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Enzymatic functionalization of vinyl phenols and evaluation their resulting antioxidant properties in cell and emulsion model systems

Lecomte J., Durand E., Villeneuve P.. 2018. In : Abstracts of the 2018 AOCS Annual Meeting & Expo. Minneapolis : AOCS, p. 3-3. 2018 AOCS Annual Meeting & Expo. 109, 2018-05-06/2018-05-09, Minneapolis (Etats-Unis).

Vinyl phenols were 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. This prevalence became more pronounced when peracids with longer alkyl chains (C10-C18) were used. The antioxidant activity of the resulting hydroxyesters was assessed by means of the conjugated autoxidizable triene (CAT) assay, and on cell model systems.

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