The 1-Hepten-3-ols

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

The Phenoxanol® (Mefrosol) Enantiomers

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Photo by permission of M. Roudintska - Art & Parfum

(R)-(+)-Phenoxanol is 'reminiscent of racemic Phenoxanol, but weaker. Its rose character is harsher, fattier and more metallic compared to the racemate and its antipod'.

Odour threshold: 12.5 ng/L air

= (R)-(+)-Mefrosol

= (R)-(+)-Phenylhexanol

= (R)-(+)-3-Methyl-5-phenyl-1-pentanol

IFF describes the commercial (racemic) material 'Phenoxanol' as "Floral, Rose, Geranium; Diffusive, fresh, floral, rose absolute type. Unusually long lasting. Very economical in use to give the expensive rose oil/absolute effect."

Givaudan describes the commercial (racemic) material as "Floral, Fresh, Rosy; Mefrosol is a diffusive, fresh, rosy floral chemical. It is used to give freshness and volume in both floral and citrus fragrances."

Firmenich describes the commercial (racemic) material 'Phenylhexanol' as "A transparent floral rose and muguet note with a slight green aspect."

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)

Phenoxanol® is a registered trademark of International Flavors & Fragrances

Mefrosol is a tradename of Givaudan (ex Quest Intl)

Phenylhexanol is a tradename of Firmenich

(S)-(-)-Phenoxanol is ‘also reminiscent of a typical Phenoxanol note, but stronger; softer, with a more powdery rose character of pronounced floralcy with fruity facets in the direction of red fruits and rhubarb, and a fresh even slightly aquatic tonality’.

Odour threshold: 5.0 ng/L air

= (S)-(-)-Mefrosol

= (S)-(-)-Phenylhexanol

= (S)-(-)-3-Methyl-5-phenyl-1-pentanol

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)

Phenoxanol® is a registered trademark of International Flavors & Fragrances

Mefrosol is a tradename of Givaudan (ex Quest Intl)

Phenylhexanol is a tradename of Firmenich

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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