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

The 1-tert-butyl-2,3,3a,4,6,7-hexahydro-3a-methylinden-5-ones

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Photo by permission of M. Roudintska - Art & Parfum

(+)-(S)-1-tert-butyl-2,3,3a,4,6,7-hexahydro-3a-methylinden-5-one - Odor description (10% DPG, blotter): dark woody (woody facet of Cashmeran), agrestic odor with slightly smoky aspects, and nuances of vetiver and oud, and with slightly floral facets (rosy in Mefrosol direction). The odor is more floral and woody than that of the (R)-enantiomer.

Odor Threshold (GC) = 10.6 ng L–1 air

= (+)-(7aS)-3-tert-Butyl-7a-methyl-4,5,7,7a-tetrahydro-1H-inden-6(2H)-one

Ref: Felker, I., Pupo, G., Kraft, P., & List, B. (2015). Design and Enantioselective Synthesis of Cashmeran Odorants by Using “Enol Catalysis”. Angewandte Chemie International Edition, 54(6), 1960-1964.

 

(-)-(R)-1-tert-butyl-2,3,3a,4,6,7-hexahydro-3a-methylinden-5-one - Odor description (10% DPG, blotter): dark woody, agrestic odor with fruity aspects in Cashmeran direction and nuances of raspberry and orris, and slightly rooty, oud and vetiver facets, somewhat recalling epoxy cedrene. The odor is sweeter and fattier than that of the antipode.

Odor Threshold (GC) = 5.95 ng L–1 air

= (-)-(7aR)-3-tert-Butyl-7a-methyl-4,5,7,7a-tetrahydro-1H-inden-6(2H)-one

Ref: Felker, I., Pupo, G., Kraft, P., & List, B. (2015). Design and Enantioselective Synthesis of Cashmeran Odorants by Using “Enol Catalysis”. Angewandte Chemie International Edition, 54(6), 1960-1964.

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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