Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1997-07-18
1999-03-09
Killos, Paul J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
554228, 560138, C07C 3912, C07C 5300, C07C 6900
Patent
active
058803149
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention is related to novel hydrochalcone compounds, cosmetic compositions containing said hydrochalcone compounds as effective components which are very safe to the skin and have good shelf life, and methods of producing the same.
BACKGROUND ART
Ultraviolet rays cause inflammation of the skin mainly in the form of erythema, in which various chemical mediators are released to stimulate melanocytes which promote the synthesis of melanin causing the skin to darken. This darkening is caused by an excessive production of melanin in the melanocytes, then transferred to epidermic cells.
Conventionally, depigmenting cosmetics containing salts and various derivatives of vitamin C, hydroquinone monobenzyl ether, hydrogen peroxide or the like have been proposed to prevent pigment deposition, spots, freckles or the like on the skin and to maintain natural white skin. Further, various plant extracts or plant-derived materials such as gallic acid and geranial or the like have been proposed for use in such cosmetics. Furthermore, hydroquinone or hydrochalcone derivatives such as phlorine, phlorizin, phlorezin (Japanese Patent Laid-open 92/235112), dihydrophloretin (WO95/11662) have been reported to have an effect in suppressing the synthesis of melanin.
However, most of these compounds were found not to be very effective in preventing pigment deposition or in depigmenting the skin because of their poor shelf life when formulated, or their poor efficacy in suppressing inflammation caused by ultraviolet irradiation. Further, when hydroquinone monobenzyl ether or the like are combined in such cosmetics, although skin darkened with deposited pigment can be effectively lightened, there are side effects such as skin allergies and irritation or other problems. Furthermore, the various plant extracts have problems, such that their efficacy is not quite satisfactory, or the quality of the extracts is not always consistent.
Furthermore, although it has been reported in U.S. Pat. No. 4,954,659 that hydrochalcone compounds have anti-oxidative activity, their potential usefulness in cosmetics has not been disclosed.
Thus, it is very difficult to obtain cosmetics which are highly effective in suppressing pigment deposition and depigmentation and which are very safe to the skin and have good shelf life. Therefore, development of cosmetics satisfying these was desirous.
DISCLOSURE OF INVENTION
Accordingly, under these circumstances, the present inventors carried out intensive research to resolve the problems in the conventional technology. As a result, the inventors have found that extracts obtained from plants of Dioscorea composita are highly active in inhibiting tyrosinase activity, are very safe to the skin, and are sufficiently stable during storage when combined in various cosmetic formulations.
Furthermore, the present inventors have found that an active component in said extracts is a novel hydrochalcone compound, and that synthetic compounds and esterified compounds of said hydrochalcone compound are highly active in inhibiting tyrosinase activity, are very safe to the skin, and are sufficiently stable during storage when combined in various cosmetic formulations. Thus the present invention has been completed.
Namely, hydrochalcone compounds of the present invention have the following formula (I): ##STR2## in which R.sup.1 to R.sup.4 are each independently H or --COR, and R is an alkyl group having 1-20 carbon atoms.
Cosmetic compositions of the present invention comprise a hydrochalcone compound represented by formula (I) above as an effective component.
Hydrochalcone compounds of formula (I) above can be obtained by extracting Dioscorea composita plants with suitable solvents to obtain extracts containing the abovementioned hydrochalcone derivatives. Furthermore, these extracts or hydrochalcone compounds isolated and purified from these extracts can be used as effective components in cosmetic compositions.
BEST MODE FOR CARRYING OUT THE INVENTION
Embodiments of the present invention ar
REFERENCES:
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patent: 4954659 (1990-09-01), Parkhurst et al.
Journal of Chemical Society, Perkin Trans. I, (7), (1979), pp. 1661-1664, Matt Karhu et al, "Acid-catalysed Rearrangement of 2,3,4,5-tetrahydrobenz(b)oxepin-2-spirocyclohexa-2',5-dien-4'-one and 3',5',7',9-tetra-t-butyl-2,3,4,5-tetrahydrobenz(b)oxepin-2-spirocyclohexa- 2',5'-dien-4'-one. Evidence for Quinone Methide Intermediate".
Journal of Chemical Society, Perkin Trans. I, (1), (1981), pp. 303-306, Matti Karhu et al., "Formation of Diphenyl Ethers from Cyclohexa-2,5-dienones via 4-Phenoxy-4-(1-alkoxy)cyclohexa-2,5-dienones as Probable Intermediates".
Patent Abstracts of Japan, vol. 017, No. 659 (C-1137), Dec. 7, 1993 & JP 05213729 A (Kao Corp), Aug. 24, 1993 *Abstract*.
Database WPI, Section Ch, Week 9436, Derwent Publications Ltd., London, GB; Class BO4, AN 94290835 XP002057894 & JP 06219934A (Dowa Mining Co., Ltd.), Aug. 9, 1994 *Abstract*.
Database WPI, Section Ch, Week 9724, Derwent Publications Ltd., London, GB; Class BO4, AN 97259816 XP002057895 & CN 1101285A (Feng Weiyuan), Apr. 12, 1995 *Abstract*.
Kaminaga Hiroko
Morimoto Shigeharu
Nozaki Shohei
Sakamoto Masahiro
Shinomiya Tatsuro
Davis Brian J.
Killos Paul J.
Mitsui Chemicals Inc.
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