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

The alpha-n-Methylionones

(10-Methyl-alpha-ionones)

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Photo by permission of M. Roudintska - Art & Parfum

(+)-(6R)-alpha-n-Methylionone (ee = 93%) - woody, powdery, floral odour in the direction of the ionone family, but less powerful and less intense. Dry-down linear, after 4 h woody-ionone, somewhat orris-like, and after 24 h woody-ionone, fruity, raspberry-type.

Odor threshold = 0.53 ng/L in air

= (+)-(R)-10-Methyl-alpha-ionone

= (+)-(1E)-1-[(1R)-2,6,6-trimethylcyclohex-2-en-1-yl]pent-1-en-3-one

Ref: Agnese Abate, Elisabetta Brenna, Claudio Fuganti, Luciana Malpezzi and Stefano Serra, The enantiomers of Iralia®: preparation and odour evaluation, Tetrahedron: Asymmetry 18 (2007) 1145–1153.

(-)-(6S)-alpha-n-Methylionone (ee = 98%) - woody, powdery, floral odour in the direction of the ionone family, but less powerful and less intense. Dry-down linear, after 4 h woody-ionone, somewhat orris-like, and after 24 h woody-ionone, only very slightly fruity.

Odor threshold = 0.24 ng/L in air

= (-)-(S)-10-Methyl-alpha-ionone

= (-)-(1E)-1-[(1S)-2,6,6-trimethylcyclohex-2-en-1-yl]pent-1-en-3-one

Ref: Agnese Abate, Elisabetta Brenna, Claudio Fuganti, Luciana Malpezzi and Stefano Serra, The enantiomers of Iralia®: preparation and odour evaluation, Tetrahedron: Asymmetry 18 (2007) 1145–1153.

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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