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

The 3,4-Didehydro-gamma-ionones

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Photo by permission of M. Roudintska - Art & Parfum

(-)-(6R)-3,4-Didehydro-gamma-ionone - weaker than (+)-(S)-isomer, fruity-floral, slightly woody

Odor threshold = 0.25 ng/L in air

= (-)-(3E)-4-[(1R)-6,6-dimethyl-2-methylenecyclohex-3-en-1-yl]but-3-en-2-one

Ref: Stefano Serra, Claudio Fuganti, and Elisabetta Brenna, Synthesis, Olfactory Evaluation, and Determination of the Absolute Configuration of the 3,4-Didehydroionone Stereoisomers, Helvetica Chimica Acta, Vol. 89 (2006), 1110-1122.

(+)-(6S)-3,4-Didehydro-gamma-ionone - stronger than (-)-(R)-isomer on blotter, floral-woody, cetonal-like, slightly fruity, damasconic, sweet

Odor threshold = 0.080 ng/L in air

= (+)-(3E)-4-[(1S)-6,6-dimethyl-2-methylenecyclohex-3-en-1-yl]but-3-en-2-one

Ref: Stefano Serra, Claudio Fuganti, and Elisabetta Brenna, Synthesis, Olfactory Evaluation, and Determination of the Absolute Configuration of the 3,4-Didehydroionone Stereoisomers, Helvetica Chimica Acta, Vol. 89 (2006), 1110-1122.

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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