JPS59122485A - コウジ酸誘導体及びこれを有効成分とする色白化粧料 - Google Patents
コウジ酸誘導体及びこれを有効成分とする色白化粧料Info
- Publication number
- JPS59122485A JPS59122485A JP22795482A JP22795482A JPS59122485A JP S59122485 A JPS59122485 A JP S59122485A JP 22795482 A JP22795482 A JP 22795482A JP 22795482 A JP22795482 A JP 22795482A JP S59122485 A JPS59122485 A JP S59122485A
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- pyran
- oxymethyl
- kojic acid
- compound
- 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
- 239000002537 cosmetic Substances 0.000 title claims abstract description 34
- BEJNERDRQOWKJM-UHFFFAOYSA-N kojic acid Chemical class OCC1=CC(=O)C(O)=CO1 BEJNERDRQOWKJM-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 239000004480 active ingredient Substances 0.000 title claims description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 102000003425 Tyrosinase Human genes 0.000 abstract description 19
- 108060008724 Tyrosinase Proteins 0.000 abstract description 19
- 230000000694 effects Effects 0.000 abstract description 19
- 229960004705 kojic acid Drugs 0.000 abstract description 18
- WZNJWVWKTVETCG-UHFFFAOYSA-N kojic acid Natural products OC(=O)C(N)CN1C=CC(=O)C(O)=C1 WZNJWVWKTVETCG-UHFFFAOYSA-N 0.000 abstract description 18
- 230000002401 inhibitory effect Effects 0.000 abstract description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract description 4
- 239000004615 ingredient Substances 0.000 abstract description 3
- 108700004121 sarkosyl Proteins 0.000 abstract description 3
- WSVIQCQIJLDTEK-UHFFFAOYSA-N 2-(chloromethyl)-5-hydroxypyran-4-one Chemical compound OC1=COC(CCl)=CC1=O WSVIQCQIJLDTEK-UHFFFAOYSA-N 0.000 abstract 1
- 230000002411 adverse Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- 239000003921 oil Substances 0.000 description 27
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 26
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 24
- 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 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000003755 preservative agent Substances 0.000 description 14
- 235000011187 glycerol Nutrition 0.000 description 13
- 239000012071 phase Substances 0.000 description 13
- 239000008213 purified water Substances 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- -1 heated and mixed Chemical compound 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 239000006210 lotion Substances 0.000 description 11
- 239000006071 cream Substances 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 10
- 239000003205 fragrance Substances 0.000 description 10
- 239000008346 aqueous phase Substances 0.000 description 9
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- 235000013871 bee wax Nutrition 0.000 description 8
- 239000012166 beeswax Substances 0.000 description 8
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 229940032094 squalane Drugs 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000004166 Lanolin Substances 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
- 235000019388 lanolin Nutrition 0.000 description 6
- 229940039717 lanolin Drugs 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000003906 humectant Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 4
- 239000005995 Aluminium silicate Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 206010040829 Skin discolouration Diseases 0.000 description 4
- 229920002125 Sokalan® Polymers 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 235000012211 aluminium silicate Nutrition 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- VJNCICVKUHKIIV-UHFFFAOYSA-N dopachrome Chemical compound O=C1C(=O)C=C2NC(C(=O)O)CC2=C1 VJNCICVKUHKIIV-UHFFFAOYSA-N 0.000 description 4
- 239000010696 ester oil Substances 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 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 4
- 239000007788 liquid Substances 0.000 description 4
- 229940057995 liquid paraffin Drugs 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000012188 paraffin wax Substances 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 229940099259 vaseline Drugs 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000002335 preservative effect Effects 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
