JP4533415B2 - 化粧料組成物 - Google Patents
化粧料組成物 Download PDFInfo
- Publication number
- JP4533415B2 JP4533415B2 JP2007237620A JP2007237620A JP4533415B2 JP 4533415 B2 JP4533415 B2 JP 4533415B2 JP 2007237620 A JP2007237620 A JP 2007237620A JP 2007237620 A JP2007237620 A JP 2007237620A JP 4533415 B2 JP4533415 B2 JP 4533415B2
- Authority
- JP
- Japan
- Prior art keywords
- pyridoxine
- group
- glucoside
- vitamin
- acid
- 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.)
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- 239000000203 mixture Substances 0.000 title claims description 90
- 239000002537 cosmetic Substances 0.000 title claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 120
- 239000003795 chemical substances by application Substances 0.000 claims description 28
- 230000002087 whitening effect Effects 0.000 claims description 19
- 230000037373 wrinkle formation Effects 0.000 claims description 13
- 125000003147 glycosyl group Chemical group 0.000 claims description 10
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 10
- 230000003712 anti-aging effect Effects 0.000 claims description 9
- 239000012190 activator Substances 0.000 claims description 8
- BJRNKVDFDLYUGJ-RMPHRYRLSA-N hydroquinone O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-RMPHRYRLSA-N 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 4
- 229960000271 arbutin Drugs 0.000 claims description 4
- 230000017531 blood circulation Effects 0.000 claims description 4
- BJRNKVDFDLYUGJ-UHFFFAOYSA-N p-hydroxyphenyl beta-D-alloside Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 230000003078 antioxidant effect Effects 0.000 claims description 3
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims description 3
- 239000007844 bleaching agent Substances 0.000 claims 1
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 description 280
- 229940011671 vitamin b6 Drugs 0.000 description 142
- 239000011677 pyridoxine Substances 0.000 description 123
- 235000008160 pyridoxine Nutrition 0.000 description 122
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 82
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 63
- RADKZDMFGJYCBB-UHFFFAOYSA-N Pyridoxal Chemical compound CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 description 55
- 150000003697 vitamin B6 derivatives Chemical class 0.000 description 53
- ZUFQODAHGAHPFQ-UHFFFAOYSA-N pyridoxine hydrochloride Chemical compound Cl.CC1=NC=C(CO)C(CO)=C1O ZUFQODAHGAHPFQ-UHFFFAOYSA-N 0.000 description 50
- 239000011764 pyridoxine hydrochloride Substances 0.000 description 50
- 235000019171 pyridoxine hydrochloride Nutrition 0.000 description 50
- 229960004172 pyridoxine hydrochloride Drugs 0.000 description 50
- -1 vitamin B6 glycosides Chemical class 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 44
- 125000006239 protecting group Chemical group 0.000 description 44
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 230000002829 reductive effect Effects 0.000 description 36
- 238000012360 testing method Methods 0.000 description 34
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 235000019441 ethanol Nutrition 0.000 description 28
- NHZMQXZHNVQTQA-UHFFFAOYSA-N pyridoxamine Chemical compound CC1=NC=C(CO)C(CN)=C1O NHZMQXZHNVQTQA-UHFFFAOYSA-N 0.000 description 28
- 239000007864 aqueous solution Substances 0.000 description 27
- 239000001488 sodium phosphate Substances 0.000 description 27
- 238000000034 method Methods 0.000 description 25
- 229910000162 sodium phosphate Inorganic materials 0.000 description 23
- 239000000243 solution Substances 0.000 description 23
- 239000002994 raw material Substances 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 21
- FAPWYRCQGJNNSJ-UBKPKTQASA-L calcium D-pantothenic acid Chemical compound [Ca+2].OCC(C)(C)[C@@H](O)C(=O)NCCC([O-])=O.OCC(C)(C)[C@@H](O)C(=O)NCCC([O-])=O FAPWYRCQGJNNSJ-UBKPKTQASA-L 0.000 description 20
- 229960002079 calcium pantothenate Drugs 0.000 description 20
- 235000011008 sodium phosphates Nutrition 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- 238000005160 1H NMR spectroscopy Methods 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 19
