Science.gov

Sample records for acid acetoxymethyl ester

  1. Cytosolic and mitochondrial [Ca2+] in whole hearts using indo-1 acetoxymethyl ester: effects of high extracellular Ca2+.

    PubMed Central

    Schreur, J H; Figueredo, V M; Miyamae, M; Shames, D M; Baker, A J; Camacho, S A

    1996-01-01

    Assessment of free cytosolic [Ca2+] ([Ca2+]c) using the acetoxymethyl ester (AM) form of indo-1 may be compromised by loading of indo-1 into noncytosolic compartments, primarily mitochondria. To determine the fraction of noncytosolic fluorescence in whole hearts loaded with indo-1 AM, Mn2+ was used to quench cytosolic fluorescence. Residual (i.e., noncytosolic) fluorescence was subtracted from the total fluorescence before calculating [Ca2+]c. Noncytosolic fluorescence was used to estimate mitochondrial [Ca2+]. In hearts paced at 5 Hz (N = 17), noncytosolic fluorescence was 0.61 +/- 0.06 and 0.56 +/- 0.07 of total fluorescence at lambda 385 and lambda 456, respectively. After taking into account noncytosolic fluorescence, systolic and diastolic [Ca2+]c was 673 +/- 72 and 132 +/- 9 nM, respectively, noncytosolic [Ca2+] was 183 +/- 36 nM and increased to 272 +/- 12 when extracellular Ca2+ was increased from 2 to 6 mM. This increase in noncytosolic [Ca2+] was inhibited by ruthenium red, a blocker of Ca2+ uptake by mitochondria. We conclude that cytosolic and mitochondrial [Ca2+] can be determined in whole hearts loaded with indo-1 AM by using Mn2+ to quench cytosolic fluorescence. PMID:8744296

  2. Non-Invasive Microbial Metabolic Activity Sensing at Single Cell Level by Perfusion of Calcein Acetoxymethyl Ester

    PubMed Central

    Krämer, Christina E. M.; Singh, Abhijeet; Helfrich, Stefan; Grünberger, Alexander; Wiechert, Wolfgang; Nöh, Katharina; Kohlheyer, Dietrich

    2015-01-01

    Phase contrast microscopy cannot give sufficient information on bacterial metabolic activity, or if a cell is dead, it has the fate to die or it is in a viable but non-growing state. Thus, a reliable sensing of the metabolic activity helps to distinguish different categories of viability. We present a non-invasive instantaneous sensing method using a fluorogenic substrate for online monitoring of esterase activity and calcein efflux changes in growing wild type bacteria. The fluorescent conversion product of calcein acetoxymethyl ester (CAM) and its efflux indicates the metabolic activity of cells grown under different conditions at real-time. The dynamic conversion of CAM and the active efflux of fluorescent calcein were analyzed by combining microfluidic single cell cultivation technology and fluorescence time lapse microscopy. Thus, an instantaneous and non-invasive sensing method for apparent esterase activity was created without the requirement of genetic modification or harmful procedures. The metabolic activity sensing method consisting of esterase activity and calcein secretion was demonstrated in two applications. Firstly, growing colonies of our model organism Corynebacterium glutamicum were confronted with intermittent nutrient starvation by interrupting the supply of iron and carbon, respectively. Secondly, bacteria were exposed for one hour to fatal concentrations of antibiotics. Bacteria could be distinguished in growing and non-growing cells with metabolic activity as well as non-growing and non-fluorescent cells with no detectable esterase activity. Microfluidic single cell cultivation combined with high temporal resolution time-lapse microscopy facilitated monitoring metabolic activity of stressed cells and analyzing their descendants in the subsequent recovery phase. Results clearly show that the combination of CAM with a sampling free microfluidic approach is a powerful tool to gain insights in the metabolic activity of growing and non

  3. Synthesis and utility of fluorogenic acetoxymethyl ethers†

    PubMed Central

    Lavis, Luke D.; Chao, Tzu-Yuan

    2011-01-01

    Phenolic fluorophores such as fluorescein, Tokyo Green, resorufin, and their derivatives are workhorses of biological science. Acylating the phenolic hydroxyl group(s) in these fluorophores masks their fluorescence. The ensuing ester is a substrate for cellular esterases, which can restore fluorescence. These esters are, however, notoriously unstable to hydrolysis, severely compromising their utility. The acetoxymethyl (AM) group is an esterase-sensitive motif that can mask polar functionalities in small molecules. Here, we report on the use of AM ether groups to mask phenolic fluorophores. The resulting profluorophores have a desirable combination of low background fluorescence, high chemical stability, and high enzymatic reactivity, both in vitro and in cellulo. These simple phenyl ether-based profluorophores could supplement or supplant the use of phenyl esters for imaging biochemical and biological systems. PMID:21394227

  4. Synthesis of pyromellitic acid esters

    NASA Technical Reports Server (NTRS)

    Fedorova, V. A.; Donchak, V. A.; Martynyuk-Lototskaya, A. N.

    1985-01-01

    The ester acids necessary for studyng the thermochemical properties of pyromellitic acid (PMK)-based peroxides were investigated. Obtaining a tetramethyl ester of a PMK was described. The mechanism of an esterification reaction is discussed, as is the complete esterification of PMK with primary alcohol.

  5. Fumaric acid esters in dermatology

    PubMed Central

    Wollina, Uwe

    2011-01-01

    Fumaric acid esters (FAE) are substances of interest in dermatology. FAE exert various activities on cutaneous cells and cytokine networks. So far only a mixture of dimethylfumarate (DMF) and three salts of monoethylfumarate (MEF) have gained approval for the oral treatment of moderate-to-severe plaque-type psoriasis in Germany. DMF seems to be the major active component. There is evidence that FAE are not only effective and safe in psoriasis but granulomatous non-infectious diseases like granuloma annulare, necrobiosis lipoidica and sarcoidosis. In vitro and animal studies suggest some activity in malignant melanoma as well. PMID:23130241

  6. 21 CFR 172.859 - Sucrose fatty acid esters.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 3 2012-04-01 2012-04-01 false 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...

  7. Carboxylic Acid Esters as Substrates of Cholinesterases

    NASA Astrophysics Data System (ADS)

    Brestkin, A. P.; Rozengart, E. V.; Abduvakhabov, A. A.; Sadykov, A. A.

    1983-10-01

    Data on the kinetics of the hydrolysis of various carboxylic acid esters by two main types of cholinesterases — acetylcholinesterase from human erythrocytes and butyrylcholinesterase from horse blood serum — are surveyed. It is shown that the rate of enzyme hydrolysis depends significantly on the structure of the acyl part of the ester molecule, the nature of the ester heteroatom, the structure of the alcohol component, and particularly the structure of the onium group. Esters based on natural products are of special interest as specific substrates of these enzymes. The role of the productive and non-productive sorption of the substrates in enzyme catalysis is demonstrated. The bibliography includes 81 references.

  8. Lipid encapsulated docosahexaenoic acid methyl ester

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Encapsulation of structurally sensitive compounds within a solid lipid matrix provides a barrier to prooxidant compounds and effectively limits the extent of oxidative degradation. Encapsulated docosahexaenoic acid (DHA) methyl ester was examined as a model compound for functional foods and feeds. S...

  9. 40 CFR 721.10685 - Phosphoric acid, mixed esters (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Phosphoric acid, mixed esters (generic... Specific Chemical Substances § 721.10685 Phosphoric acid, mixed esters (generic). (a) Chemical substance... phosphoric acid, mixed esters (PMN P-13-170) is subject to reporting under this section for the...

  10. 40 CFR 721.10431 - Phosphoric acid esters (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Phosphoric acid esters (generic). 721... Substances § 721.10431 Phosphoric acid esters (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substances identified generically as phosphoric acid esters (PMNs...

  11. 40 CFR 721.1732 - Nitrobenzoic acid octyl ester.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 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...

  12. 40 CFR 721.4215 - Hexanedioic acid, diethenyl ester.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 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...

  13. 40 CFR 721.4158 - Hexadecanoic acid, ethenyl ester.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 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...

  14. 40 CFR 721.1732 - Nitrobenzoic acid octyl ester.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 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...

  15. 40 CFR 721.10431 - Phosphoric acid esters (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Phosphoric acid esters (generic). 721... Substances § 721.10431 Phosphoric acid esters (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substances identified generically as phosphoric acid esters (PMNs...

  16. 40 CFR 721.1732 - Nitrobenzoic acid octyl ester.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 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...

  17. 40 CFR 721.1732 - Nitrobenzoic acid octyl ester.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 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...

  18. 40 CFR 721.5310 - Neononanoic acid, ethenyl ester.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 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...

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

    Code of Federal Regulations, 2010 CFR

    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.

    Code of Federal Regulations, 2010 CFR

    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 721.1732 - Nitrobenzoic acid octyl ester.

    Code of Federal Regulations, 2010 CFR

    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...

  2. 40 CFR 721.4158 - Hexadecanoic acid, ethenyl ester.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 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...

  3. 40 CFR 721.10664 - Alkenedioic acid dialkyl ester, reaction products with alkenoic acid alkyl esters and diamine...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ..., reaction products with alkenoic acid alkyl esters and diamine (generic). 721.10664 Section 721.10664... SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10664 Alkenedioic acid dialkyl ester, reaction products with alkenoic acid alkyl esters and diamine (generic)....

  4. 40 CFR 721.10664 - Alkenedioic acid dialkyl ester, reaction products with alkenoic acid alkyl esters and diamine...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ..., reaction products with alkenoic acid alkyl esters and diamine (generic). 721.10664 Section 721.10664... SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10664 Alkenedioic acid dialkyl ester, reaction products with alkenoic acid alkyl esters and diamine (generic)....

  5. Affinity labelling enzymes with esters of aromatic sulfonic acids

    DOEpatents

    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.

  6. Plant-mediated stereoselective biotransformation of phenylglyoxylic acid esters.

    PubMed

    Maczka, Wanda Krystyna; Grabarczyk, Małgorzata; Wińska, Katarzyna; Anioł, Mirosław

    2014-01-01

    Enantioselective reduction of the carbonyl group of three phenylglyoxylic acid esters (methyl, ethyl, and n-propyl esters, 2-4) was conducted using blended plant materials (roots of carrot, beetroot, celeriac and parsley; apple). All used biocatalysts transformed these esters to the corresponding mandelic acid esters with high yield, preferably into the respective R-enantiomer. Butanedione addition improved the enantioselectivity of the reaction. PMID:25265851

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

    DOEpatents

    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.

  8. 40 CFR 721.8660 - Propionic acid methyl ester (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 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...

  9. 40 CFR 721.8660 - Propionic acid methyl ester (generic).

    Code of Federal Regulations, 2010 CFR

    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...

  10. 40 CFR 721.2950 - Carboxylic acid glycidyl esters.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 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...

  11. 40 CFR 721.2950 - Carboxylic acid glycidyl esters.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 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...

  12. 40 CFR 721.3110 - Polycarboxylic acid ester (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 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...

  13. 40 CFR 721.2950 - Carboxylic acid glycidyl esters.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 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...

  14. 40 CFR 721.3110 - Polycarboxylic acid ester (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 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...

  15. 40 CFR 721.2950 - Carboxylic acid glycidyl esters.

    Code of Federal Regulations, 2010 CFR

    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...

  16. 40 CFR 721.3110 - Polycarboxylic acid ester (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 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...

  17. 40 CFR 721.3110 - Polycarboxylic acid ester (generic).

    Code of Federal Regulations, 2010 CFR

    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...

  18. Activated sludge degradation of adipic acid esters.

    PubMed Central

    Saeger, V W; Kalley, R G; Hicks, O; Tucker, E S; Mieure, J P

    1976-01-01

    The biodegradability of three aliphatic adipic acid diesters and a 1,3-butylene glycol adipic acid polyester was determined in acclimated, activated sludge systems. Rapid primary biodegradation from 67 to 99+% was observed at 3- and 13-mg/liter feed levels for di-n-hexyl adipate, di(2-ethylhexyl) adipate, and di(heptyl, nonyl) adipate in 24 h. When acclimated, activated sludge microorganisms were employed as the seed for two carbon dioxide evolution procedures, greater than 75% of the theoretical carbon dioxide was evolved for the three diesters and the polyester in a 35-day test period. The essentially complete biodegradation observed in these studies suggests that these esters would not persist when exposed to similar mixed microbial populations in the environment. PMID:1275494

  19. 40 CFR 721.10255 - Vinyl carboxylic acid ester (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Vinyl carboxylic acid ester (generic... Specific Chemical Substances § 721.10255 Vinyl carboxylic acid ester (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as...

  20. 40 CFR 721.10255 - Vinyl carboxylic acid ester (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Vinyl carboxylic acid ester (generic... Specific Chemical Substances § 721.10255 Vinyl carboxylic acid ester (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as...

  1. 40 CFR 721.10255 - Vinyl carboxylic acid ester (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Vinyl carboxylic acid ester (generic... Specific Chemical Substances § 721.10255 Vinyl carboxylic acid ester (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as...

  2. MICROBIAL TRANSFORMATION OF ESTERS OF CHLORINATED CARBOXYLIC ACIDS

    EPA Science Inventory

    Two groups of compounds were selected for microbial transformation studies. In the first group were carboxylic acid esters having a fixed aromatic moiety and an increasing length of the alkyl component. Ethyl esters of chlorine-substituted carboxylic acids were in the second grou...

  3. Preparation of .alpha.,.beta.-unsaturated carboxylic acids and esters

    DOEpatents

    Gogate, Makarand Ratnakar; Spivey, James Jerry; Zoeller, Joseph Robert

    1998-01-01

    Disclosed is a process for the preparation of .alpha.,.beta.-unsaturated carboxylic acids and esters thereof which comprises contacting formaldehyde or a source of formaldehyde with a carboxylic acid, ester or anhydride in the presence of a catalyst comprising an oxide of niobium.

  4. Preparation of {alpha},{beta}-unsaturated carboxylic acids and esters

    DOEpatents

    Gogate, M.R.; Spivey, J.J.; Zoeller, J.R.

    1998-09-15

    Disclosed is a process for the preparation of {alpha},{beta}-unsaturated carboxylic acids and esters thereof which comprises contacting formaldehyde or a source of formaldehyde with a carboxylic acid, ester or anhydride in the presence of a catalyst comprising an oxide of niobium.

  5. Adamantane dicarboxylic acid esters as possible additives to semisolid lubricants

    SciTech Connect

    Novikova, I.A.; Dolgopolova, T.N.; Apryatkin, A.D.

    1993-12-31

    The high efficiency of adamantane carboxylic acid esters as antiwear additives to lubricating compounds based on polysiloxane liquids has been demonstrated. Dibutyl and dihexyl esters of 5,7-dimethyl-1,3-adainantane dicarboxylic acid, increasing by several factors the efficiency of a semisolid lubricant based on liquid methyldichlorophenylsiloxane, have been synthesized and characterized.

  6. 40 CFR 721.10125 - Alkenedioic acid, dialkyl ester, reaction products with polyaminocarbomonocycle and alkenoic acid...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    .... (1) The chemical substances identified generically as alkenedioic acid, dialkyl ester, reaction..., reaction products with polyaminocarbomonocycle and alkenoic acid alkyl ester (generic). 721.10125 Section... CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific...

  7. 40 CFR 721.10125 - Alkenedioic acid, dialkyl ester, reaction products with polyaminocarbomonocycle and alkenoic acid...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    .... (1) The chemical substances identified generically as alkenedioic acid, dialkyl ester, reaction..., reaction products with polyaminocarbomonocycle and alkenoic acid alkyl ester (generic). 721.10125 Section... CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific...

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

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    .... (1) The chemical substances identified generically as alkenedioic acid, dialkyl ester, reaction..., reaction products with polyaminocarbomonocycle and alkenoic acid alkyl ester (generic). 721.10125 Section... CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific...

  9. 40 CFR 721.10125 - Alkenedioic acid, dialkyl ester, reaction products with polyaminocarbomonocycle and alkenoic acid...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    .... (1) The chemical substances identified generically as alkenedioic acid, dialkyl ester, reaction..., reaction products with polyaminocarbomonocycle and alkenoic acid alkyl ester (generic). 721.10125 Section... CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific...

  10. 40 CFR 721.10125 - Alkenedioic acid, dialkyl ester, reaction products with polyaminocarbomonocycle and alkenoic acid...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    .... (1) The chemical substances identified generically as alkenedioic acid, dialkyl ester, reaction..., reaction products with polyaminocarbomonocycle and alkenoic acid alkyl ester (generic). 721.10125 Section... CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific...

  11. 40 CFR 721.10679 - Carboxylic acid, substituted alkylstannylene ester, reaction products with inorganic acid tetra...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... alkylstannylene ester, reaction products with inorganic acid tetra alkyl ester (generic). 721.10679 Section 721... SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10679 Carboxylic acid, substituted alkylstannylene ester, reaction products with inorganic acid tetra alkyl...

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

    PubMed

    Layton, Donovan S; Trinh, Cong T

    2016-08-01

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

  13. 21 CFR 172.854 - Polyglycerol esters of fatty acids.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ...) Polyglycerol esters of a mixture of stearic, oleic, and coconut fatty acids are used as a cloud inhibitor in... used at a level not in excess of the amount required to perform its cloud-inhibiting effect. Oleic...

  14. ESTIMATION OF CARBOXYLIC ACID ESTER HYDROLYSIS RATE CONSTANTS

    EPA Science Inventory

    SPARC chemical reactivity models were extended to calculate hydrolysis rate constants for carboxylic acid esters from molecular structure. The energy differences between the initial state and the transition state for a molecule of interest are factored into internal and external...

  15. Fatty acid alcohol ester-synthesizing activity of lipoprotein lipase.

    PubMed

    Tsujita, T; Sumiyoshi, M; Okuda, H

    1999-12-01

    The fatty acid alcohol ester-synthesizing activity of lipoprotein lipase (LPL) was characterized using bovine milk LPL. Synthesizing activities were determined in an aqueous medium using oleic acid or trioleylglycerol as the acyl donor and equimolar amounts of long-chain alcohols as the acyl acceptor. When oleic acid and hexadecanol emulsified with gum arabic were incubated with LPL, palmityl oleate was synthesized, in a time- and dose-dependent manner. Apo-very low density lipoprotein (apoVLDL) stimulated LPL-catalyzed palmityl oleate synthesis. The apparent equilibrium ratio of fatty acid alcohol ester/oleic acid was estimated using a high concentration of LPL and a long (20 h) incubation period. The equilibrium ratio was affected by the incubation pH and the alcohol chain length. When the incubation pH was below pH 7.0 and long chain fatty acyl alcohols were used as substrates, the fatty acid alcohol ester/free fatty acid equilibrium ratio favored ester formation, with an apparent equilibrium ratio of fatty acid alcohol ester/fatty acid of about 0.9/0.1. The equilibrium ratio decreased sharply at alkaline pH (above pH 8.0). The ratio also decreased when fatty alcohols with acyl chains shorter than dodecanol were used. When a trioleoylglycerol/fatty acyl alcohol emulsion was incubated with LPL, fatty acid alcohol esters were synthesized in a dose- and time-dependent fashion. Fatty acid alcohol esters were easily synthesized from trioleoylglycerol when fatty alcohols with acyl chains longer than dodecanol were used, but synthesis was decreased with fatty alcohols with acyl chain lengths shorter than decanol, and little synthesizing activity was detected with shorter-chain fatty alcohols such as butanol or ethanol. PMID:10578059

  16. gamma-Aminobutyric acid uptake inhibition and anticonvulsant activity of nipecotic acid esters.

    PubMed

    Crider, A M; Wood, J D; Tschappat, K D; Hinko, C N; Seibert, K

    1984-11-01

    n-Alkyl esters of nipecotic acid were prepared by Fischer esterification, and the esters were evaluated against bicuculline-induced seizures in mice. Evaluation of the alkyl esters for inhibition of gamma-aminobutyric acid uptake into mouse whole brain mini-slices revealed that the order of potency was proportional to chain length. The octyl ester inhibited gamma-aminobutyric acid and beta-alanine uptakes by apparently nonspecific mechanisms. A variety of phenyl esters of nipecotic acid were also synthesized utilizing either dicyclohexylcarbodiimide or 1,1'-carbonyldiimidazole as the condensing agent. Most of the phenyl esters were potent inhibitors of gamma-aminobutyric acid uptake. The uptake inhibition appeared to involve specific and nonspecific (detergent-like) mechanisms. The m-nitrophenyl and p-nitrophenyl esters were particularly potent against bicuculline-induced seizures in mice. PMID:6520765

  17. Branched Fatty Acid Esters of Hydroxy Fatty Acids Are Preferred Substrates of the MODY8 Protein Carboxyl Ester Lipase.

    PubMed

    Kolar, Matthew J; Kamat, Siddhesh S; Parsons, William H; Homan, Edwin A; Maher, Tim; Peroni, Odile D; Syed, Ismail; Fjeld, Karianne; Molven, Anders; Kahn, Barbara B; Cravatt, Benjamin F; Saghatelian, Alan

    2016-08-23

    A recently discovered class of endogenous mammalian lipids, branched fatty acid esters of hydroxy fatty acids (FAHFAs), possesses anti-diabetic and anti-inflammatory activities. Here, we identified and validated carboxyl ester lipase (CEL), a pancreatic enzyme hydrolyzing cholesteryl esters and other dietary lipids, as a FAHFA hydrolase. Variants of CEL have been linked to maturity-onset diabetes of the young, type 8 (MODY8), and to chronic pancreatitis. We tested the FAHFA hydrolysis activity of the CEL MODY8 variant and found a modest increase in activity as compared with that of the normal enzyme. Together, the data suggest that CEL might break down dietary FAHFAs. PMID:27509211

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

  19. 21 CFR 184.1101 - Diacetyl tartaric acid esters of mono- and diglycerides.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Diacetyl tartaric acid esters of mono- and... acid esters of mono- and diglycerides. (a) Diacetyl tartaric acid esters of mono- and diglycerides... groups of glycerin has been esterified by diacetyl tartaric acid and by fatty acids. The ingredient...

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

    PubMed

    van den Broek, Lambertus A M; Boeriu, Carmen G

    2013-03-01

    Amphiphilic oligo- and polysaccharides (e.g. polysaccharide alkyl or alkyl-aryl esters) form a new class of polymers with exceptional properties. They function as polymeric surfactants, whilst maintaining most of the properties of the starting polymeric material such as emulsifying, gelling, and film forming properties combined with partial water solubility or permeability. At present carbohydrate fatty acid esters are generally obtained by chemical methods using toxic solvents and organic and inorganic catalysts that leave residual traces in the final products. Enzymatic reactions offer an attractive alternative route for the synthesis of polysaccharide esters. In this review the state of the art of enzymatic synthesis of oligo- and polysaccharides fatty esters has been described. PMID:23465902

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

    DOEpatents

    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.

  2. 40 CFR 417.140 - Applicability; description of the neutralization of sulfuric acid esters and sulfonic acids...

    Code of Federal Regulations, 2010 CFR

    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...

  3. 40 CFR 417.140 - Applicability; description of the neutralization of sulfuric acid esters and sulfonic acids...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 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...

  4. 40 CFR 417.140 - Applicability; description of the neutralization of sulfuric acid esters and sulfonic acids...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 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...

  5. 40 CFR 417.140 - Applicability; description of the neutralization of sulfuric acid esters and sulfonic acids...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 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...

  6. 40 CFR 417.140 - Applicability; description of the neutralization of sulfuric acid esters and sulfonic acids...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 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...

  7. Preparation and physical properties of chitin fatty acids esters.

    PubMed

    Yang, Byung Y; Ding, Qiong; Montgomery, Rex

    2009-02-17

    Trifluoroacetic anhydride is an effective promoter for the preparation of chitin single- and mixed-acid esters. Complete dissolution is achieved within 30 min when powdered chitin is heated at 70 degrees C in a mixed solution of carboxylic acid(s) and trifluoroacetic anhydride. Chitin esters prepared are chitin acetate, chitin butyrate, chitin hexanoate and chitin octanoate, chitin co-acetate/butyrate, chitin co-acetate/hexanoate, chitin co-acetate/octanoate, chitin co-acetate/palmitate, each from a solution of the respective reactants. The products have degrees of O-acyl substitution in a range of DS 1-2 depending on the nature of acyl group, as analyzed by gas-liquid and high-pressure liquid chromatography. Acetic acid as a mutual component for the mixed-acid esters increases the total degree of substitution, and the acetyl substitution is close to the relative distribution in the reaction mixture for chitin co-acetate/butyrate. It is favored over hexanoate, octanoate, and palmitate. The parent molecules, as calculated by the composition of the chitin esters and their molecular weights by light-scattering spectroscopy, are 30 kDa for the smallest and 150-151 kDa for the largest. Films of these chitin derivatives when cast from solution are strong and flexible with limited extensibility. By dynamic mechanical analysis of the ester film, it was found that both the glass transition temperature (T(g)) and the tensile modulus (E' at 25 degrees C) are highest for chitin acetate (218 degrees C and 5.8 GPa), and lowest for chitin octanoate (182 degrees C and 1.5 GPa). For the other esters, these values lie between the above-cited values, where the T(g) and the E' decrease with an increase in the chain length of the acyl constituent. PMID:19091309

  8. Electron driven processes in chlorodifluoroacetic acid methyl ester

    NASA Astrophysics Data System (ADS)

    Kopyra, Janina

    2014-07-01

    Dissociative electron attachment to gas phase 2-chloro-2,2-difluoroacetic acid methyl ester (CClF2COOCH3) is studied by means of a crossed beams apparatus. Effective cleavage of the C-Cl bond is observed within a broad resonance in the energy range 0-1 eV and visible via the appearance of the light fragment Cl-. In chlorodifluoroacetic acid cleavage of the C-Cl bond was observed not only via the Cl- anion formation but predominantly via expulsion of the neutral chlorine atom leading to the formation of the (M-Cl)- anion. Similar to the previously studied esters CF3COOCH3 and CF3COOC2H5[I. Martin, J. Langer, E. Illenberger, Z. Phys. Chem. 222, 1185 (2008)], we observe reaction due to the cleavage of the ester bond resulting in the formation of the closed shell (M-CH3)- anion.

  9. 21 CFR 172.859 - Sucrose fatty acid esters.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Sucrose fatty acid esters. 172.859 Section 172.859 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION Multipurpose Additives §...

  10. Fungicidal Activities of Dihydroferulic Acid Alkyl Ester Analogues

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The natural product dihydroferulic acid (DFA, 1) and the synthesized DFA methyl (4a), ethyl (4b), propyl (4c), hexyl (4d), octyl (4e), and decyl (4f) esters were examined for antifungal activity. Test fungi included Saccharomyces cerevisiae (wild type, and deletion mutants slt2delta and bck1delta), ...

  11. 40 CFR 721.4215 - Hexanedioic acid, diethenyl ester.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Hexanedioic acid, diethenyl ester. 721.4215 Section 721.4215 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.4215 Hexanedioic...

  12. 40 CFR 721.5310 - Neononanoic acid, ethenyl ester.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Neononanoic acid, ethenyl ester. 721.5310 Section 721.5310 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.5310 Neononanoic...

  13. Fungicidal Activities of Dihydroferulic Acid Alkyl Ester Analogs

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The natural product dihydroferulic acid (DFA, 1) and the synthesized DFA methyl (4a), ethyl (4b), propyl (4c), hexyl (4d), octyl (4e), and decyl (4f) esters were examined for antifungal activity. Test fungi included Saccharomyces cerevisiae (wild type, and deletion mutants slt2' and bck1'), Aspergil...

  14. 21 CFR 172.852 - Glyceryl-lacto esters of fatty acids.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... § 172.852 Glyceryl-lacto esters of fatty acids. Glyceryl-lacto esters of fatty acids (the lactic acid... conditions: (a) They are manufactured from glycerin, lactic acid, and fatty acids conforming with § 172.860 and/or oleic acid derived from tall oil fatty acids conforming with § 172.862 and/or edible fats...

  15. Encapsulating fatty acid esters of bioactive compounds in starch

    NASA Astrophysics Data System (ADS)

    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

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

    DOEpatents

    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.

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

    SciTech Connect

    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.

  18. 21 CFR 175.260 - Partial phosphoric acid esters of polyester resins.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Partial phosphoric acid esters of polyester resins... of polyester resins. Partial phosphoric acid esters of polyester resins identified in this section... prescribed conditions: (a) For the purpose of this section, partial phosphoric acid esters of...

  19. 40 CFR 721.6110 - Alkyldi(alkyloxyhydroxypropyl) derivative, phosphoric acid esters, potassium salts.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...) 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...

  20. 40 CFR 721.6110 - Alkyldi(alkyloxyhydroxypropyl) derivative, phosphoric acid esters, potassium salts.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...) 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...

  1. 40 CFR 721.6110 - Alkyldi(alkyloxyhydroxypropyl) derivative, phosphoric acid esters, potassium salts.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...) 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...

  2. 40 CFR 721.6110 - Alkyldi(alkyloxyhydroxypropyl) derivative, phosphoric acid esters, potassium salts.

    Code of Federal Regulations, 2010 CFR

    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...

  3. 40 CFR 721.6110 - Alkyldi(alkyloxyhydroxypropyl) derivative, phosphoric acid esters, potassium salts.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...) 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...

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

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 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,...

