Optimal production of 7,10-epoxy-octadeca-7,9-dienoic acid from 7,10-dihydroxy-8(E)-octadecenoic acid by heat treatment

Furan fatty acids (F-acid) are known to have strong antioxidant properties, including radical scavenging activity, which play important roles in biological systems including humans. F-acids are widely distributed in most biological systems as trace components and their biosyntheses are complicated. Although several studies were reported on the chemical synthesis of various types of F-acids, it required complicated and multistep chemical reactions. Recently, a simple one-step heat treatment method was developed for the production of a novel furan fatty acid, 7,10-epoxy-octadeca-7,9-dienoic acid (7,10-EODA) from 7,10-dihydroxy-8(E)-octadecenoic acid (DOD). (Journal of Agricultural and Food Chemistry, 2011, 59, 8175–8179). In this report, we optimized reaction conditions for the efficient production of 7,10-EODA from DOD by heat treatment. Under optimal conditions tested, the maximum production yield of 7,10-EODA was 80% with incubation in hexane for at least 48 h at 85 °C or above.