CN1223853A - 含有抗坏血酸衍生物的化妆品及药品制剂 - Google Patents
含有抗坏血酸衍生物的化妆品及药品制剂 Download PDFInfo
- Publication number
- CN1223853A CN1223853A CN98122464.4A CN98122464A CN1223853A CN 1223853 A CN1223853 A CN 1223853A CN 98122464 A CN98122464 A CN 98122464A CN 1223853 A CN1223853 A CN 1223853A
- Authority
- CN
- China
- Prior art keywords
- group
- hydrogen
- ascorbic acid
- acid
- alkoxy carbonyl
- 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 25
- 239000000825 pharmaceutical preparation Substances 0.000 title claims abstract description 7
- 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
- -1 alkaline earth metal cations Chemical class 0.000 claims abstract description 49
- 239000001257 hydrogen Substances 0.000 claims abstract description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 36
- 150000001768 cations Chemical group 0.000 claims abstract description 13
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 12
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 12
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 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 84
- 229960005070 ascorbic acid Drugs 0.000 claims description 45
- 235000010323 ascorbic acid Nutrition 0.000 claims description 33
- 239000011668 ascorbic acid Substances 0.000 claims description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 230000003078 antioxidant effect Effects 0.000 claims description 4
- 235000006708 antioxidants Nutrition 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 2
- 125000005910 alkyl carbonate group Chemical group 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 239000001301 oxygen Substances 0.000 description 16
- 229910052760 oxygen Inorganic materials 0.000 description 16
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- 239000002211 L-ascorbic acid Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 239000011734 sodium Substances 0.000 description 9
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 8
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- 229910052749 magnesium Inorganic materials 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 229960001295 tocopherol Drugs 0.000 description 6
- 239000011732 tocopherol Substances 0.000 description 6
- 235000000069 L-ascorbic acid Nutrition 0.000 description 5
- 239000004359 castor oil Substances 0.000 description 5
- 238000005660 chlorination reaction Methods 0.000 description 5
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 235000013599 spices Nutrition 0.000 description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 4
- 239000005639 Lauric acid Substances 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
- 235000021319 Palmitoleic acid Nutrition 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 235000021355 Stearic acid Nutrition 0.000 description 4
- 229930003268 Vitamin C Natural products 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 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 4
- 125000004429 atom Chemical group 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- 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 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical class CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- ISYWECDDZWTKFF-UHFFFAOYSA-N nonadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCCC(O)=O ISYWECDDZWTKFF-UHFFFAOYSA-N 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
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- 235000021313 oleic acid Nutrition 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000008117 stearic acid Substances 0.000 description 4
- 239000004577 thatch Substances 0.000 description 4
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
- 235000019154 vitamin C Nutrition 0.000 description 4
- 239000011718 vitamin C Substances 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- WSSJONWNBBTCMG-UHFFFAOYSA-N 2-hydroxybenzoic acid (3,3,5-trimethylcyclohexyl) ester Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C1=CC=CC=C1O WSSJONWNBBTCMG-UHFFFAOYSA-N 0.000 description 3
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 125000005908 glyceryl ester group Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 3
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 3
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 3
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 3
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 3
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 3
- 229960003415 propylparaben Drugs 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 3