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

    Code of Federal Regulations, 2010 CFR

    2010-07-01

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

  6. 40 CFR 721.3800 - Formaldehyde, condensated polyoxyethylene fatty acid, ester with styrenated phenol, ethylene...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 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,...

  7. 40 CFR 721.3800 - Formaldehyde, condensated polyoxyethylene fatty acid, ester with styrenated phenol, ethylene...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 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,...

  8. 40 CFR 721.3800 - Formaldehyde, condensated polyoxyethylene fatty acid, ester with styrenated phenol, ethylene...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 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,...

  9. 40 CFR 721.4250 - Hexanoic acid, 2-ethyl-, ethenyl ester.

    Code of Federal Regulations, 2010 CFR

    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...

  10. 40 CFR 721.2900 - Substituted aminobenzoic acid ester (generic name).

    Code of Federal Regulations, 2010 CFR

    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...

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

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 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 721.8340 - Mono esters from 2- propenoic acid (generic).

    Code of Federal Regulations, 2010 CFR

    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...

  13. 40 CFR 721.6475 - Alkyl polycarboxylic acids, esters with ethoxylated fatty alcohols.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 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...

  14. 40 CFR 721.8340 - Mono esters from 2- propenoic acid (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 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...

  15. 40 CFR 721.6475 - Alkyl polycarboxylic acids, esters with ethoxylated fatty alcohols.

    Code of Federal Regulations, 2010 CFR

    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...

  16. Synthesis of Alkyl Methylphosphonic Acid Esters

    SciTech Connect

    Mong, Gary M.; Harvey, Scott D.; Campbell, James A.

    2005-08-01

    This manuscript describes a simple synthesis and purification of cyclohexyl methylphosphonic and isopropyl methylphosphonic acids that provides high purity (>95% purity) product in gram quantities. Based on needs for improved analytical methods for indirect detection of nerve agent use, there is an increasing demand for these nerve agent hydrolysis products. These products are not commercially available. Synthesis is based on reaction of equimolar amounts of alcohol with methylphosphonic dichloride in toluene followed by the addition of excess water (two mole equivalents). The product was then extracted from the resulting aqueous layer into chloroform. The extraction scheme proved highly effective in removing unreacted starting materials and reaction by-products.

  17. Changes in Esters of Fatty Acids of Rhizopus arrhizus During Germination and Growth

    PubMed Central

    Hess, S. L.; Weber, D. J.; Gunasekaran, M.

    1972-01-01

    Natural esters of fatty acids of Rhizopus arrhizus Fischer increased during the first 48 hr of growth. During the 48- to 72-hr period, there was a shift in concentration from the methyl esters to the ethyl esters of fatty acids. PMID:5079078

  18. 4-Dimenthylaminopyridine or Acid-Catalyzed Synthesis of Esters: A Comparison

    ERIC Educational Resources Information Center

    van den Berg, Annemieke W. C.; Hanefeld, Ulf

    2006-01-01

    A set of highly atom-economic experiments was developed to highlight the differences between acid- and base-catalyzed ester syntheses and to introduce the principles of atom economy. The hydrochloric acid-catalyzed formation of an ester was compared with the 4-dimethylaminopyradine-catalyzed ester synthesis.

  19. 40 CFR 721.1579 - 1,2,4-Benzenetricarboxylic acid, tris [4-(ethenyloxy) butyl] ester.

    Code of Federal Regulations, 2010 CFR

    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...

  20. 40 CFR 721.3680 - Ethylene oxide adduct of fatty acid ester with pentaerythritol.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 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)...

  1. 40 CFR 721.10133 - 2-Propenoic acid, 2-methyl, 2-hydroxyethyl ester, homopolymer.

    Code of Federal Regulations, 2010 CFR

    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....

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

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...)-, 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...

  3. 40 CFR 721.1579 - 1,2,4-Benzenetricarboxylic acid, tris [4-(ethenyloxy) butyl] ester.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 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...

  4. 40 CFR 721.10165 - Carbonotrithioic acid, bis(phenylmethyl) ester.

    Code of Federal Regulations, 2010 CFR

    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...

  5. 40 CFR 721.9965 - Fatty acids, C10-13 - branched, vinyl esters.

    Code of Federal Regulations, 2010 CFR

    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...

  6. 40 CFR 721.3680 - Ethylene oxide adduct of fatty acid ester with pentaerythritol.

    Code of Federal Regulations, 2010 CFR

    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)...

  7. 40 CFR 721.1577 - 1,4-Benzenedicarboxylic acid, bis [4-(ethenyloxy) butyl] ester.

    Code of Federal Regulations, 2010 CFR

    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...

  8. 40 CFR 721.7290 - Propanoic acid, 2-(trimethoxysilyl)-, ethyl ester.

    Code of Federal Regulations, 2010 CFR

    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...

  9. 40 CFR 721.1577 - 1,4-Benzenedicarboxylic acid, bis [4-(ethenyloxy) butyl] ester.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 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...

  10. 40 CFR 721.9965 - Fatty acids, C10-13 - branched, vinyl esters.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 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...

  11. 40 CFR 721.987 - Dialkylaminophenyl imino pyrazole acid ester (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 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...

  12. 40 CFR 721.10133 - 2-Propenoic acid, 2-methyl, 2-hydroxyethyl ester, homopolymer.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...-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....

  13. 40 CFR 721.10165 - Carbonotrithioic acid, bis(phenylmethyl) ester.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...(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...

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

    Code of Federal Regulations, 2010 CFR

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

    PubMed

    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. PMID:25227993

  16. Lysosomal Acid Lipase Hydrolyzes Retinyl Ester and Affects Retinoid Turnover.

    PubMed

    Grumet, Lukas; Eichmann, Thomas O; Taschler, Ulrike; Zierler, Kathrin A; Leopold, Christina; Moustafa, Tarek; Radovic, Branislav; Romauch, Matthias; Yan, Cong; Du, Hong; Haemmerle, Guenter; Zechner, Rudolf; Fickert, Peter; Kratky, Dagmar; Zimmermann, Robert; Lass, Achim

    2016-08-19

    Lysosomal acid lipase (LAL) is essential for the clearance of endocytosed cholesteryl ester and triglyceride-rich chylomicron remnants. Humans and mice with defective or absent LAL activity accumulate large amounts of cholesteryl esters and triglycerides in multiple tissues. Although chylomicrons also contain retinyl esters (REs), a role of LAL in the clearance of endocytosed REs has not been reported. In this study, we found that murine LAL exhibits RE hydrolase activity. Pharmacological inhibition of LAL in the human hepatocyte cell line HepG2, incubated with chylomicrons, led to increased accumulation of REs in endosomal/lysosomal fractions. Furthermore, pharmacological inhibition or genetic ablation of LAL in murine liver largely reduced in vitro acid RE hydrolase activity. Interestingly, LAL-deficient mice exhibited increased RE content in the duodenum and jejunum but decreased RE content in the liver. Furthermore, LAL-deficient mice challenged with RE gavage exhibited largely reduced post-prandial circulating RE content, indicating that LAL is required for efficient nutritional vitamin A availability. In summary, our results indicate that LAL is the major acid RE hydrolase and required for functional retinoid homeostasis. PMID:27354281

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

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... esters of fatty acids (the lactic acid esters of mono- and diglycerides) may be safely used in food in accordance with the following prescribed conditions: (a) They are manufactured from glycerin, lactic acid, and fatty acids conforming with § 172.860 and/or oleic acid derived from tall oil fatty...

  18. 21 CFR 172.852 - Glyceryl-lacto esters of fatty acids.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... esters of fatty acids (the lactic acid esters of mono- and diglycerides) may be safely used in food in accordance with the following prescribed conditions: (a) They are manufactured from glycerin, lactic acid, and fatty acids conforming with § 172.860 and/or oleic acid derived from tall oil fatty...

  19. 21 CFR 172.852 - Glyceryl-lacto esters of fatty acids.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... esters of fatty acids (the lactic acid esters of mono- and diglycerides) may be safely used in food in accordance with the following prescribed conditions: (a) They are manufactured from glycerin, lactic acid, and fatty acids conforming with § 172.860 and/or oleic acid derived from tall oil fatty...

  20. 21 CFR 172.852 - Glyceryl-lacto esters of fatty acids.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... esters of fatty acids (the lactic acid esters of mono- and diglycerides) may be safely used in food in accordance with the following prescribed conditions: (a) They are manufactured from glycerin, lactic acid, and fatty acids conforming with § 172.860 and/or oleic acid derived from tall oil fatty...

  1. Electron-impact ionization of benzoic acid, nicotinic acid and their n-butyl esters

    NASA Astrophysics Data System (ADS)

    Opitz, Joachim

    2007-08-01

    Electron-impact ionization mass spectra, the decay of metastable ions, ionization and appearance energies and bond energies, as dissociation energies, are reported for the title compounds. An ionization energy of 9.47 eV was obtained for benzoic acid, 9.43 eV for benzoic acid n-butyl ester, 9.61 eV for nicotinic acid and 9.97 eV for nicotinic acid n-butyl ester. Molecular ions of both butyl esters show two common main fragmentation pathways: the first process is a McLafferty rearrangement, characterized by the transfer of one H-atom from the aliphatic ester chain, which leads to the ions of either the organic acid or 1-butene. From their appearance energies and known thermodynamic data, gas-phase formation enthalpies () of the parent n-butyl esters are calculated. Values of for benzoic acid n-butyl ester and for nicotinic acid n-butyl ester were obtained. The second process is characterized by the transfer of two H-atoms from the ester chain leading to a protonated form of the corresponding organic acids and C4H7 radicals. Good evidence is provided for the formation of methylallyl radicals. Appearance energies are used to calculate a proton affinity (PA) for benzoic acid. The obtained value of PA = (8.73 ± 0.3) eV, corresponding to a protonation of the carbonyl group, is in close corroboration with published data (PA = 8.51 eV). Activation energies for the intermediate H-transfers were found to be insignificant. This methodic gateway is applied to the system of nicotinic acid and its butyl ester. Adopting the formation of a methylallyl radical, the obtained proton affinity of nicotinic acid, PA = 8.58 eV, is very near to the published data of benzoic acid. An alternative fragmentation mechanism leading to a value of PA [approximate] 9.5 eV (typical for a protonation of the pyridine-nitrogen) is very unlikely. It is concluded that this transfer of two H-atoms from the ester chain is controlled by a charge switching between the carboxylic oxygen atoms which leads to

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

  3. 40 CFR 721.6200 - Fatty acid polyamine condensate, phosphoric acid ester salts.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Fatty acid polyamine condensate, phosphoric acid ester salts. 721.6200 Section 721.6200 Protection of Environment ENVIRONMENTAL PROTECTION... New Uses for Specific Chemical Substances § 721.6200 Fatty acid polyamine condensate, phosphoric...

  4. 40 CFR 721.6200 - Fatty acid polyamine condensate, phosphoric acid ester salts.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Fatty acid polyamine condensate, phosphoric acid ester salts. 721.6200 Section 721.6200 Protection of Environment ENVIRONMENTAL PROTECTION... New Uses for Specific Chemical Substances § 721.6200 Fatty acid polyamine condensate, phosphoric...

  5. 40 CFR 721.6200 - Fatty acid polyamine condensate, phosphoric acid ester salts.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Fatty acid polyamine condensate, phosphoric acid ester salts. 721.6200 Section 721.6200 Protection of Environment ENVIRONMENTAL PROTECTION... New Uses for Specific Chemical Substances § 721.6200 Fatty acid polyamine condensate, phosphoric...

  6. 40 CFR 721.6200 - Fatty acid polyamine condensate, phosphoric acid ester salts.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Fatty acid polyamine condensate, phosphoric acid ester salts. 721.6200 Section 721.6200 Protection of Environment ENVIRONMENTAL PROTECTION... New Uses for Specific Chemical Substances § 721.6200 Fatty acid polyamine condensate, phosphoric...

  7. 40 CFR 721.6200 - Fatty acid polyamine condensate, phosphoric acid ester salts.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Fatty acid polyamine condensate, phosphoric acid ester salts. 721.6200 Section 721.6200 Protection of Environment ENVIRONMENTAL PROTECTION... New Uses for Specific Chemical Substances § 721.6200 Fatty acid polyamine condensate, phosphoric...

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

    PubMed

    Shi, Xueyan; Liu, Feipeng; Bian, Qinghua

    2016-01-01

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

  9. 40 CFR 721.10142 - Oxabicycloalkane carboxylic acid alkanediyl ester (generic).

    Code of Federal Regulations, 2010 CFR

    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)...

  10. 40 CFR 721.10142 - Oxabicycloalkane carboxylic acid alkanediyl ester (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 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)...

  11. 40 CFR 721.6075 - Phosphonic acid, 1,1-methylenebis-tetrakis(1-methylethyl) ester.

    Code of Federal Regulations, 2010 CFR

    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)...

  12. 40 CFR 721.6075 - Phosphonic acid, 1,1-methylenebis-tetrakis(1-methylethyl) ester.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...-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)...

  13. 40 CFR 721.10289 - Hexanedioic acid polymer with aliphatic polyol dihydrogen phosphate aromatic ester (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... aliphatic polyol dihydrogen phosphate aromatic ester (generic). 721.10289 Section 721.10289 Protection of... polymer with aliphatic polyol dihydrogen phosphate aromatic ester (generic). (a) Chemical substance and... acid polymer with aliphatic polyol dihydrogen phosphate aromatic ester (PMN P-11-333) is subject...

  14. 40 CFR 721.10289 - Hexanedioic acid polymer with aliphatic polyol dihydrogen phosphate aromatic ester (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... aliphatic polyol dihydrogen phosphate aromatic ester (generic). 721.10289 Section 721.10289 Protection of... polymer with aliphatic polyol dihydrogen phosphate aromatic ester (generic). (a) Chemical substance and... acid polymer with aliphatic polyol dihydrogen phosphate aromatic ester (PMN P-11-333) is subject...

  15. 40 CFR 721.10289 - Hexanedioic acid polymer with aliphatic polyol dihydrogen phosphate aromatic ester (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... aliphatic polyol dihydrogen phosphate aromatic ester (generic). 721.10289 Section 721.10289 Protection of... polymer with aliphatic polyol dihydrogen phosphate aromatic ester (generic). (a) Chemical substance and... acid polymer with aliphatic polyol dihydrogen phosphate aromatic ester (PMN P-11-333) is subject...

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

    EPA Science Inventory

    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...

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

    PubMed

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

    2016-10-01

    A new sesquiterpene lactone glycoside (1) and a new quinic acid methyl ester (2) were isolated from Patrinia villosa, together with another two known compounds chlorogenic acid n-butyl ester (3), 3, 4-di-O-caffeoylquinic acid methyl ester (4). Their structures were established using 1D/2D-NMR spectroscopy, mass spectrometry, and comparing with spectroscopic data reported in the literature. PMID:27156969

  18. 40 CFR 721.9965 - Fatty acids, C10-13 - branched, vinyl esters.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Fatty acids, C10-13 - branched, vinyl... 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...

  19. 40 CFR 721.9965 - Fatty acids, C10-13 - branched, vinyl esters.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Fatty acids, C10-13 - branched, vinyl... 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...

  20. 40 CFR 721.9965 - Fatty acids, C10-13 - branched, vinyl esters.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Fatty acids, C10-13 - branched, vinyl... 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...

  1. 21 CFR 172.850 - Lactylated fatty acid esters of glycerol and propylene glycol.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ...) The additive meets the following specifications: Water insoluble combined lactic acid, 14-18 percent... 21 Food and Drugs 3 2014-04-01 2014-04-01 false Lactylated fatty acid esters of glycerol and... CONSUMPTION Multipurpose Additives § 172.850 Lactylated fatty acid esters of glycerol and propylene...

  2. Presystemic metabolism and intestinal absorption of antipsoriatic fumaric acid esters.

    PubMed

    Werdenberg, D; Joshi, R; Wolffram, S; Merkle, H P; Langguth, P

    2003-09-01

    Psoriasis is a chronic inflammatory skin disease. Its treatment is based on the inhibition of proliferation of epidermal cells and interference in the inflammatory process. A new systemic antipsoriasis drug, which consists of dimethylfumarate and ethylhydrogenfumarate in the form of their calcium, magnesium and zinc salts has been introduced in Europe with successful results. In the present study, a homologous series of mono- and diesters of fumaric acid has been studied with respect to the sites and kinetics of presystemic ester degradation using pancreas extract, intestinal perfusate, intestinal homogenate and liver S9 fraction. In addition, intestinal permeability has been determined using isolated intestinal mucosa as well as Caco-2 cell monolayers, in order to obtain estimates of the fraction of the dose absorbed for these compounds. Relationships between the physicochemical properties of the fumaric acid esters and their biological responses were investigated. The uncharged diester dimethylfumarate displayed a high presystemic metabolic lability in all metabolism models. It also showed the highest permeability in the Caco-2 cell model. However, in permeation experiments with intestinal mucosa in Ussing-type chambers, no undegraded DMF was found on the receiver side, indicating complete metabolism in the intestinal tissue. The intestinal permeability of the monoesters methyl hydrogen fumarate, ethyl hydrogen fumarate, n-propylhydrogen fumarate and n-pentyl hydrogen fumarate increased with an increase in their lipophilicity, however, their presystemic metabolism rates likewise increased with increasing ester chain length. It is concluded that for fumarates, an increase in intestinal permeability of the more lipophilic derivatives is counterbalanced by an increase in first-pass extraction. PMID:12973823

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

    PubMed Central

    Bruns, Hilke; Riclea, Ramona

    2011-01-01

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

  4. Synthesis, Evaluation of Anticancer Activity and QSAR Study of Heterocyclic Esters of Caffeic Acid

    PubMed Central

    Hajmohamad Ebrahim Ketabforoosh, Shima; Amini, Mohsen; Vosooghi, Mohsen; Shafiee, Abbas; Azizi, Ebrahim; Kobarfard, Farzad

    2013-01-01

    Caffeic acid phenethyl ester (CAPE) suppresses the growth of transformed cells such as human breast cancer cells, hepatocarcinoma , myeloid leukemia, colorectal cancer cells, fibrosarcoma, glioma and melanoma. A group of heterocyclic esters of caffeic acid was synthesized using Mitsunobu reaction and the esters were subjected to further structural modification by electrooxidation of the catechol ring of caffeic acid esters in the presence of sodium benzenesulfinate and sodium toluensulfinate as nucleophiles. Both heterocyclic esters of caffeic acid and their arylsulfonyl derivatives were evaluated for their cytotoxic activity against HeLa, SK-OV-3, and HT-29 cancer cell lines. HeLa cells showed the highest sensitivity to the compounds and heterocyclic esters with no substituent on catechol ring showed better activity compared to their substituted counterparts. QSAR studies reemphasized the importance of molecular shape of the compounds for their cytotoxic activity. PMID:24523750

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

    PubMed

    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. PMID:26506263

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

    DOEpatents

    Arnold, Jr., Wesley D.

    1977-01-01

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

  7. Complexes of polyadenylic acid and the methyl esters of amino acids

    NASA Technical Reports Server (NTRS)

    Khaled, M. A.; Mulins, D. W., Jr.; Swindle, M.; Lacey, J. C., Jr.

    1983-01-01

    A study of amino acid methyl esters binding to polyadenylic acid supports the theory that the genetic code originated through weak but selective affinities between amino acids and nucleotides. NMR, insoluble complex analysis, and ultraviolet spectroscopy are used to illustrate a correlation between the hydrophybicities of A amino acids and their binding constants, which, beginning with the largest, are in the order of Phe (having nominally a hydrophobic AAA anticodon), Ile, Leu, Val and Gly (having a hydrophilic anticodon with no A). In general, the binding constants are twice the values by Reuben and Polk (1980) for monomeric AMP, which suggests that polymer amino acids are interacting with only one base. No real differences are found betwen poly A binding for free Phe, Phe methyl ester or Phe amide, except that the amide value is slightly lower.

  8. 21 CFR 178.3780 - Polyhydric alcohol esters of long chain monobasic acids.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... produced by the reaction of either ethylene glycol or glycerol with long chain monobasic acids containing... 21 Food and Drugs 3 2014-04-01 2014-04-01 false Polyhydric alcohol esters of long chain monobasic... Adjuvants and Production Aids § 178.3780 Polyhydric alcohol esters of long chain monobasic acids....

  9. 40 CFR 721.10555 - Benzoic acid nonyl ester, branched and linear.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Benzoic acid nonyl ester, branched and... Specific Chemical Substances § 721.10555 Benzoic acid nonyl ester, branched and linear. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as...

  10. 40 CFR 721.10555 - Benzoic acid nonyl ester, branched and linear.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Benzoic acid nonyl ester, branched and... Specific Chemical Substances § 721.10555 Benzoic acid nonyl ester, branched and linear. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as...

  11. 40 CFR 721.3700 - Fatty acid, ester with styrenated phenol, ethylene oxide adduct.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... phenol, ethylene oxide adduct. 721.3700 Section 721.3700 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.3700 Fatty acid, ester with styrenated phenol... chemical substance identified generically as fatty acid, ester with styrenated phenol, ethylene...

  12. 40 CFR 721.3700 - Fatty acid, ester with styrenated phenol, ethylene oxide adduct.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... phenol, ethylene oxide adduct. 721.3700 Section 721.3700 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.3700 Fatty acid, ester with styrenated phenol... chemical substance identified generically as fatty acid, ester with styrenated phenol, ethylene...

  13. 40 CFR 721.3700 - Fatty acid, ester with styrenated phenol, ethylene oxide adduct.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... phenol, ethylene oxide adduct. 721.3700 Section 721.3700 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.3700 Fatty acid, ester with styrenated phenol... chemical substance identified generically as fatty acid, ester with styrenated phenol, ethylene...

  14. 40 CFR 721.3700 - Fatty acid, ester with styrenated phenol, ethylene oxide adduct.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... phenol, ethylene oxide adduct. 721.3700 Section 721.3700 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.3700 Fatty acid, ester with styrenated phenol... chemical substance identified generically as fatty acid, ester with styrenated phenol, ethylene...

  15. 40 CFR 721.3700 - Fatty acid, ester with styrenated phenol, ethylene oxide adduct.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... phenol, ethylene oxide adduct. 721.3700 Section 721.3700 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.3700 Fatty acid, ester with styrenated phenol... chemical substance identified generically as fatty acid, ester with styrenated phenol, ethylene...

  16. 21 CFR 178.3450 - Esters of stearic and palmitic acids.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false 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...

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

    PubMed

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

    2004-06-01

    An aspartame analogue, L-asparaginyl L-3-phenyllactic acid methyl ester was synthesized with aspartic acid replaced by asparagine and peptide bond replaced by ester bond. The aspartic acid of aspartame could be replaced by asparagine as reported in the literature. In this analogue, the hydrogen of amide group could still form a hydrogen bond with the oxygen of ester bond and the ester bond was isosteric with peptide bond. However, the product was not sweet, showing that the peptide bond could not be replaced by ester bond. The peptide C-N bond behaves as a double bond that is not free to rotate and the C, O, N and H atoms are in the same plane. The replacement of peptide bond by ester bond destroyed the unique conformation of peptide bond, resulting in the loss of sweet taste. PMID:15188052

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

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

  19. Green chromatography determination of fatty acid methyl esters in biodiesel.

    PubMed

    Mayo, Carlos Molina; Alayón, Andrea Brito; García Rodríguez, María Teresa; Jiménez Abizanda, Ana Isabel; Moreno, Francisco Jiménez

    2015-01-01

    This work proposes a green, simple and rapid chromatographic methodology for separation and determination of a group of 13 fatty acids methyl esters (FAMEs) by using a capillary gas chromatography with a flame ionization detector. The method was successfully applied for the determination of FAMEs in biodiesel samples from commercial and waste cooking oils, synthesized by homogeneous catalysis. Detection and quantification limits were in the μg L(-1) level. Direct injection of sample solution was compared with solid-phase extraction and solid-phase microextraction procedures, giving similar results. The lower analysis time represent considerable improvement compared with other papers. The described methodology is especially suitable for process control applications. The samples analysed showed total contents of FAMEs higher than 96.5%, which verifies the European regulations. PMID:25666201

  20. Glycerol Ester Hydrolase Activity of Lactic Acid Bacteria

    PubMed Central

    Oterholm, Anders; Ordal, Z. John; Witter, Lloyd D.

    1968-01-01

    Seventeen strains of lactic acid bacteria were assayed for their glycerol ester hydrolase activity by using an improved agar-well technique, and eight strains by determining the activity in cell-free extracts using a pH-stat procedure. All cultures tested showed activity and hydrolyzed tributyrin more actively than they did tricaproin. The cell extract studies demonstrated that the cells contained intracellular esterases and lipases. The culture supernatant fluid was without activity. The lipase and the esterase differed in their relative activity to each other in the different extracts and in the ease by which they could be freed from the cellular debris. It is suggested that the lipase of these organisms is an endoenzyme and the esterase an ectoenzyme. PMID:5649866

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

    NASA Astrophysics Data System (ADS)

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

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

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

    NASA Technical Reports Server (NTRS)

    Weber, Arthur L.; Hsu, Victor

    1990-01-01

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

  3. Destruction of Leishmania mexicana amazonensis amastigotes within macrophages by lysosomotropic amino acid esters

    PubMed Central

    1986-01-01

    Leishmania amastigotes parasitize almost exclusively the mononuclear phagocytes of mammals. The organisms survive and multiply within acidified vacuoles (parasitophorous vacuoles; p.v.) akin to phagolysosomes. Certain amino acid esters are known to accumulate in and disrupt lysosomes. We postulated that, since Leishmania possess lysosome-like organelles, they may be susceptible to the potentially high ester concentrations attained in the p.v. We report here that L- amino acid esters can rapidly destroy intracellular Leishmania at concentrations that do not appear to damage the host cells. L-leu-OMe, which cured greater than or equal to 90% of infected macrophages at 0.8 mM concentrations, was used in most of the experiments. L-leu-OMe was only active after infection, implying inefficient transfer from secondary lysosomes to the p.v. Parasite destruction had several features in common with lysosomal and leukocyte damage induced by the esters, i.e., inactivity of D-amino acid esters, a marked pH dependence and increased killing after ester pulses at lower temperatures. Killing depended on the amino acid and on the ester substitution. The most active of the methyl esters assayed was that of leucine, followed by those of tryptophan, glutamic acid, methionine, phenylalanine, and tyrosine. Methyl esters of seven other amino acids were inactive when tested at up to 10 mM concentrations. Among leucine esters studied, benzyl ester was sixfold more active than the methyl homolog. The dipeptide L-leu-leu-OMe produced 90% cure at 0.08 mM concentrations. Leishmanicidal activity could be related to penetration of the parasites by the esters or to toxic ester hydrolysis products released in the p.v. The first hypothesis is supported by the pH-dependent destruction of isolated amastigotes by the esters. Furthermore, relatively high concentrations of L-leucine, methanol, or benzyl alcohol were not demonstrably toxic to the amastigotes. We postulate that ester concentrations

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

    PubMed

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

    2015-04-20

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

  5. Development of a Method for the N-Arylation of Amino Acid Esters with Aryl Triflates.

    PubMed

    King, Sandra M; Buchwald, Stephen L

    2016-08-19

    A general method for the N-arylation of amino acid esters with aryl triflates is described. Both α- and β-amino acid esters, including methyl, tert-butyl, and benzyl esters, are viable substrates. Reaction optimization was carried out by design of experiment (DOE) analysis using JMP software. The mild reaction conditions, which use t-BuBrettPhos Pd G3 or G4 precatalyst, result in minimal racemization of the amino acid ester. This method is the first synthetic application of the t-BuBrettPhos Pd G4 precatalyst. Mechanistic studies show that the observed erosion in enantiomeric excess is due to racemization of the amino acid ester starting material and not of the product. PMID:27498618

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

    PubMed

    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. PMID:26179516

  7. 40 CFR 721.3100 - Oligomeric silicic acid ester compound with a hy-droxyl-al-kyla-mine.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 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...

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

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 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 721.3100 - Oligomeric silicic acid ester compound with a hy-droxyl-al-kyla-mine.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 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...

  10. 40 CFR 721.3100 - Oligomeric silicic acid ester compound with a hy-droxyl-al-kyla-mine.

    Code of Federal Regulations, 2010 CFR

    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...

  11. 40 CFR 721.3100 - Oligomeric silicic acid ester compound with a hy-droxyl-al-kyla-mine.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 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...

  12. 40 CFR 721.10410 - Polyether ester acid compound with a polyamine amide (generic) (P-05-714).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Polyether ester acid compound with a... Significant New Uses for Specific Chemical Substances § 721.10410 Polyether ester acid compound with a.... (1) The chemical substance identified generically as polyether ester acid compound with a...

  13. 40 CFR 721.10410 - Polyether ester acid compound with a polyamine amide (generic) (P-05-714).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Polyether ester acid compound with a... Significant New Uses for Specific Chemical Substances § 721.10410 Polyether ester acid compound with a.... (1) The chemical substance identified generically as polyether ester acid compound with a...

  14. 40 CFR 721.10410 - Polyether ester acid compound with a polyamine amide (generic) (P-05-714).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Polyether ester acid compound with a... Significant New Uses for Specific Chemical Substances § 721.10410 Polyether ester acid compound with a.... (1) The chemical substance identified generically as polyether ester acid compound with a...

