Peter

    2012-05-01

    During stress or senescence, thylakoid membranes in chloroplasts are disintegrated, and chlorophyll and galactolipid are broken down, resulting in the accumulation of toxic intermediates, i.e., tetrapyrroles, free phytol, and free fatty acids. Chlorophyll degradation has been studied in detail, but the catabolic pathways for phytol and fatty acids remain unclear. A large proportion of phytol and fatty acids is converted into fatty acid phytyl esters and triacylglycerol during stress or senescence in chloroplasts. We isolated two genes (PHYTYL ESTER SYNTHASE1 [PES1] and PES2) of the esterase/lipase/thioesterase family of acyltransferases from Arabidopsis thaliana that are involved in fatty acid phytyl ester synthesis in chloroplasts. The two proteins are highly expressed during senescence and nitrogen deprivation. Heterologous expression in yeast revealed that PES1 and PES2 have phytyl ester synthesis and diacylglycerol acyltransferase activities. The enzymes show broad substrate specificities and can employ acyl-CoAs, acyl carrier proteins, and galactolipids as acyl donors. Double mutant plants (pes1 pes2) grow normally but show reduced phytyl ester and triacylglycerol accumulation. These results demonstrate that PES1 and PES2 are involved in the deposition of free phytol and free fatty acids in the form of phytyl esters in chloroplasts, a process involved in maintaining the integrity of the photosynthetic membrane during abiotic stress and senescence.

  19. 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.

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

    Science.gov (United States)

    Díaz, Jimena E; Mollo, María C

    2016-01-01

    Summary The first general procedure for the synthesis of 5 to 7-membered 1-aryl-2-iminoazacycloalkanes is presented, by microwave-assisted ring closure of ω-arylaminonitriles promoted by polyphosphoric acid (PPA) esters. 1-Aryl-2-iminopyrrolidines were easily prepared from the acyclic precursors employing a chloroformic solution of ethyl polyphosphate (PPE). The use of trimethylsilyl polyphosphate (PPSE) in solvent-free conditions allowed for the synthesis of 1-aryl-2-iminopiperidines and hitherto unreported 1-aryl-2-iminoazepanes. The cyclization reaction involves good to high yields and short reaction times, and represents a novel application of PPA esters in heterocyclic synthesis. PMID:27829907

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

    Directory of Open Access Journals (Sweden)

    Jimena E. Díaz

    2016-09-01

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

  2. 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

  3. 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.

  4. 21 CFR 184.1101 - Diacetyl tartaric acid esters of mono- and diglycerides.

    Science.gov (United States)

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Diacetyl tartaric acid esters of mono- and... acid esters of mono- and diglycerides. (a) Diacetyl tartaric acid esters of mono- and diglycerides, also know as DATEM, are composed of mixed esters of glycerin in which one or more of the...

  5. 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.

  6. 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.

  7. 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.

  8. Feoforbídeo (etoxi-purpurina-18 isolado de Gossypium mustelinum (Malvaceae Ethyl ester putpurin-18 from Gossypium mustelinum (Malvaceae

    Directory of Open Access Journals (Sweden)

    Tania Maria Sarmento Silva

    2010-01-01

    Full Text Available The phaeophorbide ethyl ester named Purpurin-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.

  9. 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...

  10. Synthesis of fatty acid starch esters in supercritical carbon dioxide

    NARCIS (Netherlands)

    Muljana, Henky; van der Knoop, Sjoerd; Keijzer, Danielle; Picchioni, Francesco; Janssen, Leon P. B. M.; Heeres, Hero J.

    2010-01-01

    This manuscript describes an exploratory study on the synthesis of fatty acid/potato starch esters using supercritical carbon dioxide (scCO(2)) as the solvent. The effects of process variables such as pressure (6-25 MPa), temperature (120-150 degrees C) and various basic catalysts and fatty acid der

  11. 76 FR 41135 - 2-Propenoic acid, 2-methyl-, phenylmethyl ester, polymer with 2-propenoic acid and sodium 2...

    Science.gov (United States)

    2011-07-13

    ... AGENCY 40 CFR Part 180 2-Propenoic acid, 2-methyl-, phenylmethyl ester, polymer with 2- propenoic acid...-Propenoic acid, 2-methyl-, phenylmethyl ester, polymer with 2-propenoic acid and sodium 2-methyl- 2- -1... for residues of 2-Propenoic acid, 2-methyl-,phenylmethyl ester, polymer with 2-propenoic acid...

  12. 21 CFR 172.850 - Lactylated fatty acid esters of glycerol and propylene glycol.

    Science.gov (United States)

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Lactylated fatty acid esters of glycerol and... esters of glycerol and propylene glycol. The food additive lactylated fatty acid esters of glycerol and... additive is a mixture of esters produced by the lactylation of a product obtained by reacting edible...

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

    Energy Technology Data Exchange (ETDEWEB)

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

    2016-06-14

    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.

  14. 40 CFR 417.140 - Applicability; description of the neutralization of sulfuric acid esters and sulfonic acids...

    Science.gov (United States)

    2010-07-01

    ... neutralization of sulfuric acid esters and sulfonic acids subcategory. 417.140 Section 417.140 Protection of... MANUFACTURING POINT SOURCE CATEGORY Neutralization of Sulfuric Acid Esters and Sulfonic Acids Subcategory § 417.140 Applicability; description of the neutralization of sulfuric acid esters and sulfonic...

  15. Vinylic polymerization of Norbornenecarboxylic Acid Esters by Palladium Complexes

    Institute of Scientific and Technical Information of China (English)

    2001-01-01

    New thermoplastic norbornene polymers containing ester groups were prepared byvinylic polymerization of norbornene-carboxylic acid esters by Pd(Ⅱ)-based catalysts. Themonomers were obtained by Diels-Alder reaction of cyclopentadiene with acrylic acid esters(methyl and butyl) as mixtures of endo/exo (ratio 40/60)-isomers and were converted topolymers in 60%~70% conversion. The endo-isomer was less reactive than the exo-isomer.To obtain higher molecular weight the more reactive pure exo-isomer was prepared andpolymerized with the Pd (Ⅱ)-catalysts, tetrakis (acetonitrile) Pd (Ⅱ) bis (tetrafluoroborate)and (η3-allyl)Pd(Ⅱ)SbF6, in high conversion. These polymers showed high glass transitiontemperatures, high transparency and good solubility in common solvents.

  16. Chiral recognition of N-phthaloyl, N-tetrachlorophthaloyl, and N-naphthaloyl α-amino acids and their esters on polysaccharide-derived chiral stationary phases.

    Science.gov (United States)

    Kim, Byoung-Hyoun; Lee, Sang Uck; Moon, Dong Cheul

    2012-12-01

    Enantiomeric separations of N-phthaloyl (N-PHT), N-tetrachlorophthaloyl (N-TCPHT), and N-naphthaloyl (N-NPHT) α-amino acids and their esters were examined on several kinds of polysaccharide-derived chiral stationary phases (CSPs). Resolution capability of CSPs was greater Chiralcel OF than the others for N-PHT and N-NPHT α-amino acids and their esters. In N-TCPHT α-amino acids and their esters, good enantioselectivities showed Chiralcel OG for N-TCPHT α-amino acids, Chiralpak AD for N-TCPHT α-amino acid methyl esters, and Chiralcel OD for N-TCPHT α-amino acid ethyl esters, respectively. From the results of liquid chromatography and computational chemistry, it is concluded that l-form is preferred and more retained with electrostatic interaction in case of interaction between N-PHT α-amino acid derivatives and Chiralcel OF, N-TCPHT α-amino acid derivatives and Chiralcel OD, and N-NPHT α-amino acid derivatives and Chiracel OF. On the other hand, d-form is preferred and more retained with van der Waals interaction in case of interaction between N-TCPHT α-amino acid ester derivatives and Chiralcel OG and Chiralpak AD.

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

    NARCIS (Netherlands)

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

    2004-01-01

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

  18. 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.

  19. 76 FR 7703 - 1,4-Benzenedicarboxylic Acid, Dimethyl Ester, Polymer With 1,4-Butanediol, Adipic Acid, and...

    Science.gov (United States)

    2011-02-11

    ... AGENCY 40 CFR Part 180 1,4-Benzenedicarboxylic Acid, Dimethyl Ester, Polymer With 1,4- Butanediol, Adipic... from the requirement of a tolerance for residues of 1,4-benzenedicarboxylic acid, dimethyl ester... residues of 1,4-benzenedicarboxylic acid, dimethyl ester, polymer with 1,4-butanediol, adipic acid,...

  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. The Benzyl Ester Group of Amino Acid Monomers Enhances Substrate Affinity and Broadens the Substrate Specificity of the Enzyme Catalyst in Chemoenzymatic Copolymerization.

    Science.gov (United States)

    Ageitos, Jose Manuel; Yazawa, Kenjiro; Tateishi, Ayaka; Tsuchiya, Kousuke; Numata, Keiji

    2016-01-11

    The chemoenzymatic polymerization of amino acid monomers by proteases involves a two-step reaction: the formation of a covalent acyl-intermediate complex between the protease and the carboxyl ester group of the monomer and the subsequent deacylation of the complex by aminolysis to form a peptide bond. Although the initiation with the ester group of the monomer is an important step, the influence of the ester group on the polymerization has not been studied in detail. Herein, we studied the effect of the ester groups (methyl, ethyl, benzyl, and tert-butyl esters) of alanine and glycine on the synthesis of peptides using papain as the catalyst. Alanine and glycine were selected as monomers because of their substantially different affinities toward papain. The efficiency of the polymerization of alanine and glycine benzyl esters was much greater than that of the other esters. The benzyl ester group therefore allowed papain to equally polymerize alanine and glycine, even though the affinity of alanine toward papain is substantially higher. The characterization of the copolymers of alanine and glycine in terms of the secondary structure and thermal properties revealed that the thermal stability of the peptides depends on the amino acid composition and resultant secondary structure. The current results indicate that the nature of the ester group drastically affects the polymerization efficiency and broadens the substrate specificity of the protease.

  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

    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.

  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.

    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.

  4. 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

  5. 40 CFR 721.8340 - Mono esters from 2- propenoic acid (generic).

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Mono esters from 2- propenoic acid... Specific Chemical Substances § 721.8340 Mono esters from 2- propenoic acid (generic). (a) Chemical... as mono esters from 2-propenoic acid (PMN P-01-85) is subject to reporting under this section for...

  6. 40 CFR 721.6475 - Alkyl polycarboxylic acids, esters with ethoxylated fatty alcohols.

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Alkyl polycarboxylic acids, esters... Significant New Uses for Specific Chemical Substances § 721.6475 Alkyl polycarboxylic acids, esters with... chemical substances identified generically as alkyl polycarboxylic acids, esters with ethoxylated...

  7. 21 CFR 175.260 - Partial phosphoric acid esters of polyester resins.

    Science.gov (United States)

    2010-04-01

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

  8. 40 CFR 721.6110 - Alkyldi(alkyloxyhydroxypropyl) derivative, phosphoric acid esters, potassium salts.

    Science.gov (United States)

    2010-07-01

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

  9. 21 CFR 573.640 - Methyl esters of higher fatty acids.

    Science.gov (United States)

    2010-04-01

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

  10. 40 CFR 721.3700 - Fatty acid, ester with styrenated phenol, ethylene oxide adduct.

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Fatty acid, ester with styrenated... 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...

  11. 40 CFR 721.2900 - Substituted aminobenzoic acid ester (generic name).

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Substituted aminobenzoic acid ester... Specific Chemical Substances § 721.2900 Substituted aminobenzoic acid ester (generic name). (a) Chemical... acid ester (PMN P-84-951) is subject to reporting under this section for the significant new...

  12. 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,...

  13. 75 FR 52269 - Acetic Acid Ethenyl Ester, Polymer With Oxirane; Tolerance Exemption

    Science.gov (United States)

    2010-08-25

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

  14. 78 FR 70878 - Octadecanoic Acid, 12-Hydroxy-, Homopolymer, Ester With 2-Methyloxirane Polymer With Oxirane...

    Science.gov (United States)

    2013-11-27

    ... AGENCY 40 CFR Part 180 Octadecanoic Acid, 12-Hydroxy-, Homopolymer, Ester With 2- Methyloxirane Polymer... residues of Octadecanoic Acid, 12-Hydroxy-, Homopolymer, Ester with 2-Methyloxirane Polymer with Oxirane... a maximum permissible level for residues of Octadecanoic Acid, 12-Hydroxy-, Homopolymer, Ester...

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

    Directory of Open Access Journals (Sweden)

    Shubhra Banerjee

    2013-01-01

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

  16. Oviposition response ofLobesia botrana females to long-chain free fatty acids and esters from its eggs.

    Science.gov (United States)

    Gabel, B; Thiéry, D

    1996-01-01

    Avoidance of occupied ovisposition sites supposes that females perceive information related to their own progency. Fatty acids identified from egg extracts have been reevaluated using a different extraction method, and we have investigated the dose-dependent oviposition response of European grape vine moths (Lobesia botrana) to myristic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid, methyl palmitate, methyl oleate, and ethyl palmitate; all except ethyl palmitate have been identified from eggs ofL. botrana. A methylene dichloride extract of eggs fromL. botrana revealed the presence of saturated free fatty acids (myristic, palmitic, and stearic) and unsaturated acids (palmitoleic, oleic, linoleic, and linolenic) in amounts ranging from 3.9 ng/egg equivalent for myristic acid to 30 ng/egg equivalent for palmitic and oleic acids. The extract also contained traces of methyl palmitate and methyl stearate. The greatest avoidance indexes were observed in response to palmitic, palmitoleic, and oleic acids. All the other compounds tested caused weaker responses. A reduction in the number of eggs laid was observed when moths were exposed to each of the esters applied at 0.3 µg per application spot. Reduction in eggs laid was also observed at a 10-fold higher dose of oleic acid. The present results confirm that general and simple molecules can be involved in the regulation of oviposition site selection and that they may participate in chemical marking of the eggs.

  17. Lipid-core nanocapsules restrained the indomethacin ethyl ester hydrolysis in the gastrointestinal lumen and wall acting as mucoadhesive reservoirs.

    Science.gov (United States)

    Cattani, Vitória Berg; Fiel, Luana Almeida; Jäger, Alessandro; Jäger, Eliézer; Colomé, Letícia Marques; Uchoa, Flavia; Stefani, Valter; Dalla Costa, Teresa; Guterres, Sivia Stanisçuaski; Pohlmann, Adriana Raffin

    2010-01-31

    The aim of this work was to investigate if the indomethacin ethyl ester (IndOEt) released from lipid-core nanocapsules (NC) is converted into indomethacin (IndOH) in the intestine lumen, intestine wall or after the particles reach the blood stream. NC-IndOEt had monomodal size distribution (242 nm; PDI 0.2) and zeta potential of -11 mV. The everted rat gut sac model showed IndOEt passage of 0.16 micromol m(-2) through the serosal fluid (30 min). From 15 to 120 min, the IndOEt concentrations in the tissue increased from 6.13 to 27.47 micromol m(-2). No IndOH was formed ex vivo. A fluorescent-NC formulation was used to determine the copolymer bioadhesion (0.012 micromol m(-2)). After NC-IndOEt oral administration to rats, IndOEt and IndOH were detected in the gastrointestinal tract (contents and tissues). In the tissues, the IndOEt concentrations decreased from 459 to 5 microg g(-1) after scrapping, demonstrating the NC mucoadhesion. In plasma (peripheric and portal vein), in spleen and liver, exclusively IndOH was detected. In conclusion, after oral dosing of NC-IndOEt, IndOEt is converted into IndOH in the intestinal lumen and wall before reaching the blood stream. The complexity of a living system was not predicted by the ex vivo gut sac model.

  18. 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).

  19. 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.

  20. 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.

  1. Aliphatic fatty acids and esters: inhibition of growth and exoenzyme production of Candida, and their cytotoxicity in vitro: anti-Candida effect and cytotoxicity of fatty acids and esters.

    Science.gov (United States)

    Souza, Juliana L S; da Silva, Adriana F; Carvalho, Pedro H A; Pacheco, Bruna S; Pereira, Cláudio M P; Lund, Rafael G

    2014-09-01

    The secretion of extracellular phospholipases and proteinases of Candida has been described as a relevant virulence factor in human infections. Aliphatic fatty acids have antimicrobial properties, but the mechanism by which they affect the virulence factors of microorganisms, such as Candida, is still unclear, and there are a few reports about their toxicity. The current study investigated the in vitro antifungal activity, exoenzyme production and cytotoxicity of some aliphatic fatty acids and their ester derivatives against the Candida species. The minimum inhibitory concentration and minimum fungicidal concentrations of aliphatic medium-chain fatty acids, methyl and ethyl esters were performed using the CLSI M27-A3 method and the cytotoxicity assay was performed according to ISO 10993-5. The influence of these compounds in the inhibition of the production of hydrolytic enzymes, phospholipases and proteinases by Candida was also investigated. Data analysis was performed using the one-way ANOVA method (p≤0.05). In relation to the MIC against Candida species, the fatty acid with the best result was Lauric acid, although its ester derivatives showed no activity. The inhibition of phospholipase production was more significant than the inhibition of proteinase production by Candida. Tested fatty acids revealed more than 80% cell viability in their MIC concentrations. Additionally, a cell viability of 100% was reported at concentrations of anti-enzymatic effect. Therefore, the potential use of these fatty acids could be the basis for more antimicrobial tests.

  2. Kinetics and thermodynamics of oxidation mediated reaction in L-cysteine and its methyl and ethyl esters in dimethyl sulfoxide-d6 by NMR spectroscopy

    Science.gov (United States)

    Dougherty, Ryan J.; Singh, Jaideep; Krishnan, V. V.

    2017-03-01

    L-Cysteine (L-Cys), L-Cysteine methyl ester (L-CysME) or L-Cysteine ethyl ester (L-CysEE), when dissolved in dimethyl sulfoxide, undergoes an oxidation process. This process is slow enough and leads to nuclear magnetic resonance (NMR) spectral changes that could be monitored in real time. The oxidation mediated transition is modeled as a pseudo-first order kinetics and the thermodynamic parameters are estimated using the Eyring's formulation. L-Cysteine and their esters are often used as biological models due to the remarkable thiol group that can be found in different oxidation states. This oxidation mediated transition is due to the combination of thiol oxidation to a disulfide followed by solvent-induced effects may be relevant in designing cysteine-based molecular models.

  3. Improved monitoring of female codling moth (Lepidoptera: Tortricidae) with pear ester plus acetic acid in sex pheromone-treated orchards.

    Science.gov (United States)

    Knight, Alan

    2010-08-01

    The performance of clear delta traps baited with 3.0 mg of pear ester, ethyl (E,Z)-2,4-decadienoate, and 5.0 ml of acetic acid in separate lures was compared with orange delta traps baited with a single lure containing 3.0 mg of both pear ester and the sex pheromone, (E,E)-8,10-dodecadien-1-ol (codlemone) for codling moth, Cydia pomonella (L.), in apple, Malus domestica (Borkhausen). Residual analyses and field tests demonstrated that both the pear ester and acetic acid lures were effective for at least 8 wk. The two trap-lure combinations caught a similar number of total moths in an orchard treated with sex pheromone dispensers during short-term trials in 2008. However, the mean catch of female moths was significantly higher and male moths significantly lower in clear traps baited with pear ester and acetic acid versus orange traps baited with pear ester and codlemone. Season-long studies were conducted with these two trap-lure combinations in orchards treated with (n = 6) and without (n = 7) sex pheromone dispensers during 2009. The two trap-lure combinations caught similar numbers of moths in dispenser-treated orchards. In contrast, total catch was significantly higher (>2-fold) in the orange compared with the clear traps in untreated orchards. The clear caught >6-fold more females than the orange trap in both types of orchards. These studies suggest that deploying clear delta traps baited with pear ester and acetic acid can be an effective monitoring tool for female codling moth and an alternative to codlemone-baited traps in sex pheromone-treated orchards.

  4. 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.

  5. 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.

  6. 21 CFR 178.3780 - Polyhydric alcohol esters of long chain monobasic acids.

