Natural Sulfur Compounds, Allyl Isothiocyanate and Diallyl Disulfide, Promote Cis to Trans Isomerization of Fatty Acid Esters during Heat Treatment.

Abstract

The effects of allyl isothiocyanate (AITC) and diallyl disulfide (DADS), widely found in edible vegetables, on thermal isomerization of unsaturated fatty acid esters (oleic acid methyl ester [OA-ME], linoleic acid methyl ester [LA-ME], and eicosapentaenoic acid ethyl ester [EPA-EE]) were investigated. Although heating with AITC and DADS significantly promoted cis to trans isomerization of all fatty acid esters, the isomerization trends varied greatly depending on the type of fatty acid. Specifically, AITC promoted thermal isomerization of OA-ME and LA-ME more efficiently than DADS; however, an opposite result was obtained for EPA-EE. For example, when OA-ME was heated at 180°C for 1 h with 1.0 equivalent of AITC and DADS, its trans isomer ratios reached 29.0 ± 7.1 and 7.6 ± 0.6%, respectively, and when EPA-EE was heated under the same conditions, its trans isomer ratios reached 4.2 ± 0.4 and 8.6 ± 0.2%, respectively. These results indicate that isothiocyanates and polysulfides would promote the formation of trans fatty acids in food processing under heating conditions.