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

    PubMed

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

    2015-07-17

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

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

    PubMed

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

    2016-03-01

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

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

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

    PubMed

    Ren, Kangzi; Lamsal, Buddhi P

    2017-01-01

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

  19. 40 CFR 721.10448 - Acetic acid, hydroxy- methoxy-, methyl ester, reaction products with substituted alkylamine...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... ester, reaction products with substituted alkylamine (generic). 721.10448 Section 721.10448 Protection... NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10448 Acetic acid, hydroxy- methoxy-, methyl ester, reaction products with substituted alkylamine (generic)....

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

    PubMed

    Petter, P J

    1984-10-01

    Synopsis A review is given of the manufacture, properties and applications of the anionic surfactants commonly known as taurates and isethionates (fatty acid sulphoalkyl amides and esters, respectively). Originally developed in the 1930s for textile processing, these surfactants are used increasingly in the cosmetic field, particularly those derived from coconut fatty acid. Both types are produced from sodium isethionate, HO degrees C(2)H(4)SO(3)Na. The acyl isethionate, R degrees COO degrees C(2)H(4)SO(3)Na, is obtained by reaction with a fatty acid ('direct process'). or fatty acid chloride ('indirect process'). The direct process is cheaper but requires extreme conditions which can lead to discoloration of the product and a loss of shorter chain fatty acid components. The N-methyl-N-acyltaurate, R degrees CON(R(1))C(2)H(4)SO(3)Na, is obtained by Schotten-Baumann reaction of a fatty acid chloride with N-methyltaurine, which is derived from sodium isethionate via methylamine. Taurates and isethionates retain the benefits of the soaps to which they are structurally similar, but chemical modifications have eliminated many undesirable features. Thus they combine good detergency and wetting with high foaming, and maintain their performance in hard or salt water. Taurates are stable to hydrolysis over the whole pH range. Isethionates are prone to hydrolysis at high (>8) or low (<5) pH, but this does not normally present a problem in cosmetic formulations. Above all, these surfactants are characterized by their extreme mildness to skin. Syndet and syndet/soap bars based on isethionate can be formulated at neutral pH ('Dove type'bars) instead of the alkaline pH of soap, and have been shown in various studies to be milder than soap and better tolerated by the young, the old and those with sensitive skins. Similarly, isethionates have been shown to be less irritating than other anionic or amphoteric surfactants used in cosmetics. The difference has been related to the

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

    PubMed

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

    2016-06-21

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

  2. Antiallergic activity of rosmarinic acid esters is modulated by hydrophobicity, and bulkiness of alkyl side chain.

    PubMed

    Zhu, Fengxian; Xu, Zhongming; Yonekura, Lina; Yang, Ronghua; Tamura, Hirotoshi

    2015-01-01

    Methyl, propyl and hexyl esters of rosmarinic, caffeic and p-coumaric acids were tested for antiallergic activity, and rosmarinic acid propyl ester exhibited the greatest β-hexosaminidase release suppression (IC50, 23.7 μM). Quadratic correlations between pIC50 and cLogP (r(2) = 0.94, 0.98, and 1.00, respectively) were observed in each acid ester series. The antiallergic activity is modulated by hydrophobicity, and alkyl chain bulkiness. PMID:25686361

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

    PubMed

    Milchert, Eugeniusz; Malarczyk, Kornelia; Kłos, Marlena

    2015-01-01

    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. PMID:26633342

  4. Direct Determination of MCPD Fatty Acid Esters and Glycidyl Fatty Acid Esters in Vegetable Oils by LC–TOFMS

    PubMed Central

    Haines, Troy D.; Adlaf, Kevin J.; Pierceall, Robert M.; Lee, Inmok; Venkitasubramanian, Padmesh

    2010-01-01

    Analysis of MCPD esters and glycidyl esters in vegetable oils using the indirect method proposed by the DGF gave inconsistent results when salting out conditions were varied. Subsequent investigation showed that the method was destroying and reforming MCPD during the analysis. An LC time of flight MS method was developed for direct analysis of both MCPD esters and glycidyl esters in vegetable oils. The results of the LC–TOFMS method were compared with the DGF method. The DGF method consistently gave results that were greater than the LC–TOFMS method. The levels of MCPD esters and glycidyl esters found in a variety of vegetable oils are reported. MCPD monoesters were not found in any oil samples. MCPD diesters were found only in samples containing palm oil, and were not present in all palm oil samples. Glycidyl esters were found in a wide variety of oils. Some processing conditions that influence the concentration of MCPD esters and glycidyl esters are discussed. PMID:21350591

  5. Oxidase-peroxidase enzymes of Datura innoxia. Oxidation of formylphenylacetic acid ethyl ester.

    PubMed Central

    Kalyanaraman, V S; Mahadevan, S; Kumar, S A

    1975-01-01

    An enzyme system from Datura innoxia roots oxidizing formylphenylacetic acid ethyl ester was purified 38-fold by conventional methods such as (NH4)2SO4 fractionation, negative adsorption on alumina Cy gel and chromatography on DEAE-cellulose. The purified enzyme was shown to catalyse the stoicheiometric oxidation of formylphenylacetic acid ethyl ester to benzoylformic acid ethyl ester and formic acid, utilizing molecular O2. Substrate analogues such as phenylacetaldehyde and phenylpyruvate were oxidized at a very low rate, and formylphenylacetonitrile was an inhilating agents, cyanide, thiol compounds and ascorbic acid. This enzyme was identical with an oxidase-peroxidase isoenzyme. Another oxidase-peroxidase isoenzyme which separated on DEAE-chromatography also showed formylphenylacetic acid ethyl ester oxidase activity, albeit to a lesser extent. The properties of the two isoenzymes of the oxidase were compared and shown to differ in their oxidation and peroxidation properties. The oxidation of formylphenylacetic acid ethyl ester was also catalysed by horseradish peroxidase. The Datura isoenzymes exhibited typical haemoprotein spectra. The oxidation of formylphenylacetic acid ethyl ester was different from other peroxidase-catalysed reactions in not being activated by either Mn2+ or monophenols. The oxidation was inhibited by several mono- and poly-phenols and by catalase. A reaction mechanism for the oxidation is proposed. PMID:997

  6. Synthesis of Branched Methyl Hydroxy Stearates Including an Ester from Bio-Based Levulinic Acid

    Technology Transfer Automated Retrieval System (TEKTRAN)

    We report the synthesis of 5 useful branched methyl alpha-hydroxy oleate esters from commercially available methyl oleate and common organic acids. Of special interest is the synthesis utilizing the natural byproduct, levulinic acid. The other common organic acids used herein were propionic acid, ...

  7. 21 CFR 172.225 - Methyl and ethyl esters of fatty acids produced from edible fats and oils.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

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

  8. 21 CFR 172.225 - Methyl and ethyl esters of fatty acids produced from edible fats and oils.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

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

  9. 21 CFR 172.225 - Methyl and ethyl esters of fatty acids produced from edible fats and oils.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

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

  10. 21 CFR 172.225 - Methyl and ethyl esters of fatty acids produced from edible fats and oils.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

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

  11. 40 CFR 721.4097 - 7-Oxabicyclo[4.1.0]heptane-3-carboxylic acid, methyl ester.

    Code of Federal Regulations, 2010 CFR

    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...

  12. 40 CFR 721.1950 - 2-Butenedioic acid (Z), mono(2-((1-oxopropenyloxy)ethyl) ester .

    Code of Federal Regulations, 2010 CFR

    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...

  13. 40 CFR 721.1950 - 2-Butenedioic acid (Z), mono(2-((1-oxopropenyloxy)ethyl) ester .

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...-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...

  14. 40 CFR 721.4097 - 7-Oxabicyclo[4.1.0]heptane-3-carboxylic acid, methyl ester.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ..., 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...

  15. Chlorsulfuron modifies biosynthesis of acyl Acid substituents of sucrose esters secreted by tobacco trichomes.

    PubMed

    Kandra, L; Wagner, G J

    1990-11-01

    Sucrose esters and duvatrienediol diterpenes are principal constituents formed in and secreted outside head cells of trichomes occurring on surfaces of Nicotiana tabacum. Using trichome-bearing epidermal peels prepared from midveins of N. tabacum cv T.I. 1068 leaves, we found that chlorsulfuron reduced and modified radiolabeling of sucrose ester acyl acids derived from branched-chain amino acid metabolism. The herbicide did not effect formation and exudation of diterpenes which are products of isoprenoid metabolism. Treatment with 1.0 micromolar chlorsulfuron affected 8.5- and 6.3-fold reductions in radiolabeling of methylvaleryl and methylbutyryl groups of sucrose esters, respectively, and concomitant increases of 9- and 9.8-fold in radiolabeling of straight chain valeryl and butyryl groups, respectively. These results and others indicate that inhibition of acetolactate synthase causes an accumulation of 2-oxo-butyric acid that is utilized by enzymes common to Leu biosynthesis to form 2-oxo-valeric acid. Coenzyme A (CoA) activation of this keto acid gives rise to butyryl CoA, which is utilized to form butyryl containing sucrose esters. Alternatively, reutilization of 2-oxo-valeric acid by the same enzymes followed by CoA activation leads to valeryl containing sucrose esters. We propose that in trichome secretory cells synthase, isomerase and dehydrogenase enzymes which catalyze Leu synthesis/degredation in most tissues, convert iso-branched, anteiso-branched and straight-chain keto acids in the formation of sucrose ester acyl groups. PMID:16667871

  16. Chlorsulfuron Modifies Biosynthesis of Acyl Acid Substituents of Sucrose Esters Secreted by Tobacco Trichomes

    PubMed Central

    Kandra, Lili; Wagner, George J.

    1990-01-01

    Sucrose esters and duvatrienediol diterpenes are principal constituents formed in and secreted outside head cells of trichomes occurring on surfaces of Nicotiana tabacum. Using trichome-bearing epidermal peels prepared from midveins of N. tabacum cv T.I. 1068 leaves, we found that chlorsulfuron reduced and modified radiolabeling of sucrose ester acyl acids derived from branched-chain amino acid metabolism. The herbicide did not effect formation and exudation of diterpenes which are products of isoprenoid metabolism. Treatment with 1.0 micromolar chlorsulfuron affected 8.5- and 6.3-fold reductions in radiolabeling of methylvaleryl and methylbutyryl groups of sucrose esters, respectively, and concomitant increases of 9- and 9.8-fold in radiolabeling of straight chain valeryl and butyryl groups, respectively. These results and others indicate that inhibition of acetolactate synthase causes an accumulation of 2-oxo-butyric acid that is utilized by enzymes common to Leu biosynthesis to form 2-oxo-valeric acid. Coenzyme A (CoA) activation of this keto acid gives rise to butyryl CoA, which is utilized to form butyryl containing sucrose esters. Alternatively, reutilization of 2-oxo-valeric acid by the same enzymes followed by CoA activation leads to valeryl containing sucrose esters. We propose that in trichome secretory cells synthase, isomerase and dehydrogenase enzymes which catalyze Leu synthesis/degredation in most tissues, convert iso-branched, anteiso-branched and straight-chain keto acids in the formation of sucrose ester acyl groups. PMID:16667871

  17. Comparative Oxidative Stability of Fatty Acid Alkyl Esters by Accelerated Methods

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Several fatty acid alkyl esters were subjected to accelerated methods of oxidation, including EN 14112 (Rancimat method) and pressurized differential scanning calorimetry (PDSC). Structural trends elucidated from both methods that improved oxidative stability included decreasing the number of doubl...

  18. Premixed ignition behavior of C{sub 9} fatty acid esters: A motored engine study

    SciTech Connect

    Zhang, Yu.; Yang, Yi; Boehman, Andre L.

    2009-06-15

    An experimental study on the premixed ignition behavior of C{sub 9} fatty acid esters has been conducted in a motored CFR engine. For each test fuel, the engine compression ratio was gradually increased from the lowest point (4.43) to the point where significant high temperature heat release (HTHR) was observed. The engine exhaust was sampled and analyzed through GC-FID/TCD and GC-MS. Combustion analysis showed that the four C{sub 9} fatty acid esters tested in this study exhibited evidently different ignition behavior. The magnitude of low temperature heat release (LTHR) follows the order, ethyl nonanoate > methyl nonanoate >> methyl 2-nonenoate > methyl 3-nonenoate. The lower oxidation reactivity for the unsaturated fatty acid esters in the low temperature regime can be explained by the reduced amount of six- or seven-membered transition state rings formed during the oxidation of the unsaturated esters due to the presence of a double bond in the aliphatic chain of the esters. The inhibition effect of the double bond on the low temperature oxidation reactivity of fatty acid esters becomes more pronounced as the double bond moves toward the central position of the aliphatic chain. GC-MS analysis of exhaust condensate collected under the engine conditions where only LTHR occurred showed that the alkyl chain of the saturated fatty acid esters participated in typical paraffin-like low temperature oxidation sequences. In contrast, for unsaturated fatty acid esters, the autoignition can undergo olefin ignition pathways. For all test compounds, the ester functional group remains largely intact during the early stage of oxidation. (author)

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

    NASA Technical Reports Server (NTRS)

    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.

  20. Synthesis and evaluation of oleic acid esters as dielectric liquids

    SciTech Connect

    Thomas, P.; Sridhar, S.; Krishnaswamy, K.R.

    1996-12-31

    The worldwide depletion of petroleum crude and the search for technologically and ecologically alternative to PCB`s has led to the development of synthetic liquid dielectric which are non-flammable, non-toxic and bio-degradable. Esters like Methyl oleate and Pentaerthritol tetra oleate were synthesized in the laboratory. These esters were evaluated for its Physical, Chemical, Electrical and Aging properties and the values obtained compare well with those of commercially available liquids like Midel 7131 and RTemp fluid. Further accelerated aging studies were performed on these esters and the data obtained reveal that the esters prepared in the laboratory has very good chemical stability towards oxidation without inhibitor when compared to Midel 7131 and RTemp fluid which have phenolic inhibitors.

  1. Ammonolysis of esters of hydroxybenzoic acids on a boron phosphate catalyst

    SciTech Connect

    Suvorov, B.V.; Bukeikhanov, N.R.; Li, L.V.; Zulkasheva, A.Z.

    1987-09-10

    In this investigation boron phosphate catalyst was used for ammonolysis of methyl and ethyl esters of salicylic and 4-hydroxybenzoic acids. It was shown that ammonolysis of methyl and ethyl esters of salicylic and 4-hydroxybenzoic acids in presence of boron phosphate catalyst at a ratio of 3-7 moles of ammonia per mole of ester in a contact time of 1-5 sec at 380-400/sub 0/ can be used for obtaining o- and p- hydroxybenzonitriles in yields of over 90% of the theoretical.

  2. Synthesis of an acid addition salt of delta-aminolevulinic acid from 5-bromo levulinic acid esters

    DOEpatents

    Moens, L.

    1999-05-25

    A process is disclosed for preparing an acid addition salt of delta-aminolevulinic acid comprising. The process involves dissolving a lower alkyl 5-bromolevulinate and an alkali metal diformylamide in an organic solvent selected from the group consisting of acetonitrile, methanol, tetrahydrofuran, 2-methyltetrahydrofuran and methylformate or mixtures to form a suspension of an alkyl 5-(N,N-diformylamino) levulinate ester; and hydrolyzing the alkyl 5-(N,N-diformylamino) levulinate with an inorganic acid to form an acid addition salt of delta-amino levulinic acid.

  3. Synthesis of an acid addition salt of delta-aminolevulinic acid from 5-bromo levulinic acid esters

    DOEpatents

    Moens, Luc

    1999-01-01

    A process of preparing an acid addition salt of delta-aminolevulinic acid comprising: dissolving a lower alkyl 5-bromolevulinate and an alkali metal diformylamide in an organic solvent selected from the group consisting of acetonitrile, methanol, tetrahydrofuran, 2-methyltetrahydrofuran and methylformate or mixtures thereof to form a suspension of an alkyl 5-(N,N-diformylamino) levulinate ester; and hydrolyzing said alkyl 5-(N,N-diformylamino) levulinate with an inorganic acid to form an acid addition salt of delta-amino levulinic acid.

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

    NASA Astrophysics Data System (ADS)

    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.

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

    PubMed

    Patil, Pramod; Pratap, Amit

    2016-01-01

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

  6. An enhanced procedure for measuring organic acids and methyl esters in PM2.5

    NASA Astrophysics Data System (ADS)

    Liu, F.; Duan, F.; He, K.; Ma, Y.; Rahn, K. A.; Zhang, Q.

    2015-03-01

    We have developed an enhanced analytical procedure to measure organic acids and methyl esters in fine aerosol with much greater specificity and sensitivity than previously available. This capability is important because of these species and their low concentrations, even in highly polluted atmospheres like Beijing, China. The procedure first separates the acids and esters from the other organic compounds with anion-exchange solid- phase extraction (SPE), then, quantifies them by gas chromatography coupled with mass spectrometry. This allows us to accurately quantify the C4-C11 dicarboxylic and the C8-C30 monocarboxylic acids. Then the acids are separated from the esters on an aminopropyl SPE cartridge, whose weak retention isolates and enriches the acids from esters prevents the fatty acids and dimethyl phthalate from being overestimated. The resulting correlations between the aliphatic acids and fatty acid methyl esters (FAMEs) suggest that FAMEs had sources similar to those of the carboxylic acids, or were formed by esterifying carboxylic acids, or that aliphatic acids were formed by hydrolyzing FAMEs. In all, 17 aromatic acids were identified and quantified using this procedure coupled with gas chromatography-tandem mass spectrometry, including the five polycyclic aromatic hydrocarbon (PAH) acids 2-naphthoic, biphenyl-4-carboxylic, 9-oxo-9H-fluorene-1-carboxylic, biphenyl-4,4´-dicarboxylic, and phenanthrene-1-carboxylic acid, plus 1,8-naphthalic anhydride. Correlations between the PAH-acids and the dicarboxylic and aromatic acids indicated that the first three acids and 1,8-naphthalic anhydride were mainly secondary, the last two mainly primary.

  7. Modified branched-chain amino acid pathways give rise to acyl acids of sucrose esters exuded from tobacco leaf trichomes.

    PubMed

    Kandra, G; Severson, R; Wagner, G J

    1990-03-10

    A major diversion of carbon from branched-chain amino acid biosynthesis/catabolism to form acyl moieties of sucrose esters (6-O-acetyl-2,3,4-tri-O-acyl-alpha-D-glucopyranosyl-beta-D- fructofuranosides) was observed to be associated with specialized trichome head cells which secrete large amounts of sucrose esters. Surface chemistry and acetyl and acyl substituent groups of tobacco (T.I. 1068) sucrose esters were identified and quantified by gas chromatography/mass spectrometry. Sucrose esters were prominent surface constituents and 3-methylvaleric acid, 2- and 3-methylbutyric acid, and methylpropionic acid accounted for 60%, 25% and 9%, respectively, of total C3--C7 acyl substituents. Radiolabeled Thr, Ile, Val, Leu, pyruvate and Asp, metabolites of branched-chain amino acid pathways, were compared with radioactively labeled acetate and sucrose as donors of carbon to sucrose, acetyl and acyl components of sucrose esters using epidermal peels with undisturbed trichomes. Preparations of biosynthetically competent trichome heads (site of sucrose ester formation) were also examined. Results indicate that 3-methylvaleryl and 2-methylbutyryl groups are derived from the Thr pathway of branched-chain amino acid metabolism, 3-methylbutyryl and methylpropionyl groups are formed via the pyruvate pathway, and that acetyl groups are principally formed directly via acetyl-CoA. Arguments are presented which rule out participation of fatty acid synthase in the formation of prominent acyl acids. Results suggest that the shunting of carbon away from the biosynthesis of Val, Leu and Ile may be due to a low level of amino acid utilization in protein synthesis in specialized glandular head cells of trichomes. This would result in the availability of corresponding oxo acids for CoA activation and esterification to form sucrose esters. Preliminary evidence was found for the involvement of cycling reactions in oxo-acid-chain lengthening and for utilization of pyruvate-derived 2

  8. Branched Chain Amino Acid Metabolism in the Biosynthesis of Lycopersicon pennellii Glucose Esters 1

    PubMed Central

    Walters, Donald S.; Steffens, John C.

    1990-01-01

    Lycopersicon pennellii Corr. (D'Arcy) an insect-resistant, wild tomato possesses high densities of glandular trichomes which exude a mixture of 2,3,4-tri-O-acylated glucose esters that function as a physical impediment and feeding deterrent to small arthropod pests. The acyl moieties are branched C4 and C5 acids, and branched and straight chain C10, C11, and C12 acids. The structure of the branched acyl constituents suggests that the branched chain amino acid biosynthetic pathway participates in their biosynthesis. [14C]Valine and deuterated branched chain amino acids (and their oxo-acid derivatives) were incorporated into branched C4 and C5 acid groups of glucose esters by a process of transamination, oxidative decarboxylation and subsequent acylation. C4 and C5 branched acids were elongated by two carbon units to produce the branched C10-C12 groups. Norvaline, norleucine, allylglycine, and methionine also were processed into acyl moieties and secreted from the trichomes as glucose esters. Changes in the acyl composition of the glucose esters following sulfonylurea herbicide administration support the participation of acetohydroxyacid synthetase and the other enzymes of branched amino acid biosynthesis in the production of glucose esters. PMID:16667654

  9. 40 CFR 721.1875 - Boric acid, alkyl and substituted alkyl esters (generic name).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Boric acid, alkyl and substituted... Significant New Uses for Specific Chemical Substances § 721.1875 Boric acid, alkyl and substituted alkyl... chemical substance boric acid, alkyl and substituted alkyl esters (PMN P-86-1252) is subject to...

  10. 40 CFR 721.1875 - Boric acid, alkyl and substituted alkyl esters (generic name).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Boric acid, alkyl and substituted... Significant New Uses for Specific Chemical Substances § 721.1875 Boric acid, alkyl and substituted alkyl... chemical substance boric acid, alkyl and substituted alkyl esters (PMN P-86-1252) is subject to...

  11. 40 CFR 721.1875 - Boric acid, alkyl and substituted alkyl esters (generic name).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

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

  12. 40 CFR 721.1875 - Boric acid, alkyl and substituted alkyl esters (generic name).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Boric acid, alkyl and substituted... Significant New Uses for Specific Chemical Substances § 721.1875 Boric acid, alkyl and substituted alkyl... chemical substance boric acid, alkyl and substituted alkyl esters (PMN P-86-1252) is subject to...

  13. 40 CFR 721.1875 - Boric acid, alkyl and substituted alkyl esters (generic name).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Boric acid, alkyl and substituted... Significant New Uses for Specific Chemical Substances § 721.1875 Boric acid, alkyl and substituted alkyl... chemical substance boric acid, alkyl and substituted alkyl esters (PMN P-86-1252) is subject to...

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

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

  15. 40 CFR 721.1728 - Benzoic acid, 2-(3-phenylbutylidene)amino-, methyl ester.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... New Uses for Specific Chemical Substances § 721.1728 Benzoic acid, 2-(3-phenylbutylidene)amino... substance identified as benzoic acid, 2-(3-phenylbutylidene)amino-, methyl ester (PMN P-85-1211) is subject... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Benzoic acid,...

  16. 40 CFR 721.1728 - Benzoic acid, 2-(3-phenylbutylidene)amino-, methyl ester.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... New Uses for Specific Chemical Substances § 721.1728 Benzoic acid, 2-(3-phenylbutylidene)amino... substance identified as benzoic acid, 2-(3-phenylbutylidene)amino-, methyl ester (PMN P-85-1211) is subject... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Benzoic acid,...

  17. 40 CFR 721.1728 - Benzoic acid, 2-(3-phenylbutylidene)amino-, methyl ester.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... New Uses for Specific Chemical Substances § 721.1728 Benzoic acid, 2-(3-phenylbutylidene)amino... substance identified as benzoic acid, 2-(3-phenylbutylidene)amino-, methyl ester (PMN P-85-1211) is subject... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Benzoic acid,...

  18. 40 CFR 721.1728 - Benzoic acid, 2-(3-phenylbutylidene)amino-, methyl ester.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... New Uses for Specific Chemical Substances § 721.1728 Benzoic acid, 2-(3-phenylbutylidene)amino... substance identified as benzoic acid, 2-(3-phenylbutylidene)amino-, methyl ester (PMN P-85-1211) is subject... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Benzoic acid,...

  19. 40 CFR 721.1728 - Benzoic acid, 2-(3-phenylbutylidene)amino-, methyl ester.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... New Uses for Specific Chemical Substances § 721.1728 Benzoic acid, 2-(3-phenylbutylidene)amino... substance identified as benzoic acid, 2-(3-phenylbutylidene)amino-, methyl ester (PMN P-85-1211) is subject... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Benzoic acid,...

  20. Investigation of the extraction properties of dibutyl ester of dibutoxymethane phosphonic acid

    SciTech Connect

    Herrmann, E.; Hala, J.

    1983-01-01

    The extraction properties of the dibutyl ester of dibutoxymethane phosphonic acid (DBDBMP), an analog of TBP with a P-C bond, were shown to be similar to those of TBP except for hydrolysis of DBDBMP in acidic solutions. The formation of acidic organophosphorus compounds during hydrolysis of DBDBMP was confirmed by /sup 31/P-N.M.R. measurements. 4 figures, 1 table.

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

  2. 40 CFR 721.10412 - Phosphonic acid ester (generic) (P-07-706).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... appropriate gas/vapor cartridges (organic vapor, acid gas, or substance-specific); NIOSH-certified powered air... (organic vapor, acid gas, or substance-specific); NIOSH-certified powered air-purifying respirator with a... Specific Chemical Substances § 721.10412 Phosphonic acid ester (generic) (P-07-706). (a) Chemical...

  3. 40 CFR 721.10412 - Phosphonic acid ester (generic) (P-07-706).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... appropriate gas/vapor cartridges (organic vapor, acid gas, or substance-specific); NIOSH-certified powered air... (organic vapor, acid gas, or substance-specific); NIOSH-certified powered air-purifying respirator with a... Specific Chemical Substances § 721.10412 Phosphonic acid ester (generic) (P-07-706). (a) Chemical...

  4. 40 CFR 721.10412 - Phosphonic acid ester (generic) (P-07-706).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... appropriate gas/vapor cartridges (organic vapor, acid gas, or substance-specific); NIOSH-certified powered air... (organic vapor, acid gas, or substance-specific); NIOSH-certified powered air-purifying respirator with a... Specific Chemical Substances § 721.10412 Phosphonic acid ester (generic) (P-07-706). (a) Chemical...

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

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... combined lactic acid, 14-18 percent; and acid number, 12 maximum. (c) It is used in amounts not in excess... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Lactylated fatty acid esters of glycerol and... DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION Multipurpose Additives § 172.850 Lactylated fatty...

  6. 21 CFR 172.850 - Lactylated fatty acid esters of glycerol and propylene glycol.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... combined lactic acid, 14-18 percent; and acid number, 12 maximum. (c) It is used in amounts not in excess... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Lactylated fatty acid esters of glycerol and... DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION Multipurpose Additives § 172.850 Lactylated fatty...

  7. 21 CFR 172.850 - Lactylated fatty acid esters of glycerol and propylene glycol.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... combined lactic acid, 14-18 percent; and acid number, 12 maximum. (c) It is used in amounts not in excess... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Lactylated fatty acid esters of glycerol and... DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION Multipurpose Additives § 172.850 Lactylated fatty...

  8. 21 CFR 172.850 - Lactylated fatty acid esters of glycerol and propylene glycol.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... combined lactic acid, 14-18 percent; and acid number, 12 maximum. (c) It is used in amounts not in excess... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Lactylated fatty acid esters of glycerol and... DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION Multipurpose Additives § 172.850 Lactylated fatty...

  9. Kinematic viscosity of fatty acid methyl esters: Prediction, calculated viscosity contribution of esters with unavailable data, and carbon-oxygen equivalents

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Many properties of biodiesel, the mono-alkyl esters of vegetable oils, animal fats or other triacylglycerol-containing feedstocks, are largely determined by its major components, the fatty acid alkyl esters. Therefore, information on the properties of individual components and their interaction is ...