- 229940088594 vitamin Drugs 0.000 description 3
- 229930003231 vitamin Natural products 0.000 description 3
- 235000013343 vitamin Nutrition 0.000 description 3
- 239000011782 vitamin Substances 0.000 description 3
- 150000003722 vitamin derivatives Chemical class 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 2
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 2
- WHQOKFZWSDOTQP-UHFFFAOYSA-N 2,3-dihydroxypropyl 4-aminobenzoate Chemical compound NC1=CC=C(C(=O)OCC(O)CO)C=C1 WHQOKFZWSDOTQP-UHFFFAOYSA-N 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 2
- 102000008186 Collagen Human genes 0.000 description 2
- 108010035532 Collagen Proteins 0.000 description 2
- 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 2
- 235000004866 D-panthenol Nutrition 0.000 description 2
- 239000011703 D-panthenol Substances 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241001597008 Nomeidae Species 0.000 description 2
- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 244000018633 Prunus armeniaca Species 0.000 description 2
- 235000009827 Prunus armeniaca Nutrition 0.000 description 2
- 235000004433 Simmondsia californica Nutrition 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 2
- 230000001153 anti-wrinkle effect Effects 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
- WXNRYSGJLQFHBR-UHFFFAOYSA-N bis(2,4-dihydroxyphenyl)methanone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1O WXNRYSGJLQFHBR-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229920001436 collagen Polymers 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 229960003949 dexpanthenol Drugs 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- UVCJGUGAGLDPAA-UHFFFAOYSA-N ensulizole Chemical compound N1C2=CC(S(=O)(=O)O)=CC=C2N=C1C1=CC=CC=C1 UVCJGUGAGLDPAA-UHFFFAOYSA-N 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- YAQXGBBDJYBXKL-UHFFFAOYSA-N iron(2+);1,10-phenanthroline;dicyanide Chemical compound [Fe+2].N#[C-].N#[C-].C1=CN=C2C3=NC=CC=C3C=CC2=C1.C1=CN=C2C3=NC=CC=C3C=CC2=C1 YAQXGBBDJYBXKL-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 229960004488 linolenic acid Drugs 0.000 description 2
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 150000004668 long chain fatty acids Chemical class 0.000 description 2
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- MJVGBKJNTFCUJM-UHFFFAOYSA-N mexenone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=C(C)C=C1 MJVGBKJNTFCUJM-UHFFFAOYSA-N 0.000 description 2
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229960003471 retinol Drugs 0.000 description 2
- 235000020944 retinol Nutrition 0.000 description 2
- 239000011607 retinol Substances 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 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 2
- 239000002453 shampoo Substances 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 description 2
- 230000000475 sunscreen effect Effects 0.000 description 2
- 239000000516 sunscreening agent Substances 0.000 description 2
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 2
- 235000010384 tocopherol Nutrition 0.000 description 2
- 229930003799 tocopherol Natural products 0.000 description 2
- 229940042585 tocopherol acetate Drugs 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
- 229940005605 valeric acid Drugs 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- WTVHAMTYZJGJLJ-UHFFFAOYSA-N (+)-(4S,8R)-8-epi-beta-bisabolol Natural products CC(C)=CCCC(C)C1(O)CCC(C)=CC1 WTVHAMTYZJGJLJ-UHFFFAOYSA-N 0.000 description 1
- RGZSQWQPBWRIAQ-CABCVRRESA-N (-)-alpha-Bisabolol Chemical compound CC(C)=CCC[C@](C)(O)[C@H]1CCC(C)=CC1 RGZSQWQPBWRIAQ-CABCVRRESA-N 0.000 description 1
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 1
- POXUQBFHDHCZAD-MHTLYPKNSA-N (2r)-2-[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxy-2h-furan-5-one Chemical compound O1C(C)(C)OC[C@H]1[C@@H]1C(O)=C(O)C(=O)O1 POXUQBFHDHCZAD-MHTLYPKNSA-N 0.000 description 1
- PDHSAQOQVUXZGQ-JKSUJKDBSA-N (2r,3s)-2-(3,4-dihydroxyphenyl)-3-methoxy-3,4-dihydro-2h-chromene-5,7-diol Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2OC)=CC=C(O)C(O)=C1 PDHSAQOQVUXZGQ-JKSUJKDBSA-N 0.000 description 1
- 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
- BSVPFHMWULCQKF-UHFFFAOYSA-N 1-(3-phenylpropyl)-4-propan-2-ylbenzene Chemical compound C1=CC(C(C)C)=CC=C1CCCC1=CC=CC=C1 BSVPFHMWULCQKF-UHFFFAOYSA-N 0.000 description 1
- KBKGPMDADJLBEM-UHFFFAOYSA-N 1-(4-pentylphenyl)ethanone Chemical compound CCCCCC1=CC=C(C(C)=O)C=C1 KBKGPMDADJLBEM-UHFFFAOYSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 description 1
