New volatile sulfur-containing constituents in a simultaneous distillation-extraction extract of red bell peppers (Capsicum annuum)

An extract of red bell peppers ( Capsicum annuum) was prepared by simultaneous distillation-extraction (SDE, Likens-Nickerson). In addition to the already known (3 E)-3-hepten-2-one ( 1), the unsaturated C9-ketones 1-nonen-4-one ( 2), (2 E)-2-nonen-4-one ( 3), and (2 E,5 E)-2,5-nonadien-4-one ( 4), 2-methoxy-3-isobutylpyrazine ( 5), and heptane-2-thiol ( 6), we identified 19 new thiols (the aliphatic saturated and unsaturated thiols 14- 16, and 22- 27, the mercapto-ketones 12 and 13, the mercapto-alcohols 17, 18, and 30, the dithiols 19 and 28, the methylthio-thiols 20 and 21, and the thiophene-thiol 31) and the two new dithiolanes 10 and 29. All of them are structurally related to the unsaturated C7- and C9-ketones 1- 4. The free thiols were enriched using Affi-Gel 501 ( p-aminophenyl-mercuric acetate grafted on an agarose gel). The new compounds were confirmed by syntheses and were organoleptically evaluated.