    Science.gov (United States)

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Polyhydric alcohol esters of long chain monobasic..., PRODUCTION AIDS, AND SANITIZERS Certain Adjuvants and Production Aids § 178.3780 Polyhydric alcohol esters of long chain monobasic acids. Polyhydric alcohol esters of long chain monobasic acids identified in...

  7. 40 CFR 721.9965 - Fatty acids, C10-13 - branched, vinyl esters.

    Science.gov (United States)

    2010-07-01

    ... esters. 721.9965 Section 721.9965 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED... Specific Chemical Substances § 721.9965 Fatty acids, C10-13 - branched, vinyl esters. (a) Chemical... acids, C10-13 - branched, vinyl esters (PMN P-97-482; CAS No. 184785-38-4) is subject to reporting...

  8. 40 CFR 721.10133 - 2-Propenoic acid, 2-methyl, 2-hydroxyethyl ester, homopolymer.

    Science.gov (United States)

    2010-07-01

    ...-hydroxyethyl ester, homopolymer. 721.10133 Section 721.10133 Protection of Environment ENVIRONMENTAL PROTECTION... New Uses for Specific Chemical Substances § 721.10133 2-Propenoic acid, 2-methyl, 2-hydroxyethyl ester... identified as 2-propenoic acid, 2-methyl, 2-hydroxyethyl ester, homopolymer (PMN P-07-401; CAS No....

  9. 40 CFR 721.10165 - Carbonotrithioic acid, bis(phenylmethyl) ester.

    Science.gov (United States)

    2010-07-01

    ...(phenylmethyl) ester. 721.10165 Section 721.10165 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.10165 Carbonotrithioic acid, bis(phenylmethyl) ester. (a) Chemical... carbonotrithioic acid, bis(phenylmethyl) ester (PMN P-08-138; CAS No.26504-29-0) is subject to reporting under...

  10. 40 CFR 721.2078 - 1-Piperidinecarboxylic acid, 2-[(dichloro-hydroxy-carbomonocycle)hydrazono]-, methyl ester...

    Science.gov (United States)

    2010-07-01

    ...- -, methyl ester (generic). 721.2078 Section 721.2078 Protection of Environment ENVIRONMENTAL PROTECTION... New Uses for Specific Chemical Substances § 721.2078 1-Piperidinecarboxylic acid, 2- -, methyl ester... generically identified as 1-piperidinecarboxylic acid, 2- -, methyl ester (PMN P-96-756) is subject...

  11. 40 CFR 721.7770 - Alkylphenoxypoly(oxyethylene) sulfuric acid ester, substituted amine salt.

    Science.gov (United States)

    2010-07-01

    ... acid ester, substituted amine salt. 721.7770 Section 721.7770 Protection of Environment ENVIRONMENTAL... ester, substituted amine salt. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as alkyl phenoxypoly(oxyethylene) sulfuric acid ester,...

  12. 40 CFR 721.1577 - 1,4-Benzenedicarboxylic acid, bis [4-(ethenyloxy) butyl] ester.

    Science.gov (United States)

    2010-07-01

    ... ester. 721.1577 Section 721.1577 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED... Specific Chemical Substances § 721.1577 1,4-Benzenedicarboxylic acid, bis ester. (a) Chemical substance and... acid, bis ester (PMN P-98-1163; CAS No. 117397-31-6) is subject to reporting under this section for...

  13. 78 FR 46283 - Modification of Significant New Uses of Ethaneperoxoic Acid, 1,1-Dimethylpropyl Ester

    Science.gov (United States)

    2013-07-31

    ...- Dimethylpropyl Ester AGENCY: Environmental Protection Agency (EPA). ACTION: Final rule. SUMMARY: Under the Toxic... chemical substance identified as ethaneperoxoic acid, 1,1- dimethylpropyl ester, which was the subject of... substance identified as ethaneperoxoic acid, 1,1-dimethylpropyl ester, (PMN P-85-680). Potentially...

  14. 40 CFR 721.987 - Dialkylaminophenyl imino pyrazole acid ester (generic).

    Science.gov (United States)

    2010-07-01

    ... ester (generic). 721.987 Section 721.987 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.987 Dialkylaminophenyl imino pyrazole acid ester (generic). (a) Chemical... as dialkylaminophenyl imino pyrazole acid ester (PMN P-98-45) is subject to reporting under...

  15. 40 CFR 721.1579 - 1,2,4-Benzenetricarboxylic acid, tris [4-(ethenyloxy) butyl] ester.

    Science.gov (United States)

    2010-07-01

    ... ester. 721.1579 Section 721.1579 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED... Specific Chemical Substances § 721.1579 1,2,4-Benzenetricarboxylic acid, tris ester. (a) Chemical substance...-benzenetricarboxylic acid, tris ester (PMN P-98-1165; CAS No. 196109-17-8) is subject to reporting under this...

  16. 40 CFR 721.3680 - Ethylene oxide adduct of fatty acid ester with pentaerythritol.

    Science.gov (United States)

    2010-07-01

    ... ester with pentaerythritol. 721.3680 Section 721.3680 Protection of Environment ENVIRONMENTAL PROTECTION... New Uses for Specific Chemical Substances § 721.3680 Ethylene oxide adduct of fatty acid ester with... identified generically as ethylene oxide adduct of fatty acid ester with pentaerythritol (PMN P-91-442)...

  17. 40 CFR 721.8160 - Propanoic acid, 2,2-dimethyl-, ethenyl ester.

    Science.gov (United States)

    2010-07-01

    ... ester. 721.8160 Section 721.8160 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED... Specific Chemical Substances § 721.8160 Propanoic acid, 2,2-dimethyl-, ethenyl ester. (a) Chemical... acid, 2,2-dimethyl-, ethenyl ester (PMN P-89-1058) is subject to reporting under this section for...

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

    Science.gov (United States)

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

    2014-11-01

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

  19. Adsorptive removal of phthalate ester (Di-ethyl phthalate) from aqueous phase by activated carbon: a kinetic study.

    Science.gov (United States)

    Venkata Mohan, S; Shailaja, S; Rama Krishna, M; Sarma, P N

    2007-07-19

    Adsorptive studies were carried out on Di-ethyl phthalate (DEP) removal from aqueous phase onto activated carbon. Batch sorption studies were performed and the results revealed that activated carbon demonstrated ability to adsorb DEP. Influence of varying experimental conditions such as DEP concentration, pH of aqueous solution, and dosage of adsorbent were investigated on the adsorption process. Sorption interaction of DEP onto activated carbon obeyed the pseudo second order rate equation. Experimental data showed good fit with both the Langmuir and Freundlich adsorption isotherm models. DEP sorption was found to be dependent on the aqueous phase pH and the uptake was observed to be greater at acidic pH.

  20. High-yield synthesis of bioactive ethyl cinnamate by enzymatic esterification of cinnamic acid.

    Science.gov (United States)

    Wang, Yun; Zhang, Dong-Hao; Zhang, Jiang-Yan; Chen, Na; Zhi, Gao-Ying

    2016-01-01

    In this paper, Lipozyme TLIM-catalyzed synthesis of ethyl cinnamate through esterification of cinnamic acid with ethanol was studied. In order to increase the yield of ethyl cinnamate, several media, including acetone, isooctane, DMSO and solvent-free medium, were investigated in this reaction. The reaction showed a high yield by using isooctane as reaction medium, which was found to be much higher than the yields reported previously. Furthermore, several parameters such as shaking rate, water activity, reaction temperature, substrate molar ratio and enzyme loading had important influences on this reaction. For instance, when temperature increased from 10 to 50 °C, the initial reaction rate increased by 18 times and the yield of ethyl cinnamate increased by 6.2 times. Under the optimum conditions, lipase-catalyzed synthesis of ethyl cinnamate gave a maximum yield of 99%, which was of general interest for developing industrial processes for the preparation of ethyl cinnamate.

  1. Cu(I)-catalyzed (11)C carboxylation of boronic acid esters: a rapid and convenient entry to (11)C-labeled carboxylic acids, esters, and amides.

    Science.gov (United States)

    Riss, Patrick J; Lu, Shuiyu; Telu, Sanjay; Aigbirhio, Franklin I; Pike, Victor W

    2012-03-12

    Rapid and direct: the carboxylation of boronic acid esters with (11)CO(2) provides [(11)C]carboxylic acids as a convenient entry into [(11)C]esters and [(11)C]amides. This conversion of boronates is tolerant to diverse functional groups (e.g., halo, nitro, or carbonyl).

  2. Exploring unsaturated fatty acid cholesteryl esters as transdermal permeation enhancers.

    Science.gov (United States)

    Rambharose, Sanjeev; Kalhapure, Rahul S; Jadhav, Mahantesh; Govender, Thirumala

    2017-04-01

    The intrinsic protective barrier property of skin, one of the major challenges in the design of transdermal drug delivery systems, can be overcome through the use of chemical permeation enhancers (CPEs). Herein, we explore the potential of unsaturated fatty acid (UFA) esters of cholesterol (Chol) viz., oleate, linoleate and linolenate, as transdermal CPEs using tenofovir (TNF) as a model drug. All Chol UFA esters at 1% w/w were found to be more effective enhancers when compared to their respective parent fatty acids (FAs) and saturated FA counterparts. Cholesteryl linolenate (Chol-LLA) showed the most superior performance (enhancement ratio (ER) = 3.71). The greatest ER for Chol-LLA (5.93) was achieved at a concentration of 2% w/w. The histomorphological and transepithelial electrical resistance (TEER) evaluations supported the results of the permeability studies. These findings showed no significant loss in the integrity of the epidermis, with drug and enhancer treatment having temporary effects on the barrier property of the epidermis. Chol UFA esters can therefore be considered as new CPEs for exploitation in topical formulations for various classes of drugs.

  3. 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...

  4. 40 CFR 721.1875 - Boric acid, alkyl and substituted alkyl esters (generic name).

    Science.gov (United States)

    2010-07-01

    ... alkyl esters (generic name). 721.1875 Section 721.1875 Protection of Environment ENVIRONMENTAL... esters (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance boric acid, alkyl and substituted alkyl esters (PMN P-86-1252) is subject to...

  5. 40 CFR 721.10142 - Oxabicycloalkane carboxylic acid alkanediyl ester (generic).

    Science.gov (United States)

    2010-07-01

    ... alkanediyl ester (generic). 721.10142 Section 721.10142 Protection of Environment ENVIRONMENTAL PROTECTION... ester (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as oxabicycloalkane carboxylic acid alkanediyl ester (PMN P-06-199)...

  6. 40 CFR 721.6075 - Phosphonic acid, 1,1-methylenebis-tetrakis(1-methylethyl) ester.

    Science.gov (United States)

    2010-07-01

    ...-tetrakis(1-methylethyl) ester. 721.6075 Section 721.6075 Protection of Environment ENVIRONMENTAL PROTECTION...-methylethyl) ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as phosphonic acid, 1,1-methylenebis-tetrakis(1-methylethyl) ester (PMN P-95-168)...

  7. 40 CFR 721.1728 - Benzoic acid, 2-(3-phenylbutylidene)amino-, methyl ester.

    Science.gov (United States)

    2010-07-01

    ...)amino-, methyl ester. 721.1728 Section 721.1728 Protection of Environment ENVIRONMENTAL PROTECTION...-, methyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as benzoic acid, 2-(3-phenylbutylidene)amino-, methyl ester (PMN P-85-1211) is...

  8. 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.

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

    Science.gov (United States)

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

  10. 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.

  11. Sensing application of an optical fiber dip coated with L-Cystein ethyl ester hydrochloride capped ZnTe quantum dots

    Directory of Open Access Journals (Sweden)

    Sundaray Madhulita

    2016-09-01

    Full Text Available Optical fiber in conjunction with ZnTe quantum dots (QDs is investigated for sensing application. ZnTe QDs, are synthesized by a simple chemical bottom up approach. Quantum dots are capped with L-Cystein ethyl ester hydrochloride (LEEH, to increase their stability. Then LEEH capped ZnTe QDs, whose size is estimated as 2.29 nm by effective mass approximation (EMA, are dip-coated on a cladding removed optical fiber. Different concentrations of alcohol and ammonia are used to investigate the sensing behavior. It is found that sensitivity of the sensor increases with the use of QDs for both alcohol and ammonia.

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

    Science.gov (United States)

    Wang, Lei; Kannan, Kurunthachalam

    2013-09-01

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

  13. 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

  14. 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.

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

    Science.gov (United States)

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

    2017-02-01

    Context. In recent years, 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 of substantial astrobiological interest are the esters. The simplest ester, methyl formate (CH3OCHO), is rather abundant in star-forming regions. The next step in the chemical complexity of esters is ethyl formate, C2H5OCHO. Despite the increase in sensitivity of current telescopes, the detection of complex molecules with more than ten atoms such as C2H5OCHO is still a challenge. 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. New detections towards additional sources with a wide range of physical conditions are crucial to differentiate between competing chemical models based on dust grain surface and gas-phase chemistry. Aims: 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. Methods: We have analyzed a spectral line survey towards the W51 e2 hot molecular core, which covers 44 GHz in the 1, 2 and 3 mm bands, carried out with the IRAM 30 m telescope. Results: We report the detection of the trans and gauche conformers of ethyl formate. A local thermodynamic equilibrium analysis indicates that the excitation temperature is 78 ± 10 K and that the two conformers have similar source-averaged column densities of (2.0 ± 0.3) × 10-16 cm-2 and an abundance of 10-8. We compare for the first time the observed molecular abundances of ethyl formate with different competing chemical models based on grain surface and gas-phase chemistry. Conclusions: We propose that

  16. 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...... configuration. Picolinyl esters of fatty acids are prepared by adding carbonyl-diimidazole, 3-hydroxy-methylpyridine and 4-pyrrolidin-o-pyridine to a solution of free fatty acids in dichloromethane. The picolinyl esters dissolved in heptane are then separated by capillary GC on a CP Sil 88 column equipped...

  17. 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.

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

    DEFF Research Database (Denmark)

    2010-01-01

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

  19. 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。

  20. 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 ...

  1. 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.

  2. 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

  3. Intramolecular interactions in ortho-methoxyalkylphenylboronic acids and their catechol esters

    Science.gov (United States)

    Adamczyk-Woźniak, Agnieszka; Borys, Krzysztof M.; Czerwińska, Karolina; Gierczyk, Błażej; Jakubczyk, Michał; Madura, Izabela D.; Sporzyński, Andrzej; Tomecka, Ewelina

    2013-12-01

    Catechol esters of ortho-methoxyalkylphenylboronic acids have been synthesized and characterized by 17O NMR spectroscopy. The results were compared with the data for the parent acids. The influence of intramolecular and intermolecular hydrogen bonds on the properties of the boronic acids has been discussed. The 17O NMR data for the boronic esters proved that there are no O → B interactions in the investigated compounds. This fact is connected with weak Lewis acidity of the parent acids and their low sugars' receptors activity. Crystal structure of ortho-methoxyphenylboronic acid catechol ester was determined.

  4. [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.

  5. 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.

  6. Proteinuria with fumaric acid ester treatment for psoriasis.

    Science.gov (United States)

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

    2011-08-01

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

  7. 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.

  8. Determination of omega-3 acids ethyl esters in Fish Oil Soft Capsules by capillary gas chromatography%毛细管气相色谱法测定鱼油软胶囊中ω-3酸乙酯含量

    Institute of Scientific and Technical Information of China (English)

    谢强胜; 李启艳; 刘春霖; 高天阳; 孙铜

    2016-01-01

    目的:毛细管气相色谱法测定鱼油软胶囊中ω-3酸乙酯含量。方法采用HP-FFAP毛细管色谱柱(30 m ×0.53 mm ×1.0μm),FID检测器,载气为N2,程序升温法,分流比10:1。结果亚麻酸乙酯、二十碳五烯酸乙酯、二十二碳五烯酸乙酯和二十二碳六烯酸乙酯分别在17.04~340.92、20.95~419.16、17.31~346.24、20.01~400.32μg·mL-1范围内呈现良好的线性关系,平均精密度RSD(n=6)分别为1.6%、1.2%、1.4%、1.6%,平均回收率分别为102.0%、100.7%、99.7%、100.4%,RSD(n=6)分别为0.6%、1.6%、1.4%、1.1%。结论该方法简单可行,结果准确、可靠,可用于鱼油软胶囊ω-3酸乙酯的测定。%Objective Todeterminethecontentlofomega-3acidlethylelterlinFilhOilbycapillarygalchromatog-raphy.Methods AchromatographiccolumnofHP-FFAPwaluledwithnitrogenalcarrier.Programmedtemperaturewal practicable. The lplit ratio wal 10:1,and the GC wal equipped with FID detector. Results The linear rangel of ethyl linole-nate,EPA ethyl elter,DPA ethyl elter,DHA ethyl elter were 17. 04 ~340. 92,20. 95 ~419. 16,17. 31 ~346. 24,20. 01 ~400. 32μg·mL-1,relpectively. The RSDs of average precilionl were 1. 6%,1. 2%,1. 4%,1. 6%(n=6). The average recov-eriel were 105%,97%,98%,109%,relpectively,and the RSDl were not more than 2. 0%. Conclusion Thil method wal lenlitive,limple and accurate,and can be uled to determine omega-3 ethyl elterl in Filh Oil Soft Caplulel.

  9. Kinetically controlled synthesis of monoglyceryl esters from chiral and prochiral acids methyl esters catalyzed by immobilized Rhizomucor miehei lipase.

    Science.gov (United States)

    Acosta, Andreina; Filice, Marco; Fernandez-Lorente, Gloria; Palomo, Jose M; Guisan, Jose M

    2011-01-01

    Partial acylation of only one primary hydroxyl group of glycerol generates a chiral center at position 2. Rhizomucor miehei lipase (RML) catalyzes the kinetically controlled transesterification of different aromatic carboxylic acids methyl esters with glycerol. High synthetic yields of glyceryl esters (around 70-80%) were obtained even in the presence of significant concentrations of water (from 5% to 20%). After a long incubation of the reaction mixture in the presence of the biocatalyst only pure free acid was obtained. Other lipases (from Geobacillus thermocatenulatus and from Thermomyces lanuginose) also catalyzed similar kinetically controlled transesterifications although less efficiently. RML immobilized on Sepharose-Q showed a high activity and specificity, compared to the immobilization by other techniques, only producing monoglyceryl esters with all substrates. In particular, monoglyceryl-phenylmalonate product was synthesized in 82% overall yield and >99% diastereomeric excess at pH 7.0 and 37°C and 90% glycerol.

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

    NARCIS (Netherlands)

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

    2014-01-01

    A novel long chain alkyl phenylboronic acid ester containing heterocyclic compound, bis (1-(benzothiazol-2-ylthio) propan-2-yl)-4-dodecylphenylboronic acid ester (DBBMT), was synthesized and characterized. The hydrolytic stability of the DBBMT was evaluated and the results show that DBBMT is of outs

  11. 21 CFR 178.3450 - Esters of stearic and palmitic acids.

    Science.gov (United States)

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Esters of stearic and palmitic acids. 178.3450 Section 178.3450 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES... SANITIZERS Certain Adjuvants and Production Aids § 178.3450 Esters of stearic and palmitic acids. The...

  12. 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.

  13. 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....

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

    Science.gov (United States)

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

    2016-09-02

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

  15. 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.

  16. Conversion of furfuryl alcohol into ethyl levulinate using solid acid catalysts.

    Science.gov (United States)

    Lange, Jean-Paul; van de Graaf, Wouter D; Haan, René J

    2009-01-01

    Furfural, a potential coproduct of levulinic acid, can be converted into levulinic acid via hydrogenation to furfuryl alcohol and subsequent ethanolysis to ethyl levulinate. The ethanolysis reaction is known to proceed in the presence of H(2)SO(4). We show here that several strongly acidic resins are comparably effective catalysts for this reaction. Optimal performance is achieved by balancing the number of acid sites with their accessibility in the resin. Acidic zeolites such as H-ZSM-5 also catalyze this reaction, although with a lower activity and a higher co-production of diethyl ether.

  17. 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)

  18. 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)

  19. 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.

  20. 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.

