WO1995005412B1 - Cosmetic melanins - Google Patents
Cosmetic melaninsInfo
- Publication number
- WO1995005412B1 WO1995005412B1 PCT/US1994/009153 US9409153W WO9505412B1 WO 1995005412 B1 WO1995005412 B1 WO 1995005412B1 US 9409153 W US9409153 W US 9409153W WO 9505412 B1 WO9505412 B1 WO 9505412B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- melanin
- acid
- monomeric units
- polymer according
- melanin polymer
- Prior art date
Links
- 239000002537 cosmetic Substances 0.000 title claims abstract 4
- 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 abstract 36
- 210000003491 Skin Anatomy 0.000 claims abstract 6
- 239000003795 chemical substances by application Substances 0.000 claims abstract 3
- 230000001590 oxidative Effects 0.000 claims abstract 3
- 230000002708 enhancing Effects 0.000 claims abstract 2
- 239000000463 material Substances 0.000 claims abstract 2
- 229920000642 polymer Polymers 0.000 claims 21
- RHMXXJGYXNZAPX-UHFFFAOYSA-N Emodin Chemical compound C1=C(O)C=C2C(=O)C3=CC(C)=CC(O)=C3C(=O)C2=C1O RHMXXJGYXNZAPX-UHFFFAOYSA-N 0.000 claims 6
- AFHJQYHRLPMKHU-XXWVOBANSA-N Aloin Natural products O=C1c2c(O)cc(CO)cc2[C@H]([C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O2)c2c1c(O)ccc2 AFHJQYHRLPMKHU-XXWVOBANSA-N 0.000 claims 4
- AFHJQYHRLPMKHU-WEZNYRQKSA-N aloin B Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1[C@H]1C2=CC(CO)=CC(O)=C2C(=O)C2=C(O)C=CC=C21 AFHJQYHRLPMKHU-WEZNYRQKSA-N 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000011780 sodium chloride Substances 0.000 claims 4
- WTDRDQBEARUVNC-LURJTMIESA-N 3-hydroxy-L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims 3
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-Aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims 3
- 239000010282 Emodin Substances 0.000 claims 3
- FBTSQILOGYXGMD-LURJTMIESA-N Nitrotyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C([N+]([O-])=O)=C1 FBTSQILOGYXGMD-LURJTMIESA-N 0.000 claims 3
- 229960004050 aminobenzoic acid Drugs 0.000 claims 3
- 229960004502 levodopa Drugs 0.000 claims 3
- HVYWMOMLDIMFJA-DPAQBDIFSA-N (3β)-Cholest-5-en-3-ol 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 claims 2
- WHNCXIBKVUPNHR-UHFFFAOYSA-N 3,4-dihydroxy-1H-indole-2-carboxylic acid Chemical compound C1=CC(O)=C2C(O)=C(C(=O)O)NC2=C1 WHNCXIBKVUPNHR-UHFFFAOYSA-N 0.000 claims 2
- POGSZHUEECCEAP-UHFFFAOYSA-N 3-(3-amino-4-hydroxyphenyl)-2-azaniumylpropanoate Chemical group OC(=O)C(N)CC1=CC=C(O)C(N)=C1 POGSZHUEECCEAP-UHFFFAOYSA-N 0.000 claims 2
- MESJRHHDBDCQTH-UHFFFAOYSA-N 3-(dimethylamino)phenol Chemical group CN(C)C1=CC=CC(O)=C1 MESJRHHDBDCQTH-UHFFFAOYSA-N 0.000 claims 2
- MRBKRZAPGUCWOS-UHFFFAOYSA-N 3-amino-4-hydroxybenzoic acid Chemical compound NC1=CC(C(O)=O)=CC=C1O MRBKRZAPGUCWOS-UHFFFAOYSA-N 0.000 claims 2
- VACHUYIREGFMSP-SJORKVTESA-N 9,10-Dihydroxystearic acid Natural products CCCCCCCC[C@@H](O)[C@@H](O)CCCCCCCC(O)=O VACHUYIREGFMSP-SJORKVTESA-N 0.000 claims 2
- WXTMDXOMEHJXQO-UHFFFAOYSA-N Gentisic acid Chemical group OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 claims 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N Linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims 2
- YQUVCSBJEUQKSH-UHFFFAOYSA-N Protocatechuic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- 239000007800 oxidant agent Substances 0.000 claims 2
- 239000000243 solution Substances 0.000 claims 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N α-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims 2
- PGNRLPTYNKQQDY-UHFFFAOYSA-N 2,3-dihydroxyindole Chemical group C1=CC=C2C(O)=C(O)NC2=C1 PGNRLPTYNKQQDY-UHFFFAOYSA-N 0.000 claims 1
- OGSZAQASQUXQOD-UHFFFAOYSA-N 2,3-dihydroxynaphthalene-1-sulfonic acid Chemical group C1=CC=C2C(S(O)(=O)=O)=C(O)C(O)=CC2=C1 OGSZAQASQUXQOD-UHFFFAOYSA-N 0.000 claims 1
- IQGMRVWUTCYCST-UHFFFAOYSA-N 3-Aminosalicylic acid Chemical compound NC1=CC=CC(C(O)=O)=C1O IQGMRVWUTCYCST-UHFFFAOYSA-N 0.000 claims 1
- HYXLGBKHTVJEKA-UHFFFAOYSA-N 4,5-dihydroxynaphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(O)=CC=CC2=C1 HYXLGBKHTVJEKA-UHFFFAOYSA-N 0.000 claims 1
- QRBSGTUCLRTVDE-UHFFFAOYSA-N 9H-carbazole-1,2-diol Chemical compound C1=CC=C2C3=CC=C(O)C(O)=C3NC2=C1 QRBSGTUCLRTVDE-UHFFFAOYSA-N 0.000 claims 1
- 229940107161 Cholesterol Drugs 0.000 claims 1
