JPH022848B2 - - Google Patents
Info
- Publication number
- JPH022848B2 JPH022848B2 JP15541881A JP15541881A JPH022848B2 JP H022848 B2 JPH022848 B2 JP H022848B2 JP 15541881 A JP15541881 A JP 15541881A JP 15541881 A JP15541881 A JP 15541881A JP H022848 B2 JPH022848 B2 JP H022848B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- ursolic acid
- ursolic
- ester
- skin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- PLSAJKYPRJGMHO-UHFFFAOYSA-N ursolic acid Natural products CC1CCC2(CCC3(C)C(C=CC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1C)C(=O)O PLSAJKYPRJGMHO-UHFFFAOYSA-N 0.000 claims description 44
- 229940096998 ursolic acid Drugs 0.000 claims description 44
- WCGUUGGRBIKTOS-GPOJBZKASA-N (3beta)-3-hydroxyurs-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C WCGUUGGRBIKTOS-GPOJBZKASA-N 0.000 claims description 32
- 239000002537 cosmetic Substances 0.000 claims description 23
- 150000003675 ursolic acids Chemical class 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 8
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- 239000002253 acid Substances 0.000 description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- -1 ursolic acids Chemical class 0.000 description 18
- 230000000694 effects Effects 0.000 description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 10
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 10
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 235000010323 ascorbic acid Nutrition 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 102000003425 Tyrosinase Human genes 0.000 description 7
- 108060008724 Tyrosinase Proteins 0.000 description 7
- 239000006071 cream Substances 0.000 description 7
- 239000003205 fragrance Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 239000004808 2-ethylhexylester Substances 0.000 description 5
- 108010024636 Glutathione Proteins 0.000 description 5
- 229960005070 ascorbic acid Drugs 0.000 description 5
- 239000011668 ascorbic acid Substances 0.000 description 5
- 238000002845 discoloration Methods 0.000 description 5
- 229960003180 glutathione Drugs 0.000 description 5
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 5
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 5
- 229960002216 methylparaben Drugs 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000006210 lotion Substances 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 150000000996 L-ascorbic acids Chemical class 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000002087 whitening effect Effects 0.000 description 3
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 206010014970 Ephelides Diseases 0.000 description 2
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 2
- 208000003351 Melanosis Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 2
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
- 239000001509 sodium citrate Substances 0.000 description 2
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229940032094 squalane Drugs 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- 150000003648 triterpenes Chemical class 0.000 description 2
- GZIFEOYASATJEH-VHFRWLAGSA-N δ-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-VHFRWLAGSA-N 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- WFSGQBNCVASPMW-UHFFFAOYSA-N 2-ethylhexanoyl chloride Chemical compound CCCCC(CC)C(Cl)=O WFSGQBNCVASPMW-UHFFFAOYSA-N 0.000 description 1
- NPSJHQMIVNJLNN-UHFFFAOYSA-N 2-ethylhexyl 4-nitrobenzoate Chemical compound CCCCC(CC)COC(=O)C1=CC=C([N+]([O-])=O)C=C1 NPSJHQMIVNJLNN-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- GZIFEOYASATJEH-UHFFFAOYSA-N D-delta tocopherol Natural products OC1=CC(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-UHFFFAOYSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 244000141359 Malus pumila Species 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 206010042496 Sunburn Diseases 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229940067596 butylparaben Drugs 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 235000010389 delta-tocopherol Nutrition 0.000 description 1
