2277-28-3Relevant academic research and scientific papers
Preparation method of trans-1, 3-diolefine
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Paragraph 0068; 0070, (2021/03/18)
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.
IONIZABLE AMINE LIPIDS AND LIPID NANOPARTICLES
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Page/Page column 87-89; 168, (2020/11/04)
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.
Preparation method of linolenic acid glyceride
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Paragraph 0015; 0016; 0017, (2017/07/04)
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.
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
Mori, Kenji
experimental part, p. 8441 - 8449 (2012/10/07)
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.
Influence of fatty acid desaturation on spontaneous acyl migration in 2-monoacylglycerols
Compton, David L.,Laszlo, Joseph A.,Appell, Michael,Vermillion, Karl E.,Evans, Kervin O.
, p. 2259 - 2267 (2013/01/15)
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.
Monoglycerides from the brown alga Sargassum sagamianum: Isolation, synthesis, and biological activity
Chang, Hyeun Wook,Jang, Kyoung Hwa,Lee, Doohyun,Kang, Hee Ryong,Kim, Tae-Yoon,Lee, Bong Ho,Choi, Byoung Wook,Kim, Sanghee,Shin, Jongheon
body text, p. 3589 - 3592 (2009/04/11)
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.
Practical syntheses of triacylglycerol regioisomers containing long-chain polyunsaturated fatty acids
Fraser, Benjamin H.,Perlmutter, Patrick,Wijesundera, Chakra
, p. 11 - 21 (2008/09/21)
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.
Lipase-catalyzed transesterification of trilinolein or trilinolenin with selected phenolic acids
Sabally, Kebba,Karboune, Salwa,St-Louis, Richard,Kermasha, Selim
, p. 101 - 107 (2007/10/03)
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
Stereospecific and regioselective opening of an oxirane system. A new efficient entry to 1- or 3-monoacyl- and 1- or 3-monoalkyl-sn-glycerols
Stamatov, Stephan D.,Stawinski, Jacek
, p. 1601 - 1605 (2007/10/03)
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.
Host-recognizing kairomones for parasitic wasp, Anisopteromalus calandrae, from larvae of azuki bean weevil, Callosobruchus chinensis.
Onodera, Junko,Matsuyama, Shigeru,Suzuki, Takahisa,Fujii, Koichi
, p. 1209 - 1220 (2007/10/03)
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.
