Sample records for methyl ester binds

  1. Binding of indomethacin methyl ester to cyclooxygenase-2. A computational study.

    PubMed

    Sárosi, Menyhárt-Botond

    2018-06-05

    Inhibitors selective towards the second isoform of prostaglandin synthase (cyclooxygenase, COX-2) are promising nonsteroidal anti-inflammatory drugs and antitumor medications. Methylation of the carboxylate group in the relatively nonselective COX inhibitor indomethacin confers significant COX-2 selectivity. Several other modifications converting indomethacin into a COX-2 selective inhibitor have been reported. Earlier experimental and computational studies on neutral indomethacin derivatives suggest that the methyl ester derivative likely binds to COX-2 with a similar binding mode as that observed for the parent indomethacin. However, docking studies followed by molecular dynamics simulations revealed two possible binding modes in COX-2 for indomethacin methyl ester, which differs from the experimental binding mode found for indomethacin. Both alternative binding modes might explain the observed COX-2 selectivity of indomethacin methyl ester. Graphical abstract Binding of indomethacin methyl ester to cyclooxygenase-2.

  2. 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.

  3. Three-dimensional quantitative structure-activity relationship modeling of cocaine binding by a novel human monoclonal antibody.

    PubMed

    Paula, Stefan; Tabet, Michael R; Farr, Carol D; Norman, Andrew B; Ball, W James

    2004-01-01

    Human monoclonal antibodies (mAbs) designed for immunotherapy have a high potential for avoiding the complications that may result from human immune system responses to the introduction of nonhuman mAbs into patients. This study presents a characterization of cocaine/antibody interactions that determine the binding properties of the novel human sequence mAb 2E2 using three-dimensional quantitative structure-activity relationship (3D-QSAR) methodology. We have experimentally determined the binding affinities of mAb 2E2 for cocaine and 38 cocaine analogues. The K(d) of mAb 2E2 for cocaine was 4 nM, indicating a high affinity. Also, mAb 2E2 displayed good cocaine specificity, as reflected in its 10-, 1500-, and 25000-fold lower binding affinities for the three physiologically relevant cocaine metabolites benzoylecgonine, ecgonine methyl ester, and ecgonine, respectively. 3D-QSAR models of cocaine binding were developed by comparative molecular similarity index analysis (CoMSIA). A model of high statistical quality was generated showing that cocaine binds to mAb 2E2 in a sterically restricted binding site that leaves the methyl group attached to the ring nitrogen of cocaine solvent-exposed. The methyl ester group of cocaine appears to engage in attractive van der Waals interactions with mAb 2E2, whereas the phenyl group contributes to the binding primarily via hydrophobic interactions. The model further indicated that an increase in partial positive charge near the nitrogen proton and methyl ester carbonyl group enhances binding affinity and that the ester oxygen likely forms an intermolecular hydrogen bond with mAb 2E2. Overall, the cocaine binding properties of mAb 2E2 support its clinical potential for development as a treatment of cocaine overdose and addiction.

  4. Binding specificity of the juvenile hormone carrier protein from the hemolymph of the tobacco hornworm Manduca sexta Johannson (Lepidoptera: Sphingidae).

    PubMed

    Peterson, R C; Reich, M F; Dunn, P E; Law, J H; Katzenellnbogen, J A

    1977-05-17

    A series of analogues of insect juvenile hormone (four geometric isomers of methyl epoxyfarnesenate, several para-substituted epoxygeranyl phenyl ethers, and epoxyfarnesol and its acetate and haloacetate derivatives) was prepared to investigate the binding specificity of the hemolymph juvenile hormone binding protein from the tobacco hornworm Manduct sexta. The relative binding affinities were determined by a competition assay against radiolabeled methyl (E,E)-3,11-dimethyl-7-ethyl-cis-10,11-epoxytrideca-2,6-dienoate (JH I). The ratio of dissociation constants was estimated by plotting competitor data according to a linear transformation of the dissociation equations describing competition of two ligands for a binding protein. The importance of the geometry of the sesquiterpene hydrocarbon chain is indicated by the fact that the binding affinity is decreased as Z (cis) double bonds are substituted for E (trans) double bonds in the methyl epoxyfarnesenate series; the unepoxidized analogues do not bind. A carboxylic ester function is important although its orientation can be reversed, as indicated by the good binding of epoxyfarnesyl acetate. In the monoterpene series, methyl epoxygeranoate shows no affinity for the binding protein, but substitution of a phenyl or p-carbomethoxyphenyl ether for the ester function imparts a low, but significant affinity. These data taken together with earlier results indicate that the binding site for juvenile hormone in the hemolymph binding protein is characterized by a sterically defined hydrophobic region with polar sites that recognize the epoxide and the ester functions.

  5. Modeling the Concentrations and Efficiencies for the Interacting Species of Pyropheophorbide Methyl Ester-Copper Association

    NASA Astrophysics Data System (ADS)

    Al-Omari, S.

    2013-07-01

    The interaction between pyropheophorbide methyl ester (PPME) and Cu2+ was investigated using UV-vis and fluorescence spectrscopy. Study of the binding interaction between PPME and Cu2+ could contribute to understanding of its pharmacokinetics and pharmacodynamics. Parameters of the static and dynamic fluorescence quenching of PPME-Cu2+ association were calculated at different temperatures. For binding site of 1:1 at 299 K, the static binding constant (kS), the static isosbestic concentration (CS{ iso}), the dynamic binding constant (kD), and the dynamic isosbestic concentration (CD{ iso }) are, respectively, 61 M-1, 0.0164 M, 75 M-1, and 0.0133 M. The concentrations and efficiencies of the intermediates species were modeled. Satisfactory correspondence between the experimental and calculated results was found.

  6. UV-induced solvent free synthesis of truxillic acid-bile acid conjugates

    NASA Astrophysics Data System (ADS)

    Koivukorpi, Juha; Kolehmainen, Erkki

    2009-07-01

    The solvent free UV-induced [2 + 2] intermolecular cycloaddition of two molecules of 3α-cinnamic acid ester of methyl lithocholate produced in 99% yield of α- and ɛ-truxillic acid-bis(methyl lithocholate) isomers, which possess two structurally different potential binding sites. A prerequisite for this effective solid state reaction is a proper self-assembled crystal structure of the starting conjugate crystallized from acetonitrile. The crystallization of cinnamic acid ester of methyl lithocholate from acetonitrile produces two different crystalline forms (polymorphs), which is the reason for the solid state formation of two isomers of truxillic acid-bis(methyl lithocholate).

  7. Structural Analysis of Substrate, Reaction Intermediate, and Product Binding in Haemophilus influenzae Biotin Carboxylase

    PubMed Central

    Broussard, Tyler C.; Pakhomova, Svetlana; Neau, David B.; Bonnot, Ross; Waldrop, Grover L.

    2015-01-01

    Acetyl-CoA carboxylase catalyzes the first and regulated step in fatty acid synthesis. In most Gram-negative and Gram-positive bacteria, the enzyme is composed of three proteins: biotin carboxylase, a biotin carboxyl carrier protein (BCCP), and carboxyltransferase. The reaction mechanism involves two half-reactions with biotin carboxylase catalyzing the ATP-dependent carboxylation of biotin-BCCP in the first reaction. In the second reaction, carboxyltransferase catalyzes the transfer of the carboxyl group from biotin-BCCP to acetyl-CoA to form malonyl-CoA. In this report, high-resolution crystal structures of biotin carboxylase from Haemophilus influenzae were determined with bicarbonate, the ATP analogue AMPPCP; the carboxyphosphate intermediate analogues, phosphonoacetamide and phosphonoformate; the products ADP and phosphate; and the carboxybiotin analogue N1′-methoxycarbonyl biotin methyl ester. The structures have a common theme in that bicarbonate, phosphate, and the methyl ester of the carboxyl group of N1′-methoxycarbonyl biotin methyl ester all bound in the same pocket in the active site of biotin carboxylase and as such utilize the same set of amino acids for binding. This finding suggests a catalytic mechanism for biotin carboxylase in which the binding pocket that binds tetrahedral phosphate also accommodates and stabilizes a tetrahedral dianionic transition state resulting from direct transfer of CO2 from the carboxyphosphate intermediate to biotin. PMID:26020841

  8. Mode of action of pectin lyase A of Aspergillus niger on differently C(6)-substituted oligogalacturonides.

    PubMed

    van Alebeek, Gert-Jan W M; Christensen, Tove M I E; Schols, Henk A; Mikkelsen, Jørn D; Voragen, Alphons G J

    2002-07-19

    A thorough investigation of the mode of action of Aspergillus niger (4M-147) pectin lyase A (PLA) on differently C(6)-substituted oligogalacturonides is described. PLA appeared to be very specific for fully methyl-esterified oligogalacturonides: removal of the methyl-ester or changing the type of ester (ethyl esterification) or transamidation resulted in (almost) complete loss of conversion. The PLA activity increased with increasing length of the substrate up to a degree of polymerization (DP) of 8 indicating the presence of at least eight subsites on the enzyme. Product analysis demonstrated the formation of several Delta 4,5 unsaturated products and their saturated counterparts. The Delta 4,5 unsaturated trimer was the main product up to DP 8. For DP 9 and 10 Delta 4,5 unsaturated tetramer was the major product. Based upon the bond cleavage frequencies, a provisional subsite map was calculated, which supports the presence of eight subsites. By limited alkaline de-esterification of fully methyl-esterified pentamer and hexamer two sets of partially methyl-esterified pentamers (x and y methyl groups) and hexamers (a and b methyl groups) were prepared. Matrix-assisted laser desorption/ionization time of flight mass spectroscopy (MALDI-TOF MS) analysis demonstrated that the methyl-ester distribution was fully random. Using these partially methyl-esterified oligogalacturonides as substrates for PLA a 10-fold decrease in reaction rate was recorded compared with the fully methyl-esterified counterparts. Analysis of the methyl-ester distribution of the products showed that PLA tolerates carboxyl groups in the substrate binding cleft. At either subsite +2, +4, or -1 to -4 a free carboxyl group could be tolerated, whereas methyl-esters were obligatory at subsite +1 and +3. So PLA is capable to cleave the bond between a methyl-esterified and a non-esterified galacturonic acid residue, where the newly formed Delta 4,5 unsaturated non-reducing end residue always contains a methyl-ester.

  9. Prevention by thioethers of the hepatotoxicity and covalent binding to macromolecules of N-hydroxy-2-acetylaminofluorene and its sulfate ester in rat liver in vivo and in vitro.

    PubMed

    van den Goorbergh, J A; de Wit, H; Tijdens, R B; Mulder, G J; Meerman, J H

    1987-02-01

    In order to find potentially effective compounds that could prevent the covalent binding of the carcinogen N-hydroxy-2-acetylaminofluorene (N-OH-AAF) to rat liver macromolecules in vivo, the prevention of the covalent binding to RNA of the sulfate ester of the carcinogen N-OH-AAF by a series of thioethers was investigated in vitro. The most effective thioethers, which inhibited the covalent binding by 70% or more, were studied for their protection against acute hepatotoxicity of N-OH-AAF in the rat in vivo. Three of these thioethers, thiazolidine, methyl 4-(methylthio)benzoate, and 2-(methylthio)benzimidazole significantly decreased the hepatoxicity of N-OH-AAF, by 45, 71 and 83%, respectively. The effects of these thioethers on the covalent binding of N-OH-AAF to cellular macromolecules in vivo were also studied. Methyl 4-(methylthio)benzoate and 2-(methylthio)benzimidazole decreased the adduct formation of N-OH-AAF to DNA by 54 and 44%, respectively, but had no effect on protein adduct formation. Only 2-(methylthio)benzimidazole caused a slight decrease (23%) in the AAF-- protein adduct formation. 2-Acetylaminofluorene (AAF) and methyl 4-(methyl-sulfinyl)benzoate were the main products in the incubation of methyl 4-(methylthio)benzoate with AAF-N-sulfate in vitro. This suggests that the thioether attacks the nitrenium ion which is formed by spontaneous breakdown of AAF-N-sulfate; the formation of a sulfonium--AAF conjugate is postulated which decomposes into AAF and a sulfinyl compound.

  10. Study of protein-probe interaction and protective action of surfactant sodium dodecyl sulphate in urea-denatured HSA using charge transfer fluorescence probe methyl ester of N,N-dimethylamino naphthyl acrylic acid.

    PubMed

    Mahanta, Subrata; Singh, Rupashree Balia; Guchhait, Nikhil

    2009-03-01

    We have demonstrated that the intramolecular charge transfer (ICT) probe Methyl ester of N,N-dimethylamino naphthyl acrylic acid (MDMANA) serves as an efficient reporter of the proteinous microenvironment of Human Serum Albumin (HSA). This work reports the binding phenomenon of MDMANA with HSA and spectral modulation thereupon. The extent of binding and free energy change for complexation reaction along with efficient fluorescence resonance energy transfer from Trp-214 of HSA to MDMANA indicates strong binding between probe and protein. Fluorescence anisotropy, red edge excitation shift, acrylamide quenching and time resolved measurements corroborate the binding nature of the probe with protein and predicts that the probe molecule is located at the hydrophobic site of the protein HSA. Due to the strong binding ability of MDMANA with HSA, it is successfully utilized for the study of stabilizing action of anionic surfactant Sodium Dodecyl Sulphate to the unfolding and folding of protein with denaturant urea in concentration range 1M to 9M.

  11. Ubiquitin vinyl methyl ester binding orients the misaligned active site of the ubiquitin hydrolase UCHL1 into productive conformation

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    Boudreaux, David A.; Maiti, Tushar K.; Davies, Christopher W.

    Ubiquitin carboxy-terminal hydrolase L1 (UCHL1) is a Parkinson disease-associated, putative cysteine protease found abundantly and selectively expressed in neurons. The crystal structure of apo UCHL1 showed that the active-site residues are not aligned in a canonical form, with the nucleophilic cysteine being 7.7 {angstrom} from the general base histidine, an arrangement consistent with an inactive form of the enzyme. Here we report the crystal structures of the wild type and two Parkinson disease-associated variants of the enzyme, S18Y and I93M, bound to a ubiquitin-based suicide substrate, ubiquitin vinyl methyl ester. These structures reveal that ubiquitin vinyl methyl ester binds primarilymore » at two sites on the enzyme, with its carboxy terminus at the active site and with its amino-terminal {beta}-hairpin at the distal site - a surface-exposed hydrophobic crevice 17 {angstrom} away from the active site. Binding at the distal site initiates a cascade of side-chain movements in the enzyme that starts at a highly conserved, surface-exposed phenylalanine and is relayed to the active site resulting in the reorientation and proximal placement of the general base within 4 {angstrom} of the catalytic cysteine, an arrangement found in productive cysteine proteases. Mutation of the distal-site, surface-exposed phenylalanine to alanine reduces ubiquitin binding and severely impairs the catalytic activity of the enzyme. These results suggest that the activity of UCHL1 may be regulated by its own substrate.« less

  12. Kinetics of the hydrolysis of N-benzoyl-l-serine methyl ester catalysed by bromelain and by papain. Analysis of modifier mechanisms by lattice nomography, computational methods of parameter evaluation for substrate-activated catalyses and consequences of postulated non-productive binding in bromelain- and papain-catalysed hydrolyses

    PubMed Central

    Wharton, Christopher W.; Cornish-Bowden, Athel; Brocklehurst, Keith; Crook, Eric M.

    1974-01-01

    1. N-Benzoyl-l-serine methyl ester was synthesized and evaluated as a substrate for bromelain (EC 3.4.22.4) and for papain (EC 3.4.22.2). 2. For the bromelain-catalysed hydrolysis at pH7.0, plots of [S0]/vi (initial substrate concn./initial velocity) versus [S0] are markedly curved, concave downwards. 3. Analysis by lattice nomography of a modifier kinetic mechanism in which the modifier is substrate reveals that concave-down [S0]/vi versus [S0] plots can arise when the ratio of the rate constants that characterize the breakdown of the binary (ES) and ternary (SES) complexes is either less than or greater than 1. In the latter case, there are severe restrictions on the values that may be taken by the ratio of the dissociation constants of the productive and non-productive binary complexes. 4. Concave-down [S0]/vi versus [S0] plots cannot arise from compulsory substrate activation. 5. Computational methods, based on function minimization, for determination of the apparent parameters that characterize a non-compulsory substrate-activated catalysis are described. 6. In an attempt to interpret the catalysis by bromelain of the hydrolysis of N-benzoyl-l-serine methyl ester in terms of substrate activation, the general substrate-activation model was simplified to one in which only one binary ES complex (that which gives rise directly to products) can form. 7. In terms of this model, the bromelain-catalysed hydrolysis of N-benzoyl-l-serine methyl ester at pH7.0, I=0.1 and 25°C is characterized by Km1 (the dissociation constant of ES)=1.22±0.73mm, k (the rate constant for the breakdown of ES to E+products, P)=1.57×10−2±0.32×10−2s−1, Ka2 (the dissociation constant that characterizes the breakdown of SES to ES and S)=0.38±0.06m, and k′ (the rate constant for the breakdown of SES to E+P+S)=0.45±0.04s−1. 8. These parameters are compared with those in the literature that characterize the bromelain-catalysed hydrolysis of α-N-benzoyl-l-arginine ethyl ester and of α-N-benzoyl-l-arginine amide; Km1 and k for the serine ester hydrolysis are somewhat similar to Km and kcat. for the arginine amide hydrolysis and Kas and k′ for the serine ester hydrolysis are somewhat similar to Km and kcat. for the arginine ester hydrolysis. 9. A previous interpretation of the inter-relationships of the values of kcat. and Km for the bromelain-catalysed hydrolysis of the arginine ester and amide substrates is discussed critically and an alternative interpretation involving substantial non-productive binding of the arginine amide substrate to bromelain is suggested. 10. The parameters for the bromelain-catalysed hydrolysis of the serine ester substrate are tentatively interpreted in terms of non-productive binding in the binary complex and a decrease of this type of binding by ternary complex-formation. 11. The Michaelis parameters for the papain-catalysed hydrolysis of the serine ester substrate (Km=52±4mm, kcat.=2.80±0.1s−1 at pH7.0, I=0.1, 25.0°C) are similar to those for the papain-catalysed hydrolysis of methyl hippurate. 12. Urea and guanidine hydrochloride at concentrations of 1m have only small effects on the kinetic parameters for the hydrolysis of the serine ester substrate catalysed by bromelain and by papain. PMID:4455211

  13. Conformational Behaviour of Azasugars Based on Mannuronic Acid.

    PubMed

    van Rijssel, Erwin R; Janssen, Antonius P A; Males, Alexandra; Davies, Gideon J; van der Marel, Gijsbert A; Overkleeft, Herman S; Codée, Jeroen D C

    2017-07-04

    A set of mannuronic-acid-based iminosugars, consisting of the C-5-carboxylic acid, methyl ester and amide analogues of 1deoxymannorjirimicin (DMJ), was synthesised and their pH-dependent conformational behaviour was studied. Under acidic conditions the methyl ester and the carboxylic acid adopted an "inverted" 1 C 4 chair conformation as opposed to the "normal" 4 C 1 chair at basic pH. This conformational change is explained in terms of the stereoelectronic effects of the ring substituents and it parallels the behaviour of the mannuronic acid ester oxocarbenium ion. Because of this solution-phase behaviour, the mannuronic acid ester azasugar was examined as an inhibitor for a Caulobacter GH47 mannosidase that hydrolyses its substrates by way of a reaction itinerary that proceeds through a 3 H 4 transition state. No binding was observed for the mannuronic acid ester azasugar, but sub-atomic resolution data were obtained for the DMJ⋅CkGH47 complex, showing two conformations- 3 S 1 and 1 C 4 -for the DMJ inhibitor. © 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

  14. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 3 2014-04-01 2014-04-01 false Methyl glucoside-coconut oil ester. 172.816... § 172.816 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in food in accordance with the following conditions: (a) It is the methyl glucoside-coconut oil ester...

  15. Synthesis of heteroaromatic tropeines and heterogeneous binding to glycine receptors.

    PubMed

    Maksay, Gábor; Vincze, Zoltán; Nemes, Péter

    2009-10-01

    Heteroaromatic carboxylic esters of (nor)tropine were synthesized. Tropine esters displaced [(3)H]strychnine binding to glycine receptors of rat spinal cord with low Hill slopes. Two-site displacement resulted in nanomolar IC(50,1) and micromolar IC(50,2) values, and IC(50,2)/IC(50,1) ratios up to 615 depending on the heteroaromatic rings and N-methyl substitution. Nortropeines displayed high affinity and low heterogeneity. IC(50,1) and IC(50,2) values of tropeines did not correlate suggesting different binding modes/sites. Glycine potentiated only the nanomolar displacement reflecting positive allosteric interactions and potentiation of ionophore function. Affinities of three (nor)tropeines were different for glycine receptors but identical for 5-HT(3) receptors.

  16. Selective time-resolved binding of copper(II) by pyropheophorbide-a methyl ester.

    PubMed

    Ghosh, Indrajit; Saleh, Na'il; Nau, Werner M

    2010-05-01

    The complexation behavior of pyropheophorbide-a methyl ester (PPME) with transition metal ions as well as other biologically relevant metal ions has been investigated in water-DMF (2 : 1 v/v) solution. PPME was found to selectively complex Cu(2+) ions, which leads to a distinct change in its absorption spectrum as well as efficient fluorescence quenching. The degree of fluorescence quenching by Cu(2+) depended on concentration and time. Upon addition of Cu(2+), the fluorescence showed a time-resolved decay on the time scale of minutes to hours, with the decay rate being dependent on the cation concentration. Fitting according to a bimolecular reaction rate law provided a rate constant of 650 +/- 90 M(-1) s(-1) at 298 K for metallochlorin formation. The potential implications of Cu(2+) binding for the use of PPME in photodynamic therapy are discussed, along with its use as a fluorescent sensor for detection of micromolar concentrations of Cu(2+).

  17. Interaction of phenolic acids and their derivatives with human serum albumin: Structure-affinity relationships and effects on antioxidant activity.

    PubMed

    Zhang, Yunyue; Wu, Simin; Qin, Yinghui; Liu, Jiaxin; Liu, Jingwen; Wang, Qingyu; Ren, Fazheng; Zhang, Hao

    2018-02-01

    In this study, 111 phenolic acids and their derivatives were chosen to investigate their structure-affinity relationships when binding to human serum albumin (HSA), and effects on their antioxidant activity. A comprehensive mathematical model was employed to calculate the binding constants, using a fluorescence quenching method, and this was corrected for the inner-filter effect to improve accuracy. We found that a hydroxy group at the 2-position of the benzene ring exerted a positive effect on the affinities, while a 4-hydroxy substituent had a negative influence. Both methylation of the hydroxy groups and replacing the hydroxy groups with methyl groups at the 3- and 4-positions of the benzene ring enhanced the binding affinities. Hydrophobic force and hydrogen bonding were binding forces for the phenolic acids, and their methyl esters, respectively. The antioxidant activity of the HSA-phenolic acid interaction compounds was higher than that of the phenolic acids alone. Copyright © 2017. Published by Elsevier Ltd.

  18. 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

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Methyl and ethyl esters of fatty acids produced... Methyl and ethyl esters of fatty acids produced from edible fats and oils. Methyl esters and ethyl esters of fatty acids produced from edible fats and oils may be safely used in food, subject to the...

  19. 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

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Methyl and ethyl esters of fatty acids produced... Methyl and ethyl esters of fatty acids produced from edible fats and oils. Methyl esters and ethyl esters of fatty acids produced from edible fats and oils may be safely used in food, subject to the...

  20. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Methyl glucoside-coconut oil ester. 178.3600... SANITIZERS Certain Adjuvants and Production Aids § 178.3600 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester identified in § 172.816(a) of this chapter may be safely used as a processing...

  1. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Methyl glucoside-coconut oil ester. 172.816... HUMAN CONSUMPTION Multipurpose Additives § 172.816 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in food in accordance with the following conditions: (a) It is the...

  2. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Methyl glucoside-coconut oil ester. 172.816 Section... HUMAN CONSUMPTION Multipurpose Additives § 172.816 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in food in accordance with the following conditions: (a) It is the...

  3. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Methyl glucoside-coconut oil ester. 172.816... HUMAN CONSUMPTION Multipurpose Additives § 172.816 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in food in accordance with the following conditions: (a) It is the...

  4. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Methyl glucoside-coconut oil ester. 178.3600... SANITIZERS Certain Adjuvants and Production Aids § 178.3600 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester identified in § 172.816(a) of this chapter may be safely used as a processing...

  5. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Methyl glucoside-coconut oil ester. 178.3600... SANITIZERS Certain Adjuvants and Production Aids § 178.3600 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester identified in § 172.816(a) of this chapter may be safely used as a processing...

  6. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 3 2014-04-01 2014-04-01 false Methyl glucoside-coconut oil ester. 178.3600 Section 178.3600 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES... Production Aids § 178.3600 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester identified...

  7. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Methyl glucoside-coconut oil ester. 172.816... HUMAN CONSUMPTION Multipurpose Additives § 172.816 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in food in accordance with the following conditions: (a) It is the...

  8. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Methyl glucoside-coconut oil ester. 178.3600... SANITIZERS Certain Adjuvants and Production Aids § 178.3600 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester identified in § 172.816(a) of this chapter may be safely used as a processing...

  9. Thermal Decomposition of Methyl Esters in Biodiesel Fuel: Kinetics, Mechanisms and Products

    NASA Astrophysics Data System (ADS)

    Chai, Ming

    Biodiesel continues to enjoy increasing popularity. However, recent studies on carbonyl compounds emissions from biodiesel fuel are inconclusive. Emissions of carbonyl compounds from petroleum diesel fuels were compared to emissions from pure biodiesel fuels and petroleum-biodiesel blends used in a non-road diesel generator. The concentration of total carbonyl compounds was the highest when the engine was idling. The carbonyl emissions, as well as ozone formation potential, from biodiesel fuel blends were higher than those emitted from petroleum diesel fuel. The sulfur content of diesel fuel and the source of biodiesel fuel were not found to have a significant impact on emissions of carbonyl compounds. Mechanism parameters of the thermal decomposition of biodiesel-range methyl esters were obtained from the results of thermal gravimetric analysis (TGA). The overall reaction orders are between 0.49 and 0.71 and the energies of activation are between 59.9 and 101.3 kJ/mole. Methyl esters in air have lower activation energies than those in nitrogen. Methyl linoleate has the lowest activation energy, followed by methyl oleate, and methyl stearate. The pyrolysis and oxidation of the three methyl esters were investigated using a semi-isothermal tubular flow reactor. The profiles of major products versus reaction temperature are presented. In the pyrolysis of methyl stearate, the primary reaction pathway is the decarboxylic reaction at the methyl ester functional group. Methyl oleate's products indicate more reactions on its carbon-carbon double bond. Methyl linoleate shows highest reactivity among the three methyl esters, and 87 products were detected. The oxidation of three methyl esters resulted in more products in all compound classes, and 55, 114, and 127 products were detected, respectively. The oxidation of methyl esters includes decarboxylation on ester group. The methyl ester's carbon chain could be oxidized as a hydrocarbon compound and form oxidized esters and unsaturated esters, which have been observed in methyl ester's oxidation products. The oxidation of methyl stearate, methyl oleate and methyl linoleate produces 16, 28 and 34 types of carbonyl compounds, respectively. The unsaturated methyl ester forms more carbonyl compounds compared to the saturated methyl ester, which indicates the formation of carbonyl compounds might be more related to the unsaturated carbon bond rather than the methyl ester group. Good agreement between results for total carbon (TC) generally has been found, but the organic and elemental carbon (OC and EC) fractions determined by different methods often disagree. Lack of reference materials has impeded progress on method standardization and understanding method biases. As part of this dissertation, uniform carbon distribution for the filter sets is prepared by using a simply aerosol generation and collection method. The relative standard deviations for the mean TC, OC, and EC results reported by the seven laboratories were below 10%, 11% and 12% (respectively). The method of filter generation is generally applicable and reproducible. Depending on the application, different filter loadings and types of OC materials can be employed. Matched filter sets prepared by this approach can be used for determining the accuracy of various OC-EC methods and thereby contribute to method standardization.

  10. Improved synthetic route to methyl 1-fluoroindan-1-carboxylate (FICA Me ester) and 4-methyl derivatives.

    PubMed

    Koyanagi, Jyunichi; Kamei, Tomoyo; Ishizaki, Miyuki; Nakamura, Hiroshi; Takahashi, Tamiko

    2014-01-01

    An improved synthetic route has been developed for the preparation of methyl 1-fluoroindan-1-carboxylate (FICA Me ester) from 1-indanone. Methyl 4-methyl-1-fluoroindan-1-carboxylate (4-Me-FICA Me ester) was also prepared following the same procedure.

  11. Molecular dynamics investigations of BioH protein substrate specificity for biotin synthesis.

    PubMed

    Xue, Qiao; Cui, Ying-Lu; Zheng, Qing-Chuan; Zhang, Hong-Xing

    2016-05-01

    BioH, an enzyme of biotin synthesis, plays an important role in fatty acid synthesis which assembles the pimelate moiety. Pimeloyl-acyl carrier protein (ACP) methyl ester, which is long known to be a biotin precursor, is the physiological substrate of BioH. Azelayl methyl ester, which has a longer chain than pimeloyl methyl ester, conjugated to ACP is also indeed accepted by BioH with very low rate of hydrolysis. To date, the substrate specificity for BioH and the molecular origin for the experimentally observed rate changes of hydrolysis by the chain elongation have remained elusive. To this end, we have investigated chain elongation effects on the structures by using the fully atomistic molecular dynamics simulations combined with binding free energy calculations. The results indicate that the substrate specificity is determined by BioH together with ACP. The added two methylenes would increase the structural flexibility by protein motions at the interface of ACP and BioH, instead of making steric clashes with the side chains of the BioH hydrophobic cavity. On the other hand, the slower hydrolysis of azelayl substrate is suggested to be associated with the loose of contacts between BioH and ACP, and with the lost electrostatic interactions of two ionic/hydrogen bonding networks at the interface of the two proteins. The present study provides important insights into the structure-function relationships of the complex of BioH with pimeloyl-ACP methyl ester, which could contribute to further understanding about the mechanism of the biotin synthetic pathway, including the catalytic role of BioH.

  12. Novel pyrrolinones as N-methyl-D-aspartate receptor antagonists.

    PubMed

    Poschenrieder, Hermann; Stachel, Hans-Dietrich; Höfner, Georg; Mayer, Peter

    2005-04-01

    A series of oximes, deriving from 2-arylidene-pyrroline-3,4-diones (7, 8, 22, 23) has been prepared. The presence of tautomers in their solutions has been established by spectroscopic means. The compounds reacted with diazomethane chiefly by N-methylation forming nitrones (10, 11). The analogously prepared 2-arylidene-4-nitropyrrolin-3-ones (12, 13, 24, 25), formally derived from nitrotetramic acids, yielded nitronic acid esters (14, 15, 26) upon reaction with diazomethane. The structures were elucidated by spectral evidence and-in the case of compounds 10 and 20b-by X-ray diffraction analysis. The binding affinity of some of the new compounds toward the N-methyl-d-aspartate (NMDA) (glycine site) receptor has been measured thus providing the basis for further structure-activity relationship studies. Oxime 8b showed the highest binding potency (Ki= 9.2 microM).

  13. 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... 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, reaction products with hexakis(alkoxyalkyl... substance identified generically as 2-propenoic acid, 2-methyl-, 2-hydroxyethyl ester, reaction products...

  14. 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... 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, reaction products with hexakis(alkoxyalkyl... substance identified generically as 2-propenoic acid, 2-methyl-, 2-hydroxyethyl ester, reaction products...

  15. The structure and mechanism of stem bromelain. Evaluation of the homogeneity of purified stem bromelain, determination of the molecular weight and kinetic analysis of the bromelain-catalysed hydrolysis of N-benzyloxycarbonyl-l-phenylalanyl-l-serine methyl ester

    PubMed Central

    Wharton, Christopher W.

    1974-01-01

    1. Purified stem bromelain (EC 3.4.22.4) was eluted from Sephadex G-100 as a single peak. The specific activity across the elution peak was approximately constant towards p-nitrophenyl hippurate but increased with elution volume with N2-benzoyl-l-arginine ethyl ester as substrate. 2. The apparent molecular weight, determined by elution analysis on Sephadex G-100, is 22500±1500, an anomalously low value. 3. Purified stem bromelain was eluted from CM-cellulose CM-32 as a single peak and behaved as a single species during column electrophoresis on Sephadex G-100. 4. Purified stem bromelain migrates as a single band during polyacrylamide-gel electrophoresis under a wide variety of conditions. 5. The molecular weight determined by polyacrylamide-gel electrophoresis in the presence of sodium dodecyl sulphate is 28500±1000. 6. Sedimentation-velocity and equilibrium-ultracentrifugation experiments, under a variety of conditions, indicate that bromelain is an apparently homogeneous single peptide chain of mol.wt. 28400±1400. 7. The N-terminal amino acid composition is 0.64±0.04mol of valine and 0.36±0.04mol of alanine per mol of enzyme of mol.wt. 28500. (The amino acid recovery of the cyanate N-terminal amino acid analysis was standardized by inclusion of carbamoyl-norleucine at the cyclization stage.) 8. The pH-dependence of the Michaelis parameters of the bromelain-catalysed hydrolysis of N-benzyloxycarbonyl-l-phenylalanyl-l-serine methyl ester was determined. 9. The magnitude and pH-dependence of the Michaelis parameters have been interpreted in terms of the mechanism of the enzyme. 10. The enzyme is able to bind N-benzyloxycarbonyl-l-phenylalanyl-l-serine methyl ester relatively strongly but seems unable to make use of the binding energy to promote catalysis. PMID:4462742

  16. Tandem mass spectrometric analysis of aspergillus niger pectin methylesterase: mode of action on fully methyl-esterified oligogalacturonates.

    PubMed

    Kester, H C; Benen, J A; Visser, J; Warren, M E; Orlando, R; Bergmann, C; Magaud, D; Anker, D; Doutheau, A

    2000-03-01

    The substrate specificity and the mode of action of Aspergillus niger pectin methylesterase (PME) was determined using both fully methyl-esterified oligogalacturonates with degrees of polymerization (DP) 2-6 and chemically synthesized monomethyl trigalacturonates. The enzymic activity on the different substrates and a preliminary characterization of the reaction products were performed by using high-performance anion-exchange chromatography at neutral pH. Electrospray ionization tandem MS (ESI-MS/MS) was used to localize the methyl esters on the (18)O-labelled reaction products during the course of the enzymic reaction. A. niger PME is able to hydrolyse the methyl esters of fully methyl-esterified oligogalacturonates with DP 2, and preferentially hydrolyses the methyl esters located on the internal galacturonate residues, followed by hydrolysis of the methyl esters towards the reducing end. This PME is unable to hydrolyse the methyl ester of the galacturonate moiety at the non-reducing end.

  17. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS FOOD ADDITIVES PERMITTED IN FEED AND DRINKING WATER OF ANIMALS Food Additive Listing § 573.660 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil... 21 Food and Drugs 6 2011-04-01 2011-04-01 false Methyl glucoside-coconut oil ester. 573.660...

  18. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS FOOD ADDITIVES PERMITTED IN FEED AND DRINKING WATER OF ANIMALS Food Additive Listing § 573.660 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil... 21 Food and Drugs 6 2014-04-01 2014-04-01 false Methyl glucoside-coconut oil ester. 573.660...

  19. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS FOOD ADDITIVES PERMITTED IN FEED AND DRINKING WATER OF ANIMALS Food Additive Listing § 573.660 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil... 21 Food and Drugs 6 2013-04-01 2013-04-01 false Methyl glucoside-coconut oil ester. 573.660...

  20. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS FOOD ADDITIVES PERMITTED IN FEED AND DRINKING WATER OF ANIMALS Food Additive Listing § 573.660 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil... 21 Food and Drugs 6 2010-04-01 2010-04-01 false Methyl glucoside-coconut oil ester. 573.660...

  1. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS FOOD ADDITIVES PERMITTED IN FEED AND DRINKING WATER OF ANIMALS Food Additive Listing § 573.660 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil... 21 Food and Drugs 6 2012-04-01 2012-04-01 false Methyl glucoside-coconut oil ester. 573.660...

  2. Synthesis and characterization of DNA minor groove binding alkylating agents.

    PubMed

    Iyer, Prema; Srinivasan, Ajay; Singh, Sreelekha K; Mascara, Gerard P; Zayitova, Sevara; Sidone, Brian; Fouquerel, Elise; Svilar, David; Sobol, Robert W; Bobola, Michael S; Silber, John R; Gold, Barry

    2013-01-18

    Derivatives of methyl 3-(1-methyl-5-(1-methyl-5-(propylcarbamoyl)-1H-pyrrol-3-ylcarbamoyl)-1H-pyrrol-3-ylamino)-3-oxopropane-1-sulfonate (1), a peptide-based DNA minor groove binding methylating agent, were synthesized and characterized. In all cases, the N-terminus was appended with an O-methyl sulfonate ester, while the C-terminus group was varied with nonpolar and polar side chains. In addition, the number of pyrrole rings was varied from 2 (dipeptide) to 3 (tripeptide). The ability of the different analogues to efficiently generate N3-methyladenine was demonstrated as was their selectivity for minor groove (N3-methyladenine) versus major groove (N7-methylguanine) methylation. Induced circular dichroism studies were used to measure the DNA equilibrium binding properties of the stable sulfone analogues; the tripeptide binds with affinity that is >10-fold higher than that of the dipeptide. The toxicities of the compounds were evaluated in alkA/tag glycosylase mutant E. coli and in human WT glioma cells and in cells overexpressing and under-expressing N-methylpurine-DNA glycosylase, which excises N3-methyladenine from DNA. The results show that equilibrium binding correlates with the levels of N3-methyladenine produced and cellular toxicity. The toxicity of 1 was inversely related to the expression of MPG in both the bacterial and mammalian cell lines. The enhanced toxicity parallels the reduced activation of PARP and the diminished rate of formation of aldehyde reactive sites observed in the MPG knockdown cells. It is proposed that unrepaired N3-methyladenine is toxic due to its ability to directly block DNA polymerization.

  3. New dicyclopeptides from Dianthus chinensis.

    PubMed

    Han, Jing; Wang, Zhe; Zheng, Yu-Qing; Zeng, Guang-Zhi; He, Wen-Jun; Tan, Ning-Hua

    2014-05-01

    One new dicyclopeptide cyclo-(L-N-methyl Glu-L-N-methyl Glu) (1), together with one new natural dicyclopeptide cyclo-(L-methyl Glu ester-L-methyl Glu ester) (2), and two known dicyclopeptides cyclo-(L-methyl Glu ester-L-Glu) (3), and cyclo-(L-Glu-L-Glu) (4), were isolated from the aerial parts of Dianthus chinensis L. Their structures were determined by spectroscopic analyses and chemical methods.

  4. Scaffold Repurposing of Nucleosides (Adenosine Receptor Agonists): Enhanced Activity at the Human Dopamine and Norepinephrine Sodium Symporters.

    PubMed

    Tosh, Dilip K; Janowsky, Aaron; Eshleman, Amy J; Warnick, Eugene; Gao, Zhan-Guo; Chen, Zhoumou; Gizewski, Elizabeth; Auchampach, John A; Salvemini, Daniela; Jacobson, Kenneth A

    2017-04-13

    We have repurposed (N)-methanocarba adenosine derivatives (A 3 adenosine receptor (AR) agonists) to enhance radioligand binding allosterically at the human dopamine (DA) transporter (DAT) and inhibit DA uptake. We extended the structure-activity relationship of this series with small N 6 -alkyl substitution, 5'-esters, deaza modifications of adenine, and ribose restored in place of methanocarba. C2-(5-Halothien-2-yl)-ethynyl 5'-methyl 9 (MRS7292) and 5'-ethyl 10 (MRS7232) esters enhanced binding at DAT (EC 50 ∼ 35 nM) and at the norepinephrine transporter (NET). 9 and 10 were selective for DAT compared to A 3 AR in the mouse but not in humans. At DAT, the binding of two structurally dissimilar radioligands was enhanced; NET binding of only one radioligand was enhanced; SERT radioligand binding was minimally affected. 10 was more potent than cocaine at inhibiting DA uptake (IC 50 = 107 nM). Ribose analogues were weaker in DAT interaction than the corresponding bicyclics. Thus, we enhanced the neurotransmitter transporter activity of rigid nucleosides while reducing A 3 AR affinity.

  5. Emissions analysis on diesel engine fuelled with cashew nut shell biodiesel and pentanol blends.

    PubMed

    Devarajan, Yuvarajan; Munuswamy, Dinesh Babu; Nagappan, BeemKumar

    2017-05-01

    The present work is intended to investigate the emission characteristics of neat cashew nut shell methyl ester (CNSME100) by adding pentanol at two different proportions and compared with the baseline diesel. CNSME100 is prepared by the conventional transesterification process. CNSME100 is chosen due to its non-edible nature. Pentanol is chosen as an additive because of its higher inbuilt oxygen content and surface to volume ratio which reduces the drawbacks of neat CNSME100. Emission characteristics were carried out in single cylinder naturally aspirated CI engine fuelled with neat cashew nut shell methyl ester (CNSME), cashew nut shell methyl ester and pentanol by 10% volume (CNSME90P10), cashew nut shell methyl ester and pentanol by 20% volume (CNSME80P20), and diesel. This work also aims to investigate the feasibility of operating an engine fuelled with neat methyl ester and alcohol blends. Experimental results showed that by blending higher alcohol to neat cashew nut shell methyl ester reduces the emissions significantly. It is also found that the emission from neat methyl ester and pentanol blends is lesser than diesel at all loads.

  6. Experimental Investigations on Diesel engine using Methyl esters of Jatropha oil and fish oil

    NASA Astrophysics Data System (ADS)

    Karthikeyan, A.; Jayaprabakar, J.; Dude Williams, Richard

    2017-05-01

    The aim of the study is to use fish oil methyl ester (FME) and Jatropha oil methyl ester (JME) as a substitute for diesel in compression ignition engine. Experiments were conducted when the engine was fuelled with Diesel, Fish oil methyl ester and Jatropha oil methyl ester. The experiment covered a range of loads. An AVL smoke meter was used to measure the smoke density in HSU (Hatridge Smoke Unit). The exhaust emissions were measured using exhaust gas analyzer. High volume sampler was employed to measure the particulate matter in exhaust. The performance of the engine was evaluated in terms of brake specific fuel consumption, brake thermal efficiency. The combustion characteristics of the engine were studied in terms of cylinder pressure with respect to crank angle. The emissions of the engine were studied in terms of concentration of CO, NOx, particulate matter and smoke density. The results obtained for Fish oil methyl ester, Jatropha oil methyl ester, were compared with the results of diesel. Bio-diesel, which can be used as an alternate diesel fuel, is made from vegetable oil and animal fats. It is renewable, non-toxic and possesses low emission profiles.

  7. 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 the...

  8. 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 the...

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

    PubMed

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

    2007-01-01

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

  10. Biodiesel production from vegetable oil and waste animal fats in a pilot plant.

    PubMed

    Alptekin, Ertan; Canakci, Mustafa; Sanli, Huseyin

    2014-11-01

    In this study, corn oil as vegetable oil, chicken fat and fleshing oil as animal fats were used to produce methyl ester in a biodiesel pilot plant. The FFA level of the corn oil was below 1% while those of animal fats were too high to produce biodiesel via base catalyst. Therefore, it was needed to perform pretreatment reaction for the animal fats. For this aim, sulfuric acid was used as catalyst and methanol was used as alcohol in the pretreatment reactions. After reducing the FFA level of the animal fats to less than 1%, the transesterification reaction was completed with alkaline catalyst. Due to low FFA content of corn oil, it was directly subjected to transesterification. Potassium hydroxide was used as catalyst and methanol was used as alcohol for transesterification reactions. The fuel properties of methyl esters produced in the biodiesel pilot plant were characterized and compared to EN 14214 and ASTM D6751 biodiesel standards. According to the results, ester yield values of animal fat methyl esters were slightly lower than that of the corn oil methyl ester (COME). The production cost of COME was higher than those of animal fat methyl esters due to being high cost biodiesel feedstock. The fuel properties of produced methyl esters were close to each other. Especially, the sulfur content and cold flow properties of the COME were lower than those of animal fat methyl esters. The measured fuel properties of all produced methyl esters met ASTM D6751 (S500) biodiesel fuel standards. Copyright © 2014 Elsevier Ltd. All rights reserved.

  11. Anaerobic biodegradation of methyl esters by Acetobacterium woodii and Eubacterium limosum

    USGS Publications Warehouse

    Liu, Shi; Suflita, Joseph M.

    1994-01-01

    The ability ofAcetobacterium woodii andEubacterium limosum to degrade methyl esters of acetate, propionate, butyrate, and isobutyrate was examined under growing and resting-cell conditions. Both bacteria hydrolyzed the esters to the corresponding carboxylates and methanol under either condition. Methanol was further oxidized to formate under growing but not resting conditions. Unlike the metabolism of phenylmethylethers, no H2 requirement was evident for ester biotransformation. The hydrolysis of methyl carboxylates is thermodynamically favorable under standard conditions and the mixotrophic metabolism of ester/CO2 allowed for bacterial growth. These results suggest that the degradation of methyl carboxylates may be a heretofore unrecognized nutritional option for acetogenic bacteria.

  12. Maternal melatonin or N-acetylcysteine therapy regulates hydrogen sulfide-generating pathway and renal transcriptome to prevent prenatal NG-Nitro-L-arginine-methyl ester (L-NAME)-induced fetal programming of hypertension in adult male offspring.

    PubMed

    Tain, You-Lin; Lee, Chien-Te; Chan, Julie Y H; Hsu, Chien-Ning

    2016-11-01

    Pregnancy is a critical time for fetal programming of hypertension. Nitric oxide deficiency during pregnancy causes hypertension in adult offspring. We examined whether maternal melatonin or N-acetylcysteine therapy can prevent N G -nitro-L-arginine-methyl ester-induced fetal programming of hypertension in adult offspring. Next, we aimed to identify potential gatekeeper pathways that contribute to N G -nitro-L-arginine-methyl ester -induced programmed hypertension using the next generation RNA sequencing technology. Pregnant Sprague-Dawley rats were assigned to 4 groups: control, N G -nitro-L-arginine-methyl ester, N G -nitro-L-arginine-methyl ester +melatonin, and N G -nitro-L-arginine-methyl ester+N-acetylcysteine. Pregnant rats received N G -nitro-L-arginine-methyl ester administration at 60 mg/kg/d subcutaneously during pregnancy alone, with additional 0.01% melatonin in drinking water, or with additional 1% N-acetylcysteine in drinking water during the entire pregnancy and lactation. Male offspring (n=8/group) were killed at 12 weeks of age. N G -nitro-L-arginine-methyl ester exposure during pregnancy induced programmed hypertension in adult male offspring, which was prevented by maternal melatonin or N-acetylcysteine therapy. Protective effects of melatonin and N-acetylcysteine against N G -nitro-L-arginine-methyl ester-induced programmed hypertension were associated with an increase in hydrogen sulfide-generating enzymes and hydrogen sulfide synthesis in the kidneys. Nitric oxide inhibition by N G -nitro-L-arginine-methyl ester in pregnancy caused >2000 renal transcripts to be modified during nephrogenesis stage in 1-day-old offspring kidney. Among them, genes belong to the renin-angiotensin system, and arachidonic acid metabolism pathways were potentially involved in the N G -nitro-L-arginine-methyl ester-induced programmed hypertension. However, melatonin and N-acetylcysteine reprogrammed the renin-angiotensin system and arachidonic acid pathway differentially. Our results indicated that antioxidant therapy, by melatonin or N-acetylcysteine, in pregnant rats with nitric oxide deficiency can prevent programmed hypertension in male adult offspring. Early intervention with specific antioxidants that target redox imbalance in pregnancy to reprogram hypertension may well allow us to reduce the future burden of hypertension. The roles of transcriptome changes that are induced by N G -nitro-L-arginine-methyl ester in the offspring kidney require further clarification. Copyright © 2016 Elsevier Inc. All rights reserved.

  13. Chikusetsusaponin IVa methyl ester induces cell cycle arrest by the inhibition of nuclear translocation of β-catenin in HCT116 cells

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    Lee, Kyung-Mi; Yun, Ji Ho; Lee, Dong Hwa

    2015-04-17

    We demonstrate that chikusetsusaponin IVa methyl ester (CME), a triterpenoid saponin from the root of Achyranthes japonica, has an anticancer activity. We investigate its molecular mechanism in depth in HCT116 cells. CME reduces the amount of β-catenin in nucleus and inhibits the binding of β-catenin to specific DNA sequences (TCF binding elements, TBE) in target gene promoters. Thus, CME appears to decrease the expression of cell cycle regulatory proteins such as Cyclin D1, as a representative target for β-catenin, as well as CDK2 and CDK4. As a result of the decrease of the cell cycle regulatory proteins, CME inhibits cellmore » proliferation by arresting the cell cycle at the G0/G1 phase. Therefore, we suggest that CME as a novel Wnt/β-catenin inhibitor can be a putative agent for the treatment of colorectal cancers. - Highlights: • CME inhibits cell proliferation in HCT116 cells. • CME increases cell cycle arrest at G0/G1 phase and apoptosis. • CME attenuates cyclin D1 and regulates cell cycle regulatory proteins. • CME inhibits β-catenin translocation to nucleus.« less

  14. Trapping Phyllophaga spp. (Coleoptera: Scarabaeidae: Melolonthinae) in the United States and Canada using sex attractants.

    PubMed Central

    Robbins, Paul S.; Alm, Steven R.; Armstrong, Charles. D.; Averill, Anne L.; Baker, Thomas C.; Bauernfiend, Robert J.; Baxendale, Frederick P.; Braman, S. Kris; Brandenburg, Rick L.; Cash, Daniel B.; Couch, Gary J.; Cowles, Richard S.; Crocker, Robert L.; DeLamar, Zandra D.; Dittl, Timothy G.; Fitzpatrick, Sheila M.; Flanders, Kathy L.; Forgatsch, Tom; Gibb, Timothy J.; Gill, Bruce D.; Gilrein, Daniel O.; Gorsuch, Clyde S.; Hammond, Abner M.; Hastings, Patricia D.; Held, David W.; Heller, Paul R.; Hiskes, Rose T.; Holliman, James L.; Hudson, William G.; Klein, Michael G.; Krischik, Vera L.; Lee, David J.; Linn, Charles E.; Luce, Nancy J.; MacKenzie, Kenna E.; Mannion, Catherine M.; Polavarapu, Sridhar; Potter, Daniel A.; Roelofs, Wendell L.; Royals, Brian M.; Salsbury, Glenn A.; Schiff, Nathan M.; Shetlar, David J.; Skinner, Margaret; Sparks, Beverly L.; Sutschek, Jessica A.; Sutschek, Timothy P.; Swier, Stanley R.; Sylvia, Martha M.; Vickers, Neil J.; Vittum, Patricia J.; Weidman, Richard; Weber, Donald C.; Williamson, R. Chris; Villani, Michael G

    2006-01-01

    The sex pheromone of the scarab beetle, Phyllophaga anxia, is a blend of the methyl esters of two amino acids, L-valine and L-isoleucine. A field trapping study was conducted, deploying different blends of the two compounds at 59 locations in the United States and Canada. More than 57,000 males of 61 Phyllophaga species (Coleoptera: Scarabaeidae: Melolonthinae) were captured and identified. Three major findings included: (1) widespread use of the two compounds [of the 147 Phyllophaga (sensu stricto) species found in the United States and Canada, males of nearly 40% were captured]; (2) in most species intraspecific male response to the pheromone blends was stable between years and over geography; and (3) an unusual pheromone polymorphism was described from P. anxia. Populations at some locations were captured with L-valine methyl ester alone, whereas populations at other locations were captured with L-isoleucine methyl ester alone. At additional locations, the L-valine methyl ester-responding populations and the L-isoleucine methyl ester-responding populations were both present, producing a bimodal capture curve. In southeastern Massachusetts and in Rhode Island, in the United States, P. anxia males were captured with blends of L-valine methyl ester and L-isoleucine methyl ester. PMID:19537965

  15. Characterization of muscarinic receptors on intact human neuroblastoma cells: coupling to phosphoinositide hydrolysis and phosphorylation by phorbol esters

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    Serra, M.; Watson, M.; Roeske, W.R.

    Cloned human neuroblastoma cells (SH-SY5Y) were grown. High affinity binding of (/sup 3/H)(-)quinuclidinyl benzilate ((/sup 3/H)(-)QNB) and its quaternary derivative (/sup 3/H)(-)methyl QNB to muscarinic receptors (MR) on intact SH-SY5Y cells was studied. A 30 min rinse time gave a ratio of specific/total binding of 90% for both ligands. Association rates of (/sup 3/H)(-)QNB and (/sup 3/H)(-)methyl QNB were determined. Both ligands reached steady state by 60 min at 37/sup 0/C. Rates of dissociation for both radioligands were biphasic, although (/sup 3/H)(-)methyl QNB was faster. Saturation studies yielded K/sub d/ (dissociation constant) values of 16 and 260 pM and B/submore » max/ (maximal MR density) values of 172 and 134 fmoles/mg prot for (/sup 3/H)(-)QNB and (/sup 3/H)(-)methyl QNB, respectively. Activation of protein kinase C by phorbol esters produced increased phosphorylation of cellular proteins. Pretreatment with 100 nM of 4..beta..-phorbol 12..beta..-myristate 13..cap alpha..-acetate (PMA) induced a decrease in agonist affinity for MR, suggesting a PMA-promoted phosphorylation of the MR protein. Phosphoinositide (PhI) turnover was measured by MR agonist-induced accumulation of inositol-1-phosphate in the presence of Li/sup + +/ (10 mM). Only carbachol and acetylcholine elicited potent responses with oxotremorine (16%) pilocarpine (17%) and McN-A-343 (8%) appearing to be weak partial agonist of low efficacy.« less

  16. Modeling Study of the Low-Temperature Oxidation of Large Methyl Esters from C11 to C19

    PubMed Central

    Herbinet, Olivier; Biet, Joffrey; Hakka, Mohammed Hichem; Warth, Valérie; Glaude, Pierre Alexandre; Nicolle, André; Battin-Leclerc, Frédérique

    2013-01-01

    The modeling of the low temperature oxidation of large saturated methyl esters really representative of those found in biodiesel fuels has been investigated. Models have been developed for these species and then detailed kinetic mechanisms have been automatically generated using a new extended version of software EXGAS, which includes reactions specific to the chemistry of esters. A model generated for a binary mixture of n-decane and methyl palmitate was used to simulate experimental results obtained in a jet-stirred reactor for this fuel. This model predicts very well the reactivity of the fuel and the mole fraction profiles of most reaction products. This work also shows that a model for a middle size methyl ester such as methyl decanoate predicts fairly well the reactivity and the mole fractions of most species with a substantial decrease in computational time. Large n-alkanes such as n-hexadecane are also good surrogates for reproducing the reactivity of methyl esters, with an important gain in computational time, but they cannot account for the formation of specific products such as unsaturated esters or cyclic ethers with an ester function. PMID:23814504

  17. Novel Strategy of Using Methyl Esters as Slow Release Methanol Source during Lipase Expression by mut+ Pichia pastoris X33

    PubMed Central

    Kumari, Arti; Gupta, Rani

    2014-01-01

    One of the major issues with heterologous production of proteins in Pichia pastoris X33 under AOX1 promoter is repeated methanol induction. To obviate repeated methanol induction, methyl esters were used as a slow release source of methanol in lipase expressing mut+ recombinant. Experimental design was based on the strategy that in presence of lipase, methyl esters can be hydrolysed to release their products as methanol and fatty acid. Hence, upon break down of methyl esters by lipase, first methanol will be used as a carbon source and inducer. Then P. pastoris can switch over to fatty acid as a carbon source for multiplication and biomass maintenance till further induction by methyl esters. We validated this strategy using recombinant P. pastoris expressing Lip A, Lip C from Trichosporon asahii and Lip11 from Yarrowia lipolytica. We found that the optimum lipase yield under repeated methanol induction after 120 h was 32866 U/L, 28271 U/L and 21978 U/L for Lip C, Lip A and Lip 11 respectively. In addition, we found that a single dose of methyl ester supported higher production than repeated methanol induction. Among various methyl esters tested, methyl oleate (0.5%) caused 1.2 fold higher yield for LipA and LipC and 1.4 fold for Lip11 after 120 h of induction. Sequential utilization of methanol and oleic acid by P. pastoris was observed and was supported by differential peroxisome proliferation studies by transmission electron microscopy. Our study identifies a novel strategy of using methyl esters as slow release methanol source during lipase expression. PMID:25170843

  18. Chemical composition of the leaf and stem essential oil of Adenophorae Radix

    NASA Astrophysics Data System (ADS)

    Lan, Weijie; Lin, Shang; Li, Xindan; Zhang, Qing; Qin, Wen

    2017-03-01

    The chemical composition of the essential oil extracted from leaves and stems of Adenophorae Radix was determined for the first time in this study. Twenty-six compounds were identified by gas chromatography coupled to mass spectrometry (GC-MS). n-Hexadecanoic acid (29.14%), 9,12-octadecadienoic acid (Z,Z)- (17.22%), hexadecanoic acid, methyl ester(8.98%), 9-octadecenoic acid, methyl ester, (E)- (7.03%), 9,12-octadecadienoic acid (Z,Z)-, methyl ester (5.93%), phytol (5.50%), and estradiol (4.43%) were measured as the major compounds in stem oil. The leaf essential oil was dominated by n-hexadecanoic acid (50.78%), 9-octadecenoic acid, methyl ester, (E)- (9.04%), phytol (8.47%), d-mannitol (5.81%), 9,12,15-octadecatrienoic acid, methyl ester, (Z,Z,Z)- (4.31%), hexadecanoic acid, methyl ester (2.19%) and 9,12-octadecadienoic acid (Z,Z)-(1.7%). The leaves yield was 0.12% (v/w) and the stems yield showed only 0.073% (v/w). The results might provide reference basis for further exploration of its application value.

  19. An Experimental and Kinetic Modeling Study of Methyl Decanoate Combustion

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    Sarathy, S M; Thomson, M J; Pitz, W J

    2009-12-04

    Biodiesel is a mixture of long chain fatty acid methyl esters derived from fats and oils. This research study presents opposed-flow diffusion flame data for one large fatty acid methyl ester, methyl decanoate, and uses the experiments to validate an improved skeletal mechanism consisting of 648 species and 2998 reactions. The results indicate that methyl decanoate is consumed via abstraction of hydrogen atoms to produce fuel radicals, which lead to the production of alkenes. The ester moiety in methyl decanoate leads to the formation of low molecular weight oxygenated compounds such as carbon monoxide, formaldehyde, and ketene.

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

    USDA-ARS?s Scientific Manuscript database

    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...

  1. Vapor movement of the synthetic auxin herbicides, aminocyclopyrachlor and its methyl ester under laboratory and enclosed chamber environments

    USDA-ARS?s Scientific Manuscript database

    Aminocyclopyrachlor (DPX MAT28) a newly discovered synthetic auxin herbicide and its methyl ester (DPX KJM44) appear to control a number of perennial broadleaf weeds. The potential volatility of this new herbicide and its methyl ester were determined under laboratory conditions and were also compar...

  2. Emissions from diesel engines using fatty acid methyl esters from different vegetable oils as blends and pure fuel

    NASA Astrophysics Data System (ADS)

    Schröder, O.; Munack, A.; Schaak, J.; Pabst, C.; Schmidt, L.; Bünger, J.; Krahl, J.

    2012-05-01

    Biodiesel is used as a neat fuel as well as in blends with mineral diesel fuel. Because of the limited availability of fossil resources, an increase of biogenic compounds in fuels is desired. To achieve this goal, next to rapeseed oil, other sustainably produced vegetable oils can be used as raw materials. These raw materials influence the fuel properties as well as the emissions. To investigate the environmental impact of the exhaust gas, it is necessary to determine regulated and non-regulated exhaust gas components. In detail, emissions of aldehydes and polycyclic aromatic hydrocarbons (PAH), as well as mutagenicity in the Ames test are of special interest. In this paper emission measurements on a Euro III engine OM 906 of Mercedes-Benz are presented. As fuel vegetable oil methyl esters from various sources and reference diesel fuel were used as well as blends of the vegetable oil methyl esters with diesel fuel. PAH were sampled according to VDI Guideline 3872. The sampling procedure of carbonyls was accomplished using DNPH cartridges coupled with potassium iodide cartridges. The carbon monoxide and hydrocarbon emissions of the tested methyl esters show advantages over DF. The particle mass emissions of methyl esters were likewise lower than those of DF, only linseed oil methyl ester showed higher particle mass emissions. A disadvantage is the use of biodiesel with respect to emissions of nitrogen oxides. They increased depending on the type of methyl ester by 10% to 30%. Emissions of polycyclic aromatic hydrocarbons (PAHs) and the results of mutagenicity tests correlate with those of the PM measurements, at which for palm oil methyl ester next to coconut oil methyl ester the lowest emissions were detected. From these results one can formulate a clear link between the iodine number of the ester and the emission behaviour. For blends of biodiesel and diesel fuel, emissions changed linearly with the proportion of biodiesel. However, especially in the non-regulated exhaust gas components, some deviations from this linear trend were detected.

  3. Complementary blending of meadowfoam seed oil methyl esters with biodiesel prepared from soybean and waste cooking oils to enhance fuel properties

    USDA-ARS?s Scientific Manuscript database

    The complementary blending of meadowfoam seed oil methyl esters (MFME) with soybean and waste cooking oil methyl esters (SME and WCME) was investigated. MFME prepared from cold-pressed meadowfoam oil exhibited an exceptionally high induction period (IP) of 66.2 h whereas SME and WCME yielded conside...

  4. Comparative study of the antioxidant activities of some lipase-catalyzed alkyl dihydrocaffeates synthesized in ionic liquid.

    PubMed

    Gholivand, Somayeh; Lasekan, Ola; Tan, Chin Ping; Abas, Faridah; Wei, Leong Sze

    2017-06-01

    The solubility limitations of phenolic acids in many lipidic environments are now greatly improved by their enzymatic esterification in ionic liquids (ILs). Herein, four different ILs were tested for the esterification of dihydrocaffeic acid with hexanol and the best IL was selected for the synthesis of four other n-alkyl esters with different chain-lengths. The effect of alkyl chain length on the anti-oxidative properties of the resulted purified esters was investigated using β-carotene bleaching (BCB) and free radical scavenging method DPPH and compared with butylated hydroxytoluene (BHT) as reference compound. All four esters (methyl, hexyl, dodecyl and octadecyl dihydrocaffeates) exhibited relatively strong radical scavenging abilities. The scavenging activity of the test compounds was in the following order: methyl ester>hexyl ester⩾dodecyl ester>octadecyl ester>BHT while the order for the BCB anti-oxidative activity was; BHT>octadecyl ester>dodecyl ester>hexyl ester>methyl ester. Copyright © 2016 Elsevier Ltd. All rights reserved.

  5. Modeling of the oxidation of methyl esters—Validation for methyl hexanoate, methyl heptanoate, and methyl decanoate in a jet-stirred reactor

    PubMed Central

    Glaude, Pierre Alexandre; Herbinet, Olivier; Bax, Sarah; Biet, Joffrey; Warth, Valérie; Battin-Leclerc, Frédérique

    2013-01-01

    The modeling of the oxidation of methyl esters was investigated and the specific chemistry, which is due to the presence of the ester group in this class of molecules, is described. New reactions and rate parameters were defined and included in the software EXGAS for the automatic generation of kinetic mechanisms. Models generated with EXGAS were successfully validated against data from the literature (oxidation of methyl hexanoate and methyl heptanoate in a jet-stirred reactor) and a new set of experimental results for methyl decanoate. The oxidation of this last species was investigated in a jet-stirred reactor at temperatures from 500 to 1100 K, including the negative temperature coefficient region, under stoichiometric conditions, at a pressure of 1.06 bar and for a residence time of 1.5 s: more than 30 reaction products, including olefins, unsaturated esters, and cyclic ethers, were quantified and successfully simulated. Flow rate analysis showed that reactions pathways for the oxidation of methyl esters in the low-temperature range are similar to that of alkanes. PMID:23710076

  6. Experimental investigation of the auto-ignition characteristics of oxygenated reference fuel compounds

    NASA Astrophysics Data System (ADS)

    Walton, Stephen Michael

    The increased use of biofuels presents an opportunity to improve combustion performance while simultaneously reducing greenhouse gases and pollutant emissions. This work focused on improving the fundamental understanding of the auto-ignition chemistry of oxygenated reference fuel compounds. A systematic study of the effects of ester structure on ignition chemistry was performed using the University of Michigan Rapid Compression Facility. The ignition properties of the ester compounds were investigated over a broad range of pressures (P=5-20 atm) and temperatures (T=850-1150 K) which are directly relevant to advanced combustion engine strategies. Ignition delay times for five esters were determined using the RCF. The esters were selected to systematically consider the chemical structure of the compounds. Three esters were saturated: methyl butanoate, butyl methanoate, and ethyl propanoate; and two were unsaturated: methyl crotonate and methyl trans-3-hexenoate. The unsaturated esters were more reactive than their saturated counterparts, with the largest unsaturated ester, methyl trans-3-hexenoate having the highest reactivity. Two isomers of the saturated esters, butyl methanoate and ethyl propanoate, were more reactive than the isomer methyl butanoate. The results are explained if we assume that butyl methanoate and ethyl propanoate form intermediate ring structures which decompose more rapidly than esters such as methyl butanoate, which do not form ring structures. Modeling studies of the reaction chemistry were conducted for methyl butanoate and ethyl propanoate, for which detailed mechanisms were available in the literature. The new experimental data indicated that literature rate coefficients for some of the methyl butanoate/HO2 reactions were too fast. Modifying these within the theoretical uncertainties for the reaction rates, led to excellent agreement between the model predictions and the experimental data. Comparison of the modeling results with the intermediates measured during methyl butanoate ignition indicated that pathways leading to the formation of small hydrocarbons are relatively well represented in the reaction mechanism. The results of this work provide archival benchmark data for improved understanding of the dominant reaction pathways and species controlling the auto-ignition of oxygenated reference fuel compounds. These data also provide a path for continued development of chemical kinetic models to optimize practical combustion systems.

  7. The sensitivity of glioma cells to pyropheophorbide-αmethyl ester-mediated photodynamic therapy is enhanced by inhibiting ABCG2.

    PubMed

    Pan, Li; Lin, Haidan; Tian, Si; Bai, Dingqun; Kong, Yuhan; Yu, Lehua

    2017-09-01

    To study the mechanisms of human glioblastoma cell resistance to methyl ester pyropheophorbide-a-mediated photodynamic therapy (MPPa-PDT) and the relationship between the cells and adenosine triphosphate-binding cassette superfamily G member 2 (ABCG2). The sensitivity of four human glioma cell lines (U87, A172, SHG-44, and U251) to MPPa-PDT was detected with a CCK-8 assay. Cell apoptosis, intracellular MPPa, and singlet oxygen were tested with flow cytometry. The mRNA and protein expression of ATP-binding cassette transporters (ABCG2, MRP1, and MDR1) were detected by PCR and Western blot, respectively. Both the sensitivity to MPPa-PDT and intracellular MPPa in A172 were the lowest among the four cell lines, while expression of ABCG2 mRNA and protein in A172 were the highest. The intracellular MPPa and ROS in A172 receiving MPPa-PDT significantly increased after using the ABCG2 inhibitor fumitremorgin C (FTC). Both cell viability and apoptosis in A172 cells undergoing MPPa-PDT were significantly improved with FTC. ABCG2 plays a significant role in the resistance of A172 to MPPa-PDT. Lasers Surg. Med. 49:719-726, 2017. © 2017 Wiley Periodicals, Inc. © 2017 Wiley Periodicals, Inc.

