CN1658864A - 稳定的抗坏血酸衍生物 - Google Patents
稳定的抗坏血酸衍生物 Download PDFInfo
- Publication number
- CN1658864A CN1658864A CN038134462A CN03813446A CN1658864A CN 1658864 A CN1658864 A CN 1658864A CN 038134462 A CN038134462 A CN 038134462A CN 03813446 A CN03813446 A CN 03813446A CN 1658864 A CN1658864 A CN 1658864A
- Authority
- CN
- China
- Prior art keywords
- ascorbic acid
- acid
- ester
- extract
- salt
- 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
- 125000003289 ascorbyl group Chemical class [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O* 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract description 51
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 239000000126 substance Substances 0.000 claims abstract description 14
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 233
- -1 fatty acid ester Chemical class 0.000 claims description 125
- 229960005070 ascorbic acid Drugs 0.000 claims description 108
- 235000010323 ascorbic acid Nutrition 0.000 claims description 107
- 239000011668 ascorbic acid Substances 0.000 claims description 107
- 238000002360 preparation method Methods 0.000 claims description 91
- 239000000203 mixture Substances 0.000 claims description 87
- 159000000000 sodium salts Chemical class 0.000 claims description 51
- 239000000194 fatty acid Substances 0.000 claims description 35
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 29
- 229930195729 fatty acid Natural products 0.000 claims description 29
- 239000003795 chemical substances by application Substances 0.000 claims description 26
- 239000000463 material Substances 0.000 claims description 24
- 239000003814 drug Substances 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 239000004615 ingredient Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 238000009472 formulation Methods 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 14
- 230000000903 blocking effect Effects 0.000 claims description 14
- 150000004665 fatty acids Chemical group 0.000 claims description 14
- 230000003796 beauty Effects 0.000 claims description 12
- 241001465754 Metazoa Species 0.000 claims description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical group OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
- 239000001117 sulphuric acid Substances 0.000 claims description 11
- 235000011149 sulphuric acid Nutrition 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 10
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 claims description 9
- 229930003268 Vitamin C Natural products 0.000 claims description 9
- 235000019154 vitamin C Nutrition 0.000 claims description 9
- 239000011718 vitamin C Substances 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 235000013305 food Nutrition 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 239000000344 soap Substances 0.000 claims description 8
- 239000003905 agrochemical Substances 0.000 claims description 7
- 230000037319 collagen production Effects 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 239000002778 food additive Substances 0.000 claims description 5
- 239000011701 zinc Substances 0.000 claims description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 230000002087 whitening effect Effects 0.000 claims description 4
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 claims description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 239000003674 animal food additive Substances 0.000 claims description 3
- 229910052797 bismuth Inorganic materials 0.000 claims description 3
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 3
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 claims description 3
- 235000016804 zinc Nutrition 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- FERWBXLFSBWTDE-UHFFFAOYSA-N 3-aminobutan-2-ol Chemical compound CC(N)C(C)O FERWBXLFSBWTDE-UHFFFAOYSA-N 0.000 claims description 2
- 159000000003 magnesium salts Chemical class 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
- 150000003751 zinc Chemical class 0.000 claims description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 239000000284 extract Substances 0.000 description 129
- 239000006210 lotion Substances 0.000 description 54
- 235000002639 sodium chloride Nutrition 0.000 description 50
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 48
- 210000003491 skin Anatomy 0.000 description 41
- 150000002148 esters Chemical class 0.000 description 39
- 229950004531 hexyldecanoic acid Drugs 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- 239000002253 acid Substances 0.000 description 29
- 239000002351 wastewater Substances 0.000 description 27
- 230000000694 effects Effects 0.000 description 26
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 22
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 21
- RSJKGSCJYJTIGS-UHFFFAOYSA-N N-undecane Natural products CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 21
- 239000000843 powder Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 18
- 102000008186 Collagen Human genes 0.000 description 16
- 108010035532 Collagen Proteins 0.000 description 16
- 229920001436 collagen Polymers 0.000 description 16
- 229920001577 copolymer Polymers 0.000 description 15
