Enzymatic synthesis of 1,3‐dicapryloyl‐2‐eicosapentaenoylglycerol

Abstract 1,3‐Dicapryloyl‐2‐eicosapentaenoylglycerol (CEC) was synthesized by interesterification of trieicosapentaenoylglycerol (EEE) with ethyl caprylate (EtC) catalyzed by Lipozyme TM . After some of the reaction conditions were optimized, the maximal molar content of CEC in the glycerides of the reaction mixture was 91%. Among the parameters studied in the optimization, the critical ones were: (i) the water content, which influenced the conversion of EEE to CEC and 1‐capryloyl‐2‐eicosapentaenoylglycerol (CEOH), and (ii) the timing of water removal under reduced pressure for the reesterification of CEOH to form CEC. The complete synthesis of CEC from ethyl eicosapentaenoate (EtE) was performed in three steps: (i) hydrolysis of EtE to free eicosapentaenoic acid (EPA), (ii) esterification of glycerol with EPA to form EEE, and (iii) interesterification of EEE with EtC under the optimized conditions. The first two steps were catalyzed by Novozym TM and the third by Lipozyme TM . The total yield over all the steps was 88%, and no purification of the intermediates was necessary. The regioisomeric purity of the product was 100% by silver‐ion high‐pressure liquid chromatography.