The 1-Hepten-3-ols

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

The Citralis Nitrile Enantiomers

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Photo by permission of M. Roudintska - Art & Parfum

(R)-(-)-Citralis Nitrile is ‘similar in smell, but slightly stronger, and with additional waxy aspects, and a more pronounced green, leafy side’ (compared to its enantiomer).

Odour threshold: 6.8 ng/L air

= (R)-(-)-3-Methyl-5-phenylpentane-1-nitrile

Innospec describes the commercial (racemic) material as "Citrus, lime, fresh, floral."

Ref: Ugo Matteoli, Alessandra Ciappa, Sara Bovo, Matheo Bertoldini, Alberto Scrivant, Asymmetric catalysis in fragrance chemistry: a new synthetic approach to enantiopure Phenoxanol®, Citralis® and Citralis Nitrile®, Tetrahedron: Asymmetry, Volume 18, Issue 6, 797-802 (2007)

Citralis Nitrile is a tradename of Innospec Inc.

(S)-(+)-Citralis Nitrile is ‘typical citrus, reminiscent of lemon peel and geranyl nitrile, with fresh, fruity and slightly green nuances’

Odour threshold: 12.5 ng/L air

= (S)-(+)-3-Methyl-5-phenylpentane-1-nitrile

Ref: Ugo Matteoli, Alessandra Ciappa, Sara Bovo, Matheo Bertoldini, Alberto Scrivant, Asymmetric catalysis in fragrance chemistry: a new synthetic approach to enantiopure Phenoxanol®, Citralis® and Citralis Nitrile®, Tetrahedron: Asymmetry, Volume 18, Issue 6, 797-802 (2007)

Citralis Nitrile is a tradename of Innospec Inc.

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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