Antioxidant mechanism studies on ferulic acid: identification of oxidative coupling products from methyl ferulate and linoleate

In our studies of the chain-breaking antioxidant mechanism of natural phenols in food components, ferulic acid, a phenolic acid widely distributed in edible plants, especially grain, was investigated. The radical oxidation reaction of a large amount of ethyl linoleate in the presence of the methyl ester of ferulic acid produced four types of peroxides as radical termination products. The isolation and structure determination of the peroxides revealed that they had tricyclic structures which consisted of ethyl linoleate, methyl ferulate, and molecular oxygen. Based on the formation pathway of the products, a radical scavenging reaction occurred at the 3'-position of the ferulate radical with the four types of peroxyl radicals of ethyl linoleate. The produced peroxides subsequently underwent intramolecular Diels-Alder reaction to afford stable tricyclic peroxides.