- KAWVQDRRFHLAPC-UHFFFAOYSA-N 2-(2,3-dimethoxyphenyl)-2-oxoacetic acid Chemical compound COC1=CC=CC(C(=O)C(O)=O)=C1OC KAWVQDRRFHLAPC-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940086681 4-aminobenzoate Drugs 0.000 description 1
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 235000019489 Almond oil Nutrition 0.000 description 1
- 241001116389 Aloe Species 0.000 description 1
- 101100345345 Arabidopsis thaliana MGD1 gene Proteins 0.000 description 1
- 241000972773 Aulopiformes Species 0.000 description 1
- VLOQYUSEMICXEZ-UHFFFAOYSA-N COC1=CC=C(C=CC(=O)OC(C)C(C)C)C=C1 Chemical compound COC1=CC=C(C=CC(=O)OC(C)C(C)C)C=C1 VLOQYUSEMICXEZ-UHFFFAOYSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- CIWBSHSKHKDKBQ-MVHIGOERSA-N D-ascorbic acid Chemical compound OC[C@@H](O)[C@@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-MVHIGOERSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-DUZGATOHSA-N D-isoascorbic acid Chemical compound OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 208000035126 Facies Diseases 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- AXISYYRBXTVTFY-UHFFFAOYSA-N Isopropyl tetradecanoate Chemical class CCCCCCCCCCCCCC(=O)OC(C)C AXISYYRBXTVTFY-UHFFFAOYSA-N 0.000 description 1
- 150000000996 L-ascorbic acids Chemical class 0.000 description 1
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 1
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 1
- CXISDVDFZMMHEI-UHFFFAOYSA-N O=C(C1=CC=C(OC)C=C1O)C1=CC=CC=C1.O=C(C1=CC=C(OC)C=C1O)C1=CC=CC=C1.C1(=CC=CC=C1)C(=O)C1=CC=CC=C1 Chemical compound O=C(C1=CC=C(OC)C=C1O)C1=CC=CC=C1.O=C(C1=CC=C(OC)C=C1O)C1=CC=CC=C1.C1(=CC=CC=C1)C(=O)C1=CC=CC=C1 CXISDVDFZMMHEI-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 244000025272 Persea americana Species 0.000 description 1
- 235000008673 Persea americana Nutrition 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- 244000173166 Pyrus ussuriensis Species 0.000 description 1
- 235000011572 Pyrus ussuriensis Nutrition 0.000 description 1
- 230000018199 S phase Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000221095 Simmondsia Species 0.000 description 1
- 244000044822 Simmondsia californica Species 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- ROUVVBLYVOSGLH-UHFFFAOYSA-N [Na].COC1=CC=C(C(=O)C(O)=O)C=C1OC Chemical compound [Na].COC1=CC=C(C(=O)C(O)=O)C=C1OC ROUVVBLYVOSGLH-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- GRTOGORTSDXSFK-XJTZBENFSA-N ajmalicine Chemical compound C1=CC=C2C(CCN3C[C@@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 GRTOGORTSDXSFK-XJTZBENFSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 239000008168 almond oil Substances 0.000 description 1
- 235000011399 aloe vera Nutrition 0.000 description 1
- RGZSQWQPBWRIAQ-LSDHHAIUSA-N alpha-Bisabolol Natural products CC(C)=CCC[C@@](C)(O)[C@@H]1CCC(C)=CC1 RGZSQWQPBWRIAQ-LSDHHAIUSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229940064734 aminobenzoate Drugs 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 235000010385 ascorbyl palmitate Nutrition 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 229940036350 bisabolol Drugs 0.000 description 1
- HHGZABIIYIWLGA-UHFFFAOYSA-N bisabolol Natural products CC1CCC(C(C)(O)CCC=C(C)C)CC1 HHGZABIIYIWLGA-UHFFFAOYSA-N 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000002704 decyl group Chemical group [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])* 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- TVQGDYNRXLTQAP-UHFFFAOYSA-N ethyl heptanoate Chemical compound CCCCCCC(=O)OCC TVQGDYNRXLTQAP-UHFFFAOYSA-N 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000013861 fat-free Nutrition 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 229960004881 homosalate Drugs 0.000 description 1
- 229920002674 hyaluronan Polymers 0.000 description 1
- 229960003160 hyaluronic acid Drugs 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 230000000640 hydroxylating effect Effects 0.000 description 1
- ZCTXEAQXZGPWFG-UHFFFAOYSA-N imidurea Chemical compound O=C1NC(=O)N(CO)C1NC(=O)NCNC(=O)NC1C(=O)NC(=O)N1CO ZCTXEAQXZGPWFG-UHFFFAOYSA-N 0.000 description 1
- UJPPXNXOEVDSRW-UHFFFAOYSA-N isopropyl dodecanoate Chemical class CCCCCCCCCCCC(=O)OC(C)C UJPPXNXOEVDSRW-UHFFFAOYSA-N 0.000 description 1
- 229940119170 jojoba wax Drugs 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- SOXAGEOHPCXXIO-UHFFFAOYSA-N meradimate Chemical compound CC(C)C1CCC(C)CC1OC(=O)C1=CC=CC=C1N SOXAGEOHPCXXIO-UHFFFAOYSA-N 0.000 description 1
