title: Production of the pepper aroma compound, (-)-rotundone, by aerial oxidation of α-guaiene.
abstract: The aroma link between pepper and wine has recently been elucidated to be due to the important aroma compound rotundone. To date, rotundone is the only known impact odorant with a peppery aroma. Although the concentration found in products of natural origin is small, the odor detection threshold is among the lowest of any natural product yet discovered. We report herein the identification of the first known precursor to rotundone, namely, α-guaiene, and that one mechanism of transformation is simple aerial oxidation.
authors.affiliation: Department of Wine Science, School of Agriculture, Food and Wine, The University of Adelaide , Waite Campus, PMB 1, Glen Osmond, South Australia 5064, Australia.
authors.forename: An-Cheng
authors.initials: AC
authors.lastname: Huang
authors.forename: Stacey
authors.initials: S
authors.lastname: Burrett
authors.forename: Mark A
authors.initials: MA
authors.lastname: Sefton
authors.forename: Dennis K
authors.initials: DK
authors.lastname: Taylor
mesh_terms: D052176:Azulenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D015394:Molecular Structure; D009812:Odorants / Q000032:analysis; D010084:Oxidation-Reduction; D029222:Piper nigrum / Q000737:chemistry*; D010936:Plant Extracts / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification; D045789:Sesquiterpenes, Guaiane / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification
chemical_list: D052176:Azulenes; D010936:Plant Extracts; D012717:Sesquiterpenes; D045789:Sesquiterpenes, Guaiane; C530290:rotundone; C019408:guaiene
keywords: (−)-rotundone; aerial oxidation; pepper; wine; α-guaiene