Use of essential oils as media for the enantioselective esterification of the monoterpene perillyl alcohol catalyzed by lipase
Abstract The synthesis of perillyl alcohol esters by direct esterification catalyzed by immobilized lipase from Candida antarctica (Novozyme 435) was studied. For this purpose, fatty acids with a chain length from 3‐16 were used. The reactions were carried out in mixtures of α‐pinene and myrcene as...
Published in: | European Journal of Lipid Science and Technology |
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Online Access: | http://dx.doi.org/10.1002/ejlt.200390026 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fejlt.200390026 https://onlinelibrary.wiley.com/doi/pdf/10.1002/ejlt.200390026 |
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crwiley:10.1002/ejlt.200390026 2024-09-09T19:02:55+00:00 Use of essential oils as media for the enantioselective esterification of the monoterpene perillyl alcohol catalyzed by lipase Skouridou, Vasso Stamatis, Haralambos Kolisis, Fragiskos N. 2003 http://dx.doi.org/10.1002/ejlt.200390026 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fejlt.200390026 https://onlinelibrary.wiley.com/doi/pdf/10.1002/ejlt.200390026 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor European Journal of Lipid Science and Technology volume 105, issue 3-4, page 115-120 ISSN 1438-7697 1438-9312 journal-article 2003 crwiley https://doi.org/10.1002/ejlt.200390026 2024-07-02T04:10:58Z Abstract The synthesis of perillyl alcohol esters by direct esterification catalyzed by immobilized lipase from Candida antarctica (Novozyme 435) was studied. For this purpose, fatty acids with a chain length from 3‐16 were used. The reactions were carried out in mixtures of α‐pinene and myrcene as well as in pure organic solvents. It was found that the esterification rates increased from 3.7‐6.9 mM/min when using decreasing concentrations of myrcene in α‐pinene (100‐0%). Higher rates and conversions were obtained with decanoic acid as the acyl donor (6.9 mM/min, 81.5%), while lower conversions were obtained with fatty acids of shorter (propionic acid, 5.6%) or longer (hexadecanoic acid, 62.5%) carbon chain. In addition, it was found that the effect of the water activity depended on the chain length of the acyl donor and the composition of the solvent mixture. Also, esterification rates increased from 1.8‐6.9 mM/min with increasing hydrophobicity of the solvent (logP from 0.9‐4.8) of the organic solvent used. Finally, it was found that Candida antarctica lipase presented a preference in the esterification of (S)‐(—)‐ and (R)‐(+)‐perillyl alcohol in favor of the (R)‐(+) enantiomer. The enantioselectivity was found increased with increasing logP, whereas the water activity of the reaction mixture did not affect the enantioselectivity significantly. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library European Journal of Lipid Science and Technology 105 3-4 115 120 |
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English |
description |
Abstract The synthesis of perillyl alcohol esters by direct esterification catalyzed by immobilized lipase from Candida antarctica (Novozyme 435) was studied. For this purpose, fatty acids with a chain length from 3‐16 were used. The reactions were carried out in mixtures of α‐pinene and myrcene as well as in pure organic solvents. It was found that the esterification rates increased from 3.7‐6.9 mM/min when using decreasing concentrations of myrcene in α‐pinene (100‐0%). Higher rates and conversions were obtained with decanoic acid as the acyl donor (6.9 mM/min, 81.5%), while lower conversions were obtained with fatty acids of shorter (propionic acid, 5.6%) or longer (hexadecanoic acid, 62.5%) carbon chain. In addition, it was found that the effect of the water activity depended on the chain length of the acyl donor and the composition of the solvent mixture. Also, esterification rates increased from 1.8‐6.9 mM/min with increasing hydrophobicity of the solvent (logP from 0.9‐4.8) of the organic solvent used. Finally, it was found that Candida antarctica lipase presented a preference in the esterification of (S)‐(—)‐ and (R)‐(+)‐perillyl alcohol in favor of the (R)‐(+) enantiomer. The enantioselectivity was found increased with increasing logP, whereas the water activity of the reaction mixture did not affect the enantioselectivity significantly. |
format |
Article in Journal/Newspaper |
author |
Skouridou, Vasso Stamatis, Haralambos Kolisis, Fragiskos N. |
spellingShingle |
Skouridou, Vasso Stamatis, Haralambos Kolisis, Fragiskos N. Use of essential oils as media for the enantioselective esterification of the monoterpene perillyl alcohol catalyzed by lipase |
author_facet |
Skouridou, Vasso Stamatis, Haralambos Kolisis, Fragiskos N. |
author_sort |
Skouridou, Vasso |
title |
Use of essential oils as media for the enantioselective esterification of the monoterpene perillyl alcohol catalyzed by lipase |
title_short |
Use of essential oils as media for the enantioselective esterification of the monoterpene perillyl alcohol catalyzed by lipase |
title_full |
Use of essential oils as media for the enantioselective esterification of the monoterpene perillyl alcohol catalyzed by lipase |
title_fullStr |
Use of essential oils as media for the enantioselective esterification of the monoterpene perillyl alcohol catalyzed by lipase |
title_full_unstemmed |
Use of essential oils as media for the enantioselective esterification of the monoterpene perillyl alcohol catalyzed by lipase |
title_sort |
use of essential oils as media for the enantioselective esterification of the monoterpene perillyl alcohol catalyzed by lipase |
publisher |
Wiley |
publishDate |
2003 |
url |
http://dx.doi.org/10.1002/ejlt.200390026 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fejlt.200390026 https://onlinelibrary.wiley.com/doi/pdf/10.1002/ejlt.200390026 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
European Journal of Lipid Science and Technology volume 105, issue 3-4, page 115-120 ISSN 1438-7697 1438-9312 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/ejlt.200390026 |
container_title |
European Journal of Lipid Science and Technology |
container_volume |
105 |
container_issue |
3-4 |
container_start_page |
115 |
op_container_end_page |
120 |
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1809816941924188160 |