JP4907137B2 - ヒドロキシクエン酸誘導体類及びこれを含む皮膚外用剤 - Google Patents
ヒドロキシクエン酸誘導体類及びこれを含む皮膚外用剤 Download PDFInfo
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- JP4907137B2 JP4907137B2 JP2005278160A JP2005278160A JP4907137B2 JP 4907137 B2 JP4907137 B2 JP 4907137B2 JP 2005278160 A JP2005278160 A JP 2005278160A JP 2005278160 A JP2005278160 A JP 2005278160A JP 4907137 B2 JP4907137 B2 JP 4907137B2
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- Prior art keywords
- acid
- group
- extract
- hydroxycitric acid
- oil
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- ZMJBYMUCKBYSCP-UHFFFAOYSA-N Hydroxycitric acid Chemical class OC(=O)C(O)C(O)(C(O)=O)CC(O)=O ZMJBYMUCKBYSCP-UHFFFAOYSA-N 0.000 title claims description 129
- 238000002360 preparation method Methods 0.000 title claims description 44
- 230000000699 topical effect Effects 0.000 title description 2
- -1 alkali metal salt Chemical class 0.000 claims description 251
- 229940089491 hydroxycitric acid Drugs 0.000 claims description 64
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 58
- 239000000126 substance Substances 0.000 claims description 50
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 46
- 229930195729 fatty acid Natural products 0.000 claims description 46
- 239000000194 fatty acid Substances 0.000 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 38
- 150000004665 fatty acids Chemical class 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 30
- 239000002537 cosmetic Substances 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 16
- 229910052783 alkali metal Inorganic materials 0.000 claims description 16
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 16
- 230000000694 effects Effects 0.000 claims description 14
- 230000009471 action Effects 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 108010055297 Sterol Esterase Proteins 0.000 claims description 8
- 102000000019 Sterol Esterase Human genes 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 230000002708 enhancing effect Effects 0.000 claims description 6
- 150000001263 acyl chlorides Chemical class 0.000 claims description 5
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 5
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 4
- 235000019626 lipase activity Nutrition 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000000284 extract Substances 0.000 description 150
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 62
- 235000002639 sodium chloride Nutrition 0.000 description 61
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 57
- 159000000000 sodium salts Chemical class 0.000 description 57
- 238000012360 testing method Methods 0.000 description 51