  8. DOE Office of Scientific and Technical Information (OSTI.GOV)

    Eler, Gabrielle Jacklin; Santos, Israel Souza; Giaretta de Moraes, Amarilis

    n-Propyl gallate and its analogs are used in foods and other products to prevent oxidation. In the liver the compound exerts several harmful effects, especially gluconeogenesis inhibition. The mode of transport and distribution of n-propyl gallate and its kinetics of biotransformation have not yet been investigated. To fill this gap the transformation, transport and distribution of n-propyl gallate and two analogs were investigated in the rat liver. Isolated perfused rat liver was used. n-Propyl gallate, methyl gallate, n-octyl gallate and transformation products were quantified by high pressure-liquid chromatography coupled to fluorescence detection. The interactions of n-propyl gallate and analogs withmore » the liver presented three main characteristics: (1) the hydrolytic release of gallic acid from n-propyl gallate and methyl gallate was very fast compared with the subsequent transformations of the gallic acid moiety; (2) transport of the esters was very fast and flow-limited in contrast to the slow and barrier-limited transport of gallic acid; (3) the apparent distribution volume of n-propyl gallate, but probably also of methyl gallate and n-octyl gallate, greatly exceeded the water space in the liver, contrary to the gallic acid space which is smaller than the water space. It can be concluded that at low portal concentrations (< 50 μM) the gallic acid esters are 100% extracted during a single passage through the liver, releasing mainly gallic acid into the systemic circulation. For the latter a considerable time is required until complete biotransformation. The exposure of the liver to the esters, however, is quite prolonged due to extensive intracellular binding. - Highlights: • The liver binds very strongly n-propyl gallate and releases basically gallic acid. • n-propyl gallate and analogs undergo concentrative flow-limited distribution. • Gallic acid undergoes barrier-limited distribution and is slowly transformed. • The long residence time of n-propyl gallate and analogs increases toxicity.« less

  9. Photophysics and morphology of poly (3-dodecylthienylenevinylene)-[6,6]-phenyl-C{sub 61}-butyric acid methyl ester composite

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    Lafalce, E.; Toglia, P.; Jiang, X.

    2012-05-21

    A series of low band gap poly(3-dodecylthienylenevinylene) (PTV) with controlled morphological order have been synthesized and blended with the electron acceptor [6,6]-phenyl-C{sub 61}-butyric acid methyl ester (PCBM) for organic photovoltaic devices. Two polymers with the most and least side chain regioregularity were chosen in this work, namely the PTV010 and PTV55, respectively. Using photoluminescence, photo-induced absorption spectroscopy, and atomic force microscopy, we find no direct evidence of photoinduced charge transfer between the two constituents, independent of the bulk-heterojunction morphology of the film, although the possibility of formation of P{sup +}/C{sub 60}{sup -} charge transfer complex was not completely ruled out.more » The large exciton binding energy (E{sub b} = 0.6 eV) in PTV inhibits the photoinduced electron transfer from PTV to PCBM. In addition, excitons formed on polymer chains suffer ultrafast (« less

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

    NASA Astrophysics Data System (ADS)

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

    2017-09-01

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

  11. Synthesis of fatty acid methyl ester from crude jatropha (Jatropha curcas Linnaeus) oil using aluminium oxide modified Mg-Zn heterogeneous catalyst.

    PubMed

    Olutoye, M A; Hameed, B H

    2011-06-01

    The synthesis of fatty acid methyl esters (FAME) as a substitute to petroleum diesel was investigated in this study from crude jatropha oil (CJO), a non-edible, low-cost alternative feedstock, using aluminium modified heterogeneous basic oxide (Mg-Zn) catalyst. The transesterification reaction with methanol to methyl esters yielded 94% in 6h with methanol-oil ratio of 11:1, catalyst loading of 8.68 wt.% at 182°C and the properties of CJO fuel produced were determine and found to be comparable to the standards according to ASTM. In the range of experimental parameters investigated, it showed that the catalyst is selective to production of methyl esters from oil with high free fatty acid (FFA) and water content of 7.23% and 3.28%, respectively in a single stage process. Thus, jatropha oil is a promising feedstock for methyl ester production and large scale cultivation will help to reduce the product cost. Copyright © 2011 Elsevier Ltd. All rights reserved.

  12. The Produce of Methyl Ester from Crude Palm Oil (CPO) Using Heterogene Catalyst Ash of Chicken Bone (CaO) using Ethanol as Solvent

    NASA Astrophysics Data System (ADS)

    Sinaga, M. S.; Fauzi, R.; Turnip, J. R.

    2017-03-01

    Methyl Ester (methyl ester) is generally made by trans esterification using heterogeneous base catalyst. To simplify the separation, the heterogeneous catalyst is used, such as CaO, which in this case was isolated from chicken bones made by softening chicken bones and do calcination process. Some other important variables other than the selection of the catalyst is the catalyst dosage, molar ratio of ethanol to the CPO and the reaction temperature. The best result from this observe is at the molar ratio of ethanol to the CPO is 17: 1, the reaction temperature is 70 ° C and 7% catalyst (w.t) with reaction time for 7 hours at 500 rpm as a constant variable, got 90,052 % purity, so that this result does not get the standard requirements of biodiesel, because of the purity of the biodiesel standard temporary must be achieve > 96.5 %. This study aims to produce methyl ester yield with the influence of the reaction temperature, percent of catalyst and molar ratio of ethanol and CPO. The most influential variable is the temperature of the reaction that gives a significant yield difference of methyl ester produced. It’s been proven by the increasing temperature used will also significantly increase the yield of methyl ester.

  13. Gallic acid-based alkyl esters synthesis in a water-free system by celite-bound lipase of Bacillus licheniformis SCD11501.

    PubMed

    Sharma, Shivika; Kanwar, Shamsher S; Dogra, Priyanka; Chauhan, Ghanshyam S

    2015-01-01

    Gallic acid (3, 4, 5- trihydroxybenzoic acid) is an important antioxidant, anti-inflammatory, and radical scavenging agent. In the present study, a purified thermo-tolerant extra-cellular lipase of Bacillus licheniformis SCD11501 was successfully immobilized by adsorption on Celite 545 gel matrix followed by treatment with a cross-linking agent, glutaraldehyde. The celite-bound lipase treated with glutaraldehyde showed 94.8% binding/retention of enzyme activity (36 U/g; specific activity 16.8 U/g matrix; relative increase in enzyme activity 64.7%) while untreated matrix resulted in 88.1% binding/retention (28.0 U/g matrix; specific activity 8.5 U/g matrix) of lipase. The celite-bound lipase was successfully used to synthesis methyl gallate (58.2%), ethyl gallate (66.9%), n-propyl gallate (72.1%), and n-butyl gallate (63.8%) at 55(o) C in 10 h under shaking (150 g) in a water-free system by sequentially optimizing various reaction parameters. The low conversion of more polar alcohols such as methanol and ethanol into their respective gallate esters might be due to the ability of these alcohols to severely remove water from the protein hydration shell, leading to enzyme inactivation. Molecular sieves added to the reaction mixture resulted in enhanced yield of the alkyl ester(s). The characterization of synthesised esters was done through fourier transform infrared (FTIR) spectroscopy and (1) H NMR spectrum analysis. © 2015 American Institute of Chemical Engineers.

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

    PubMed

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

    1981-12-01

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

  15. Determination of Acylglycerols in Diesel Oils by GC

    PubMed Central

    Wawrzyniak, Rafał; Wasiak, Wiesław

    2008-01-01

    In many EU countries and outside the EU, besides the addition of pure methyl ester B-100 to diesel oil, mixtures of methyl esters are also added to fuel. To be used as fuel, methyl esters must meet certain requirements, one of which is a certain level of acylglycerols. The paper presents results of determination of acylglycerols in diesel oil dotted with fatty acid methyl esters. The compounds were determined by gas chromatography using a high-temperature capillary column DB-5HT, made by J&W, and 1,2,3-tricaproylglycerol as internal standard. The analytical method proposed permits not only determination of acylglycerols, but also differentiation if the FAME added originated from pure vegetation oil or used cooking oil. PMID:19696907

  16. 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 boric...

  17. 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 boric...

  18. 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 boric...

  19. 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 boric...

  20. 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 boric...

  1. Preparation and characterization of bio-diesels from various bio-oils.

    PubMed

    Lang, X; Dalai, A K; Bakhshi, N N; Reaney, M J; Hertz, P B

    2001-10-01

    Methyl, ethyl, 2-propyl and butyl esters were prepared from canola and linseed oils through transesterification using KOH and/ or sodium alkoxides as catalysts. In addition, methyl and ethyl esters were prepared from rapeseed and sunflower oils using the same catalysts. Chemical composition of the esters was determined by HPLC for the class of lipids and by GC for fatty acid compositions. The bio-diesel esters were characterized for their physical and fuel properties including density, viscosity, iodine value, acid value, cloud point, pure point, gross heat of combustion and volatility. Methyl and ethyl esters prepared from a particular vegetable oil had similar viscosities, cloud points and pour points, whereas methyl, ethyl, 2-propyl and butyl esters derived from a particular vegetable oil had similar gross heating values. However, their densities, which were 2 7% higher than those of diesel fuels, statistically decreased in the order of methyl approximately 2-propyl > ethyl > butyl esters. Butyl esters showed reduced cloud points (-6 degrees C to -10 degrees C) and pour points (-13 degrees C to -16 degrees C) similar to those of summer diesel fuel having cloud and pour points of -8 degrees C and -15 degrees C, respectively. The viscosities of bio-diesels (3.3-7.6 x 10(-4) Pa s at 40 degrees C) were much less than those of pure oils (22.4-45.1 x 10(-4) Pa s at 40 degrees C) and were twice those of summer and winter diesel fuels (3.50 and 1.72 x 10(-4) Pa s at 40 degrees C), and their gross heat contents of approximately 40 MJ/kg were 11% less than those of diesel fuels (approximately 45 MJ/kg). For different esters from the same vegetable oil, methyl esters were the most volatile, and the volatility decreased as the alkyl group grew bulkier. However, the bio-diesels were considerably less volatile than the conventional diesel fuels.

  2. Partially esterified oligogalacturonides are the preferred substrates for pectin methylesterase of Aspergillus niger.

    PubMed

    van Alebeek, Gert-Jan W M; van Scherpenzeel, Katrien; Beldman, Gerrit; Schols, Henk A; Voragen, Alphons G J

    2003-05-15

    Investigations on the mode of action of Aspergillus niger pectin methylesterase (PME) towards differently C(6)- and C(1)-substituted oligogalacturonides (oligoGal p A) are described. De-esterification of methyl-esterified (un)saturated oligoGal p A proceeds via a specific pattern, depending on the degree of polymerization. Initially, a first methyl ester of the oligomer is hydrolysed, resulting in one free carboxyl group. Subsequently, this first product is preferred as a substrate and is de-esterified for a second time. This product is then accumulated and hereafter de-esterified further to the final product, i.e. oligoGal p A containing one methyl ester located at the non-reducing end residue for both saturated and unsaturated oligoGal p A, as found by post-source decay matrix-assisted laser-desorption/ionization-time-of-flight MS. The saturated hexamer is an exception to this: three methyl esters are removed very rapidly, instead of two methyl esters. When unsaturated oligoGal p A were used, the formation of the end product differed slightly, suggesting that the unsaturated bond at the non-reducing end influences the de-esterification process. In vivo, PME prefers methyl esters, but the enzyme appeared to be tolerant for other C(6)- and C(1)-substituents. Changing the type of ester (ethyl esterification) or addition of a methyl glycoside (C(1)) only reduced the activity or had no effect respectively. The specific product pattern was identical for all methyl- and ethyl-esterified oligoGal p A and methyl-glycosidated oligoGal p A, which strongly indicates that one or perhaps two non-esterified oligoGal p A are preferred in the active-site cleft.

  3. Partially esterified oligogalacturonides are the preferred substrates for pectin methylesterase of Aspergillus niger.

    PubMed Central

    van Alebeek, Gert-Jan W M; van Scherpenzeel, Katrien; Beldman, Gerrit; Schols, Henk A; Voragen, Alphons G J

    2003-01-01

    Investigations on the mode of action of Aspergillus niger pectin methylesterase (PME) towards differently C(6)- and C(1)-substituted oligogalacturonides (oligoGal p A) are described. De-esterification of methyl-esterified (un)saturated oligoGal p A proceeds via a specific pattern, depending on the degree of polymerization. Initially, a first methyl ester of the oligomer is hydrolysed, resulting in one free carboxyl group. Subsequently, this first product is preferred as a substrate and is de-esterified for a second time. This product is then accumulated and hereafter de-esterified further to the final product, i.e. oligoGal p A containing one methyl ester located at the non-reducing end residue for both saturated and unsaturated oligoGal p A, as found by post-source decay matrix-assisted laser-desorption/ionization-time-of-flight MS. The saturated hexamer is an exception to this: three methyl esters are removed very rapidly, instead of two methyl esters. When unsaturated oligoGal p A were used, the formation of the end product differed slightly, suggesting that the unsaturated bond at the non-reducing end influences the de-esterification process. In vivo, PME prefers methyl esters, but the enzyme appeared to be tolerant for other C(6)- and C(1)-substituents. Changing the type of ester (ethyl esterification) or addition of a methyl glycoside (C(1)) only reduced the activity or had no effect respectively. The specific product pattern was identical for all methyl- and ethyl-esterified oligoGal p A and methyl-glycosidated oligoGal p A, which strongly indicates that one or perhaps two non-esterified oligoGal p A are preferred in the active-site cleft. PMID:12589708

  4. Navy Coalescence Test on Petroleum F-76 Fuel with FAME Additive at 1%

    DTIC Science & Technology

    2012-06-20

    sponsored studies have shown that in many countries there is an undesirable concentration of Fatty Acid Methyl - Ester ( FAME ) present in the F-76. This...have shown that in many countries there may be an undesirable concentration of Fatty Acid Methyl - Ester ( FAME ) present in the F-76. This study was...Acid Methyl - Ester DEFINITIONS Turnover ..................amount of time it takes to flow the entire volume of fluid in a container, also

  5. 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

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false 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[2-methylbutanenitrile]- and 2,2'-(1,2-diazenediyl)bis[2-methylpropanenitrile]-initiated. 721.10326...

  6. A 13C NMR study of the structure of four cinnamic acids and their methyl esters

    NASA Astrophysics Data System (ADS)

    Silva, A. M. S.; Alkorta, I.; Elguero, J.; Silva, V. L. M.

    2001-09-01

    The 13C NMR spectra, both in DMSO solution and in the solid state of four cinnamic acids (p-methoxy, p-hydroxy, p-methyl, p-chloro) and their corresponding methyl esters have been recorded. The two main results in the solid state are: (i) the only significant difference between acids and esters chemical shifts concerns the Cdbnd O group which, on average, appears at 173 ppm in the acids and 168 ppm in the esters; (ii) the signals of the ortho and meta carbons both in the acids and the esters are splitted. The two 'anomalies' disappear in DMSO solution. These observations can be rationalized using simple GIAO/B3LYP/6-31G∗ calculations.

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

    PubMed

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

    2018-04-11

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

  8. Experimental studies on natural aspirated diesel engine fuelled with corn seed oil methyl ester as a bio-diesel.

    NASA Astrophysics Data System (ADS)

    Rama Krishna Reddy, E.; Dhana Raju, V.

    2018-03-01

    This paper evaluates the possibilities of using corn seed oil methyl ester as a fuel for compression ignition engines. The biodiesels are contained high oxygen content, and high Cetane number, due to this properties efficiency of biodiesel is higher than diesel fuel. The experiments were conducted with different biodiesel blends of (B10, B15, B20 and B25) corn seed oil on single cylinder four stroke natural aspirated diesel engines. Performance parameters and exhaust emissions are investigated in this experimental with the blends of the corn seed oil methyl ester and diesel fuel. The test results showed that the bio-diesel blends gives improved results for brake thermal efficiency and specific fuel consumption when compared with the diesel fuel. The emissions of corn seed methyl esters follow the same trend of diesel but the smoke opacity was reduces for all blends. From the investigation, corn seed methyl ester is also having the properties similar to diesel fuel; it is biodegradable and renewable fuel, so it will be used as an alternative for diesel fuel.

  9. A Lactobacillus plantarum Esterase Active on a Broad Range of Phenolic Esters

    PubMed Central

    Esteban-Torres, María; Landete, José María; Reverón, Inés; Santamaría, Laura; de las Rivas, Blanca

    2015-01-01

    Lactobacillus plantarum is the lactic acid bacterial species most frequently found in the fermentation of food products of plant origin on which phenolic compounds are abundant. L. plantarum strains showed great flexibility in their ability to adapt to different environments and growth substrates. Of 28 L. plantarum strains analyzed, only cultures from 7 strains were able to hydrolyze hydroxycinnamic esters, such as methyl ferulate or methyl caffeate. As revealed by PCR, only these seven strains possessed the est_1092 gene. When the est_1092 gene was introduced into L. plantarum WCFS1 or L. lactis MG1363, their cultures acquired the ability to degrade hydroxycinnamic esters. These results support the suggestion that Est_1092 is the enzyme responsible for the degradation of hydroxycinnamic esters on the L. plantarum strains analyzed. The Est_1092 protein was recombinantly produced and biochemically characterized. Surprisingly, Est_1092 was able to hydrolyze not only hydroxycinnamic esters, since all the phenolic esters assayed were hydrolyzed. Quantitative PCR experiments revealed that the expression of est_1092 was induced in the presence of methyl ferulate, an hydroxycinnamic ester, but was inhibited on methyl gallate, an hydroxybenzoic ester. As Est_1092 is an enzyme active on a broad range of phenolic esters, simultaneously possessing feruloyl esterase and tannase activities, its presence on some L. plantarum strains provides them with additional advantages to survive and grow on plant environments. PMID:25746986

  10. Corrosion-Related Consequences of Biodiesel in Contact with Natural Seawater

    DTIC Science & Technology

    2010-03-01

    petroleum diesel, biodiesel contains no sulfur. In the U.S. the term “biodiesel” is standardized as fatty acid methyl ester ( FAME ). Biodiesel content is...Form 298 (Rev. 8-98) Prescribed by ANSI Std Z39-18 to methyl (or ethyl) esters with a process known as transesterification.4 The transesterification...biodegradation of the vegetable methyl esters in agitated San Francisco Bay water was less than 4 days at 17 °C.4,22 The highest corrosion rates

  11. 40 CFR 721.10326 - 2-Propenoic acid, 2-methyl-, methyl ester, polymer with butyl 2-propenoate, ethyl 2-propenoate...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false 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), 2,2â²-(1,2-diazenediyl)bis[2-methylbutanenitrile]- and 2,2â²-(1,2-diazenediyl)bis[2-methylpropanenitrile]-initiated. 721.10326...

  12. 40 CFR 721.10326 - 2-Propenoic acid, 2-methyl-, methyl ester, polymer with butyl 2-propenoate, ethyl 2-propenoate...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false 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), 2,2â²-(1,2-diazenediyl)bis[2-methylbutanenitrile]- and 2,2â²-(1,2-diazenediyl)bis[2-methylpropanenitrile]-initiated. 721.10326...

  13. 40 CFR 156.206 - General statements.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... (i.e., an organophosphorus ester that inhibits cholinesterase) or an N-methyl carbamate (i.e., an N-methyl carbamic acid ester that inhibits cholinesterase), the label shall so state. The statement shall...

  14. 40 CFR 156.206 - General statements.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... (i.e., an organophosphorus ester that inhibits cholinesterase) or an N-methyl carbamate (i.e., an N-methyl carbamic acid ester that inhibits cholinesterase), the label shall so state. The statement shall...

  15. 40 CFR 156.206 - General statements.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... (i.e., an organophosphorus ester that inhibits cholinesterase) or an N-methyl carbamate (i.e., an N-methyl carbamic acid ester that inhibits cholinesterase), the label shall so state. The statement shall...

  16. 40 CFR 156.206 - General statements.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... (i.e., an organophosphorus ester that inhibits cholinesterase) or an N-methyl carbamate (i.e., an N-methyl carbamic acid ester that inhibits cholinesterase), the label shall so state. The statement shall...

  17. A Simple, Safe Method for Preparation of Biodiesel

    ERIC Educational Resources Information Center

    Behnia, Mahin S.; Emerson, David W.; Steinberg, Spencer M.; Alwis, Rasika M.; Duenas, Josue A.; Serafino, Jessica O.

    2011-01-01

    An experiment suitable for organic chemistry students is described. Biodiesel, a "green" fuel, consists of methyl or ethyl esters of long-chain fatty acids called FAMES (fatty acid methyl esters) or FAEES (fatty acid ethyl esters). A quick way to make FAMES is a base-catalyzed transesterification of oils or fats derived from plants or from animal…

  18. Density of Jatropha curcas Seed Oil and its Methyl Esters: Measurement and Estimations

    NASA Astrophysics Data System (ADS)

    Veny, Harumi; Baroutian, Saeid; Aroua, Mohamed Kheireddine; Hasan, Masitah; Raman, Abdul Aziz; Sulaiman, Nik Meriam Nik

    2009-04-01

    Density data as a function of temperature have been measured for Jatropha curcas seed oil, as well as biodiesel jatropha methyl esters at temperatures from above their melting points to 90 ° C. The data obtained were used to validate the method proposed by Spencer and Danner using a modified Rackett equation. The experimental and estimated density values using the modified Rackett equation gave almost identical values with average absolute percent deviations less than 0.03% for the jatropha oil and 0.04% for the jatropha methyl esters. The Janarthanan empirical equation was also employed to predict jatropha biodiesel densities. This equation performed equally well with average absolute percent deviations within 0.05%. Two simple linear equations for densities of jatropha oil and its methyl esters are also proposed in this study.

  19. Application of ethyl esters and d3-methyl esters as internal standards for the gas chromatographic quantification of transesterified fatty acid methyl esters in food.

    PubMed

    Thurnhofer, Saskia; Vetter, Walter

    2006-05-03

    Ethyl esters (FAEE) and trideuterium-labeled methyl esters (d3-FAME) of fatty acids were prepared and investigated regarding their suitability as internal standards (IS) for the determination of fatty acids as methyl esters (FAME). On CP-Sil 88, ethyl esters of odd-numbered fatty acids eluted approximately 0.5 min after the respective FAME, and only coelutions with minor FAME were observed. Depending on the problem, one or even many FAEE can be added as IS for the quantification of FAME by both GC-FID and GC-MS. By contrast, d3-FAME coeluted with FAME on the polar GC column, and the use of the former as IS requires application of GC-MS. In the SIM mode, m/z 77 and 90 are suggested for d3-methyl esters of saturated fatty acids, whereas m/z 88 and 101 are recommended for ethyl esters of saturated fatty acids. These m/z values give either no or very low response for FAME and can thus be used for the analysis of FAME in food by GC-MS in the SIM mode. Fatty acids in sunflower oil and mozzarella cheese were quantified using five saturated FAEE as IS. Gravimetric studies showed that the transesterification procedure could be carried out without of loss of fatty acids. GC-EI/MS full scan analysis was suitable for the quantitative determination of all unsaturated fatty acids in both food samples, whereas GC-EI/MS in the SIM mode was particularly valuable for quantifying minor fatty acids. The novel GC-EI/MS/SIM method using fatty acid ethyl esters as internal standards can be used to quantify individual fatty acids only, that is, without determination of all fatty acids (the common 100% method), although this is present. This was demonstrated by the exclusive quantification of selected fatty acids including methyl-branched fatty acids, erucic acid (18:1n-9trans), and polyunsaturated fatty acids in cod liver oil and goat's milk fat.

  20. A Lactobacillus plantarum esterase active on a broad range of phenolic esters.

    PubMed

    Esteban-Torres, María; Landete, José María; Reverón, Inés; Santamaría, Laura; de las Rivas, Blanca; Muñoz, Rosario

    2015-05-01

    Lactobacillus plantarum is the lactic acid bacterial species most frequently found in the fermentation of food products of plant origin on which phenolic compounds are abundant. L. plantarum strains showed great flexibility in their ability to adapt to different environments and growth substrates. Of 28 L. plantarum strains analyzed, only cultures from 7 strains were able to hydrolyze hydroxycinnamic esters, such as methyl ferulate or methyl caffeate. As revealed by PCR, only these seven strains possessed the est_1092 gene. When the est_1092 gene was introduced into L. plantarum WCFS1 or L. lactis MG1363, their cultures acquired the ability to degrade hydroxycinnamic esters. These results support the suggestion that Est_1092 is the enzyme responsible for the degradation of hydroxycinnamic esters on the L. plantarum strains analyzed. The Est_1092 protein was recombinantly produced and biochemically characterized. Surprisingly, Est_1092 was able to hydrolyze not only hydroxycinnamic esters, since all the phenolic esters assayed were hydrolyzed. Quantitative PCR experiments revealed that the expression of est_1092 was induced in the presence of methyl ferulate, an hydroxycinnamic ester, but was inhibited on methyl gallate, an hydroxybenzoic ester. As Est_1092 is an enzyme active on a broad range of phenolic esters, simultaneously possessing feruloyl esterase and tannase activities, its presence on some L. plantarum strains provides them with additional advantages to survive and grow on plant environments. Copyright © 2015, American Society for Microbiology. All Rights Reserved.

  1. Effect of reaction temperature on biodiesel production from waste cooking oil using lipase as biocatalyst

    NASA Astrophysics Data System (ADS)

    Istiningrum, Reni Banowati; Aprianto, Toni; Pamungkas, Febria Lutfi Udin

    2017-12-01

    This study aims to determine the effect of temperature on conversion of biodiesel from waste cooking oil enzymatically using lipase extracted from rice bran. The feedstock was simulated waste cooking oil and lipase enzyme was extracted with buffer pH variation. The enzyme activity was titrimetrically determined and the optimum pH buffer was used to study the effect of temperature on the transesterification reaction. Temperature effects were assessed in the range of 45-60 °C and the content of methyl esters in biodiesel was determined by GC-MS. The reaction temperature significantly influences the transesterification reaction with optimum biodiesel conversion occurred at 55 °C with methyl ester content of 81.19%. The methyl ester composition in the resulting biodiesel is methyl palmitate, methyl oleate and methyl stearate.

  2. Temperature-enhanced alumina HPLC method for the analysis of wax esters, sterol esters, and methyl esters.

    PubMed

    Moreau, Robert A; Kohout, Karen; Singh, Vijay

    2002-12-01

    Previous attempts at separating nonpolar lipid esters (including wax esters, sterol esters, and methyl esters) have achieved only limited success. Among the several normal-phase methods tested, a single recent report of a method employing an alumina column at 30 degrees C with a binary gradient system was the most promising. In the current study, modification of the alumina method by increasing the column temperature to 75 degrees C improved the separation of standards of wax esters and sterol esters. Elevated column temperature also enhanced the separation of FAME with differing degrees of unsaturation. Evidence was also presented to indicate that the method similarly separated phytosterol esters, based on their levels of unsaturation. With the increased interest in phytosterol- and phytostanol-ester enriched functional foods, this method should provide a technique to characterize and compare these products.

  3. Technology advances & new applications for biodiesel

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    Holmberg, B.

    1994-12-31

    Biodiesel, as the term is used in the United States, is a blend of methyl and/or ethyl esters with petrodiesel. The esters are biodegradable, non-toxic and essentially free of sulfur or aromatic compounds. The blend level is a function of economics, the desired emissions profile, material compatibility, and combustion characteristics. The focus at the moment is on a 20 vol% blend of a methyl ester (methyl soyate) in petrodiesel (known as B20). The name {open_quotes}biodiesel{close_quotes} was introduced by the National SoyDiesel Development Board (now the National Biodiesel Board), which has pioneered the commercialization of biodiesel in the United States. Themore » American Biofuels Association (ABA) and Information Resources Inc. (IRI) have, in the past, been part of their support team. Methyl or ethyl esters are made from vegetable and tree oils, animal fats, and used oils and fats. These oils are blended with an alcohol (usually methanol, although ethanol can be used as well) and a catalyst such as sodium hydroxide. The resulting chemical reaction (which occurs at moderate temperatures and pressures) produces a methyl or ethyl ester and glycerine, a valuable material used extensively in the manufacture of soaps and other consumer products.« less

  4. Practical method for the confirmation of authentic flours of different types of cereals and pseudocereals.

    PubMed

    Ačanski, Marijana M; Vujić, Djura N; Psodorov, Djordje B

    2015-04-01

    Gas chromatography with mass spectrometry was used to perform a qualitative analysis of the liposoluble flour extract of different types of cereals (bread wheat and spelt) and pseudocereals (amaranth and buckwheat). In addition to major fatty acids, the liposoluble extract also contained minor fatty acids with more than 20 carbon atoms, higher hydrocarbons and phytosterols. TMSH (trimethylsulfonium hydroxide, 0.2 mol/l in methanol) was used as a trans-esterification reagent. In a trans-esterification reaction, triglycerides esterified from acilglycerols to methyl-esters. SIM (selected ion monitoring) was applied to isolate fatty acid methyl esters on TIC (total ion current) chromatograms, using the 74 Da fragment ion, which originated from McLafferty rearrangement, and is typical for methyl-esters. GC-MS system was used for the trans-esterification of triglycerides to fatty acid methyl esters in the gas chromatographic injector. This eliminated laboratory preparation for fatty acid methyl esters. Cluster analysis was applied to compare the liposoluble flour extract from different types of cereals and pseudocereals. Statistical data showed the liposoluble extract analysis enabled determination of flour origin and, because the results were unambiguous, this approach could be used for quality control. Copyright © 2014 Elsevier Ltd. All rights reserved.

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

    PubMed

    Takakuwa, Naoya; Saito, Katsuichi

    2010-01-01

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

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

    PubMed

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

    2004-01-19

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

  7. DOE Office of Scientific and Technical Information (OSTI.GOV)

    S.I. Zherebtsov; A.I. Moiseev

    Changes in the group and individual compositions of the wax fractions of bitumen in the course of brown coal methylation were studied. With the use of IR and NMR spectroscopy and chromatography-mass spectrometry, it was found that the esters of methylated coal waxes consisted of the native esters of fatty acids and the methyl esters of these acids formed as a result of an alkylation treatment. Esterification and transesterification were predominant among the reactions of aliphatic fraction components. A positive effect of methanol alkylation on an increase in the yield of the aliphatic fractions was found.

  8. Preparation and Evaluation of Jojoba Oil Methyl Ester as Biodiesel and as Blend Components in Ultra Low Sulfur Diesel Fuel

    USDA-ARS?s Scientific Manuscript database

    The jojoba plant (Simmondsia chinensis L.) produces seeds that contain around 50 to 60 weight percent of inedible long-chain wax esters that are suitable as a potential feedstock for biodiesel production. A Jojoba oil methyl ester (JME) was prepared in effort to evaluate an important fuel propertie...

  9. 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) The...

  10. Gas Chromatography-Mass Spectrometry Analysis of Constituent Oil from Lingzhi or Reishi Medicinal Mushroom, Ganoderma lucidum (Agaricomycetes), from Nigeria.

    PubMed

    Ohiri, Reginald Chibueze; Bassey, Essien Eka

    2016-01-01

    Gas chromatography-mass spectrometry analysis of constituent oil from dried Ganoderma lucidum was carried out. Fresh G. lucidum obtained from its natural environment was thoroughly washed with distilled water and air-dried for 2 weeks and the component oils were extracted and analyzed. Four predominant components identified were pentadecanoic acid, 14-methyl-ester (retention time [RT] = 19.752 minutes; percentage total = 25.489), 9,12-octadecadienoic acid (Z,Z)- (RT = 21.629 minutes and 21.663 minutes; percentage total = 25.054), n-hexadecanoic acid (RT = 20.153 minutes; percentage total = 24.275), and 9-octadecenoic acid (Z)-, methyl ester (RT = 21.297 minutes; percentage total = 13.027). The two minor oils identified were 9,12-octadecadienoic acid, methyl ester, (E,E)- and octadecanoic acid, methyl ester (RT = 21.246 minutes and 21.503 minutes; percentage total = 7.057 and 5.097, respectively).

  11. 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. © 2013 The Society for Applied Microbiology.

  12. Processing Of Neem And Jatropha Methyl Esters -Alternative Fuels From Vegetable Oil

    NASA Astrophysics Data System (ADS)

    Ramasubramanian, S.; Manavalan, S.; Gnanavel, C.; Balakrishnan, G.

    2017-03-01

    Biodiesel is an alternative fuel for diesel engine. The methyl esters of vegetable oils, known as biodiesel are becoming increasingly popular because of their low environmental impact and potential as a green alternative fuel for diesel engine. This paper deals with the manufacturing process of Biodiesel from jatropha and neem oil. Biodiesel was prepared from neem oil and jatropha oil, the transestrified having kinematic viscosity of 3 & 2.6 centistokes, methanol ratio is 6:1 & 5.1respectively. The secondary solution is preheated at 65 C & 60 C and reaction temperature is maintained at 60C & 55 C and reaction time is 60 minutes approximately with NaOH catalyst and low viscosity oil is allowed to settle 24 hours. The average yield of neem and jatropha methyl esters was about 85%. These methyl esters shows excellent alternative under optimum condition for fossil fuels.

  13. Hydrogen bond docking site competition in methyl esters

    NASA Astrophysics Data System (ADS)

    Zhao, Hailiang; Tang, Shanshan; Du, Lin

    2017-06-01

    The Osbnd H ⋯ O hydrogen bonds in the 2,2,2-trifluoroethanol (TFE)-methyl ester complexes in the gas phase have been investigated by FTIR spectroscopy and DFT calculations. Methyl formate (MF), methyl acetate (MA), and methyl trifluoroacetate (MTFA) were chosen as the hydrogen bond acceptors. A dominant inter-molecular hydrogen bond was formed between the OH group of TFE and different docking sites in the methyl esters (carbonyl oxygen or ester oxygen). The competition of the two docking sites decides the structure and spectral properties of the complexes. On the basis of the observed red shifts of the OH-stretching transition with respect to the TFE monomer, the order of the hydrogen bond strength can be sorted as TFE-MA (119 cm- 1) > TFE-MF (93 cm- 1) > TFE-MTFA (44 cm- 1). Combining the experimental infrared spectra with the DFT calculations, the Gibbs free energies of formation were determined to be 1.5, 4.5 and 8.6 kJ mol- 1 for TFE-MA, TFE-MF and TFE-MTFA, respectively. The hydrogen bonding in the MTFA complex is much weaker than those of the TFE-MA and TFE-MF complexes due to the effect of the CF3 substitution on MTFA, while the replacement of an H atom with a CH3 group in methyl ester only slightly increases the hydrogen bond strength. Topological analysis and localized molecular orbital energy decomposition analysis was also applied to compare the interactions in the complexes.

  14. Zeolite/magnetite composites as catalysts on the Synthesis of Methyl Esters (MES) from cooking oil

    NASA Astrophysics Data System (ADS)

    Sriatun; Darmawan, Adi; Sriyanti; Cahyani, Wuri; Widyandari, Hendri

    2018-05-01

    The using of zeolite/magnetite composite as a catalyst for the synthesis of methyl esters (MES) of cooking oil has been performed. In this study the natural magnetite was extracted from the iron sand of Semarang marina beach and milled by high energy Milling (HEM) with ball: magnetite ratio: 1:1. The composites prepared from natural zeolite and natural magnetite with zeolite: magnetite ratio 1:1; 2:1; 3:1 and 4:1. Preparation of methyl ester was catalyzed by composite of zeolite/magnetite through transeserification reaction, it was studied on variation of catalyst concentration (w/v) 1%, 3%, 5% and 10% to feed volume. The reaction product are mixture of methyl Oleic (MES), methyl Palmitic (MES) and methyl Stearic (MES). Character product of this research include density, viscosity, acid number and iodine number has fulfilled to SNI standard 7182: 2015.

  15. Single-Walled Carbon Nanotubes Targeted to the Tumor Vasculature for Breast Cancer Treatment

    DTIC Science & Technology

    2009-09-01

    using 1 -ethyl- 3 -[ dimethylaminopropyl ]carbodiimide hydrochloride (EDC). The binding of SWNT-annexin V to PS will be measured using PS immobilized on...ADDRESS. 1 . REPORT DATE (DD-MM-YYYY) -09-200 2. REPORT TYPE Final 3 . DATES COVERED (From - To) 16 Aug 2007 – 15 Aug 2009 4. TITLE AND SUBTITLE...Conjugation of Annexin V to SWNTs Using the Linker Fluorenylmethoxycarbonyl (Fmoc)-amine-PEG-succinimidyl Carboxy Methyl Ester 1 . Add 3 mg of SWNTs to 7

  16. Glucuronoyl esterase--novel carbohydrate esterase produced by Schizophyllum commune.

    PubMed

    Spániková, Silvia; Biely, Peter

    2006-08-21

    The cellulolytic system of the wood-rotting fungus Schizophyllum commune contains an esterase that hydrolyzes methyl ester of 4-O-methyl-d-glucuronic acid. The enzyme, called glucuronoyl esterase, was purified to electrophoretic homogeneity from a cellulose-spent culture fluid. Its substrate specificity was examined on a number of substrates of other carbohydrate esterases such as acetylxylan esterase, feruloyl esterase and pectin methylesterase. The glucuronoyl esterase attacks exclusively the esters of MeGlcA. The methyl ester of free or glycosidically linked MeGlcA was not hydrolysed by other carbohydrate esterases. The results suggest that we have discovered a new type of carbohydrate esterase that might be involved in disruption of ester linkages connecting hemicellulose and lignin in plant cell walls.

  17. Kapok oil methyl esters

    USDA-ARS?s Scientific Manuscript database

    The increased need for biodiesel feedstocks has caused various vegetable oils to be examined for this purpose. In the present work, the methyl esters of kapok (Ceiba pentandra) oil were prepared. The essential fuel properties were comprehensively determined and evaluated in comparison to specificati...

  18. Kenaf methyl esters

    USDA-ARS?s Scientific Manuscript database

    Additional or alternative feedstocks are one of the major areas of interest regarding biodiesel. In this paper, for the first time, the fuel properties of kenaf (Hibiscus cannabinus L.) seed oil methyl esters are comprehensively reported. This biodiesel is also relatively unique by containing small ...

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

    PubMed

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

    2012-01-01

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

  20. Computer-aided rational design of novel EBF analogues with an aromatic ring.

    PubMed

    Wang, Shanshan; Sun, Yufeng; Du, Shaoqing; Qin, Yaoguo; Duan, Hongxia; Yang, Xinling

    2016-06-01

    Odorant binding proteins (OBPs) are important in insect olfactory recognition. These proteins bind specifically to insect semiochemicals and induce their seeking, mating, and alarm behaviors. Molecular docking and molecular dynamics simulations were performed to provide computational insight into the interaction mode between AgamOBP7 and novel (E)-β-farnesene (EBF) analogues with an aromatic ring. The ligand-binding cavity in OBP7 was found to be mostly hydrophobic due to the presence of several nonpolar residues. The interactions between the EBF analogues and the hydrophobic residues in the binding cavity increased in strength as the distance between them decreased. The EBF analogues with an N-methyl formamide or ester linkage had higher docking scores than those with an amide linkage. Moreover, delocalized π-π and electrostatic interactions were found to contribute significantly to the binding between the ligand benzene ring and nearby protein residues. To design new compounds with higher activity, four EBF analogues D1-D4 with a benzene ring were synthesized and evaluated based on their docking scores and binding affinities. D2, which had an N-methyl formamide group linkage, exhibited stronger binding than D1, which had an amide linkage. D4 exhibited particularly strong binding due to multiple hydrophobic interactions with the protein. This study provides crucial foundations for designing novel EBF analogues based on the OBP structure. Graphical abstract The design strategy of new EBF analogues based on the OBP7 structure.

  1. VvMJE1 of the grapevine (Vitis vinifera) VvMES methylesterase family encodes for methyl jasmonate esterase and has a role in stress response

    USDA-ARS?s Scientific Manuscript database

    The known members of the plant methyl esterase (MES) family catalyze hydrolysis of a C-O ester linkage of methyl esters of several phytohormones including indole-3-acetic acid, salicylic acid, and jasmonic acid. The genome of grapevine (Vitis vinifera) was found to contain 15 MES genes, designated V...

  2. Site-directed decapsulation of bolaamphiphilic vesicles with enzymatic cleavable surface groups.

    PubMed

    Popov, Mary; Grinberg, Sarina; Linder, Charles; Waner, Tal; Levi-Hevroni, Bosmat; Deckelbaum, Richard J; Heldman, Eliahu

    2012-06-10

    Stable nano-sized vesicles with a monolayer encapsulating membrane were prepared from novel bolaamphiphiles with choline ester head groups. The head groups were covalently bound to the alkyl chain of the bolaamphiphiles either via the nitrogen atom of the choline moiety, or via the choline ester's methyl group. Both types of bolaamphiphiles competed with acetylthiocholine for binding to acetylcholine esterase (AChE), yet, only the choline ester head groups bound to the alkyl chain via the nitrogen atom of the choline moiety were hydrolyzed by the enzyme. Likewise, only vesicles composed of bolaamphiphiles with head groups that were hydrolyzed by AChE released their encapsulated material upon exposure to the enzyme. Injection of carboxyfluorescein (CF)-loaded vesicles with cleavable choline ester head groups into mice resulted in the accumulation of CF in tissues that express high AChE activity, including the brain. By comparison, when vesicles with choline ester head groups that are not hydrolyzed by AChE were injected into mice, there was no accumulation of CF in tissues that highly express the enzyme. These results imply that bolaamphiphilic vesicles with surface groups that are substrates to enzymes which are highly expressed in target organs may potentially be used as a drug delivery system with controlled site-directed drug release. Copyright © 2011 Elsevier B.V. All rights reserved.

  3. New bis(alkythio) fatty acid methyl esters

    USDA-ARS?s Scientific Manuscript database

    The addition reaction of dimethyl disulfide (DMDS) to mono-unsaturated fatty acid methyl esters is well-known for analytical purposes to determine the position of double bonds by mass spectrometry. In this work, the classical iodine-catalyzed reaction is expanded to other dialkyl disulfides (RSSR), ...

  4. Oxygenated N-Acyl Alanine Methyl Esters (NAMEs) from the Marine Bacterium Roseovarius tolerans EL-164.

    PubMed

    Bruns, Hilke; Herrmann, Jennifer; Müller, Rolf; Wang, Hui; Wagner Döbler, Irene; Schulz, Stefan

    2018-01-26

    The marine bacterium Roseovarius tolerans EL-164 (Rhodobacteraceae) can produce unique N-acylalanine methyl esters (NAMEs) besides strucutrally related N-acylhomoserine lactones (AHLs), bacterial signaling compounds widespread in the Rhodobacteraceae. The structures of two unprecedented NAMEs carrying a rare terminally oxidized acyl chain are reported here. The compounds (Z)-N-16-hydroxyhexadec-9-enoyl-l-alanine methyl ester (Z9-16-OH-C16:1-NAME, 3) and (Z)-N-15-carboxypentadec-9-enoyl-l-alanine methyl ester (16COOH-C16:1-NAME, 4) were isolated, and the structures were determined by NMR and MS experiments. Both compounds were synthesized to prove assignments and to test their biological activity. Finally, non-natural, structurally related Z9-3-OH-C16:1-NAME (18) was synthesized to investigate the mass spectroscopy of structurally related NAMEs. Compound 3 showed moderate antibacterial activity against microorganisms such as Bacillus, Streptococcus, Micrococcus, or Mucor strains. In contrast to AHLs, quorum-sensing or quorum-quenching activity was not observed.

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

    PubMed

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

    2013-02-01

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

  6. Analysis of biodiesel by high performance liquid chromatography using refractive index detector.

    PubMed

    Syed, Mahin Basha

    2017-01-01

    High-performance liquid chromatography (HPLC) was used for the determination of compounds occurring during the production of biodiesel from karanja and jatropha oil. Methanol was used for fast monitoring of conversion of karanja and jatropha oil triacylglycerols to fatty acid methyl esters and for quantitation of residual triacylglycerols (TGs), in the final biodiesel product. The individual sample compounds were identified using HPLC. Analysis of fatty acid methyl esters (FAMES) in blends of biodiesel by HPLC using a refractive index and a UV detector at 238 nm. Individual triacylglycerols, diacylglycerols, monoacylglycerols and methyl esters of oleic, linoleic and linolenic acids and free fatty acids were separated within 40 min. Hence HPLC was found to be best for the analysis of biodiesel. Analysis of biodiesel by HPLC using RID detector. Estimation of amount of FAMES in biodiesel. Individual triacylglycerols, diacylglycerols, monoacylglycerols and methyl esters of oleic, linoleic and linolenic acids and free fatty acids were separated within 40 min.

  7. Preparation and Evaluation at the Delta Opioid Receptor of a Series of Linear Leu-Enkephalin Analogues Obtained by Systematic Replacement of the Amides

    PubMed Central

    2013-01-01

    Leu-enkephalin analogues, in which the amide bonds were sequentially and systematically replaced either by ester or N-methyl amide bonds, were prepared using classical organic chemistry as well as solid phase peptide synthesis (SPPS). The peptidomimetics were characterized using competition binding, ERK1/2 phosphorylation, receptor internalization, and contractility assays to evaluate their pharmacological profile over the delta opioid receptor (DOPr). The lipophilicity (LogD7.4) and plasma stability of the active analogues were also measured. Our results revealed that the last amide bond can be successfully replaced by either an ester or an N-methyl amide bond without significantly decreasing the biological activity of the corresponding analogues when compared to Leu-enkephalin. The peptidomimetics with an N-methyl amide function between residues Phe and Leu were found to be more lipophilic and more stable than Leu-enkephalin. Findings from the present study further revealed that the hydrogen-bond donor properties of the fourth amide of Leu-enkephalin are not important for its biological activity on DOPr. Our results show that the systematic replacement of amide bonds by isosteric functions represents an efficient way to design and synthesize novel peptide analogues with enhanced stability. Our findings further suggest that such a strategy can also be useful to study the biological roles of amide bonds. PMID:23650868

  8. Efficient and scalable synthesis of bardoxolone methyl (cddo-methyl ester).

    PubMed

    Fu, Liangfeng; Gribble, Gordon W

    2013-04-05

    Bardoxolone methyl (2-cyano-3,12-dioxooleane-1,9(11)-dien-28-oic acid methyl ester; CDDO-Me) (1), a synthetic oleanane triterpenoid with highly potent anti-inflammatory activity (levels below 1 nM), has completed a successful phase I clinical trial for the treatment of cancer and a successful phase II trial for the treatment of chronic kidney disease in type 2 diabetes patients. Our synthesis of bardoxolone methyl (1) proceeds in ∼50% overall yield in five steps from oleanolic acid (2), requires only one to two chromatographic purifications, and can provide gram quantities of 1.

  9. 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

    ... 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 30 2010-07-01 2010-07-01 false Benzoic acid, 3,3â²-methyl-enebis [6...

  10. 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

    ... 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 2011-07-01 2011-07-01 false Benzoic acid, 3,3â²-methyl-enebis [6...

  11. Methyl esters (biodiesel) from Pachyrhizus erosus seed oil

    USDA-ARS?s Scientific Manuscript database

    The search for additional or alternative feedstocks is one of the major areas of interest regarding biodiesel. In this paper, the fuel properties of Pachyrhizus erosus (commonly known as yam bean or Mexican potato or jicama) seed oil methyl esters were investigated by methods prescribed in biodiesel...

  12. A simple and sensitive fluorescent sensor for methyl parathion based on L-tyrosine methyl ester functionalized carbon dots.

    PubMed

    Hou, Juying; Dong, Jing; Zhu, Haishuang; Teng, Xue; Ai, Shiyun; Mang, Minglin

    2015-06-15

    In this paper, a simple and sensitive fluorescent sensor for methyl parathion is developed based on L-tyrosine methyl ester functionalized carbon dots (Tyr-CDs) and tyrosinase system. The carbon dots are obtained by simple hydrothermal reaction using citric acid as carbon resource and L-tyrosine methyl ester as modification reagent. The carbon dots are characterized by transmission electron microscope, high resolution transmission electron microscopy, X-ray diffraction spectrum, Fourier transform infrared spectroscopy, and X-ray photoelectron spectroscopy. The carbon dots show strong and stable photoluminescence with a quantum yield of 3.8%. Tyrosinase can catalyze the oxidation of tyrosine methyl ester on the surface of carbon dots to corresponding quinone products, which can quench the fluorescence of carbon dots. When organophosphorus pesticides (OPs) are introduced in system, they can decrease the enzyme activity, thus decrease the fluorescence quenching rate. Methyl parathion, as a model of OPs, was detected. Experimental results show that the enzyme inhibition rate is proportional to the logarithm of the methyl parathion concentration in the range 1.0×10(-10)-1.0×10(-4) M with the detection limit (S/N=3) of 4.8×10(-11) M. This determination method shows a low detection limit, wide linear range, good selectivity and high reproducibility. This sensing system has been successfully used for the analysis of cabbage, milk and fruit juice samples. Copyright © 2014 Elsevier B.V. All rights reserved.

  13. Progesterone up-regulates vasodilator effects of calcitonin gene-related peptide in N(G)-nitro-L-arginine methyl ester-induced hypertension.

    PubMed

    Gangula, P R; Wimalawansa, S J; Yallampalli, C

    1997-04-01

    We recently reported that calcitonin gene-related peptide can reverse the hypertension produced by N(G)-nitro-L-arginine methyl ester in pregnant rats. In the current study we investigated whether these vasodilator effects of calcitonin gene-related peptide were progesterone dependent. Calcitonin gene-related peptide or N(G)-nitro-L-arginine methyl ester was infused through osmotic minipumps, either separately or in combination, to groups of five pregnant rats from day 17 of gestation until day 8 post partum or to nonpregnant ovariectomized rats for 8 days. Progesterone was injected during days 1 to 6 post partum and for 6 days after ovariectomy. Systolic blood pressure was measured daily. Animals receiving N(G)-nitro-L-arginine methyl ester exhibited significant elevations of blood pressure during pregnancy and post partum. Coadministration of calcitonin gene-related peptide to these rats reversed the hypertension during pregnancy but not during the postpartum period. At the dose used in this study calcitonin gene-related peptide administered alone was without significant effects on blood pressure. However, it reduced both the mortality and growth restriction of the fetus associated with N(G)-nitro-L-arginine methyl ester in these animals. Calcitonin gene-related peptide reversed the hypertension in N(G)-nitro-L-arginine methyl ester-infused postpartum rats during the periods of progesterone treatment only, and these effects were lost when progesterone treatment was stopped. Neither progesterone nor calcitonin gene-related peptide alone were effective. To further confirm these observations, progesterone effects were tested in ovariectomized adult rats. Similar to the findings in postpartum rats, calcitonin gene-related peptide completely reversed the elevation in blood pressure in N(G)-nitro-L-arginine methyl ester-treated rats receiving progesterone injections. The effects of calcitonin gene-related peptide were apparent only during the progesterone treatment period, and these effects were lost when progesterone treatment was stopped. Again, at these doses calcitonin gene-related peptide and progesterone were each ineffective alone. Calcitonin gene-related peptide reverses the N(G)-nitro-L-arginine methyl ester-induced hypertension during pregnancy, when progesterone levels are elevated, but not post partum or in ovariectomized nonpregnant rats. The blood pressure-lowering effects of calcitonin gene-related peptide were restored in both postpartum and ovariectomized rats with progesterone treatment. Therefore we conclude that progesterone modulates vasodilator effects of calcitonin gene-related peptide in hypertensive rats.

  14. Electrode Potentials of l-Tryptophan, l-Tyrosine, 3-Nitro-l-tyrosine, 2,3-Difluoro-l-tyrosine, and 2,3,5-Trifluoro-l-tyrosine.

    PubMed

    Mahmoudi, Leila; Kissner, Reinhard; Nauser, Thomas; Koppenol, Willem H

    2016-05-24

    Electrode potentials for aromatic amino acid radical/amino acid couples were deduced from cyclic voltammograms and pulse radiolysis experiments. The amino acids investigated were l-tryptophan, l-tyrosine, N-acetyl-l-tyrosine methyl ester, N-acetyl-3-nitro-l-tyrosine ethyl ester, N-acetyl-2,3-difluoro-l-tyrosine methyl ester, and N-acetyl-2,3,5-trifluoro-l-tyrosine methyl ester. Conditional potentials were determined at pH 7.4 for all compounds listed; furthermore, Pourbaix diagrams for l-tryptophan, l-tyrosine, and N-acetyl-3-nitro-l-tyrosine ethyl ester were obtained. Electron transfer accompanied by proton transfer is reversible, as confirmed by detailed analysis of the current waves, and because the slopes of the Pourbaix diagrams obey Nernst's law. E°'(Trp(•),H(+)/TrpH) and E°'(TyrO(•),H(+)/TyrOH) at pH 7 are 0.99 ± 0.01 and 0.97 ± 0.01 V, respectively. Pulse radiolysis studies of two dipeptides that contain both amino acids indicate a difference in E°' of approximately 0.06 V. Thus, in small peptides, we recommend values of 1.00 and 0.96 V for E°'(Trp(•),H(+)/TrpH) and E°'(TyrO(•),H(+)/TyrOH), respectively. The electrode potential of N-acetyl-3-nitro-l-tyrosine ethyl ester is higher, while because of mesomeric stabilization of the radical, those of N-acetyl-2,3-difluoro-l-tyrosine methyl ester and N-acetyl-2,3,5-trifluoro-l-tyrosine methyl ester are lower than that of tyrosine. Given that the electrode potentials at pH 7 of E°'(Trp(•),H(+)/TrpH) and E°'(TyrO(•),H(+)/TyrOH) are nearly equal, they would be, in principle, interchangeable. Proton-coupled electron transfer pathways in proteins that use TrpH and TyrOH are thus nearly thermoneutral.

  15. Bifunctional heterogeneous catalysts from oil palm empty fruit bunches ash and alum for biodiesel synthesis simultaneously

    NASA Astrophysics Data System (ADS)

    Astar, Ismail; Usman, Thamrin; Wahyuni, Nelly; Rudiyansyah, Alimuddin, Andi Hairil

    2017-03-01

    Free fatty acids (FFA) contained in crude palm oil (CPO) and sludge oil has been used as the base material of biodiesel with the aid of a catalyst in the transesterification and esterification reactions. This study aims to synthesize and characterize bifunctional catalysts were synthesized from the ashes of palm empty fruit bunches (EFB) and alum based on the analysis of XRD, XRF and acidity test. Bifunctional catalyst obtained was used as a catalyst to production of biodiesel with different levels of FFA. The optimum ratio alum added was 0.2 mol at 3 hours of reaction time and 3% of catalyst by the FFA samples were used 67,40%. The catalyst with optimum alum mole variations subsequently used on samples with varying levels of FFA, namely 1.29%, 4.98%, 29.21%, 67.40% and 74.47%. Optimum conversion of methyl ester in the esterification reaction occurs in the sample with 67.40% FFA content, which reached 86.17%, while the conversion of methyl ester transesterification process optimum amounted to 45.70% in the samples with 4.98% FFA content. Methyl ester produced has a refractive index of 1.448 (29.8 ° C), density of 0.883 g / mL (25 °C) and a viscosity of 8.933 cSt (25 ° C). The results of GC-MS analysis showed that the main composition of methyl ester result of esterification of sludge oil methyl palmitate (36.84%), while the CPO transesterification shows the main composition of methyl ester is methyl oleic (38.87%). Based on the research results, the catalyst synthesized from alum and EFB ash can be used as a Bifunctional catalysts for biodiesel synthesis.

  16. Photoelectron spectroscopy of a series of acetate and propionate esters

    NASA Astrophysics Data System (ADS)

    Śmiałek, Małgorzata A.; Guthmuller, Julien; MacDonald, Michael A.; Zuin, Lucia; Delwiche, Jacques; Hubin-Franskin, Marie-Jeanne; Lesniewski, Tadeusz; Mason, Nigel J.; Limão-Vieira, Paulo

    2017-10-01

    The electronic state and photoionization spectroscopy of a series of acetate esters: methyl acetate, isopropyl acetate, butyl acetate and pentyl acetate as well as two propionates: methyl propionate and ethyl propionate, have been determined using vacuum-ultraviolet photoelectron spectroscopy. These experimental investigations are complemented by ab initio calculations. The measured first adiabatic and vertical ionization energies were determined as: 10.21 and 10.45 eV for methyl acetate, 9.99 and 10.22 eV for isopropyl acetate, 10.07 and 10.26 eV for butyl acetate, 10.01 and 10.22 eV for pentyl acetate, 10.16 and 10.36 eV for methyl propionate and 9.99 and 10.18 eV for ethyl propionate. For the four smaller esters vibrational transitions were calculated and compared with those identified in the photoelectron spectrum, revealing the most distinctive ones to be a Csbnd O stretch combined with a Cdbnd O stretch. The ionization energies of methyl and ethyl esters as well as for a series of formates and acetates were compared showing a clear dependence of the value of the ionization energy on the size of the molecule with very little influence of its conformation.

  17. Proton-Ionizable Crown Ethers. A Short Review

    DTIC Science & Technology

    1989-05-30

    acid methyl ester using sodium hydride as the base in tetrahydrofuran. The m3thyl ester group was hydrolyzed to the carboxylic acid as shown in Procedure...prepared via the appropriate hydroxydibenzo-crown ether and allyl bromide RýIý R2 or ethyl acrylate as shown in Procedure N. 5 2 . 5 6 Disulfonic acid ...similar to Procedure p. 7 4 Once the precursor binrephtho-crown was obtained, it was coupled with bromoacetic acid methyl ester and R, , - R

  18. 40 CFR 721.10072 - Benzene, 1,1′-methylenebis[4-isocyanato-, polymer with benzenedicarboxylic acid, butyl dialkyl...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...-isocyanato-, polymer with benzenedicarboxylic acid, butyl dialkyl ester, poly[oxy(methyl-1,2-ethanediyl)], .alpha.-hydro-.omega.-hydroxy-, oxirane, alkyl-, polymer with oxirane, ether with propanepolyol and...-isocyanato-, polymer with benzenedicarboxylic acid, butyl dialkyl ester, poly[oxy(methyl-1,2-ethanediyl...

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

    USDA-ARS?s Scientific Manuscript database

    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...

  20. Efficacy of Myricetin as an Antioxidant in Methyl Esters of Soybean Oil

    USDA-ARS?s Scientific Manuscript database

    The antioxidant activity of myricetin, a natural flavonol found in fruits and vegetables, was determined in soybean oil methyl esters (SME) and compared with alpha-tocopherol and tert-butylhydroquinone (TBHQ) over a 90 day period employing EN 14112, acid value, and kinematic viscosity methods. Myri...

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

    Treesearch

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

    2017-01-01

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

  2. Effects of Blending Alcohols with Poultry Fat Methyl Esters on Cold Flow Properties

    USDA-ARS?s Scientific Manuscript database

    The low temperature operability, kinematic viscosity, and acid value of poultry fat methyl esters were improved with addition of ethanol, isopropanol, and butanol in a linear fashion with increasing alcohol content. The flash point decreased and moisture content increased upon addition of alcohols t...

  3. Correlating the cold flow and melting properties of fatty acid methyl ester (FAME) mixtures

    USDA-ARS?s Scientific Manuscript database

    Fatty acid methyl ester (FAME) mixtures derived from plant oils or animal fats are used to make biodiesel, lubricants, surfactants, plasticizers, ink solvents, paint strippers and other products. Processing requires a precise knowledge of the physico-chemical properties of mixtures with diverse and ...

  4. Fuel property enhancement of biodiesel fuels from common and alternative feedstocks via complementary blending

    USDA-ARS?s Scientific Manuscript database

    Fatty acid methyl esters (biodiesel) prepared from field pennycress and meadowfoam seed oils were blended with methyl esters from camelina, cottonseed, palm, and soybean oils in an effort to ameliorate technical deficiencies inherent to these biodiesel fuels. For instance, camelina, cottonseed, and ...

  5. Methyl esters (biodiesel) from and fatty acid profile of Gliricidia sepium seed oil

    USDA-ARS?s Scientific Manuscript database

    Increasing the supply of biodiesel by defining and developing additional feedstocks is important to overcome the still limited amounts available of this alternative fuel. In this connection, the methyl esters of the seed oil of Gliricidia sepium were synthesized and the significant fuel-related prop...

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

    USDA-ARS?s Scientific Manuscript database

    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...

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

    USDA-ARS?s Scientific Manuscript database

    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...

  8. A compound-based proteomic approach discloses 15-ketoatractyligenin methyl ester as a new PPARγ partial agonist with anti-proliferative ability

    NASA Astrophysics Data System (ADS)

    Vasaturo, Michele; Fiengo, Lorenzo; de Tommasi, Nunziatina; Sabatino, Lina; Ziccardi, Pamela; Colantuoni, Vittorio; Bruno, Maurizio; Cerchia, Carmen; Novellino, Ettore; Lupo, Angelo; Lavecchia, Antonio; Piaz, Fabrizio Dal

    2017-01-01

    Proteomics based approaches are emerging as useful tools to identify the targets of bioactive compounds and elucidate their molecular mechanisms of action. Here, we applied a chemical proteomic strategy to identify the peroxisome proliferator-activated receptor γ (PPARγ) as a molecular target of the pro-apoptotic agent 15-ketoatractyligenin methyl ester (compound 1). We demonstrated that compound 1 interacts with PPARγ, forms a covalent bond with the thiol group of C285 and occupies the sub-pocket between helix H3 and the β-sheet of the ligand-binding domain (LBD) of the receptor by Surface Plasmon Resonance (SPR), mass spectrometry-based studies and docking experiments. 1 displayed partial agonism of PPARγ in cell-based transactivation assays and was found to inhibit the AKT pathway, as well as its downstream targets. Consistently, a selective PPARγ antagonist (GW9662) greatly reduced the anti-proliferative and pro-apoptotic effects of 1, providing the molecular basis of its action. Collectively, we identified 1 as a novel PPARγ partial agonist and elucidated its mode of action, paving the way for therapeutic strategies aimed at tailoring novel PPARγ ligands with reduced undesired harmful side effects.

  9. A compound-based proteomic approach discloses 15-ketoatractyligenin methyl ester as a new PPARγ partial agonist with anti-proliferative ability

    PubMed Central

    Vasaturo, Michele; Fiengo, Lorenzo; De Tommasi, Nunziatina; Sabatino, Lina; Ziccardi, Pamela; Colantuoni, Vittorio; Bruno, Maurizio; Cerchia, Carmen; Novellino, Ettore; Lupo, Angelo; Lavecchia, Antonio; Piaz, Fabrizio Dal

    2017-01-01

    Proteomics based approaches are emerging as useful tools to identify the targets of bioactive compounds and elucidate their molecular mechanisms of action. Here, we applied a chemical proteomic strategy to identify the peroxisome proliferator-activated receptor γ (PPARγ) as a molecular target of the pro-apoptotic agent 15-ketoatractyligenin methyl ester (compound 1). We demonstrated that compound 1 interacts with PPARγ, forms a covalent bond with the thiol group of C285 and occupies the sub-pocket between helix H3 and the β-sheet of the ligand-binding domain (LBD) of the receptor by Surface Plasmon Resonance (SPR), mass spectrometry-based studies and docking experiments. 1 displayed partial agonism of PPARγ in cell-based transactivation assays and was found to inhibit the AKT pathway, as well as its downstream targets. Consistently, a selective PPARγ antagonist (GW9662) greatly reduced the anti-proliferative and pro-apoptotic effects of 1, providing the molecular basis of its action. Collectively, we identified 1 as a novel PPARγ partial agonist and elucidated its mode of action, paving the way for therapeutic strategies aimed at tailoring novel PPARγ ligands with reduced undesired harmful side effects. PMID:28117438

  10. A compound-based proteomic approach discloses 15-ketoatractyligenin methyl ester as a new PPARγ partial agonist with anti-proliferative ability.

    PubMed

    Vasaturo, Michele; Fiengo, Lorenzo; De Tommasi, Nunziatina; Sabatino, Lina; Ziccardi, Pamela; Colantuoni, Vittorio; Bruno, Maurizio; Cerchia, Carmen; Novellino, Ettore; Lupo, Angelo; Lavecchia, Antonio; Piaz, Fabrizio Dal

    2017-01-24

    Proteomics based approaches are emerging as useful tools to identify the targets of bioactive compounds and elucidate their molecular mechanisms of action. Here, we applied a chemical proteomic strategy to identify the peroxisome proliferator-activated receptor γ (PPARγ) as a molecular target of the pro-apoptotic agent 15-ketoatractyligenin methyl ester (compound 1). We demonstrated that compound 1 interacts with PPARγ, forms a covalent bond with the thiol group of C285 and occupies the sub-pocket between helix H3 and the β-sheet of the ligand-binding domain (LBD) of the receptor by Surface Plasmon Resonance (SPR), mass spectrometry-based studies and docking experiments. 1 displayed partial agonism of PPARγ in cell-based transactivation assays and was found to inhibit the AKT pathway, as well as its downstream targets. Consistently, a selective PPARγ antagonist (GW9662) greatly reduced the anti-proliferative and pro-apoptotic effects of 1, providing the molecular basis of its action. Collectively, we identified 1 as a novel PPARγ partial agonist and elucidated its mode of action, paving the way for therapeutic strategies aimed at tailoring novel PPARγ ligands with reduced undesired harmful side effects.

  11. Interaction of amphotericin B and its low toxic derivative, N-methyl-N-D-fructosyl amphotericin B methyl ester, with fungal, mammalian and bacterial cells measured by the energy transfer method.

    PubMed

    Szlinder-Richert, Joanna; Cybulska, Barbara; Grzybowska, Jolanta; Bolard, Jacques; Borowski, Edward

    2004-04-01

    Amphotericin B (AMB) derivative, N-methyl-N-D-fructosyl amphotericin B methyl ester (MFAME) retains the broad antifungal spectrum and potency of the parent antibiotic, whereas its toxicity towards mammalian cells is reduced by about two orders of magnitude. The purpose of this work was to find out whether the differences observed in the toxicity of MFAME and native AMB are due to the differential drugs affinity to fungal and mammalian cell membranes. Comparative studies on AMB and MFAME biological activity and their affinity to fungal, mammalian and bacterial cells were performed. The interaction of AMB and MFAME with cells have been studied by fluorescence method based on the energy transfer between membrane fluorescent probe (donor) and the polyenic chromophore of the antibiotic (acceptor) simultaneously present in the cell membrane. The amount of the antibiotic bound to cells was indicated by the extent of fluorescence quenching of 1-(4-trimethylammoniumphenyl)-6-phenyl-1,3,5-hexatriene (TMA-DPH) or 1,6-diphenyl-1,3,5-hexatriene (DPH) by polyenic chromophore of the antibiotic. The results obtained indicate that binding extent and characteristics for both antibiotics are comparable in the three types of cells studied. Dramatically lower toxicity of MFAME as compared to AMB towards mammalian cells is not related to the antibiotic-cell affinity, but rather to different consequences of these interactions for cells, reflected in membrane permeabilization. MFAME is definitely less effective than parent AMB in the permeabilizing species formation in mammalian cell membrane.

  12. 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.

  13. The Comparison of Hydrotreated Vegetable Oils With Respect to Petroleum Derived Fuels and the Effects of Transient Plasma Ignition in a Compression-Ignition Engine

    DTIC Science & Technology

    2012-09-01

    Content per Combustion J FAME Fatty Acid Methyl Ester FMEP Friction Mean Effective Pressure PSI or Bar FT Fischer-Tropsch h Heat...recently, algae-derived oils. Biodiesel has gained popularity in North America over the past decade, but the ester content of Fatty Acid Methyl ... Ester ( FAME ) fuel creates both cold weather and water- based operational issues. The Fischer-Tropsch (FT) process produces liquid fuels from “syngas,” a

  14. Update on the Us Army’s Fuel Contamination Detection Efforts

    DTIC Science & Technology

    2011-04-04

    Dual Eng flameout Contaminated with water and particulate 14 2009 C-130 USAF Jet Fuel Contamination with Fatty Acid Methyl Ester ( FAME ) BioFuel 15 20...DRNEN. WARRGHTER FOCUSED. Summary of Incidents • US Air Force – 2 - T-37 Super Absorbent Polymer 1 C 130 FAME Fatty Methyl Ester

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

    USDA-ARS?s Scientific Manuscript database

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

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.304 Acetic acid, [(5-chloro-8-quinolinyl)oxy-], 1-methyl hexyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The...