- 150000003839 salts Chemical class 0.000 description 19
- 235000019158 vitamin B6 Nutrition 0.000 description 19
- 239000011726 vitamin B6 Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000004128 high performance liquid chromatography Methods 0.000 description 17
- 239000000843 powder Substances 0.000 description 17
- 229960003581 pyridoxal Drugs 0.000 description 17
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 16
- 239000011521 glass Substances 0.000 description 16
- 235000008164 pyridoxal Nutrition 0.000 description 16
- 239000011674 pyridoxal Substances 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 15
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 235000013305 food Nutrition 0.000 description 14
- 239000008213 purified water Substances 0.000 description 14
- 150000001298 alcohols Chemical class 0.000 description 13
- 229940024606 amino acid Drugs 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- 235000011118 potassium hydroxide Nutrition 0.000 description 13
- 235000008151 pyridoxamine Nutrition 0.000 description 13
- 239000011699 pyridoxamine Substances 0.000 description 13
- 235000011121 sodium hydroxide Nutrition 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 229940088594 vitamin Drugs 0.000 description 13
- 229930003231 vitamin Natural products 0.000 description 13
- 235000013343 vitamin Nutrition 0.000 description 13
- 239000011782 vitamin Substances 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 11
- 235000001014 amino acid Nutrition 0.000 description 11
- 239000007810 chemical reaction solvent Substances 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 239000006210 lotion Substances 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 11
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 10
- 239000003708 ampul Substances 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- 239000003814 drug Substances 0.000 description 10
- 230000035484 reaction time Effects 0.000 description 10
- 229960001153 serine Drugs 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 150000001413 amino acids Chemical group 0.000 description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 9
- 238000005984 hydrogenation reaction Methods 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 235000000346 sugar Nutrition 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 7
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- 239000012046 mixed solvent Substances 0.000 description 7
- 229960003330 pentetic acid Drugs 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
- 150000003722 vitamin derivatives Chemical class 0.000 description 7
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 description 6
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 6
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- 125000004036 acetal group Chemical group 0.000 description 6
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 6
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- 238000011156 evaluation Methods 0.000 description 6
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 6
- GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 6
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- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
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- PFIPZKASKUWLHH-UHFFFAOYSA-N pyridoxamine hydrochloride Chemical compound Cl.CC1=NC=C(CO)C(CN)=C1O PFIPZKASKUWLHH-UHFFFAOYSA-N 0.000 description 4
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- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
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- 208000017520 skin disease Diseases 0.000 description 1
- 206010040882 skin lesion Diseases 0.000 description 1
- 231100000444 skin lesion Toxicity 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007974 sodium acetate buffer Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229960002668 sodium chloride Drugs 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- WTWSHHITWMVLBX-DKWTVANSSA-M sodium;(2s)-2-aminobutanedioate;hydron Chemical compound [Na+].[O-]C(=O)[C@@H](N)CC(O)=O WTWSHHITWMVLBX-DKWTVANSSA-M 0.000 description 1
