One-Step Production of a Biologically Active Novel Furan Fatty Acid from 7,10-Dihydroxy-8(E)-octadecenoic Acid

摘要

Furan fatty acids (F-acids) gain special attention because they are known to play important roles in biological systems including humans. Specifically, F-acids are known to have strong antioxidant activitis such as radical scavenging activity. Although widely distributed in most biological systems, F-acids are trace components and their biosynthesis is complicated and quite different by sources. On the basis of biochemical study, they are considered to be an essential nutritional factor for mammals and should be provided through the diet. Hence, several studies reported the chemical synthesis of F-acids using chemical catalysts. However, chemical synthesis required complicated multiple steps. In this study was developed a simple one-step synthesis of a novel F-acid, 7,10-epoxyoctadeca-7,9-dienoic acid (EODA), from a dihydroxyl fatty acid, 7,10-dihydroxy-8(E)-octadecenoic acid (DOD), by heat treatment. The structure of EODA was confirmed by GC-MS, NMR, and FTIR analyses, and maximum production yield under the reaction conditions of 90 °C and 24 h reached 80%.