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

    USDA-ARS?s Scientific Manuscript database

    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...

  18. 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, 2-(3-phenylbutylidene...

  19. 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, 2-(3-phenylbutylidene...

  20. Methyl esters (biodiesel) from Melanolepis multiglandulosa (alim) seed oil and their properties

    USDA-ARS?s Scientific Manuscript database

    Sufficient supply of feedstock oils is a major issue facing biodiesel in order to increase the still limited amounts available. In this work, the fatty acid methyl esters, also known as biodiesel, of the seed oil of Melanolepsi multiglandulosa, a member of the Euphorbiaceae family, were prepared and...

  1. Characterization of Microalgal Lipids for Optimization of Biofuels

    DTIC Science & Technology

    2014-05-09

    SUBJECT TERMS algae, biofuel, biodiesel , fatty acid methyl ester, extremophile, Galdieria 16. SECURITY CLASSIFICATION OF: 17. LIMITATION OF...percentages in algal culture. KEYWORDS algae, biofuel, biodiesel , fatty acid methyl ester, extremophile, Galdieria 2...Most biofuels can be categorized as biodiesel products (to include biodistillates) or bioethanol. Corn and sugar cane undergo fermentation in order

  2. 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. Copyright © 2015 Elsevier Ltd. All rights reserved.

  3. Degradation of cyanidin-3-rutinoside and formation of protocatechuic acid methyl ester in methanol solution by gamma irradiation.

    PubMed

    Lee, Seung Sik; Kim, Tae Hoon; Lee, Eun Mi; Lee, Min Hee; Lee, Ha Yeong; Chung, Byung Yeoup

    2014-08-01

    Anthocyanins are naturally occurring phenolic compounds having broad biological activities including anti-mutagenesis and anti-carcinogenesis. We studied the effects and the degradation mechanisms of the most common type of anthocyanins, cyanidin-3-rutinoside (cya-3-rut), by using gamma ray. Cya-3-rut in methanol (1mg/ml) was exposed to gamma-rays from 1 to 10kGy. We found that the reddish colour of cya-3-rut in methanol disappeared gradually in a dose-dependent manner and effectively disappeared (>97%) at 10kGy of gamma ray. Concomitantly, a new phenolic compound was generated and identified as a protocatechuic acid methyl ester by liquid chromatography, (1)H, and (13)C NMR. The formation of protocatechuic acid methyl ester increased with increasing irradiation and the amount of protocatechuic acid methyl ester formed by decomposition of cya-3-rut (20μg) at 10kGy of gamma ray was 1.95μg. In addition, the radical-scavenging activities were not affected by gamma irradiation. Copyright © 2014 Elsevier Ltd. All rights reserved.

  4. A Biotin Biosynthesis Gene Restricted to Helicobacter

    PubMed Central

    Bi, Hongkai; Zhu, Lei; Jia, Jia; Cronan, John E.

    2016-01-01

    In most bacteria the last step in synthesis of the pimelate moiety of biotin is cleavage of the ester bond of pimeloyl-acyl carrier protein (ACP) methyl ester. The paradigm cleavage enzyme is Escherichia coli BioH which together with the BioC methyltransferase allows synthesis of the pimelate moiety by a modified fatty acid biosynthetic pathway. Analyses of the extant bacterial genomes showed that bioH is absent from many bioC-containing bacteria and is replaced by other genes. Helicobacter pylori lacks a gene encoding a homologue of the known pimeloyl-ACP methyl ester cleavage enzymes suggesting that it encodes a novel enzyme that cleaves this intermediate. We isolated the H. pylori gene encoding this enzyme, bioV, by complementation of an E. coli bioH deletion strain. Purified BioV cleaved the physiological substrate, pimeloyl-ACP methyl ester to pimeloyl-ACP by use of a catalytic triad, each member of which was essential for activity. The role of BioV in biotin biosynthesis was demonstrated using a reconstituted in vitro desthiobiotin synthesis system. BioV homologues seem the sole pimeloyl-ACP methyl ester esterase present in the Helicobacter species and their occurrence only in H. pylori and close relatives provide a target for development of drugs to specifically treat Helicobacter infections. PMID:26868423

  5. Molecular modeling studies of novel retro-binding tripeptide active-site inhibitors of thrombin.

    PubMed

    Lau, W F; Tabernero, L; Sack, J S; Iwanowicz, E J

    1995-08-01

    A novel series of retro-binding tripeptide thrombin active-site inhibitors was recently developed (Iwanowicz, E. I. et al. J. Med. Chem. 1994, 37, 2111(1)). It was hypothesized that the binding mode for these inhibitors is similar to that of the first three N-terminal residues of hirudin. This binding hypothesis was subsequently verified when the crystal structure of a member of this series, BMS-183,507 (N-[N-[N-[4-(Aminoiminomethyl)amino[-1-oxobutyl]-L- phenylalanyl]-L-allo-threonyl]-L-phenylalanine, methyl ester), was determined (Taberno, L.J. Mol. Biol. 1995, 246, 14). The methodology for developing the binding models of these inhibitors, the structure-activity relationships (SAR) and modeling studies that led to the elucidation of the proposed binding mode is described. The crystal structure of BMS-183,507/human alpha-thrombin is compared with the crystal structure of hirudin/human alpha-thrombin (Rydel, T.J. et al. Science 1990, 249,227; Rydel, T.J. et al. J. Mol Biol. 1991, 221, 583; Grutter, M.G. et al. EMBO J. 1990, 9, 2361) and with the computational binding model of BMS-183,507.

  6. Optimization of gas chromatographic method for the enantioseparation of arylpropionic non-steroidal anti-inflammatory drug methyl esters.

    PubMed

    Petrović, Marinko; Debeljak, Zeljko; Blazević, Nikola

    2005-09-15

    The gas chromatography (GC) method for enantioseparation of well-known non-steroidal anti-inflammatory drugs ibuprofen, fenoprofen and ketoprofen methyl esters mixture was developed. Best enantioseparation was performed on capillary column with heptakis-(2,3-di-O-methyl-6-O-t-butyldimethyl-silyl)-beta-cyclodextrin stationary phase and hydrogen used as a carrier gas. Initial temperature, program rate and carrier pressure were optimized to obtain best resolution between enantiomers.

  7. Binding characteristics of [125I]Bolton-Hunter [Sar9,Met(O2)11]substance P, a new selective radioligand for the NK1 receptor.

    PubMed

    Lew, R; Geraghty, D P; Drapeau, G; Regoli, D; Burcher, E

    1990-08-02

    The selective tachykinin agonist [Sar9,Met(O2)11]substance P (Sar-SP) was radioiodinated with [125I]Bolton-Hunter reagent and the product [125I]Bolton-Hunter-[Sar9,Met(O)2)11]SP (BHSar-SP) purified using reverse phase HPLC. Autoradiographic studies showed dense specific binding of BHSar-SP over the rat submandibular gland and over several regions in rat brain, with very low nonspecific binding, identical with the pattern of binding sites seen in a parallel study with [125I]Bolton-Hunter SP (BHSP). In homogenate binding experiments, BHSar-SP bound with high affinity to a single site in membranes from rat brain (KD 261 pM) and rat submandibular gland (KD 105 pM). Comparative values for BHSP were 495 and 456 pM, i.e. of two and four fold lower affinity than BHSar-SP. Association of BHSar-SP to membranes from brain (k+1 3.7 x 10(9) M-1 min-1) was faster than to membranes from salivary gland (k+1 5.6 x 10(8) M-1 min-1). In competition studies, BHSar-SP was displaced from salivary gland membranes by substance P (SP) approximately physalaemin greater than or equal to Sar-SP approximately SP-(3-11) greater than SP-(5-11) much greater than neurokinin A (NKA) approximately eledoisin = kassinin = SP-methyl ester greater than or equal to neurokinin B (NKB) much greater than [Nle10]NKA-(4-10) greater than [MePhe7]NKB-(4-10). In brain membranes, the rank potency order was SP greater than Sar-SP greater than or equal to physalaemin greater than SP-(3-11) greater than SP-(5-11) greater than NKA greater than or equal to eledoisin much greater than NKB greater than kassinin greater than SP-methyl ester: however [MePhe7]NKB-(4-10) and [Nle10]NKA-(4-10) were ineffective competitors at concentrations up to 1 microM. Both binding patterns are consistent with BHSar-SP binding to an NK1 site. With the exception of SP, Sar-SP, SP-(3-11) and physalaemin, all competitors were 5 to 54 times less potent at BHSar-SP binding sites in brain than in salivary gland. These data reveal some differences in characteristics of NK1 binding sites in brain and submandibular gland. Although of higher affinity, BHSar-SP does not appear greatly more selective than BHSP in its ability to define NK1 binding sites.

  8. Synthesis of (nor)tropeine (di)esters and allosteric modulation of glycine receptor binding.

    PubMed

    Maksay, Gábor; Nemes, Péter; Vincze, Zoltán; Bíró, Timea

    2008-02-15

    (Hetero)aromatic mono- and diesters of tropine and nortropine were prepared. Modulation of [3H]strychnine binding to glycine receptors of rat spinal cord was examined with a ternary allosteric model. The esters displaced [3H]strychnine binding with nano- or micromolar potencies and strong negative cooperativity. Coplanarity and distance of the ester moieties of diesters affected the binding affinity being nanomolar for isophthaloyl-bistropane and nortropeines. Nortropisetron had the highest affinity (K(A) approximately 10 nM). Two esters displayed negative cooperativity with glycine in displacement, while three esters of low-affinity and nortropisetron exerted positive cooperativity with glycine.

  9. Separation and determination of secoisolariciresinol diglucoside oligomers and their hydrolysates in the flaxseed extract by high-performance liquid chromatography.

    PubMed

    Li, Xin; Yuan, Jian-Ping; Xu, Shi-Ping; Wang, Jiang-Hai; Liu, Xin

    2008-03-28

    Flaxseed contains the largest amount of lignan secoisolariciresinol diglucoside (SDG) oligomers and is the richest dietary source of SDG. SDG oligomers in the flaxseed extract are often hydrolyzed to break the ester linkages for the release of SDG and the glycosidic bonds for the release of secoisolariciresinol (SECO). The hydrolysates of SDG oligomers are complicated because of the production of esters in an alcohol-containing medium. In this study, a new gradient reversed-phase high-performance liquid chromatography (HPLC) method has been developed to be suitable for the separation and determination of: (1) SDG oligomers extracted from the defatted flaxseed powder by a 70% aqueous methanol solution; (2) SDG oligomers and their alkaline hydrolysates, including SDG, p-coumaric acid glucoside and its methyl ester, ferulic acid glucoside and its methyl ester in an alkaline hydrolytic solution; and (3) the succedent acid hydrolysates, including secoisolariciresinol monoglucoside (SMG), SECO, anhydrosecoisolariciresinol (anhydro-SECO), p-coumaric acid and its methyl ester, ferulic acid and its methyl ester, 5-hydroxymethyl-2-furfural (HMF) and its degradation product in an acid hydrolytic solution. The content of SDG oligomers in a defatted flaxseed powder was found to be 38.5 mg/g on a dry matter basis, corresponding to a SDG content of 15.4 mg/g, which was determined after alkaline hydrolysis. Furthermore, this study presented a major reaction pathway for the hydrolysis of SDG oligomers.

  10. Fertility of male rats treated with 15(S)-15-methyl prostaglandin F2 alpha methyl ester-containing silastic implants.

    PubMed

    Kimball, F A; Frielink, R D; Porteus, S E

    1978-01-01

    Male Spraque-Dawley rats receiving implants of silicone rubber discs containing 1% or 2% 15(S)-15-methyl prostaglandin F2 alpha methyl ester (15-Me-PGF 2 alpha) or no prostaglandin were tested in successive breeding trials for potency and fertility. One week after implantation, discs containing 1% 15-Me-PGF2 alpha reduced potency and fertility, which returned 2 weeks after implantation. Animals receiving implants of the 2% discs were apparently impotent the 1st week following implantation; potency returned before full fertility returned 11 weeks after implantation.

  11. Targeted mutations and MD simulations of a methanol-stable lipase YLIP9 from Yarrowia lipolytica MSR80 to develop a biodiesel enzyme.

    PubMed

    Syal, Poonam; Verma, Ved Vrat; Gupta, Rani

    2017-11-01

    Biodiesel, an environment friendly alternative for fuels, contains methyl esters of long-chain fatty acids. Our group has reported a methanol-stable YLIP9 from Yarrowia lipolytica MSR80 that shows poor catalysis of long-chain fatty acids. To shift its substrate specificity, residues within lid and binding pocket were identified for sequential mutations using YLIP2 as the template. Of the two point mutations (Glu116Leu and Ser119Val) introduced in the lid, the former mutation (YLIP9L1) increased the catalytic rate by ∼2-fold without any change in substrate specificity. In this mutant, six binding pocket residues (Bp2-Bp7) were further mutated to obtain six double mutants. YLIP9L1Bp3 showed significant shift in substrate specificity towards long-chain pNPesters with 11-fold increase in catalytic efficiency than YLIP9. Double mutations also led to increased thermostability and lowered activation energy of YLIP9L1Bp3 thereby shifting its optimum temperature from 60°C to 50°C. In silico molecular dynamics simulations revealed improved lid flexibility and increased catalytic triad volume in YLIP9L1Bp3. The enzyme YLIP9L1Bp3 was methanol-stable having selectivity for long-chain fatty acids with improved catalytic efficiency. Its application as a biodiesel enzyme was validated by transesterification of palm oil in presence of methanol, where it showed 8-fold increase in conversion of oil to methyl esters. Copyright © 2017 Elsevier B.V. All rights reserved.

  12. Thermomyces lanuginosus lipase-catalyzed synthesis of natural flavor esters in a continuous flow microreactor.

    PubMed

    Gumel, Ahmad Mohammed; Annuar, M S M

    2016-06-01

    Enzymatic catalysis is considered to be among the most environmental friendly processes for the synthesis of fine chemicals. In this study, lipase from Thermomyces lanuginosus (Lecitase Ultra™) was used to catalyze the synthesis of flavor esters, i.e., methyl butanoate and methyl benzoate by esterification of the acids with methanol in a microfluidic system. Maximum reaction rates of 195 and 115 mM min -1 corresponding to catalytic efficiencies (k cat /K M ) of 0.30 and 0.24 min -1  mM -1 as well as yield conversion of 54 and 41 % were observed in methyl butanoate and methyl benzoate synthesis, respectively. Catalytic turnover (k cat ) was higher for methyl butanoate synthesis. Rate of synthesis and yield decreased with increasing flow rates. For both esters, increase in microfluidic flow rate resulted in increased advective transport over molecular diffusion and reaction rate, thus lower conversion. In microfluidic synthesis using T. lanuginosus lipase, the following reaction conditions were 40 °C, flow rate 0.1 mL min -1 , and 123 U g -1 enzyme loading found to be the optimum operating limits. The work demonstrated the application of enzyme(s) in a microreactor system for the synthesis of industrially important esters.

  13. The impact of cold storage and ethylene on volatile ester production and aroma perception in 'Hort16A' kiwifruit.

    PubMed

    Günther, Catrin S; Marsh, Ken B; Winz, Robert A; Harker, Roger F; Wohlers, Mark W; White, Anne; Goddard, Matthew R

    2015-02-15

    Fruit esters are regarded as key volatiles for fruit aroma. In this study, the effects of cold storage on volatile ester levels of 'Hort16A' (Actinidia chinensis Planch. var chinensis) kiwifruit were examined and the changes in aroma perception investigated. Cold storage (1.5°C) for two or four months of fruit matched for firmness and soluble solids concentration resulted in a significant reduction in aroma-related esters such as methyl/ethyl propanoate, methyl/ethyl butanoate and methyl/ethyl hexanoate. Levels of these esters, however, were restored by ethylene treatment (100ppm, 24h) before ripening. A sensory panel found that "tropical" and "fruit candy" aroma was stronger and "green" odour notes less intensively perceived in kiwifruit which were ethylene-treated after cold storage compared to untreated fruit. The key findings presented in this study may lead to further work on the ethylene pathway, and innovative storage and marketing solutions for current and novel fruit cultivars. Copyright © 2014 Elsevier Ltd. All rights reserved.

  14. 21 CFR 175.210 - Acrylate ester copolymer coating.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Acrylate ester copolymer coating. 175.210 Section... COATINGS Substances for Use as Components of Coatings § 175.210 Acrylate ester copolymer coating. Acrylate...) The acrylate ester copolymer is a fully polymerized copolymer of ethyl acrylate, methyl methacrylate...

  15. Production of Fatty Acid Methyl Esters via the In Situ Transesterification of Soybean Oil in Carbon Dioxide-Expanded Methanol

    USDA-ARS?s Scientific Manuscript database

    The production of fatty acid methyl esters (FAME) by direct alkali- and acid-catalyzed in situ transesterification of soybean flakes in CO2-expanded methanol was examined at various temperatures and pressures. Attempts to synthesize FAME from soy flakes via alkaline catalysis, using sodium methoxid...

  16. Preparation of Chemicals and Bulk Drug Substances for the U.S. Army Drug Development Program.

    DTIC Science & Technology

    1997-12-01

    4(R)-rio (,) -dihydroartemisininoxy]-; artemisinin ; dihydroartemisinin; artelinic acid, methyl ester; artelinic acid. -I- TABLE OF CONTENTS I...acid, 4-(4-chloro- phenyl) -4(R) -[10(P) -dihydro- artemisininoxy]-......................... 49 10. Artemisinin ................................. 58 11...dihydroartemisininoxy]-; artemisinin ; dihydroartemisinin; artelinic acid, methyl ester; artelinic acid. -V- II FOREWORD opinions, interpretations, conclusions and

  17. 40 CFR 721.8485 - 2-Propenoic acid, 2-methyl-, (octahydro-4,7-methano-1H- indene-5-diyl)bis(methylene) ester.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.8485 2-Propenoic acid, 2-methyl-, (octahydro-4,7-methano-1H- indene-5-diyl)bis(methylene) ester. (a) Chemical substance and...

  18. 40 CFR 721.304 - Acetic acid, [(5-chloro-8-quinolinyl)oxy-], 1-methyl hexyl ester.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Acetic acid, [(5-chloro-8-quinolinyl)oxy-], 1-methyl hexyl ester. 721.304 Section 721.304 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.304 Acetic acid, [(5-chloro-8-quinolinyl)oxy-], 1...

  19. 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

    ... PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES 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) The...

  20. 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

    ... PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES 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) The...

  1. 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

    ... PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES 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) The...

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

    USDA-ARS?s Scientific Manuscript database

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

  3. High-methionine diets accelerate atherosclerosis by HHcy-mediated FABP4 gene demethylation pathway via DNMT1 in ApoE(-/-) mice.

    PubMed

    Yang, An-Ning; Zhang, Hui-Ping; Sun, Yue; Yang, Xiao-Ling; Wang, Nan; Zhu, Guangrong; Zhang, Hui; Xu, Hua; Ma, Sheng-Chao; Zhang, Yue; Li, Gui-Zhong; Jia, Yue-Xia; Cao, Jun; Jiang, Yi-Deng

    2015-12-21

    Homocysteine (Hcy) is an independent risk factor for atherosclerosis, but the underlying molecular mechanisms are not known. We investigated the effects of Hcy on fatty acid-binding protein 4 (FABP4), and tested our hypothesis that Hcy-induced atherosclerosis is mediated by increased FABP4 expression and decreased methylation. The FABP4 expression and DNA methylation was assessed in the aorta of ApoE(-/-) mice fed high-methionine diet for 20weeks. Over-expression of FABP4 enhanced accumulation of total cholesterol and cholesterol ester in foam cells. The up-regulation of DNA methyltransferase 1 (DNMT1) promoted the methylation process and decreased FABP4 expression. These data suggest that FABP4 plays a key role in Hcy-mediated disturbance of lipid metabolism and that DNMT1 may be a novel therapeutic target in Hcy-related atherosclerosis. Copyright © 2015 Federation of European Biochemical Societies. Published by Elsevier B.V. All rights reserved.

  4. Experimental and modeling study of the thermal decomposition of methyl decanoate

    PubMed Central

    Herbinet, Olivier; Glaude, Pierre-Alexandre; Warth, Valérie; Battin-Leclerc, Frédérique

    2013-01-01

    The experimental study of the thermal decomposition of methyl decanoate was performed in a jet-stirred reactor at temperatures ranging from 773 to 1123 K, at residence times between 1 and 4 s, at a pressure of 800 Torr (106.6 kPa) and at high dilution in helium (fuel inlet mole fraction of 0.0218). Species leaving the reactor were analyzed by gas chromatography. Main reaction products were hydrogen, carbon oxides, small hydrocarbons from C1 to C3, large 1-olefins from 1-butene to 1-nonene, and unsaturated esters with one double bond at the end of the alkyl chain from methyl-2-propenoate to methyl-8-nonenoate. At the highest temperatures, the formation of polyunsaturated species was observed: 1,3-butadiene, 1,3-cyclopentadiene, benzene, toluene, indene, and naphthalene. These results were compared with previous ones about the pyrolysis of n-dodecane, an n-alkane of similar size. The reactivity of both molecules was found to be very close. The alkane produces more olefins while the ester yields unsaturated oxygenated compounds. A detailed kinetic model for the thermal decomposition of methyl decanoate has been generated using the version of software EXGAS which was updated to take into account the specific chemistry involved in the oxidation of methyl esters. This model contains 324 species and 3231 reactions. It provided a very good prediction of the experimental data obtained in jet-stirred reactor. The formation of the major products was analyzed. The kinetic analysis showed that the retro-ene reactions of intermediate unsaturated methyl esters are of importance in low reactivity systems. PMID:23710078

  5. Plant-derived juvenile hormone III analogues and other sesquiterpenes from the stem bark of Cananga latifolia.

    PubMed

    Yang, Heejung; Kim, Hye Seong; Jeong, Eun Ju; Khiev, Piseth; Chin, Young-Won; Sung, Sang Hyun

    2013-10-01

    Juvenile hormone III (JH III) is a larval metamorphosis-regulating hormone present in most insect species. JH III was first isolated from the plant, Cyperus iria L., but the presence of JH III has not been reported in other plant species. In the present study, proof of the existence of JH III and its analogues from Cananga latifolia was established. From an aqueous MeOH extract of C. latifolia stem bark, six compounds were isolated along with nine known compounds. These were identified by using spectroscopic analyses as: (2E,6E,10R)-11-butoxy-10-hydroxy-3,7,11-trimethyldodeca-2,6-dienoic acid methyl ester, (2E,6E)-3,7,11-trimethyl-10-oxododeca-2,6-dienoic acid methyl ester, (2E)-3-methyl-5-[(1S,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]-pent-2-enoic acid methyl ester, 1β-hydroxy-3-oxo-4β, 5α,7α-H-eudesmane 11-O-α-l-rhamnopyranoside, 4-epi-aubergenone 11-O-2',3'-di-O-acetyl-α-l-rhamnopyranoside and 4-epi-aubergenone 11-O-2',4'-di-O-acetyl-α-l-rhamnopyranoside. Three of the previously known compounds, (2E,6E,10R)-10-hydroxy-3,7,11-trimethyldodeca-2,6,11-trienoaic acid methyl ester, (2E,6E,10R)-10,11-dihydroxy-3,7,11-trimethyldodeca-2,6-dienoic acid and (2E,6S)-3-methyl-6-hydroxy-6-[(2R,5R)-5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran-2-yl]-hex-2-enoaic acid methyl ester have now been found in a plant species. Ultra performance liquid chromatography-quadruple time-of-flight mass spectroscopy (UPLC-QTOF/MS) analysis of the chemical constituents of C. latifolia showed that several were predominant in the sub-fractions of a C. latifolia stem bark extract. Copyright © 2013 Elsevier Ltd. All rights reserved.

  6. Biodiesel fuels

    USDA-ARS?s Scientific Manuscript database

    The mono-alkyl esters, most commonly the methyl esters, of vegetable oils, animal fats or other materials consisting mainly of triacylglycerols, often referred to as biodiesel, are an alternative to conventional petrodiesel for use in compression-ignition engines. The fatty acid esters that thus com...

  7. Synthesis of molecularly imprinted polymers by atom transfer radical polymerization for the solid-phase extraction of phthalate esters in edible oil.

    PubMed

    Chen, Ningning; He, Juan; Wu, Chaojun; Li, Yuanyuan; Suo, An; Wei, Hongliang; He, Lijun; Zhang, Shusheng

    2017-03-01

    Novel molecularly imprinted polymers of phthalate esters were prepared by atom transfer radical polymerization using methyl methacrylate as functional monomer, cyclohexanone as solvent, cuprous chloride as catalyst, 1-chlorine-1-ethyl benzene as initiator and 2,2-bipyridyl as cross-linker in the mixture of methanol and water (1:1, v/v). The effect of reaction conditions such as monomer ratio and template on the adsorption properties was investigated. The optimum condition was obtained by an orthogonal experiment. The obtained polymers were characterized using scanning electron microscopy. The binding property was studied with both static and dynamic methods. Results showed that the polymers exhibited excellent recognition capacity and outstanding selectivity for ten phthalate esters. Factors affecting the extraction efficiency of the molecularly imprinted solid-phase extraction were systematically investigated. An analytical method based on the molecularly imprinted coupled with gas chromatography and flame ionization detection was successfully developed for the simultaneous determination of ten phthalate esters from edible oil. The method detection limits were 0.10-0.25 μg/mL, and the recoveries of spiked samples were 82.5-101.4% with relative standard deviations of 1.24-5.37% (n = 6). © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  8. Engineering Escherichia coli for Biodiesel Production Utilizing a Bacterial Fatty Acid Methyltransferase▿†

    PubMed Central

    Nawabi, Parwez; Bauer, Stefan; Kyrpides, Nikos; Lykidis, Athanasios

    2011-01-01

    The production of low-cost biofuels in engineered microorganisms is of great interest due to the continual increase in the world's energy demands. Biodiesel is a renewable fuel that can potentially be produced in microbes cost-effectively. Fatty acid methyl esters (FAMEs) are a common component of biodiesel and can be synthesized from either triacylglycerol or free fatty acids (FFAs). Here we report the identification of a novel bacterial fatty acid methyltransferase (FAMT) that catalyzes the formation of FAMEs and 3-hydroxyl fatty acid methyl esters (3-OH-FAMEs) from the respective free acids and S-adenosylmethionine (AdoMet). FAMT exhibits a higher specificity toward 3-hydroxy free fatty acids (3-OH-FFAs) than FFAs, synthesizing 3-hydroxy fatty acid methyl esters (3-OH-FAMEs) in vivo. We have also identified bacterial members of the fatty acyl-acyl carrier protein (ACP) thioesterase (FAT) enzyme family with distinct acyl chain specificities. These bacterial FATs exhibit increased specificity toward 3-hydroxyacyl-ACP, generating 3-OH-FFAs, which can subsequently be utilized by FAMTs to produce 3-OH-FAMEs. PhaG (3-hydroxyacyl ACP:coenzyme A [CoA] transacylase) constitutes an alternative route to 3-OH-FFA synthesis; the coexpression of PhaG with FAMT led to the highest level of accumulation of 3-OH-FAMEs and FAMEs. The availability of AdoMet, the second substrate for FAMT, is an important factor regulating the amount of methyl esters produced by bacterial cells. Our results indicate that the deletion of the global methionine regulator metJ and the overexpression of methionine adenosyltransferase result in increased methyl ester synthesis. PMID:21926202

  9. Statistical optimization for lipase production from solid waste of vegetable oil industry.

    PubMed

    Sahoo, Rajesh Kumar; Kumar, Mohit; Mohanty, Swati; Sawyer, Matthew; Rahman, Pattanathu K S M; Sukla, Lala Behari; Subudhi, Enketeswara

    2018-04-21

    The production of biofuel using thermostable bacterial lipase from hot spring bacteria out of low-cost agricultural residue olive oil cake is reported in the present paper. Using a lipase enzyme from Bacillus licheniformis, a 66.5% yield of methyl esters was obtained. Optimum parameters were determined, with maximum production of lipase at a pH of 8.2, temperature 50.8°C, moisture content of 55.7%, and biosurfactant content of 1.693 mg. The contour plots and 3D surface responses depict the significant interaction of pH and moisture content with biosurfactant during lipase production. Chromatographic analysis of the lipase transesterification product was methyl esters, from kitchen waste oil under optimized conditions, generated methyl palmitate, methyl stearate, methyl oleate, and methyl linoleate.

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

    DOE Office of Scientific and Technical Information (OSTI.GOV)

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

    2016-01-13

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

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

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... RELATED PRODUCTS FOOD ADDITIVES PERMITTED IN FEED AND DRINKING WATER OF ANIMALS Food Additive Listing...-octadecadienoic acids). The food additive, methyl esters of conjugated linoleic acid (cis-9, trans-11 and trans-10... conditions: (a) The food additive is manufactured by the reaction of refined sunflower oil with methanol to...

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

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... RELATED PRODUCTS FOOD ADDITIVES PERMITTED IN FEED AND DRINKING WATER OF ANIMALS Food Additive Listing...-octadecadienoic acids). The food additive, methyl esters of conjugated linoleic acid (cis-9, trans-11 and trans-10... conditions: (a) The food additive is manufactured by the reaction of refined sunflower oil with methanol to...

  13. 21 CFR 573.637 - Methyl esters of conjugated linoleic acid (cis-9, trans-11 and trans-10, cis-12-octadecadienoic...

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... RELATED PRODUCTS FOOD ADDITIVES PERMITTED IN FEED AND DRINKING WATER OF ANIMALS Food Additive Listing...-octadecadienoic acids). The food additive, methyl esters of conjugated linoleic acid (cis-9, trans-11 and trans-10... conditions: (a) The food additive is manufactured by the reaction of refined sunflower oil with methanol to...

  14. 21 CFR 573.637 - Methyl esters of conjugated linoleic acid (cis-9, trans-11 and trans-10, cis-12-octadecadienoic...

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... RELATED PRODUCTS FOOD ADDITIVES PERMITTED IN FEED AND DRINKING WATER OF ANIMALS Food Additive Listing...-octadecadienoic acids). The food additive, methyl esters of conjugated linoleic acid (cis-9, trans-11 and trans-10... conditions: (a) The food additive is manufactured by the reaction of refined sunflower oil with methanol to...

  15. 21 CFR 573.637 - Methyl esters of conjugated linoleic acid (cis-9, trans-11 and trans-10, cis-12-octadecadienoic...

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... RELATED PRODUCTS FOOD ADDITIVES PERMITTED IN FEED AND DRINKING WATER OF ANIMALS Food Additive Listing...-octadecadienoic acids). The food additive, methyl esters of conjugated linoleic acid (cis-9, trans-11 and trans-10... conditions: (a) The food additive is manufactured by the reaction of refined sunflower oil with methanol to...

  16. Optimization of biodiesel production in a hydrodynamic cavitation reactor using used frying oil.

    PubMed

    Ghayal, Dyneshwar; Pandit, Aniruddha B; Rathod, Virendra K

    2013-01-01

    The present work demonstrates the application of a hydrodynamic cavitation reactor for the synthesis of biodiesel with used frying oil as a feedstock. The synthesis involved the transesterification of used frying oil (UFO) with methanol in the presence of potassium hydroxide as a catalyst. The effect of geometry and upstream pressure of a cavitating orifice plate on the rate of transesterification reaction has been studied. It is observed that the micro level turbulence created by hydrodynamic cavitation somewhat overcomes the mass transfer limitations for triphasic transesterification reaction. The significant effects of upstream pressure on the rate of formation of methyl esters have been seen. It has been observed that flow geometry of orifice plate plays a crucial role in process intensification. With an optimized plate geometry of 2mm hole diameter and 25 holes, more than 95% of triglycerides have been converted to methyl esters in 10 min of reaction time with cavitational yield of 1.28 × 10(-3) (Grams of methyl esters produced per Joule of energy supplied). The potential of UFO to produce good quality methyl esters has been demonstrated. Copyright © 2012 Elsevier B.V. All rights reserved.

  17. cis-fumagillin, a new methionine aminopeptidase (type 2) inhibitor produced by Penicillium sp. F2757.

    PubMed

    Kwon, J Y; Jeong, H W; Kim, H K; Kang, K H; Chang, Y H; Bae, K S; Choi, J D; Lee, U C; Son, K H; Kwon, B M

    2000-08-01

    Selective inhibition against the yeast MetAP2 (methionine aminopeptidase type 2) was detected in the fermentation broth of a fungus F2757 that was later identified as Penicillium janczewskii. A new compound cis-fumagillin methyl ester (1) was isolated from the diazomethane treated fermentation extracts together with the known compound fumagillin methyl ester (2). The cis-fumagillin methyl ester, a stereoisomer of fumagillin methyl ester at the C2'-C3' position of the aliphatic side chain, selectively inhibited growth of the map1 mutant yeast strain (MetAP1 deletion strain) at a concentration as low as 1 ng. However, the wild type yeast w303 and the mutant map2 (MetAP2 deleted) strains were resistant up to 10 microg of the compound. In enzyme experiments, compound 1 inhibited the MetAP2 with an IC50 value of 6.3 nM, but it did not inhibit the MetAP1 (IC50 >200 microM). Compound 2 also inhibited the MetAP2 with an IC50 value of 9.2 nM and 105 microM against MetAP1.

  18. Rape oil methyl ester (RME) and used cooking oil methyl ester (UOME) as alternative fuels

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    Hohl, G.H.

    1995-12-31

    The author presents a review about the fleet tests carried out by the Austrian Armed Forces concerning the practical application of a vegetable oil, i.e Rape Oil Methyl Ester (RME) and Used Cooking Oil Methyl Ester (UOME) as alternative fuels for vehicles under military conditions, and reviews other research results carried out in Austria. As a result of over-production in Western European agriculture, the increase in crop yields has led to tremendous surpluses. Alternative agricultural products have been sought. One alternative can be seen in biological fuel production for tractors, whereby the farmer is able to produce his own fuelmore » supply as was the case when he previously provided self-made feed for his horses. For the market introduction different activities were necessary. A considerable number of institutes and organizations including the Austrian Armed Forces have investigated, tested and developed these alternative fuels. The increasing disposal problems of used cooking oil have initiated considerations for its use. The recycling of this otherwise waste product, and its preparation for use as an alternative fuel to diesel oil, seems to be most promising.« less

  19. Biodiesel production using fatty acids from food industry waste using corona discharge plasma technology.

    PubMed

    Cubas, A L V; Machado, M M; Pinto, C R S C; Moecke, E H S; Dutra, A R A

    2016-01-01

    This article aims to describe an alternative and innovative methodology to transform waste, frying oil in a potential energy source, the biodiesel. The biodiesel was produced from fatty acids, using a waste product of the food industry as the raw material. The methodology to be described is the corona discharge plasma technology, which offers advantages such as acceleration of the esterification reaction, easy separation of the biodiesel and the elimination of waste generation. The best conditions were found to be an oil/methanol molar ratio of 6:1, ambient temperature (25 °C) and reaction time of 110 min and 30 mL of sample. The acid value indicates the content of free fatty acids in the biodiesel and the value obtained in this study was 0.43 mg KOH/g. Peaks corresponding to octadecadienoic acid methyl ester, octadecanoic acid methyl ester and octadecenoic acid methyl ester, from the biodiesel composition, were identified using GC-MS. A major advantage of this process is that the methyl ester can be obtained in the absence of chemical catalysts and without the formation of the co-product (glycerin). Copyright © 2015 Elsevier Ltd. All rights reserved.

  20. Discovery and characterizaton of a novel lipase with transesterification activity from hot spring metagenomic library.

    PubMed

    Yan, Wei; Li, Furong; Wang, Li; Zhu, Yaxin; Dong, Zhiyang; Bai, Linhan

    2017-03-01

    A new gene encoding a lipase (designated as Lip-1 ) was identified from a metagenomic bacterial artificial chromosome(BAC) library prepared from a concentrated water sample collected from a hot spring field in Niujie, Eryuan of Yunnan province in China. The open reading frame of this gene encoded 622 amino acid residues. It was cloned, fused with the oleosin gene and over expressed in Escherichia coli to prepare immobilized lipase artificial oil body AOB-sole-lip-1. The monomeric Sole-lip-1 fusion protein presented a molecular mass of 102.4 kDa. Enzyme assays using olive oil and methanol as the substrates in petroleum ether confirmed its transesterification activity. Hexadecanoic acid methyl ester, 8,11-Octadecadienoic acid methyl ester, 8-Octadecenoic acid methyl ester, and Octadecanoic acid methyl ester were detected. It showed favorable transesterification activity with optimal temperature 45 °C. Besides, the maximal biodiesel yield was obtained when the petroleum ether system as the organic solvent and the substrate methanol in 350 mmol/L (at a molar ratio of methanol of 10.5:1) and the water content was 1%. In light of these advantages, this lipase presents a promising resource for biodiesel production.

  1. Separation behavior of octadecadienoic acid isomers and identification of cis- and trans-isomers using gas chromatography.

    PubMed

    Shibamoto, Shigeaki; Gooley, Andrew; Yamamoto, Kouhei

    2015-01-01

    Using a strongly polar cyanopropyl capillary column we have investigated the gas chromatography (GC) separation behaviors of 24 octadecadienoic acid methyl ester (18:2ME) isomers compared against saturated methyl stearate (18:0ME) and arachidic acid methyl ester (20:0ME), and the dependency on the GC column temperature. The 24 isomers were obtained by performing cis-to trans-isomerization of six regioisomers: five of the 18:2ME isomers were prepared by the partial reduction of methyl α-linolenate and methyl γ-linolenate C18 trienoic acids with different double bond positions, whereas the sixth isomer, 18:2ME (c5, c9), was obtained from a raw constituent fatty acid methyl ester (FAME) sample extracted from Japanese yew seeds. There are no reference standards commercially available for 18:2ME isomers, and in elucidating the elution order of these isomers this study should help the future identification of cis- and trans-type of 18:2ME. We also report the identification method of cis- and trans-type of FAME using equivalent chain lengths and attempt the identification of cis- and trans-type of 18:2ME isomers from partially hydrogenated canola oil.

  2. Utilization of crude karanj (Pongamia pinnata) oil as a potential feedstock for the synthesis of fatty acid methyl esters.

    PubMed

    Khayoon, M S; Olutoye, M A; Hameed, B H

    2012-05-01

    Methyl esters were synthesized from crude karanj oil (CKO) by single step esterification with methanol using sulfuric acid (H(2)SO(4)) and phosphoric acid (H(3)PO(4)) as catalysts in a homogeneous batch process. H(3)PO(4) was less active than H(2)SO(4) during the process as it presented very low ester yields (<20%) for the various molar ratios of fatty acid to alcohol studied. With H(2)SO(4) as catalyst, the yield was as high as 89.8% at 65°C after 5h. The fatty acids profile of the oil (palmitic acid: ≈ 12%; stearic acid: ≈ 8%; oleic acid: ≈ 52% and linolenic acid of 17%) and the different reactivities of the acids were responsible for the observed differences in conversion to methyl esters. The findings attained with this study might contribute to the economic utilization of a non-edible feedstock. Copyright © 2012 Elsevier Ltd. All rights reserved.

  3. [Inhibition of oxidation of unsaturated fatty acid methyl esters by essential oils].

    PubMed

    Misharina, T A; Alinkina, E S; Vorobjeva, A K; Terenina, M B; Krikunova, N I

    2016-01-01

    The essential oils from 16 various spice plants were studied as natural antioxidants for the inhibition of autooxidation of polyunsaturated fatty acids methyl esters isolated from linseed oil. The content of methyl oleate, methyl linoleate, and methyl linolenoate after 1, 2, and 4 months of autooxidation were used as criteria to estimate the antioxidant efficiencies of essential oils. In 4 months, 92% of the methyl linolenoate and 79% of the methyl linoleate were oxidized in a control sample of a model system. It was found that the most effective antioxidants were essential oils from clove bud, cinnamon leaves, and oregano. They inhibited autooxidation of methyl linolenoate by 76–85%. The antioxidant properties of these essential oils were due to phenols— eugenol, carvacrol, and thymol. Essential oil from coriander did not contain phenols, but it inhibited methyl linolenoate oxidation by 38%. Essential oils from thyme, savory, mace, lemon, and tea tree inhibited methyl linolenoate oxidation by 17–24%. The other essential oils had no antioxidant properties.

  4. Antifungal Attributes of Lactobacillus plantarum MYS6 against Fumonisin Producing Fusarium proliferatum Associated with Poultry Feeds

    PubMed Central

    Deepthi, B. V.; Poornachandra Rao, K.; Chennapa, G.; Naik, M. K.; Chandrashekara, K. T.; Sreenivasa, M. Y.

    2016-01-01

    Fumonisins, being common in occurrence in maize-based feeds, pose a great threat to animal and human health. The present study is aimed at determining the antifungal activity of Lactobacillus plantarum MYS6 against a fumonisin producing fungus, Fusarium proliferatum MYS9. The isolate was subjected to standard tests for determining its probiotic attributes and antifungal properties. L. plantarum MYS6 thrived well at pH 3.0 and 6.0, and exhibited strong resistance up to 3% bile. The isolate showed a high degree of cell surface hydrophobicity corresponding to its strong adhesion to chicken crop epithelial cells. Co-inoculation with the fungus on modified de Man Rogosa Sharpe medium revealed the inhibitory effect of L. plantarum MYS6 on fungal growth and biomass. Observation using scanning electron microscopy showed distortion of hyphal structures, swollen tips and disrupted conidia. Conidia germination inhibition assay restrained germination and showed deformed hyphae. The bioprotective feature of the isolate was evident by the inhibition of fungal development in maize-kernel treated with the cell free supernatant of L. plantarum MYS6. Both the isolate and its extracellular metabolites lowered fumonisin content in feed model up to 0.505 mg/Kg of feed and 0.3125 mg/Kg of feed respectively when compared to the level of 0.870 mg/Kg of feed in control. The major antifungal compounds produced by the isolate were 10-Octadecenoic acid, methyl ester; palmitic acid, methyl ester; heptadecanoic acid, 16-methyl ester; stearic acid and lauric acid. L. plantarum MYS6 reduced 61.7% of fumonisin possibly by a binding mechanism. These findings suggest the application of L. plantarum MYS6 as an efficient probiotic additive and biocontrol agent in feed used in poultry industry. Additionally, the antifungal metabolites pose a conspicuous inhibition of Fusarium growth and fumonisin production. PMID:27285317

  5. Antifungal Attributes of Lactobacillus plantarum MYS6 against Fumonisin Producing Fusarium proliferatum Associated with Poultry Feeds.

    PubMed

    Deepthi, B V; Poornachandra Rao, K; Chennapa, G; Naik, M K; Chandrashekara, K T; Sreenivasa, M Y

    2016-01-01

    Fumonisins, being common in occurrence in maize-based feeds, pose a great threat to animal and human health. The present study is aimed at determining the antifungal activity of Lactobacillus plantarum MYS6 against a fumonisin producing fungus, Fusarium proliferatum MYS9. The isolate was subjected to standard tests for determining its probiotic attributes and antifungal properties. L. plantarum MYS6 thrived well at pH 3.0 and 6.0, and exhibited strong resistance up to 3% bile. The isolate showed a high degree of cell surface hydrophobicity corresponding to its strong adhesion to chicken crop epithelial cells. Co-inoculation with the fungus on modified de Man Rogosa Sharpe medium revealed the inhibitory effect of L. plantarum MYS6 on fungal growth and biomass. Observation using scanning electron microscopy showed distortion of hyphal structures, swollen tips and disrupted conidia. Conidia germination inhibition assay restrained germination and showed deformed hyphae. The bioprotective feature of the isolate was evident by the inhibition of fungal development in maize-kernel treated with the cell free supernatant of L. plantarum MYS6. Both the isolate and its extracellular metabolites lowered fumonisin content in feed model up to 0.505 mg/Kg of feed and 0.3125 mg/Kg of feed respectively when compared to the level of 0.870 mg/Kg of feed in control. The major antifungal compounds produced by the isolate were 10-Octadecenoic acid, methyl ester; palmitic acid, methyl ester; heptadecanoic acid, 16-methyl ester; stearic acid and lauric acid. L. plantarum MYS6 reduced 61.7% of fumonisin possibly by a binding mechanism. These findings suggest the application of L. plantarum MYS6 as an efficient probiotic additive and biocontrol agent in feed used in poultry industry. Additionally, the antifungal metabolites pose a conspicuous inhibition of Fusarium growth and fumonisin production.

  6. Olfactory Perception of Oviposition-Deterring Fatty Acids and Their Methyl Esters by the Asian Corn Borer, Ostrinia furnacalis

    PubMed Central

    Guo, Lei; Qing Li, Guo

    2009-01-01

    Olfactory perception of myristic, palmitic, stearic and oleic acids and their corresponding methyl esters by Asian corn borer moths, Ostrinia furnacalis (Guenée) (Lepidoptera: Crambidae) was investigated. It was found that mated females with both antennae amputated, in contrast to intact females and females with one antenna removed, could not discriminate between simultaneously provided control filter papers and filters treated with a blend of oviposition-deterring fatty acids. Oviposition by mated females exhibited a very marked periodicity, with all egg masses deposited during the scotophase and most egg masses laid before midnight. According to the peak and trough period of oviposition, electroantennogram (EAG) responses from both mated females and males to the four fatty acids and four methyl esters were tested within two two-hour periods from 3 to 5 hours after the start of darkness and from 1 to 3 hours after light onset, respectively. Significant EAG responses above solvent and background were elicited by all test chemicals from females, and by most of the test compounds from males. EAG values of all test chemicals from mated females were not statistically different between the two test periods except for methyl myristate. Conversely, EAG responses from mated males to myristic acid, stearic acid and their methyl esters significantly differed between the two test periods. PMID:20053122

  7. Synthesis and odor evaluation of five new sulfur-containing ester flavor compounds from 4-ethyloctanoic acid.

    PubMed

    Liu, Yuping; Chen, Haitao; Yin, Decai; Sun, Baoguo

    2010-07-29

    Five sulfur-containing flavor compounds were synthesized for the first time by the reaction of 4-ethyloctanoyl chloride with sulfur-containing alcohols or mercaptans. The synthesized compounds are 3-(methylthio)propyl 4-ethyloctanoate, 2-methyl-3-tetrahydro-furanthiol 4-ethyloctanoate, 4-methyl-5-thiazoleethanol 4-ethyloctanoate, 2-furan-methanethiol 4-ethyloctanoate and 2-methyl-3-furanthiol 4-ethyloctanoate. These five synthetic sulfur-containing ester flavor compounds all have meaty odor and might be used in foods if approved for this purpose in the future.

  8. Antioxidant effect of mono- and dihydroxyphenols in sunflower oil with different levels of naturally present tocopherols

    PubMed Central

    Hrádková, Iveta; Merkl, Roman; Šmidrkal, Jan; Kyselka, Jan; Filip, Vladimír

    2013-01-01

    Antioxidant properties of mono- and dihydroxyphenolic acids and their alkyl esters were examined, with emphasis on the relationship between their molecular structure and antioxidant activity. Test media with different tocopherol level were used for determining the oxidative stability: original refined sunflower oil (total tocopherols 149.0 mg/kg), partially tocopherol-stripped sunflower oil (total tocopherols 8.7 mg/kg) and distilled fatty acid methyl esters (FAME) as a tocopherol-free medium. The chemical reaction of tocopherols with diazomethane tested for the purpose to eliminate their antioxidant activity failed due to the negligible degree of methylation of hydroxyl group in the tocopherol molecule. Caffeic acid and protocatechuic acid (3,4-dihydroxyphenolic acids) and their alkyl esters were found to be more active antioxidants than monohydroxyphenolic acid (p-hydroxybenzoic acid), 2,5-dihydroxyphenolic acid (gentisic acid), 3-methoxy-4-hydroxyphenolic acids (vanillic and ferulic acids) and their corresponding alkyl esters. Naturally present tocopherols in refined sunflower oil proved to have a synergistic effect on gentisic acid but not on its alkyl esters. In contrast, tocopherols showed an antagonistic effect on alkyl esters of caffeic acid, because their protection factors decreased with increasing level of tocopherols in the test medium. Moreover, the antioxidant activity of these alkyl esters decreased with increasing length of their alkyl chain in conformity with the polar paradox hypothesis. Practical applications: Tocopherols as naturally present antioxidants influence considerably the antioxidant activity of other antioxidants added to plant oils used as a test medium. Distilled fatty acid methyl esters prepared from refined sunflower oil may serve as an optimal tocopherol-free test medium. Some alkyl esters of phenolic acids were evaluated to be applicable as natural more lipophilic antioxidants in comparison with phenolic acids. PMID:23997655

  9. 21 CFR 73.3100 - 1,4-Bis[(2-hydroxyethyl)amino]-9,10-anthracenedione bis(2-methyl-2-propenoic)ester copolymers.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 1 2014-04-01 2014-04-01 false 1,4-Bis[(2-hydroxyethyl)amino]-9,10-anthracenedione bis(2-methyl-2-propenoic)ester copolymers. 73.3100 Section 73.3100 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES GENERAL LISTING OF COLOR ADDITIVES EXEMPT FROM...

  10. Evaluation of peanut fatty acid methyl ester sprays, combustion, and emissions, for use in an indirect injection diesel engine

    USDA-ARS?s Scientific Manuscript database

    The paper provides an analysis of 100% peanut fatty acid methyl esters (FAMEs) and peanut FAME/ULSD#2 blends (P20, P35, and P50) in an indirect injection (IDI) diesel engine (for auxiliary power unit applications) in comparison to ultralow sulfur diesel no. 2 (ULSD#2) at various speeds and 100% load...

  11. Gas chromatographic-mass spectrometric determination of alkylphosphonic acids from aqueous samples by ion-pair solid-phase extraction on activated charcoal and methylation.

    PubMed

    Vijaya Saradhi, U V R; Prabhakar, S; Jagadeshwar Reddy, T; Murty, M R V S

    2007-07-20

    In the present paper, we report an improved ion-pair solid-phase extraction (IP-SPE) method for the analysis of alkylphosphonic acids, namely, methyl, ethyl and propylphosphonic acids, present in the aqueous sample. The aqueous sample was mixed with an ion-pair reagent, phenyltrimethylammonium hydroxide (PTMAH) and passed through activated charcoal SPE cartridge. The retained chemicals in the cartridge were extracted with methanol and analysed by gas chromatography-mass spectrometry (GC-MS) under the electron impact ionization (EI) mode. The analytes were converted to their methyl esters by pyrolytic methylation in the hot GC injection port. The recoveries of alkylphosphonic acids were above 95% and the minimum detection limits were as low as 10 ng/mL. The recovery of the test chemicals was tested with solvents, dichloromethane, n-hexane, ethyl acetate, acetone, acetonitrile and methanol. The chemicals could be efficiently extracted by the hydrophilic solvents. The method did not work at the highly acidic pH (when acidified with dilute HCl) but worked well from pH 4.0 to 14.0. The present method was also tested with other tetra-(methyl, ethyl, propyl and n-butyl)ammonium hydroxides. The test chemicals were not converted to their methyl and ethyl esters with tetramethyl and tetraethylammonium hydroxides, whereas they were converted to their corresponding propyl and n-butyl esters with tetrapropyl and tetra(n-butyl)ammonium hydroxides. The method was also applied to two highly cross-linked polymeric sorbents DSC-6S and Oasis HLB. The recovery of the chemicals on these sorbents was observed to be poor. Methylation using phenyltrimethylammonium hydroxide is non-hazardous and advantageous over methylation using diazomethane. The method was applied to the analysis of aqueous samples given in one of the official proficiency tests conducted by the Organization for the Prohibition of Chemical Weapons and all the spiked chemicals were identified as methyl esters.

  12. The impact of intrarenal nitric oxide synthase inhibition on renal blood flow and function in mild and severe hyperdynamic sepsis.

    PubMed

    Ishikawa, Ken; Bellomo, Rinaldo; May, Clive N

    2011-04-01

    In experimental hyperdynamic sepsis, renal function deteriorates despite renal vasodilatation and increased renal blood flow. Because nitric oxide is increased in sepsis and participates in renal blood flow control, we investigated the effects of intrarenal Nω-nitro-L-arginine methyl ester, a nonspecific nitric oxide synthase inhibitor, in mild and severe sepsis. Prospective crossover and randomized control interventional studies. University-affiliated research institute. Thirty-two merino ewes. Examination of responses to intrarenal infusion of Nω-nitro-L-arginine methyl ester for 8 hrs in unilaterally nephrectomized normal sheep and in sheep administered Escherichia coli. : In normal sheep, Nω-nitro-L-arginine methyl ester decreased renal blood flow (301 ± 30 to 228 ± 26 mL/min) and creatinine clearance (40.0 ± 5.8 to 31.1 ± 2.8 mL/min), whereas plasma creatinine increased, but fractional excretion of sodium was unchanged. In sheep with nonhypotensive hyperdynamic sepsis, plasma creatinine increased and there were decreases in creatinine clearance (34.5 ± 4.6 to 20.1 ± 3.7 mL/min) and fractional excretion of sodium despite increased renal blood flow. Infusion of Nω-nitro-L-arginine methyl ester normalized renal blood flow and increased urine output, but creatinine clearance did not improve and plasma creatinine and fractional excretion of sodium increased. In sheep with severe hypotensive sepsis, creatinine clearance decreased further (31.1 ± 5.4 to 16.0 ± 1.7 mL/min) despite increased renal blood flow. Infusion of Nω-nitro-L-arginine methyl ester restored mean arterial pressure and reduced renal blood flow but did not improve plasma creatinine or creatinine clearance. In hyperdynamic sepsis, with or without hypotension, creatinine clearance decreased despite increasing renal blood flow. Intrarenal Nω-nitro-L-arginine methyl ester infusion reduced renal blood flow but did not improve creatinine clearance. These data indicate that septic acute kidney injury is not the result of decreased renal blood flow nor is it improved by nonspecific nitric oxide synthase inhibition.

  13. Differences in neurokinin receptor pharmacology between rat and guinea-pig superior cervical ganglia.

    PubMed Central

    Seabrook, G. R.; Main, M.; Bowery, B.; Wood, N.; Hill, R. G.

    1992-01-01

    1. The depolarizations elicited by seven neurokinin receptor agonists were examined in both rat and guinea-pig superior cervical ganglia by use of grease-gap methodology in the presence of tetrodotoxin (0.1 microM). Responses were normalised with respect to 1 microM eledoisin. 2. The rank order of agonist potency in the rat ganglia was senktide greater than substance P greater than substance P methyl ester = eleidosin = Sar-Met-substance P greater than neurokinin B greater than neurokinin A, whereas in guinea-pig superior cervical ganglion (SCG) the rank order was senktide greater than Sar-Met-substance P greater than neurokinin B = eledoisin = substance P methyl ester. The concentration-effect curves for substance P and neurokinin A in guinea-pig ganglia were biphasic which precluded the determination of meaningful potency values. 3. The maximal depolarization achieved by subtype selective ligands was different between these two species. On rat and guinea-pig SCG, the NK3-selective ligand, senktide, produced a maximal depolarization of 27% and 274% respectively, whereas the NK1-selective ligand, substance P methyl ester, produced depolarizations of 77% and 64% respectively. 4. The depolarizations induced by substance P methyl ester and senktide in either species were unaffected by atropine (1 microM), suggesting a lack of involvement of presynaptic neurokinin receptors in the generation of the response. 5. The potency of substance P methyl ester, senktide, and neurokinin A were unaffected by pretreating ganglia with the peptidase inhibitors bacitracin (40 micrograms ml-1), leupeptin (4 micrograms ml-1), and chymostatin (2 micrograms ml-1). Similarly, these peptidase inhibitors had no effect on the maximal depolarizations achieved by any of these agonists.(ABSTRACT TRUNCATED AT 250 WORDS) PMID:1380375

  14. The main chemical composition and in vitro antifungal activity of the essential oils of Ocimum basilicum Linn. var. pilosum (Willd.) Benth.

    PubMed

    Zhang, Ji-Wen; Li, Sheng-Kun; Wu, Wen-Jun

    2009-01-08

    The essential oils of the aerial parts of Ocimum basilicum Linn.var. pilosum (Willd.) Benth., an endemic medicinal plant growing in China, was obtained by hydrodistillation and analysed by GC-MS. Fifteen compounds, representing 74.19% of the total oil were identified. The main components were as follows: linalool (29.68%), (Z)-cinnamic acid methyl ester (21.49%), cyclohexene (4.41%), alpha- cadinol (3.99%), 2,4-diisopropenyl-1-methyl-1-vinylcyclohexane (2.27%), 3,5-pyridine-dicarboxylic acid, 2,6-dimethyl-diethyl ester (2.01%), beta-cubebene (1.97%), guaia-1(10),11-diene (1.58%), cadinene (1.41%) (E)-cinnamic acid methyl ester (1.36%) and beta-guaiene (1.30%). The essential oils showed significant antifungal activity against some plant pathogenic fungi.

  15. Synthesis of β-Peptide Standards for Use in Model Prebiotic Reactions

    NASA Astrophysics Data System (ADS)

    Forsythe, Jay G.; English, Sloane L.; Simoneaux, Rachel E.; Weber, Arthur L.

    2018-05-01

    A one-pot method was developed for the preparation of a series of β-alanine standards of moderate size (2 to ≥12 residues) for studies concerning the prebiotic origins of peptides. The one-pot synthesis involved two sequential reactions: (1) dry-down self-condensation of β-alanine methyl ester, yielding β-alanine peptide methyl ester oligomers, and (2) subsequent hydrolysis of β-alanine peptide methyl ester oligomers, producing a series of β-alanine peptide standards. These standards were then spiked into a model prebiotic product mixture to confirm by HPLC the formation of β-alanine peptides under plausible reaction conditions. The simplicity of this approach suggests it can be used to prepare a variety of β-peptide standards for investigating differences between α- and β-peptides in the context of prebiotic chemistry.

  16. Is there evidence for man-made nanoparticles in the Dutch environment?

    PubMed

    Bäuerlein, Patrick S; Emke, Erik; Tromp, Peter; Hofman, Jan A M H; Carboni, Andrea; Schooneman, Ferry; de Voogt, Pim; van Wezel, Annemarie P

    2017-01-15

    Only very limited information is available on measured environmental concentrations of nanoparticles. In this study, several environmental compartments in The Netherlands were probed for the presence of nanoparticles. Different types of water were screened for the presence of inorganic (Ag, Au, TiO 2 ) and organic nanoparticles (C 60 , C 70 , [6,6]-phenyl-C 61 -butyric acid octyl ester, [6,6]-phenyl-C 61 -butyric acid butyl ester, [6,6]-phenyl-C 61 -butyric acid methyl ester, [6,6]-bis-phenyl-C 61 -butyric acid methyl ester, [6,6]-phenyl-C 71 -butyric acid methyl ester, [6,6]-thienyl-C 61 -butyric acid methyl ester). Air samples were analysed for the presence of nanoparticulate Mo, Ag, Ce, W, Pd, Pt, Rh, Zn, Ti, Si, B as well as Fe and Cu. ICP-MS, Orbitrap-HRMS, SEM and EDX were used for this survey. Water samples included dune and bank filtrates, surface waters and ground waters as well as influents, effluents and sludge of sewage treatment plants (STPs), and surface waters collected near airports and harbours. Air samples included both urban and rural samples. C 60 was detected in air, sewage treatment plants, influents, effluents and sludge, but in no other aqueous samples despite the low detection limit of 0.1ng/L. C 70 and functionalised fullerenes were not detected at all. In STP sludge and influent the occurrence of Ag and Au nanoparticles was verified by SEM/EDX and ICP-MS. In air up to about 25m% of certain metals was found in the nanosize fraction. Overall, between 1 and 6% of the total mass from metals in the air samples was found in the size fraction <100nm. Copyright © 2016 Elsevier B.V. All rights reserved.

  17. Preparation of polyol esters based on vegetable and animal fats.

    PubMed

    Gryglewicz, S; Piechocki, W; Gryglewicz, G

    2003-03-01

    The possibility of using some natural fats: rapeseed oil, olive oil and lard, as starting material for the preparation of neopentyl glycol (NPG) and trimethylol propane (TMP) esters is reported. The syntheses of final products were performed by alcoholysis of fatty acid methyl esters, obtained from natural fats studied, with the appropriate polyhydric alcohol using calcium methoxide as a catalyst. The basic physicochemical properties of the NPG and TMP esters synthesized were the following: viscosity at 40 degrees C in the range of 13.5-37.6 cSt, pour point between -10.5 and -17.5 degrees C and very high viscosity indices, higher than 200. Generally, the esters of neopentyl alcohols were characterized by higher stability in thermo-oxidative conditions in comparison to native triglycerides. Due to the low content of polyunsaturated acids, the olive oil based esters showed the highest thermo-oxidative resistance. Also, methyl esters of fatty acids of lard would constitute a good raw material for the synthesis of lubricating oils, provided that their saturated acids content was lowered. This permits synthesis of NPG and TMP esters with a lower pour point (below -10 degrees C) than natural lard (+33 degrees C).

  18. High-throughput screening of Erwinia chrysanthemi pectin methylesterase variants using carbohydrate microarrays.

    PubMed

    Øbro, Jens; Sørensen, Iben; Derkx, Patrick; Madsen, Christian T; Drews, Martin; Willer, Martin; Mikkelsen, Jørn D; Willats, William G T

    2009-04-01

    Pectin methylesterases (PMEs) catalyse the removal of methyl esters from the homogalacturonan (HG) backbone domain of pectin, a ubiquitous polysaccharide in plant cell walls. The degree of methyl esterification (DE) impacts upon the functional properties of HG within cell walls and plants produce numerous PMEs that act upon HG in muro. Many microbial plant pathogens also produce PMEs, the activity of which renders HG more susceptible to cleavage by pectin lyase and polygalacturonase enzymes and hence aids cell wall degradation. We have developed a novel microarray-based approach to investigate the activity of a series of variant enzymes based on the PME from the important pathogen Erwinia chrysanthemi. A library of 99 E. chrysanthemi PME mutants was created in which seven amino acids were altered by various different substitutions. Each mutant PME was incubated with a highly methyl esterified lime pectin substrate and, after digestion the enzyme/substrate mixtures were printed as microarrays. The loss of activity that resulted from certain mutations was detected by probing arrays with a mAb (JIM7) that preferentially binds to HG with a relatively high DE. Active PMEs therefore resulted in diminished JIM7 binding to the lime pectin substrate, whereas inactive PMEs did not. Our findings demonstrate the feasibility of our approach for rapidly testing the effects on PME activity of substituting a wide variety of amino acids at different positions.

  19. Synthesis of methyl ester sulfonate surfactant from crude palm oil as an active substance of laundry liquid detergent

    NASA Astrophysics Data System (ADS)

    Slamet, Ibadurrohman, Muhammad; Wulandari, Pangiastika Putri

    2017-11-01

    Liquid detergent with combination of MES surfactant and TiO2 nanoparticles to remove and degrade the dirt in the form of methylene blue and produce waste with the lowest surfactant residual concentration has been done. The formation of MES is carried out by esterification and transesterification of crude palm oil, sulfonation, refining, and neutralization. The photocatalyst TiO2 nanoparticles is added as an additive to improve surfactant performance in removing dirt and degrading organic compounds. MES formation is performed by varying the mole ratio of the reactants in the esterification and transesterification reactions, and the mole ratios between methyl esters and NaHSO3 during the sulfonation reaction. Variations of MES surfactant and TiO2 nanoparticles compositions were performed to obtain detergent stability. Data analysis technique in this research is characterization of methyl ester, MES surfactant, and detergent using UV-Vis spectrophotometer instrument, FTIR, GC-MS, and LC-MS. The optimum conditions in the esterification and transesterification process were each mole ratio of 1: 6 between CPO and methanol based on the highest conversion, 99%. The optimum condition of the sulfonation process is the 1: 1.5 mole ratio between methyl ester and NaHSO3 based on the lowest surface tension value, which is about 36 dyne/cm.

  20. Effect of chirality on cellular uptake, imaging and photodynamic therapy of photosensitizers derived from chlorophyll-a.

    PubMed

    Srivatsan, Avinash; Pera, Paula; Joshi, Penny; Wang, Yanfang; Missert, Joseph R; Tracy, Erin C; Tabaczynski, Walter A; Yao, Rutao; Sajjad, Munawwar; Baumann, Heinz; Pandey, Ravindra K

    2015-07-01

    We have previously shown that the (124)I-analog of methyl 3-(1'-m-iodobenzyloxy) ethyl-3-devinyl-pyropheophorbide-a derived as racemic mixture from chlorophyll-a can be used for PET (positron emission tomography)-imaging in animal tumor models. On the other hand, as a non-radioactive analog, it showed excellent fluorescence and photodynamic therapy (PDT) efficacy. Thus, a single agent in a mixture of radioactive ((124)I-) and non-radioactive ((127)I) material can be used for both dual-imaging and PDT of cancer. Before advancing to Phase I human clinical trials, we evaluated the activity of the individual isomers as well as the impact of a chiral center at position-3(1) in directing in vitro/in vivo cellular uptake, intracellular localization, epithelial tumor cell-specific retention, fluorescence/PET imaging, and photosensitizing ability. The results indicate that both isomers (racemates), either as methyl ester or carboxylic acid, were equally effective. However, the methyl ester analogs, due to subcellular deposition into vesicular structures, were preferentially retained. All derivatives containing carboxylic acid at the position-17(2) were noted to be substrate for the ABCG2 (a member of the ATP binding cassette transporters) protein explaining their low retention in lung tumor cells expressing this transporter. The compounds in which the chirality at position-3 has been substituted by a non-chiral functionality showed reduced cellular uptake, retention and lower PDT efficacy in mice bearing murine Colon26 tumors. Copyright © 2015 Elsevier Ltd. All rights reserved.

  1. Isolation, characterization, and purification to homogeneity of an endogenous polypeptide with agonistic action on benzodiazepine receptors.

    PubMed Central

    Guidotti, A; Forchetti, C M; Corda, M G; Konkel, D; Bennett, C D; Costa, E

    1983-01-01

    A brain polypeptide termed diazepam-binding inhibitor (DBI) and thought to be chemically and functionally related to the endogenous effector of the benzodiazepine recognition site was purified to homogeneity. This peptide gives a single band of protein on NaDodSO4 and acidic urea gel electrophoresis. A single UV-absorbing peak was obtained by HPLC using three different columns and solvent systems. DBI has a molecular mass of approximately equal to 11,000 daltons. Carboxyl-terminus analysis shows that tyrosine is the only residue while the amino-terminus was blocked. Cyanogen bromide treatment of DBI yields three polypeptide fragments, and the sequences of two of them have been determined for a total of 45 amino acids. DBI is a competitive inhibitor for the binding of [3H]diazepam, [3H]flunitrazepam, beta-[3H]carboline propyl esters, and 3H-labeled Ro 15-1788. The Ki for [3H]-diazepam and beta-[3H]carboline binding were 4 and 1 microM, respectively. Doses of DBI that inhibited [3H]diazepam binding by greater than 50% fail to change [3H]etorphine, gamma-amino[3H]butyric acid, [3H]-quinuclidinyl benzilate, [3H]dihydroalprenolol, [3H]adenosine, and [3H]imipramine binding tested at their respective Kd values. DBI injected intraventricularly at doses of 5-10 nmol completely reversed the anticonflict action of diazepam on unpunished drinking and, similar to the anxiety-inducing beta-carboline derivative FG 7142 (beta-carboline-3-carboxylic acid methyl ester), facilitated the shock-induced suppression of drinking by lowering the threshold for this response. Images PMID:6304714

  2. Gas chromatographic separation of fatty acid methyl esters on weakly polar capillary columns.

    PubMed

    Yamamoto, Kouhei; Kinoshita, Akemi; Shibahara, Akira

    2008-02-22

    It was found that weakly polar columns, routinely used in capillary GC for analyzing sterols, food additives, etc., can also be used for separating fatty acid methyl esters (FAMEs). On these columns, FAMEs elute in the order of their unsaturation. The equivalent chain-length value of methyl 22:6 is below 23.00. This means FAMEs within a carbon chain length, having up to six double bonds, elute before the next (one carbon longer) saturated FAME elutes. Peak identification is easy. Weakly polar columns are compatible in both GC and GC/MS systems.

