title: Synthesis of Lipophilic Antioxidants by a Lipase-B-Catalyzed Addition of Peracids to the Double Bond of 4-Vinyl-2-methoxyphenol.
abstract: 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.
authors.affiliation: L'Unité Mixte de Recherche Ingénierie des Agro-polymères et Technologies Émergentes (UMR IATE), Centre de Coopération Internationale en Recherche Agronomique pour le Développement (CIRAD) , F-34060 Montpellier, France.
authors.forename: Erika
authors.initials: E
authors.lastname: Zago
authors.affiliation: L'Unité Mixte de Recherche Ingénierie des Agro-polymères et Technologies Émergentes (UMR IATE), Centre de Coopération Internationale en Recherche Agronomique pour le Développement (CIRAD) , F-34060 Montpellier, France.
authors.forename: Erwann
authors.initials: E
authors.lastname: Durand
authors.affiliation: L'Unité Mixte de Recherche Ingénierie des Agro-polymères et Technologies Émergentes (UMR IATE), Centre de Coopération Internationale en Recherche Agronomique pour le Développement (CIRAD) , F-34060 Montpellier, France.
authors.forename: Nathalie
authors.initials: N
authors.lastname: Barouh
authors.affiliation: L'Unité Mixte de Recherche Ingénierie des Agro-polymères et Technologies Émergentes (UMR IATE), Centre de Coopération Internationale en Recherche Agronomique pour le Développement (CIRAD) , F-34060 Montpellier, France.
authors.forename: Jérôme
authors.initials: J
authors.lastname: Lecomte
authors.affiliation: L'Unité Mixte de Recherche Ingénierie des Agro-polymères et Technologies Émergentes (UMR IATE), Centre de Coopération Internationale en Recherche Agronomique pour le Développement (CIRAD) , F-34060 Montpellier, France.
authors.forename: Pierre
authors.initials: P
authors.lastname: Villeneuve
authors.affiliation: L'Unité Mixte de Recherches (UMR) 1083 Sciences Pour l'Oenologie (SPO), Institut National de la Recherche Agronomique (INRA) , F-34060 Montpellier, France.
authors.forename: Chahinez
authors.initials: C
authors.lastname: Aouf
mesh_terms: D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry; D055162:Biocatalysis; D004800:Enzymes, Immobilized / Q000737:chemistry; D005656:Fungal Proteins / Q000737:chemistry*; D008049:Lipase / Q000737:chemistry*; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry*
chemical_list: D000975:Antioxidants; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D010636:Phenols; D008049:Lipase; C431349:lipase B, Candida antarctica
keywords: antioxidant activity; electrophilic addition; lipophilization; vinylphenols