- VJNCICVKUHKIIV-UHFFFAOYSA-N dopachrome Chemical compound O=C1C(=O)C=C2NC(C(=O)O)CC2=C1 VJNCICVKUHKIIV-UHFFFAOYSA-N 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229940105132 myristate Drugs 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000005375 photometry Methods 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002446 δ-tocopherol Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/63—Steroids; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/74—Biological properties of particular ingredients
- A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
- A61K2800/782—Enzyme inhibitors; Enzyme antagonists
Description
本発明は新規な化粧料、更に詳しくはウルソー
ル酸、その塩類もしくはウルソール酸誘導体の少
なくとも一種又は二種以上を配合してなる皮膚の
黒化を防止した化粧料、所謂美白化粧料に関する
ものである。
従来より、ウルサン系トリテルペノイドの一つ
として挙げられるウルソール酸は、リンゴ、サク
ランボなどの果実や葉のロウ状被覆物質中に広く
分布することで知られているが、本発明者は、ウ
ルソール酸をはじめとする各種ウルソール酸類に
ついて鋭意研究した結果、これらを化粧料基剤に
配合し皮膚に塗布すると、本物質においてはこれ
まで全く知られていなかつた効果、すなわちチロ
シナーゼ活性阻害に基づく著しい皮膚の黒化を防
止する効果を見出すことに到つた。
一般に皮膚に対して日光からの紫外線が照射さ
れると、皮膚内のチロシナーゼ活性作用によりメ
ラニンが著しく生成して皮膚が黒化する傾向があ
る。このような日焼けによる皮膚の黒化を防止す
る目的で化粧料に配合されてきた物質としては、
かねてよりアスコルビン酸類、過酸化水素、グル
タチオン、コロイド硫黄等や各種天然物が知られ
ているが、アスコルビン酸類は湿性製品の如き水
分を多く含む系においては酸化されやすく不安定
であり、変色、変臭の原因となりがちである。過
酸化水素については過酸化物という特性上、安全
性、保存面、安定性面から充分なものとは云い難
い。グルタチオンやコロイド硫黄は異臭を放つた
め化粧料へ使用することは避けられている。ま
た、天然物については効果の確認されたものは殆
んどなく、しかも前記の各物質と同様に皮膚の黒
化を防止する効果は充分に満足すべきものではな
い。いずれにしても、本発明に係るウルソール酸
類の如きトリテルペノイド化合物についてのチロ
シナーゼ阻害作用を応用した例は皆無である。
すなわち、本発明の主たる目的はウルソール
酸、その塩類、又はウルソール酸各種誘導体を化
粧料基剤に配合することにより、上記公知の皮膚
の黒化を防止する物質では得られない極めて優れ
た効果を有する新規な化粧料を提供することにあ
る。
本発明に適用されるウルソール酸、その塩頼又
はウルソール酸誘導体は下記一般式（）で示さ
れるもので、式中３位の水酸基を無置換又は各種
アシル基で置換し、また、28位のカルボキシル基
を無置換あるいは塩基で置換又は各種アルキル基
によりエステル化したものである。
一般式（）
（式中R1は水素原子又はNa、Ｋ、NH4、H2N
（CH3）2、Ca、Mgもしくは直鎖、分岐アルコー
ルアルキル残基であり、R2は水素原子又は直鎖、
分岐脂肪酸アシル残基であることを表わす。）
上記一般式（）で示されるウルソール酸、そ
の塩類の具体例としては、ウルソール酸、ウルソ
ール酸ナトリウム、ウルソール酸カリウム、ウル
ソール酸アンモニウム、ウルソール酸ジメチルア
ンモニウム、ウルソール酸カルシウム、ウルソー
ル酸マグネシウムなどが挙げられ、一方、ウルソ
ール酸誘導体であるアシルウルソール酸及びその
エステル誘導体の具体例としては、ブタノイルウ
ルソール酸、ブタノイルウルソール酸ナトリウ
ム、オクタノイルウルソール酸、ウラロイルウル
ソール酸、ラウロイルウルソール酸アンモニウ
ム、パルミトイルウルソール酸、パルミトイルウ
ルソール酸マグネシウム、２−エチルヘキサノイ
ルウルソール酸、ヘキシルデカノイルウルソール
酸、オクタノイルウルソール酸エチルエステル、
パルミトイルウルソール酸エチルエステル、２−
エチルヘキサノイルウルソール酸−２−エチルヘ
キシルエステル、２−ヘキシルデカノイルウルソ
ール酸オクチルドデシルエステル、ジラウロイル
ウルソール酸セチルエステル、ジブタノイルウル
ソール酸−２−ヘキシルデシルエステルがあげら
れ、また、ウルソール酸アルキルエステル誘導体
の具体例としては、ウルソール酸エチルエステ
ル、ウルソール酸２−エチルヘキシルエステル、
ウルソール酸オクチドデシルエステル、ウルソー
ル酸セチルエステル、ウルソール酸−２−ヘキシ
ルデシルエステルなどがあげられる。一般式
（）中のR2で示されたアシル基が炭素数２〜
20、R1で示されたアルキル基が炭素数１〜20の
ものが安定性ならびに化粧料への取り扱いのしや
すさの面から挙げられ、これらは各種化粧料剤型
に応じて適宜選択されるものである。
本発明に適用されるアシルウルソール酸及びそ
のアルキルエステル誘導体を合成する方法として
は種々あるが、例えばアシルウルソール酸におい
ては、ウルソール酸にテトラヒドロフラン等非極
性溶媒下、トリエチルアミン等塩基存在下、所望
の脂肪酸クロライドを反応させ目的物を得る方法
が有利であり、またアシルウルソール酸アルキル
エステル誘導体においては、まずウルソール酸を
クロロホルム等適当溶媒下、トリエチルアミン等
塩基存在下、塩化チオニル等塩素化剤を作用さ
せ、ウルソール等クロライドを生成せしめ、これ
にエタノール、セタノール等所望のアルコールを
トリエチルアミン等塩基存在下反応させ、ウルソ
ール酸アルキルエステルとなし、アシル化は前記
手法に従つて目的物を得る方法が同じく有利であ
る。
次にアシルウルソール酸及びそのアルキルエス
テル誘導体の合成例を示す。
合成例 １
ブタノイルウルソール酸
ウルソール酸45.7ｇをテトラヒドロフラン200
mlに溶解し、トリエチルアミン32ｇを加えた混合
液に、酪酸クロライド12ｇを氷冷下において滴下
しながら１時間撹拌反応させ、次いで室温で２時
間撹拌後、未反応酪酸クロライド、トリエチルア
ミンをエタノール及び２％塩酸でそれぞれ処理
後、反応物を酢酸エチルで抽出し、さらに抽出溶
媒を留去し粗反応物を得た。精製はカラムを用
い、ヘキサン／エーテル（98／２）溶媒により溶
出させ、白色結晶のブタノイルウルソール酸34.2
ｇを得る。収率65％であつた。
合成例 ２
オクタノイルウルソール酸エチル
ウルソール酸45.7ｇとトリエチルアミン10.1ｇ
をクロロホルム100mlに溶解した混合液に、別に
新しく蒸留した塩化チオニル11.9ｇをクロロホル
ム30mlに溶解したものを、氷冷下において滴下し
ながら１時間撹拌反応させ、生成するウルソール
酸クロライドを取り出すことなく、エタノール32
ｇを加え、トリエチルアミン10.1ｇをクロロホル
ム30mlに溶解した溶液をさらに氷冷下滴下し３時
間反応させた後、生成したトリエチルアミン塩酸
塩を別し、40℃以下で留去する。
次いで得られたウルソール酸エチルをベンゼン
200mlに溶解し、さらにトリエチルアミンを32ｇ