- QWSZRRAAFHGKCH-UHFFFAOYSA-M sodium;hexane-1-sulfonate Chemical compound [Na+].CCCCCCS([O-])(=O)=O QWSZRRAAFHGKCH-UHFFFAOYSA-M 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 235000021055 solid food Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- PZDOWFGHCNHPQD-VNNZMYODSA-N sophorose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](C=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O PZDOWFGHCNHPQD-VNNZMYODSA-N 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229940001941 soy protein Drugs 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 208000003265 stomatitis Diseases 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- 150000004044 tetrasaccharides Chemical class 0.000 description 1
- JHYAVWJELFKHLM-UHFFFAOYSA-H tetrasodium;2-hydroxypropane-1,2,3-tricarboxylate;iron(2+) Chemical compound [Na+].[Na+].[Na+].[Na+].[Fe+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O JHYAVWJELFKHLM-UHFFFAOYSA-H 0.000 description 1
- 239000000892 thaumatin Substances 0.000 description 1
- 235000010436 thaumatin Nutrition 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical class [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- AUALKMYBYGCYNY-UHFFFAOYSA-E triazanium;2-hydroxypropane-1,2,3-tricarboxylate;iron(3+) Chemical compound [NH4+].[NH4+].[NH4+].[Fe+3].[Fe+3].[Fe+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O AUALKMYBYGCYNY-UHFFFAOYSA-E 0.000 description 1
- XPDWGBQVDMORPB-UHFFFAOYSA-N trifluoromethane acid Natural products FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 150000004043 trisaccharides Chemical class 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- FUCBQMFTYFQCOB-UHFFFAOYSA-N trityl perchlorate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCl(=O)(=O)=O)C1=CC=CC=C1 FUCBQMFTYFQCOB-UHFFFAOYSA-N 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 208000026188 vitamin metabolic disease Diseases 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 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
- 229960002675 xylitol Drugs 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 235000013904 zinc acetate Nutrition 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000011478 zinc gluconate Nutrition 0.000 description 1
- 239000011670 zinc gluconate Substances 0.000 description 1
- 229960000306 zinc gluconate Drugs 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
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- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
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- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
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Description
R6−X (III)
(式中、R6は保護基を有していてもよいグリコシル基を示し、Xは脱離基を示す)で表される化合物とを反応させて上記の一般式(IV)で表される化合物を得る工程、及び必要に応じて上記一般式(IV)で表される化合物を脱保護する工程を含む方法が提供される。
ピリドキシン 3-β-グルコシド
ピリドキシン 3-α-グルコシド
ピリドキサミン 3-β-グルコシド
ピリドキサミン 3-α-グルコシド
ピリドキサール 3-β-グルコシド
ピリドキサール 3-α-グルコシド
ピリドキシン 3-β-ガラクトシド
ピリドキシン 3-α-ガラクトシド
N-(4-ピリドキシルメチレン)-L-セリン 3-β-グルコシド
N-(4-ピリドキシルメチレン)-L-セリン 3-α-グルコシド
ピリドキシン 3-リン酸
ピリドキシン 3,4'-環状リン酸
N-(4-ピリドキシルメチレン)-L-セリン 3-リン酸
などを挙げることができる。また、これらの化合物のD-異性体をさらに好ましい例として挙げることができる。もっとも、本発明の化合物はこれらの具体例に限定されることはない。
a) 3-(2,3,4,6-テトラ-O-アセチル-β-D-グルコピラノシル)-α4,α5-ジ-O-アセチルピリドキシン
α4,α5-ジ-O-アセチルピリドキシン塩酸塩 (4.90 g、17.2 mmol)にCHCl3(150 ml)と飽和NaHCO3水溶液(100 ml)を加え、室温で1時間攪拌した後、有機層を飽和食塩水で洗浄した。有機層を無水MgSO4で乾燥後、溶媒を減圧留去した。得られた白色固体(4.0 g)、2,3,4,6-テトラ−O−アセチル−α−D−グルコピラノシルブロマイド(9.74 g、23.7 mmol)をCH2Cl2(70 ml)に溶解し、炭酸銀(4.36 g、15.8 mmol)を加え、遮光、窒素雰囲気及び還流下、一晩攪拌した。反応液を減圧濃縮後、残渣をカラムクロマトグラム(シリカゲル;600 g、n-ヘキサン:酢酸エチル=1:2の混合溶媒で溶出)で精製して白色固体の表記化合物(7.17 g、収率78%)を得た。
融点:89-93℃
比旋光度 [α]D=-20°(c=0.2、CHCl3)
1H-NMR (CDCl3) δ ppm ; 2.03(3H,s), 2.04(3H,s), 2.07(3H,s), 2.08(3H,s), 2.09(3H,s), 2.14(3H,s), 2.55(3H,s), 3.5-3.6(1H,m), 4.0-4.2(2H,m), 4.83(1H,d), 5.1-5.4(7H,m), 8.38(1H,s)
