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. Lipase-catalyzed synthesis of chlorogenate fatty esters in solvent-free medium. Enzyme and Microbial Technology, 41 : 721-726.

https://doi.org/10.1016/j.enzmictec.2007.06.004

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Résumé : 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.

Mots-clés Agrovoc : ester, acide chlorogénique, synthèse chimique, estérification, estérase, Candida, lipase

Mots-clés complémentaires : Ester gras, Transestérification, Lipophilisation, Candida antarctica

Classification Agris : Q02 - Traitement et conservation des produits alimentaires

Champ stratégique Cirad : Axe 3 (2005-2013) - Alimentation accessible et de qualité

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