  1. Occurrence of fatty acid esters of 3-MCPD, 2-MCPD and glycidol in infant formula.

    Science.gov (United States)

    Wöhrlin, Friederike; Fry, Hildburg; Lahrssen-Wiederholt, Monika; Preiß-Weigert, Angelika

    2015-01-01

    The discovery of fatty acid esters of monochloropropanediol (MCPD) and glycidol generated during the refinement process in vegetable fats and oils caused concerns about possible adverse health effects. As these fats are components of infant formula, the current investigation of the MCPD and glycidyl ester contents in infant formula was necessary to update the data for risk assessment purposes. For the analysis of 3-MCPD, 2-MCPD and glycidyl esters in infant formula, an existing method for fats and oils had to be modified and validated. The fat fraction containing MCPD and glycidyl esters was extracted from infant formula by accelerated solvent extraction (ASE). The extracted fat was then analysed according to an established method for fats and oils. Glycidyl esters are converted to monobrompropanediol (3-MBPD) esters, MCPD and 3-MBPD esters hydrolysed subsequently and after derivatisation detected by GC-MS. Seven different products of infant formula, covering two types and five lots each, altogether 70 samples, were bought in retail markets and analysed. In all samples, 3-MCPD and glycidyl esters could be detected. Both 3-MCPD and glycidyl esters' concentration levels were found to be lower in comparison with earlier investigations described in the literature. The occurrence of 2-MCPD esters in infant formula was investigated for the first time and revealed concentrations about half of 3-MCPD ester concentrations.

  2. 75 FR 50926 - 2-propenoic acid, 2-methyl-, C12-16-alkyl esters, telomers with 1-dodecanethiol, polyethylene...

    Science.gov (United States)

    2010-08-18

    ... AGENCY 40 CFR Part 180 2-propenoic acid, 2-methyl-, C12-16-alkyl esters, telomers with 1-dodecanethiol... tolerance for residues of 2-propenoic acid, 2-methyl-, C12-16- alkyl esters, telomers with 1-dodecanethiol... residues of 2-propenoic acid, 2-methyl-, C12-16-alkyl esters, telomers with 1-dodecanethiol,...

  3. 40 CFR 721.6477 - Alkyl polycarboxylic acids, esters with ethoxylated fatty alcohols, reaction products with maleic...

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Alkyl polycarboxylic acids, esters... Alkyl polycarboxylic acids, esters with ethoxylated fatty alcohols, reaction products with maleic... identified generically as alkyl polycarboxylic acids, esters with ethoxylated fatty alcohols,...

  4. 40 CFR 721.6100 - Phosphoric acid, C6-12-alkyl esters, compounds with 2-(dibutylamino) ethanol.

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Phosphoric acid, C6-12-alkyl esters... Significant New Uses for Specific Chemical Substances § 721.6100 Phosphoric acid, C6-12-alkyl esters... reporting. (1) The chemical substances identified as phosphoric acid, C6-12-alkyl esters, compounds with...

  5. 75 FR 70254 - Typographical Error in Summary Notice of Filing in Docket for Polymerized Fatty Acid Esters With...

    Science.gov (United States)

    2010-11-17

    ... AGENCY Typographical Error in Summary Notice of Filing in Docket for Polymerized Fatty Acid Esters With...), concerning the Notice of Filing (NOF) for Pesticide Petition (PP) 0E7699 for polymerized fatty acid esters... Notice of Filing (NOF) for Pesticide Petition (PP) 0E7699 for polymerized fatty acid esters...

  6. 75 FR 4292 - 2-Propenoic acid, 2-ethylhexyl ester, polymer with ethenylbenzene and 2-methylpropyl 2-methyl-2...

    Science.gov (United States)

    2010-01-27

    ... AGENCY 40 CFR Part 180 2-Propenoic acid, 2-ethylhexyl ester, polymer with ethenylbenzene and 2... residues of 2-propenoic acid, 2-ethylhexyl ester, polymer with ethenylbenzene and 2-methylpropyl 2-methyl-2... permissible level for residues of 2-propenoic acid, 2-ethylhexyl ester, polymer with ethenylbenzene and...

  7. 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,...

  8. 40 CFR 721.3100 - Oligomeric silicic acid ester compound with a hy-droxyl-al-kyla-mine.

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Oligomeric silicic acid ester compound... Significant New Uses for Specific Chemical Substances § 721.3100 Oligomeric silicic acid ester compound with a... chemical substance identified generically as oligomeric silicic acid ester compound with...

  9. 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...

  10. Study on ethyl esterification of unsaturated fatty acids of tea oil%茶油不饱和脂肪酸乙酯化工艺研究

    Institute of Scientific and Technical Information of China (English)

    李琼; 叶勇; 刘华鼐

    2014-01-01

    In this article,unsaturated acid esterification(fatty acid ethyl ester)is prepared with tea oil used as material,ethyl alcohol as solvent,and alkaline as catalyst. By single factor test and orthogonal test,the following optimum processing parameters are obtained:reactant mol ratio(absolute alcohol/tea oil)6∶1,concentration of alkaline catalyst 0.6%,reaction time 2.5 h,and reaction temperature 75℃. The yield of ethyl is 93.4%.%以茶油为原料,无水乙醇为溶剂,在碱性催化剂作用下制备脂肪酸乙酯。通过单因素、正交试验确定最佳乙酯化工艺是:醇油比为6∶1(摩尔比),催化剂的浓度0.6%(质量比),反应时间为2.5 h,反应温度为75℃。该工艺脂肪酸乙酯得率为93.4%。

  11. Relative oral bioavailability of glycidol from glycidyl fatty acid esters in rats.

    Science.gov (United States)

    Appel, Klaus E; Abraham, Klaus; Berger-Preiss, Edith; Hansen, Tanja; Apel, Elisabeth; Schuchardt, Sven; Vogt, Carla; Bakhiya, Nadiya; Creutzenberg, Otto; Lampen, Alfonso

    2013-09-01

    In order to quantify the relative bioavailability of glycidol from glycidyl fatty acid esters in vivo, glycidyl palmitoyl ester and glycidol were orally applied to rats in equimolar doses. The time courses of the amounts of glycidol binding to hemoglobin as well as the excretion of 2,3-dihydroxypropyl mercapturic acids were determined. The results indicate that glycidol is released from the glycidyl ester by hydrolysis and rapidly distributed in the organism. In relation to glycidol, there was only a small timely delay in the binding to hemoglobin for the glycidol moiety released from the ester which may be certainly attributed to enzymatic hydrolysis. In both cases, however, an analogous plateau was observed representing similar amounts of hemoglobin binding. With regard to the urinary excretion of mercapturic acids, also similar amounts of dihydroxypropyl mercapturic acids could be detected. In an ADME test using a virtual double tag (³H, ¹⁴C) of glycidyl palmitoyl ester, a diverging isotope distribution was detected. The kinetics of the ¹⁴C-activity reflected the kinetics of free glycidol released after hydrolysis of the palmitoyl ester. In view of this experimental data obtained in rats, it is at present justified for the purpose of risk assessment to assume complete hydrolysis of the glycidyl ester in the gastrointestinal tract. Therefore, assessment of human exposure to glycidyl fatty acid ester should be regarded as an exposure to the same molar quantity of glycidol.

  12. 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.

  13. 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...

  14. 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.

  15. 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.

  16. Temperature-Triggered Switchable Helix-Helix Inversion of Poly(phenylacetylene Bearing l-Valine Ethyl Ester Pendants and Its Chiral Recognition Ability

    Directory of Open Access Journals (Sweden)

    Yanli Zhou

    2016-11-01

    Full Text Available A phenylacetylene containing the l-valine ethyl ester pendant (PAA-Val was synthesized and polymerized by an organorhodium catalyst (Rh(nbdBPh4 to produce the corresponding one-handed helical cis-poly(phenylacetylene (PPAA-Val. PPAA-Val showed a unique temperature-triggered switchable helix-sense in chloroform, while it was not observed in highly polar solvents, such as N,N′-dimethylformamide (DMF. By heating the solution of PPAA-Val in chloroform, the sign of the CD absorption became reversed, but recovered after cooling the solution to room temperature. Even after six cycles of the heating-cooling treatment, the helix sense of the PPAA-Val’s backbone was still switchable without loss of the CD intensity. The PPAA-Val was then coated on silica gel particles to produce novel chiral stationary phases (CSPs for high-performance liquid chromatography (HPLC. These novel PPAA-Val based CSPs showed a high chiral recognition ability for racemic mandelonitrile (α = 2.18 and racemic trans-N,N′-diphenylcyclohexane-1,2-dicarboxamide (α = 2.60. Additionally, the one-handed helical cis-polyene backbone of PPAA-Val was irreversibly destroyed to afford PPAA-Val-H by heating in dimethyl sulfoxide (DMSO accompanied by the complete disappearance of the Cotton effect. Although PPAA-Val-H had the same l-valine ethyl ester pendants as its cis-isomer PPAA-Val, it showed no chiral recognition. It was concluded that the one-handed helical cis-polyene backbone of PPAA-Val plays an important role in the chiral recognition ability.

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

    Science.gov (United States)

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

    2010-03-31

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

  18. 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.

  19. Technological Aspects of Chemoenzymatic Epoxidation of Fatty Acids, Fatty Acid Esters and Vegetable Oils: A Review

    Directory of Open Access Journals (Sweden)

    Eugeniusz Milchert

    2015-12-01

    Full Text Available The general subject of the review is analysis of the effect of technological parameters on the chemoenzymatic epoxidation processes of vegetable oils, fatty acids and alkyl esters of fatty acids. The technological parameters considered include temperature, concentration, amount of hydrogen peroxide relative to the number of unsaturated bonds, the amounts of enzyme catalysts, presence of solvent and amount of free fatty acids. Also chemical reactions accompanying the technological processes are discussed together with different technological options and significance of the products obtained.

  20. Lipase catalyzed synthesis of organic acid esters of lactic acid in non-aqueous media.

    Science.gov (United States)

    Kiran, K R; Divakar, S

    2001-05-04

    Lipases from Rhizomucor miehei (Lipozyme IM20) and porcine pancreas (PPL) were employed as catalysts for the esterification reaction between the hydroxyl group of lactic acid and the carboxyl group of organic acids. Reactions were carried out at both shake-flask and bench-scale levels. Various parameters, such as solvent, temperature, substrate and enzyme concentrations, effect of buffer volume, buffer pH and water volume, were investigated for optimization of yields. While ethylmethyl ketone (EMK) was found to be the best solvent for shake-flask reactions, chloroform gave higher yields at bench-scale level. Detailed studies were carried out with respect to the synthesis of palmitoyl and stearoyl lactic acids. At shake-flask level, maximum yields of 37.5 and 40% were observed in case of palmitoyl and stearoyl lactic acids, respectively, with Lipozyme IM20; at bench-scale level, the maximum yields were 85.1 and 99% respectively, when PPL was employed. Of all the organic acids employed (C(2)--C(18)), only lauric, palmitic and stearic acids gave yields above 50%. At bench-scale level, PPL could be reused for up to three cycles with yields above 40%. Esters prepared were found to conform to Food Chemical Codex (FCC) specifications in terms of acid value, ester value, sodium and lactic acid contents.

  1. 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.

  2. 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.

  3. Fatty acid alkyl esters: perspectives for production of alternative biofuels.

    Science.gov (United States)

    Röttig, Annika; Wenning, Leonie; Bröker, Daniel; Steinbüchel, Alexander

    2010-02-01

    The global economy heads for a severe energy crisis: whereas the energy demand is going to rise, easily accessible sources of crude oil are expected to be depleted in only 10-20 years. Since a serious decline of oil supply and an associated collapse of the economy might be reality very soon, alternative energies and also biofuels that replace fossil fuels must be established. In addition, these alternatives should not further impair the environment and climate. About 90% of the biofuel market is currently captured by bioethanol and biodiesel. Biodiesel is composed of fatty acid alkyl esters (FAAE) and can be synthesized by chemical, enzymatic, or in vivo catalysis mainly from renewable resources. Biodiesel is already established as it is compatible with the existing fuel infrastructure, non-toxic, and has superior combustion characteristics than fossil diesel; and in 2008, the global production was 12.2 million tons. The biotechnological production of FAAE from low cost and abundant feedstocks like biomass will enable an appreciable substitution of petroleum diesel. To overcome high costs for immobilized enzymes, the in vivo synthesis of FAAE using bacteria represents a promising approach. This article points to the potential of different FAAE as alternative biofuels, e.g., by comparing their fuel properties. In addition to conventional production processes, this review presents natural and genetically engineered biological systems capable of in vivo FAAE synthesis.

  4. 77 FR 20314 - 2-Propenoic Acid, 2-Methyl-, 2-Ethylhexyl Ester, Telomer With 1-Dodecanethiol, Ethenylbenzene and...

    Science.gov (United States)

    2012-04-04

    ... AGENCY 40 CFR Part 180 2-Propenoic Acid, 2-Methyl-, 2-Ethylhexyl Ester, Telomer With 1- Dodecanethiol...-methyl-, 2- ethylhexyl ester, telomer with 1-dodecanethiol, ethenylbenzene and 2- methyloxirane polymer...-Propenoic acid, 2-methyl-, 2-ethylhexyl ester, telomer with 1-dodecanethiol, ethenylbenzene and...

  5. 40 CFR 721.4097 - 7-Oxabicyclo[4.1.0]heptane-3-carboxylic acid, methyl ester.

    Science.gov (United States)

    2010-07-01

    ..., methyl ester. 721.4097 Section 721.4097 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.4097 7-Oxabicyclo heptane-3-carboxylic acid, methyl ester. (a) Chemical...-oxabicyclo heptane-3-carboxylic acid, methyl ester (PMN P-98-101) is subject to reporting under this...

  6. 78 FR 5761 - Proposed Modification of Significant New Uses of Ethaneperoxoic Acid, 1,1-Dimethylpropyl Ester

    Science.gov (United States)

    2013-01-28

    ..., 1,1-Dimethylpropyl Ester AGENCY: Environmental Protection Agency (EPA). ACTION: Proposed rule... rule (SNUR) for the chemical substance identified as ethaneperoxoic acid, 1,1-dimethylpropyl ester..., process, or use the chemical substance identified as ethaneperoxoic acid, 1,1-dimethylpropyl ester (PMN...

  7. Ultrasound-assisted synthesis of aliphatic acid esters at room temperature.

    Science.gov (United States)

    Hobuss, Cristiane B; Venzke, Dalila; Pacheco, Bruna S; Souza, Alexander O; Santos, Marco A Z; Moura, Sidnei; Quina, Frank H; Fiametti, Karina G; Vladimir Oliveira, J; Pereira, Claudio M P

    2012-05-01

    This work describes the ultrasound-assisted synthesis of saturated aliphatic esters from synthetic aliphatic acids and either methanol or ethanol. The products were isolated in good yields after short reaction times under mild conditions.

  8. 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

  9. Isolation and characterization of esters of indole-3-acetic acid from the liquid endosperm of the horse chestnut (Aesculus species)

    Science.gov (United States)

    Domagalski, W.; Schulze, A.; Bandurski, R. S.

    1987-01-01

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

  10. 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%.

  11. High Performance Fatty Acid-Based Vinyl Ester Resin for Liquid Molding

    Science.gov (United States)

    2007-07-01

    novolac epoxy, and Epon 828, a diglycidyl ether of bisphenol A ( DGEBA ), were purchased from Hexion Specialty Chemicals and was used to synthesize vinyl... DGEBA vinyl ester resins with n~0.1 and containing no styrene, CN 151 and RDX 26936, were obtained from Sartomer and Cytec Surface Specialties Inc...Diglycidyl ether of bisphenol-A ( DGEBA ) Methacrylic Acid Figure 1: The reaction of DGEBA and methacrylic acid to produce the vinyl ester 2.3

  12. 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....

  13. Research on the Sizing Performance of Starch Grafted Poly-hydroxy Alkyl-acid Esters

    Institute of Scientific and Technical Information of China (English)

    GUO La-mei; GUO Liang-hong

    2010-01-01

    Starch grafted poly-hydroxy alkyl-acid esters were prepared via graft polymerization. Different characteristics of grafted starches were tested such as viscosity, viscosity stability, adhesion as well as properties of sized yams. Sizing performance was analyzed from the aspect of physical and chemical reactions between polymer molecules. It shows that starch grafted poly-hydroxy alkyl-acid esters have excellent sizing performance and could absolutely be used as sizes for polyester-cotton yarns.

  14. 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%).

  15. 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

  16. 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.

  17. 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.

  18. Stereocontrolled Synthesis of (E)-β, γ-Unsaturated Esters via Palladium-Catalyzed Cross-Coupling of (E)-Alkenylboronic Acids with a-Bromoacetic Esters

    Institute of Scientific and Technical Information of China (English)

    DUAN Yazhen; ZHANG Jianshe; YANG Jun; DENG Minzhi

    2009-01-01

    The cross-coupling reaction of trans-alkenylboronic acids with α-bromoacetic esters was firstly studied. It was found that using Pd(OAc)2 as catalyst, a bulky electron-rich phospine, (2-dicyclohexylphospino-biphenyl) as ligand, the reaction can be readily accomplished to give specific (E)-β,γ-unsaturated esters in high yields.

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

    Science.gov (United States)

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

  20. 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.

  1. 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.

  2. 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

  3. Synthesis of esters of androgens with unsaturated fatty acids for androgen requiring therapy.

    Science.gov (United States)

    Aiello, F; Garofalo, A; Aloisi, A M; Lamponi, S; Magnani, A; Petroni, A

    2013-06-01

    Androgens' metabolism and activity are gaining a more and more important role in human physiology particularly referring to aging and to neurodegenerative diseases. Androgen treatment is often required for long-lasting disorders. In order to improve their duration and effects, androgens can be administered as esters of carboxylic acids. The novelty of our research is the use of esters of androgens with specific unsaturated fatty acids, in order to reduce possible side effects particularly related to chronic pathologies with altered lipid homeostasis such as X-linked adrenoleukodystrophy and cardiovascular disorders. Thus the esters of the main androgenic substances testosterone, dihydrotestosterone (DHT) and their metabolite 5α-androstan-3α,17β-diol were chemically obtained by coupling with different unsaturated fatty acids. To this aim, fatty acids with various degree of unsaturation and belonging to different series were selected. Specifically, oleic acid (18:1, n-9), linoleic acid (18:2, n-6), and the n-3 fatty acids, α-linolenic acid (18:3), eicosapentaenoic acid (EPA, 20:5), and docosahexaenoic acid (DHA, 22:6) were used obtaining corresponding esters with acceptable yields and good degree of purity. All the synthesized compounds were tested for their cytotoxic activities in mouse NIH3T3 and human astrocyte cell lines. The esters demonstrated good tolerability and no in vitro cytotoxic effect in both cell cultures. After these promising preliminary results, the esters will be suitable for in vivo studies in order to ascertain their pharmacokinetic characteristics and their biological effects.

  4. Resolution of 4-amino-cyclopentanecarboxylic acid methyl esters using hydrolytic enzymes.

    Science.gov (United States)

    Mahmoudian, M; Baines, B S; Dawson, M J; Lawrence, G C

    1992-11-01

    A number of esterases (EC 3.1.1.1) and lipases (EC 3.1.1.3) of microbial and mammalian origin were screened for the ability to resolve racemic 4-amino-cyclopentanecarboxylic acid methyl ester derivatives as potential intermediates in the production of carbocyclic nucleosides. Surprisingly, functionalization of the remote amino group had a profound effect on both the rate and enantioselectivity of hydrolysis of the methyl ester. 4-(Benzoylamino)-2-cyclopentenecarboxylic acid, methyl ester (V) with pig liver esterase gave the highest enantioselectivity. The residual ester, which was of the correct absolute stereochemistry [(+) 1S, 4R] for carbocyclic nucleoside synthesis, could be obtained in high optical purity. Optimization of pH, solvent type, and concentration improved the enantioselectivity of the process by a further twofold.

  5. 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.

  6. 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

    2016-07-08

    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.

  7. 40 CFR 721.8500 - 2-Propenoic acid, 2-methyl-, 7-oxabicyclo [4.1.0]hept-3-ylmethyl ester.

    Science.gov (United States)

    2010-07-01

    ...-oxabicyclo hept-3-ylmethyl ester. 721.8500 Section 721.8500 Protection of Environment ENVIRONMENTAL... hept-3-ylmethyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance 2-propenoic acid, 2-methyl-, 7-oxabicyclo hept-3-ylmethyl ester (PMN P-89-30) is...

