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

The alpha-Iso-Methylionones

(8-Methyl-alpha-ionones)

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Photo by permission of M. Roudintska - Art & Parfum

(+)-(6R)-alpha-Iso-methylionone (ee = 94%) - typical dry warm ionone note, irisone, clean tea-like, also on blotter more intense and dryer than (-)-enantiomer.

Odor threshold = 0.079 ng/L in air

= (+)-(R)-8-Methyl-alpha-ionone

= (+)-(3E)-3-methyl-4-[(1R)-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-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-Iso-methylionone (ee = 98%) - about ten times weaker floral note in the direction of iris and ionone, with hesperidic—citric elements and sweet fruity damascone-like aspects. More rich and complex in odour than (+)-enantiomer.

Odor threshold = 0.83 ng/L in air

= (-)-(S)-8-Methyl-alpha-ionone

= (-)-(3E)-3-methyl-4-[(1S)-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-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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