- 210000003491 skin Anatomy 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
- 238000003786 synthesis reaction Methods 0.000 description 40
- 230000015572 biosynthetic process Effects 0.000 description 37
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 34
- 238000003756 stirring Methods 0.000 description 34
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 33
- 239000008213 purified water Substances 0.000 description 32
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- 235000019198 oils Nutrition 0.000 description 31
- 239000000047 product Substances 0.000 description 31
- 239000011734 sodium Substances 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 229910052708 sodium Inorganic materials 0.000 description 28
- 229940083542 sodium Drugs 0.000 description 28
- 235000019864 coconut oil Nutrition 0.000 description 27
- 239000003240 coconut oil Substances 0.000 description 27
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 26
- 239000002609 medium Substances 0.000 description 26
- 239000000203 mixture Substances 0.000 description 24
- 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 23
- 238000000034 method Methods 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 125000000217 alkyl group Chemical group 0.000 description 21
- 239000003925 fat Substances 0.000 description 21
- 235000019197 fats Nutrition 0.000 description 21
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 20
- 210000004027 cell Anatomy 0.000 description 20
- 239000000499 gel Substances 0.000 description 19
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 17
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 17
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 17
- 229960002216 methylparaben Drugs 0.000 description 17
- 239000004359 castor oil Substances 0.000 description 16
- 235000019438 castor oil Nutrition 0.000 description 16
- 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 16
- 150000002430 hydrocarbons Chemical group 0.000 description 15
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- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 15
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- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 14
- 239000007788 liquid Substances 0.000 description 14
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 13
- 125000002252 acyl group Chemical group 0.000 description 13
- 238000013329 compounding Methods 0.000 description 13
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- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 12
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- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 12
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 11