  8. 40 CFR 721.4792 - 2-propenoic acid, 2-methyl-, C11-14-isoalkyl esters, C13-rich.

    Science.gov (United States)

    2010-07-01

    ...-isoalkyl esters, C13-rich. 721.4792 Section 721.4792 Protection of Environment ENVIRONMENTAL PROTECTION... esters, C13-rich. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as 2-propenoic acid, 2-methyl-, C11-14-isoalkyl esters, C13-rich (PMN P-99-1189; CAS...

  9. 40 CFR 721.1578 - 1,4-Benzenedicarboxylic acid, bis[[4-[(ethenyloxy)methyl] cyclohexyl] methyl] ester.

    Science.gov (United States)

    2010-07-01

    ... cyclohexyl] methyl] ester. 721.1578 Section 721.1578 Protection of Environment ENVIRONMENTAL PROTECTION...] methyl] ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as 1,4-benzenedicarboxylic acid, bis cyclohexyl] methyl] ester (PMN P-98-1164; CAS...

  10. 40 CFR 721.1725 - Benzoic acid, 3,3′-methyl-enebis [6 amino-, di-2-propenyl ester.

    Science.gov (United States)

    2010-07-01

    ... amino-, di-2-propenyl ester. 721.1725 Section 721.1725 Protection of Environment ENVIRONMENTAL...-, di-2-propenyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The..., Benzoic acid, 3,3′-methylenebis [6 amino-, di-2-propenyl ester. (2) The significant new uses are: (i)...

  11. 40 CFR 721.1576 - 1,3-Benzenedicarboxylic acid, bis[[4-[(ethenyloxy)methyl] cyclohexyl] methyl] ester.

    Science.gov (United States)

    2010-07-01

    ... cyclohexyl] methyl] ester. 721.1576 Section 721.1576 Protection of Environment ENVIRONMENTAL PROTECTION...] methyl] ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as 1,3-benzenedicarboxylic acid, bis cyclohexyl] methyl] ester (PMN P-98-1162; CAS...

  12. 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.

  13. 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.

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

    Science.gov (United States)

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

    2015-12-01

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

  15. 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.

  16. Quantitation using a stable isotope dilution assay (SIDA) and thresholds of taste-active pyroglutamyl decapeptide ethyl esters (PGDPEs) in sake.

    Science.gov (United States)

    Hashizume, Katsumi; Ito, Toshiko; Igarashi, Shinya

    2017-03-01

    A stable isotope dilution assay (SIDA) for two taste-active pyroglutamyl decapeptide ethyl esters (PGDPE1; (pGlu)LFGPNVNPWCOOC2H5, PGDPE2; (pGlu)LFNPSTNPWCOOC2H5) in sake was developed using deuterated isotopes and high-resolution mass spectrometry. Recognition thresholds of PGDPEs in sake were estimated as 3.8 μg/L for PGDPE1 and 8.1 μg/L for PGDPE2, evaluated using 11 student panelists aged in their twenties. Quantitated concentrations in 18 commercial sake samples ranged from 0 to 27 μg/L for PGDPE1 and from 0 to 202 μg/L for PGDPE2. The maximum levels of PGDPE1 and PGDPE2 in the sake samples were approximately 8 and 25 times higher than the estimated recognition thresholds, respectively. The results indicated that PGDPEs may play significant sensory roles in the sake. The level of PGDPEs in unpasteurized sake samples decreased during storage for 50 days at 6 °C, suggesting PGDPEs may be enzymatically decomposed.

  17. 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.

  18. Gamma-Glutamylcysteine Ethyl Ester Protects against Cyclophosphamide-Induced Liver Injury and Hematologic Alterations via Upregulation of PPARγ and Attenuation of Oxidative Stress, Inflammation, and Apoptosis

    Science.gov (United States)

    Alqahtani, Sultan

    2016-01-01

    Gamma-glutamylcysteine ethyl ester (GCEE) is a precursor of glutathione (GSH) with promising hepatoprotective effects. This investigation aimed to evaluate the hepatoprotective effects of GCEE against cyclophosphamide- (CP-) induced toxicity, pointing to the possible role of peroxisome proliferator activated receptor gamma (PPARγ). Wistar rats were given GCEE two weeks prior to CP. Five days after CP administration, animals were sacrificed and samples were collected. Pretreatment with GCEE significantly alleviated CP-induced liver injury by reducing serum aminotransferases, increasing albumin, and preventing histopathological and hematological alterations. GCEE suppressed lipid peroxidation and nitric oxide production and restored GSH and enzymatic antioxidants in the liver, which were associated with downregulation of COX-2, iNOS, and NF-κB. In addition, CP administration significantly increased serum proinflammatory cytokines and the expression of liver caspase-3 and BAX, an effect that was reversed by GCEE. CP-induced rats showed significant downregulation of PPARγ which was markedly upregulated by GCEE treatment. These data demonstrated that pretreatment with GCEE protected against CP-induced hepatotoxicity, possibly by activating PPARγ, preventing GSH depletion, and attenuating oxidative stress, inflammation, and apoptosis. Our findings point to the role of PPARγ and suggest that GCEE might be a promising agent for the prevention of CP-induced liver injury. PMID:28074115

  19. Effect of Ethyl Ester L-Lysine Triisocyanate addition to produce reactive PLA/PCL bio-polyester blends for biomedical applications.

    Science.gov (United States)

    Visco, Annamaria; Nocita, Davide; Giamporcaro, Alberto; Ronca, Sara; Forte, Giuseppe; Pistone, Alessandro; Espro, Claudia

    2017-02-16

    We report in this paper the effects of Ethyl Ester L-Lysine Triisocyanate (LTI) on the physical-mechanical properties of Poly(lactide)/Poly(ε-caprolactone) (PLA/PCL) polyesters blends. The PLA/PCL ratios considered were 20/80, 50/50 and 80/20 (wt/wt %) and LTI was added in amounts of 0.0-0.5-1.0 phr. PLA and PCL reacted with LTI during processing in a Brabender twin screw internal mixer to produce block copolymers in-situ. The resulting blends have been characterized by torque measurements, uniaxial tensile tests, Differential Scanning Calorimeter, contact angle measurements with a Phosphate Buffered Saline (PBS) solution, ATR analysis and morphological SEM observations. Experimental results highlighted how LTI enhanced interaction and dispersion of the two components, resulting into a synergic effect in mechanical properties. Mechanical and physical properties can be tailored by changing the blend composition. The most noticeable trend was an increase in ductility of the mixed polymers. Besides, LTI decreased blend's wet ability in PBS and lowered the starting of crystalline phase formation for both polymers, confirming an interaction among them. These reactive blends could find use as biomedical materials, e.g. absorbable suture threads or scaffolds for cellular growth.

  20. 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.

  1. 40 CFR 721.3130 - Sulfuric acid, mono-C9-11-alkyl esters, sodium salts.

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Sulfuric acid, mono-C9-11-alkyl esters... Specific Chemical Substances § 721.3130 Sulfuric acid, mono-C9-11-alkyl esters, sodium salts. (a) Chemical... acid, mono-C9-11-alkyl esters, sodium salts (PMN P-01-149; CAS No. 84501-49-5) is subject to...

  2. Synthesis and biological evaluation of nigranoic acid esters as novel human neutrophil elastase inhibitors.

    Science.gov (United States)

    Huang, Guoli; Feng, Li; Liu, Bo; He, Yi; Li, Yiming; Chen, Yegao

    2015-01-01

    Human neutrophil elastase (HNE) has been implicated as a major contributor in the pathogenesis of diseases, such as lung disorders and other inflammatory diseases. A series of 12 new nigranoic acid esters were regioselectively synthesised in good yields and evaluated for HNE inhibitory activity. Nigranoic acid exhibited significant inhibitory activity against HNE with the IC50 value of 3.77 μM, and six esters displayed considerable inhibitory effects on HNE with IC50 values in the range of 2.61-8.95 μM. The nigranoic acid esters having phenyls substituted with bromine and trimethoxyls (3h and 3b) showed stronger inhibitory activity on HNE than nigranoic acid.

  3. Identification of 19 phthalic acid esters in dairy products by gas chromatography with mass spectrometry.

    Science.gov (United States)

    Wu, Pinggu; Cai, Chenggang; Yang, Dajin; Wang, Liyuan; Zhou, Yan; Shen, Xianghong; Ma, Bingjie; Tang, Jun

    2015-01-01

    A detection method for 19 kinds of phthalic acid ester compounds analyzed by n-hexane/ether/acetonitrile 1:7:8 v/v/v mixed solvent extraction, quick, easy, cheap, effective, rugged, and safe purification and internal standard method of quantitative gas chromatography with mass spectrometry was established. This method can effectively remove interfering materials, such as lipids, fatty acids, and pigments, from dairy products. The 19 kinds of phthalic acid ester compounds were within a 0.025-0.2 mg/kg range, the recovery rate was 65.2-125.7%, relative standard deviation was 7.9-15.4% (n = 6), and the limit of detection was 0.005-0.02 mg/kg. Concentrations of the 19 kinds of phthalic acid ester compounds ranged between 0.01 and 0.12 mg/kg in ten dairy materials and 20 dairy products. The established method is simple, rapid, accurate, and highly sensitive.

  4. 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.

  5. 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.

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

    Directory of Open Access Journals (Sweden)

    Hui Shen

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

  7. Highly selective and effective solid phase microextraction of benzoic acid esters using ionic liquid functionalized multiwalled carbon nanotubes-doped polyaniline coating.

    Science.gov (United States)

    Ai, Youhong; Wu, Mian; Li, Lulu; Zhao, Faqiong; Zeng, Baizhao

    2016-03-11

    The present work reports the electrochemical fabrication of an ionic liquid functionalized multiwalled carbon nanotubes-polyaniline (MWCNT@IL/PANI) nanocomposite coating and its application in the headspace-solid phase microextraction (HS-SPME) and gas chromatography (GC) determination of benzoic acid esters (i.e., methyl benzoate, ethyl benzoate, propyl benzoate and butyl benzoate). The MWCNTs was firstly functionalized with amine-terminated IL (MWCNT@IL) through chemical reduction, and then was doped in PANI during the electropolymerization of aniline. The resulting coating was characterized by infrared spectroscopy, field emission scanning electron microscopy and thermo gravimetry. It showed net-like structure and had high thermal stability (up to 330°C). Furthermore, it presented high selectivity for the four benzoic acid esters and thus suited for their HS-SPME-GC determination. Results showed that under optimized extraction conditions, the detection limits were less than 6.1ngL(-1) (S/N=3) and the linear detection ranges were 0.012-50μgL(-1) (R≥0.9957) for these analytes. The relative standard deviations (RSDs) were lower than 6.4% for five successive measurements with one fiber, and the RSDs for fiber-to-fiber were 4.4-9.6% (n=5). The developed method was successfully applied to the determination of these benzoic acid esters in perfume samples.

  8. 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...

  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. 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...

  11. Coriander Seed Oil Methyl Esters as Biodiesel Fuel: Unique Fatty Acid Composition and Excellent Oxidative Stability

    Science.gov (United States)

    Coriander (Coriandrum sativum L.) seed oil methyl esters were prepared and evaluated as an alternative biodiesel fuel and contained an unusual fatty acid (FA) hitherto unreported as the principle component in biodiesel fuels: petroselinic (6Z-octadecenoic; 68.5 wt %) acid. Most of the remaining FA...

  12. 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...

  13. Molecular assembly, interfacial rheology and foaming properties of oligofructose fatty acid esters.

    Science.gov (United States)

    van Kempen, Silvia E H J; Schols, Henk A; van der Linden, Erik; Sagis, Leonard M C

    2014-01-01

    Two major types of food-grade surfactants used to stabilize foams are proteins and low molecular weight (LMW) surfactants. Proteins lower the surface tension of interfaces and tend to unfold and stabilize the interface by the formation of a visco-elastic network, which leads to high surface moduli. In contrast, LMW surfactants lower the surface tension more than proteins, but do not form interfaces with a high modulus. Instead, they stabilize the interface through the Gibbs-Marangoni mechanism that relies on rapid diffusion of surfactants, when surface tension gradients develop as a result of deformations of the interface. A molecule than can lower the surface tension considerably, like a LMW surfactant, but also provide the interface with a high modulus, like a protein, would be an excellent foam stabilizer. In this article we will discuss molecules with those properties: oligofructose fatty acid esters, both in pure and mixed systems. First, we will address the synthesis and structural characterization of the esters. Next, we will address self-assembly and rheological properties of air/water interfaces stabilized by the esters. Subsequently, this paper will deal with mixed systems of mono-esters with either di-esters and lauric acid, or proteins. Then, the foaming functionality of the esters is discussed.

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

    Science.gov (United States)

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

    2017-02-01

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

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

    Science.gov (United States)

    Madl, Tobias; Mittelbach, Martin

    2005-04-01

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

  16. 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.

  17. Synthesis of (S)-ricinoleic acid and its methyl ester with the participation of ionic liquid.

    Science.gov (United States)

    Kula, Józef; Bonikowski, Radoslaw; Szewczyk, Malgorzata; Ciolak, Kornelia

    2014-10-01

    (R)-ricinoleic acid methyl ester obtained from commercial castor oil was transformed in a three-step procedure into its S-enantiomer in overall 36% yield using ionic liquid (1-butyl-3-methylimidazolium acetate) in the key step process. The developed procedure provides easy access to (S)-ricinoleic acid and its methyl ester of over 95% enantiomeric excess. Optical rotations of the newly obtained compounds as well as their chromatographic and spectral characteristics are provided and discussed in the context of enantiopurity both of the substrate material and the final products.

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

    OpenAIRE

    Wakita, M; Hoshino, S.

    1987-01-01

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

  19. Characterization and properties of a polythiophene with a malonic acid dimethyl ester side group

    OpenAIRE

    Armelín Diggroc, Elaine Aparecida; Bertran Cànovas, Òscar; Estrany Coda, Francesc; Salvatella, Roser; Alemán Llansó, Carlos

    2009-01-01

    A new polythiophene derivative bearing a malonic acid dimethyl ester substituent attached to the 3-position of the repeat unit has been prepared by chemical oxidative-coupling polymerization. The chemical structure of poly(2-thiophen-3-yl-malonic acid dimethyl ester) has been analyzed by FTIR and 1H NMR spectroscopy and, additionally, the distribution of the head-to-tail and head-to-head diads arising from polymerization was found to be a 75–25%. The glass transition temperature identified fo...

  20. 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.

  1. 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.

  2. n-3 PUFA Esterified to Glycerol or as Ethyl Esters Reduce Non-Fasting Plasma Triacylglycerol in Subjects with Hypertriglyceridemia

    DEFF Research Database (Denmark)

    Hedengran, Anne; Szecsi, Pal B; Dyerberg, Jørn;

    2015-01-01

    To date, treatment of hypertriglyceridemia with long-chain n-3 polyunsaturated fatty acids (n-3 PUFA) has been investigated solely in fasting and postprandial subjects. However, non-fasting triacylglycerols are more strongly associated with risk of cardiovascular disease. The objective......-PUFA group and 58.5 % in the EE-PUFA group (P heart rate in the AG-PUFA group decreased by three beats per minute (P = 0.045). High-density lipoprotein (HDL) cholesterol increased in the AG-PUFA group (P ...-associated phospholipase A2 (LpPLA2) decreased in the EE-PUFA group (P = 0.001). No serious adverse events were observed. Supplementation with long-chain n-3 PUFA lowered non-fasting triacylglycerol levels, suggestive of a reduction in cardiovascular risk. Regardless of the different effects on heart rate, HDL, and LpPLA2...

  3. [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.

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

    Directory of Open Access Journals (Sweden)

    Cvetković Ivana

    2008-01-01

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

  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. 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

    ... 21 Food and Drugs 6 2010-04-01 2010-04-01 false Diacetyl tartaric acid esters of mono- 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,...

  8. 21 CFR 573.637 - Methyl esters of conjugated linoleic acid (cis-9, trans-11 and trans-10, cis-12-octadecadienoic...

    Science.gov (United States)

    2010-04-01

    ... 21 Food and Drugs 6 2010-04-01 2010-04-01 false Methyl esters of conjugated linoleic acid (cis-9... § 573.637 Methyl esters of conjugated linoleic acid (cis-9, trans-11 and trans-10, cis-12-octadecadienoic acids). The food additive, methyl esters of conjugated linoleic acid (cis-9, trans-11 and...

  9. 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.

  10. 40 CFR 721.3635 - Octadecanoic acid, ester with 1,2-propanediol, phosphate, anhydride with silicic acid (H4SiO4).

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Octadecanoic acid, ester with 1,2..., ester with 1,2-propanediol, phosphate, anhydride with silicic acid (H4SiO4). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as octadecanoic acid,...

  11. 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.

  12. Fatty acid esters of monochloropropanediol (MCPD) and glycidol in refined edible oils.

    Science.gov (United States)

    Craft, B D; Chiodini, A; Garst, J; Granvogl, M

    2013-01-01

    Recently, fatty acid esters of monochloropropanediol (MCPD) and that of glycidol have been reported in refined edible oils. Since then a wealth of research has been published on the factors influencing the formation of these contaminants in foods. It can be noted that the predominant precursors in a given matrix will not necessarily be the same as in other matrices. Further, proven relationships in the past between precursors responsible for free MCPD or free glycidol formation will not necessarily be valid for their fatty acid-esterified counterparts. This review attempts to summarise the current status of the literature as it pertains to the reasons surrounding the manifestation of MCPD esters and glycidyl esters in oils and fats. Recent efforts to mitigate the levels of these contaminants were highlighted and put into the context of their respective reaction matrices. As more accurate occurrence data for MCPD esters and glycidyl esters in other foods are collected, more targeted mitigation experiments can be formulated with respect to the reaction matrices under investigation.

  13. Atmospheric Oxidation Mechanisms for Diethyl Ether and its Oxidation Products, Ethyl Formate and Ethyl Acetate.

    Science.gov (United States)

    Orlando, J. J.; Tyndall, G. S.

    2006-12-01

    Carbon-containing compounds are present in the earth's atmosphere as the result of emissions from natural and anthropogenic sources. Their oxidation in the atmosphere, initiated by such oxidants as OH, ozone, and nitrate radicals, leads to potentially harmful secondary pollutants such as ozone, carbonyl species, organic acids and aerosols. Ethers and esters are two classes of compounds that contribute to the complex array of organic compounds found in anthropogenically-influenced air. Additional ester is present as a result of the oxidation of the ethers. In this paper, the oxidation of diethyl ether and its two main oxidation products, ethyl formate and ethyl acetate, are studied over ranges of temperature, oxygen partial pressure, and NOx concentration, using an environmental chamber / FTIR absorption technique. Major end-products (the esters from diethyl ether; organic acids and anhydrides from the esters) are quantified, and these data are interpreted in terms of the chemistry of the various alkoxy and peroxy radicals generated. Emphasis is placed on the effects of chemical activation on the behavior of the alkoxy radicals, as well as on a novel peroxy radical rearrangement that may contribute to the observed products of ether oxidation under some conditions. Finally, the data are used, in conjunction with data on similar species, to provide a general representation of ether and ester oxidation in the atmosphere.

  14. 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.

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

    DEFF Research Database (Denmark)

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

    2008-01-01

    in enrichment cultures degrading phthalic acid esters under methanogenic conditions. A selection pressure was applied by adding DBP at 10 and 200 mg L(-1) in semi-continuous anaerobic reactors. The microbial dynamics were monitored using single strand conformation polymorphism (SSCP). While only limited abiotic...

  16. 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...

  17. 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

  18. 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...

  19. 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.

  20. 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.

  1. 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...

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

    NARCIS (Netherlands)

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

    2016-01-01

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

  3. Esterification and transesterification of greases to fatty acid methyl esters with highly active diphanylammonium salts

    Science.gov (United States)

    We have conducted an investigation designed to identify alternate catalysts for the production of fatty acid methyl esters (FAME) to be used as biodiesel. Diphenylammonium sulfate (DPAS) and diphenylammonium chloride (DPA-HCl) salts were found to be highly active homogeneous catalysts for the simu...