- YFTGOBNOJKXZJC-UHFFFAOYSA-N DHICA Chemical group OC1=C(O)C=C2NC(C(=O)O)=CC2=C1 YFTGOBNOJKXZJC-UHFFFAOYSA-N 0.000 claims 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 1
- 229960004488 Linolenic Acid Drugs 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 150000001491 aromatic compounds Chemical class 0.000 claims 1
- -1 aromatic glycoside Chemical class 0.000 claims 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M buffer Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 150000001716 carbazoles Chemical class 0.000 claims 1
- 235000012000 cholesterol Nutrition 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- 150000004665 fatty acids Chemical class 0.000 claims 1
- 235000020778 linoleic acid Nutrition 0.000 claims 1
- 239000002502 liposome Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 230000000379 polymerizing Effects 0.000 claims 1
- 150000003431 steroids Chemical class 0.000 claims 1
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims 1
- 102000014961 Protein Precursors Human genes 0.000 abstract 3
- 108010078762 Protein Precursors Proteins 0.000 abstract 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N precursor Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 2
- 238000002835 absorbance Methods 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000003086 colorant Substances 0.000 abstract 1
- 230000000295 complement Effects 0.000 abstract 1
- 239000008278 cosmetic cream Substances 0.000 abstract 1
- 239000008341 cosmetic lotion Substances 0.000 abstract 1
- 230000037308 hair color Effects 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
Abstract
Synthetic melanins suitable for cosmetic uses are produced through oxidative polymerization of monomeric precursors that possess aromatic rings with ionizeable side groups. Agents that enhance adherence of the melanins to skin and hair are co-polymerized with the precursors to become part of the melanin molecules. Potential new precursors and adherence-enhancing agents are screened for efficacy by subjecting them to six separate synthetic procedures, and testing the resulting melanins for color, ultraviolet absorbance charcteristics, and substantivity (adherence) to skin and hair. Melanins of different colors can be blended together in cosmetic creams and lotions to complement the natural skin, eye, and hair colors of an individual. The synthetic procedures are amendable to industrial-scale production of cosmetic melanins. The materials reduce the incidence of solar damage to the skin.
Claims
1. A melanin polymer comprising monomeric units selected from the group consisting of 3- am.'.notyrosine, dihydroxyindole-2-carboxylic acid, 3,4- dihydroxybenzoic acid, 3-amino, 4-hydroxybenzoic acid, aloin, dihydroxyphenylalanine, 4,5-dihydroxynaphthalene-2- sulfonic acid, 3-nitrotyrosine and p-aminobenzoic acid, said melanin polymer characterized by being substantive to human skin and hair and being soluble in aqueous cosmetic buffers at physiological pH and temperature.
2. A melanin polymer according to claim 1, further comprising a comonomer which is an agent that enhances substantivity of the melanin polymer to human skin.
3. A melanin polymer according to claim 2, wherein the comonomer comprises an aromatic glycoside.
4. A melanin polymer according to claim 2, wherein the comonomer comprises aloin.
5. A melanin polymer according to claim 2, wherein the comonomer comprises emodin.
6. A melanin according to claim 2, wherein the comonomer comprises a steroid.
7. A melanin according to claim 2, wherein the comonomer comprises cholesterol.
8. A melanin polymer according to claim 2, wherein the comonomer comprises a carbazole alkaloid.
-27-
9. A melanin polymer according to claim 2, wherein the comonomer comprises dihydroxycarbazole.
10. A melanin polymer according to claim 2, wherein the comonomer comprises a fatty acid.
11. A melanin polymer according to claim 2, wherein the comonomer comprises 9,10-dihydroxystearic acid.
12. A melanin polymer according to claim 2, wherein the comonomer comprises linoleic acid.
13. A melanin polymer according to claim 2, wherein the comonomer comprises linolenic acid.
14. A melanin polymer according to claim 1, comprising monomeric units of an aromatic compound carrying an ionizable side group.
