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

The Tonalides  Th

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Photo by permission of M. Roudintska - Art & Parfum

(R)-(+)-Tonalide - light and sweet aromatic odor

= (+)-1-((R)-1,2,3,4-tetrahydro-1,1,2,4,4,7-hexamethylnaphthalen-6-yl)ethanone

= (+)-1-[(6R)-3,5,5,6,8,8-hexamethyl-5,6,7,8-tetrahydronaphthalen-2-yl]ethanone

Ref: Suzukamo, Gohfu, and Yoji Sakito. "Tetrahydronaphthalene derivatives and their production." U.S. Patent 4,767,882, issued August 30, 1988; Ohloff, Günther, Beat Winter, and Charles Fehr. "Chemical Classification and Structure-Odour Relationships." In Perfumes, p. 321. Springer Netherlands, 1994.

(S)-(-)-Tonalide - strongly musky odor with a good fixation property

= (-)-1-((S)-1,2,3,4-tetrahydro-1,1,2,4,4,7-hexamethylnaphthalen-6-yl)ethanone

= (-)-1-[(6S)-3,5,5,6,8,8-hexamethyl-5,6,7,8-tetrahydronaphthalen-2-yl]ethanone

Ref: Suzukamo, Gohfu, and Yoji Sakito. "Tetrahydronaphthalene derivatives and their production." U.S. Patent 4,767,882, issued August 30, 1988; Ohloff, Günther, Beat Winter, and Charles Fehr. "Chemical Classification and Structure-Odour Relationships." In Perfumes, p. 321. Springer Netherlands, 1994.

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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