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

The Menthyloxypyrazines

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Photo by permission of M. Roudintska - Art & Parfum

(+)-2-(1S,2R,5S)-menthyloxypyrazine - Fruity, sweet. Qualitatively, there appears to be no significant difference between the organoleptic properties of the enantiomers or racemate.

Odor Threshold = 10 ppb

= (+)-2-{[(1S,2R,5S)-2-isopropyl-5-methylcyclohexyl]oxy}pyrazine

Ref: H. Masuda & S. Mihara, Preparation and Odor Evaluation of Both Enantiomers of Alkoxypyrazines, Agric. Biol. Chem. Vol. 53, 3367-3368, 1989.

(-)-2-(1R,2S,5R)-menthyloxypyrazine - Fruity, sweet.

Odor Threshold = 2 ppb

= (-)-2-{[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]oxy}pyrazine

Ref: H. Masuda & S. Mihara, Preparation and Odor Evaluation of Both Enantiomers of Alkoxypyrazines, Agric. Biol. Chem. Vol. 53, 3367-3368, 1989.

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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