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(+)-Methyl
(1R,2S)-delta-cyclogeranate - Perfumers have
also noticed some differences between the two
enantiomers - although the odor of both
enantiomers is clearly damascone-like and in the
same trend described below, the fragrance of the
(1R,2S)-(+)- enantiomer is stronger than the
(1S,2R)-(-)- enantiomer which, in the other
hand, is more aromatic.
Also known as
(+)-Methyl
(1R,2S)-2,6,6-trimethyl-3-cyclohexene-1-carboxylate
Methyl
trans-2,6,6-trimethyl-3-cyclohexene-1-carboxylate
is much appreciated for its odor which presents
a remarkable damascone, rosy note associated
with citronellol like and slightly saffrony
notes. The damascone note is particularly nice
and has a very natural, very rosy, more
precisely red rose odor. Moreover, said odor is
devoid of the fermented-apple aspect present for
example in the alpha damascone fragrance. From
an olfactory point of view, the odor character
of methyl trans-2,6,6-trimethyl-3-cyclo-
hexene-1-carboxylate is intermediate between
that of delta and alpha damascone.
Indeed, the
trans methyl ester of formula (I) possesses an
odor closer to that of damascones than its gamma
or alpha isomers, namely methyl
2,2-dimethyl-6-methylene-1-cyclohexanecarboxylate
(described in U.S. Pat. No. 5,015,625, to
Firmenich S A) and methyl
2,6,6-trimethyl-2-cyclohexene-1-carboxylate
(described in EP 56109) respectively. This
effect is mainly due to the fact that, when
compared with the mentioned isomers, the trans
methyl ester presents a more pure damascone-rosy
connotation, which is almost devoid of the
typical herbaceous-thujonic and red-fruity,
green apple notes of said gamma and alpha
isomer.
Ref: Fehr,
Charles; Blanc, Pierre-Alain, Unsaturated ester
as perfuming ingredient, United States Patent
Application 20030119712, June 26,
2003
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-2,6,6-trimethyl-3-cyclohexene-1-carboxylate.gif)
-2,6,6-trimethyl-3-cyclohexene-1-carboxylate.gif)