- Preparation method of trans-1, 3-diolefine
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The invention discloses a preparation method of trans-1, 3-diolefine, which comprises the following step: under the action of 4-dimethylaminopyridine and triethylamine, reacting 2, 3-dihydroxy propyl(9E, 12E)-9, 12-octadecadienoic acid ester with (9E, 12E)-9, 12-octadecadienoyl chloride to obtain the trans-1, 3-diolefine. Compared with the prior art, the method disclosed by the invention is simpleto operate, high in reaction selectivity and high in product yield.
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Paragraph 0068; 0070
(2021/03/18)
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- IONIZABLE AMINE LIPIDS AND LIPID NANOPARTICLES
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The disclosure provides ionizable amine lipids and salts thereof (e.g., pharmaceutically acceptable salts thereof) useful for the delivery of biologically active agents, for example delivering biologically active agents to cells to prepare engineered cells. The ionizable amine lipids disclosed herein are useful as ionizable lipids in the formulation of lipid nanoparticle-based compositions.
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Page/Page column 167
(2020/11/04)
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- Preparation method of linolenic acid glyceride
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The invention relates to the field of chemical synthesis, in particular to a preparation method of linolenic acid glyceride. The preparation method of the linolenic acid glyceride comprises the steps that low sodium alcoholate or low potassium alcoholate is used as a catalyst, low fatty acid alcohol ester and glycerol are blended according to the mole ratio of 2:1 and react for 10-20 h at 100-170 DEG C under a vacuum condition so as to obtain a crude glyceride product; and the crude glyceride product is subjected to subsequent processing and treatment, and a corresponding product is prepared. By adoption of the preparation method under a solvent-free system, a remarkable effect is achieved on improving of the productivity and the quality, and the content of linolenic acid monoester in products is high.
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Paragraph 0015; 0016; 0017
(2017/07/04)
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- Influence of fatty acid desaturation on spontaneous acyl migration in 2-monoacylglycerols
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The effect of desaturation from the C9 to the C15 carbon of 2-monoacylglycerol (2-MAG) fatty acids on spontaneous acyl migration is described. Three 2-MAG species, 2-monooleoylglycerol (C18:1 cis-Δ9), 2-monolinoleoylglycerol (C18:2 cis-Δ9,12), and 2-monolinolenoylglycerol (C18:3 cis-Δ9,12,15) were synthesized by lipase-catalyzed ethanolysis of their respective triacylglycerols and isolated in >60 % yield and at 2-MAG purities of >95 % relative to 1-monoacylglycerol (1-MAG). 1H-NMR spectroscopy was used to monitor the spontaneous acyl migration of the 2-MAG species over a temperature range from 20 to 80 °C. The relative energies of activation calculated from the Arrhenius relationships of the 2-MAG acyl migration rate constants were 73.3, 68.0, and 72.9 kJ mol-1 for the three 2-MAG species, respectively. Density functional calculations performed using the B3LYP functional at the 6-31+G* basis set on the three ketal ring intermediate of the three 2-MAG species followed a similar trend with a lack of relative energetic preference associated with the degree of desaturation. The kinetically determined relative activation energies were approximately twofold higher than the theoretical relative Gibbs free energies of the intermediates, suggesting that other factors influence acyl migration. In general, increasing desaturation after the C9 carbon of 2-MAG fatty acids had no appreciable effect on acyl migration rates. AOCS (outside the USA) 2012.
- Compton, David L.,Laszlo, Joseph A.,Appell, Michael,Vermillion, Karl E.,Evans, Kervin O.
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p. 2259 - 2267
(2013/01/15)
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- Pheromone synthesis. Part 253: Synthesis of the racemates and enantiomers of triglycerides of male Drosophila fruit flies with special emphasis on the preparation of enantiomerically pure 1-monoglycerides
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The racemates and enantiomers of triglycerides 1aee (2,3-ditigloyloxypropyl esters of palmitic, palmitoleic, stearic, oleic, and linoleic acids) of male Drosophila fruit flies were synthesized in three steps from the racemate and enantiomers of 2,3-acetoneglycerol (2) via 1-monoglycerides 4aee derived from the above fatty acids. Appropriate conditions were established for the preparation of enantiomerically pure 1-monoglycerides 4aee, and their enantiomeric purities were determined by NMR analysis of the corresponding bis-(R)-MTPA esters.
- Mori, Kenji
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p. 8441 - 8449
(2012/10/07)
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- Monoglycerides from the brown alga Sargassum sagamianum: Isolation, synthesis, and biological activity
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Polyunsaturated fatty acid-derived monoglycerides were characterized from the marine brown alga Sargassum sagamianum, collected from Jeju Island, Korea. A new compound of this structural class was isolated and determined to be 1-octadecatetraenoyl glycerol, by combined spectroscopic methods. Based on the structures and bioactivity of these compounds, a series of monoglycerides were synthesized using glycerol and various fatty acids. Several compounds exhibited moderate to significant inhibition of phospholipase A2 and cyclooxygenase-2.
