Perfume compositions – Perfume compositions
Reexamination Certificate
2001-05-23
2003-11-25
Clardy, S. Mark (Department: 1616)
Perfume compositions
Perfume compositions
C424S047000, C424S070100, C424S401000, C510S102000, C510S105000, C510S119000, C512S008000, C512S014000, C512S015000, C512S019000, C512S025000
Reexamination Certificate
active
06653276
ABSTRACT:
BACKGROUND OF THE INVENTION
(1) Field of the Invention
This invention relates to a composition comprising a cyclopentanone or cyclopentanol compound having cyclopentylidene and/or cyclopentyl substituents at a high concentration, a process for preparing the same, and a perfume composition comprising the same as a fragrant odor-emitting ingredient.
The perfume composition is used, for example, for a perfume, a soap, a shampoo, a hair-treatment, a body shampoo, a detergent, a cosmetic, a hair-spray and an aromatic.
(2) Description of the Related Art
It is known that cyclopentanone derivatives include those which are useful as a perfume. As specific examples of the cyclopentanone derivatives used as a perfume, there can be mentioned methyl 3-oxo-2-(cis-2-pentenyl)-cyclopentaneacetate (trivial name: methyl jasmonate) and methyl 2-pentyl-3-oxocyclopent-1-yl-acetate (trivial name: methyl dihydrojasmonate), which are known as a perfume emitting a jasmine-like floral scent or odor; and 2-cyclopentyl cyclopentylcrotonate which is known as a perfume emitting a fruity and juicy scent or odor. That is, cyclopentanone derivatives having various substituents or functional groups are known as a perfume emitting a fragrant scent or odor.
As a perfume having a cyclopentanone structure with a cyclopentyl derivative substituent, only a few perfumes are knwon which include 2-cyclopentyl cyclopentylcrotonate, mentioned above, and 2-cyclopentylcyclopentanone.
As for a cyclopentanone compound having two cyclopentyl derivative substituents, it is taught in Bull. Soc. Chim. Fr., (1973) 4(2), 1509 that, when cyclopentanone is treated with metallic sodium, 2-cyclopentylidenecyclopentanone and 2,5-dicyclopentylidenecyclopentanone are produced. But, this literature is silent on yield of the dipentylidene compound. Further it is taught in J. Am. Chem. Soc., (1974), 116, 1962 that, when cyclopentanone is heated in the presence of a zeolite in a toluene medium, 2-cyclopentylidenecyclopentanone and 2,5-dicyclopentylidenecyclopentanone are produced. The yield of 2,5-dicyclopentylidenecyclopentanone is only 8%. The two literatures are silent on the use of 2,5-dicyclopentylidenecyclopentanone as a perfume.
Further, it is described in Shin Jikken Kagaku Kouza, vol. 14 (II), p852 (published by Maruzen, Japan) that, when cyclopentanone is allowed to react with potassium hydroxide in an ethanol medium, 2,5-dicyclopentylidenecyclopentanone is produced in a yield of 12-51%. However, the inventors' experiments following the same procedures and conditions revealed that 2-cyclopentylidenecyclopentanone, i.e., a dimer of cyclopentanone, was preferentially produced and the yield of the target compound was below 1%. This literature is also silent on the use of the target compound as a perfume.
It is generally accepted that fragrances of compounds used as a perfume greatly vary even though there exists only a minor difference in chemical structure. Therefore, it is crucial for the development of novel perfumes to synthesize compounds having various substituents and closely examine fragrances of the compounds.
SUMMARY OF THE INVENTION
A primary object of the present invention is to provide a novel compound having a cyclopentanone structure or a cyclopentanol structure, which emits a floral or musk-tone fragrance.
Other objects of the present invention are to provide processes for producing the cyclopentanone or cyclopentanol compound, and a perfume composition comprising the same.
The present inventors have synthesized compounds with a cyclopentanone or cyclopentanol structure having introduced therein various cyclopentyl derivatives as substituent, and have closely examined fragrance of the cyclopentanone or cyclopentanol compounds. As the results of examination, it has been found that perfume compositions comprising a cyclopentanone or cyclopentanol compound having a specific cyclopentyl derivative substituent emit floral and powdery cosmetic-like fragrances and are useful for imparting the fragrances, and natural and fresh scent to variety of toiletries.
