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Antioxidant effect of naturally occurring furan fatty acids on oxidation of linoleic acid in aqueous dispersion
Author(s) -
Okada Youji,
Okajima Haruo,
Konishi Hirokazu,
Terauchi Misaka,
Ishii Kazuo,
Liu IMin,
Watanabe Hiroshi
Publication year - 1990
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02540506
Subject(s) - furan , chemistry , antioxidant , linoleic acid , fatty acid , organic chemistry , medicinal chemistry
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.