(3R)-(-)-3-mercaptohexan-1-ol - In dilution, the (R)-enantiomer is distinctly weaker, showing only sulfury and herbaceous odor impressions - (description of Werkhoff, et. al.); The two enantiomers have quite different aromas; Tominaga et. al. (2006) indicates "The R form is fruitier, with a zesty aroma reminiscent of grapefruit, while the S form smells more of passion fruit". Flavor perception threshold = 0.05 ppb in 12% alcohol/water (Tominaga, et al.) Odor threshold = 0.08 ng/L in air (Steinhaus, et al.)  Ref: Werkhoff, P.; Guntert, M.; Krammer G.; Sommer, H.; Kaulen, J.; Vacuum Headspace Method in Aroma Research: Flavor Chemistry of Yellow Passion Fruits, J. Agric. Food Chem., 46(3); 1076-1093, 1998; Takatoshi Tominaga, Yvan Niclass, Eric Frerot, and Denis Dubourdieu, Stereoisomeric Distribution of 3-Mercaptohexan-1-ol and 3-Mercaptohexyl Acetate in Dry and Sweet White Wines Made from Vitis vinifera (Var. Sauvignon Blanc and Semillon), J. Agric. Food Chem., 54 (19), 7251 -7255, 2006. Martin Steinhaus, Diana Sinuco, Johannes Polster, Coralia Osorio, and Peter Schieberle, Characterization of the Aroma-Active Compounds in Pink Guava (Psidium guajava, L.) by Application of the Aroma Extract Dilution Analysis, J. Agric. Food Chem., 56 (11), 4120–4127, 2008 See also Georg Heusinger and Armin Mosandl, Chirale, schwefelhaltige aromastoffe der gelben passionsfrucht (passiflora edulis f. flavicarpa), darstellung der enantiomeren und absolute konfiguration, Tetrahedron Letters, 25(5), 507-510 1984;

(3S)-(+)-3-mercaptohexan-1-ol - In dilution, posseses interesting exotic and tropical fruit notes - (description of Werkhoff, et. al.); Werkhoff, et. al. described the 3-mercaptohexanols as fruity, juicy, tropical fruits, grapefruit, black currant, buccu, mango, guava; Tominaga et. al. (2006) indicates "The R form is fruitier, with a zesty aroma reminiscent of grapefruit, while the S form smells more of passion fruit". Flavor perception threshold = 0.06 ppb in 12% alcohol/water (Tominaga, et al.) Odor threshold = 0.07 ng/L in air (Steinhaus, et al.) Ref: Werkhoff, P.; Guntert, M.; Krammer G.; Sommer, H.; Kaulen, J.; Vacuum Headspace Method in Aroma Research: Flavor Chemistry of Yellow Passion Fruits, J. Agric. Food Chem., 46(3); 1076-1093, 1998; Takatoshi Tominaga, Yvan Niclass, Eric Frerot, and Denis Dubourdieu, Stereoisomeric Distribution of 3-Mercaptohexan-1-ol and 3-Mercaptohexyl Acetate in Dry and Sweet White Wines Made from Vitis vinifera (Var. Sauvignon Blanc and Semillon), J. Agric. Food Chem., 54 (19), 7251 -7255, 2006. Martin Steinhaus, Diana Sinuco, Johannes Polster, Coralia Osorio, and Peter Schieberle, Characterization of the Aroma-Active Compounds in Pink Guava (Psidium guajava, L.) by Application of the Aroma Extract Dilution Analysis, J. Agric. Food Chem., 56 (11), 4120–4127, 2008 See also Georg Heusinger and Armin Mosandl, Chirale, schwefelhaltige aromastoffe der gelben passionsfrucht (passiflora edulis f. flavicarpa), darstellung der enantiomeren und absolute konfiguration, Tetrahedron Letters, 25(5), 507-510 1984;

Ionones, Irones, Damascones & Structurally Related Odorants

Acyclics (Alcohols, Esters, Acids, Aldehydes)

Lactones

Sesquiterpenoid Related Odorants