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- 229920001296 polysiloxane Polymers 0.000 description 14
- 210000004209 hair Anatomy 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 238000013019 agitation Methods 0.000 description 12
- 239000002537 cosmetic Substances 0.000 description 11
- 229940079593 drug Drugs 0.000 description 11
- 238000012545 processing Methods 0.000 description 11
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 10
- 206010052428 Wound Diseases 0.000 description 10
- 208000027418 Wounds and injury Diseases 0.000 description 10
- 210000000582 semen Anatomy 0.000 description 10
- 241000628997 Flos Species 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229910019142 PO4 Inorganic materials 0.000 description 9
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 9
- 150000001721 carbon Chemical group 0.000 description 9
- 239000006071 cream Substances 0.000 description 9
- 239000010452 phosphate Substances 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 239000001509 sodium citrate Substances 0.000 description 9
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 9
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 208000034189 Sclerosis Diseases 0.000 description 8
- 238000005282 brightening Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 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 8
- 229920000642 polymer Polymers 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 235000015424 sodium Nutrition 0.000 description 8
- 229920001285 xanthan gum Polymers 0.000 description 8
- 235000010493 xanthan gum Nutrition 0.000 description 8
- 239000000230 xanthan gum Substances 0.000 description 8
- 229940082509 xanthan gum Drugs 0.000 description 8
- 239000003513 alkali Substances 0.000 description 7
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 7
- 239000000049 pigment Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 241000251468 Actinopterygii Species 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 235000001014 amino acid Nutrition 0.000 description 6
- 150000001413 amino acids Chemical class 0.000 description 6
- 229960003237 betaine Drugs 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 6
- 230000019612 pigmentation Effects 0.000 description 6
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- 239000004094 surface-active agent Substances 0.000 description 6
- 241000700199 Cavia porcellus Species 0.000 description 5
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 241000277275 Oncorhynchus mykiss Species 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 5
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 5
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- 235000019438 castor oil Nutrition 0.000 description 5
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 238000010438 heat treatment Methods 0.000 description 5
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 5
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- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 5
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 5
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 5
- 229960002216 methylparaben Drugs 0.000 description 5
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 5
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- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 4
- MIJPAVRNWPDMOR-ZAFYKAAXSA-N L-ascorbic acid 2-phosphate Chemical compound OC[C@H](O)[C@H]1OC(=O)C(OP(O)(O)=O)=C1O MIJPAVRNWPDMOR-ZAFYKAAXSA-N 0.000 description 4
- 239000005639 Lauric acid Substances 0.000 description 4
- 235000021360 Myristic acid Nutrition 0.000 description 4
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
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- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 description 4
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- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 4
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 3
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- 229910052623 talc Inorganic materials 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- DZKXJUASMGQEMA-UHFFFAOYSA-N tetradecyl tetradecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC DZKXJUASMGQEMA-UHFFFAOYSA-N 0.000 description 1
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- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- ZXKBZSUZLCNLAQ-UHFFFAOYSA-M trimethyl(octadecanoyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC(=O)[N+](C)(C)C ZXKBZSUZLCNLAQ-UHFFFAOYSA-M 0.000 description 1
- AISMNBXOJRHCIA-UHFFFAOYSA-N trimethylazanium;bromide Chemical compound Br.CN(C)C AISMNBXOJRHCIA-UHFFFAOYSA-N 0.000 description 1
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
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- 229940118846 witch hazel Drugs 0.000 description 1
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- 239000003357 wound healing promoting agent Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
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- CKLHRQNQYIJFFX-UHFFFAOYSA-K ytterbium(III) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Yb+3] CKLHRQNQYIJFFX-UHFFFAOYSA-K 0.000 description 1