例1−aの化合物 (7.10 g、12.2 mmol)をメタノール(40 ml)と水(20 ml)に溶解し、氷冷攪拌下、水酸化カリウム(3.38 g、51.8 mmol)を加え、溶解させた後、室温で1時間攪拌した。反応液を1N塩酸で中和し、減圧濃縮後、残渣をカラムクロマトグラム(SP850 ; 100 ml、水から20% メタノール水溶液で溶出)で精製した。得られた固体を水(200 ml)に溶解し、活性炭(50% 湿体、150 mg)を投入し、60℃で30分間、攪拌した。活性炭を濾別後、水を減圧留去し、エタノール−水(10:1、88 ml)から再結晶することにより、白色結晶の表記化合物(3.14 g、収率78%)を得た。この化合物のアノマー型は、α−グルコシダーゼ(ロッシュ社製、Saccharomyces cerevisiae 由来)によって加水分解されず、β−グルコシダーゼ(オリエンタル酵母社製、アーモンド由来)によって完全に加水分解されピリドキシンが遊離したことから、β型であることが確認された。
融点;211-212℃
比旋光度 [α]D= -6.0°(c=1.0、H2O)、
1H-NMR (DMSO-d6) δppm ; 2.49(3H,s), 3.0-3.7(6H,m), 4.3-5.2(10H,m), 5.59(1H,d,J = 4.8 Hz), 8.25(1H,s)
a) 3-(2,3,4,6-テトラ-O-アセチル-β-D-グルコピラノシル)-ピリドキサ−ル モノエチルアセタール
窒素雰囲気下でピリドキサ−ルモノエチルアセタール塩酸塩(11.0 g、47.5 mmol)をCH2Cl2(100 ml)に懸濁し、氷冷下、トリエチルアミン(6.63 ml、47.5 mmol)を加え、室温に昇温後、2,3,4,6-テトラ-O-アセチル-α-D-グルコピラノシルブロマイド(23.4 g 、57.0 mmol)を加えた。反応容器を遮光後、炭酸銀(13.1 g 、47.5 mmol)を加え、室温で18時間攪拌した後、35℃で24時間攪拌を続けた。反応液をろ過、減圧濃縮後、残渣をカラムクロマトグラム(シリカゲル;600 g、n-Hexane:酢酸エチル=1:2の混合溶媒で溶出)で精製して、表記化合物(20.8 g、84%)を得た。
1H-NMR (CDCl3)δppm; 1.2-1.4(3H,m), 2.0-2.1(12H,m), 2.45(1.7H,s), 2.54(1.3H,s), 3.5-4.3(5H,m), 4.9-5.6(6H,m), 6.24(0.5H,d,J=1.8Hz), 6.42(0.5H,d,J=1.7Hz), 8.16(0.5H,s), 8.30(0.5H,s)
例2-a )の化合物(20.0 g、38.1 mmol)に水(200 ml)及び1N 塩酸 (38 ml)を加え、還流下、30分間攪拌した。反応液を室温まで冷却後、飽和重曹水(200 ml)を加え、酢酸エチル (300 ml)で抽出した。無水MgSO4乾燥、減圧濃縮後、残渣をカラムクロマトグラム(シリカゲル;600 g、CHCl3:MeOH(メタノール)=50:1の混合溶媒で溶出)で精製して、表記化合物(10.8 g、57.0%)を得た。
1H-NMR (CDCl3)δppm; 2.0-2.1(12H,m), 2.45(1.8H,s), 2.54(1.2H,s), 3.6-4.3(4H,m), 4.9-5.5(6H,m), 6.6-6.7(1H,m), 8.19(0.6H,s), 8.29(0.4H,s)
例2-b)の化合物(2.0 g、4.02 mmol)をMeOH(25 ml)と水(3 ml)に溶解し、氷冷攪拌下、水酸化カリウム(262 mg、4.02 mmol)を水(2 ml)に溶解したものを加え、室温で1時間攪拌した。TLCで原料の消失を確認後、反応液を1N塩酸で中和し、減圧濃縮後、残渣をカラムクロマトグラム(SP850 ; 100 ml、水から30% MeOH水溶液で溶出)で精製した。
得られた固体を水(200 ml)に溶解し、活性炭(50%湿体、150 mg)を投入し、60℃で30分間攪拌した。活性炭をろ別後、ろ液を凍結乾燥し、白色無定形粉末の表記化合物(1.16g、88%)を得た。
融点:130〜140℃
比旋光度[α]D= -38.4°(c=1.0、H2O)
1H-NMR (DMSO-d6) δppm ; 2.42(3H,s), 3.0-3.5(5H,m), 3.6-3.8(1H,m), 4.6-5.5(7H,m), 6.5-6.6(1H,m), 6.84(0.4H,d,J=6.6Hz), 6.98(0.6H,d,J=7.0Hz), 8.05(0.6H,s), 8.20(0.4H,s)
a) 3-(2,3,4,6-テトラ-O-アセチル-β-D-グルコピラノシル)-ピリドキサ−ル オキシム
例2-b)の化合物(6.0 g、12.1 mmol)を水(200 ml)に懸濁し、酢酸ナトリウム(1.29 g 、15.7 mmol) と塩化ヒドロキシルアンモニウム(1.26 g、18.2 mmol)を加え、還流下、30分間攪拌した。室温まで冷却後、酢酸エチル(300 ml)で抽出し、無水MgSO4乾燥後、溶媒を減圧留去し、残渣にジエチルエーテルを加え、析出した固体をろ取し、ジエチルエーテルで洗浄後、減圧乾燥し、表記化合物(5.49 g、89%)を得た。
1H-NMR (CDCl3) δppm; 2.03(3H,s), 2.03(3H,s), 2.05(3H,s), 2.19(3H,s), 2.56(3H,s), 3.5-3.7(1H,m), 4.0-4.2(2H,m), 4.61(2H,brs), 4.80(1H,d,J=7.9Hz), 5.0(1H,brs), 5.1-5.5(3H,m), 8.40(1H,s), 8.57(1H,s), 10.9(1H,brs)
例3-a)の化合物(2.28 g、4.41 mmol)を酢酸(60 ml)に溶解し、5% Pd-C(AD、50%wet、1.2g)の存在下、室温で1時間接触水素化した。触媒をろ別後、酢酸を減圧留去し、残渣をカラムクロマトグラム(シリカゲル;50 g、CHCl3:MeOH:AcOH(酢酸)=10:1:0.01で溶出)で精製し、表記化合物 (1.97g、90%)を得た。
1H-NMR (CDCl3) δppm; 2.01(3H,s), 2.05(6H,s), 2.16(3H,s), 2.53(3H,s), 3.5-5.4(14H,m), 8.32(1H,s)
例3-b)の化合物(1.90 g 、3.81 mmol)をメタノール(25 ml)と水(3 ml)に溶解し、氷冷攪拌下、水酸化カリウム(498 mg、7.62 mmol)を水(4 ml)に溶解したものを加え、室温で1時間攪拌した。原料の消失を確認後、6N 塩酸で中和し、減圧濃縮し、残渣を水(50 ml)に溶解し、1N 水酸化ナトリウムでpH 10とし、カラムクロマトグラム(SP850 ; 100 ml、水から30% MeOH水溶液で溶出)で精製した。得られた固体を水(200 ml)に溶解し、活性炭(50% 湿体、250 mg)を加え、60℃で30分間攪拌した。活性炭をろ別後、ろ液を凍結乾燥し、白色無定形粉末の表記化合物(189 mg、18%)を得た。
融点:205〜212℃
比旋光度[α]D= -6.1°(c=1.0、H2O)、
1H-NMR (DMSO-d6) δppm ; 2.49(3H,s), 3.0-3.5(10H,m), 3.6-3.8(2H,m), 4.02(1H,d,J=12.0Hz), 4.3-4.7(3H,m), 5.0-5.1(2H,m), 8.15(1H,s)
a) 3-(2,3,4,6-テトラ-O-アセチル-β-D-ガラクトピラノシル)-α4,α5-ジ-O-アセチル-ピリドキシン
α4,α5−ジ−O−アセチルピリドキシン塩酸塩(7.82 g、27.0 mmol)にCHCl3 (300 ml)と飽和NaHCO3水溶液 (200 ml)を加え、室温で1時間攪拌した後、有機層を飽和食塩水で洗浄した。有機層を無水MgSO4で乾燥後、溶媒を減圧留去した。得られた白色固体(11.4 g、27.0 mmol)と2,3,4,6-テトラ-O-アセチル-β-D-ガラクトピラノシルブロミドをCH2Cl2 (60 ml)に溶解し、炭酸銀(6.70 g、24.3 mmol)を加え、遮光、窒素雰囲気下、室温で15時間、還流下、7時間攪拌した。不溶物をろ別後、溶媒を減圧留去し、残渣をカラムクロマトグラム(シリカゲル;700 g、Hexane:酢酸エチル=1:3の混合溶媒で溶出)で精製し、白色固体の表記化合物(8.23 g、58%)を得た。
1H-NMR (CDCl3) δ ppm ; 1.97(3H,s), 2.02(3H,s), 2.09(3H,s), 2.10(3H,s), 2.15(3H,s), 2.22(3H,s), 2.56(3H,s), 3.7-3.9(1H,m), 4.0-4.2(2H,m), 4.79(1H,d,J=8.1Hz), 5.0-5.6(7H,m), 8.39(1H,s)
例4-a)の化合物(8.20 g、14.1mmol)をメタノール(80 ml)に溶解後、氷冷下、水酸化カリウム(5.99 g、91.8 mmol)を水(20 ml)に溶解したものを加え、室温で30分間攪拌した。原料の消失を確認後、6N 塩酸で中和し、減圧濃縮後、残渣をカラムクロマトグラム(SP850 ; 100 ml、水から15% MeOH水溶液で溶出)で精製した。得られた固体を水(400 ml)に溶解し、活性炭(50% 湿体、500 mg)を加え、60℃で30分間攪拌した。活性炭をろ別後、水を減圧留去し、残渣をエタノール−水(2:1)(150 ml)から再結晶することにより無色針状結晶の表記化合物(3.67g 、79%)を得た。
融点:215℃以上
比旋光度[α]D= +4.5°(c=1.0、H2O)
