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

Lecomte Jérôme, Durand Erwann, Villeneuve Pierre. 2018. Enzymatic functionalization of vinyl phenols and evaluation their resulting antioxidant properties in cell and emulsion model systems. In : Abstracts of the 2018 AOCS Annual Meeting & Expo. AOCS. Minneapolis : AOCS, Résumé, 3. 2018 AOCS Annual Meeting & Expo. 109, Minneapolis, États-Unis, 6 Mai 2018/9 Mai 2018.

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2018_AOCS lipid oxidation.pdf

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Résumé : 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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