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Lipase-catalyzed synthesis of chlorogenate fatty esters in solvent-free medium

Paper ID Volume ID Publish Year Pages File Format Full-Text
18079 42711 2007 6 PDF Available
Title
Lipase-catalyzed synthesis of chlorogenate fatty esters in solvent-free medium
Abstract

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.

Keywords
Fatty chlorogenate esters; Lipophilization; Lipase; Candida antarctica B; Esterification; Transesterification; 5-Caffeoyl quinic acid
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Lipase-catalyzed synthesis of chlorogenate fatty esters in solvent-free medium
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Publisher
Database: Elsevier - ScienceDirect
Journal: Enzyme and Microbial Technology - Volume 41, Issues 6–7, 1 November 2007, Pages 721–726
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us