JPH0322848B2 - - Google Patents
Info
- Publication number
- JPH0322848B2 JPH0322848B2 JP7150183A JP7150183A JPH0322848B2 JP H0322848 B2 JPH0322848 B2 JP H0322848B2 JP 7150183 A JP7150183 A JP 7150183A JP 7150183 A JP7150183 A JP 7150183A JP H0322848 B2 JPH0322848 B2 JP H0322848B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- melanin
- ester
- acetyloxycinnamic
- suppressant
- 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
- 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 claims description 46
- 150000001851 cinnamic acid derivatives Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229940124200 Melanin inhibitor Drugs 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 208000012641 Pigmentation disease Diseases 0.000 description 13
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 230000019612 pigmentation Effects 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000049 pigment Substances 0.000 description 9
- 239000006071 cream Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 8
- 210000003491 skin Anatomy 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000003205 fragrance Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 239000000126 substance Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 206010042496 Sunburn Diseases 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- -1 p-hydroxycinnamic acid ester Chemical class 0.000 description 5
- ZYIYIOLQECDIGK-UHFFFAOYSA-N propan-2-yl 3-(4-propanoyloxyphenyl)prop-2-enoate Chemical compound CCC(=O)OC1=CC=C(C=CC(=O)OC(C)C)C=C1 ZYIYIOLQECDIGK-UHFFFAOYSA-N 0.000 description 5
- PEBQLOWGSPVPEU-UHFFFAOYSA-N propyl 3-(4-acetyloxyphenyl)prop-2-enoate Chemical compound CCCOC(=O)C=CC1=CC=C(OC(C)=O)C=C1 PEBQLOWGSPVPEU-UHFFFAOYSA-N 0.000 description 5
- 239000008213 purified water Substances 0.000 description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- 206010020751 Hypersensitivity Diseases 0.000 description 4
- 208000003351 Melanosis Diseases 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 4
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 4
- 229960002216 methylparaben Drugs 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 230000001603 reducing effect Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 3
- 241000700198 Cavia Species 0.000 description 3
- 206010014970 Ephelides Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 3
- 229940067596 butylparaben Drugs 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- IFUFLGMRDPXNFA-UHFFFAOYSA-N ethyl 3-(4-acetyloxyphenyl)prop-2-enoate Chemical compound CCOC(=O)C=CC1=CC=C(OC(C)=O)C=C1 IFUFLGMRDPXNFA-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 230000008099 melanin synthesis Effects 0.000 description 3
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 3
- 230000037311 normal skin Effects 0.000 description 3
- 229940032094 squalane Drugs 0.000 description 3
- 229940099259 vaseline Drugs 0.000 description 3
- BYHBHNKBISXCEP-UHFFFAOYSA-N 3-(4-acetyloxyphenyl)prop-2-enoic acid Chemical compound CC(=O)OC1=CC=C(C=CC(O)=O)C=C1 BYHBHNKBISXCEP-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 239000000637 Melanocyte-Stimulating Hormone Substances 0.000 description 2
- 108010007013 Melanocyte-Stimulating Hormones Proteins 0.000 description 2
- 235000019482 Palm oil Nutrition 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 description 2
- 208000026935 allergic disease Diseases 0.000 description 2