  3. Lithium Ion Electrolytes and Lithium Ion Cells With Good Low Temperature Performance

    NASA Technical Reports Server (NTRS)

    Bugga, Ratnakumar V. (Inventor); Smart, Marshall C. (Inventor)

    2014-01-01

    There is provided in one embodiment of the invention an electrolyte for use in a lithium ion electrochemical cell. The electrolyte comprises a mixture of an ethylene carbonate (EC), an ethyl methyl carbonate (EMC), an ester cosolvent, and a lithium salt. The ester cosolvent comprises methyl propionate (MP), ethyl propionate (EP), methyl butyrate (MB), ethyl butyrate (EB), propyl butyrate (PB), or butyl butyrate (BB). The electrochemical cell operates in a temperature range of from about -60 C to about 60 C. In another embodiment there is provided a lithium ion electrochemical cell using the electrolyte of the invention.

  4. Evaluation of the antibacterial efficacy of diesters of azelaic acid.

    PubMed

    Charnock, Colin; Brudeli, Bjarne; Klaveness, Jo

    2004-04-01

    A number of diesters of the topical dermatosis treatment azelaic (nonanedioic) acid were prepared and tested for antibacterial effect. Two esters, bis-[(hexanoyloxy)methyl] nonanedioate and especially bis-[(butanoyloxy)methyl] nonanedioate showed promising activity against acne related bacteria in vitro. No activity of azelaic acid was detected in Mueller Hinton II agar at pH 7.3 when using the agar diffusion method, whereas both esters gave zones of growth inhibition. At pH 5.6, activity of azelaic acid was detected. At this pH, the zones of inhibition and MIC values obtained with azelaic acid were smaller than those of bis-[(butanoyloxy)methyl] nonanedioate for all test organisms. A preparation for topical use containing 20% (w/w) bis-[(butanoyloxy)methyl] nonanedioate, and the commercially available Skinoren (20% (w/w) azelaic acid), were compared for antibacterial effect against cutaneous bacteria using contact plate analyses of the skin. Though Skinoren was usually most effective, the differences were not statistically significant. Furthermore, bacteria surviving contact with the topical preparations were invariably more sensitive to the ester than to azelaic acid upon subculturing onto agar (pH 5.6) containing either preparation at 0.2-0.7 mg/ml. This might indicate that other factors, such as the composition of the cream base, mitigate the antibacterial activity of the ester. It is proposed that the pharmacological and microbiological properties of bis-[(butanoyloxy)methyl] nonanedioate are worthy of further study based on an extended screening of acne sufferers.

  5. Biodiesel: Fuel properties, its “Design” and a source of “Designer” fuel

    USDA-ARS?s Scientific Manuscript database

    The fuel properties of biodiesel, a biogenic alternative to petrodiesel, are largely determined by its component fatty acid alkyl esters, most commonly methyl esters. These esters have vastly different properties. The properties of biodiesel are an aggregate of the properties of its components and t...

  6. Characterization of a Feruloyl Esterase from Lactobacillus plantarum

    PubMed Central

    Esteban-Torres, María; Reverón, Inés; Mancheño, José Miguel; de las Rivas, Blanca

    2013-01-01

    Lactobacillus plantarum is frequently found in the fermentation of plant-derived food products, where hydroxycinnamoyl esters are abundant. L. plantarum WCFS1 cultures were unable to hydrolyze hydroxycinnamoyl esters; however, cell extracts from the strain partially hydrolyze methyl ferulate and methyl p-coumarate. In order to discover whether the protein Lp_0796 is the enzyme responsible for this hydrolytic activity, it was recombinantly overproduced and enzymatically characterized. Lp_0796 is an esterase that, among other substrates, is able to efficiently hydrolyze the four model substrates for feruloyl esterases (methyl ferulate, methyl caffeate, methyl p-coumarate, and methyl sinapinate). A screening test for the detection of the gene encoding feruloyl esterase Lp_0796 revealed that it is generally present among L. plantarum strains. The present study constitutes the description of feruloyl esterase activity in L. plantarum and provides new insights into the metabolism of hydroxycinnamic compounds in this bacterial species. PMID:23793626

  7. Characterization of a feruloyl esterase from Lactobacillus plantarum.

    PubMed

    Esteban-Torres, María; Reverón, Inés; Mancheño, José Miguel; de Las Rivas, Blanca; Muñoz, Rosario

    2013-09-01

    Lactobacillus plantarum is frequently found in the fermentation of plant-derived food products, where hydroxycinnamoyl esters are abundant. L. plantarum WCFS1 cultures were unable to hydrolyze hydroxycinnamoyl esters; however, cell extracts from the strain partially hydrolyze methyl ferulate and methyl p-coumarate. In order to discover whether the protein Lp_0796 is the enzyme responsible for this hydrolytic activity, it was recombinantly overproduced and enzymatically characterized. Lp_0796 is an esterase that, among other substrates, is able to efficiently hydrolyze the four model substrates for feruloyl esterases (methyl ferulate, methyl caffeate, methyl p-coumarate, and methyl sinapinate). A screening test for the detection of the gene encoding feruloyl esterase Lp_0796 revealed that it is generally present among L. plantarum strains. The present study constitutes the description of feruloyl esterase activity in L. plantarum and provides new insights into the metabolism of hydroxycinnamic compounds in this bacterial species.

  8. Aroma enhancement and enzymolysis regulation of grape wine using β-glycosidase

    PubMed Central

    Zhu, Feng-Mei; Du, Bin; Li, Jun

    2014-01-01

    Adding β-glycosidase into grape wine for enhancing aroma was investigated using gas chromatography-mass spectrometry (GC-MS) and Kramer sensory evaluation. Compared with the extract from control wines, the extract from enzyme-treated wines increased more aromatic compounds using steam distillation extraction (SDE) and GC-MS analyses. Theses aromatic compounds were as follows: 3-methyl-1-butanol formate, 3-pentanol, furfural, 3-methyl-butanoic acid, 2-methyl-butanoic acid, 3-hydroxy-butanoic acid ethyl ester, hexanoic acid, hexanoic acid ethyl ester, benzyl alcohol, octanoic acid, octanoic acid ethyl ester, dodecanoic acid, and ethyl ester. The enzymolysis regulation conditions, including enzymolysis temperature, enzymolysis time, and enzyme amount, were optimized through L9(34) orthogonal test. Kramer sensory evaluation was performed by an 11-man panel of judges. The optimum enzymolysis regulation conditions were found to be temperature of 45°C, enzymolysis time of 90 min, and enzyme amount of 58.32 U/mL grape wine, respectively. The Kramer sensory evaluation supported that the enzyme-treated wines produced a stronger fragrance. PMID:24804072

  9. Efficient and Scalable Synthesis of 4-Carboxy-Pennsylvania Green Methyl Ester: A Hydrophobic Building Block for Fluorescent Molecular Probes.

    PubMed

    Woydziak, Zachary R; Fu, Liqiang; Peterson, Blake R

    2014-01-01

    Fluorinated fluorophores are valuable tools for studies of biological systems. However, amine-reactive single-isomer derivatives of these compounds are often very expensive. To provide an inexpensive alternative, we report a practical synthesis of 4-carboxy-Pennsylvania Green methyl ester. Derivatives of this hydrophobic fluorinated fluorophore, a hybrid of the dyes Oregon Green and Tokyo Green, are often cell permeable, enabling labeling of intracellular targets and components. Moreover, the low pKa of Pennsylvania Green (4.8) confers bright fluorescence in acidic cellular compartments such as endosomes, enhancing its utility for chemical biology investigations. To improve access to the key intermediate 2,7-difluoro-3,6-dihydroxyxanthen-9-one, we subjected bis-(2,4,5-trifluorophenyl)methanone to iterative nucleophilic aromatic substitution by hydroxide on scales of > 40 g. This intermediate was used to prepare over 15 grams of pure 4-carboxy-Pennsylvania Green methyl ester in 28% overall yield without requiring chromatography. This compound can be converted into the amine reactive N -hydroxysuccinimidyl ester in essentially quantitative yield for the synthesis of a wide variety of fluorescent molecular probes.

  10. Thermal Decomposition of Potential Ester Biofuels. Part I: Methyl Acetate and Methyl Butanoate

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    Porterfield, Jessica P.; Bross, David H.; Ruscic, Branko

    2017-06-09

    Two methyl esters have been examined as models for the pyrolysis of biofuels. Dilute samples (0.06 - 0.13%) of methyl acetate (CH 3COOCH 3) and methyl butanoate (CH 3CH 2CH 2COOCH 3) were entrained in (He, Ar) carrier gas and decomposed in a set of flash-pyrolysis micro-reactors. The pyrolysis products resulting from the methyl esters were detected and identified by vacuum ultraviolet photoionization mass spectrometry. Complementary product identification was provided by matrix infrared absorption spectroscopy. Pyrolysis pressures in the pulsed micro-reactor were roughly 20 Torr and residence times through the reactors were approximately 25 - 150 µs. Reactor temperatures ofmore » 300 – 1600 K were explored. Decomposition of CH 3COOCH 3 commences at 1000 K and the initial products are (CH 2=C=O and CH 3OH). As the micro-reactor is heated to 1300 K, a mixture of (CH 2=C=O and CH 3OH, CH 3, CH 2=O, H, CO, CO 2) appears. The thermal cracking of CH 3CH 2CH 2COOCH 3 begins at 800 K with the formation of (CH 3CH 2CH=C=O, CH 3OH). By 1300 K, the pyrolysis of methyl butanoate yields a complex mixture of (CH 3CH 2CH=C=O, CH 3OH, CH 3, CH 2=O, CO, CO 2, CH 3CH=CH 2, CH 2CHCH 2, CH 2=C=CH 2, HCCCH 2, CH 2=C=C=O, CH 2=CH 2, HCΞCH, CH 2=C=O). Based on the results from the thermal cracking of methyl acetate and methyl butanoate, we predict several important decomposition channels for the pyrolysis of fatty acid methyl esters, R CH 2-COOCH 3. The lowest energy fragmentation will be a 4-center elimination of methanol to form the ketene, RCH=C=O. At higher temperatures, concerted fragmentation to radicals will ensue to produce a mixture of species: (RCH 2 + CO 2 + CH 3) and (RCH 2 + CO + CH 2=O + H). Thermal cracking of the β C-C bond of the methyl ester will generate the radicals (R and H) as well as CH 2=C=O + CH 2=O. The thermochemistry of methyl acetate and its fragmentation products have been obtained via the Active Thermochemical Tables (ATcT) approach, resulting in Δ fH 298(CH 3COOCH 3) = -98.7 ± 0.2 kcal mol -1, Δ fH 298(CH 3CO 2) = -45.7 ± 0.3 kcal mol -1, and Δ fH 298(COOCH 3) = -38.3 ± 0.4 kcal mol -1.« less

  11. Action of a new cholinergic agonist, aclatonium napadisilate, on isolated rat pancreatic acini

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    Fujii, M.; Okabayashi, Y.; Nakamura, T.

    1990-07-01

    The effect of aclatonium napadisilate, a newly synthesized choline ester, on pancreatic exocrine function was compared with that of the muscarinic agonist carbamylcholine in isolated rat pancreatic acini. Both compounds increased amylase release and {sup 45}Ca{sup 2+} efflux in a dose-dependent fashion, and similarly decreased the binding of (N-methyl-{sup 3}H)scopolamine to isolated rat pancreatic acini. While aclatonium napadisilate was 20-30 times less potent than carbamylcholine in stimulations of amylase release and {sup 45}Ca{sup 2+} efflux, the potency of aclatonium napadisilate in inhibiting (N-methyl-{sup 3}H)scopolamine binding was nearly the same as that of carbamylcholine. These results indicate that aclatonium napadisilate stimulatesmore » pancreatic exocrine secretion via muscarinic receptors and Ca{sup 2+} mobilization, and its intrinsic activity is less than carbamylcholine in the isolated rat pancreatic acini. Since aclatonium napadisilate is known to increase motility and peristalsis of the gastrointestinal tract, stimulatory effects of aclatonium napadisilate, shown in the present study, on digestive enzyme secretion from the pancreas may provide additional benefit of aclatonium napadisilate in the treatment of various gastrointestinal disorders.« less

  12. 40 CFR 721.10271 - 3′H-Cyclopropa[1,9][5,6]fullerene-C60-Ih-3′-butanoic acid, 3′-phenyl-, methyl ester.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10271 3′H-Cyclopropa[1,9][5,6]fullerene-C60-Ih-3′-butanoic acid, 3′-phenyl-, methyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as 3′H-Cyclopropa[1,9][5,6...

  13. 40 CFR 721.10271 - 3′H-Cyclopropa[1,9][5,6]fullerene-C60-Ih-3′-butanoic acid, 3′-phenyl-, methyl ester.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10271 3′H-Cyclopropa[1,9][5,6]fullerene-C60-Ih-3′-butanoic acid, 3′-phenyl-, methyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as 3′H-Cyclopropa[1,9][5,6...

  14. Occurrence of fatty acid chlorohydrins in jellyfish lipids.

    PubMed

    White, R H; Hager, L P

    1977-11-01

    Fatty acid chlorohydrins are characterized as lipid components of an edible jellyfish. The four isomers 9-chloro-10-hydroxypalmitic acid, 10-chloro-9-hydroxypalmitic acid, 9-chloro-10-hydroxystearic acid, and 10-chloro-9-hydroxystearic acid were identified by gas chromatography-mass spectrometry comparison of the methyl esters and their trimethylsilyl derivatives with known synthetic samples. Two additional isomers, 11-chloro-12-hydroxystearic acid and 12-chloro-11-hydroxystearic acid, were also found in the lipid by the identification of the expected mass spectral fragments of the trimethylsilyl (Me3Si) derivative of their methyl esters. These six isomeric compounds represented approximately 1.4% of the total extractable jellyfish lipid and were released from the lipid as methyl esters by boron trifluoride-methanol treatment. These isomers account for only about 30% of the organic chlorine in the lipid. Evidence is given that the remaining organic chlorine is also present as fatty acid chlorohydrins containing more than one hydroxyl group.

  15. Production of Biodiesel from Thespesiapopulnea seed oil through rapid in situ transesterification - an optimization study and assay of fuel properties

    NASA Astrophysics Data System (ADS)

    Bhargavi, G.; Nageswara Rao, P.; Renganathan, S.

    2018-03-01

    Biodiesel production was carried out from Thespesia populnea seed oil through rapid insitu transesterification. Influence of reaction parameters such as catalyst type and concentration, methanol to biomass ratio, co-solvent volume, temperature and agitation speed on conversion of oil into methyl esters was investigated. The effect of different co-solvents on conversion was evaluated. Optimum methyl ester conversion of 97.80% was achieved at 1.5wt% of KOH catalyst, 5.5:1 (v/w) methanol to biomass ratio, 25vol%tetrahydrofuranco-solvent, 60°C and 500 rpm within 120min of reaction time. Fuel properties of produced methyl esters were well fitted within the limits of ASTMD 6751 standards. Considering the properties of produced biodiesel, Thespesia populnea seed derived biodiesel can be used as potential alternate to fossil diesel fuel.

  16. Enhancement effect on the chemiluminescence of acridinium esters under neutral conditions.

    PubMed

    Nakazono, Manabu; Nanbu, Shinkoh

    2018-03-01

    Enhancement effect on the chemiluminescence of acridinium ester derivatives under neutral conditions was investigated. Additions of phenols did not enhance the chemiluminescence intensities of acridinium ester derivatives in the presence of horseradish peroxidase and hydrogen peroxide. Additions of cetyltrimethylammonium bromide apparently enhanced the chemiluminescence intensities of phenyl 10-methyl-10λ 4 -acridine-9-carboxylate derivatives with electron-withdrawing groups at the 4-position of the phenyl group. In particular, the chemiluminescence intensity of 4-(trifluoromethyl)phenyl 10-methyl-10λ 4 -acridine-9-carboxylate trifluoromethanesulfonate salt was 5.5 times stronger in the presence of cetyltrimethylammonium bromide than in its absence at pH 7. The chemiluminescence intensity of 3,4-dicyano-phenyl 10-methyl-10λ 4 -acridine-9-carboxylate trifluoromethanesulfonate salt was 46 times stronger in the presence of cetyltrimethylammonium bromide at pH 7 than in its absence at pH 10. Copyright © 2017 John Wiley & Sons, Ltd.

  17. Optimized Carbonate and Ester-Based Li-Ion Electrolytes

    NASA Technical Reports Server (NTRS)

    Smart, Marshall; Bugga, Ratnakumar

    2008-01-01

    To maintain high conductivity in low temperatures, electrolyte co-solvents have been designed to have a high dielectric constant, low viscosity, adequate coordination behavior, and appropriate liquid ranges and salt solubilities. Electrolytes that contain ester-based co-solvents in large proportion (greater than 50 percent) and ethylene carbonate (EC) in small proportion (less than 20 percent) improve low-temperature performance in MCMB carbon-LiNiCoO2 lithium-ion cells. These co-solvents have been demonstrated to enhance performance, especially at temperatures down to 70 C. Low-viscosity, ester-based co-solvents were incorporated into multi-component electrolytes of the following composition: 1.0 M LiPF6 in ethylene carbonate (EC) + ethyl methyl carbonate (EMC) + X (1:1:8 volume percent) [where X = methyl butyrate (MB), ethyl butyrate EB, methyl propionate (MP), or ethyl valerate (EV)]. These electrolyte formulations result in improved low-temperature performance of lithium-ion cells, with dramatic results at temperatures below 40 C.

  18. Distribution of C22-, C24- and C26-alpha-unit-containing mycolic acid homologues in mycobacteria.

    PubMed

    Kaneda, K; Imaizumi, S; Yano, I

    1995-01-01

    There are three mycolic acid homologues with C22-, C24- and C26-alpha-units in Mycobacterium. In order to reveal the composition and distribution of these homologues in each subclass and molecular species of mycolic acids and to compare them with the composition of constitutive non-polar fatty acids (free and bound forms), we have separated non-polar fatty acids and each subclass of mycolic acids from 21 mycobacterial species by thin-layer chromatography, and analyzed non-polar fatty acid methyl esters by gas chromatography (GC) and the cleavage products of methyl mycolate by pyrolysis GC. We further performed mass chromatographic analysis of trimethylsilyl (TMS) ether derivatives of mycolic acid methyl esters by monitoring [B-29]+ ions (loss of CHO from the alpha-branched-chain structure of mycolic acids) of m/z 426, 454 and 482 which are attributed to C22-, C24- and C26-alpha-units of TMS ether derivatives of methyl mycolates, respectively, (Kaneda, K. et al, J. Clin. Microbiol. 24: 1060-1070, 1986). By pyrolysis GC, C22:0, C24:0 and C26:0 fatty acid methyl esters generated by the C2-C3 cleavage of C22-, C24- and C26-alpha-unit-containing mycolic acid methyl esters, respectively, were detected. Their proportion was almost the same among subclasses of mycolic acids in every Mycobacterium and also similar to the proportion of constitutive non-polar C22:0, C24:0 and C26:0 fatty acids. By mass chromatography, the composition and distribution of C22- and C24-alpha-unit-containing homologues were revealed to be similar between alpha- and alpha'-mycolic acids in every Mycobacterium.(ABSTRACT TRUNCATED AT 250 WORDS)

  19. Modulation of the degree and pattern of methyl-esterification of pectic homogalacturonan in plant cell walls. Implications for pectin methyl esterase action, matrix properties, and cell adhesion.

    PubMed

    Willats, W G; Orfila, C; Limberg, G; Buchholt, H C; van Alebeek, G J; Voragen, A G; Marcus, S E; Christensen, T M; Mikkelsen, J D; Murray, B S; Knox, J P

    2001-06-01

    Homogalacturonan (HG) is a multifunctional pectic polysaccharide of the primary cell wall matrix of all land plants. HG is thought to be deposited in cell walls in a highly methyl-esterified form but can be subsequently de-esterified by wall-based pectin methyl esterases (PMEs) that have the capacity to remove methyl ester groups from HG. Plant PMEs typically occur in multigene families/isoforms, but the precise details of the functions of PMEs are far from clear. Most are thought to act in a processive or blockwise fashion resulting in domains of contiguous de-esterified galacturonic acid residues. Such de-esterified blocks of HG can be cross-linked by calcium resulting in gel formation and can contribute to intercellular adhesion. We demonstrate that, in addition to blockwise de-esterification, HG with a non-blockwise distribution of methyl esters is also an abundant feature of HG in primary plant cell walls. A partially methyl-esterified epitope of HG that is generated in greatest abundance by non-blockwise de-esterification is spatially regulated within the cell wall matrix and occurs at points of cell separation at intercellular spaces in parenchymatous tissues of pea and other angiosperms. Analysis of the properties of calcium-mediated gels formed from pectins containing HG domains with differing degrees and patterns of methyl-esterification indicated that HG with a non-blockwise pattern of methyl ester group distribution is likely to contribute distinct mechanical and porosity properties to the cell wall matrix. These findings have important implications for our understanding of both the action of pectin methyl esterases on matrix properties and mechanisms of intercellular adhesion and its loss in plants.

  20. Diatomite-supported Pd-M (M=Cu, Co, Ni) bimetal nanocatalysts for selective hydrogenation of long-chain aliphatic esters.

    PubMed

    Huang, Changliang; Zhang, Hongye; Zhao, Yanfei; Chen, Sha; Liu, Zhimin

    2012-11-15

    Diatomite supported Pd-M (M=Cu, Co, Ni) bimetal nanocatalysts with various metal compositions were prepared and characterized by means of X-ray diffraction, transmission electron microscopy, and X-ray photoelectron spectroscopy. It was demonstrated that the metal nanoparticles were uniformly distributed on the support, and their size was centered around 8 nm with a relatively narrow size distribution. The catalysts were used to catalyze hydrogenation of long-chain aliphatic esters, including methyl palmitate, methyl stearate, and methyl laurate. It was indicated that the all diatomite-supported Pd-based bimetal catalysts were active to the selective hydrogenation of long-chain esters to corresponding alcohols at 270°C, originated from the synergistic effect between the metal particles and the diatomite support. For the selective hydrogenation of methyl palmitate, Pd-Cu/diatomite with metal loading of 1% and Pd/Cu=3 displayed the highest performance, giving a 1-hexadecanol yield of 82.9% at the substrate conversion of 98.8%. Copyright © 2012 Elsevier Inc. All rights reserved.

  1. Synthesis, structural and conformational study of some esters derived from 3-methyl-3-azabicyclo[3.2.1]octan-8(α and β)-ols

    NASA Astrophysics Data System (ADS)

    Iriepa, I.; Bellanato, J.

    2014-09-01

    A series of α and β-esters bearing a 3-methyl-3-azabicyclo[3.2.1]octane moiety as well as methyl and aryl substituents were synthesized and studied by 1H and 13C NMR spectroscopies. In CDCl3 solution, at room temperature, a chair-envelope conformation for the bicycle moiety with the N-CH3 group in equatorial position with respect to the chair ring is proposed for both, α and β-esters. The chair conformation of the piperidine ring is puckered at C8 in the α-epimers and it is flattened at N3, in the β-epimers. Free rotation of the acyloxy group around the C8sbnd O bond has also been deduced. Analgesic activity of four of these substances was studied. 8β-Benzoyloxy-3-methyl-3-azabicyclo[3.2.1]octane demonstrated significant analgesic activity in the hot plate test compared to morphine. By measuring the rectal temperature in mice, results also showed a significant antipyretic activity of this compound.

  2. Regulation of Hippocampal Glutamate Receptors: Evidence for the Involvement of a Calcium-Activated Protease

    NASA Astrophysics Data System (ADS)

    Baudry, Michel; Lynch, Gary

    1980-04-01

    Specific [3H]glutamate binding to rat hippocampal membranes and the calcium-induced increase in this binding are markedly temperature-sensitive and are inhibited by alkylating or reducing agents as well as by various protease inhibitors. N-Ethylmaleimide, chloromethyl ketone derivatives of lysine and phenylalanine, and tosylarginine methyl ester decrease the maximum number of [3H]glutamate binding sites without changing their affinity for glutamate. Preincubation of the membranes with glutamate does not protect the glutamate ``receptors'' from the suppressive effects of these agents. The proteases trypsin and α -chymotrypsin increase the maximum number of [3H]glutamate binding sites. The effects of calcium on glutamate binding are different across brain regions. Cerebellar membranes are almost insensitive whereas hippocampal and striatal membranes exhibit a strong increase in the number of binding sites after exposure to even low concentrations of calcium. These results suggest that an endogenous membrane-associated thiol protease regulates the number of [3H]glutamate binding sites in hippocampal membranes and that this is the mechanism by which calcium stimulates glutamate binding. The possibility is discussed that the postulated mechanisms participate in synaptic physiology and in particular may be related to the long-term potentiation of transmission found in hippocampus under certain conditions.

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

    NASA Astrophysics Data System (ADS)

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

    2017-03-01

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

  4. Hydrolysis of Synthetic Esters by the Antibacterial Agent in Serum

    PubMed Central

    Yotis, William W.

    1966-01-01

    Yotis, William W. (Loyola University, Chicago, Ill.). Hydrolysis of synthetic esters by the antibacterial agent in serum. J. Bacteriol. 91:488–493. 1966.—An antistaphylococcal serum agent was assayed colorimetrically, manometrically, and titrimetrically for esterase activity. p-Nitrophenol acetate, triacetin, l-lysine methyl and ethyl ester, and norleucine methyl ester were hydrolyzed by the antistaphylococcal agent. Acetylcholine and benzoylcholine esters, triolein, tristearin, and p-tosylarginine methyl ester were not attacked by this agent. With p-nitrophenol acetate as substrate, optimal activity occurred at pH 7.4. Incubation at 60 C for 30 min reduced drastically the esterase activity of the antistaphylococcal agent, and incubation at 75 C for 30 min abolished the esterase activity of this agent. Almost complete inhibition of esterase activity was observed with 0.001 m HgCl2, ZnSO4, and ethylenediaminetetraacetic acid (EDTA). EDTA inhibition could be reversed by the addition of CaCl2, but not MgCl2. Cysteine reversed the inhibition of HgCl2. NaF, atoxyl, diisopropyl fluorophosphate, quinine, and physostigmine did not influence the esterase activity of the antibacterial agent. The demonstration of esterase activity of both the antistaphylococcal agent and coagulase may shed further light on the reported ability of coagulase to neutralize the antistaphylococcal activity of this agent, or the prevention of absorption of the agent on the staphylococcal cell surface. In addition, the colorimetric procedure described in this report may be a convenient tool in assaying the potency of the antistaphylococcal agent. Images PMID:4956776

  5. Synthesis of fatty acid methyl ester from used vegetable cooking oil by solid reusable Mg 1-x Zn 1+x O2 catalyst.

    PubMed

    Olutoye, M A; Hameed, B H

    2011-02-01

    Fatty acid methyl ester was produced from used vegetable cooking oil using Mg(1-)(x) Zn(1+)(x)O(2) solid catalyst and the performance monitored in terms of ester content obtained. Used vegetable cooking oil was employed to reduce operation cost of biodiesel. The significant operating parameters which affect the overall yield of the process were studied. The highest ester content, 80%, was achieved with the catalyst during 4h 15 min reaction at 188°C with methanol to oil ratio of 9:1 and catalyst loading of 2.55 wt% oil. Also, transesterification of virgin oil gave higher yield with the heterogeneous catalyst and showed high selectivity towards ester production. The used vegetable cooking oil did not require any rigorous pretreatment. Catalyst stability was examined and there was no leaching of the active components, and its performance was as good at the fourth as at the first cycle. Copyright © 2010 Elsevier Ltd. All rights reserved.

  6. Molecular Modulation of Inhibitors of Apoptosis as a Novel Approach for Radiosensitization of Human Prostate Cancer

    DTIC Science & Technology

    2008-11-01

    was purified from natural racemic gossypol. Briefly, racemic gossypol was reacted with L - phenylalanine methyl ester hydrochloride overnight at room...solution of the resolved (F)-gossypol- phenylalanine methyl ester Schiff’s base was hydrolyzed by a mixture of tetrahydro- furan, glacial acetic acid...suppression of NF-kappaB-regulated antiapoptotic and metastatic gene products. Mol Pharmacol 2007; 71: 209-19. [136]Wang L , Du F, Wang X. TNF- alpha induces

  7. An evidence of C16 fatty acid methyl esters extracted from microalga for effective antimicrobial and antioxidant property.

    PubMed

    Davoodbasha, MubarakAli; Edachery, Baldev; Nooruddin, Thajuddin; Lee, Sang-Yul; Kim, Jung-Wan

    2018-02-01

    Fatty acid methyl esters (FAME) derived from lipids of microalgae is known to have wide bio-functional materials including antimicrobials. FAME is an ideal super-curator and superior anti-pathogenic. The present study evaluated the efficiency of FAME extracted from microalgae Scenedesmus intermedius as an antimicrobial agent against Gram positive (Staphylococcus aureus, Streptococcus mutans, and Bacillus cereus) Gram negative (Escherichia coli and Pseudomonas aeruginosa) bacteria and Fungi (Aspergillus parasiticus and Candida albicans). The minimal inhibitory concentration (MIC) for the gram negative bacteria was determined as 12-24 μg mL -1 , whereas MIC for gram positive bacteria was 24-48 μg mL -1 . MIC for the fungi was as high as 60-192 μg mL -1 . The FAME profiles determined by gas chromatography showed 18 methyl esters. Among them, pharmacologically active FAME such as palmitic acid methyl ester (C16:0) was detected at high percentage (23.08%), which accounted for the bioactivity. FAME obtained in this study exhibited a strong antimicrobial activity at the lowest MIC than those of recent reports. This result clearly indicated that FAME of S. intermedius has a strong antimicrobial and antioxidant property and that could be used as an effective resource against microbial diseases. Copyright © 2017. Published by Elsevier Ltd.

  8. Effects of Alumina Nano Metal Oxide Blended Palm Stearin Methyl Ester Bio-Diesel on Direct Injection Diesel Engine Performance and Emissions

    NASA Astrophysics Data System (ADS)

    Krishna, K.; Kumar, B. Sudheer Prem; Reddy, K. Vijaya Kumar; Charan Kumar, S.; Kumar, K. Ravi

    2017-08-01

    The Present Investigation was carried out to study the effect of Alumina Metal Oxide (Al2O3) Nano Particles as additive for Palm Stearin Methyl Ester Biodiesel (B 100) and their blends as an alternate fuel in four stroke single cylinder water cooled, direct injection diesel engine. Alumina Nano Particles has high calorific value and relatively high thermal conductivity (30-1 W m K-1) compare to diesel, which helps to promote more combustion in engines due to their higher thermal efficiency. In the experimentation Al2O3 were doped in various proportions with the Palm Stearin Methyl Ester Biodiesel (B-100) using an ultrasonicator and a homogenizer with cetyl trimethyl ammonium bromide (CTAB) as the cationic surfactant. The test were performed on a Kirsloskar DI diesel engine at constant speed of 1500 rpm using different Nano Biodiesel Fuel blends (psme+50 ppm, psme+150 ppm, and psme+200 ppm) and results were compared with those of neat conventional diesel and Palm Stearin Methyl Ester Bio diesel. It was observed that for Nano Biodiesel Fuel blend (psme+50ppm) there is an significant reduction in carbon monoxide (CO) emissions and Nox emissions compared to diesel and the brake thermal efficiency for (psme+50ppm) was almost same as diesel.

  9. Control of postharvest Botrytis fruit rot of strawberry by volatile organic compounds of Candida intermedia.

    PubMed

    Huang, R; Li, G Q; Zhang, J; Yang, L; Che, H J; Jiang, D H; Huang, H C

    2011-07-01

    A study was conducted to identify volatile organic compounds or volatiles produced by Candida intermedia strain C410 using gas chromatography-mass spectrometry, and to determine efficacy of the volatiles of C. intermedia in suppression of conidial germination and mycelial growth of Botrytis cinerea and control of Botrytis fruit rot of strawberry. Results showed that, among 49 volatiles (esters, alcohols, alkenes, alkanes, alkynes, organic acids, ketones, and aldehydes) identified from C. intermedia cultures on yeast extract peptone dextrose agar, two compounds, 1,3,5,7-cyclooctatetraene and 3-methyl-1-butanol, were the most abundant. Synthetic chemicals of 1,3,5,7-cyclooctatetraene; 3-methyl-1-butanol; 2-nonanone; pentanoic acid, 4-methyl-, ethyl ester; 3-methyl-1-butanol, acetate; acetic acid, pentyl ester; and hexanoic acid, ethyl ester were highly inhibitory to conidial germination and mycelial growth of B. cinerea. Inhibition of conidial germination and mycelial growth of B. cinerea by volatiles of C. intermedia was also observed. Meanwhile, results showed that incidence and severity of Botrytis fruit rot of strawberry was significantly (P < 0.01) reduced by exposure of the strawberry fruit to the volatiles from C. intermedia cultures or C. intermedia-infested strawberry fruit. These results suggest that the volatiles of C. intermedia C410 are promising biofumigants for control of Botrytis fruit rot of strawberry.

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

    NASA Astrophysics Data System (ADS)

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

    2017-05-01

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

  11. 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

  12. Structural characterization of saturated branched chain fatty acid methyl esters by collisional dissociation of molecular ions generated by electron ionization.

    PubMed

    Ran-Ressler, Rinat R; Lawrence, Peter; Brenna, J Thomas

    2012-01-01

    Saturated branched chain fatty acids (BCFA) are present as complex mixtures in numerous biological samples. The traditional method for structure elucidation, electron ionization (EI) mass spectrometry, sometimes does not unambiguously enable assignment of branching in isomeric BCFA. Zirrolli and Murphy (Zirrolli , J. A. , and R. A. Murphy. 1993. Low-energy tandem mass spectrometry of the molecular ion derived from fatty acid methyl esters: a novel method for analysis of branched-chain fatty acids. J. Am. Soc. Mass Spectrom. 4: 223-229.) showed that the molecular ions of four BCFA methyl ester (BCFAME) yield highly characteristic fragments upon collisional dissociation using a triple quadrupole instrument. Here, we confirm and extend these results by analysis using a tabletop 3-D ion trap for activated molecular ion EI-MS/MS to 30 BCFAME. iso-BCFAME produces a prominent ion (30-100% of base peak) for [M-43] (M-C₃H₇), corresponding to the terminal isopropyl moiety in the original iso-BCFAME. Anteiso-FAME yield prominent ions (20-100% of base peak) corresponding to losses on both side of the methyl branch, [M-29] and [M-57], and tend to produce more prominent m/z 115 peaks corresponding to a cyclization product around the ester. Dimethyl and tetramethyl FAME, with branches separated by at least one methylene group, yield fragment on both sides of the sites of methyl branches that are more than 6 C away from the carboxyl carbon. EI-MS/MS yields uniquely specific ions that enable highly confident structural identification and quantification of BCFAME.

  13. Structural characterization of saturated branched chain fatty acid methyl esters by collisional dissociation of molecular ions generated by electron ionization[S

    PubMed Central

    Ran-Ressler, Rinat R.; Lawrence, Peter; Brenna, J. Thomas

    2012-01-01

    Saturated branched chain fatty acids (BCFA) are present as complex mixtures in numerous biological samples. The traditional method for structure elucidation, electron ionization (EI) mass spectrometry, sometimes does not unambiguously enable assignment of branching in isomeric BCFA. Zirrolli and Murphy (Zirrolli , J. A. , and R. A. Murphy. 1993. Low-energy tandem mass spectrometry of the molecular ion derived from fatty acid methyl esters: a novel method for analysis of branched-chain fatty acids. J. Am. Soc. Mass Spectrom. 4: 223–229.) showed that the molecular ions of four BCFA methyl ester (BCFAME) yield highly characteristic fragments upon collisional dissociation using a triple quadrupole instrument. Here, we confirm and extend these results by analysis using a tabletop 3-D ion trap for activated molecular ion EI-MS/MS to 30 BCFAME. iso-BCFAME produces a prominent ion (30-100% of base peak) for [M-43] (M-C3H7), corresponding to the terminal isopropyl moiety in the original iso-BCFAME. Anteiso-FAME yield prominent ions (20-100% of base peak) corresponding to losses on both side of the methyl branch, [M-29] and [M-57], and tend to produce more prominent m/z 115 peaks corresponding to a cyclization product around the ester. Dimethyl and tetramethyl FAME, with branches separated by at least one methylene group, yield fragment on both sides of the sites of methyl branches that are more than 6 C away from the carboxyl carbon. EI-MS/MS yields uniquely specific ions that enable highly confident structural identification and quantification of BCFAME. PMID:22021637

  14. High enantiomeric excess of the flavor relevant 4-alkyl-branched Fatty acids in milk fat and subcutaneous adipose tissue of sheep and goat.

    PubMed

    Kaffarnik, Stefanie; Heid, Carolina; Kayademir, Yasemin; Eibler, Dorothee; Vetter, Walter

    2015-01-21

    Volatile 4-alkyl-branched fatty acids are characteristic flavor compounds of sheep and goat. Due to the methyl branch, the carbon C-4 represents a stereogenic center with the possible presence of one or both enantiomers in the respective samples. In this study, we used enantioselective gas chromatography to study the enantiomeric composition of 4-methyloctanoic acid (4-Me-8:0) and 4-ethyloctanoic acid (4-Et-8:0) in milk and dairy products from sheep and goat as well as in goat subcutaneous tissue. Different columns coated with modified cyclodextrins were tested to resolve racemic 4-alkyl-branched fatty acid methyl ester standards. The best enantiomer resolution was obtained on 25% octakis(2,3,6-tri-O-ethyl)-γ-cyclodextrin (γ-TECD) diluted in OV-1701. For analysis of the food samples, the lipids were extracted and fatty acids in the extracts were converted into fatty acid methyl esters. Non-aqueous reversed-phase high-performance liquid chromatography was used to fractionate the samples in order to gain one solution enriched in 4-Me-8:0 methyl ester and one solution enriched with 4-Et-8:0 methyl ester. Subsequent analysis by enantioselective gas chromatography with mass spectrometry allowed only the detection of one enantiomer of 4-Me-8:0 and 4-Et-8:0 in the samples. By means of a non-racemic standard of 4-Me-8:0, it was found that the predominant enantiomer was (R)-4-Me-8:0.

  15. 40 CFR 721.10526 - 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, telomers with C18-26-alkyl acrylate, 1...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...-dodecanethiol, N-(hydroxymethyl)-2-methyl-2-propenamide, polyfluorooctyl methacrylate and vinylidene chloride, 2...-alkyl acrylate, 1-dodecanethiol, N-(hydroxymethyl)-2-methyl-2-propenamide, polyfluorooctyl methacrylate... 40 Protection of Environment 32 2013-07-01 2013-07-01 false 2-Propenoic acid, 2-methyl-, 2...

  16. 40 CFR 721.10526 - 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, telomers with C18-26-alkyl acrylate, 1...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...-dodecanethiol, N-(hydroxymethyl)-2-methyl-2-propenamide, polyfluorooctyl methacrylate and vinylidene chloride, 2...-alkyl acrylate, 1-dodecanethiol, N-(hydroxymethyl)-2-methyl-2-propenamide, polyfluorooctyl methacrylate... 40 Protection of Environment 31 2014-07-01 2014-07-01 false 2-Propenoic acid, 2-methyl-, 2...

  17. Glucuronoyl esterases are active on polymeric substrate, methyl esterified glucuronoxylan

    USDA-ARS?s Scientific Manuscript database

    Alkali extracted beechwood glucuronoxylan methyl ester prepared by esterification of 4-O-methyl-D-glucuronic acid side residues by methanol was found to serve as substrate of microbial glucuronoyl esterases from Ruminococcus flavefaciens, Schizophyllum commune and Trichoderma reesei. The enzymatic d...

  18. Use of MIDI-fatty acid methyl ester analysis to monitor the transmission of Campylobacter during commercial poultry processing.

    PubMed

    Hinton, Arthur; Cason, J A; Hume, Michael E; Ingram, Kimberly D

    2004-08-01

    The presence of Campylobacter spp. on broiler carcasses and in scald water taken from a commercial poultry processing facility was monitored on a monthly basis from January through June. Campylobacter agar, Blaser, was used to enumerate Campylobacter in water samples from a multiple-tank scalder; on prescalded, picked, eviscerated, and chilled carcasses; and on processed carcasses stored at 4 degrees C for 7 or 14 days. The MIDI Sherlock microbial identification system was used to identify Campylobacter-like isolates based on the fatty acid methyl ester profile of the bacteria. The dendrogram program of the Sherlock microbial identification system was used to compare the fatty acid methyl ester profiles of the bacteria and determine the degree of relatedness between the isolates. Findings indicated that no Campylobacter were recovered from carcasses or scald tank water samples collected in January or February, but the pathogen was recovered from samples collected in March, April, May, and June. Processing generally produced a significant (P < 0.05) decrease in the number of Campylobacter recovered from broiler carcasses, and the number of Campylobacter recovered from refrigerated carcasses generally decreased during storage. Significantly (P < 0.05) fewer Campylobacter were recovered from the final tank of the multiple-tank scald system than from the first tank. MIDI similarity index values ranged from 0.104 to 0.928 based on MIDI-fatty acid methyl ester analysis of Campylobacterjejuni and Campylobacter coli isolates. Dendrograms of the fatty acid methyl ester profile of the isolates indicated that poultry flocks may introduce several strains of C. jejuni and C. coli into processing plants. Different populations of the pathogen may be carried into the processing plant by successive broiler flocks, and the same Campylobacter strain may be recovered from different poultry processing operations. However, Campylobacter apparently is unable to colonize equipment in the processing facility and contaminate broilers from flocks processed at later dates in the facility.

  19. Fatty acid alkyl esters as solvents: An evaluation of the kauri-butanol value. Comparison to hydrocarbons, dimethyl diesters and other oxygenates

    USDA-ARS?s Scientific Manuscript database

    Esters, most commonly methyl esters, of vegetable oils or animal fats or other lipid feedstocks have found increasing use as an alternative diesel fuel known as biodiesel. However, biodiesel also has good solvent properties, a feature rendered additionally attractive by its biodegradability, low tox...

  20. Receptor model for the molecular basis of tissue selectivity of 1,4-dihydropyridine calcium channel drugs

    NASA Astrophysics Data System (ADS)

    Langs, David A.; Strong, Phyllis D.; Triggle, David J.

    1990-09-01

    Our analysis of the solid state conformations of nifedipine [dimethyl 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinecarboxylate] and its 1,4-dihydropyridine (1,4-DHP) analogues produced a cartoon description of the important interactions between these drugs and their voltage-dependent calcium channel receptor. In the present study a molecular-level detailed model of the 1,4-DHP receptor binding site has been built from the published amino acid sequence of the 215-1 subunit of the voltage-dependent calcium channel isolated from rabbit skeletal muscle transverse tubule membranes. The voltage-sensing component of the channel described in this work differs from others reported for the homologous sodium channel in that it incorporates a water structure and a staggered, rather than eclipsed, hydrogen bonded S4 helix conformation. The major recognition surfaces of the receptor lie in helical grooves on the S4 or voltagesensing α-helix that is positioned in the center of the bundle of transmembrane helices that define each of the four calcium channel domains. Multiple binding clefts defined by Arg-X-X-Arg-P-X-X-S `reading frames' exist on the S4 strand. The tissue selectivity of nifedipine and its analogues may arise, in part, from conservative changes in the amino acid residues at the P and S positions of the reading frame that define the ester-binding regions of receptors from different tissues. The crystal structures of two tissue-selective nifedipine analogues, nimodipine [isopropyl (2-methoxyethyl) 1,4-dihydro-2,6- dimethyl-4-(3-nitrophenyl)-3,5-pyridinecarboxylate] and nitrendipine [ethyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinecarboxylate] are reported. Nimodipine was observed to have an unusual ester side chain conformation that enhances the fit to the proposed ester-sensing region of the receptor.

  1. 40 CFR 414.70 - Applicability; description of the bulk organic chemicals subcategory.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ..., Calcium Salt Maleic Anhydride Methacrylic Acid *Methacrylic Acid Esters Methane Methyl Ethyl Ketone Methyl Methacrylate Methyl Tert-Butyl Ether Methylisobutyl Ketone *n-Alkanes n-Butyl Alcohol n-Butylacetate n... Acid Nylon Salt Oxalic Acid *Oxo Aldehydes—Alcohols Pentaerythritol Pentane *Pentenes *Petroleum...

  2. 40 CFR 414.70 - Applicability; description of the bulk organic chemicals subcategory.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ..., Calcium Salt Maleic Anhydride Methacrylic Acid *Methacrylic Acid Esters Methane Methyl Ethyl Ketone Methyl Methacrylate Methyl Tert-Butyl Ether Methylisobutyl Ketone *n-Alkanes n-Butyl Alcohol n-Butylacetate n... Acid Nylon Salt Oxalic Acid *Oxo Aldehydes—Alcohols Pentaerythritol Pentane *Pentenes *Petroleum...

  3. 40 CFR 414.70 - Applicability; description of the bulk organic chemicals subcategory.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ..., Calcium Salt Maleic Anhydride Methacrylic Acid *Methacrylic Acid Esters Methane Methyl Ethyl Ketone Methyl Methacrylate Methyl Tert-Butyl Ether Methylisobutyl Ketone *n-Alkanes n-Butyl Alcohol n-Butylacetate n... Acid Nylon Salt Oxalic Acid *Oxo Aldehydes—Alcohols Pentaerythritol Pentane *Pentenes *Petroleum...

  4. 40 CFR 414.70 - Applicability; description of the bulk organic chemicals subcategory.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ..., Calcium Salt Maleic Anhydride Methacrylic Acid *Methacrylic Acid Esters Methane Methyl Ethyl Ketone Methyl Methacrylate Methyl Tert-Butyl Ether Methylisobutyl Ketone *n-Alkanes n-Butyl Alcohol n-Butylacetate n... Acid Nylon Salt Oxalic Acid *Oxo Aldehydes—Alcohols Pentaerythritol Pentane *Pentenes *Petroleum...

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

    PubMed

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

    2004-09-06

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

  6. 40 CFR 721.10273 - 3′H-Cyclopropa[7,22][5,6]fullerene-C70-D5h(6)-3′-butanoic acid, 3′-phenyl-, methyl ester.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10273 3′H-Cyclopropa[7,22][5,6]fullerene-C70-D5h(6)-3′-butanoic acid, 3′-phenyl-, methyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substances identified as 3′H-Cyclopropa[7,22][5,6...

  7. 40 CFR 721.10272 - 3′H-Cyclopropa[8,25][5,6]fullerene-C70-D5h(6)-3′-butanoic acid, 3′-phenyl-,methyl ester.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10272 3′H-Cyclopropa[8,25][5,6]fullerene-C70-D5h(6)-3′-butanoic acid, 3′-phenyl-,methyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substances identified as 3′H-Cyclopropa[8,25][5,6...

  8. 40 CFR 721.10272 - 3′H-Cyclopropa[8,25][5,6]fullerene-C70-D5h(6)-3′-butanoic acid, 3′-phenyl-,methyl ester.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10272 3′H-Cyclopropa[8,25][5,6]fullerene-C70-D5h(6)-3′-butanoic acid, 3′-phenyl-,methyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substances identified as 3′H-Cyclopropa[8,25][5,6...

  9. 40 CFR 721.10273 - 3′H-Cyclopropa[7,22][5,6]fullerene-C70-D5h(6)-3′-butanoic acid, 3′-phenyl-, methyl ester.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10273 3′H-Cyclopropa[7,22][5,6]fullerene-C70-D5h(6)-3′-butanoic acid, 3′-phenyl-, methyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substances identified as 3′H-Cyclopropa[7,22][5,6...

  10. Biodiesel Production from Chlorella protothecoides Oil by Microwave-Assisted Transesterification

    PubMed Central

    Gülyurt, Mustafa Ömer; Özçimen, Didem; İnan, Benan

    2016-01-01

    In this study, biodiesel production from microalgal oil by microwave-assisted transesterification was carried out to investigate its efficiency. Transesterification reactions were performed by using Chlorella protothecoides oil as feedstock, methanol, and potassium hydroxide as the catalyst. Methanol:oil ratio, reaction time and catalyst:oil ratio were investigated as process parameters affected methyl ester yield. 9:1 methanol/oil molar ratio, 1.5% KOH catalyst/oil ratio and 10 min were optimum values for the highest fatty acid methyl ester yield. PMID:27110772

  11. Biodiesel Production from Chlorella protothecoides Oil by Microwave-Assisted Transesterification.

    PubMed

    Gülyurt, Mustafa Ömer; Özçimen, Didem; İnan, Benan

    2016-04-22

    In this study, biodiesel production from microalgal oil by microwave-assisted transesterification was carried out to investigate its efficiency. Transesterification reactions were performed by using Chlorella protothecoides oil as feedstock, methanol, and potassium hydroxide as the catalyst. Methanol:oil ratio, reaction time and catalyst:oil ratio were investigated as process parameters affected methyl ester yield. 9:1 methanol/oil molar ratio, 1.5% KOH catalyst/oil ratio and 10 min were optimum values for the highest fatty acid methyl ester yield.

  12. Bacillus sp. PS35 Lipase-Immobilization on Styrene-Divinyl Benzene Resin and Application in Fatty Acid Methyl Ester Synthesis.

    PubMed

    Palanisamy, Kanmani; Kuppamuthu, Kumaresan; Jeyaseelan, Aravind

    2015-09-01

    Lipase is an enzyme with immense application potential. Ester synthesis by lipase catalysis in organic media is an area of key industrial relevance. Enzymatic preparations with traits that cater to the needs of this function are hence being intensely researched. The objectives of the study were to immobilize the lipase from Bacillus sp. PS35 by cross-linking and adsorption onto styrene-divinyl benzene (Sty-Dvb) hydrophobic resin and to comparatively characterize the free and immobilized lipase preparations. The work also aimed to apply the immobilized lipase for catalysing the fatty acid methyl ester (FAME) synthesis from palm oil and optimize the process parameters for maximizing the yield. In this study, the purified lipase from Bacillus sp. PS35 was immobilized by adsorption onto styrene-divinyl benzene hydrophobic resin with gluteraldehyde cross-linking. The immobilized enzyme showed better pH and temperature stabilities than the free lipase. Organic solvent stability was also enhanced, with the relative activity in the presence of methanol being shifted from 53% to 81%, thereby facilitating the enzyme's application in fatty acid methyl ester synthesis. It exhibited remarkable storage stability over a 30-day period and after 20 repetitive uses. Cross-linking also reduced enzyme leakage by 49%. The immobilized lipase was then applied for biodiesel production from palm oil. Methanol and oil molar ratio of 5:1, three step methanol additions, and an incubation temperature of 50°C were established to be the ideal conditions favoring the transesterification reaction, resulting in 97% methyl ester yield. These promising results offer scope for further investigation and process scale up, permitting the enzyme's commercial application in a practically feasible and economically agreeable manner.

  13. Bacillus sp. PS35 Lipase-Immobilization on Styrene-Divinyl Benzene Resin and Application in Fatty Acid Methyl Ester Synthesis

    PubMed Central

    Palanisamy, Kanmani; Kuppamuthu, Kumaresan; Jeyaseelan, Aravind

    2015-01-01

    Background Lipase is an enzyme with immense application potential. Ester synthesis by lipase catalysis in organic media is an area of key industrial relevance. Enzymatic preparations with traits that cater to the needs of this function are hence being intensely researched. Objective The objectives of the study were to immobilize the lipase from Bacillus sp. PS35 by cross-linking and adsorption onto styrene-divinyl benzene (Sty-Dvb) hydrophobic resin and to comparatively characterize the free and immobilized lipase preparations. The work also aimed to apply the immobilized lipase for catalysing the fatty acid methyl ester (FAME) synthesis from palm oil and optimize the process parameters for maximizing the yield. Materials and Methods In this study, the purified lipase from Bacillus sp. PS35 was immobilized by adsorption onto styrene-divinyl benzene hydrophobic resin with gluteraldehyde cross-linking. Results The immobilized enzyme showed better pH and temperature stabilities than the free lipase. Organic solvent stability was also enhanced, with the relative activity in the presence of methanol being shifted from 53% to 81%, thereby facilitating the enzyme’s application in fatty acid methyl ester synthesis. It exhibited remarkable storage stability over a 30-day period and after 20 repetitive uses. Cross-linking also reduced enzyme leakage by 49%. The immobilized lipase was then applied for biodiesel production from palm oil. Methanol and oil molar ratio of 5:1, three step methanol additions, and an incubation temperature of 50°C were established to be the ideal conditions favoring the transesterification reaction, resulting in 97% methyl ester yield. Conclusions These promising results offer scope for further investigation and process scale up, permitting the enzyme’s commercial application in a practically feasible and economically agreeable manner. PMID:28959298

  14. Vapor Pressure of Methyl Salicylate and n-Hexadecane

    DTIC Science & Technology

    2014-01-01

    VAPOR PRESSURE OF METHYL SALICYLATE AND N-HEXADECANE ECBC-TR-1184 David E. Tevault Leonard C. Buettner...REPORT TYPE Final 3. DATES COVERED (From - To) Mar 2000-Dec 2001 4. TITLE AND SUBTITLE Vapor Pressure of Methyl Salicylate and n-Hexadecane 5a...ABSTRACT Vapor pressure data are reported for O-hydroxybenzoic acid, methyl ester, more commonly known as methyl salicylate (MeS), and n-hexadecane in

  15. Effects of a cocaine hydrolase engineered from human butyrylcholinesterase on metabolic profile of cocaine in rats.

    PubMed

    Chen, Xiabin; Zheng, Xirong; Zhou, Ziyuan; Zhan, Chang-Guo; Zheng, Fang

    2016-11-25

    Accelerating cocaine metabolism through enzymatic hydrolysis at cocaine benzoyl ester is recognized as a promising therapeutic approach for cocaine abuse treatment. Our more recently designed A199S/F227A/S287G/A328W/Y332G mutant of human BChE, denoted as cocaine hydrolase-3 (CocH3), has a considerably improved catalytic efficiency against cocaine and has been proven active in blocking cocaine-induced toxicity and physiological effects. In the present study, we have further characterized the effects of CocH3 on the detailed metabolic profile of cocaine in rats administrated intravenously (IV) with 5 mg/kg cocaine, demonstrating that IV administration of 0.15 mg/kg CocH3 dramatically changed the metabolic profile of cocaine. Without CocH3 administration, the dominant cocaine-metabolizing pathway in rats was cocaine methyl ester hydrolysis to benzoylecgonine (BZE). With the CocH3 administration, the dominant cocaine-metabolizing pathway in rats became cocaine benzoyl ester hydrolysis to ecgonine methyl ester (EME), and the other two metabolic pathways (i.e. cocaine methyl ester hydrolysis to BZE and cocaine oxidation to norcocaine) became insignificant. The CocH3-catalyzed cocaine benzoyl ester hydrolysis to EME was so efficient such that the measured maximum blood cocaine concentration (∼38 ng/ml) was significantly lower than the threshold blood cocaine concentration (∼72 ng/ml) required to produce any measurable physiological effects. Copyright © 2016 Elsevier Ireland Ltd. All rights reserved.

  16. 76 FR 36109 - Certain New Chemicals; Receipt and Status Information

    Federal Register 2010, 2011, 2012, 2013, 2014

    2011-06-21

    ...-, dodecyl ester, telomer with methyl 2-methyl- 2-propenoate, tridecyl 2- methyl-2- propenoate, 3... (retard) n6-bis (3- set times in carboxy-1- calcium sulfate oxopropyl)-, based binders sodium salt such as..., hydroxyalkyl methacrylates, epoxypropyl acrylates and polyalkene glycol hydrogen sulfate, alkyloxyalkyl...

  17. Evaluation of substituted ebselen derivatives as potential trypanocidal agents.

    PubMed

    Gordhan, Heeren M; Patrick, Stephen L; Swasy, Maria I; Hackler, Amber L; Anayee, Mark; Golden, Jennifer E; Morris, James C; Whitehead, Daniel C

    2017-02-01

    Human African trypanosomiasis is a disease of sub-Saharan Africa, where millions are at risk for the illness. The disease, commonly referred to as African sleeping sickness, is caused by an infection by the eukaryotic pathogen, Trypanosoma brucei. Previously, a target-based high throughput screen revealed ebselen (EbSe), and its sulfur analog, EbS, to be potent in vitro inhibitors of the T. brucei hexokinase 1 (TbHK1). These molecules also exhibited potent trypanocidal activity in vivo. In this manuscript, we synthesized a series of sixteen EbSe and EbS derivatives bearing electron-withdrawing carboxylic acid and methyl ester functional groups, and evaluated the influence of these substituents on the biological efficacy of the parent scaffold. With the exception of one methyl ester derivative, these modifications ablated or blunted the potent TbHK1 inhibition of the parent scaffold. Nonetheless, a few of the methyl ester derivatives still exhibited trypanocidal effects with single-digit micromolar or high nanomolar EC 50 values. Copyright © 2016 Elsevier Ltd. All rights reserved.

  18. Thermally reversible gels based on acryloyl- L-proline methyl ester as drug delivery systems

    NASA Astrophysics Data System (ADS)

    Martellini, Flavia; Higa, Olga Z.; Takacs, Erzsebet; Safranj, Agneza; Yoshida, Masaru; Katakai, Ryoichi; Carenza, Mario

    1999-06-01

    Thermally reversible hydrogels were synthesized by radiation-induced copolymerization of acryloyl- L-proline methyl ester with hydrophilic or hydrophobic monomers. The swelling behaviour was found to be affected by a proper balance of the latter. In particular, the transition temperature of the different hydrogels shifted to higher or lower values depending on the presence of hydrophilic or hydrophobic moieties in the polymer chain, respectively. Acetaminophen, an analgesic and antipyretic drug, was entrapped into some hydrogels and a wide range of release rates was obtained according to the nature of the comonomers. A novel thermoresponsive hydrogel was also prepared by radiation polymerization of acryloyl- L-proline methyl ester in the presence of 4-acryloyloxy acetanilide, an acrylic derivative of acetaminophen. Again, the swelling curves showed an inverse function of temperature. It was shown that with this hydrogel bearing the drug covalently attached to the polymer backbone, the hydrolysis process was the rate-determining process of the drug release.

  19. Synthesis of methyl esters from waste cooking oil using construction waste material as solid base catalyst.

    PubMed

    Balakrishnan, K; Olutoye, M A; Hameed, B H

    2013-01-01

    The current research investigates synthesis of methyl esters by transesterification of waste cooking oil in a heterogeneous system, using barium meliorated construction site waste marble as solid base catalyst. The pretreated catalyst was calcined at 830 °C for 4h prior to its activity test to obtained solid oxide characterized by scanning electron microscopy/energy dispersive spectroscopy, BET surface area and pore size measurement. It was found that the as prepared catalyst has large pores which contributed to its high activity in transesterification reaction. The methyl ester yield of 88% was obtained when the methanol/oil molar ratio was 9:1, reaction temperature at 65 °C, reaction time 3h and catalyst/oil mass ratio of 3.0 wt.%. The catalyst can be reused over three cycles, offer low operating conditions, reduce energy consumption and waste generation in the production of biodiesel. Copyright © 2012 Elsevier Ltd. All rights reserved.

  20. Iridoid glycosides from Gardeniae Fructus for treatment of ankle sprain.

    PubMed

    Chen, Quan Cheng; Zhang, Wei Yun; Youn, Uijoung; Kim, Hongjin; Lee, IkSoo; Jung, Hyun-Ju; Na, MinKyun; Min, Byung-Sun; Bae, KiHwan

    2009-04-01

    The iridoid glycosides, genipin 1-O-beta-D-isomaltoside (1) and genipin 1,10-di-O-beta-D-glucopyranoside (2), together with six known iridoid glycosides, genipin 1-O-beta-D-gentiobioside (3), geniposide (4), scandoside methyl ester (5), deacetylasperulosidic acid methyl ester (6), 6-O-methyldeacetylasperulosidic acid methyl ester (7), and gardenoside (8) were isolated from an EtOH extract of Gardeniae Fructus. The structures and relative stereochemistries of the metabolites were elucidated on the basis of 1D- and 2D-NMR spectroscopic techniques, high-resolution mass spectrometry, and chemical evidence. Geniposide (4), one of the main compounds of Gardeniae Fructus, was tested for treatment of ankle sprain using an ankle sprain model in rats. From the second to fifth day, the geniposide (4) (100mg/ml) treated group exhibited significant differences (p<0.01) with approximately 21-34% reduction in swelling ratio compared with those of the vehicle treated control group. This indicated the potential effect of geniposide (4) for the treatment of disorders such as ankle sprain.

  1. Safety Assessment of Methyl Glucose Polyethers and Esters as Used in Cosmetics.

    PubMed

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

    2016-11-01

    The Cosmetic Ingredient Review Expert Panel (Panel) reviewed the safety of methyl glucose polyethers and esters which function in cosmetics as skin/hair-conditioning agents, surfactants, or viscosity increasing agents. The esters included in this assessment are mono-, di-, or tricarboxyester substituted methyl glucosides, and the polyethers are mixtures of various chain lengths. The Panel reviewed available animal and clinical data, including the molecular weights, log K ow s, and other properties in making its determination of safety on these ingredients. Where there were data gaps, similarities between molecular structures, physicochemical and biological characteristics, and functions and concentrations in cosmetics allowed for extrapolation of the available toxicological data to assess the safety of the entire group. The Panel concluded that there likely would be no significant systemic exposure from cosmetic use of these ingredients, and that these ingredients are safe in cosmetic formulations in the present practices of use and concentration. © The Author(s) 2016.

  2. Identification and Synthesis of Branched Wax-type Esters, Novel Surface Lipids from the Spider Argyrodes elevatus (Araneae: Theridiidae).

    PubMed

    Chinta, Satya Prabhakar; Goller, Stephan; Uhl, Gabriele; Schulz, Stefan

    2016-09-01

    The analysis of cuticular extracts from the kleptoparasitic spider Argyrodes elevatus revealed the presence of unusual esters, new for arthropods. These novel compounds proved to be methyl-branched long-chain fatty acid esters with methyl branches located either close or remote from the internally located ester group. The GC/MS analysis of the prosoma lipid blend from the male cuticle contained one major component, undecyl 2-methyltridecanoate (1). In contrast, four major wax-type esters, 2-methylundecyl 2,8-dimethylundecanoate (2), 2,8-dimethylundecyl 2,8-dimethylundecanoate (3), heptadecyl 4-methylheptanoate (4), and 14-methylheptadecyl 4-methylheptanoate (5), were identified in the lipid blend of female prosomata. Structure assignments were based on mass spectra, gas chromatographic retention indices, and microderivatization. Unambiguous proof of postulated structures was ensured by an independent synthesis of all five esters. Preferentially, odd-numbered carbon chains pointed to a distinct biosynthetic pathway, different from that of common fatty acids, because one or two C 3 starter units are incorporated during the biosynthesis of all acid and alcohol building blocks present in the five esters. The striking sexual dimorphism together with the unique biosynthesis points to a function of the esters in chemical communication of the spiders, although no behavioral data are currently available to test this assumption. © 2016 Wiley-VHCA AG, Zürich.

  3. Process for the synthesis of unsaturated alcohols

    DOEpatents

    Maughon, Bob R.; Burdett, Kenneth A.; Lysenko, Zenon

    2007-02-13

    A process of preparing an unsaturated alcohol (olefin alcohol), such as, a homo-allylic mono-alcohol or homo-allylic polyol, involving protecting a hydroxy-substituted unsaturated fatty acid or fatty acid ester, such as methyl ricinoleate, derived from a seed oil, to form a hydroxy-protected unsaturated fatty acid or fatty acid ester; homo-metathesizing or cross-metathesizing the hydroxy-protected unsaturated fatty acid or fatty acid ester to produce a product mixture containing a hydroxy-protected unsaturated metathesis product; and deprotecting the hydroxy-protected unsaturated metathesis product under conditions sufficient to prepare the unsaturated alcohol. Preferably, methyl ricinoleate is converted by cross-metathesis or homo-metathesis into the homo-allylic mono-alcohol 1-decene-4-ol or the homo-allylic polyol 9-octadecene-7,12-diol, respectively.

  4. Synthesis and characterization of a thermo-sensitive poly( N-methyl acryloylglycine methyl ester) used as a drug release carrier

    NASA Astrophysics Data System (ADS)

    Deng, Kui-Lin; Zhong, Hai-Bin; Jiao, Yi-Suo; Fan, Ting; Qiao, Xiao; Zhang, Peng-Fei; Ren, Xiao-Bo

    2010-06-01

    In this article, poly( N-methyl acryloylglycine methyl ester) (PNMAME) was prepared as a novel thermosensitive material with a lower critical solution temperature (LCST) at around 49.5°C. The chemical structures of the monomer NMAME and PNMAME were characterized by 1H NMR and IR measurements. The LCST was investigated systematically as a function of PNMAME concentration, inorganic salt solution and pH value. The results indicated that LCST of PNMAME was obviously dependent on PNMAME concentration and pH. The LCST was increased with a decrease in pH value and PNMAME concentration. To obtain a thermo-sensitive hydrogel with the phase transition temperature close to human body temperature, the copolymerization was conducted between NMAME and N-acryloylglycine ethyl ester (NAGEE). The release behavior of caffeine was evaluated at different temperatures and contents of cross-linkers ( N, N-methylenebis(acrylamide) (NMBA)). The increase of cross-linker content led to a decrease in the release rate of caffeine due to higher crossing density in the hydrogel network. In addition, a faster release of caffeine from the hydrogel with 3% NMBA at 37°C was found in contrast to that at 18°C.

  5. Molecular characterization of primary humic-like substances in fine smoke particles by thermochemolysis-gas chromatography-mass spectrometry

    NASA Astrophysics Data System (ADS)

    Fan, Xingjun; Wei, Siye; Zhu, Mengbo; Song, Jianzhong; Peng, Ping'an

    2018-05-01

    In this study, the molecular structures of primary humic-like substances (HULIS) in fine smoke particles emitted from the combustion of biomass materials (including rice straw, corn straw, and pine branches) and coal, and atmospheric HULIS were determined by off-line tetramethylammonium hydroxide thermochemolysis coupled with gas chromatography and mass spectrometry (TMAH-GC/MS). A total of 89 pyrolysates were identified by the thermochemolysis of primary and atmospheric HULIS. The main groups were polysaccharide derivatives, N-containing compounds, lignin derivatives, aromatic acid methyl ester, aliphatic acid methyl ester, and diterpenoid derivatives. Both the type and distribution of pyrolysates among primary HULIS were comparable to those in atmospheric HULIS. This indicates that primary HULIS from combustion processes are important contributors to atmospheric HULIS. Some distinct differences were also observed. The aromatic compounds, including lignin derivatives and aromatic acid methyl ester, were the major pyrolysates (53.0%-84.9%) in all HULIS fractions, suggesting that primary HULIS significantly contributed aromatic structures to atmospheric HULIS. In addition, primary HULIS from biomass burning (BB) contained a relatively high abundance of lignin and polysaccharide derivatives, which is consistent with the large amounts of lignin and cellulose structures contained in biomass materials. Aliphatic acid methyl ester and benzyl methyl ether were prominent pyrolysates in atmospheric HULIS. Moreover, some molecular markers of specific sources were obtained from the thermochemolysis of primary and atmospheric HULIS. For example, polysaccharide derivatives, pyridine and pyrrole derivatives, and lignin derivatives can be used as tracers of fresh HULIS emitted from BB. Diterpenoid derivatives are important markers of HULIS from pine wood combustion sources. Finally, the differences in pyrolysate types and the distributions between primary and atmospheric HULIS suggested that the primary HULIS would undergo many atmospheric processes to reconstruct the macromolecular organic matter in atmospheric aerosols.

  6. Determination of fatty acid methyl esters derived from algae Scenedesmus dimorphus biomass by GC-MS with one-step esterification of free fatty acids and transesterification of glycerolipids.

