(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  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. 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 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. 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