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

    PubMed

    Anantharaj, S; Jayakannan, M

    2012-08-13

    A new dual ester-urethane melt condensation methodology for biological monomers-amino acids was developed to synthesize new classes of thermoplastic polymers under eco-friendly and solvent-free polymerization approach. Naturally abundant L-amino acids were converted into dual functional ester-urethane monomers by tailor-made synthetic approach. Direct polycondensation of these amino acid monomers with commercial diols under melt condition produced high molecular weight poly(ester-urethane)s. The occurrence of the dual ester-urethane process and the structure of the new poly(ester-urethane)s were confirmed by (1)H and (13)C NMR. The new dual ester-urethane condensation approach was demonstrated for variety of amino acids: glycine, β-alanine, L-alanine, L-leucine, L-valine, and L-phenylalanine. MALDI-TOF-MS end group analysis confirmed that the amino acid monomers were thermally stable under the melt polymerization condition. The mechanism of melt process and the kinetics of the polycondensation were studied by model reactions and it was found that the amino acid monomer was very special in the sense that their ester and urethane functionality could be selectively reacted by polymerization temperature or catalyst. The new polymers were self-organized as β-sheet in aqueous or organic solvents and their thermal properties such as glass transition temperature and crystallinity could be readily varied using different l-amino acid monomers or diols in the feed. Thus, the current investigation opens up new platform of research activates for making thermally stable and renewable engineering thermoplastics from natural resource amino acids. PMID:22713137

  11. Reductive Etherification of Fatty Acids or Esters with Alcohols using Molecular Hydrogen.

    PubMed

    Erb, Benjamin; Risto, Eugen; Wendling, Timo; Gooßen, Lukas J

    2016-06-22

    In the presence of a catalyst system consisting of a ruthenium/triphos complex and the Brønsted acid trifluoromethanesulfonimide, mixtures of fatty acids and aliphatic alcohols are converted into the corresponding ethers at 70 bar H2 . The protocol allows the sustainable one-step synthesis of valuable long-chain ether fragrances, lubricants, and surfactants from renewable sources. The reaction protocol is extended to various fatty acids and esters both in pure form and as mixtures, for example, tall oil acids or rapeseed methyl ester (RME). Even the mixed triglyceride rapeseed oil was converted in one step. PMID:27214823

  12. Caffeic acid phenethyl ester inhibits liver fibrosis in rats

    PubMed Central

    Li, Mei; Wang, Xiu-Fang; Shi, Juan-Juan; Li, Ya-Ping; Yang, Ning; Zhai, Song; Dang, Shuang-Suo

    2015-01-01

    AIM: To investigate the hepatoprotective effects and antioxidant activity of caffeic acid phenethyl ester (CAPE) in rats with liver fibrosis. METHODS: A total of 75 male Sprague-Dawley rats were randomly assigned to seven experimental groups: a normal group (n = 10), a vehicle group (n = 10), a model group (n = 15), a vitamin E group (n = 10), and three CAPE groups (CAPE 3, 6 and 12 mg/kg, n = 10, respectively). Liver fibrosis was induced in rats by injecting CCl4 subcutaneously, feeding with high fat forage, and administering 30% alcohol orally for 10 wk. Concurrently, CAPE (3, 6 and 12 mg/kg) was intraperitoneally administered daily for 10 wk. After that, serum total bilirubin (TBil), aminotransferase (ALT) and aspartate aminotransferase (AST) levels were measured to assess hepatotoxicity. To investigate antioxidant activity of CAPE, malondialdehyde (MDA), glutathione (GSH) levels, catalase (CAT) and superoxide dismutase (SOD) activities in liver tissue were determined. Moreover, the effect of CAPE on α-smooth muscle actin (α-SMA), a characteristic hallmark of activated hepatic stellate cells (HSCs), and NF-E2-related factor 2 (Nrf2), a key transcription factor for antioxidant systems, was investigated by immunohistochemistry. RESULTS: Compared to the model group, intraperitoneal administration of CAPE decreased TBil, ALT, and AST levels in liver fibrosis rats (P < 0.05), while serum TBil was decreased by CAPE in a dose-dependent manner. In addition, the liver hydroxyproline contents in both the 6 and 12 mg/kg CAPE groups were markedly lower than that in the model group (P < 0.05 and P < 0.001, respectively). CAPE markedly decreased MDA levels and, in turn, increased GSH levels, as well as CAT and SOD activities in liver fibrosis rats compared to the model group (P < 0.05). Moreover, CAPE effectively inhibited α-SMA expression while increasing Nrf2 expression compared to the model group (P < 0.01). CONCLUSION: The protective effects of CAPE against liver

  13. Asymmetric Synthesis of Diverse Glycolic Acid Scaffolds via Dynamic Kinetic Resolution of α-Keto Esters

    PubMed Central

    Steward, Kimberly M.; Corbett, Michael T.; Goodman, C. Guy; Johnson, Jeffrey S.

    2012-01-01

    The dynamic kinetic resolution of α-keto esters via asymmetric transfer hydrogenation has been developed as a technique for the highly stereoselective construction of structurally diverse β-substituted-α-hydroxy carboxylic acid derivatives. Through the development of a privileged m-terphenylsulfonamide for (arene)RuCl(monosulfonamide) complexes with a high affinity for selective α-keto ester reduction, excellent levels of chemo-, diastereo-, and enantiocontrol can be realized in the reduction of β-aryl- and β-chloro-α-keto esters. PMID:23186551

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

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...-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...

  15. 40 CFR 721.1576 - 1,3-Benzenedicarboxylic acid, bis[[4-[(ethenyloxy)methyl] cyclohexyl] methyl] ester.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 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...

  16. 40 CFR 721.1576 - 1,3-Benzenedicarboxylic acid, bis[[4-[(ethenyloxy)methyl] cyclohexyl] methyl] ester.

    Code of Federal Regulations, 2010 CFR

    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...

  17. 40 CFR 721.4792 - 2-propenoic acid, 2-methyl-, C11-14-isoalkyl esters, C13-rich.

    Code of Federal Regulations, 2010 CFR

    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...

  18. 40 CFR 721.1578 - 1,4-Benzenedicarboxylic acid, bis[[4-[(ethenyloxy)methyl] cyclohexyl] methyl] ester.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 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...

  19. 40 CFR 721.1578 - 1,4-Benzenedicarboxylic acid, bis[[4-[(ethenyloxy)methyl] cyclohexyl] methyl] ester.

    Code of Federal Regulations, 2010 CFR

    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...

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

    NASA Technical Reports Server (NTRS)

    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.

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

    SciTech Connect

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

    1984-05-01

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

  2. Aminocarbonyloxymethyl ester prodrugs of flufenamic acid and diclofenac: suppressing the rearrangement pathway in aqueous media.

    PubMed

    Ribeiro, Lina; Silva, Nuno; Iley, Jim; Rautio, Jarkko; Järvinen, Tomi; Mota-Filipe, Hélder; Moreira, Rui; Mendes, Eduarda

    2007-01-01

    Aminocarbonyloxymethyl ester prodrugs are known to undergo rearrangement in aqueous solutions to form the corresponding N-acylamine side product via an O-->N intramolecular acyl transfer from the carbamate conjugate base. Novel aminocarbonyloxymethyl esters of diclofenac and flufenamic acid containing amino acid amide carriers were synthesized and evaluated as potential prodrugs displaying less ability to undergo rearrangement. These compounds were prepared in reasonable yield by a four-step synthetic method that uses the appropriate N-Boc-protected amino acid N-hydroxysuccinimide ester and secondary amine and chloromethyl chloroformate as key reactants. Their reactivity in pH 7.4 buffer and 80% human plasma at 37 degrees C was assessed by RP-HPLC. The aminocarbonyloxymethyl esters containing a secondary carbamate group derived from amino acids such as glycine or phenylalanine were hydrolyzed quantitatively to the parent drug both in non-enzymatic and enzymatic conditions, with no rearrangement product being detected. The oral bioavailability in rats was determined for selected diclofenac derivatives. These derivatives displayed a bioavailability of 25 to 68% relative to that of diclofenac, probably due to their poor aqueous solubility and lipophilicity. These results suggest that further optimization of aminocarbonyloxymethyl esters as potential prodrugs for non-steroidal anti-inflammatory drugs require the use of amino acid carriers with ionizable groups to improve aqueous solubility. PMID:17206608

  3. 21 CFR 172.848 - Lactylic esters of fatty acids.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... are prepared from lactic acid and fatty acids meeting the requirements of § 172.860(b) and/or oleic acid derived from tall oil fatty acids meeting the requirements of § 172.862. (b) They are used...

  4. 21 CFR 172.848 - Lactylic esters of fatty acids.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... accordance with the following prescribed conditions: (a) They are prepared from lactic acid and fatty acids meeting the requirements of § 172.860(b) and/or oleic acid derived from tall oil fatty acids meeting...

  5. 21 CFR 172.848 - Lactylic esters of fatty acids.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... are prepared from lactic acid and fatty acids meeting the requirements of § 172.860(b) and/or oleic acid derived from tall oil fatty acids meeting the requirements of § 172.862. (b) They are used...

  6. 21 CFR 172.848 - Lactylic esters of fatty acids.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... are prepared from lactic acid and fatty acids meeting the requirements of § 172.860(b) and/or oleic acid derived from tall oil fatty acids meeting the requirements of § 172.862. (b) They are used...

  7. 40 CFR 721.10300 - Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester. 721.10300 Section 721.10300 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.10300 Benzeneacetic acid,...

  8. 40 CFR 721.10300 - Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester. 721.10300 Section 721.10300 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.10300 Benzeneacetic acid,...

  9. 40 CFR 721.10300 - Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester. 721.10300 Section 721.10300 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.10300 Benzeneacetic acid,...

  10. A comprehensive evaluation of the density of neat fatty acids and esters

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Density is one of the most important physical properties of a chemical compound, affecting numerous applications. An application in the case of fatty acid esters (biodiesel) is that density is specified in some biodiesel standards. In the present work, the density of fatty acid methyl, ethyl, propyl...

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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. Fuel and lubricant additives from acid treated mixtures of vegetable oil derived amides and esters

    SciTech Connect

    Bonazza, B.R.; Devault, A.N.

    1981-05-26

    Vegetable oils such as corn oil, peanut oil, and soy oil are reacted with polyamines to form a mixture containing amides, imides, half esters, and glycerol with subsequent treatment with a strong acid such as sulfonic acid to produce a product mix that has good detergent properties in fuels and lubricants.

  13. 40 CFR 721.7770 - Alkylphenoxypoly(oxyethylene) sulfuric acid ester, substituted amine salt.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... Significant New Uses for Specific Chemical Substances § 721.7770 Alkylphenoxypoly(oxyethylene) sulfuric acid...) The chemical substance identified as alkyl phenoxypoly(oxyethylene) sulfuric acid ester, substituted... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Alkylphenoxypoly(oxyethylene)...

  14. 40 CFR 721.7770 - Alkylphenoxypoly(oxyethylene) sulfuric acid ester, substituted amine salt.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... Significant New Uses for Specific Chemical Substances § 721.7770 Alkylphenoxypoly(oxyethylene) sulfuric acid...) The chemical substance identified as alkyl phenoxypoly(oxyethylene) sulfuric acid ester, substituted... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Alkylphenoxypoly(oxyethylene)...

  15. 40 CFR 721.7770 - Alkylphenoxypoly(oxyethylene) sulfuric acid ester, substituted amine salt.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... Significant New Uses for Specific Chemical Substances § 721.7770 Alkylphenoxypoly(oxyethylene) sulfuric acid...) The chemical substance identified as alkyl phenoxypoly(oxyethylene) sulfuric acid ester, substituted... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Alkylphenoxypoly(oxyethylene)...

  16. 40 CFR 721.7770 - Alkylphenoxypoly(oxyethylene) sulfuric acid ester, substituted amine salt.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... Significant New Uses for Specific Chemical Substances § 721.7770 Alkylphenoxypoly(oxyethylene) sulfuric acid...) The chemical substance identified as alkyl phenoxypoly(oxyethylene) sulfuric acid ester, substituted... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Alkylphenoxypoly(oxyethylene)...

  17. 40 CFR 721.7770 - Alkylphenoxypoly(oxyethylene) sulfuric acid ester, substituted amine salt.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... Significant New Uses for Specific Chemical Substances § 721.7770 Alkylphenoxypoly(oxyethylene) sulfuric acid...) The chemical substance identified as alkyl phenoxypoly(oxyethylene) sulfuric acid ester, substituted... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Alkylphenoxypoly(oxyethylene)...

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

  19. 40 CFR 721.1950 - 2-Butenedioic acid (Z), mono(2-((1-oxopropenyloxy)ethyl) ester .

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false 2-Butenedioic acid (Z), mono(2-((1... 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...

  20. 40 CFR 721.1950 - 2-Butenedioic acid (Z), mono(2-((1-oxopropenyloxy)ethyl) ester .

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false 2-Butenedioic acid (Z), mono(2-((1... 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...

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

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false 2-Butenedioic acid (Z), mono(2-((1... 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...

  2. 40 CFR 721.10243 - Phosphonic acid, P-[2-[bis(2-hydroxyethyl)amino]ethyl]-, bis(2-chloroethyl) ester.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Phosphonic acid, P- ethyl]-, bis(2... Specific Chemical Substances § 721.10243 Phosphonic acid, P- ethyl]-, bis(2-chloroethyl) ester. (a... phosphonic acid, P- ethyl]-, bis(2-chloroethyl) ester (PMN P-09-193; CAS No. 55088-28-3) is subject...

  3. 40 CFR 721.10243 - Phosphonic acid, P-[2-[bis(2-hydroxyethyl)amino]ethyl]-, bis(2-chloroethyl) ester.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Phosphonic acid, P- ethyl]-, bis(2... Specific Chemical Substances § 721.10243 Phosphonic acid, P- ethyl]-, bis(2-chloroethyl) ester. (a... phosphonic acid, P- ethyl]-, bis(2-chloroethyl) ester (PMN P-09-193; CAS No. 55088-28-3) is subject...

  4. 40 CFR 721.10243 - Phosphonic acid, P-[2-[bis(2-hydroxyethyl)amino]ethyl]-, bis(2-chloroethyl) ester.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Phosphonic acid, P- ethyl]-, bis(2... Specific Chemical Substances § 721.10243 Phosphonic acid, P- ethyl]-, bis(2-chloroethyl) ester. (a... phosphonic acid, P- ethyl]-, bis(2-chloroethyl) ester (PMN P-09-193; CAS No. 55088-28-3) is subject...

  5. Lewis acid catalysis of photochemical reactions. 5. Selective isomerization of conjugated butenoic and dienoic esters

    SciTech Connect

    Lewis, F.D.; Howard, D.K.; Barancyk, S.V.; Oxman, J.D.

    1986-05-28

    The effects of Lewis and Broensted acids upon the photoisomerization reactions of several conjugated butenoic and dienoic esters have been investigated. Lewis acids inhibit the photochemical deconjugation of ..cap alpha..,..beta..- to ..beta..,..gamma..-unsaturated butenoic esters and shift the photoequilibrium between E and Z isomers toward the Z isomer. As such, irradiation of E ..cap alpha..,..beta..-unsaturated esters in the presence of EtAlCl/sub 2/ provides a convenient method for the preparation of the thermodynamically less stable Z isomer. Irradiation of methyl (E,E)-2,4-hexadienoate and methyl (E,E)-5-phenyl-2,4-pentadienoate in the absence of added catalysts results in nonselective E,Z isomerization to give mixtures of all four stereoisomers in roughly comparable yields. In the presence of the Broensted acid trifluoroacetic acid, quantitative conversion of methyl 2,4-hexadienoates to methyl 3,4-hexadienoate is observed. The acid serves as a catalyst for the thermal 1,3-hydrogen shift of an allenic enol ester formed via a photochemical 1,5-hydrogen shift of the conjugated esters. Irradiation of the ground-state complexes of the conjugated esters with the Lewis acids EtAlCl/sub 2/ or BF/sub 3/ results in selective E,Z isomerization about the ..cap alpha..,..beta..-double bond in methyl 2,4-hexadienoate and the ..gamma..,delta-double bond in methyl 5-phenyl-24-pentadienoate. The mechanistic bases for the observed effects of Lewis acids are selective excitation of the more strongly absorbing E complex and more efficient isomerization of the excited E vs. Z complex.

  6. Facile synthesis of acid-labile polymers with pendent ortho esters.

    PubMed

    Cheng, Jing; Ji, Ran; Gao, Shi-Juan; Du, Fu-Sheng; Li, Zi-Chen

    2012-01-01

    This work presents a facile approach for preparation of acid-labile and biocompatible polymers with pendent cyclic ortho esters, which is based on the efficient and mild reactions between cyclic ketene acetal (CKA) and hydroxyl groups. Three CKAs, 2-ethylidene-1,3-dioxane (EDO), 2-ethylidene-1,3-dioxolane (EDL), and 2-ethylidene-4- methyl-1,3-dioxolane (EMD) were prepared from the corresponding cyclic vinyl acetals by catalytic isomerization of the double bond. The reaction of CKAs with different alcohols and diols was examined using trace of p-toluenesulfonic acid as a catalyst. For the monohydroxyl alcohols, cyclic ortho esters were formed by simple addition of the hydroxyl group toward CKAs with ethanol showing a much greater reactivity than iso-propanol. When 1,2- or 1,3-diols were used to react with the CKAs, we observed the isomerized cyclic ortho esters besides the simple addition products. Biocompatible polyols, that is, poly(2-hydroxyethyl acrylate) (PHEA) and poly(vinyl alcohol) (PVA) were then modified with CKAs, and the degree of substitution of the pendent ortho esters can be easily tuned by changing feed ratio. Both the small molecule ortho esters and the CKA-modified polymers demonstrate the pH-dependent hydrolysis profiles, which depend also on the chemical structure of the ortho esters as well as the polymer hydrophobicity. PMID:22176024

  7. 21 CFR 172.854 - Polyglycerol esters of fatty acids.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... acids are used as a cloud inhibitor in vegetable and salad oils when use is not precluded by standards... to perform its cloud-inhibiting effect. Oleic acid derived from tall oil fatty acids conforming...

  8. 21 CFR 172.854 - Polyglycerol esters of fatty acids.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... acids are used as a cloud inhibitor in vegetable and salad oils when use is not precluded by standards... to perform its cloud-inhibiting effect. Oleic acid derived from tall oil fatty acids conforming...

  9. 21 CFR 172.854 - Polyglycerol esters of fatty acids.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... acids are used as a cloud inhibitor in vegetable and salad oils when use is not precluded by standards... to perform its cloud-inhibiting effect. Oleic acid derived from tall oil fatty acids conforming...

  10. 21 CFR 172.854 - Polyglycerol esters of fatty acids.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... acids are used as a cloud inhibitor in vegetable and salad oils when use is not precluded by standards... to perform its cloud-inhibiting effect. Oleic acid derived from tall oil fatty acids conforming...

  11. Effect of physical ageing on properties of PLA plasticized with oligomeric esters of lactic acid

    NASA Astrophysics Data System (ADS)

    Castaldo, R.; Ambrogi, V.; Avella, M.; Avolio, R.; Carfagna, C.; Cocca, M.; Errico, M. E.; Gentile, G.

    2014-05-01

    Two oligomeric esters of lactic acid with carboxyl or hydroxyl terminal groups were employed to plasticize polylactic acid. The miscibility of the blends as well as the mechanical, thermal and gas/vapour transport properties were tested as a function of plasticizer content and of physical ageing. A ductile PLA behavior was obtained with the addition of at least 20 wt% of both esters supplying an increase of elongation at break values higher than 400%. These blends retain their ductile feature also after ageing. Finally migration tests proved the compliance of these materials with the EU regulation for food contact plastics.

  12. Study on Synthesis, Characterization and Antiproliferative Activity of Novel Diisopropylphenyl Esters of Selected Fatty Acids.

    PubMed

    Reddy, Yasa Sathyam; Kaki, Shiva Shanker; Rao, Bala Bhaskara; Jain, Nishant; Vijayalakshmi, Penumarthy

    2016-01-01

    The present study describes the synthesis, characterization and evaluation of antiproliferative activity of novel diisopropylphenyl esters of alpha-linolenic acid (ALA), valproic acid (VA), butyric acid (BA) and 2-ethylhexanoic acid (2-EHA). These esters were chemically synthesized by the esterification of fatty acids with 2,6-diisopropylphenol and 2,4-diisopropylphenol (propofol). The structure of new conjugates viz. propofol-(alpha-linolenic acid) (2,6P-ALA and 2,4P-ALA), propofol-valproic acid (2,6P-VA and 2,4P-VA), propofol-butyric acid (2,6P-BA and 2,4P-BA) and propofol-(2-ethylhexanoic acid) (2,6P2-EHA and 2,4P-2-EHA) were characterized by FT-IR, NMR ((1)H, (13)C) and mass spectral data. The synthesized conjugates having more lipophilic character were tested for antiproliferative in vitro studies on A549, MDA-MB-231, HeLa, Mia-Pa-Ca and HePG2 cancer cell lines. All the conjugates showed specific growth inhibition on studied cancer cell lines. Among the synthesized esters, the conjugates synthesized from BA, VA and 2-EHA exhibited prominent growth inhibition against A549, HeLa, Mia-Pa-Ca and HePG2 cancer cell lines. The preliminary results suggest that the entire novel conjugates possess antiproliferative properties that reduce the proliferation of cancer cells in vitro. PMID:26666272

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

    PubMed

    Goodger, Jason Q D; Woodrow, Ian E

    2011-12-01

    The glycosylation of lipophilic small molecules produces many important plant secondary metabolites. The majority of these are O-glycosides with relatively fewer occurring as glucose esters of aromatic or aliphatic acids. In particular, monoterpene acid glucose esters have much lower structural diversity and distribution compared to monoterpene glycosides. Nevertheless, there have been over 20 monoterpene acid glucose esters described from trees in the genus Eucalyptus (Myrtaceae) in recent years, all based on oleuropeic acid, menthiafolic acid or both. Here we review all of the glucose esters containing these monoterpenoids identified in plants to date. Many of the compounds contain phenolic aglycones and all contain at least one α,β-unsaturated carbonyl, affording a number of important potential therapeutic reactivities such as anti-tumor promotion, carcinogenesis suppression, and anti-oxidant and anti-inflammatory activities. Additional properties such as cytotoxicity, bitterness, and repellency are suggestive of a role in plant defence, but we also discuss their localization to the exterior of foliar secretory cavity lumina, and suggest they may also protect secretory cells from toxic terpenes housed within these structures. Finally we discuss how the use of a recently developed protocol to isolate secretory cavities in a functional state could be used in conjunction with systems biology approaches to help characterize their biosynthesis and roles in plants. PMID:21945720

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

    SciTech Connect

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

    2008-07-08

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

  15. Behavioral and electrophysiological responses of Culex quinquefasciatus to certain fatty acid esters.

    PubMed

    Seenivasagan, Thangaraj; Guha, Lopamudra; Iqbal, S Thanvir

    2013-12-01

    Oviposition response of gravid Culex quinquefasciatus females to a series of synthetic fatty acid esters was evaluated at 10ppm under laboratory conditions. Octyl tridecanoate and propyl octadecanoate elicited 85% and 73% increased ovipositional responses respectively, compared to control, among the 16 esters tested. Other 14 esters showed highly significant repellency (67-96%) to gravid females. Standard 3-methyl indole received 69% increased egg deposition compared to control. In the Y-tube olfactometer, gravid C. quinquefasciatus females exhibited 78, 64% and 58% orientation respectively to octyl tridecanoate, propyl octadecanoate and 3-methyl indole. Gravid females exhibited 19-41% reduced orientation toward treatment odors of other esters significantly different from respective control. Electroantennogram studies revealed 4-18-fold increased antennal response, in which 3-methyl indole, octyl tridecanoate and propyl octadecanoate elicited 8-, 18- and 15-fold EAG response respectively, compared to control. Relative EAG response of octyl tridecanoate compared to standard 3-methyl indole was significantly different. Reduced EAG responses were elicited by FAE-06, -08, -13, -14 and -15, while the relative EAG responses of other esters were at par with the standard stimulus. These, esters could be utilized potentially as oviposition attractants and repellents against C. quinquefasciatus females to reduce the breeding in polluted water along with existing integrated vector control methods. PMID:24055543

  16. Hydrolysis of Indole-3-Acetic Acid Esters Exposed to Mild Alkaline Conditions 1

    PubMed Central

    Baldi, Bruce G.; Maher, Barbara R.; Cohen, Jerry D.

    1989-01-01

    Ester conjugates of indole-3-acetic acid are hydrolyzed easily in basic solutions; however, quantitative data have not been available on the relationship between pH and rate of hydrolysis of the known ester conjugates. The use of basic conditions during extraction or purification of IAA by several laboratories suggested that a more systematic analysis of this process was needed. In this report we present data indicating: (a) that measurable hydrolysis of IAA-glucose (from standard solutions) and IAA-esters (from maize kernel extracts) occurs with only a few hours of treatment at pH 9 or above; (b) that the lability of some ester conjugates is even greater than that of IAA-glucose; and (c) that ester hydrolysis of standard compounds, IAA-glucose and IAA-p-nitrophenol, occurs in the `three phase extraction system' proposed by Liu and Tillberg ([1983] Physiol Plant 57: 441-447). These data indicate that the potential for problems with inadvertent hydrolysis of ester conjugates of IAA exists even at moderate pH values and in the multiphase system where exposure to basic conditions was thought to be limited. PMID:16667049

  17. 21 CFR 172.225 - Methyl and ethyl esters of fatty acids produced from edible fats and oils.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

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

  18. 40 CFR 721.3130 - Sulfuric acid, mono-C9-11-alkyl esters, sodium salts.

    Code of Federal Regulations, 2010 CFR

    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 substance and significant new uses subject to reporting. (1) The chemical substance identified as...

  19. 40 CFR 721.3130 - Sulfuric acid, mono-C9-11-alkyl esters, sodium salts.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Sulfuric acid, mono-C9-11-alkyl esters... Specific Chemical Substances § 721.3130 Sulfuric acid, mono-C9-11-alkyl esters, sodium salts. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as...

  20. 40 CFR 721.3130 - Sulfuric acid, mono-C9-11-alkyl esters, sodium salts.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Sulfuric acid, mono-C9-11-alkyl esters... Specific Chemical Substances § 721.3130 Sulfuric acid, mono-C9-11-alkyl esters, sodium salts. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as...

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

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Sulfuric acid, mono-C9-11-alkyl esters... Specific Chemical Substances § 721.3130 Sulfuric acid, mono-C9-11-alkyl esters, sodium salts. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as...

  2. 40 CFR 721.3130 - Sulfuric acid, mono-C9-11-alkyl esters, sodium salts.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Sulfuric acid, mono-C9-11-alkyl esters... Specific Chemical Substances § 721.3130 Sulfuric acid, mono-C9-11-alkyl esters, sodium salts. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as...

  3. 40 CFR 721.304 - Acetic acid, [(5-chloro-8-quinolinyl)oxy-], 1-methyl hexyl ester.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical 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...

  4. 40 CFR 721.304 - Acetic acid, [(5-chloro-8-quinolinyl)oxy-], 1-methyl hexyl ester.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical 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...

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

    PubMed

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

    2006-11-01

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

  6. Process for the generation of .alpha., .beta.-unsaturated carboxylic acids and esters using niobium catalyst

    DOEpatents

    Gogate, Makarand Ratnakav; Spivey, James Jerome; Zoeller, Joseph Robert

    1999-01-01

    A process using a niobium catalyst includes the step of reacting an ester or carboxylic acid with oxygen and an alcohol in the presence a niobium catalyst to respectively produce an .alpha.,.beta.-unsaturated ester or carboxylic acid. Methanol may be used as the alcohol, and the ester or carboxylic acid may be passed over the niobium catalyst in a vapor stream containing oxygen and methanol. Alternatively, the process using a niobium catalyst may involve the step of reacting an ester and oxygen in the presence the niobium catalyst to produce an .alpha.,.beta.-unsaturated carboxylic acid. In this case the ester may be a methyl ester. In either case, niobium oxide may be used as the niobium catalyst with the niobium oxide being present on a support. The support may be an oxide selected from the group consisting of silicon oxide, aluminum oxide, titanium oxide and mixtures thereof. The catalyst may be formed by reacting niobium fluoride with the oxide serving as the support. The niobium catalyst may contain elemental niobium within the range of 1 wt % to 70 wt %, and more preferably within the range of 10 wt % to 30 wt %. The process may be operated at a temperature from 150 to 450.degree. C. and preferably from 250 to 350.degree. C. The process may be operated at a pressure from 0.1 to 15 atm. absolute and preferably from 0.5-5 atm. absolute. The flow rate of reactants may be from 10 to 10,000 L/kg.sub.(cat) /h, and preferably from 100 to 1,000 L/kg.sub.(cat) /h.

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

    PubMed

    MacGee, J; Williams, M G

    1981-01-30

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

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

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

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

    PubMed

    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. PMID:23020600

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

    PubMed

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

    2016-06-01

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

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

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ...-packaging materials when used in accordance with the following prescribed conditions: (a) They are used or... 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...

  12. 40 CFR 721.2078 - 1-Piperidinecarboxylic acid, 2-[(dichloro-hydroxy-carbomonocycle)hydrazono]-, methyl ester...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... generically identified as 1-piperidinecarboxylic acid, 2- -, methyl ester (PMN P-96-756) is subject to....125 (a), (b), (c), (d), (f), (g), (h), and (i) are applicable to manufacturers, importers, and... AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES...

  13. 40 CFR 721.2078 - 1-Piperidinecarboxylic acid, 2-[(dichloro-hydroxy-carbomonocycle)hydrazono]-, methyl ester...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... generically identified as 1-piperidinecarboxylic acid, 2- -, methyl ester (PMN P-96-756) is subject to....125 (a), (b), (c), (d), (f), (g), (h), and (i) are applicable to manufacturers, importers, and... AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES...

  14. 40 CFR 721.6075 - Phosphonic acid, 1,1-methylenebis-tetrakis(1-methylethyl) ester.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... substance identified as phosphonic acid, 1,1-methylenebis-tetrakis(1-methylethyl) ester (PMN P-95-168) is... paragraph. (1) Recordkeeping. Recordkeeping requirements as specified in § 721.125 (a) through (h) are... AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES...