- 235000002597 Solanum melongena Nutrition 0.000 description 11
- 210000001789 adipocyte Anatomy 0.000 description 11
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- 235000011187 glycerol Nutrition 0.000 description 11
- 229940105132 myristate Drugs 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 229920002125 Sokalan® Polymers 0.000 description 10
- 235000019437 butane-1,3-diol Nutrition 0.000 description 10
- 229940070765 laurate Drugs 0.000 description 10
- 125000004430 oxygen atom Chemical group O* 0.000 description 10
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 10
- 229940058015 1,3-butylene glycol Drugs 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 8
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- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 229940032094 squalane Drugs 0.000 description 8
- RVEPHTVUPANNSH-UHFFFAOYSA-H tricalcium;1,2-dihydroxypropane-1,2,3-tricarboxylate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]C(=O)C(O)C(O)(C([O-])=O)CC([O-])=O.[O-]C(=O)C(O)C(O)(C([O-])=O)CC([O-])=O RVEPHTVUPANNSH-UHFFFAOYSA-H 0.000 description 8
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
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- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 7
- 229910019142 PO4 Inorganic materials 0.000 description 7
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- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 7
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- 150000003627 tricarboxylic acid derivatives Chemical class 0.000 description 1
- NRLLZRJXDKUVHM-UHFFFAOYSA-N tridecyl 7-methyloctanoate Chemical compound CCCCCCCCCCCCCOC(=O)CCCCCC(C)C NRLLZRJXDKUVHM-UHFFFAOYSA-N 0.000 description 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- 229940029614 triethanolamine stearate Drugs 0.000 description 1
- WEAPVABOECTMGR-UHFFFAOYSA-N triethyl 2-acetyloxypropane-1,2,3-tricarboxylate Chemical compound CCOC(=O)CC(C(=O)OCC)(OC(C)=O)CC(=O)OCC WEAPVABOECTMGR-UHFFFAOYSA-N 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- PDSVZUAJOIQXRK-UHFFFAOYSA-N trimethyl(octadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)C PDSVZUAJOIQXRK-UHFFFAOYSA-N 0.000 description 1
- SZEMGTQCPRNXEG-UHFFFAOYSA-M trimethyl(octadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C SZEMGTQCPRNXEG-UHFFFAOYSA-M 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 229940118594 trimethylolpropane triisostearate Drugs 0.000 description 1
- APVVRLGIFCYZHJ-UHFFFAOYSA-N trioctyl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CCCCCCCCOC(=O)CC(O)(C(=O)OCCCCCCCC)CC(=O)OCCCCCCCC APVVRLGIFCYZHJ-UHFFFAOYSA-N 0.000 description 1
