Perfume compositions – Perfume compositions – Ring containing active ingredient
Patent
1987-11-23
1989-12-05
Reamer, James H.
Perfume compositions
Perfume compositions
Ring containing active ingredient
568326, A61K 746
Patent
active
048852740
DESCRIPTION:
BRIEF SUMMARY
FIELD OF TECHNOLOGY
This invention relates to a perfume composition or, more particularly, relates to a perfume composition containing a novel compound represented by the formula (I) given below [in the formula, R.sub.1 is a methyl or ethyl group and either one of R.sub.2 and R.sub.3 is a methyl group, the other being a hydrogen atom]. ##STR1##
This perfume composition can be used effectively in soaps, liquid scents, cosmetics, room aromatics, masking agents and the like.
BACKGROUND TECHNOLOGY
In view of the extreme expensiveness and unstable supply of natural musk obtained from a musk deer, works have been undertaken intensively from old times to develop compounds having musk-like tone of fragrance and a large number of compounds have been discovered including those belonging to the types of nitro-musks, indan musks, Tetralin musks, macrocyclic musks and the like.
In recent years, however, several of these compounds have become banned for use in soaps, cosmetics and the like in respect of the safety concern. Therefore, it is desired to have advent of a compound having musk-like tone of fragrance but less problems in safety. As such a compound, compounds having a skeleton of cyclopentanaphthalene are known and disclosures are already given for ##STR2## in German Pat. No. 2,114,216 and for ##STR3## in Japanese Patent Publication 42-6491 while they are each not satisfactory in respect of the quality and strength of the fragrance although they have no problem in respect of safety.
Accordingly, the object of the present invention is to provide a compound of musk-like fragrance having a skeleton of cyclopentanaphthalene with high safety, low costs for manufacturing and fragrance excellent in both of quality and strength.
DISCLOSURE OF THE INVENTION
In the course of the comparative investigations for the synthetic methods and fragrance characteristics of a large number of compounds having a skeleton of cyclopentanaphthalene, the inventors have arrived at a discovery that acylation of a mixture composed of 1,1-dimethyl-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]-naphthalene (referred to as the 1,1-[b] compound hereinbelow), 1,1-dimethyl-2,3,6,7,8,9-hexahydro-1H-cyclopenta[a]naphthalene (referred to as the 1,1-[a] compound hereinbelow) and 3,3-dimethyl-1,2,6,7,8,9-hexahydro-1H-cyclopenta[a]naphthalene (referred to as the 3,3-[a] compound hereinbelow) produced by the cyclization reaction of Tetralin and isoprene gives a mixture composed of the 4-acyl-1,1-[b] compound and 4-(or 5-)acyl-1,1-(or 3,3-)-[a] compound, which in itself has only ionone-like weak musk fragrance but is capable of giving a perfume composition having unexpectedly strong and noble musk fragrance by removing the 4-acyl-1,1-[b] compound, which is a known compound, by column chromatography and that the entity of the musk fragrance is the 4-(or 5-)acyl-1,1-(or 3,3-)-[a] compound, which is a novel compound, leading to completion of the present invention.
Namely, the present invention relates to a perfume composition containing the 4-(or 5-)-acyl-1,1-(or 3,3-)-[a] compound represented by the formula ##STR4## [in the formula, R.sub.1 is a methyl group or ethyl group and either one of R.sub.2 and R.sub.3 is a methyl group, the other being a hydrogen atom] .
BRIEF DESCRIPTION OF THE DRAWING
FIG. 1 is a gas chromatogram of the acylated mixture obtained in Preparatory Example 2,
FIG. 2 is an infrared spectrum of the 5-acetyl-3,3-[a] compound obtained in Preparatory Example 4,
FIG. 3 is an NMR spectrum of the 5-acetyl-3,3-[a] compound obtained in Preparatory Example 4,
FIG. 4 is an infrared spectrum of the 5-acetyl-1,1-[a] compound obtained in Preparatory Example 4,
FIG. 5 is an NMR spectrum of the 5-acetyl-1,1-[a] compound obtained in Preparatory Example 4,
FIG. 6 is an infrared spectrum of the 4-acetyl-1,1-[a] compound obtained in Preparatory Example 4, and
FIG. 7 is an NMR spectrum of the 4-acetyl-1,1-[a] compound obtained in Preparatory Example 4.
THE BEST MODE TO PRACTICE THE INVENTION
In order to obtain the perfume composition of the present i
REFERENCES:
patent: 4284819 (1981-08-01), Sprecker et al.
patent: 4541948 (1985-09-01), Joulain
Kobayashi Toyohiko
Yamada Nobuo
Reamer James H.
Takasago Perfumery Co. Ltd.
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