Synthesis of lipophilic antioxidants by a lipase-B-catalyzed addition of peracids to the double bond of 4-vinyl-2-methoxyphenol

SPO/SPIRAL 4-Vinyl guaiacol (2) was lipophilized through the electrophilic addition of peracids to its vinylic double bond. Those peracids were formed in situ, by the Candida antarctica lipase-B-assisted perhydrolysis of carboxylic acids ranging from C2 to C18, in hydrogen peroxide solution. The add...

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Bibliographic Details
Published in:Journal of Agricultural and Food Chemistry
Main Authors: Zago, Erika, Durand, Erwann, Barouh, Nathalie, Lecomte, Jérôme, Villeneuve, Pierre, Aouf, Chahinaz
Other Authors: Ingénierie des Agro-polymères et Technologies Émergentes (UMR IATE), Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA)-Université Montpellier 2 - Sciences et Techniques (UM2)-Centre international d'études supérieures en sciences agronomiques (Montpellier SupAgro)-Université de Montpellier (UM)-Institut national d’études supérieures agronomiques de Montpellier (Montpellier SupAgro), Sciences Pour l'Oenologie (SPO), Université Montpellier 1 (UM1)-Institut National de la Recherche Agronomique (INRA)-Université de Montpellier (UM)-Institut national d’études supérieures agronomiques de Montpellier (Montpellier SupAgro)
Format: Article in Journal/Newspaper
Language:English
Published: HAL CCSD 2015
Subjects:
lipophilization
vinylphenols
electrophilic addition
antioxidant activity
[SDV.SA]Life Sciences [q-bio]/Agricultural sciences
[SDV.IDA]Life Sciences [q-bio]/Food engineering
[SDV.BIO]Life Sciences [q-bio]/Biotechnology
Antarc*
Antarctica
Online Access:https://hal.science/hal-01269365
https://doi.org/10.1021/acs.jafc.5b03551
Description
Summary:SPO/SPIRAL 4-Vinyl guaiacol (2) was lipophilized through the electrophilic addition of peracids to its vinylic double bond. Those peracids were formed in situ, by the Candida antarctica lipase-B-assisted perhydrolysis of carboxylic acids ranging from C2 to C18, in hydrogen peroxide solution. The addition of peracids with 4-8 carbons in their alkyl chains led to the formation of two regioisomers, with the prevalence of hydroxyesters bearing a primary free hydroxyl (4c-4e). This prevalence became more pronounced when peracids with longer alkyl chains (C10-C18) were used. In this case, only isomers 4f-4h were formed. The antioxidant activity of the resulting hydroxyesters was assessed by means of the conjugated autoxidizable triene (CAT) assay, and it was found out that the 4-vinyl guaiacol antioxidant activity was significantly increased by grafting alkyl chains with 2-8 carbons.

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