  4. Esterification and Transesterification of greases to fatty acid methyl esters with highly active diphenylamine salts

    Science.gov (United States)

    Diphenylamine sulfate (DPAS) and diphenylamine hydrochloride (DPACl) salts were found to be highly active catalysts for esterification and transesterification of inexpensive greases to fatty acid methyl esters (FAME). In the presence of catalytic amounts of DPAS or DPACl and excess methanol, the fr...

  5. Chemically modified fatty acid methyl esters: their potential for use as lubrication fluids and surfactants

    Science.gov (United States)

    A review of recent developments in the synthesis and characterization of lubrication fluids and surfactants from methyl oleate. The synthesis of materials made using an epoxidation route is the focus. This versatile method of chemical modification of fatty acid methyl esters improves their oxidati...

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

    DEFF Research Database (Denmark)

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

    2012-01-01

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

  7. 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.

  8. ESTIMATION OF PHOSPHATE ESTER HYDROLYSIS RATE CONSTANTS. II. ACID AND GENERAL BASE CATALYZED HYDROLYSIS

    Science.gov (United States)

    SPARC (SPARC Performs Automated Reasoning in Chemistry) chemical reactivity models were extended to calculate acid and neutral hydrolysis rate constants of phosphate esters in water. The rate is calculated from the energy difference between the initial and transition states of a ...

  9. 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.

  10. 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

  11. 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.

  12. 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), 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.

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

    DEFF Research Database (Denmark)

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

    1986-01-01

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

  14. Enzymatic production of fructose fatty acid ester using lipases from C. antarctica and porcine pancreatic

    OpenAIRE

    2009-01-01

    The aim of this work was to produce fructose fatty acid ester by enzymatic esterification of a fatty acid (oleic acid or linoleic acid) with fructose, using lipases (CALB) from Candida antarctica type B and porcine pancreas. The esterification reaction was conducted at 150 rpm and 40 °C during 72 hours. Equimolar (0.5 mmol) amounts of fructose and fatty acid were mixed with 0.6 ml of ethanol and sodium sulfate anhydrous (0.1 g) was added for the adsorption of the water generate...

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

    Directory of Open Access Journals (Sweden)

    AYE YUSUFOGLU

    2007-05-01

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

  16. Origin of Kinetic Resolution of Hydroxy Esters through Catalytic Enantioselective Lactonization by Chiral Phosphoric Acids.

    Science.gov (United States)

    Changotra, Avtar; Sunoj, Raghavan B

    2016-08-05

    Kinetic resolution is a widely used strategy for separation and enrichment of enantiomers. Using density functional theory computations, the origin of how a chiral BINOL-phosphoric acid catalyzes the selective lactonization of one of the enantiomers of α-methyl γ-hydroxy ester is identified. In a stepwise mechanism, the stereocontrolling transition state for the addition of the hydroxyl group to the si face of the ester carbonyl in the case of the S isomer exhibits a network of more effective noncovalent interactions between the substrate and the chiral catalyst.

  17. 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.

  18. 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.

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

    OpenAIRE

    2006-01-01

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

  20. Synthesis of oleic acid based esters as potential basestock for biolubricant production

    OpenAIRE

    Salih, Nadia; Salimon, Jumat; Yousif, Emad

    2011-01-01

    Ester derivatives of 9, 10-dihydroxystearic acid were prepared and characterized. The processes involved were epoxidation of oleic acid, opening of the oxirane ring, and esterification. The structures of the products were confirmed by FTIR, 1H- and 13C-NMR. The low-temperature properties of each product were characterized using the pour point test. Other physical properties, such as flash point and viscosity, were also determined. The results show that desirable low temperature pro...

  1. 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...

  2. 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}.

  3. Synthesis and Primary Research on Antitumor Activity of Three New Panaxadiol Fatty Acid Esters

    Institute of Scientific and Technical Information of China (English)

    2007-01-01

    For making use of Ginseng resources that exhibit an antitumor activity and for finding new anticancer drugs,three new fatty acid ester compounds: 3β-acetoxy panaxadiol ( Ⅰ ), 3β-palmitic acid aceloxy panaxadiol ( Ⅱ ), and 3β-octadecanoic acid aceloxy panaxadiol( Ⅰ , Ⅱ , and Ⅲ ) were synthesized with panaxadiol, diacetyl oxide, palmityl chloride and stearyl chloride, and their structures were determined via MS, 13C NMR, IR, TLC, and so on. The molar yields of the three compounds are 75.14%, 79. 08%, and 72. 57%, respectively. Meanwhile, the antitumor activity of the three new panaxadiol fatty acid ester derivatives and panaxadiol was compared by using the method of MTT. Tumor cell used was Vero cell line. Positive control was 5-FU, blank was an RPMI1640 culture medium, negative control was an RPMI1640 culture medium and the solvent for drugs to be tested. Compound Ⅰ has the strongest antitumor activity followed by panaxadiol; compounds Ⅱ and Ⅲ have similar and weakest antitumor activities.Furthermore, the antitumor activities of the panaxadiol fatty acid ester derivatives show positive correlation with the concentration of the test group, but show no relationship with the molecular weight of fatty acid. The methods that are used to synthesize the three compounds with high yields and strong antitumor activities are simple and show a great potential for meeting the needs of industrial manufacture of these drugs.

  4. Fatty acid esters of 3-chloropropane-1,2-diol in edible oils.

    Science.gov (United States)

    Zelinková, Z; Svejkovská, B; Velísek, J; Dolezal, M

    2006-12-01

    A series of 25 virgin and refined edible oils, obtained from retailers, was analyzed for levels of free 3-chloropropane-1,2-diol (3-MCPD) and 3-MCPD released from esters with higher fatty acids (bound 3-MCPD). Oils containing free 3-MCPD ranging from 280 degrees C, and heating at 230 degrees C (260 degrees C) for up to 8 h, led to an increase in bound 3-MCPD levels. On the other hand, heating of olive oil resulted in a decrease in bound 3-MCPD levels. For comparison, fat isolated from salami was analyzed for intact fatty acid esters of 3-MCPD. This fat contained bound 3-MCPD at a level of 1670 microg kg-1 and the fatty acid esters of 3-MCPD mainly consisted of 3-MCPD diesters; monoesters of 3-MCPD were present in smaller amounts. The major types of 3-MCPD diesters (about 85%) were mixed diesters of palmitic acid with C18 fatty acids (stearic, oleic, linoleic acids). These diesters were followed by 3-MCPD distearate (11%) and 3-MCPD dipalmitate (4%). Generally, very little 3-MCPD existed as the free compound (31 microg kg-1).

  5. Synthesis of acylamino acid esters of nucleoside 5'-phosphates and their investigation with PMR and CD spectra.

    Science.gov (United States)

    Azhayev, A V; Popovkina, S V; Tarussova, N B; Kirpichnikov, M P; Florentiev, V L; Krayevsky, A A; Kukhanova, M K; Gottikh, B P

    1977-01-01

    The acylamino acid esters of nucleoside 5'-phosphates are synthesized via condensation of N-(N'-acylaminoacyl) imidazoles with nucleoside 5'-phosphates. The PMR and CD spectra of the esters obtained are studied. The 3'-isomers of the substances under study are observed to have a shift in the conformational N in equilibrium S equilibrium of the carbohydrate moiety in favour of the S-form as compared to the initial nucleosides and their 2'-acyl esters. PMID:909771

  6. 40 CFR 721.2140 - Carbo-poly-cycli-col azo-alkyl-aminoalkyl-carbo-mono-cyclic ester, halogen acid salt.

    Science.gov (United States)

    2010-07-01

    ...-aminoalkyl-carbo-mono-cyclic ester, halogen acid salt. 721.2140 Section 721.2140 Protection of Environment...-aminoalkyl-carbo-mono-cyclic ester, halogen acid salt. (a) Chemical substance and significant new uses...-mino-al-kyl-car-bo-mon-o-cyc-lic ester, halogen acid salt (PMN P-88-1682) is subject to reporting...

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

    Science.gov (United States)

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

    2011-04-01

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

  8. Kinematic viscosity of biodiesel components (fatty acid alkyl esters) and related compounds at low temperatures

    Energy Technology Data Exchange (ETDEWEB)

    Gerhard Knothe; Kevin R. Steidley [US Department of Agriculture, Peoria, IL (United States). National Center for Agricultural Utilization Research

    2007-11-15

    Biodiesel, defined as the mono-alkyl esters of vegetable oils and animal fats is, has undergone rapid development and acceptance as an alternative diesel fuel. Kinematic viscosity is one of the fuel properties specified in biodiesel standards, with 40{sup o}C being the temperature at which this property is to be determined and ranges of acceptable kinematic viscosity given. While data on kinematic viscosity of biodiesel and related materials at higher temperatures are available in the literature, this work reports on the kinematic viscosity of biodiesel and a variety of fatty acid alkyl esters at temperatures from 40{sup o}C down to -10{sup o}C in increments of 5{sup o}C using the appropriately modified standard reference method ASTM D445. Investigating the low-temperature properties of biodiesel, including viscosity, of biodiesel and its components is important because of the problems associated with the use of biodiesel under these conditions. Such data may aid in developing biodiesel fuels optimized for fatty ester composition. An index termed here the low-temperature viscosity ratio (LTVR) using data at 0{sup o}C and 40{sup o}C (divide viscosity value at 0{sup o}C by viscosity value at 40{sup o}C) was used to evaluate individual compounds but also mixtures by their low-temperature viscosity behavior. Compounds tested included a variety of saturated, monounsaturated, diunsaturated and triunsaturated fatty esters, methyl ricinoleate, in which the OH group leads to a significant increase in viscosity as well as triolein, as well as some fatty alcohols and alkanes. Esters of oleic acid have the highest viscosity of all biodiesel components that are liquids at low temperatures. The behavior of blends of biodiesel and some fatty esters with a low-sulfur diesel fuel was also investigated. 28 refs., 3 figs., 10 tabs.

  9. 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).

  10. Protective effects of luteolin-7-O-beta-D-glucuronide methyl ester from the ethyl acetate fraction of Lycopi Herba against pro-oxidant reactive species and low-density lipoprotein peroxidation.

    Science.gov (United States)

    Lee, Min-Ja; Lee, Hye-Sook; Park, Sun-Dong; Moon, Hyung-In; Park, Won-Hwan

    2010-10-01

    In this study the potent scavenging activity of "Lycopi Herba" (LH) extract was studied using the following: evaluation of the total phenolics, measuring the antioxidant activity by Trolox equivalent antioxidant concentration, measuring the scavenging effects on reactive oxygen species, on reactive nitrogen species, and measuring the inhibitory effect on Cu(2+) induced human low-density lipoprotein oxidation in vitro. The ethyl acetate fraction from the LH extracts were found to have a potent scavenging activity against all of the reactive species tested, as well as an inhibitory effect on LDL oxidation. Therefore, we isolated and identified luteolin-7-O-beta-D-glucuronide methyl ester as the major compound from the ethyl acetate fraction of LH and their antioxidant activities were evaluated.

  11. Field study of the urinary excretion of ethoxyacetic acid during repeated daily exposure to the ethyl ether of ethylene glycol and the ethyl ether of ethylene glycol acetate.

    Science.gov (United States)

    Veulemans, H; Groeseneken, D; Masschelein, R; Van Vlem, E

    1987-06-01

    The urinary excretion of ethoxyacetic acid (EAA) was studied in a group of five women daily exposed to the ethyl ether of ethylene glycol (EGEE) and the ethyl ether of ethylene glycol acetate (EGEE-Ac) during 5 d of normal production and 7 d after a 12-d production stop. The mean combined exposure concentration of EGEE and EGEE-Ac (expressed in equivalent weight of EGEE) was 14.0 mg/m3 with occasional slight excursions above the current Belgian occupational exposure limit. The daily combined exposure profiles for EGEE and EGEE-Ac were rather constant during the first observation period, but they tended to decrease during the last week. The urinary EAA excretion clearly increased during the work week. Over the weekends the elimination was far from complete, and even after a prolonged nonexposure period of 12 d traces of the metabolite were still detectable. Based on the observations from the first period, a good linear correlation (r = 0.92) was found between the average exposure over 5 d (14.4 mg/m3) and the EAA excretion at the end of the week (105.7 mg/g creatinine). An EAA estimate of 150 +/- 35 mg/g was found to correspond with repeated 5-d full-shift exposures to the respective occupational exposure limit of EGEE (19 mg/m3) or EGEE-Ac (27 mg/m3).

  12. Enzymatic esterification of tapioca maltodextrin fatty acid ester.

    Science.gov (United States)

    Udomrati, Sunsanee; Gohtani, Shoichi

    2014-01-01

    In this work new types of hydrophobically modified maltodextrin were prepared by enzyme-catalyzed reaction of maltodextrin and three fatty acids: decanoic acid (C-10), lauric acid (C-12) and palmitic acid (C-16). Lipase obtained from Thermomyces lanuginosus was found to be a useful biocatalyst in the maltodextrin esterification. Esterified maltodextrin with a degree of substitution (DS) 0.015-0.084 was prepared at the optimum conditions of 60 °C for 4 h. The DS was found to be at its highest when maltodextrin and fatty acids were taken in the ratio 1:0.5. The functional properties of these esterified maltodextrin were investigated. All esterified maltodextrin did not completely dissolve in water. Esterified maltodextrin at a concentration of 25% (w/w) exhibited Newtonian flow behavior similar to that of native maltodextrin. Esterified maltodextrin had a higher viscosity compare to native maltodextrin. X-ray diffraction pattern of esterified maltodextrin indicated crystallization of the fatty acid side chains. The thermal stability of esterified maltodextrin was checked by differential scanning calorimetry (DSC). Esterified maltodextrin was then used as an emulsifier to make n-hexadecane O/W emulsions. The emulsions were characterized according to their oil droplet characteristics and emulsification index.

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

    Directory of Open Access Journals (Sweden)

    Rosanna Solinas

    2008-12-01

    Full Text Available The imidazole-4,5-dicarboxylic acid scaffold is readily derivatized with amino acid esters and alkanamines to afford compounds with intramolecularly hydrogen bonded conformations that mimic substituted purines and therefore are hypothesized to be potential inhibitors of kinases through competitive binding to the ATP site. In this work, a total of 126 dissymmetrically disubstituted imidazole-4,5-dicarboxamides with amino acid ester and alkanamide substituents were prepared by parallel synthesis. The library members were purified by column chromatography on silica gel and the purified compounds characterized by LC-MS with LC detection at 214 nm. A selection of the final compounds was also analyzed by 1H-NMR spectroscopy. The analytically pure final products have been submitted to the Molecular Library Small Molecule Repository (MLSMR for screening in the Molecular Library Screening Center Network (MLSCN as part of the NIH Roadmap.

  14. Synergistic extraction of praseodymium with 2-ethylhexyl phosphonic acid mono-2-ethylhexyl ester and 8-Hydroxyquinoline

    Institute of Scientific and Technical Information of China (English)

    ZHANG Qian; WU Dong-bei; BAO Bo-rong

    2009-01-01

    The synergistic extraction of Pr3+ from hydrochloric medium using mixture of 2-ethylhexyl phosphonic acid mono-2-ethylhexyl ester (P507, HL) and 8-Hydroxyquinoline (HQ) in heptane was investigated. The effect of equilibrium of aqueous acidity on extraction of Pr3+ was discussed. The effect of extractant concentraction, different diluents, equilibrium time and acetate ion concentration on extraction reaction were also studied. With a method of double-logarithmic slope, composition of the extracted species on 2-ethylhexyl phosphonic acid mono-2-ethylhexyl ester and 8-Hydroxyquinolinc was derived. The result shows that the synergistic extraction system not only overcomes emulsification of 8-Hydroxyquinoline, but also shows perfect capacity of synergistic extraction. The largest synergistic enhancement factor can be calculated to be 5.49 at pH 3.6 for Pr3+.

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

    Science.gov (United States)

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

    2016-03-01

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

  16. 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.

  17. 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.

  18. Synthesis of allyl esters of fatty acids and their ovicidal effect on Cydia pomonella (L.).

    Science.gov (United States)

    Escribà, Marc; Barbut, Montserrat; Eras, Jordi; Canela, Ramon; Avilla, Jesús; Balcells, Mercè

    2009-06-10

    Eight allyl esters of fatty acids were synthesized in moderate to high yields with a novel two-step procedure using glycerol as a starting material. The two-step methodology avoids the use of allyl alcohol. The first step consisted of heating at 80 degrees C for 48 h a 2:1:5 mmol mixture of glycerol, a fatty acid, and chlorotrimethylsilane in a solvent-free medium. The crude compound was then dissolved in butanone and heated at 115 degrees C in the presence of NaI. A tandem Finkelstein rearrangement-elimination reaction occurs, producing the corresponding allyl ester. The activity of these esters against Cydia pomonella (L.) (Lepidoptera: Tortricidae) eggs was tested in the laboratory by topical application of one 0.1 microL drop. All of the compounds showed a concentration-mortality response and caused 100% mortality at the highest concentration tested (10 mg/mL). There was an inverse relationship between the alkyl chain length and the ovicidal activity of the allyl ester; the LC(50) and the LC(90) of the two compounds that have the longer alkyl chains were significantly higher than those of the rest of the compounds. The ovicidal and IGR activities of this kind of compound appear to be unprecedented.

  19. Hydrocracking of ethyl laurate on bifunctional micro-/mesoporous composite materials

    Energy Technology Data Exchange (ETDEWEB)

    Adam, M.; Busse, O.; Reschetilowski, W. [Technische Univ. Dresden (Germany). Inst. for Industrial Chemistry

    2011-07-01

    Hydrocracking of ethyl laurate (dodecanoic acid ethyl ester) as a representative model compound of vegetable oil has been investigated in a fixed bed reactor under integral conditions. A synthesized micro-/mesoporous composite support material Al-MCM-41/ZSM-5 modified by different metal loadings (NiMo, NiW, PtNiW) was used as catalyst system. It could be demonstrated that the metal loading and reducibility influence product selectivity as well as deactivation behavior of catalyst samples. (orig.)

  20. 40 CFR 721.990 - 1,4-Benzedicarboxylic acid, dimethyl ester, polymer with 1,4 - butanediol, cyclized.

    Science.gov (United States)

    2010-07-01

    ... ester, polymer with 1,4 - butanediol, cyclized. 721.990 Section 721.990 Protection of Environment..., dimethyl ester, polymer with 1,4 - butanediol, cyclized. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as 1,4-benzedicarboxylic acid, dimethyl...

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

    NARCIS (Netherlands)

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

    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

  2. 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

  3. 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.

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

    Science.gov (United States)

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

    2016-10-01

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

  5. 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.

  6. The stereodirecting effect of the glycosyl C5-carboxylate ester: stereoselective synthesis of beta-mannuronic acid alginates.

    Science.gov (United States)

    Codée, Jeroen D C; van den Bos, Leendert J; de Jong, Ana-Rae; Dinkelaar, Jasper; Lodder, Gerrit; Overkleeft, Herman S; van der Marel, Gijsbert A

    2009-01-02

    Glycosylations of mannuronate ester donors proceed highly selectively to produce the 1,2-cis-linked products. We here forward a mechanistic rationale for this counterintuitive selectivity, based on the remote stereodirecting effect of the C5-carboxylate ester, which has been demonstrated using pyranosyl uronate ester devoid of ring substituents other than the C5- carboxylate ester. It is postulated that the C5-carboxylate ester prefers to occupy an axial position in the oxacarbenium intermediate, thereby favoring the formation of the (3)H4 half-chair over the (4)H3 conformer. Nucleophilic attack on the (3)H4 half-chair intermediate occurs in a beta-fashion, providing the 1,2-cis-mannuronates with excellent stereoselectivity. The potential of the mannuronate ester donors in the formation of the beta-mannosidic linkage has been capitalized upon in the construction of a mannuronic acid alginate pentamer using a convergent orthogonal glycosylation strategy.

