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Enzymatic synthesis of symmetrical 1,3‐diacylglycerols by direct esterification of glycerol in solvent‐free system
Author(s) -
Rosu Roxana,
Yasui Mamoru,
Iwasaki Yugo,
Yamane Tsuneo
Publication year - 1999
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-999-0074-7
Subject(s) - chemistry , yield (engineering) , glycerol , glyceride , solvent , chromatography , stoichiometry , molar ratio , catalysis , organic chemistry , fatty acid , materials science , metallurgy
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.