DE3415413A1 - Melanin-inhibitor - Google Patents
Melanin-inhibitorInfo
- Publication number
- DE3415413A1 DE3415413A1 DE19843415413 DE3415413A DE3415413A1 DE 3415413 A1 DE3415413 A1 DE 3415413A1 DE 19843415413 DE19843415413 DE 19843415413 DE 3415413 A DE3415413 A DE 3415413A DE 3415413 A1 DE3415413 A1 DE 3415413A1
- Authority
- DE
- Germany
- Prior art keywords
- melanin
- pigment
- inhibitor
- formulation
- propyl
- 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.)
- Granted
Links
- 239000003112 inhibitor Substances 0.000 title description 10
- 229940124200 Melanin inhibitor Drugs 0.000 claims description 23
- 150000001851 cinnamic acid derivatives Chemical class 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 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 30
- 239000000049 pigment Substances 0.000 description 28
- 239000000203 mixture Substances 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 238000009472 formulation Methods 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 19
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 18
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- -1 2-ethylhexyl Chemical group 0.000 description 14
- 230000000694 effects Effects 0.000 description 14
- QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 description 12
- 239000006071 cream Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 208000003351 Melanosis Diseases 0.000 description 11
- 239000002304 perfume Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000008213 purified water Substances 0.000 description 10
- 235000011187 glycerol Nutrition 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 8
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 8
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 8
- 229960002216 methylparaben Drugs 0.000 description 8
- 210000003491 skin Anatomy 0.000 description 8
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 7
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241000700198 Cavia Species 0.000 description 6
- 229940067596 butylparaben Drugs 0.000 description 6
- 229960000541 cetyl alcohol Drugs 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 229940099259 vaseline Drugs 0.000 description 6
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 5
- 208000012641 Pigmentation disease Diseases 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 5
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000019612 pigmentation Effects 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
- 229940031439 squalene Drugs 0.000 description 5
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 241000700199 Cavia porcellus Species 0.000 description 4
- 206010020751 Hypersensitivity Diseases 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 235000019482 Palm oil Nutrition 0.000 description 4
- 235000021355 Stearic acid Nutrition 0.000 description 4
- 206010042496 Sunburn Diseases 0.000 description 4
- 238000010171 animal model Methods 0.000 description 4
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 4
- 239000000920 calcium hydroxide Substances 0.000 description 4
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 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 4
- 238000001816 cooling Methods 0.000 description 4
- 239000002537 cosmetic Substances 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
- 239000002540 palm oil Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 239000008117 stearic acid Substances 0.000 description 4
- 206010008570 Chloasma Diseases 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid Chemical compound OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 3
- APEJMQOBVMLION-UHFFFAOYSA-N cinnamic acid amide Natural products NC(=O)C=CC1=CC=CC=C1 APEJMQOBVMLION-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 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 3
- 239000011888 foil Substances 0.000 description 3
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 3
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 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
- 238000000034 method Methods 0.000 description 3
