title: Enantioselective syntheses and sensory properties of the 3-mercapto-2-methylpentanols.
abstract: 3-Mercapto-2-methylpentanol, a new powerful flavor compound, exhibits two stereocenters giving rise to two pairs of diastereomers. To determine differences in the sensory properties, all four diastereomers and enantiomers were stereo- and enantioselectively synthesized. A highly diastereoselective aldol reaction using a chiral auxiliary was one of the key steps in the synthesis. Further derivatization yielded the enantiopure compounds. Odor thresholds in air and water were determined.
authors.affiliation: Corporate Research, DRAGOCO Gerberding & Company, AG D-37601, Holzminden, Germany.
authors.forename: C
authors.initials: C
authors.lastname: Sabater Lüntzel
authors.forename: S
authors.initials: S
authors.lastname: Widder
authors.forename: T
authors.initials: T
authors.lastname: Vössing
authors.forename: W
authors.initials: W
authors.lastname: Pickenhagen
mesh_terms: D008956:Models, Chemical; D009812:Odorants; D000439:Pentanols / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis*; D013649:Taste
chemical_list: D000439:Pentanols; D013438:Sulfhydryl Compounds; C406689:3-mercapto-2-methylpentan-1-ol