Tobacco smoke chemistry. 1. A chemical and mass spectrometric study of tobacco smoke alkyl 2-hydroxy-2-cyclopentenones.

A series of alkyl 2-hydroxy-2-cyclopentenones, which comprise biologically and organoleptically active compounds, have been synthesized and subjected to high resolution mass spectrometric studies to clarify structurally significant fragmentation pathways. On the basis of these results, 26 alkyl 2-hydroxy-2-cyclopentenones were identified in the weakly acidic fraction of smoke condensate from American blend type cigarettes, eighteen of which had not been detected in tobacco smoke previously. The utility for identification purposes of the corresponding quinoxaline derivatives, obtained through condensation with o-phenylenediamine, is discussed.