- 230000007815 allergy Effects 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- MYJODVWDBIHKMD-UHFFFAOYSA-N cyclohexyl 3-(4-acetyloxyphenyl)prop-2-enoate Chemical compound C1=CC(OC(=O)C)=CC=C1C=CC(=O)OC1CCCCC1 MYJODVWDBIHKMD-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000009982 effect on human Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 210000002615 epidermis Anatomy 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 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 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 210000002752 melanocyte Anatomy 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- IVNWLXAJTPUMJK-UHFFFAOYSA-N methyl 3-(4-acetyloxyphenyl)prop-2-enoate Chemical compound COC(=O)C=CC1=CC=C(OC(C)=O)C=C1 IVNWLXAJTPUMJK-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000002540 palm oil Substances 0.000 description 2
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 2
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- WPOOFQPGJZGUPR-UHFFFAOYSA-N propyl 3-(4-propanoyloxyphenyl)prop-2-enoate Chemical compound CCCOC(=O)C=CC1=CC=C(OC(=O)CC)C=C1 WPOOFQPGJZGUPR-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 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
- SCCCIUGOOQLDGW-UHFFFAOYSA-N 1,1-dicyclohexylurea Chemical compound C1CCCCC1N(C(=O)N)C1CCCCC1 SCCCIUGOOQLDGW-UHFFFAOYSA-N 0.000 description 1
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 1
- WHYVHFCYQWZTSB-UHFFFAOYSA-N 3-(4-butanoyloxyphenyl)prop-2-enoic acid Chemical compound CCCC(=O)OC1=CC=C(C=CC(O)=O)C=C1 WHYVHFCYQWZTSB-UHFFFAOYSA-N 0.000 description 1
- AZEZFYGMKJKDTI-UHFFFAOYSA-N 3-(4-hexanoyloxyphenyl)prop-2-enoic acid Chemical compound CCCCCC(=O)OC1=CC=C(C=CC(O)=O)C=C1 AZEZFYGMKJKDTI-UHFFFAOYSA-N 0.000 description 1
- OLEPAVNUBCCRPT-UHFFFAOYSA-N 3-(4-pentanoyloxyphenyl)prop-2-enoic acid Chemical compound CCCCC(=O)OC1=CC=C(C=CC(O)=O)C=C1 OLEPAVNUBCCRPT-UHFFFAOYSA-N 0.000 description 1
- QFIJQJNGZZITLH-UHFFFAOYSA-N 3-(4-propanoyloxyphenyl)prop-2-enoic acid Chemical compound CCC(=O)OC1=CC=C(C=CC(O)=O)C=C1 QFIJQJNGZZITLH-UHFFFAOYSA-N 0.000 description 1
- ZIFRCRVAFSSTNH-UHFFFAOYSA-N 3-[4-(2-methylpropanoyloxy)phenyl]prop-2-enoic acid Chemical compound CC(C)C(=O)OC1=CC=C(C=CC(O)=O)C=C1 ZIFRCRVAFSSTNH-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- POJWUDADGALRAB-PVQJCKRUSA-N Allantoin Natural products NC(=O)N[C@@H]1NC(=O)NC1=O POJWUDADGALRAB-PVQJCKRUSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 208000019300 CLIPPERS Diseases 0.000 description 1
- 206010008570 Chloasma Diseases 0.000 description 1
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 239000004378 Glycyrrhizin Substances 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
- 239000002211 L-ascorbic acid Substances 0.000 description 1
- 235000000069 L-ascorbic acid Nutrition 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 241000772415 Neovison vison Species 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 206010047642 Vitiligo Diseases 0.000 description 1
- WBWBFAYVHBKQFX-UHFFFAOYSA-N [4-(3-ethoxy-3-oxoprop-1-enyl)phenyl] butanoate Chemical compound CCCC(=O)OC1=CC=C(C=CC(=O)OCC)C=C1 WBWBFAYVHBKQFX-UHFFFAOYSA-N 0.000 description 1
- KUCWLMHCBBUIKN-UHFFFAOYSA-N [4-(3-methoxy-3-oxoprop-1-enyl)phenyl] butanoate Chemical compound CCCC(=O)OC1=CC=C(C=CC(=O)OC)C=C1 KUCWLMHCBBUIKN-UHFFFAOYSA-N 0.000 description 1
- XRTOXUBKEFCXNA-UHFFFAOYSA-N [4-(3-methoxy-3-oxoprop-1-enyl)phenyl] hexanoate Chemical compound CCCCCC(=O)OC1=CC=C(C=CC(=O)OC)C=C1 XRTOXUBKEFCXNA-UHFFFAOYSA-N 0.000 description 1