- GPYYEEJOMCKTPR-UHFFFAOYSA-L zinc;dodecanoate Chemical compound [Zn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O GPYYEEJOMCKTPR-UHFFFAOYSA-L 0.000 description 1
- GJAPSKMAVXDBIU-UHFFFAOYSA-L zinc;hexadecanoate Chemical compound [Zn+2].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O GJAPSKMAVXDBIU-UHFFFAOYSA-L 0.000 description 1
- CPYIZQLXMGRKSW-UHFFFAOYSA-N zinc;iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+3].[Fe+3].[Zn+2] CPYIZQLXMGRKSW-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- A61K31/66—Phosphorus compounds
- A61K31/665—Phosphorus compounds having oxygen as a ring hetero atom, e.g. fosfomycin
-
- 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
- A61K8/67—Vitamins
- A61K8/676—Ascorbic acid, i.e. vitamin C
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/16—Emollients or protectives, e.g. against radiation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Organic Chemistry (AREA)
- Dermatology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Birds (AREA)
- Molecular Biology (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Hematology (AREA)
- Toxicology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Nutrition Science (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
抗坏血酸衍生物,其为由通式(1)代表的化合物或其盐:其中X和Y各自代表H或OH保护基团,R1和R2各自代表具有1至19个碳原子的烷基,所述烷基可以是直链或支链的,且R1和R2中的碳原子总数是5至22的整数。
Description
本申请要求基于美国临时申请序号60/373609(2002年4月9日提交)的申请的优先权。
技术领域
本发明涉及新颖的抗坏血酸衍生物。更具体而言,本发明涉及为稳定化合物的抗坏血酸衍生物和制备该化合物的方法。本发明还涉及含有这种抗坏血酸衍生物的各种形式或实施方式,例如维生素C制剂或试剂、胶原产生促进剂、增白剂、外部使用或应用的皮肤用药、医学或药学制剂、农业化学制剂、动物或兽医药物制剂、食品添加剂和动物饲料添加剂,各自含有抗坏血酸衍生物。
背景技术
抗坏血酸具有某些活性,例如抑制脂质过氧化物的产生、促进胶原的产生、延迟黑素的生成和增强免疫功能或表现。为此,抗坏血酸已经用在医学或药学制剂、农业化学制剂、动物或兽医药物制剂、食品、动物饲料、美容制剂等领域。不过,抗坏血酸随时间的推移具有较差的稳定性,和较差的脂溶性。因此,抗坏血酸渗透通过细胞膜并且蓄积在细胞中的量是相当有限的,如果使用抗坏血酸本身,那么维生素C的生理作用不能达到令人满意的程度。为了提高抗坏血酸的稳定性,人们已经提出了各种其衍生物,例如将对氧化作用敏感的2-或3-位烯二醇部分中的羟基转化为磷酸酯,例如如JP-B(已审日本专利公报)52-1819(专利文献1)和JP-A(未审公开的日本专利申请)02-279690(专利文献2)所述,或者利用脂肪酸进行酰化作用,以便提高脂溶性,例如如JP-A-59-170085(专利文献3)所述。不过,很少有衍生物既提高稳定性又提高脂溶性。
至于稳定性和脂溶性均被提高的抗坏血酸,JP-A-61-152613(专利文献4)描述了含有6-O-高级-酰基抗坏血酸-2-磷酸酯盐的美容组合物。不过,在这份专利公报中,描述了制备其硫酸酯(而非磷酸酯)的方法,没有描述制备其磷酸酯的方法,并且没有鉴别由这份公报所提供的抗坏血酸衍生物。从这些方面来看,难以认可这份公报公开了6-O-高级-酰基抗坏血酸-2-磷酸酯至能够实施的程度。
JP-A-10-298174(专利文献5)描述了制备6-O-高级-酰基抗坏血酸-2-磷酸酯的方法和该物质的结构测定结果。据称由这种方法所制备的6-O-高级-酰基抗坏血酸-2-磷酸酯在稳定性和脂溶性上都有提高,其细胞摄取也得以促进。不过,在这些物质中,抗坏血酸-2-磷酸酯-6-棕榈酸酯钠盐及其水溶液早其稳定性方面尚不令人满意。
专利文献1:JP-B-52-1819
专利文献2:JP-A-02-279690
专利文献3:JP-A-59-170085
专利文献4:JP-A-61-152613
专利文献5:JP-A-10-298174
发明内容
本发明的目的是提供已经克服了现有技术所面临的上述问题的抗坏血酸衍生物和制备这样一种抗坏血酸衍生物的方法。
本发明的另一目的是提供6-O-高级-酰基抗坏血酸-2-磷酸酯和/或其盐,它在稳定性上已得以提高并且具有新颖的结构,还提供制备它的方法和采用6-O-高级-酰基抗坏血酸-2-磷酸酯和/或其盐的制剂(例如美容材料)。
作为认真研究的结果,本发明人已经发现,与具有直链脂肪酸残基的常规6-O-高级-酰基抗坏血酸-2-磷酸酯和/或其盐相比,新合成的其中6-位酰基(脂肪酸残基)是在α-位分支的6-O-高级-酰基抗坏血酸-2-磷酸酯和/或其盐在其稳定性方面已有大幅提高。基于这种发现而完成了本发明。
由通式(1)代表的根据本发明的抗坏血酸衍生物的特征在于6-位高级脂肪酸酯是在α-碳上分支的脂肪酸酯。
根据本发明人的实验,已经发现常规6-O-高级直链脂肪酸酯的酯键在其贮存期间分解或裂解,导致在贮存后剩余的抗坏血酸-2-磷酸酯的比例减少。相反,根据本发明的抗坏血酸-2-磷酸-6-脂肪酸酯具有提高了的稳定性。根据本发明人的研究和认识,假定作为原料的脂肪酸酯如从α-碳分支的脂肪酸合成的抗坏血酸-2-磷酸-6-脂肪酸酯具有加强或强化了的酯键。
更具体而言,本发明涉及下列主题。
[1]抗坏血酸衍生物,它是由下列通式(1)代表的化合物或其盐:
[化学式1]
其中X和Y各自代表H或OH保护基团,R1和R2各自代表具有1至19个碳原子的烷基,所述烷基可以是直链或支链的,且R1和R2中的碳原子总数是5至22的整数。
[2]根据[1]的抗坏血酸衍生物,它是一种或多种金属的盐,所述金属选自碱金属、碱土金属、铝、铁、锌和铋。
[3]根据[1]的抗坏血酸衍生物,它是氨、单乙醇胺、二乙醇胺、三乙醇胺、二环己胺或2-氨基-1-甲基丙醇的盐。
[4]根据[1]至[3]任意一项的抗坏血酸衍生物,其中通式(1)中R1和R2的碳原子总数是8至18的整数。
[5]根据[4]的抗坏血酸衍生物,其中通式(1)的R1和R2是直链烷基,且R1和R2直链烷基中的碳原子总数是14或16。
[6]根据[5]的抗坏血酸衍生物,其中在通式(1)中,R1是n-C9H19,且R2是n-C7H15;或者R1是n-C8H17,且R2是n-C6H13。
[7]制备根据[1]至[6]任意一项的抗坏血酸衍生物的方法,包含下列步骤:使由下列通式(2)代表的化合物和/或其盐:
[化学式2]
其中X和Y各自代表H或OH保护基团,
与选自脂肪酸、脂肪酸盐、脂肪酸酯、脂肪酰卤和/或脂肪酸酐的至少一种反应。
[8]根据[7]的制备抗坏血酸衍生物的方法,其中所述反应在缩合剂和/或脱水剂的存在下进行。
[9]根据[8]的制备抗坏血酸衍生物的方法,其中所述脱水剂是硫酸。
[10]根据[7]至[9]任意一项的制备抗坏血酸衍生物的方法,其中所述反应在溶剂中进行,所述溶剂选自水、丙酮、二噁烷、甲苯、乙基苯、甲基叔丁基醚和硫酸。
[11]维生素C制剂,包含根据[1]至[6]任意一项的抗坏血酸衍生物作为有效成分。
[12]胶原产生促进剂,包含根据[1]至[6]任意一项的抗坏血酸衍生物作为有效成分。
[13]增白制剂,包含根据[1]至[6]任意一项的抗坏血酸衍生物作为有效成分。
[14]外用皮肤制剂,包含根据[1]至[6]任意一项的抗坏血酸衍生物作为有效成分。
[15]根据[14]的外用皮肤制剂,其含有抗坏血酸-2-磷酸酯和/或其盐。
[16]根据[14]的外用皮肤制剂,其含有抗坏血酸-2-磷酸酯的钠盐、钾盐、镁盐或锌盐。
[17]美容材料,包含根据[14]至[16]任意一项的外用皮肤制剂。
[18]组合物,包含根据[1]至[6]任意一项的抗坏血酸衍生物,为医学或药学制剂、农业化学制剂或动物药物制剂的形式。
[19]组合物,包含根据[1]至[6]任意一项的抗坏血酸衍生物,为食品或饲料添加剂的形式。
实施本发明的最佳方式
下面,将根据需要参照附图详细描述本发明。下列说明中,代表量化比例的“%”和“份”是基于质量而言,另有具体注解除外。
抗坏血酸衍生物
根据本发明的抗坏血酸衍生物是由下列通式(1)代表的化合物和/或其盐:
[化学式3]
其中X和Y各自代表H或OH保护基团,R1和R2各自代表具有1至19个碳原子的烷基,所述烷基可以是直链或支链的,且R1和R2的碳原子总数是5至22的整数。
本发明中,除非另有具体注解,抗坏血酸或抗坏血酸衍生物可以优选地是L-型。
根据本发明的抗坏血酸衍生物不太易于被氧化,具有优异的稳定性,这是因为抗坏血酸的2-位被酯化为磷酸酯。
进而,在根据本发明的抗坏血酸衍生物中,其6-位被酯化为高级脂肪酸酯,因此,这种化合物能够具有适当的脂溶性,并具有促进细胞摄取的特征。另外,这种化合物中2-位磷酸基团容易被活体内的磷酸酶水解,且6-位高级脂肪酸酯是伯醇(6-位)的酯,它对脂肪酶或酯酶的作用敏感,这种化合物可以在活体内容易地转化为抗坏血酸。
抗坏血酸衍生物的制备方法1
根据本发明的由通式(1)代表的化合物和/或盐例如可以按照下列反应式制备:
[化学式4]
其中X和Y各自代表H或OH保护基团,R1和R2各自代表具有1至19个碳原子的烷基,且R1和R2的碳原子总数是5至22,且R3代表氢原子、阳离子或具有1至5个碳原子的烷基。
更具体而言,使由式(2)代表的化合物和/或其盐与至少由式(3)代表的在α-碳分支的脂肪酸及其酯和盐之一反应,生成抗坏血酸-2-磷酸-6-脂肪酸酯(1)和/或其盐。
脱水剂或缩合剂
上述反应可以优选地在脱水或缩合剂的存在下进行。
用在这样一种情况中的脱水或缩合剂没有特别限制。缩合剂的优选实例可以包括N,N’-二环己基碳二亚胺、N,N’-二异丙基碳二亚胺、N-乙基-N’-3-二甲氨基丙基碳二亚胺、苯并三唑-1-基-三(二甲氨基)鏻六氟磷化物盐、二苯基磷酰叠氮化物,这些是最佳的缩合剂。其中,优选地使用N,N’-二异丙基碳二亚胺。脱水剂的优选实例可以包括五氧化二磷、固体磷酸、氧化钛、氧化铝和硫酸。其中,优选地使用硫酸(优选95质量%或以上的浓硫酸),将浓硫酸、抗坏血酸-2-磷酸酯和脂肪酸或其酯或盐混合并反应。
在式(3)的脂肪酸酯中,R3代表具有1至5个碳原子的烷基酯,可以优选为具有1至3个碳原子的低级烷基酯,更优选甲基酯或乙基酯。
反应时间和反应温度可以因脂肪酸是游离酸、酯或盐或者缩合剂的种类与用量而异。不过,反应时间可以一般为1至120小时,优选4至10小时,反应温度可以一般为5至70℃,优选30至50℃。
