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

The Carvones

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Photo by permission of M. Roudintska - Art & Parfum

(4S)-(+)-carvone - caraway, fresh herbal

Odor Threshold = 600 ppb (Pelosi & Viti)

Odor Threshold = 85-130 ppb (Leitereg et al)

Ref: G. F. Russell & J. I. Hills, Odor Differences between Enantiomeric Isomers, Science, Vol. 172, 1043-1044 (1971); L. Friedman & J. G. Miller, Odor Incongruity and Chirality, Science, Vol. 172, 1044-1046 (1971); G . F. Russell and J. I. Hills, Abstr. 158th Am. Chern. Soc. Natl. Mtg., September 1969, paper No. AGFD-6; Theodore J. Leitereg, Dante G. Guadagni, Jean Harris, Thomas R. Mon, Roy Teranishi, Chemical and Sensory Data Supporting the Difference between the Odors of the Enantiomeric Carvones, J. Agr. Food Chem., Vol. 19, No. 4, 785-787 (1971); P. Pelosi, & R. Viti , Specific anosmia to l-carvone: the minty primary odour, Chem. Senses Flavour, Vol. 3, 331-337 (1978) Mans H. Boelens, Harrie Boelens & Leo J. van Gemert, Perfumer & Flavorist, Vol. 18, No. 6, 1-15, 1993 and numerous sources cited therein.

(4R)-(-)-carvone - Sweet spearmint, fresh herbal

Odor Threshold = 43 ppb (Pelosi & Viti)

Odor Threshold = 2 ppb (Leitereg et al)

Ref: G. F. Russell & J. I. Hills, Odor Differences between Enantiomeric Isomers, Science, Vol. 172, 1043-1044 (1971); L. Friedman & J. G. Miller, Odor Incongruity and Chirality, Science, Vol. 172, 1044-1046 (1971); G . F. Russell and J. I. Hills, Abstr. 158th Am. Chern. Soc. Natl. Mtg., September 1969, paper No. AGFD-6; Theodore J. Leitereg, Dante G. Guadagni, Jean Harris, Thomas R. Mon, Roy Teranishi, Chemical and Sensory Data Supporting the Difference between the Odors of the Enantiomeric Carvones, J. Agr. Food Chem., Vol. 19, No. 4, 785-787 (1971); P. Pelosi, & R. Viti , Specific anosmia to l-carvone: the minty primary odour, Chem. Senses Flavour, Vol. 3, 331-337 (1978) Mans H. Boelens, Harrie Boelens & Leo J. van Gemert, Perfumer & Flavorist, Vol. 18, No. 6, 1-15, 1993 and numerous sources cited therein.

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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