Perfume compositions – Perfume compositions – Ring containing active ingredient
Patent
1998-02-02
1999-10-05
Kelly, C. H.
Perfume compositions
Perfume compositions
Ring containing active ingredient
512 3, 510101, 510102, 424 764, A61K 746, C11D 350, A61L 904
Patent
active
059624035
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a perfume base composition which excellently retains its fragrance. This composition can be used for the production of perfume and other products to be scented such as detergents, cosmetics and sprays.
BACKGROUND ART
A great number of perfume base materials having a floral fragrance have heretofore been known. Among others, aldehyde type perfume bases are the most important perfume base materials. However, since aldehydes are not always stable in fragrant products having different pHs and product forms, these products often do not smell fresh and natural. Moreover, these products do not retain their fragrance for a very long time, which is disadvantageous.
It is accordingly the object of the present invention to provide a perfume base composition which has a floral fragrance and high stability and can impart excellent retentivity of fragrance to blending systems.
DISCLOSURE OF THE INVENTION
This object is achieved by the use of specific benzyl-substituted cyclohexanols, which compounds can impart freshness to the perfume base composition and the products made therefrom. Due to the use of these benzyl-substituted cyclohexanols the articles made from the perfume base composition additionally have a natural, soft and voluminous feeling.
According to the present invention, there is thus provided a perfume base composition comprising a benzyl-substituted cyclohexanol having the following formula (1): ##STR2## wherein the dashed line denotes an optional double bond and the benzyl group is in the 2-, 3- or 4-position of the cyclohexanol ring, with the proviso that the benzyl group is in the 4-position when a double bond is present in the cyclohexanol ring.
BEST MODE FOR CARRYING OUT THE INVENTION
The benzyl-substituted cyclohexanols (1) are known compounds. For example, 2-benzylcyclohexanol is described in Tetrahedron, 48, 2059 (1992), Tetrahedron Lett., 36, 123 (1994) and J. Chem. Soc., 1809 (1956); 3-benzylcyclohexanol is described in J. Chem. Soc., 1809 (1956); and 4-benzylcyclohexanol and 4-benzyl-2-cyclohexen-1-ol are described in Tetrahedron, 48, 2059 (1992). These documents, however, do not disclose the use of benzylcyclohexanols as a fragrance. Moreover, the prior art does not suggest to use these compounds to retain the fragrance of perfume base compositions and of the products made therefrom.
Examples of the benzyl-substituted cyclohexanols (1) useful in the practice of the present invention include 2-benzylcyclohexanol, 3-benzylcyclohexanol, 4-benzylcyclohexanol and 4-benzyl-2-cyclohexen-1-ol. Of these, 2-benzylcyclohexanol, 3-benzylcyclohexanol and 4-benzylcyclohexanol are preferred with 3-benzylcyclohexanol being particularly preferred.
Cis-trans isomerism exists in the benzyl-substituted cyclohexanols (1) according to the substitution state between the benzyl group and the hydroxyl group on the cyclohexane ring (or cyclohexene ring). In the present invention both cis- and trans-benzylcyclohexanols and mixtures thereof may be used. Among these isomers, the cis-form is particularly preferred.
The benzyl-substituted cyclohexanols (1) can be prepared in accordance with the processes described in the above literature. For example, 2-benzylcyclohexanol (1a) can be prepared by subjecting benzaldehyde (2) and cyclohexanone (3) to aldol condensation and hydrogenating the resulting enone (4) (see the following reaction scheme). ##STR3##
3-Benzylcyclohexanol (1b) can be prepared by subjecting a Grignard reagent (5) prepared from a benzyl halide, and 2-cyclohexen-1-one (6) to 1,4-addition and hydrogenating the resulting ketone (7) (see the following reaction scheme). ##STR4##
4-Benzylcyclohexanol (1c) and 4-benzyl-2-cyclohexen-1-ol (1d) can be prepared by using an enamine (9) obtained by the dehydration-condensation of 3-phenylpropionaldehyde (8) and morpholine to form 4-benzyl-2-cyclohexen-1-ol (10) by Robinson annellation and selectively hydrogenating only the carbonyl of the compound (10) to form 4-benzyl-2-cyclohexen-1-ol (1d) or hydrogenating both
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Fukuda Kazuyuki
Kohama Makoto
Koshino Junji
Toi Nao
Cole Monique T.
Kao Corporation
Kelly C. H.
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