- 229940026256 trioctyldodecyl citrate Drugs 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 229940117972 triolein Drugs 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- COXJMKGEQAWXNP-UHFFFAOYSA-N tris(14-methylpentadecyl) 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CC(C)CCCCCCCCCCCCCOC(=O)CC(O)(C(=O)OCCCCCCCCCCCCCC(C)C)CC(=O)OCCCCCCCCCCCCCC(C)C COXJMKGEQAWXNP-UHFFFAOYSA-N 0.000 description 1
- BIEMOBPNIWQLMF-UHFFFAOYSA-N tris(2-octyldodecyl) 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CCCCCCCCCCC(CCCCCCCC)COC(=O)CC(O)(C(=O)OCC(CCCCCCCC)CCCCCCCCCC)CC(=O)OCC(CCCCCCCC)CCCCCCCCCC BIEMOBPNIWQLMF-UHFFFAOYSA-N 0.000 description 1
- VXYADVIJALMOEQ-UHFFFAOYSA-K tris(lactato)aluminium Chemical compound CC(O)C(=O)O[Al](OC(=O)C(C)O)OC(=O)C(C)O VXYADVIJALMOEQ-UHFFFAOYSA-K 0.000 description 1
- 229960005066 trisodium edetate Drugs 0.000 description 1
- CCXAYLQLOLXXKE-DWJAGBRCSA-K trisodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4s,5s,6s)-2-[[(3s,4ar,6ar,6bs,8as,11s,12ar,14ar,14bs)-11-carboxylato-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1h-picen-3-yl]oxy]-6-carboxylato-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-t Chemical compound [Na+].[Na+].[Na+].O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@H]1CC[C@]2(C)[C@H]3C(=O)C=C4[C@@H]5C[C@](C)(CC[C@@]5(CC[C@@]4(C)[C@]3(C)CC[C@H]2C1(C)C)C)C([O-])=O)C([O-])=O)[C@@H]1O[C@H](C([O-])=O)[C@@H](O)[C@H](O)[C@H]1O CCXAYLQLOLXXKE-DWJAGBRCSA-K 0.000 description 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
- 239000008513 turmeric extract Substances 0.000 description 1
- 229940052016 turmeric extract Drugs 0.000 description 1
- 235000020240 turmeric extract Nutrition 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
- 150000003669 ubiquinones Chemical class 0.000 description 1
- GAAKLDANOSASAM-UHFFFAOYSA-N undec-10-enoic acid;zinc Chemical compound [Zn].OC(=O)CCCCCCCCC=C GAAKLDANOSASAM-UHFFFAOYSA-N 0.000 description 1
- 235000020767 valerian extract Nutrition 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 1
- 235000010374 vitamin B1 Nutrition 0.000 description 1
- 239000011691 vitamin B1 Substances 0.000 description 1
- 235000019163 vitamin B12 Nutrition 0.000 description 1
- 239000011715 vitamin B12 Substances 0.000 description 1
- 235000019164 vitamin B2 Nutrition 0.000 description 1
- 239000011716 vitamin B2 Substances 0.000 description 1
- 235000019158 vitamin B6 Nutrition 0.000 description 1
- 239000011726 vitamin B6 Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 1
- 235000001892 vitamin D2 Nutrition 0.000 description 1
- 239000011653 vitamin D2 Substances 0.000 description 1
- 235000019168 vitamin K Nutrition 0.000 description 1
- 239000011712 vitamin K Substances 0.000 description 1
