Perfume compositions – Perfume compositions – Ring containing active ingredient
Patent
1998-05-13
2000-02-15
Harris, Cynthia
Perfume compositions
Perfume compositions
Ring containing active ingredient
512 24, 512 25, 512 26, 512 27, 568303, 568338, 568376, 568700, 568822, 568832, A61K 746, C07C 4900, C07C 4500, C07C 49105, C07C 3508
Patent
active
060253231
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to the field of perfumery. It concerns, more particularly, the use of a compound according to the formula ##STR2## in which R stands for a methyl or ethyl radical, as a perfuming ingredient.
PRIOR ART
In spite of the fact that the chemical structure of the compounds according to formula (I) has been known for a long time (see, for example, B. Guiard et al, Bull. Soc. Chim. Fr. 1974, 3021), we were not able to find in the literature any description of potential odor properties of the named compounds. In fact, to our knowledge, no document of the prior art suggests the use of the compounds according to the present invention as perfuming ingredients for the preparation of perfuming bases or perfumes, as well as perfumed consumer products.
DESCRIPTION OF THE INVENTION
Now, we have discovered that the ketones of formula (I) are very useful perfuming ingredients, in particular for the preparation of perfuming compositions or a variety of perfumed products, to which they impart an odor of the aromatic and thujonic type.
Amongst the compounds of formula (I), 2-ethyl-4,4-dimethyl-1-cyclohexanone is cited as a preferred compound. This compound possesses an asymmetric carbon atom (in position 2 in the cycle) and may present itself as a racemic mixture of enantiomers when prepared in a conventional organic synthesis, or in the form of one of the enantiomers. We were able not only to prepare said mixture, but also the two enantiomers in a pure state and found differences in their odor notes.
The racemic mixture develops an odor of the thujonic type which is reminiscent of the typical odor of cedarleaf and of hyssop, accompanied by a natural fruity, damascenone character which is very much appreciated. The hyssop type character is quite natural as well.
The odor of this compound is moreover reminiscent of that of 3,3-dimethyl-cyclohexyl-methyl-ketone (see FR 1.543.320), but its aromatic-thujonic note is distinctly less camphoraceous and possesses a fruity aspect which is more pronounced than in the latter one. Furthermore, even if the odor of 2-ethyl-4,4-dimethyl-1-cyclohexanone is reminiscent of the odor of 5-methyl-exo-tricyclo[6.2.1.0(2,7)]undecan-4-one (see U.S. Pat. No. 5,538,944), this compound of formula (I) develops a fragrance which is distinctly more natural in its thujonic connotation.
As regards the two pure enantiomers of this compound (-)-(2R)-2-ethyl-4,4-dimethyl-1-cyclohexanone develops the more strongly herbaceous and thujonic odor of the two, with a pronounced fruity subnote having almost a spicy-berry-like character.
(+)-(2S)-2-Ethyl-4,4-dimethyl-1-cyclohexanone also possesses a herbaceous odor note, which however is less thujonic and drier than that of its enantiomer. Additionally, an earthy, rooty cellar aspect is also present.
By preparing mixtures which contain the enantiomers in different amounts, a person skilled in the art will be able to create fragrances according to the invention in which the characteristics of the enantiomers are combined at their best. In fact, hereinafter, whenever we refer to 2-ethyl-4,4-dimethyl-1-cyclohexanone this is meant to designate either one of its pure enantiomers or any mixture thereof.
The methylated homologue, namely 2,4,4-trimethyl-1-cyclohexanone, possesses a nice aromatic note which is appreciated for its fruity-eucalyptus connotation.
From the foregoing, it is evident that the compounds of formula (I) bring a new range of fragrant tones to the perfumer's palette.
Due to their fragrant properties, the compounds of formula (I), in the form of a mixture of enantiomers or as one of the pure enantiomers, find applications in fine fragrances as well as in technical perfumery. They may be used as such or in admixture with other perfuming ingredients, solvents or adjuvants of current use in the art.
The proportions in which these compounds can be used depend of the desired olfactory effect, as well as on the nature of the other perfuming coingredients. As an example, one can cite concentrations in the order of
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Arctander et al., "Perfume and flavor chemical", see 967:dihydro-iso-phorone (1969).
Garnero et al., "New constituents of essential oil of iris rhizomes", Chemical Abstracts 95:327.
Guiard et al., "Reactivite des Dimethyl-4,4 cyclohexanones substituees en 2", Bulletin de la Societe Chimique de France, No. 12, pp. 3021-3030 (1974).
Smith et al., "The Reduction-Methylation of Cyclohexenone Derivatives", J. Org. Chem. 32:2851-2856 (1967).
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Fehr Charles
Margot Christian
Cole Monique
Firmenich SA
Harris Cynthia
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