- GWEYIZUAQPNBAO-UHFFFAOYSA-N n-hexyl-3-(4-hydroxyphenyl)prop-2-enamide Chemical compound CCCCCCNC(=O)C=CC1=CC=C(O)C=C1 GWEYIZUAQPNBAO-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- CUNWUEBNSZSNRX-RKGWDQTMSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;(z)-octadec-9-enoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O CUNWUEBNSZSNRX-RKGWDQTMSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- VNDDFIQMUQVYDJ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-n-methylprop-2-enamide Chemical compound CNC(=O)C=CC1=CC=C(O)C=C1 VNDDFIQMUQVYDJ-UHFFFAOYSA-N 0.000 description 2
- MZQTYFUVASWKRX-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-n-propylprop-2-enamide Chemical compound CCCNC(=O)C=CC1=CC=C(O)C=C1 MZQTYFUVASWKRX-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
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 208000019300 CLIPPERS Diseases 0.000 description 2
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 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
- 239000004166 Lanolin Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 239000004909 Moisturizer Substances 0.000 description 2
- 241000772415 Neovison vison Species 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 229930003268 Vitamin C Natural products 0.000 description 2
- 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 2
- 239000004480 active ingredient Substances 0.000 description 2
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 208000021930 chronic lymphocytic inflammation with pontine perivascular enhancement responsive to steroids Diseases 0.000 description 2
- 229940114081 cinnamate Drugs 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
- 230000008021 deposition Effects 0.000 description 2
- 210000002615 epidermis Anatomy 0.000 description 2
- 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 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
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- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229940039717 lanolin Drugs 0.000 description 2
- 235000019388 lanolin Nutrition 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
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- 239000000463 material Substances 0.000 description 2
- 230000003061 melanogenesis Effects 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 230000001333 moisturizer Effects 0.000 description 2
- 230000003020 moisturizing effect Effects 0.000 description 2
- XOOAHGQKVZNTHU-UHFFFAOYSA-N n-ethyl-3-(4-hydroxyphenyl)prop-2-enamide Chemical compound CCNC(=O)C=CC1=CC=C(O)C=C1 XOOAHGQKVZNTHU-UHFFFAOYSA-N 0.000 description 2
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- 150000002978 peroxides Chemical class 0.000 description 2
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- 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 2
- 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 2
- 239000011541 reaction mixture Substances 0.000 description 2
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- HYRLWUFWDYFEES-UHFFFAOYSA-M sodium;2-oxopyrrolidine-1-carboxylate Chemical compound [Na+].[O-]C(=O)N1CCCC1=O HYRLWUFWDYFEES-UHFFFAOYSA-M 0.000 description 2
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- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- VLEGKXSJUXLEJG-UHFFFAOYSA-N 2-hydroxy-3-phenylprop-2-enamide Chemical compound NC(=O)C(O)=CC1=CC=CC=C1 VLEGKXSJUXLEJG-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 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 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
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-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
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 206010004950 Birth mark Diseases 0.000 description 1
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- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 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
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
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- 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
- 230000035876 healing Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- DLINORNFHVEIFE-UHFFFAOYSA-N hydrogen peroxide;zinc Chemical compound [Zn].OO DLINORNFHVEIFE-UHFFFAOYSA-N 0.000 description 1
