Gas chromatography-mass spectrometry of nitriles, isothiocyanates and oxazolidinethiones derived from cruciferous glucosinolates

Hydrolysis/autolysis of the glucosinolates found in wild and cultivated cruciferous plants can yield a variety of nitrogenous compounds for the alkyl or aryl moiety. These products include nitriles, isothiocyanates and oxazolidinethiones, all of which may present potential hazards in foods and feeds. More than 70 glucosinolates are known, and almost all the hydrolysis products are amenable to analysis by gas chromatography. The reaction can proceed in different ways, depending upon the conditions of hydrolysis or treatment of the plant during harvest or storage, and confirmation of the identifications made by retention data is sometimes needed. Gas chromatography‐mass spectrometry can usually provide this additional structural information. Spectra of alkyl or aryl nitriles and isothiocyanates that contain other functional groups (hydroxyl, episulphide, methylthio, sulphinyl, sulphonyl) and oxazolidinethiones are presented and discussed.