15. A melanin according to claim 1, comprising monomeric units of tyrosine.
16. A melanin according to claim 1, comprising monomeric units of dihydroxyphenylalanine.
17. A melanin according to claim 1, comprising monomeric units of 3-amino-tyrosine.
18. A melanin according to claim 1, comprising monomeric units of 3-nitro-tyrosine.
19. A melanin according to claim 1, comprising monomeric units of dihydroxybenzoic acid.
20. A melanin according to claim 1, comprising monomeric units of 3-amino-4-hydroxybenzoic acid.
21. A melanin according to claim 1, comprising monomeric units of 3-dimethylamino phenol.
22. A melanin according to claim 1, comprising monomeric units of p-aminobenzoic acid.
23. A melanin according to claim 1, comprising monomeric units of an indole.
24. A melanin according to claim 1, comprising monomeric units of dihydroxyindole.
25. A melanin according to claim 1, comprising monomeric units of 5,6-dihydroxyindole-2-carboxylic acid.
26. A melanin according to claim 1, comprising monomeric units of dihydroxynaphthalenesulfonic acid.
27. A melanin polymer according to claim 1, consisting essentially of aloin.
28. A melanin polymer according to claim 1, consisting essentially of emodin.
29. A method of obtaining a melanin polymer according to claim 1, which comprises polymerizing a monomeric material selected from the group consisting of aloin, dihydroxyphthalenesulfonic acid, p-aminobenzoic acid, emodin, dihydroxybenzoic acid, aminohydroxybenzoic acid, tyrosine, dihydroxyphenylalanine, dihydroxyindole-2- carboxylic acid, 3-aminotyrosine, 3-dimethylamino phenol and 3-nitrotyrosine in aqueous solution by oxidation in the presence of air:
-29- (a) in the presence of a weak base; or
(b) in the presence of a weak base and a salt of Cu++ or Fe++; or
(c) in the presence of a weak base, a salt of Cu++ or Fe++ and an oxidant; or
(d) in the presence of a strong base; or
(e) in the presence of a strong base and a salt of Cu++ or Fe++; or
(f) in the presence of a strong base, a salt of Cu++ or Fe++ and an oxidant; and thereafter adding to the resulting solution of formed melanin polymer a lower alkanol, thereby to precipitate from said solution the melanin polymer.
30. The method according to claim 29, wherein the lower alkanol comprises ethanol.
31. A composition comprising a melanin polymer according to claim 1 and urea.
32. A liposome containing a melanin polymer according to claim 1.
-30-
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE69426204T DE69426204T2 (en) | 1993-08-19 | 1994-08-11 | COSMETIC MELANINE |
| CA002169831A CA2169831C (en) | 1993-08-19 | 1994-08-11 | Cosmetic melanins |
| DK94925861T DK0714418T3 (en) | 1993-08-19 | 1994-08-11 | Cosmetic melanins |
| KR1019960700848A KR960703564A (en) | 1993-08-19 | 1994-08-11 | COSMETIC MELANINS |
| AU75640/94A AU702191B2 (en) | 1993-08-19 | 1994-08-11 | Cosmetic melanins |
| AT94925861T ATE197163T1 (en) | 1993-08-19 | 1994-08-11 | COSMETIC MELANIN |
| BR9407304A BR9407304A (en) | 1993-08-19 | 1994-08-11 | Melanin polymer, melanin, screening procedure to test potential precursor and optionally an improving agent for the production of a new malanine polymer, composition, liposome, and process for obtaining a melanin polymer |
| JP7507094A JPH09501961A (en) | 1993-08-19 | 1994-08-11 | Melanin for cosmetics |
| EP94925861A EP0714418B1 (en) | 1993-08-19 | 1994-08-11 | Cosmetic melanins |
| GR20000402855T GR3035168T3 (en) | 1993-08-19 | 2000-12-29 | Cosmetic melanins |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10928693A | 1993-08-19 | 1993-08-19 | |
| US109,286 | 1993-08-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1995005412A1 WO1995005412A1 (en) | 1995-02-23 |
| WO1995005412B1 true WO1995005412B1 (en) | 1995-03-16 |
Family
ID=22326854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1994/009153 WO1995005412A1 (en) | 1993-08-19 | 1994-08-11 | Cosmetic melanins |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP0714418B1 (en) |
