Decomposition of Allyl Isothiocyanate in Aqueous Solution

Abstract

Allyl isothiocyanate was gradually decomposed in aqueous solution to produe a garlic like odor. The decomposition of this isothiocyanate was not ased on hydrolysis of R-NCS as in the case of p-hydroxybenzyl isothiocyanate, but the addition reaction on -N-C-S. Four substances formed with the decomposithion of the disothiocyanate were isolated, and their chemical constitutuons were clarified. Allyl isothiocyanate was decomposed to allyl allyldithiocarbamate (III), which was degradated to diallyl tetra- and penta-sulfide (II), and this Poly-sulfide was further degradated to paraffin like hydrocarbon (I) and ssulfur. Moreove, N, N'-diallylthourea (IV) was produced by the addition reaction of allylamine, formed from the isothiocyanate by action of water, to residual isohtiocyanate. © 1969, Japan Society for Bioscience, Biotechnology, and Agrochemistry. All rights reserved.