Study of TAG ethanolysis to 2‐MAG by immobilized Candida antarctica lipase and synthesis of symmetrically structured TAG
Abstract Regiospecific ethanolysis of homogenous TAG with immobilized Candida antarctica lipase (Novozym 435) was studied using trioleoylglycerol (TO) as a model substrate. Optimization of the reactant weight ratio revealed that the 2‐MAG reaction yield increased when a larger amount of ethanol was...
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crwiley:10.1007/s11746-002-0573-8 2024-06-23T07:46:36+00:00 Study of TAG ethanolysis to 2‐MAG by immobilized Candida antarctica lipase and synthesis of symmetrically structured TAG Irimescu, Roxana Iwasaki, Yugo Hou, Ching T. 2002 http://dx.doi.org/10.1007/s11746-002-0573-8 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1007%2Fs11746-002-0573-8 https://onlinelibrary.wiley.com/doi/full/10.1007/s11746-002-0573-8 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Journal of the American Oil Chemists' Society volume 79, issue 9, page 879-883 ISSN 0003-021X 1558-9331 journal-article 2002 crwiley https://doi.org/10.1007/s11746-002-0573-8 2024-05-31T08:14:06Z Abstract Regiospecific ethanolysis of homogenous TAG with immobilized Candida antarctica lipase (Novozym 435) was studied using trioleoylglycerol (TO) as a model substrate. Optimization of the reactant weight ratio revealed that the 2‐MAG reaction yield increased when a larger amount of ethanol was used. These results suggested that Novozym 435 showed strict regiospecificity in an excess amount of ethanol. The process optimization (reaction temperature and reactant molar ratio) and a study of lipase specificity for various substrates were performed. Under the optimized conditions (ethanol/TO molar ratio=77∶1 and 25°C), 2‐monooleoylglycerol (2‐MO) was obtained in more than 98% content among glycerides of the reaction mixture and approximately 88% reaction yield in 4 h. The above reaction conditions were applied for ethanolysis of tridocosahexaenoylglycerol, trieicosapentaenoylglycerol, triarachidonoylglycerol, tri‐α‐linolenoylglycerol, and trilinoleoylglycerol. Reaction yields ranging from 71.9 to 93.7% were obtained in short reaction times (2.5 to 8 h). Purified (>98%) 2‐MO and 2‐monodocosahexaenoylglycerol (2‐MD) were reesterified with caprylic acid by immobilized Rhizomucor miehei lipase (Lipozyme IM) to afford symmetrical structured TAG. At a stoichiometric ratio of 2‐MAG/caprylic acid, 25°C and 2–5 mm Hg vacuum, the glyceride composition of the esterification mixture was approximately 95% 1,3‐dicapryloyl‐2‐oleoylglycerol (COC) at 4 h, and 96% 1,3‐dicapryloyl‐2‐docosahexaenoylglycerol (CDC) at 4 h, and 96% 1,3‐dicapryloyl‐2‐docosahexaenoylglycerol (CDC) at 8 h. The regioisomeric purity of both COC and CDC was 100%. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library Journal of the American Oil Chemists' Society 79 9 879 883 |
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Wiley Online Library |
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English |
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Abstract Regiospecific ethanolysis of homogenous TAG with immobilized Candida antarctica lipase (Novozym 435) was studied using trioleoylglycerol (TO) as a model substrate. Optimization of the reactant weight ratio revealed that the 2‐MAG reaction yield increased when a larger amount of ethanol was used. These results suggested that Novozym 435 showed strict regiospecificity in an excess amount of ethanol. The process optimization (reaction temperature and reactant molar ratio) and a study of lipase specificity for various substrates were performed. Under the optimized conditions (ethanol/TO molar ratio=77∶1 and 25°C), 2‐monooleoylglycerol (2‐MO) was obtained in more than 98% content among glycerides of the reaction mixture and approximately 88% reaction yield in 4 h. The above reaction conditions were applied for ethanolysis of tridocosahexaenoylglycerol, trieicosapentaenoylglycerol, triarachidonoylglycerol, tri‐α‐linolenoylglycerol, and trilinoleoylglycerol. Reaction yields ranging from 71.9 to 93.7% were obtained in short reaction times (2.5 to 8 h). Purified (>98%) 2‐MO and 2‐monodocosahexaenoylglycerol (2‐MD) were reesterified with caprylic acid by immobilized Rhizomucor miehei lipase (Lipozyme IM) to afford symmetrical structured TAG. At a stoichiometric ratio of 2‐MAG/caprylic acid, 25°C and 2–5 mm Hg vacuum, the glyceride composition of the esterification mixture was approximately 95% 1,3‐dicapryloyl‐2‐oleoylglycerol (COC) at 4 h, and 96% 1,3‐dicapryloyl‐2‐docosahexaenoylglycerol (CDC) at 4 h, and 96% 1,3‐dicapryloyl‐2‐docosahexaenoylglycerol (CDC) at 8 h. The regioisomeric purity of both COC and CDC was 100%. |
format |
Article in Journal/Newspaper |
author |
Irimescu, Roxana Iwasaki, Yugo Hou, Ching T. |
spellingShingle |
Irimescu, Roxana Iwasaki, Yugo Hou, Ching T. Study of TAG ethanolysis to 2‐MAG by immobilized Candida antarctica lipase and synthesis of symmetrically structured TAG |
author_facet |
Irimescu, Roxana Iwasaki, Yugo Hou, Ching T. |
author_sort |
Irimescu, Roxana |
title |
Study of TAG ethanolysis to 2‐MAG by immobilized Candida antarctica lipase and synthesis of symmetrically structured TAG |
title_short |
Study of TAG ethanolysis to 2‐MAG by immobilized Candida antarctica lipase and synthesis of symmetrically structured TAG |
title_full |
Study of TAG ethanolysis to 2‐MAG by immobilized Candida antarctica lipase and synthesis of symmetrically structured TAG |
title_fullStr |
Study of TAG ethanolysis to 2‐MAG by immobilized Candida antarctica lipase and synthesis of symmetrically structured TAG |
title_full_unstemmed |
Study of TAG ethanolysis to 2‐MAG by immobilized Candida antarctica lipase and synthesis of symmetrically structured TAG |
title_sort |
study of tag ethanolysis to 2‐mag by immobilized candida antarctica lipase and synthesis of symmetrically structured tag |
publisher |
Wiley |
publishDate |
2002 |
url |
http://dx.doi.org/10.1007/s11746-002-0573-8 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1007%2Fs11746-002-0573-8 https://onlinelibrary.wiley.com/doi/full/10.1007/s11746-002-0573-8 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Journal of the American Oil Chemists' Society volume 79, issue 9, page 879-883 ISSN 0003-021X 1558-9331 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1007/s11746-002-0573-8 |
container_title |
Journal of the American Oil Chemists' Society |
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79 |
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9 |
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879 |
op_container_end_page |
883 |
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1802646950439288832 |