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...
Published in: | Journal of the American Oil Chemists' Society |
---|---|
Main Authors: | , , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
Wiley
2003
|
Subjects: | |
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 |
id |
crwiley:10.1007/s11746-003-0805-y |
---|---|
record_format |
openpolar |
spelling |
crwiley:10.1007/s11746-003-0805-y 2024-06-02T07:57:37+00:00 Synthesis of 1,3‐dicapryloyl‐2‐docosahexaenoylglycerol by a combination of nonselective and sn‐1,3‐selective lipase reactions Negishi, Satoshi Arai, Yuri Arimoto, Shin Tsuchiya, Kinya Takahashi, Isamu 2003 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 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Journal of the American Oil Chemists' Society volume 80, issue 10, page 971-974 ISSN 0003-021X 1558-9331 journal-article 2003 crwiley https://doi.org/10.1007/s11746-003-0805-y 2024-05-03T10:45:10Z 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. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library Journal of the American Oil Chemists' Society 80 10 971 974 |
institution |
Open Polar |
collection |
Wiley Online Library |
op_collection_id |
crwiley |
language |
English |
description |
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. |
format |
Article in Journal/Newspaper |
author |
Negishi, Satoshi Arai, Yuri Arimoto, Shin Tsuchiya, Kinya Takahashi, Isamu |
spellingShingle |
Negishi, Satoshi Arai, Yuri Arimoto, Shin Tsuchiya, Kinya Takahashi, Isamu Synthesis of 1,3‐dicapryloyl‐2‐docosahexaenoylglycerol by a combination of nonselective and sn‐1,3‐selective lipase reactions |
author_facet |
Negishi, Satoshi Arai, Yuri Arimoto, Shin Tsuchiya, Kinya Takahashi, Isamu |
author_sort |
Negishi, Satoshi |
title |
Synthesis of 1,3‐dicapryloyl‐2‐docosahexaenoylglycerol by a combination of nonselective and sn‐1,3‐selective lipase reactions |
title_short |
Synthesis of 1,3‐dicapryloyl‐2‐docosahexaenoylglycerol by a combination of nonselective and sn‐1,3‐selective lipase reactions |
title_full |
Synthesis of 1,3‐dicapryloyl‐2‐docosahexaenoylglycerol by a combination of nonselective and sn‐1,3‐selective lipase reactions |
title_fullStr |
Synthesis of 1,3‐dicapryloyl‐2‐docosahexaenoylglycerol by a combination of nonselective and sn‐1,3‐selective lipase reactions |
title_full_unstemmed |
Synthesis of 1,3‐dicapryloyl‐2‐docosahexaenoylglycerol by a combination of nonselective and sn‐1,3‐selective lipase reactions |
title_sort |
synthesis of 1,3‐dicapryloyl‐2‐docosahexaenoylglycerol by a combination of nonselective and sn‐1,3‐selective lipase reactions |
publisher |
Wiley |
publishDate |
2003 |
url |
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 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Journal of the American Oil Chemists' Society volume 80, issue 10, page 971-974 ISSN 0003-021X 1558-9331 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1007/s11746-003-0805-y |
container_title |
Journal of the American Oil Chemists' Society |
container_volume |
80 |
container_issue |
10 |
container_start_page |
971 |
op_container_end_page |
974 |
_version_ |
1800740799918374912 |