- RZBCIKDGZPVRQN-UHFFFAOYSA-N [4-(3-methoxy-3-oxoprop-1-enyl)phenyl] pentanoate Chemical compound CCCCC(=O)OC1=CC=C(C=CC(=O)OC)C=C1 RZBCIKDGZPVRQN-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229960000458 allantoin Drugs 0.000 description 1
- 208000030961 allergic reaction Diseases 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- SXPWTBGAZSPLHA-UHFFFAOYSA-M cetalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SXPWTBGAZSPLHA-UHFFFAOYSA-M 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 208000021930 chronic lymphocytic inflammation with pontine perivascular enhancement responsive to steroids Diseases 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- BCRBCFHAEIVJDM-UHFFFAOYSA-N cyclohexyl 3-(4-propanoyloxyphenyl)prop-2-enoate Chemical compound C1=CC(OC(=O)CC)=CC=C1C=CC(=O)OC1CCCCC1 BCRBCFHAEIVJDM-UHFFFAOYSA-N 0.000 description 1
- ZAKOWWREFLAJOT-UHFFFAOYSA-N d-alpha-Tocopheryl acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-UHFFFAOYSA-N 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 210000005175 epidermal keratinocyte Anatomy 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- ZSBHOEMPFPFKIO-UHFFFAOYSA-N ethyl 3-(4-propanoyloxyphenyl)prop-2-enoate Chemical compound CCOC(=O)C=CC1=CC=C(OC(=O)CC)C=C1 ZSBHOEMPFPFKIO-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- LPLVUJXQOOQHMX-UHFFFAOYSA-N glycyrrhetinic acid glycoside Natural products C1CC(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2=O)C(O)=O)C)(C)CC2)(C)C2C(C)(C)C1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O LPLVUJXQOOQHMX-UHFFFAOYSA-N 0.000 description 1
- 229960004949 glycyrrhizic acid Drugs 0.000 description 1
- UYRUBYNTXSDKQT-UHFFFAOYSA-N glycyrrhizic acid Natural products CC1(C)C(CCC2(C)C1CCC3(C)C2C(=O)C=C4C5CC(C)(CCC5(C)CCC34C)C(=O)O)OC6OC(C(O)C(O)C6OC7OC(O)C(O)C(O)C7C(=O)O)C(=O)O UYRUBYNTXSDKQT-UHFFFAOYSA-N 0.000 description 1
- 235000019410 glycyrrhizin Nutrition 0.000 description 1
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- DLINORNFHVEIFE-UHFFFAOYSA-N hydrogen peroxide;zinc Chemical compound [Zn].OO DLINORNFHVEIFE-UHFFFAOYSA-N 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 230000003780 keratinization Effects 0.000 description 1
- 210000002510 keratinocyte Anatomy 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- ARRGFEIYBFJUDU-UHFFFAOYSA-N methyl 3-(4-propanoyloxyphenyl)prop-2-enoate Chemical compound CCC(=O)OC1=CC=C(C=CC(=O)OC)C=C1 ARRGFEIYBFJUDU-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- XIHCFYPMUSHONB-UHFFFAOYSA-N propan-2-yl 3-(4-acetyloxyphenyl)prop-2-enoate Chemical compound C(C)(C)OC(C=CC1=CC=C(C=C1)OC(C)=O)=O XIHCFYPMUSHONB-UHFFFAOYSA-N 0.000 description 1
- WVDDMJTWFGHTGZ-UHFFFAOYSA-N propan-2-yl 3-(4-hydroxyphenyl)prop-2-enoate Chemical compound CC(C)OC(=O)C=CC1=CC=C(O)C=C1 WVDDMJTWFGHTGZ-UHFFFAOYSA-N 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- AJOXHZKDNCMEKC-UHFFFAOYSA-N propyl 3-(4-hydroxyphenyl)prop-2-enoate Chemical compound CCCOC(=O)C=CC1=CC=C(O)C=C1 AJOXHZKDNCMEKC-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- 229940045920 sodium pyrrolidone carboxylate Drugs 0.000 description 1
- HYRLWUFWDYFEES-UHFFFAOYSA-M sodium;2-oxopyrrolidine-1-carboxylate Chemical compound [Na+].[O-]C(=O)N1CCCC1=O HYRLWUFWDYFEES-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229940042585 tocopherol acetate Drugs 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 239000009538 yokuinin Substances 0.000 description 1
- 229940105296 zinc peroxide Drugs 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
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0208—Tissues; Wipes; Patches
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