- 150000003721 vitamin K derivatives Chemical class 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 229940046010 vitamin k Drugs 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 235000010930 zeaxanthin Nutrition 0.000 description 1
- 239000001775 zeaxanthin Substances 0.000 description 1
- 229940043269 zeaxanthin Drugs 0.000 description 1
- 229940098697 zinc laurate Drugs 0.000 description 1
- 229940105125 zinc myristate Drugs 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229940012185 zinc palmitate Drugs 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 229940057977 zinc stearate Drugs 0.000 description 1
- 229940118257 zinc undecylenate Drugs 0.000 description 1
- GPYYEEJOMCKTPR-UHFFFAOYSA-L zinc;dodecanoate Chemical compound [Zn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O GPYYEEJOMCKTPR-UHFFFAOYSA-L 0.000 description 1
- GJAPSKMAVXDBIU-UHFFFAOYSA-L zinc;hexadecanoate Chemical compound [Zn+2].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O GJAPSKMAVXDBIU-UHFFFAOYSA-L 0.000 description 1
- GBFLQPIIIRJQLU-UHFFFAOYSA-L zinc;tetradecanoate Chemical compound [Zn+2].CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O GBFLQPIIIRJQLU-UHFFFAOYSA-L 0.000 description 1
- 239000001243 zingiber officinale rosc. root absolute Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
- 235000007680 β-tocopherol Nutrition 0.000 description 1
- 239000011590 β-tocopherol Substances 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
- GZIFEOYASATJEH-VHFRWLAGSA-N δ-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-VHFRWLAGSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0212—Face masks
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
- A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/08—Antiseborrheics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
- A61Q19/06—Preparations for care of the skin for countering cellulitis
-
- 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
- A61Q19/10—Washing or bathing preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
- C07C59/285—Polyhydroxy dicarboxylic acids having five or more carbon atoms, e.g. saccharic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/28—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with dihydroxylic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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- Anti-Oxidant Or Stabilizer Compositions (AREA)
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Description
さらに詳しくは、本発明は、痩身効果を有するヒドロキシクエン酸誘導体類、該誘導体類の製造方法及び該誘導体類を含む皮膚外用剤に関する。
体脂肪の蓄積により招聘される肥満は、外見上好ましくないばかりでなく、動脈硬化等の様々な疾病を引き起こすことから、健康上からも外見上からも引き締まった身体が望まれる傾向にある。
特許文献2に記載されている。
