Perfume compositions – Perfume compositions – Ring containing active ingredient
Reexamination Certificate
1998-06-26
2003-04-15
Warden, Jill (Department: 1721)
Perfume compositions
Perfume compositions
Ring containing active ingredient
C424S070100, C510S101000, C512S015000
Reexamination Certificate
active
06548474
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to disubstituted cycloalkanones for use as fragrance materials. More particularly, the present invention relates to disubstituted cycloalkanones of the following general formula (I) or (II):
wherein R
1
is a straight-chain or branched saturated or unsaturated hydrocarbon group having between 1 and 6 carbon atoms, and m and n are each either 1 or 2.
Disubstituted cycloalkanones are prepared by alkylation of cycloalkylidenecycloalkanones (Qi et al., Hecheng Huaxue 4(4):296-299 (1996)). Disubstituted cycloalkanones are of interest as potential antiinflammatory compounds and anticancer compounds. Qi et al. synthesized 2-(1-cyclopentenyl)-2-alkylcyclopentanone Mannich base hydrochlorides, and performed studies on their anticancer and antiinflammatory properties (Zhongguo Yaowu Juaxue Zazhi 5(4):235-42 (1995)). They showed that some species had significant antitumor activity against cultured cancer cell lines, and others showed significant antiinflammatory activity comparable to that of indomethacin. In a separate work, the same authors synthesized &agr;,&bgr;-unsaturated and &bgr;-aminomethylcyclopentanones containing &agr;-(1-cyclopentenyl) and showed these compounds exhibited significant levels of anticancer activity in vitro against cultured cancer cell lines (Chin. Chem. Lett. 6(10):847-850 (1995)).
Various monosubstituted cycloalkanones have been investigated for use as fragrances. In particular, 2-cyclohexylcyclohexanone (reviewed in Food Cosmet. Toxicol. 12(3):399 (1974)) and 2-cyclopentenones (Ger. Offen. DE 83-3338853) have been prepared for use as fragrances. In addition, 2-cyclopentylcyclopentanone was used in preparation of a dentrifice, a soap, and a fragrance or flavoring composition giving a jasmine-like smell (European Patent EP 16650 801001). Furthermore, Japanese Patent Publication JP 82-230558 discloses the use of &dgr;-cyclopentyl-&dgr;-lactone in perfume preparations.
Mekhtiev et al. studied the structure/odor relationships among selected monosubstituted cycloalkanones (Dokl. Akad. Nauk Az. SSR 32(12):46-52 (1976)). They concluded that introduction of an n-alkyl group at the &agr;-position in a cyclopentanone ring caused a fatty odor increasing in intensity from methyl to propyl, and a strong jasmine scent for C4 to C7 groups. Cyclohexanone derivatives had a weaker jasmine scent than their cyclopentanone analogs. Branched amyl- and hexylcyclopentanones with geminal terminal methyl groups also gave a jasmine scent, with strong fruity or woody overtones. Substitution of a methyl or ethyl group at the &agr;′-position of the cyclopentanone ring carrying an n-alkyl group weakened the jasmine scent, and increased the fruity tones.
While monosubstituted and disubstituted cycloalkanones are known in the art, the use of di substituted cycloalkanones as fragrance materials has not been investigated. More particularly, the use of disubstituted cycloalkanones as fragrance materials for consumer products has not been investigated.
OBJECTS AND SUMMARY OF THE INVENTION
It is an object of the present invention to provide disubstituted cycloalkanones for use as fragrance material.
It is another object of the present invention to provide disubstituted cycloalkanones suitable for use as fragrance materials in commercial consumer products, such as cleaning materials, perfumes, and personal hygiene products.
Briefly stated, di substituted cycloalkanones are prepared from one of 2-cyclopentylidenecyclopentan-1-one, 2-cyclohexylidenecyclohexan-1-one, 2-cyclopentylidenecyclohexan-1-one, or 2-cyclohexylidenecyclopentan-1-one. The resulting compounds were analyzed for their odor characteristics. The different compounds exhibit varied odor characteristics, which are not predictable from the structures of the compounds. The compounds are useful in the preparation of fragrance compositions suitable for use in consumer products.
According to an embodiment of the present invention, a fragrance composition consisting of a disubstituted cycloalkanone of the following general formula (I) or (II):
wherein R
1
is a member selected from the group consisting of a straight-chain saturated hydrocarbon group, a branched saturated hydrocarbon group, a straight-chain unsaturated hydrocarbon group, and a branched unsaturated hydrocarbon group, and wherein R
1
has between 1 and 6 carbon atoms, and wherein m and n are each either 1 or 2.
The above, and other objects, features and advantages of the present invention will become apparent from the following description read in conjunction with the accompanying drawing.
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Green Carter B.
Lupo, Jr. Andrew T.
Nakatsu Tetsuo
Cole Monique T.
Darby & Darby
Takasago International Corporation
Warden Jill
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