    PubMed

    Avula, Satya Girish Chandra; Belovich, Joanne M; Xu, Yan

    2017-05-01

    Algae can synthesize, accumulate and store large amounts of lipids in its cells, which holds immense potential as a renewable source of biodiesel. In this work, we have developed and validated a GC-MS method for quantitation of fatty acids and glycerolipids in forms of fatty acid methyl esters derived from algae biomass. Algae Scenedesmus dimorphus dry mass was pulverized by mortar and pestle, then extracted by the modified Folch method and fractionated into free fatty acids and glycerolipids on aminopropyl solid-phase extraction cartridges. Fatty acid methyl esters were produced by an optimized one-step esterification of fatty acids and transesterification of glycerolipids with boron trichloride/methanol. The matrix effect, recoveries and stability of fatty acids and glycerolipids in algal matrix were first evaluated by spiking stable isotopes of pentadecanoic-2,2-d 2 acid and glyceryl tri(hexadecanoate-2,2-d 2 ) as surrogate analytes and tridecanoic-2,2-d 2 acid as internal standard into algal matrix prior to sample extraction. Later, the method was validated in terms of lower limits of quantitation, linear calibration ranges, intra- and inter-assay precision and accuracy using tridecanoic-2,2-d 2 acid as internal standard. The method developed has been applied to the quantitation of fatty acid methyl esters from free fatty acid and glycerolipid fractions of algae Scenedesmus dimorphus. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  7. Oil industry waste: a potential feedstock for biodiesel production.

    PubMed

    Abbas, Javeria; Hussain, Sabir; Iqbal, Muhammad Javid; Nadeem, Habibullah; Qasim, Muhammad; Hina, Saadia; Hafeez, Farhan

    2016-08-01

    The worldwide rising energy demands and the concerns about the sustainability of fossil fuels have led to the search for some low-cost renewable fuels. In this scenario, the production of biodiesel from various vegetable and animal sources has attracted worldwide attention. The present study was conducted to evaluate the production of biodiesel from the oil industry waste following base-catalysed transesterification. The transesterification reaction gave a yield of 83.7% by 6:1 methanol/oil molar ratio, at 60°C over 80 min of reaction time in the presence of NaOH. The gas chromatographic analysis of the product showed the presence of 16 fatty acid methyl esters with linoleic and oleic acid as principal components representing about 31% and 20.7% of the total methyl esters, respectively. The fourier transform infrared spectroscopy spectrum of oil industry waste and transesterified product further confirmed the formation of methyl esters. Furthermore, the fuel properties of oil industry waste methyl esters, such as kinematic viscosity, cetane number, cloud point, pour point, flash point, acid value, sulphur content, cold filter plugging point, copper strip corrosion, density, oxidative stability, higher heating values, ash content, water content, methanol content and total glycerol content, were determined and discussed in the light of ASTM D6751 and EN 14214 biodiesel standards. Overall, this study presents the production of biodiesel from the oil industry waste as an approach of recycling this waste into value-added products.

  8. Energetics and electronic structures of chemically decorated C60 chains

    NASA Astrophysics Data System (ADS)

    Furutani, Sho; Okada, Susumu

    2018-06-01

    We studied the energetics and electronic structures of one-dimensional molecular chains of [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) using the density functional theory (DFT). Our DFT calculations show that the binding energies of PCBM range from 90 to 300 meV, depending on not only the intermolecular spacing but also the intermolecular arrangements owing to the interaction between functional groups and C60. The electronic structure of PCBM chains are also sensitive to the mutual arrangements of PCBM in their chain structure. The calculated effective masses of the conduction band range from 0.58 to 634.97m e, giving rise to anisotropic transport properties in their condensed phase.

  9. Effect of pressure on the selectivity of polymeric C18 and C30 stationary phases in reversed-phase liquid chromatography. Increased separation of isomeric fatty acid methyl esters, triacylglycerols, and tocopherols at high pressure.

    PubMed

    Okusa, Kensuke; Iwasaki, Yuki; Kuroda, Ikuma; Miwa, Shohei; Ohira, Masayoshi; Nagai, Toshiharu; Mizobe, Hoyo; Gotoh, Naohiro; Ikegami, Tohru; McCalley, David V; Tanaka, Nobuo

    2014-04-25

    A high-density, polymeric C18 stationary phase (Inertsil ODS-P) or a polymeric C30 phase (Inertsil C30) provided improved resolution of the isomeric fatty acids (FAs), FA methyl esters (FAMEs), triacylglycerols (TAGs), and tocopherols with an increase in pressure of 20-70MPa in reversed-phase HPLC. With respect to isomeric C18 FAMEs with one cis-double bond, ODS-P phase was effective for recognizing the position of a double bond among petroselinic (methyl 6Z-octadecenoate), oleic (methyl 9Z-octadecenoate), and cis-vaccenic (methyl 11Z-octadecenoate), especially at high pressure, but the differentiation between oleic and cis-vaccenic was not achieved by C30 phase regardless of the pressure. A monomeric C18 phase (InertSustain C18) was not effective for recognizing the position of the double bond in monounsaturated FAME, while the separation of cis- and trans-isomers was achieved by any of the stationary phases. The ODS-P and C30 phases provided increased separation for TAGs and β- and γ-tocopherols at high pressure. The transfer of FA, FAME, or TAG molecules from the mobile phase to the ODS-P stationary phase was accompanied by large volume reduction (-30∼-90mL/mol) resulting in a large increase in retention (up to 100% for an increase of 50MPa) and improved isomer separation at high pressure. For some isomer pairs, the ODS-P and C30 provided the opposite elution order, and in each case higher pressure improved the separation. The two stationary phases showed selectivity for the isomers having rigid structures, but only the ODS-P was effective for differentiating the position of a double bond in monounsaturated FAMEs. The results indicate that the improved isomer separation was provided by the increased dispersion interactions between the solute and the binding site of the stationary phase at high pressure. Copyright © 2014 Elsevier B.V. All rights reserved.

  10. Synethesis of cyclic ketal from soybean oil and fatty esters

    USDA-ARS?s Scientific Manuscript database

    In this work we have shown a facile and environmentally friendly reaction to form a cyclic ketal out of soybean oil, methyl soyate, methyl linoleate, and methyl oleate. There are many advantages of this reaction. First, the ketal reaction produces a branched fatty acid moiety and is reversible. S...

  11. Liner Technology Program. Volume 3. Liner Development Methodology Manual

    DTIC Science & Technology

    1982-05-01

    derivative of trimesic acid, trimenoyl-l- (2-ethyl) aziridine BNO Hydroxyl ethyl ester of carboxy-terminated polybutadiene Catocene Liquid ferrocene ...diisocyanate MAPO rris-l-(2-methyl) aziridinyl phosphine oxide I.’ lNA Methyl nedic anhydride; methyl endo-cis-cicyolo-2,2,1-5- heptene-2,3-dicarboxylic

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

    PubMed Central

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

    2017-01-01

    Background: Fatty acids occur in nearly all living organisms as the important predominant constituents of lipids. While all fatty acids have essentially the same chemical nature, they are an extremely diverse group of compounds. Materials and Methods: To test the hypothesis, fatty acids of alkaliphiles isolates, Bacillus subtilis SVUNM4, Bacillus licheniformis SVUNM8, Bacillus methylotrohicus SVUNM9, and Paenibacillus dendritiformis SVUNM11, were characterized compared using gas chromatography-mass spectrometry (GC-MS) analysis. Results: The content of investigated ten fatty acids, 1, 2-benzenedicarboxylic acid butyl 2-methylpropyl ester, phthalic acid, isobutyl 2-pentyl ester, dibutyl phthalate, cyclotrisiloxane, hexamethyl, cyclotetrasiloxane, octamethyl, dodecamethyl, heptasiloxane 1,1,3,3,5,5,7,7,9,9,11,11,13,13-etradecamethyl, 7,15-dihydroxydehydroabietic acid, methyl ester, di (trimethylsilyl) ether, hentriacontane, 2-thiopheneacetic acid, undec-2-enyl ester, obviously varied among four species, suggesting each species has its own fatty acid pattern. Conclusions: These findings demonstrated that GC-MS-based fatty acid profiling analysis provides the reliable platform to classify these four species, which is helpful for ensuring their biotechnological interest and novel chemotaxonomic. PMID:28717333

  13. Fatty acid methyl ester from Neurospora intermedia N-1 isolated from Indonesian red peanut cake (oncom merah).

    PubMed

    Priatni, S; Hartati, S; Dewi, P; Kardono, L B S; Singgih, M; Gusdinar, T

    2010-08-01

    The objective of this study was to identify the Fatty Acid Methyl Ester (FAME) from Neurospora intermedia N-1 that isolated from Indonesian red peanut cake (oncom). FAME profiles have been used as biochemical characters to study many different groups of organisms, such as bacteria and yeasts. FAME from N. intermedia N-1 was obtained by some stages of extraction the orange spores and fractination using a chromatotron. The pure compound (1) was characterized by 500 mHz NMR (1H and 13C), FTIR and LC-MS. Summarized data's of 1H and 13C NMR spectra of compound 1 contained 19 Carbon, 34 Hydrogen and 2 Oxygen (C19H34O2). The position of the double bonds at carbon number 8 and 12 were indicated in the HMBC spectrum (2D-NMR). LC-MS spectrum indicates molecular weight of the compound 1 as 294 which is visible by the presence of protonated molecular ion [M+H] at m/z 295. Methyl esters of long chain fatty acids was presented by a 3 band pattern of IR spectrum with bands near 1249, 1199 and 1172 cm(-1). We suggested that the structure of the pure compound 1 is methyl octadeca-8,12-dienoate. The presence methyl octadeca-8,12-dienoate in N. intermedia is the first report.

  14. Chemical Kinetic Influences of Alkyl Chain Structure on the High Pressure and Temperature Oxidation of a Representative Unsaturated Biodiesel: Methyl Nonenoate.

    PubMed

    Fridlyand, Aleksandr; Goldsborough, S Scott; Brezinsky, Kenneth

    2015-07-16

    The high pressure and temperature oxidation of methyl trans-2-nonenoate, methyl trans-3-nonenoate, 1-octene, and trans-2-octene are investigated experimentally to probe the influence of the double bond position on the chemical kinetics of long esters and alkenes. Single pulse shock tube experiments are performed in the ranges p = 3.8-6.2 MPa and T = 850-1500 K, with an average reaction time of 2 ms. Gas chromatographic measurements indicate increased reactivity for trans-2-octene compared to 1-octene, whereas both methyl nonenoate isomers have reactivities similar to that of 1-octene. A difference in the yield of stable intermediates is observed for the octenes when compared to the methyl nonenoates. Chemical kinetic models are developed with the aid of the Reaction Mechanism Generator to interpret the experimental results. The models are created using two different base chemistry submodels to investigate the influence of the foundational chemistry (i.e., C0-C4), whereas Monte Carlo simulations are performed to examine the quality of agreement with the experimental results. Significant uncertainties are found in the chemistry of unsaturated esters with the double bonds located close to the ester groups. This work highlights the importance of the foundational chemistry in predictive chemical kinetics of biodiesel combustion at engine relevant conditions.

  15. Separation of the fatty acids in menhaden oil as methyl esters with a highly polar ionic liquid gas chromatographic column and identification by time of flight mass spectrometry.

    PubMed

    Fardin-Kia, Ali Reza; Delmonte, Pierluigi; Kramer, John K G; Jahreis, Gerhard; Kuhnt, Katrin; Santercole, Viviana; Rader, Jeanne I

    2013-12-01

    The fatty acids contained in marine oils or products are traditionally analyzed by gas chromatography using capillary columns coated with polyethylene glycol phases. Recent reports indicate that 100 % cyanopropyl siloxane phases should also be used when the analyzed samples contain trans fatty acids. We investigated the separation of the fatty acid methyl esters prepared from menhaden oil using the more polar SLB-IL111 (200 m × 0.25 mm) ionic liquid capillary column and the chromatographic conditions previously optimized for the separation of the complex mixture of fatty acid methyl esters prepared from milk fat. Identifications of fatty acids were achieved by applying Ag(+)-HPLC fractionation and GC-TOF/MS analysis in CI(+) mode with isobutane as the ionization reagent. Calculation of equivalent chain lengths confirmed the assignment of double bond positions. This methodology allowed the identification of 125 fatty acids in menhaden oil, including isoprenoid and furanoid fatty acids, and the novel 7-methyl-6-hexadecenoic and 7-methyl-6-octadecenoic fatty acids. The chromatographic conditions applied in this study showed the potential of separating in a single 90-min analysis, among others, the short chain and trans fatty acids contained in dairy products, and the polyunsaturated fatty acids contained in marine products.

  16. Extraction and identification of bioactive components in Sida cordata (Burm.f.) using gas chromatography-mass spectrometry.

    PubMed

    Ganesh, Mani; Mohankumar, Murugan

    2017-09-01

    Sida cordata (Burm.f.) is a pineal tropical plant in the family Malvaceae that is found throughout India and used to treat various diseases and ailments in many complementary and alternative medicine systems. This study identified the bioactive components present in whole-plant ethanol extracts of S . cordata using gas chromatography-mass spectrometry (GC-MS). Based on their retention times (RT) and mass-to-charge ratios (m/z), 29 bioactive compounds were identified: nonanoic acid, vitamin D 3 , 3-trifluroacetoxypentadecane, α-d-glucopyranoside, O-α-d-glucopyranosyl-(1.fwdarw.3)-α-d-fructofuranosyl,3,7,11,15-tetramethyl-2-hexadecan-1-ol, octadecanoic acid, ethyl ester, phytol, 9,12-octadecadienoic acid, methyl ester (E,E), 9,12,15-octadecadienoic acid, methyl ester (Z,Z,Z), oleic acid, 1,2-15,16-diepoxyhexadecane, 3-hexadecyloxycarbonyl-5-(2-hydroxyethyl)-4-methylimidazolium ion, methoxyacetic acid, 4-tetradecyl ester, 1,2-benzenedicarboxylic acid, mono (2-ethylhexyl) ester, 1-iodo-2-methylundecane, dodecane, 2,6,10-trimethyl-, 2-piperidinone-N-[4-bromo-n-butyl]-, squalene, octadecane-1-(ethenyloxy)-, Z,Z-2,5-pentadecadien-1-ol, 1-hexadecanol, 2-methyl-, spiro[androst-5ene-17,1'-cyclobutan]-2'-one-3-hydroxy-, (3a,17a)-, diethylene glycol monododecyl ether, vitamin E, cholestan-3-ol, 2-methylene-, (3a,5a)-, 2H-pyran, 2-(7-heptadecynyloxy)tetrahydro-, and cis -Z-α-bisabolene epoxide. The presence of various bioactive compounds justifies the use of this plant for treating various ailments by traditional practitioners.

  17. A phorbol ester-binding protein is required downstream of Rab5 in endosome fusion.

    PubMed

    Aballay, A; Barbieri, M A; Colombo, M I; Arenas, G N; Stahl, P D; Mayorga, L S

    1998-12-28

    Previous observations indicate that a zinc and phorbol ester binding factor is necessary for endosome fusion. To further characterize the role of this factor in the process, we used an in vitro endosome fusion assay supplemented with recombinant Rab5 proteins. Both zinc depletion and addition of calphostin C, an inhibitor of protein kinase C, inhibited endosome fusion in the presence of active Rab5. Addition of the phorbol ester PMA (phorbol 12-myristate 13-acetate) reversed the inhibition of endosome fusion caused by a Rab5 negative mutant. Moreover, PMA stimulated fusion in the presence of Rab5 immunodepleted cytosol. These results suggest that the phorbol ester binding protein is acting downstream of Rab5 in endosome fusion.

  18. [Studies on the chemical constituents of Phlomis younghusbandii].

    PubMed

    Gao, Yong-li; Lin, Rui-chao; Wang, Gang-li; Zhao, Han-ru; Gao, Yuan; Ciren, Bianha

    2007-10-01

    To study the chemical constituents of Phlomis younghusbandii. Compounds were isolated from the ethanolic extract by silica gel column chromatography, and their structures were identified by physical and chemical evidences and spectral methods. Eight compounds were isolated and identified respectively as 8-acetylshanzhiside methyl ester (1), shanzhiside methyl ester (2), phlomiol (3), 2-butoxy-2-(hydroxymthyl) tetrahydro-2H-3,4,5-pyrantriol (4), sesamoside (5), pulchelloside-I (6), luteolin-7-O-beta-D-glucopyranoside (7) and daucosterol (8). All the compounds were isolated from the plant for the first time.

  19. Photodynamic activity of pyropheophorbide methyl ester and pyropheophorbide a in dimethylformamide solution.

    PubMed

    Al-Omari, Saleh; Ali, Ahmad

    2009-03-01

    Comparative spectroscopic study including the photosensitizers of pyropheophorbide methyl ester (PPME) and pyropheophorbide a (PPa) was performed to study their photodynamic activity. The investigated photosensitizers in a homogeneous system of dimethylformamide (DMF) are not photostable upon irradiation. The photobleaching efficiency of PPa is higher than that of PPME. Combining these results with the data obtained by measuring the singlet oxygen quantum yield and the hydroxyl group generation, it was revealed that the photobleaching efficiency could be correlated with the singlet oxygen quantum yield and the hydroxyl group production of the photosensitizer.

  20. Facile solvolysis of a surprisingly twisted tertiary amide

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    Bloomfield, Aaron J.; Chaudhuri, Subhajyoti; Mercado, Brandon Q.

    2016-01-05

    In this study, a bicyclo[2.2.2]octane derivative containing both a tertiary amide and a methyl ester was shown crystallographically to adopt a conformation in which the amide is in the cis configuration, which is sterically disfavored, but electronically favored. The steric strain induces a significant torsion (15.9°) of the amide, thereby greatly increasing the solvolytic lability of the amide to the extent that we see competitive amide solvolysis in the presence of the normally more labile methyl ester also present in the molecule.

  1. Fabrication of One-Dimensional Zigzag [6,6]-PhenylC61-Butyric Acid Methyl Ester Nanoribbons from Two-Dimensional Nanosheets (Open Access: Author’s Final)

    DTIC Science & Technology

    2015-09-18

    a derivative is the [6,6]-phenyl-C61-butyric acid methyl ester (PCBM), a C60 fullerene with a chemically bonded functional group. The addition of the...functional group, on the other hand, decreases the fullerene symmetry and conse- quently affects its crystallization.8 Although growth of crystalline C60...possibility to tune the grown structures to different morphologies.8 One-dimensional fullerene (C60) struc- tures, namely, nanorods and nanoribbons, are of

  2. Lipid oxidation. Part 2. Oxidation products of olive oil methyl esters.

    PubMed

    Pokorný, J; Tài, P; Parízková, H; Smidrkalová, E; El-Tarras, M F; Janícek, G

    1976-01-01

    Olive oil was converted into methyl esters which were autoxidized at 60 degrees C. The composition of oxidized products was determined by the comparison of infrared spectra and NMR spectra of the original and acetylated samples, the sample reduced with potassium iodide and the acetylated reduced sample. Oxidized products were separated by preparative thin layer chromatography on silica gel and characterized by selective detection and by infrared spectrometry of the fractions. The oxidation products consisted of hydroperoxido butyl oleate, substituted hydroperoxides, mono- and disubstituted monomeric derivatives and a small amount of oligomers.

  3. Chemical Composition and Vasorelaxant and Antispasmodic Effects of Essential Oil from Rosa indica L. Petals

    PubMed Central

    Rasheed, Hafiz Majid; Khan, Taous; Wahid, Fazli; Khan, Rasool; Shah, Abdul Jabbar

    2015-01-01

    Rosa indica L. belongs to the family Rosaceae and is locally known as gulaab. It has different traditional uses in cardiovascular and gastrointestinal disorders but there is no scientific data available in this regard. Therefore, the basic aim of this study was to explore the chemical composition and gastrointestinal and cardiovascular effects of the essential oil obtained from R. indica. The chemical composition of the essential oil was investigated using gas chromatography-mass spectrometry (GC-MS) technique. The cardiovascular and gastrointestinal effects were investigated using electrophysiological measurements. The GC-MS analysis of the essential oil showed various chemical components including acetic acid, mercaptohexyl ester, butanoic acid, 2-methyl-5-oxo-1-cyclopentene-1-yl ester, artemiseole, methyl santonilate, isosteviol, caryophyllene oxide, pentyl phenyl acetate, dihydromyrcene, 1,5-octadecadien, octadecanoic acid, ethyl ester, palmitic acid (2-phenyl-1,3-dioxolan-4-yl methyl ester), santolina epoxide, and 9-farnesene. The electrophysiological measurements revealed that essential oil was more potent against K+ (80 mM) than phenylephrine precontractions using isolated rabbit aorta preparations. In isolated rabbit jejunum preparations, it showed more potency against high K+ induced contractions than spontaneous contractions. Considering these evidences, it can be concluded that R. indica essential oil may work as a complementary and alternative medicine in gastrointestinal and cardiovascular diseases. PMID:26357519

  4. 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.

  5. One-pot process combining transesterification and selective hydrogenation for biodiesel production from starting material of high degree of unsaturation.

    PubMed

    Yang, Ru; Su, Mengxing; Li, Min; Zhang, Jianchun; Hao, Xinmin; Zhang, Hua

    2010-08-01

    A one-pot process combining transesterification and selective hydrogenation was established to produce biodiesel from hemp (Cannabis sativa L.) seed oil which is eliminated as a potential feedstock by a specification of iodine value (IV; 120 g I(2)/100g maximum) contained in EN 14214. A series of alkaline earth metal oxides and alkaline earth metal supported copper oxide were prepared and tested as catalysts. SrO supported 10 wt.% CuO showed the superior catalytic activity for transesterification with a biodiesel yield of 96% and hydrogenation with a reduced iodine value of 113 and also exhibited a promising selectivity for eliminating methyl linolenate and increasing methyl oleate without rising methyl stearate in the selective hydrogenation. The fuel properties of the selective hydrogenated methyl esters are within biodiesel specifications. Furthermore, cetane numbers and iodine values were well correlated with the compositions of the hydrogenated methyl esters according to degrees of unsaturation. (c) 2010 Elsevier Ltd. All rights reserved.

  6. Improving the Cold Temperature Properties of Tallow-Based Methyl Ester Mixtures Using Fractionation, Blending, and Additives

    NASA Astrophysics Data System (ADS)

    Elwell, Caleb

    Beef tallow is a less common feedstock source for biodiesel than soy or canola oil, but it can have economic benefits in comparison to these traditional feedstocks. However, tallow methyl ester (TME) has the major disadvantage of poor cold temperature properties. Cloud point (CP) is an standard industry metric for evaluating the cold temperature performance of biodiesel and is directly related to the thermodynamic properties of the fuel's constituents. TME has a CP of 14.5°C compared with 2.3°C for soy methyl ester (SME) and -8.3°C for canola methyl ester (CME). In this study, three methods were evaluated to reduce the CP of TME: fractionation, blending with SME and CME, and using polymer additives. TME fractionation (i.e. removal of specific methyl ester constituents) was simulated by creating FAME mixtures to match the FAME profiles of fractionated TME. The fractionation yield was found to be highest at the eutectic point of methyl palmitate (MP) and methyl stearate (MS), which was empirically determined to be at a MP/(MP+MS) ratio of approximately 82%. Since unmodified TME has a MP/(MP+MS) ratio of 59%, initially only MS should be removed to produce a ratio closer to the eutectic point to reduce CP and maximize yield. Graphs relating yield (with 4:1 methyl stearate to methyl oleate carryover) to CP were produced to determine the economic viability of this approach. To evaluate the effect of blending TME with other methyl esters, SME and CME were blended with TME at blend ratios of 0 to 100%. Both the SME/TME and CME/TME blends exhibited decreased CPs with increasing levels of SME and CME. Although the CP of the SME/TME blends varied linearly with SME content, the CP of the CME/TME blends varied quadratically with CME content. To evaluate the potential of fuel additives to reduce the CP of TME, 11 different polymer additives were tested. Although all of these additives were specifically marketed to enhance the cold temperature properties of petroleum diesel or biodiesel, only two of the additives had any significant effect on TME CP. The additive formulated by Meat & Livestock Australia (MLA) outperformed Evonik's Viscoplex 10-530. The MLA additive was investigated further and its effect on CP was characterized in pure TME and in CME/TME blends. When mixed in CME/TME blends, the MLA additive had a synergistic effect and produced lower CPs than the addition of mixing MLA in TME and blending CME with TME. To evalulate the cold temperature properties of TME blended with petroleum diesel, CPs of TME/diesel blends from 0 to 100% were measured. The TME/diesel blends were treated with the MLA additives to determine the effects of the additives under these blend conditions. The MLA additive also had a synergistic effect when mixed in TME/diesel blends. Finally, all three of the TME CP reduction methods were evaluated in an economic model to determine the conditions under which each method would be economically viable. Each of the CP reduction methods were compared using a common metric based on the cost of reducing the CP of 1 gallon of finished biodiesel by 1°C (i.e. $/gal/°C). Since the cost of each method is dependent on varying commodity prices, further development of the economic model (which was developed and tested with 2012 prices) to account for stochastic variation in commodity prices is recommended.

  7. A direct and fast method to monitor lipid oxidation progress in model fatty acid methyl esters by high-performance size-exclusion chromatography.

    PubMed

    Márquez-Ruiz, G; Holgado, F; García-Martínez, M C; Dobarganes, M C

    2007-09-21

    A new method based on high-performance size-exclusion chromatography (HPSEC) is proposed to quantitate primary and secondary oxidation compounds in model fatty acid methyl esters (FAMEs). The method consists on simply injecting an aliquot sample in HPSEC, without preliminary isolation procedures neither addition of standard internal. Four groups of compounds can be quantified, namely, unoxidised FAME, oxidised FAME monomers including hydroperoxides, FAME dimers and FAME polymers. Results showed high repeatability and sensitivity, and substantial advantages versus determination of residual substrate by gas-liquid chromatography. Applicability of the method is shown through selected data obtained by numerous oxidation experiments on pure FAME, mainly methyl linoleate, at ambient and moderate temperatures.

  8. Experimental and numerical investigations on spray characteristics of fatty acid methyl esters

    NASA Astrophysics Data System (ADS)

    Lanjekar, R. D.; Deshmukh, D.

    2018-02-01

    A comparative experimental and numerical study is conducted to establish the significance of the use of single-component over multi-component representatives of biodiesel, diesel and their blend for predicting spray tip penetration. Methyl oleate and methyl laurate are used as single-component representative fuels for biodiesel. The pure components n-heptane, n-dodecane and n-tetradecane are used as single-component representative fuels for diesel. Methyl laurate is found to represent biodiesel of coconut, whereas methyl oleate is found to represent biodiesel having high percentage of long-chain fatty acid esters. The spray tip penetration of methyl oleate is found to be in good agreement with the measured spray tip penetration of karanja biodiesel. The spray tip penetration prediction of n-heptane fuel is closely following diesel spray tip penetration along with that of n-tetradecane and n-dodecane. The study suggests that the knowledge of the single-component representatives of biodiesel, diesel and their blend is sufficient to predict the spray tip penetration of the corresponding biodiesel, diesel and their blend under non-evaporating environment.

  9. Experimental and numerical investigations on spray characteristics of fatty acid methyl esters.

    PubMed

    Lanjekar, R D; Deshmukh, D

    2018-02-01

    A comparative experimental and numerical study is conducted to establish the significance of the use of single-component over multi-component representatives of biodiesel, diesel and their blend for predicting spray tip penetration. Methyl oleate and methyl laurate are used as single-component representative fuels for biodiesel. The pure components n -heptane, n -dodecane and n -tetradecane are used as single-component representative fuels for diesel. Methyl laurate is found to represent biodiesel of coconut, whereas methyl oleate is found to represent biodiesel having high percentage of long-chain fatty acid esters. The spray tip penetration of methyl oleate is found to be in good agreement with the measured spray tip penetration of karanja biodiesel. The spray tip penetration prediction of n -heptane fuel is closely following diesel spray tip penetration along with that of n -tetradecane and n -dodecane. The study suggests that the knowledge of the single-component representatives of biodiesel, diesel and their blend is sufficient to predict the spray tip penetration of the corresponding biodiesel, diesel and their blend under non-evaporating environment.

  10. Experimental and numerical investigations on spray characteristics of fatty acid methyl esters

    PubMed Central

    Deshmukh, D.

    2018-01-01

    A comparative experimental and numerical study is conducted to establish the significance of the use of single-component over multi-component representatives of biodiesel, diesel and their blend for predicting spray tip penetration. Methyl oleate and methyl laurate are used as single-component representative fuels for biodiesel. The pure components n-heptane, n-dodecane and n-tetradecane are used as single-component representative fuels for diesel. Methyl laurate is found to represent biodiesel of coconut, whereas methyl oleate is found to represent biodiesel having high percentage of long-chain fatty acid esters. The spray tip penetration of methyl oleate is found to be in good agreement with the measured spray tip penetration of karanja biodiesel. The spray tip penetration prediction of n-heptane fuel is closely following diesel spray tip penetration along with that of n-tetradecane and n-dodecane. The study suggests that the knowledge of the single-component representatives of biodiesel, diesel and their blend is sufficient to predict the spray tip penetration of the corresponding biodiesel, diesel and their blend under non-evaporating environment. PMID:29515835

  11. The Ability of Bacterial Cocaine Esterase to Hydrolyze Cocaine Metabolites and Their Simultaneous Quantification Using High-Performance Liquid Chromatography-Tandem Mass Spectrometry

    PubMed Central

    Brim, Remy L.; Noon, Kathleen R.; Collins, Gregory T.; Nichols, Joseph; Narasimhan, Diwahar; Sunahara, Roger K.

    2011-01-01

    Cocaine toxicity is a widespread problem in the United States, responsible for more than 500,000 emergency department visits a year. There is currently no U.S. Food and Drug Administration-approved pharmacotherapy to directly treat cocaine toxicity. To this end, we have developed a mutant bacterial cocaine esterase (DM-CocE), which has been previously shown to rapidly hydrolyze cocaine into inert metabolites, preventing and reversing toxicity with limited immunogenic potential. Herein we describe the ability of DM-CocE to hydrolyze the active cocaine metabolites norcocaine and cocaethylene and its inability to hydrolyze benzoylecgonine. DM-CocE hydrolyzes norcocaine and cocaethylene with 58 and 45% of its catalytic efficiency for cocaine in vitro as measured by a spectrophotometric assay. We have developed a mass spectrometry method to simultaneously detect cocaine, benzoylecgonine, norcocaine, and ecgonine methyl ester to quantify the effect of DM-CocE on normal cocaine metabolism in vivo. DM-CocE administered to rats 10 min after a convulsant dose of cocaine alters the normal metabolism of cocaine, rapidly decreasing circulating levels of cocaine and norcocaine while increasing ecgonine methyl ester formation. Benzoylecgonine was not hydrolyzed in vivo, but circulating concentrations were reduced, suggesting that DM-CocE may bind and sequester this metabolite. These findings suggest that DM-CocE may reduce cocaine toxicity by eliminating active and toxic metabolites along with the parent cocaine molecule. PMID:21885621

  12. Enzymatic degradation of lignin-carbohydrate complexes (LCCs): model studies using a fungal glucuronoyl esterase from Cerrena unicolor.

    PubMed

    d'Errico, Clotilde; Jørgensen, Jonas O; Krogh, Kristian B R M; Spodsberg, Nikolaj; Madsen, Robert; Monrad, Rune Nygaard

    2015-05-01

    Lignin-carbohydrate complexes (LCCs) are believed to influence the recalcitrance of lignocellulosic plant material preventing optimal utilization of biomass in e.g. forestry, feed and biofuel applications. The recently emerged carbohydrate esterase (CE) 15 family of glucuronoyl esterases (GEs) has been proposed to degrade ester LCC bonds between glucuronic acids in xylans and lignin alcohols thereby potentially improving delignification of lignocellulosic biomass when applied in conjunction with other cellulases, hemicellulases and oxidoreductases. Herein, we report the synthesis of four new GE model substrates comprising α- and ɣ-arylalkyl esters representative of the lignin part of naturally occurring ester LCCs as well as the cloning and purification of a novel GE from Cerrena unicolor (CuGE). Together with a known GE from Schizophyllum commune (ScGE), CuGE was biochemically characterized by means of Michaelis-Menten kinetics with respect to substrate specificity using the synthesized compounds. For both enzymes, a strong preference for 4-O-methyl glucuronoyl esters rather than unsubstituted glucuronoyl esters was observed. Moreover, we found that α-arylalkyl esters of methyl α-D-glucuronic acid are more easily cleaved by GEs than their corresponding ɣ-arylalkyl esters. Furthermore, our results suggest a preference of CuGE for glucuronoyl esters of bulky alcohols supporting the suggested biological action of GEs on LCCs. The synthesis of relevant GE model substrates presented here may provide a valuable tool for the screening, selection and development of industrially relevant GEs for delignification of biomass. © 2014 Wiley Periodicals, Inc.

  13. A Comparison Study: The New Extended Shelf Life Isopropyl Ester PMR Technology versus The Traditional Methyl Ester PMR Approach

    NASA Technical Reports Server (NTRS)

    Alston, William B.; Scheiman, Daniel A.; Sivko, Gloria S.

    2005-01-01

    Polymerization of Monomeric Reactants (PMR) monomer solutions and carbon cloth prepregs of PMR II-50 and VCAP-75 were prepared using both the traditional limited shelf life methanol based PMR approach and a novel extended shelf life isopropanol based PMR approach. The methyl ester and isopropyl ester based PMR monomer solutions and PMR prepregs were aged for up to four years at freezer and room temperatures. The aging products formed were monitored using high pressure liquid chromatography (HPLC). The composite processing flow characteristics and volatile contents of the aged prepregs were also correlated versus room temperature storage time. Composite processing cycles were developed and six ply cloth laminates were fabricated with prepregs after various extended room temperature storage times. The composites were then evaluated for glass transition temperature (Tg), thermal decomposition temperature (Td), initial flexural strength (FS) and modulus (FM), long term (1000 hours at 316 C) thermal oxidative stability (TOS), and retention of FS and FM after 1000 hours aging at 316 C. The results for each ester system were comparable. Freezer storage was found to prevent the formation of aging products for both ester systems. Room temperature storage of the novel isopropyl ester system increased PMR monomer solution and PMR prepreg shelf life by at least an order of magnitude while maintaining composite properties.

  14. Three approaches to fuels from fatty compounds

    USDA-ARS?s Scientific Manuscript database

    Biodiesel, the alkyl esters, usually methyl esters, of vegetable oils, animal fats, or other triacylglycerol-containing materials, are the most common approach to producing a fuel from the mentioned materials. This fuel is obtained by transesterifying the oil or fat with an alcohol, usually methanol...

  15. Ester carbonyl vibration as a sensitive probe of protein local electric field.

    PubMed

    Pazos, Ileana M; Ghosh, Ayanjeet; Tucker, Matthew J; Gai, Feng

    2014-06-10

    The ability to quantify the local electrostatic environment of proteins and protein/peptide assemblies is key to gaining a microscopic understanding of many biological interactions and processes. Herein, we show that the ester carbonyl stretching vibration of two non-natural amino acids, L-aspartic acid 4-methyl ester and L-glutamic acid 5-methyl ester, is a convenient and sensitive probe in this regard, since its frequency correlates linearly with the local electrostatic field for both hydrogen-bonding and non-hydrogen-bonding environments. We expect that the resultant frequency-electric-field map will find use in various applications. Furthermore, we show that, when situated in a non-hydrogen-bonding environment, this probe can also be used to measure the local dielectric constant (ε). For example, its application to amyloid fibrils formed by Aβ(16-22) revealed that the interior of such β-sheet assemblies has an ε value of approximately 5.6. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  16. Synthesis, biological evaluation, and 3D QSAR study of 2-methyl-4-oxo-3-oxetanylcarbamic acid esters as N-acylethanolamine acid amidase (NAAA) inhibitors.

    PubMed

    Ponzano, Stefano; Berteotti, Anna; Petracca, Rita; Vitale, Romina; Mengatto, Luisa; Bandiera, Tiziano; Cavalli, Andrea; Piomelli, Daniele; Bertozzi, Fabio; Bottegoni, Giovanni

    2014-12-11

    N-(2-Oxo-3-oxetanyl)carbamic acid esters have recently been reported to be noncompetitive inhibitors of the N-acylethanolamine acid amidase (NAAA) potentially useful for the treatment of pain and inflammation. In the present study, we further explored the structure-activity relationships of the carbamic acid ester side chain of 2-methyl-4-oxo-3-oxetanylcarbamic acid ester derivatives. Additional favorable features in the design of potent NAAA inhibitors have been found together with the identification of a single digit nanomolar inhibitor. In addition, we devised a 3D QSAR using the atomic property field method. The model turned out to be able to account for the structural variability and was prospectively validated by designing, synthesizing, and testing novel inhibitors. The fairly good agreement between predictions and experimental potency values points to this 3D QSAR model as the first example of quantitative structure-activity relationships in the field of NAAA inhibitors.

  17. Stereocontrolled reduction of alpha- and beta-keto esters with micro green algae, Chlorella strains.

    PubMed

    Ishihara, K; Yamaguchi, H; Adachi, N; Hamada, H; Nakajima, N

    2000-10-01

    The stereocontrolled reduction of alpha- and beta-keto esters using micro green algae was accomplished by a combination of the cultivation method and the introduction of an additive. The reduction of ethyl pyruvate and ethyl benzoylformate by the photoautotrophically cultivated Chlorella sorokiniana gave the corresponding alcohol in high e.e. (>99% e.e. (S) and >99% e.e. (R), respectively). In the presence of glucose as an additive, the reduction of ethyl 3-methyl-2-oxobutanoate by the heterotrophically cultivated C. sorokiniana afforded the corresponding (R)-alcohol. On the other hand, the reduction in the presence of ethyl propionate gave the (S)-alcohol. Ethyl 2-methyl-3-oxobutanoate was reduced in the presence of glycerol by the photoautotrophically cultivated C. sorokiniana or the heterotrophically cultivated C. sorokiniana to the corresponding syn-(2R,3S)-hydroxy ester with high diastereo- and enantiomeric excess (e.e.). Some additives altered the stereochemical course in the reduction of alpha- and beta-keto esters.

  18. Anti-allergic Hydroxy Fatty Acids from Typhonium blumei Explored through ChemGPS-NP

    PubMed Central

    Korinek, Michal; Tsai, Yi-Hong; El-Shazly, Mohamed; Lai, Kuei-Hung; Backlund, Anders; Wu, Shou-Fang; Lai, Wan-Chun; Wu, Tung-Ying; Chen, Shu-Li; Wu, Yang-Chang; Cheng, Yuan-Bin; Hwang, Tsong-Long; Chen, Bing-Hung; Chang, Fang-Rong

    2017-01-01

    Increasing prevalence of allergic diseases with an inadequate variety of treatment drives forward search for new alternative drugs. Fatty acids, abundant in nature, are regarded as important bioactive compounds and powerful nutrients playing an important role in lipid homeostasis and inflammation. Phytochemical study on Typhonium blumei Nicolson and Sivadasan (Araceae), a folk anti-cancer and anti-inflammatory medicine, yielded four oxygenated fatty acids, 12R-hydroxyoctadec-9Z,13E-dienoic acid methyl ester (1) and 10R-hydroxyoctadec-8E,12Z-dienoic acid methyl ester (2), 9R-hydroxy-10E-octadecenoic acid methyl ester (3), and 12R*-hydroxy-10E-octadecenoic acid methyl ester (4). Isolated compounds were identified by spectroscopic methods along with GC-MS analysis. Isolated fatty acids together with a series of saturated, unsaturated and oxygenated fatty acids were evaluated for their anti-inflammatory and anti-allergic activities in vitro. Unsaturated (including docosahexaenoic and eicosapentaenoic acids) as well as hydroxylated unsaturated fatty acids exerted strong anti-inflammatory activity in superoxide anion generation (IC50 2.14–3.73 μM) and elastase release (IC50 1.26–4.57 μM) assays. On the other hand, in the anti-allergic assays, the unsaturated fatty acids were inactive, while hydroxylated fatty acids showed promising inhibitory activity in A23187- and antigen-induced degranulation assays (e.g., 9S-hydroxy-10E,12Z-octadecadienoic acid, IC50 92.4 and 49.7 μM, respectively). According to our results, the presence of a hydroxy group in the long chain did not influence the potent anti-inflammatory activity of free unsaturated acids. Nevertheless, hydroxylation of fatty acids (or their methyl esters) seems to be a key factor for the anti-allergic activity observed in the current study. Moreover, ChemGPS-NP was explored to predict the structure-activity relationship of fatty acids. The anti-allergic fatty acids formed different cluster distant from clinically used drugs. The bioactivity of T. blumei, which is historically utilized in folk medicine, might be related to the content of fatty acids and their metabolites. PMID:28674495

  19. Differences in neurokinin receptor pharmacology between rat and guinea-pig superior cervical ganglia.

    PubMed

    Seabrook, G R; Main, M; Bowery, B; Wood, N; Hill, R G

    1992-04-01

    1. The depolarizations elicited by seven neurokinin receptor agonists were examined in both rat and guinea-pig superior cervical ganglia by use of grease-gap methodology in the presence of tetrodotoxin (0.1 microM). Responses were normalised with respect to 1 microM eledoisin. 2. The rank order of agonist potency in the rat ganglia was senktide greater than substance P greater than substance P methyl ester = eleidosin = Sar-Met-substance P greater than neurokinin B greater than neurokinin A, whereas in guinea-pig superior cervical ganglion (SCG) the rank order was senktide greater than Sar-Met-substance P greater than neurokinin B = eledoisin = substance P methyl ester. The concentration-effect curves for substance P and neurokinin A in guinea-pig ganglia were biphasic which precluded the determination of meaningful potency values. 3. The maximal depolarization achieved by subtype selective ligands was different between these two species. On rat and guinea-pig SCG, the NK3-selective ligand, senktide, produced a maximal depolarization of 27% and 274% respectively, whereas the NK1-selective ligand, substance P methyl ester, produced depolarizations of 77% and 64% respectively. 4. The depolarizations induced by substance P methyl ester and senktide in either species were unaffected by atropine (1 microM), suggesting a lack of involvement of presynaptic neurokinin receptors in the generation of the response. 5. The potency of substance P methyl ester, senktide, and neurokinin A were unaffected by pretreating ganglia with the peptidase inhibitors bacitracin (40 micrograms ml-1), leupeptin (4 micrograms ml-1), and chymostatin (2 micrograms ml-1). Similarly, these peptidase inhibitors had no effect on the maximal depolarizations achieved by any of these agonists.6. It is evident that rat and guinea-pig superior cervical ganglia possess both NK, and NK3 receptors, but that their net contribution to depolarizations are different between the two species. The depolarizations in guinea-pig SCG are mediated predominantly by an NK3 subtype and in rat SCG by an NK, receptor subtype.

  20. The Rotational Spectrum and Conformational Structures of Methyl Valerate

    NASA Astrophysics Data System (ADS)

    Nguyen, Ha Vinh Lam; Stahl, Wolfgang

    2015-06-01

    Methyl valerate, C4H9COOCH3, belongs to the class of fruit esters, which play an important role in nature as odorants of different fruits, flowers, and wines. A sufficient explanation for the structure-odor relation of is not available. It is known that predicting the odor of a substance is not possible by knowing only its chemical formula. A typical example is the blueberry- or pine apple-like odor of ethyl isovalerate while its isomers ethyl valerate and isoamyl acetate smell like green apple and banana, respectively. Obviously, not only the composition but also the molecular structures are not negligible by determining the odor of a substance. Gas phase structures of fruit esters are thus important for a first step towards the determination of structure-odor relation since the sense of smell starts from gas phase molecules. For this purpose, a combination of microwave spectroscopy and quantum chemical calculations (QCCs) is an excellent tool. Small esters often have sufficient vapor pressure to be transferred easily in the gas phase for a rotational study but already contain a large number of atoms which makes them too big for classical structure determination by isotopic substitution and requires nowadays a comparison with the structures optimized by QCCs. On the other hand, the results from QCCs have to be validated by the experimental values. About the internal dynamics, the methoxy methyl group -COOCH3 of methyl acetate shows internal rotation with a barrier of 424.581(56) wn. A similar barrier height of 429.324(23) wn was found in methyl propionate, where the acetyl group is extended to the propionyl group. The investigation on methyl valerate fits well in this series of methyl alkynoates. In this talk, the structure of the most energetic favorable conformer as well as the internal rotation shown by the methoxy methyl group will be reported. It could be confirmed that the internal rotation barrier of the methoxy methyl group remains by longer alkyl chain.

  1. Lubricant Foaming and Aeration Study. Part 2.

    DTIC Science & Technology

    1985-12-01

    phosphate. The blend 0-77-10, composed of tmp-heptanoate plus neopentyl glycol esters, tested in the same way and with the same combination of solutes at...the same concentrations, showed about half the foaminess of the unblended tmp-heptanoate. The neopentyl glycol esters are, therefore, less...substituent methyl groups in a solute confer profoaming activity in these neopentyl glycol esters as solvents. Also, not forgotten, is that the

  2. Construction of combustion models for rapeseed methyl ester bio-diesel fuel for internal combustion engine applications.

    PubMed

    Golovitchev, Valeri I; Yang, Junfeng

    2009-01-01

    Bio-diesel fuels are non-petroleum-based diesel fuels consisting of long chain alkyl esters produced by the transesterification of vegetable oils, that are intended for use (neat or blended with conventional fuels) in unmodified diesel engines. There have been few reports of studies proposing theoretical models for bio-diesel combustion simulations. In this study, we developed combustion models based on ones developed previously. We compiled the liquid fuel properties, and the existing detailed mechanism of methyl butanoate ester (MB, C(5)H(10)O(2)) oxidation was supplemented by sub-mechanisms for two proposed fuel constituent components, C(7)H(16) and C(7)H(8)O (and then, by mp2d, C(4)H(6)O(2) and propyne, C(3)H(4)) to represent the combustion model for rapeseed methyl ester described by the chemical formula, C(19)H(34)O(2) (or C(19)H(36)O(2)). The main fuel vapor thermal properties were taken as those of methyl palmitate C(19)H(36)O(2) in the NASA polynomial form of the Burcat database. The special global reaction was introduced to "crack" the main fuel into its constituent components. This general reaction included 309 species and 1472 reactions, including soot and NO(x) formation processes. The detailed combustion mechanism was validated using shock-tube ignition-delay data under diesel engine conditions. For constant volume and diesel engine (Volvo D12C) combustion modeling, this mechanism could be reduced to 88 species participating in 363 reactions.

  3. 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

  4. Catalytic pyrolysis of model compounds and waste cooking oil for production of light olefins over La/ZSM-5 catalysts

    NASA Astrophysics Data System (ADS)

    Li, F. W.; Ding, S. L.; Li, L.; Gao, C.; Zhong, Z.; Wang, S. X.; Li, Z. X.

    2016-08-01

    Waste cooking oil (WCO) and its model compounds (oleic acid and methyl laurate) are catalytically pyrolyzed in a fixed-bed reactor over La modified ZSM-5 catalysts (La/ZSM-5) aiming for production of C2-C4 light olefins. The LaO content in catalysts was set at 0, 2, 6, 10 and 14 wt%. The gas and liquid products are analyzed. The La/ZSM-5 catalyst with 6% LaO showed higher selectivity to light olefins when WCO and methyl laurate were pyrolyzed, and olefin content was 26% for WCO and 21% for methyl laurate. The catalyst with 10% LaO showed high selectivity to light olefins (28.5%) when oleic acid was pyrolyzed. The liquid products from WCO and model compounds mainly contain esters and aromatic hydrocarbons. More esters were observed in liquid products from methyl laurate and WCO pyrolysis, indicating that it is more difficult to pyrolyze esters and WCO than oleic acid. The coked catalysts were analyzed by temperature-programmed oxidation. The result shows that graphite is the main component of coke. The conversion of WCO to light olefins potentially provides an alternative and sustainable route for production of the key petrochemicals.

  5. Selected physical properties of various diesel blends

    NASA Astrophysics Data System (ADS)

    Hlaváčová, Zuzana; Božiková, Monika; Hlaváč, Peter; Regrut, Tomáš; Ardonová, Veronika

    2018-01-01

    The quality determination of biofuels requires identifying the chemical and physical parameters. The key physical parameters are rheological, thermal and electrical properties. In our study, we investigated samples of diesel blends with rape-seed methyl esters content in the range from 3 to 100%. In these, we measured basic thermophysical properties, including thermal conductivity and thermal diffusivity, using two different transient methods - the hot-wire method and the dynamic plane source. Every thermophysical parameter was measured 100 times using both methods for all samples. Dynamic viscosity was measured during the heating process under the temperature range 20-80°C. A digital rotational viscometer (Brookfield DV 2T) was used for dynamic viscosity detection. Electrical conductivity was measured using digital conductivity meter (Model 1152) in a temperature range from -5 to 30°C. The highest values of thermal parameters were reached in the diesel sample with the highest biofuel content. The dynamic viscosity of samples increased with higher concentration of bio-component rapeseed methyl esters. The electrical conductivity of blends also increased with rapeseed methyl esters content.

  6. Comparison of in vitro and in vivo phototoxicity tests with S-(-)-10,11-dihydroxyfarnesic acid methyl ester produced by Beauveria bassiana KACC46831.

    PubMed

    Kim, Min-A; Son, Hyeong-U; Yoon, Cheol-Sik; Nam, Sung-Hee; Choi, Young-Cheol; Lee, Sang-Han

    2014-09-01

    Beauveria bassiana is a fungi that is well-known for demonstrating a resistance to environmental change. To confirm whether S-(-)-10,11-dihydroxyfarnesic acid methyl ester (DHFAME) produced by Beauveria bassiana KACC46831 causes phototoxicity when used for cosmetic purposes due to its anti-tyrosinase activity, we conducted in vitro and in vivo phototoxicity tests. There were no significant changes or damage observed in the compound-treated group with regards to skin phototoxicity, while 8-methoxypsoralen, which served as a positive control, induced toxic effects. The in vitro 3T3 neutral red uptake assay, an alternative assessment, was used for further confirmation of the phototoxicity. The results showed that DHFAME did not exhibit phototoxicity at the designated concentrations, with or without UV irradiation in the 3T3 cells. These results indicated that the methyl ester produced by Beauveria bassiana KACC46831 does not induce phototoxicity in the skin. Therefore, the results of the present study indicate that DHFAME shows potential for use as a cosmetic ingredient that does not cause skin phototoxicity.

  7. Extraction of extracellular lipids from chemoautotrophic bacteria Serratia sp. ISTD04 for production of biodiesel.

    PubMed

    Bharti, Randhir K; Srivastava, Shaili; Thakur, Indu Shekhar

    2014-08-01

    A CO2 sequestering bacterial strain, Serratia sp. ISTD04, that produces a significant amount of extracellular lipids was isolated from marble mine rocks. (14)C labeling analysis revealed that the rate of assimilation of CO2 by the strain is 0.756×10(-9)μmolCO2fixedcell(-1)h(-1). It was found to produce 466mg/l of extracellular lipid which was characterized using (1)H NMR. After transesterification of lipids, the total saturated and unsaturated FAME was found to be 51% and 49% respectively. The major FAME contained in the biodiesel were palmitic acid methyl ester (C16:0), oleic acid methyl ester (C18:1) and 10-nonadecenoic acid methyl ester (C19:1). Biodiesel produced by Serratia sp. ISTD04 is balanced in terms of FAME composition of good quality. It also contained higher proportion of oleic acid (35%) which makes it suitable for utilization in existing engines. Thus, the strain can be harnessed commercially to sequester CO2 into biodiesel. Copyright © 2014 Elsevier Ltd. All rights reserved.

  8. Poly(styrene-co-N-methacryloyl-l-phenylalanine methyl ester)-functionalized magnetic nanoparticles as sorbents for the analysis of sodium benzoate in beverages.

    PubMed

    Ji, Shilei; Li, Nan; Qi, Li; Wang, Minglin

    2017-01-01

    In this study, poly(styrene-co-N-methacryloyl-l-phenylalanine methyl ester)-functionalized magnetic nanoparticles were constructed and used as magnetic solid-phase extraction sorbents for analysis of food preservatives in beverages. To prepare the poly(amino acid)-based sorbents, N-methacryloyl-l-phenylalanine methyl ester, and styrene served as the functional monomers and modified onto the magnetic nanoparticles via free radical polymerization. Interestingly, compared with propylparaben and potassium sorbate, the proposed poly(amino acid)-based sorbents showed a good selectivity to sodium benzoate. The adsorption capacity of the sorbents to sodium benzoate was 6.08 ± 0.31 mg/g. Moreover, the fast adsorption equilibrium could be reached within 5 min. Further, the resultant poly(amino acid)-based sorbents were applied in the analysis of sodium benzoate in real beverage samples. The results proved that the proposed magnetic solid-phase extraction sorbents have a great potential for the analysis of preservatives in food samples. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  9. Epoxy Phosphonate Crosslinkers for Providing Flame Resistance to Cotton Textiles

    USDA-ARS?s Scientific Manuscript database

    Two new monomers (2-methyl-oxiranylmethyl)-phosphonic acid dimethyl ester (3) and [2-(dimethoxy-phosphorylmethyl)-oxyranylmethyl]-phosphonic acid dimethyl ester (6) were prepared and used with dicyandiamide (7) and citric acid (8) to impart flame resistance to cotton plain weave, twill, and 80:20-co...

  10. 76 FR 32332 - BASF Corp.; Filing of Food Additive Petition (Animal Use); Methyl Esters of Conjugated Linoleic...

    Federal Register 2010, 2011, 2012, 2013, 2014

    2011-06-06

    ... esters of conjugated linoleic acid (CLA) as a source of fatty acids in lactating dairy cow diets and for... a source of fatty acids in lactating dairy cow diets. BASF's FAP 2269 further proposes the use of...

  11. Binding Mode and Structure-Activity Relationships of ITE as an Aryl Hydrocarbon Receptor (AhR) Agonist.

    PubMed

    Dolciami, Daniela; Gargaro, Marco; Cerra, Bruno; Scalisi, Giulia; Bagnoli, Luana; Servillo, Giuseppe; Fazia, Maria Agnese Della; Puccetti, Paolo; Quintana, Francisco J; Fallarino, Francesca; Macchiarulo, Antonio

    2018-02-06

    Discovered as a modulator of the toxic response to environmental pollutants, aryl hydrocarbon receptor (AhR) has recently gained attention for its involvement in various physiological and pathological pathways. AhR is a ligand-dependent transcription factor activated by a large array of chemical compounds, which include metabolites of l-tryptophan (l-Trp) catabolism as endogenous ligands of the receptor. Among these, 2-(1'H-indole-3'-carbonyl)thiazole-4-carboxylic acid methyl ester (ITE) has attracted interest in the scientific community, being endowed with nontoxic, immunomodulatory, and anticancer AhR-mediated functions. So far, no information about the binding mode and interactions of ITE with AhR is available. In this study, we used docking and molecular dynamics to propose a putative binding mode of ITE into the ligand binding pocket of AhR. Mutagenesis studies were then instrumental in validating the proposed binding mode, identifying His 285 and Tyr 316 as important key residues for ligand-dependent receptor activation. Finally, a set of ITE analogues was synthesized and tested to further probe molecular interactions of ITE to AhR and characterize the relevance of specific functional groups in the chemical structure for receptor activity. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  12. Solvation of Esters and Ketones in Supercritical CO2.

    PubMed

    Kajiya, Daisuke; Imanishi, Masayoshi; Saitow, Ken-ichi

    2016-02-04

    Vibrational Raman spectra for the C═O stretching modes of three esters with different functional groups (methyl, a single phenyl, and two phenyl groups) were measured in supercritical carbon dioxide (scCO2). The results were compared with Raman spectra for three ketones involving the same functional groups, measured at the same thermodynamic states in scCO2. The peak frequencies of the Raman spectra of these six solute molecules were analyzed by decomposition into the attractive and repulsive energy components, based on the perturbed hard-sphere theory. For all solute molecules, the attractive energy is greater than the repulsive energy. In particular, a significant difference in the attractive energies of the ester-CO2 and ketone-CO2 systems was observed when the methyl group is attached to the ester or ketone. This difference was significantly reduced in the solute systems with a single phenyl group and was completely absent in those with two phenyl groups. The optimized structures among the solutes and CO2 molecules based on quantum chemical calculations indicate that greater attractive energy is obtained for a system where the oxygen atom of the ester is solvated by CO2 molecules.

  13. In vitro antifungal activity of fatty acid methyl esters of the seeds of Annona cornifolia A.St.-Hil. (Annonaceae) against pathogenic fungus Paracoccidioides brasiliensis.

    PubMed

    Lima, Luciana Alves Rodrigues dos Santos; Johann, Susana; Cisalpino, Patrícia Silva; Pimenta, Lúcia Pinheiro Santos; Boaventura, Maria Amélia Diamantino

    2011-01-01

    Fatty acids are abundant in vegetable oils. They are known to have antibacterial and antifungal properties. Antifungal susceptibility was evaluated by broth microdilution assay following CLSI (formerly the NCCLS) guidelines against 16 fungal strains of clinical interest. In this work, fatty acid methyl esters (FAME) was able to inhibit 12 clinical strains of the pathogenic fungus Paracoccidioides brasiliensis and were also active in the bioautographic assay against Cladosporium sphaerospermum. FAME was a more potent antifungal than trimethoprim-sulfamethoxazole against P. brasiliensis under the experimental conditions tested.

  14. Covalent modification of proteins by cocaine

    NASA Astrophysics Data System (ADS)

    Deng, Shi-Xian; Bharat, Narine; Fischman, Marian C.; Landry, Donald W.

    2002-03-01

    Cocaine covalently modifies proteins through a reaction in which the methyl ester of cocaine acylates the -amino group of lysine residues. This reaction is highly specific in vitro, because no other amino acid reacts with cocaine, and only cocaine's methyl ester reacts with the lysine side chain. Covalently modified proteins were present in the plasma of rats and human subjects chronically exposed to cocaine. Modified endogenous proteins are immunogenic, and specific antibodies were elicited in mouse and detected in the plasma of human subjects. Covalent modification of proteins could explain cocaine's autoimmune effects and provide a new biochemical approach to cocaine's long-term actions.

  15. L-Leucyl-L-Leucine Methyl Ester Treatment of Canine Marrow and Peripheral Blood Cells: Inhibition of Proliferative Responses with Maintenance of the Capacity for Autologous Marrow Engraftment

    DTIC Science & Technology

    1988-11-01

    Copyright 0 198 by The Winiams & Wilkins Co. Printed in U.S.A. L-LEUCYL-L-LEUCINE METHYL ESTER TREATMENT OF CANINE MARROW AND PERIPHERAL BLOOD CELLS...Reearch CeThs eatetle, Washington 9%104 tInaiyuba on o canine UMrrowt and peripher hi Recently, Thiele and Lipsky have described adipeptide nionon clear...that marrow iincubation with Leu-Leu. Leu-Leu-OMe is a feasible method to deplete canine marrows of aloreactive and cytotoxic T cells prior to OMe

  16. Critical aggregates concentration of fatty esters present in biodiesel determined by turbidity and fluorescence.

    PubMed

    Froehner, Sandro; Sánez, Juan; Dombroski, Luiz Fernando; Gracioto, Maria Paula

    2017-09-01

    Biodiesel for combustible engine is available as mixture of fossil diesel and fatty esters obtained by transesterification of vegetable oils. The use of biodiesel reduces the amount of SO x , mainly. However, it was already observed that biodiesel has a different behavior in environment in cases of accidental spill and groundwater contamination. It was noticed that the biodegradation of hydrocarbons (cyclic and aliphatic) in the presence of biodiesel are speeded, although the mechanism is still unclear. Considering the chemical structure of fatty esters, it was investigated the formation of aggregates in water solution by fatty esters present in commercial biodiesel. In Brazil, biodiesel is composed by 95% of fossil diesel and 5% of fatty esters mixture. In this work, fatty esters were treated as neutral surfactant, i.e., it was treated as a molecule with polar and non-polar part. Turbidity and fluorescence were used to determine the critical aggregates concentration (CAC). Water solutions containing fatty esters were examined exploiting changes in turbidity and fluorescence intensity of pyrene. Abrupt changes were attributed to aggregates formation, following the same behavior of traditional amphiphilic compounds. It was determined the CAC for ethyl palmitate, ethyl stearate, ethyl oleate, and ethyl linoleate. The values of CAC for fatty esters varied from 1.91 to 4.27 μmol/L, while CAC for the mixture of esters (biodiesel) was 2.01 for methyl esters and 1.19 for ethyl esters, both prepared using soybean oil. The aggregates formation was also determined by fluorescence measurements considering the changes in intensity of peaks I and III of pyrene. Pyrene senses the changes in environment polarity. The values found of CAC by fluorescence for individual ethyl esters varied from 1.85 to 3.21 μmol/L, while mixtures of ethyl esters was 2.23 and 2.07 μmol/L for mixture of methyl esters. The results clearly showed that fatty esters form aggregates and might be responsible for speed degradation of compounds by accommodation of them in inner part of aggregates.

  17. UPLC-MS/MS analysis of ochratoxin A metabolites produced by Caco-2 and HepG2 cells in a co-culture system.

    PubMed

    González-Arias, Cyndia A; Marín, Sonia; Rojas-García, Aurora E; Sanchis, Vicente; Ramos, Antonio J

    2017-11-01

    Ochatoxin A (OTA) is one of the most important mycotoxins based on its toxicity. The oral route is the main gateway of entry of OTA into the human body, and specialized epithelial cells constitute the first barrier. The present study investigated the in vitro cytotoxic effect of OTA (5, 15 and 45 μM) and production of OTA metabolities in Caco-2 and HepG2 cells using a co-culture Transwell System to mimic the passage through the intestinal epithelium and hepatic metabolism. The results derived from MTS cell viability assays and transepithelial electrical resistance measurements showed that OTA was slightly cytotoxic at the lowest concentration at 3 h, but significant toxicity was observed at all concentrations at 24 h. OTA metabolites generated in this co-culture were ochratoxin B (OTB), OTA methyl ester, OTA ethyl ester and the OTA glutathione conjugate (OTA-GSH). OTA methyl ester was the major metabolite found in both Caco-2 and HepG2 cells after all treatments. Our results showed that OTA can cause cell damage through several mechanisms and that the OTA exposure time is more important that the dosage in in vitro studies. OTA methyl ester is proposed as an OTA exposure biomarker, although future studies should be conducted. Copyright © 2017 Elsevier Ltd. All rights reserved.

  18. Effective methylation of phosphonic acids related to chemical warfare agents mediated by trimethyloxonium tetrafluoroborate for their qualitative detection and identification by gas chromatography-mass spectrometry

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    Valdez, Carlos A.; Leif, Roald N.; Alcaraz, Armando

    The effective methylation of phosphonic acids related to chemical warfare agents (CWAs) employing trimethyloxonium tetrafluoroborate (TMO·BF 4) for their qualitative detection and identification by gas chromatography-mass spectrometry (GC-MS) is presented. The methylation occurs in rapid fashion (1 h) and can be conveniently carried out at ambient temperature, thus providing a safer alternative to the universally employed diazomethane-based methylation protocols. Optimization of the methylation parameters led us to conclude that methylene chloride was the ideal solvent to carry out the derivatization, and that even though methylated products can be observed surfacing after only 1 h, additional time was not found tomore » be detrimental but beneficial to the process particularly when dealing with analytes at low concentrations (~10 μg mL -1). Due to its insolubility in methylene chloride, TMO·BF 4 conveniently settles to the bottom during the reaction and does not produce additional interfering by-products that may further complicate the GC-MS analysis. We demonstrated the method to successfully methylate a variety of Schedule 2 phosphonic acids, including their half esters, resulting in derivatives that were readily detected and identified using the instrument's spectral library. Most importantly, the method was shown to simultaneously methylate a mixture of the organophosphorus-based nerve agent hydrolysis products: pinacolyl methylphosphonate (PMPA), cyclohexyl methylphosphonate (CyMPA) and ethyl methylphosphonate (EMPA) (at a 10 μg mL -1 concentration each) in a fatty acid ester-rich organic matrix (OPCW-PT-O 3) featured in the 38th Organisation for the Prohibition of Chemical Weapons (OPCW) Proficiency Test. Additionally, the protocol was found to effectively methylate N,N-diethylamino ethanesulfonic acid and N,N-diisopropylamino ethanesulfonic acid that are products arising from the oxidative degradation of the V-series agents VR and VX respectively. This work described herein represents the first report on the use of TMO·BF 4 as a viable, stable and safe agent for the methylation of phosphonic acids and their half esters and within the context of an OPCW Proficiency Test sample analysis.« less

  19. Effective methylation of phosphonic acids related to chemical warfare agents mediated by trimethyloxonium tetrafluoroborate for their qualitative detection and identification by gas chromatography-mass spectrometry

    DOE PAGES

    Valdez, Carlos A.; Leif, Roald N.; Alcaraz, Armando

    2016-06-01

    The effective methylation of phosphonic acids related to chemical warfare agents (CWAs) employing trimethyloxonium tetrafluoroborate (TMO·BF 4) for their qualitative detection and identification by gas chromatography-mass spectrometry (GC-MS) is presented. The methylation occurs in rapid fashion (1 h) and can be conveniently carried out at ambient temperature, thus providing a safer alternative to the universally employed diazomethane-based methylation protocols. Optimization of the methylation parameters led us to conclude that methylene chloride was the ideal solvent to carry out the derivatization, and that even though methylated products can be observed surfacing after only 1 h, additional time was not found tomore » be detrimental but beneficial to the process particularly when dealing with analytes at low concentrations (~10 μg mL -1). Due to its insolubility in methylene chloride, TMO·BF 4 conveniently settles to the bottom during the reaction and does not produce additional interfering by-products that may further complicate the GC-MS analysis. We demonstrated the method to successfully methylate a variety of Schedule 2 phosphonic acids, including their half esters, resulting in derivatives that were readily detected and identified using the instrument's spectral library. Most importantly, the method was shown to simultaneously methylate a mixture of the organophosphorus-based nerve agent hydrolysis products: pinacolyl methylphosphonate (PMPA), cyclohexyl methylphosphonate (CyMPA) and ethyl methylphosphonate (EMPA) (at a 10 μg mL -1 concentration each) in a fatty acid ester-rich organic matrix (OPCW-PT-O 3) featured in the 38th Organisation for the Prohibition of Chemical Weapons (OPCW) Proficiency Test. Additionally, the protocol was found to effectively methylate N,N-diethylamino ethanesulfonic acid and N,N-diisopropylamino ethanesulfonic acid that are products arising from the oxidative degradation of the V-series agents VR and VX respectively. This work described herein represents the first report on the use of TMO·BF 4 as a viable, stable and safe agent for the methylation of phosphonic acids and their half esters and within the context of an OPCW Proficiency Test sample analysis.« less

  20. AVOIDING PITFALLS IN THE DETERMINATION OF HALOCARBOXYLIC ACIDS: THE PHOTOCHEMISTRY OF METHYLATION

    EPA Science Inventory

    Haloethanoic (haloacetic) acids are formed during chlorination of drinking water and are regulated by the Environmental Protection Agency (EPA). These compounds are normally quantified by gas chromatography with electron capture detection (GC-ECD) ad the methyl esters. EPA Meth...

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

    PubMed

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

    2017-12-06

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

  2. Tension cost correlates with mechanical and biochemical parameters in different myocardial contractility conditions

    PubMed Central

    Moreira, Cleci M.; Meira, Eduardo F.; Vestena, Luis; Stefanon, Ivanita; Vassallo, Dalton V.; Padilha, Alessandra S.