- 229960002248 meradimate Drugs 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229950000999 mexenone Drugs 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical class C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 1
- QXVUGSHEKWUGTL-UHFFFAOYSA-N octyl 2-methoxy-3-phenylprop-2-enoate Chemical class CCCCCCCCOC(=O)C(OC)=CC1=CC=CC=C1 QXVUGSHEKWUGTL-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229940101267 panthenol Drugs 0.000 description 1
- 235000020957 pantothenol Nutrition 0.000 description 1
- 239000011619 pantothenol Substances 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- CGIHFIDULQUVJG-UHFFFAOYSA-N phytantriol Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)(O)C(O)CO CGIHFIDULQUVJG-UHFFFAOYSA-N 0.000 description 1
- CGIHFIDULQUVJG-VNTMZGSJSA-N phytantriol Natural products CC(C)CCC[C@H](C)CCC[C@H](C)CCC[C@@](C)(O)[C@H](O)CO CGIHFIDULQUVJG-VNTMZGSJSA-N 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- NEOZOXKVMDBOSG-UHFFFAOYSA-N propan-2-yl 16-methylheptadecanoate Chemical class CC(C)CCCCCCCCCCCCCCC(=O)OC(C)C NEOZOXKVMDBOSG-UHFFFAOYSA-N 0.000 description 1
- ZPWFUIUNWDIYCJ-UHFFFAOYSA-N propan-2-yl octadecanoate Chemical class CCCCCCCCCCCCCCCCCC(=O)OC(C)C ZPWFUIUNWDIYCJ-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- WWDMJSSVVPXVSV-YCNIQYBTSA-N retinyl ester Chemical compound CC1CCCC(C)(C)C1\C=C\C(\C)=C\C=C\C(\C)=C\C(O)=O WWDMJSSVVPXVSV-YCNIQYBTSA-N 0.000 description 1
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N salicylic acid phenyl ester Natural products OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 1
- 235000019515 salmon Nutrition 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000010352 sodium erythorbate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- PESXGULMKCKJCC-UHFFFAOYSA-M sodium;4-methoxycarbonylphenolate Chemical compound [Na+].COC(=O)C1=CC=C([O-])C=C1 PESXGULMKCKJCC-UHFFFAOYSA-M 0.000 description 1
- IXMINYBUNCWGER-UHFFFAOYSA-M sodium;4-propoxycarbonylphenolate Chemical compound [Na+].CCCOC(=O)C1=CC=C([O-])C=C1 IXMINYBUNCWGER-UHFFFAOYSA-M 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 229960000368 sulisobenzone Drugs 0.000 description 1
- 230000037072 sun protection Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OHOTVSOGTVKXEL-UHFFFAOYSA-K trisodium;2-[bis(carboxylatomethyl)amino]propanoate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C(C)N(CC([O-])=O)CC([O-])=O OHOTVSOGTVKXEL-UHFFFAOYSA-K 0.000 description 1
- UEVAMYPIMMOEFW-UHFFFAOYSA-N trolamine salicylate Chemical compound OCCN(CCO)CCO.OC(=O)C1=CC=CC=C1O UEVAMYPIMMOEFW-UHFFFAOYSA-N 0.000 description 1
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 150000003700 vitamin C derivatives Chemical class 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 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 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
- A61K31/375—Ascorbic acid, i.e. vitamin C; Salts thereof
-
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of 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
- A61Q19/007—Preparations for dry skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/522—Antioxidants; Radical scavengers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Birds (AREA)
- Chemical & Material Sciences (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Medicinal Preparation (AREA)
Abstract
描述了在化妆品和药物制剂中使用式Ⅰ的抗坏血酸衍生物其中可变基团相互独立地具有如下意义:R1是氢,C1－C20－酰基,C1－C12－烷氧羰基,C1－C12－烷基;R2是氢,C1－C20－酰基,C1－C12－烷氧羰基,C1－C12－烷基;其中R1和R2,与和它们键连的氧原子以及键连至氧原子的碳原子一起,可以形成一个未取代的或取代的杂环;R3是氢或选自包括NH4 +,碱金属和碱土金属阳离子的阳离子;R4是C1－C12－烷氧羰基。
Description
抗坏血酸(维生素C)是一种抗氧化剂，广泛使用于化妆品中。同维生素E一起，它对抗不饱和脂肪酸的氧化作用并因此防止脂过氧化物的生成(O.Isler,G.Brubacher,S.Ghisla,B.Krutler eds.；维生素Ⅱ(维生素Ⅱ)，G.Thieme Verlag,Stuttgart,N.Y.,431,1988)。作为一种维生素，抗坏血酸也参与代谢作用，例如参与在胶原合成中对脯氨酸的羟基化(J.J.Burns,J.M.Rivers,L.J.Machin eds.；维生素C第三次会议，Ann.N.Y.Acad.Sci.,498(1987)1-533)。
因为在化妆品制剂中抗坏血酸极低的稳定性，所以经常需要使用抗坏血酸的稳定衍生物。这样的实例包括L-抗坏血酸单磷酸酯钠，(JP07082127,JP 05331020),L-抗坏血酸2-O-D葡萄糖苷(T.Sakamoto et al.；19th IFSCC Congress,Sydney,1996,Vol.2,PaperNo.14)和5,6-异亚丙基-L-抗坏血酸2-磷酸酯(JP 08269074)。
然而，上述稳定的抗坏血酸衍生物往往有缺点，即在化妆品或药物油剂中有太差的溶解性。
因此本发明的一个目的是制造用于化妆品和药物制剂中的稳定的，没有上述缺点的抗坏血酸衍生物。
我们发现按照本发明使用式Ⅰ的抗坏血酸衍生物已经达到了这个目的，
其中可变化基团互相独立地具有如下意义：R1是氢，C1-C20-酰基，C1-C12-烷氧羰基，C1-C12-烷基；R2是氢，C1-C20-酰基，C1-C12-烷氧羰基，C1-C12-烷基；其中R1和R2与和它们键连的氧原子以及键连至氧原子的碳原子一起，可以形成非取代或取代的杂环：R3是氢或选自一组包括NH4 +，碱金属和碱土金属阳离子的阳离子；R4是C1-C12-烷氧羰基。用于化妆品和药物制剂中。
式Ⅰ优选的化合物是那些可变基团具有如下意义：R1是氢，C1-C20-酰基，C1-C12-烷氧羰基，C1-C12-烷基；R2是氢，C1-C20-酰基，C1-C12-烷氧羰基，C1-C12-烷基；其中R1和R2，与和它们键连的氧原子以及与键连至氧原子的碳原子一起，可以形成非取代或取代的杂环并且如果R2是氢R1必须不是C1-C12-烷氧羰基基团，R3是氢或选自一组包括NH4 +，碱金属和碱土金属阳离子的阳离子；R4是C1-C12-烷氧羰基。
