Identification and synthesis of 2-heptanethiol, a new flavor compound found in bell peppers.
2-Heptanethiol was identified for the first time as a constituent of red and green bell pepper extracts. The chemical structure of this new aroma compound was proposed on the basis of mass spectra and retention indices and confirmed by chemical synthesis and nuclear magnetic resonance spectroscopy measurements. Its aroma properties were described as sulfury, onion-like, and vegetable-like, reminiscent of bell pepper at lower concentrations, with an orthonasal detection threshold of 10 microg/L of water. No differences in odor note and threshold value were observed for the enantiomeric forms, which were prepared from enantiopure 2-heptanol by tosylation, followed by thioacetylation and reduction, giving the target thiol enantiomers.
Simian
Hervé
H
Nestlé Research Center, P.O. Box 44, 1000 Lausanne 26, Switzerland.
Robert
Fabien
F
Blank
Imre
I
D002212:Capsicum / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D006536:Heptanes / Q000032:analysis* / Q000138:chemical synthesis*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009812:Odorants / Q000032:analysis*; D010936:Plant Extracts / Q000737:chemistry; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000032:analysis* / Q000138:chemical synthesis*; D014835:Volatilization
D006536:Heptanes; D010936:Plant Extracts; D013438:Sulfhydryl Compounds; C482407:2-heptanethiol