    2012-01-01

    OBJECTIVES: Tension cost, the ratio of myosin ATPase activity to tension, reflects the economy of tension development in the myocardium. To evaluate the mechanical advantage represented by the tension cost, we studied papillary muscle contractility and the activity of myosin ATPase in the left ventricles in normal and pathophysiological conditions. METHODS: Experimental protocols were performed using rat left ventricles from: (1) streptozotocin-induced diabetic and control Wistar rats; (2) N-nitro-L-arginine methyl ester (L-NAME) hypertensive and untreated Wistar rats; (3) deoxycorticosterone acetate (DOCA) salt-treated, nephrectomized and salt- and DOCA-treated rats; (4) spontaneous hypertensive rats (SHR) and Wistar Kyoto (WKY) rats; (5) rats with myocardial infarction and sham-operated rats. The isometric force, tetanic tension, and the activity of myosin ATPase were measured. RESULTS: The results obtained from infarcted, diabetic, and deoxycorticosterone acetate-salt-treated rats showed reductions in twitch and tetanic tension compared to the control and sham-operated groups. Twitch and tetanic tension increased in the N-nitro-L-arginine methyl ester-treated rats compared with the Wistar rats. Myosin ATPase activity was depressed in the infarcted, diabetic, and deoxycorticosterone acetate salt-treated rats compared with control and sham-operated rats and was increased in N-nitro-L-arginine methyl ester-treated rats. These parameters did not differ between SHR and WKY rats. In the studied conditions (e.g., post-myocardial infarction, deoxycorticosterone acetate salt-induced hypertension, chronic N-nitro-L-arginine methyl ester treatment, and streptozotocin-induced diabetes), a positive correlation between force or plateau tetanic tension and myosin ATPase activity was observed. CONCLUSION: Our results suggest that the myocardium adapts to force generation by increasing or reducing the tension cost to maintain myocardial contractility with a better mechanical advantage. PMID:22666794

  3. Arginine methylation of REF/ALY promotes efficient handover of mRNA to TAP/NXF1

    PubMed Central

    Hung, Ming-Lung; Hautbergue, Guillaume M.; Snijders, Ambrosius P. L.; Dickman, Mark J.; Wilson, Stuart A.

    2010-01-01

    The REF/ALY mRNA export adaptor binds TAP/NXF1 via an arginine-rich region, which overlaps with its RNA-binding domain. When TAP binds a REF:RNA complex, it triggers transfer of the RNA from REF to TAP. Here, we have examined the effects of arginine methylation on the activities of the REF protein in mRNA export. We have mapped the arginine methylation sites of REF using mass spectrometry and find that several arginines within the TAP and RNA binding domains are methylated in vivo. However, arginine methylation has no effect on the REF:TAP interaction. Instead, arginine methylation reduces the RNA-binding activity of REF in vitro and in vivo. The reduced RNA-binding activity of REF in its methylated state is essential for efficient displacement of RNA from REF by TAP in vivo. Therefore, arginine methylation fine-tunes the RNA-binding activity of REF such that the RNA–protein interaction can be readily disrupted by export factors further down the pathway. PMID:20129943

  4. Theoretical and kinetic study of the hydrogen atom abstraction reactions of esters with H(O.)2 radicals.

    PubMed

    Mendes, Jorge; Zhou, Chong-Wen; Curran, Henry J

    2013-12-27

    This work details an ab initio and chemical kinetic study of the hydrogen atom abstraction reactions by the hydroperoxyl radical (HȮ2) on the following esters: methyl ethanoate, methyl propanoate, methyl butanoate, methyl pentanoate, methyl isobutyrate, ethyl ethanoate, propyl ethanoate, and isopropyl ethanoate. Geometry optimizations and frequency calculations of all of the species involved, as well as the hindrance potential descriptions for reactants and transition states, have been performed with the Møller-Plesset (MP2) method using the 6-311G(d,p) basis set. A validation of all of the connections between transition states and local minima was performed by intrinsic reaction coordinate calculations. Electronic energies for all of the species are reported at the CCSD(T)/cc-pVTZ level of theory in kcal mol(-1) with the zero-point energy corrections. The CCSD(T)/CBS (extrapolated from CCSD(T)/cc-pVXZ, in which X = D, T, Q) was used for the reactions of methyl ethanoate + HȮ2 radicals as a benchmark in the electronic energy calculations. High-pressure limit rate constants, in the temperature range 500-2000 K, have been calculated for all of the reaction channels using conventional transition state theory with asymmetric Eckart tunneling corrections. The 1-D hindered rotor approximation has been used for the low frequency torsional modes in both reactants and transition states. The calculated individual and total rate constants are reported for all of the reaction channels in each reaction system. A branching ratio analysis for each reaction site has also been investigated for all of the esters studied in this work.

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

    NASA Astrophysics Data System (ADS)

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

    2017-02-01

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

  6. Methyl group reorientation under ligand binding probed by pseudocontact shifts.

    PubMed

    Lescanne, Mathilde; Ahuja, Puneet; Blok, Anneloes; Timmer, Monika; Akerud, Tomas; Ubbink, Marcellus

    2018-06-02

    Liquid-state NMR spectroscopy is a powerful technique to elucidate binding properties of ligands on proteins. Ligands binding in hydrophobic pockets are often in close proximity to methyl groups and binding can lead to subtle displacements of methyl containing side chains to accommodate the ligand. To establish whether pseudocontact shifts can be used to characterize ligand binding and the effects on methyl groups, the N-terminal domain of HSP90 was tagged with caged lanthanoid NMR probe 5 at three positions and titrated with a ligand. Binding was monitored using the resonances of leucine and valine methyl groups. The pseudocontact shifts (PCS) caused by ytterbium result in enhanced dispersion of the methyl spectrum, allowing more resonances to be observed. The effects of tag attachment on the spectrum and ligand binding are small. Significant changes in PCS were observed upon ligand binding, indicating displacements of several methyl groups. By determining the cross-section of PCS iso-surfaces generated by two or three paramagnetic centers, the new position of a methyl group can be estimated, showing displacements in the range of 1-3 Å for methyl groups in the binding site. The information about such subtle but significant changes may be used to improve docking studies and can find application in fragment-based drug discovery.

  7. Fatty acid methyl esters with two vicinal alkylthio side chains and their NMR characterization

    USDA-ARS?s Scientific Manuscript database

    The addition reaction of dimethyl disulfide (DMDS) to double bonds in alkenes and monounsaturated fatty acid esters in the presence of iodine or other catalysts to give bis(methylthio) derivatives has largely served analytical purposes in mass spectrometry with scattered reports on the addition of o...

  8. Oligomeric secoiridoid glucosides from Jasminum abyssinicum.

    PubMed

    Gallo, Francesca Romana; Palazzino, Giovanna; Federici, Elena; Iurilli, Raffaella; Monache, Franco Delle; Chifundera, Kusamba; Galeffi, Corrado

    2006-03-01

    From the root bark of Jasminum abyssinicum (Oleaceae) collected in Congo was isolated tree oligomeric secoiridoid glucosides named craigosides A-C. The three compounds are esters of a cyclopentanoid monoterpene with an iridane skeleton, esterified with three, two and two, respectively, units of oleoside 11-methyl ester. The structures were elucidated by spectroscopic methods and chemical correlations.

  9. Ultraviolet absorbing copolymers

    DOEpatents

    Gupta, Amitava; Yavrouian, Andre H.

    1982-01-01

    Photostable and weather stable absorping copolymers have been prepared from acrylic esters such as methyl methacrylate containing 0.1 to 5% of an 2-hydroxy-allyl benzophenone, preferably the 4,4' dimethoxy derivative thereof. The pendant benzophenone chromophores protect the acrylic backbone and when photoexcited do not degrade the ester side chain, nor abstract hydrogen from the backbone.

  10. Targeting mitochondria: Esters of rhodamine B with triterpenoids are mitocanic triggers of apoptosis.

    PubMed

    Wolfram, Ratna Kancana; Heller, Lucie; Csuk, René

    2018-05-25

    Triterpenoic acids, ursolic acid (1), oleanolic acid (2), glycyrrhetinic acid (3) and betulinic acid (4) were converted into their corresponding methyl 5-8 and benzyl esters 9-12 or benzyl amides 21-24. These derivatives served as starting materials for the synthesis of pink colored rhodamine B derivatives 25-36 which were screened for cytotoxicity in colorimetric SRB assays. All of the compounds were cytotoxic for a variety of human tumor cell lines. The activity of the benzyl ester derivatives 29-32 was lower than the cytotoxicity of the methyl esters 25-28. The benzyl amides 33-36 were the most cytotoxic compounds of this series. The most potential compound was a glycyrrhetinic acid rhodamine B benzyl amide 35. This compound showed activity against the different cancer cell lines in a two-digit to low three-digit nano-molar range. Staining experiments combined with fluorescence microscopy showed that this compound triggered apoptosis in A2780 ovarian carcinoma cells and acted as a mitocan. Copyright © 2018 Elsevier Masson SAS. All rights reserved.

  11. Synthesis and characterization of a novel long-alkyl-chain ester-substituted benzimidazole gelator and its octan-1-ol solvate.

    PubMed

    Geiger, H Cristina; Zick, Patricia L; Roberts, William R; Geiger, David K

    2017-04-01

    The synthesis of a novel benzimidazole derivative with a long-chain-ester substituent, namely methyl 8-[4-(1H-benzimidazol-2-yl)phenoxy]octanoate, (3), is reported. Ester (3) shows evidence of aggregation in solution and weak gelation ability with toluene. The octan-1-ol solvate, methyl 8-[4-(1H-benzimidazol-2-yl)phenoxy]octanoate octan-1-ol monosolvate, C 22 H 26 N 2 O 3 ·C 8 H 18 O, (4), exhibits a four-molecule hydrogen-bonded motif in the solid state, with N-H...O hydrogen bonds between benzimidazole molecules and O-H...N hydrogen bonds between the octan-1-ol solvent molecules and the benzimidazole unit. The alkyl chains of the ester and the octan-1-ol molecules are in unfolded conformations. The phenylene ring is canted by 10.27 (6)° from the plane of the benzimidazole ring system. H...C contacts make up 20.7% of the Hirshfeld surface coverage. Weak C-H...π interactions involving the benzimidazole alkyl chain and three aromatic rings are observed.

  12. 21 CFR 182.60 - Synthetic flavoring substances and adjuvants.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... aldehyde). N-Butyric acid (butanoic acid). d- or l-Carvone (carvol). Cinnamaldehyde (cinnamic aldehyde... aldehyde, caprinaldehyde, aldehyde C-10). Ethyl acetate. Ethyl butyrate. 3-Methyl-3-phenyl glycidic acid ethyl ester (ethyl-methyl-phenyl-glycidate, so-called strawberry aldehyde, C-16 aldehyde). Ethyl...

  13. Isolation, identification and antioxidant activity of bound phenolic compounds present in rice bran.

    PubMed

    Wang, Wei; Guo, Jia; Zhang, Junnan; Peng, Jie; Liu, Tianxing; Xin, Zhihong

    2015-03-15

    The bound phenolic compounds in rice bran were released and extracted with ethyl acetate based on alkaline digestion. An investigation of the chemical constituents of EtOAc extract has led to the isolation of a new compound, para-hydroxy methyl benzoate glucoside (8), together with nine known compounds, cycloeucalenol cis-ferulate (1), cycloeucalenol trans-ferulate (2), trans-ferulic acid (3), trans-ferulic acid methyl ester (4), cis-ferulic acid (5), cis-ferulic acid methyl ester (6), methyl caffeate (7), vanillic aldehyde (9) and para-hydroxy benzaldehyde (10). The structures of these compounds were determined using a combination of spectroscopic methods and chemical analysis. Among the compounds isolated, compound 3, 5 and 7 exhibited strong DPPH and ABTS(+) radical scavenging activities, followed by compounds 4 and 6. Compound 1 and 2 showed potent DPPH and ABTS(+) radical scavenging activities, compound 8 displayed moderate antioxidant activity against ABTS(+) radical, whereas compound 9 and 10 showed weak antioxidant activity. Copyright © 2014 Elsevier Ltd. All rights reserved.

  14. Functional Characterization of a Novel Marine Microbial Esterase and its Utilization in the Enantioselective Preparation of (R)-Methyl 2-Chloropropionate.

    PubMed

    Cao, Yingying; Deng, Dun; Sun, Aijun; Zhang, Yun; Hu, Yunfeng

    2016-09-01

    Chiral 2-chloropropanoic acids and their ester derivatives are crucial intermediates in the synthesis of many chemicals, especially herbicides. The enzymatic synthesis of chiral 2-chloropropanoic acids and their ester derivatives by esterases was not easily achieved, because the structural difference between the two enantiomers was too small to be recognized by esterases. Herein, we report the expression and functional characterization of one novel low temperature-resistant esterase EST12-7 identified from the genome of Pseudonocardia antitumoralis SCSIO 01299 isolated from the sediments of the South China Sea. Biocatalyst EST12-7 could hydrolyze racemic methyl 2-chloropropinate and generate optically pure (R)-methyl 2-chloropropinate with high enantiomeric excess (>99 %) and conversion (>49 %) after process optimization. Notably, the addition of different surfactants and using surfactants of different concentrations in the kinetic resolution catalyzed by EST12-7 could greatly affect the enantiomeric excess and conversion rate of product (R)-methyl 2-chloropropinate.

  15. Carbodithioic acid esters of fluoxetine, a novel class of dual-function spermicides.

    PubMed

    Kiran Kumar, S T V S; Kumar, Lalit; Sharma, Vishnu L; Jain, Ashish; Jain, Rajeev K; Maikhuri, Jagdamba P; Kumar, Manish; Shukla, Praveen K; Gupta, Gopal

    2008-10-01

    Carbodithioic acid esters of fluoxetine have been prepared by replacing the methylamino function in aminopropane chain with carbodithioic acid ester group and by adding various S-2-hydroxypropyl ester of dialkyl carbodithioic acid at 3-methylamino group. Some of these compounds showed spermicidal, antifungal and anti-Trichomonas activities. The study revealed that incorporation of carbodithioic acid residue directly into fluoxetine structure leads to compounds with better antifungal and anti-Trichomonas activities, and N-methyl-[3-phenyl-3-(4-trifluoromethyl-phenoxy)-propyl]carbodithioic acid S-(2-pyrrolidino-ethyl) ester (14) has shown better profile than both fluoxetine and nonoxynol-9. Further lead optimization may yield a potent dual-function spermicide.

  16. Resveratrol inhibits phorbol ester-induced membrane translocation of presynaptic Munc13-1.

    PubMed

    Pany, Satyabrata; Ghosh, Anamitra; You, Youngki; Nguyen, Nga; Das, Joydip

    2017-11-01

    Resveratrol (1) is a naturally occurring polyphenol that has been implicated in neuroprotection. One of resveratrol's several biological targets is Ca 2+ -sensitive protein kinase C alpha (PKCα). Resveratrol inhibits PKCα by binding to its activator-binding C1 domain. Munc13-1 is a C1 domain-containing Ca 2+ -sensitive SNARE complex protein essential for vesicle priming and neurotransmitter release. To test if resveratrol could also bind and inhibit Munc13-1, we studied the interaction of resveratrol and its derivatives, (E)-1,3-dimethoxy-5-(4-methoxystyryl)benzene, (E)-5,5'-(ethene-1,2-diyl)bis(benzene-1,2,3-triol), (E)-1,2-bis(3,4,5-trimethoxyphenyl)ethane, and (E)-5-(4-(hexadecyloxy)-3,5-dihydroxystyryl)benzene-1,2,3-triol with Munc13-1 by studying its membrane translocation from cytosol to plasma membrane in HT22 cells and primary hippocampal neurons. Resveratrol, but not the derivatives inhibited phorbol ester-induced Munc13-1 translocation from cytosol to membrane in HT22 cells and primary hippocampal neurons, as evidenced by immunoblot analysis and confocal microscopy. Resveratrol did not show any effect on Munc13-1 H567K , a mutant which is not sensitive to phorbol ester. Binding studies with Munc13-1 C1 indicated that resveratrol competes with phorbol ester for the binding site. Molecular docking and dynamics studies suggested that hydroxyl groups of resveratrol interact with phorbol-ester binding residues in the binding pocket. This study characterizes Munc13-1 as a target of resveratrol and highlights the importance of dietary polyphenol in the management of neurodegenerative diseases. Copyright © 2017 Elsevier B.V. All rights reserved.

  17. Multiple binding sites involved in the effect of choline esters on decarbamoylation of monomethylcarbamoyl- or dimethylcarbamoly-acetylcholinesterase.

    PubMed Central

    Sok, D E; Kim, Y B; Choi, S J; Jung, C H; Cha, S H

    1994-01-01

    Multiple binding sites for inhibitory choline esters in spontaneous decarbamoylation of dimethylcarbamoyl-acetylcholinesterase (AChE) were suggested from a wide range of IC50 values, in contrast with a limited range of AC50 values (concentration giving 50% of maximal activation) at a peripheral activatory site. Association of choline esters containing a long acyl chain (C7-C12) with the hydrophobic zone in the active site could be deduced from a linear relationship between the size of the acyl group and the inhibitory potency in either spontaneous decarbamoylation or acetylthiocholine hydrolysis. Direct support for laurylcholine binding to the active site might come from the competitive inhibition (Ki 33 microM) of choline-catalysed decarbamoylation by laurylcholine. Moreover, its inhibitory action was greater for monomethylcarbamoyl-AChE than for dimethylcarbamoyl-AChE, where there is a greater steric hindrance at the active centre. In further support, the inhibition of pentanoylthiocholine-induced decarbamoylation by laurylcholine was suggested to be due to laurylcholine binding to a central site rather than a peripheral site, similar to the inhibition of spontaneous decarbamoylation by laurylcholine. Supportive data for acetylcholine binding to the active site are provided by the results that acetylcholine is a competitive inhibitor (Ki 7.6 mM) of choline-catalysed decarbamoylation, and its inhibitory action was greater for monomethylcarbamoyl-AChE than for dimethylcarbamoyl-AChE. Meanwhile, choline esters with an acyl group of an intermediate size (C4-C6), more subject to steric exclusion at the active centre, and less associable with the hydrophobic zone, appear to bind preferentially to a peripheral activity site. Thus the multiple effects of choline esters may be governed by hydrophobicity and/or a steric effect exerted by the acyl moiety at the binding sites. PMID:8053896

  18. Autoignition Studies of Diesel Alternative Biofuels

    NASA Astrophysics Data System (ADS)

    Wang, Weijing

    The autoignition of biofuel compounds that offer potential as diesel fuel alternatives was studied under high-pressure engine-like conditions using the shock tube technique. Ignition delay times were determined in reflected shock experiments using measured pressure and electronically-excited OH emission. Measurements were made at conditions ranging from 650 to 1350 K, pressures from 6 to 50 atm, and for fuel/air/diluent mixtures at equivalence ratios from 0.5 to 2. The wide range of temperatures examined provides observation of autoignition in three reactivity regimes, including the negative temperature coefficient (NTC) regime which is characteristic of fuels containing alkyl functionalities. Compounds studied include biodiesel-related compounds and real biodiesel fuels, dimethyl ether, and 3-methylheptane which is representative of compounds found in synthetic diesel fuels produced using the Fischer-Tropsch and hydrotreatment processes. Biodiesel compounds studied include biodiesel surrogates, methyl decanoate, methyl-5-decenoate, and methyl-9-decenoate; compounds found in large quantities in biodiesels, methyl palmitate, methyl stearate, methyl oleate, and methyl linoleate; and soy-based and animal fat based methyl ester biodiesels. Comparison of biodiesel compounds illustrates the influence of molecular structure (e.g., chain length, double bonds, and ester functionality) on reactivity. For methyl decanoate, the effect of high pressure exhaust gas recirculation (EGR) conditions relevant to internal combustion engines was also determined. Results showed that the first-order influence of EGR by displacing fuel and O2 to decrease radical branching. Measurements were compared to kinetic modeling results from models available in the literature providing varying degrees of model validation. Reaction flux analyses were also carried out to further examine the kinetic differences in different temperature regimes for fuel compounds. For example, reaction flux analyses illustrates the importance of the long alkyl chain in controlling the overall reactivity of methyl ester biodiesel compounds and the subtle role the ester group has on inhibiting low-temperature reactivity as well as the influence of branching on reactivity for lightly branched alkanes. This thesis work provides a rich database of kinetic information for biofuel-related compounds at conditions relevant to real engine operations, offering quantitative kinetic targets for the development and evaluation of future kinetic models for important alternative fuel compounds. The results quantify the reactivity variability of biodiesel alternatives and illustrate that at temperature greater than 900 to 1000 K fuel structure has little influence on reactivity, as fuel fragmentation results in an intermediate pool that is largely the same for the fuels studied. On the other hand at temperature lower than 900 K, where fuel-specific low-temperature chemistry plays a role, different fuel structures can result in vast differences in reactivity, up to factors of three or more in ignition delay.

  19. Simultaneous enzymatic synthesis of FAME and triacetyl glycerol from triglycerides and methyl acetate.

    PubMed

    Usai, E M; Gualdi, E; Solinas, V; Battistel, E

    2010-10-01

    In the presence of methyl acetate triglycerides such as vegetable oils are transformed simultaneously into the corresponding fatty acid methyl esters and triacetyl glycerol (triacetin). The reaction, catalyzed by lipases, was studied as a function of some critical parameters, such as type of catalyst, enzyme hydration and immobilization support. The aim of the work was to achieve a conversion of the triglyceride as high as possible and to maximize the yield of the triacetin, the reaction end point. It was found that by using the immobilized lipase from Candida antarctica yields as high as 80% of both fatty acid esters and triacetin could be achieved. These results were obtained by carefully controlling the amount of water present in the reaction medium and the hydration level of the enzyme macromolecule. Copyright © 2010 Elsevier Ltd. All rights reserved.

  20. The use of fatty acid methyl esters as biomarkers to determine aerobic, facultatively aerobic and anaerobic communities in wastewater treatment systems.

    PubMed

    Quezada, Maribel; Buitrón, Germán; Moreno-Andrade, Iván; Moreno, Gloria; López-Marín, Luz M

    2007-01-01

    The use of fatty acid methyl esters (FAME) as biomarkers to identify groups of microorganisms was studied. A database was constructed using previously published results that identify FAME biomarkers for aerobic, anaerobic and facultatively aerobic bacteria. FAME profiles obtained from pure cultures were utilized to confirm the predicted presence of biomarkers. Principal component analysis demonstrated that the FAME profiles can be used to determine the incidence of these bacterial groups. The presence of aerobic, anaerobic and facultatively aerobic bacteria in the communities, in four bioreactors being used to treat different wastewaters, was investigated by applying FAME biomarkers.

  1. Identification of Abscisic Acid in Tulipa gesneriana L. by Gas-Liquid Chromatography with Electron Capture and Combined Gas-Liquid Chromatography and Mass Spectrometry

    PubMed Central

    Terry, Paul H.; Aung, Louis H.; De Hertogh, August A.

    1982-01-01

    A major growth inhibitory substance of tulip bulbs (Tulipa gesneriana L. cv Paul Richter) has been unequivocally shown to be abscisic acid (ABA). The ABA methyl ester of the free ether-soluble acid fractions of tulip organs had the identical retention time on gas-liquid chromatography with electron capture detector as authentic ABA methyl ester. In addition, the mass spectra were the same. On a unit dry matter basis, the basalplate and floral shoot contained 3.6 and 2.6 times more ABA than the fleshy scales, respectively. PMID:16662721

  2. Thielavin B methyl ester: a cytotoxic benzoate trimer from an unidentified fungus (MSX 55526) from the Order Sordariales.

    PubMed

    Ayers, Sloan; Ehrmann, Brandie M; Adcock, Audrey F; Kroll, David J; Wani, Mansukh C; Pearce, Cedric J; Oberlies, Nicholas H

    2011-11-02

    As part of our ongoing investigation of filamentous fungi for anticancer leads, an active fungal extract was identified from the Mycosynthetix library (MSX 55526; from the Order Sordariales). Bioactivity-directed fractionation yielded the known ergosterol peroxide (2) and 5α,8α-epidioxyergosta-6,9(11),22-trien-3β-ol(3), and a new benzoate trimer, termed thielavin B methyl ester (1). The structure elucidation of 1 was facilitated by the use of HRMS coupled to an APPI (atmospheric pressure photoionization) source. Compound 1 proved to be moderately active against a panel of three cancer cell lines.

  3. Sequential Diels–Alder/[3,3]-sigmatropic rearrangement reactions of β-nitrostyrene with 3-methyl-1,3-pentadiene

    PubMed Central

    Pipic, Alma; Zeller, Matthias; Tsetsakos, Panagiota

    2013-01-01

    Summary The tin(IV)-catalyzed reaction of β-nitrostyrene with (E)-3-methyl-1,3-pentadiene in toluene afforded two major nitronic ester cycloadducts in 27% and 29% yield that arise from the reaction at the less substituted diene double bond. Also present were four cycloadducts from the reaction at the higher substituted diene double bond, two of which were the formal cycloadducts of (Z)-3-methyl-1,3-pentadiene. A Friedel–Crafts alkylation product from the reaction of the diene, β-nitrostyrene, and toluene was also obtained in 10% yield. The tin(IV)-catalyzed reaction of β-nitrostyrene with (Z)-3-methyl-1,3-pentadiene in dichloromethane afforded four nitronic ester cycloadducts all derived from the reaction at the higher substituted double bond. One cycloadduct was isolated in 45% yield and two others are formal adducts of the E-isomer of the diene. The product formation in these reactions is consistent with a stepwise mechanism involving a zwitterionic intermediate. The initially isolated nitronic ester cycloadducts underwent tin(IV)-catalyzed interconversion, presumably via zwitterion intermediates. Cycloadducts derived from the reaction at the less substituted double bond of (E)-3-methyl-1,3-pentadiene underwent a [3,3]-sigmatropic rearrangement on heating to afford 4-nitrocyclohexenes. Cycloadducts derived from the reaction at the higher substituted diene double bond of either diene failed to undergo a thermal rearrangement. Rates and success of the rearrangement are consistent with a concerted mechanism possessing a dipolar transition state. An initial assessment of substituent effects on the rearrangement process is presented. PMID:24204426

  4. The oxidation products of crude mesobilirubinogen

    PubMed Central

    Stoll, M. S.; Gray, C. H.

    1970-01-01

    Bile pigment esters were separated by ascending t.l.c. Apparently pure pigments, obtained by ferric chloride oxidation of crude mesobilirubinogen, derived from commercial bilirubin by reduction with sodium amalgam, were shown to be complex mixtures. Successive chromatography of their dimethyl esters on silica gel in methyl acetate–methyl propionate–dichloromethane–carbon tetrachloride (1:1:1:1, by vol.), ethyl methyl ketone–1,2-dichloroethane (1:2, v/v) and benzene–ethanol (100:3, v/v) revealed two major blue pigments (verdins), six major violet pigments (violins) and a red pigment (rhodin) together with numerous minor components. i-Urobilin dimethyl ester, prepared from mesobilirubinogen by dehydrogenation with aqueous iodine, was resolved into three major and at least four minor components on silica gel–kieselguhr (3:1, w/w) in benzene–ethanol (25:2, v/v). The chemical nature of these pigments was investigated by oxidation, by visible and u.v. spectroscopy, by mass spectrometry and by n.m.r. spectrometry. The evidence suggests unusual rearrangement of bilirubin during reduction leading to the formation of IIIα and XIIIα isomers. Isomeric forms of mesobiliviolin IXα and of i-urobilin IXα may also be formed. PMID:5420035

  5. Polyphenolic profile and bioactivity study of Oenothera speciosa Nutt. aerial parts.

    PubMed

    Marzouk, Mohamed S; Moharram, Fatma A; El Dib, Rabab A; El-Shenawy, Siham M; Tawfike, Ahmed F

    2009-04-07

    Two new flavonol glycosides, myricetin 4'-O-alpha-L-rhamnopyranoside (1) and quercetin 3'-O-alpha-L-rhamnopyranoside (2), together with a novel biflavonol compound, speciin (3), as well as eleven phenolic metabolites, namely myricitrin (4), europetin 3-O-alpha-L-(1)C(4)-rhamnopyranoside (5), quercitrin (6), hyperin (7), rhamnetin 3-O-beta-galacto-pyranoside (8), caffeic acid (9), caffeic acid methyl ester (10), chlorogenic acid (11), chlorogenic acid methyl ester (12), gallic acid (13) and gallic acid methyl ester (14), were identified from the 80 % methanol extract of the aerial parts (leaves and stems) of Oenothera speciosa Nutt. (Onagraceae). In addition myricetin (15), quercetin (16) and ellagic acid (17) were identified from the chloroform extract. The structures were established depending on their chemical and physical analyses (UV, HR-ESIMS, 1D and 2D NMR). It was found that 80 % aqueous methanol extract of O. speciosa is non-toxic to mice up to 5 g kg(-1)b wt. The investigated extract exhibited significant antihyperglycaemic and anti-inflammatory activities in a dose dependant manner. Also, the 80 % methanol extract, myricitrin(4) and hyperin(7) showed potent antioxidant activity in vitro using 1,1-diphenyl 2-picryl hydrazyl (DPPH) radical assay.

  6. Development of an HPLC Method with an ODS Column to Determine Low Levels of Aspartame Diastereomers in Aspartame

    PubMed Central

    Ohtsuki, Takashi; Nakamura, Ryoichiro; Kubo, Satoru; Otabe, Akira; Oobayashi, Yoko; Suzuki, Shoko; Yoshida, Mika; Yoshida, Mitsuya; Tatebe, Chiye; Sato, Kyoko; Akiyama, Hiroshi

    2016-01-01

    α-L-Aspartyl-D-phenylalanine methyl ester (L, D-APM) and α-D-aspartyl-L-phenylalanine methyl ester (D, L-APM) are diastereomers of aspartame (N-L-α-Aspartyl-L-phenylalanine-1-methyl ester, L, L-APM). The Joint FAO/WHO Expert Committee on Food Additives has set 0.04 wt% as the maximum permitted level of the sum of L, D-APM and D, L-APM in commercially available L, L-APM. In this study, we developed and validated a simple high-performance liquid chromatography (HPLC) method using an ODS column to determine L, D-APM and D, L-APM in L, L-APM. The limits of detection and quantification, respectively, of L, D-APM and D, L-APM were found to be 0.0012 wt% and 0.004 wt%. This method gave excellent accuracy, repeatability, and reproducibility in a recovery test performed on five different days. Moreover, the method was successfully applied to the determination of these diastereomers in commercial L, L-APM samples. Thus, the developed method is a simple, useful, and practical tool for determining L, D-APM and D, L-APM levels in L, L-APM. PMID:27015640

  7. Development of an HPLC Method with an ODS Column to Determine Low Levels of Aspartame Diastereomers in Aspartame.

    PubMed

    Ohtsuki, Takashi; Nakamura, Ryoichiro; Kubo, Satoru; Otabe, Akira; Oobayashi, Yoko; Suzuki, Shoko; Yoshida, Mika; Yoshida, Mitsuya; Tatebe, Chiye; Sato, Kyoko; Akiyama, Hiroshi

    2016-01-01

    α-L-Aspartyl-D-phenylalanine methyl ester (L, D-APM) and α-D-aspartyl-L-phenylalanine methyl ester (D, L-APM) are diastereomers of aspartame (N-L-α-Aspartyl-L-phenylalanine-1-methyl ester, L, L-APM). The Joint FAO/WHO Expert Committee on Food Additives has set 0.04 wt% as the maximum permitted level of the sum of L, D-APM and D, L-APM in commercially available L, L-APM. In this study, we developed and validated a simple high-performance liquid chromatography (HPLC) method using an ODS column to determine L, D-APM and D, L-APM in L, L-APM. The limits of detection and quantification, respectively, of L, D-APM and D, L-APM were found to be 0.0012 wt% and 0.004 wt%. This method gave excellent accuracy, repeatability, and reproducibility in a recovery test performed on five different days. Moreover, the method was successfully applied to the determination of these diastereomers in commercial L, L-APM samples. Thus, the developed method is a simple, useful, and practical tool for determining L, D-APM and D, L-APM levels in L, L-APM.

  8. Mechanisms of Decreased Moisture Uptake in ortho- Methylated Di(Cyanate Esters)

    DTIC Science & Technology

    2014-10-01

    Distribution A: Approved for public release; distribution is unlimited. 1 Mechanisms of Decreased Moisture Uptake in ortho- Methylated Di(Cyanate...when analogous networks containing a single methyl group ortho- to each aryl- cyanurate linkage were prepared by reduction and acid-catalyzed coupling...of salicylic acid followed by treatment with cyanogen bromide and subsequent cyclotrimerization. The differences in water uptake were observed

  9. Low-molecular-weight poly(alpha-methyl beta,L-malate) of microbial origin: synthesis and crystallization.

    PubMed

    Fernández, Carlos E; Mancera, Manuel; Holler, Eggehard; Bou, Jordi J; Galbis, Juan A; Muñoz-Guerra, Sebastián

    2005-02-23

    Low-molecular-weight poly(alpha-methyl beta,L-malate) made of approximately 25-30 units was prepared from microbial poly(beta,L-malic acid) by treatment with diazomethane. The thermal characterization of the polymalate methyl ester was carried out and its crystalline structure was preliminary examined. Its ability to crystallize both from solution and from the melt was comparatively evaluated.

  10. Two-Carbon Homologation of Ketones to 3-Methyl Unsaturated Aldehydes

    USDA-ARS?s Scientific Manuscript database

    The usual scheme of two-carbon homologation of ketones to 3-methyl unsaturated aldehydes by Horner-Wadsworth-Emmons condensations with phosphonate esters, such as triethyl-2-phosphonoacetate, involves three steps. The phosphonate condensation step results in extension of the carbon chain by two carb...

  11. Brucine diol-copper-catalyzed asymmetric synthesis of endo-pyrrolidines: the mechanistic dichotomy of imino esters.

    PubMed

    Li, Jian-Yuan; Kim, Hun Young; Oh, Kyungsoo

    2015-03-06

    Enantio- and diastereodivergent approaches to pyrrolidines are described by using catalyst- and substrate-controlled reaction pathways. A concerted endo-selective [3 + 2]-cycloaddition pathway is developed for the reaction of methyl imino ester, whereas endo-pyrrolidines with an opposite absolute stereochemical outcome are prepared by using the stepwise reaction pathway of tert-butyl imino ester. The development of catalyst- and substrate-controlled stereodivergent approaches highlights the inherent substrate-catalyst interactions in the [3 + 2]-cycloaddition reactions of metalated azomethine ylides.

  12. Floral benzenoid carboxyl methyltransferases: From in vitro to in planta function

    PubMed Central

    Effmert, Uta; Saschenbrecker, Sandra; Ross, Jeannine; Negre, Florence; Fraser, Chris M.; Noel, Joseph P.; Dudareva, Natalia; Piechulla, Birgit

    2010-01-01

    Benzenoid carboxyl methyltransferases synthesize methyl esters (e.g., methyl benzoate and methyl salicylate), which are constituents of aromas and scents of many plant species and play important roles in plant communication with the surrounding environment. Within the past five years, eleven such carboxyl methyltransferases were isolated and most of them were comprehensively investigated at the biochemical, molecular and structural level. Two types of enzymes can be distinguished according to their substrate preferences: the SAMT-type enzymes isolated from Clarkia breweri, Stephanotis floribunda, Antirrhinum majus, Hoya carnosa, and Petunia hybrida, which have a higher catalytic efficiency and preference for salicylic acid, while BAMT-type enzymes from A. majus, Arabidopsis thaliana, Arabidopsis lyrata, and Nicotiana suaveolens prefer benzoic acid. The elucidation of C. breweri SAMT’s three-dimensional structure allowed a detailed modelling of the active sites of the carboxyl methyltransferases and revealed that the SAM binding pocket is highly conserved among these enzymes while the methyl acceptor binding site exhibits some variability, allowing a classification into SAMT-type and BAMT-type enzymes. The analysis of expression patterns coupled with biochemical characterization showed that these carboxyl methyltransferases are involved either in floral scent biosynthesis or in plant defense responses. While the latter can be induced by biotic or abiotic stress, the genes responsible for floral scent synthesis exhibit developmental and rhythmic expression pattern. The nature of the product and efficiency of its formation in planta depend on the availability of substrates, the catalytic efficiency of the enzyme toward benzoic acid and/or salicylic acid, and the transcriptional, translational, and post-translational regulation at the enzyme level. The biochemical properties of benzenoid carboxyl methyltransferases suggest that the genes involved in plant defenses might represent the ancestor for the presently existing floral genes which during evolution gained different expression profiles and encoded enzymes with the ability to accept structurally similar substrates. PMID:15946712

  13. Surface-enhanced Raman scattering spectroscopy of explosive 2,4-dinitroanisole using modified silver nanoparticles.

    PubMed

    Xu, Zhonghou; Hao, Jumin; Braida, Washington; Strickland, David; Li, Fasheng; Meng, Xiaoguang

    2011-11-15

    2,4-Dinitroanisole (DNAN) is being used as a replacement for 2,4,6-trinitrotoluene (TNT) as a less-sensitive melt-cast medium explosive than TNT. In this paper, we studied the surface-enhanced Raman spectroscopy (SERS) analysis of DNAN using Ag nanoparticles (AgNPs) modified by L-cysteine methyl ester hydrochloride. Due to the formation of a Meisenheimer complex between DNAN and the modifier, the modified AgNPs can detect 20 μg/L (0.2 ng) and 0.1 mg/L (1 ng) DNAN in deionized water and aged tap water, respectively. Three other chemicals (L-cysteine, N-acetyl-L-cysteine, and L-cysteine ethyl ester hydrochloride) were used as AgNPs modifiers to study the mechanism of the SERS of DNAN. It was confirmed that the amino group of L-cysteine methyl ester hydrochloride was the active group and that the methyl ester group significantly contributed to the high SERS sensitivity of DNAN. In order to further test the mechanism of Meisenheimer complex formation, the effect of anions and cations present in natural water on the SERS of DNAN was studied. It was found that CO(3)(2-), Cl(-), and K(+) at 100 mg/L did not negatively affect the SERS of 10 mg/L DNAN, while SO(4)(2-), Na(+), Mg(2+), and Ca(2+) at 100 mg/L significantly quenched the SERS of 10 mg/L DNAN. The negative effect of the bivalent cations could be offset by SO(4)(2-).

  14. Cyclic Tetrapyrrolic Photosensitisers from the leaves of Phaeanthus ophthalmicus

    PubMed Central

    2011-01-01

    Background Twenty-seven extracts from 26 plants were identified as photo-cytotoxic in the course of our bioassay guided screening program for photosensitisers from 128 extracts prepared from 64 terrestrial plants in two different collection sites in Malaysia - Royal Belum Forest Reserve in the State of Perak and Gunung Nuang in the State of Selangor. One of the photo-cytotoxic extracts from the leaves of Phaeanthus ophtalmicus was further investigated. Results The ethanolic extract of the leaves from Phaeanthus ophtalmicus was able to reduce the in vitro viability of leukaemic HL60 cells to < 50% when exposed to 9.6 J/cm2 of a broad spectrum light at a concentration of 20 μg/mL. Dereplication of the photo-cytotoxic fractions from P. ophthalmicus extracts based on TLC Rf values and HPLC co-injection of reference tetrapyrrolic compounds enabled quick identification of known photosensitisers, pheophorbide-a, pheophorbide-a methyl ester, 132-hydroxypheophorbide-a methyl ester, pheophytin-a and 151-hydroxypurpurin 7-lactone dimethyl ester. In addition, compound 1 which was not previously isolated as a natural product was also identified as 7-formyl-151-hydroxypurpurin-7-lactone methyl ester using standard spectroscopic techniques. Conclusions Our results suggest that the main photosensitisers in plants are based on the cyclic tetrapyrrole structure and photosensitisers with other structures, if present, are present in very minor amounts or are not as active as those with the cyclic tetrapyrrole structure. PMID:21682931

  15. Impact of fatty ester composition on low temperature properties of biodiesel-petroleum diesel blends

    USDA-ARS?s Scientific Manuscript database

    Several biodiesel fuels along with neat fatty acid methyl esters (FAMEs) commonly encountered in biodiesel were blended with ultra-low sulfur diesel (ULSD) fuel at low blend levels permitted by ASTM D975 (B1-B5) and cold flow properties such as cloud point (CP), cold filter plugging point (CFPP), an...

  16. 21 CFR 177.2800 - Textiles and textile fibers.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... ethyl sulfate For use only as a lubricant in the manufacture of polyethylene terephthalate fibers...-octadecenamido)ethyl-2-imidazolinium ethyl sulfate. Hexylene glycol (2-methyl,-2,4-pentanediol) Isobutyl alcohol Isopropyl alcohol Kerosene Methyl ester of sulfated ricebran oil Mineral oil For use only at a level not to...

  17. 21 CFR 177.2800 - Textiles and textile fibers.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... ethyl sulfate For use only as a lubricant in the manufacture of polyethylene terephthalate fibers...-octadecenamido)ethyl-2-imidazolinium ethyl sulfate. Hexylene glycol (2-methyl,-2,4-pentanediol) Isobutyl alcohol Isopropyl alcohol Kerosene Methyl ester of sulfated ricebran oil Mineral oil For use only at a level not to...

  18. Preparation of metal adsorbent from poly(methyl acrylate)-grafted-cassava starch via gamma irradiation

    NASA Astrophysics Data System (ADS)

    Suwanmala, Phiriyatorn; Hemvichian, Kasinee; Hoshina, Hiroyuki; Srinuttrakul, Wannee; Seko, Noriaki

    2012-08-01

    Metal adsorbent containing hydroxamic acid groups was successfully synthesized by radiation-induced graft copolymerization of methyl acrylate (MA) onto cassava starch. The optimum conditions for grafting were studied in terms of % degree of grafting (Dg). Conversion of the ester groups present in poly(methyl acrylate)-grafted-cassava starch copolymer into hydroxamic acid was carried out by treatment with hydroxylamine (HA) in the presence of alkaline solution. The maximum percentage conversion of the ester groups of the grafted copolymer, % Dg=191 (7.63 mmol/g of MA), into the hydroxamic groups was 70% (5.35 mmol/g of MA) at the optimum condition. The adsorbent of 191%Dg had total adsorption capacities of 2.6, 1.46, 1.36, 1.15 and 1.6 mmol/g-adsorbent for Cd2+, Al3+, UO22+, V5+ and Pb2+, respectively, in the batch mode adsorption.

  19. Bioconcentration of haloxyfop-methyl in bluegill (Lepomis macrochirus Rafinesque)

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    Murphy, P.G.; Lutenske, N.E.

    1990-01-01

    Bluegill (Lepomis macrochirus Rafinesque) were exposed to a {sup 14}C haloxyfop-methyl (methyl 2-(4-((3-chloro-5-(trifluoromethyl)-2-pyridinyl)oxy)phenoxy)propanoate) concentration averaging 0.29 {mu}g/L under flow-through conditions for 28 days. At the end of 28 days, the fish were transferred to clean water for a 4-day flow-through clearance period. Bluegill were found to rapidly absorb the ester from water which was then biotransformed at an extremely fast rate within the fish, such that essentially no haloxyfop-methyl was detected in the fish. The estimated bioconcentration factor for haloxyfop-methyl in whole fish was <17, based upon the detection limit for the ester in fish (0.005 {mu}g/g) and the averagemore » concentration of haloxyfop-methyl in exposure water (0.29 {mu}g/L). The principal component of the {sup 14}C residue within whole fish was haloxyfop acid (2-(4-((3-chloro-5-(trifluoromethyl)-2-pyridinyl)oxy)phenoxy)propanoic acid) which accounted for an average of about 60% of the total radioactivity. The high rate of biotransformation of the parent compound within the fish demonstrates the importance of basing the bioconcentration factor upon the actual concentration of parent material within the organism rather than the total radioactive residue levels for bioconcentration studies with radiolabeled compounds.« less

  20. Direct methylation procedure for converting fatty amides to fatty acid methyl esters in feed and digesta samples.

    PubMed

    Jenkins, T C; Thies, E J; Mosley, E E

    2001-05-01

    Two direct methylation procedures often used for the analysis of total fatty acids in biological samples were evaluated for their application to samples containing fatty amides. Methylation of 5 mg of oleamide (cis-9-octadecenamide) in a one-step (methanolic HCl for 2 h at 70 degrees C) or a two-step (sodium methoxide for 10 min at 50 degrees C followed by methanolic HCl for 10 min at 80 degrees C) procedure gave 59 and 16% conversions of oleamide to oleic acid, respectively. Oleic acid recovery from oleamide was increased to 100% when the incubation in methanolic HCl was lengthened to 16 h and increased to 103% when the incubation in methoxide was modified to 24 h at 100 degrees C. However, conversion of oleamide to oleic acid in an animal feed sample was incomplete for the modified (24 h) two-step procedure but complete for the modified (16 h) one-step procedure. Unsaturated fatty amides in feed and digesta samples can be converted to fatty acid methyl esters by incubation in methanolic HCl if the time of exposure to the acid catalyst is extended from 2 to 16 h.

  1. Structural insights into the methyl donor recognition model of a novel membrane-binding protein UbiG.

    PubMed

    Zhu, Yuwei; Jiang, Xuguang; Wang, Chongyuan; Liu, Yang; Fan, Xiaojiao; Zhang, Linjuan; Niu, Liwen; Teng, Maikun; Li, Xu

    2016-03-15

    UbiG is a SAM-dependent O-methyltransferase, catalyzing two O-methyl transfer steps for ubiquinone biosynthesis in Escherichia coli. UbiG possesses a unique sequence insertion between β4 and α10, which is used for membrane lipid interaction. Interestingly, this sequence insertion also covers the methyl donor binding pocket. Thus, the relationship between membrane binding and entrance of the methyl donor of UbiG during the O-methyl transfer process is a question that deserves further exploration. In this study, we reveal that the membrane-binding region of UbiG gates the entrance of methyl donor. When bound with liposome, UbiG displays an enhanced binding ability toward the methyl donor product S-adenosylhomocysteine. We further employ protein engineering strategies to design UbiG mutants by truncating the membrane interacting region or making it more flexible. The ITC results show that the binding affinity of these mutants to SAH increases significantly compared with that of the wild-type UbiG. Moreover, we determine the structure of UbiG∆(165-187) in complex with SAH. Collectively, our results provide a new angle to cognize the relationship between membrane binding and entrance of the methyl donor of UbiG, which is of benefit for better understanding the O-methyl transfer process for ubiquinone biosynthesis.

  2. Regulation of expression of the ada gene controlling the adaptive response. Interactions with the ada promoter of the Ada protein and RNA polymerase.

    PubMed

    Sakumi, K; Sekiguchi, M

    1989-01-20

    The Ada protein of Escherichia coli catalyzes transfer of methyl groups from methylated DNA to its own molecule, and the methylated form of Ada protein promotes transcription of its own gene, ada. Using an in vitro reconstituted system, we found that both the sigma factor and the methylated Ada protein are required for transcription of the ada gene. To elucidate molecular mechanisms involved in the regulation of the ada transcription, we investigated interactions of the non-methylated and methylated forms of Ada protein and the RNA polymerase holo enzyme (the core enzyme and sigma factor) with a DNA fragment carrying the ada promoter region. Footprinting analyses revealed that the methylated Ada protein binds to a region from positions -63 to -31, which includes the ada regulatory sequence AAAGCGCA. No firm binding was observed with the non-methylated Ada protein, although some DNase I-hypersensitive sites were produced in the promoter by both types of Ada protein. RNA polymerase did bind to the promoter once the methylated Ada protein had bound to the upstream sequence. To correlate these phenomena with the process in vivo, we used the DNAs derived from promoter-defective mutants. No binding of Ada protein nor of RNA polymerase occurred with a mutant DNA having a C to G substitution at position -47 within the ada regulatory sequence. In the case of a -35 box mutant with a T to A change at position -34, the methylated Ada protein did bind to the ada regulatory sequence, yet there was no RNA polymerase binding. Thus, the binding of the methylated Ada protein to the upstream region apparently facilitates binding of the RNA polymerase to the proper region of the promoter. The Ada protein possesses two known methyl acceptor sites, Cys69 and Cys321. The role of methylation of each cysteine residue was investigated using mutant forms of the Ada protein. The Ada protein with the cysteine residue at position 69 replaced by alanine was incapable of binding to the ada promoter even when the cysteine residue at position 321 of the protein was methylated. When the Ada protein with alanine at position 321 was methylated, it acquired the potential to bind to the ada promoter. These results are compatible with the notion that methylation of the cysteine residue at position 69 causes a conformational change of the Ada protein, thereby facilitating binding of the protein to the upstream regulatory sequence.

  3. FTIR study of hydrogen bonding interaction between fluorinated alcohol and unsaturated esters

    NASA Astrophysics Data System (ADS)

    Sheng, Xia; Jiang, Xiaotong; Zhao, Hailiang; Wan, Dongjin; Liu, Yongde; Ngwenya, Cleopatra Ashley; Du, Lin

    2018-06-01

    The 1:1 complexes of two unsaturated esters with 2,2,2-trifluoroethanol (TFE) were investigated experimentally and computationally. The experimental observations of the spectral shifts of the OH-stretching vibrational transitions were obtained at 113 cm-1 for TFE-methyl acrylate (MA) and 92 cm-1 for TFE-vinyl acetate (VA). There are three docking sites in the two unsaturated esters for the incoming TFE. The predicted red shifts of the OH-stretching vibrational transitions were found to be larger for the Osbnd H⋯Odbnd C hydrogen bonded conformer than those for the Osbnd H⋯π and Osbnd H⋯O ones. The binding energies further prove that the Osbnd H⋯Odbnd C hydrogen bonded conformers are the most stable ones. On the basis of the DFT calculations as well as previous works, the carbonyl group is the best docking site for TFE. Furthermore, the thermodynamic equilibrium constants of TFE-MA and TFE-VA were obtained at 0.28 and 0.15 by combining the experimental spectra data and the DFT calculations. Consequently, the Gibbs free energies of formation were determined to be 3.2 and 4.8 kJ mol-1 for TFE-MA and TFE-VA, respectively. The quantum theory of atoms in molecules (AIM) and generalized Kohn-Sham energy decomposition analysis (GKS-EDA) were carried out for further characterization of the hydrogen bonding interactions. GKS-EDA shows an "electrostatic" dominated hydrogen bonding character for the Osbnd H⋯Odbnd C hydrogen bonds.

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

    PubMed

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

    2017-08-01

    The objective of this study was to evaluate the antioxidant effects of propolis, caffeic acid phenethyl ester (CAPE; active compound in propolis), and pollen on biochemical oxidative stress biomarkers in rat kidney tissue inhibited by N ω -nitro-L-arginine methyl ester (L-NAME). The biomarkers evaluated were paraoxonase (PON1), oxidative stress index (OSI), total antioxidant status (TAS), total oxidant status (TOS), asymmetric dimethylarginine (ADMA), and nuclear factor kappa B (NF-κB). TAS levels and PON1 activity were significantly decreased in kidney tissue samples in the L-NAME-treated group (P < 0.05). The levels of TAS and PONI were higher in the L-NAME plus propolis, CAPE, and pollen groups compared with the L-NAME-treated group. TOS, ADMA, and NF-κB levels were significantly increased in the kidney tissue samples of the L-NAME-treated group (P < 0.05). However, these parameters were significantly lower in the L-NAME plus propolis, CAPE, and pollen groups (P < 0.05) compared with rats administered L-NAME alone (P < 0.05). Furthermore, the binding energy of CAPE within catalytic domain of glutathione reductase (GR) enzyme as well as its inhibitory mechanism was determined using molecular modeling approaches. In conclusion, experimental and theoretical data suggested that oxidative alterations occurring in the kidney tissue of chronic hypertensive rats may be prevented via active compound of propolis, CAPE administration. Copyright © 2017 John Wiley & Sons, Ltd.

  5. Effective methylation of phosphonic acids related to chemical warfare agents mediated by trimethyloxonium tetrafluoroborate for their qualitative detection and identification by gas chromatography-mass spectrometry.

    PubMed

    Valdez, Carlos A; Leif, Roald N; Alcaraz, Armando

    2016-08-24

    The effective methylation of phosphonic acids related to chemical warfare agents (CWAs) employing trimethyloxonium tetrafluoroborate (TMO·BF4) for their qualitative detection and identification by gas chromatography-mass spectrometry (GC-MS) is presented. The methylation occurs in rapid fashion (1 h) and can be conveniently carried out at ambient temperature, thus providing a safer alternative to the universally employed diazomethane-based methylation protocols. Optimization of the methylation parameters led us to conclude that methylene chloride was the ideal solvent to carry out the derivatization, and that even though methylated products can be observed surfacing after only 1 h, additional time was not found to be detrimental but beneficial to the process particularly when dealing with analytes at low concentrations (∼10 μg mL(-1)). Due to its insolubility in methylene chloride, TMO·BF4 conveniently settles to the bottom during the reaction and does not produce additional interfering by-products that may further complicate the GC-MS analysis. The method was demonstrated to successfully methylate a variety of Schedule 2 phosphonic acids, including their half esters, resulting in derivatives that were readily detected and identified using the instrument's spectral library. Most importantly, the method was shown to simultaneously methylate a mixture of the organophosphorus-based nerve agent hydrolysis products: pinacolyl methylphosphonate (PMPA), cyclohexyl methylphosphonate (CyMPA) and ethyl methylphosphonate (EMPA) (at a 10 μg mL(-1) concentration each) in a fatty acid ester-rich organic matrix (OPCW-PT-O3) featured in the 38th Organisation for the Prohibition of Chemical Weapons (OPCW) Proficiency Test. In addition, the protocol was found to effectively methylate N,N-diethylamino ethanesulfonic acid and N,N-diisopropylamino ethanesulfonic acid that are products arising from the oxidative degradation of the V-series agents VR and VX respectively. The work described herein represents the first report on the use of TMO·BF4 as a viable, stable and safe agent for the methylation of phosphonic acids and their half esters and within the context of an OPCW Proficiency Test sample analysis. Copyright © 2016 Elsevier B.V. All rights reserved.

  6. Protonation switching to the least-basic heteroatom of carbamate through cationic hydrogen bonding promotes the formation of isocyanate cations.

    PubMed

    Kurouchi, Hiroaki; Sumita, Akinari; Otani, Yuko; Ohwada, Tomohiko

    2014-07-07

    We found that phenethylcarbamates that bear ortho-salicylate as an ether group (carbamoyl salicylates) dramatically accelerate OC bond dissociation in strong acid to facilitate generation of isocyanate cation (N-protonated isocyanates), which undergo subsequent intramolecular aromatic electrophilic cyclization to give dihydroisoquinolones. To generate isocyanate cations from carbamates in acidic media as electrophiles for aromatic substitution, protonation at the ether oxygen, the least basic heteroatom, is essential to promote CO bond cleavage. However, the carbonyl oxygen of carbamates, the most basic site, is protonated exclusively in strong acids. We found that the protonation site can be shifted to an alternative basic atom by linking methyl salicylate to the ether oxygen of carbamate. The methyl ester oxygen ortho to the phenolic (ether) oxygen of salicylate is as basic as the carbamate carbonyl oxygen, and we found that monoprotonation at the methyl ester oxygen in strong acid resulted in the formation of an intramolecular cationic hydrogen bond (>CO(+) H⋅⋅⋅O<) with the phenolic ether oxygen. This facilitates OC bond dissociation of phenethylcarbamates, thereby promoting isocyanate cation formation. In contrast, superacid-mediated diprotonation at the methyl ester oxygen of the salicylate and the carbonyl oxygen of the carbamate afforded a rather stable dication, which did not readily undergo CO bond dissociation. This is an unprecedented and unknown case in which the monocation has greater reactivity than the dication. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  7. Esterification of oil adsorbed on palm decanter cake into methyl ester using sulfonated rice husk ash as heterogeneous acid catalyst

    NASA Astrophysics Data System (ADS)

    Hindryawati, Noor; Erwin, Maniam, Gaanty Pragas

    2017-02-01

    Palm Decanter cake (PDC) which is categorized as the waste from palm oil mill has been found to contain residual crude palm oil. The oil adsorbed on the PDC (PDC-oil) can be extracted and potentially used as feedstock for biodiesel production. Feedstock from waste like PDC-oil is burdened with high free fatty acids (FFAs) which make the feedstock difficult to be converted into biodiesel using basic catalyst. Therefore, in this study, a solid acid, RHA-SO3H catalyst was synthesized by sulfonating rice husk ash (RHA) with concentrated sulfuric acid. The RHA-SO3H prepared was characterized with TGA, FTIR, BET, XRD, FE-SEM, and Hammett indicators (methyl red, bromophenol blue, and crystal violet). PDC was found to have about 11.3 wt. % oil recovered after 1 hour extraction using ultrasound method. The presence of sulfonate group was observed in IR spectrum, and the surface area of RHA-SO3H was reduced to 37 m2.g-1 after impregnation of sulfonate group. The RHA-SO3H catalyst showed that it can work for both esterification of free fatty acid which is present in PDC-oil, and transesterification of triglycerides into methyl ester. The results showed highest methyl ester content of 70.2 wt.% at optimal conditions, which was 6 wt.% catalyst amount, methanol to oil molar ratio of 17:1 for 5 hours at 120 °C.

  8. RXRα transcriptional inhibitors from the stems of Calophyllum membranaceum.

    PubMed

    Ming, Meng; Zhang, Xue; Chen, Hai-Feng; Zhu, Ling-Juan; Zeng, De-Quan; Yang, Jian; Wu, Guang-Xun; Wu, Yu-Zhuo; Yao, Xin-Sheng

    2016-01-01

    Bioassay-guided fractionation of the 60% ethanol extract of the stems of Calophyllum membranaceum using the RXRα transcription activation assay led to the isolation of two new chromanones, calopolyanic acid methyl ester (1) and isopinetoric acid methyl ester (2), two new xanthones, calophylixanthones A-B (3-4), and one new C-glycoside, calophymembranside C (5), along with 13 known compounds. Their structures were elucidated on the basis of extensive spectroscopic data. Compounds 5, 11 and 18 showed transcriptional inhibitory activity of RXRα with 50% inhibitory concentration (IC50) values of 29.95 ± 1.08, 31.06 ± 9.02, and 25.88 ± 1.62 μM, respectively. Copyright © 2015 Elsevier B.V. All rights reserved.

  9. Antimicrobial activity of fatty acid methyl esters of some members of Chenopodiaceae.

    PubMed

    Chandrasekaran, Manivachagam; Kannathasan, Krishnan; Venkatesalu, Venugopalan

    2008-01-01

    Fatty acid methyl ester (FAME) extracts of four halophytic plants, viz. Arthrocnemum indicum, Salicornia brachiata, Suaeda maritima and Suaeda monoica belonging to the family Chenopodiaceae, were prepared and their composition was analyzed by GC-MS. The FAME extracts were also screened for antibacterial and antifungal activities. The GC-MS analysis revealed the presence of more saturated fatty acids than unsaturated fatty acids. Among the fatty acids analyzed, the relative percentage of lauric acid was high in S. brachiata (61.85%). The FAME extract of S. brachiata showed the highest antibacterial and antifungal activities among the extracts tested. The other three extracts showed potent antibacterial and moderate anticandidal activities.

  10. Three new amino acid derivatives from edible mushroom Pleurotus ostreatus.

    PubMed

    Lu, Xiao-Jie; Feng, Bao-Min; Chen, Shao-Fei; Zhao, Dan; Chen, Gang; Wang, Hai-Feng; Pei, Yue-Hu

    2017-12-01

    Three new amino acid derivatives, oxalamido-L-phenylalanine methyl ester (1), oxalamido-L-leucine methyl ester (2), and lumichrome hydrolyzate (3), together with nine known compounds (4-12), were isolated from the solid culture of edible mushroom Pleurotus ostreatus. Their structures were elucidated on the basis of extensive spectroscopic analysis. The absolute configurations of 1 and 2 were established by the chiral synthesis and confirmed by circular dichroism (CD) analysis of their total synthesis products and natural isolates. All new compounds were evaluated for their antioxidant effects, antimicrobial activities, and cytotoxic activity. Compounds 1-3 showed weak antifungal activities against Candida albicans with minimum inhibitory concentration (MIC) value of 500 μg/ml.

  11. Synthesis of perfluoroalkylene aromatic diamines

    NASA Technical Reports Server (NTRS)

    Paciorek, K. L.; Ito, T. I.; Nakahara, J. H.; Kratzer, R. H.

    1978-01-01

    Analogues of methylene dianilines were synthesized, in which the methylene group between the two aromatic nuclei was replaced by various perfluoroalkylene linkage. The hydrolytic thermal, and thermal oxidative stabilities of PMR Polyimides derived from these diamines were determined. Three types of PMR Polyimide discs were fabricated from the dimethyl ester of 3,3', 4,4'-benzophenonetetracarboxylic acid, the methyl ester of 5-norbornene-2,3-dicarboxylic acid, and one of the following three diamines: methyl dianiline, 1,3-bis(4-aminophenyl)hexafluoropropane, and 2,2-bis(4-aminophenyl)hexafluoropropane. The polyimide based on 2,2-bis(4-aminophenyl)hexafluoropropane exhibited the best hydrolytic, thermal, and thermal oxidative stability as determined by moisture uptake and thermogravimetric analysis.

  12. [Synthesis and monolayer behaviors of 4-methyl-5-hydroxy-ethyl isothiazole stearic ester].

    PubMed

    Shen, Yu-hua; Kong, Lin; Yang, Jia-xiang; Xie, An-jian; Qian, Jia-sheng; Ouyang, Jian-ming; Xia, Bing

    2002-12-01

    4-methyl-5-hydroxy-ethyl isothiazole stearic ester (HISE) was synthesized and characterized by FTIR spectroscopy, 1H NMR and MS. The monolayer-forming ability of HISE was studied in subphases with different pH values using isotherms of surface pressure-area per molecule (pi-A). It was observed that the collapse pressure and the film-forming ability of the monolayers of HISE increased gradually as pH values ascended. Research of differentiated pi-A curves (d pi(/dA-A) indicated that there were one or two phase change points during the compressing process, and the incompressibility and the stability of HISE monolayers on alkalescent subphases were better than on acid subphases.

  13. Enrichment, separation, and gas-chromatographic and mass-spectrometric analyses of fission products from irradiated or heated fats, oils, and test substances (in German)

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    Beck, B.

    1973-01-01

    From international colloquium: the identification of irradiated foodstuffs; Karlsrahe, Germany (24 Oct 1973). Tripalmitate, tristearate, trioleate, oleic acid methyl ester, linoleic acid methyl ester, lauric acid, lard, coconut butter, sunflower oil, and olive oil were irradiated at 0.5-6 Mrad,or heated up to 174 deg C for 24 hr. The fission products were fractionally distilled with silica gel according to polarity into elutropic series. Subsequent identification and quantitative determination were done by gas chromatography and mass spectrometry. Approximately 28 hydrocarbons and 24 oxygen compounds are dealt with, the typical substances being described individually as regards their identification and quantitative distribution. (GE)

  14. Electronic properties of electron-doped [6,6]-phenyl-C61-butyric acid methyl ester and silylmethylfullerene

    NASA Astrophysics Data System (ADS)

    Furutani, Sho; Okada, Susumu

    2017-06-01

    Electronic properties of electron-doped chemically decorated C60 fullerenes, [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) and silylmethylfullerene (SIMEF), by a planar electrode were studied using density functional theory combined with the effective screening medium method to simulate the heterointerface between the chemically decorated C60 and cationic counter materials. We find that the distribution of accumulated electrons and induced electric field depend on the molecular arrangement with respect to the external electric field of the electrode. We also show that the quantum capacitance of the molecule is sensitive to molecular arrangement owing to the asymmetric distribution of the accumulated electrons.

  15. Production of MAG via enzymatic glycerolysis

    NASA Astrophysics Data System (ADS)

    Jamlus, Norul Naziraa Ahmad; Derawi, Darfizzi; Salimon, Jumat

    2015-09-01

    Enzymatic glycerolysis of a medium chain methyl ester, methyl laurate was performed using lipase Candida antarctica (Novozyme 435) for 6 hours at 55°C. The percentage of components mixture of product were determined by using gas chromatography technique. The enzymatic reaction was successfully produced monolaurin (45.9 %), dilaurin (47.1 %) and trilaurin (7.0 %) respectively. Thin layer chromatography (TLC) plate also showed a good separation of component spots. Fourier transformation infra-red (FTIR) spectrum showed the presence of ester carbonyl at wavenumber 1739.99 cm-1 and hydrogen bonded O-H at 3512.03 cm-1. The product is potentially to be used as emulsifier and additive in food industry, pharmaceutical, as well as antibacterial.

  16. Effects of Mutations and Ligands on the Thermostability of the l-Arginine/Agmatine Antiporter AdiC and Deduced Insights into Ligand-Binding of Human l-Type Amino Acid Transporters

    PubMed Central

    Ilgü, Hüseyin; Jeckelmann, Jean-Marc; Colas, Claire; Ucurum, Zöhre; Schlessinger, Avner; Fotiadis, Dimitrios

    2018-01-01

    The l-arginine/agmatine transporter AdiC is a prokaryotic member of the SLC7 family, which enables pathogenic enterobacteria to survive the extremely acidic gastric environment. Wild-type AdiC from Escherichia coli, as well as its previously reported point mutants N22A and S26A, were overexpressed homologously and purified to homogeneity. A size-exclusion chromatography-based thermostability assay was used to determine the melting temperatures (Tms) of the purified AdiC variants in the absence and presence of the selected ligands l-arginine (Arg), agmatine, l-arginine methyl ester, and l-arginine amide. The resulting Tms indicated stabilization of AdiC variants upon ligand binding, in which Tms and ligand binding affinities correlated positively. Considering results from this and previous studies, we revisited the role of AdiC residue S26 in Arg binding and proposed interactions of the α-carboxylate group of Arg exclusively with amide groups of the AdiC backbone. In the context of substrate binding in the human SLC7 family member l-type amino acid transporter-1 (LAT1; SLC7A5), an analogous role of S66 in LAT1 to S26 in AdiC is discussed based on homology modeling and amino acid sequence analysis. Finally, we propose a binding mechanism for l-amino acid substrates to LATs from the SLC7 family. PMID:29558430

  17. Effects of Mutations and Ligands on the Thermostability of the l-Arginine/Agmatine Antiporter AdiC and Deduced Insights into Ligand-Binding of Human l-Type Amino Acid Transporters.

    PubMed

    Ilgü, Hüseyin; Jeckelmann, Jean-Marc; Colas, Claire; Ucurum, Zöhre; Schlessinger, Avner; Fotiadis, Dimitrios

    2018-03-20

    The l-arginine/agmatine transporter AdiC is a prokaryotic member of the SLC7 family, which enables pathogenic enterobacteria to survive the extremely acidic gastric environment. Wild-type AdiC from Escherichia coli, as well as its previously reported point mutants N22A and S26A, were overexpressed homologously and purified to homogeneity. A size-exclusion chromatography-based thermostability assay was used to determine the melting temperatures ( T m s) of the purified AdiC variants in the absence and presence of the selected ligands l-arginine (Arg), agmatine, l-arginine methyl ester, and l-arginine amide. The resulting T m s indicated stabilization of AdiC variants upon ligand binding, in which T m s and ligand binding affinities correlated positively. Considering results from this and previous studies, we revisited the role of AdiC residue S26 in Arg binding and proposed interactions of the α-carboxylate group of Arg exclusively with amide groups of the AdiC backbone. In the context of substrate binding in the human SLC7 family member l-type amino acid transporter-1 (LAT1; SLC7A5), an analogous role of S66 in LAT1 to S26 in AdiC is discussed based on homology modeling and amino acid sequence analysis. Finally, we propose a binding mechanism for l-amino acid substrates to LATs from the SLC7 family.

  18. Colloidal Properties of Aqueous Fullerenes: Isoelectric Points and Aggregation Kinetics of C60 and C60 Derivatives

    EPA Science Inventory

    Aqueous colloidal suspensions of C-60 (aqu/C-60) and the C-60 derivatives PCBM ([6,6]-phenyl C-61-butyric acid methyl ester) and the corresponding butyl and octyl esters, PCBB and PCBO (aqu/PCB-R, where R is an alkyl group), were produced by stirring in double deionized water for...