を加えた混合液にオクチル酸クロライド36ｇを氷
冷下において滴下しながら１時間撹拌反応させ、
次いで室温で２時間撹拌後、反応を停止し、未反
応トリエチルアミンを２％塩酸で処理後、反応物
を酢酸エチルで抽出し、抽出溶媒を留去し粗反応
物を得た。精製はカラムを用いヘキサン／エーテ
ル（98／２）溶媒により溶出させ、無色液体のオ
クタノイルウルソール酸エチルエステル36ｇを得
る。収率59％。
合成例 ３
２−エチルヘキサノイルウルソール酸−２−エ
チルヘキシルエステル
ウルソール酸45.7ｇとトリエチルアミン10.1ｇ
をベンゼン100mlに溶解した混合液に、別に新し
く蒸留した塩化チオニル11.9ｇをベンゼン30mlに
溶解したものを、氷冷下において滴下しながら１
時間撹拌反応させ、生成するウルソール酸クロラ
イドを取り出すことなく、２−エチルヘキシルア
ルコール12ｇ、トリエチルアミン10.1ｇをベンゼ
ン30mlに溶解した混合液をさらに氷冷下滴下し３
時間反応させた後、生成したトリエチルアミン塩
酸塩別し、溶媒を40℃以下で留去する。次いで
得られたウルソール酸−２−エチルヘキシルエス
テルをベンゼン200mlに溶解し、さらにトリエチ
ルアミン32ｇを加えた混合液に、２−エチルヘキ
サン酸クロライド36ｇを氷冷下において滴下しな
がら１時間撹拌反応させ、次いで室温で２時間撹
拌、さらにベンゼンの沸点で還流を１時間行なつ
た後、反応を停止し、未反応トリエチルアミンを
２％塩酸で処理後、反応物を酢酸エチルで抽出
し、さらに抽出溶媒を留去し粗反応物を得た。精
製はカラムを用いヘキサン／エーテル（98／２）
溶媒により溶出させ、無色液体の２−エチルヘキ
サノイルウルソール酸−２−エチルヘキシルエス
テル30ｇを得る。収率49％
本発明化粧料に配合されるウルソール酸、その
塩類およびその誘導体の配合量はそれぞれ全重量
中0.01〜５重量％好ましくは0.1〜１重量％であ
る。0.01重量％未満では皮膚に対し本発明化粧料
を塗布しても、経皮吸収量が皮膚の黒化を防止す
る効果を発現する必要量とならず、また５重量％
超える場合は、皮膚に対する影響の点から避ける
べきである。
上記ウルソール酸、その塩類又はウルソール酸
誘導体を化粧料基剤に配合する場合には、これら
を単独あるいは併用しても、またその他の還元性
皮膚黒化防止物質と共に用いてもよい。ウルソー
ル酸ならびにウルソール酸誘導体の一つであるブ
タノイルウルソール酸のチロシナーゼ阻害作用に
ついて、ハーデイング−パツセイ（Harding−
Passay）マウスメラノーマから抽出した酵素チ
ロシナーゼを使用し、その酵母活性をドーパーク
ロームの475nｍの吸光度を測定するフオトメト
リー法で行なつた。試験物質ウルソール酸及びウ
ルソール酸誘導体の３×10-5molをモルモツト皮
膚ホモジネートをインキユベーシヨンしたのちそ
の反応液を該皮膚ホモジネートを対照にとりドー
パークローム反応をみるとウルソール酸ならびに
ウルソール酸誘導体は12分間の誘導期を示したの
に対し、皮膚ホモジネートのみの誘導期は約２分
間であつた。また誘導期終了後の反応速度も皮膚
ホモジネートのみの反応初速度の50％阻害を示し
た。これらより、ウルソール酸、ウルソール酸誘
導体はチロシナーゼ活性を阻害しドーパククロー
ムの生成を低下させることが実証された。
以上詳述した如く、本発明は生体活性に優れた
ウルソール酸、その塩類およびその各種ウルソー
ル酸誘導体を効果的に配合した皮膚の黒化を防止
する化粧料に関するものであり、従来知られてい
る各種アスコルビン酸類、過酸化水素、グルタチ
オン、コロイド硫黄等の公知物質特にチロシナー
ゼ活性阻害を有するグルタチオンに比し、優れた
効能を有しかつ安定な、所謂美白化粧料を提供す
るものである。
又、本発明の化粧料の有効成分であるウルソー
ル酸及びその誘導体は極めて安定であり、製剤と
した場合も変色、変臭、分解失活などの経時変化
を起さないので各種の化粧料に対して安定かつ容
易に配合することができる点で、極めて有利であ
る。
次に、ウルソール酸誘導体としてブタノイルウ
ルソール酸セチルエステルＡを1.0％配合した実
施例５に示される水中油型エマルジヨンタイプの
クリームと、この実施例５中のウルソール酸誘導
体をアスコルビン酸ジステアレートＢで置換して
なる同一処方のクリームについて、40℃下放置に
よる熱安定性を経時的に観察した結果を以下に示
す。第１図は経時下における有効成分〔Ａまたは
Ｂ〕の残存率、表１は変臭の度合、表２は変色の
度合をそれぞれ表わしたものである。
The present invention relates to a novel cosmetic, and more particularly to a cosmetic that prevents darkening of the skin, which is a so-called whitening cosmetic that contains at least one or two or more of ursolic acid, its salts, or ursolic acid derivatives. . It has been known that ursolic acid, which is one of the ursan triterpenoids, is widely distributed in the waxy coating of fruits and leaves of apples, cherries, etc. As a result of intensive research on various ursolic acids including ursolic acids, we found that when these are blended into a cosmetic base and applied to the skin, this substance has an effect that was completely unknown until now, namely, a significant skin darkening due to inhibition of tyrosinase activity. We have discovered an effect that prevents this from occurring. Generally, when the skin is irradiated with ultraviolet rays from sunlight, melanin is significantly produced due to the activation of tyrosinase in the skin, and the skin tends to darken. Substances that have been added to cosmetics to prevent skin darkening caused by sunburn include:
Various natural products such as ascorbic acids, hydrogen peroxide, glutathione, colloidal sulfur, etc. have been known for some time, but ascorbic acids are easily oxidized and unstable in systems containing a lot of water such as wet products, causing discoloration and discoloration. It tends to cause odor. Due to the characteristics of hydrogen peroxide, it is difficult to say that it is sufficient in terms of safety, storage, and stability. Glutathione and colloidal sulfur are avoided in cosmetics because they emit a strange odor. Moreover, there are almost no natural products whose effects have been confirmed, and like the above-mentioned substances, their effect on