  7. Unambiguous detection of astaxanthin and astaxanthin fatty acid esters in krill (Euphausia superba Dana).

    Science.gov (United States)

    Grynbaum, Marc David; Hentschel, Petra; Putzbach, Karsten; Rehbein, Jens; Krucker, Manfred; Nicholson, Graeme; Albert, Klaus

    2005-09-01

    HPLC atmospheric pressure chemical ionization (APCI)/MS, GC MS, HPLC diode array detection (DAD), and NMR were used for the identification of astaxanthin and astaxanthin fatty acid esters in krill (Euphausia superba Dana). Matrix solid phase dispersion was applied for the extraction of the carotenoids. This gentle and expeditious extraction technique for solid and viscous samples leads to distinct higher enrichment rates than the conventional liquid-liquid extraction. The chromatographic separation was achieved employing a C30 RP column that allows the separation of shape-constrained geometrical isomers. A methanol/tert-butylmethyl ether/water gradient was applied. (all-E) Astaxanthin and the geometrical isomers were identified by HPLC APCI/MS, by coelution with isomerized authentical standard, by UV spectroscopy (DAD), and three isomers were unambiguously assigned by microcoil NMR spectroscopy. In this method, microcoils are transversally aligned to the magnetic field and have an increased sensitivity compared to the conventional double-saddle Helmholtz coils, thus enabling the measurement on small samples. The carotenol fatty acid esters were saponified enzymatically with Lipase type VII from Candida rugosa. The fatty acids were detected by GC MS after transesterification, but also without previous derivatization by HPLC APCI/MS. C14:0, C16:0, C16:1, C18:1, C20:0, C20:5, and C22:6 were found in astaxanthin monoesters and in astaxanthin diesters. (all-E) Astaxanthin was identified as the main isomer in six fatty acid ester fractions by NMR. Quantitation was carried out by the method of internal standard. (13-cis) Astaxanthin (70 microg/g), 542 microg/g (all-E) astaxanthin, 36 microg/g unidentified astaxanthin isomer, 62 microg/g (9-cis) astaxanthin, and 7842 microg/g astaxanthin fatty acid esters were found.

  8. 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.

  9. 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

  10. Biochemical mechanism of Caffeic Acid Phenylethyl Ester (CAPE) selective toxicity towards melanoma cell lines

    OpenAIRE

    Kudugunti, Shashi K.; Vad, Nikhil M.; Whiteside, Amanda J.; Naik, Bhakti U.; Yusuf, Mohd. A.; Srivenugopal, Kalkunte S.; Moridani, Majid Y.

    2010-01-01

    In the current work, we investigated the in-vitro biochemical mechanism of caffeic acid phenylethyl ester (CAPE) toxicity and eight hydroxycinnamic/caffeic acid derivatives in-vitro, using tyrosinase enzyme as a molecular target in human SK-MEL-28 melanoma cells. Enzymatic reaction models using tyrosinase/O2 and HRP/H2O2 were used to delineate the role of one- and two-electron oxidation. Ascorbic acid (AA), NADH and GSH depletion were used as markers of quinone formation and oxidative stress ...

  11. 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.

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

    Science.gov (United States)

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

    2016-06-07

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

  13. 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.

  14. Heating Two Types of Enriched Margarine: Complementary Analysis of Phytosteryl/Phytostanyl Fatty Acid Esters and Phytosterol/Phytostanol Oxidation Products.

    Science.gov (United States)

    Scholz, Birgit; Menzel, Nicole; Lander, Vera; Engel, Karl-Heinz

    2016-04-06

    Two phytosteryl and/or phytostanyl fatty acid ester-enriched margarines were subjected to common heating procedures. UHPLC-APCI-MS analysis resulted for the first time in comprehensive quantitative data on the decreases of individual phytosteryl/-stanyl fatty acid esters upon heating of enriched foods. These data were complemented by determining the concurrently formed phytosterol/-stanol oxidation products (POPs) via online LC-GC. Microwave-heating led to the least decreases of esters of approximately 5% in both margarines. Oven-heating of the margarine in a casserole caused the greatest decreases, with 68 and 86% esters remaining, respectively; the impact on individual esters was more pronounced with increasing degree of unsaturation of the esterified fatty acids. In the phytosteryl/-stanyl ester-enriched margarine, approximately 20% of the ester losses could be explained by the formation of POPs; in the phytostanyl ester-enriched margarine, the POPs accounted for <1% of the observed ester decreases.

  15. 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.

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

    Energy Technology Data Exchange (ETDEWEB)

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

    2010-04-15

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

  17. 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.

  18. Calculations of phase equilibria for mixtures of triglycerides, fatty acids, and their esters in lower alcohols

    Science.gov (United States)

    Stepanov, D. A.; Ermakova, A.; Anikeev, V. I.

    2011-01-01

    The objects of study were mixtures containing triglycerides and lower alcohols and also the products of the transesterification of triglycerides, glycerol and fatty acid esters. The Redlich-Kwong-Soave equation of state was used as a thermodynamic model for the phase state of the selected mixtures over wide temperature, pressure, and composition ranges. Group methods were applied to determine the critical parameters of pure substances and their acentric factors. The parameters obtained were used to calculate the phase diagrams and critical parameters of mixtures containing triglycerides and lower alcohols and the products of the transesterification of triglycerides, glycerol and fatty acid esters, at various alcohol/oil ratios. The conditions of triglyceride transesterification in various lower alcohols providing the supercritical state of reaction mixtures were selected.

  19. 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.

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

    Science.gov (United States)

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

    2017-03-01

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

  1. 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

  2. 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

  3. Characterization of Lipids and Fatty Acid Methyl Ester Contents in Leaves and Roots of Crocus vallicola

    OpenAIRE

    YAYLI, Nurettin; KIRAN, Zerrin; SEYMEN, Hasan; GENÇ, Hasan

    2001-01-01

    The chemical composition of the fatty acids methyl esters (FAMEs) and other lipids in leaves and roots of Crocusvallicola were analyzed by gas chromatography-mass spectrometry(GC-MS). In this work, twenty-eight compounds, including 22 FAMEs, 1 aldehyde, 3 hydrocarbons (substitute alkane and alkene), 2 alcohols in the leaves and twenty-one compounds (17 FAMEs, 1 anhydride, 1 substitute alcohol, 1 ketone, 1 substitute amide) in the roots were identified by GC-MS from C. vallicola. Th...

  4. [Determination of phthalic acid esters in textiles by solid phase extraction-gas chromatography].

    Science.gov (United States)

    Niu, Zengyuan; Ye, Xiwen; Fang, Liping; Xue, Qiuhong; Sun, Zhongsong

    2006-09-01

    A method was established for the simultaneous determination of some phthalic acid esters, namely, dimethyl phthalate (DMP), diethyl phthalate (DEP), dipropyl phthalate (DPrP), dibutyl phthalate (DBP), diamyl phthalate (DAP), dihexyl phthalate (DHP), benzyln-butyl phthalate (BBP), di-(2-ethylhexyl) phthalate (DEHP), dicyclohexyl phthalate (DCHP), di-n-octyl phthalate (DNOP), diisononyl phthalate (DINP) and diisodecyl phthalate (DIDP) in textiles by solid phase extraction (SPE) coupled with gas chromatography (GC). The phthalic acid esters in textiles were extracted by Soxhlet extraction with hexane, the extracts were then cleaned up and enriched by a strong anion exchange (SAX) SPE cartridge. The parameters affecting the purification efficiency of SPE cartridge, such as solvent conditioning, rinsing, and elution, were studied. Conditioning with 5 mL hexane and rinsing with 3 mL isooctane were proved to be the optimal conditions. Of the several solvent ratios (ethylacetate in hexane) used for selective elution of phthalic acid esters from the SAX SPE cartridge, the 15% (v/v) content for ethylacetate in hexane gave the best result. Under the optimized conditions, the recoveries of phthalic acid esters for spiked standards (n=7) were 86.3%-102.7%, and the relative standard deviations (RSDs) were less than 5%. In this method the detection limits for DMP, DEP, DPrP, DBP, DAP, BBP, DCHP, DEHP, DNOP were all below 1 mg/kg, and the detection limits for DINP and DIDP were 1.74 mg/kg and 1.55 mg/kg respectively. This SPE-GC method is sensitive, accurate and suitable for the analysis of phthalate environmental hormones in textiles.

  5. Preferential cytotoxicity on tumor cells by caffeic acid phenethyl ester isolated from propolis.

    Science.gov (United States)

    Grunberger, D; Banerjee, R; Eisinger, K; Oltz, E M; Efros, L; Caldwell, M; Estevez, V; Nakanishi, K

    1988-03-15

    The honeybee hive product, propolis, is a folk medicine employed for treating various ailments. Many important pharmaceutical properties have been ascribed to propolis, including anti-inflammatory, antiviral, immunostimulatory and carcinostatic activities. Propolis extracts have provided an active component identified as caffeic acid phenethyl ester (CAPE), which was readily prepared in one step. Differential cytotoxicity has been observed in normal rat/human versus transformed rat/human melanoma and breast carcinoma cell lines in the presence of CAPE.

  6. 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 ℃.

  7. 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.

  8. 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.

  9. Evaluation of eye irritation by S-(-)-10,11-dihydroxyfarnesic acid methyl ester secreted by Beauveria bassiana CS1029.

    Science.gov (United States)

    Son, Hyeong-U; Lee, Sang-Han

    2013-10-01

    The aim of this study was to investigate whether S-(-)-10,11-dihydroxyfarnesic acid methyl ester produced by cell subtype Beauveria bassiana CS1029 causes acute toxicity when used for cosmetic purposes by performing an eye irritation test. New Zealand white (NZW) rabbits were treated with a 100 mg/dose of S-(-)-10,11-dihydroxyfarnesic acid methyl ester according to standard procedure guidelines. No significant changes in terms of ocular lesions of the cornea, turbidity of the cornea, swelling of the eyelid or ocular discharge were observed in the methyl ester-treated groups, while sodium dioctyl sulfosuccinate, a positive control, caused severe toxicity. The anatomical and pathological observations indicate that the methyl ester produced by Beauveria bassiana CS1029 did not induce eye irritation in the lenses of the rabbits. The data suggest that the methyl ester evaluated in this study has promising potential as a cosmetic ingredient that does not irritate the eye.

  10. 40 CFR 721.1730 - Poly(oxy-1,2-ethanediyl), α-butyl-ω-hydroxy, ester with boric acid (H3BO3).

    Science.gov (United States)

    2010-07-01

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

  11. 40 CFR 721.1731 - Poly(oxy-1,2-ethanediyl), α-methyl-ω-hydroxy, ester with boric acid (H3BO3).

    Science.gov (United States)

    2010-07-01

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

  12. 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.

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

    Science.gov (United States)

    Kimura, Wataru; Endo, Yasushi

    2017-03-01

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

  14. Joint effects of dithiophosphoric acid ester and antioxidants on performance properties of mineral oil

    Energy Technology Data Exchange (ETDEWEB)

    Borshchevskii, S.B.; Shabanova, Ye.V.; Zagorodnyy, N.G.; Trofimov, G.A.

    1982-05-01

    High temperatures, catalytic effects of metals and environmental oxidation bring significant changes in lubricating oils. The joint effects of the methylbenzyl ester of diisobutyldithiophosphoric acid and various phenol and amine antioxidant additives were studied. At 200/sup 0/C, 2,2-methylene-bis(4-methyl-6-tert-butylphenol) and 2,6-di(tert-butyl)-4-methylphenol had a prooxidational effect, while 4,4-methylene-bis(2,6(tert-butyl)phenol), phenol-alpha-naphthylamine and the mixed products of phenol alkylation by styrene (A0-20) inhibited oxidation. A0-20 reduced the methylbenzyl ester's prooxidational action, while the others had little effect. At 180/sup 0/C in the presence of copper, all tested antioxidants but A0-20 inhibited oxidation and the methylbenzyl ester increased that action. Little change was noted in the M-11 lubricating oil tested because of the additives. The combination of A0-20 and the ester improved antiwear, antiscratch and antioxidation properties better than other combinations. 4 references, 2 figures.

  15. 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.)

  16. 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)

  17. 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.

  18. 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.

  19. Catalytic Autoxidation of Fatty Acid Methyl Esters from Jatropha Oil

    Directory of Open Access Journals (Sweden)

    Abebe K. Endalew

    2014-01-01

    Full Text Available Metal catalysts for transesterification of vegetable oils can cause autoxidation side reactions which reduces the fuel quality of the biodiesel. On the other side, oxidation of highly unsaturated oils can open opportunities for the synthesis of other important renewable chemical products. This study reports catalytic oxidation of fatty acids of Jatropha curcas oil (JCO by Li-CaO/Fe2(SO43 catalyst during transesterification at mild reaction conditions. The catalytic oxidation of the triglycerides was shown to be enhanced by the presence of lithium incorporated in the otherwise active catalyst combination of CaO/Fe2(SO43 used for high conversion into FAME. Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS was used to assess the reaction products.

  20. 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.

  1. 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.

  2. Antioxidant activity of propolis: role of caffeic acid phenethyl ester and galangin.

    Science.gov (United States)

    Russo, A; Longo, R; Vanella, A

    2002-11-01

    Propolis, a natural product produced by the honeybee, has been used for thousands of years in folk medicine for several purposes. The extract contains amino acids, phenolic acids, phenolic acid esters, flavonoids, cinnamic acid, terpenes and caffeic acid. It possesses several biological activities such as antiinflammatory, immunostimulatory, antiviral and antibacterial. The exact mode of physiological or biochemical mechanisms responsible for the medical effects, however, is yet to be determined. In this work, we have investigated the antioxidant activity of a propolis extract deprived of caffeic acid phenethyl ester (CAPE). In addition, the activity of CAPE and galangin was also examined. Propolis extract (with and without CAPE) and its active components showed a dose-dependent free radical scavenging effect, a significant inhibition of xanthine oxidase activity, and an antilipoperoxidative capacity. Propolis extract with CAPE was more active than propolis extract without CAPE. CAPE, used alone, exhibited a strong antioxidant activity, higher than galangin. The experimental evidence, therefore, suggests that CAPE plays an important role in the antioxidant activity of propolis.

  3. Synthesis and structural characterization of derivatives of 2- and 3-benzo[b]furan carboxylic acids with potential cytotoxic activity.

    Science.gov (United States)

    Kossakowski, Jerzy; Ostrowska, Kinga; Hejchman, Elzbieta; Wolska, Irena

    2005-01-01

    Derivatives of 2- and 3-benzo[b]furancarboxylic acids were prepared and evaluated for their cytotoxic potential in the National Cancer Institute, Bethesda, USA. Six compounds: 7-acetyl-6-hydroxy-3-methyl-2-benzofurancarboxylic acid (2), 6-hydroxy-7-(p-methoxycinnamoyl)-3-methyl-2-benzofurancarboxylic acid (4), 5-bromo-7-hydroxy-6-methoxy-2-benzofurancarboxylic acid methyl ester (6a), 6-acetyl-5-(O-ethyl-2'-diethylamino)-2-methyl-3-benzofurancarboxylic acid methyl ester (1f), 6-(O-ethyl-2'-diethylamino)-7-p-methoxycinnamoyl)-3-methyl-2-benzofurancarboxylic acid methyl ester hydrochloride (4b), 5-bromo-7-(O-ethyl-2'-diethylamino)-6-methoxy-2-benzofurancarboxylic acid methyl ester (6b) showed significant cytotoxic activities against human cancer cell lines. In addition the crystal structures of 7-methoxy-2-benzofurancarboxylic acid methyl ester (7a) has been solved by X-ray structure analysis of single crystals.

  4. Extraction and Analysis of Polyenoic Fatty Acyl Ethyl Esters and Taurine in Mytilus edulis%紫贻贝多烯脂肪酸乙酯及牛磺酸的提取与分析

    Institute of Scientific and Technical Information of China (English)

    张翼; 穆军; 吕红丽; 顾晓洁; 史继诚

    2011-01-01

    For comprehensive utilization of the functional health products from the low-value shells, the poly-unsaturated fatty acyl ethyl esters in Mytilus edulis were extracted by Soxhlet/supersonic extraction and urea complexation, and taurine in the residue after the fatty extraction was extracted by hot water digestion and ionexchange chromatography. The contents of eicosapentaenoic acyl ether ester (EPA-E) and docosahexaenoic acyl ethyl esters (DHA-E) in the product were analyzed by HPLC-DAD. By thin layer chromatography and spectrophotometry, taurine in the crude product was qualitatively and quantitatively analyzed, respectively.The results show that the Mytilus edulis contains rich EPA, DHA and taurine and it is an expectable resource of high-value functional health food.%为综合开发利用低价值贝类中的功能保健品成分,利用索氏/超声提取、尿素包合法提取了紫贻贝中的多烯脂肪酸乙酯,对提油后的残渣利用热水提取、离子交换层析富集的方法提取了其中的牛磺酸,利用高效液相色谱-二极管阵列检测器(HPLC-DAD)分析测定了产品中二十碳五烯酸乙酯(EPA-E)、二十二碳六烯酸乙酯(DHA-E)的含量,利用薄层色谱法、吸光光度法定性定量测定了产品中的牛磺酸,结果显示紫贻贝中含有相当量的多烯脂肪酸乙酯及牛磺酸成分,有望作为高价值功能保健食品的来源.

  5. 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.

  6. Sunscreens derived from paraaminobenzoic acid. Identification and dosage of N-propoxylated ethyl paraaminobenzoates in sun-creams.

    Science.gov (United States)

    Masse, M O; Herpol-Borremans, M; Et, R G; Gleviczky, S

    1982-12-01

    Summary The derivatives of paraaminobenzoic acid listed by the council of Europe (February 1981) as 'Sunscreen agents used to protect the skin'can be determined by simple chromatographie methods (TLC + GLC) described in a previous article. In Amerscreen (R)-P*, (trade name of N-propoxylated ethyl paraaminobenzoate), four constituants are identified by means of nuclear magnetic resonance spectroscopy (NMR) and quantitatively measured by high pressure liquid chromatography (HPLC) in sun-creams.

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

    Science.gov (United States)

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

    2015-11-04

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

  8. Studies on the mechanism of synthesis of ethyl acetate in Kluyveromyces marxianus DSM 5422.

    Science.gov (United States)

    Löser, Christian; Urit, Thanet; Keil, Peter; Bley, Thomas

    2015-02-01

    Kluyveromyces marxianus converts whey-borne sugar into ethyl acetate, an environmentally friendly solvent with many applications. K. marxianus DSM 5422 presumably synthesizes ethyl acetate from acetyl-SCoA. Iron limitation as a trigger for this synthesis is explained by a diminished aconitase and succinate dehydrogenase activity (both enzymes depend on iron) causing diversion of acetyl-SCoA from the tricarboxic acid cycle to ester synthesis. Copper limitation as another trigger for ester synthesis in this yeast refers to involvement of the electron transport chain (all ETC complexes depend on iron and complex IV requires copper). This hypothesis was checked by using several ETC inhibitors. Malonate was ineffective but carboxin partially inhibited complex II and initiated ester synthesis. Antimycin A and cyanide as complexes III and IV inhibitors initiated ester synthesis only at moderate levels while higher concentrations disrupted all respiration and caused ethanol formation. A restricted supply of oxygen (the terminal electron acceptor) also initiated some ester synthesis but primarily forced ethanol production. A switch from aerobic to anaerobic conditions nearly stopped ester synthesis and induced ethanol formation. Iron-limited ester formation was compared with anaerobic ethanol production; the ester yield was lower than the ethanol yield but a higher market price, a reduced number of process stages, a faster process, and decreased expenses for product recovery by stripping favor biotechnological ester production.

  9. Deuterium Exchange in Ethyl Acetoacetate: An Undergraduate GC-MS [Gas Chromatography-Mass Spectroscopy] Experiment

    Science.gov (United States)

    Heinson, C. D.; Williams, J. M.; Tinnerman, W. N.; Malloy, T. B.

    2005-01-01

    The role of ethanol O-d in nullifying the deuterolysis may be demonstrated by determining that transesterification of methyl acetoacetate of the ethyl ester occurs as well as deuterium exchange of the five acetoacetate hydrogens. The significant acidity of the methylene protons in the acetoacetate group, the efficacy of base catalysis, the role of…

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

    DEFF Research Database (Denmark)

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

    2011-01-01

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

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

    Directory of Open Access Journals (Sweden)

    Adewale Adewuyi

    2016-12-01

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

  12. 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.