  19. Dissection of the methyl-CpG binding domain from the chromosomal protein MeCP2.

    PubMed Central

    Nan, X; Meehan, R R; Bird, A

    1993-01-01

    MeCP2 is a chromosomal protein which binds to DNA that is methylated at CpG. In situ immunofluorescence in mouse cells has shown that the protein is most concentrated in pericentromeric heterochromatin, suggesting that MeCP2 may play a role in the formation of inert chromatin. Here we have isolated a minimal methyl-CpG binding domain (MBD) from MeCP2. MBD is 85 amino acids in length, and binds exclusively to DNA that contains one or more symmetrically methylated CpGs. MBD has negligable non-specific affinity for DNA, confirming that non-specific and methyl-CpG specific binding domains of MeCP2 are distinct. In vitro footprinting indicates that MBD binding can protect a 12 nucleotide region surrounding a methyl-CpG pair, with an approximate dissociation constant of 10(-9) M. Images PMID:8177735

  20. Total enzymatic synthesis of cholecystokinin CCK-5.

    PubMed

    Xiang, H; Xiang, G Y; Lu, Z M; Guo, L; Eckstein, H

    2004-08-01

    This paper describes the enzymatic synthesis of the C-terminal fragment H-Gly-Trp-Met-Asp-Phe-NH2 of cholecystokinin. Immobilized enzymes were used for the formation of all peptide bonds except thermolysin. Beginning the synthesis with phenylacetyl (PhAc) glycine carboxamidomethyl ester (OCam) and H-Trp-OMe by using immobilized papain as biocatalyst in buffered ethyl acetate, the dipeptide methyl ester was then coupled directly with Met-OEt.HCl by alpha-chymotrypsin/Celite 545 in a solvent free system. For the 3+2 coupling PhAc-Gly-Trp-Met-OEt had to be converted into its OCam ester. The other fragment H-Asp(OMe)-Phe-NH2 resulted from the coupling of Cbo-Asp(OMe)-OH with H-Phe-NH2.HCl and thermolysin as catalyst, followed by catalytic hydrogenation. Finally PhAc-Gly-Trp-Met-Asp-Phe-NH2 was obtained in a smooth reaction from PhAc-Gly-Trp-Met-OCam and H-Asp(OMe)-Phe-NH2 with alpha-chymotrypsin/Celite 545 in acetonitrile, followed by basic hydrolysis of the beta-methyl ester. The PhAc-group is removed with penicillin G amidase and CCK-5 is obtained in an overall isolated yield of 19.6%.

  1. Quantitative analysis of fatty-acid-based biofuels produced by wild-type and genetically engineered cyanobacteria by gas chromatography-mass spectrometry.

    PubMed

    Guan, Wenna; Zhao, Hui; Lu, Xuefeng; Wang, Cong; Yang, Menglong; Bai, Fali

    2011-11-11

    Simple and rapid quantitative determination of fatty-acid-based biofuels is greatly important for the study of genetic engineering progress for biofuels production by microalgae. Ideal biofuels produced from biological systems should be chemically similar to petroleum, like fatty-acid-based molecules including free fatty acids, fatty acid methyl esters, fatty acid ethyl esters, fatty alcohols and fatty alkanes. This study founded a gas chromatography-mass spectrometry (GC-MS) method for simultaneous quantification of seven free fatty acids, nine fatty acid methyl esters, five fatty acid ethyl esters, five fatty alcohols and three fatty alkanes produced by wild-type Synechocystis PCC 6803 and its genetically engineered strain. Data obtained from GC-MS analyses were quantified using internal standard peak area comparisons. The linearity, limit of detection (LOD) and precision (RSD) of the method were evaluated. The results demonstrated that fatty-acid-based biofuels can be directly determined by GC-MS without derivation. Therefore, rapid and reliable quantitative analysis of fatty-acid-based biofuels produced by wild-type and genetically engineered cyanobacteria can be achieved using the GC-MS method founded in this work. Copyright © 2011 Elsevier B.V. All rights reserved.

  2. Evaluation of HDPE water sample bottles and PVC sampler tubing used in herbicide dissipation studies.

    Treesearch

    J. B. Fischer; J. L. Michael; H. L. Gibbs

    2009-01-01

    The recovery of six herbicides (triclopyr, triclopyr ester, sulfometuron methyl, metsulfuron methyl, imazapyr, and hexazinone) was evaluated in two stream water samples, one from Weogufka Creek in the Alabama Piedmont and one from a stagnant stream in the Escambia Experimental Forest near Florida. Simulated field study conditions were...

  3. Classification of bacteria by simultaneous methylation-solid phase microextraction and gas chromatography/mass spectrometry analysis of fatty acid methyl esters.

    PubMed

    Lu, Yao; Harrington, Peter B

    2010-08-01

    Direct methylation and solid-phase microextraction (SPME) were used as a sample preparation technique for classification of bacteria based on fatty acid methyl ester (FAME) profiles. Methanolic tetramethylammonium hydroxide was applied as a dual-function reagent to saponify and derivatize whole-cell bacterial fatty acids into FAMEs in one step, and SPME was used to extract the bacterial FAMEs from the headspace. Compared with traditional alkaline saponification and sample preparation using liquid-liquid extraction, the method presented in this work avoids using comparatively large amounts of inorganic and organic solvents and greatly decreases the sample preparation time as well. Characteristic gas chromatography/mass spectrometry (GC/MS) of FAME profiles was achieved for six bacterial species. The difference between Gram-positive and Gram-negative bacteria was clearly visualized with the application of principal component analysis of the GC/MS data of bacterial FAMEs. A cross-validation study using ten bootstrap Latin partitions and the fuzzy rule building expert system demonstrated 87 +/- 3% correct classification efficiency.

  4. Experimental and theoretical studies of the molecular structure of 7-Methyl-3-[(3-methyl-3-mesityl-cyclobutyl]-5-phenyl-5H-thiazolo[3,2-α]pyrimidine-6-carboxylic acid ethyl ester

    NASA Astrophysics Data System (ADS)

    Acar, Betül; Yilmaz, Ibrahim; Çalışkan, Nezihe; Cukurovali, Alaaddin

    2017-07-01

    In this work, the title molecule, 7-Methyl-3-[(3-methyl-3-mesityl-cyclobutyl]-5-phenyl-5H-thiazolo[3,2-α]pyrimidine-6-carboxylic acid ethyl ester (C30H34N2O2S1), was synthesized and characterized by FT-IR spectroscopy and single crystal X-ray diffraction. The compound crystallizes in the triclinic space group P21/c. with Z = 4, a = 14.1988(6), b = 19.0893(5), c = 10.1325(4) Å, V = 2674.56(17) A3. The optimized structure parameters of the studied molecule was determined theoretically using HF/6-31G(d) and B3LYP/6-31G(d) methods for ground state, and compared with previously reported experimental findings. The calculated harmonic vibrational frequencies are scaled and they are compared with experimental frequencies obtained by FT-IR spectra. The electronic properties, such as HOMO and LUMO energies, and molecular electrostatic potential (MEP) are also performed.

  5. Parallel synthesis: a new approach for developing analytical internal standards. Application to the analysis of patulin by gas chromatography-mass spectrometry.

    PubMed

    Llovera, Montserrat; Balcells, Mercè; Torres, Mercè; Canela, Ramon

    2005-08-24

    The polymer-assisted reaction of 4-(hydroxymethyl)furan-2(5H)-one (4HM2F) with 21 carboxylic acids using polystyrene-carbodiimide (PS-carbodiimide) yielded an ester library. Four of the esters, (5-oxo-2,5-dihydrofuran-3-yl)methyl acetate (IS-1), (5-oxo-2,5-dihydrofuran-3-yl)methyl butyrate (IS-2), (5-oxo-2,5-dihydrofuran-3-yl)methyl 2-methylpropanoate (IS-3), and (5-oxo-2,5-dihydrofuran-3-yl)methyl chloroacetate (IS-4), were tested as internal standards for the quantification of patulin in apple juice by gas chromatography-mass spectrometry in the selected ion monitoring mode (GC-MS-SIM). The developed method combines an AOAC official extractive step and a GC-MS-SIM analysis. Using a chromatographic column containing trifluoropropylmethylpolysiloxane as the stationary phase and IS-1 as the internal standard, it was possible to perform an accurate and precise quantification of underivatizated patulin in apple juice at concentrations down to 6 microg/L. A detection limit of 1 microg/L was established.

  6. Tumour-promoting phorbol esters increase basal and inhibit insulin-stimulated lipogenesis in rat adipocytes without decreasing insulin binding.

    PubMed Central

    van de Werve, G; Proietto, J; Jeanrenaud, B

    1985-01-01

    In isolated rat adipocytes, tumour-promoting phorbol esters caused (1) dose-dependent stimulation of lipogenesis in the absence of insulin and (2) inhibition of the lipogenic effect of submaximal concentrations of insulin, but without affecting insulin binding. The possible involvement of protein kinase C in insulin action is discussed. PMID:3883992

  7. Optimization of one-step in situ transesterification method for accurate quantification of EPA in Nannochloropsis gaditana

    DOE PAGES

    Tang, Yuting; Zhang, Yue; Rosenberg, Julian N.; ...

    2016-11-08

    Microalgae are a valuable source of lipid feedstocks for biodiesel and valuable omega-3 fatty acids. Nannochloropsis gaditana has emerged as a promising producer of eicosapentaenoic acid (EPA) due to its fast growth rate and high EPA content. In the present study, the fatty acid profile of Nannochloropsis gaditana was found to be naturally high in EPA and devoid of docosahexaenoic acid (DHA), thereby providing an opportunity to maximize the efficacy of EPA production. Using an optimized one-step in situ transesterification method (methanol:biomass = 90 mL/g; HCl 5% by vol.; 70 °C; 1.5 h), the maximum fatty acid methyl ester (FAME)more » yield of Nannochloropsis gaditana cultivated under rich condition was quantified as 10.04% ± 0.08% by weight with EPA-yields as high as 4.02% ± 0.17% based on dry biomass. The total FAME and EPA yields were 1.58- and 1.23-fold higher separately than that obtained using conventional two-step method (solvent system: methanol and chloroform). Furthermore, this one-step in situ method provides a fast and simple method to measure fatty acid methyl ester (FAME) yields and could serve as a promising method to generate eicosapentaenoic acid methyl ester from microalgae.« less

  8. Performance of Surfactant Methyl Ester Sulphonate solution for Oil Well Stimulation in reservoir sandstone TJ Field

    NASA Astrophysics Data System (ADS)

    Eris, F. R.; Hambali, E.; Suryani, A.; Permadi, P.

    2017-05-01

    Asphaltene, paraffin, wax and sludge deposition, emulsion and water blocking are kinds ofprocess that results in a reduction of the fluid flow from the reservoir into formation which causes a decrease of oil wells productivity. Oil well Stimulation can be used as an alternative to solve oil well problems. Oil well stimulation technique requires applying of surfactant. Sodium Methyl Ester Sulphonate (SMES) of palm oil is an anionic surfactant derived from renewable natural resource that environmental friendly is one of potential surfactant types that can be used in oil well stimulation. This study was aimed at formulation SMES as well stimulation agent that can identify phase transitions to phase behavior in a brine-surfactant-oil system and altered the wettability of rock sandstone and limestone. Performance of SMES solution tested by thermal stability test, phase behavioral examination and rocks wettability test. The results showed that SMES solution (SMES 5% + xylene 5% in the diesel with addition of 1% NaCl at TJformation water and SMES 5% + xylene 5% in methyl ester with the addition of NaCl 1% in the TJ formation water) are surfactant that can maintain thermal stability, can mostly altered the wettability toward water-wet in sandstone reservoir, TJ Field.

  9. Visualizing morphogenesis in transgenic zebrafish embryos using BODIPY TR methyl ester dye as a vital counterstain for GFP.

    PubMed

    Cooper, Mark S; Szeto, Daniel P; Sommers-Herivel, Greg; Topczewski, Jacek; Solnica-Krezel, Lila; Kang, Hee-Chol; Johnson, Iain; Kimelman, David

    2005-02-01

    Green fluorescent protein (GFP) technology is rapidly advancing the study of morphogenesis, by allowing researchers to specifically focus on a subset of labeled cells within the living embryo. However, when imaging GFP-labeled cells using confocal microscopy, it is often essential to simultaneously visualize all of the cells in the embryo using dual-channel fluorescence to provide an embryological context for the cells expressing GFP. Although various counterstains are available, part of their fluorescence overlaps with the GFP emission spectra, making it difficult to clearly identify the cells expressing GFP. In this study, we report that a new fluorophore, BODIPY TR methyl ester dye, serves as a versatile vital counterstain for visualizing the cellular dynamics of morphogenesis within living GFP transgenic zebrafish embryos. The fluorescence of this photostable synthetic dye is spectrally separate from GFP fluorescence, allowing dual-channel, three-dimensional (3D) and four-dimensional (4D) confocal image data sets of living specimens to be easily acquired. These image data sets can be rendered subsequently into uniquely informative 3D and 4D visualizations using computer-assisted visualization software. We discuss a variety of immediate and potential applications of BODIPY TR methyl ester dye as a vital visualization counterstain for GFP in transgenic zebrafish embryos. Copyright 2004 Wiley-Liss, Inc.

  10. 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

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

    PubMed

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

    2012-02-01

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

  12. Optimization of one-step in situ transesterification method for accurate quantification of EPA in Nannochloropsis gaditana

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    Tang, Yuting; Zhang, Yue; Rosenberg, Julian N.

    Microalgae are a valuable source of lipid feedstocks for biodiesel and valuable omega-3 fatty acids. Nannochloropsis gaditana has emerged as a promising producer of eicosapentaenoic acid (EPA) due to its fast growth rate and high EPA content. In the present study, the fatty acid profile of Nannochloropsis gaditana was found to be naturally high in EPA and devoid of docosahexaenoic acid (DHA), thereby providing an opportunity to maximize the efficacy of EPA production. Using an optimized one-step in situ transesterification method (methanol:biomass = 90 mL/g; HCl 5% by vol.; 70 °C; 1.5 h), the maximum fatty acid methyl ester (FAME)more » yield of Nannochloropsis gaditana cultivated under rich condition was quantified as 10.04% ± 0.08% by weight with EPA-yields as high as 4.02% ± 0.17% based on dry biomass. The total FAME and EPA yields were 1.58- and 1.23-fold higher separately than that obtained using conventional two-step method (solvent system: methanol and chloroform). Furthermore, this one-step in situ method provides a fast and simple method to measure fatty acid methyl ester (FAME) yields and could serve as a promising method to generate eicosapentaenoic acid methyl ester from microalgae.« less

  13. Microwave-assisted biodiesel production by esterification of palm fatty acid distillate.

    PubMed

    Lokman, Ibrahim M; Rashid, Umer; Zainal, Zulkarnain; Yunus, Robiah; Taufiq-Yap, Yun Hin

    2014-01-01

    In the current research work, effect of microwave irradiation energy on the esterification of palm fatty acid distillate (PFAD) to produce PFAD methyl ester / biodiesel was intensively appraised. The PFAD is a by-product from refinery of crude palm oil consisting >85% of free fatty acid (FFA). The esterification reaction process with acid catalyst is needed to convert the FFA into fatty acid methyl ester or known as biodiesel. In this work, fabricated microwave-pulse width modulation (MPWM) reactor with controlled temperature was designed to be capable to increase the PFAD biodiesel production rate. The classical optimization technique was used in order to study the relationship and the optimum condition of variables involved. Consequently, by using MPWM reactor, mixture of methanol-to-PFAD molar ratio of 9:1, 1 wt.% of sulfuric acid catalyst, at 55°C reaction temperature within 15 min reaction time gave 99.5% of FFA conversion. The quality assessment and properties of the product were analyzed according to the American Society for Testing and Materials (ASTM), European (EN) standard methods and all results were in agreement with the standard requirements. It revealed that the use of fabricated MPWM with controlled temperature was significantly affecting the rate of esterification reaction and also increased the production yield of PFAD methyl ester.

  14. Rhodium(III)-Catalyzed ortho-Alkylation of Phenoxy Substrates with Diazo Compounds via C-H Activation: A Case of Decarboxylative Pyrimidine/Pyridine Migratory Cyclization Rather than Removal of Pyrimidine/Pyridine Directing Group.

    PubMed

    Ravi, Manjula; Allu, Srinivasarao; Swamy, K C Kumara

    2017-03-03

    An efficient Rh(III)-catalyzed ortho-alkylation of phenoxy substrates with diazo compounds has been achieved for the first time using pyrimidine or pyridine as the directing group. Furthermore, bis-alkylation has also been achieved using para-substituted phenoxypyrimidine and 3 mol equiv of the diazo ester. The ortho-alkylated derivatives of phenoxy products possessing the ester functionality undergo decarboxylative pyrimidine/pyridine migratory cyclization (rather than deprotection of pyrimidine/pyridine group) using 20% NaOEt in EtOH affording a novel class of 3-(pyrimidin-2(1H)-ylidene)benzofuran-2(3H)-ones and 6-methyl-3-(pyridin-2(1H)-ylidene)benzofuran-2(3H)-one. The ortho-alkylated phenoxypyridine possessing ester functionality also undergoes decarboxylative pyridine migratory cyclization using MeOTf/NaOMe in toluene providing 6-methyl-3-(1-methylpyridin-2(1H)-ylidene)benzofuran-2(3H)-one.

  15. 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.

  16. Methyl ester of [Maclura pomifera (Rafin.) Schneider] seed oil: biodiesel production and characterization.

    PubMed

    Saloua, Fatnassi; Saber, Chatti; Hedi, Zarrouk

    2010-05-01

    Oil extracted from seeds of Maclura pomifera fruits grown in Tunisia was investigated as an alternative feedstock for the production of biodiesel fuel. Biodiesel was prepared by transesterification of the crude oil with methanol in the presence of NaOH as catalyst. Maximum oil to ester conversion was 90%. The viscosity of the biodiesel oil (4.66 cSt) is similar to that of petroleum diesel (2.5-3.5 cSt). The density (0.889 g/cm(3)), kinematic viscosity (4.66 cSt), flash point (180 degrees Celsius), iodine number (125 degrees Celsius), neutralization number (0.4), pour point (-9 degrees Celsius), cloud point (-5 degrees Celsius), cetane number (48) are very similar to the values set forth by the ASTM and EN biodiesel standards for petroleum diesel (No. 2). The comparison shows that the methyl esters of M. pomifera oil could be possible diesel fuel replacements. Copyright 2009 Elsevier Ltd. All rights reserved.

  17. Determination of selected fate and aquatic toxicity characteristics of acrylic acid and a series of acrylic esters.

    PubMed

    Staples, C A; Murphy, S R; McLaughlin, J E; Leung, H W; Cascieri, T C; Farr, C H

    2000-01-01

    Acrylic acid, methyl acrylate, ethyl acrylate, and butyl acrylate are commercially important and widely used materials. This paper reports the results of a series of fate and aquatic toxicity studies. The mobility in soil of acrylic acid and its esters ranged from 'medium' to 'very high'. Calculated bioconcentration factors ranged from 1 to 37, suggesting a low bioconcentration potential. Acrylic acid and methyl acrylate showed limited biodegradability in the five day biochemical oxygen demand (BOD5) test, while ethyl acrylate and butyl acrylate were degraded easily (77% and 56%, respectively). Using the OECD method 301D 28-d closed bottle test, degradability for acrylic acid was 81% at 28 days, while the acrylic esters ranged from 57% to 60%. Acrylic acid degraded rapidly to carbon dioxide in soil (t1/2 < 1 day). Toxicity tests were conducted using freshwater and marine fish, invertebrates, and algae. Acrylic acid effect concentrations for fish and invertebrates ranged from 27 to 236 mg/l. Effect concentrations (LC50 or EC50) for fish and invertebrates using methyl acrylate, ethyl acrylate, and butyl acrylate ranged from 1.1 to 8.2 mg/l. The chronic MATC for acrylic acid with Daphnia magna was 27 mg/l based on length and young produced per adult reproduction day and for ethyl acrylate was 0.29 mg/l based on both the reproductive and growth endpoints. Overall these studies show that acrylic acid and the acrylic esters studied can rapidly biodegrade, have a low potential for persistence or bioaccumulation in the environment, and have low to moderate toxicity.

  18. Highly efficient conversion of plant oil to bio-aviation fuel and valuable chemicals by combination of enzymatic transesterification, olefin cross-metathesis, and hydrotreating.

    PubMed

    Wang, Meng; Chen, Mojin; Fang, Yunming; Tan, Tianwei

    2018-01-01

    The production of fuels and chemicals from renewable resources is increasingly important due to the environmental concern and depletion of fossil fuel. Despite the fast technical development in the production of aviation fuels, there are still several shortcomings such as a high cost of raw materials, a low yield of aviation fuels, and poor process techno-economic consideration. In recent years, olefin metathesis has become a powerful and versatile tool for generating new carbon-carbon bonds. The cross-metathesis reaction, one kind of metathesis reaction, has a high potential to efficiently convert plant oil into valuable chemicals, such as α-olefin and bio-aviation fuel by combining with a hydrotreatment process. In this research, an efficient, four-step conversion of plant oil into bio-aviation fuel and valuable chemicals was developed by the combination of enzymatic transesterification, olefin cross-metathesis, and hydrotreating. Firstly, plant oil including oil with poor properties was esterified to fatty acid methyl esters by an enzyme-catalyzed process. Secondly, the fatty acid methyl esters were partially hydrotreated catalytically to transform poly-unsaturated fatty acid such as linoleic acid into oleic acid. The olefin cross-metathesis then transformed the oleic acid methyl ester (OAME) into 1-decene and 1-decenoic acid methyl ester (DAME). The catalysts used in this process were prepared/selected in function of the catalytic reaction and the reaction conditions were optimized. The carbon efficiency analysis of the new process illustrated that it was more economically feasible than the traditional hydrotreatment process. A highly efficient conversion process of plant oil into bio-aviation fuel and valuable chemicals by the combination of enzymatic transesterification, olefin cross-metathesis, and hydrotreatment with prepared and selected catalysts was designed. The reaction conditions were optimized. Plant oil was transformed into bio-aviation fuel and a high value α-olefin product with high carbon utilization.

  19. Genotypic differences in Al resistance and the role of cell-wall pectin in Al exclusion from the root apex in Fagopyrum tataricum

    PubMed Central

    Yang, Jian Li; Zhu, Xiao Fang; Zheng, Cheng; Zhang, Yue Jiao; Zheng, Shao Jian

    2011-01-01

    Background and Aims Aluminium (Al) toxicity is one of the factors limiting crop production on acid soils. However, genotypic differences exist among plant species or cultivars in response to Al toxicity. This study aims to investigate genotypic differences among eight cultivars of tatary buckwheat (Fagopyrum tataricum) for Al resistance and explore the possible mechanisms of Al resistance. Methods Al resistance was evaluated based on relative root elongation (root elongation with Al/root elongation without Al). Root apex Al content, pectin content and exudation of root organic acids were determined and compared. Key Results Genotypic differences among the eight cultivars were correlated with exclusion of Al from the root apex. However, there was a lack of correlation between Al exclusion and Al-induced oxalate secretion. Interestingly, cell-wall pectin content of the root apex was generally lower in Al-resistant cultivars than in Al-sensitive cultivars. Although we were unable to establish a significant correlation between Al exclusion and pectin content among the eight cultivars, a strong correlation could be established among six cultivars, in which the pectin content in the most Al-resistant cultivar ‘Chuan’ was significantly lower than that in the most Al-sensitive cultivar ‘Liuku2’. Furthermore, root apex cell-wall pectin methylesterase activity (PME) was similar in ‘Chuan’ and ‘Liuku2’ in the absence of Al, but Al treatment resulted in increased PME activity in ‘Liuku2’ compared with ‘Chuan’. Immunolocalization of pectins also showed that the two cultivars had similar amounts of either low-methyl-ester pectins or high-methyl-ester pectins in the absence of Al, but Al treatment resulted in a more significant increase of low-methyl-ester pectins and decrease of high-methyl-ester pectins in ‘Liuku2’. Conclusions Cell-wall pectin content may contribute, at least in part, to differential Al resistance among tatary buckwheat cultivars. PMID:21183454

  20. Studies on piston bowl geometries using single blend ratio of various non-edible oils.

    PubMed

    Viswanathan, Karthickeyan; Pasupathy, Balamurugan

    2017-07-01

    The depletion of fossil fuels and hike in crude oil prices were some of the main reasons to explore new alternatives from renewable source of energy. This work presents the impact of various bowl geometries on diesel engine with diesel and biodiesel samples. Three non-edible oils were selected, namely pumpkin seed oil, orange oil and neem oil. These oils were converted into respective biodiesel using transesterification process in the presence of catalyst and alcohol. After transesterification process, the oils were termed as pumpkin seed oil methyl ester (PSOME), orange oil methyl ester (OME) and neem oil methyl ester (NOME), respectively. The engine used for experimentation was a single-cylinder four-stroke water-cooled direct-injection diesel engine and loads were applied to the engine using eddy current dynamometer. Two bowl geometries were developed, namely toroidal combustion chamber (TCC) and trapezoidal combustion chamber (TRCC). Also, the engine was inbuilt with hemispherical combustion chamber (HCC). The base line readings were recorded using neat diesel fuel with HCC for various loads. Followed by 20% of biodiesel mixed with 80% neat diesel for all prepared methyl esters and termed as B1 (20% PSOME with 80% diesel), B2 (20% OME with 80% diesel) and B3 (20% NOME with 80% diesel). All fuel samples were tested in HCC, TCC and TRCC bowl geometries under standard injection timing and with compression ratio of 18. Increased brake thermal efficiency and reduced brake specific fuel consumption were observed with diesel in TCC geometry. Also, higher heat release and cylinder pressures with lower ignition delay were recorded with TCC bowl geometry. TCC bowl geometry showed lower CO, HC and smoke emissions with B2 fuel sample than diesel and other biodiesel samples. But, higher NOx emission was observed in HCC and TCC than that in TRCC bowl geometry. Graphical abstract ᅟ.

  1. Elucidation of in-vitro anti-inflammatory bioactive compounds isolated from Jatropha curcas L. plant root.

    PubMed

    Othman, Ahmad Razi; Abdullah, Norhani; Ahmad, Syahida; Ismail, Intan Safinar; Zakaria, Mohamad Pauzi

    2015-02-05

    The Jatropha curcas plant or locally known as "Pokok Jarak" has been widely used in traditional medical applications. This plant is used to treat various conditions such as arthritis, gout, jaundice, wound and inflammation. However, the nature of compounds involved has not been well documented. Hence, this study was conducted to investigate the anti-inflammatory activity of different parts of J. curcas plant and to identify the active compounds involved. In this study, methanol (80%) extraction of four different parts (leaves, fruits, stem and root) of J. curcas plant was carried out. Phenolic content of each part was determined by using Folin-Ciocalteau reagent. Gallic acid was used as the phenol standard. Each plant part was screened for anti-inflammatory activity using cultured macrophage RAW 264.7 cells. The active plant part was then partitioned with hexane, chloroform, ethyl acetate and water. Each partition was again screened for anti-inflammatory activity. The active partition was then fractionated using an open column chromatography system. Single spots isolated from column chromatography were assayed for anti-inflammatory and cytotoxicity activities. Spots that showed activity were subjected to gas chromatography mass spectrophotometry (GC-MS) analysis for identification of active metabolites. The hexane partition from root extract showed the highest anti-inflammatory activity. However, it also showed high cytotoxicity towards RAW 264.7 cells at 1 mg/mL. Fractionation process using column chromatography showed five spots. Two spots labeled as H-4 and H-5 possessed anti-inflammatory activity, without cytotoxicity activity. Analysis of both spots by GC-MS showed the presence of hexadecanoic acid methyl ester, octadecanoic acid methyl ester and octadecanoic acid. This finding suggests that hexadecanoic acid methyl ester, octadecanoic acid methyl ester and octadecanoic acid could be responsible for the anti-inflammatory activity of the J. curcas root extract.

  2. Role of endothelial nitric oxide synthase as a trigger and mediator of isoflurane-induced delayed preconditioning in rabbit myocardium.

    PubMed

    Chiari, Pascal C; Bienengraeber, Martin W; Weihrauch, Dorothee; Krolikowski, John G; Kersten, Judy R; Warltier, David C; Pagel, Paul S

    2005-07-01

    Isoflurane produces delayed preconditioning in vivo. The authors tested the hypothesis that endothelial, inducible, or neuronal nitric oxide synthase (NOS) is a trigger or mediator of this protective effect. In the absence or presence of exposure to isoflurane (1.0 minimum alveolar concentration) 24 h before experimentation, pentobarbital-anesthetized rabbits (n = 128) instrumented for hemodynamic measurement received 0.9% saline (control), the nonselective NOS inhibitor N-nitro-l-arginine methyl ester (10 mg/kg), one of two of the selective inducible NOS antagonists aminoguanidine (300 mg/kg) or 1400W (0.5 mg/kg), or the selective neuronal NOS inhibitor 7-nitroindazole (50 mg/kg) administered before exposure to isoflurane (trigger; day 1) or left anterior descending coronary artery occlusion (mediator; day 2). All rabbits underwent 30 min of coronary occlusion followed by 3 h of reperfusion. Tissue samples for reverse-transcription polymerase chain reaction and immunohistochemistry were also obtained in the presence or absence of N-nitro-l-arginine methyl ester with or without isoflurane pretreatment. Isoflurane significantly (P < 0.05) reduced infarct size (23 +/- 5% [mean +/- SD] of the left ventricular area at risk; triphenyltetrazolium chloride staining) as compared with control (42 +/- 7%). N-nitro-l-arginine methyl ester administered before isoflurane or coronary occlusion abolished protection (49 +/- 7 and 43 +/- 10%, respectively). Aminoguanidine, 1400W, and 7-nitroindazole did not alter infarct size or affect isoflurane-induced delayed preconditioning. Isoflurane increased endothelial but not inducible NOS messenger RNA transcription and protein translation immediately and 24 h after administration of the volatile agent. Pretreatment with N-nitro-l-arginine methyl ester attenuated isoflurane-induced increases in endothelial NOS expression. The results suggest that endothelial NOS but not inducible or neuronal NOS is a trigger and mediator of delayed preconditioning by isoflurane in vivo.

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

    PubMed

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

    2012-06-01

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

  4. Effects of parabens on adipocyte differentiation.

    PubMed

    Hu, Pan; Chen, Xin; Whitener, Rick J; Boder, Eric T; Jones, Jeremy O; Porollo, Aleksey; Chen, Jiangang; Zhao, Ling

    2013-01-01

    Parabens are a group of alkyl esters of p-hydroxybenzoic acid that include methylparaben, ethylparaben, propylparaben, butylparaben, and benzylparaben. Paraben esters and their salts are widely used as preservatives in cosmetics, toiletries, food, and pharmaceuticals. Humans are exposed to parabens through the use of such products from dermal contact, ingestion, and inhalation. However, research on the effects of parabens on health is limited, and the effects of parabens on adipogenesis have not been systematically studied. Here, we report that (1) parabens promote adipogenesis (or adipocyte differentiation) in murine 3T3-L1 cells, as revealed by adipocyte morphology, lipid accumulation, and mRNA expression of adipocyte-specific markers; (2) the adipogenic potency of parabens is increased with increasing length of the linear alkyl chain in the following potency ranking order: methyl- < ethyl- < propyl- < butylparaben. The extension of the linear alkyl chain with an aromatic ring in benzylparaben further augments the adipogenic ability, whereas 4-hydroxybenzoic acid, the common metabolite of all parabens, and the structurally related benzoic acid (without the OH group) are inactive in promoting 3T3-L1 adipocyte differentiation; (3) parabens activate glucocorticoid receptor and/or peroxisome proliferator-activated receptor γ in 3T3-L1 preadipocytes; however, no direct binding to, or modulation of, the ligand binding domain of the glucocorticoid receptor by parabens was detected by glucocorticoid receptor competitor assays; and lastly, (4) parabens, butyl- and benzylparaben in particular, also promote adipose conversion of human adipose-derived multipotent stromal cells. Our results suggest that parabens may contribute to obesity epidemic, and the role of parabens in adipogenesis in vivo needs to be examined further.

  5. A rumen unprotected conjugated linoleic acid supplement inhibits milk fat synthesis and improves energy balance in lactating goats.

    PubMed

    Baldin, M; Gama, M A S; Dresch, R; Harvatine, K J; Oliveira, D E

    2013-07-01

    Feeding trans-10, cis-12 CLA supplements in a rumen-protected form has been shown to cause milk fat depression (MFD) in cows, ewes, and goats. Methyl esters of CLA were shown to be as effective as FFA in inducing MFD when infused postruminally, but their efficacy as a feed supplement has not been addressed in studies with lactating ruminants. In the present study, we investigated the effects of an unprotected trans-10, cis-12 CLA supplement as methyl esters on performance, milk composition, and energy status of dairy goats. Eighteen multiparous Toggenburg goats were randomly assigned to dietary treatments in a crossover experimental design (14 d treatment periods separated by a 7 d washout interval): 30 g/d of calcium salts of fatty acids (Control) or 30 g/d of a rumen unprotected CLA supplement containing 29.9% of trans-10, cis-12 CLA as methyl esters (CLA). Lipid supplements were mixed into a concentrate and fed individually to animals 3 times a day as a total mixed ration component. The DMI, milk yield, milk protein and lactose content and secretion, and somatic cell count were unaffected by CLA treatment. On the other hand, milk fat content and yield were reduced by 19.9 and 17.9% in CLA-fed goats. Reduced milk fat yield in CLA-fed goats was a consequence of a lower secretion of both preformed and de novo synthesized fatty acids. The CLA treatment also changed the milk fatty acid profile, which included a reduction in the concentration of SFA (2.5%), increased MUFA and PUFA (5.6 and 5.4%, respectively), and a pronounced increase (1576%) in milk fat trans-10, cis-12 CLA. Consistent with the high milk fat trans-10, cis-12 CLA content, all desaturase indexes were reduced in milk fat from CLA-fed goats. The MFD induced by CLA reduced the energy required for milk production by 22%, which was accompanied by an improvement in the estimated energy balance (P < 0.001), greater blood glucose concentration (P < 0.05), and a trend for increased BW (P = 0.08). Approximately 7.2% of trans-10, cis-12 CLA was estimated to escape from rumen biohydrogenation and indirect comparisons with data obtained from other studies suggest equivalent MFD between dietary CLA in the methyl ester form and rumen protected sources. Thus, despite the apparent low degree of rumen protection, our results suggest that methyl esters of CLA could be an alternative to rumen protected CLA supplements due to manufacturing and cost advantages.

  6. Dibenzothiophene-Substituted Fullerene Derivative as Electron Acceptor for Polymer Solar Cells.

    PubMed

    Kim, Hee Un; Park, Jong Baek; Hwang, Do-Hoon

    2016-05-01

    A new fullerene derivative, [6,6]-dibenzo[b,d]thiophene-C61-butyric acid methyl ester (DBTC61BM) was synthesized from C60 using tosylhydrazone, and used as an electron-acceptor material for poly(3-hexylthiophene) (P3HT)-based organic photovoltaic cells. The synthesized DBTC61BM was used to modify the basic structure of [6,6]-phenyl-C61-butyric acid methyl ester (PC61BM) by replacing the aromatic part with dibenzo[b,d]thiophene. The solubilities of DBTC61BM and PC61BM are similar; they have good solubilities in common organic solvents such as dichloromethane, chloroform, toluene, and 1,2-dichlorobenzene. The Stern-Volmer quenching constant (K(sv)) of DBTC61BM was 7.14 x 10(3) M(-1), and was correlated with the binding affinity between the fluorophore and a quencher. The lowest unoccupied molecular orbital energy level of DBTC61BM was -3.71 eV. The charge-carrier mobility of a P3HT:DBTC61BM blend film was determined using the space-charge-limited current method; the electron mobility value obtained for the P3HT:DBTC61BM blend film was 2.13 x 10(-4) cm2 V(-1) s(-1). Photovoltaic devices were fabricated using P3HT as the electron donor and DBTC61BM as the electron acceptor. Among the fabricated devices, photovoltaic cells with the structure ITO/PEDOT:PSS/P3HT:DBTC61BM/LiF/Al showed the highest power conversion efficiency, namely 3.23%, with an open-circuit voltage of 0.64 V, short-circuit-current density of 8.14 mA cm(-2), and fill factor of 0.59, under AM 1.5 G (100 mW cm(-2)) illumination.

  7. Binding Energies of Proton-Bound Dimers of Imidazole and n-Acetylalanine Methyl Ester Obtained by Blackbody Infrared Radiative Dissociation

    PubMed Central

    Jockusch, Rebecca A.; Williams*, Evan R.

    2005-01-01

    The dissociation kinetics of protonated n-acetyl-L-alanine methyl ester dimer (AcAlaMEd), imidazole dimer, and their cross dimer were measured using blackbody infrared radiative dissociation (BIRD). Master equation modeling of these data was used to extract threshold dissociation energies (Eo) for the dimers. Values of 1.18 ± 0.06, 1.11 ± 0.04, and 1.12 ± 0.08 eV were obtained for AcAlaMEd, imidazole dimer, and the cross dimer, respectively. Assuming that the reverse activation barrier for dissociation of the ion–molecule complex is negligible, the value of Eo can be compared to the dissociation enthalpy (ΔHd°) from HPMS data. The Eo values obtained for the imidazole dimer and the cross dimer are in agreement with HPMS values; the value for AcAlaMEd is somewhat lower. Radiative rate constants used in the master equation modeling were determined using transition dipole moments calculated at the semiempirical (AM1) level for all dimers and compared to ab initio (RHF/3-21G*) calculations where possible. To reproduce the experimentally measured dissociation rates using master equation modeling, it was necessary to multiply semiempirical transition dipole moments by a factor between 2 and 3. Values for transition dipole moments from the ab initio calculations could be used for two of the dimers but appear to be too low for AcAlaMEd. These results demonstrate that BIRD, in combination with master equation modeling, can be used to determine threshold dissociation energies for intermediate size ions that are in neither the truncated Boltzmann nor the rapid energy exchange limit. PMID:16604163

  8. 4-Hydroxy-3-Methoxybenzoic Acid Methyl Ester: A Curcumin Derivative Targets Akt/NFκB Cell Survival Signaling Pathway: Potential for Prostate Cancer Management

    PubMed Central

    Kumar, Addanki P; Garcia, Gretchen E; Ghosh, Rita; Rajnarayanan, Rajendran V; Alworth, William L; Slaga, Thomas J

    2003-01-01

    Abstract Transcription factor NFκB and the serine/threonine kinase Akt play critical roles in mammalian cell survival signaling and have been shown to be activated in various malignancies including prostate cancer (PCA). We have developed an analogue of curcumin called 4-hydroxy-3-methoxybenzoic acid methyl ester (HMBME) that targets the Akt/NFκB signaling pathway. Here, we demonstrate the ability of this novel compound to inhibit the proliferation of human and mouse PCA cells. HMBME-induced apoptosis in these cells was tested by using multiple biochemical approaches, in addition to morphological analysis. Overexpression of constitutively active Akt reversed the HMBME-induced growth inhibition and apoptosis, illustrating the direct role of Akt signaling in HMBME-mediated growth inhibition and apoptosis. Further, investigation of the molecular events associated with its action in LNCaP cells shows that: 1) HMBME reduces the level of activated form of Akt (phosphorylated Akt); and 2) inhibits the Akt kinase activity. Further, the transcriptional activity of NFκB, the DNA-binding activity of NFκB, and levels of p65 were all significantly reduced following treatment with HMBME. Overexpression of constitutively active Akt, but not the kinase dead mutant of Akt, activated the basal NFκB transcriptional activity. HMBME treatment had no influence on this constitutively active Aktaugmented NFκB transcriptional activity. These data indicate that HMBME-mediated inhibition of Akt kinase activity may have a potential in suppressing/decreasing the activity of major survival/antiapoptotic pathways. The potential use of HMBME as an agent that targets survival mechanisms in PCA cells is discussed. PMID:12869308

  9. Gallic acid attenuates hypertension, cardiac remodeling, and fibrosis in mice with NG-nitro-L-arginine methyl ester-induced hypertension via regulation of histone deacetylase 1 or histone deacetylase 2.

    PubMed

    Jin, Li; Lin, Ming Quan; Piao, Zhe Hao; Cho, Jae Yeong; Kim, Gwi Ran; Choi, Sin Young; Ryu, Yuhee; Sun, Simei; Kee, Hae Jin; Jeong, Myung Ho

    2017-07-01

    Gallic acid, a natural chemical found in plants, has been reported to show antioxidant, anticancer, and anti-inflammatory effects. We investigated the efficacy of a short-term or long-term treatment with gallic acid in N-nitro-L-arginine methyl ester (L-NAME)-induced hypertensive mice and the underlying regulatory mechanism. Hypertension was sufficiently induced after 2 weeks of L-NAME administration. Cardiac remodeling was assessed by echocardiography. Hypertrophic markers, transcription factors, and fibrosis-related gene expression were evaluated by quantitative real-time polymerase chain reaction and western blotting. Gallic acid effectively lowered SBP, regardless of the administration route (intraperitoneal or oral). L-NAME increased the left ventricular (LV) thickness without an increase in the total heart weight. Weekly echocardiography demonstrated that gallic acid significantly reduced LV posterior wall and septum thickness in chronic L-NAME mice from 3 to 7 weeks. The administration of gallic acid to mice showed a dual preventive and therapeutic effect on the L-NAME-induced LV remodeling. The effect was associated with the suppression of the gene expression of hypertrophy markers and the GATA-binding factor 6 (GATA6) transcription factor. Short-term or long-term treatment with gallic acid attenuated cardiac fibrosis and reduced the expression of histone deacetylase 1 and 2 in H9c2 cells and in rat primary cardiac fibroblasts, as well as in vivo. Small interfering RNA knockdown confirmed the association of these enzymes with L-NAME-induced cardiac remodeling and fibrosis. These results suggested that gallic acid may be a potential therapeutic agent for the treatment of cardiovascular diseases with hypertension and cardiac fibrosis.

  10. Trail Pheromones: Responses of the Texas Leafcutting Ant, Atta texana to Select Halo- and Cyanopyrrole-2-Aldehydes, Ketones, and Esters

    Treesearch

    P. E. Sonnet; John C. Moser

    1973-01-01

    Several halo- and cyanopyrroles related to the trail pheromone of Atta texana (Buckley), were prepared and tested by a faster and more sensitive bioassay that was previously available. Responsiveness of the ants in descending order to these compounds, based on the substituent in the number two position, is: esters, methyl ketones, aldehydes. Slight...

  11. Structural insights into the interactions of phorbol ester and bryostatin complexed with protein kinase C: a comparative molecular dynamics simulation study.

    PubMed

    Thangsunan, Patcharapong; Tateing, Suriya; Hannongbua, Supa; Suree, Nuttee

    2016-07-01

    Protein kinase C (PKC) isozymes are important regulatory enzymes that have been implicated in many diseases, including cancer, Alzheimer's disease, and in the eradication of HIV/AIDS. Given their potential clinical ramifications, PKC modulators, e.g. phorbol esters and bryostatin, are also of great interest in the drug development. However, structural details on the binding between PKC and its modulators, especially bryostatin - the highly potent and non-tumor promoting activator for PKCs, are still lacking. Here, we report the first comparative molecular dynamics study aimed at gaining structural insight into the mechanisms by which the PKC delta cys2 activator domain is used in its binding to phorbol ester and bryostatin-1. As anticipated in the phorbol ester binding, hydrogen bonds are formed through the backbone atoms of Thr242, Leu251, and Gly253 of PKC. However, the opposition of H-bond formation between Thr242 and Gly253 may cause the phorbol ester complex to become less stable when compared with the bryostatin binding. For the PKC delta-bryostatin complex, hydrogen bonds are formed between the Gly253 backbone carbonyl and the C30 carbomethoxy substituent of the ligand. Additionally, the indole Nε1 of the highly homologous Trp252 also forms an H-bond to the C20 ester group on bryostatin. Backbone fluctuations also suggest that this latter H-bond formation may abrogate the transient interaction between Trp252 and His269, thus dampening the fluctuations observed on the nearby Zn(2+)-coordinating residues. This new dynamic fluctuation dampening model can potentially benefit future design of new PKC modulators.

  12. Determination of the ratio between mercaptalbumin and nonmercaptalbumin by HPLC with fluorescence probe specifically binding to albumin.

    PubMed

    Ohyama, Kaname; Kishikawa, Naoya; Matsuo, Aya; Imazato, Takahiro; Ueki, Yukitaka; Wada, Mitsuhiro; Nakashima, Kenichiro; Kuroda, Naotaka

    2014-01-01

    A simple and selective HPLC-fluorescence (FL) method with FL probe, 4-[4-(4-dimethylaminophenyl)-5-phenyl-1H-imidazol-2-yl]benzoic acid methyl ester (DAPIM), for simultaneous determination of mercaptalbumin (HMA) and nonmercaptalbumin (HNA1) was developed. After HMA and HNA1 were separated on an ion-exchange column, they were on-line and post-column mixed with DAPIM. The DAPIM-albumin complex produces FL (λex 370nm and λem 510nm); however, DAPIM solution never gives the FL. Based on this mechanism, selective determination of HMA and HNA1 were achieved without any pretreatment and interfering peak. The proposed method was applied to the measurement of HMA and HNA1 in human serum of healthy volunteers and diabetes mellitus patients. Copyright © 2013 Elsevier B.V. All rights reserved.

  13. Effect of temperature on carrier formation efficiency in organic photovoltaic cells

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    Moritomo, Yutaka, E-mail: moritomo.yutaka.gf@u.tsukuba.ac.jp; Yonezawa, Kouhei; Yasuda, Takeshi

    2014-08-18

    The internal quantum efficiency (ϕ{sub IQ}) of an organic photovoltaic cell is governed by plural processes. Here, we propose that ϕ{sub IQ} can be experimentally decomposed into carrier formation (ϕ{sub CF}) and carrier transfer (ϕ{sub CT}) efficiencies. By combining femtosecond time-resolved and electrochemical spectroscopy, we clarified the effect of temperature on ϕ{sub CF} in a regioregular poly(3-hexylthiophene) (rr-P3HT)/[6,6]-phenyl C{sub 61}-butyric acid methyl ester blend film. We found that ϕ{sub CF} (=0.55) at 80 K is the same as that (=0.55) at 300 K. The temperature insensitivity of ϕ{sub CF} indicates that the electron-hole pairs at the D/A interface are seldom subjected to coulombicmore » binding energy.« less

  14. 76 FR 32196 - Certain New Chemicals; Receipt and Status Information; Correction

    Federal Register 2010, 2011, 2012, 2013, 2014

    2011-06-03

    ... use (S) 2-propenoic Inc. of this polymer is acid, 2-methyl-, 2- for refinishing hydroxyethyl ester, vehicles. through polymer with rel- the hydroxyl groups (1r,2r,4r)-1,7,7- on the polymer, the...)-, (t-4)-, polymers; polymer with 3- surfactant, flow, methyl-3-[(2,2,2- leveling, and trifluoroethoxy...

  15. Complex investigation of the effects of lambertianic acid amide in female mice under conditions of social discomfort.

    PubMed

    Avgustinovich, D F; Fomina, M K; Sorokina, I V; Tolstikova, T G

    2014-09-01

    The effects of chronic administration of a new substance lambertianic acid amide and previously synthesized methyl ester of this acid were compared in female mice living under conditions of social discomfort. For modeling social discomfort, female mouse was housed for 30 days in a cage with aggressive male mouse kept behind a transparent perforated partition and observed its confrontations with another male mouse daily placed to the cage. The new agent more effectively than lambertianic acid methyl ester improved communicativeness and motor activity of animals, reduced hypertrophy of the adrenal glands, and enhanced catalase activity in the blood. These changes suggest that lambertianic acid amide produces a pronounced stress-protective effect under conditions of social discomfort.

  16. The origin of the ligand-controlled regioselectivity in Rh-catalyzed [(2 + 2) + 2] carbocyclizations: steric vs. stereoelectronic effects.

    PubMed

    Crandell, Douglas W; Mazumder, Shivnath; Evans, P Andrew; Baik, Mu-Hyun

    2015-12-01

    Density functional theory calculations demonstrate that the reversal of regiochemical outcome of the addition for substituted methyl propiolates in the rhodium-catalyzed [(2 + 2) + 2] carbocyclization with PPh 3 and ( S )-xyl-binap as ligands is both electronically and sterically controlled. For example, the ester functionality polarizes the alkyne π* orbital to favor overlap of the methyl-substituted terminus of the alkyne with the p π -orbital of the alkenyl fragment of the rhodacycle during alkyne insertion with PPh 3 as the ligand. In contrast, the sterically demanding xyl-binap ligand cannot accommodate the analogous alkyne orientation, thereby forcing insertion to occur at the sterically preferred ester terminus, overriding the electronically preferred orientation for alkyne insertion.

  17. Multispectroscopic investigation of the interaction of BSA and DNA with the anticancer drug, N-(6-ferrocenyl-2-naphthoyl)-gamma-amino butyric acid methyl ester

    NASA Astrophysics Data System (ADS)

    Rajina, S. R.; Sudhi, Geethu; Austin, P.; Praveen, S. G.; Xavier, T. S.; Kenny, Peter T. M.; Binoy, J.

    2018-05-01

    The interaction of a drug with DNA and BSA play a great role in studying anti cancer activity and drug transport properties, which can be effectively, investigated using vibrational spectroscopy, UV visible spectroscopy and Fluorescence spectroscopy. The present work reports the structural features of N-(6-ferrocenyl-2-naphthoyl)-gamma-amino butyric acid Methyl ester (FNGABME) based on FTIR and FTRaman spectroscopy. The absorption and fluorescence spectroscopic methods were used to study the efficiency of the interaction of the compound FNGABME with BSA and DNA and also molecular docking were performed computationally to validate the results which shows that the title compound may exhibit inhibitory activity against the cancer cells.

  18. LFER and CoMFA studies on optical resolution of alpha-alkyl alpha-aryloxy acetic acid methyl esters on DACH-DNB chiral stationary phase.

    PubMed

    Carotti, A; Altomare, C; Cellamare, S; Monforte, A; Bettoni, G; Loiodice, F; Tangari, N; Tortorella, V

    1995-04-01

    The HPLC resolution of a series of racemic alpha-substituted alpha-aryloxy acetic acid methyl esters I on a pi-acid N,N'-(3,5-dinitrobenzoyl)-trans-1,2-diaminocyclohexane as chiral selector was modelled by linear free energy-related (LFER) equations and comparative molecular field analysis (CoMFA). Our results indicate that the retention process mainly depends on solute lipophilicity and steric properties, whereas enantioselectivity is primarily influenced by electrostatic and steric interactions. CoMFA provided additional information with respect to the LFER study, allowed the mixing of different subsets of I and led to a quantitative 3D model of steric and electrostatic factors responsible for chiral recognition.

  19. In vitro microbiological evaluation of novel bis pyrazolones.

    PubMed

    Narayana Rao, D V; Raghavendra Guru Prasad, A; Spoorthy, Y N; Raghunatha Rao, D; Ravindranath, L K

    2014-03-01

    Two series of bis pyrazolones (one with 3-methyl substituent and the other one with 3-amino substituent on the pyrazolone ring) were synthesized by the cyclization reaction between various hydrazides with esters/cyano esters in ethanolic medium. Structures of newly synthesized compounds were confirmed by elemental analysis, IR, (1)H NMR and mass spectral data. These compounds were screened for antibacterial and antifungal activities. The compounds of series 3 with amino substituent demonstrated better activity than the compounds of series 2 with methyl substituent on the pyrazolone ring. Compounds "e, f, c and d" showed higher antimicrobial activity than the compounds "b and a". The antimicrobial potentials of the synthesized compounds were compared with that of standards. Copyright © 2013 Elsevier Masson SAS. All rights reserved.

  20. Cytotoxic principles from the formosan milkweed, Asclepias curassavica.

    PubMed

    Roy, Michael C; Chang, Fang-Rong; Huang, Hsiao-Chu; Chiang, Michael Y-N; Wu, Yang-Chang

    2005-10-01

    A series of cardenolides and related compounds have been isolated from the aerial parts and roots of the ornamental milkweed, Asclepias curassavica. Their structures were determined by spectroscopic and chemical methods. Among them, three derivatives of calactinic acid methyl ester (13-15), 19-nor-16 alpha-acetoxy-10 beta-hydroxyasclepin (16), 20 beta,21-dihydroxypregna-4,6-dien-3-one (19), and 3,4-seco-urs-20(30)-en-3-oic acid (22) are new compounds. The relative configuration of calactinic acid methyl ester (12) has been confirmed by X-ray diffraction analysis on its derivative 13. Most of the cardenolides obtained showed pronounced cytotoxicity against four cancer cell lines (IC(50) 0.01 to 2.0 microg/mL).

  1. Druggability of methyl-lysine binding sites

    NASA Astrophysics Data System (ADS)

    Santiago, C.; Nguyen, K.; Schapira, M.

    2011-12-01

    Structural modules that specifically recognize—or read—methylated or acetylated lysine residues on histone peptides are important components of chromatin-mediated signaling and epigenetic regulation of gene expression. Deregulation of epigenetic mechanisms is associated with disease conditions, and antagonists of acetyl-lysine binding bromodomains are efficacious in animal models of cancer and inflammation, but little is known regarding the druggability of methyl-lysine binding modules. We conducted a systematic structural analysis of readers of methyl marks and derived a predictive druggability landscape of methyl-lysine binding modules. We show that these target classes are generally less druggable than bromodomains, but that some proteins stand as notable exceptions.

  2. Monoalkyl sulfates as alkylating agents in water, alkylsulfatase rate enhancements, and the “energy-rich” nature of sulfate half-esters

    PubMed Central

    Wolfenden, Richard; Yuan, Yang

    2007-01-01

    Alkyl sulfate monoesters are involved in cell signaling and structure. Alkyl sulfates are also present in many commercial detergents. Here, we show that monomethyl sulfate acts as an efficient alkylating agent in water, reacting spontaneously with oxygen nucleophiles >100-fold more rapidly than do alkylsulfonium ions, the usual methyl donors in living organisms. These reactions of methyl sulfate, which are much more rapid than its hydrolysis, are insensitive to the nature of the attacking nucleophile, with a Brønsted βnuc value of −0.01. Experiments at elevated temperatures indicate a rate constant of 2 × 10−11 s−1 for the uncatalyzed hydrolysis of methyl sulfate at 25°C (t1/2 = 1,100 y), corresponding to a rate enhancement of ≈1011-fold by a human alkylsulfatase. Equilibria of formation of methyl sulfate from methanol and sodium hydrogen sulfate indicate a group transfer potential (ΔG′pH7) of −8.9 kcal/mol for sulfate ester hydrolysis. The magnitude of that value, involving release of the strong acid HSO4−, helps to explain the need for harnessing the free energy of hydrolysis of two ATP molecules in activating sulfate for the biosynthesis of sulfate monoesters. The “energy-rich” nature of monoalkyl sulfate esters, coupled with their marked resistance to hydrolysis, renders them capable of acting as sulfating or alkylating agents under relatively mild conditions. These findings raise the possibility that, under appropriate circumstances, alkyl groups may undergo transfer from alkyl sulfate monoesters to biological target molecules. PMID:17182738

  3. Electrostatic interaction of positive charges on the surface of Psb31 with photosystem II in the diatom Chaetoceros gracilis.

    PubMed

    Nagao, Ryo; Suzuki, Takehiro; Okumura, Akinori; Kihira, Tomohiro; Toda, Ayaka; Dohmae, Naoshi; Nakazato, Katsuyoshi; Tomo, Tatsuya

    2017-09-01

    Psb31, a novel extrinsic protein found in diatom photosystem II (PSII), directly binds to PSII core subunits, independent of the other extrinsic proteins, and functions to maintain optimum oxygen evolution. However, how Psb31 electrostatically interacts with PSII intrinsic proteins remains to be clarified. In this study, we examined electrostatic interaction of Psb31 with PSII complexes isolated from the diatom Chaetoceros gracilis. Positive or negative charges of isolated Psb31 proteins were modified with N-succinimidyl propionate (NSP) or glycine methyl ester (GME), respectively, resulting in formation of uncharged groups. NSP-modified Psb31 did not bind to PSII with a concomitant increase in NSP concentration, whereas GME-modified Psb31 clearly bound to PSII with retention of oxygen-evolving activity, indicating that positive charges of Lys residues and the N-terminus on the surface of Psb31 are involved in electrostatic interactions with PSII intrinsic proteins. Mass spectrometry analysis of NSP-modified Psb31 and sequence comparisons of Psb31 from C. gracilis with other chromophyte algae led to identification of three Lys residues as possible binding sites to PSII. Based on these findings, together with our previous cross-linking study in diatom PSII and a red algal PSII structure, we discuss binding properties of Psb31 with PSII core proteins. Copyright © 2017 Elsevier B.V. All rights reserved.

  4. A germination bioassay as a toxicological screening system for studying the effects of potential prodrugs of naproxen.

    PubMed

    Gonzalez-de la Parra, M; Ramos-Mundo, C; Jimenez-Estrada, M; Ponce-de Leon, C; Castillo, R; Tejeda, V; Cuevas, K G; Enriquez, R G

    1998-01-01

    A germination bioassay with radish (Raphanus sativus L.) seeds was developed as a toxicological screening system for assessing the effects of new potential prodrugs of naproxen, as an alternative to animals and animal cell toxicity screens. Both enantiomers of naproxen (6-methoxy-α-methyl-2-naphthaleneacetic acid) and naproxol (6-methoxy-β-2-naphthaleneethanol), and their racemic mixtures, inhibited the radicle growth of R. sativus at a concentration of 1mM, while only (R)-(+ )-naproxol and racemic naproxol inhibited the hypocotyl growth of R. sativus at the same concentration. Four novel combinatorial esters, naproxen naproxyl esters (6-methoxy-β-methyl-2-naphthaleneethyl 6-methoxy-α-methyl-2-naphthaleneacetate), resulting from the combinatorial chemistry of the esterification reaction between naproxen and naproxol, were synthesised and then tested in the germination bioassay, at a concentration of 0.5mM. It was found that they did not inhibit either the radicle or the hypocotyl growth of R. sativus. 1998 FRAME.

  5. Pyrogenic transformation of Nannochloropsis oceanica into fatty acid methyl esters without oil extraction for estimating total lipid content.

    PubMed

    Kim, Jieun; Jung, Jong-Min; Lee, Jechan; Kim, Ki-Hyun; Choi, Tae O; Kim, Jae-Kon; Jeon, Young Jae; Kwon, Eilhann E

    2016-07-01

    This study fundamentally investigated the pseudo-catalytic transesterification of dried Nannochloropsis oceanica into fatty acid methyl esters (FAMEs) without oil extraction, which was achieved in less than 5min via a thermo-chemical pathway. This study presented that the pseudo-catalytic transesterification reaction was achieved in the presence of silica and that its main driving force was identified as temperature: pores in silica provided the numerous reaction space like a micro-reactor, where the heterogeneous reaction was developed. The introduced FAME derivatization showed an extraordinarily high tolerance of impurities (i.e., pyrolytic products and various extractives). This study also explored the thermal cracking of FAMEs derived from N. oceanica: the thermal cracking of saturated FAMEs was invulnerable at temperatures lower than 400°C. Lastly, this study reported that N. oceanica contained 14.4wt.% of dried N. oceanica and that the introduced methylation technique could be applicable to many research fields sharing the transesterification platform. Copyright © 2016 Elsevier Ltd. All rights reserved.

  6. Fatty acids composition of Caenorhabditis elegans using accurate mass GCMS-QTOF

    PubMed Central

    Henry, Parise; Owopetu, Olufunmilayo; Adisa, Demilade; Nguyen, Thao; Anthony, Kevin; Ijoni-Animadu, David; Jamadar, Sakha; Abdel-Rahman, Fawzia; Saleh, Mahmoud A.

    2016-01-01

    The free living nematode Caenorhabditis elegans is a proven model organism for lipid metabolism research. Total lipids of C. elegans were extracted using chloroform, methanol 2:1(v/v). Fatty acids composition of the extracted total lipids were converted to their corresponding methyl esters (FAMEs) and analyzed by gas chromatography/accurate mass quadrupole time of flight mass spectrometry (GCMS-QTOF) using both electron ionization (EI) and chemical ionization (CI) techniques. 28 fatty acids consisting of 12 to 22 carbon atoms were identified, 65% of them were unsaturated. Fatty acids containing 12 to 17 carbons were mostly saturated with stearic acid (18:0) as the major constituent. Several branched-chain fatty acids were identified. Methyl-14-methylhexadecanoate (iso-17:0) was the major identified branched fatty acid. This is the first report to detect the intact molecular parent ions of the identified fatty acids using chemical ionization compared to electron ionization which produced fragmentations of the fatty acids methyl esters (FAMEs). PMID:27166662

  7. Overcoming the Gas-Liquid Mass Transfer of Oxygen by Coupling Photosynthetic Water Oxidation with Biocatalytic Oxyfunctionalization.

    PubMed

    Hoschek, Anna; Bühler, Bruno; Schmid, Andreas

    2017-11-20

    Gas-liquid mass transfer of gaseous reactants is a major limitation for high space-time yields, especially for O 2 -dependent (bio)catalytic reactions in aqueous solutions. Herein, oxygenic photosynthesis was used for homogeneous O 2 supply via in situ generation in the liquid phase to overcome this limitation. The phototrophic cyanobacterium Synechocystis sp. PCC6803 was engineered to synthesize the alkane monooxygenase AlkBGT from Pseudomonas putida GPo1. With light, but without external addition of O 2 , the chemo- and regioselective hydroxylation of nonanoic acid methyl ester to ω-hydroxynonanoic acid methyl ester was driven by O 2 generated through photosynthetic water oxidation. Photosynthesis also delivered the necessary reduction equivalents to regenerate the Fe 2+ center in AlkB for oxygen transfer to the terminal methyl group. The in situ coupling of oxygenic photosynthesis to O 2 -transferring enzymes now enables the design of fast hydrocarbon oxyfunctionalization reactions. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  8. Intricate Conformational Tunneling in Carbonic Acid Monomethyl Ester.

    PubMed

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

    2018-04-05

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

  9. Catalytic conversion of lactic acid and its derivatives

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    Kokitkar, P.B.; Langford, R.; Miller, D.J.

    1993-12-31

    The catalytic upgrading of lactic acid and methyl lactate is being investigated. With the commercialization of inexpensive starch fermentation technologies, US production of lactic acid is undergoing a surge. Dropping cost and increased availability offer a major opportunity to develop lactic acid as a renewable feedstock for chemicals production. IT can be catalytically converted into several important chemical intermediates currently derived from petroleum including acrylic acid, propanoic acid, and 2,3-pentanedione. The process can expand the potential of biomass as a substitute feedstock for petroleum and can benefit both the US chemical process industry and US agriculture via increased production ofmore » high-value, non-food products from crops and crop byproducts. Reaction studies of lactic acid and its ester are conducted in fixed bed reactors at 250-380{degrees}C and 0.1-0.5 MPa (1-5 atm) using salt catalysts on low surface area supports. Highest selectivities achieved are 42% to acrylic acid and 55% to 2,3-pentanedione from lactic acid over NaNO{sub 3} catalyst on low surface area silica support. High surface area (microporous) or highly acidic supports promote fragmentation to acetaldehyde and thus reduce yields of desirable products. The support acidity gives rice to lactic acid from neat methyl lactate feed but the lactic acid yield goes down after the nitrate salt is impregnated on the support. Both lactic acid and methyl lactate form 2,3-pentanedione. Methyl lactate reactions are more complex since it forms all the products obtained from lactic acid as well as many corresponding esters of the acids obtained from lactic acid (mainly methyl acrylate, methyl propionate, methyl acetate). At high temperatures, methyl acetate and acetic acid yields become significant from methyl lactate whereas lactic acid gives significant amount of acetol at high temperatures.« less

  10. Synthesis, QSAR and calcium channel modulator activity of new hexahydroquinoline derivatives containing nitroimidazole.

    PubMed

    Miri, Ramin; Javidnia, Katayoun; Mirkhani, Hossein; Hemmateenejad, Bahram; Sepeher, Zahra; Zalpour, Masomeh; Behzad, Taherh; Khoshneviszadeh, Mehdi; Edraki, Najmeh; Mehdipour, Ahmad R

    2007-10-01

    The discovery that 1,4-dihydropyridine class of calcium channel antagonists inhibit Ca2+ influx represented a major therapeutic advance in the treatment of cardiovascular disease. In contrast to the effects of known calcium channel blockers of the Nifedipine-type, the so-called calcium channel agonists, such as Bay K8644 and CGP 28392, increase calcium influx by binding at the same receptor regions. Our goal was to discover a dual cardioselective Ca2+-channel agonist/vascular selective smooth muscle Ca2+ channel antagonist third-generation 1,4-dihydropyridine drug which would have a suitable therapeutic profile for treating congestive heart failure (CHF) patients. A series of unsymmetrical alkyl, cycloalkyl and aryl ester analogues of 2-methyl-4-(1-methyl)-5-nitro-2-imidazolyl-5-oxo-1,4,5,6,7, 8-hexahydroquinolin-3-arboxylate were synthesized using modified Hantzsch reaction. All compounds show calcium antagonist activity on guinea-pig ileum longitudinal smooth muscle and some of them show agonist effect activity on guinea-pig auricle. Effect of structural parameters on the Ca2+ channel agonist/antagonist was evaluated by quantitative structure-activity relationship analysis. These compounds could be considered as a synthon for developing a suitable drug for treating CHF patients.

  11. Synthesis and properties of a new water-soluble prodrug of the adenosine A 2A receptor antagonist MSX-2.

    PubMed

    Vollmann, Karl; Qurishi, Ramatullah; Hockemeyer, Jörg; Müller, Christa E

    2008-02-12

    The compound L-valine-3-{8-[(E)-2-[3-methoxyphenyl)ethenyl]-7-methyl-1-propargylxanthine-3-yl}propyl ester hydrochloride (MSX-4) was synthesized as an amino acid ester prodrug of the adenosine A2A receptor antagonist MSX-2. It was found to be stable in artificial gastric acid, but readily cleaved by pig liver esterase.

  12. The influence of oscillations on product selectivity during the palladium-catalysed phenylacetylene oxidative carbonylation reaction.

    PubMed

    Novakovic, Katarina; Grosjean, Christophe; Scott, Stephen K; Whiting, Andrew; Willis, Mark J; Wright, Allen R

    2008-02-07

    This paper reports on the influence of oscillations on product selectivity as well as the dynamics of product formation during the palladium-catalysed phenylacetylene oxidative carbonylation reaction in a catalytic system (PdI2, KI, Air, NaOAc in methanol). The occurrence of the pH oscillations is related to PdI2 granularity and the initial pH drop after phenylacetylene addition. To achieve pH and reaction exotherm oscillations regulation of the amount of PdI2 is required, ensuring that the initial pH does not fall significantly below 1 after phenylacetylene addition. Experiments in both oscillatory and non-oscillatory pH regimes were performed in an HEL SIMULAR reaction calorimeter with the concentration-time profiles measured using a GC-MS. It is demonstrated that when operating in an oscillatory pH regime product formation may be suppressed until oscillations occur after which there is a steep increase in the formation of Z-2-phenyl-but-2-enedioic acid dimethyl ester. When operating in non-oscillatory pH mode the products are formed steadily over time with the main products being Z-2-phenyl-but-2-enedioic acid dimethyl ester, 2-phenyl-acrylic acid methyl ester and E-3-phenyl-acrylic acid methyl ester.

  13. Electrochemical preparation of polyaniline-polypyrrole solid-phase microextraction coating and its application in the GC determination of several esters.

    PubMed

    Zhao, Shasha; Wu, Mian; Zhao, Faqiong; Zeng, Baizhao

    2013-12-15

    A novel polyaniline-polypyrrole (PANI-PPY) composite film coated stainless steel wire was prepared by cyclic voltammetry. Firstly, PANI was electrodeposited on a stainless steel wire from a solution containing 0.1 M aniline and 1M HNO3, after the PANI coating was dried in air PPY was electrodeposited on it from a solution containing 0.1 M pyrrole and 0.1 M p-methylbenzene sulfonic acid. The resulting PANI-PPY fiber showed reticulate structure and had large specific surface area. When it was used for the headspace solid-phase microextraction of several esters (i.e. methyl anthranilate, ethyl-o-aminobenzoate, dimethyl phthalate, methyl laurate, and diethyl phthalate), followed by gas chromatographic determination, it presented higher extraction capability in comparison with PPY and PANI coatings. Under the optimized conditions, the linear ranges were 0.07-300 μg L(-1) and the detection limits were 0.05-0.38 μg L(-1) for different esters. The PANI-PPY fiber also showed high durability, after being used for about 160 times its extraction capacity only changed a little. The proposed method was successfully applied to the determination of these esters in real samples and the recoveries were 90-102%. © 2013 Elsevier B.V. All rights reserved.

