Degradation of Alkyl Isothiocyanates in Methanol Solution

Studies on the Volatile Components of Wasabi and Horse Radish Part II

Abstract

Alkyl isothiocyanates were gradually changed into the components having an alkyl sulfides like odor in methanol solution. To clarify the structures of these components, they were separated by silica gel column chromatography, and examined by IR, NMR and mass spectrometry. Alkyl isothiocyanates were found to be converted to methyl alkyl thiocarbamates by the addition of methanol in the solution. Ten % of allyl isothiocyanate changed into methyl allyl thiocarbamate in methanol solution for a week. It is assumed that alkyl thiocarbamates will be produced from alkyl isothiocyanates by the attack of reagents having electron-releasing property.