从原料或催化剂带入反应溶液中的水含量可以适宜地为10%或以下,优选2%或以下。
溶剂
当在该反应中使用溶剂时,本身作为缩合剂的硫酸也可以作为溶剂使用。或者,也有可能从其他能够溶解原料的溶剂中选择溶剂。这类其他溶剂的具体实例可以包括水、丙酮、二噁烷、甲苯、乙基苯和甲基叔丁基醚等。
抗坏血酸衍生物的制备方法2
根据本发明的由通式(1)代表的化合物和/或盐例如还可以按照下列反应式制备:
[化学式5]
其中X和Y各自代表H或OH保护基团,R1和R2各自代表具有1至19个碳原子的烷基,R1和R2中的碳原子总数为5至22,且Z代表卤化物。
更具体而言,使由通式(2)代表的抗坏血酸-2-磷酸和/或盐与由通式(4)代表的在α-碳分支的脂肪酰卤反应,生成抗坏血酸-2-磷酸-6-脂肪酸酯(1)和/或其盐。
碱
上述反应可以优选地在碱的存在下进行。该碱没有特别限制,只要它是通常在醇与酰卤的反应中可用作脱卤化氢剂的碱即可。其优选实例可以包括叔胺,例如吡啶和三乙胺。
抗坏血酸衍生物的制备方法3
由通式(1)代表的化合物和/或其盐例如还可以按照下列反应式制备:
[化学式6]
其中X和Y各自代表H或OH保护基团,R1和R2各自代表具有1至19个碳原子的烷基,且R1和R2中的碳原子总数是5至22。
更具体而言,使由式(5)代表的在α-碳分支的脂肪酸酐与由通式(2)代表的抗坏血酸-2-磷酸和/或其盐反应,生成由式(1)代表的抗坏血酸-2-磷酸-6-脂肪酸酯和/或其盐。
摩尔比
在根据本发明的制备方法中,在任意上述反应中可以使用等摩尔量的原料。不过,有可能使用略微过量的任意一种原料(例如原料之任一种可以是1.0-3.0、更优选约1.0-1.5,按它们之间的摩尔比计),只要在预定反应之后所要进行的纯化或分离期间基本上没有问题产生即可。
纯化和/或分离
纯化或分离方法没有特别限制。更具体而言,纯化或分离可以利用一般方法进行,例如溶剂萃取、洗涤、盐析或柱色谱。例如,反应产物可以借助醚萃取或用非极性溶剂如己烷洗涤加以分离或纯化。如果需要的话,所得产物可以进一步借助反相色谱等加以纯化。
由式(2)的抗坏血酸的3-和5-位X和Y代表的基团都可以优选地是H。不过,在任意上述反应中,这些基团可以被基本上不受反应影响的保护基团取代。
不敏感的保护基团的具体实例:酰基、烷磺酰基、可以被取代的苯磺酰基、二烷基氨甲酰基、苄基、烷基、甲硅烷基。
抗坏血酸衍生物的盐
由下列通式(1)代表的化合物的盐可以按照下列方式得到:
[化学式7]
其中X和Y各自代表H或OH保护基团,R1和R2各自代表具有1至19个碳原子的烷基,所述烷基可以是直链或支链的,且R1和R2中的碳原子总数是5至22的整数。
因而,在能够溶解酯的溶剂如水或甲醇中,将所得抗坏血酸-2-磷酸-6-高级脂肪酸酯例如用适当的碱(例如氢氧化钠、氢氧化钾、氧化镁、氢氧化钙、氨、单乙醇胺、二乙醇胺、三乙醇胺或二环己胺)中和,由此可以得到该碱的盐。
抗坏血酸衍生物的盐的种类没有特别限制,只要抗坏血酸衍生物盐的使用或应用基本上不受损害即可。鉴于易获得性和将其配制成制剂,该盐可以优选地是含有碱金属、碱土金属、铝、铁、锌和铋的那些。其中,优选的是碱金属如钠和钾,和碱土金属如钙和镁。它们可以单独使用或者两种或多种联合使用。
羟基的保护
在由上列通式(1)代表的化合物中,3-或5-位羟基还可以被公知的易于转化为羟基的基团保护。本发明可以包括具有这样一种保护基团(例如酰基、烷磺酰基、可以被取代的苯磺酰基或二烷基氨甲酰基、苄基、烷基、甲硅烷基等)的化合物。保护基团可以在6-位酯化反应之前或之后被引入到预定化合物中。
这种反应不仅可以应用于制备根据本发明的抗坏血酸-2-磷酸的6-O-高级脂肪酸酯的方法中,而且可以应用于制备公知的其中上列通式(1)中的R1和R2各自独立地代表CH3或C2H5的6-O-低级脂肪酸酯。
制剂
根据本发明的抗坏血酸衍生物表现维生素C活性,与公知的抗坏血酸衍生物相比在稳定性和脂溶性方面都有显著提高。因此,维生素C可以由根据本发明的抗坏血酸衍生物本身供应,或者由含有根据本发明的抗坏血酸衍生物的制剂(维生素C制剂)供应。根据本发明的抗坏血酸衍生物的使用或应用没有特别限制。例如,在将根据本发明的抗坏血酸衍生物掺入医学或药学制剂、农业化学品、食品、饲料或美容制剂等时,能够有效地供应维生素C。
高级脂肪酸酯
鉴于其维生素C活性,根据本发明的抗坏血酸衍生物可以适宜为L-型。进而,6-位高级脂肪酸酯的特征在于它是在α-碳分支的脂肪酸酯。如上所述,根据本发明人的实验,已经发现常规6-O-高级直链脂肪酸酯的酯键在其贮存期间分解或裂解,导致在贮存后剩余的抗坏血酸-2-磷酸酯的比例减少。相反,假定在根据本发明的抗坏血酸衍生物(例如从α-碳分支的脂肪酸合成的抗坏血酸-2-磷酸-6-脂肪酸酯)中,酯键被加强或强化,因此根据本发明的抗坏血酸衍生物在稳定性试验中显示出提高的稳定性。
鉴于脂溶性,6-O-高级脂肪酸酯的优选实例可以包括2-丁基己酸酯、2-己基癸酸酯和2-庚基十一烷酸酯。
胶原产生促进剂、外用皮肤用药等
由根据本发明的制备方法所得到的抗坏血酸衍生物具有胶原产生促进效果和增白效果,因此,它还可以用作胶原产生促进剂或增白剂。进而,抗坏血酸衍生物可以有效地用作外用皮肤用药,例如将其与另一种皮肤用药一起配制。
当抗坏血酸衍生物用作皮肤用药时,根据本发明的外用皮肤用药可以含有由下列通式(2)代表的抗坏血酸-2-磷酸酯和/或其盐,此外还有由根据本发明的制备方法所得到的抗坏血酸衍生物(由通式(1)代表):
[化学式8]
其中X和Y各自代表H或OH保护基团。在其中含有由下列通式(2)代表的抗坏血酸-2-磷酸酯和/或其盐的实施方式中,也有可能获得向表皮(或角质层)和真皮(dermis)(或真皮(corium))提供抗坏血酸源的有利效果。
抗坏血酸-2-磷酸酯
下面更加详细地描述抗坏血酸-2-磷酸酯和/或其盐。
根据本发明的抗坏血酸-2-磷酸酯可以是D-型、L-型和DL-型的任意一种,但是可以优选地是L-型。抗坏血酸-2-磷酸酯的盐例如可以是这样一种化合物,其中磷酸酯与抗坏血酸2-位键合,磷酸酯的磷酸基团与碱生成盐。
抗坏血酸-2-磷酸酯的盐的具体实例可以包括碱金属盐、碱土金属盐、Zn盐、Al盐、Ti盐等。其中,从经济观点来看,优选的是Na盐、K盐、Mg盐和Zn盐,更优选的是Na盐和Mg盐。
胶原产生促进效果
本发明中,胶原产生促进效果意味着在借助氨基酸分析法测量例如皮肤组织中的羟脯氨酸含量、并且利用所得数据作为胶原产生促进效果的指标时,供试区域(或节段)中的羟脯氨酸的量是对照区域的至少1.2至2倍。
本发明中,胶原产生促进剂、增白剂或外用皮肤用药可以在使用的同时强调其本身的效果作为主要效果。不过,也有可能向其中进一步加入另一种成分,以修饰或调整该效果。
在胶原产生促进剂、增白剂或外用皮肤用药中,已被掺入到这些制剂中的、由根据本发明的制备方法所得到的抗坏血酸衍生物的量可以鉴于所需效果的程度或者与其他联用成分的关系加以适当选择。不过,基于制剂的全部质量,这例如可以是0.01至30质量%,优选0.03至20质量%。
为了利用胶原产生促进效果和/或增白效果,可以加入另一种添加剂(例如已知有效对抗皮肤老化的成分、已知有效促进胶原产生与抑制皱纹的成分、已知增白剂等)。
作为这样一种添加剂,有可能掺入下列这些:茶提取物、t-AMCHA、L-赖氨酸、L-精氨酸、咖啡因、鞣酸、维拉帕米、氨甲环酸、氨甲环酸衍生物、透明质酸、甘草提取物、光甘草定、果实如榅桲(quince)、覆盆子(raspberry)和鳄梨的热水提取物、白葡萄酒酵母提取物、各种日本与中国生药或其提取物、香料(aroma)提取物、生育酚乙酸酯、甘草酸、甘草酸衍生物、熊果苷、日本酒曲(或麦芽)、葡萄糖、果糖、甘露糖、蔗糖、海藻糖、藻糖原、视黄酸、视黄醇、乙酸视黄醇和棕榈酸视黄醇。
还可以联合使用后面所要描述的可以用作增白剂的生物活性物质。
而且,可以根据外用皮肤用药的剂型或形状加入各种基质成分。
这样一种基质成分可以根据各种具体用途、应用或目的加入。基质成分的具体实例可以包括液体油脂、固体油脂、蜡、酯油、烃油、有机硅树脂、硅酮、阴离子表面活性剂、阴离子型表面活性剂、阳离子表面活性剂、两性表面活性剂、非离子表面活性剂、低级醇、甾醇、水溶性聚合物、螯合剂(例如乙二胺四乙酸二钠、乙二酸四乙酸三钠、柠檬酸钠、多磷酸钠、偏磷酸钠、葡萄糖酸)、中和剂、pH调节剂、杀细菌剂或抗真菌剂和香料。
在本发明抗坏血酸应用于皮肤的情况下,可以掺入另一种一般可用在皮肤制剂中的成分,只要这类加入基本上不会损害本发明的效果即可。所用成分的具体实例可以包括药剂、试剂、药物、药品、介质、成药、药物制剂,如下文献所述:“日本化妆品成分标准(JSCI),第2版注释”(JapaneseStandards of Cosmetic Ingredients(JSCI),2nd Edition,Annotation),由Nippon Koteisho Kyokai汇编,由Yakuji Nippo,Ltd.发行(1984);“除JSCI所列之外成分的说明-增补”(Specifications of Ingredient Other Than ThoseListed in JSCI,supplement),由卫生福利部药事局审查分部监督,由YakujiNippo,Ltd.发行(1993);“The Comprehensive Licensing Standards ofCosmetics by Category”,由卫生福利部药事局审查分部监督,由YakujiNippo,Ltd.发行(1993)和Kesho-hin Genryo Jiten(化妆品成分手册),NikkoChemicals(1991)等。
下面将列举可以加入到根据本发明的制剂中的材料或试剂的具体实例。这些实例例如包括油、高级醇、脂肪酸、紫外吸收剂、药粉、色素、表面活性剂、多元醇与糖、聚合物、生物活性成分、溶剂、抗氧化剂、香料和防腐剂。不过,事实上,可用于本发明的那些并不限于这些实例。
(1)油的具体实例
酯型油相成分
2-乙基己酸三甘油酯、2-乙基己酸鲸蜡酯、肉豆蔻酸异丙酯、肉豆蔻酸丁酯、棕榈酸异丙酯、硬脂酸乙酯、棕榈酸辛酯、异硬脂酸异鲸蜡酯、硬脂酸丁酯、肉豆蔻酸丁酯、亚油酸乙酯、亚油酸异丙酯、油酸乙酯、肉豆蔻酸异鲸蜡酯、肉豆蔻酸异十八酯、棕榈酸异十八酯、肉豆蔻酸辛基十二醇酯、异硬脂酸异鲸蜡酯、癸二酸二乙酯、己二酸二异丙酯、新戊酸异花生醇酯、辛酸-癸酸三甘油酯、三羟甲基丙烷三-2-乙基己酸酯、三羟甲基丙烷三异硬脂酸酯、季戊四醇四-2-乙基己酸酯、辛酸鲸蜡酯、月桂酸癸酯、月桂酸己酯、肉豆蔻酸癸酯、肉豆蔻酸肉豆蔻酯、肉豆蔻酸鲸蜡酯、硬脂酸十八酯、油酸癸酯、蓖麻醇酸鲸蜡酯、月桂酸异十八酯、肉豆蔻酸异十三烷基酯、肉豆蔻酸异鲸蜡酯、肉豆蔻酸异十八酯、棕榈酸异鲸蜡酯、棕榈酸异十八酯、硬脂酸辛酯、硬脂酸异鲸蜡酯、油酸异癸酯、油酸辛基十二醇酯、亚油酸辛基十二醇酯、异硬脂酸异丙酯、2-乙基己酸鲸蜡十八酯、2-乙基己酸十八酯、异硬脂酸己酯、乙二醇二辛酸酯、乙二醇二油酸酯、丙二醇二癸酸酯、丙二醇二(辛酸酯/癸酸酯)、丙二醇二辛酸酯、新戊二醇二癸酸酯、新戊二醇二辛酸酯、甘油三辛酸酯、甘油三-十一烷酸酯、甘油三异棕榈酸酯、甘油三异硬脂酸酯、新戊酸辛基十二醇酯、辛酸异十八酯、异壬酸辛基酯、新癸酸己基癸基酯、新癸酸辛基十二醇酯、异硬脂酸异鲸蜡酯、异硬脂酸异十八酯、异硬脂酸辛癸酯、聚甘油油酸酯、聚甘油异硬脂酸酯、碳酸二丙酯、碳酸二烷基酯(C12-18)、柠檬酸三异鲸蜡酯、柠檬酸三异花生醇酯、柠檬酸三异辛酯、乳酸月桂酯、乳酸肉豆蔻酯、乳酸鲸蜡酯、乳酸辛癸酯、柠檬酸三乙酯、柠檬酸乙酰三乙酯、柠檬酸乙酰三丁酯、柠檬酸三辛酯、苹果酸二异十八酯、羟硬脂酸2-乙基己基酯、琥珀酸2-乙基己基酯、己二酸二异丁酯、癸二酸二异丙酯、癸二酸二辛酯、硬脂酸胆甾醇酯、异硬脂酸胆甾醇酯、羟硬脂酸胆甾醇酯、油酸胆甾醇酯、油酸二氢胆甾醇酯、异硬脂酸植物甾醇酯、油酸植物甾醇酯、12-硬脂酰羟硬脂酸异鲸蜡酯、12-硬脂酰羟硬脂酸十八酯和12-硬脂酰羟硬脂酸异十八酯。
烃型油相成分
角鲨烷、液体石蜡、α-烯烃低聚物、异链烷烃、地蜡、石蜡、液体异链烷烃、聚丁烯、微晶蜡和矿脂。
动物与植物油、其硬化油和天然来源的蜡