  14. Oxidation of Peptides by Methyl(trifluoromethyl)dioxirane: the Protecting Group Matters

    PubMed Central

    Rella, Maria Rosaria; Williard, Paul G.

    2011-01-01

    Representative Boc protected and acetyl protected peptide methyl esters bearing alkyl side chains undergo effective oxidation using methyl(trifluoromethyl)dioxirane (1b) under mild conditions. We observe a protecting group dependency in the chemoselectivity displayed by the dioxirane 1b. N-hydroxylation occurs in the case of the Boc protected peptides, side chain hydroxylation takes place in the case of acetyl protected peptides. Both are attractive transformations since they yield derivatized peptides that serve as valuable synthons. PMID:17221970

  15. Interaction of Sodium Hyaluronate with a Biocompatible Cationic Surfactant from Lysine: A Binding Study.

    PubMed

    Bračič, Matej; Hansson, Per; Pérez, Lourdes; Zemljič, Lidija F; Kogej, Ksenija

    2015-11-10

    Mixtures of natural and biodegradable surfactants and ionic polysaccharides have attracted considerable research interest in recent years because they prosper as antimicrobial materials for medical applications. In the present work, interactions between the lysine-derived biocompatible cationic surfactant N(ε)-myristoyl-lysine methyl ester, abbreviated as MKM, and the sodium salt of hyaluronic acid (NaHA) are investigated in aqueous media by potentiometric titrations using the surfactant-sensitive electrode and pyrene-based fluorescence spectroscopy. The critical micelle concentration in pure surfactant solutions and the critical association concentration in the presence of NaHA are determined based on their dependence on the added electrolyte (NaCl) concentration. The equilibrium between the protonated (charged) and deprotonated (neutral) forms of MKM is proposed to explain the anomalous binding isotherms observed in the presence of the polyelectrolyte. The explanation is supported by theoretical model calculations of the mixed-micelle equilibrium and the competitive binding of the two MKM forms to the surface of the electrode membrane. It is suggested that the presence of even small amounts of the deprotonated form can strongly influence the measured electrode response. Such ionic-nonionic surfactant mixtures are a special case of mixed surfactant systems where the amount of the nonionic component cannot be varied independently as was the case for some of the earlier studies.

  16. Arylthioindole inhibitors of tubulin polymerization. 3. Biological evaluation, structure-activity relationships and molecular modeling studies.

    PubMed

    La Regina, Giuseppe; Edler, Michael C; Brancale, Andrea; Kandil, Sahar; Coluccia, Antonio; Piscitelli, Francesco; Hamel, Ernest; De Martino, Gabriella; Matesanz, Ruth; Díaz, José Fernando; Scovassi, Anna Ivana; Prosperi, Ennio; Lavecchia, Antonio; Novellino, Ettore; Artico, Marino; Silvestri, Romano

    2007-06-14

    The new arylthioindole (ATI) derivatives 10, 14-18, and 21-24, which bear a halogen atom or a small size ether group at position 5 of the indole moiety, were compared with the reference compounds colchicine and combretastatin A-4 for biological activity. Derivatives 10, 11, 16, and 21-24 inhibited MCF-7 cell growth with IC50 values <50 nM. A halogen atom (14-17) at position 5 caused a significant reduction in the free energy of binding of compound to tubulin, with a concomitant reduction in cytotoxicity. In contrast, methyl (21) and methoxy (22) substituents at position 5 caused an increase in cytotoxicity. Compound 16, the most potent antitubulin agent, led to a large increase (56%) in HeLa cells in the G2/M phase at 24 h, and at 48 h, 26% of the cells were hyperploid. Molecular modeling studies showed that, despite the absence of the ester moiety present in the previously examined analogues, most of the compounds bind in the colchicine site in the same orientation as the previously studied ATIs. Binding to beta-tubulin involved formation of a hydrogen bond between the indole and Thr179 and positioning of the trimethoxy phenyl group in a hydrophobic pocket near Cys241.

  17. Characterization of a small acyl-CoA-binding protein (ACBP) from Helianthus annuus L. and its binding affinities.

    PubMed

    Aznar-Moreno, Jose A; Venegas-Calerón, Mónica; Du, Zhi-Yan; Garcés, Rafael; Tanner, Julian A; Chye, Mee-Len; Martínez-Force, Enrique; Salas, Joaquín J

    2016-05-01

    Acyl-CoA-binding proteins (ACBPs) bind to acyl-CoA esters and promote their interaction with other proteins, lipids and cell structures. Small class I ACBPs have been identified in different plants, such as Arabidopsis thaliana (AtACBP6), Brassica napus (BnACBP) and Oryza sativa (OsACBP1, OsACBP2, OsACBP3), and they are capable of binding to different acyl-CoA esters and phospholipids. Here we characterize HaACBP6, a class I ACBP expressed in sunflower (Helianthus annuus) tissues, studying the specificity of its corresponding recombinant HaACBP6 protein towards various acyl-CoA esters and phospholipids in vitro, particularly using isothermal titration calorimetry and protein phospholipid binding assays. This protein binds with high affinity to de novo synthetized derivatives palmitoly-CoA, stearoyl-CoA and oleoyl-CoA (Kd 0.29, 0.14 and 0.15 μM respectively). On the contrary, it showed lower affinity towards linoleoyl-CoA (Kd 5.6 μM). Moreover, rHaACBP6 binds to different phosphatidylcholine species (dipalmitoyl-PC, dioleoyl-PC and dilinoleoyl-PC), yet it displays no affinity towards other phospholipids like lyso-PC, phosphatidic acid and lysophosphatidic acid derivatives. In the light of these results, the possible involvement of this protein in sunflower oil synthesis is considered. Copyright © 2016 Elsevier Masson SAS. All rights reserved.

  18. Computational Modeling Approach in Probing the Effects of Cytosine Methylation on the Transcription Factor Binding to DNA.

    PubMed

    Tenayuca, John; Cousins, Kimberley; Yang, Shumei; Zhang, Lubo

    2017-01-01

    Cytosine methylation at CpG dinucleotides is a chief mechanism in epigenetic modification of gene expression patterns. Previous studies demonstrated that increased CpG methylation of Sp1 sites at -268 and -346 of protein kinase C ε promoter repressed the gene expression. The present study investigated the impact of CpG methylation on the Sp1 binding via molecular modeling and electrophoretic mobility shift assay. Each of the Sp1 sites contain two CpGs. Methylation of either CpG lowered the binding affinity of Sp1, whereas methylation of both CpGs produced a greater decrease in the binding affinity. Computation of van der Waals (VDW) energy of Sp1 in complex with the Sp1 sites demonstrated increased VDW values from one to two sites of CpG methylation. Molecular modeling indicated that single CpG methylation caused underwinding of the DNA fragment, with the phosphate groups at C1, C4 and C5 reoriented from their original positions. Methylation of both CpGs pinched the minor groove and increased the helical twist concomitant with a shallow, hydrophobic major groove. Additionally, double methylation eliminated hydrogen bonds on recognition helix residues located at positions -1 and 1, which were essential for interaction with O6/N7 of G-bases. Bonding from linker residues Arg565, Lys595 and Lys596 were also reduced. Methylation of single or both CpGs significantly affected hydrogen bonding from all three Sp1 DNA binding domains, demonstrating that the consequences of cytosine modification extend beyond the neighboring nucleotides. The results indicate that cytosine methylation causes subtle structural alterations in Sp1 binding sites consequently resulting in inhibition of side chain interactions critical for specific base recognition and reduction of the binding affinity of Sp1. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

  19. Application of AlkBGT and AlkL from Pseudomonas putida GPo1 for Selective Alkyl Ester ω-Oxyfunctionalization in Escherichia coli

    PubMed Central

    Eggink, Gerrit; Weusthuis, Ruud A.

    2016-01-01

    ABSTRACT The enzyme system AlkBGT from Pseudomonas putida GPo1 can efficiently ω-functionalize fatty acid methyl esters. Outer membrane protein AlkL boosts this ω-functionalization. In this report, it is shown that whole cells of Escherichia coli expressing the AlkBGT system can also ω-oxidize ethyl nonanoate (NAEE). Coexpression of AlkBGT and AlkL resulted in 1.7-fold-higher ω-oxidation activity on NAEE. With this strain, initial activity on NAEE was 70 U/g (dry weight) of cells (gcdw), 67% of the initial activity on methyl nonanoate. In time-lapse conversions with 5 mM NAEE the main product was 9-hydroxy NAEE (3.6 mM), but also 9-oxo NAEE (0.1 mM) and 9-carboxy NAEE (0.6 mM) were formed. AlkBGT also ω-oxidized ethyl, propyl, and butyl esters of fatty acids ranging from C6 to C10. Increasing the length of the alkyl chain improved the ω-oxidation activity of AlkBGT on esters of C6 and C7 fatty acids. From these esters, application of butyl hexanoate resulted in the highest ω-oxidation activity, 82 U/gcdw. Coexpression of AlkL only had a positive effect on ω-functionalization of substrates with a total length of C11 or longer. These findings indicate that AlkBGT(L) can be applied as a biocatalyst for ω-functionalization of ethyl, propyl, and butyl esters of medium-chain fatty acids. IMPORTANCE Fatty acid esters are promising renewable starting materials for the production of ω-hydroxy fatty acid esters (ω-HFAEs). ω-HFAEs can be used to produce sustainable polymers. Chemical conversion of the fatty acid esters to ω-HFAEs is challenging, as it generates by-products and needs harsh reaction conditions. Biocatalytic production is a promising alternative. In this study, biocatalytic conversion of fatty acid esters toward ω-HFAEs was investigated using whole cells. This was achieved with recombinant Escherichia coli cells that produce the AlkBGT enzymes. These enzymes can produce ω-HFAEs from a wide variety of fatty acid esters. Medium-chain-length acids (C6 to C10) esterified with ethanol, propanol, or butanol were applied. This is a promising production platform for polymer building blocks that uses renewable substrates and mild reaction conditions. PMID:27084021

  20. Fully convergent chemical synthesis of ester insulin: determination of the high resolution X-ray structure by racemic protein crystallography.

    PubMed

    Avital-Shmilovici, Michal; Mandal, Kalyaneswar; Gates, Zachary P; Phillips, Nelson B; Weiss, Michael A; Kent, Stephen B H

    2013-02-27

    Efficient total synthesis of insulin is important to enable the application of medicinal chemistry to the optimization of the properties of this important protein molecule. Recently we described "ester insulin"--a novel form of insulin in which the function of the 35 residue C-peptide of proinsulin is replaced by a single covalent bond--as a key intermediate for the efficient total synthesis of insulin. Here we describe a fully convergent synthetic route to the ester insulin molecule from three unprotected peptide segments of approximately equal size. The synthetic ester insulin polypeptide chain folded much more rapidly than proinsulin, and at physiological pH. Both the D-protein and L-protein enantiomers of monomeric DKP ester insulin (i.e., [Asp(B10), Lys(B28), Pro(B29)]ester insulin) were prepared by total chemical synthesis. The atomic structure of the synthetic ester insulin molecule was determined by racemic protein X-ray crystallography to a resolution of 1.6 Å. Diffraction quality crystals were readily obtained from the racemic mixture of {D-DKP ester insulin + L-DKP ester insulin}, whereas crystals were not obtained from the L-ester insulin alone even after extensive trials. Both the D-protein and L-protein enantiomers of monomeric DKP ester insulin were assayed for receptor binding and in diabetic rats, before and after conversion by saponification to the corresponding DKP insulin enantiomers. L-DKP ester insulin bound weakly to the insulin receptor, while synthetic L-DKP insulin derived from the L-DKP ester insulin intermediate was fully active in binding to the insulin receptor. The D- and L-DKP ester insulins and D-DKP insulin were inactive in lowering blood glucose in diabetic rats, while synthetic L-DKP insulin was fully active in this biological assay. The structural basis of the lack of biological activity of ester insulin is discussed.

  1. Fully Convergent Chemical Synthesis of Ester Insulin: Determination of the High Resolution X-ray Structure by Racemic Protein Crystallography

    PubMed Central

    Avital-Shmilovici, Michal; Mandal, Kalyaneswar; Gates, Zachary P.; Phillips, Nelson B.; Weiss, Michael A.; Kent, Stephen B.H.

    2013-01-01

    Efficient total synthesis of insulin is important to enable the application of medicinal chemistry to the optimization of the properties of this important protein molecule. Recently we described ‘ester insulin’ – a novel form of insulin in which the function of the 35 residue C-peptide of proinsulin is replaced by a single covalent bond – as a key intermediate for the efficient total synthesis of insulin. Here we describe a fully convergent synthetic route to the ester insulin molecule from three unprotected peptide segments of approximately equal size. The synthetic ester insulin polypeptide chain folded much more rapidly than proinsulin, and at physiological pH. Both the D-protein and L-protein enantiomers of monomeric DKP ester insulin (i.e. [AspB10, LysB28, ProB29]ester insulin) were prepared by total chemical synthesis. The atomic structure of the synthetic ester insulin molecule was determined by racemic protein X-ray crystallography to a resolution of 1.6 Å. Diffraction quality crystals were readily obtained from the racemic mixture of {D-DKP ester insulin + L-DKP ester insulin}, whereas crystals were not obtained from the L-ester insulin alone even after extensive trials. Both the D-protein and L-protein enantiomers of monomeric DKP ester insulin were assayed for receptor binding and in diabetic rats, before and after conversion by saponification to the corresponding DKP insulin enantiomers. L-DKP ester insulin bound weakly to the insulin receptor, while synthetic L-DKP insulin derived from the L-DKP ester insulin intermediate was fully active in binding to the insulin receptor. The D- and L-DKP ester insulins and D-DKP insulin were inactive in lowering blood glucose in diabetic rats, while synthetic L-DKP insulin was fully active in this biological assay. The structural basis of the lack of biological activity of ester insulin is discussed. PMID:23343390

  2. Production of Biodiesel Using a Membrane Reactor to Minimize Separation Cost

    NASA Astrophysics Data System (ADS)

    Olagunju, O. A.; Musonge, P.

    2017-07-01

    This study investigates the performance of a packed bed membrane reactor in the transesterification process of triglycerides to methyl ester using soyabean oil as feedstock. A TiO2/Al2O3 ceramic microporous membrane was selected due to its chemical inert nature and thermal stability to selectively remove the product from the reaction medium. CaO impregnated on the surface of activated carbon was packed into the membrane and acted as catalyst. The synthesized catalyst had a total loading of 40.50 % and was characterized by XRD and temperature-programmed desorption of CO2 (CO2-TPD). The crude biodiesel produced was micro-filtered by the ceramic membrane with a pore size of 0.02 μm to retain the unreacted oil and free glycerol, at the transmembrane pressure of 100 KPa. The best condition was achieved with a temperature of 65 °C, methanol/oil molar ratio of 6:1 for 150 minutes, which resulted in the highest FAME yield of 94 %. Methyl ester produced met the ASTM D6751 and SANS 1935 specifications. The product obtained was mainly composed of methyl esters. Glycerol was not detected in the product stream due to the ability of the membrane to retain the glycerol and the unreacted oil in the medium, which solved the issue of glycerol separation from biodiesel.

  3. The surface chemistry of nanocrystalline MgO catalysts for FAME production: An in situ XPS study of H2O, CH3OH and CH3OAc adsorption

    NASA Astrophysics Data System (ADS)

    Montero, J. M.; Isaacs, M. A.; Lee, A. F.; Lynam, J. M.; Wilson, K.

    2016-04-01

    An in situ XPS study of water, methanol and methyl acetate adsorption over as-synthesised and calcined MgO nanocatalysts is reported with a view to gaining insight into the surface adsorption of key components relevant to fatty acid methyl esters (biodiesel) production during the transesterification of triglycerides with methanol. High temperature calcined NanoMgO-700 adsorbed all three species more readily than the parent material due to the higher density of electron-rich (111) and (110) facets exposed over the larger crystallites. Water and methanol chemisorb over the NanoMgO-700 through the conversion of surface O2 - sites to OH- and coincident creation of Mg-OH or Mg-OCH3 moieties respectively. A model is proposed in which the dissociative chemisorption of methanol occurs preferentially over defect and edge sites of NanoMgO-700, with higher methanol coverages resulting in physisorption over weakly basic (100) facets. Methyl acetate undergoes more complex surface chemistry over NanoMgO-700, with C-H dissociation and ester cleavage forming surface hydroxyl and acetate species even at extremely low coverages, indicative of preferential adsorption at defects. Comparison of C 1s spectra with spent catalysts from tributyrin transesterification suggest that ester hydrolysis plays a key factor in the deactivation of MgO catalysts for biodiesel production.

  4. Constituents of Mediterranean Spices Counteracting Vascular Smooth Muscle Cell Proliferation: Identification and Characterization of Rosmarinic Acid Methyl Ester as a Novel Inhibitor.

    PubMed

    Liu, Rongxia; Heiss, Elke H; Waltenberger, Birgit; Blažević, Tina; Schachner, Daniel; Jiang, Baohong; Krystof, Vladimir; Liu, Wanhui; Schwaiger, Stefan; Peña-Rodríguez, Luis M; Breuss, Johannes M; Stuppner, Hermann; Dirsch, Verena M; Atanasov, Atanas G

    2018-04-01

    Aberrant vascular smooth muscle cell (VSMC) proliferation is involved in atherosclerotic plaque formation and restenosis. Mediterranean spices have been reported to confer cardioprotection, but their direct influence on VSMCs has largely not been investigated. This study aims at examining rosmarinic acid (RA) and 11 related constituents for inhibition of VSMC proliferation in vitro, and at characterizing the most promising compound for their mode of action and influence on neointima formation in vivo. RA, rosmarinic acid methyl ester (RAME), and caffeic acid methyl ester inhibit VSMC proliferation in a resazurin conversion assay with IC 50 s of 5.79, 3.12, and 6.78 µm, respectively. RAME significantly reduced neointima formation in vivo in a mouse femoral artery cuff model. Accordingly, RAME leads to an accumulation of VSMCs in the G 0 /G 1 cell-cycle phase, as indicated by blunted retinoblastoma protein phosphorylation upon mitogen stimulation and inhibition of cyclin-dependent kinase 2 in vitro. RAME represses PDGF-induced VSMC proliferation in vitro and reduces neointima formation in vivo. These results recommend RAME as an interesting compound with VSMC-inhibiting potential. Future metabolism and pharmacokinetics studies might help to further evaluate the potential relevance of RAME and other spice-derived polyphenolics for vasoprotection. © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  5. Structure and Rotational Dynamics of Isoamyl Acetate and Methyl Propionate Studied by Microwave Spectroscopy

    NASA Astrophysics Data System (ADS)

    Stahl, W.; Nguyen, H. V. L.; Sutikdja, L. W.; Jelisavac, D.; Mouhib, H.; Kleiner, I.

    2012-06-01

    The microwave spectra of a number of organic aliphatic esters have been recorded for the first time in the 3-26.5 GHz frequency range, using the molecular beam Fourier-transform microwave (MB-FTMW) spectrometer in Aachen, with an instrumental uncertainty of a few kHz for unblended lines. The combined use of ab initio quantum chemical calculations and spectral analysis allowed us to determine the spectroscopic parameters and potential barriers to internal rotation of the methyl groups for the lowest energy conformers. We will compare here the results from ab initio calculations and from two different hamiltonian methods (the XIAM and BELGI codes) for isoamyl acetate H3C-COO-(CH2)2-CH(CH3)2, an one-top internal rotor molecule with a C1 symmetry and for methyl propionate CH3CH2COOCH3 containing two inequivalent methyl tops (C3v), with different barrier heights. This study is part of a larger project which aims at determining the structures of the lowest energy conformers for a serie of organic esters and ketones which are of interest for flavour or perfume applications.

  6. CpG methylation increases the DNA binding of 9-aminoacridine carboxamide Pt analogues.

    PubMed

    Kava, Hieronimus W; Murray, Vincent

    2016-10-01

    This study investigated the effect of CpG methylation on the DNA binding of cisplatin analogues with an attached aminoacridine intercalator. DNA-targeted 9-aminoacridine carboxamide Pt complexes are known to bind at 5'-CpG sequences. Their binding to methylated and non-methylated 5'-CpG sequences was determined and compared with cisplatin. The damage profiles of each platinum compound were quantified via a polymerase stop assay with fluorescently labelled primers and capillary electrophoresis. Methylation at 5'-CpG was shown to significantly increase the binding intensity for the 9-aminoacridine carboxamide compounds, whereas no significant increase was found for cisplatin. 5'-CpG methylation had the largest effect on the 9-ethanolamine-acridine carboxamide Pt complex, followed by the 9-aminoacridine carboxamide Pt complex and the 7-fluoro complex. The methylation state of a cell's genome is important in maintaining normal gene expression, and is often aberrantly altered in cancer cells. An analogue of cisplatin which differentially targets methylated DNA may be able to improve its therapeutic activity, or alter its range of targets and evade the chemoresistance which hampers cisplatin efficacy in clinical use. Copyright © 2016 Elsevier Ltd. All rights reserved.

  7. ApoA-II modulates the association of HDL with class B scavenger receptors SR-BI and CD36.

    PubMed

    de Beer, Maria C; Castellani, Lawrence W; Cai, Lei; Stromberg, Arnold J; de Beer, Frederick C; van der Westhuyzen, Deneys R

    2004-04-01

    The class B scavenger receptors SR-BI and CD36 exhibit a broad ligand binding specificity. SR-BI is well characterized as a HDL receptor that mediates selective cholesteryl ester uptake from HDL. CD36, a receptor for oxidized LDL, also binds HDL and mediates selective cholesteryl ester uptake, although much less efficiently than SR-BI. Apolipoprotein A-II (apoA-II), the second most abundant HDL protein, is considered to be proatherogenic, but the underlying mechanisms are unclear. We previously showed that apoA-II modulates SR-BI-dependent binding and selective uptake of cholesteryl ester from reconstituted HDL. To investigate the effect of apoA-II in naturally occurring HDL on these processes, we compared HDL without apoA-II (from apoA-II null mice) with HDLs containing differing amounts of apoA-II (from C57BL/6 mice and transgenic mice expressing a mouse apoA-II transgene). The level of apoA-II in HDL was inversely correlated with HDL binding and selective cholesteryl ester uptake by both scavenger receptors, particularly CD36. Interestingly, for HDL lacking apoA-II, the efficiency with which CD36 mediated selective uptake reached a level similar to that of SR-BI. These results demonstrate that apoA-II exerts a marked effect on HDL binding and selective lipid uptake by the class B scavenger receptors and establishes a potentially important relationship between apoA-II and CD36.

  8. Effect of Ion Binding in Palmitoyl-Oleoyl Phosphatidylserine Monolayers

    NASA Astrophysics Data System (ADS)

    Eckler, Matthew; Matysiak, Silvina

    2013-03-01

    Molecular dynamics simulations of palmitoyl-oleoyl phosphatidylserine (POPS) monolayers at the air-water interface were performed with different ionic strengths with the aim of determining the specific organization and dynamics of counterion binding events. Na + ions penetrated the monolayers into both the ester carbonyl and carboxylate regions of the phospholipids. The binding events increase with the addition of salt. Differences in lipid order parameter, headgroup orientation, and prevalence of inter- and intramolecular hydrogen bonding events between the amine group of the lipid and oxygen groups are observed depending on whether the Na + is binding near the carboxylate or ester region of the lipid. The observed changes are explained in terms of the salting-out effect.

  9. Lipids of the Tail Gland, Body and Muzzle Fur of the Red Fox, Vulpes vulpes.

    PubMed

    McLean, Stuart; Davies, Noel W; Nichols, David S

    2017-07-01

    The tail gland of the red fox (Vulpes vulpes) secretes lipids containing volatile terpenes used in social communication. We have analysed lipids extracted from fur of the tail gland, body (flanks) and muzzle of foxes. GC-MS showed a novel group of iso-valerate and tiglate monoesters of alkane-1,2-diols (C18:0-22:0). There was also a larger group of Type II diesters in which a second, longer chain, fatty acid (FA) was attached to the free alcohol group. LC-MS showed the full range of diol diesters, mostly C36:0-50:0, with smaller amounts of the corresponding mono-unsaturated tiglate esters. An additional group of diesters with higher MW (C49:0-62:0) containing two long-chain FA was present in the lipids of body and muzzle fur. After saponification and GC-MS, 98 fatty acids were characterized as their methyl esters. Apart from the C5 FA, most were saturated n-, iso-, anteiso- or other methyl-branched FA (C12:0-28:0) whose structures were determined by a combination of their mass spectra and Kovats retention indices. Several FA have not previously been found in nature or in vertebrates. Thirty-four alkane-1,2-diols were found as their TMS derivatives, mostly n-, iso- or anteiso-isomers of C16:0-25:0. The tail gland had the greatest amount of wax esters, from a greater variety of FA and diols, but lacked the esters with two long-chain FA. These findings show that fox skin lipids comprise mono- and di-esters of alkane-1,2-diols, and exhibit enormous complexity due to the diversity of their constituent FA, diols and the many possible isomers of their esters.

  10. Ternary borate-nucleoside complex stabilization by Ribonuclease A demonstrates phosphate mimicry

    PubMed Central

    Gabel, Scott A.; London, Robert E.

    2010-01-01

    Phosphate esters play a central role in cellular energetics, biochemical activation, signal transduction and conformational switching. The structural homology of the borate anion with phosphate, combined with its ability to spontaneously esterify hydroxyl groups, suggested that phosphate-ester recognition sites on proteins might exhibit significant affinity for non-enzymatically formed borate esters. 11B NMR studies and activity measurements on ribonuclease A in the presence of borate and several cytidine analogs demonstrate the formation of a stable ternary RNase A•3′-deoxycytidine-2′-borate ternary complex that mimics the complex formed between RNase A and a 2′-cytidine monophosphate (2′-CMP) inhibitor. Alternatively, no slowly exchanging borate resonance is observed for a ternary RNase A, borate, 2′-deoxycytidine mixture, demonstrating the critical importance of the 2′-hydroxyl group for complex formation. Titration of the ternary complex with 2′-CMP shows that it can displace the bound borate ester with a binding constant that is close to the reported inhibition constant of RNase A by 2′CMP. RNase A binding of a cyclic cytidine-2′,3′-borate ester, which is a structural homolog of the cytidine-2′,3′-cyclic phosphate substrate, could also be demonstrated. The apparent dissociation constant for the cytidine-2′,3′-borate•RNase A complex is 0.8 mM, which compares with a Michaelis constant of 11 mM for cCMP at pH 7, indicating considerably stronger binding. However, the value is 1000-fold larger than the reported dissociation constant of the RNase A complex with uridine-vanadate. These results are consistent with recent reports suggesting that in situ formation of borate esters that mimic the corresponding phosphate esters support enzyme catalysis. PMID:17957392

  11. HDL surface lipids mediate CETP binding as revealed by electron microscopy and molecular dynamics simulation

    PubMed Central

    Zhang, Meng; Charles, River; Tong, Huimin; Zhang, Lei; Patel, Mili; Wang, Francis; Rames, Matthew J.; Ren, Amy; Rye, Kerry-Anne; Qiu, Xiayang; Johns, Douglas G.; Charles, M. Arthur; Ren, Gang

    2015-01-01

    Cholesteryl ester transfer protein (CETP) mediates the transfer of cholesterol esters (CE) from atheroprotective high-density lipoproteins (HDL) to atherogenic low-density lipoproteins (LDL). CETP inhibition has been regarded as a promising strategy for increasing HDL levels and subsequently reducing the risk of cardiovascular diseases (CVD). Although the crystal structure of CETP is known, little is known regarding how CETP binds to HDL. Here, we investigated how various HDL-like particles interact with CETP by electron microscopy and molecular dynamics simulations. Results showed that CETP binds to HDL via hydrophobic interactions rather than protein-protein interactions. The HDL surface lipid curvature generates a hydrophobic environment, leading to CETP hydrophobic distal end interaction. This interaction is independent of other HDL components, such as apolipoproteins, cholesteryl esters and triglycerides. Thus, disrupting these hydrophobic interactions could be a new therapeutic strategy for attenuating the interaction of CETP with HDL. PMID:25737239

  12. HDL surface lipids mediate CETP binding as revealed by electron microscopy and molecular dynamics simulation

    DOE PAGES

    Zhang, Meng; Charles, River; Tong, Huimin; ...

    2015-03-04

    Cholesteryl ester transfer protein (CETP) mediates the transfer of cholesterol esters (CE) from atheroprotective high-density lipoproteins (HDL) to atherogenic low-density lipoproteins (LDL). CETP inhibition has been regarded as a promising strategy for increasing HDL levels and subsequently reducing the risk of cardiovascular diseases (CVD). Although the crystal structure of CETP is known, little is known regarding how CETP binds to HDL. Here, we investigated how various HDL-like particles interact with CETP by electron microscopy and molecular dynamics simulations. Results showed that CETP binds to HDL via hydrophobic interactions rather than protein-protein interactions. The HDL surface lipid curvature generates a hydrophobicmore » environment, leading to CETP hydrophobic distal end interaction. This interaction is independent of other HDL components, such as apolipoproteins, cholesteryl esters and triglycerides. Thus, disrupting these hydrophobic interactions could be a new therapeutic strategy for attenuating the interaction of CETP with HDL.« less

  13. HDL surface lipids mediate CETP binding as revealed by electron microscopy and molecular dynamics simulation

    NASA Astrophysics Data System (ADS)

    Zhang, Meng; Charles, River; Tong, Huimin; Zhang, Lei; Patel, Mili; Wang, Francis; Rames, Matthew J.; Ren, Amy; Rye, Kerry-Anne; Qiu, Xiayang; Johns, Douglas G.; Charles, M. Arthur; Ren, Gang

    2015-03-01

    Cholesteryl ester transfer protein (CETP) mediates the transfer of cholesterol esters (CE) from atheroprotective high-density lipoproteins (HDL) to atherogenic low-density lipoproteins (LDL). CETP inhibition has been regarded as a promising strategy for increasing HDL levels and subsequently reducing the risk of cardiovascular diseases (CVD). Although the crystal structure of CETP is known, little is known regarding how CETP binds to HDL. Here, we investigated how various HDL-like particles interact with CETP by electron microscopy and molecular dynamics simulations. Results showed that CETP binds to HDL via hydrophobic interactions rather than protein-protein interactions. The HDL surface lipid curvature generates a hydrophobic environment, leading to CETP hydrophobic distal end interaction. This interaction is independent of other HDL components, such as apolipoproteins, cholesteryl esters and triglycerides. Thus, disrupting these hydrophobic interactions could be a new therapeutic strategy for attenuating the interaction of CETP with HDL.

  14. Hydrocarbon emission fingerprints from contemporary vehicle/engine technologies with conventional and new fuels

    NASA Astrophysics Data System (ADS)

    Montero, Larisse; Duane, Matthew; Manfredi, Urbano; Astorga, Covadonga; Martini, Giorgio; Carriero, Massimo; Krasenbrink, Alois; Larsen, B. R.

    2010-06-01

    The present paper presents results from the analysis of 29 individual C 2-C 9 hydrocarbons (HCs) specified in the European Commission Ozone Directive. The 29 HCs are measured in exhaust from common, contemporary vehicle/engine/fuel technologies for which very little or no data is available in the literature. The obtained HC emission fingerprints are compared with fingerprints deriving from technologies that are being phased out in Europe. Based on the total of 138 emission tests, thirteen type-specific fingerprints are extracted (Mean ± SD percentage contributions from individual HCs to the total mass of the 29 HCs), essential for receptor modelling source apportionment. The different types represent exhaust from Euro3 and Euro4 light-duty (LD) diesel and petrol-vehicles, Euro3 heavy-duty (HD) diesel exhaust, and exhaust from 2-stroke preEuro, Euro1 and Euro2 mopeds. The fuels comprise liquefied petroleum gas, petrol/ethanol blends (0-85% ethanol), and mineral diesel in various blends (0-100%) with fatty acid methyl esters, rapeseed methyl esters palm oil methyl esters, soybean oil methyl or sunflower oil methyl esters. Type-specific tracer compounds (markers) are identified for the various vehicle/engine/fuel technologies. An important finding is an insignificant effect on the HC fingerprints of varying the test driving cycle, indicating that combining HC fingerprints from different emission studies for receptor modelling purposes would be a robust approach. The obtained results are discussed in the context of atmospheric ozone formation and health implications from emissions (mg km -1 for LD and mopeds and mg kW h -1 for HD, all normalised to fuel consumption: mg dm -3 fuel) of the harmful HCs, benzene and 1,3-butadiene. Another important finding is a strong linear correlation of the regulated "total" hydrocarbon emissions (tot-HC) with the ozone formation potential of the 29 HCs (ΣPO 3 = (1.66 ± 0.04) × tot-RH; r2 = 0.93). Tot-HC is routinely monitored in emission control laboratories, whereas C 2-C 9 are not. The revealed strong correlations broadens the usability of data from vehicle emission control laboratories and facilitates the comparison of the ozone formation potential of HCs in exhaust from of old and new vehicle/engine/fuel technologies.

  15. Synthesis and biological evaluation of amino acid methyl ester conjugates of 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid against the production of nitric oxide (NO).

    PubMed

    Onyango, Evans O; Fu, Liangfeng; Cao, Martine; Liby, Karen T; Sporn, Michael B; Gribble, Gordon W

    2014-01-15

    2-Cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid (CDDO, 2) was condensed with various amino acid methyl esters at the C-28 carboxylic acid. The new amide conjugates were evaluated for their inhibition of nitric oxide (NO) production in RAW264.7 cells stimulated with interferon-γ (IFNγ). Of these new compounds, CDDO conjugates with alanine, valine, and serine are nearly equipotent to CDDO-ethyl amide (4), a triterpenoid with promising biological activity in numerous disease models. Some of these conjugates also induce the in vitro expression of heme oxygenase-1, and inhibit the proliferation of Panc-1343 pancreatic cells. Copyright © 2013 Elsevier Ltd. All rights reserved.

  16. Amonia gas: an improved reagent for chemical ionization mass spectrometry of bile acid methyl ester acetates

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    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 thesemore » studies for the detection and quantitation of bile acids is discussed. 2 tables.« less

  17. Facile and High-Yielding Synthesis of TAM Biradicals and Monofunctional TAM Radicals.

    PubMed

    Trukhin, Dmitry V; Rogozhnikova, Olga Yu; Troitskaya, Tatiana I; Vasiliev, Vladimir G; Bowman, Michael K; Tormyshev, Victor M

    2016-04-01

    Facile and high-yielding procedures for synthesis of monocarboxylic acid derivatives of triarylmethyl radicals (TAMs) were developed. Reaction of methyl thioglycolate with tris(2,3,5,6-tetrathiaaryl)methyl cation smoothly afforded the monosubstituted TAM derivative, which was hydrolyzed to a monocarboxylic acid, with the TAM moiety attached to thioglycolic acid via the sulfur atom. Alternatively, the diamagnetic tricarboxylic acid precursor of Finland trityl was transformed to a trimethyl ester and partially hydrolyzed under controlled conditions. The diester product was isolated and the remaining fractions were converted back to the trimethyl ester for production of more diester. The first representatives of TAM biradicals with different TAM cores and interspin distances were obtained by reaction of these new TAM monocaboxylic acids with N,N'-dimethylethylenediamine.

  18. Expanding the chemical diversity of natural esters by engineering a polyketide-derived pathway into Escherichia coli.

    PubMed

    Menendez-Bravo, Simón; Comba, Santiago; Sabatini, Martín; Arabolaza, Ana; Gramajo, Hugo

    2014-07-01

    Microbial fatty acid (FA)-derived molecules have emerged as promising alternatives to petroleum-based chemicals for reducing dependence on fossil hydrocarbons. However, native FA biosynthetic pathways often yield limited structural diversity, and therefore restricted physicochemical properties, of the end products by providing only a limited variety of usually linear hydrocarbons. Here we have engineered into Escherichia coli a mycocerosic polyketide synthase-based biosynthetic pathway from Mycobacterium tuberculosis and redefined its biological role towards the production of multi-methyl-branched-esters (MBEs) with novel chemical structures. Expression of FadD28, Mas and PapA5 enzymes enabled the biosynthesis of multi-methyl-branched-FA and their further esterification to an alcohol. The high substrate tolerance of these enzymes towards different FA and alcohol moieties resulted in the biosynthesis of a broad range of MBE. Further metabolic engineering of the MBE producer strain coupled this system to long-chain-alcohol biosynthetic pathways resulting in de novo production of branched wax esters following addition of only propionate. Copyright © 2014 International Metabolic Engineering Society. Published by Elsevier Inc. All rights reserved.

  19. Aroma Volatile Compounds from Two Fresh Pineapple Varieties in China

    PubMed Central

    Zheng, Liang-Yong; Sun, Guang-Ming; Liu, Yu-Ge; Lv, Ling-Ling; Yang, Wen-Xiu; Zhao, Wei-Feng; Wei, Chang-Bin

    2012-01-01

    Volatile compounds from two pineapples varieties (Tainong No.4 and No.6) were isolated by headspace solid phase microextraction (HS-SPME) and identified and quantified by gas chromatography-mass spectrometry (GC/MS). In the Tainong No. 4 and No. 6 pineapples, a total of 11 and 28 volatile compounds were identified according to their retention time on capillary columns and their mass spectra, and quantified with total concentrations of 1080.44 μg·kg−1 and 380.66 μg·kg−1 in the Tainong No.4 and No. 6 pineapples, respectively. The odor active values (OAVs) of volatile compounds from pineapples were also calculated. According to the OAVs, four compounds were defined as the characteristic aroma compounds for the Tainong No. 4 pineapple, including furaneol, 3-(methylthio)propanoic acid methyl ester, 3-(methylthio)propanoic acid ethyl ester and δ-octalactone. The OAVs of five compounds including ethyl-2-methylbutyrate, methyl-2-methylbutyrate, 3-(methylthio)propanoic acid ethyl ester, ethyl hexanoate and decanal were considered to be the characteristic aroma compounds for the Tainong No. 6 pineapple. PMID:22837701

  20. Arginine methylation of translocated in liposarcoma (TLS) inhibits its binding to long noncoding RNA, abrogating TLS-mediated repression of CBP/p300 activity.

    PubMed

    Cui, Wei; Yoneda, Ryoma; Ueda, Naomi; Kurokawa, Riki

    2018-05-21

    Translocated in liposarcoma (TLS) is an RNA-binding protein and a transcription-regulatory sensor of DNA damage. TLS binds promoter-associated noncoding RNA (pncRNA) and inhibits histone acetyltransferase (HAT) activity of CREB-binding protein (CBP)/E1A-binding protein P300 (p300) on the cyclin D1 (CCND1) gene. Although post-translational modifications of TLS, such as arginine methylation, are known to regulate TLS's nucleocytoplasmic shuttling and assembly in stress granules, its interactions with RNAs remain poorly characterized. Herein, using various biochemical assays, we confirmed the earlier observations that TLS is methylated by protein arginine methyltransferase 1 (PRMT1) in vitro. The arginine methylation of TLS disrupted binding to pncRNA and also prevented binding of TLS to and inhibition of CBP/p300. This result indicated that arginine methylation of TLS abrogates both binding to pncRNA and TLS-mediated inhibition of CBP/p300 HAT activities. We also report that an arginine residue within the Arg-Gly-Gly domain of TLS, Arg-476, serves as the major determinant for binding to pncRNA. Either methylation or mutation of Arg-476 of TLS significantly decreased pncRNA binding and thereby prevented a pncRNA-induced allosteric alteration in TLS that is required for its interaction with CBP/p300. Moreover, unlike wildtype TLS, an R476A TLS mutant did not inhibit CCND1 promoter activity in luciferase reporter assays. Taken together, we propose the hypothesis that arginine methylation of TLS regulates both TLS-nucleic acid and TLS-protein interactions and thereby participates in transcriptional regulation. Published under license by The American Society for Biochemistry and Molecular Biology, Inc.

  1. Genome-wide DNA methylation measurements in prostate tissues uncovers novel prostate cancer diagnostic biomarkers and transcription factor binding patterns.

    PubMed

    Kirby, Marie K; Ramaker, Ryne C; Roberts, Brian S; Lasseigne, Brittany N; Gunther, David S; Burwell, Todd C; Davis, Nicholas S; Gulzar, Zulfiqar G; Absher, Devin M; Cooper, Sara J; Brooks, James D; Myers, Richard M

    2017-04-17

    Current diagnostic tools for prostate cancer lack specificity and sensitivity for detecting very early lesions. DNA methylation is a stable genomic modification that is detectable in peripheral patient fluids such as urine and blood plasma that could serve as a non-invasive diagnostic biomarker for prostate cancer. We measured genome-wide DNA methylation patterns in 73 clinically annotated fresh-frozen prostate cancers and 63 benign-adjacent prostate tissues using the Illumina Infinium HumanMethylation450 BeadChip array. We overlaid the most significantly differentially methylated sites in the genome with transcription factor binding sites measured by the Encyclopedia of DNA Elements consortium. We used logistic regression and receiver operating characteristic curves to assess the performance of candidate diagnostic models. We identified methylation patterns that have a high predictive power for distinguishing malignant prostate tissue from benign-adjacent prostate tissue, and these methylation signatures were validated using data from The Cancer Genome Atlas Project. Furthermore, by overlaying ENCODE transcription factor binding data, we observed an enrichment of enhancer of zeste homolog 2 binding in gene regulatory regions with higher DNA methylation in malignant prostate tissues. DNA methylation patterns are greatly altered in prostate cancer tissue in comparison to benign-adjacent tissue. We have discovered patterns of DNA methylation marks that can distinguish prostate cancers with high specificity and sensitivity in multiple patient tissue cohorts, and we have identified transcription factors binding in these differentially methylated regions that may play important roles in prostate cancer development.

  2. Absorption of CO2 from modified flue gases of power generation Tarahan chemically using NaOH and Na2CO3 and biologically using microalgae

    NASA Astrophysics Data System (ADS)

    Purba, Elida; Agustina, Dewi; Putri Pertama, Finka; Senja, Fita

    2018-03-01

    This research was carried out on the absorption of CO2 from the modified flue gases of power generation Tarahan using NaOH (sodium hydroxide) and Na2CO3 (sodium carbonate). The operation was conducted in a packed column absorber and then the output gases from the packed column was fed into photo-bioreactor for biological absorption. In the photo-bioreactor, two species of microalgae, N. occulata and T. chuii, were cultivated to both absorb CO2 gas and to produce biomass for algal oil. The aims of this research were, first, to determine the effect of absorbent flow rate on the reduction of CO2 and on the decrease of output gas temperature, second, to determine the characteristics of methyl ester obtained from biological absorption process. Flow rates of the absorbent were varied as 1, 2, and 3 l/min. The concentrations of NaOH and Na2CO3 were 1 M at a constant gas flow rate of 6 l/min. The output concentrations of CO2 from the absorber was analyzed using Gas Chromatography 2014-AT SHIMADZU Corp 08128. The results show that both of the absorbents give different trends. From the absorption using NaOH, it can be concluded that the higher the flow rate, the higher the absorption rate obtained. The highest flow rate achieved maximum absorption of 100%. On the other hand, absorption with Na2CO3 revealed the opposite trend where the higher the flow rates the lower the absorption rate. The highest absorption using Na2CO3 was obtained with the lowest flow rate, 1 l/min, that was 45,5%. As the effect of flow rate on output gas temperature, the temperature decreased with increasing flow rates for both absorbents. The output gas temperature for NaOH and Na2CO3 were consecutively 35 °C and 31 °C with inlet gas temperature of 50°C. Absorption of CO2 biologically resulted a reduction of CO2 up to 60% from the input gas concentration. Algal oil was extracted with mixed hexane and chloroform to obtain algal oil. Extracted oil was transesterified to methyl ester using sodium hydroxide as a catalyst. The results of in-situ transesterification method cannot be identified. Both microalgae achieved maximum yield at 2% catalyst concentration. Nannochloropsis occulata achieved the highest yield of algal oil that is 88.5%. The highest content of methyl ester from Nannochloropsis occulata was undecanoic acid methyl ester by 55.42% and the result from Tetraselmis chuii was palmitic acid methyl ester by 81.58%.

  3. Purification and Characterization of Phosphonoglycans from Glycomyces sp. Strain NRRL B-16210 and Stackebrandtia nassauensis NRRL B-16338

    PubMed Central

    Yu, Xiaomin; Price, Neil P. J.; Evans, Bradley S.

    2014-01-01

    Two related actinomycetes, Glycomyces sp. strain NRRL B-16210 and Stackebrandtia nassauensis NRRL B-16338, were identified as potential phosphonic acid producers by screening for the gene encoding phosphoenolpyruvate (PEP) mutase, which is required for the biosynthesis of most phosphonates. Using a variety of analytical techniques, both strains were subsequently shown to produce phosphonate-containing exopolysaccharides (EPS), also known as phosphonoglycans. The phosphonoglycans were purified by sequential organic solvent extractions, methanol precipitation, and ultrafiltration. The EPS from the Glycomyces strain has a mass of 40 to 50 kDa and is composed of galactose, xylose, and five distinct partially O-methylated galactose residues. Per-deutero-methylation analysis indicated that galactosyl residues in the polysaccharide backbone are 3,4-linked Gal, 2,4-linked 3-MeGal, 2,3-linked Gal, 3,6-linked 2-MeGal, and 4,6-linked 2,3-diMeGal. The EPS from the Stackebrandtia strain is comprised of glucose, galactose, xylose, and four partially O-methylated galactose residues. Isotopic labeling indicated that the O-methyl groups in the Stackebrandtia phosphonoglycan arise from S-adenosylmethionine. The phosphonate moiety in both phosphonoglycans was shown to be 2-hydroxyethylphosphonate (2-HEP) by 31P nuclear magnetic resonance (NMR) and mass spectrometry following strong acid hydrolysis of the purified molecules. Partial acid hydrolysis of the purified EPS from Glycomyces yielded 2-HEP in ester linkage to the O-5 or O-6 position of a hexose and a 2-HEP mono(2,3-dihydroxypropyl)ester. Partial acid hydrolysis of Stackebrandtia EPS also revealed the presence of 2-HEP mono(2,3-dihydroxypropyl)ester. Examination of the genome sequences of the two strains revealed similar pepM-containing gene clusters that are likely to be required for phosphonoglycan synthesis. PMID:24584498

  4. SYTO probes: markers of apoptotic cell demise.

    PubMed

    Wlodkowic, Donald; Skommer, Joanna

    2007-10-01

    As mechanistic studies on tumor cell death advance towards their ultimate translational goal, there is a need for specific, rapid, and high-throughput analytical tools to detect diverse cell demise modes. Patented DNA-binding SYTO probes, for example, are gaining increasing interest as easy-to-use markers of caspase-dependent apoptotic cell death. They are proving convenient for tracking apoptosis in diverse hematopoietic cell lines and primary tumor samples, and, due to their spectral characteristics, appear to be useful for the development of multiparameter flow cytometry assays. Herein, several protocols for multiparametric assessment of apoptotic events using SYTO probes are provided. There are protocols describing the use of green fluorescent SYTO 16 and red fluorescent SYTO 17 dyes in combination with plasma membrane permeability markers. Another protocol highlights the multiparametric use of SYTO 16 dye in conjunction with the mitochondrial membrane potential sensitive probe, tetramethylrhodamine methyl ester (TMRM), and the plasma membrane permeability marker, 7-aminoactinomycin D (7-AAD).

  5. Protein-Lipid Interactions and Mechanisms of Antioxidant Activity of Proteins.

    DTIC Science & Technology

    1984-06-25

    lysozyme and peroxidizing methyl fatty acid esters 3 F.~~~ ~ ~ -: 7 7-7777- 77.:1 71 7: .and decreases lipid hydroperoxide and malonadelhyde...freeze-dried emulsions of methyl linoleate with chicken egg lysozyme and other proteins, and in solution with amino acids and several aldehydes. Generation...4 Z,. ..- : , , , , . .:: . . ,.. -. , . . . .b - ? . Egg lecithin liposomes with hen- egg lysozyme localized either inside or outside the vesicles

  6. Switching catalysis from hydrolysis to perhydrolysis in P. fluorescens esterase

    PubMed Central

    Yin, De Lu (Tyler); Bernhardt, Peter; Morley, Krista L.; Jiang, Yun; Cheeseman, Jeremy D.; Purpero, Vincent; Schrag, Joseph D.; Kazlauskas, Romas J.

    2010-01-01

    Many serine hydrolases catalyze perhydrolysis – the reversible formation of per-acids from carboxylic acids and hydrogen peroxide. Recently we showed that a single amino acid substitution in the alcohol binding pocket - L29P - in Pseudomonas fluorescens (SIK WI) aryl esterase (PFE) increased the specificity constant of PFE for peracetic acid formation >100-fold [Bernhardt et al. Angew. Chem. Intl. Ed. 2005, 44, 2742]. In this paper, we extend this work to address the three following questions. First, what is the molecular basis of the increase in perhydrolysis activity? We previously proposed that the L29P substitution creates a hydrogen bond between the enzyme and hydrogen peroxide in the transition state. Here we report two x-ray structures of L29P PFE that support this proposal. Both structures show a main chain carbonyl oxygen closer to the active-site serine as expected. One structure further shows acetate in the active site in an orientation consistent with reaction by an acyl-enzyme mechanism. We also detected an acyl-enzyme intermediate in the hydrolysis of ε-caprolactone by mass spectrometry. Second, can we further increase perhydrolysis activity? We discovered that the reverse reaction – hydrolysis of peracetic acid to acetic acid and hydrogen peroxide – occurs at nearly the diffusion limited rate. Since the reverse reaction cannot increase further, neither can the forward reaction. Consistent with this prediction, two variants with additional amino acid substitutions showed two fold higher kcat, but Km also increased so the specificity constant, kcat/Km, remained similar. Third, how does the L29P substitution change the esterase activity? Ester hydrolysis decreased for most esters (75-fold for ethyl acetate), but not for methyl esters. In contrast, L29P PFE catalyzed hydrolysis of ε-caprolactone five times more efficiently than wild-type PFE. Molecular modeling suggests that moving the carbonyl group closer to the active site blocks access for larger alcohol moieties, but binds ε-caprolactone more tightly. These results are consistent with the natural function of perhydrolases being either hydrolysis of peroxycarboxylic acids or hydrolysis of lactones. PMID:20112920

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

    PubMed

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

    2017-10-01

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

  8. 6-methyl-8-hexadecenoic acid: A novel fatty acid from the marine spongeDesmapsama anchorata.

    PubMed

    Carballeira, N M; Maldonado, M E

    1988-07-01

    The novel fatty acid 7-methyl-8-hexadecenoic (1) was identified in the marine spongeDesmapsama anchorata. Other interesting fatty acids identified were 14-methyl-8-hexadecenoic (2), better known through its methyl ester as one of the components of the sex attractant of the female dermestid beetle, and the saturated fatty acid 3-methylheptadecanoic (3), known to possess larvicidal activity. The main phospholipid fatty acids encountered inD. anchorata were palmitic (16∶0), behenic (22∶0) and 5,9-hexacosadienoic acid (26∶2), which together accounted for 50% of the total phospholipid fatty acid mixture.

  9. Synthesis and molecular crystal of 3-Chloro-2-(1-chloro-1-methyl-ethyl)-2,3-dihydro-1H-naphtho[2,1-b]oxepin-4-one

    NASA Astrophysics Data System (ADS)

    Tittal, Ram Kumar

    2018-03-01

    CuCl/TMEDA-promoted halogen atom transfer radical cyclization (HATRC) of dichloroacetic acid 1-(3-methyl-but-2-enyl)-naphthalen-2-yl ester in refluxing DCE gave chlorine containing 7-member lactone 3-Chloro-2-(1-chloro-1-methyl-ethyl)-2,3-dihydro-1H-naphtho[2,1-b]oxepin-4-one via 7-exo trig radical cyclization reaction. The structure of the Lactone was confirmed by X-ray diffraction data.

  10. Occurrence of 7-methyl-7-hexadecenoic acid, the corresponding alcohol, 7-methyl-6-hexadecenoic acid, and 5-methyl-4hexadecenoic acid in sperm whale oils.

    PubMed

    Pascal, J C; Ackman, R G

    1975-08-01

    Two sperm whale oils from the northern hemisphere and two from the southern hemisphere were fractionated. Triglyceride and wax esters were examined for fatty acids and alcohols with monoethylenic unsaturation bearing a methyl branch on an ethylenic carbon. The 7-methyl-7-hexadecenoic acid (0.37-1.37%) was accompanied by the corresponding alcohol (0.28-0.72%), but these materials were not accompanied by shorter chain homologues. The 7-methyl-6-hexadecenoic acid was relatively less important (0.23-0.68%), but was accompanied by 5-methyl-4-hexadecenoic acid (0.10-0.39%), and a partially identified C13 compound. Chromatographic properties on silver nitrate impregnated silicic acid TLC and on three GLC liquid phases are reported.

  11. Probing the Active Center of Benzaldehyde Lyase with Substitutions and the Pseudosubstrate Analogue Benzoylphosphonic Acid Methyl Ester

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    Brandt, Gabriel S.; Nemeria, Natalia; Chakraborty, Sumit

    2008-07-28

    Benzaldehyde lyase (BAL) catalyzes the reversible cleavage of (R)-benzoin to benzaldehyde utilizing thiamin diphosphate and Mg{sup 2+} as cofactors. The enzyme is important for the chemoenzymatic synthesis of a wide range of compounds via its carboligation reaction mechanism. In addition to its principal functions, BAL can slowly decarboxylate aromatic amino acids such as benzoylformic acid. It is also intriguing mechanistically due to the paucity of acid-base residues at the active center that can participate in proton transfer steps thought to be necessary for these types of reactions. Here methyl benzoylphosphonate, an excellent electrostatic analogue of benzoylformic acid, is used tomore » probe the mechanism of benzaldehyde lyase. The structure of benzaldehyde lyase in its covalent complex with methyl benzoylphosphonate was determined to 2.49 {angstrom} (Protein Data Bank entry 3D7K) and represents the first structure of this enzyme with a compound bound in the active site. No large structural reorganization was detected compared to the complex of the enzyme with thiamin diphosphate. The configuration of the predecarboxylation thiamin-bound intermediate was clarified by the structure. Both spectroscopic and X-ray structural studies are consistent with inhibition resulting from the binding of MBP to the thiamin diphosphate in the active centers. We also delineated the role of His29 (the sole potential acid-base catalyst in the active site other than the highly conserved Glu50) and Trp163 in cofactor activation and catalysis by benzaldehyde lyase.« less

  12. Probing the active center of benzaldehyde lyase with substitutions and the pseudo-substrate analog benzoylphosphonic acid methyl ester

    PubMed Central

    Brandt, Gabriel S.; Nemeria, Natalia; Chakraborty, Sumit; McLeish, Michael J.; Yep, Alejandra; Kenyon, George L.; Petsko, Gregory A.; Jordan, Frank; Ringe, Dagmar

    2009-01-01

    Benzaldehyde lyase (BAL) catalyzes the reversible cleavage of (R)-benzoin to benzaldehyde utilizing thiamin diphosphate and Mg2+ as cofactors. The enzyme is important for the chemoenzymatic synthesis of a wide range of compounds via its carboligation reaction mechanism. In addition to its principal functions, BAL can slowly decarboxylate aromatic amino acids such as benzoylformic acid. It is also intriguing mechanistically due to the paucity of acid-base residues at the active center that can participate in proton transfer steps thought to be necessary for these type of reactions. Here methyl benzoylphosphonate, an excellent electrostatic analog of benzoylformic acid, is used to probe the mechanism of benzaldehyde lyase. The structure of benzaldehyde lyase in its covalent complex with methyl benzoylphosphonate was determined to 2.49 Å (PDB ID: 3D7K) and represents the first structure of this enzyme with a compound bound in the active site. No large structural reorganization was detected compared to the complex of the enzyme with thiamin diphosphate. The configuration of the predecarboxylation thiamin-bound intermediate was clarified by the structure. Both spectroscopic and X-ray structural studies are consistent with inhibition resulting from the binding of MBP to the thiamin diphosphate in the active centers. We also delineated the role of His29 (the sole potential acid-base catalyst in the active site other than the highly conserved Glu50) and Trp163 in cofactor activation and catalysis by benzaldehyde lyase. PMID:18570438

  13. Changes in volatile profile of soybean residue (okara) upon solid-state fermentation by yeasts.

    PubMed

    Vong, Weng Chan; Liu, Shao-Quan

    2017-01-01

    Soybean residue (okara), a by-product of soymilk, is produced in large volumes by the soy food industry and is often discarded due to its undesirable flavour. As it contains a considerable amount of protein and fats, biotransformation of okara to improve its flavour presents an opportunity for alternative utilisation. This paper evaluated 10 yeasts in the solid-state fermentation of okara based on their volatile profiles as analysed with HS-SPME GC-MS/FID. Four 'dairy yeasts' (Geotrichum candidum, Yarrowia lipolytica, Debaryomyces hansenii and Kluyveromyces lactis) and six 'wine yeasts' (Saccharomyces cerevisiae, Lachancea thermotolerans, Metschnikowia pulcherrima, Pichia kluyveri, Torulaspora delbrueckii, and Williopsis saturnus) were studied. The main off-odourants in okara, hexanal and trans-2-hexenal, significantly decreased after fermentation due to their bioconversion into methyl ketones and/or esters. The okara fermented by dairy yeasts contained greater proportions of methyl ketones, while that by wine yeasts contained more ethyl and acetyl esters. Notably, the okara fermented by W. saturnus contained 13 esters and the total GC-FID peak area of esters was about 380 times that in fresh okara, leading to a perceptible fruity note. Okara can be exploited as an inexpensive substrate for bioflavour extraction and/or a more pleasant food ingredient via yeast fermentation. © 2016 Society of Chemical Industry. © 2016 Society of Chemical Industry.

  14. Evaluation of [(11)C]methyl-losartan and [(11)C]methyl-EXP3174 for PET imaging of renal AT1receptor in rats.

    PubMed

    Ismail, Basma; Hadizad, Tayebeh; Antoun, Rawad; Lortie, Mireille; deKemp, Robert A; Beanlands, Rob S B; DaSilva, Jean N

    2015-11-01

    The angiotensin II type 1 receptor (AT1R) is responsible for the main effects of the renin-angiotensin system (RAS), and its expression pattern is altered in several diseases. The [(11)C]methylated derivatives of the clinically used AT1R blocker (ARB) losartan and its active metabolite EXP3174, that binds with higher affinity to AT1R, were evaluated as potential PET imaging tracers in rat kidneys. [(11)C]Methyl-losartan and [(11)C]methyl-EXP3174 were synthesized by [(11)C]methylation of the tetrazole-protected analogs using [11C]methyl iodide. Tissue uptake and binding selectivity of [(11)C]methyl-losartan were assessed by ex-vivo biodistribution and in-vitro autoradiography. Radiolabeled metabolites in rat plasma and kidneys were analysed by column-switch HPLC. Both tracers were evaluated with small animal PET imaging. Due to better pharmacokinetics, [(11)C]methyl-EXP3174 was further investigated via PET by co-injection with AT1R antagonist candesartan or the AT2R antagonist PD123,319. Binding selectivity to renal AT1 over AT2 and Mas receptors was demonstrated for [(11)C]methyl-losartan. Plasma metabolite analysis at 10 min revealed stability of [(11)C]methyl-losartan and [(11)C]methyl-EXP3174 with the presence of unchanged tracer at 70.8 ± 9.9% and 81.4 ± 6.0%, of total radioactivity, respectively. Contrary to [(11)C]methyl-losartan, co-injection of candesartan with [(11)C]methyl-EXP3174 reduced the proportion of unchanged tracer (but not metabolites), indicating that these metabolites do not bind to AT1R in rat kidneys. MicroPET images for both radiotracers displayed high kidney-to-background contrast. Candesartan significantly reduced [(11)C]methyl-EXP3174 uptake in the kidney, whereas no difference was observed following PD123,319 indicating binding selectivity for AT1R. [(11)C]Methyl-EXP3174 displayed a favorable binding profile compared to [(11)C]methyl-losartan for imaging renal AT1Rs supporting further studies to assess its full potential as a quantitative probe for AT1R via PET. Copyright © 2015. Published by Elsevier Inc.

  15. Oxidative stability and ignition quality of algae derived methyl esters containing varying levels of methyl eicosapentaenoate and methyl docosahexaenoate

    NASA Astrophysics Data System (ADS)

    Bucy, Harrison

    Microalgae is currently receiving strong consideration as a potential biofuel feedstock to help meet the advanced biofuels mandate of the 2007 Energy Independence and Security Act because of its theoretically high yield (gallons/acre/year) in comparison to current terrestrial feedstocks. Additionally, microalgae also do not compete with food and can be cultivated with wastewater on non-arable land. Microalgae lipids can be converted into a variety of biofuels including fatty acid methyl esters (e.g. FAME biodiesel), renewable diesel, renewable gasoline, or jet fuel. For microalgae derived FAME, the fuel properties will be directly related to the fatty acid composition of the lipids produced by the given microalgae strain. Several microalgae species under consideration for wide scale cultivation, such as Nannochloropsis, produce lipids with fatty acid compositions containing substantially higher quantities of long chainpolyunsaturated fatty acids (LC-PUFA) in comparison to terrestrial feedstocks. It is expected that increased levels of LC-PUFA will be problematic in terms of meeting all of the current ASTM specifications for biodiesel. For example, it is known that oxidative stability and cetane number decrease with increasing levels of LC-PUFA. However, these same LC-PUFA fatty acids, such as eicosapentaenoic acid (EPA: C20:5) and docosahexaenoic acid (DHA: C22:6) are known to have high nutritional value thereby making separation of these compounds economically attractive. Given the uncertainty in the future value of these LC-PUFA compounds and the economic viability of the separation process, the goal of this study was to examine the oxidative stability and ignition quality of algae-based FAME with varying levels of EPA and DHA removal. Oxidative stability tests were conducted at a temperature of 110°C and airflow of 10 L/h using a Metrohm 743 Rancimat with automatic induction period determination following the EN 14112 Method from the ASTM D6751 and EN 14214 Standards, which call for induction periods of at least three hours and six hours, respectively. Derived Cetane Number testing was conducted using a Waukesha FIT following the ASTM D7170 Method. Tests were conducted with synthetic algal oil blends manufactured from various sources to match the fatty acid compositions of several algae strains subjected to varying removal amounts of roughly 0 -- 100 percent LC-PUFA. In addition, tests were also conducted with real algal methyl esters produced from multiple sources. The bis-allylic position equivalent (BAPE) was calculated for each fuel sample to quantify the level of unsaturation. The induction period was then plotted as a function of BAPE, which showed that the oxidative stability varied exponentially with the amount of LC-PUFA. The results suggest that removal of 45 -- 65 percent of the LC-PUFA from Nannochloropsis-based algal methyl esters would be sufficient for meeting existing ASTM specifications for oxidative stability and 75 -- 85 percent removal would be needed to meet the EN specification. The oxidative stability additive tert-butylhydroquinone (THBQ) was found to increase Nannochloropsis-based algal methyl esters' oxidative stability to ASTM and EN specifications at only 0.03 percent and 0.06 percent additions by mass, respectively, when no LC-PUFA was removed. The ignition quality tests showed that the Derived Cetane Number varied linearly with BAPE and the algae formulations were found to pass the ASTM cetane specification of 47 only if all the LC-PUFA were removed.

  16. Opiate receptor binding properties of morphine-, dihydromorphine-, and codeine 6-O-sulfate ester congeners.

    PubMed

    Crooks, Peter A; Kottayil, Santosh G; Al-Ghananeem, Abeer M; Byrn, Stephen R; Butterfield, D Allan

    2006-08-15

    A series of 3-O-acyl-6-O-sulfate esters of morphine, dihydromorphine, N-methylmorphinium iodide, codeine, and dihydrocodeine were prepared and evaluated for their ability to bind to mu-, delta-, kappa(1)-, kappa(2)-, and kappa(3)-opiate receptors. Several compounds exhibited good affinity for the mu-opiate receptor. Morphine-3-O-propionyl-6-O-sulfate had four times greater affinity than morphine at the mu-opiate receptor and was the most selective compound at this receptor subtype.

  17. 77 FR 63829 - Product Cancellation Order for Certain Pesticide Registrations

    Federal Register 2010, 2011, 2012, 2013, 2014

    2012-10-17

    .... 053883-00259 Termini 9.1 SC... Fipronil. CO080003 Endura Fungicide. Boscalid. MD080002 Ridomil Gold Copper hydroxide Copper. D-Alanine, N-(2,6- dimethylphenyl)-N- (methoxyacetyl)-, methyl ester. OR000023...

  18. A simplified and efficient method for the analysis of fatty acid methyl esters suitable for large clinical studies.

    PubMed

    Masood, Athar; Stark, Ken D; Salem, Norman

    2005-10-01

    Conventional sample preparation for fatty acid analysis is a complicated, multiple-step process, and gas chromatography (GC) analysis alone can require >1 h per sample to resolve fatty acid methyl esters (FAMEs). Fast GC analysis was adapted to human plasma FAME analysis using a modified polyethylene glycol column with smaller internal diameters, thinner stationary phase films, increased carrier gas linear velocity, and faster temperature ramping. Our results indicated that fast GC analyses were comparable to conventional GC in peak resolution. A conventional transesterification method based on Lepage and Roy was simplified to a one-step method with the elimination of the neutralization and centrifugation steps. A robotics-amenable method was also developed, with lower methylation temperatures and in an open-tube format using multiple reagent additions. The simplified methods produced results that were quantitatively similar and with similar coefficients of variation as compared with the original Lepage and Roy method. The present streamlined methodology is suitable for the direct fatty acid analysis of human plasma, is appropriate for research studies, and will facilitate large clinical trials and make possible population studies.

  19. Apoptosis triggered by pyropheophorbide-α methyl ester-mediated photodynamic therapy in a giant cell tumor in bone

    NASA Astrophysics Data System (ADS)

    Li, K.-T.; Zhang, J.; Duan, Q.-Q.; Bi, Y.; Bai, D.-Q.; Ou, Y.-S.

    2014-06-01

    A giant cell tumor in bone is the common primary bone tumor with aggressive features, occurring mainly in young adults. Photodynamic therapy is a new therapeutic technique for tumors. In this study, we investigated the effects of Pyropheophorbide-α methyl ester (MPPa)-mediated photodynamic therapy on the proliferation of giant cell tumor cells and its mechanism of action. Cell proliferation was evaluated using an MTT assay. Cellular apoptosis was detected by Hoechst nuclear staining, and flow cytometric assay. Mitochondrial membrane potential changes and cytochrome c, caspase-9, caspase-3, and Bcl-2 expression was assessed. Finally, we found that MPPa-mediated photodynamic therapy could effectively suppress the proliferation of human giant cell tumor cells and induce apoptosis. The mitochondrial pathway was involved in the MPPa-photodynamic therapy-induced apoptosis.

  20. Environmental effect of antioxidant additives on exhaust emission reduction in compression ignition engine fuelled with Annona methyl ester.

    PubMed

    Senthil, R; Silambarasan, R

    2015-01-01

    The aim of the present study is to analyse the effect of antioxidant l-ascorbic acid on engine performance and emissions of a diesel engine fuelled with methyl ester of Annona oil (MEAO). The antioxidant is mixed in various concentrations (100-400 mg) with MEAO. Result shows that the antioxidant additive mixture (MEAO+LA200) is effective in control of nitrogen oxides (NOx) and hydrocarbon (HC) emission of MEAO-fuelled engine without doing any engine modification. In this study by using MEAO, the NOx emission is reduced by about 23.38% at full load while compared with neat diesel fuel. Likewise there is a reduction in carbon monoxide, smoke, and HC by about 48%, 28.57% and 29.71% at full load condition compared with neat diesel fuel.

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