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

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

  16. Chemically Modified Fatty Acid Methyl Esters: Potential as Lubricant and Surfactant

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Renewable raw materials are going to play a noteworthy role in the development of sustainable green chemistry because of their eco-friendly and non-toxic nature. A novel process was developed for the production of biodegradable lubricant base stocks from epoxidized fatty acid methyl esters and comm...

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

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Polyhydric alcohol esters of long chain monobasic acids. 178.3780 Section 178.3780 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) INDIRECT FOOD ADDITIVES: ADJUVANTS, PRODUCTION AIDS, AND SANITIZERS...

  18. 21 CFR 178.3780 - Polyhydric alcohol esters of long chain monobasic acids.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Polyhydric alcohol esters of long chain monobasic acids. 178.3780 Section 178.3780 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) INDIRECT FOOD ADDITIVES: ADJUVANTS, PRODUCTION AIDS, AND SANITIZERS...

  19. 21 CFR 573.640 - Methyl esters of higher fatty acids.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 6 2014-04-01 2014-04-01 false Methyl esters of higher fatty acids. 573.640 Section 573.640 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS FOOD ADDITIVES PERMITTED IN FEED AND DRINKING WATER OF ANIMALS Food Additive Listing §...

  20. 21 CFR 178.3780 - Polyhydric alcohol esters of long chain monobasic acids.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Polyhydric alcohol esters of long chain monobasic acids. 178.3780 Section 178.3780 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) INDIRECT FOOD ADDITIVES: ADJUVANTS, PRODUCTION AIDS, AND SANITIZERS...

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

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 6 2012-04-01 2012-04-01 false Methyl esters of higher fatty acids. 573.640 Section 573.640 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS FOOD ADDITIVES PERMITTED IN FEED AND DRINKING WATER OF ANIMALS Food Additive Listing §...

  2. 21 CFR 178.3780 - Polyhydric alcohol esters of long chain monobasic acids.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Polyhydric alcohol esters of long chain monobasic acids. 178.3780 Section 178.3780 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) INDIRECT FOOD ADDITIVES: ADJUVANTS, PRODUCTION AIDS, AND SANITIZERS...

  3. 21 CFR 573.640 - Methyl esters of higher fatty acids.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 6 2011-04-01 2011-04-01 false Methyl esters of higher fatty acids. 573.640 Section 573.640 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS FOOD ADDITIVES PERMITTED IN FEED AND DRINKING WATER OF ANIMALS Food Additive Listing §...

  4. 21 CFR 573.640 - Methyl esters of higher fatty acids.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 6 2013-04-01 2013-04-01 false Methyl esters of higher fatty acids. 573.640 Section 573.640 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS FOOD ADDITIVES PERMITTED IN FEED AND DRINKING WATER OF ANIMALS Food Additive Listing §...

  5. 21 CFR 573.640 - Methyl esters of higher fatty acids.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 6 2010-04-01 2010-04-01 false Methyl esters of higher fatty acids. 573.640 Section 573.640 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS FOOD ADDITIVES PERMITTED IN FEED AND DRINKING WATER OF ANIMALS Food Additive Listing §...

  6. 21 CFR 184.1101 - Diacetyl tartaric acid esters of mono- and diglycerides.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Diacetyl tartaric acid esters of mono- and diglycerides. 184.1101 Section 184.1101 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) DIRECT FOOD SUBSTANCES AFFIRMED AS GENERALLY RECOGNIZED AS SAFE Listing...

  7. Catalytic synthesis of fatty acid methyl esters from extremely low quality greases

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Biodiesel (BD) is a renewable fuel for compression ignition engines that is composed of the simple alkyl esters, usually methyl-, of fatty acids (FAME). It is typically produced via base-catalyzed transesterification between refined vegetable oil or animal fat (e.g., soybean oil, tallow) and an alc...

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

    PubMed Central

    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

  9. 21 CFR 175.260 - Partial phosphoric acid esters of polyester resins.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 3 2014-04-01 2014-04-01 false Partial phosphoric acid esters of polyester resins. 175.260 Section 175.260 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) INDIRECT FOOD ADDITIVES: ADHESIVES AND COMPONENTS OF COATINGS Substances for Use as Components of Coatings § 175.260...

  10. 21 CFR 175.260 - Partial phosphoric acid esters of polyester resins.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Partial phosphoric acid esters of polyester resins. 175.260 Section 175.260 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) INDIRECT FOOD ADDITIVES: ADHESIVES AND COMPONENTS OF COATINGS Substances for Use...

  11. 21 CFR 175.260 - Partial phosphoric acid esters of polyester resins.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Partial phosphoric acid esters of polyester resins. 175.260 Section 175.260 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) INDIRECT FOOD ADDITIVES: ADHESIVES AND COMPONENTS OF COATINGS Substances for Use...

  12. 21 CFR 175.260 - Partial phosphoric acid esters of polyester resins.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Partial phosphoric acid esters of polyester resins. 175.260 Section 175.260 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) INDIRECT FOOD ADDITIVES: ADHESIVES AND COMPONENTS OF COATINGS Substances for Use...

  13. Synthesis and bioactivity of novel caffeic acid esters from Zuccagnia punctata.

    PubMed

    Ramachandra, M S; Subbaraju, G V

    2006-12-01

    Synthesis of novel caffeic acid esters (1 and 2) was accomplished starting from appropriately substituted benzaldehydes (3 and 9). While compound 2 exhibited potent anti-oxidative activity in both the nitroblue tetrazolium and 1,1-diphenyl-2-picrylhydrazyl radical-scavenging models, compound 1 showed moderate 5-lipoxygenase inhibitory activity. PMID:17145655

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

    EPA Science Inventory

    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 ...

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

    EPA Science Inventory

    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...

  16. 40 CFR 721.8160 - Propanoic acid, 2,2-dimethyl-, ethenyl ester.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Propanoic acid, 2,2-dimethyl-, ethenyl ester. 721.8160 Section 721.8160 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances §...

  17. 40 CFR 721.4250 - Hexanoic acid, 2-ethyl-, ethenyl ester.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Hexanoic acid, 2-ethyl-, ethenyl ester. 721.4250 Section 721.4250 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.4250 Hexanoic...

  18. Prediction of preweaning ADG in beef calves from milk fatty acid methyl esters

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Research has shown milk yield (MWT) has an important influence on calf preweaning ADG (PRWADG), but MWT accounts for only a moderate amount of variation in PRWADG. The objective of this study was to determine if milk fatty acid methyl esters (FAME), alone and in combination with MWT, could improve a...

  19. SEPARATION OF T-MAZ ETHOXYLATED SORBITAN FATTY ACID ESTERS BY REVERSE PHASE CHROMATOGRAPHY

    EPA Science Inventory

    The method for determination of T-MAZ ethoxylated sorbitan fatty acid esters is described. This work demonstrates that with a less retentive C8 alkyl bonded phase packing, reverse phase chromatography can be used to analyze nonionic polymer mixtures with a molecular weight range ...

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

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

    PubMed

    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

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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. Clerodane diterpenoids, long chain esters of coumaric acid and other compounds from Baccharis myrsinites.

    PubMed

    Li, C J; Ahmed, A A; Arias, A C; Mabry, T J

    1997-06-01

    A new clerodane diterpenoid and two new long chain esters of trans- and cis-coumaric acid, in addition to known triterpenoids and one known clerodane diterpenoid, have been isolated and characterized from Baccharis myrsinites. The structures were determined by spectroscopic techniques. PMID:9190087

  6. 21 CFR 184.1101 - Diacetyl tartaric acid esters of mono- and diglycerides.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Diacetyl tartaric acid esters of mono- and diglycerides. 184.1101 Section 184.1101 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) DIRECT FOOD SUBSTANCES AFFIRMED AS GENERALLY RECOGNIZED AS SAFE Listing...

  7. Organocatalytic enantioselective γ-aminoalkylation of unsaturated ester: access to pipecolic acid derivatives.

    PubMed

    Xu, Jianfeng; Jin, Zhichao; Chi, Yonggui Robin

    2013-10-01

    The direct γ-carbon functionalization of α,β-unsaturated esters via N-Heterocyclic Carbene (NHC) catalysis is disclosed. This catalytically generated nucleophilic γ-carbon undergoes highly enantioselective additions to hydrazones. The resulting δ-lactam products can be readily transformed to optically enriched pipecolic acid derivatives. PMID:24067098

  8. Self-assembly modes of glycyrrhetinic acid esters in view of the crystal packing of related triterpene molecules.

    PubMed

    Langer, Dominik; Wicher, Barbara; Szczołko, Wojciech; Gdaniec, Maria; Tykarska, Ewa

    2016-08-01

    The crystal structures of three ester derivatives of glycyrrhetinic acid (GE) are reported. X-ray crystallography revealed that despite differences in the size of the ester substituents (ethyl, isopropyl and 2-morpholinoethyl) the scheme of molecular self-assembly is similar in all three cases but differs significantly from that observed in other known GE esters. According to our analysis, the two basic patterns of self-assembly of GE esters observed in their unsolvated crystals correspond to two distinct orientations of the ester groups relative to the triterpene backbone. Moreover, comparison of the self-assembly modes of GE esters in their unsolvated forms with the supramolecular organization of GE and carbenoxolone in their solvated crystals revealed that ester substituents replace solvent molecules hydrogen bonded to the COOH group at the triterpene skeleton, resulting in similar packing arrangements of these compounds. PMID:27484379

  9. Antimicrobial effects of esters and amides of 3-(5-nitro-2-furyl)acrylic acid.

    PubMed

    Kellová, G; Sturdík, E; Stibrányi, L; Drobnica, L; Augustín, J

    1984-01-01

    The effect of 18 newly synthesized esters and amides of 3-(5-nitro-2-furyl)acrylic acid on bacteria (Escherichia coli, Staphylococcus aureus), yeasts (Saccharomyces cerevisiae, Candida albicans), molds (Aspergillus niger, Penicillium cyclopium, Rhizopus oryzae) and algae (Chlorella pyrenoidosa, Euglena gracilis, Scenedesmus obliquus) was investigated. The MIC values revealed antimycotic, antialgal and antibacterial activity of the studied derivatives. The antimycotic activity was found to decrease with increasing the length of the alkyl chain of esters and after introduction of amino nitrogen into the furylethylene backbone. The inhibitory effect on growth is caused by blocking bioenergetic processes, glycolysis in particular. PMID:6714854

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

    PubMed

    Changotra, Avtar; Sunoj, Raghavan B

    2016-08-01

    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. PMID:27463593

  11. Synthesis of acid addition salt of delta-aminolevulinic acid from 5-bromo levulinic acid esters

    DOEpatents

    Moens, Luc

    2003-06-24

    A process of preparing an acid addition salt of delta-aminolevulinc acid comprising: a) dissolving a lower alkyl 5-bromolevulinate and hexamethylenetetramine in a solvent selected from the group consisting of water, ethyl acetate, chloroform, acetone, ethanol, tetrahydrofuran and acetonitrile, to form a quaternary ammonium salt of the lower alkyl 5-bromolevulinate; and b) hydrolyzing the quaternary ammonium salt with an inorganic acid to form an acid addition salt of delta-aminolevulinic acid.

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

    PubMed

    Jonas, A J; Butler, I J

    1989-07-01

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

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

    PubMed Central

    Jonas, A J; Butler, I J

    1989-01-01

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

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

    PubMed

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

    2016-04-01

    The Botryosphaeriaceae are a family of trunk disease fungi that cause dieback and death of various plant hosts. This work sought to characterize fatty acid derivatives in a highly virulent member of this family, Lasiodiplodia theobromae. Nuclear magnetic resonance and gas chromatography-mass spectrometry of an isolated compound revealed (Z, Z)-9,12-ethyl octadecadienoate, (trivial name ethyl linoleate), as one of the most abundant fatty acid esters produced by L. theobromae. A variety of naturally produced esters of fatty acids were identified in Botryosphaeriaceae. In comparison, the production of fatty acid esters in the soil-borne tomato pathogen Fusarium oxysporum, and the non-phytopathogenic fungus Trichoderma asperellum was found to be limited. Ethyl linoleate, ethyl hexadecanoate (trivial name ethyl palmitate), and ethyl octadecanoate, (trivial name ethyl stearate), significantly inhibited tobacco seed germination and altered seedling leaf growth patterns and morphology at the highest concentration (0.2 mg/mL) tested, while ethyl linoleate and ethyl stearate significantly enhanced growth at low concentrations, with both still inducing growth at 98 ng/mL. This work provides new insights into the role of naturally esterified fatty acids from L. theobromae as plant growth regulators with similar activity to the well-known plant growth regulator gibberellic acid. PMID:26926564

  15. Neuroprotective effect of caffeic acid phenethyl ester in 3-nitropropionic acid-induced striatal neurotoxicity.

    PubMed

    Bak, Jia; Kim, Hee Jung; Kim, Seong Yun; Choi, Yun-Sik

    2016-05-01

    Caffeic acid phenethyl ester (CAPE), derived from honeybee hives, is a bioactive compound with strong antioxidant activity. This study was designed to test the neuroprotective effect of CAPE in 3-nitropropionic acid (3NP)-induced striatal neurotoxicity, a chemical model of Huntington's disease (HD). Initially, to test CAPE's antioxidant activity, a 2,2'-azino-bis-3-ethylbenzthiazoline-6-sulfonic acid (ABTS) antioxidant assay was employed, and CAPE showed a strong direct radical-scavenging eff ect. In addition, CAPE provided protection from 3NP-induced neuronal cell death in cultured striatal neurons. Based on these observations, the in vivo therapeutic potential of CAPE in 3NP-induced HD was tested. For this purpose, male C57BL/6 mice were repeatedly given 3NP to induce HD-like pathogenesis, and 30 mg/kg of CAPE or vehicle (5% dimethyl sulfoxide and 95% peanut oil) was administered daily. CAPE did not cause changes in body weight, but it reduced mortality by 29%. In addition, compared to the vehicle-treated group, robustly reduced striatal damage was observed in the CAPE-treated animals, and the 3NP-induced behavioral defi cits on the rotarod test were signifi cantly rescued after the CAPE treatment. Furthermore, immunohistochemical data showed that immunoreactivity to glial fibrillary acidic protein (GFAP) and CD45, markers for astrocyte and microglia activation, respectively, were strikingly reduced. Combined, these data unequivocally indicate that CAPE has a strong antioxidant eff ect and can be used as a potential therapeutic agent against HD. PMID:27162482

  16. Neuroprotective effect of caffeic acid phenethyl ester in 3-nitropropionic acid-induced striatal neurotoxicity

    PubMed Central

    Bak, Jia; Kim, Hee Jung; Kim, Seong Yun

    2016-01-01

    Caffeic acid phenethyl ester (CAPE), derived from honeybee hives, is a bioactive compound with strong antioxidant activity. This study was designed to test the neuroprotective effect of CAPE in 3-nitropropionic acid (3NP)-induced striatal neurotoxicity, a chemical model of Huntington's disease (HD). Initially, to test CAPE's antioxidant activity, a 2,2'-azino-bis-3-ethylbenzthiazoline-6-sulfonic acid (ABTS) antioxidant assay was employed, and CAPE showed a strong direct radical-scavenging eff ect. In addition, CAPE provided protection from 3NP-induced neuronal cell death in cultured striatal neurons. Based on these observations, the in vivo therapeutic potential of CAPE in 3NP-induced HD was tested. For this purpose, male C57BL/6 mice were repeatedly given 3NP to induce HD-like pathogenesis, and 30 mg/kg of CAPE or vehicle (5% dimethyl sulfoxide and 95% peanut oil) was administered daily. CAPE did not cause changes in body weight, but it reduced mortality by 29%. In addition, compared to the vehicle-treated group, robustly reduced striatal damage was observed in the CAPE-treated animals, and the 3NP-induced behavioral defi cits on the rotarod test were signifi cantly rescued after the CAPE treatment. Furthermore, immunohistochemical data showed that immunoreactivity to glial fibrillary acidic protein (GFAP) and CD45, markers for astrocyte and microglia activation, respectively, were strikingly reduced. Combined, these data unequivocally indicate that CAPE has a strong antioxidant eff ect and can be used as a potential therapeutic agent against HD. PMID:27162482

  17. 40 CFR 721.2140 - Carbo-poly-cycli-col azo-alkyl-aminoalkyl-carbo-mono-cyclic ester, halogen acid salt.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...-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...

  18. 40 CFR 721.2140 - Carbo-poly-cycli-col azo-alkyl-aminoalkyl-carbo-mono-cyclic ester, halogen acid salt.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...-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...

  19. 40 CFR 721.2140 - Carbo-poly-cycli-col azo-alkyl-aminoalkyl-carbo-mono-cyclic ester, halogen acid salt.

    Code of Federal Regulations, 2010 CFR

    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...

  20. 40 CFR 721.2140 - Carbo-poly-cycli-col azo-alkyl-aminoalkyl-carbo-mono-cyclic ester, halogen acid salt.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...-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...

  1. 40 CFR 721.2140 - Carbo-poly-cycli-col azo-alkyl-aminoalkyl-carbo-mono-cyclic ester, halogen acid salt.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...-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...

  2. Production of organic acid esters from biomass - novel processes and concepts

    SciTech Connect

    Datta, R.

    1981-01-01

    After low cost, low energy pretreatment, lignocellulose can be converted directly to volatile (C/sub 2/-C/sub 6/) organic acids by mixed-culture acidogenic fermentation. The principal components of lignocellulose (pectins, hemicellulose, cellulose, and lignin) are all converted to organic acids in high yields. Esterification from dilute aqueous solutions using novel techniques based on adsorption, solvent extraction, or biochemical conversion could be an important method for recovering these acids and simultaneously producing liquid fuels or chemical feedstocks. Uses of organic acid esters and conceptual biomass conversion processes are outlined. The significance of these processes for substantially increasing liquid fuel productivity from biomass feedstocks are discussed.

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

    PubMed

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

    2016-09-01

    White adipose tissue (WAT) is a complex organ with both metabolic and endocrine functions. Dysregulation of all of these functions of WAT, together with low-grade inflammation of the tissue in obese individuals, contributes to the development of insulin resistance and type 2 diabetes. n-3 polyunsaturated fatty acids (PUFAs) of marine origin play an important role in the resolution of inflammation and exert beneficial metabolic effects. Using experiments in mice and overweight/obese patients with type 2 diabetes, we elucidated the structures of novel members of fatty acid esters of hydroxy fatty acids-lipokines derived from docosahexaenoic acid (DHA) and linoleic acid, which were present in serum and WAT after n-3 PUFA supplementation. These compounds contained DHA esterified to 9- and 13-hydroxyoctadecadienoic acid (HLA) or 14-hydroxydocosahexaenoic acid (HDHA), termed 9-DHAHLA, 13-DHAHLA, and 14-DHAHDHA, and were synthesized by adipocytes at concentrations comparable to those of protectins and resolvins derived from DHA in WAT. 13-DHAHLA exerted anti-inflammatory and proresolving properties while reducing macrophage activation by lipopolysaccharides and enhancing the phagocytosis of zymosan particles. Our results document the existence of novel lipid mediators, which are involved in the beneficial anti-inflammatory effects attributed to n-3 PUFAs, in both mice and humans. PMID:27313314

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

    PubMed

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

    2016-07-01

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

  5. Water chemical ionization mass spectrometry of aldehydes, ketones esters, and carboxylic acids

    SciTech Connect

    Hawthorne, S.B.; Miller, D.J.

    1986-11-01

    Chemical ionization mass spectrometry (CI) of aliphatic and aromatic carbonyl compounds using water as the reagent gas provides intense pseudomolecular ions and class-specific fragmentation patterns that can be used to identify aliphatic aldehydes, ketones, carboxylic acids, and esters. The length of ester acyl and alkyl groups can easily be determined on the basis of loss of alcohols from the protonated parent. Water CI provides for an approximately 200:1 selectivity of carbonyl species over alkanes. No reagent ions are detected above 55 amu, allowing species as small as acetone, propanal, acetic acid, and methyl formate to be identified. When deuterate water was used as the reagent, only the carboxylic acids and ..beta..-diketones showed significant H/D exchange. The use of water CI to identify carbonyl compounds in a wastewater from the supercritical water extraction of lignite coal, in lemon oil, and in whiskey volatiles is discussed.

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

    PubMed

    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. PMID:26471553

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

    PubMed

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

    2016-02-01

    Saccharomyces cerevisiae has previously been engineered to become a cell factory for the production of fatty acid ethyl esters (FAEEs), molecules suitable for crude diesel replacement. To find new metabolic engineering targets for the improvement of FAEE cell factories, three different FAEE-producing strains of S. cerevisiae, constructed previously, were compared and characterized by quantification of key fluxes and genome-wide transcription analysis. From both the physiological and the transcriptional data, it was indicated that strain CB2I20, with high expression of a heterologous wax ester synthase gene (ws2) and strain BdJ15, containing disruptions of genes DGA1, LRO1, ARE1, ARE2 and POX1, which prevent the conversion of acyl-CoA to sterol esters, triacylglycerides and the degradation to acetyl-CoA, triggered oxidative stress that consequently influenced cellular growth. In the latter strain, stress was possibly triggered by disabling the buffering capacity of lipid droplets in encapsulating toxic fatty acids such as oleic acid. Additionally, it was indicated that there was an increased demand for NADPH required for the reduction steps in fatty acid biosynthesis. In conclusion, our analysis clearly shows that engineering of fatty acid biosynthesis results in transcriptional reprogramming and has a significant effect on overall cellular metabolism. PMID:26590613

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

    PubMed

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

    2001-11-01

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

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

    PubMed

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

    2015-08-01

    Most lipids are best characterized by their fatty acids which may differ in (a) chain length, (b) degree of unsaturation, (c) configuration and position of the double bonds, and (d) the presence of other functionalities. Thus, a fast, simple, and quantitative analytical technique to determine naturally occurring free fatty acids (FFA) in different samples is very important. Just as for saponified acylglycerols, the determination of FFA's has generally been carried out by high resolution gas chromatography (HRGC). The use of an open tubular capillary column coupled with a flame ionization or mass spectrometric detector provides for both high resolution and quantification of FFA's but only after conversion of all free fatty acids to fatty acid methyl esters (FAME) or pentafluorobenzyl esters. Unfortunately, volatilization of labile ester derivatives of mono- and poly-unsaturated FFA's can cause both thermal degradation and isomerization of the fatty acid during HRGC. The employment of a second generation instrument (here referred to as UltraHigh Performance Supercritical Fluid Chromatograph, UHPSFC) with high precision for modified flow and repeated back pressure adjustment in conjunction with sub-2μm various bonded silica particles (coupled with evaporative light scattering, ELSD, and mass spectrometric, MS, detection) for separation and detection of the following mixtures is described: (a) 31 free fatty acids, (b) isomeric FFA's, and (c) lipophilic materials in two real world fish oil samples. Limits of detection for FFA's via UHPSFC/MS and UHPSFC/ELSD versus detection of FAME's via HRGC/MS are quantitatively compared. PMID:26093119

  10. 40 CFR 721.10074 - Acetic acid, 2-chloro-, 1-(3,3-dimethylcyclohexyl)ethyl ester.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

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

  11. 40 CFR 721.10074 - Acetic acid, 2-chloro-, 1-(3,3-dimethylcyclohexyl)ethyl ester.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Acetic acid, 2-chloro-, 1-(3,3... Specific Chemical Substances § 721.10074 Acetic acid, 2-chloro-, 1-(3,3-dimethylcyclohexyl)ethyl ester. (a... acetic acid, 2-chloro-, 1-(3,3-dimethylcyclohexyl)ethyl ester (PMN P-05-568; CAS No. 477218-59-0)...

  12. An enhanced procedure for measuring organic acids and methyl esters in PM2.5

    NASA Astrophysics Data System (ADS)

    Liu, F.; Duan, F. K.; He, K. B.; Ma, Y. L.; Rahn, K. A.; Zhang, Q.

    2015-11-01

    A solid-phase extraction (SPE) pretreatment procedure allowing organic acids to be separated from methyl esters in fine aerosol has been developed. The procedure first separates the organic acids from fatty acid methyl esters (FAMEs) and other nonacid organic compounds by aminopropyl-based SPE cartridge and then quantifies them by gas chromatography/mass spectrometry. The procedure prevents the fatty acids and dimethyl phthalate from being overestimated, and so allows us to accurately quantify the C4-C11 dicarboxylic acids (DCAs) and the C8-C30 monocarboxylic acids (MCAs). Results for the extraction of DCAs, MCAs, and AMAs in eluate and FAMEs in effluate by SAX and NH2 SPE cartridges exhibited that the NH2 SPE cartridge gave higher extraction efficiency than the SAX cartridge. The recoveries of analytes ranged from 67.5 to 111.3 %, and the RSD ranged from 0.7 to 10.9 %. The resulting correlations between the aliphatic acids and FAMEs suggest that the FAMEs had sources similar to those of the carboxylic acids, or were formed by esterifying carboxylic acids, or that aliphatic acids were formed by hydrolyzing FAMEs. Through extraction and cleanup using this procedure, 17 aromatic acids in eluate were identified and quantified by gas chromatography/tandem mass spectrometry, including five polycyclic aromatic hydrocarbon (PAH): acids 2-naphthoic, biphenyl-4-carboxylic, 9-oxo-9H-fluorene-1-carboxylic, biphenyl-4,4´-dicarboxylic, and phenanthrene-1-carboxylic acid, plus 1,8-naphthalic anhydride. Correlations between the PAH acids and the dicarboxylic and aromatic acids suggested that the first three acids and 1,8-naphthalic anhydride were secondary atmospheric photochemistry products and the last two mainly primary.

  13. Hepatoprotective effect of trimethylgallic acid esters against carbon tetrachloride-induced liver injury in rats.

    PubMed

    Sachdeva, Mamta; Chadha, Renu; Kumar, Anil; Karan, Maninder; Singh, Tejvir; Dhingra, Sameer

    2015-12-01

    Gallic acid and its derivatives are potential therapeutic agents for treating various oxidative stress mediated disorders. In the present study, we investigated the hepatoprotective effects of newly synthesized conjugated trimethylgallic acid (TMGA) esters against carbon tetrachloride (CCl4)-induced hepatotoxicity in rats. Animals were pre-treated with TMGA esters at their respective doses for 7 days against CCl4-induced hepatotoxicity. The histopathological changes were evaluated to find out degenerative fatty changes including vacuole formation, inflammation and tissue necrosis. Various biomarkers of oxidative stress (lipid peroxidation, glutathione levels, and endogenous antioxidant enzyme activities), liver enzymes (AST and ALT), triacylglycerol and cholesterol were evaluated. Pre-treatment with TMGA esters (MRG, MGG, MSG, and MUG at the dose of 28.71, 30.03, 31.35, 33.62 mg/kg/day), respectively reversed the CCl4-induced liver injury scores (reduced vacuole formation, inflammation and necrosis), biochemical parameters of plasma (increased AST, ALT, TG, and cholesterol), antioxidant enzymes (increased lipid peroxidation and nitrite levels; decreased glutathione levels, superoxide dismutase and catalase activities) in liver tissues and inflammatory surge (serum TNF-α) significantly. The study revealed that TMGA esters exerted hepatoprotective effects in CCl4-induced rats, specifically by modulating oxidative-nitrosative stress and inflammation. PMID:26742325

  14. 40 CFR 721.10326 - 2-Propenoic acid, 2-methyl-, methyl ester, polymer with butyl 2-propenoate, ethyl 2-propenoate...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... ester, polymer with butyl 2-propenoate, ethyl 2-propenoate, zinc 2-methyl-2-propenoate (1:2) and zinc 2... 2-Propenoic acid, 2-methyl-, methyl ester, polymer with butyl 2-propenoate, ethyl 2-propenoate, zinc 2-methyl-2-propenoate (1:2) and zinc 2-propenoate (1:2), 2,2'-(1,2-diazenediyl)bis - and...

  15. 40 CFR 721.1725 - Benzoic acid, 3,3′-methyl-enebis [6 amino-, di-2-propenyl ester.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... amino-, di-2-propenyl ester. 721.1725 Section 721.1725 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.1725 Benzoic acid, 3,3′-methyl-enebis [6 amino-, di-2-propenyl ester. (a) Chemical substance and significant new uses subject to reporting. (1)...

  16. The adjuvant activity of fatty acid esters. The role of acyl chain length and degree of saturation.

    PubMed Central

    Bomford, R

    1981-01-01

    Water-in-oil emulsions of metabolizable fatty acid esters, with the non-toxic surfactant Pluronic L122 as emulsifying agent, potentiated the humoral response to bovine serum albumin and staphylococcal toxoid in the mouse. Adjuvant activity was increased by changing the chemical nature of the esters as follows: (i) using a series of ethyl esters, adjuvant activity appeared when the acyl chain length of the fatty acid component was 16 or greater; (ii) isobutyl and isopropyl esters of palmitic acid (C16:0) were superior to ethyl; (iii) the ethyl esters of oleic (C18:1) and linoleic (C18:2) acids were better than stearic (C18:0). Since emulsions prepared with longer chain saturated esters are very viscous or solid at room temperature, and unsaturated esters are chemically reactive, emulsions were prepared with differing proportions of ethyl caprate (C10:0) and butyl stearate. At a ratio of 9:1 the emulsions possessed the low viscosity of ethyl caprate, but gained the adjuvant activity of butyl stearate. 125I-labelled BSA was retained in the footpad to a significantly greater extent than with a caprate emulsion, but reasons are given for believing that slow release of antigen is not the only mechanism of adjuvant activity. The ester emulsions caused more acute but less chronic local inflammation (footpad swelling) than Freund's incomplete adjuvant. PMID:7275184

  17. 40 CFR 721.1725 - Benzoic acid, 3,3′-methyl-enebis [6 amino-, di-2-propenyl ester.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... amino-, di-2-propenyl ester. 721.1725 Section 721.1725 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.1725 Benzoic acid, 3,3′-methyl-enebis [6 amino-, di-2-propenyl ester. (a) Chemical substance and significant new uses subject to reporting. (1)...

