Lipase-catalyzed synthesis of chlorogenate fatty esters in solvent-free medium
Chlorogenic acid (5-caffeoylquinic acid or 5-CQA) is an hydrophilic phenolic compound with antioxidant properties. Because of its high polarity, its antioxidant properties may be altered when formulated in oil based food or cosmetic preparations. Therefore, there is an interest in trying to enhance...
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Online Access: | http://agritrop.cirad.fr/540835/ http://agritrop.cirad.fr/540835/1/document_540835.pdf https://doi.org/10.1016/j.enzmictec.2007.06.004 |
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ftcirad:oai:agritrop.cirad.fr:540835 2023-05-15T13:54:33+02:00 Lipase-catalyzed synthesis of chlorogenate fatty esters in solvent-free medium Lopez Giraldo, Luis Javier Laguerre, Mickaël Lecomte, Jérôme Figueroa-Espinoza, Maria-Cruz Barouh, Nathalie Baréa, Bruno Villeneuve, Pierre 2007 application/pdf http://agritrop.cirad.fr/540835/ http://agritrop.cirad.fr/540835/1/document_540835.pdf https://doi.org/10.1016/j.enzmictec.2007.06.004 eng eng http://agritrop.cirad.fr/540835/ Lipase-catalyzed synthesis of chlorogenate fatty esters in solvent-free medium. Lopez Giraldo Luis Javier, Laguerre Mickaël, Lecomte Jérôme, Figueroa-Espinoza Maria-Cruz, Barouh Nathalie, Baréa Bruno, Villeneuve Pierre. 2007. Enzyme and Microbial Technology, 41 : 721-726.https://doi.org/10.1016/j.enzmictec.2007.06.004 <https://doi.org/10.1016/j.enzmictec.2007.06.004> http://agritrop.cirad.fr/540835/1/document_540835.pdf Cirad license info:eu-repo/semantics/restrictedAccess https://agritrop.cirad.fr/mention_legale.html Enzyme and Microbial Technology Q02 - Traitement et conservation des produits alimentaires Ester Acide chlorogénique Synthèse chimique Estérification Estérase Candida Lipase http://aims.fao.org/aos/agrovoc/c_2671 http://aims.fao.org/aos/agrovoc/c_36179 http://aims.fao.org/aos/agrovoc/c_28580 http://aims.fao.org/aos/agrovoc/c_28361 http://aims.fao.org/aos/agrovoc/c_2670 http://aims.fao.org/aos/agrovoc/c_1247 http://aims.fao.org/aos/agrovoc/c_12194 article info:eu-repo/semantics/article Journal Article info:eu-repo/semantics/publishedVersion 2007 ftcirad https://doi.org/10.1016/j.enzmictec.2007.06.004 2023-01-03T23:47:24Z Chlorogenic acid (5-caffeoylquinic acid or 5-CQA) is an hydrophilic phenolic compound with antioxidant properties. Because of its high polarity, its antioxidant properties may be altered when formulated in oil based food or cosmetic preparations. Therefore, there is an interest in trying to enhance its hydrophobicity by grafting of an aliphatic chain. Such lipophilization reactions can be generally achieved through enzymatic catalysis. Our study consisted in synthesizing fatty cholorogenate esters in a two steps reaction. Firstly, 5-CQA was chemically esterified by methanol using an Amberlite IR120 H resin to obtain methyl chlorogenate that is more soluble in the fatty alcohols than 5-CQA. Secondly, this chlorogenate intermediate was transesterified with fatty alcohols of various chain lengths (C4, C8, C12, or C16) in the presence of Candida antarctica B lipase. Under optimal reaction conditions (aw = 0.05; 5% (w/w) of biocatalyst), the transesterification rates were until two-fold higher than in the direct lipase-catalyzed esterification of chlorogenic acid by the same alcohols. The two-step reaction overall yield was between 61 and 93% depending on the alcohol chain length, whereas it was 40-60% for the direct esterification with the same alcohols. © 2007 Elsevier Inc. All rights reserved. Article in Journal/Newspaper Antarc* Antarctica CIRAD: Agritrop (Centre de coopération internationale en recherche agronomique pour le développement) Enzyme and Microbial Technology 41 6-7 721 726 |
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Open Polar |
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CIRAD: Agritrop (Centre de coopération internationale en recherche agronomique pour le développement) |
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ftcirad |
language |
English |
topic |
Q02 - Traitement et conservation des produits alimentaires Ester Acide chlorogénique Synthèse chimique Estérification Estérase Candida Lipase http://aims.fao.org/aos/agrovoc/c_2671 http://aims.fao.org/aos/agrovoc/c_36179 http://aims.fao.org/aos/agrovoc/c_28580 http://aims.fao.org/aos/agrovoc/c_28361 http://aims.fao.org/aos/agrovoc/c_2670 http://aims.fao.org/aos/agrovoc/c_1247 http://aims.fao.org/aos/agrovoc/c_12194 |