preventing skin darkening is not fully satisfactory. In any case, there are no examples of applying the tyrosinase inhibitory effect of triterpenoid compounds such as ursolic acids according to the present invention. That is, the main purpose of the present invention is to achieve extremely excellent effects that cannot be obtained with the above-mentioned known skin tanning prevention substances by incorporating ursolic acid, its salts, or various ursolic acid derivatives into a cosmetic base. The object of the present invention is to provide a novel cosmetic material that has the following properties. The ursolic acid, its base salt, or ursolic acid derivatives applied to the present invention are those represented by the following general formula (), in which the hydroxyl group at the 3-position is unsubstituted or substituted with various acyl groups, and the 28-position hydroxyl group is unsubstituted or substituted with various acyl groups. The carboxyl group is unsubstituted, substituted with a base, or esterified with various alkyl groups. General formula () (In the formula, R 1 is a hydrogen atom or Na, K, NH 4 , H 2 N
(CH 3 ) 2 , Ca, Mg or a straight chain, branched alcohol alkyl residue, R 2 is a hydrogen atom or a straight chain,
Indicates that it is a branched fatty acid acyl residue. ) Specific examples of ursolic acid represented by the above general formula () and its salts include ursolic acid, sodium ursolic acid, potassium ursolic acid, ammonium ursolic acid, dimethylammonium ursolic acid, calcium ursolic acid, magnesium ursolic acid, etc. On the other hand, specific examples of acylursolic acid and its ester derivatives, which are ursolic acid derivatives, include butanoylursolic acid, sodium butanoylursolic acid, octanoylursolic acid, uraloylursolic acid, ammonium lauroylursolic acid, and palmitoylursole. acid, magnesium palmitoylursolic acid, 2-ethylhexanoylursolic acid, hexyldecanoylursolic acid, octanoylursolic acid ethyl ester,
Palmitoylursolic acid ethyl ester, 2-
Examples include ethylhexanoylursolic acid-2-ethylhexyl ester, 2-hexyldecanoylursolic acid octyldodecyl ester, dilauroylursolic acid cetyl ester, dibutanoylursolic acid-2-hexyldecyl ester, and ursolic acid alkyl ester. Specific examples of derivatives include ursolic acid ethyl ester, ursolic acid 2-ethylhexyl ester,
Examples include octidodecyl ursolic acid ester, cetyl ursolic acid ester, and 2-hexyldecyl ursolic acid ester. The acyl group represented by R 2 in the general formula () has 2 or more carbon atoms.
20. Those in which the alkyl group represented by R 1 has 1 to 20 carbon atoms are listed from the viewpoint of stability and ease of handling in cosmetics, and these are selected as appropriate depending on the type of cosmetic preparation. It is something that There are various methods for synthesizing acyl ursolic acid and its alkyl ester derivatives that can be applied to the present invention. The method of obtaining the desired product by reacting chloride is advantageous, and in the case of acyl ursolic acid alkyl ester derivatives, first, ursolic acid is reacted with a chlorinating agent such as thionyl chloride in an appropriate solvent such as chloroform in the presence of a base such as triethylamine, and It is equally advantageous to generate a chloride such as ursole, react it with a desired alcohol such as ethanol or cetanol in the presence of a base such as triethylamine to form an alkyl ursolic acid ester, and obtain the desired product by following the above-mentioned method for acylation. . Next, examples of synthesis of acyl ursolic acid and its alkyl ester derivatives will be shown. Synthesis example 1 Butanoyl ursolic acid 45.7 g of ursolic acid was mixed with 200 g of tetrahydrofuran.
