The 1-Hepten-3-ols

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

The Citralis (Mefranal) Enantiomers

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Photo by permission of M. Roudintska - Art & Parfum

(R)-(+)-Citralis is ‘very close to racemic Citralis, and stronger than its antipode; aldehydic, fresh, floral, citronellal-like odour, reminiscent of verbena and lemongrass; a somewhat slightly latex and plastic connotation is present as well’

Odour threshold: 2.5 ng/L air

= (R)-(+)-Mefranal

= (R)-(+)-3-Methyl-5-phenylpentanal

Innospec describes the commercial (racemic) material as "Fresh, rosy-citrus-ozone with a hint of lily of the valley".

Givaudan describes the commercial (racemic) material as Citrus, Aldehydic, Geranium; Mefranal has a refreshing lemon geranium note with an aldehydic floral heart.

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 is a tradename of Innospec Inc.

Mefranal is a tradename of Givaudan (ex Quest Intl)

(S)-(-)-Citralis is ‘citronellal-like, floral-aldehydic, but less fresh, more fruity in the direction of red fruits, and with a fatty-rosy undertone that somewhat even reminds of Phenoxanol’

Odour threshold: 7.9 ng/L air

= (S)-(-)-Mefranal

= (S)-(-)-3-Methyl-5-phenylpentanal

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 is a tradename of Innospec Inc.

Mefranal is a tradename of Givaudan (ex Quest Intl)

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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