式Ⅰ特别优选的化合物是那些其中可变基团具有如下意义的：R1是氢，C1-C20-酰基，C1-C6-烷氧羰基；R2是氢，C1-20-酰基，C1-C6-烷氧羰基，其中如果R2是氢，R1必须不是C1-C6-烷氧羰基基团；R3是氢或选自一组包括NH4 +，碱金属和碱土金属阳离子的阳离子；R4是C1-C6-烷氧羰基。
按照本发明，在式Ⅰ的抗坏血酸衍生物中，应理解R1和R2的酰基基团为分支或不分支的饱和的或不饱和的，如果合适为多不饱和的C1-C20-酰基链。
这些实例是甲酸，乙酸，丙酸，正丁酸，异丁酸，山梨酸，正戊酸，异戊酸，己酸，辛酸，癸酸，十一烷酸，月桂酸，十三烷酸，肉豆蔻酸，十五烷酸，棕榈酸，棕榈油酸，硬脂酸，油酸，亚油酸，亚麻酸，十九烷酸和花生四烯酸的酰基基团。
优选的酰基基团是那些有C10至C20碳链的长链脂肪酸，尤其是月桂酸，棕榈酸，棕榈油酸，硬脂酸，油酸，和亚油酸的酰基基团。
可提及的烷基基团R1和R2是分支的或不分支的C1-C12-烷基链，优选地为甲基，乙基，正丙基，1-甲基乙基，正丁基，1-甲基丙基，2-甲基丙基，1,1-二甲基乙基，正戊基，1-甲基丁基，2-甲基丁基，3-甲基丁基，2,2-二甲基丙基，1-乙基丙基，正己基，1,1-二甲基丙基，1,2-二甲基丙基，1-甲基戊基，2-甲基戊基，3-甲基戊基，4-甲基戊基，1,1-二甲基丁基，1,2-二甲基丁基，1,3-二甲基丁基，2,2-二甲基丁基，2,3-二甲基丁基，3,3-二甲基丁基，1-乙基丁基，2-乙基丁基，1,1,2-三甲基丙基，1,2,2-三甲基丙基，1-乙基-1-甲基丙基，1-乙基-2-甲基丙基，正庚基，正辛基，正壬基、正癸基，正十一烷基，正十二烷基。
特别优选的烷基基团是C1-C6-烷基链，尤其是甲基，乙基，正丙基，1-甲基乙基，正丁基，1-甲基丙基，2-甲基丙基，1,1-二甲基乙基，正戊基，1-甲基丁基，2-甲基丁基，3-甲基丁基，2,2-二甲基丙基，1-乙基丙基，正己基。
基团R1和R2，与和它们键连的氧原子以及键连至氧原子的碳原子一起，能形成非取代或取代的杂环。它们也包括，例如，环状缩醛及缩酮，特别是用作抗坏血酸中两个末端羟基功能团(在5和6位)的保护基。优选的杂环系统特别是5,6-异亚丙基基团，它是由两个位于5和6位的游离羟基基团与丙酮反应形成的。
合适的R1,R2和R4烷氧羰基基团是那些含有1至12C原子的烷氧基，优选为1至6C原子，特别优选为1至4C原子。
可提及的优选基团的实例是：甲氧羰基 乙氧羰基异丙氧羰基 正丙氧羰基1-甲氧丙氧羰基 正丁氧羰基正戊氧羰基 2-甲基丙氧羰基3-甲基丁氧羰基 1,1-二甲基丙氧羰基2,2-二甲基丙氧羰基 己氧羰基1-甲基-1-乙基丙氧羰基特别优选的烷氧羰基基团是：甲氧羰基 乙氧羰基异丙氧羰基 正丙氧羰基1-甲基丙氧羰基 正丁氧羰基
R3可能的阳离子是NH4 +和碱金属和碱土金属，优选是Na,K,Li,Ca和Mg，特别优选是Na、K和Mg。
术语抗坏血酸衍生物应理解为意指L-和D-抗坏血酸(异抗坏血酸)，优选地是L-抗坏血酸。
一些抗坏血酸的双和三碳酸酯是已知的。因此美国2,980,702描叙了2,5,6-三-O-(C1-C3-烷氧羰基)-L-抗坏血酸类化合物和它们在食品中用作耐热添加剂，尤其是在烤制食品中。JP 42020050描叙2,6-二-O(C1-C3-烷氧羰基)-L-抗坏血酸的合成，作为抗坏血酸的热稳定衍生物。
然而，在化妆品及药物应用中使用上述抗坏血酸衍生物是新颖的。
按照本发明，式Ⅰ的稳定的抗坏血酸衍生物是非常合适用于化妆品及药品制剂中的活性化合物。
因此这些化合物是出色的，首先在于，通过可变化基团R1,R2和R4，可以以控制的方式调节抗坏血酸衍生物的亲脂性，依据化妆品及药品制剂中配方的要求，对于本领域专业人员大范围的稳定的维生素C衍生物因此是可获得的。维生素C，尤其是三碳酸酯和2-单碳酸酯的脂肪酸酯，因为它们好的油溶性，可以非常容易地混合至制剂中例如，软膏，洗剂，凝胶剂，乳剂。
因此，本发明也涉及含有有效量的式Ⅰ的至少一种化合物的化妆品和药品制剂，和通常的化妆品和药品辅助剂及添加剂。
上述制剂可以含有按化妆品或药品制剂总重量计从0.01至10％比例的式Ⅰ化合物，优选地按重量计为0.1至8％，特别优选地按重量计为0.5至5％。
式Ⅰ的抗坏血酸衍生物首先可使用于所有的化妆品和药品制剂中，它们除了水，还含有乳化剂，稳定剂，天然油，化妆品油，脂肪，蜡，硅油，硅油衍生物，增溶剂，防晒剂，湿润剂，活性化合物，稠度分配剂，凝胶形成剂，抗氧化剂或防腐剂。
例如，使用的乳化剂是如下物质：多聚甘油脂肪酸酯，脂肪酸乙氧基酯，脱水山梨脂肪酸脂，脂肪酸的磷酸酯，膦酯，甘油单硬脂酸酯和自乳化的甘油单硬酯酸酯。
稳定剂是指：
脂肪酸的镁和铝盐，络合剂如EDTA,NTA,MGDA，抗氧化剂如BHT,BHA,2-生育酚，没食子酸，以及它们的盐和酯。
天然油是，例如，希蒙得木油，向日葵油，花生油，杏仁油，鳄梨油，昆士兰果油，蓖麻油，玉米胚芽油，葡萄籽油。
化妆品油是，例如，脂肪酸的异丙基酯，非常特别是硬脂酸异丙基酯，棕榈酸异丙基酯，异硬脂酸异丙基酯，肉豆蔻酸异丙基酯、月桂酸异丙基酯，石蜡油，中性油。
化妆品的活性化合物是，例如，泛酰醇红没药醇。2-生育酚，2-生育酚乙酸酯，芦荟，藻类的提取物，透明质酸，视黄醇和视黄基酯，植烷三醇，泛酰基乙基醚，阿巍酸。
可单独使用或与式Ⅰ化合物混合使用的防晒剂是例如
| 号 | 物质 | CAS号.(=酸) |
| 1 | 4-氨基苯甲酸 | 150-13-0 |
| 2 | 3-(4＇-三甲基铵)亚苄基茨烷-2-酮甲基硫酸酯 | 52793-97-2 |
| 3 | 3,3,5-三甲基环己基水杨酸酯(homosalate) | 118-56-9 |
| 4 | 2-羟基-4-甲氧基-二苯酮(羟苯酮) | 131-57-7 |
| 5 | 2-苯基苯并咪唑-5-磺酸和其钾，钠和三乙醇胺盐 | 27503-81-7 |
| 6 | 3,3＇-(1,4-苯二亚甲基)双(7,7-二甲基-2-氧代双环〔2.2.1〕庚烷-1-甲烷-磺酸)和其盐 | 90457-82-2 |
| 7 | 聚乙氧乙基-4-双(聚乙氧)氨基苯甲酸酯， | 113010-52-9 |
| 8 | 2-乙基己基4-二甲基氨基苯甲酸酯 | 21245-02-3 |
| 9 | 2-乙基己基水杨酸酯 | 11 8-60-5 |
| 10 | 2-异戊基4-甲氧基肉桂酸酯 | 71617-10-2 |
| 11 | 2-乙基己基4-甲氧基肉桂酸酯 | 5466-77-3 |
| 12 | 2-羟基-4-甲氧基二苯酮-5-磺酸(sulisobenzone)和其钠盐 | 4065-45-6 |
| 13 | 3-(4＇-甲基)亚苄基茨烷-2-酮 | 36861-47-9 |
| 14 | 3-亚苄基茨烷-2-酮 | 15087-24-8 |
| 15 | 1-(4′-异丙基苯基)-3-苯基丙烷1,3-二酮 | 63250-25-9 |
| 16 | 4-异丙基苯基水杨酸酯 | 94134-93-7 |
| 17 | 2,4,6-三苯胺-(O-碳-2＇-乙基-己基-1＇-氧)-1,3,5-三嗪 | 88122-99-0 |
| 号 | 物质 | CAS号.(=酸) |
| 18 | 3-咪唑-4-基丙烯酸和其乙基酯 | 104-98-3 |
| 19 | 乙基2-腈基-3,3-二苯基丙烯酸酯 | 5232-99-5 |
| 20 | 2′-乙基己基2-腈基-3,3-二苯基丙烯酸酯 | 6197-30-4 |
| 21 | 甲基O-氨基苯甲酸酯或：5-甲基-2-1-甲基-2-(1-甲基乙基)-2-氨基苯甲酸酯 | 134-09-8 |
| 22 | 甘油基对氨基苯甲酸酯或：1-甘油基4-氨基苯甲酸酯 | 136-44-7 |
| 23 | 2,2＇-二羟基-4-甲氧基二苯酮(dioxybenzone) | 131-53-3 |
| 24 | 2-羟基-4-甲氧基-4-甲基二苯酮(mexenone) | 1641-17-4 |
| 25 | 三乙醇胺水杨酸盐 | 2174-16-5 |
| 26 | 二甲氧基苯基乙醛酸或3,4-二甲氧基苯基乙醛酸钠 | 4732-70-01 |
| 27 | 3-(4′-硫代)亚苄基茨烷-2-酮和其盐 | 56039-58-8 |
| 28 | 4-叔丁基-4＇-甲氧基二苯甲酰基甲烷 | 70356-09-1 |
| 29 | 2,2＇,4,4＇-四羟基二苯酮 | 131-55-5 |
式Ⅰ的抗坏血酸衍生物也适宜作表面活性剂配方。
因此可以制造含有式Ⅰ稳定维生素C的洗发剂，香波，和泡沫而无问题。
在化妆产品中不限制使用阴离子与阳离子表面活性剂的组合。
本发明还进一步涉及式Ⅰa的抗坏血酸衍生物，
其中可变基团互相独立地具有下述意义：R1和R2相互独立地是氢或C1-C20-酰基；R3是氢或选自一组包括碱金属和碱土金属的阳离子；R4是C1-C6-烷氧羰基。本申请也要求式Ⅰb的抗坏血酸衍生物，
其中R3是氢或选自一组包括碱金属和碱土金属的阳离子；和R4是C1-C6-烷氧羰基。
R1和R2的酰基基团是指分支或非分支的，饱和的或不饱和的，如果合适是多不饱和的C1-C20-酰基链。
这些实例是甲酸，乙酸，丙酸，正丁酸，异丁酸，正戊酸，异戊酸，己酸，辛酸，癸酸，十一烷酸，月桂酸，十三烷酸，肉豆蔻酸，十五烷酸，棕榈酸，棕榈油酸，硬脂酸，油酸，亚油酸，亚麻酸，十九烷酸和花生四烯酸的酰基基团。
优选的酰基基团是那些有C10至C20碳链的长链脂肪酸，尤其是月桂酸，棕榈酸，棕榈油酸，硬脂酸，油酸和亚油酸的酰基基团。
R4的合适的烷氧羰基基团是那些烷氧基团，它含有从1至6C原子，尤其优选地是1至4C原子。
尤其优选的烷氧羰基基团是：甲氧基羰基 乙氧羰基异丙氧羰基 正丙氧羰基1-甲基丙氧羰基 正丁氧羰基
R3的可能的阳离子是一组包括碱金属及碱土金属，优选地是Na,K,Li,Ca和Mg，尤其优选地是Na、K和Mg。
式Ⅰa和Ⅰb抗坏血酸衍生物的合成，是从起始物质Ⅱa和Ⅱb开始，按日本专利公布JP42020050的方法类似地进行。就进一步的细节可参阅该出版物。
在以下实例中，更详细地说明按本发明的式Ⅰ抗坏血酸衍生物的制备和含有这些抗坏血酸衍生物的化妆品配方的组成。实例1
2,5,6-三-O-(异丙氧羰基)-L-抗坏血酸