ml and added 32 g of triethylamine, 12 g of butyric acid chloride was added dropwise under ice cooling and reacted with stirring for 1 hour. After stirring at room temperature for 2 hours, unreacted butyric acid chloride and triethylamine were dissolved in ethanol and 2% After each treatment with hydrochloric acid, the reaction product was extracted with ethyl acetate, and the extraction solvent was distilled off to obtain a crude reaction product. For purification, use a column and elute with hexane/ether (98/2) solvent to obtain white crystals of butanoylursolic acid (34.2%).
get g. The yield was 65%. Synthesis example 2 Ethyl octanoylursolic acid 45.7g of ursolic acid and 10.1g of triethylamine
Separately, 11.9 g of freshly distilled thionyl chloride dissolved in 30 ml of chloroform was added dropwise to a mixed solution of 100 ml of chloroform, and stirred and reacted for 1 hour, without removing the ursolic acid chloride produced. ethanol 32
A solution of 10.1 g of triethylamine dissolved in 30 ml of chloroform was further added dropwise under ice cooling and reacted for 3 hours. The triethylamine hydrochloride formed was separated and distilled off at below 40°C. Then, the obtained ethyl ursolic acid was mixed with benzene.
Dissolve in 200ml and add 32g of triethylamine
36 g of octylic acid chloride was added dropwise to the mixed solution under ice cooling, and the mixture was stirred and reacted for 1 hour.
After stirring at room temperature for 2 hours, the reaction was stopped, unreacted triethylamine was treated with 2% hydrochloric acid, the reaction product was extracted with ethyl acetate, and the extraction solvent was distilled off to obtain a crude reaction product. Purification was carried out using a column and eluting with a hexane/ether (98/2) solvent to obtain 36 g of octanoylursolic acid ethyl ester as a colorless liquid. Yield 59%. Synthesis Example 3 2-ethylhexanoylursolic acid-2-ethylhexyl ester 45.7g of ursolic acid and 10.1g of triethylamine
Separately, 11.9 g of freshly distilled thionyl chloride dissolved in 30 ml of benzene was added dropwise to a mixture of 100 ml of benzene while cooling on ice.
The reaction was stirred for hours, and a mixture of 12 g of 2-ethylhexyl alcohol and 10.1 g of triethylamine dissolved in 30 ml of benzene was added dropwise under ice cooling without taking out the ursolic acid chloride produced.
After reacting for an hour, the triethylamine hydrochloride produced is separated and the solvent is distilled off at 40°C or below. Next, the obtained ursolic acid-2-ethylhexyl ester was dissolved in 200 ml of benzene, and 32 g of triethylamine was further added to the mixture. 36 g of 2-ethylhexanoic acid chloride was added dropwise under ice cooling, and the reaction was stirred for 1 hour. After stirring at room temperature for 2 hours and refluxing at the boiling point of benzene for 1 hour, the reaction was stopped, unreacted triethylamine was treated with 2% hydrochloric acid, the reaction product was extracted with ethyl acetate, and the extraction solvent was distilled off. A crude reaction product was obtained. Purification using a column with hexane/ether (98/2)
Elution with a solvent yields 30 g of 2-ethylhexanoylursolic acid-2-ethylhexyl ester as a colorless liquid. Yield: 49% The amounts of ursolic acid, its salts and its derivatives to be blended into the cosmetic composition of the present invention are 0.01 to 5% by weight, preferably 0.1 to 1% by weight, based on the total weight. If it is less than 0.01% by weight, even if the cosmetic of the present invention is applied to the skin, the amount of transdermal absorption will not be the required amount to exhibit the effect of preventing skin darkening, and if it is less than 5% by weight.
Exceeding the amount should be avoided in view of the effects on the skin. When the above-mentioned ursolic acid, its salts or ursolic acid derivatives are incorporated into a cosmetic base, they may be used alone or in combination, or together with other reducing skin darkening inhibiting substances. The tyrosinase inhibitory effect of ursolic acid and butanoylursolic acid, one of the ursolic acid derivatives, was studied by Harding-Putsey.
Using the enzyme tyrosinase extracted from mouse melanoma (Passay), its yeast activity was determined by photometry, which measures the absorbance of Doperchrome at 475 nm. After incubating guinea pig skin homogenate with 3 x 10 -5 mol of the test substance ursolic acid and ursolic acid derivatives, the reaction solution was compared with the skin homogenate and the doperchrome reaction was observed. It showed an lag period of 12 minutes, whereas the lag period of skin homogenate alone was approximately 2 minutes. Furthermore, the reaction rate after the induction period was inhibited by 50% of the initial reaction rate of the skin homogenate alone. These results demonstrated that ursolic acid and ursolic acid derivatives inhibit tyrosinase activity and reduce the production of dopachrome. As detailed above, the present invention relates to cosmetics for preventing skin darkening that are effectively formulated with highly bioactive ursolic acid, its salts, and its various ursolic acid derivatives, and which are conventionally known. The present invention provides a so-called whitening cosmetic that has superior efficacy and stability compared to known substances such as various ascorbic acids, hydrogen peroxide, glutathione, and colloidal sulfur, especially glutathione, which inhibits tyrosinase activity. In addition, ursolic acid and its derivatives, which are the active ingredients of the cosmetics of the present invention, are extremely stable and do not undergo changes over time such as discoloration, odor, or decomposition and inactivation even when made into formulations, so they can be used in various cosmetics. It is extremely advantageous in that it can be stably and easily blended. Next, an oil-in-water emulsion type cream shown in Example 5 containing 1.0% butanoylursolic acid cetyl ester A as an ursolic acid derivative and ascorbic acid distearate B were added to the ursolic acid derivative in Example 5. The results of the thermal stability observation over time of creams with the same formulation after being left at 40°C are shown below. Figure 1 shows the residual rate of the active ingredient [A or B] over time, Table 1 shows the degree of odor change, and Table 2 shows the degree of discoloration.
