Antioxidant effect of naturally occurring furan fatty acids on oxidation of linoleic acid in aqueous dispersion

Naturally occurring furan fatty acids were synthesized and their antioxidant activity has been studied during the oxidation of linoleic acid in the phosphate buffer, pH 6.9, in the dark. The extent of the oxidation was followed both by the accumulation of conjugated diene and by the measurement of the residual amounts of linoleic acid. The tetra-alkylsubstituted furan fatty acids were found to suppress the oxidation. The trialkylsubstituted compound also showed antioxidant activity, being about 50% as effective as the tetra-alkylsubstituted ones. The di-alkylsubstituted one revealed no significant activity. The antioxidant activity of furan fatty acids depended on the number of substituents on the furan ring. Therefore, a tetra-alkylsubstituted furan ring may be necessary for the antioxidant action of furan fatty acids. The tetra-alkylsubstituted furan fatty acids reduced 1,1-diphenyl-2-picrylhydrazyl, reacted with the peroxyl radical generated from the thermal decomposition of a radical initiator, 2,2′-azobis(2-amidinopropane)hydrochloride (AAPH), and also suppressed the AAPH-induced oxidation of linoleic acid, indicating that, by scavenging, the peroxyl radical furan fatty acids inhibit the oxidation.