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

The 9-Hydroxy-1,8-cineoles

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Photo by permission of M. Roudintska - Art & Parfum

(8S)-(+)-9-Hydroxy-1,8-cineole - Eucalyptus (5), pine needle (1), fatty (1) as evaluated by 5-6 panelists by GC-O (Kirsch and Buettner)

 = [(3S)-1,3-dimethyl-2-oxabicyclo[2.2.2]oct-3-yl]methanol

Ref: Kirsch, Frauke, and Andrea Buettner. "Odor Qualities and Thresholds of Physiological Metabolites of 1,8-Cineole as an Example for Structure Activity Relationships Considering Chirality Aspects." Chemistry & biodiversity 10, no. 9 (2013): 1683-1695. See Carman, R. M., and Karel D. Klika. "Partially racemic compounds as brushtail possum urinary metabolites." Australian Journal of Chemistry 45, no. 4 (1992): 651-657 for determination of the absolute configurations.

 

(8R)-(-)-9-Hydroxy-1,8-cineole - Eucalyptus (4), plastic (4), musty (2), rotten (1), sweet (1), dusty (1) as evaluated by 5-6 panelists by GC-O (Kirsch and Buettner)

= [(3R)-1,3-dimethyl-2-oxabicyclo[2.2.2]oct-3-yl]methanol

Ref: Kirsch, Frauke, and Andrea Buettner. "Odor Qualities and Thresholds of Physiological Metabolites of 1,8-Cineole as an Example for Structure Activity Relationships Considering Chirality Aspects." Chemistry & biodiversity 10, no. 9 (2013): 1683-1695. See Carman, R. M., and Karel D. Klika. "Partially racemic compounds as brushtail possum urinary metabolites." Australian Journal of Chemistry 45, no. 4 (1992): 651-657 for determination of the absolute configurations.

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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