1H-NMR (DMSO-d6) δppm ; 2.49(3H,s), 3.2-3.7(6H,m), 4.4-4.9(9H,m), 5.20(1H,t), 5.45(1H,d,J=5.0Hz), 8.25(1H,s)
L-セリン(1.06 g、10.1 mmol)をMeOH(50 ml)に懸濁攪拌し、50%水酸化カリウム(1.12 ml、10 mmol)を加え溶解した。そこへ例2-b)の化合物(5.0 g 、10.1mmol)を加え、室温で30分間攪拌した後、5% Pd-C(AD、50%wet、5.0g)の存在下、室温で16時間接触水素化した。析出した結晶をAcOH(1.2 ml)と水(10 ml)を加え溶解し、触媒をろ別後、溶媒を減圧留去した。残渣を逆相カラムクロマトグラム(Chromatorex ODS-1020T;250 g、水で溶出)で精製した。得られた固体を水(100 ml)に溶解し、活性炭(50% 湿体、500 mg)を加え、60℃で30分間攪拌した。活性炭をろ別後、ろ液を濃縮乾固した。得られた白色固体を90% エタノール(100 ml)で再結晶し、白色結晶の表記化合物(2.38 g、56.9%)を得た。
融点:165〜175℃
比旋光度[α]D= +8.8°(c=1.0、H2O)、
1H-NMR (DMSO-d6) δppm ;2.49(3H,s), 3.0-3.7(14H,m), 4.0-4.2(2H,m), 4.56(2H,s), 4.68(1H,d,J=7.5Hz),5.1(3H,brs), 8.21(1H,s)。
a) 3-ホスホリル-α4,α5-ジ-O-アセチルピリドキシン
α4,α5−ジ−O−アセチルピリドキシン塩酸塩(33.3 g、131 mmol)をピリジン(350 ml)に溶解し、水冷下でオキシ塩化リン(61.3 ml、657 mmol)のピリジン(150 ml)溶液を1.5時間かけて滴下した。1時間攪拌を続けた後、40℃に昇温し、15時間攪拌した。反応液を減圧濃縮し、残渣に氷冷下、アセトニトリル (100 ml)及び水(400 ml)を加え1.5時間攪拌した。28%アンモニア水を加え、溶液のpHを7.0とした後、減圧濃縮し、残渣をカラムクロマトグラム (シリカゲル250g、CHCl3:MeOH=10:1→5:1の混合溶媒で溶出)で精製し、表記化合物(25.6 g、59%)を得た。
1H-NMR (DMSO-d6) δppm ; 1.98(3H,s), 2.05(3H,s), 2.49(3H,s), 5.14(2H,s), 5.31(2H,s), 6.9-7.3(1H,m), 8.22(1H,s)
例6-a)の化合物(25.6 g、76.8 mmol)をメタノール(150 ml)と水(100 ml)に溶解後、氷水冷下、水酸化ナトリウム(6.34 g、154 mmol)を水(100 ml)で溶解したものを加え、室温で1時間攪拌した。原料の消失を確認後、2N-塩酸で中和し、減圧濃縮後、残渣をカラムクロマトグラム(シリカゲル250 g、CHCl3:MeOH= 5:1→4:1→2:1の混合溶媒で溶出)で精製した。これを水(254 ml)に溶解、イオン交換樹脂(DOWEX50WX8、15g)を投入しpH3.2とした後、カラムクロマトグラム(SP207;800 ml、水で溶出)で脱塩した。目的フラクションを減圧濃縮後、水(300 ml)に溶解し、活性炭(50% 湿体、1.5 g)を投入し、50℃で30分間攪拌した。メンブランろ過後、凍結乾燥し、白色無定形粉末の表記化合物(10.4 g、58%)を得た。
1H-NMR (DMSO-d6) δppm ; 2.44(3H,s), 3.89(2H,brs), 4.50(2H,s), 5.22(2H,d,J=11.7Hz), 8.12(1H,s)
例6-b)の化合物(10.4 g、45 mmol)を水(80 ml)に溶解し1N 水酸化ナトリウムを加えてpH 10とし、カラムクロマトグラム(SP207;800 ml、水で溶出)で脱塩した。目的フラクションを集め、活性炭(50% 湿体、1 g)を投入し、50℃で30分間攪拌した。メンブランろ過後、減圧乾固し、エタノール(40 ml)とジエチルエーテル(300 ml)を加え、析出した結晶をろ取し、減圧下乾燥し、白色結晶の表記化合物 (9.63 g、85%)を得た。
融点:190〜200℃
1H-NMR (DMSO-d6) δppm ; 2.28(3H,s), 4.37(2H,d,J=3.5Hz), 5.07(2H,d,J=5.9Hz), 5.22(1H,brs), 7.89(1H,s)
例6-b)の化合物(20.0 g、86.5 mmol)を水(500 ml)に溶解し酸化マグネシウム(1.6 g)を加えてpH 7.5 とし、カラムクロマトグラム(SP207;1,000 ml、水で溶出)で脱塩した。目的フラクションを集め、活性炭(50% 湿体、1 g)を投入し、50℃で30分間攪拌した。メンブランろ過後、減圧乾固し、アセトン(40 ml)を加え、析出した結晶をろ取し、減圧下乾燥し、白色結晶の表記化合物 (12.2 g、58%)を得た。
融点:230℃以上
1H-NMR (D2O) δppm ; 2.42(3H,s), 4.60(2H,s), 4.83(1H,s), 5.38(2H,d,J=12.3Hz), 8.02(1H,s)
例6-a)の化合物(1.0 g、3.0 mmol)をメタノール(10 ml)に溶解後、氷水冷下、炭酸水素ナトリウム(0.50 g、6.0 mmol)を水(10 ml)で溶解したものを加え、室温で24時間攪拌した。2N塩酸で中和し、減圧濃縮後、残渣をカラムクロマトグラム(シリカゲル30 g、CHCl3:MeOH= 4:1→2:1の混合溶媒で溶出)で精製した。目的フラクションを減圧濃縮後、残渣を水(10 ml)に溶解し、逆相カラムクロマトグラム(Chromatorex ODS-1020T;30g、水で溶出)で精製した。目的フラクションを30mlまで減圧濃縮後、活性炭(50% 湿体、1 g)を投入し、50℃で30分間攪拌した。メンブランろ過後、凍結乾燥し、白色無定形粉末の表記化合物(0.299 g、34%)を得た。
融点:137〜140℃
1H-NMR (DMSO-d6) δppm ; 2.39(3H,s), 4.49(2H,d,J=6.6Hz), 4.61(2H,d,J=4.2Hz), 5.14(1H,t), 5.93(1H,t), 8.17(1H,s)
例1-b)の化合物 (2.0 g、6.0 mmol)を水(150 ml)に溶解し、1N塩酸(6.0 ml)を加え、室温で1時間攪拌した後、水を減圧留去した。残渣をエタノール(130 ml)と水(10 ml)に還流下溶解し、冷蔵庫(5℃)で5日間冷却した。晶出した結晶をろ過し、減圧乾燥し、白色結晶の表記化合物(1.84 g、収率83%)を得た。
比旋光度[α]D= +1.7°(c=1.0、H2O)、融点:166〜170℃
1H-NMR (DMSO-d6) δppm ; 2.73(3H,s), 3.3-3.4(1H,m), 3.5-3.7(2H,m), 3.7-3.9(3H,m), 4.7-5.0(12H,m), 8.47(1H,s)
a) 3-(3,4,6‐トリ‐O‐アセチル‐α‐D‐グルコピラノシル)-α4,α5‐ジ‐O‐アセチルピリドキシン
α4,α5‐ジ‐O‐アセチルピリドキシン塩酸塩 (0.67 g、2.34 mmol)にCHCl3(10 ml)と飽和NaHCO3水溶液(10 ml)を加え、室温で1時間攪拌した後、有機層を飽和食塩水で洗浄した。有機層を無水MgSO4で乾燥後、溶媒を減圧留去した。得られた白色固体(0.59 g)と3,4,6‐トリ‐O‐アセチル‐β‐D‐グルコピラノシルクロライド(0.50 g、1.54 mmol)をトルエン(10 ml)に溶解し、モレキュラーシーブス4A(0.50 g)を加え、窒素雰囲気下、100℃で2時間、攪拌した。反応液を減圧濃縮後、残渣をカラムクロマトグラム(シリカゲル;50 g、n-ヘキサン:酢酸エチル=1:2の混合溶媒で溶出)で精製して薄黄色オイルの表記化合物と3-(3,4,6-トリ‐O‐アセチル‐β‐D‐グルコピラノシル)‐α4,α5‐ジ‐O‐アセチルピリドキシンの混合物(0.38g、収率46%、α:β=0.3:0.7)を得た。
1H-NMR (CDCl3) δ ppm ; 2.0-2.2(15H,m), 2.59(2.3H,s), 2.67(0.7H,s), 3.4-4.8(6H,m), 5.0-5.6(6H,m), 8.35(0.2H,s), 8.38(0.8H,s)
例10-a)の化合物 (0.37 g、0.69 mmol)をメタノール(4 ml)と水(2 ml)に溶解し、氷冷攪拌下、水酸化カリウム(0.34 g、5.15 mmol)を加え、溶解させた後、室温で1時間攪拌した。反応液を1N塩酸で中和し、減圧濃縮後、残渣を水(14 ml)に溶解し、1M酢酸ナトリウム緩衝液(1.6 ml)とβ−グルコシダーゼ(オリエンタル酵母社製、アーモンド由来、4mg、147 U)を加え、37℃で14時間、インキュベートした。反応液を減圧濃縮後、カラムクロマトグラム(Chromatorex ODS-1020T;10 g、水で溶出)で精製した。得られた固体を水(10 ml)に溶解し、活性炭(50% 湿体、10 mg)を投入し、60℃で30分間、攪拌した。活性炭を濾別後、水を減圧留去し、白色結晶粉末の表記化合物(54 mg、収率 24%)を得た。この化合物はβ−グルコシダーゼ(オリエンタル酵母社製、アーモンド由来)によって加水分解されず、α−グルコシダーゼ(ロッシュ社製、Saccharomyces cerevisiae 由来)によって完全に加水分解されピリドキシンが遊離したことから、この化合物のアノマー型はα型であることが確認された。