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- 239000002085 irritant Substances 0.000 description 1
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- 230000000622 irritating effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000002463 lignoceryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UYEKGCPLNBQNSM-UHFFFAOYSA-N n-cyclohexyl-3-(4-hydroxyphenyl)prop-2-enamide Chemical compound C1=CC(O)=CC=C1C=CC(=O)NC1CCCCC1 UYEKGCPLNBQNSM-UHFFFAOYSA-N 0.000 description 1
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- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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- 239000003755 preservative agent Substances 0.000 description 1
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- 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
- 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 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 208000031019 skin pigmentation disease Diseases 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 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
- 239000002562 thickening agent Substances 0.000 description 1
- 229940042585 tocopherol acetate Drugs 0.000 description 1
- NGSWKAQJJWESNS-ZZXKWVIFSA-N trans-4-coumaric acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C=C1 NGSWKAQJJWESNS-ZZXKWVIFSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
-
- 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
- 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/42—Amides
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/13—Burn treatment
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)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7150183A JPS59196813A (ja) | 1983-04-25 | 1983-04-25 | メラニン抑制剤 |
| JP4684984A JPS60190713A (ja) | 1984-03-12 | 1984-03-12 | メラニン抑制剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3415413A1 true DE3415413A1 (de) | 1984-11-15 |
| DE3415413C2 DE3415413C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-07-16 |
Family
ID=26386989
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843415413 Granted DE3415413A1 (de) | 1983-04-25 | 1984-04-25 | Melanin-inhibitor |
Country Status (4)
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1989000849A1 (en) * | 1987-07-28 | 1989-02-09 | Baylor College Of Medicine | Cell growth inhibitors and methods of treating cancer and cell proliferative diseases |
| DE10063660A1 (de) * | 2000-12-20 | 2002-07-04 | Beiersdorf Ag | Kosmetische und dermatologische Zubereitungen in Form von O/W-Emulsionen mit einem Gehalt an Sterinen und/oder C¶1¶¶2¶-C¶4¶¶0¶-Fettsäuren |
| DE10063658A1 (de) * | 2000-12-20 | 2002-07-04 | Beiersdorf Ag | Kosmetische und dermatologische Zubereitungen in Form von W/O/W-Emulsionen mit einem Gehalt an Sterinen und /oder C12-C-40-Fettsäure |
| DE10139580A1 (de) * | 2001-08-10 | 2003-02-20 | Beiersdorf Ag | Kosmetische und dermatologische Zubereitungen in Form von O/W-Emulsionen mit einem Gehalt an Sterinen und/oder C12-C40-Fettsäuren |
| DE10139582A1 (de) * | 2001-08-10 | 2003-02-20 | Beiersdorf Ag | Kosmetische und dermatologische Zubereitungen in Form von W/O/W-Emulsionen mit einem Gehalt an Sterinen und/oder C12-C40-Fettsäuren |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2579461B1 (fr) * | 1985-03-28 | 1988-08-26 | Strasbourg Universite L Pasteu | Amides de l'acide para-methoxycinnamique et de l'acide urocanique utilises comme filtres solaires; procedes d'obtention, compositions dermo-pharmaceutiques et cosmetiques les contenant et applications |
| US4876084A (en) * | 1986-08-04 | 1989-10-24 | Kao Corporation | P-hydroxycinnamamide derivatives and melanin inhibitor comprising the same |
| GB8913708D0 (en) * | 1989-06-14 | 1989-08-02 | Unilever Plc | Cosmetic composition |
| IT1255729B (it) * | 1992-05-19 | 1995-11-15 | Giuseppe Raspanti | Derivati di s-triazina come agenti fotostabilizzanti |
| ATE365530T1 (de) * | 1992-07-13 | 2007-07-15 | Shiseido Co Ltd | Retinolthaltiges, stabilisiertes hautpflegemittel zur äusserlichen anwendung |
| US5759525A (en) * | 1996-12-26 | 1998-06-02 | 3V Inc. | Concentrated solutions of a 1,3,5-triazine derivative sunscreen and their use for the preparation of cosmetic compositions |
