140670-41-3Relevant articles and documents
The Synthesis of Homogeneous Triglycerides of Eicosapentaenoic Acid and Docosahexaenoic Acid by Lipase
Haraldsson, Gudmundur G.,Gudmundsson, Birgir Oe.,Almarsson, Oern
, p. 941 - 952 (1995)
A highly efficient synthesis of homogeneous triglycerides of either pure eicosapentaenoic acid, 1, or docosahexaenoic acid, 2, by an immobilized non-regiospecific yeast lipase from Candida antarctica is described.Two methods were used: Interesterification of tributyrin and direct esterification of glycerol with stoichiometric amount of 99percent EPA or DHA as ethyl esters and free fatty acids, respectively.Both processes were performed under vacuum at 65 deg C in the absence of any solvent.The volatile co-products were condensed into a cooled trap, thus shifting the equilibrium toward completion.Complete incorporation was reached in less than 72 h for all cases, but the direct esterification was found to proceed considerably faster than the transesterification as were both processes involving EPA as compared to DHA.High-field 1H NMR spectroscopy analysis offered detailed investigation of the intermediate glycerides during the direct esterification reaction.The purity of the resulting crude products which were afforded in excellent yields was very high.
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.