-
- 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/42—Amides
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Cosmetics (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7150183A JPS59196813A (ja) | 1983-04-25 | 1983-04-25 | メラニン抑制剤 |
| GB08410127A GB2141626B (en) | 1983-04-25 | 1984-04-18 | Cinnamic acid derivatives for lightening melanin pigmentation of skin |
| DE19843415413 DE3415413A1 (de) | 1983-04-25 | 1984-04-25 | Melanin-inhibitor |
| FR8406503A FR2545355B1 (fr) | 1983-04-25 | 1984-04-25 | Inhibiteur de melanine, a base d'un derive d'acide cinnamique |
| US06/814,172 US4978523A (en) | 1983-04-25 | 1985-12-24 | Melanin inhibitor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7150183A JPS59196813A (ja) | 1983-04-25 | 1983-04-25 | メラニン抑制剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59196813A JPS59196813A (ja) | 1984-11-08 |
| JPH0322848B2 true JPH0322848B2 (enrdf_load_stackoverflow) | 1991-03-27 |
Family
ID=13462482
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7150183A Granted JPS59196813A (ja) | 1983-04-25 | 1983-04-25 | メラニン抑制剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59196813A (enrdf_load_stackoverflow) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0729911B2 (ja) * | 1986-05-15 | 1995-04-05 | 株式会社資生堂 | 皮膚外用剤 |
| JP5057646B2 (ja) * | 2004-12-10 | 2012-10-24 | 株式会社ノエビア | チロシナーゼ活性抑制剤、及び皮膚外用剤 |
| FR2892923B1 (fr) | 2005-11-08 | 2009-01-16 | Engelhard Lyon Sa | Utilisatiion des derives de l'acide para-coumarique ou para- hydroxycinnamique dans des compositions cosmetiques ou dermatologiques. |
| JP6178601B2 (ja) * | 2013-03-29 | 2017-08-09 | 株式会社コーセー | ｐ−クマル酸を含有した組成物 |
| CN106687100B (zh) * | 2014-09-12 | 2020-09-04 | 宝洁公司 | 用于抑制黑素合成的化妆品组合物和方法 |
-
1983
- 1983-04-25 JP JP7150183A patent/JPS59196813A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59196813A (ja) | 1984-11-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2147806C (fr) | Composes polyeniques, compositions pharmaceutiques et cosmetiques les contenant et utilisations | |
| US4978523A (en) | Melanin inhibitor | |
| WO1986006064A1 (fr) | Derives naphtaleniques a action de type retinoide, leur procede de preparation et compositions medicamenteuse et cosmetique les contenant | |
| FR2719043A1 (fr) | Nouveaux composés bicycliques-aromatiques, compositions pharmaceutiques et cosmétiques les contenant et utilisations. | |
| KR100457949B1 (ko) | 3,4,5-트리메톡시 페닐아세트산, 3,4,5-트리메톡시 신남산또는 3,4,5-트리메톡시 히드로 신남산의 에스테르화합물 및 이를 함유하는 미백 화장료조성물 | |
| JPH05213729A (ja) | メラニン抑制剤 | |
| JP2957123B2 (ja) | アミド由来のビアロマティック化合物、これを含有する製薬及び化粧品組成物及びその使用 | |
| FR2764604A1 (fr) | Composes bi-aromatiques relies par un radical propynylene ou allenylene et compositions pharmaceutiques et cosmetiques les contenant | |
| JPH0322848B2 (enrdf_load_stackoverflow) | ||
| US4981680A (en) | P-hydroxycinnamamide derivatives and melanin inhibitor comprising the same | |
| ES2241580T3 (es) | Composicion de resorcinol. | |
| JPH05105643A (ja) | 桂皮酸誘導体およびこれを有効成分とする美白化粧料 | |
| JP3071990B2 (ja) | 皮膚外用剤 | |
| JPH05105621A (ja) | 桂皮酸エステル誘導体を有効成分とする美白化粧料 | |
| JP4658898B2 (ja) | メラニン生成抑制剤及び美白化粧料 | |
| CH673027A5 (enrdf_load_stackoverflow) | ||
| JPH0853332A (ja) | 美白化粧料 | |
| JPS6256459A (ja) | Ｎ，Ｎ−ジアルキル−ｐ−ヒドロキシシンナムアミド及びこれを含有するメラニン抑制剤 | |
| JPH0632727A (ja) | 皮膚外用剤 | |
| JPS6339847A (ja) | ｐ−ヒドロキシシンナムアミド誘導体およびこれを含有するメラニン抑制剤 | |
| JPH0977651A (ja) | 美白化粧料 | |
| JPH07330569A (ja) | 美白化粧料 | |
| JPH0848621A (ja) | 美白化粧料 | |
| JPH05105620A (ja) | ｐ−ヒドロキシ桂皮酸誘導体を有効成分とする美白化粧料 | |
| JPH0425922B2 (enrdf_load_stackoverflow) |