【表】【table】
【表】【table】
【表】
第１図、表１及び表２の結果に示される如く、
本発明に係るウルソール酸誘導体Ａは４週間後に
おいても分解失活せず高い安定性（残存率）を有
しているのに対し、従来品であるアスコルビン酸
ジステアレートＢは分解失活が著しく、結果とし
て変臭、変色を引起こしていることは明らかであ
る。
尚、上記アスコルビン酸ジステアレートに代え
てグルタチオンについても同様の観察を行なつた
が、ほゞ同一の結果となつた。
更に上記Ａを１％配合した本発明クリームと該
物質を配合しないでアスコルビン酸ジステアレー
トを配合した従来クリームを統計的に同等な各々
100名の女性集団に１ケ月連用させたところ、前
者の本発明クリームはしみそばかすの改善におい
て、対照の従来クリームに比較し明らかに有効で
あることが証明された。（表−３参照）[Table] As shown in the results of Figure 1, Table 1 and Table 2,
Ursolic acid derivative A according to the present invention does not decompose and lose its activity even after 4 weeks and has high stability (residual rate), whereas the conventional product ascorbic acid distearate B shows significant decomposition and deactivation. It is clear that this results in odor and discoloration. Incidentally, similar observations were made using glutathione instead of ascorbic acid distearate, but almost the same results were obtained. Furthermore, the cream of the present invention containing 1% of the above A and the conventional cream containing ascorbic acid distearate without containing this substance were statistically equivalent to each other.
When a group of 100 women used it continuously for one month, the former cream of the present invention was proven to be clearly more effective in improving dark spots and freckles than the conventional control cream. (See Table-3)
【表】
上記の他に、本発明に係る化粧料と上記公知物
質を配合した化粧料を用いて皮膚に対する色白効
果、シミ・ソバカスの解消、美肌効果等の使用テ
ストを行なつたが、ここにおいても本発明化粧料
の効果が格段に優れていることが実証された。
次に本発明化粧料の実施例を示す。配合割合は
重量部である。
実施例 １
化粧水
エタノール 10.0
プロピレングリコール 5.0
ポリオキシエチレン（50）水添ヒマシ油 0.5
クエン酸 0.015
クエン酸ナトリウム 0.1
メチルパラベン 0.05
ウルソール酸ブチルエステル 1.0
香 料 適量
水 83.0
実施例 ２
化粧オイル
スクワラン 47.5
ヒマシ油 49.9
ステアロイルウルソール酸ブチルエステル 1.0
ブチルヒドロキシトルエン 0.01
香 料 適量
実施例 ３
パツク
ポリビニルアルコール 20.0
エタノール 20.0
ブタノイルウルソール酸 1.0
グリセリン 5.0
香 料 適量
水 53.5
実施例 ４
二層タイプ化粧水
Ａエタノール
１，３−ブチルグリコール 15.0
4.0
Ｂ流動パラフイン
ミリスチン酸イソプロピル
ラウロイルウルソール酸
エチルエステル 5.0
1.0
0.5
Ｃ香 料
メチルパラベン
水 適量
0.1
74.4
実施例 ５
クリーム
ステアリン酸 8.0
ゲイロウ 4.0
セタノール 4.0
ラノリン 2.0
ミリスチン酸イソプロピル 6.0
スクワラン 7.0
オリーブ油 2.0
モノステアリン酸ポリオキシエチレンソルビタン
5.0
モノステアリン酸ソルビタン 1.0
プロピレングリコール 5.0
ブチルパラベン 0.1
メチルパラベン 0.1
ブチルヒドロキシトルエン 0.05
香 料 適量
水 54.5
ブタノイルウルソール酸セチルエステル 1.0
実施例 ６
化粧水
エタノール 7.0
プロピレングリコール 5.0
ポリオキシエチレン（50）硬化ヒマシ油 0.5
クエン酸 0.02
クエン酸ナトリウム 0.1
メチルパラベン 0.05
δ−トコフエロール 0.2
ウルソール酸 0.1
ウルソール酸ナトリウム 0.2
香 料 0.4
水 87.0
実施例 ７
化粧水
エタノール 10.0
グリセリン 5.0
プロピレングリコール 4.0
オレイルアルコール 0.1
ウルソール酸アンモニウム 0.1
ウルソール酸マグネシウム 0.05
ポリオキシエチレン（20）ソルビタンモノラウレ
ート 1.5
ポリオキシエチレン（20）ラウリルエーテル 0.5
メチルパラベン 0.05
香 料 0.3
水 78.4[Table] In addition to the above, we conducted use tests on the skin whitening effect, eliminating spots and freckles, beautifying the skin, etc. using cosmetics containing the cosmetics according to the present invention and the above-mentioned known substances. It was also demonstrated that the effects of the cosmetics of the present invention were extremely excellent. Next, examples of the cosmetics of the present invention will be shown. The blending ratio is in parts by weight. Example 1 Lotion ethanol 10.0 Propylene glycol 5.0 Polyoxyethylene (50) Hydrogenated castor oil 0.5 Citric acid 0.015 Sodium citrate 0.1 Methylparaben 0.05 Ursolic acid butyl ester 1.0 Fragrance Appropriate amount of water 83.0 Example 2 Cosmetic oil Squalane 47.5 Castor oil 49.9 Stearoylursolic acid butyl ester 1.0 Butylated hydroxytoluene 0.01 Fragrance Appropriate amount Example 3 Packaging polyvinyl alcohol 20.0 Ethanol 20.0 Butanoylursolic acid 1.0 Glycerin 5.0 Fragrance Appropriate amount Water 53.5 Example 4 Two-layer type lotion A Ethanol 1,3-butyl glycol 15.0 4.0 B Liquid paraffin myristate isopropyl lauroyl ursolic acid ethyl ester 5.0 1.0 0.5 C Fragrance methylparaben water Appropriate amount 0.1 74.4 Example 5 Cream stearic acid 8.0 Gaylow 4.0 Setanol 4.0 Lanolin 2.0 Isopropyl myristate 6.0 Squalane 7.0 Olive oil 2.0 Polyoxy monostearate ethylene sorbitan