- Chang, Hyeun Wook,Jang, Kyoung Hwa,Lee, Doohyun,Kang, Hee Ryong,Kim, Tae-Yoon,Lee, Bong Ho,Choi, Byoung Wook,Kim, Sanghee,Shin, Jongheon
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body text
p. 3589 - 3592
(2009/04/11)
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- Practical syntheses of triacylglycerol regioisomers containing long-chain polyunsaturated fatty acids
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Docosahexaenoic acid (DHA, 22:6n-3) is known to protect against a range of degenerative disease conditions and aid in the development of eye and brain function in infants. In dietary lipids DHA is found primarily in the triacylglycerol (TAG) form. However, the effects of the positional distribution of DHA in TAG on lipid functional properties such as bioactivity and oxidative stability are not clearly understood. Studies on this subject for the most part are limited by a lack of regioisomerically pure TAG model compounds containing DHA or similar long-chain (LC)-polyunsaturated fatty acids (PUFA). This paper reports on the development of a practical procedure, based on chemical and enzymatic reactions, for the syntheses of regioisomerically enriched, symmetrical and unsymmetrical TAG isomers containing two palmitic acid and one of linoleic acid, linolenic acid, or DHA. 1,3-Selective acylation of glycerol with vinyl esters of fatty acids catalyzed by Candida antarctica lipase and direct coupling with fatty acids in the presence of the coupling agents 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 4-dimethylaminopyridine furnished 1,3-dihexadecanoyl-2-docosahexaenoyl glycerol and its unsymmetrical isomer 1,2-dihexadecanoyl-3-docosahexaenoyl glycerol in 99 and 60% yield, respectively. Critical to the success of the unsymmetrical TAG synthesis is the demonstration that PUFA-containing glycerol acetonides can readily survive appropriately tailored acid-catalyzed conditions. In this way, sufficient quantities of highly regioisomerically enriched PUFA-containing unsymmetrical monoacylglycerols (MAG) and TAG have now become routinely accessible. The methods are amenable to scale-up and could be adopted for regioenriched synthesis of a wide range of TAG. AOCS 2007.
- Fraser, Benjamin H.,Perlmutter, Patrick,Wijesundera, Chakra
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- Lipase-catalyzed transesterification of trilinolein or trilinolenin with selected phenolic acids
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The enzymatic transesterification of selected phenolic acids with TAG, including trilinolein (TLA) and trilinolenin (TLNA), was investigated in an organic solvent medium. Maximal bioconversion of 66% was obtained with a dihydrocaffeic acid (DHCA) to TLA ratio of 1:2 after 5 d of reaction. Similarly, the highest bioconversion of 62% was obtained with a DHCA to TLNA ratio of 1:2, but after 12 d of reaction. However, a ratio of 1:4 DHCA/TLA decreased the bioconversion to 53%. Transesterification reactions of ferulic acid with both TAG, using a ratio of 1:2, resulted in low bioconversion of 16 and 14% with TLA and TLNA, respectively. The overall results indicated that bioconversion of phenolic MAG was higher than that of phenolic DAG. The structures of mono- and dilinoleyl dihydrocaffeate as well as those of mono- and dilinolenyl dihydrocaffeate were confirmed by LC-MS analyses. The phenolic lipids demonstrated moderate radical-scavenging activity. Copyright
- Sabally, Kebba,Karboune, Salwa,St-Louis, Richard,Kermasha, Selim
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p. 101 - 107
(2007/10/03)
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- Stereospecific and regioselective opening of an oxirane system. A new efficient entry to 1- or 3-monoacyl- and 1- or 3-monoalkyl-sn-glycerols
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Acyl or alkyl glycidols in the presence of trifluoroacetic anhydride (TFAA) and trifluoroacetate anions, undergo a regioselective and stereospecific opening of the oxirane system to produce the bis(trifluoroacetylated) derivatives, from which the corresponding 1(3)-monoacyl-sn-glycerols or 1(3)-monoalkyl-sn-glycerols can be obtained directly in high purity (>99%) and in quantitative yields.
- Stamatov, Stephan D.,Stawinski, Jacek
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p. 1601 - 1605
(2007/10/03)
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- Host-recognizing kairomones for parasitic wasp, Anisopteromalus calandrae, from larvae of azuki bean weevil, Callosobruchus chinensis.
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Host-recognizing kairomones for the stinging behavior of the parasitic wasp, Anisopteromalus calandrae, were identified on host azuki bean weevil larvae, Callosobruchus chinensis (L.). The kairomones were extracted with acetone from Chinese green beans, from which emerged wasps and host weevils had been removed. The kairomones are a mixture of triacylglycerols and fatty acids, each of which is separately active, and with no observable synergistic effect between them. These compounds are known to be constituents of an oviposition-marking pheromone of host azuki bean weevils. However, they differ from the previously reported saturated hydrocarbons and diacylglycerols of the kairomone that another parasitic wasp, Dinarmus basalis, uses for the host recognition of C. chinensis. Thus, A. calandrae and D. basalis selectively utilize different constituents of the oviposition-marking pheromone of C. chinensis as host-recognizing kairomones.