| JP (1) | JPH09501961A (en) |
| KR (1) | KR960703564A (en) |
| AT (1) | ATE197163T1 (en) |
| AU (1) | AU702191B2 (en) |
| BR (1) | BR9407304A (en) |
| CA (1) | CA2169831C (en) |
| DE (1) | DE69426204T2 (en) |
| DK (1) | DK0714418T3 (en) |
| ES (1) | ES2153428T3 (en) |
| GR (1) | GR3035168T3 (en) |
| IL (1) | IL110674A0 (en) |
| PT (1) | PT714418E (en) |
| WO (1) | WO1995005412A1 (en) |
| ZA (1) | ZA946327B (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5744125A (en) * | 1993-08-19 | 1998-04-28 | Yale University | Cosmetic melanins |
| US5766214A (en) * | 1996-04-18 | 1998-06-16 | Mehl, Sr.; Thomas L. | Melanin enhanced photothermolysis hair removal |
| US7201815B2 (en) | 2003-09-02 | 2007-04-10 | H.B. Fuller Licensing & Financing Inc. | Paper laminates manufactured using foamed adhesive systems |
| JP5403568B2 (en) * | 2005-07-15 | 2014-01-29 | Ｍｇｃフィルシート株式会社 | Method for producing melanin and melanin produced by the method |
| FR2951373B1 (en) * | 2009-10-16 | 2012-04-13 | Oreal | COMPOSITION COMPRISING AT LEAST ONE 1,8-DIHYROXY-NAPHTHALENE DERIVATIVE AND AT LEAST ONE ALKALINIZING AGENT DIFFERENT FROM AMMONIA, PROCESS FOR COLORING KERATIN FIBERS FROM THE COMPOSITION |
| CA2943604A1 (en) * | 2014-03-25 | 2015-10-01 | Northwestern University | Dopa-melanin formation in high ionic strength solutions |
| CN116115512B (en) * | 2023-04-17 | 2023-08-04 | 知想(南京)生物科技有限公司 | Oligomeric melanin inclusion, and preparation method and application thereof |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4515773A (en) * | 1983-07-05 | 1985-05-07 | Repligen Corporation | Skin tanning composition and method |
| LU85320A1 (en) * | 1984-04-17 | 1985-11-27 | Oreal | COSMETIC COMPOSITION CONTAINING ALOESIN AS A PROTECTIVE AGENT AGAINST SUNLIGHT AND ITS USE FOR PROTECTING SKIN AND HAIR |
| DE3612305A1 (en) * | 1986-04-11 | 1987-10-22 | Roehm Pharma Gmbh | LIQUID MEDICINE FOR THERAPY OF PSORIASIS BASED ON FILM-FORMING POLYMERS |
| US5256403A (en) * | 1987-01-05 | 1993-10-26 | Gaskin Frances C | Composition and method for protecting the skin from UV-rays |
| US4855144A (en) * | 1987-10-23 | 1989-08-08 | Advanced Polymer Systems | Synthetic melanin aggregates |
| US4968497A (en) * | 1988-08-26 | 1990-11-06 | Clairol Incorporated | Skin tanning composition and method |
| AU5195090A (en) * | 1989-03-07 | 1990-10-09 | Plough Inc. | Liposome compositions |
| US5252628A (en) * | 1989-12-07 | 1993-10-12 | Lions Eye Institute Of Western Australia, Inc. | Method of making photoprotective hydrophilic polymers and ocular devices thereof |
| US5227459A (en) * | 1990-05-18 | 1993-07-13 | Yale University | Synthetic melanin |
-
1994
- 1994-08-11 EP EP94925861A patent/EP0714418B1/en not_active Expired - Lifetime
- 1994-08-11 DE DE69426204T patent/DE69426204T2/en not_active Expired - Fee Related
- 1994-08-11 JP JP7507094A patent/JPH09501961A/en active Pending
- 1994-08-11 WO PCT/US1994/009153 patent/WO1995005412A1/en active IP Right Grant
- 1994-08-11 AT AT94925861T patent/ATE197163T1/en not_active IP Right Cessation
- 1994-08-11 AU AU75640/94A patent/AU702191B2/en not_active Ceased
- 1994-08-11 KR KR1019960700848A patent/KR960703564A/en not_active Application Discontinuation
- 1994-08-11 ES ES94925861T patent/ES2153428T3/en not_active Expired - Lifetime
- 1994-08-11 CA CA002169831A patent/CA2169831C/en not_active Expired - Fee Related
- 1994-08-11 PT PT94925861T patent/PT714418E/en unknown
- 1994-08-11 BR BR9407304A patent/BR9407304A/en not_active Application Discontinuation
- 1994-08-11 DK DK94925861T patent/DK0714418T3/en active
- 1994-08-16 IL IL11067494A patent/IL110674A0/en unknown
- 1994-08-19 ZA ZA946327A patent/ZA946327B/en unknown
-
2000
- 2000-12-29 GR GR20000402855T patent/GR3035168T3/en not_active IP Right Cessation
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