  18. 40 CFR 721.10136 - 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, reaction products with hexakis(alkoxyalkyl...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...-hydroxyethyl ester, reaction products with hexakis(alkoxyalkyl)melamine (generic). 721.10136 Section 721.10136... SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10136 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, reaction products with...

  19. 40 CFR 721.10136 - 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, reaction products with hexakis(alkoxyalkyl...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...-hydroxyethyl ester, reaction products with hexakis(alkoxyalkyl)melamine (generic). 721.10136 Section 721.10136... SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10136 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, reaction products with...

  20. 40 CFR 721.10363 - Alkenoic acid, 2-methyl-, 2-oxiranylmethyl ester, reaction products with 4,4′ -methylenebis...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...-oxiranylmethyl ester, reaction products with 4,4â² -methylenebis (cyclohexanamine) (generic). 721.10363 Section... CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10363 Alkenoic acid, 2-methyl-, 2-oxiranylmethyl ester, reaction products with...

  1. 40 CFR 721.10363 - Alkenoic acid, 2-methyl-, 2-oxiranylmethyl ester, reaction products with 4,4′ -methylenebis...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...-oxiranylmethyl ester, reaction products with 4,4â² -methylenebis (cyclohexanamine) (generic). 721.10363 Section... CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10363 Alkenoic acid, 2-methyl-, 2-oxiranylmethyl ester, reaction products with...

  2. 40 CFR 721.10136 - 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, reaction products with hexakis(alkoxyalkyl...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...-hydroxyethyl ester, reaction products with hexakis(alkoxyalkyl)melamine (generic). 721.10136 Section 721.10136... SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10136 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, reaction products with...

  3. 40 CFR 721.10363 - Alkenoic acid, 2-methyl-, 2-oxiranylmethyl ester, reaction products with 4,4′ -methylenebis...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...-oxiranylmethyl ester, reaction products with 4,4â² -methylenebis (cyclohexanamine) (generic). 721.10363 Section... CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10363 Alkenoic acid, 2-methyl-, 2-oxiranylmethyl ester, reaction products with...

  4. 40 CFR 721.10136 - 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, reaction products with hexakis(alkoxyalkyl...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...-hydroxyethyl ester, reaction products with hexakis(alkoxyalkyl)melamine (generic). 721.10136 Section 721.10136... SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10136 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, reaction products with...

  5. 40 CFR 721.10136 - 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, reaction products with hexakis(alkoxyalkyl...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...-hydroxyethyl ester, reaction products with hexakis(alkoxyalkyl)melamine (generic). 721.10136 Section 721.10136... SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10136 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, reaction products with...

  6. Nitrogen Derivatives of Soybean Oil and Fatty Acid Methyl Esters

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Vegetable oil based products are eco-friendly and non-toxic in nature, which is increasing their utilization in lot of applications. The presence of double bonds in some of the fatty acids, are attractive sites for functionalization. In this study we have used these sites for functionalization usi...

  7. Synthesis and physical properties of isostearic acids and their esters

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Saturated branched-chain fatty acids (sbc-FAs) are found as minor constituents in several natural fats and oils. Sbc-FAs are of interest since they have lower melting points than their linear counterparts and exhibit good oxidative stability; properties that make them ideally suited in a number of ...

  8. Thermochemistry of C-O, (CO)-O, and (CO)-C bond breaking in fatty acid methyl esters

    SciTech Connect

    Osmont, Antoine; Yahyaoui, Mohammed; Catoire, Laurent; Goekalp, Iskender; Swihart, Mark T.

    2008-10-15

    Density functional theory quantum chemical calculations corrected with empirical atomic increments have been used to examine C-O, (CO)-O, and (CO)-C bond scission enthalpies in gas-phase fatty acid methyl esters (FAMEs) present in biodiesel derived from rapeseed oil methyl ester and soybean oil methyl ester. Mechanistic information, currently not available elsewhere for these large species, is obtained based on thermochemical considerations and compared to thermochemical considerations reported for methyl butanoate, a small methyl ester sometimes used as a model for FAMEs. These results are compared to previously reported C-C and C-H bond scissions in these FAMEs, derived using this same protocol. (author)

  9. Identification of β-hydroxy fatty acid esters and primary, secondary-alkanediol esters in cuticular waxes of the moss Funaria hygrometrica.

    PubMed

    Busta, Lucas; Budke, Jessica M; Jetter, Reinhard

    2016-01-01

    The plant cuticle, a multi-layered membrane that covers plant aerial surfaces to prevent desiccation, consists of the structural polymer cutin and surface-sealing waxes. Cuticular waxes are complex mixtures of ubiquitous, typically monofunctional fatty acid derivatives and taxon-specific, frequently bifunctional specialty compounds. To further our understanding of the chemical diversity of specialty compounds, the waxes on the aerial structures of the leafy gametophyte, sporophyte capsule, and calyptra of the moss Funaria hygrometrica were surveyed. Respective moss surfaces were extracted, and resulting lipid mixtures were analyzed by gas chromatography-mass spectrometry (GC-MS). The extracts contained ubiquitous wax compound classes along with two prominent, unidentified classes of compounds that exhibited some characteristics of bifunctional structures. Microscale transformations led to derivatives with characteristic MS fragmentation patterns suggesting possible structures for these compounds. To confirm the tentative structure assignments, one compound in each of the suspected homologous series was synthesized. Based on GC-MS comparison with the authentic standards, the first series of compounds was identified as containing esters formed by β-hydroxy fatty acids and wax alcohols, with ester chain lengths varying from C42 to C50 and the most prominent homolog being C46. The second series consisted of fatty acid esters of 1,7-alkanediols, linked via the primary hydroxyl group, with ester chain lengths C40-C52 also dominated by the C46 homolog. The β-hydroxy acid esters were restricted to the sporophyte capsule, and the diol esters to the leafy gametophyte and calyptra. Based on their homolog and isomer distributions, and the presence of free 1,7-triacontanediol, possible biosynthetic reactions leading to these compounds are discussed. PMID:26553812

  10. Metabolic pathway engineering for fatty acid ethyl ester production in Saccharomyces cerevisiae using stable chromosomal integration.

    PubMed

    de Jong, Bouke Wim; Shi, Shuobo; Valle-Rodríguez, Juan Octavio; Siewers, Verena; Nielsen, Jens

    2015-03-01

    Fatty acid ethyl esters are fatty acid derived molecules similar to first generation biodiesel (fatty acid methyl esters; FAMEs) which can be produced in a microbial cell factory. Saccharomyces cerevisiae is a suitable candidate for microbial large scale and long term cultivations, which is the typical industrial production setting for biofuels. It is crucial to conserve the metabolic design of the cell factory during industrial cultivation conditions that require extensive propagation. Genetic modifications therefore have to be introduced in a stable manner. Here, several metabolic engineering strategies for improved production of fatty acid ethyl esters in S. cerevisiae were combined and the genes were stably expressed from the organisms' chromosomes. A wax ester synthase (ws2) was expressed in different yeast strains with an engineered acetyl-CoA and fatty acid metabolism. Thus, we compared expression of ws2 with and without overexpression of alcohol dehydrogenase (ADH2), acetaldehyde dehydrogenase (ALD6) and acetyl-CoA synthetase (acs SE (L641P) ) and further evaluated additional overexpression of a mutant version of acetyl-CoA decarboxylase (ACC1 (S1157A,S659A) ) and the acyl-CoA binding protein (ACB1). The combined engineering efforts of the implementation of ws2, ADH2, ALD6 and acs SE (L641P) , ACC1 (S1157A,S659A) and ACB1 in a S. cerevisiae strain lacking storage lipid formation (are1Δ, are2Δ, dga1Δ and lro1Δ) and β-oxidation (pox1Δ) resulted in a 4.1-fold improvement compared with sole expression of ws2 in S. cerevisiae. PMID:25422103

  11. Recovery of sterols as fatty acid steryl esters from waste material after purification of tocopherols.

    PubMed

    Nagao, Toshihiro; Hirota, Yoshinori; Watanabe, Yomi; Kobayashi, Takashi; Kishimoto, Noriaki; Fujita, Tokio; Kitano, Motohiro; Shimada, Yuji

    2004-08-01

    Tocopherols are purified industrially from soybean oil deodorizer distillate by a process comprising distillation and ethanol fractionation. The waste material after ethanol fractionation (TC waste) contains 75% sterols, but a purification process has not yet been developed. We thus attempted to purify sterols by a process including a lipase-catalyzed reaction. Candida rugosa lipase efficiently esterified sterols in TC waste with oleic acid (OA). After studying several factors affecting esterification, the reaction conditions were determined as follows: ratio of TC waste/OA, 1:2 (wt/wt); water content, 30%; amount of lipase, 120 U/g-reaction mixture; temperature, 40 degrees C. Under these conditions, the degree of esterification reached 82.7% after 24 h. FA steryl esters (steryl esters) in the oil layer were purified successfully by short-path distillation (purity, 94.9%; recovery, 73.1%). When sterols in TC waste were esterified with FFA originating from olive, soybean, rapeseed, safflower, sunflower, and linseed oils, the FA compositions of the steryl esters differed somewhat from those of the original oils: The content of saturated FA was lower and that of unsaturated FA was higher. The m.p. of the steryl esters synthesized (21.7-36.5 degrees C) were remarkably low compared with those of the steryl esters purified from high-b.p. soybean oil deodorizer distillate substances (56.5 degrees C; JAOCS 80, 341-346, 2003). The low-m.p. steryl esters were soluble in rapeseed oil even at a final concentration of 10%. PMID:15638248

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

    PubMed

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

    2016-08-01

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

  13. Fatty Acid Esters of Phloridzin Induce Apoptosis of Human Liver Cancer Cells through Altered Gene Expression

    PubMed Central

    Nair, Sandhya V. G.; Ziaullah; Rupasinghe, H. P. Vasantha

    2014-01-01

    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 mediated

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

    PubMed

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

    2016-01-01

    A series of isoquercitrin (quercetin-3-O-β-d-glucopyranoside) esters with mono- or dicarboxylic acids was designed to modulate hydro- and lipophilicity and biological properties. Esterification of isoquercitrin was accomplished by direct chemoenzymatic reaction using Novozym 435 (lipase from Candida antarctica), which accepted C₅- to C12-dicarboxylic acids; the shorter ones, such as oxalic (C₂), malonic (C₃), succinic (C₄) and maleic (C₄) acids were not substrates of the lipase. Lipophilicity of monocarboxylic acid derivatives, measured as log P, increased with the chain length. Esters with glutaric and adipic acids exhibited hydrophilicity, and the dodecanedioic acid hemiester was more lipophilic. All derivatives were less able to reduce Folin-Ciocalteau reagent (FCR) and scavenge DPPH (1,1-diphenyl-2-picrylhydrazyl) than isoquercitrin; ABTS (2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid)) radical-scavenging activity was comparable. Dodecanoate and palmitate were the least active in FCR and ABTS scavenging; dodecanoate and hemiglutarate were the strongest DPPH scavengers. In contrast, most derivatives were much better inhibitors of microsomal lipoperoxidation than isoquercitrin; butyrate and hexanoate were the most efficient. Anti-lipoperoxidant activity of monocarboxylic derivatives, except acetates, decreased with increasing aliphatic chain. The opposite trend was noted for dicarboxylic acid hemiesters, isoquercitrin hemidodecanedioate being the most active. Overall, IQ butyrate, hexanoate and hemidodecanedioate are the most promising candidates for further studies. PMID:27338349

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

    PubMed Central

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

    2016-01-01

    A series of isoquercitrin (quercetin-3-O-β-d-glucopyranoside) esters with mono- or dicarboxylic acids was designed to modulate hydro- and lipophilicity and biological properties. Esterification of isoquercitrin was accomplished by direct chemoenzymatic reaction using Novozym 435 (lipase from Candida antarctica), which accepted C5- to C12-dicarboxylic acids; the shorter ones, such as oxalic (C2), malonic (C3), succinic (C4) and maleic (C4) acids were not substrates of the lipase. Lipophilicity of monocarboxylic acid derivatives, measured as log P, increased with the chain length. Esters with glutaric and adipic acids exhibited hydrophilicity, and the dodecanedioic acid hemiester was more lipophilic. All derivatives were less able to reduce Folin–Ciocalteau reagent (FCR) and scavenge DPPH (1,1-diphenyl-2-picrylhydrazyl) than isoquercitrin; ABTS (2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid)) radical-scavenging activity was comparable. Dodecanoate and palmitate were the least active in FCR and ABTS scavenging; dodecanoate and hemiglutarate were the strongest DPPH scavengers. In contrast, most derivatives were much better inhibitors of microsomal lipoperoxidation than isoquercitrin; butyrate and hexanoate were the most efficient. Anti-lipoperoxidant activity of monocarboxylic derivatives, except acetates, decreased with increasing aliphatic chain. The opposite trend was noted for dicarboxylic acid hemiesters, isoquercitrin hemidodecanedioate being the most active. Overall, IQ butyrate, hexanoate and hemidodecanedioate are the most promising candidates for further studies. PMID:27338349

  16. Antimicrobial activity of n-6, n-7 and n-9 fatty acids and their esters for oral microorganisms

    PubMed Central

    Huang, Chifu B.; George, Brian; Ebersole, Jeffery L.

    2010-01-01

    Objective This study is to assess the antibacterial activity of omega-6, -7, -9 (n-6, n-7, n-9) fatty acids against various oral microorganisms. Methods The n-6, n-7, n-9 fatty acids, such as γ-linoleic acid (GLA), linoleic acid (LA), arachidonic acid (ARA), palmitoleic acid (PA), and oleic acid (OA), their fatty acid ethyl esters, GLA-EE, LA-EE, ARA-EE, PA-EE, OA-EE, and their fatty acid methyl esters, GLA-ME, LA-ME, ARA-ME, PA-ME, OA-ME were investigated for antimicrobial activity against oral pathogens Streptococcus mutans, Candida albicans, Aggregatibacter actinomycetemcomitans, Fusobacterium nucleatum, and Porphyromonas gingivalis. Various concentrations of the fatty acids, their methyl and ethyl esters were tested against various oral pathogens in 96-well plates and blood-agar plate. The plates were incubated anaerobically or aerobically at 37°C for 48 hours, and the colony forming units (CFU) were determined. Results The data demonstrated that select n-6, n-7, n-9 fatty acids and their esters exhibited strong antimicrobial activity against these oral microorganisms, demonstrating some specificity for individual microbial species. Conclusion The potential use or the combinations of the n-6, n-7, n-9 fatty acids and/or their esters, provided in a local delivery vehicle to infected sites in the oral cavity, could be considered as an additional therapeutic approach to improving oral health. PMID:20541177

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

    NASA Technical Reports Server (NTRS)

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

    1985-01-01

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

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

    PubMed

    Shi, Xueyan; Liu, Feipeng; Mao, Jianyou

    2016-03-17

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

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

    NASA Astrophysics Data System (ADS)

    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.

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

    PubMed

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

    2014-12-26

    Six new (erinarols A-F, 1-6) and five known (7-11) ergostane-type sterol fatty acid esters were isolated from the methanol extract of the dried fruiting bodies of Hericium erinaceum. Their chemical structures were elucidated using chemical and physical methods as well as through comparison of NMR and mass spectral data with those reported previously. This is the first comprehensive investigation on ergostane-type sterol fatty acid esters from H. erinaceum. The isolated compounds were evaluated for their PPAR transactivational effects using a luciferase reporter system. Compounds 1 and 2 significantly activated the transcriptional activity of PPARs in a dose-dependent manner, with EC50 values of 8.2 and 6.4 μM, respectively. Moreover, compounds 1 and 2 also activated PPARα and PPARγ transcriptional activity, with stimulation from 1.3- to 3.9-fold at 20 μM concentrations. PMID:25437304

  1. Preparation of polyimides from mixtures of monomeric diamines and esters of polycarboxylic acids

    NASA Technical Reports Server (NTRS)

    Serafini, T. T.; Delvigs, P.; Lightsey, G. R. (Inventor)

    1973-01-01

    Polyimides having high thermal and oxidative stability are prepared by the reaction of a mixture of monomers comprising (1) a dialkyl or tetraalkyl ester of an aromatic tetracarboxylic acid; (2) an aromatic diamine; and (3) a monoalkyl or dialkyl ester of a dicarboxylic acid where in the ratio of a:b:c is n:(n+1):2, wherein n has a value from 1 to 20. The mixture of monomers is prepared in a 30 to 70 percent by weight solution of an organic solvent, a substrate impregnated with the solution and heated at 50 to 205 C to remove said solvent and form a low molecular weight prepolymer, and thereafter heated at 275 to 350 C to cure to a high molecular weight polyimide.

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

    PubMed

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

    1985-02-01

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

  3. Decarboxylative Allylation of Amino Alkanoic Acids and Esters via Dual Catalysis

    PubMed Central

    2015-01-01

    A combination of photoredox and palladium catalysis has been employed to facilitate the room temperature decarboxylative allylation of recalcitrant α-amino and phenylacetic allyl esters. This operationally simple process produces CO2 as the only byproduct and provides direct access to allylated alkanes. After photochemical oxidation, the carboxylate undergoes radical decarboxylation to site-specifically generate radical intermediates which undergo allylation. A radical dual catalysis mechanism is proposed. Free phenylacetic acids were also allylated utilizing similar reactions conditions. PMID:25228064

  4. Bioactivity and chemical synthesis of caffeic acid phenethyl ester and its derivatives.

    PubMed

    Zhang, Pengxuan; Tang, Yuping; Li, Nian-Guang; Zhu, Yue; Duan, Jin-Ao

    2014-01-01

    Caffeic acid phenethyl ester (CAPE), as one of the main active ingredients of the natural product propolis, shows the unique biological activities such as anti-tumor, anti-oxidation, anti-inflammatory, immune regulation, and so on. These have attracted the attention of many researchers to explore the compound with potent biological activities. This review aims to summarize its bioactivities, synthetic methods and derivatives, which will be helpful for further study and development of CAPE and its derivatives. PMID:25314606

  5. Lewis Acid Catalyzed Synthesis of α-Trifluoromethyl Esters and Lactones by Electrophilic Trifluoromethylation.

    PubMed

    Katayev, Dmitry; Matoušek, Václav; Koller, Raffael; Togni, Antonio

    2015-12-01

    An electrophilic trifluoromethylation of ketene silyl acetals (KSAs) by hypervalent iodine reagents 1 and 2 has been developed. The reaction proceeds under very mild conditions in the presence of a catalytic amount of trimethylsilyl bis(trifluoromethanesulfonyl)imide (up to 2.5 mol %) as a Lewis acid providing a direct access to a variety of secondary, tertiary, and quaternary α-trifluoromethyl esters and lactones in high yield (up to 98%). PMID:26588788

  6. Effects of phthalic acid esters (PAEs) on the neonate and aspects of teratogenic actions.

    PubMed Central

    Thomas, J A; Wienckowski, D B; Gillies, B A; Thomas, M J; Youkilis, E J

    1986-01-01

    A review of the literature reveals that several different phthalic acid esters (PAEs) are capable of causing testicular damage. Phthalate-induced zinc deficiency is consistent with germinal epithelial damage. Among experimental animals, mice perhaps show the greatest sensitivity to phthalate-induced terata, but high doses/exposure are required. Little toxicologic information is available with regard to phthalate-induced effects upon the neonate. PMID:3709448

  7. Surface components of chylomicrons from rats fed glyceryl or alkyl esters of fatty acids: minor components.

    PubMed

    Yang, L Y; Kuksis, A; Myher, J J; Pang, H

    1992-08-01

    The lipid class, fatty acid and molecular species composition of the minor polar surface components of rat lymph chylomicrons were determined during absorption of menhaden oil and corn oil or of the corresponding fatty acid ethyl esters. In addition to the previously reported minor polar lipids (sphingomyelin, phosphatidylserine, phosphatidylinositol, phosphatidic acid and lysophosphatidylcholine), we identified phosphatidylglycerol, dimethylphosphatidylethanolamine, ceramide and cholesteryl sulfate in the chylomicrons from both oil and ester feeding. The dietary fatty acids were found to be incorporated to a variable extent into the different phospholipid classes, the proportions of which remained the same during both types of feeding. No evidence was obtained for the presence of the minor glycerophospholipids characteristic of the lysosomal membranes (e.g., bis-phosphatidic, lysobisphosphatidic and semilysobis-phosphatidic acids), although special efforts were made to identify them. These results indicate that the chylomicrons arising from the monoacylglycerol and phosphatidic acid pathways of triacylglycerol biosynthesis become enveloped in closely similar monolayers of phospholipids. Hence, all triacylglycerols may be secreted from the villus cells via a common mechanism as suggested by the previously demonstrated convergence (at the 2-monoacylglycerol stage) of the monoacylglycerol and the phosphatidic acid pathways of mucosal triacylglycerol formation [Yang, Y.L., and Kuksis, A. (1991) J. Lipid Res. 32, 1173-1186]. PMID:1406072

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

    PubMed

    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. PMID:24137288

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

    PubMed Central

    SON, HYEONG-U; LEE, SANG-HAN

    2013-01-01

    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. PMID:24137288

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

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...-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).

    Code of Federal Regulations, 2010 CFR

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

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...-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...

  13. 40 CFR 721.1731 - Poly(oxy-1,2-ethanediyl), α-methyl-ω-hydroxy, ester with boric acid (H3BO3).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...-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...

  14. 40 CFR 721.1730 - Poly(oxy-1,2-ethanediyl), α-butyl-ω-hydroxy, ester with boric acid (H3BO3).

    Code of Federal Regulations, 2010 CFR

    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...

  15. 40 CFR 721.1731 - Poly(oxy-1,2-ethanediyl), α-methyl-ω-hydroxy, ester with boric acid (H3BO3).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...-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...

  16. 40 CFR 721.1731 - Poly(oxy-1,2-ethanediyl), α-methyl-ω-hydroxy, ester with boric acid (H3BO3).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...-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...

  17. 40 CFR 721.1731 - Poly(oxy-1,2-ethanediyl), α-methyl-ω-hydroxy, ester with boric acid (H3BO3).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...-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...

  18. 40 CFR 721.1730 - Poly(oxy-1,2-ethanediyl), α-butyl-ω-hydroxy, ester with boric acid (H3BO3).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...-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...

  19. 40 CFR 721.1730 - Poly(oxy-1,2-ethanediyl), α-butyl-ω-hydroxy, ester with boric acid (H3BO3).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...-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...

  20. 40 CFR 721.8450 - 2-Propenoic acid, 2-methyl-, 2-[3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl]ethyl ester.

    Code of Federal Regulations, 2010 CFR

    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...

  1. Stereospecific analysis of fatty acid esters of chloropropanediol isolated from fresh goat milk.

    PubMed

    Myher, J J; Kuksis, A; Marai, L; Cerbulis, J

    1986-05-01

    The fatty acid esters of chloropropanediol isolated from goat milk fat in small quantities were subjected to a stereospecific analysis via phospholipase C and phosphocholine esters as intermediates. Synthetic rac-1-chloro-2,3-dioleoyl-propanediol was prepared by standard methods and was used as a control. The stereospecific analyses were performed following a release of the fatty acids from the primary positions of each chloropropanediol diester with pancreatic lipase. The resulting X-1-chloro-2-acylpropanediols were then converted into the corresponding phosphocholine derivatives by a stepwise reaction with phosphorus oxychloride and choline chloride. The X-1-chloro-2-acyl-3-phosphocholinepropanediols were subjected to hydrolysis with phospholipase C (C. perfringens), which hydrolyzed 50% of the phosphatide within two min and the rest of it in two hr. From previous experience with glycerol esters, it was assumed that the more rapidly hydrolyzed molecules were the sn-1-chloro-2-acyl-propanediol derivatives and the more slowly hydrolyzed ones the sn-2-acyl-3-chloropropanediol derivatives. A hydrolysis with phospholipase A2 (Crotalus adamanteus) released 50% of the total fatty acid along with the corresponding lyso compound within 10 min, after which there was no further reaction. The hydrolysis products were assayed directly by gas liquid chromatography (GLC) or were isolated by thin layer chromatography (TLC) prior to quantitation by GLC. Both naturally occurring and synthetic chloropropanediol diesters behaved similarly on stereospecific analysis and were therefore concluded to be racemic. PMID:3724368

  2. Electron paramagnetic resonance studies of gamma-irradiated DL-alanine ethyl ester hydrochloride, L-theanine and L-glutamic acid dimethyl ester hydrochloride.

    PubMed

    Başkan, M Halim; Aydın, Murat

    2013-08-01

    The electron paramagnetic resonance (EPR) of gamma irradiated powders of DL-alanine ethyl ester hydrochloride, L-theanine and L-glutamic acid dimethyl ester hydrochloride were investigated at room temperature. The observed paramagnetic species were attributed to the CH3ĊHCOOC2H5, -CH2ĊHCOOH and -CH2ĊHCOOCH3 radicals, respectively. Hyperfine structure constants and g-values were determined for these three radicals. Some spectroscopic properties and suggestions concerning the possible structure of the radicals were also discussed. PMID:23680512

  3. Electron paramagnetic resonance studies of gamma-irradiated DL-alanine ethyl ester hydrochloride, L-theanine and L-glutamic acid dimethyl ester hydrochloride

    NASA Astrophysics Data System (ADS)

    Başkan, M. Halim; Aydın, Murat

    2013-08-01

    The electron paramagnetic resonance (EPR) of gamma irradiated powders of DL-alanine ethyl ester hydrochloride, L-theanine and L-glutamic acid dimethyl ester hydrochloride were investigated at room temperature. The observed paramagnetic species were attributed to the CH3ĊHCOOC2H5, -CH2ĊHCOOH and -CH2ĊHCOOCH3 radicals, respectively. Hyperfine structure constants and g-values were determined for these three radicals. Some spectroscopic properties and suggestions concerning the possible structure of the radicals were also discussed.

  4. Determination of enthalpy of formation of methyl and ethyl esters of fatty acids.

    PubMed

    Lapuerta, Magín; Rodríguez-Fernández, José; Oliva, Fermín

    2010-02-01

    Biofuels composed by fatty acid methyl esters are widely used as partly substituting fuels for diesel fossil fuels. Additionally, it is expected that the diesel biofuel norms will be extended to ethyl esters produced from bioethanol in the upcoming years. A precise knowledge of the standard enthalpy of formation is necessary for the calculation of some parameters useful for the analysis of the combustion process and emissions of a diesel engine operating with different fuels, such as the heating value, the adiabatic flame temperature or the kinetic mechanisms. However, experimental data for this property are scarce, and only available for short-chain, saturated methyl esters. In this work, four estimation methods for the calculation of the enthalpy of formation are examined and compared. Three of them are simple methods based on groups or bonds contribution, and another one is a computational method (with Gaussian 03 software). After presenting the implementation rules for each of them, conclusions are stated based on the results attained. Gaussian and Benson-Groups methods seem to be more accurate in predicting the actual values of the enthalpy of formation, both methods considering the separation between double bonds and the edge effects in the molecule. However, only the Gaussian method considers the effect of the position of the double bond in the molecule for all the unsaturated esters. PMID:19917272

  5. Determination of the specific radioactivity of fatty acids separated as their methyl esters by gas-liquid chromatography.