比旋光度 [α]D= +141,8°(c=1.0、H2O)、融点;201〜202℃
1H-NMR (DMSO-d6) δppm ; 2.49(3H,s), 3.1-3.5(3H,m), 3.5-3.7(2H,m), 3.8-3.9(1H,m), 4.5-4.8(5H,m), 4.9-5.1(3H,m), 5.1-5.3(2H,m), 5.45(1H,d,J=5.3Hz), 8.16(1H,s)
ピリドキシン 3-β-D-グルコシドの0.5%(w/v)水溶液(pH 6.7)0.3 mlを1 ml容ガラスアンプルに封入し、D65蛍光ランプ(東芝)を14日間、照射した。照射は室温で行い、照度は13,000Lxとした。照射前、照射1日後、照射7日後、照射14日後のサンプルをHPLCで分析し、ピリドキシン 3-β-D-グルコシド含量を測定した。同濃度の塩酸ピリドキシン(pH 6.7に調整)について同様の処理を行い、結果を比較した。HPLC測定条件は以下の通りである。
カラム Inertsil ODS-3 (5μm,φ 4.6×150 mm, GL Science Inc.)
溶離液 アセトニトリル:0.1%(v/v)トリフルオロ酢酸, 5mM sodium 1-hexanesulfonate = 1:9
流速 0.5 ml / min
検出 UV 280 nm
カラム温度 40℃
結果を第1図に示す。塩酸ピリドキシンが1日でほとんど分解されるのに対し、ピリドキシン 3-β-D-グルコシドは14日間ランプ照射しても分解が見られず、光安定性が格段に向上していることがわかった。また、塩酸ピリドキシン水溶液が光照射により淡黄色に着色するのに対して、ピリドキシン 3-β-D-グルコシド水溶液では着色が認められなかった。
ピリドキシン 3-β-D-グルコシドの0.5%(w/v)水溶液(pH 6.7)0.3mlを1ml容ガラスアンプルに封入し、遮光状態で50℃に保った。90日間加温し、その間サンプルをHPLCで分析(分析条件は試験例1と同様)し、ピリドキシン 3-β-D-グルコシド含量を測定した。同濃度の塩酸ピリドキシン(pH6.7に調整)について同様の処理を行い、結果を比較した。
結果を第2図に示す。50℃、90日間の加温で塩酸ピリドキシンが約20%が分解するのに対し、ピリドキシン 3-β-D-グルコシドはほとんど分解しなかった。また、50℃、90日間の加温で塩酸ピリドキシン水溶液が黄色に着色するのに対し、ピリドキシン 3-β-D-グルコシド水溶液は着色しなかった。
ピリドキシン 3-β-D-グルコシド塩酸塩、ピリドキサール 3-β-D-グルコシド、ピリドキサミン 3-β-D-グルコシド、ピリドキシン 3-β-D-ガラクトシド及び塩酸ピリドキシンそれぞれの0.5% (w/v) 水溶液(pH6.3-7.2にHCl又はNaOHで調整)0.3mlを1ml容ガラスアンプルに封入し、試験例1と同様の光照射及びHPLC定量をおこなった。結果を第3図に示す。塩酸ピリドキシンが1日でほとんど分解されるのに対し、ピリドキシン 3-β-D-グルコシド塩酸塩、ピリドキサミン 3-β-D-グルコシド、ピリドキシン 3-β-D-ガラクトシドは14日間ランプ照射しても分解がみられず、光安定性が格段に向上していることがわかった。ピリドキサール 3-β-D-グルコシドについても安定性は明らかに向上していた。また、塩酸ピリドキシン水溶液が光照射により、淡黄色に着色するのに対し、ピリドキシン 3-β-D-グルコシド塩酸塩、ピリドキサール 3-β-D-グルコシド、ピリドキサミン 3-β-D-グルコシド、ピリドキシン 3-β-D-ガラクトシドの各水溶液は着色しなかった。
ピリドキシン 3-β-D-グルコシド塩酸塩、ピリドキサール 3-β-D-グルコシド、ピリドキサミン 3-β-D-グルコシド、ピリドキシン 3-β-D-ガラクトシド、塩酸ピリドキシン、ピリドキサール塩酸塩及びピリドキサミン塩酸塩それぞれの0.5% (w/v) 水溶液(pH6.3-7.2にHCl又はNaOHで調整) 0.3 mlを1 ml容ガラスアンプルに封入し、試験例2と同様に、50℃加温及びHPLC分析を行った。結果を第4図に示す。50℃、90日間の加温で塩酸ピリドキシンが約15%、ピリドキサール塩酸塩が55%、ピリドキサミン塩酸塩が85%が分解するのに対し、ピリドキシン 3-β-D-グルコシド塩酸塩、ピリドキサール 3-β-D-グルコシド、ピリドキサミン 3-β-D-グルコシド、ピリドキシン 3-β-D-ガラクトシドはほとんど分解しなかった。また、50℃、90日間の加温で塩酸ピリドキシン、ピリドキサール塩酸塩、ピリドキサミン塩酸塩水溶液が黄色に着色するのに対し、ピリドキシン 3-β-D-グルコシド塩酸塩、ピリドキサール 3-β-D-グルコシド、ピリドキサミン 3-β-D-グルコシド、ピリドキシン 3-β-D-ガラクトシドの各水溶液は着色しなかった。
N-(4-ピリドキシルメチレン)-L-セリン 3-β-D-グルコシド及び塩酸ピリドキシンそれぞれの0.5% (w/v) 水溶液(pHにHCl又はNaOHで調整)0.3 mlを1 ml容ガラスアンプルに封入し、試験例1と同様の光照射及びHPLC定量をおこなった。結果を第5図に示す。塩酸ピリドキシンが1日でほとんど分解されるのに対し、N-(4-ピリドキシルメチレン)-L-セリン 3-β-D-グルコシドは14日間ランプ照射しても分解がみられず、光安定性が格段に向上していることがわかった。
ピリドキシン 3,4'-環状リン酸ナトリウム及びピリドキシン 3-リン酸二ナトリウム0.5% (w/v) 水溶液(pH6.5−6.8に調整) 0.3 mlを1ml容ガラスアンプルに封入し、試験例1と同様の光照射及びHPLC定量をおこなった。結果を第6図に示す。塩酸ピリドキシンが1日でほとんど分解されるのに対し、ピリドキシン 3,4'-環状リン酸ナトリウムは14日間ランプ照射しても分解がみられず、光安定性が格段に向上していることがわかった。ピリドキシン 3-リン酸二ナトリウムも明らかに光安定性が向上していた。また、塩酸ピリドキシン水溶液が光照射により、淡黄色に着色するのに対し、ピリドキシン 3,4'-環状リン酸ナトリウム水溶液及びピリドキシン 3-リン酸二ナトリウム水溶液は着色しなかった。
ピリドキシン3,4'-環状リン酸マグネシウム 0.5%(w/v)水溶液(pH6.5-6.8に調整)0.3 mlを1 ml 容ガラスアンプルに封入し、試験例1と同様に7日間の光照射及びHPLC定量を行なった。結果を第7図に示す。
ピリドキシン 3-α-D-グルコシド 0.5%(w/v)水溶液(pH6.5-6.8に調整)0.3 mlを1 ml容ガラスアンプルに封入し、試験例1と同様に1日間の光照射及びHPLC定量を行なった。結果を第8図に示す。
ピリドキシン3-硫酸ナトリウムを文献(The Journal of Biological Chemistry, 262, pp.2642-2644, 1987)に従って合成した。ピリドキシン 3-硫酸ナトリウム 0.5%(w/v)水溶液(pH6.5−6.8に調整)0.3 mlを1 ml容ガラスアンプルに封入し、試験例1と同様に14日間の光照射及びHPLC定量を行なった。結果を第9図に示す。
ピリドキシン 3,4'-環状リン酸ナトリウム及び塩酸ピリドキシン0.5% (w/v) 水溶液(pH6.5−6.8に調整)0.3 mlを1ml容ガラスアンプルに封入し、試験例2と同様に、50℃加温及びHPLC分析を行った。結果を第10図に示す。50℃、90日間の加温で塩酸ピリドキシンが、約15%分解するのに対し、ピリドキシン 3,4'-環状リン酸ナトリウムはほとんど分解しなかった。また、50℃、90日間の加温で塩酸ピリドキシン水溶液が黄色に着色するのに対し、ピリドキシン 3,4'-環状リン酸ナトリウム水溶液は着色しなかった。
セラミド配合物 0.1 g、1,3-ブチレングリコール 2.5 g、ジプロピレングリコール 2.5 g、メチルパラベン 0.01 gを80℃にて加温し透明になるまで攪拌した。35℃まで冷却後、攪拌しながら ビタミンB6誘導体(ピリドキシン3-β-D-グルコシド、ピリドキシン3-β-D-グルコシド塩酸塩、又はピリドキシン 3,4'-環状リン酸ナトリウム;以下、試験例11〜16において「ビタミンB6誘導体」という場合には上記3つのいずれかの物質を意味する)0.1 g又はピリドキシン 3-硫酸ナトリウム 0.1 gのいずれかと、ソルビトール発酵多糖 1.0 g及び精製水 90 mlを加えて溶解するまで攪拌し、10%クエン酸水溶液にてpH6.4とし、その後、精製水にて100 mlに調製しローションとした。この調製液には沈殿等が認められなかった。調製したローションをガラス瓶に6 ml入れ、D65蛍光ランプにて総照度として0、6万18万、及び30万lux・hr の光に曝しビタミンB6誘導体の定量を行い、別途、50℃に保存し、0、14日、1ヶ月、2ヶ月後に試験例1に記載のHPLC法によりビタミンB6誘導体の定量を行った。
50℃に保存した結果を第12図に示す。ビタミンB6誘導体は、全く分解されないかほとんど分解が認められず、塩酸ピリドキシンより熱安定性が良好であった。
