Synthesis of 1,3‐dicapryloyl‐2‐docosahexaenoylglycerol by a combination of nonselective and sn‐1,3‐selective lipase reactions

Abstract A two‐step consecutive synthetic method for the production of symmetrical, structured lipids by a combination of nonselective and sn ‐1,3 regioselective ester exchange reactions was investigated. In the first step, TAG with unspecifically substituted DHA were obtained by reacting tricaprylo...

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Bibliographic Details
Published in:Journal of the American Oil Chemists' Society
Main Authors: Negishi, Satoshi, Arai, Yuri, Arimoto, Shin, Tsuchiya, Kinya, Takahashi, Isamu
Format: Article in Journal/Newspaper
Language:English
Published: Wiley 2003
Subjects:
Antarc*
Antarctica
Online Access:http://dx.doi.org/10.1007/s11746-003-0805-y
https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1007%2Fs11746-003-0805-y
https://onlinelibrary.wiley.com/doi/full/10.1007/s11746-003-0805-y
Description
Summary:Abstract A two‐step consecutive synthetic method for the production of symmetrical, structured lipids by a combination of nonselective and sn ‐1,3 regioselective ester exchange reactions was investigated. In the first step, TAG with unspecifically substituted DHA were obtained by reacting tricapryloylglycerol (CCC) with ethyl docosahexanoate (EtDHA) using the lipase QLM (from Alcaligenes sp.), followed by removing the ethyl ester and CCC by molecular distillation. In the second step, sn ‐1,3 regioselective ester exchange was achieved by reacting the resulting TAG with ethyl caprylate (EtC) using the immobilized lipase Novozyme 435 ( Candida antarctica lipase), followed by distillation of the ethyl ester and CCC to give sn ‐1,3‐dicapryloyl‐ sn ‐2‐docosahexaenoylglycerol (CDC). The acylglycerol composition of CDC was analyzed by GLC, which showed that the content of dicapryloyl‐docosahexaenoylglycerols (2CD) in the product was 76.4%, and that the ratio of CDC to sn ‐1,2‐dicapryloyl‐ sn ‐3‐docosahexaenoylglycerol contained in 2CD was 82.7∶17.3 (%). The distillates CCC, EtDHA, and EtC could be recycled repeatedly to produce CDC as the substrate for the consecutive ester exchange reaction. In addition, separation of CCC and EtDHA was unnecessary for reuse. The present method is considered to meet the requirements for industrial utilization, in which simplicity in scaleup, high yields, compact reaction system, and minimal formation of by‐products are important factors.

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