动物油及其硬化油例如牛脂、硬化牛脂、猪油、硬化猪油、马油、硬化马油、貂油、粗橙油、鱼油、硬化鱼油和卵黄油;植物油及其硬化油例如鳄梨油、杏仁油(almond oil)、橄榄油、可可油、杏仁油(apricot kernel oil)、椰子油、芝麻油、麦胚油、米胚油、米糠油、红花油、牛油树脂、大豆油、月见草油、椿油(tsubaki oil)、玉米油、菜籽油、硬化菜籽油、棕榈仁油、硬化棕榈仁油、棕榈油、硬化棕榈油、花生油、硬化花生油、蓖麻油、氢化蓖麻油、葵花油、葡萄籽油、霍霍巴油、硬化霍霍巴油、夏威夷果油(macadamia nut oil)、白芒花籽油(meadowfoam seed oil)、棉籽油、硬化棉籽油;蜡例如蜂蜡、高酸值蜂蜡、羊毛脂、还原羊毛脂、液体羊毛脂、巴西棕榈蜡和褐煤蜡。
硅酮型油相成分
聚二甲基硅氧烷、聚甲基苯基硅氧烷、甲基环聚硅氧烷(methylcyclopolysiloxane)、八甲基聚硅氧烷(octamethylpolysiloxane)、十甲基聚硅氧烷(decamethylpolysiloxane)、十二甲基环硅氧烷、聚甲基氢硅氧烷、聚醚修饰的有机聚硅氧烷、二甲基硅氧烷-甲基鲸蜡氧基硅氧烷共聚物、二甲基硅氧烷-甲基硬脂酰氧基硅氧烷共聚物、烷基修饰的有机聚硅氧烷、末端修饰的有机聚硅氧烷、聚二甲基硅氧烷醇、硅酮凝胶、丙烯酰基硅酮、三甲代甲硅烷氧基硅酸和硅酮RTV橡胶。
氟型油相成分
全氟聚醚、氟修饰的有机聚硅氧烷、氟化沥青(fluorinated pitch)、碳氟化合物、氟代醇和氟代烷基-聚氧化亚烷基共同修饰的有机聚硅氧烷。
(2)高级醇的具体实例
月桂醇、肉豆蔻醇、鲸蜡醇、硬脂醇、异硬脂醇、油醇、山嵛醇、2-乙基己醇、十六烷醇和辛基十二烷醇。
(3)脂肪酸的具体实例
辛酸、癸酸、十一碳烯酸、月桂酸、肉豆蔻酸、棕榈酸、棕榈油酸、硬脂酸、异硬脂酸、油酸、亚油酸、亚麻酸、花生酸、花生四烯酸、山嵛酸、芥酸和2-乙基己酸。
(4)紫外吸收剂的具体实例
对-氨基苯甲酸、对-氨基苯甲酸戊酯、对-氨基苯甲酸乙基二羟基丙基酯、对-氨基苯甲酸甘油酯、对-氨基苯甲酸乙酯、对-氨基苯甲酸辛酯、对-氨基苯甲酸辛基二甲基酯、乙二醇水杨酸酯、水杨酸辛酯、三乙醇胺水杨酸酯、水杨酸苯酯、水杨酸丁基苯基酯、水杨酸苄酯、对-甲氧基肉桂酸辛酯、对-甲氧基肉桂酸2-乙基己基酯、甘油单-2-乙基己酸酯二-对-甲氧基肉桂酸酯、对-甲氧基肉桂酸异丙酯、二乙醇胺对-甲氧基氢化肉桂酸盐、二异丙基·二异丙基肉桂酸酯混合物、尿刊酸、尿刊酸乙酯、羟基甲氧基二苯酮、羟基甲氧基二苯酮磺酸及其盐、二羟基甲氧基二苯酮、二羟基甲氧基二苯酮二磺酸钠、二羟基二苯酮、二羟基二甲氧基二苯酮、羟基辛氧基二苯酮、四羟基二苯酮、丁基甲氧基二苯甲酰基甲烷、2,4,6-三苯胺基-p-(2-乙基己-1-酯基)-1,3,5-三嗪、2-(2-羟基-5-甲基苯基)苯并三唑、o-氨基苯甲酸甲基酯、2-乙基己基-2-氰基-3,3-二苯基丙烯酸酯、苯基苯并咪唑硫酸、3-(4-甲基亚苄基)樟脑、异丙基二苯甲酰基甲烷、4-(3,4-二甲氧基苯基亚甲基)-2,5-二氧基-1-咪唑烷丙酸2-乙基己基酯和它们的聚合物衍生物与硅烷衍生物。
(5)粉末和颜料的具体实例
颜料例如Food Red 104、Food Red 201、Food Yellow 4、Food Blue 1和Food Black 401;色淀颜料例如Food Yellow 4 AL色淀和Food Yellow203 BA色淀;聚合物例如尼龙粉、蚕丝粉、尿烷粉、硅酮粉、聚甲基丙烯酸甲酯粉、纤维素粉、淀粉、硅氧烷弹性体球形粉和聚乙烯粉;有色颜料例如黄氧化铁、红氧化铁、黑氧化铁、氧化铬、碳黑、佛青和铁蓝;白色颜料例如氧化锌、二氧化钛和二氧化铈;体质色素例如滑石、云母、绢云母、高岭土和板状硫酸钡;珍珠颜料例如云母钛;金属盐例如硫酸钡、碳酸钙、碳酸镁、硅酸铝和硅酸镁;无机粉末例如二氧化硅和氧化铝;金属皂例如硬脂酸铝、硬脂酸镁、棕榈酸锌、肉豆蔻酸锌、肉豆蔻酸镁、月桂酸锌和十一碳烯酸锌;膨润土;绿土;和氮化硼。这些粉末的形状(例如球状、棒状、针状、板状、无定形、鳞状、梭状)和粒径没有特别限制。
可以任选将这些粉末用公知的表面处理方法进行处理,例如氟化合物处理、硅氧烷处理、硅酮树脂处理、悬垂处理(pendent treatment)、盐水偶联剂处理、钛偶联剂处理、润滑剂处理、N-酰化赖氨酸处理、聚丙烯酸处理、金属皂处理、氨基酸处理、卵磷脂处理、无机化合物处理、血浆处理和机械化学处理。
(6)表面活性剂的具体实例
阴离子表面活性剂
脂肪酸皂、α-酰基磺酸盐、烷基磺酸盐、烷基烯丙基磺酸盐、烷基萘磺酸盐、烷基硫酸盐、POE烷基醚硫酸盐、烷基酰胺硫酸盐、烷基磷酸盐、POE烷基磷酸盐、烷基酰胺磷酸盐、烷酰基烷基牛磺酸盐、N-酰基氨基酸盐、POE烷基醚碳酸盐、烷基磺基琥珀酸盐、烷基磺基乙酸钠、酰化水解的胶原肽盐和全氟代烷基磷酸酯。
阳离子表面活性剂
烷基三甲基氯化铵、硬脂酰三甲基氯化铵、硬脂酰三甲基溴化铵、鲸蜡硬脂酰三甲基氯化铵、二硬脂酰二甲基氯化铵、硬脂酰二甲基苄基氯化铵、山嵛基三甲基溴化铵、苯扎氯铵、山嵛酸酰氨基丙基二甲基羟丙基氯化铵、二乙氨基乙基酰胺硬脂酸盐、二甲氨基乙基酰胺硬脂酸盐、二甲氨基丙基酰胺硬脂酸盐和羊毛脂衍生物季铵盐。
两性表面活性剂
羧基内铵盐型、酰氨基内铵盐型、磺基内铵盐型、羟基磺基内铵盐型、酰氨基磺基内铵盐型、二氧磷基内铵盐(phosphobetaine)型、氨基羧酸盐型、咪唑啉衍生物型和酰氨基胺型。
非离子表面活性剂
丙二醇脂肪酸酯、甘油脂肪酸酯、聚甘油脂肪酸酯、脱水山梨糖醇脂肪酸酯、POE脱水山梨糖醇脂肪酸酯、POE山梨糖醇脂肪酸酯、POE甘油脂肪酸酯、POE烷基醚、POE脂肪酸酯、POE氢化蓖麻油、POE蓖麻油、POE-POP共聚物、POE-POP烷基醚、聚醚修饰的硅氧烷月桂酸烷醇酰胺、烷基胺氧化物(alkylamine oxide)和氢化大豆磷脂。
天然型表面活性剂
卵磷脂、皂角苷和糖型表面活性剂。
(7)多元醇与糖的具体实例
乙二醇、二甘醇、聚乙二醇、丙二醇、双丙甘醇、聚丙二醇、甘油、双甘油、聚甘油、3-甲基-1,3-丁二醇、1,3-丁二醇、山梨糖醇、甘露糖醇、棉子糖、赤藓糖、葡萄糖、蔗糖、果糖、木糖醇、乳糖、麦芽糖、麦芽糖醇、海藻糖、烷基化海藻糖、混合型异构化糖、硫酸海藻糖和支链淀粉。还可以使用它们的化学修饰产物。
(8)聚合物化合物的具体实例
阴离子聚合物化合物例如丙烯酸酯/甲基丙烯酸酯共聚物(PLUS-SIZE,Go′o Kagaku K.K.生产)、乙酸乙烯酯/巴豆酸共聚物(Resin 28-1310,NSC生产)、乙酸乙烯酯/巴豆酸/新癸酸乙烯酯共聚物(28-2930,NSC生产)、甲基乙烯基醚马来酸半酯(GANTREZ ES,ISP生产)、丙烯酸叔丁酯/丙烯酸乙酯/甲基丙烯酸共聚物(RUBIMER,BASF生产)、乙烯基吡咯烷酮/乙酸乙烯酯/丙酸乙烯酯共聚物(RUBISCOL VAP,BASF生产)、乙酸乙烯酯/巴豆酸共聚物(RUBISET CA,BASF生产)、乙酸乙烯酯/巴豆酸/乙烯基吡咯烷酮共聚物(RUBISET CAP,BASF生产)、乙烯基吡咯烷酮/丙烯酸酯共聚物(RUBIFLEX,BASF生产)、丙烯酸酯/丙烯酰胺共聚物(ULTRAHOLD,BASF)、乙酸乙烯酯/马来酸丁酯-丙烯酸冰片酯共聚物(ADVANTAGE,ISP生产)、羧基乙烯基聚合物(CARBOPOL,BF Goodrich生产)和丙烯酸-甲基丙烯酸烷基酯共聚物(PAMUREN,BF Goodrich生产);两性聚合物化合物例如甲基丙烯酸二烷基氨基乙基酯聚合物(YUKAFORMER,MitsubishiChemical生产)和辛基丙烯酰胺丙烯酸酯/丙烯酸羟丙酯/甲基丙烯酸丁氨基乙基酯共聚物(AMPHOMER,NSC生产)的乙酸两性化合物;阳离子聚合物化合物例如乙烯基吡咯烷酮/甲基丙烯酸二甲氨基乙基酯的季铵化化合物(GAFQUAT,ISP生产)和甲基乙烯基氯化咪唑鎓/乙烯基吡咯烷酮共聚物(RUBICOTE,BASF生产);和非离子聚合物化合物例如聚乙烯基吡咯烷酮/乙酸乙烯酯共聚物(RUBISCOL VA,BASF生产)和乙烯基吡咯烷酮/甲基丙烯酸二甲氨基乙基酯共聚物(Copolymer VC713,ISP生产)。
另外,还可以适当地使用天然来源的聚合物化合物,例如纤维素及其衍生物、藻酸钙、支链淀粉、琼脂、明胶、罗望子多糖、黄原酸胶、角叉菜胶、高甲氧基果胶、低甲氧基果胶、瓜尔胶、阿拉伯胶、结晶纤维素、阿拉伯半乳聚糖、刺梧桐树胶、黄蓍胶、藻酸、白蛋白、酪蛋白、cardrun、吉兰胶(gellan gum)和葡聚糖。
(9)生物活性成分的具体实例
生物活性成分可以包括这样的物质,当这样一种物质应用于皮肤时,能够为皮肤带来一定的生物活性。其具体实例可以包括增白成分、抗炎剂、抗老化剂、紫外防护剂、减肥剂、紧肤剂、抗氧化剂、头发修补剂、生发剂、保湿剂、血液循环促进剂、抗菌剂、杀菌剂、干燥剂、冷却剂、保温剂、维生素化合物、氨基酸、伤口愈合促进剂、缓和剂(torpent)、止痛剂、细胞活化剂和酶成分。
掺入其中的成分的适合实例可以包括当归(angelica)提取物、鳄梨提取物、绣球花(hydrangea)提取物、蜀葵(althea)提取物、山金车花(arnica)提取物、芦荟(aloe)提取物、杏提取物、杏核提取物、银杏提取物、茴香提取物、姜黄(tumeric)提取物、乌龙荼提取物、蔷薇果实提取物、松果菊(echinacea)叶提取物、黄芩(scutellaria)根提取物、黄柏树(phellodendron)皮提取物、黄连提取物、大麦提取物、金丝桃(hypericum)提取物、白荨麻(white nettle)提取物、水田芥提取物、柑橘提取物、海盐、海草提取物、水解弹性蛋白、水解小麦粉、水解蚕丝、春黄菊(chamomile)提取物、胡萝卜提取物、菌陈蒿(artemisia capillaris)提取物、甘草提取物、玫瑰茄(sabdariffa)提取物、火棘(pyracantha fortuneana)果实提取物、猕猴桃(kiwi)提取物、金鸡纳(cinchona)树皮提取物、黄瓜提取物、鸟苷、栀子提取物、维奇氏箬竹(sasa albo-marginata)提取物、槐树(sophora)根提取物、胡桃提取物、葡萄柚提取物、铁线莲(clematis)提取物、小球藻(chlorella)提取物、桑树皮提取物、龙胆(gentian)提取物、红茶提取物、酵母提取物、牛蒡(burdock)提取物、发酵米糠提取物、米胚油、紫草(comfrey)提取物、胶原、越桔提取物、细辛(asiasarum)根提取物、柴胡(bupleurum falcatum)根提取物、脐带提取物、鼠尾草(salvia)提取物、肥皂草(saponaria)提取物、竹草提取物、山楂(crataegus)提取物、花椒(zanthoxylum)果实提取物、什塔克菇(shiitake mushroom)提取物、地黄(rehmannia)根提取物、紫草(lithospermum)根提取物、紫苏(perilla)提取物、椴树提取物、蚊子草(filipendula)提取物、芍药根提取物、菖蒲根茎(calamus rhizome)提取物、桦树提取物、马尾提取物、常春藤(ivy)提取物、山楂(hawthorn)提取物、西洋接骨木(sambucus nigra)提取物、蓍草(yarrow)提取物、胡椒薄荷提取物、鼠尾草(sage)提取物、锦葵(mallow)提取物、蛇床根茎(cnidium rhizome)提取物、獐牙菜(swertia herb)提取物、大豆提取物、枣提取物、野百里香(wild thyme)提取物、绿茶提取物、丁香提取物、白茅(cogon)提取物、温州蜜柑(citrus unshiu)皮提取物、当归根提取物、金盏花(calendula)提取物、桃仁提取物、苦橙提取物、蕺菜(houttuynia)提取物、番茄提取物、纳豆(natto)提取物、人参提取物、大蒜提取物、野蔷薇提取物、玫瑰茄(hibiscussabdariffa)花提取物、麦冬(ophiopogon)块茎提取物、欧芹(parsley)提取物、蜂蜜、金缕梅(witch-hazel)提取物、墙草(pellitory)提取物、isodonis提取物、母菊(matricaria)提取物、枇杷提取物、款冬(coltsfoot)提取物、蜂豆菜(butterbur)柄节提取物、茯苓(poria cocos)提取物、假叶树(butcher bloom)提取物、葡萄提取物、蜂胶、丝瓜(luffa)提取物、红花(safflower)提取物、胡椒薄荷提取物、椴树提取物、芍药提取物、啤酒花(hop)提取物、松树提取物、七叶树(horse-chestnut)提取物、臭菘(skunk cabbage)提取物、无患子科(sapindaceae)提取物、香薄荷(balm mint)提取物、桃提取物、矢车菊(cornflower)提取物、桉树(eucalyptus)提取物、虎耳草(saxifrage)提取物、柑桔(citrus)提取物、薏苡(coix)仁提取物、艾蒿(mugwort)提取物、薰衣草(1avender)提取物、苹果提取物、莴苣(lettuce)提取物、柠檬提取物、华黄芪(Chinese milkvetch)提取物、蔷薇提取物、迷迭香提取物、白花春黄菊(Roman chamomile)提取物和蜂王浆提取物。