于-15℃将151(1.5mol)1M氯甲酸异丙酯在甲苯的溶液逐滴加入至80g(0.454mol)L-抗坏血酸在350ml(4.3mol)的吡啶中。沉积出的吡啶氯化氢盐为白色沉淀。将所得悬浊液在室温下另外搅拌1.5小时然后过滤掉吡啶氯化氢盐。真空浓缩黄色滤液并将从中生成的红色，油状粗产品溶解于二氯甲烷中，然后用1M HCl溶液洗涤二次。用饱和的(10％浓度)碳酸氢钠溶液将下层有机相萃取四次，并将合并的水性萃取部分(每次的上层相)用浓盐酸处理直至出现混浊(约pH1)。然后用二氯甲烷三次萃取该水悬浊液并用Na2SO4干燥合并的有机萃取液(每次的下层相)，并于真空中浓缩。真空干燥后得到黄色蜡状物。收率：68.0g(34.5％)13C-NMR:δ=165.82(CO-抗坏血酸基)，154.90(C-3-抗坏血酸基)，154.06,153.58,153.09(3xCO-碳酸酯)，115.04(C-2-抗坏血酸基)，76.02(C-4-抗坏血酸基)，73.63；73.25,73.13(3x CH(CH3)2),72.88(C-5-抗血酸基)，64.44(C-6-抗坏血酸基)，12.70,21.69,21.56,21.54,21.48,21.47(6x CH3)ppm。实例26-O-棕榈酰-2-O-(异丙氧羰基)-L-抗坏血酸
于-15℃将45ml(0.045mol)的1M氯甲酸异丙基酯在甲苯的溶液逐滴加入至17.8g(0.042mol)的6-O-棕榈酰-L-抗坏血酸在100ml(1.24mol)的吡啶中。将反应混合物在室温下继续搅拌一小时并过滤掉沉积的吡啶氯化氢盐。真空下与甲苯重复共蒸馏来浓缩黄液滤液。
将棕色油状剩余物溶解于二氯甲烷/甲苯(1∶1)并用1M HCl溶液洗涤两次。将有机相用Na2SO4干燥并于真空浓缩，得到深黄至棕色固体，它以分散形式在少量冷乙酸乙酯中悬浮两次之后，过滤得白色固体。最终重量：13.3g(61.9％)13C-NMR:δ=174.11(CO-棕榈酰)，166.80(CO-抗坏血酸基)，156.62(OCOO-碳酸酯)，153.23(C-3-抗坏血酸基)，114.60(C-2-抗坏血酸基)75.98(C-4-抗坏血酸基)；75.60(OCH(CH3)2)；67.94(C-5-抗坏血酸基)；64.43(C-6-抗坏血酸基)；34.10(C-2-棕榈酰)ppm。实例35,6-O-异亚丙基-2-O-(异丙氧羰基)-L-抗坏血酸
于-15℃将415ml(0.415mol)的1M氯甲酸异丙酯在甲苯的溶液逐滴加入至85.3g(0.395mol)的5,6-O-异亚丙基-L-抗坏血酸在300ml(3.7mol)的吡啶中，吡啶氯化氢盐以白色固体沉积。将混合物于室温继续搅拌一小时并过滤掉吡啶氯化氢盐。于真空下将黄色滤液用甲苯重复共蒸馏浓缩。将所得的澄红色浆状物溶于二氯甲烷/甲苯(1∶1)，用1M HCl溶液洗涤两次并每次用饱和(10％浓度)碳酸氢钠溶液萃取四次。用浓盐酸处理合并的上层水相直到溶液变混浊。因而形成水悬浊液并用二氯甲烷萃取三次以溶解沉积的固体。将合并的有机萃取液用Na2SO4干燥并真空浓缩，得到黄色固体。收率：86g(72.1％)
将该有色粗品固体从少量热二氯甲烷中重结晶并在少量冷乙酸乙酯中悬浮该结晶，随之过滤得到白色结晶。重结晶后收率：47.2g(39.5％)13C-NMR:δ=166.21(CO-抗坏血酸基)，155.13(CO-碳酸酯)153.46(C-2-抗坏血酸基)，114.79(C-3-抗坏血酸基)，110.71(C(CH3)2),76.03(C-4-抗坏血酸基)，74.74(CH(CH3)2)，73.52(C-5-抗坏血酸基)，65,28(C-6-抗坏血酸基)，25.78,25.55(C(CH3)2),21.51,21.50(CH(CH3)2)ppm。实例42-O-(异丙氧羰基)-L-抗坏血酸
于室温下将47g(0.155mol)的5,6-O-异亚丙基-2-O-(异丙基氧羰基)-L-抗坏血酸在200ml三氟醋酸/水混合物(1∶4)中搅拌12小时。真空下以重复的共蒸馏将无色反应溶液浓缩。得到淡棕色浆状物(56.4g,138.3％)，用硅胶纯化(展开剂：二氯甲烷/甲醇3∶1)。收率：43g(92％)1H-NMR:δ=4.81(H-4),4.77(OCH(CH3)2),3.77(H-5),3.49(2xH-6),1.30-1.25(OCH(CH3)2)ppm.化妆品的制备实例5无脂肪防晒凝胶的组成物质含量(重量％)0.40 丙烯酸酯/C10-C20烷基丙烯酸酯交叉聚合物0.25 羟乙基纤维素8.00 甲氧肉桂酸辛酯1.00 4-甲基亚苄基樟脑0.50 6-O-棕榈酰基-2-O-(异丙氧羰基)-L-抗坏血酸0.20 EDTA二钠5.00 甘油0.15 香料0.30 咪唑烷基脲0.25 对羟基苯甲酸甲酯钠0.15 对羟基苯甲酸丙酯钠5.00 PEG-25 PABA0.10 氢氧化钠至100 水实例6湿润霜的组成物质含量(重量％)6.00 PEG-7-氢化的蓖麻油5.00 棕榈酸异丙酯6.00 矿物油5.00 希蒙得木油5.00 杏仁油0.50 生育酚乙酸酯2.00 6-O-棕榈酰-2-O-(异丙氧羰基)-L-抗坏血酸0.60 硬脂酸镁2.00 PEG-45/十二烷基1,2乙二醇共聚合物5.00 甘油0.25 对羟基苯甲酸甲酯0.15 对羟基苯甲酸丙酯5.00 咪唑烷基脲0.15 香料0.20 EDTA二钠至100 水实例7湿润霜的组成物质含量(重量％)6.00 PEG-7-氢化的蓖麻油5.00 棕榈酸异丙酯6.00 矿物油5.00 希蒙得木油5.00 杏仁油0.50 生育酚乙酸酯2.00 5,6-O-异丙基亚基-2-O-(异丙氧羰基)-L-抗坏血酸0.60 硬脂酸镁2.00 PEG-45/十二烷基1,2-乙二醇共聚合物5.00 甘油0.25 对羟基苯甲酸甲酯0.15 对羟基苯甲酸丙酯5.00 咪唑烷基脲0.15 香料0.20 EDTA钠至100 水实例8
不含防腐剂的晚霜组成物质含量(重量％)5.00 PEG-7-氢化的蓖麻油4.00 棕榈酸异丙酯4.00 辛酸/辛酸三甘油酯3.00 6-O-棕榈酰-2-O-(异丙氧羰基)-L-抗坏血酸1.50 PEG-45/十二烷基1,2-乙二醇共聚合物0.50 硬脂酸镁1.50 二甲聚硅氧烷4.00 1,2-丙二醇4.00 甘油8.00 611醇2.00 胶原0.15 香料至100 水实例9抗皱霜组成物质含量(重量％)6.00 PEG-7-氢化的蓖麻油5.00 棕榈酰异丙酯10.00 矿物油3.00 辛酸/辛酸三甘油酯0.60 硬脂肪镁1.00 6-O-棕榈酰-2-O-(异丙氧羰基)-L-抗坏血酸1.50 生育酚乙酸酯2.00 PEG-45/十二烷基1,2-乙二醇共聚合物0.05 生育酚0.20 视黄醇0.30 甘油0.70 硫酸镁0.25 对羟基苯甲酸甲酯0.15 对羟基苯甲酸丙酯0.20 抗坏血酸单磷酸钠0.10 2-生育酚0.10 抗坏血酸棕榈酸酯0.15 香料至100 水实例10抗皱霜的组成物质含量(重量％)6.00 PEG-7-氢化的蓖麻油5.00 棕榈酸异丙酯10.00 矿物油3.00 辛酸/辛酸三甘油酯0.60 硬脂酸镁1.00 2,5,6-三-O-(异丙氧羰基)-L-抗坏血酸1.50 生育酚乙酸酯2.00 PEG-45/十二烷基1,2-乙二醇共聚合物0.05 生育酚0.20 视黄醇0.30 甘油0.70 硫酸镁0.25 对羟基苯甲酸甲酯0.15 对羟基苯甲酸丙酯0.20 抗坏血酸单磷酸钠0.10 2-生育酚0.10 棕榈酸抗坏血酸酯0.15 香料至100 水实例11湿润日霜的组成物质含量(重量％)2.00 Ceteareth 162.00 Ceteareth 12510.00 矿物油3.00 辛酸/辛酸三甘油酯3.00 异硬脂酸3.00 6-O-棕榈酰-2-O-(异丙氧羰基)-L-抗坏血酸1.50 生育酚乙酸酯2.00 D-Panthenol USP0.05 生育酚0.20 视黄醇0.30 甘油0.15 二溴氰基丁烷0.20 抗坏血酸单磷酸钠0.10 2-生育酚0.10 抗坏血酸棕榈酸酯0.15 香料至100 水实例12湿润日霜的组成物质含量(重量％)2.00 Ceteareth 162.00 Ceteareth 12510.00 矿物油3.00 辛酸/辛酸三甘油酯3.00 异硬脂酸3.00 2-O-(异丙氧羰基)-L-抗坏血酸1.50 生育酚乙酸酯2.00 D-Panthenol USP0.05 生育酚0.20 视黄醇0.30 甘油0.15 二溴氰基丁烷0.20 抗坏血酸单磷酸钠0.10 2-生育酚0.10 抗坏血酸棕榈酸酯0.15 香料至100 水
Claims (10)
1．式Ⅰ的抗坏血酸衍生物在化妆品和药物制剂中的应用，
其中可变化基团相互独立地具有以下意义：R1是氢，C1-C20-酰基，C1-C12-烷氧羰基，C1-C12-烷基；R2是氢，C1-C20-酰基，C1-C12-烷氧羰基，C1-C12-烷基；其中R1和R2，和与它们键连的氧原子以及键连至氧原子的碳原子一起，可以形成一个未取代的或取代的杂环：R3是氢或选自一组包含NH4 +，碱金属和碱土金属的阳离子；R4是C1-C12-烷氧羰基。
2．权利要求1中要求的抗坏血酸衍生物的用途，其中可变基团有如下意义：R1是氢，C1-C20-酰基，C1-C12-烷氧羰基，C1-C12-烷基；R2是氢，C1-20-酰基，C1-C12-烷氧羰基，C1-C12-烷基；其中R1和R2，与和它们键连的氧原子以及键连至氧原子的碳原子一起，可以形成未取代的或取代的杂环和如果R2是氢R1必须不是C1-C12-烷氧羰基基团；R3是氢或选自NH4 +，碱金属和碱土金属阳离子的阳离子；R4是C1-C12-烷氧羰基。
3．权利要求1和2中要求的抗坏血酸衍生物的用途，其中可变化基团有如下意义：R1是氢，C1-C20-酰基，C1-C6-烷氧羰基；R2是氢，C1-20-酰基，C1-C6-烷氧羰基，如果R2是氢，R1必须不是C1-C6-烷氧羰基基团；R3是氢或选自包括NH4 +，碱金属和碱土金属阳离子的阳离子；R4是C1-C6-烷氧羰基。
4．权利要求1至3要求的在化妆品和药物制剂中抗坏血酸衍生物作为抗氧化剂的用途。
5．一种化妆品和药物制剂，它包含有效量的至少一种权利要求1至3中的式Ⅰ化合物，和常用的化妆品和药物辅助剂和添加剂。
6．式Ⅰa的抗坏血酸衍生物，其中可变基团相互独立地具有如下意义：R1和R2相互独立地是氢或C1-20-酰基，R3是氢或选自包含NH4 +，碱金属和碱土金属阳离子的一组阳离子；R4是C1-C6-烷氧羰基。
7．式Ⅰb的抗坏血酸衍生物，
其中，R3是氢或选自包含NH4 +，碱金属和碱土金属阳离子的一组阳离子；和R4是C1-C6-烷氧羰基。
8．制备式Ⅰa抗坏血酸衍生物的方法，它包括将式Ⅱa的抗坏血酸衍生物与链长C1至C6的卤代碳酸烷基酯反应，
其中取代基R1至R3具有权利要求6中提及的意义。
9．制备式Ⅰb的抗坏血酸衍生物的方法，它包括将式Ⅱb的抗坏血酸衍生物与链长C1至C6的卤代碳酸烷基酯反应，其中R3有权利要求7中所提及的意义。
