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

The 3-Oxo-1,8-cineoles

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Photo by permission of M. Roudintska - Art & Parfum

(1S,4S)-(-)-3-Oxo-cineole - spicy

= (1S,4S)-1,5,5-trimethyl-6-oxa-bicyclo[2.2.2]octan-3-one

= (1S,4S)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-5-one

Ref: Loandos, María del H., Margarita B. Villecco, Eleuterio Burgueño-Tapia, Pedro Joseph-Nathan and César A. N. Catalán, Preparation and Absolute Configuration of (1R,4R)-(+)-3-Oxo-, (1S,4S)-(-)-3-Oxo- and (1R,3S,4R)- (+)-3-Acetyloxy-5-oxo-1,8-cineole, Natural product communications 4, no. 11 (2009): 1537-1545.

(1R,4R)-(+)-3-Oxo-cineole - sweet, cineole-like (weak)

= (1R,4R)-1,5,5-trimethyl-6-oxa-bicyclo[2.2.2]octan-3-one

= (1R,4R)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-5-one

Ref: Loandos, María del H., Margarita B. Villecco, Eleuterio Burgueño-Tapia, Pedro Joseph-Nathan and César A. N. Catalán, Preparation and Absolute Configuration of (1R,4R)-(+)-3-Oxo-, (1S,4S)-(-)-3-Oxo- and (1R,3S,4R)- (+)-3-Acetyloxy-5-oxo-1,8-cineole, Natural product communications 4, no. 11 (2009): 1537-1545.

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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