    PubMed

    Bishop, C; Glascock, R F; Newell, E M; Welch, V A

    1971-11-01

    Free or combined (3)H-labeled fatty acids are converted to their methyl-(14)C esters or, if labeled with (14)C, to their methyl-(3)H esters. For a given specific radioactivity of the methyl group, the nuclide ratio in the esters separated by GLC is a direct measure of the specific radioactivity of the fatty acids, and quantitative collection is unnecessary. Methods of methylation with minimum quantities of labeled methanol, and of deriving nuclide ratios from channel ratios in a scintillation spectrometer, are given. PMID:5124543

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

    PubMed

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

    2011-10-01

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

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

    SciTech Connect

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

    PubMed

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

    2014-09-01

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

  9. Phytyl Fatty Acid Esters in the Pulp of Bell Pepper (Capsicum annuum).

    PubMed

    Krauß, Stephanie; Hammann, Simon; Vetter, Walter

    2016-08-17

    Phytyl fatty acid esters (PFAE) are esters of fatty acids with the isoprenoid alcohol phytol (3,7R,11R,15-tetramethylhexadec-2E-enol). In this study, PFAE were identified and quantified in bell pepper using gas chromatography with mass spectrometry (GC-MS). All red (n = 14) and yellow (n = 6) samples contained six or seven PFAE at 0.9-11.2 mg/100 g fresh weight. By contrast, PFAE were not detected in green bell pepper samples (n = 3). PFAE might eventually be a source for bioavailable phytol, which can be transformed into phytanic acid by humans. Phytanic acid cannot be properly degraded by patients who suffer from Refsum's disease (tolerable daily intake (TDI) ≤ 10 mg of phytanic acid). The phytol moiety of the PFAE (0.4-5.4 mg/100 g fresh weight) would contribute up to ∼50% to the TDI with the consumption of only one portion of bell pepper fruit pulp. PMID:27458658

  10. Chemical cross-linking with NHS esters: a systematic study on amino acid reactivities.

    PubMed

    Mädler, Stefanie; Bich, Claudia; Touboul, David; Zenobi, Renato

    2009-05-01

    Structure elucidation of tertiary or quaternary protein structures by chemical cross-linking and mass spectrometry (MS) has recently gained importance. To locate the cross-linker modification, dedicated software is applied to analyze the mass or tandem mass spectra (MS/MS). Such software requires information on target amino acids to limit the data analysis time. The most commonly used homobifunctional N-hydroxy succinimide (NHS) esters are often described as reactive exclusively towards primary amines, although side reactions with tyrosine and serine have been reported. Our goal was to systematically study the reactivity of NHS esters and derive some general rules for their attack of nucleophilic amino acid side chains in peptides. We therefore studied the cross-linking reactions of synthesized and commercial model peptides with disuccinimidyl suberate (DSS). The first reaction site in all cases was expectedly the alpha-NH(2)-group of the N-terminus or the epsilon-NH(2)-group of lysine. As soon as additional cross-linkers were attached or loops were formed, other amino acids were also involved in the reaction. In addition to the primary amino groups, serine, threonine and tyrosine showed significant reactivity due to the effect of neighboring amino acids by intermediate or permanent Type-1 cross-link formation. The reactivity is highly dependent on the pH and on adjacent amino acids. PMID:19132714

  11. 75 FR 20785 - Polyglyceryl Phthalate Ester of Coconut Oil Fatty Acids; Exemption from the Requirement of a...

    Federal Register 2010, 2011, 2012, 2013, 2014

    2010-04-21

    ... . II. What Does this Correction Do? In the Federal Register of July 8, 2009, (74 FR 32456), EPA's... of polyglyceryl phthalate ester of coconut oil fatty acids, including fatty acid coco polymers with... acid coco of surfactants polymers with glyceryl and phthalic anhydride (CAS No. 67746-02-5) and...

  12. 40 CFR 721.10457 - 1,2-Benzenedicarboxylic acid, mixed esters with benzyl alc., cyclohexanol, 2-ethyl-1-hexanol...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... esters with benzyl alc., cyclohexanol, 2-ethyl-1-hexanol, fumaric acid and propylene glycol. 721.10457...-hexanol, fumaric acid and propylene glycol. (a) Chemical substance and significant new uses subject to... alc., cyclohexanol, 2-ethyl-1-hexanol, fumaric acid and propylene glycol (PMN P-03-154; CAS No....

  13. 40 CFR 721.10457 - 1,2-Benzenedicarboxylic acid, mixed esters with benzyl alc., cyclohexanol, 2-ethyl-1-hexanol...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... esters with benzyl alc., cyclohexanol, 2-ethyl-1-hexanol, fumaric acid and propylene glycol. 721.10457...-hexanol, fumaric acid and propylene glycol. (a) Chemical substance and significant new uses subject to... alc., cyclohexanol, 2-ethyl-1-hexanol, fumaric acid and propylene glycol (PMN P-03-154; CAS No....

  14. 21 CFR 582.4101 - Diacetyl tartaric acid esters of mono- and diglycerides of edible fats or oils, or edible fat...

    Code of Federal Regulations, 2010 CFR

    2010-04-01

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

  15. 21 CFR 582.4101 - Diacetyl tartaric acid esters of mono- and diglycerides of edible fats or oils, or edible fat...

    Code of Federal Regulations, 2013 CFR

    2013-04-01

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

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

    Code of Federal Regulations, 2014 CFR

    2014-04-01

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

  17. 21 CFR 582.4101 - Diacetyl tartaric acid esters of mono- and diglycerides of edible fats or oils, or edible fat...

    Code of Federal Regulations, 2011 CFR

    2011-04-01

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

  18. 21 CFR 582.4101 - Diacetyl tartaric acid esters of mono- and diglycerides of edible fats or oils, or edible fat...

    Code of Federal Regulations, 2012 CFR

    2012-04-01

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

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

    NASA Astrophysics Data System (ADS)

    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.

  20. 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.

    PubMed

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

    2016-04-01

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

  1. Characterization of Benthic Microbial Community Structure by High-Resolution Gas Chromatography of Fatty Acid Methyl Esters

    PubMed Central

    Bobbie, Ronald J.; White, David C.

    1980-01-01

    Fatty acids are a widely studied group of lipids of sufficient taxonomic diversity to be useful in defining microbial community structure. The extraordinary resolution of glass capillary gas-liquid chromatography can be utilized to separate and tentatively identify large numbers of fatty acid methyl esters derived from the lipids of estuarine detritus and marine benthic microbiota without the bias of selective methods requiring culture or recovery of the microbes. The gas-liquid chromatographic analyses are both reproducible and highly sensitive, and the recovery of fatty acids is quantitative. The analyses can be automated, and the diagnostic technique of mass spectral fragmentation analysis can be readily applied. Splitless injection on glass capillary gas chromatographic columns detected by mass spectral selective ion monitoring provides an ultrasensitive and definitive monitoring system. Reciprocal mixtures of bacteria and fungi, when extracted and analyzed, showed progressive changes of distinctive fatty acid methyl esters derived from the lipids. By manipulating the environment of an estuarine detrital microbial community with antibiotics and culture conditions, it was possible to produce a community greatly enriched in eucaryotic fungi, as evidenced by scanning electron microscopic morphology. The fatty acid methyl esters from the lipids in the fungus-enriched detritus showed enrichment of the C18 dienoic and the C18 and C20 polyenoic esters. Manipulation of the detrital microbiota that increased the procaryotic population resulted in an absence of large structures typical of fungal mycelia or diatoms, as evidenced by scanning electron microscopy, and a significantly larger proportion of anteiso- and isobranched C15 fatty acid esters, C17 cyclopropane fatty acid esters, and the cis-vaccenic isomer of the C18 monoenoic fatty acid esters. As determined by these techniques, a marine settling community showed greater differences in bacterial as contrasted to

  2. Simultaneous analysis of low plasma levels of deuterium-labeled saturated and unsaturated fatty acids as t-butyldimethylsilyl esters

    SciTech Connect

    Parsons, H.; Emken, E.M.; Marai, L.; Kuksis, A.

    1986-03-01

    A sensitive and accurate method for detection and quantitation of deuterated fatty acids in the presence of large amounts of unlabeled fatty acids is described using mass fragmentography in combination with the preparation of tertiarybutyldimethylsilyl esters (t-BDMS). The method has been applied to determination of deuterated stearic, oleic, elaidic and linoleic acids in human plasma lipoproteins following duodenal perfusion with a micellar mixture of acids. Over a concentration range of 10-1000 ng/ml, the average coefficient of variation for the linoleate was 3% and for the oleate (elaidate) ester was 2%.

  3. Synthesis and Biological Evaluation of Novel Mono Acid Esters Derived from the Constituents of Urtica pilulifera

    PubMed Central

    I. Husein, Ahmad; J. Jondi, Waheed; A. Zatar, Nidal; S. Ali-Shtayeh, Mohammed

    2014-01-01

    New mono acid esters have been synthesized from the reaction of benzoic acid and mono-hydroxybenzoic acids with 2-phenoxyethanol separated from Urtica pilulifera, characterized, and screened for possible antioxidant, antifungal, antimicrobial and anticancer activities. These phenolic acid esters gave various degrees of free radical scavenging, but the values were lower than that of α-tocopherol. The concentrations of the tested compounds needed to reduce DPPH absorption by 50% at 517 nm were nearly in the range of 900-1100 µg/mL. While for α-tocopherol was 40 µg /mL. The compounds were tested in-vitro against six bacterial species which are known to cause dermic and mucosal infections in human. 2-phenoxyethyl benzoate showed significant activity in the range of 30% against P. aeruginosa to 70% against E. coli compared with the activity of Streptomycin. On the other hand 2-phenoxyethyl 2-hydroxybenzoate reveals 70% of gentamicin against K. pneumoniae. The tested compounds also showed complete inhibition at a concentration less than 37.5 µg/mL against M. canis and less than 50 µg/mL against T. rubrum. 2-phenoxyethyl 4-hydroxybenzoate showed considerable activity against MCF-7 with IC50 is less than 62.5 µg/mL. PMID:25587305

  4. Synthesis and Biological Evaluation of Novel Mono Acid Esters Derived from the Constituents of Urtica pilulifera.

    PubMed

    I Husein, Ahmad; J Jondi, Waheed; A Zatar, Nidal; S Ali-Shtayeh, Mohammed

    2014-01-01

    New mono acid esters have been synthesized from the reaction of benzoic acid and mono-hydroxybenzoic acids with 2-phenoxyethanol separated from Urtica pilulifera, characterized, and screened for possible antioxidant, antifungal, antimicrobial and anticancer activities. These phenolic acid esters gave various degrees of free radical scavenging, but the values were lower than that of α-tocopherol. The concentrations of the tested compounds needed to reduce DPPH absorption by 50% at 517 nm were nearly in the range of 900-1100 µg/mL. While for α-tocopherol was 40 µg /mL. The compounds were tested in-vitro against six bacterial species which are known to cause dermic and mucosal infections in human. 2-phenoxyethyl benzoate showed significant activity in the range of 30% against P. aeruginosa to 70% against E. coli compared with the activity of Streptomycin. On the other hand 2-phenoxyethyl 2-hydroxybenzoate reveals 70% of gentamicin against K. pneumoniae. The tested compounds also showed complete inhibition at a concentration less than 37.5 µg/mL against M. canis and less than 50 µg/mL against T. rubrum. 2-phenoxyethyl 4-hydroxybenzoate showed considerable activity against MCF-7 with IC50 is less than 62.5 µg/mL. PMID:25587305

  5. Preparation of fatty acid methyl esters for gas-liquid chromatography[S

    PubMed Central

    Ichihara, Ken'ichi; Fukubayashi, Yumeto

    2010-01-01

    A convenient method using commercial aqueous concentrated HCl (conc. HCl; 35%, w/w) as an acid catalyst was developed for preparation of fatty acid methyl esters (FAMEs) from sterol esters, triacylglycerols, phospholipids, and FFAs for gas-liquid chromatography (GC). An 8% (w/v) solution of HCl in methanol/water (85:15, v/v) was prepared by diluting 9.7 ml of conc. HCl with 41.5 ml of methanol. Toluene (0.2 ml), methanol (1.5 ml), and the 8% HCl solution (0.3 ml) were added sequentially to the lipid sample. The final HCl concentration was 1.2% (w/v). This solution (2 ml) was incubated at 45°C overnight or heated at 100°C for 1–1.5 h. The amount of FFA formed in the presence of water derived from conc. HCl was estimated to be <1.4%. The yields of FAMEs were >96% for the above lipid classes and were the same as or better than those obtained by saponification/methylation or by acid-catalyzed methanolysis/methylation using commercial anhydrous HCl/methanol. The method developed here could be successfully applied to fatty acid analysis of various lipid samples, including fish oils, vegetable oils, and blood lipids by GC. PMID:19759389

  6. Studies of the acidic components of the Colorado Green River formation oil shale-Mass spectrometric identification of the methyl esters of extractable acids.

    NASA Technical Reports Server (NTRS)

    Haug, P.; Schnoes, H. K.; Burlingame, A. L.

    1971-01-01

    Study of solvent extractable acidic constituents of oil shale from the Colorado Green River Formation. Identification of individual components is based on gas chromatographic and mass spectrometric data obtained for their respective methyl esters. Normal acids, isoprenoidal acids, alpha, omega-dicarboxylic acids, mono-alpha-methyl dicarboxylic acids and methyl ketoacids were identified. In addition, the presence of monocyclic, benzoic, phenylalkanoic and naphthyl-carboxylic acids, as well as cycloaromatic acids, is demonstrated by partial identification.

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

    PubMed

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

    2015-01-01

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

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

    PubMed

    Porto, Anthony F

    2014-09-01

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

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

    NASA Astrophysics Data System (ADS)

    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.

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

    PubMed

    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

    2016-01-01

    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 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. PMID:26916830

  11. The conformational properties of α,β-dehydroamino acids with a C-terminal ester group.

    PubMed

    Siodłak, Dawid; Grondys, Justyna; Broda, Małgorzata A

    2011-10-01

    α,β-Dehydroamino acid esters occur in nature. To investigate their conformational properties, a systematic theoretical analysis was performed on the model molecules Ac-ΔXaa-OMe [ΔXaa = ΔAla, (E)-ΔAbu, (Z)-ΔAbu, ΔVal] at the B3LYP/6-311+ + G(d,p) level in the gas phase as well as in chloroform and water solutions with the self-consistent reaction field-polarisable continuum model method. The Fourier transform IR spectra in CCl(4) and CHCl(3) have been analysed as well as the analogous solid state conformations drawn from The Cambridge Structural Database. The ΔAla residue has a considerable tendency to adopt planar conformations C5 (ϕ, ψ ≈ - 180°, 180°) and β2 (ϕ, ψ ≈ - 180°, 0°), regardless of the environment. The ΔVal residue prefers the conformation β2 (ϕ, ψ ≈ - 120°, 0°) in a low polar environment, but the conformations α (ϕ, ψ ≈ - 55°, 35°) and β (ϕ, ψ ≈ - 55°, 145°) when the polarity increases. The ΔAbu residues reveal intermediate properties, but their conformational dispositions depend on configuration of the side chain of residue: (E)-ΔAbu is similar to ΔAla, whereas (Z)-ΔAbu to ΔVal. Results indicate that the low-energy conformation β2 is the characteristic feature of dehydroamino acid esters. The studied molecules constitute conformational patterns for dehydroamino acid esters with various side chain substituents in either or both Z and E positions. PMID:21805538

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

    PubMed

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

    2014-07-01

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

  13. 40 CFR 721.3025 - Fatty acids C12-18, C18 unsaturated, C12-18 alkyl esters (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ..., 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...

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

    NASA Astrophysics Data System (ADS)

    Tamber, Harinder Singh

    1997-12-01

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

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

    PubMed Central

    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

  16. Synthesis and biological activity of arylspiroborate salts derived from caffeic Acid phenethyl ester.

    PubMed

    Hébert, Martin J G; Flewelling, Andrew J; Clark, Trevor N; Levesque, Natalie A; Jean-François, Jacques; Surette, Marc E; Gray, Christopher A; Vogels, Christopher M; Touaibia, Mohamed; Westcott, Stephen A

    2015-01-01

    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. PMID:25834744

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

    PubMed

    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

  18. A new steroidal glycoside and fatty acid esters from the stem bark of Tectona grandis Linn.

    PubMed

    Khan, Zeba; Ali, M; Bagri, Priyanka

    2010-07-01

    The phytochemical investigation of the bark of Tectona grandis Linn. afforded a new steroidal glycoside identified as beta-sitosterol-beta-D-[4'-linolenyl-6'-(tridecan-4'''-one-1'''-oxy)] glucuranopyranoside and three new fatty esters, 7'-hydroxy-n-octacosanoyl n-decanoate, 20'-hydroxy eicosanyl linolenate and 18'-hydroxy n-hexacosanyl n-decanoate, along with the known compounds n-docosane, lup-20(29)-en-3beta-ol, betulinic acid and stigmast-5-en-3-O-beta-D-glucopyranoside. Their stereostructures have been elucidated on the basis of spectral data analyses and chemical reactions. PMID:20552529

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

    NASA Astrophysics Data System (ADS)

    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.

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

    PubMed Central

    Hébert, Martin J. G.; Flewelling, Andrew J.; Clark, Trevor N.; Jean-François, Jacques; Surette, Marc E.; Gray, Christopher A.; Vogels, Christopher M.; Touaibia, Mohamed; Westcott, Stephen A.

    2015-01-01

    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. PMID:25834744

  1. Chan-Evans-Lam Amination of Boronic Acid Pinacol (BPin) Esters: Overcoming the Aryl Amine Problem.

    PubMed

    Vantourout, Julien C; Law, Robert P; Isidro-Llobet, Albert; Atkinson, Stephen J; Watson, Allan J B

    2016-05-01

    The Chan-Evans-Lam reaction is a valuable C-N bond forming process. However, aryl boronic acid pinacol (BPin) ester reagents can be difficult coupling partners that often deliver low yields, in particular in reactions with aryl amines. Herein, we report effective reaction conditions for the Chan-Evans-Lam amination of aryl BPin with alkyl and aryl amines. A mixed MeCN/EtOH solvent system was found to enable effective C-N bond formation using aryl amines while EtOH is not required for the coupling of alkyl amines. PMID:27045570

  2. Sterically controlled azomethine ylide cycloaddition polymerization of phenyl-C61-butyric acid methyl ester.

    PubMed

    Stephen, Meera; Ramanitra, Hasina H; Santos Silva, Hugo; Dowland, Simon; Bégué, Didier; Genevičius, Kristijonas; Arlauskas, Kęstutis; Juška, Gytis; Morse, Graham E; Distler, Andreas; Hiorns, Roger C

    2016-05-01

    Phenyl-C61-butyric acid methyl ester (PCBM) is polymerized simply using a one-pot reaction to yield soluble, high molecular weight polymers. The sterically controlled azomethine ylide cycloaddition polymerization (SACAP) is demonstrated to be highly adaptable and yields polymers with probable Mn≈ 24 600 g mol(-1) and Mw≈ 73 800 g mol(-1). Products are metal-free and of possible benefit to organic and hybrid photovoltaics and electronics as they form thin films from solution and have raised LUMOs. The promising electronic properties of this new polymer are discussed. PMID:27066898

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

    PubMed

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

    2016-01-01

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

  4. Influence of fatty acid methyl esters from hydroxylated vegetable oils on diesel fuel lubricity.

    PubMed

    Goodrum, John W; Geller, Daniel P

    2005-05-01

    Current and future regulations on the sulfur content of diesel fuel have led to a decrease in lubricity of these fuels. This decreased lubricity poses a significant problem as it may lead to wear and damage of diesel engines, primarily fuel injection systems. Vegetable oil based diesel fuel substitutes (biodiesel) have been shown to be clean and effective and may increase overall lubricity when added to diesel fuel at nominally low levels. Previous studies on castor oil suggest that its uniquely high level of the hydroxy fatty acid ricinoleic acid may impart increased lubricity to the oil and its derivatives as compared to other vegetable oils. Likewise, the developing oilseed Lesquerella may also increase diesel lubricity through its unique hydroxy fatty acid composition. This study examines the effect of castor and Lesquerella oil esters on the lubricity of diesel fuel using the High-Frequency Reciprocating Rig (HFRR) test and compares these results to those for the commercial vegetable oil derivatives soybean and rapeseed methyl esters. PMID:15607199

  5. Generation of anticalins with specificity for a nonsymmetric phthalic acid ester.

    PubMed

    Mercader, Josep V; Skerra, Arne

    2002-09-15

    A set of engineered lipocalins, so-called anticalins, that bind benzyl butyl phthalate, a potential pollutant of environmental and food samples or medical plastic ware, has been generated. To this end, the synthesis of a derivative of the target analyte carrying an activatable carboxylate group at the end of an aliphatic spacer arm was established. This compound was covalently coupled to amino-functionalized paramagnetic beads. Using phage display technology three variants were selected from a random library of the bilin-binding protein (BBP), a prototypic lipocalin, which exhibit binding activity toward the nonsymmetric phthalic acid ester. These anticalins (denominated PhtA, PhtB, and PhtC) possess dissociation constants of 9.1, 6.2, and 11.6 microM, respectively. Specificity for the binding of other phthalic acid esters was studied. No cross-reactivity was found for diethyl phthalate, while binding to dibutyl phthalate was observed with higher dissociation constants. Interestingly, two differing types of binding behavior were observed among the three selected anticalins. Sequence comparison of these engineered lipocalins with the wild-type BBP revealed that all of the 16 randomized positions carried an amino acid exchange and that a certain sequence pattern had been selected, thus pointing toward a peculiar mode of structural interaction. Our data suggest that the generation of anticalins may provide an alternative to antibodies for the creation of stable receptor proteins against haptens with bioanalytical relevance. PMID:12419339

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

    PubMed

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

    2016-06-01

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

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

    PubMed

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

    2009-10-01

    Polyvinylphosphonic acid (PVPA), a biomimetic analog of phosphoproteins, is crucial for recruiting polyacrylic acid (PAA)-stabilized amorphous calcium phosphate nanoprecursors during biomimetic remineralization of dentin collagen matrices. This study tested the null hypothesis that phosphoric acid esters of methacrylates in dentin adhesives cannot replace PVPA during bimimetic remineralization of resin-dentin interfaces. Human dentin specimens were bonded with: (I) XP Bond, an etch-and-rinse adhesive using moist bonding; (II) XP Bond using dry bonding; (III) Adper Prompt L-Pop, a self-etching adhesive. The control medium contained only set Portland cement and a simulated body fluid (SBF) without any biomimetic analog. Two experimental Portland cement/SBF remineralization media were evaluated: the first contained PAA as the sole biomimetic analog, the second contained PAA and PVPA as dual biomimetic analogs. No remineralization of the resin-dentin interfaces could be identified from specimens immersed in the control medium. After 2-4 months in the first experimental medium, specimens exhibited either no remineralization or large crystal formation within hybrid layers. Only specimens immersed in the second remineralization medium produced nanocrystals that accounted for intrafibrillar remineralization within hybrid layers. The null hypothesis could not be rejected; phosphoric acid esters in dentin adhesives cannot replace PVPA during biomimetic remineralization of adhesive-bonded dentin. PMID:19481792

  8. Terpolymers of ethyl acrylate/methacrylic acid/unsaturated acid ester of alcohols and acids as anti-settling agents in coal water slurries

    SciTech Connect

    Savoly, A.; Villa, J.L.; Grinstein, R.H.; Nachfolger, S.J.

    1988-05-17

    This patent describes a pumpable stabilized coal water slurry, having a coal content of at least about 50% by weight wherein at least 80% of the coal particles are about 200 mesh or finer, containing from about 0.01% to about 1% by weight of the slurry of a water soluble terpolymer of ethylacrylate (A), metacrylic acid (B) and a third monomer (C) selected from the group consisting of an unsaturated carboxylic acid ester of an alcohol and an ethoxylated carboxylic acid. The unsaturated carboxylic acid is a mono- or di- basic unsaturated carboxylic acid of 3 to 10 carbon atoms selected from the group consisting of acrylic acid, methacrylic acid, itaconic acid, fumaric acid, and maleic acid.

  9. Identification of Organic Sulfate Esters in d-Limonene Ozonolysis SOA Under Acidic Condition

    NASA Astrophysics Data System (ADS)

    Iinuma, Y.; Mueller, C.; Boege, O.; Herrmann, H.

    2006-12-01

    Secondary organic aerosol (SOA) components from gas phase ozonolysis of d-limonene were investigated in a series of indoor chamber experiments. The compounds smaller than 300 Da were quantified using capillary electrophoresis coupled to electrospray ionisation ion trap mass spectrometry (CE/ESI-ITMS). HPLC coupled to an ESI-TOFMS and an ESI-ITMS was used for structural study of dimmers and oligomers. Only 10% of the produced SOA could be attributed to low molecular weight carboxylic acids (Mw<300). The oxidation products which have molecular weights over 300 were detected regardless of the seed particle acidity but the concentrations of these compounds were much higher for acidic seed particle experiments. Strong signals of the compounds with mass to charge ratios (m/z) 281, 465 and 481 were detected when sulphuric acid was used in the seed particles. These compounds showed a strong fragment of m/z 97 in MS2 or MS3 spectra indicating the presence of sulfate in the structures. HPLC/ESI-TOFMS analysis suggests the elemental compositions of C10H17O7S-, C20H33O10S- and C20H33O11S- for m/z 281, 465 and 481, respectively. Based on MS^{n} and TOFMS results, they are most likely organic sulfate esters, possibly formed by a heterogeneous acid catalyzed reaction of a limonene oxidation product and sulfuric acid in the particle phase. The concentrations of the organic sulfate ester were as high as 3.7 μgm-3 for m/z 281.

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

    PubMed

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

    2013-09-01

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

  11. Theoretical studies of fundamental pathways for alkaline hydrolysis of carboxylic acid esters in gas phase

    SciTech Connect

    Zhan, C.G.; Landry, D.W.; Ornstein, R.L.

    2000-02-23

    Fundamental reaction pathways for the alkaline hydrolysis of carboxylic acid esters, RCOOR{prime}, were examined through a series of first-principle calculations. The reactions of six representative esters with hydroxide ion were studied in the gas phase. A total of three competing reaction pathways were found and theoretically confirmed for each of the esters examined: bimolecular base-catalyzed acyl-oxygen cleavage (B{sub AC}2), bimolecular base-catalyzed alkyl-oxygen cleavage (B{sub AL}2), and carbonyl oxygen exchange with hydroxide. For the two-step B{sub AC}2 process, this is the first theoretical study to consider the individual sub-steps of the reaction process and to consider substituent effects. For the carbonyl oxygen exchange with hydroxide and for the one-step B{sub AL}2 process, the authors report here the first quantitative theoretical results for the reaction pathways and for the energy barriers. The energy barrier calculated for the second step of the B{sub AC}2 process, that is, the decomposition of the tetrahedral intermediate, is larger in the gas phase than that of the first step, that is, the formation of the tetrahedral intermediate, for all but one of the esters examined. The exception, CH{sub 3}COOC(CH{sub 3}){sub 3}, does not have an {alpha} hydrogen in the leaving group. The highest energy barrier calculated for the B{sub AC}2 process is always lower than the barriers for the oxygen exchange and for the B{sub AL}2 process. The difference between the barrier for the B{sub AL}2 process and the highest barrier for the B{sub AC}2 process is only {approximately}1--3 kcal/mol for the methyl esters, but becomes much larger for the others. Substitution of an {alpha} hydrogen in R{prime} with a methyl group considerably increases the energy barrier for the B{sub AL}2 process, and significantly decreases the energy barrier for the second step of the B{sub AC}2 process. The calculated substituent shifts of the energy barrier for the first step of the

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

    PubMed

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

    2014-01-01

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

  13. Cholestane as a digestibility marker in the absorption of polyunsaturated fatty acid ethyl esters in Atlantic salmon.

    PubMed

    Sigurgisladottir, S; Lall, S P; Parrish, C C; Ackman, R G

    1992-06-01

    Salmonid fish require long-chain n-3 fatty acids in their diet. The digestibility of different chemical forms of fish oil fatty acids, fed as triacylglycerols, free fatty acids or ethyl esters, was examined in 300 g farmed Atlantic salmon (Salmo salar) using cholestane as an indicator of fat absorption in lieu of the chromium oxide (Cr2O3) which is commonly used as a marker in digestibility studies. It was established that the two digestibility markers gave similar results. Conveniently, cholestane does not require a separate analysis if fatty acids are to be determined by appropriate gas-liquid chromatography. The long-chain polyunsaturated fatty acids were particularly well absorbed, the apparent digestibility being 90-98% when feeding triacylglycerols or free fatty acids. However, the digestibility of monounsaturated fatty acids (75-94%) was lower, and lower still for saturated fatty acids (50-80%). Ethyl esters of fatty acids were significantly less well absorbed (P less than 0.05) than were the corresponding fatty acids in free acid or triacylglycerol form. Irrespective of dietary fat type, only free fatty acids were identified in feces, indicating total hydrolysis of triacylglycerols and ethyl esters. PMID:1630276

  14. Computational study of the acid dissociation of esters and lactones. A case study of diketene.

    PubMed

    Gómez-Bombarelli, Rafael; González-Pérez, Marina; Pérez-Prior, María Teresa; Calle, Emilio; Casado, Julio

    2009-07-17

    A computational study of the aqueous pK(a) of some saturated and unsaturated cyclic and linear esters and ketones was carried out at the DFT-B3LYP 6-31++G(2df,2pd), CBS-Q, and G2 levels, with the integral equation formalism polarizable continuum model for solvation, using a proton exchange mechanism. The influence of unsaturation, position of the double bond, and cyclization were studied. The computational results show that (a) in all cases studied except that of diketene (4-methylene-2-oxetanone), the alpha-beta unsaturated isomer is 20-30 kJ mol(-1) lower in energy that the beta-gamma unsaturated one; (b) alpha-beta unsaturation lowers the pK(a) of an ester approximately 6 units, whereas beta-gamma unsaturation lowers it by approximately 10 units, and cyclization lowers the pK(a) by approximately 3 units. In order to check the predictive power of the methodology, the acid dissociation constant of diketene in water was measured via kinetic study of its base-catalyzed hydrolysis. The pK(a) value obtained (15.2 +/- 0.3) is in keeping with the expected value for a beta-gamma unsaturated beta-lactone. This low value also suggests that deprotonated diketene does not interconvert to a more stable, less acidic alpha-beta unsaturated isomer, which is also consistent with computational results. PMID:19459649

  15. The effect of elevated temperature on the strength parameters of silica acid ester consolidated porous limestones

    NASA Astrophysics Data System (ADS)

    Pápay, Zita; Török, Ákos

    2013-04-01

    The porous limestone is one of the most widespread construction materials of the monuments in Central Europe, with emblematic buildings in Vienna, Bratislava, Budapest and many other cities of Austria, Slovakia, Czech Republic and Hungary. The restoration of these monuments very often requires the consolidation of the porous limestone material, where various types of consolidants are used to strengthen the highly weathered stone. Our research focused on the understanding of the behaviour of consolidated porous limestone when the material is subjected to higher temperatures. Test procedure included the preparation of cylindrical test specimens from the Miocene porous limestone which was followed by consolidation by four various types of silica acid ester. The samples after consolidation were heated to 300 and 600 °C in electric oven. The material properties such as ultrasonic pulse velocity, density were tested before and after the treatment. Indirect tensile strength (Brazilian test) was used to compare the strength parameters of non treated and consolidated samples. Silica acid ester treated samples after heating were also measured in terms of strength, density and ultrasonic pulse velocity. The results show that there are significant changes in strength of various pre-treated samples after heating indicating the sensitivity of the materials to temperature changes and accidental fire.