  13. 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.

  14. SYNTHESIS AND CHARACTERIZATION OF HYPERBRANCHED POLY(ESTER-AMIDE)S BASED ON GALLIC ACID AND DL-2-AMINOBUTYRIC ACID

    Institute of Scientific and Technical Information of China (English)

    Ya-li Su; Xiu-ru Li; Yue-jin Tong; Yue-sheng Li

    2004-01-01

    A novel AB3-type monomer was prepared from gallic acid and DL-2-aminobutyric acid, and used for the synthesis of the biocompatible hyperbranched poly(ester-amide)s by self-polycondensation. The polymers were characterized via FTIR and NMR spectroscopy and thermal analysis, and the average degree of branching of the polymers was estimated to be 0.75.The polymers with abundant acetyl end groups were found to be amorphous with lower intrinsic viscosity, better thermal stability and excellent solubility.

  15. Features of separation on polymeric reversed phase for two classes of higher saturated fatty acids esters

    Science.gov (United States)

    Deineka, V. I.; Lapshova, M. S.; Zakharenko, E. V.; Deineka, L. A.

    2013-11-01

    The principles of sorption on polymeric reversed phase (PRP) YMS C30 for members of the two classes of esters formed by higher saturated fatty acids, i.e., lutein diesters ( I) and triacylglycerols ( II), are investigated. It is shown that the logarithm of the retention factor increases nonlinearly with an increase of the length of the acid radical, although the retention on PRP is higher in the case of I and lower in the case of II, compared to their retention on traditional monomeric reversed phase (MRP) Kromasil-100 5C18; however, the equivalence of the contributions to the retention of I that correspond to an identical change in acids, does not depend on the length of the hydrocarbon radical of the second acid. It is noted that the Van't Hoff plot for PRP contains a curve break, indicating a change in the retention mechanism upon a rise in temperature.

  16. 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.

  17. Effect of caffeic acid esters on carcinogen-induced mutagenicity and human colon adenocarcinoma cell growth.

    Science.gov (United States)

    Rao, C V; Desai, D; Kaul, B; Amin, S; Reddy, B S

    1992-11-16

    Propolis, a honey bee hive product, is thought to exhibit a broad spectrum of activities including antibiotic, antiviral, anti-inflammatory and tumor growth inhibition; some of the observed biological activities may be due to caffeic acid (cinnamic acid) esters that are present in propolis. In the present study we synthesized three caffeic acid esters, namely methyl caffeate (MC), phenylethyl caffeate (PEC) and phenylethyl dimethylcaffeate (PEDMC) and tested them against the 3,2'-dimethyl-4-aminobiphenyl, (DMAB, a colon and mammary carcinogen)-induced mutagenicity in Salmonella typhimurium strains TA 98 and TA 100. Also, the effect of these agents on the growth of human colon adenocarcinoma, HT-29 cells and activities of ornithine decarboxylase (ODC) and protein tyrosine kinase (PTK) was studied. Mutagenicity was induced in Salmonella typhimurium strains TA 98 and TA 100 plus S9 activation using 5 and 10 micrograms DMAB and antimutagenic activities of 0-150 microM MC, 0-60 microM PEC and 0-80 microM PEDMC were determined. The results indicate that MC, PEC and PEDMC were not mutagenic in the Salmonella tester system. DMAB-induced mutagenicity was significantly inhibited with 150 microM MC, 40-60 microM PEC and 40-80 microM PEDMC in both tester systems. Treatment of HT-29 colon adenocarcinoma cells with > 150 microM MC, 30 microM PEC and 20 microM PEDMC significantly inhibited the cell growth and syntheses of RNA, DNA and protein. ODC and PTK activities were also inhibited in HT-29 cells treated with different concentrations of MC, PEC and PEDMC. These results demonstrate that caffeic acid esters which are present in Propolis possess chemopreventive properties when tested in short-term assay systems.

  18. Analytical method for the trace determination of esterified 3- and 2-monochloropropanediol and glycidyl fatty acid esters in various food matrices.

    Science.gov (United States)

    Samaras, Vasilios G; Giri, Anupam; Zelinkova, Zuzana; Karasek, Lubomir; Buttinger, Gerhard; Wenzl, Thomas

    2016-09-30

    Fatty acid esters of 3-monochloro-1,2-propanediol (3-MCPDEs), of 2-monochloro-1,3-propanediol (2-MCPDEs) and of 2,3-epoxy-1-propanol or glycidol (GEs), which are considered to be deleterious to human health, may occur in a broad variety of food samples. A proper risk assessment of those substances requires the availability of robust occurrence data; in this respect concerns have been raised regarding the reliability of results obtained with the currently available methods to determine those substances in processed food. This article presents an indirect analytical procedure for the simultaneous determination of 3-MCPDEs, 2-MCPDEs and GEs in a wide variety of food products after extraction by pressurised liquid extraction (PLE) and determination by gas chromatography mass-spectrometry (GC-MS). For the differentiation of MCPDEs and GEs, the latter were first converted to monobromopropanediol esters (MBPDEs) in acid aqueous solution of sodium bromide. MCPDEs and MBPDEs were then hydrolysed under acidic conditions followed by derivatisation of the released free (non-esterified) form in ethyl acetate with phenyl boronic acid (PBA). Quantification of the analytes was carried out using the isotopic labelled analogues of both MCPDEs and GEs. Limits of detection (LODs) and limits of quantitation (LOQs) were in the range of 7-17mgkg(-1) and 13-31mgkg(-1) respectively, while the working range of the method was between LOQ and 1850mgkg(-1) expressed on fat basis. The developed method was successfully applied for the analysis of the target compounds in more than 650 different food samples covering the following commodities: bread and rolls, fine bakery wares, smoked fish products, fried and roasted meat, potato based snacks and fried potato products, cereal-based snacks and margarines.

  19. 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.

  20. 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.

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

    KAUST Repository

    Batool, Farhat

    2016-11-18

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

  2. 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.)

  3. 40 CFR 721.3025 - Fatty acids C12-18, C18 unsaturated, C12-18 alkyl esters (generic).

    Science.gov (United States)

    2010-07-01

    ..., C12-18 alkyl esters (generic). 721.3025 Section 721.3025 Protection of Environment ENVIRONMENTAL... alkyl esters (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as fatty acids C12-18, C18 unsaturated, C12-18 alkyl esters...

  4. 40 CFR 180.486 - Phosphorothioic acid, 0,0-diethyl 0-(1,2,2,2-tetrachloroethyl) ester; tolerances for residues.

    Science.gov (United States)

    2010-07-01

    ...,2,2,2-tetrachloroethyl) ester; tolerances for residues. 180.486 Section 180.486 Protection of...,2-tetrachloroethyl) ester; tolerances for residues. Tolerances are established permitting the residue of the insecticide phosphorothioic acid, 0,0-diethyl 0-(1,2,2,2-tetrachloroethyl) ester in or...

  5. 40 CFR 721.8350 - 2-Propenoic acid, 7-oxa-bi-cy-clo[4.1.0]hept-3-ylmethyl ester.

    Science.gov (United States)

    2010-07-01

    ...-3-ylmethyl ester. 721.8350 Section 721.8350 Protection of Environment ENVIRONMENTAL PROTECTION... ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance 2-propenoic acid, 7-oxabicyclo hept-3-ylmethyl ester (PMN P-89-31) is subject to reporting...

  6. 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.

  7. Can propolis and caffeic acid phenethyl ester be promising agents against cyclophosphamide toxicity?

    Science.gov (United States)

    Akyol, Sumeyya; Gulec, Mehmet Akif; Erdemli, Haci Kemal; Akyol, Omer

    2016-01-01

    Propolis is a mixture having hundreds of polyphenols including caffeic acid phenethyl ester (CAPE). They have been using in several medical conditions/diseases in both in vitro and in vivo experimental setup. Cyclophosphamide (CP) has been used to treat a broad of malignancies including Hodgkin’s and non-Hodgkin’s lymphoma, Burkitt’s lymphoma, chronic lymphocytic leukemia, Ewing’s sarcoma, breast cancer, testicular cancer, etc. It may cause several side effects after treatment. In this mini review, the protective effects of propolis and CAPE were compared each other in terms of effectiveness against CP-induced injuries. PMID:27069732

  8. 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.

  9. 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.

  10. Preparation and Characterization of Ester from Rosin Acrylic Acid Adduct and Hydroxyethyl Methacrylate

    Institute of Scientific and Technical Information of China (English)

    C.L.Yu; F.A.Zhang

    2007-01-01

    1 Results Rosin is a sort of important renewable resources,which is a foremost product of our country forestry. It has very important meaning to modify the rosin based on its molecule structure and active group, to develop some deep processing products, and to endure with rosin new characteristic[1]. This work uses the rosin and acrylic acid to form rosin adduct, and then reacted with 2-hydroxyethyl methacrylate (HEMA) to form ester under the different condition. The effect of different ratios with the ...

  11. 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.

  12. 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.

  13. 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.

  14. Caffeic acid phenethyl ester (CAPE): correlation of structure and antioxidant properties.

    Science.gov (United States)

    Göçer, Hülya; Gülçin, Ilhami

    2011-12-01

    Caffeic acid phenethyl ester (CAPE), a plant polyphenolic concentrated in honeybee propolis, has been found to be biologically active in a variety of pathways. The aim of this study was to determine the antioxidant activity of CAPE using different methods such as total antioxidant activity by the thiocyanate method, 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid radicals, 1,1-diphenyl-2-picryl-hydrazyl free radicals, N,N-dimethyl-p-phenylenediamine dihydrochloride radicals and superoxide anion radicals scavenging activities, reducing power and ferrous ions (Fe(2+)) chelating activities. CAPE showed 97.9% inhibition on lipid peroxidation of linoleic acid emulsion. On the other hand, butylated hydroxyanisole, butylated hydroxytoluene, α-tocopherol and trolox indicated an inhibition of 87.3, 97.6, 75.3 and 90.3% on peroxidation in the same system, respectively.

  15. 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…

  16. 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.

  17. Chloroindolyl-3-acetic Acid and its Methyl Ester Incorporation of 36Cl in Immature Seeds of Pea and Barley

    DEFF Research Database (Denmark)

    Engvild, Kjeld Christensen

    1974-01-01

    compounds besides Cl−. One compound, present in pea and probably in barley, cochromatographed with a mixture of 4- and 6-chloroindolyl-3-acetic acid methyl esters. Another, detected in pea, but probably not in barley, cochromatographed with a mixture of 4-and 6-chloroindolyl-3-acetic acids....

  18. Synthesis, stability studies, anti-inflammatory activity and ulcerogenicity of morpholinoalkyl ester prodrugs of niflumic acid.

    Science.gov (United States)

    Talath, Sirajunisa; Gadad, Andanappa K

    2006-01-01

    In search for potential prodrugs for anti-inflammatory drug candidates in the niflumate series, novel morpholinoalkyl ester prodrugs of niflumic acid (CAS 4394-00-7) 5a-b were prepared by esterification of appropriate morpholinylalkyl alcohols 3a-b with niflumic acid 4 in the presence of dicyclohexyl carbodiimide (DCC) and catalyst dimethylamino pyridine (DMAP) at 0-5 degrees C. The structures were confirmed by elemental and spectral data (UV, IR, 1H-NMR, 13C-NMR, and EI-MS). The ester prodrugs 5a-b showed better solubility than the parent drug niflumic acid 4 in simulated gastric fluid (SGF) and phosphate buffer (pH 7.4). The in vitro hydrolysis studies were conducted at pH 1.3 (SGF), phosphate buffer (pH 7.4) and in human plasma diluted with phosphate buffer (pH 7.4) at 37+/-0.5 degrees C using HPLC with UV detection. The ester prodrugs 5a-b were quantitatively hydrolyzed to the parent drug niflumic acid 4 by enzymatic and/or chemical means. It is observed that an increase in the carbon chain length rendered the prodrugs 5a-b more stable in phosphate buffer (pH 7.4) than in pH 1.3 (SGF), but they were rapidly hydrolyzed in human plasma at 37+/-0.5 degrees C. They exhibited longer hydrolytic half-lives of 16.11-53.30 h in aqueous buffer solutions (pH 1.3 and 7.4) and 1.63-2.73 min in human plasma, respectively. The title compounds were evaluated in vivo for anti-inflammatory activity in carrageenan induced rat paw oedema model in rats at the doses 45, 90, 150 mg/kg b.w. The test compounds exhibited good anti-inflammatory activity (46.6-53.2 % at the dose of 150 mg/kg b. w.) with respect to niflumic acid (78.7 % at the dose of 90 mg/kg b.w.). The compounds were also screened for in vivo ulcerogenicity, it was observed that the prodrug 5b was significantly less irritating to gastric mucosa than compound 5a and the parent drug niflumic acid 4 following single and chronic oral administration in rats.

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

    Science.gov (United States)

    2005-12-01

    standard DGEBA -based vinyl ester resins and low VOC/HAP resins. 15. SUBJECT TERMS low VOC vinyl esters, styrene, viscosity 16. SECURITY CLASSIFICATION...B) vinyl-ester monomer and (C) styrene (5). Note the definition of m (m = 1 represents the lowest possible value of m for DGEBA -based resins...of vinyl-ester molecular weight and temperature that is required to achieve η = 500 cP for DGEBA -based vinyl esters. ..............22 1 1

  20. Application of hollow fiber supported liquid membrane as a chemical reactor for esterification of lactic acid and ethanol to ethyl lactate

    Energy Technology Data Exchange (ETDEWEB)

    Teerachaiyapat, Thanyarutt; Ramakul, Prakorn [Faculty of Engineering and Industrial Technology, Silpakorn University, Nakhon Pathom (Thailand)

    2016-01-15

    Hollow fiber supported liquid membrane was applied as a reactor to synthesize ethyl lactate from lactic acid. Lactic acid in the feed solution was extracted by tri-n-octylamine (TOA) and stripped by ethanol with p-toluene sulfonic acid acting as the catalyst to form ethyl lactate. Central composite design (CCD) was used to determine the significant factors and their interactions. The response surface was applied for optimization. An optimized yield of 30% was predicted and its validity was evaluated by comparison with experimental results at different concentrations of lactic acid in the feed solution, with good agreement achieved.

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

    NARCIS (Netherlands)

    Hoogenboom, L.A.P.

    2016-01-01

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

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

    Science.gov (United States)

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

    2012-02-01

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

  3. 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.

  4. Antioxidant activity of ferulic acid alkyl esters in a heterophasic system: a mechanistic insight.

    Science.gov (United States)

    Anselmi, Cecilia; Centini, Marisanna; Granata, Paola; Sega, Alessandro; Buonocore, Anna; Bernini, Andrea; Facino, Roberto Maffei

    2004-10-20

    The antioxidant activity of some esters of ferulic acid with the linear fatty alcohols C7, C8 (branched and linear), C9, C11, C12, C13, C15, C16, and C18 has been studied in homogeneous and heterogeneous phases. Whereas in homogeneous phase all of the alkyl ferulates possessed similar radical-scavenging abilities, in rat liver microsomes they showed striking differences, the more effective being C12 (7) (IC50 = 11.03 M), linear C8 (3) (IC50 = 12.40 microM), C13 (8) (IC50 = 18.60 microM), and C9 (5) (IC50 = 19.74 microM), followed by C7 (2), C15 (9), C11 (6), branched C8 (4), C16 (10), and C18 (11) (ferulic acid was the less active, IC50 = 243.84 microM). All of the molecules showed similar partition coefficients in an octanol-buffer system. Three-dimensional studies (NMR in solution, modeling in vacuo) indicate that this behavior might be due to a different anchorage of the molecules with the ester side chain to the microsomal phospholipid bilayer and to a consequent different orientation/positioning of the scavenging phenoxy group outside the membrane surface against the flux of oxy radicals.

  5. Synthesis and fungicidal activity of aryl carbamic acid-5-aryl-2-furanmethyl ester.

    Science.gov (United States)

    Li, Ying; Li, Bao-Ju; Ling, Yun; Miao, Hong-Jian; Shi, Yan-Xia; Yang, Xin-Ling

    2010-03-10

    Chitin, a major structural component of insect cuticle and fungus cell wall but absent in plants and vertebrates, is regarded as a safe and selective target for pest control agents. Chitin synthesis inhibitors (CSIs) have been well-known as insect growth regulators (IGRs) but rarely found as fungicides in agriculture. To find novel CSIs with good activity, benzoylphenylurea, a typical kind of CSIs, was chosen as the lead compound and 26 novel aryl carbamic acid-5-aryl-2-furanmethyl esters were designed by converting the urea linkages of benzoylphenylureas to carbamic acid esters and changing the aniline parts into furanmethyl groups. The title compounds were synthesized and their structures confirmed by IR, (1)H NMR, and elemental analysis. Preliminary insecticidal and fungicidal bioassays were carried out. The results indicated that the title compounds had no insecticidal effect on Culex pipiens pallens and Plutella xylostella Linnaeus , but most compounds exhibited good fungicidal activities against Corynespora cassiicola , Thanatephorus cucumeris , Botrytis cinerea , and Fusarium oxysporum . In particular, compounds V-4, V-6, V-7, and V-8 showed better activities against the four strains than those of the commercialized fungicides. The morphologic result suggested that compound V-21 had disturbed the cell wall formation of C. cassiicola. The results indicated that modification on the urea linkage of benzoylphenylurea was an effective way to discover new candidates for fungicides.

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

    Directory of Open Access Journals (Sweden)

    Paula Pérez-Faginas

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

  7. Effect of fatty acid methyl esters from plastrum testudinis on proliferation of rat bone mesenchymal stem cells

    Institute of Scientific and Technical Information of China (English)

    Yuehua ZHANG; Heping ZENG; Dongfeng CHEN

    2008-01-01

    The ointment of plastrum testudinis was extracted using petroleum ether,ether and dichloromethane sequentially and the extracts were methyl,esteri,fled. The effects on the proliferation of bone marrow mesenchymal stem cells (bMMSCs) were examined by MTT[3,(4,5,dimethylthiazol,2,yl),2,5,diphenyl tetrazolium bromide] assay and flow cytometry analysis. The volatile components of the samples were studied by gas chromatography,mass spectrometry (GC,MS) and high performance liquid chromatography (HPLC). The results show that the methyl,esterified parts can promote the proliferation of stem cells and they all contain palmitic acid methyl ester. Palmitic acid methyl ester can promote proliferation when the concentration was 0.15 μg/μL. It may be concluded that the palmitic acid methyl ester is important for the methyl,esterified parts that have effects on proliferation.

  8. Perennial peanut (Arachis glabrata Benth.) leaves contain hydroxycinnamoyl-CoA:tartaric acid hydroxycinnamoyl transferase activity and accumulate hydroxycinnamoyl-tartaric acid esters.

    Science.gov (United States)

    Sullivan, Michael L

    2014-05-01

    Many plants accumulate hydroxycinnamoyl esters to protect against abiotic and biotic stresses. Caffeoyl esters in particular can be substrates for endogenous polyphenol oxidases (PPOs). Recently, we showed that perennial peanut (Arachis glabrata Benth.) leaves contain PPO and identified one PPO substrate, caftaric acid (trans-caffeoyl-tartaric acid). Additional compounds were believed to be cis- and trans-p-coumaroyl tartaric acid and cis- and trans-feruloyl-tartaric acid, but lack of standards prevented definitive identifications. Here we characterize enzymatic activities in peanut leaves to understand how caftaric acid and related hydroxycinnamoyl esters are made in this species. We show that peanut leaves contain a hydroxycinnamoyl-CoA:tartaric acid hydroxycinnamoyl transferase (HTT) activity capable of transferring p-coumaroyl, caffeoyl, and feruloyl moieties from CoA to tartaric acid (specific activities of 11 ± 2.8, 8 ± 1.8, 4 ± 0.8 pkat mg(-1) crude protein, respectively). The HTT activity was used to make cis- and trans-p-coumaroyl- and -feruloyl-tartaric acid in vitro. These products allowed definitive identification of the corresponding cis- and trans-hydroxycinnamoyl esters extracted from leaves. We tentatively identified sinapoyl-tartaric acid as another major phenolic compound in peanut leaves that likely participates in secondary reactions with PPO-generated quinones. These results suggest hydroxycinnamoyl-tartaric acid esters are made by an acyltransferase, possibly a BAHD family member, in perennial peanut. Identification of a gene encoding HTT and further characterization of the enzyme will aid in identifying determinants of donor and acceptor substrate specificity for this important class of biosynthetic enzymes. An HTT gene could also provide a means by genetic engineering for producing caffeoyl- and other hydroxycinnamoyl-tartaric acid esters in forage crops that lack them.