其他实例可以包括生物聚合物,例如脱氧核糖核酸、粘多糖、透明质酸钠、硫酸软骨素钠、胶原、弹性蛋白、甲壳质、壳聚糖和水解蛋壳膜;保湿成分,例如氨基酸、水解肽、乳酸钠、脲、吡咯烷酮羧酸钠、甜菜碱、乳清和三甲基甘氨酸;油性成分,例如鞘脂、神经酰胺、植物鞘氨醇、胆甾醇、胆甾醇衍生物和磷脂;抗炎剂,例如ε-氨基己酸、甘草酸、甘草次酸、氯化溶菌酶、愈创
(guaiazlene)和氢化可的松;维生素,例如维生素A、维生素B2、维生素B6、维生素D、维生素E、泛酸钙、生物素和烟酸酰胺;活性成分,例如尿囊素、二异丙胺二氯乙酸盐和4-氨甲基环己烷羧酸;抗氧化剂,例如生育酚、类胡萝卜素、类黄酮、鞣酸、木质素和皂角苷;细胞活化剂,例如α-羟基酸和β-羟基酸;血液循环促进剂,例如阿魏酸酯(γ-orizanol)和维生素E衍生物;伤口愈合剂,例如视黄醇和视黄醇衍生物;增白剂,例如白蛋白、曲酸、胎盘提取物、硫磺、鞣花酸、亚油酸、氨甲环酸和谷胱甘肽;和生发剂,例如头花千金藤碱、甘草提取物、辣椒酊、扁柏酚、碘化大蒜提取物、盐酸吡哆醇、DL-α-生育酚、DL-α-生育酚乙酸酯、烟酸、烟酸衍生物、泛酸钙、D-泛醇、乙酰基泛酰乙基醚、生物素、尿囊素、异丙基甲基苯酚、雌二醇、乙炔雌二醇、氯化镱(caproniumchloride)、苯扎氯铵、盐酸苯海拉明、Takanal、樟脑、水杨酸、香草基酰胺壬酸酯(nonylate)、香草基酰胺壬酸酯(nonanoate)、Pyroctone Olamine、甘油十五烷酸酯、L-薄荷醇、单硝基愈创木酚、间苯二酚、γ-氨基丁酸、氯化苄乙铵、盐酸美西律、生长素、雌性激素、斑蝥酊、环孢菌素、吡硫锌、氢化可的松、米诺地尔、聚氧乙烯脱水山梨糖醇单硬脂酸酯、薄荷油和SADANISHIKI提取物。
(10)抗氧化剂的具体实例
亚硫酸氢钠、亚硫酸钠、赤藻糖酸、赤藻糖酸钠、硫代二丙酸二月桂酯、生育酚、甲苯双胍、去甲二氢愈创木酸、对羟基茴香醚、丁羟基茴香醚、二丁羟基甲苯、硬脂酸抗坏血酸酯、棕榈酸抗坏血酸酯、没食子酸辛酯、没食子酸丙酯、类胡萝卜素、类黄酮、鞣酸、木质素、皂角苷和具有抗氧化作用的植物提取物,例如苹果提取物和丁香提取物。
(11)溶剂的具体实例
净化水、乙醇、低级醇、醚、LPG、碳氟化合物、N-甲基吡咯烷酮、氟代醇、挥发性直链硅氧烷和下一代氟利昂(fleon)(例如碳氟化合物、氯氟碳化合物CFC)。
美容组合物
根据本发明的美容组合物可以进一步含有一般浓度的现有或已知乳化剂等。
皮肤用药
根据本发明的外用皮肤用药还可以作为美容材料使用,例如皮肤乳剂、皮肤霜剂、底霜、按摩霜、清洁霜、剃须霜、清洁泡沫、皮肤洗剂、洗剂、药包(pack)、香波、润丝、生发剂、养发剂、染发剂、护发剂、洁齿剂、含漱剂、永久烫发剂(permanent waving agent)、软膏、浴用配制品和浴皂。
美容材料
将根据本发明的外用皮肤用药与例如下列成分掺合,可以得到美容材料:醇,例如乙醇或丙二醇;防腐剂,例如对-羟基苯甲酸甲酯、对-羟基苯甲酸乙酯、对-羟基苯甲酸丁酯或对-羟基苯甲酸丙酯;和净化水。不过,美容材料并不特别限于这些具体实例。
根据本发明的美容材料分为例如下列种类:化妆品,例如粉底、扑面粉、眼影、眼线、眉笔、腮红、唇膏和指甲油;基础美容品,例如乳状洗液、霜剂、洗剂、炉甘石洗剂、防晒剂、晒黑剂(suntan agent)、剃须后洗剂、剃须前洗剂、药包、痤疮对抗用品和香精剂;头发护理美容品,例如香波、润丝、调理剂、染发剂、头发滋养剂、头发固定剂、养发剂和永久烫发剂;体用粉剂、除臭剂、脱毛剂、香皂、体用香波、浴用配制品、洗手皂和香水。本发明可以作为各美容材料使用。
根据本发明的美容材料的形状或形式没有特别限制。美容材料可以具有公知的形状或形式,例如双层结构、油包水型乳剂、水包油型乳剂、凝胶、喷雾剂、摩丝、油剂、固体、面膜(sheet)和粉剂。
抗坏血酸衍生物的用途
根据本发明的抗坏血酸衍生物可以用作医学或药学制剂、农业化学制剂、动物药物制剂、食品添加剂和饲料添加剂。抗坏血酸衍生物的含量可以因用途而异,因此不能普遍地指定。不过,可以根据目的和用途适当地增加或减少用量。可以按照下列规范适当地调整所需用量,以抗坏血酸计:药事法、农药管理法、动物药管理规范和食品管理法。
[实施例]
下面参照实施例详细描述本发明。不过,本发明并不限于这些实施例。
<实施例A-1>
L-抗坏血酸-2-磷酸-6-(2’-己基癸酸酯)钠盐
在40℃下,将131mmol(35g)2-己基癸酸溶于500g 95%硫酸。向所得溶液加入146mmol(50g)L-抗坏血酸-2-磷酸酯钠盐并均匀搅拌6小时。将所得混合物在室温下放置24小时,然后将反应混合物倒入780g冰水中,所得沉淀用590g甲基叔丁基醚萃取。向所得醚溶液加入590g 13%盐水,然后加入20%氢氧化钠水溶液,直至混合物的pH变为约8。借助分液漏斗分离甲基叔丁基醚层,向甲基叔丁基醚层加入300g甲醇,由此沉淀沉积下来。离心分离该沉淀,用少量甲醇洗涤,然后在减压下干燥,得到21g L-抗坏血酸-2-磷酸-6-(2’-己基癸酸酯)钠盐,为粉末形式(产率:27%)。
借助核磁共振光谱鉴别结构。
1H NMR(270MHz,D2O;1H NMR仪器,牌号:JNM-EX270,NihonDenshi K.K.(JEOL Ltd.)制造)δ:0.89ppm(t,6H,J=6.6Hz),1.30-1.63(b,24H),2.45(hep,1H,J=6.6Hz),4.20-4.35(m,3H),4.47(s,1H)
13C NMR(67.8MHz,D2O;13C NMR仪器,牌号:JNM-EX270,NihonDenshi K.K.制造)δ:16.4ppm(s,1C),25.0(s,1C),25.2(s,1C),29.4(s,1C),29.6(s,1C),31.5(s,1C),31.9(s,1C),32.1(s,1C),34.0(s,1C),34.5(s,1C),47.6(s,1C),67.6(s,1C),69.6(s,1C),80.8(s,1C),115.3(d,1C,J=7.3Hz),178.2(s,1C),179.4(s,1C),180.4(s,1C)
31P NMR(109MHz,D2O;31P NMR仪器,牌号:JNM-EX270,NihonDenshi K.K.制造)δ:4.3ppm
<实施例A-2>
L-抗坏血酸-2-磷酸-6-(2′-正庚基十一烷酸酯)钠盐
重复与实施例A-1相同的工艺,但使用根据本发明的2-正庚基十一烷酸代替实施例A-1所用2-己基癸酸,得到16g L-抗坏血酸-2-磷酸-6-(2′-正庚基十一烷酸酯)钠盐,为粉末形式(产率:26%)。
借助核磁共振光谱鉴别结构。
1H NMR(270MHz,D2O)δ:0.89 ppm(t,6H,J=6.6Hz),1.30-1.63(b,24H),2.43(hep,1H,J=6.3Hz),4.18-4.36(m,3H),4.57(s,1H)
13C NMR(67.8MHz,D2O)δ:16.5ppm(s,1C),25.2(s,1C),25.3(s,1C),29.5(s,1C),29.6(s,1C),31.6(s,1C),31.9(s,1C),32.1(s,1C),32.3(s,1C),33.9(s,1C),34.4(s,1C),34.6(s,1C),47.5(s,1C),67.2(s,1C),69.4(s,1C),80.3(s,1C),115.8(d,1C,J=6.1 Hz),173.8(s,1C),178.3(d,1C,J=3.7 Hz),179.9(s,1C)
31P NMR(109MHz,D2O)δ:4.1ppm
<试验例A-1>
将实施例A-1所得L-抗坏血酸-2-磷酸-6-(2′-己基癸酸酯)钠盐溶于净化水,至浓度为2质量%,将所得溶液装入带盖玻璃瓶中并在40℃下(在遮光条件下)放置10天。利用配备有Shodex(Showa Denko K.K.注册商标)SB802.5 HQ(Showa Denko K.K.制造)柱的高效液相色谱仪分析贮存后剩余化合物的比例。
高效液相色谱的测量条件
柱子:Shodex(Showa Denko K.K.注册商标)OHpak SB802.5 HQ
温度:40℃
洗脱剂:0.03M Na2SO4+0.03M H3PO4/四氢呋喃=1∶2
流速:0.5ml/min
注射量:20μL
检测:UV 270nm
<试验例A-2>
按照与实施例A-1相同的方式进行稳定性试验,但使用实施例A-2所得的L-抗坏血酸-2-磷酸-6-(2′-正庚基十一烷酸酯)钠盐代替实施例A-1所得的L-抗坏血酸-2-磷酸-6-(2′-己基癸酸酯)钠盐。
<对比例A-1>
按照与实施例A-1相同的方式进行稳定性试验,但使用如前述专利文献5(JP-A-10-298174)所述工艺制备的L-抗坏血酸-2-磷酸-6-棕榈酸酯钠盐代替实施例A-1所得的L-抗坏血酸-2-磷酸-6-(2′-己基癸酸酯)钠盐。
<对比例A-2>
按照与实施例A-1相同的方式进行稳定性试验,但使用具有优异稳定性的L-抗坏血酸-2-磷酸酯钠盐(Showa Denko K.K.制造)代替实施例A-1所得的L-抗坏血酸-2-磷酸-6-(2′-己基癸酸酯)钠盐。
上述实施例、对比例和试验例所得结果一起如下表1所示。
[表1]
抗坏血酸衍生物 | 残留比例(%) | |
实施例A-1 | L-抗坏血酸-2-磷酸-6-(2′-己基癸酸酯)钠盐 | 95.3 |
实施例A-2 | L-抗坏血酸-2-磷酸-6-(2′-正庚基十一烷酸酯)钠盐 | 95.5 |
对比例A-1 | L-抗坏血酸-2-磷酸-6-棕榈酸酯钠盐 | 88.6 |
对比例A-2 | L-抗坏血酸-2-磷酸酯钠盐 | 96.9 |
美容材料的制剂实施例如下所示。这些实施例中,“%”表示质量%。
[制剂实施例A-1]
霜剂(1):
缩合六甘油蓖麻醇酸酯
(condensed hexaglyceryl ricinoleate) 1.0%
细粒二氧化钛 5.0%
新戊酸2-辛基十二醇基酯 8.0%
甘油三(辛酸酯-癸酸酯) 3.0%
聚甲基苯基硅氧烷 7.0%
十甲基环戊硅氧烷 2.0%
鲸蜡醇 2.0%
对-甲氧基肉桂酸2-乙基己基酯 6.0%
4-叔丁基-4-甲氧基苯甲酰基甲烷 2.0%
十甘油单异硬脂酸酯
(decaglyceryl monoisostearate) 3.0%
黄原酸胶 0.3%
L-抗坏血酸-2-磷酸-6-(2’-己基癸酸酯)钠盐 4.0%
净化水,至总量 100%
[制剂实施例A-2]
霜剂(2):
缩合六甘油蓖麻醇酸酯 1.0%
新戊酸2-辛基十二醇酯 8.0%
甘油三(辛酸酯-癸酸酯) 3.0%
聚甲基苯基硅氧烷 7.0%
十甲基环戊硅氧烷 2.0%
鲸蜡醇 2.0%
十甘油单异硬脂酸酯 3.0%
黄原酸胶 0.3%
L-抗坏血酸-2-磷酸-6-(2’-正庚基十一烷酸酯)钠盐 4.0%
净化水,至总量 100%
[制剂实施例A-3]
皮肤洗剂:
L-抗坏血酸-2-磷酸-6-(2’-正庚基十一烷酸酯)钠盐 4.0%
柠檬酸 0.016%