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

    PubMed

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

    2009-03-01

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

  17. Effect of Linker Structure on Salicylic Acid-Derived Poly(anhydride–esters)

    PubMed Central

    Prudencio, Almudena; Schmeltzer, Robert C.; Uhrich, Kathryn E.

    2013-01-01

    A series of salicylic acid-derived poly(anhydride–esters) were synthesized by melt polym erization methods, in which the structures of the molecule (“linker”) linking together the two salicylic acids were varied. To determine the relationship between the linker and the physical properties of the corresponding poly(anhydride–ester), several linkers were evaluated including linear aliphatic, aromatic, and aliphatic branched structures. For the linear aliphatic linkers, higher molecular weights were obtained with longer linear alkyl chains. The most sterically hindered linkers yielded lower molecular weight polymers. The thermal decomposition temperature increased with the alkyl chain length, but the glass transition temperature decreased, due to the enhanced flexibility of the polymer. The highest glass transition temperatures were obtained by using aromatic linkers as a result of increased π–π interactions. Water contact angles determined the relative hydrophobicity of the polymers, which correlated to hydrolytic degradation rates; i.e., the highest contact angle values yielded the slowest degrading polymers. PMID:23976793

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

    PubMed Central

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

    2011-01-01

    An enzymatic reactor with lipase immobilized on a monolithic polymer support has been prepared and used to catalyze the transesterification of triacylglycerides into the fatty acid methyl esters commonly used for biodiesel. A design of experiments procedure was used to optimize the monolithic reactor with variables including control of the surface polarity of the monolith via variations in the length of the hydrocarbon chain in alkyl methacrylate monomer, time of grafting of 1-vinyl-4,4-dimethylazlactone used to activate the monolith, and time used for the immobilization of porcine lipase. Optimal conditions involved the use of a poly(stearyl methacrylate-co-ethylene dimethacrylate) monolith, grafted first with vinylazlactone, then treated with lipase for 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. PMID:21915852

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

    PubMed

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

    2016-09-01

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

  20. Rhythms in cholesterol, cholesteryl esters, free fatty acids, and triglycerides in blood of lactating dairy cows.

    PubMed

    Bitman, J; Wood, D L; Lefcourt, A M

    1990-04-01

    Blood samples from six lactating dairy cows were analyzed to determine whether circulating neutral lipids exhibit rhythmic variations. Plasma neutral lipids were measured by quantitative TLC on every fourth integrated 15-min blood sample taken over 48-h periods. Cows were housed in an environmental chamber at 20 degrees C with 16 h light:8 h dark (lights on at 0700 h), fed daily at 0900 h, and milked at 0830 and 2000 h. Other variables monitored included: body temperature, ammonia nitrogen, urea nitrogen, glucose, triiodothyronine, thyroxine, somatotropin, insulin, cortisol, and prolactin. Mean concentrations of cholesterol, cholesteryl esters, free fatty acids, and triglycerides were 21.4, 175.4, 3.1, and 6.3 mg/dl, respectively. Visual and power spectral analysis of the pulsatile fluctuations in lipids indicated rhythms with periods of 2 to 3 h. Amplitudes of rhythms for free fatty acids and triglycerides were 60% of mean concentrations and for cholesterol and cholesteryl esters were 20% of mean concentrations. The presence of these rhythms was conserved when data were averaged across time by cow. However, because of nonstationary conditions, rhythms identified by spectral analysis were not statistically significant. There was no evidence of circadian patterns in circulating neutral lipid components. All other metabolic and hormonal variables except cortisol exhibited distinct circadian rhythms. PMID:2345205

  1. Amonia gas: an improved reagent for chemical ionization mass spectrometry of bile acid methyl ester acetates

    SciTech Connect

    DeMark, B.R.; Klein, P.D.

    1981-01-01

    The ammonia chemical ionization mass spectra of 28 methyl ester acetate derivatives of bile acids and related compounds have been determined by gas-liquid chromatography-mass spectrometry. Advantages of ammonia ionization over the previously studied isobutane ionization include a 130 to 270% enhancement in the sensitivity of base peak monitoring, and direct determination of molecular weight from the base peak (M + NH/sub 4//sup +/) in the mass spectrum of any of the derivatives. Minor ions in the ammonia spectra also allow selective detection of 3-keto compounds and can indicate unsaturation or double bond conjugation in the molecule. The significance of these studies for the detection and quantitation of bile acids is discussed. 2 tables.

  2. Molecular recognition of isomeric protonated amino acid esters monitored by ESI-mass spectrometry.

    PubMed

    Liesenfeld, Andrea; Lützen, Arne

    2014-01-01

    Two new 9,9'-spirobifluorene-derived crown ethers were prepared and used to recognise constitutionally isomeric amino acid derivatives. The performance of the receptors was evaluated by ESI-mass spectrometry using the isomer labelled guest method (ILGM). This method revealed the preferred binding of L-norleucine and L-leucine compared to L-isoleucine for both receptors. Furthermore, non-covalent isotope effects demonstrate the relevance of dispersive interactions for the overall binding event. These effects also provide hints for the relative spatial orientation of the guest molecules within the host-guest complex, and thereby prove the importance of the spirobifluorene moiety for the observed binding of the protonated amino acid esters. PMID:24778737

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

    PubMed

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

    1999-04-01

    Fatty acid ethyl esters (FAEE), nonoxidative ethanol metabolites present in human organs commonly damaged by ethanol abuse, have been implicated as mediators of organ damage. FAEE are additives in various foods and beverages to provide flavor or fragrance, and therefore are common dietary lipid constituents. We hypothesized that FAEE could be generated during alcoholic beverage production because fatty acids are present within microorganisms and ethanol is generated during the fermentation process. In this report, we demonstrate that FAEE are present in commercially available scotch beverages, and that in the preparation of scotch, FAEE can be produced during the fermentation reaction as a result of FAEE synthase activity in the yeast. Following ingestion of scotch, preformed FAEE are delivered to GI tract. The consequences of ingestion of FAEE in scotch, if any, remain to be determined. PMID:10231172

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

    SciTech Connect

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

    2014-12-21

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

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

    PubMed

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

    2016-02-10

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

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

    USGS Publications Warehouse

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

    1994-01-01

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

  7. Inhibition of mammalian carbonic anhydrase isoforms I-XIV with a series of phenolic acid esters.

    PubMed

    Maresca, Alfonso; Akyuz, Gulay; Osman, Sameh M; AlOthman, Zeid; Supuran, Claudiu T

    2015-11-15

    A series of phenolic acid esters incorporating caffeic, ferulic, and p-coumaric acid, and benzyl, m/p-hydroxyphenethyl- as well as p-hydroxy-phenethoxy-phenethyl moieties were investigated for their inhibitory effects against the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1). Many of the mammalian isozymes of human (h) or murine (m) origin, hCA I-hCA XII, mCA XIII and hCA XIV, were inhibited in the submicromolar range by these derivatives (with KIs of 0.31-1.03 μM against hCA VA, VB, VI, VII, IX and XIV). The off-target, highly abundant isoforms hCA I and II, as well as hCA III, IV and XII were poorly inhibited by many of these esters, although the original phenolic acids were micromolar inhibitors. These phenols, like others investigated earlier, possess a CA inhibition mechanism distinct of the sulfonamides/sulfamates, clinically used drugs for the treatment of a multitude of pathologies, but with severe side effects due to hCA I/II inhibition. Unlike the sulfonamides, which bind to the catalytic zinc ion, phenols are anchored at the Zn(II)-coordinated water molecule, binding more externally within the active site cavity, and making contacts with amino acid residues at the entrance of the active site. As this is the region with the highest variability between the many CA isozymes found in mammals, this class of compounds shows isoform-selective inhibitory profiles, which may be exploited for obtaining pharmacological agents with less side effects compared to other classes of inhibitors. PMID:26498394

  8. The fusion of erythrocytes by fatty acids, esters, retinol and alpha-tocopherol.

    PubMed

    Ahkong, Q F; Fisher, D; Tampion, W; Lucy, J A

    1973-09-01

    1. The ability of a number of carboxylic acids, their esters, retinol and alpha-tocopherol to induce fusion of hen erythrocytes in vitro was investigated. 2. Some 30 different fat-soluble substances (100mug/ml) were found to cause the formation of multinucleated erythrocytes with a suspension of 3x10(8) erythrocytes/ml. The most effective agents induced fusion within 5-10min at 37 degrees C; some substances required about 1h. 3. Inclusion of Dextran 60C in the test medium minimized colloid osmotic lysis caused by exogenous lipids that induce cell fusion. 4. Cell swelling, followed by cell adhesion, was then seen to precede cell fusion. 5. Fusion occurred with C(10)-C(14) saturated carboxylic acids, with unsaturated, longer-chain carboxylic acids and their mono-esters; retinol, and to a lesser extent alpha-tocopherol, also caused cell fusion. 6. C(6)-C(9), C(15), C(16) and C(18) saturated carboxylic acids did not induce fusion within 4h; glyceryl dioleate was only weakly active, and glyceryl trioleate was inactive in the test system. 7. Fusion was facilitated by a high ratio of chemical agents to cell number and by incubation between pH5 and 6. It was inhibited by EDTA and by serum albumin. 8. Glyceryl mono-oleate caused both a similar fusion of several species of mammalian erythrocyte and the interspecific fusion of human and chicken erythrocytes. 9. The term ;fusogenic' is proposed to describe chemical, viral and physical agents that cause membranes to fuse. 10. The biochemical mechanisms involved and the possible biological significance of membrane fusion by fusogenic lipids are discussed. PMID:4204034

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

    NASA Astrophysics Data System (ADS)

    Britton, Stephanie Lynne

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

  10. Application of modified attapulgite in phthalate acid ester-contaminated soil: Effects on phthalate acid ester dissipation and the composition of soil microbial community.

    PubMed

    Gao, Jun; Shi, Yi-Ying; Zhou, Hai-Feng; Ren, Xu-Qin; Ji, Huai

    2016-08-01

    The effects of modified attapulgite (MA) on the dissipations of the plasticizers di-n-butyl phthalate (DBP) and di-(2-ethylhexyl) phthalate (DEHP) in soil, as well as on the composition of soil microbial community, were studied. DBP, DEHP (50 mg kg(-1) in soil, respectively), and MA (1, 5, and 10 % in soil) were mixed thoroughly with soil and incubated for 60 days. DBP- and DEHP-contaminated soils without MA were used as the controls. Both of DBP and DEHP residues in bulk soils and four soil fractions were measured at five incubation times 1, 7, 15, 30, and 60 days, and their dissipation kinetic equations were analyzed. The microbial phospholipid fatty acid (PLFA) concentrations were also measured at the end of experiment. Our results showed that the effect of modified attapulgite on DBP dissipation was related to its dosage in soil. The DEHP dissipation was both inhibited by MA at the 5 and 10 % rates in soils. The application of MA changed the content percentages but did not change the concentration order of phthalate acid esters (PAEs) in soil particle-size fractions. The total microbial PLFA content was significantly increased by 5 and 10 % MA in the contaminated soils. Meanwhile, the gram-negative (GN)/gram-positive (GP) ratios increased when MA was applied at the dosages of 5 and 10 % in DBP and 10 % in DEHP-contaminated soils. Principal component analysis (PCA) indicated that the change of bacteria PLFA, especially the GN bacterial PLFA, depended on the dosages of MA added into soil. The application of MA into soil has a positive effect on reducing the eco-toxicity of PAEs in soil based on the analysis of the soil microbial PLFA. PMID:27094276

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

    PubMed Central

    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

    2016-01-01

    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. PMID:26916830

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

    PubMed

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

    2014-12-22

    A novel, Cu(OAc)2/TEMPO promoted one-step approach for the preparation of fully substituted pyrimidines from readily available amino acid esters has been described. In this reaction, the amino acid esters act as the only N-C sources for the construction of corresponding pyrimidines. The mechanism of this process includes oxidative dehydrogenation, the generation of an imine radical, and a formal [3+3] cycloaddition. This methodology proves to be a high atom-economic and straightforward strategy for the synthesis of pyrimidines and diverse substrates which are substituted by various functional groups have been afforded in moderate to good yield. PMID:25377658

  13. Identification of Fatty Acid Glucose Esters as Os9BGlu31 Transglucosidase Substrates in Rice Flag Leaves.

    PubMed

    Komvongsa, Juthamath; Mahong, Bancha; Phasai, Kannika; Hua, Yanling; Jeon, Jong-Seong; Ketudat Cairns, James R

    2015-11-11

    Rice Os9BGlu31 transglucosidase transfers glucosyl moieties between various carboxylic acids and alcohols, including phenolic acids and flavonoids, in vitro. The role of Os9BGlu31 transglucosidase in rice plant metabolism has only been suggested to date. Methanolic extracts of rice bran and leaves were found to contain oleic acid and linoleic acid to which Os9BGlu31 could transfer glucose from the 4-nitrophenyl β-D-glucoside (4NPGlc) donor to form 1-O-acyl glucose esters. Os9BGlu31 showed higher activity with oleic acid (18:1) and linoleic acid (18:2) than with stearic acid (18:0) and had both a higher kcat and a higher Km for linoleic than oleic acid in the presence of 8 mM 4NPGlc donor. Os9BGlu31 knockout mutant rice lines were found to have significantly larger amounts of fatty acid glucose esters than wild-type control lines. Because the transglucosylation reaction is reversible, these data suggest that fatty acid glucose esters act as glucosyl donor substrates for Os9BGlu31 transglucosidase in rice. PMID:26477245

  14. Retention indices, relative response factors, and mass spectra of trifluoroethyl and heptafluorobutyl esters of carboxylic acids determined by capillary GC/MS

    SciTech Connect

    Yu, S.K.-T.; Vrana, R.P.; Green, J.B.

    1990-11-01

    The GC/MS characteristics of carboxylic acid esters prepared from fluorine-containing alcohols were compared to those of methyl esters. The GC retention of 2,2,2-trifluoroethyl (TFE) esters was less than, and 2,2,3,3,4,4,4-heptafluoro-1-butyl (HFB) esters approximately equivalent to that of methyl esters. The peak shape of both TFE and HFB esters was slightly superior to that of methyl esters. Mass spectra of TFE and HFB aliphatic esters show significantly more intense molecular and key fragment ions than those of methyl esters. Also, owing to their significantly higher molecular weights, TFE or HFB ester molecular ions and most fragment ions of interest occur at significantly higher m/z values than most potential interfering ions. The GC retention indices, relative GC/MS total ion current response factors, and 70 eV electron impact mass spectra of about 70 TFE and 70 HFB carboxylic acid esters are reported. Results from analysis of a TFE/HFB esterified petroleum carboxylic acid concentrate are discussed in detail. 26 refs., 17 figs., 3 tabs.

  15. 40 CFR 721.1725 - Benzoic acid, 3,3′-methyl-enebis [6 amino-, di-2-propenyl ester.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... Significant New Uses for Specific Chemical Substances § 721.1725 Benzoic acid, 3,3′-methyl-enebis [6 amino..., Benzoic acid, 3,3′-methylenebis [6 amino-, di-2-propenyl ester. (2) The significant new uses are: (i) Any... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Benzoic acid, 3,3â²-methyl-enebis...

  16. 40 CFR 721.1725 - Benzoic acid, 3,3′-methyl-enebis [6 amino-, di-2-propenyl ester.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... Significant New Uses for Specific Chemical Substances § 721.1725 Benzoic acid, 3,3′-methyl-enebis [6 amino..., Benzoic acid, 3,3′-methylenebis [6 amino-, di-2-propenyl ester. (2) The significant new uses are: (i) Any... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Benzoic acid, 3,3â²-methyl-enebis...

  17. 40 CFR 721.1725 - Benzoic acid, 3,3′-methyl-enebis [6 amino-, di-2-propenyl ester.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... Significant New Uses for Specific Chemical Substances § 721.1725 Benzoic acid, 3,3′-methyl-enebis [6 amino..., Benzoic acid, 3,3′-methylenebis [6 amino-, di-2-propenyl ester. (2) The significant new uses are: (i) Any... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Benzoic acid, 3,3â²-methyl-enebis...

  18. 40 CFR 721.1729 - Boric acid (H3BO3), mixed esters with polyethylene glycol mono-Bu ether and polyethylene glycol...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Boric acid (H3BO3), mixed esters with... identified as boric acid (H3BO3), mixed esters with polyethylene glycol mono-Bu ether and polyethylene glycol... NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.1729...

  19. 40 CFR 721.1729 - Boric acid (H3BO3), mixed esters with polyethylene glycol mono-Bu ether and polyethylene glycol...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Boric acid (H3BO3), mixed esters with... identified as boric acid (H3BO3), mixed esters with polyethylene glycol mono-Bu ether and polyethylene glycol... NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.1729...

  20. 40 CFR 721.1729 - Boric acid (H3BO3), mixed esters with polyethylene glycol mono-Bu ether and polyethylene glycol...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Boric acid (H3BO3), mixed esters with... identified as boric acid (H3BO3), mixed esters with polyethylene glycol mono-Bu ether and polyethylene glycol... NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.1729...

  1. 40 CFR 721.1729 - Boric acid (H3BO3), mixed esters with polyethylene glycol mono-Bu ether and polyethylene glycol...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

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

  2. 40 CFR 721.1729 - Boric acid (H3BO3), mixed esters with polyethylene glycol mono-Bu ether and polyethylene glycol...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Boric acid (H3BO3), mixed esters with... identified as boric acid (H3BO3), mixed esters with polyethylene glycol mono-Bu ether and polyethylene glycol... NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.1729...

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

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

    PubMed

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

    2016-02-18

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

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

    PubMed

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

    2016-08-01

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

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

    PubMed

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

    2015-12-01

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

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

    PubMed

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

    2015-12-01

    We investigated the protective effect of caffeic acid phenethyl ester (CAPE) on cyclophosphamide-induced hemorrhagic cystitis in rats in comparison with 2-mercaptoethane sulfonate (MESNA). Forty male rats were randomized into four groups: group 1 (control), group 2 (cyclophosphamide), group 3 (cyclophosphamide + MESNA), group 4 (cyclophosphamide + CAPE). Cyclophosphamide injection increased malondialdehyde levels indicating oxidative stress, whereas CAPE and MESNA ameliorated malondialdehyde levels in the bladder (p < 0.05). Only catalase activities were decreased significantly in both groups (cyclophosphamide + MESNA and cyclophosphamide + CAPE, p < 0.05). Pretreatment with CAPE (p < 0.01) resulted in a significant decrease in nitric oxide levels when compared with the cyclophosphamide group. When we consider the studies that show the critical importance of increased nitric oxide levels in pathogenesis of cyclophosphamide-induced hemorrhagic cystitis, we suggest that it would be more beneficial to use MESNA with CAPE to prevent histological damage. PMID:26207616

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

    PubMed

    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. PMID:26649239

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

    PubMed

    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. PMID:25975288

  10. Intraparticle diffusion limitations in the hydrogenation of monounsaturated edible oils and their fatty acid methyl esters

    SciTech Connect

    Jonker, G.H.; Veldsink, J.W.; Beenackers, A.A.C.M.

    1998-12-01

    Intraparticle diffusion limitation in the hydrogenation and isomerization of fatty acid methyl esters (FAMEs) and edible oils (triacylglycerol, TAG) in porous nickel catalyst was investigated both under reactive and under inert conditions. Under reactive conditions, the diffusion coefficients were determined from the best fits of the model simulations applying the intrinsic reacting kinetics of monounsaturated FAME hydrogenation to experiments under diffusion limited conditions. Due to the absence of reaction (hydrogenation of double bonds), the obtained effective H{sub z} diffusion coefficient (D{sub e}) with the HPLC technique is volume averaged and thereby determined by the larger intercrystalline pores (<30% of the total pore volume) only. Moreover, D{sub e} measured under reaction conditions reflected the influence of the micropores, resulting in a 10-fold lower value.

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

    PubMed

    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. PMID:25100535

  12. Relationship between hydrophobicity parameters and the strength and selectivity of phytotoxicity of sulfosuccinic acid esters.

    PubMed

    Oros, G; Cserháti, T; Forgács, E; Vrbanová, A

    1999-09-01

    The strength and selectivity of the phytotoxicity of 11 sulfosuccinic acid ester surfactants were determined on the leaves of Tradescantia bicolor, and the data were evaluated by multivariate mathematical-statistical methods. Spectral mapping technique combined with stepwise regression analysis indicated that both the strength and the selectivity of the effect depend significantly on the specific hydrophobic surface area of the anionic surfactants determined in the presence of ions. The significant relationship between this hydrophobicity parameter and phytotoxic activity suggests the involvement of apolar (hydrophobic) forces in the plant-surfactant interaction. It was assumed that the apolar alkyl chains of the surfactants may insert in the hydrophobic part of the phospholipid bilayers causing membrane disorder and malfunction. PMID:10703744

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

    PubMed

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

    2015-11-01

    A series of liquid hydrocarbons (alkylbenzenes, alkanes, and alkenes) were obtained by a synergetic deoxy reforming (SDR) process of cellulose and linoleic acid methyl ester (LAME) at 350°C and 4-6MPa in a closed system without external source of hydrogen. The liquid product was obtained with a yield of 15wt% at a LAME/cellulose ratio of 0.2. In contrast, the direct deoxy reforming of cellulose produces oil that contains plenty of phenols and oxygen-containing compounds. Due to the insufficiency of water employed (30wt%), a radical reaction pathway was proposed. Quantum chemical calculations indicate that the radicals from LAME interfere with the reactions of the intermediate products from cellulose, being responsible for the removal of phenols and the formation of hydrocarbons. The SDR process offers an embryonic insight in an alternative technique for preparation of hydrocarbon fuels. PMID:26241841

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

    PubMed Central

    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. PMID:26649239

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

    PubMed

    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. PMID:26138876

  16. The influence of molecular structure of fatty acid monoalkyl esters on diesel combustion

    SciTech Connect

    Schoenborn, Alessandro; Ladommatos, Nicos; Williams, John; Allan, Robert; Rogerson, John

    2009-07-15

    The subject of this paper is a series of experiments conducted on a single-cylinder research engine investigating the influence of molecular structure on the combustion behaviour of fatty acid alcohol ester (biodiesel) molecules under diesel engine conditions. The fuels employed in these experiments comprised various samples of pure individual fatty acid alcohol ester molecules of different structure, as well as several mixtures of such molecules. The latter consisted in biodiesel fuels produced by the transesterification of naturally occurring plant oils or animal fat with a monohydric alcohol. It was observed that the molecular structure of the fuel significantly influenced the formation of NO{sub x} and particulate matter and their respective concentration in the exhaust gas. The influence on the formation of NO{sub x} in particular, appeared to be exerted first through the effect which the molecular structure had on the auto-ignition delay occurring after the fuel was injected into the combustion chamber, and second through the flame temperature at which the various molecules burned. The emission of particulates on the other hand showed correlation with the number of double bonds in the fuel molecules for the case of larger accumulation mode particles, and with the boiling point of the fuel samples for the case of the smaller, nucleation mode particles. The effect of ignition delay on the exhaust emissions of these pollutants was isolated by adding the ignition promoting molecule 2-ethylhexyl nitrate to some of the fuel samples in closely specified concentrations, so as to equalise the ignition delay for the relevant fuel samples. The removal of the ignition delay as a main influence on the combustion process enabled the observation of the lesser effects of adiabatic flame temperature. (author)

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

    SciTech Connect

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

    2014-11-15

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

  18. Synthesis of p-aminophenyl aryl H-phosphinic acids and esters via cross-coupling reactions: elaboration to phosphinic acid pseudopeptide analogues of pteroyl glutamic acid and related antifolates.

    PubMed

    Yang, Yonghong; Coward, James K

    2007-07-20

    The synthesis of suitably protected p-aminophenyl H-phosphinic acids and esters from the corresponding para-substituted aryl halides has been accomplished via the Pd-catalyzed cross-coupling reaction of anilinium hypophosphite, either in the absence or presence of a tetraalkyl orthosilicate, to provide the free H-phosphinic acid or the corresponding ester, respectively. Subsequent conjugate addition of either a PIII species or phosphorus anion, generated in situ from either the free H-phosphinic acid or ester, to a 2-methylene glutaric acid ester provided the aryl phosphinic acid analogue of p-aminobenzoyl glutamic acid. Alkylation of these suitably protected p-aminophenyl phosphinic acid esters with a 6-(bromomethyl)pteridine or the corresponding (bromomethyl)pyridopyrmidine, followed by hydrolytic removal of protecting groups, provided the target aryl phosphinic acid analogues of folic acid and related antifolates. Alternatively, for the synthesis of the folate or 5-deazafolate analogues on a slightly larger scale, reductive amination with either N2-acetyl or N2-pivaloyl-6-formylpterin or the corresponding formylpyridopyrmidine and the same suitably protected p-aminophenyl phosphinic acid esters, followed by removal of protecting groups, is preferred. In the course of this research, it was observed that the nucleophilicity of both the aniline nitrogen and various PIII species derived from p-aminophenyl phosphinic acid derivatives is significantly reduced compared to that of the unsubstituted counterpart. PMID:17602593

  19. Stimulation of phospholipid hydrolysis and arachidonic acid mobilization in human uterine decidua cells by phorbol ester.

    PubMed Central

    Schrey, M P; Read, A M; Steer, P J

    1987-01-01

    Vasopressin and oxytocin both stimulated inositol phosphate accumulation in isolated uterine decidua cells. Pretreatment of cells with the phorbol ester 12-O-tetradecanoylphorbol 13-acetate (TPA) prevented this agonist-induced phosphoinositide hydrolysis. TPA (0.1 microM) alone had no effect on basal inositol phosphate accumulation, but stimulated phosphoinositide deacylation, as indicated by a 2-fold increase in lysophosphatidylinositol and glycerophosphoinositol. TPA also stimulated a dose-related release of arachidonic acid from decidua-cell phospholipid [phosphatidylcholine (PC) much greater than phosphatidylinositol (PI) greater than phosphatidylethanolamine]. The phorbol ester 4 beta-phorbol 12,13-diacetate (PDA) at 0.1 microM had no effect on arachidonic acid mobilization. The TPA-stimulated increase in arachidonic acid release was apparent by 2 1/2 min (116% of control), maximal after 20 min (283% of control), and remained around this value (306% of control) after 120 min incubation. TPA also stimulated significant increases in 1,2-diacylglycerol and monoacylglycerol production at 20 and 120 min. Although the temporal increases in arachidonic acid and monoacylglycerol accumulation in the presence of TPA continued up to 120 min, that of 1,2-diacylglycerol declined after 20 min. In decidua cells prelabelled with [3H]choline, TPA also stimulated a significant decrease in radiolabelled PC after 20 min, which was accompanied by an increased release of water-soluble metabolites into the medium. Most of the radioactivity in the extracellular pool was associated with choline, whereas the main cellular water-soluble metabolite was phosphorylcholine. TPA stimulated extracellular choline accumulation to 183% and 351% of basal release after 5 and 20 min respectively and cellular phosphorylcholine production to 136% of basal values after 20 min. These results are consistent with a model in which protein kinase C activation by TPA leads to arachidonic acid mobilization

  20. Combined effects of carbonation with heating and fatty acid esters on inactivation and growth inhibition of various bacillus spores.

    PubMed

    Klangpetch, Wannaporn; Nakai, Tomoe; Noma, Seiji; Igura, Noriyuki; Shimoda, Mitsuya

    2013-09-01

    The effects of carbonation treatment (1 to 5 MPa, 30 min) plus heat treatment (30 to 80°C, 30 min) in the presence of various fatty acid esters (FAEs; 0.05 and 0.1%, wt/vol) on counts of viable Bacillus subtilis spores were investigated. FAEs or carbonation alone had no inactivation or growth inhibition effects on B. subtilis spores. However, carbonation plus heat (CH; 80°C, 5 MPa, 30 min) in the presence of mono- and diglycerol fatty acid esters markedly decreased counts of viable spores, and the spore counts did not change during storage for 30 days. The greatest decrease in viable spore counts occurred in the presence of monoglycerol fatty acid esters. Under CH conditions, inactivation and/or growth inhibition occurred at only 80°C and increased with increasing pressure. The greatest decrease in spore counts (more than 4 log units) occurred with CH (80°C, 5 MPa, 30 min) in the presence of monoglycerol fatty acid esters. However, this treatment was less effective against Bacillus coagulans and Geobacillus stearothermophilus spores. PMID:23992501