5.0 Sorbitan monostearate 1.0 Propylene glycol 5.0 Butylparaben 0.1 Methylparaben 0.1 Butylated hydroxytoluene 0.05 Fragrance Appropriate amount of water 54.5 Butanoylursolic acid cetyl ester 1.0 Example 6 Lotion ethanol 7.0 Propylene glycol 5.0 Polyoxyethylene (50) hydrogenated castor oil 0.5 Citric acid 0.02 Sodium citrate 0.1 Methylparaben 0.05 δ-tocopherol 0.2 Ursolic acid 0.1 Sodium ursolic acid 0.2 Fragrance 0.4 Water 87.0 Example 7 Lotion ethanol 10.0 Glycerin 5.0 Propylene glycol 4.0 Oleyl alcohol 0.1 Ammonium ursolic acid 0.1 Magnesium ursolic acid 0 .05 Polyoxy Ethylene (20) Sorbitan Monolaurate 1.5 Polyoxyethylene (20) Lauryl Ether 0.5 Methylparaben 0.05 Fragrance 0.3 Water 78.4
第１図は有効成分の残存率を表わしたもので、
Ａはブタノイルウルソール酸セチルエステル、Ｂ
はアスコルビン酸ジステアレートである。
Figure 1 shows the residual rate of the active ingredient.
A is butanoylursolic acid cetyl ester, B
is ascorbic acid distearate.
Claims (1)
（CH3）2、Ca、Mgもしくは直鎖、分岐アルコー
ルアルキル残基であり、R2は水素原子又は直鎖、
分岐脂肪酸アシル残基であることを表わす。）で
示されるウルソール酸、その塩類もしくはウルソ
ール酸誘導体のうち少なくとも一種又は二種以上
を配合することを特徴とする化粧料。[Claims] 1 General formula () (In the formula, R 1 is a hydrogen atom or Na, K, NH 4 , H 2 N
(CH 3 ) 2 , Ca, Mg or a straight chain, branched alcohol alkyl residue, R 2 is a hydrogen atom or a straight chain,
Indicates that it is a branched fatty acid acyl residue. ) A cosmetic comprising at least one or two or more of ursolic acid, its salts, or ursolic acid derivatives.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15541881A JPS5857307A (en) | 1981-09-30 | 1981-09-30 | Cosmetic |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15541881A JPS5857307A (en) | 1981-09-30 | 1981-09-30 | Cosmetic |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5857307A JPS5857307A (en) | 1983-04-05 |
| JPH022848B2 true JPH022848B2 (en) | 1990-01-19 |
Family
ID=15605560
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15541881A Granted JPS5857307A (en) | 1981-09-30 | 1981-09-30 | Cosmetic |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5857307A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006083070A (en) * | 2004-09-14 | 2006-03-30 | Ichimaru Pharcos Co Ltd | Active oxygen scavenger, bleaching agent, anti-inflammatory agent, collagenase activity inhibitor or collagenase production inhibitor comprising calycinal extract of diospyros kaki l as active ingredient |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6223749A (en) * | 1985-07-25 | 1987-01-31 | 永大産業株式会社 | Manufacture of reinforcing board |
| JP2954634B2 (en) * | 1990-02-13 | 1999-09-27 | 協和醗酵工業株式会社 | Cosmetics |
| US5723139A (en) * | 1996-09-27 | 1998-03-03 | Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. | Skin care compositions containing a polycyclic triterpene carboxylic acid and a retinoid |
| JP3616708B2 (en) * | 1997-06-20 | 2005-02-02 | ポーラ化成工業株式会社 | Skin improvement cosmetics |
| FR2775686B1 (en) * | 1998-03-09 | 2006-07-28 | Pascal Commenil | INDUSTRIAL AND COMMERCIAL EXPLOITATION OF CUTICULAR LIPIDS IN THE BAY OF GRAPE IN PHARMACOLOGY AND COSMETOLOGY |
| WO2001072265A1 (en) * | 2000-03-31 | 2001-10-04 | The Nisshin Oil Mills, Ltd. | External preparation for the skin and beautifying agents |
| KR100355953B1 (en) * | 2000-03-31 | 2002-10-11 | 주식회사 코리아나화장품 | Skin Care Composition Containing Ursolic Acid and Synthetic Palmitoyl Pentapeptide |
| CA2430346A1 (en) * | 2000-11-30 | 2002-06-06 | The Nisshin Oillio, Ltd. | Beautifying foods and drinks and peroral beautifying preparations |
| CN1558722A (en) * | 2001-09-28 | 2004-12-29 | 日清奥利友株式会社 | Feeds and fertilizers containing pentacyclic triterpenes |
