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

1-Methoxyhexane-3-thiols

Characteristic impact compounds of Clary Sage Flowers

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Photo by permission of M. Roudintska - Art & Parfum

(+)-3S-1-Methoxyhexane-3-thiol is described as follows: In addition to the herbaceous and (clary) sage odor tonalities it has strong connotations of burnt sulfur and alliaceous notes and evokes associations with human olfactory axillary perspiration.

Odor threshold (in air) is 0.04 x 10-3 ng/liter (25X lower than for (-)-3R-1-Methoxyhexane-3-thiol

In Clary sage the natural ratio of enantiomers is 60:40 (+)-3S-1-methoxyhexane-3-thiol : (-)-3R-1-methoxyhexane-3-thiol and the odor is described as: sulfury, herbaceous, green, exceedingly strong, diffusive and key to natural clary sage (flowers). In Ruta chalepensis L. the ratio was 70:30 of (+)-3S : (-)-3R

 Ref: Matthijs van de Waal, Yvan Niclass, Roger L. Snowden, Gerard Bernardinelli & Sina Escher, 1-Methoxyhexane-3-thiol, a powerful odorant of clary sage, Helv. Chim. Acta, 85, 1246-1260 (2002); Sina Dorothea Escher & Matthijs Van De Waal, 1-methoxy-3-hexanethiol and its S-acetyl derivative as perfuming and flavoring ingredients, United States Patent 6,129,941 (October 10, 2000) assigned to Firmenich

(-)-3R-1-methoxyhexane-3-thiol is perceived as sulfury, herbaceous and onion-like and definitely lacks the unique clary-sage signal.

Odor threshold (in air) is 1.09 x 10-3 ng/liter

 Ref: Matthijs van de Waal, Yvan Niclass, Roger L. Snowden, Gerard Bernardinelli & Sina Escher, 1-Methoxyhexane-3-thiol, a powerful odorant of clary sage, Helv. Chim. Acta, 85, 1246-1260 (2002); Sina Dorothea Escher & Matthijs Van De Waal, 1-methoxy-3-hexanethiol and its S-acetyl derivative as perfuming and flavoring ingredients, United States Patent 6,129,941 (October 10, 2000) assigned to Firmenich

 

 

 

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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