ヤシ油脂肪酸メチルタウリンナトリウム 10.0 g、ポリオキシエチレンアルキルエーテル硫酸ナトリウム 20.0 g、ラウリルジメチルアミノ酢酸ベタイン 10.0 g、ヤシ油脂肪酸ジエタノールアミド 4.0 g、プロピレングリコール 2.0 g、ビタミンB6誘導体 0.1 g、パラオキシ安息香酸メチル 0.01 g を精製水 40 mlに加えて70℃に加温し溶解した。35℃以下まで冷却後、10%クエン酸水溶液にてpH6.8とし、その後、精製水にて100 mlに調製しシャンプーとした。この調製液には沈殿等が認められなかった。調製したシャンプーはガラス瓶に6 ml入れ、D65蛍光ランプにて総照度として0、6万、18万、及び30万lux・hr の光に曝しビタミンB6誘導体の定量を行い、別途、50℃に保存し、0日、14日、1ヶ月、2ヶ月後にビタミンB6誘導体の定量を上記実施例11と同様にHPLC法により行った。
50℃に保存した結果を第14図に示す。ビタミンB6誘導体は、全く分解されないかほとんど分解が認められず、塩酸ピリドキシンより熱安定性が良好であった。
メチル硫酸ネオスチグミン 5 mg、L-アスパラギン酸カリウム 0.4 g、ホウ酸 5 mg、ホウ砂 5 mg、ホウ砂 5 mg、パラオキシ安息香酸メチル10 mg、クロロブタノール 0.1 g、ビタミンB6誘導体0.1 gを滅菌した精製水70 mlにて溶解した。溶解後、滅菌した精製水にて100 mlに調製し目薬とした。この調製液には沈殿等が認められなかった。調製した目薬はガラス瓶に6 ml入れ、D65蛍光ランプにて総照度として0、6万、18万及び、30万lux・hr の光に曝しビタミンB6誘導体の定量を上記実施例11と同様にHPLC法により行なった。
ブドウ糖 4.6 g、アスパルテーム 0.01 g、クエン酸 0.1 g、塩化ナトリウム 0.02 g、塩化カリウム 0.02 g、塩化マグネシウム 0.01 g、乳酸カルシウム 0.04 g、ビタミンB6誘導体 0.01 g、L-アスパラギン酸ナトリウム 0.07 g、L-グルタミン酸ナトリウム 0.02 g、L-アルギニン 0.02 g、香料 0.1 g を精製水 70 mlにて溶解し、その後、精製水にて100 mlに調整し飲料水とした。この調製液には沈殿などが認められなかった。調製した飲料水をガラス瓶に6 ml入れ、D65蛍光ランプにて総照度として0、6万、18万及び30万lux・hr の光に曝しビタミンB6誘導体の定量を上記実施例11と同様にHPLC法により行った。
小麦粉 10gにビタミンB6誘導体 0.1 gを加えて均一に混合した。さらに、ササミ 40.0 g、大豆タンパク30.0 g、ブドウ糖 5.0 g、クエン酸 0.001 g、塩化ナトリウム 1.0 g、硫酸銅 0.01 g、硫酸鉄 0.01 g、ソルビン酸 0.3 g、プロピレングリコール 5.0 gを順じ加えて均一に混合する。これに精製水を加えて100 gに調製し均一に混合し、ドッグフードとした。
ランプ照射の結果を第17図に示す。塩酸ピリドキシンが照射3日の18万lux・hrで90%残存となり、5日の30万lux・hrでは85%残存にまで分解されるのに対し、ビタミンB6誘導体は5日間ランプ照射しても分解はほとんど見られず、光安定性が格段に良好であった。
パントテン酸カルシウム 1 gとビタミンB6誘導体 1 gを乳鉢で均一に混合し、粉体の安定性試料とした。ガラス瓶に入れた試料を開封状態で40℃、75%湿度下のオーブンに保存た。0日、14日及び1ヶ月後に目視で性状を観察しビタミンB6誘導体及びパントテン酸カルシウム定量を上記実施例11と同様にHPLC法により行なった。但し、パントテン酸カルシウムのみ検出波長は210 nmを使用した。
試験例17(培養細胞によるメラニン生成抑制及び細胞生存率試験)
マウス由来のB16メラノーマ培養細胞を使用した。精製水に所定濃度溶解したビタミンB6誘導体(ピリドキシン 3-β-D-グルコシド)及びアルブチン(和光純薬社製)100μMを培地中に添加した。途中培地交換を行い、5日間培養後、細胞を回収し、細胞数を測定した後、細胞内のメラニンを定量した。溶媒コントロールとして、精製水を加えたものを用いた。溶媒コントロールのメラニン量を1として、各試料濃度における細胞内メラニン量をメラニン生成率とした。結果を第20図に示す。
紫外線照射によるシワ形成を下記調製方法により調製した試料が抑制するかどうかについて評価をおこなった。
[試料(抗皮膚障害製剤)の調製]
ピリドキシン 3-β-D-グルコシド塩酸塩及びジエチレントリアミン五酢酸五ナトリウム液(DETAPAC)を基剤(ポリエチレングリコール1000:エチルアルコール=1:1)に溶解し、2% 濃度に試料を調製し、ヘアレスマウス紫外線照射による皮膚評価試験に用いた。なお、DETAPACは陽性コントロールとして用いた。
1群8匹とし、紫外線照射90分前に上述の試料をヘアレスマウス(10週齢)背中に0.1 g塗布し、一定量の紫外線(東芝FL20S・BLBランプ)を1日2時間(5回/週)10週間照射し、シワ形成抑制効果を調べた。
これらの試料の紫外線吸収スペクトルを測定し、評価試験に影響を与えないことを確認した。
(シワ形成抑制効果)
紫外線照射10週後のシワ形成について、下記に示す「光皮膚老化グレード」に基づいてシワグレードを判定した。なお、結果は、8匹の評点の平均値で表し評価した。試験及び評価法はBissettらの文献(Photochem Photobiol, Volume:46, Issue:3, Page:367-78, Year:1987)を参考に改変して用いた。
下記成分(3)〜(5)及び(9)〜(11)を混合溶解した溶液と、成分(1)、(2)、(6)〜(8)及び(12)を混合溶解した溶液とを混合して、均一にし、化粧水を得た。
(処方) (%)
(1)グリセリン 5.0
(2)1,3-ブチレングリコール 6.5
(3)ポリオキシエチレン(20E.O.)ソルビタン 1.2
モノラウリン酸エステル
(4)エチルアルコール 8.0
(5)ビタミンB6誘導体(ピリドキシン 3-β-D-グルコシド) 0.001
(6)L−アスコルビン酸グルコシド 0.5
(7)乳酸 0.05
(8)乳酸ナトリウム 0.1
(9)パラメトキシケイ皮酸−2−エチルヘキシル 3.0
(10)防腐剤 適量
(11)香料 適量
(12)精製水 残量
例20で調製した化粧水は、肌に適用することによって、肌を白く滑らかにする優れた化粧料であった。また、この化粧水には、沈殿等が認められず、安定性も良好であった。
下記成分(13)、(16)及び(18)を加熱混合し、70℃に保った混合物を、成分(1)〜(9)、(12)及び(15)を加熱混合し、70℃に保った混合物に加えて混合し、均一に乳化した。さらにこの乳化物を、冷却後(10)及び(11)を加え均一に混合した。この混合物に(14)を加え、十分に攪拌し、さらに(17)を加え、均一に混合して乳液を得た。
(処方) (%)
(1)ポリオキシエチレン(10E.O.)ソルビタン 1.0
モノステアレート
(2)ポリオキシエチレン(60E.O.)ソルビット 0.5
テトラオレエート
(3)グリセリルモノステアレート 1.0
(4)ステアリン酸 0.5
(5)ベヘニルアルコール 0.5
(6)スクワラン 8.0
(7)パルミチン酸レチノール*1 0.002
(8)グリチルリチン酸ジカリウム*2 0.3
(9)ビタミンB6誘導体(ピリドキシン 3-β-D-グルコシド) 0.01
(10)カンゾウ抽出物*3 0.1
(11)ヒアルロン酸 0.1
(12)防腐剤 0.1
(13)カルボキシビニルポリマー 0.1
(14)水酸化ナトリウム 0.05
(15)エチルアルコール 5.0
(16)精製水 残量
(17)香料 適量
(18)酸化亜鉛*4 5.0
*1 日本ロシュ社製
*2 丸善製薬社製
*3 丸善製薬社製
*4 シグマ社製
試験例21で調製した乳液は、肌に適用することによって、肌を白く滑らかにする優れた化粧料であった。また、この乳液には、沈殿等が認められず、安定性も良好であった。
Claims (3)
- 下記の一般式(V):
- (A)請求項1に記載の一般式(V)で表される化合物、及び(B)美白剤、酸化防止剤、消炎剤、血行促進剤、細胞賦活剤、及び紫外線吸収剤からなる群から選ばれる1種又は2種以上の物質を含有する化粧料のための組成物であって、美白剤、老化防止剤、及び/又は紫外線暴露によるシワ形成の抑制剤として用いる組成物。
- (A)請求項1に記載の一般式(V)で表される化合物、及び(B)アルブチンを含有する美白剤。
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US (2) | US8003615B2 (ja) |
EP (2) | EP1679316A4 (ja) |
JP (2) | JP4680775B2 (ja) |
KR (1) | KR101073303B1 (ja) |
CN (1) | CN100460414C (ja) |
CA (1) | CA2544574C (ja) |
ES (1) | ES2412274T3 (ja) |
WO (1) | WO2005033123A1 (ja) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
