(+)-(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
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