l-5-Alk(en)ylthiomethylhydantoin-(±)-S-oxides: Non-enzymatical Precursors of Fresh Flavors of Allium Plants

Abstract

The antimicrobial l-5-alk(en)ylthiomethylhydantoin-(±)-S-oxides (RHSO) decompose via β-elimination reaction under physiological conditions to give alk(en)yl thiosulfinates as antimicrobial principles. The resemblance of the reaction and reaction products to those of alliin–alliinase system prompted us to examine the evaluation of RHSO as non-enzymatical precursors of allium flavors. The volatiles arising out of a mixture of l-5-allylthiomethylhydantoin-(±)-S-oxide (AHSO) and l-5-methylthiomethylhydantoin-(±)-S-oxide (MHSO) were compared with those of comminuted garlic. Both flavors were organoleptically quite similar to each other, and the gas Chromatographic and mass spectroscopic evidences are shown. Application of AHSO as a standard compound to quantitative analysis of alliin or allicin is also described.