さらに、ヒドロキシクエン酸の水溶性と安定性を高めるため、カルシウム塩やナトリウム塩などとして用いることが、特許文献4に記載されている。
性が不充分であり、結果として脂肪代謝を行う組織にまで充分な量を到達させることが困難であったことによると考えられる。
これに対して、効果を得るために多量のヒドロキシクエン酸類を外用剤に配合すると、外用剤としての使用感が損なわれたり、変臭や変色が発生したりする等、剤型の安定性に問題が有ると考えられる。
また、本発明は、当該新規なヒドロキシクエン酸誘導体又はその塩の製造方法の提供をその目的の一つとする。
また、本発明はその他に、天然抽出物由来のヒドロキシクエン酸誘導体及び/又はその塩を含有する皮膚外用剤および化粧料の提供をも目的の1つとする。
[1]下記式(a)で示されるヒドロキシクエン酸誘導体又はその塩;
長鎖カルボン酸、長鎖アシルクロライド、長鎖カルボン酸無水物、長鎖カルボン酸エステル又は長鎖アルキルニトリルと前記第一工程で得られた化合物とを反応させ、前記第一工程で得られた化合物の水酸基をエステル化する第二工程と、
前記第二工程で得られた化合物のエステル結合部位のうち、第一工程で形成されたエステル結合部位の全部を切断する第三工程とを有することを特徴とする上記[1]に記載のヒドロキシクエン酸誘導体又はその塩を製造する方法。
[5]前記ヒドロキシクエン酸誘導体及び/又はその塩を、0.01質量%〜20質量%の量で含有することを特徴とする上記[4]に記載の皮膚外用剤。
性が高く、体内に吸収された後は生体酵素反応で分解されてヒドロキシクエン酸となるため、本発明のヒドロキシクエン酸誘導体又はその塩によれば、ヒドロキシクエン酸の体内吸収効率を高め、脂肪合成を行う組織にまでヒドロキシクエン酸を充分な量で到達させることができる。
成を行う組織における脂肪合成抑制効果を期待する皮膚外用剤の成分として使用することにより、効果的で使用感が良く、安定性に優れた皮膚外用剤を提供することができる。
さらに、上記ヒドロキシクエン酸誘導体及び/又はその塩と、ホルモン感受性リパーゼ
活性を高める作用を持つ物質や脂肪酸の分解を高める作用を持つ物質を、皮膚外用剤の成分として併用することにより、脂肪合成抑制効果のみならず脂肪分解促進効果を期待することができる。
まず、本発明のヒドロキシクエン酸誘導体について説明する。
及びR2が同時に水素原子になることはない。)。
される群から選択される生体酵素反応で離脱可能ないずれかの基であり、R2が水素原子
である態様がより好ましい。
る。
素数7〜23、好ましくは13〜21の鎖状炭化水素基、より好ましくは分岐を有していてもよい炭素数13〜21の鎖状飽和炭化水素基であり、R7およびR8は、それぞれ独立に水素原子、又は分岐、不飽和結合、もしくは置換基を有していてもよい、炭素数8〜24の鎖状炭化水素基、好ましくは、水素原子又は炭素数14〜22の鎖状炭化水素基、より好ましくは水素原子である。
これらのうち、上記式(Ia)で示される群から選択される生体酵素反応で脱離可能ないずれかの基は、炭素数8〜24、好ましくは炭素数14〜22の基であることが望ましい。
分子中の水酸基が修飾された誘導体の例としては、具体的には、上記式(I)中のR1
及び/又はR2が、ヘキサノイル基、2−メチルペンタノイル基、3−メチルペンタノイ
ル基、4−メチルペンタノイル基、2−エチルブタノイル基、ヘプタノイル基、2−メチルヘキサノイル基、3−メチルヘキサノイル基、4−メチルヘキサノイル基、2−エチルペンタノイル基、3−エチルペンタノイル基、オクタノイル基、2−メチルヘプタノイル基、3−メチルヘプタノイル基、4−メチルヘプタノイル基、5−メチルヘプタノイル基、6−メチルヘプタノイル基、2−エチルヘキサノイル基、3−エチルヘキサノイル基、4−エチルヘキサノイル基、2−プロピルペンタノイル基、ノナノイル基、デカノイル基、ウンデカノイル基、10−ウンデセノイル基、ドデカノイル基、トリデカノイル基、テトラデカノイル基、ペンタデカノイル基、ヘキサデカノイル基、9−ヘキサデセノイル基、
、ドデカノイル基、ヘキサデカノイル基、オクタデカノイル基、イソステアリル基のいず
れかであって、R2が水素原子である化合物が挙げられる。
R4,R5,R3',R4',R5'は、それぞれ独立に水素原子、又は分岐もしくは不飽和結合を有していてもよい、炭素数1〜30の鎖状炭化水素基を表す(但し、X1,X2,X3が
それぞれ酸素原子の場合は、対応するR3',R4',R5'は存在しない。)。
X1〜X3のいずれかが窒素原子の場合は−CONRmRm'(mおよびm’は、X1〜X3
に対応して3,4,5のいずれか同じ数を表す。)は生体酵素反応で分解可能な置換又は無置換のアミド基を表し、またX1〜X3のいずれかが酸素原子の場合は−COORm(m
は、X1〜X3に対応して3,4,5のいずれかの数を表す。)は、カルボキシル基又は生体酵素反応で分解可能なエステル基を表す。
て、それぞれ独立に水素原子、又は炭素原子数1〜30、好ましくは8〜24、より好ましくは14〜22の分岐もしくは不飽和結合を有していてもよい鎖状炭化水素基であり、さらに好ましくは水素原子又は炭素数14〜22の分岐を有していてもよい鎖状飽和炭化水素基である。また、その他、単糖及び多糖から誘導される糖残基であってもよい。
、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、1−メチルプロピル基、2−メチルプロピル基、ペンチル基、1−メチルブチル基、2−メチルブチル基、3−メチルブチル基、1−エチルプロピル基、ヘキシル基、1−メチルペンチル基、2−メチルペンチル基、3−メチルペンチル基、4−メチルペンチル基、1−エチルブチル基、2−エチルブチル基、ヘプチル基、1−メチルヘキシル基、2−メチルヘキシル基、3−メチルヘキシル基、4−メチルヘキシル基、5−メチルヘキシル基、1−エチルペンチル基、2−エチルペンチル基、3−エチルペンチル基、オクチル基、1−メチルヘプチル基、2−メチルヘプチル基、3−メチルヘプチル基、4−メチルヘプチル基、5−メチルヘプチル基、6−メチルヘプチル基、1−エチルヘキシル基、2−エチルヘキシル基、3−エチルヘキシル基、4−エチルヘキシル基、1−プロピルペンチル基、2−プロピルペンチル基、ノニル基、デシル基、ウンデシル基、10−ウンデセニル基、ドデシル基、トリデシル基、テトラデシル基、ペンタデシル基、ヘキサデシル基、9−ヘキサデセニル基、ヘプタデシル基、オクタデシル基、イソステアリル基、シス−9−オクタデセニル基、11−オクタデセニル基、