Thus, in a first aspect of the present invention, there is provided a composition comprising at least 60% by weight, based on the weight of the composition, of a cyclopentane compound having an oxygen-containing group and cyclopentylidene and/or cyclopentyl substituents, which is represented by the following general formula (1):
wherein
independently represents a single bond or a double bond, R
1
through R
10
independently represent hydrogen or an alkyl group having 1 to 4 carbon atoms, and —Y is —OH or ═O.
In a second aspect of the invention, there is provided a perfume composition comprising as a fragrant odor-emitting ingredient a cyclopentane compound having an oxygen-containing group and cyclopentilidene and/or cyclopentyl substituents, which is represented by the above formula (1).
In a third aspect of the invention, there is provided a process for preparing a 2,5-dicyclopentylidenecyclopentanone compound represented by the following general formula (4):
wherein R
1
through R
10
independently represent hydrogen or an alkyl group having 1 to 4 carbon atoms, which comprises allowing a 2-cyclopentylidenecyclopentanone compound represented by the following general formula (2):
wherein R
1
through R
4
, R
9
and R
10
independently represent hydrogen or an alkyl group having 1 to 4 carbon atoms, to react with a cyclopentanone compound represented by the following general formula (3):
wherein R
5
through R
8
independently represent hydrogen or an alkyl group having 1 to 4 carbon atoms, under alkaline conditions.
In a fourth aspect of the invention, there is provided a process for preparing a 2,5-dicyclopentylcyclopentanone compound represented by the following general formula (5):
wherein R
1
through R
10
independently represent hydrogen or an alkyl group having 1 to 4 carbon atoms, which comprises reducing with hydrogen a 2,5-dicyclopentylidenecyclopentanone compound represented by the above formula (4).
In a fifth aspect of the invention, there is provided a process for preparing a 2,5-dicyclopentylidenecyclopentanol compound represented by the following general formula (6):
wherein R
1
through R
10
independently represent hydrogen or an alkyl group having 1 to 4 carbon atoms, which comprises reducing a 2,5-dicyclopentylidenecyclopentanone compound represented by the above formula (4).
In a sixth aspect of the invention, there is provided a process for preparing a 2,5-dicyclopentylcyclopentanol compound represented by the following general formula (7):
wherein R
1
through R
10
independently represent hydrogen or an alkyl group having 1 to 4 carbon atoms, which comprises reducing with hydrogen a 2,5-dicyclopentylcyclopentanone compound represented by the above formula (5).
In a seventh aspect of the invention, there is provided a process for preparing a 2,5-dicyclopentylcyclopentanol compound represented by the above formula (7), which comprises reducing with hydrogen a 2,5-dicyclopentylidenecyclopentanol compound represented by the above formula (6).
DESCRIPTION OF THE PREFERRED EMBODIMENTS
Composition Comprising Cyclopentane Compound Having Oxygen-Containing Group and Cyclopentylidene and/or Cyclopentyl Substituents, of Formula (1)
The cyclopentane compounds having an oxygen-containing group and cyclopentylidene and/or cyclopentyl substituents, which are represented by the above formula (1), are classified into two types, i.e., those which have a cyclopentanonol structure (in formula (1), —Y is —OH), and those which have a cyclopentanone structure (in formula (1), —Y is ═O). These compounds of formula (1) have 2,5-dicyclopentylidene substituents; 2,5-dicyclopentyl substituents; or 2-cyclopentilidene-5-cyclopentyl substituents.
Among the compounds of formula (1), those in which —Y is —OH include, for example, 2,5-dicyclopentylcyclopentan-1-ol, 2-cyclopentylidene-5-cyclopentylcyclopentan-1-ol and 2,5-dicyclopentylidene-cyclopentan-1-ol. Of these, 2,5-dicyclopentylcyclopentan-1-ol is preferable.
Among the compounds of formula (1), thos
Fujisawa Hiroshi
Yamada Masafumi
Armstrong Westerman & Hattori, LLP
Clardy S. Mark
Lamm Marina
Zeon Corporation
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