- DSEKYWAQQVUQTP-XEWMWGOFSA-N (2r,4r,4as,6as,6as,6br,8ar,12ar,14as,14bs)-2-hydroxy-4,4a,6a,6b,8a,11,11,14a-octamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1h-picen-3-one Chemical compound C([C@H]1[C@]2(C)CC[C@@]34C)C(C)(C)CC[C@]1(C)CC[C@]2(C)[C@H]4CC[C@@]1(C)[C@H]3C[C@@H](O)C(=O)[C@@H]1C DSEKYWAQQVUQTP-XEWMWGOFSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- 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 2
- 239000004909 Moisturizer Substances 0.000 description 2
- BACYUWVYYTXETD-UHFFFAOYSA-N N-Lauroylsarcosine Chemical compound CCCCCCCCCCCC(=O)N(C)CC(O)=O BACYUWVYYTXETD-UHFFFAOYSA-N 0.000 description 2
- 239000004264 Petrolatum Substances 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- CVQUWLDCFXOXEN-UHFFFAOYSA-N Pyran-4-one Chemical compound O=C1C=COC=C1 CVQUWLDCFXOXEN-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000001980 alanyl group Chemical group 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 230000008099 melanin synthesis Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000001333 moisturizer Effects 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 235000019271 petrolatum Nutrition 0.000 description 2
- 229940066842 petrolatum Drugs 0.000 description 2
- 229940093430 polyethylene glycol 1500 Drugs 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229960005078 sorbitan sesquioleate Drugs 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- JLXUMEOGFJZVOH-UHFFFAOYSA-N 2,3-dihydroxypropanoic acid propane-1,2,3-triol Chemical compound OCC(O)CO.OCC(O)C(O)=O JLXUMEOGFJZVOH-UHFFFAOYSA-N 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 235000008853 Zanthoxylum piperitum Nutrition 0.000 description 1
- 244000131415 Zanthoxylum piperitum Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229930194563 aspergillus acid Natural products 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/40—Oxygen atoms attached in positions 3 and 4, e.g. maltol
-
- 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
- A61K8/0212—Face masks
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
- Pyrane Compounds (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22795482A JPS59122485A (ja) | 1982-12-29 | 1982-12-29 | コウジ酸誘導体及びこれを有効成分とする色白化粧料 |
| PCT/JP1984/000331 WO1986000306A1 (en) | 1982-12-29 | 1984-06-28 | Kojic acid derivatives and whitening cosmetics containing same |
| GB08605067A GB2175584B (en) | 1982-12-29 | 1984-06-28 | Kojic acid derivatives and whitening cosmetics containing same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22795482A JPS59122485A (ja) | 1982-12-29 | 1982-12-29 | コウジ酸誘導体及びこれを有効成分とする色白化粧料 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59122485A true JPS59122485A (ja) | 1984-07-14 |
| JPH0145472B2 JPH0145472B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-10-03 |
Family
ID=16868863
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22795482A Granted JPS59122485A (ja) | 1982-12-29 | 1982-12-29 | コウジ酸誘導体及びこれを有効成分とする色白化粧料 |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS59122485A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
| GB (1) | GB2175584B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61197506A (ja) * | 1985-02-27 | 1986-09-01 | Yakurigaku Chuo Kenkyusho:Kk | γ−ピロン誘導体による生物の体色黒変防止方法 |
| KR100456974B1 (ko) * | 2002-05-10 | 2004-11-10 | 주식회사 태평양 | 신규한 크로만 유도체 및 이의 제조방법, 및 이를함유하는 피부 외용제 조성물 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR960016127B1 (ko) * | 1994-02-01 | 1996-12-04 | 주식회사 태평양 | 코지산 유도체 |
| FR2751331A1 (fr) * | 1996-07-18 | 1998-01-23 | Oreal | Nouveau derive de l'acide kojique et son utilisation comme agent depigmentant |
-
1982
- 1982-12-29 JP JP22795482A patent/JPS59122485A/ja active Granted
-
1984
- 1984-06-28 GB GB08605067A patent/GB2175584B/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61197506A (ja) * | 1985-02-27 | 1986-09-01 | Yakurigaku Chuo Kenkyusho:Kk | γ−ピロン誘導体による生物の体色黒変防止方法 |
| KR100456974B1 (ko) * | 2002-05-10 | 2004-11-10 | 주식회사 태평양 | 신규한 크로만 유도체 및 이의 제조방법, 및 이를함유하는 피부 외용제 조성물 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0145472B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-10-03 |
| GB8605067D0 (en) | 1986-04-09 |
| GB2175584B (en) | 1987-12-31 |
| GB2175584A (en) | 1986-12-03 |
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