Study of the fragmentation of 3(2H)-furanones by mass spectrometry

Fragmentation of 4-hydroxy-5-methyl-3(2H)-furanone, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, and 2(or 5)-ethyl-4-hydroxy-5(or 2)-methyl-3(2H)-furanone was studied by gas chromatography/mass spectrometry and by gas chromatography/tandem mass spectrometry. Experiments were carried out using unlabeled reference compounds and isotopically labeled molecules. The latter were obtained either by synthesis or through the Maillard reaction based on xylose and alanine or glycine. A general fragmentation pathway of alkylated 4-hydroxy-3(2H)-furanones is proposed on the basis of cross-examination of the mass spectrometric data obtained from these different compounds.