  9. 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.

  10. Development of N-ferrocenyl(benzoyl)amino-acid esters stationary phase for high performance liquid chromatography.

    Science.gov (United States)

    Zhou, Xiaohua; Li, Xiaole; Cao, Aijuan; Lijun, Qiao; Yu, Ajuan; Zhang, Shusheng; Wu, Yangjie

    2015-11-01

    A new stationary phase for high-performance liquid chromatography was prepared by covalently bonding N-ferrocenyl(benzoyl)amino-acid esters (L(1)) onto silica gel using 3-aminopropyltriethoxysilane as coupling reagent. The structure of new material was characterized by infrared spectroscopy, elemental analysis and thermogravimetric analysis. The chromatographic behavior of the phase was illustrated in reversed-phase (RP) and normal-phase (NP) modes using polycyclic aromatic hydrocarbons (PAHs), aromatics positional isomers, amines, 5-nitroimidazoles, organophosphorus pesticides and phenols as probes. Multiple mechanisms including hydrophobic, hydrogen bonding, π-π, dipole-dipole, charge-transfer and acid-base equilibrium interactions are involved. Thus, multi-interaction mechanisms and mixed-mode separation of the new phase can very likely guarantee its excellent chromatographic performance for the analysis of complex samples. The L(1) AminoSil column was successfully employed for the analysis of organophosphorus pesticides in vegetable.

  11. Comparison of indirect and direct quantification of glycidol fatty acid ester in edible oils.

    Science.gov (United States)

    Shimizu, Masao; Kudo, Naoto; Shiro, Hiroki; Yasunaga, Koichi; Masukawa, Yoshinori; Katsuragi, Yoshihisa; Yasumasu, Takeshi

    2010-01-01

    Two different methods for determining the levels of glycidol fatty acid esters (GEs) in edible oil-the German official indirect method and the direct LC-MS method-are compared. In some cases, the indirect method showed lower GE levels than the direct method. This was investigated using model studies, which revealed two possible causative factors during the acid treatment of the indirect method: (1) incomplete elimination of GE in oil that was high in GEs initially and (2) generation of GEs and/or its relevant compounds in oil that was rich in partial acylglycerol. Both these factors contributed to the subsequent underestimation of GE levels. The above technical limitations of the indirect method found in the present study has led to the inference that the direct method can more precisely determine the GE levels for a wider range of fats and oil products than the indirect method.

  12. Correlation for the estimation of the density of fatty acid esters fuels and its implications. A proposed Biodiesel Cetane Index.

    Science.gov (United States)

    Lapuerta, Magín; Rodríguez-Fernández, José; Armas, Octavio

    2010-09-01

    Biodiesel fuels (methyl or ethyl esters derived from vegetables oils and animal fats) are currently being used as a means to diminish the crude oil dependency and to limit the greenhouse gas emissions of the transportation sector. However, their physical properties are different from traditional fossil fuels, this making uncertain their effect on new, electronically controlled vehicles. Density is one of those properties, and its implications go even further. First, because governments are expected to boost the use of high-biodiesel content blends, but biodiesel fuels are denser than fossil ones. In consequence, their blending proportion is indirectly restricted in order not to exceed the maximum density limit established in fuel quality standards. Second, because an accurate knowledge of biodiesel density permits the estimation of other properties such as the Cetane Number, whose direct measurement is complex and presents low repeatability and low reproducibility. In this study we compile densities of methyl and ethyl esters published in literature, and proposed equations to convert them to 15 degrees C and to predict the biodiesel density based on its chain length and unsaturation degree. Both expressions were validated for a wide range of commercial biodiesel fuels. Using the latter, we define a term called Biodiesel Cetane Index, which predicts with high accuracy the Biodiesel Cetane Number. Finally, simple calculations prove that the introduction of high-biodiesel content blends in the fuel market would force the refineries to reduce the density of their fossil fuels.

  13. Separation of Long and Short Chain Fatty Acids as Naphthacyl and Substituted Phenacyl Esters by High Performance Liquid Chromatography.

    Science.gov (United States)

    High performance liquid chromatography of various C2 - C24 fatty acids was run on their p-bromophenacyl, p-nitrophenacyl, p-chlorophenacyl, and 2--naphthacyl esters. All the separations were accomplished using reversed phase columns with the eluent consisting of an acetonitrile:water gradient. For all derivatives tested the separations were well defined and analogous although certain esters eluted together as one peak. Quantitative results indicate that the limit of detection in the present study was two picograms of n-caproic acid and 10 picograms of

  14. A Novel Method for the Synthesis of Bioactive Benzimidazolyl-Phenoxyacetic Acid O-Acetylglucosyl Saccharide Esters

    Institute of Scientific and Technical Information of China (English)

    2006-01-01

    A novel method of synthesis of nitro or trifluoromethyl substituted benzimidazolyl-phenoxyacetic acid O-acetylglucosyl saccharide esters by the reaction of O-acetylglucosyl bromide with substituted benzimidazolyl -phenoxyacetic acid at room temperature was developed. 4-dimethylaminopyridine (DMAP) was used as catalyst, triethylamine (Et3N) was used as deacid reagent, three saccharide esters were synthesized in the system of DMAP/ Et3N. The catalytic mechanism of DMAP/Et3N was discussed. The results show that DMAP is an effective catalyst, the yields can reach 50%. The test indicates that the title compounds show better antiplantviral activity.

  15. 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.

  16. Synthesis and pharmacological evaluation of some dual-acting amino-alcohol ester derivatives of flurbiprofen and 2-[1,1'-biphenyl-4-yl]acetic acid: a potential approach to reduce local gastrointestinal toxicity.

    Science.gov (United States)

    Halen, Parmeshwari Kuldeep Kumar; Chagti, Kewal Krishna; Giridhar, Rajani; Yadav, Mange Ram

    2006-11-01

    The search for safer non-steroidal anti-inflammatory drugs (NSAIDs) continues with the failure of anticipated 'ideal' anti-inflammatory agents, the coxibs, on long-term usage. Increased gastric motility and acidity due to the free carboxy group are involved in the etiology of gastric toxicity, common to conventional NSAIDs. Keeping this fact in mind, it was planned to modify some of the conventional NSAIDs to amino-alcohol ester derivatives, which satisfied the structural requirements for these compounds to possess anticholinergic activity in the intact form. Besides blocking the acidic carboxylic group, incorporation of anticholinergic acivity in these molecules was expected to reduce the gastric toxicity by decreasing gastric acid secretion and motility. Synthesis and pharmacological evaluation of six different N,N-disubstituted amino-ethyl ester derivatives, structurally resembling the amino-alcohol ester class of anticholinergic agents, each for [1,1'-biphenyl]-4-acetic acid (3) and flurbiprofen (10), have been reported as potential substitutes for these NSAIDs, with improved therapeutic profile. All the ester derivatives were found to have sufficient chemical stability in buffers (pH 2.0 and 7.4), ensuring them to be absorbed as intact moieties from the gastrointestinal tract. A significant reduction in ulcerogenic potency in comparison to the parent drugs with a slightly higher anti-inflammatory potency suggests that the majority of these candidates have an improved therapeutic profile over their parent drugs. Hence, a promising novel approach, different from the conventional prodrug concept, has been successfully worked out to overcome the local gastric toxicity, yielding therapeutically better compounds for long-term oral anti-inflammatory therapy.

  17. Ultrasound in fatty acid chemistry: synthesis of a 1-pyrroline fatty acid ester isomer from methyl ricinoleate.

    Science.gov (United States)

    Lie Ken Jie, M S; Syed-Rahmatullah, M S; Lam, C K; Kalluri, P

    1994-12-01

    A novel 1-pyrroline fatty acid ester isomer (viz. 8-5-hexyl-1-pyrrolin-2-yl) octanoate) has been synthesized from methyl ricinoleate by two routes with an overall yield of 42 and 30%, respectively. Most of the reactions are carried out under concomitant ultrasonic irradiation (20 KHz, ca. 53 watts/cm2). Under such a reaction condition, the reaction time is considerably shortened, and product yields are high. Dehydrobromination under concomitant ultrasonic irradiation of methyl 9, 10-dibromo-12-hydroxyoctadecanoate with KOH in EtOH furnishes methyl 12-hydroxy-9-octadecynoate (66%) within 15 min. Hydration of the latter under ultrasound with mercury(II)acetate in aqueous tetrahydrofuran yields exclusively methyl 12-hydroxy-9-oxo-octadecanoate (95%) in 30 min. The hydroxy group in the latter compound is transformed to the azido function via the mesylate, and treatment of the azido-oxo intermediate (methyl 12-azido-9-oxooctadecanoate) with Ph3P under ultrasonic irradiation furnishes the requisite 1-pyrroline fatty acid ester (77%). The same azido-oxo intermediate has also been obtained by the oxidation of methyl 12-azido-9-cis-octadecenoate using benzoquinone and a catalytic amount of Pd(II)chloride in aqueous tetrahydrofuran under concomitant ultrasonic irradiation (90 min) to give the product in 45% yield. The latter reaction does not take place even under prolonged silent stirring of the reaction mixture.

  18. Fatty acid composition in major depression: decreased omega 3 fractions in cholesteryl esters and increased C20: 4 omega 6/C20:5 omega 3 ratio in cholesteryl esters and phospholipids.

    Science.gov (United States)

    Maes, M; Smith, R; Christophe, A; Cosyns, P; Desnyder, R; Meltzer, H

    1996-04-26

    Recently, there were some reports that major depression may be accompanied by alterations in serum total cholesterol, cholesterol ester and omega 3 essential fatty acid levels and by an increased C20: 4 omega 6/C20: 5 omega 3, i.e., arachidonic acid/eicosapentaenoic, ratio. The present study aimed to examine fatty acid composition of serum cholesteryl esters and phospholipids in 36 major depressed, 14 minor depressed and 24 normal subjects. Individual saturated (e.g., C14:0; C16:0, C18:0) and unsaturated (e.g., C18:1, C18:2, C20:4) fatty acids in phospholipid and cholesteryl ester fractions were assayed and the sums of the percentages of omega 6 and omega 3, saturated, branched chain and odd chain fatty acids, monoenes as well as the ratios omega 6/omega 3 and C20:4 omega 6/C20:5 omega 3 were calculated. Major depressed subjects had significantly higher C20:4 omega 6/C20:5 omega 3 ratio in both serum cholesteryl esters and phospholipids and a significantly increased omega 6/omega 3 ratio in cholesteryl ester fraction than healthy volunteers and minor depressed subjects. Major depressed subjects had significantly lower C18:3 omega 3 in cholesteryl esters than normal controls. Major depressed subjects showed significantly lower total omega 3 polyunsaturated fatty acids in cholesteryl esters and significantly lower C20:5 omega 3 in serum cholesteryl esters and phospholipids than minor depressed subjects and healthy controls. These findings suggest an abnormal intake or metabolism of essential fatty acids in conjunction with decreased formation of cholesteryl esters in major depression.

  19. 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.

  20. 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.

  1. V-shaped crystalline structures of di-n-alkyl esters of phosphoric acid.

    Science.gov (United States)

    Thünemann, Andreas F; Kurth, Dirk G; Beinhoff, Matthias; Bienert, Ralf; Schulz, Burkhard

    2006-06-20

    We prepared crystals of di-n-alkyl esters of phosphoric acid with chain lengths of n = 10, 12, 14, 16, and 18. These were characterized by single-crystal X-ray analysis and differential scanning calorimetry (DSC). It was found that the alkyl chains are in an extended all-trans conformation and aligned close to perpendicular, forming V-shaped molecules. This is in strong contrast to the typical arrangement of the alkyl chains of phospholipids where the two alkyl chains are arranged parallel in the same direction (e.g., tuning fork configuration in bilayers). Additionally, it was found that the arrangement of the V-shaped molecules of the di-n-alkyl esters in neighboring stacks of the lamellar crystals is antiparallel for short chain lengths (n = 10 and 12) and parallel for the longer (n = 14 and 16). DSC reveals that the melting of the crystals increases systematically with increasing chain lengths from 48 to 82 degrees C. The contribution of each methylene group to the melting enthalpy (70-133 kJ/mol) is independent of the chain length (3.9 kJ per mol CH2).

  2. 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.

  3. 乙酸乙酯酯缩合法合成乙酰乙酸乙酯的热力学分析%Thermodynamics analysis of ethyl acetoacetate synthesis from ethyl acetate by ester condensation

    Institute of Scientific and Technical Information of China (English)

    李丹; 丁同梅; 田恒水

    2016-01-01

    The formation enthalpy, Gibbs free energy and equilibrium constant for the reaction of ethyl acetate condensation to ethyl acetoacetatewere estimated by Benson group contribution method and Joback method. The results showed that, in 25 to 240℃, the formation enthalpy is positive, which indicated that the reaction is endothermic, and the heat absorption capacity decreases with the rise of temperature; the Gibbs free energy is positive, which indicated the reaction could not occur spontaneously; and the equilibrium constant is small but increases with the rise of temperature. So it required adding suitable catalysts to let the reaction take place smoothly, raising the reaction temperature to increase the conversion, or removing the products from the reaction system to promote the positive reaction.%用Benson基团贡献法和Joback法对乙酸乙酯酯缩合法生成乙酰乙酸乙酯反应的焓变,吉布斯自由能和反应平衡常数进行了计算与分析。结果显示,在25~240℃内,反应的焓变均为正,说明此反应为吸热反应,随着反应温度的升高吸热量减少;反应的吉布斯自由能一直为正,理论上是不能自发进行的;该反应的平衡常数很小,但是随着温度的升高,平衡常数相应有所增大。要使反应顺利进行需加入适当的催化剂,而为了提高反应的转化率,可以采取升高反应温度,或在反应过程中移走生成物的手段使反应不断向所需方向进行。

  4. Identification and quantitation of urinary dicarboxylic acids as their dicyclohexyl esters in disease states by gas chromatography mass spectrometry.

    Science.gov (United States)

    Norman, E J; Berry, H K; Denton, M D

    1979-12-01

    Clinical studies were conducted by gas chromatography mass spectrometry selected ion monitoring of urinary dicarboxylic acids as dicyclohexyl esters. The dicyclohexyl esters of the dicarboxylic acids give characteristic electron impact mass spectra suitable for selected ion monitoring. The mass spectra exhibit a prominent acid + 1H ion and an (acid + 1H)-H2O ion for use as quantitating and confirming ions. The cyclohexyl esters are stable for days at room temperature and have excellent chromatographic properties. Dicarboxylic acid quantitation is performed within one hour using only 50 microliter of unpurified urine. A rapid method specifically for methylmalonic acid quantitation is described which has assisted physicians in the diagnosis of pernicious anemia and methylmalonic aciduria. This procedure is applicable for screening urinary organic acids for detection of inborn errors of metabolism. The detection of a child with elevated medium length dicarboxylic acids in the terminal urine specimen is reported. This condition, previously described as an inborn error, is attributed to a terminal event. Finally, an increase in urinary succinic acid paralleling putrescine levels is described during a response to cancer chemotherapy.

  5. 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.

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

    Science.gov (United States)

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

    2013-02-01

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

  7. Preparation of five 3-MCPD fatty acid esters and the effects of their chemical structures on acute oral toxicity in Swiss mice

    Science.gov (United States)

    Fatty acid esters of 3-monochloro-1, 2-propanediol (3-MCPDEs), including 1-stearic, 1-oleic, 1-linoleic, 1-linoleic-2-palmitic and 1-palmitic-2-linoleic acid esters, were synthetized and examined for their acute oral toxicities in Swiss mice. 3-MCPDEs were obtained through the reaction of 3-MCPD and...

  8. 40 CFR 721.1729 - Boric acid (H3BO3), mixed esters with polyethylene glycol mono-Bu ether and polyethylene glycol...

    Science.gov (United States)

    2010-07-01

    ... polyethylene glycol mono-Bu ether and polyethylene glycol mono Me ether. 721.1729 Section 721.1729 Protection... acid (H3BO3), mixed esters with polyethylene glycol mono-Bu ether and polyethylene glycol mono Me ether... identified as boric acid (H3BO3), mixed esters with polyethylene glycol mono-Bu ether and......

  9. 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.

  10. 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....

  11. 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.

  12. 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.

  13. 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.

  14. Fatty acid alkyl esters presence in olive oil vs. organoleptic assessment.

    Science.gov (United States)

    Gómez-Coca, R B; Moreda, W; Pérez-Camino, M C

    2012-12-01

    The scientific work on the authenticity and quality of olive oil is an ever-growing area. Olive oil genuineness is not only valuable for the producers, but also for the consumers who expect an actual correspondence between the products they purchase and the information on the packaging labels. Sometimes oil's rejection by consumers is just a matter of taste, sometimes is a more objective question. Low quality olive oils with weak organoleptic defects are the targets of illegal blends that can be detected by determining the content of fatty acid alkyl esters (FAAEs). In this line we have established a relationship between the FAAEs concentration of olive oils and their sensory classification. Besides, a connection between the presence of large quantities of FAAEs and fermentative organoleptic defects has been proven.

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

    Science.gov (United States)

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

    2015-06-01

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

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

    Directory of Open Access Journals (Sweden)

    Haci Kemal Erdemli

    2015-12-01

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

  17. Antiviral properties of caffeic acid phenethyl ester and its potential application.

    Science.gov (United States)

    Erdemli, Hacı Kemal; Akyol, Sumeyya; Armutcu, Ferah; Akyol, Omer

    2015-01-01

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

  18. Future opportunities in preventing ototoxicity: Caffeic acid phenethyl ester may be a candidate (Review).

    Science.gov (United States)

    Akyol, Sumeyya; Isik, Bunyamin; Altuntas, Aynur; Erden, Gonul; Cakmak, Ozlem; Kurşunlu, S Fatih; Adam, Bahattin; Akyol, Omer

    2015-09-01

    Caffeic acid phenethyl ester (CAPE) is an important active component of propolis, which is derived from honeybee hives. It has received increasing attention in a variety of medical and pharmaceutical research, due to its anti‑oxidant, antiproliferative, anti‑inflammatory, antiviral and antifungal activity, in addition to its antineoplastic properties. Besides the use of CAPE as an antioxidant and anti‑inflammatory agent in a number of in vivo studies of ear disease, its beneficial effects have been reported in the treatment of cancer, arthritis, allergies, heart disease, diabetes, kidney disease, liver disease and neurological disease. CAPE influences a number of biochemical pathways, as well as several targets involved in ear diseases, in particular, in ototoxicity. The protective effects of CAPE in ototoxicity, which may be induced by a number factors, including lipopolysaccharides, hydrogen peroxide and streptomycin, are evaluated and discussed in the present review.

  19. Caffeic acid phenethyl ester: its protective role against certain major eye diseases.

    Science.gov (United States)

    Akyol, Sumeyya; Ugurcu, Veli; Balci, Mehmet; Gurel, Ayse; Erden, Gonul; Cakmak, Ozlem; Akyol, Omer

    2014-11-01

    As an effective compound found mainly in the honeybee product propolis, caffeic acid phenethyl ester (CAPE) has been commonly utilized as a medicine and remedial agent, in a number of countries. Specifically, it might inhibit nuclear factor kappa B at micromolar concentrations and demonstrate antioxidant, antineoplastic, antiproliferative, cytostatic, antiviral, antibacterial, antifungal, and anti-inflammatory features. This review article summarizes the recent progress regarding the favorable effects of CAPE on a number of eye disease models, including cataract and posterior capsule opacification, corneal diseases, retina and optic nerve-related diseases, ischemia/reperfusion injury of retina, inflammation and infection-related diseases. CAPE has been found to exhibit promising efficacy, with minimal adverse effects, in animal and cell culture studies of several eye diseases.

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

    Science.gov (United States)

    Haq, I; Muhammad, A; Hameed, U

    2014-01-01

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