Studies on the enzymatic synthesis of lipophilic derivatives of natural antioxidants
Abstract The esterification of some natural antioxidants such as cinnamic acid derivatives and ascorbic acid in non‐aqueous media, catalyzed by immobilized lipases from Candida antarctica and Rhizomucor miehei , was investigated. The alcohol chain length affected the rate of esterification of cinnam...
Published in: | Journal of the American Oil Chemists' Society |
---|---|
Main Authors: | , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
Wiley
1999
|
Subjects: | |
Online Access: | http://dx.doi.org/10.1007/s11746-999-0193-1 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1007%2Fs11746-999-0193-1 https://onlinelibrary.wiley.com/doi/full/10.1007/s11746-999-0193-1 |
id |
crwiley:10.1007/s11746-999-0193-1 |
---|---|
record_format |
openpolar |
spelling |
crwiley:10.1007/s11746-999-0193-1 2024-09-15T17:44:15+00:00 Studies on the enzymatic synthesis of lipophilic derivatives of natural antioxidants Stamatis, H. Sereti, V. Kolisis, F. N. 1999 http://dx.doi.org/10.1007/s11746-999-0193-1 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1007%2Fs11746-999-0193-1 https://onlinelibrary.wiley.com/doi/full/10.1007/s11746-999-0193-1 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Journal of the American Oil Chemists' Society volume 76, issue 12 ISSN 0003-021X 1558-9331 journal-article 1999 crwiley https://doi.org/10.1007/s11746-999-0193-1 2024-07-30T04:21:03Z Abstract The esterification of some natural antioxidants such as cinnamic acid derivatives and ascorbic acid in non‐aqueous media, catalyzed by immobilized lipases from Candida antarctica and Rhizomucor miehei , was investigated. The alcohol chain length affected the rate of esterification of cinnamic acids by both lipases. Higher reaction rates were observed when the esterification was carried out with medium‐ or long‐chain alcohols. The rate also depended on aromatic acid structure. The reactivity of the carboxylic function of the cinnamic acids was affected by electron‐donating substituents in the aromatic ring. Higher yields were observed for the esterification of p ‐hydroxyphenylacetic acid (97%) catalyzed by C. antarctica lipase and for the esterification of cinnamic acid (59%) catalyzed by R. miehei lipase. Candida antarctica lipase was more suitable for producing ascorbic acid fatty esters, catalyzing with a relatively high yield (up to 65% within 24 h) the regioselective esterification of ascorbic acid with various fatty acids in 2‐methyl‐2‐propanol. The reaction rate and yield depended on the fatty acid chain length and on the molar ratio of reactants. All ascorbic acid fatty esters produced by this procedure exhibited a significant antioxidant activity in a micellar substrate composed of linoleic acid. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library Journal of the American Oil Chemists' Society 76 12 |
institution |
Open Polar |
collection |
Wiley Online Library |
op_collection_id |
crwiley |
language |
English |
description |
Abstract The esterification of some natural antioxidants such as cinnamic acid derivatives and ascorbic acid in non‐aqueous media, catalyzed by immobilized lipases from Candida antarctica and Rhizomucor miehei , was investigated. The alcohol chain length affected the rate of esterification of cinnamic acids by both lipases. Higher reaction rates were observed when the esterification was carried out with medium‐ or long‐chain alcohols. The rate also depended on aromatic acid structure. The reactivity of the carboxylic function of the cinnamic acids was affected by electron‐donating substituents in the aromatic ring. Higher yields were observed for the esterification of p ‐hydroxyphenylacetic acid (97%) catalyzed by C. antarctica lipase and for the esterification of cinnamic acid (59%) catalyzed by R. miehei lipase. Candida antarctica lipase was more suitable for producing ascorbic acid fatty esters, catalyzing with a relatively high yield (up to 65% within 24 h) the regioselective esterification of ascorbic acid with various fatty acids in 2‐methyl‐2‐propanol. The reaction rate and yield depended on the fatty acid chain length and on the molar ratio of reactants. All ascorbic acid fatty esters produced by this procedure exhibited a significant antioxidant activity in a micellar substrate composed of linoleic acid. |
format |
Article in Journal/Newspaper |
author |
Stamatis, H. Sereti, V. Kolisis, F. N. |
spellingShingle |
Stamatis, H. Sereti, V. Kolisis, F. N. Studies on the enzymatic synthesis of lipophilic derivatives of natural antioxidants |
author_facet |
Stamatis, H. Sereti, V. Kolisis, F. N. |
author_sort |
Stamatis, H. |
title |
Studies on the enzymatic synthesis of lipophilic derivatives of natural antioxidants |
title_short |
Studies on the enzymatic synthesis of lipophilic derivatives of natural antioxidants |
title_full |
Studies on the enzymatic synthesis of lipophilic derivatives of natural antioxidants |
title_fullStr |
Studies on the enzymatic synthesis of lipophilic derivatives of natural antioxidants |
title_full_unstemmed |
Studies on the enzymatic synthesis of lipophilic derivatives of natural antioxidants |
title_sort |
studies on the enzymatic synthesis of lipophilic derivatives of natural antioxidants |
publisher |
Wiley |
publishDate |
1999 |
url |
http://dx.doi.org/10.1007/s11746-999-0193-1 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1007%2Fs11746-999-0193-1 https://onlinelibrary.wiley.com/doi/full/10.1007/s11746-999-0193-1 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Journal of the American Oil Chemists' Society volume 76, issue 12 ISSN 0003-021X 1558-9331 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1007/s11746-999-0193-1 |
container_title |
Journal of the American Oil Chemists' Society |
container_volume |
76 |
container_issue |
12 |
_version_ |
1810491678436360192 |