99660-94-3Relevant articles and documents
Enzymatic synthesis of symmetrical 1,3-diacylglycerols by direct esterification of glycerol in solvent-free system
Rosu, Roxana,Yasui, Mamoru,Iwasaki, Yugo,Yamane, Tsuneo
, p. 839 - 843 (2007/10/03)
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.
Synthesis of Triacylglycerol from Polyunsaturated Fatty Acid by Immobilized Lipase
Kosugi, Yoshitsugu,Azuma, Naoki
, p. 1397 - 1403 (2007/10/02)
More than 95percent of polyunsaturated acid (PUFA) was converted to triacylglycerol by immobilized lipase from Candida antarctica or Rhizomucor miehei.The esterification was carried out at 50-60 deg C with shaking and dehydration for 24 h.The substrates consisted of glycerol and free fatty acid or ethyl esters of the fatty acid at a 1:3 molar ratio.The docosahexaenoic acid (DHA) or eicosapentaenoic acid (EPA) in the substrate polymerized during the reaction, and they required 5-10percent more than the stoichiometric amount to compensate for the PUFA loss.On the contrary, ethyl esters of DHA and EPA were not polymerized.Pure tridocosahexaenoyl, trieicosapentaenoyl and triarachidonoyl glycerol were isolated after passing the product through a basic aluminum oxide column.Industrial feasibility of this process was discussed for the ethyl ester as substrate. KEY WORDS: Docosahexaenoic acid, docosahexaenoyl ethyl ester, eicosapentaenoic acid, immobilized lipase, lipase, polyunsaturated fatty acid, triacylglycerol, triarachidonoyl glycerol, tridocosahexaenoyl glycerol, trieicosapentaenoyl glycerol.
