title: Antioxidant properties and efficacies of synthesized alkyl caffeates, ferulates, and coumarates.
abstract: Caffeic, ferulic, and coumaric acids were lipophilized with saturated fatty alcohols (C1-C20). The antioxidant properties of these hydroxycinnamic acids and their alkyl esters were evaluated in various assays. Furthermore, the antioxidant efficiency of the compounds was evaluated in a simple o/w microemulsion using the conjugated autoxidizable triene (CAT) assay. All evaluated phenolipids had radical scavenging, reducing power, and metal chelating properties. Only caffeic acid and caffeates were able to form a complex with iron via their catechol group in the phenolic ring. In the o/w emulsion, the medium chain phenolipids of the three homologues series were most efficient. The antioxidant properties and efficacies were dependent upon functional groups substituted to the ring structure and were in the following order: caffeic acid and caffeates > ferulic acid and ferulates > coumaric acid and coumarates. Moreover, the results demonstrated that the test system has an impact on the antioxidative properties measured.
authors.affiliation: Division of Industrial Food Research, National Food Institute (DTU Food), Technical University of Denmark , DK-2800 Kgs. Lyngby, Denmark.
authors.forename: Ann-Dorit Moltke
authors.initials: AD
authors.lastname: Sørensen
authors.forename: Erwann
authors.initials: E
authors.lastname: Durand
authors.forename: Mickaël
authors.initials: M
authors.lastname: Laguerre
authors.forename: Christelle
authors.initials: C
authors.lastname: Bayrasy
authors.forename: Jérôme
authors.initials: J
authors.lastname: Lecomte
authors.forename: Pierre
authors.initials: P
authors.lastname: Villeneuve
authors.forename: Charlotte
authors.initials: C
authors.lastname: Jacobsen
mesh_terms: D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry*; D002109:Caffeic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D003373:Coumaric Acids / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D000975:Antioxidants; D002109:Caffeic Acids; D003373:Coumaric Acids; C004999:ferulic acid; C040048:caffeic acid
keywords: caffeic acid; conjugated autoxidizable triene (CAT) assay; coumaric acid; cut-off effect; ferulic acid; lipophilization; phenolipids