The delta-Octathionolactones

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

The Rosamusks

or

The 1-[3,3-dimethylcyclohexyl]ethyl acetates

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Photo by permission of M. Roudintska - Art & Parfum

(+)-(1S,1'R)-Rosamusk - powerful rose/ionone character with fruity and musk-like undertones

IFF's commercial Rosamusk (~85% sum of isomers) is described as Floral, Musk, Geranium, Fruity. Unusual combination of rose with musky modifications. Also discernible are fruity and geranium aspects. We believe this material is primarily the (+)-(1S,1'R)-acetate.

The ((1S,1'R)-dextro acetate ester is particularly useful because its odour has a powerful rose/ionone character with fruity and musk-like undertones. The (+)-, (-)-, and (+/-)- forms were evaluated in three fragrance types by a panel of trained perfumers with the results showing the spontaneous and outstanding preference for the use of the ester in its dextro form. The tests are also accompanied by unanimous remarks that each of the compositions containing the racemic ester was liked least of all.

The novel (+)-stereoisomers of this invention possess generally similar odours to the corresponding racemic esters, but the odour note has a greater depth, thickness and character.

It should be noted that in most literature references that BASF's Cyclomusk® is considered to be the first major example of an alicyclic musk. However Rosamusk actually preceeded Cyclomusk by six years.

= (+)-(1S,1'R)-1-(3',3'-dimethyl-1'-cyclohexyl)-1-ethanol acetate or (+)-(1S)-1-[(1R)-3,3-dimethylcyclohexyl]ethyl acetate

 Ref: Hifzur Rahman Ansari and Brian George Jaggers, Esters of alpha,3,3-trimethylcyclohexylmethanol and their use in perfumery, British Patent No. 1254198, November 17, 1971; H. R. Ansari, Cyclisation of optically active dihydromyrcenes (2,6-dimethyl-2,7-octadiene) : A stereospecific ring contraction, Tetrahedron, Volume 29, Issue 11, 1973, Pages 1559-1564; Jack H. Blumenthal, Process for preparing alpha, 3,3-trimethylcyclohexane methyl alkanoates, US Patent No. 3,487,102, Dec. 30, 1969

Rosamusk is a tradename of International Flavors & Fragrances

 Cyclomusk is a tradename of BASF

(-)-(1R,1'S)-Rosamusk - This compound is less preferred than the (1S, 1'R) enantiomer.

= (+)-(1S,1'R)-1-(3',3'-dimethyl-1'-cyclohexyl)-1-ethanol acetate or (+)-(1S)-1-[(1R)-3,3-dimethylcyclohexyl]ethyl acetate

Ref: Hifzur Rahman Ansari and Brian George Jaggers, Esters of alpha,3,3-trimethylcyclohexylmethanol and their use in perfumery, British Patent No. 1254198, November 17, 1971; H. R. Ansari, Cyclisation of optically active dihydromyrcenes (2,6-dimethyl-2,7-octadiene) : A stereospecific ring contraction, Tetrahedron, Volume 29, Issue 11, 1973, Pages 1559-1564; Jack H. Blumenthal, Process for preparing alpha, 3,3-trimethylcyclohexane methyl alkanoates, US Patent No. 3,487,102, Dec. 30, 1969

Rosamusk is a tradename of International Flavors & Fragrances

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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