- Onodera, Junko,Matsuyama, Shigeru,Suzuki, Takahisa,Fujii, Koichi
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p. 1209 - 1220
(2007/10/03)
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- Study of the effect of DATEM. 1. Influence of fatty acid chain length on rheology and baking
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To answer the question of which fatty acid residue is the most effective, diacetyltartaric esters of monoglycerides (DATEMs) with fatty acids of chain lengths 6:0-20:0 were synthesized. The activity of synthesized DATEMs and commercial DATEM products was studied by means of rheological methods and a microscale baking test with 10 g of flour. Variation of the acyl residue from 6:0 to 22:0 showed that stearic acid (18:0) had the best effect on the baking activity of DATEM (loaf volume increased by 62%). DATEMs containing unsaturated fatty acids (18:1, 18:2) or DATEMs produced from diacylglycerols instead of monoacylglycerols showed a slight increase of the loaf volumes. A slight effect of DATEM on the rheology of dough was observed. However, much greater was the effect on the gluten isolated from doughs prepared with DATEM. The resistance of gluten to extension was increased after the addition of increasing amounts of DATEM (0.1-0.5%). Within the series of DATEMs derived from the homologous series of monoacylglycerols the product based on glycerol monostearate (18:0) showed a maximum increase of the gluten resistance.
- Koehler, Peter,Grosch, Werner
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p. 1863 - 1869
(2007/10/03)
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- Enzymatic synthesis of symmetrical 1,3-diacylglycerols by direct esterification of glycerol in solvent-free system
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1,3-Diacylglycerols were synthesized by direct esterification of glycerol with free fatty acids in a solvent-free system. Free fatty acids with relatively low melting points (45°C) such as unsaturated and medium-chain saturated fatty acids were used. With stoichiometric ratios of the reactants and water removal by evaporation at 3 mm Hg vacuum applied at 1 h and thereafter, the maximal 1,3-diacylglycerol content in the reaction mixture was: 84.6% for 1,3-dicaprylin, 84.4% for 1,3-dicaprin, 74.3% for 1,3-dilinolein, 71.7% for 1,3-dieicosapentaenoin, 67.4% for 1,3-dilaurin, and 61.1% for 1,3-diolein. Some of the system's parameters (temperature, water removal, and molar ratio of the reactants) were optimized for the production of 1,3-dicaprylin, and the maximal yield reached 98%. The product was used for the chemical synthesis of 1,3-dicapryloyl-2-eicosapentaenoylglycerol. The yield after purification was 42%, and the purity of the triacylglycerol was 98% (both 1,3-dicapryloyl-2-eicosapentaenoylglycerol and 1,2-dicapryloyl-3-eicosapentaenoylglycerol included) by gas chromatographic analysis, of which 90% was the desired structured triacylglycerol (1,3-dicapryloyl-2-eicosapentaenoylglycerol) as determined by silver ion high-performance liquid chromatographic analysis.
- Rosu, Roxana,Yasui, Mamoru,Iwasaki, Yugo,Yamane, Tsuneo
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p. 839 - 843
(2007/10/03)
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- Enzymatic esterification of glycerol III. Lipase-catalyzed synthesis of regioisomerically pure 1,3-sn-diacylglycerols and 1(3)-rac-monoacylglycerols derived from unsaturated fatty acids
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Lipases that display high regioselectivities and broad substrate tolerance were used as catalysts for the efficient esterification of glycerol under the conditions of irreversible acyl transfer. A variety of unsaturated fatty acids, such as oleic, linoleic, erucic, ricinolic, hydroxystearic and coriolic acid, were used for this purpose in the form of their vinyl esters. Suitable biocatalysts were chosen on the basis of systematic screening experiments regarding their regioselectivities (RE) and substrate tolerances. Distinct differences were found and expressed in numerical RE values as a measure for differences of these biocatalysts as being specific, selective, and nonspecific. Based on these experiments, a variety of molecules were synthesized on a preparative scale (>150 mmol) in good yield (ca. 85%) and with high regioisomerical purities (>95% RE).
- Waldinger,Schneider
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p. 1513 - 1519
(2007/10/03)
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- Synthesis of Triacylglyceride Hydroperoxides Derived from Linoleic Acid
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Four triacylglyceride hydroperoxides were synthesized by DCC-mediated esterification of a dimethylperketal of 13-hydroperoxyoctadecadienoic acid with glycerides, in which on e or two linoleoyl groups were linked, and by final removal of the protective group with a mixture of THF, acetic acid and water.
- Baba, Naomichi,Hirota, Naohisa,Umino, Hitoshi,Matsuo, Kyowa,Nakajima, Shuhei,et al.
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p. 1547 - 1548
(2007/10/02)
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- Biologically active lipids binding membrane receptors
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Neutral lipids are provided characterized by binding to phorboid and ingenoid receptors. These lipids are found in a wide variety of cellular sources as well as milk and may be isolated by specific extraction and chromatographic procedures. Depending upon the source, the glycerides may be mono- or di-glycerides, wherein the total number of carbon atoms of the fatty acids is in the range of 18 to 26, so that the monoglyceride has a fatty acid of at least 18 carbon atoms, while the di-glyceride has a fatty acid of at least 14 carbon atoms.
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