spellingShingle |
Q02 - Traitement et conservation des produits alimentaires Ester Acide chlorogénique Synthèse chimique Estérification Estérase Candida Lipase http://aims.fao.org/aos/agrovoc/c_2671 http://aims.fao.org/aos/agrovoc/c_36179 http://aims.fao.org/aos/agrovoc/c_28580 http://aims.fao.org/aos/agrovoc/c_28361 http://aims.fao.org/aos/agrovoc/c_2670 http://aims.fao.org/aos/agrovoc/c_1247 http://aims.fao.org/aos/agrovoc/c_12194 Lopez Giraldo, Luis Javier Laguerre, Mickaël Lecomte, Jérôme Figueroa-Espinoza, Maria-Cruz Barouh, Nathalie Baréa, Bruno Villeneuve, Pierre Lipase-catalyzed synthesis of chlorogenate fatty esters in solvent-free medium |
topic_facet |
Q02 - Traitement et conservation des produits alimentaires Ester Acide chlorogénique Synthèse chimique Estérification Estérase Candida Lipase http://aims.fao.org/aos/agrovoc/c_2671 http://aims.fao.org/aos/agrovoc/c_36179 http://aims.fao.org/aos/agrovoc/c_28580 http://aims.fao.org/aos/agrovoc/c_28361 http://aims.fao.org/aos/agrovoc/c_2670 http://aims.fao.org/aos/agrovoc/c_1247 http://aims.fao.org/aos/agrovoc/c_12194 |
description |
Chlorogenic acid (5-caffeoylquinic acid or 5-CQA) is an hydrophilic phenolic compound with antioxidant properties. Because of its high polarity, its antioxidant properties may be altered when formulated in oil based food or cosmetic preparations. Therefore, there is an interest in trying to enhance its hydrophobicity by grafting of an aliphatic chain. Such lipophilization reactions can be generally achieved through enzymatic catalysis. Our study consisted in synthesizing fatty cholorogenate esters in a two steps reaction. Firstly, 5-CQA was chemically esterified by methanol using an Amberlite IR120 H resin to obtain methyl chlorogenate that is more soluble in the fatty alcohols than 5-CQA. Secondly, this chlorogenate intermediate was transesterified with fatty alcohols of various chain lengths (C4, C8, C12, or C16) in the presence of Candida antarctica B lipase. Under optimal reaction conditions (aw = 0.05; 5% (w/w) of biocatalyst), the transesterification rates were until two-fold higher than in the direct lipase-catalyzed esterification of chlorogenic acid by the same alcohols. The two-step reaction overall yield was between 61 and 93% depending on the alcohol chain length, whereas it was 40-60% for the direct esterification with the same alcohols. © 2007 Elsevier Inc. All rights reserved. |
format |
Article in Journal/Newspaper |
author |
Lopez Giraldo, Luis Javier Laguerre, Mickaël Lecomte, Jérôme Figueroa-Espinoza, Maria-Cruz Barouh, Nathalie Baréa, Bruno Villeneuve, Pierre |
author_facet |
Lopez Giraldo, Luis Javier Laguerre, Mickaël Lecomte, Jérôme Figueroa-Espinoza, Maria-Cruz Barouh, Nathalie Baréa, Bruno Villeneuve, Pierre |
author_sort |
Lopez Giraldo, Luis Javier |
title |
Lipase-catalyzed synthesis of chlorogenate fatty esters in solvent-free medium |
title_short |
Lipase-catalyzed synthesis of chlorogenate fatty esters in solvent-free medium |
title_full |
Lipase-catalyzed synthesis of chlorogenate fatty esters in solvent-free medium |
title_fullStr |
Lipase-catalyzed synthesis of chlorogenate fatty esters in solvent-free medium |
title_full_unstemmed |
Lipase-catalyzed synthesis of chlorogenate fatty esters in solvent-free medium |
title_sort |
lipase-catalyzed synthesis of chlorogenate fatty esters in solvent-free medium |
publishDate |
2007 |
url |
http://agritrop.cirad.fr/540835/ http://agritrop.cirad.fr/540835/1/document_540835.pdf https://doi.org/10.1016/j.enzmictec.2007.06.004 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Enzyme and Microbial Technology |
op_relation |
http://agritrop.cirad.fr/540835/ Lipase-catalyzed synthesis of chlorogenate fatty esters in solvent-free medium. Lopez Giraldo Luis Javier, Laguerre Mickaël, Lecomte Jérôme, Figueroa-Espinoza Maria-Cruz, Barouh Nathalie, Baréa Bruno, Villeneuve Pierre. 2007. Enzyme and Microbial Technology, 41 : 721-726.https://doi.org/10.1016/j.enzmictec.2007.06.004 <https://doi.org/10.1016/j.enzmictec.2007.06.004> http://agritrop.cirad.fr/540835/1/document_540835.pdf |
op_rights |
Cirad license info:eu-repo/semantics/restrictedAccess https://agritrop.cirad.fr/mention_legale.html |
op_doi |
https://doi.org/10.1016/j.enzmictec.2007.06.004 |
container_title |
Enzyme and Microbial Technology |
container_volume |
41 |
container_issue |
6-7 |
container_start_page |
721 |
op_container_end_page |
726 |
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1766260533735981056 |