3,R4,R5,R3',R4',R5'がそれぞれ独立に、水素原子、メチル基、エチル基、プ
ロピル基、イソプロピル基、ブチル基、ヘキシル基、オクチル基、デシル基、ウンデシル基、ドデシル基、トリデシル基、テトラデシル基、ペンタデシル基、ヘキサデシル基、ヘプタデシル基、オクタデシル基、イソステアリル基のいずれかである態様が挙げられる。
チル基、エチル基、プロピル基、イソプロピル基、ブチル基、ヘキシル基、オクチル基、デシル基、ウンデシル基、ドデシル基、トリデシル基、テトラデシル基、ペンタデシル基、ヘキサデシル基、ヘプタデシル基、オクタデシル基、イソステアリル基のいずれかであり、他が水素原子である態様が挙げられる。
ルボキシル基又は生体酵素反応で分解可能なエステル基を表す。この場合には、R3',R4',R5'は存在しない。
また、分子中のカルボキシル基が修飾された誘導体の例としては、既に述べた分子中の水酸基が修飾された誘導体のカルボキシル基部位の少なくとも1つが、生体酵素反応で分解可能な置換又は無置換のアミド基、又は生体酵素反応で分解可能なエステル基となっている化合物が挙げられる。
子である下記式(IIa)に示す化合物、または、
R2が水素原子であり、R3〜R5がそれぞれ独立に水素原子又は分岐もしくは不飽和結
合を有していてもよい、炭素数1〜30の鎖状炭化水素基であり(但し、R3〜R5が同時に水素原子となることはない。)、且つX1〜X3がすべて酸素原子である下記式(IIb)に示す化合物が好ましい例として挙げられる。
これらの場合、R1は上記式(Ia)で示される群から選択される生体酵素反応で離脱
可能ないずれかの基を表す。さらに式(Ia)において、R6は、分岐、不飽和結合もし
くは置換基を有していてもよい、炭素数13〜21の鎖状炭化水素基であることが好ましく、さらにR1としては、炭素数14〜22のアシル基が望ましい。
本発明のヒドロキシクエン酸誘導体の塩としては、上記ヒドロキシクエン酸誘導体のアルカリ金属塩、アルカリ土類金属塩が挙げられる。
アルカリ金属塩としては、ナトリウム塩、カリウム塩等が挙げられ、アルカリ土類金属塩としては、カルシウム塩等が挙げられる。
次に、本発明のヒドロキシクエン酸誘導体又はその塩の製造方法について説明する。
本発明のヒドロキシクエン酸誘導体又はその塩の製造方法には特に制限はなく、ヒドロキシクエン酸及び/又はそのアルカリ金属塩及び/又はそのアルカリ土類金属塩と、生体内で切断可能なカルボン酸誘導体又はリン酸誘導体又はスルホン酸誘導体とを、適当な溶媒中で反応させることによって製造することが可能である。
(1)ヒドロキシクエン酸の水酸基を直接エステル化する方法、
(2)ヒドロキシクエン酸のカルボキシル基をエステル化してから、水酸基をエステル化し、前者のエステル結合部位を切断してカルボキシル基に戻す方法、
(3)ヒドロキシクエン酸のカルボキシル基をエステル化してから、水酸基をエステル化する方法、
(4)ヒドロキシクエン酸の水酸基をエステル化してから、カルボキシル基をエステル化する方法、
(5)ヒドロキシクエン酸のカルボキシル基をアミド化してから、水酸基をエステル化する方法、
(6)ヒドロキシクエン酸のカルボキシル基をアミド化してから、水酸基をエステル化し、前者のアミド結合部位を切断してカルボキシル基に戻す方法、
(7)ヒドロキシクエン酸の水酸基をエステル化してから、カルボキシル基をアミド化する方法等を挙げることができる。
ル基であって、R2が水素原子であり、R3〜R5がすべて水素原子であり、且つX1〜X3
がすべて酸素原子である前記式(IIa)に示す化合物の製造方法にも、特に制限はない。例えば、市販されているヒドロキシクエン酸を原料として、上記(1)または(2)の方法で製造することができる。
リカルボン酸部位をいったん保護(たとえば、ベンジルエステルで保護)する第一工程と、第一工程で得られた化合物の水酸基を上記方法のいずれかでエステル化する第二工程と、第二工程で得られた化合物の第一工程で製造したエステル部位を脱保護(エステル結合部位を切断)する第三工程とを実施することによって形成することができる。
ル基であって、R2が水素原子であり、R3〜R5がそれぞれ独立に水素原子、又は分岐も
しくは不飽和結合を有していてもよい、炭素数1〜30の鎖状炭化水素基であり(但し、R3〜R5が同時に水素原子となることはない。)、且つX1〜X3がすべて酸素原子である前記式(IIb)に示す化合物の製造方法にも、特に制限はない。例えば、市販されているヒドロキシクエン酸を原料として、上記(2)〜(4)の方法で製造することができる。
反応濃度はとくに限定はないが、0.0001mol/dm3〜10mol/dm3の範囲が好ましく、0.1mol/dm3〜1mol/dm3の範囲がさらに好ましい。
また、このようなpH調節を行うことにより、ヒドロキシクエン酸誘導体の塩を容易に製造することができる。たとえば、pH調整剤としてNaOHを用いれば、ヒドロキシクエン酸誘導体のNa塩を得ることができる。
<皮膚外用剤、化粧料>
本発明の皮膚外用剤においては、ヒドロキシクエン酸誘導体、ヒドロキシクエン酸誘導体の塩は、それぞれ単独であるいは組み合わせて用いることができる。これらのヒドロキシクエン酸誘導体及び/又はその塩は、皮膚外用剤全量中に、通常0.01質量%〜20質量%、好ましくは0.05質量%〜12質量%、より好ましくは0.1質量%〜10質量%の量で含まれている。ヒドロキシクエン酸誘導体及び/又はその塩がこのような量で皮膚外用剤に含まれていると、皮膚への移行が速やかであり、皮膚外用剤に求められる効能効果を発揮できるため好ましい。
て、既存の痩身効果を目的として配合される物質と併用することで、相乗的な効果を得ることができる。
