title: Influence of the stereochemistry on the sensory properties of 4-mercapto-2-heptanol and its acetyl-derivatives.
abstract: 4-Mercapto-2-heptanol, previously described in cooked bell pepper, was used to determine the impact of the stereochemistry on the sensory properties of a thiol with a 1,3-oxygen-sulfur functionality. In addition, the acetyl-derivatives 4-acetylthio-2-heptanol, 4-mercapto-2-heptyl acetate and 4-acetylthio-2-heptyl acetate were investigated. The synthesized stereoisomers were separated via capillary gas chromatography (GC) using chiral stationary phases. The GC orders of elution were determined by assigning the absolute configurations via NMR analysis in combination with lipase-catalyzed kinetic resolutions. Odor thresholds and odor properties were determined by means of GC/Olfactometry. The data revealed that the sensory properties of the investigated compounds are not only significantly influenced by the acetylation but also by the configurations of the two asymmetric centers.
authors: Lehrstuhl für Allgemeine Lebensmitteltechnologie, Technische Universität München , Maximus-von-Imhof-Forum 2, D-85350 Freising-Weihenstephan, Germany.
authors: Svenja
authors: S
authors: Nörenberg
authors: Bastian
authors: B
authors: Reichardt
authors: Verena
authors: V
authors: Andelfinger
authors: Wolfgang
authors: W
authors: Eisenreich
authors: Karl-Heinz
authors: KH
authors: Engel
mesh_terms: D000107:Acetylation; D002849:Chromatography, Gas; D019850:Heptanol / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009812:Odorants / Q000032:analysis; D012677:Sensation; D012903:Smell; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D013438:Sulfhydryl Compounds; D019850:Heptanol