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ES2412274T3 (es) | 2003-10-01 | 2013-07-10 | Daiichi Fine Chemical Co., Ltd. | Composición que contiene un derivado de vitamina B6 estable |
US9101160B2 (en) | 2005-11-23 | 2015-08-11 | The Coca-Cola Company | Condiments with high-potency sweetener |
JP2007277134A (ja) * | 2006-04-05 | 2007-10-25 | Kose Corp | インターロイキン−6産生抑制剤 |
US8017168B2 (en) | 2006-11-02 | 2011-09-13 | The Coca-Cola Company | High-potency sweetener composition with rubisco protein, rubiscolin, rubiscolin derivatives, ace inhibitory peptides, and combinations thereof, and compositions sweetened therewith |
WO2008139965A1 (ja) * | 2007-05-07 | 2008-11-20 | Daiichi Fine Chemical Co., Ltd. | 新規なビタミンb6誘導体 |
EP2334298B1 (en) * | 2008-09-18 | 2014-07-30 | Manu Chaudhary | Novel single unit carbapenem aminoglycoside formulations |
KR20120065371A (ko) | 2009-09-11 | 2012-06-20 | 다이이치 파인 케미칼 가부시키가이샤 | 판테틴인산에스테르를 함유하는 외용제 |
US9198840B1 (en) | 2010-05-18 | 2015-12-01 | Skindinavia, Inc. | Use of cooling agent to improve cosmetics |
CN102958520A (zh) * | 2010-05-20 | 2013-03-06 | 郑忠铉 | 具抗细菌及抗真菌效果的皮肤外用组合物 |
JP6403946B2 (ja) * | 2012-10-31 | 2018-10-10 | 株式会社ミルボン | シャンプー組成物 |
US9724285B1 (en) | 2013-07-17 | 2017-08-08 | Skindinavia, Inc. | Use of stabilized vitamin B-6 (pyridoxine cyclic phosphate) in conjunction with skin cosmetics |
CN104418892A (zh) * | 2013-08-28 | 2015-03-18 | 江西天新药业有限公司 | 一种吡哆醇环磷酸衍生物及其制备方法和应用 |
CN104414871A (zh) * | 2013-08-28 | 2015-03-18 | 江西天新药业有限公司 | 一种化妆品组合物及其应用 |
JP2016008204A (ja) * | 2014-06-25 | 2016-01-18 | 協和ファーマケミカル株式会社 | 皮膚外用剤 |
CN105148987A (zh) * | 2015-07-15 | 2015-12-16 | 上海师范大学 | 一种吡哆醛类催化剂及其合成方法与应用 |
CN110403945B (zh) * | 2018-04-28 | 2022-11-18 | 上海泽生科技开发股份有限公司 | 促进胃肠系统动力的复合维生素组合物及其制备方法 |
JP2020100594A (ja) * | 2018-12-21 | 2020-07-02 | 小林製薬株式会社 | 口唇用組成物 |
US20220248687A1 (en) * | 2019-03-25 | 2022-08-11 | Kabushiki Kaisha Yakult Honsha | Method for promoting bacterial cell wall degradation |
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FR2349330A1 (fr) * | 1976-04-29 | 1977-11-25 | Savini Emile | Composition destinee au traitement des hyperlipidemies |
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JP2002265368A (ja) * | 2001-03-09 | 2002-09-18 | Pentapharm Japan Kk | ピリドキシン配糖体含有製剤または食品 |
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ES2412274T3 (es) * | 2003-10-01 | 2013-07-10 | Daiichi Fine Chemical Co., Ltd. | Composición que contiene un derivado de vitamina B6 estable |
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- 2004-09-30 WO PCT/JP2004/014768 patent/WO2005033123A1/ja active Application Filing
- 2004-09-30 EP EP04773642A patent/EP1679316A4/en not_active Withdrawn
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- 2004-09-30 JP JP2005514496A patent/JP4680775B2/ja active Active
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FR2196793A2 (en) * | 1972-08-24 | 1974-03-22 | Shionogi & Co | Corticotrophin peptide compsns - contg complex former and amines |
JP2001342110A (ja) * | 2000-06-02 | 2001-12-11 | Ezaki Glico Co Ltd | 皮膚外用剤 |
JP2003535880A (ja) * | 2000-06-20 | 2003-12-02 | ヘンケル・コマンディットゲゼルシャフト・アウフ・アクチエン | 組織改良毛髪ケア剤 |
JP2002265316A (ja) * | 2001-03-09 | 2002-09-18 | Pentapharm Japan Kk | 皮膚外用剤 |
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Also Published As
Publication number | Publication date |
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EP2311847B1 (en) | 2013-03-27 |
US20070148108A1 (en) | 2007-06-28 |
US8003615B2 (en) | 2011-08-23 |
ES2412274T3 (es) | 2013-07-10 |
KR101073303B1 (ko) | 2011-10-12 |
CN1863811A (zh) | 2006-11-15 |
EP1679316A4 (en) | 2010-05-26 |
CN100460414C (zh) | 2009-02-11 |
JPWO2005033123A1 (ja) | 2006-12-14 |
EP2311847B9 (en) | 2013-07-24 |
CA2544574C (en) | 2013-07-23 |
JP2008013578A (ja) | 2008-01-24 |
JP4680775B2 (ja) | 2011-05-11 |
KR20060092230A (ko) | 2006-08-22 |
WO2005033123A1 (ja) | 2005-04-14 |
US20090117064A1 (en) | 2009-05-07 |
EP2311847A1 (en) | 2011-04-20 |
CA2544574A1 (en) | 2005-04-14 |
EP1679316A1 (en) | 2006-07-12 |
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