- New volatile sulfur-containing constituents in a simultaneous distillation-extraction extract of red bell peppers (Capsicum annuum)
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An extract of red bell peppers (Capsicum annuum) was prepared by simultaneous distillation-extraction (SDE, Likens-Nickerson). In addition to the already known (3E)-hepten-2-one (1), the unsaturated C9-ketones 1-nonen-4-one (2), (2E)-2-nonen-4-one (3), and (2E,5E)-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.
- Naef, Regula,Velluz, Alain,Jaquier, Alain
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experimental part
p. 517 - 527
(2009/04/10)
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- Synthesis of Z,Z-Skipped Diene Macrolide Pheromones for Cryptolestes and Oryzaephilus Grain Beetles (Coleoptera Cucujidae)
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Three macrolide aggregation pheromones for Cryptolestes pusillus, Cryptolestes turcicus, and Oryzaephilus mercator were synthesized stereoselectively from acyclic precursors.The first, 13-methyl-(5Z,8Z)-tridecadienolide (I), is an aggregation pheromone for C. turcicus and had been tentatively identified previously in Phoracantha synonyma.The second, 11-methyl-(3Z,6Z)-undecadienolide (II), is an aggregation pheromone for O. mercator.The third, (3Z,6Z)-dodecadienolide (III) is an aggregation pheromone for O. mercator and is also slightly attractive to C. pusillus.The racemic and enantiomeric forms of I were synthesized.
- Millar, Jocelyn G.,Oehlschlager, Allan C.
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p. 2332 - 2338
(2007/10/02)
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