柠檬酸钠 2.0%
1,3-丁二醇 3.0%
乙醇 3.0%
净化水,至总量 100%
制备方法
将上述成分溶于50℃加热下的净化水中,在搅拌下冷却所得溶液。然后当温度变为30℃时停止搅拌,所得溶液静置。
[制剂实施例A-4]
乳状洗液:
L-抗坏血酸-2-磷酸-6-(2′-己基癸酸酯)钠盐 4.0%
甘油 8.0%
丁二醇 2.0%
氢化卵磷脂 0.1%
透明质酸钠 0.05%
羟乙基纤维素 0.3%
黄原酸胶 0.3%
柠檬酸钠 1.0%
聚乙二醇-50氢化蓖麻油 0.5%
对羟基苯甲酸甲酯 0.2%
净化水,至总量 100%
制备方法
将上述除L-抗坏血酸-2-磷酸-6-(2′-己基癸酸酯)钠盐以外的成分溶于80℃加热下的净化水中,在搅拌下冷却所得溶液。然后在50℃、搅拌下向所得溶液逐渐加入L-抗坏血酸-2-磷酸-6-(2′-己基癸酸酯)钠盐,当温度变为40至35℃时停止搅拌,并将所得溶液静置。
[实施例B-1]
向人皮肤组织三维模型(商标:TESTSKIN LSD-d,Toyobo Co.,Ltd.制造)表面施用将每种供试物质(1)至(3)溶于Dulbecco PBS(-)所得40μL溶液,在5%CO2存在下将所得皮肤组织模型在37℃下培养两小时。然后,吸除供试溶液,随后在5%CO2存在下将皮肤组织模型在37℃下分别培养2、6和12小时。
将在每一培养时间取样的每部分皮肤模型用Dulbecco PBS(-)洗涤,利用直径6mm的冲头在表面部分打孔,在HEPES缓冲溶液(pH 7.2)中均质化,得到匀化物。使用所得匀化物,利用高效液相色谱定量分析皮肤模型中所含有的抗坏血酸的量。利用Lowry法定量分析皮肤模型中的蛋白质含量。
1)2%抗坏血酸-2-磷酸酯钠盐
2)0.5%抗坏血酸-2-磷酸-6-(2′-己基癸酸酯)钠盐
3)0.5%抗坏血酸-2-磷酸-6-(2′-正庚基十一烷酸酯)钠盐
高效液相色谱的测量条件
<抗坏血酸>
柱子:Shodex(Showa Denko K.K.注册商标)Asahipak NH2P-50 4E
温度:40℃
洗脱剂:乙腈∶60mM H3PO4=80∶20
流速:0.8ml/min
检测:UV 245nm
每一培养时间时的抗坏血酸量结果(单位:nmol/mg皮肤蛋白质)。
培养后2小时 培养后6小时 培养后12小时
1) 30 24 5
2) 6 10 23
3) 5 11 26
如上结果所示,发现当将抗坏血酸-2-磷酸-6-(2′-己基癸酸酯)钠盐或0.5%抗坏血酸-2-磷酸-6-(2′-正庚基十一烷酸酯)钠盐施用于皮肤模型,能够容易地有效增强组织中的抗坏血酸浓度,以提供施用后较长的时间的有效促进胶原合成的浓度。
[实施例B-2]
利用带有切开(或切割)伤口的豚鼠模型系统比较下列1)至3)供试物质之间的胶原合成促进效果。用于溶解每种供试物质的基质材料是含有20%乙醇和3%丙二醇的净化水。
1)2%抗坏血酸-2-磷酸酯钠盐
2)1%抗坏血酸-2-磷酸-6-(2′-己基癸酸酯)钠盐
3)1%抗坏血酸-2-磷酸-6-(2′-正庚基十一烷酸酯)钠盐
本实验中,利用解剖刀在豚鼠背部切开两条伤口,各长2cm,以使所切开的伤口相对于背部中心是对称的。然后,向其施用0.2ml供试物质溶液,每天两次达四天。最后一次施用结束后,从豚鼠背部手术取下一片2cm× 2cm皮肤(正方形),以使所切开的伤口部分基本上位于皮肤片的中心。然后,测量脱离所切开伤口表面所需的张力。对于每种供试物质使用五只豚鼠。
在测量上述张力之后,从皮肤片上取一段皮肤,以使所切开的伤口部分包含在该皮肤段中,在所切开的伤口部分两侧具有5mm的宽度(即所得皮肤段的总宽度为10mm)。将所得皮肤段在0.5M乙酸中均质化,得到匀化物。向一体积份匀化物溶液加入两体积份二乙醚-乙醇混合物(体积比=1∶3),在搅拌下混合,离心后从中除去溶剂层。向所得溶剂层加入胃蛋白酶(Wako Pure Chemical Industries,Ltd.生产),与溶剂层在15℃下反应16小时。离心分离后,将所得上清液冷冻干燥。将所得皮肤样本的蛋白质成分用盐酸水解,利用AccQ-Tag氨基酸分析仪(Waters Co.制造)进行氨基酸分析。
已施用每种供试物质的所切开伤口部分的脱离张力测量结果及其羟脯氨酸含量如下。这里,羟脯氨酸是能够作为胶原指示物的物质。
脱离张力(g/cm) 羟脯氨酸含量(nmol/皮肤湿重)
1) 123 32.1
2) 181 38.5
3) 187 37.6
如上结果所示,发现施用每种抗坏血酸-2-磷酸-6-(2′-己基癸酸酯)钠盐或抗坏血酸-2-磷酸-6-(2′-正庚基十一烷酸酯)钠盐具有促进胶原合成的效果,从而促进所切开伤口表面的复原。
[制剂实施例B-1]
皮肤洗剂:
抗坏血酸-2-磷酸-6-(2′-己基癸酸酯)钠盐 2.0%
柠檬酸 0.016%
柠檬酸钠 2.0%
1,3-丁二醇 3.0%
乙醇 3.0%
净化水,至总量 100%
制备方法
将上述成分溶于50℃温热下的净化水中,在搅拌下冷却所得混合物。当混合物的温度变为30℃时,停止搅拌,并将混合物静置。
[制剂实施例B-2]
皮肤洗剂:
抗坏血酸-2-磷酸-6-(2′-正庚基十一烷酸酯)钠盐 2.0%
柠檬酸 0.016%
柠檬酸钠 2.0%
1,3-丁二醇 3.0%
乙醇 3.0%
净化水,至总量 100%
制备方法
将上述成分溶于50℃温热下的净化水,在搅拌下冷却所得混合物。当混合物的温度变为30℃时,停止搅拌,并将混合物静置。
[制剂实施例B-3]
霜剂:
抗坏血酸-2-磷酸-6-(2′-己基癸酸酯)钠盐 2.0%
鲸蜡醇 5.0%
环甲基硅酮 4.0%
辛酸鲸蜡酯 4.0%
trioctanion 2.0%
棕榈醇 1.0%
二甲基硅氧烷 0.3%
丁二醇 7.0%
氢化卵磷脂 1.0%
肉豆蔻酸聚甘油-10
(myristic acid poly glyceryl-10) 1.0%
柠檬酸钠 2.0%
对羟基苯甲酸甲酯 0.15%
对羟基苯甲酸丙酯 0.05%
黄原酸胶 0.1%
净化水,至总量 100%
制备方法
将上述成分(抗坏血酸-2-磷酸-6-(2′-己基癸酸酯)钠盐除外)溶于80℃加热下的净化水中,在搅拌下冷却所得混合物。在50℃下,向该混合物逐渐加入抗坏血酸-2-磷酸-6-(2′-己基癸酸酯)钠盐。当混合物的温度变为35-30℃时,停止搅拌,并将混合物静置。
[制剂实施例B-4]
霜剂:
抗坏血酸-2-磷酸-6-(2′-正庚基十一烷酸酯)钠盐 2.0%
鲸蜡醇 5.0%
环甲基硅酮 4.0%
辛酸鲸蜡酯 4.0%
trioctanion 2.0%
棕榈醇 1.0%
二甲基硅氧烷 0.3%
丁二醇 7.0%
氢化卵磷脂 1.0%
肉豆蔻酸聚甘油-10 1.0%
柠檬酸钠 2.0%
对羟基苯甲酸甲酯 0.15%
对羟基苯甲酸丙酯 0.05%
黄原酸胶 0.1%
净化水,至总量 100%
制备方法
将上述成分(抗坏血酸-2-磷酸-6-(2′-正庚基十一烷酸酯)钠盐除外)溶于80℃温热下的净化水中,在搅拌下冷却所得混合物。在50℃下,向该混合物逐渐加入抗坏血酸-2-磷酸-6-(2′-正庚基十一烷酸酯)钠盐。当混合物的温度变为35-30℃时,停止搅拌,并将混合物静置。
[制剂实施例B-5]
乳状洗液:
L-抗坏血酸-2-磷酸-6-(2′-己基癸酸酯)钠盐 2.0%
甘油 8.0%
丁二醇 2.0%
氢化卵磷脂 0.1%
透明质酸钠 0.05%
羟乙基纤维素 0.3%
黄原酸胶 0.3%
柠檬酸钠 1.0%
聚乙二醇-50氢化蓖麻油 0.5%
对羟基苯甲酸甲酯 0.2%
净化水,至总量 100%
制备方法
将上述除L-抗坏血酸-2-磷酸-6-(2′-己基癸酸酯)钠盐以外的成分溶于80℃加热下的净化水中,在搅拌下冷却所得溶液。然后在50℃、搅拌下,向所得溶液逐渐加入L-抗坏血酸-2-磷酸-6-(2′-己基癸酸酯)钠盐,当温度变为40至35℃时,停止搅拌,并将所得溶液静置。
[制剂实施例B-6]
L-抗坏血酸-2-磷酸-6-(2′-庚基十一烷酸酯)钠盐 2.0%
甘油 8.0%
丁二醇 2.0%
氢化卵磷脂 0.1%
透明质酸钠 0.05%
羟乙基纤维素 0.3%
黄原酸胶 0.3%
柠檬酸钠 1.0%
聚乙二醇-50氢化蓖麻油 0.5%
对羟基苯甲酸甲酯 0.2%
净化水,至总量 100%
制备方法
将上述除L-抗坏血酸-2-磷酸-6-(2′-庚基十一烷酸酯)钠盐以外的成分溶于80℃加热下的净化水中,在搅拌下冷却所得溶液。然后在50℃、搅拌下,向所得溶液逐渐加入L-抗坏血酸-2-磷酸-6-(2′-庚基十一烷酸酯)钠盐,当温度变为40至35℃时,停止搅拌,并将所得溶液静置。
实施例C-1(增白)
以下实施例的组合物中的含量以质量%(wt.%)描述。
洗剂(1):
将下列成分1)至4)彼此均匀分散并溶解,以提供下列最终浓度。在搅拌下将所得混合物加入到成分5)中,得到洗剂(1)。
1)抗坏血酸-2-磷酸-6-(2′-己基癸酸酯)钠盐 2.00
2)乙醇 5.00
3)丙二醇 5.00
4)对-羟基苯甲酸甲酯 0.20
5)净化水 87.8
洗剂(2)至(4)
按照与制备洗剂(1)相同的方式制备洗剂(2)至(4),但分别使用每种下列成分代替洗剂(1)的成分1),以提供相同的浓度。
洗剂(2):
抗坏血酸-2-磷酸-6-(2′-正庚基十一烷酸酯)钠盐
洗剂(3)(对对比对照参照):
抗坏血酸-2-磷酸钠盐
洗剂(4)(阴性对照):
净化水
在每种上述洗剂中,将各成分均匀溶解,随着时间的推移,全部洗剂显示良好的稳定性。
实施例C-2
洗剂(5)
将下列成分1)至4)彼此均匀分散并溶解,以提供下列最终浓度。在搅拌下将所得混合物加入到成分5)中,得到洗剂(5)。
1)抗坏血酸-2-磷酸-6-(2′-己基癸酸酯)钠盐 0.10
2)乙醇 5.00
3)丙二醇 5.00
4)对-羟基苯甲酸甲酯 0.20
5)净化水 89.7
洗剂(6)至(8)
按照与制备洗剂(5)相同的方式制备洗剂(6)至(8),但分别使用每种下列成分代替洗剂(5)的成分1),以提供相同的浓度。
洗剂(6):
抗坏血酸-2-磷酸-6-(2′-正庚基十一烷酸酯)钠盐
洗剂(7)(对比对照参照):
抗坏血酸-2-磷酸钠盐
洗剂(8)(阴性对照):
净化水
在每种上述洗剂中,将各成分均匀溶解,随着时间的推移,全部洗剂显示良好的稳定性。
实施例C-3
外用凝胶型制剂(1)
将下列成分1)均匀分散在下列成分2)中,以提供下列最终浓度,在搅拌下将所得混合物加入到成分3)中,得到预期的凝胶型外用制剂(1)。
1)抗坏血酸-2-磷酸-6-(2′-己基癸酸酯)钠盐 10
2)甘油 20
3)肉豆蔻酸辛基十二醇酯 70
外用凝胶型制剂(2)至(4)
按照与制备凝胶型外用制剂(1)相同的方式制备凝胶型外用制剂(2)至(4),但分别使用下列每种成分代替凝胶型制剂(1)的成分1),以提供相同的浓度。
凝胶型制剂(2):
抗坏血酸-2-磷酸-6-(2′-正庚基十一烷酸酯)钠盐
凝胶型制剂(3)(对比对照参照):
抗坏血酸-2-磷酸钠盐
凝胶型制剂(4)(阴性对照):
净化水
在每种上述凝胶型外用制剂中,将各成分均匀溶解,随着时间的推移,全部凝胶型外用制剂显示良好的稳定性。
实施例C-4
预防色素沉着的效果
利用电动毛发剪(0.05mm刀片)将30只七周龄雄性Wizer-Maple豚鼠(WM,SPF)的每只背部完整表面的毛发修剪整齐,然后利用电动剃刀剃去表面毛发。然后,向背部表面覆盖可伸展的胶布绷带(Silky-tex,其外部覆盖有铝箔),绷带具有四个开口窗,每个窗口的尺寸为1.5cm×1.5cm。对于各个窗口,向十个部位先后施用实施例C-1至C-3所制备的每种洗剂(1)至(8)和凝胶型外用制剂(1)至(4),各自用量为0.05ml。制剂施用四小时后,利用浸有水的吸水棉洗涤用药部位,然后干燥。然后,将每只动物固定在固定装置上,利用紫外线照射装置(Shinano Seisakusho,ToshibaFL40S/E30-型荧光灯,配备有六个SE灯)向各个部位照射中等波长紫外线(UVB),照射暴露量为300mJ/cm2,距离为约10cm。照射后,向相应的部位再次施用各同一洗剂(1)至(8)和凝胶型外用制剂(1)至(4),各自用量为0.05ml。