| EP1084269B1 (en) * | 1998-06-04 | 2007-04-25 | PerkinElmer LAS, Inc. | Novel peroxidase substrates and their use in catalyzed reporter deposition |
| US20040101593A1 (en) * | 2001-03-02 | 2004-05-27 | Nobutaka Suzuki | Preventives or remedies for tumor of human papillomaviral disease |
| KR100457949B1 (ko) * | 2001-09-24 | 2004-11-18 | 주식회사 태평양 | 3,4,5-트리메톡시 페닐아세트산, 3,4,5-트리메톡시 신남산또는 3,4,5-트리메톡시 히드로 신남산의 에스테르화합물 및 이를 함유하는 미백 화장료조성물 |
| KR100492809B1 (ko) * | 2001-11-23 | 2005-06-03 | 한국화학연구원 | 항산화 활성을 갖는 4-히드록시 신남아미드 유도체, 그의제조방법 및 이를 포함하는 약학적 조성물 |
| JP2008526963A (ja) * | 2005-01-14 | 2008-07-24 | リポ ケミカルズ インコーポレイテッド | 過度に色素沈着した皮膚を処置するための組成物および方法 |
| 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. |
| KR100698703B1 (ko) * | 2006-03-28 | 2007-03-23 | 삼성에스디아이 주식회사 | 화소 및 이를 이용한 유기전계발광 표시장치 |
| CN119486704A (zh) * | 2022-06-21 | 2025-02-18 | 莱雅公司 | 包含硫代吡啶酮化合物的抗氧化组合物 |
| WO2023249912A1 (en) * | 2022-06-21 | 2023-12-28 | L'oreal | Cosmetic composition comprising hydrophilic antioxidants and thiopyridinone compounds |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD108036A2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-11-05 | 1974-09-12 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3256312A (en) * | 1961-10-02 | 1966-06-14 | Gen Aniline & Film Corp | Esters of alpha-cyano-beta-alkyl cinnamic acid |
| GB1370236A (en) * | 1972-01-11 | 1974-10-16 | Unilever Ltd | Skin composition |
| US4263212A (en) * | 1979-02-28 | 1981-04-21 | Rikagaku Kenkyusho | Process for preparation of substituted olefins |
| DE3028417A1 (de) * | 1980-07-26 | 1982-02-25 | Basf Ag | Neue veraetherte p-hydroxyzimtsaeureester, ihre herstellung und diese enthaltende zubereitungen als lichtschutzmittel |
| JPS5746915A (en) * | 1980-09-03 | 1982-03-17 | Banyu Pharmaceut Co Ltd | Antiallergic agent |
| FR2520233A1 (fr) * | 1982-01-28 | 1983-07-29 | Oreal | Composition d'anthraline ou de l'un de ses derives dans un ester aromatique et son utilisation dans le traitement des maladies de la peau |
-
1984
- 1984-04-18 GB GB08410127A patent/GB2141626B/en not_active Expired
- 1984-04-25 FR FR8406503A patent/FR2545355B1/fr not_active Expired
- 1984-04-25 DE DE19843415413 patent/DE3415413A1/de active Granted
-
1985
- 1985-12-24 US US06/814,172 patent/US4978523A/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD108036A2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-11-05 | 1974-09-12 |
Non-Patent Citations (1)
| Title |
|---|
| DE-B.: NASEMANN, T. und SAUERBREY, W.: Lehr- buch der Hautkrankheiten und venerischen In- fektionen, 3. Aufl., Springer-Verlag, Berlin, 1979, S. 291-292 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1989000849A1 (en) * | 1987-07-28 | 1989-02-09 | Baylor College Of Medicine | Cell growth inhibitors and methods of treating cancer and cell proliferative diseases |
| US5216024A (en) * | 1987-07-28 | 1993-06-01 | Baylor College Of Medicine | Cell growth inhibitors and methods of treating cancer and cell proliferative diseases |
| DE10063660A1 (de) * | 2000-12-20 | 2002-07-04 | Beiersdorf Ag | Kosmetische und dermatologische Zubereitungen in Form von O/W-Emulsionen mit einem Gehalt an Sterinen und/oder C¶1¶¶2¶-C¶4¶¶0¶-Fettsäuren |
| DE10063658A1 (de) * | 2000-12-20 | 2002-07-04 | Beiersdorf Ag | Kosmetische und dermatologische Zubereitungen in Form von W/O/W-Emulsionen mit einem Gehalt an Sterinen und /oder C12-C-40-Fettsäure |
| DE10139580A1 (de) * | 2001-08-10 | 2003-02-20 | Beiersdorf Ag | Kosmetische und dermatologische Zubereitungen in Form von O/W-Emulsionen mit einem Gehalt an Sterinen und/oder C12-C40-Fettsäuren |
| DE10139582A1 (de) * | 2001-08-10 | 2003-02-20 | Beiersdorf Ag | Kosmetische und dermatologische Zubereitungen in Form von W/O/W-Emulsionen mit einem Gehalt an Sterinen und/oder C12-C40-Fettsäuren |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2141626B (en) | 1987-01-28 |
| DE3415413C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-07-16 |
| GB8410127D0 (en) | 1984-05-31 |
| US4978523A (en) | 1990-12-18 |
| FR2545355A1 (fr) | 1984-11-09 |
| GB2141626A (en) | 1985-01-03 |
| FR2545355B1 (fr) | 1988-11-18 |
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