| DE10238449A1 (en) * | 2002-08-22 | 2004-03-04 | Beiersdorf Ag | Cosmetic and / or dermatological preparation |
| JP4528745B2 (en) * | 2006-06-14 | 2010-08-18 | 日光ケミカルズ株式会社 | Tyrosinase production inhibitor |
| JP5165299B2 (en) * | 2007-07-20 | 2013-03-21 | ポーラ化成工業株式会社 | Topical skin preparation |
| FR2932088B1 (en) * | 2008-06-06 | 2013-04-05 | Lvmh Rech | USE OF A LEPECHINIA CAULESCENS EXTRACT AS A COSMETIC AGENT, AND A COSMETIC COMPOSITION CONTAINING SAME |
| FR2932086A1 (en) * | 2008-06-06 | 2009-12-11 | Lvmh Rech | ANTI-AGE COSMETIC CARE METHOD BY STIMULATING THE EXPRESSION OF SURVIVAL |
| JP2010138154A (en) * | 2008-12-15 | 2010-06-24 | Pola Chem Ind Inc | External preparation for skin for dealing with aging |
| US9161958B2 (en) | 2010-08-19 | 2015-10-20 | Johnson & Johnson Consumer Inc. | Methods of treating cellulite |
| US9962326B2 (en) | 2010-08-19 | 2018-05-08 | Johnson & Johnson Consumer Inc. | Compositions comprising paulownia tomentosa wood extracts and uses thereof |
| US9387349B2 (en) | 2010-08-19 | 2016-07-12 | Johnson & Johnson Consumer Inc. | Compositions comprising Paulownia tomentosa wood extracts and uses thereof |
| US9168279B2 (en) | 2010-08-19 | 2015-10-27 | Johnson & Johnson Consumer Inc. | Compositions comprising paulownin and/or Paulownia extracts and uses thereof |
| US9168207B2 (en) | 2010-08-19 | 2015-10-27 | Johnson & Johnson Consumer Inc. | Compositions comprising Paulownia tomentosa wood extracts and uses thereof |
| US9168219B2 (en) | 2010-08-19 | 2015-10-27 | Johnson & Johnson Consumer Inc. | Compositions comprising Paulownia tomentosa wood extracts and uses thereof |
| US9173913B2 (en) | 2010-08-19 | 2015-11-03 | Johnson & Johnson Consumer Inc. | Compositions comprising Paulownia tomentosa wood extracts and uses thereof |
| JP6180817B2 (en) * | 2013-06-24 | 2017-08-16 | ポーラ化成工業株式会社 | Topical skin preparation |
| JP5768114B2 (en) * | 2013-11-29 | 2015-08-26 | ポーラ化成工業株式会社 | Method for producing an external preparation for aging |
-
1981
- 1981-09-30 JP JP15541881A patent/JPS5857307A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006083070A (en) * | 2004-09-14 | 2006-03-30 | Ichimaru Pharcos Co Ltd | Active oxygen scavenger, bleaching agent, anti-inflammatory agent, collagenase activity inhibitor or collagenase production inhibitor comprising calycinal extract of diospyros kaki l as active ingredient |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5857307A (en) | 1983-04-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH022848B2 (en) | ||
| JP3076787B2 (en) | Skin whitening composition containing fermented acerola cherry | |
| US4369174A (en) | Cosmetic composition containing kojic acid ester | |
| JP2502318B2 (en) | Whitening cosmetics | |
| JP2890212B2 (en) | Cosmetics | |
| JPH0616531A (en) | Cosmetic | |
| US6077503A (en) | Skin whitener composition containing mercaptodextran | |
| JP2903412B2 (en) | Cosmetics | |
| US4425327A (en) | Method of suppressing body odor with aminobenzoic acid amides | |
| JPH05271046A (en) | Dermal medicine for external use | |
| JP3460100B2 (en) | Whitening agent | |
| JPH0532531A (en) | Cosmetic | |
| JP2552298B2 (en) | Beautiful skin cosmetics | |
| JP2780803B2 (en) | External preparation for skin | |
| JP2663136B2 (en) | Whitening cosmetics | |
| JPH10279428A (en) | Cosmetic | |
| JP2565516B2 (en) | Topical skin | |
| JPH0114202B2 (en) | ||
| JPH0118044B2 (en) | ||
| JPH0655664B2 (en) | Beautiful skin cosmetics | |
| JPH0128002B2 (en) | ||
| JP3150841B2 (en) | External preparation for skin | |
| JPH07242542A (en) | Cosmetic | |
| JPH0692833A (en) | Skin external agent | |
| JPS62226910A (en) | Skin cosmetic |