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 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.
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Subjects: | 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, |
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dig-cirad-fr-5408352024-01-28T15:21:31Z http://agritrop.cirad.fr/540835/ 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> 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 eng 2007 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 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 info:eu-repo/semantics/article Journal Article info:eu-repo/semantics/publishedVersion http://agritrop.cirad.fr/540835/1/document_540835.pdf application/pdf Cirad license info:eu-repo/semantics/restrictedAccess https://agritrop.cirad.fr/mention_legale.html https://doi.org/10.1016/j.enzmictec.2007.06.004 10.1016/j.enzmictec.2007.06.004 info:eu-repo/semantics/altIdentifier/doi/10.1016/j.enzmictec.2007.06.004 info:eu-repo/semantics/altIdentifier/purl/https://doi.org/10.1016/j.enzmictec.2007.06.004 |
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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 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 |
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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 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 |
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 |
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 |
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 |
url |
http://agritrop.cirad.fr/540835/ http://agritrop.cirad.fr/540835/1/document_540835.pdf |
work_keys_str_mv |
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_version_ |
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