The electron impact mass spectral behaviour of 14 synthetically prepared mercapturic acid methyl esters was examined. The most important and characteristic fragmentation reactions are discussed and special emphasis is made on the occurrence and the mechanism of two fragmentation pathways, which were recognized as 'retro-Michael' reactions. In principle, each reaction may result in the formation of two typical ions. In addition, three characteristic 'key-ions' originating from the N-acetyl( -I-)cysteine methyl ester part of the mercapturic acids were recognized in all mercapturic acid methyl esters investigated; these 'key-ions' can most probably be used as a tool for the qualitative as well as the quantitative analysis of mercapturic acids by gas chromatography mass spectrometry in biological fluids.
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