将这些步骤重复三天。最后一次照射14天后,按照下列接纳标准测定所致色素沉着(或着色)的程度,以得分计。进而,利用色差计(MINOLTA,CR-20)测定每一用药/照射部位四角与中心部分(总共五个部位)的皮肤亮度。对于每种制剂,从得分平均值(每种制剂的十个数据)和亮度平均值(每种制剂的50个数据)判断预防色素沉着的效果。
色素沉着的接纳标准
没有色素沉着:0(零)分
轻微的色素沉着:1分
低度的色素沉着:2分
中度的色素沉着:3分
高度的色素沉着:4分
结果(平均)
制剂
得分
亮度
洗剂(1) 0.8 63.0
洗剂(2) 1.0 61.1
洗剂(3) 2.1 61.8
洗剂(4) 3.0 59.5
洗剂(5) 2.0 61.7
洗剂(6) 2.2 62.1
洗剂(7) 3.0 59.9
洗剂(8) 3.0 60.1
凝胶型外用制剂(1) 0.5 63.5
凝胶型外用制剂(2) 0.8 62.8
凝胶型外用制剂(3) 1.2 62.1
凝胶型外用制剂(4) 3.0 59.9
如上所述,发现任意含有根据本发明的抗坏血酸衍生物的洗剂和凝胶型外用制剂均显示优异的预防色素沉着的效果。
实施例C-5
除去色素沉着的效果
利用电动毛发剪(0.05mm刀片)将30只六周龄雄性Wizer-Maple豚鼠(WM,SPF)每只背部完整表面的毛发修剪整齐,然后利用电动剃刀剃去表面毛发。然后,向背部表面覆盖可伸展的胶布绷带(Silky-tex,其外部覆盖有铝箔),绷带具有四个开口窗,每个窗口的尺寸为1.5cm×1.5cm。然后,将每只动物固定在固定装置上,利用紫外线照射装置(Shinano Seisakusho制造,Toshiba FL40S/E30-型荧光灯,配备有六个SE灯)向各个部位照射中等波长紫外线(UVB),照射暴露量为750mJ/cm2,距离为约10cm。在照射后四天至照射后28天的时间里,对于各个窗口,每天两次(早上和晚上)向十个部位先后施用实施例C-1至C-3所制备的每种洗剂(1)至(8)和凝胶型外用制剂(1)至(4),各自用量为0.05ml。最后一次照射28天后,按照接纳标准测定所致色素沉着的程度,以得分计,方式与实施例C-4相同。对于每种制剂,从得分平均值(每种制剂的十个数据)判断除去色素沉着的效果。
结果(平均)
制剂
得分
洗剂(1) 2.2
洗剂(2) 2.4
洗剂(3) 3.3
洗剂(4) 3.5
洗剂(5) 2.9
洗剂(6) 3.0
洗剂(7) 3.5
洗剂(8) 3.8
凝胶型外用制剂(1) 2.2
凝胶型外用制剂(2) 2.5
凝胶型外用制剂(3) 2.9
凝胶型外用制剂(4) 3.5
如上所述,发现任意含有根据本发明的抗坏血酸衍生物的洗剂和凝胶型外用制剂均显示显著的除去色素沉着的效果。
<实施例D-1>
将5kg基础成分进行混合,包含43质量%墨鱼粉、15质量%龙虾(或小虾)粉、10质量%鱼粉、10质量%粗(未精制)鱼油(Nippon Suisan K.K.生产)、10质量%啤酒酵母、3质量%活性谷蛋白、2质量%淀粉、2质量%实施例A-1所制备的抗坏血酸-2-磷酸-6-(2′-己基癸酸酯)钠盐和5质量%矿质混合物。然后调整所得混合物的水分,以提供45%的水分含量。利用挤压机挤出混合物,以提供115℃的产品温度,然后借助干燥机干燥,以提供约10%的水分含量,得到饲料颗粒。
<对比例D-1>
按照与实施例D-1相同的方式制备饲料颗粒,但不使用抗坏血酸-2-磷酸-6-(2′-己基癸酸酯)钠盐。
<对比例D-2,实施例D-3>
使用虹鳟进行饲喂试验。准备20条虹鳟(平均鱼重0.79kg),放养在循环过滤型水罐的两个隔间中,以使每个隔间容纳10条虹鳟。对于这些虹鳟,使用实施例D-1所制备的饲料进行饲喂试验。这里,对于对照实验隔间饲喂对比例D-1所制备的饲料。饲喂期间的水温调节至18℃,饲喂率设置在鱼重的4%。饲喂试验结束后,取出全部十条鱼,测量鱼重。对于试验区域的虹鳟,平均鱼重变为0.85kg,而对照区域的平均鱼重变为0.82kg。
由上述结果确认了根据本发明的抗坏血酸-2-磷酸-6-(2′-己基癸酸酯)钠盐的效果。
<实施例E-1>
将25g蜂蜡(Noda wax Co.,Ltd.生产,熔点60℃)加入到1kg蛋黄卵磷脂(Kewpie Co.,Ltd.生产,牌号″PL-30″,PC含量约25%)中,将所得混合物在约70℃温热下搅拌直至形成均匀的混合物。维持这种条件达五分钟,然后冷却。随后加入25g实施例A-1所制备的抗坏血酸-2-磷酸-6-(2′-己基癸酸酯)钠盐,将所得混合物搅拌直至形成均匀的混合物,得到混合物。另一方面,将2kg明胶、1kg甘油和1.5kg水彼此充分混合,将所得混合物成形为薄片。将两片所形成的明胶片置于旋转型制胶囊机中,向每粒胶囊注入300mg上述混合物。在压力下密封每粒胶囊的注射口,制成3500粒胶囊。
工业实用性
由根据本发明的制备方法所制备的新颖的抗坏血酸衍生物易于结合到细胞中,因此它能够升高抗坏血酸在细胞中的蓄积浓度,即使对细胞少量施用也是如此。另外,与常规抗坏血酸衍生物相比,这种抗坏血酸衍生物的贮存稳定性提高。因此,根据本发明的抗坏血酸衍生物能够被广泛用于各种含有抗坏血酸衍生物作为有效成分的制剂,例如维生素C制剂、外用皮肤制剂、医学或药学制剂、农业化学制剂、动物药物制剂、食品添加剂和饲料添加剂。
另外,当根据本发明的抗坏血酸衍生物被掺入到美容品中用于预防皱纹等时,抗坏血酸衍生物具有优异的促进胶原合成的效果和优异的抑制胶原分解的效果,因此它能够预防或改善皮肤由老化引起的外形或形状的变化。因此,根据本发明的抗坏血酸衍生物可被广泛应用于医学或药学制剂、准药物产品、美容品等。
Claims (19)
2、根据权利要求1的抗坏血酸衍生物,其为一种或多种金属的盐,所述金属选自碱金属、碱土金属、铝、铁、锌和铋。
3、根据权利要求1的抗坏血酸衍生物,其为氨、单乙醇胺、二乙醇胺、三乙醇胺、二环己胺或2-氨基-1-甲基丙醇的盐。
4、根据权利要求1至3任意一项的抗坏血酸衍生物,其中通式(1)中R1和R2的碳原子总数是8至18的整数。
5、根据权利要求4的抗坏血酸衍生物,其中通式(1)中的R1和R2是直链烷基,且R1和R2直链烷基中的碳原子总数是14或16。
6、根据权利要求5的抗坏血酸衍生物,其中在通式(1)中,R1是n-C9H19,且R2是n-C7H15;或者R1是n-C8H17,且R2是n-C6H13。
8、根据权利要求7的制备抗坏血酸衍生物的方法,其中所述反应在缩合剂和/或脱水剂的存在下进行。
9、根据权利要求8的制备抗坏血酸衍生物的方法,其中所述脱水剂是硫酸。
10、根据权利要求7至9任意一项的制备抗坏血酸衍生物的方法,其中所述反应在溶剂中进行,所述溶剂选自水、丙酮、二噁烷、甲苯、乙基苯、甲基叔丁基醚和硫酸。
11、维生素C制剂,包含根据权利要求1至6任意一项的抗坏血酸衍生物作为有效成分。
12、胶原产生促进剂,包含根据权利要求1至6任意一项的抗坏血酸衍生物作为有效成分。
13、增白制剂,包含根据权利要求1至6任意一项的抗坏血酸衍生物作为有效成分。
14、外用皮肤制剂,包含根据权利要求1至6任意一项的抗坏血酸衍生物作为有效成分。
15、根据权利要求14的外用皮肤制剂,其含有抗坏血酸-2-磷酸酯和/或其盐。
16、根据权利要求14的外用皮肤制剂,其含有抗坏血酸-2-磷酸酯的钠盐、钾盐、镁盐或锌盐。
17、美容材料,包含根据权利要求14至16任意一项的外用皮肤制剂。
18、组合物,包含根据权利要求1至6任意一项的抗坏血酸衍生物,为医学或药学制剂、农业化学制剂或动物药物制剂的形式。
19、组合物,包含根据权利要求1至6任意一项的抗坏血酸衍生物,为食品或饲料添加剂的形式。
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2003
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- 2003-04-11 AU AU2003222450A patent/AU2003222450A1/en not_active Abandoned
- 2003-04-11 AT AT03717570T patent/ATE302001T1/de not_active IP Right Cessation
- 2003-04-11 DE DE60301345T patent/DE60301345T2/de not_active Expired - Lifetime
- 2003-04-11 CA CA002481591A patent/CA2481591C/en not_active Expired - Fee Related
- 2003-04-11 ES ES03717570T patent/ES2243901T3/es not_active Expired - Lifetime
-
2007
- 2007-02-08 US US11/672,677 patent/US7507750B2/en not_active Expired - Lifetime
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101484126B (zh) * | 2006-07-04 | 2011-10-12 | 昭和电工株式会社 | 乳液组合物 |
CN105121451A (zh) * | 2013-04-23 | 2015-12-02 | 株式会社日冷生物科学 | 新型美白剂 |
CN105121451B (zh) * | 2013-04-23 | 2017-05-31 | 株式会社日冷生物科学 | 新型美白剂 |
CN105792810A (zh) * | 2013-07-25 | 2016-07-20 | 绮丽儿·李·艾柏汀 | 用于表皮修复的配方 |
CN103445018A (zh) * | 2013-08-22 | 2013-12-18 | 福建天马科技集团股份有限公司 | 虹鳟稚鱼浮性膨化颗粒配合饲料 |
CN103445018B (zh) * | 2013-08-22 | 2014-11-12 | 福建天马科技集团股份有限公司 | 虹鳟稚鱼浮性膨化颗粒配合饲料 |
CN103554070A (zh) * | 2013-11-08 | 2014-02-05 | 李玉成 | 抗坏血酸氧铋、其制备方法及应用 |
CN115154349A (zh) * | 2022-07-19 | 2022-10-11 | 何直源 | 一种基于硫代二丙酸和抗坏血酸的美白组合物 |
Also Published As
Publication number | Publication date |
---|---|
US20060100177A1 (en) | 2006-05-11 |
DE60301345T2 (de) | 2006-06-29 |
ATE302001T1 (de) | 2005-09-15 |
ES2243901T3 (es) | 2005-12-01 |
EP1496889B1 (en) | 2005-08-17 |
JP4111856B2 (ja) | 2008-07-02 |
US7507750B2 (en) | 2009-03-24 |
CN1297266C (zh) | 2007-01-31 |
DE60301345D1 (de) | 2005-09-22 |
WO2003086384A1 (en) | 2003-10-23 |
CA2481591C (en) | 2009-08-18 |
CA2481591A1 (en) | 2003-10-23 |
AU2003222450A1 (en) | 2003-10-27 |
US7223775B2 (en) | 2007-05-29 |
JP2004002359A (ja) | 2004-01-08 |
US20070141000A1 (en) | 2007-06-21 |
EP1496889A1 (en) | 2005-01-19 |
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