The delta-Octathionolactones

Chirality & Odour Perception
John C. Leffingwell, Ph.D.

The 3-Mercaptohexyl acetates

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Photo by permission of M. Roudintska - Art & Parfum

(3R)-(-)-3-mercaptohexyl acetate - In dilution, posseses attractive tropical fruity notes (for the (3R)-3-mercaptohexyl acetate and (3R)-3-mercaptohexyl butanoate) - (description of Werkhoff, et. al.); Werkhoff, et. al. described the 3-mercaptohexyl acetates as grapefruit, black currant, buccu, mango, passion fruit, guava; Tominga et.al. (2006) indicates "The less odoriferous R form is reminiscent of passion fruit, while the S form has a more herbaceous odor of boxwood"

Flavor perception threshold = 0.009 ppb in 12% alcohol/water (Tominaga, et al.)

Odor threshold = 0.10 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; See also Engel, K. H., Tressl, R., Identification of new sulfur-containing volatiles in yellow passion fruits (Passiflora edulis f. flavicarpa). J. Agric. Food Chem., 39, 2249-2252, 1991; Tominaga, T., Darriet, P., Dubourdieu, D., Identification de l’acétate de 3-mercaptohexanol, composé à forte odeur de buis, intervenant dans l’arôme des vins de Sauvignon. Vitis, 35, 4, 207-210, 1996; Weber, B; Haag, H.-P.; Mosandl, A., 3-Mercaptohexyl- and 3-methylthioalkanoates - structure and properties of the enantiomers, Z. Lebensm. Unters. Forsch., 195, 426-428, 1992; 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

 

 

(3S)-(+)-3-mercaptohexyl acetate - In dilution, posseses insignificant sulfury, herbaceous and oniony characteristics (for the (3S)-3-mercaptohexyl acetate and (3S)-3-mercaptohexyl butanoate) - (description of Werkhoff, et. al.); Tominga et.al. (2006) indicates "The less odoriferous R form is reminiscent of passion fruit, while the S form has a more herbaceous odor of boxwood"

Flavor perception threshold = 0.0025 ppb in 12% alcohol/water (Tominaga, et al.)

Odor threshold = 0.03 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; See also Engel, K. H., Tressl, R., Identification of new sulfur-containing volatiles in yellow passion fruits (Passiflora edulis f. flavicarpa). J. Agric. Food Chem., 39, 2249-2252, 1991; Tominaga, T., Darriet, P., Dubourdieu, D., Identification de l’acétate de 3-mercaptohexanol, composé à forte odeur de buis, intervenant dans l’arôme des vins de Sauvignon. Vitis, 35, 4, 207-210, 1996; Weber, B; Haag, H.-P.; Mosandl, A., 3-Mercaptohexyl- and 3-methylthioalkanoates - structure and properties of the enantiomers, Z. Lebensm. Unters. Forsch., 195, 426-428, 1992; 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

Cyclic Terpenoid Odorants

Bicyclic Terpenoid Odorants

Acyclic Terpenoid Odorants

Ionones, Irones, Damascones & Structurally Related Odorants

Acyclics (Alcohols, Esters, Acids, Aldehydes)

Lactones

Sesquiterpenoid Related Odorants

Steroid Urine Type Odorants

Sandalwood Type Odorants

Musk Odorants

Miscellaneous

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