10．权利要求8和9中制备抗坏血酸衍生物的方法，它包括使用链长C1至C6的氯代或溴代碳酸烷基酯。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19750526.0 | 1997-11-14 | ||
| DE19750526A DE19750526A1 (de) | 1997-11-14 | 1997-11-14 | Ascorbinsäurederivate enthaltende kosmetische und pharmazeutische Zubereitungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1223853A true CN1223853A (zh) | 1999-07-28 |
| CN1211082C CN1211082C (zh) | 2005-07-20 |
Family
ID=7848769
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN98122464.4A Expired - Fee Related CN1211082C (zh) | 1997-11-14 | 1998-11-16 | 含有抗坏血酸衍生物的化妆品及药品制剂 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US6346254B1 (zh) |
| EP (1) | EP0917871B1 (zh) |
| JP (1) | JPH11236332A (zh) |
| CN (1) | CN1211082C (zh) |
| DE (2) | DE19750526A1 (zh) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101686925B (zh) * | 2006-08-11 | 2013-04-03 | 默克专利股份有限公司 | 抗坏血酸衍生物用于官能化基质的用途 |
| TWI462913B (zh) * | 2009-05-07 | 2014-12-01 | Cosmol Co Ltd | 製備抗壞血酸衍生物之方法 |
| CN115260170A (zh) * | 2021-04-30 | 2022-11-01 | 禾美生物科技(浙江)有限公司 | 抗坏血酸多肽衍生物及其制备方法和应用 |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19750526A1 (de) * | 1997-11-14 | 1999-05-20 | Basf Ag | Ascorbinsäurederivate enthaltende kosmetische und pharmazeutische Zubereitungen |
| DE19962267A1 (de) * | 1999-12-23 | 2001-06-28 | Beiersdorf Ag | Verwendung von Wirkstoffkombinationen aus einem oder mehreren NO-Synthasehemmern und einer oder mehreren Ascorbylverbindungen zur Stärkung der Barrierefunktion der Haut |
| FR2807320B1 (fr) * | 2000-04-10 | 2002-05-24 | Oreal | Utilisation de derives d'acide ascorbique pour augmenter la synthese des creramides epidermiques |
| AU7688301A (en) * | 2000-07-13 | 2002-01-30 | Skinmedica Inc | Composition for topically delivering vitamin c |
| DE10048125A1 (de) * | 2000-09-28 | 2002-04-18 | Beiersdorf Ag | Zubereitungen von Emulsionstyp W/O mit erhöhtem Wassergehalt, mit mittelpolaren und/oder unpolaren Lipiden und einem oder mehreren grenzflächenaktiven Polyethern vom Typ A-O-B-O-A |
| DE10048427A1 (de) * | 2000-09-29 | 2002-04-11 | Beiersdorf Ag | Zubereitungen vom Emulsionstyp W/O mit erhöhtem Wassergehalt, mit mittelpolaren und/oder unpolaren Lipiden und einem oder mehreren grenzflächenaktiven Polyet hern vom Typ A-O-B-O-A sowie mindestens einer Substanz gewählt aus der Gruppe der anionischen und oder amphoteren Polymere |
| DE10048429A1 (de) * | 2000-09-29 | 2002-04-11 | Beiersdorf Ag | Zubereitungen vom Emulsionstyp W/O mit erhöhtem Wassergehalt, mit mittelpolaren und/oder unpolaren Lipiden und einem oder mehreren grenzflächenaktiven Polyethern von Typ A-O-B-O-A sowie einer Substanz gewählt aus der Gruppe der nichtionischen Polymere |
| JP2002212037A (ja) * | 2001-01-15 | 2002-07-31 | Showa Denko Kk | ヘア保護剤 |
| FR2825922B1 (fr) * | 2001-06-15 | 2005-01-21 | Oreal | 2-hexadecanoate d'ascorbyle comme inhibiteur de no-synthase et utilisations |
| WO2003018575A1 (en) * | 2001-08-24 | 2003-03-06 | Wyeth Holdings Corporation | 5-substituted-3(2h)-furanones useful for inhibition of farnesyl-protein transferase |
| EP1620419A4 (en) * | 2003-04-21 | 2008-07-23 | Tagra Biotechnologies Ltd | STABILIZED DERIVATIVES OF ASCORBIC ACID |
| EP1742710B1 (en) * | 2004-01-13 | 2009-06-03 | L'Oréal USA Creative, Inc. | Stabilized ascorbic acid compositions and methods therefor |
| JP4574384B2 (ja) * | 2005-02-17 | 2010-11-04 | 日光ケミカルズ株式会社 | コラーゲン産生促進用の皮膚外用剤 |
| CA2642726C (en) | 2006-02-21 | 2015-11-03 | Mary Kay, Inc. | Stable vitamin c compositions |
| US20070225360A1 (en) * | 2006-03-22 | 2007-09-27 | L'oreal | Anti-aging composition containing phloretin |
| EP2231111A4 (en) * | 2007-11-28 | 2015-11-04 | Colgate Palmolive Co | PRODUCT FOR ADDING ETHOXYLATED AND / OR HYDROGENATED OIL |
| WO2009097953A1 (de) * | 2008-02-06 | 2009-08-13 | Merck Patent Gmbh | Uvb filter auf der basis von ascorbinsäurederivaten |
| EP2238121A1 (de) * | 2008-02-06 | 2010-10-13 | Merck Patent GmbH | Uva filter auf der basis von ascorbinsäurederivaten |
| WO2011145112A1 (en) * | 2010-05-17 | 2011-11-24 | Dynadis Biotehc (India) Private Limited | Process for isolation and purification of carotenoids |
| US8846723B2 (en) | 2010-07-29 | 2014-09-30 | Eastman Chemical Company | Esters of O-substituted hydroxy carboxylic acids and preparations thereof |
| US8613940B2 (en) | 2010-09-03 | 2013-12-24 | Eastman Chemical Company | Carbonate derivatives as skin care |
| US8329938B2 (en) | 2011-02-21 | 2012-12-11 | Eastman Chemical Company | Hydroxyalkanoic acid and hydroxyalkanoice acid oligomer esters of retinol |
| EP3092220B1 (en) | 2013-09-25 | 2021-01-20 | University of Florida Research Foundation, Inc. | Vitamin c prodrugs and uses thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2980702A (en) * | 1958-11-15 | 1961-04-18 | Merck Ag E | Heat resistant derivatives of l-ascorbic acid |
| JPH05331020A (ja) | 1992-05-26 | 1993-12-14 | Kanebo Ltd | 皮膚化粧料 |
| JP2613865B2 (ja) | 1993-09-14 | 1997-05-28 | 鐘紡株式会社 | 化粧料 |
| JPH08269074A (ja) | 1995-03-29 | 1996-10-15 | Pola Chem Ind Inc | 新規なアスコルビン酸誘導体及びこれを含有する化粧料 |
| DE19750526A1 (de) * | 1997-11-14 | 1999-05-20 | Basf Ag | Ascorbinsäurederivate enthaltende kosmetische und pharmazeutische Zubereitungen |
-
1997
- 1997-11-14 DE DE19750526A patent/DE19750526A1/de not_active Withdrawn
-
1998
- 1998-10-16 EP EP98119590A patent/EP0917871B1/de not_active Expired - Lifetime
- 1998-10-16 DE DE59813619T patent/DE59813619D1/de not_active Expired - Fee Related
- 1998-11-05 US US09/186,385 patent/US6346254B1/en not_active Expired - Fee Related
- 1998-11-11 JP JP10320704A patent/JPH11236332A/ja not_active Withdrawn
- 1998-11-16 CN CN98122464.4A patent/CN1211082C/zh not_active Expired - Fee Related
-
2001
- 2001-10-01 US US09/967,530 patent/US7102019B2/en not_active Expired - Fee Related
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101686925B (zh) * | 2006-08-11 | 2013-04-03 | 默克专利股份有限公司 | 抗坏血酸衍生物用于官能化基质的用途 |
| TWI462913B (zh) * | 2009-05-07 | 2014-12-01 | Cosmol Co Ltd | 製備抗壞血酸衍生物之方法 |
| CN115260170A (zh) * | 2021-04-30 | 2022-11-01 | 禾美生物科技(浙江)有限公司 | 抗坏血酸多肽衍生物及其制备方法和应用 |
| WO2022228475A1 (zh) * | 2021-04-30 | 2022-11-03 | 禾美生物科技(浙江)有限公司 | 抗坏血酸多肽衍生物及其制备方法和应用 |
| CN115260170B (zh) * | 2021-04-30 | 2024-05-28 | 禾美生物科技(浙江)有限公司 | 抗坏血酸多肽衍生物及其制备方法和应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0917871B1 (de) | 2006-06-28 |
| US6346254B1 (en) | 2002-02-12 |
| JPH11236332A (ja) | 1999-08-31 |
| US20020034527A1 (en) | 2002-03-21 |
| EP0917871A2 (de) | 1999-05-26 |
| DE19750526A1 (de) | 1999-05-20 |
| CN1211082C (zh) | 2005-07-20 |
| DE59813619D1 (de) | 2006-08-10 |
| EP0917871A3 (de) | 2003-05-28 |
| US7102019B2 (en) | 2006-09-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1223853A (zh) | 含有抗坏血酸衍生物的化妆品及药品制剂 | |
| AU748711B2 (en) | Cosmetic and pharmaceutical preparations containing photostable UV filters | |
| US6037487A (en) | Photo-stable cosmetic and pharmaceutical formulations containing UV-filters | |
| US6436373B1 (en) | Oligomeric diarylbutadienes | |
| AU759300B2 (en) | Use of cholesteric, liquid-crystalline compositions as UV filters in cosmetic and pharmaceutical preparations | |
| AU757965B2 (en) | 4,4-diarylbutadienes as water-soluble photostable UV filters for cosmetics and pharmaceutical preparations | |
| CA1315201C (fr) | Compositions pharmaceutiques a base de composes benzamido aromatiques | |
| US20050152858A1 (en) | Solubilizing agents for active or functional organic compounds | |
| KR20100052497A (ko) | 화장용 제형에서 수용성 성분을 보호하기 위한 나노분산액의 용도 | |
| AU2886900A (en) | Use of amino-substituted hydroxybenzophenones as photostable UV filters in cosmetic and pharmaceutical preparations | |
| US6143906A (en) | Ascorbyl sorbates | |
| US7727948B2 (en) | Mixture, comprising a surfactant and a cosurfactant that is an amphiphilic polymer | |
| ES2766259T3 (es) | Malonatos de bencilideno | |
| AU778388B2 (en) | Use of cyclic enamines as light protection agents | |
| US6407247B1 (en) | Photo-stable cosmetic and pharmaceutical formulations containing UV-filters | |
| AU742274B2 (en) | Cosmetic preparations comprising photostable UV-A filters | |
| AU755281B2 (en) | Cosmetic and pharmaceutical preparations comprising photostable UV filters | |
| EP1092721A1 (de) | Chirale Glucoside und deren Verwendung als chirale Dotierstoffe zur Herstellung von cholestrisch-flüssigkristallinen Zusammensetzungen | |
| JP2018501352A (ja) | 炭水化物部分エステルを含有する組成物 | |
| JP2963730B2 (ja) | ポリスルフィド化合物及びこれを有効成分とする脂質過酸化抑制剤 | |
| DE102006051088A1 (de) | Verwendung der 3,3'-Dihydroxyisorenieratin und verwandter Carotinoide | |
| AU754785B2 (en) | Use of isoindolinone derivatives as stabilizers for organic materials | |
| CA2528311C (en) | Mixture consisting of uv-a and uv-b filters | |
| KR101451401B1 (ko) | 비타민 c와 비타민 e의 컨쥬게이트 및 그를 포함하는 항산화제 | |
| KR20170076091A (ko) | 살리실산 유도체와 그 제조방법 및 이를 함유하는 미백용 화장료 조성물 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C06 | Publication | ||
| PB01 | Publication | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C17 | Cessation of patent right | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20050720 Termination date: 20091216 |