ホルモン感受性リパーゼの脂肪分解により生じた脂肪酸は、遊離脂肪酸として血中に放出される。過剰の遊離脂肪酸は脂肪再合成原料と成りうるため、脂肪酸の分解を促進する物質が痩身効果を目的として配合される。このような脂肪酸の分解を高める作用を持つ物質として化粧品に配合される例としては、たとえば、カルニチン、セサミン、グレープフルーツエキス、コショウ、ウイキョウ、タラゴンなどの物質が挙げられる。
これらの物質とヒドロキシクエン酸は脂質代謝における役割が異なることから、相乗効果を期待することができる。これらの物質は、皮膚外用剤全量中に、通常0.01〜20質量%、好ましくは0.5〜15質量%、より好ましくは1〜10質量%の量で含まれている。
また、本発明の皮膚外用剤の別の態様として、下記式(III)で示されるヒドロキシク
エン酸誘導体及び/又はその塩を含む皮膚外用剤が挙げられる。
前記式(III)で表されるヒドロキシクエン酸誘導体は、天然物、たとえば、とうもろ
こし、コーヒー、タマゴノキなどから抽出されるものであるが、本発明の新規なヒドロキシクエン酸誘導体と似た構造を有しているため、この化合物も皮膚親和性及び/又は経皮吸収性が高く、体内に吸収された後は加水分解されてヒドロキシクエン酸となり、痩身効果が期待できるものと推測される。該誘導体の塩としては、アルカリ金属塩、アルカリ土類金属塩が挙げられる。
このような成分としては、たとえば、オゾケライト、α−オレフィンオリゴマー、軽質イソパラフィン、軽質流動イソパラフィン、スクワレン、スクワラン、合成スクワラン、植物性スクワラン、セレシン、パラフィン、ポリエチレン末、ポリブテン、マイクロクリスタリンワックス、流動イソパラフィン、流動パラフィン、ミネラル油、ワセリン等の炭化水素類;
イソステアリルアルコール、オクチルドデカノール、ヘキシルデカノール、コレステロール、フィトステロール、ラウリルアルコール、ミリスチルアルコール、セタノール、ステアリルアルコール、オレイルアルコール、ベヘニルアルコール、セトステアリルアルコール等の高級アルコール類;
バチルアルコール、キミルアルコール、セラキルアルコール、イソステアリルグリセリルエーテル等のアルキルグリセリルエーテル類;
リン酸エチル、ステアリン酸ブチル、オレイン酸エチル、リノール酸エチル、リノール酸イソプロピル、カプリル酸セチル、ラウリン酸ヘキシル、ミリスチン酸イソオクチル、ミリスチン酸デシル、ミリスチン酸ミリスチル、ミリスチン酸セチル、ミリスチン酸オクタデシル、パルミチン酸セチル、ステアリン酸ステアリル、オレイン酸デシル、オレイン酸オレイル、リシノール酸セチル、ラウリン酸イソステアリル、ミリスチン酸イソトリデシル、ミリスチン酸イソセチル、ミリスチン酸イソステアリル、ミリスチン酸オクチルドデシル、パルミチン酸2−エチルヘキシル、パルミチン酸イソセチル、パルミチン酸イソステアリル、ステアリン酸2−エチルヘキシル、ステアリン酸イソセチル、オレイン酸イソデシル、オレイン酸オクチルドデシル、リシノール酸オクチルドデシル、イソステアリン酸エチル、イソステアリン酸イソプロピル、2−エチルヘキサン酸セチル、2−エチルヘキサン酸セトステアリル、2−エチルヘキサン酸ステアリル、イソステアリン酸ヘキシル、ジオクタン酸エチレングリコール、ジオレイン酸エチレングリコール、ジカプリル酸プロピレングリコール、ジ(カプリル・カプリン酸)プロピレングリコール、ジカプリン酸プロピレングリコール、ジオレイン酸プロピレングリコール、ジカプリン酸ネオペンチルグリコール、ジオクタン酸ネオペンチルグリコール、トリカプリル酸グリセリル、トリ2−エチルヘキサン酸グリセリル、トリ(カプリル・カプリン酸) グリセリル、トリ(カプリル酸・カプリン酸・ステアリン酸) グリセリル、
ロピレン)シロキサン共重合体、ジメチルシロキサン・メチルセチルオキシシロキサン共重合体、ジメチルシロキサン・メチルステアロキシシロキサン共重合体、ポリエーテル変性シリコーン、アルコール変性シリコーン、アルキル変性シリコーン、アミノ変性シリコーン等のシリコーン油類;
高分子類;
エチレングリコール、ジエチレングリコール、ポリエチレングリコール、プロピレングリコール、ポリプロピレングリコール、グリセリン、ジグリセリン、ポリグリセリン、1,3−ブタンジオール、トリエチレングリコール、ジプロピレングリコール、3−メチル−1,3−ブタンジオール、1,2−ペンタンジオール、1,4−ペンタンジオール、1,5−ペンタンジオール、2,4−ペンタンジオール、2-メチルー2,4−ペンタンジ
オール、3−メチル−1,5−ペンタンジオール、1,2−ヘキサンジオール、1,6−ヘキサンジオール等の多価アルコール類;
リウム、アルキル(12,13)硫酸トリエタノールアミン、アルキル(12,14,16)硫
酸アンモニウム、アルキル(12〜13)硫酸ジエタノールアミン、アルキル(12〜14)硫酸トリエタノールアミン、アルキル(12〜15)硫酸トリエタノールアミン、ヤシ油アルキル硫酸マグネシウム・トリエタノールアミン、ラウリル硫酸アンモニウム、ラウリル硫酸カリウム、ラウリル硫酸マグネシウム、ラウリル硫酸モノエタノールアミン、ラウリル硫酸ジエタノールアミン、ミリスチル硫酸ナトリウム、ステアリル硫酸ナトリウム、オレイル硫酸ナトリウム、オレイル硫酸トリエタノールアミン、ポリオキシエチレンラウリルエーテル硫酸ナトリウム、ポリオキシエチレンラウリルエーテル硫酸トリエタノールアミン、ポリオキシエチレン(1)アルキル(11,13,15)エーテル硫酸ナトリウム、ポリオキシエチレン(1)アルキル(11,13,15)エーテル硫酸トリエタノールアミン、ポリオキシエチレン(3)アルキル(11〜15)エーテル硫酸ナトリウム、ポリオキシエチレン(2)アルキル(12,13)エーテル硫酸ナトリウム、
酸、ポリオキシエチレンラウリルエーテルリン酸トリエタノールアミン、ポリオキシエチレンオレイルエーテルリン酸ジエタノールアミン等の陰イオン界面活性剤;
25)ジエチルメチルアンモニウム、塩化トリ(ポリオキシエチレン)ステアリルアンモ
ニウム(5EO)、塩化ジステアリルジメチルアンモニウム、塩化ジアルキル(12〜15)ジメチルアンモニウム、塩化ジアルキル(12〜18)ジメチルアンモニウム、塩化ジアルキル(14〜18)ジメチルアンモニウム、塩化ジココイルジメチルアンモニウム、塩化ジセチルジメチルアンモニウム、塩化イソステアリルラウリルジメチルアンモニウム、塩化ベンザルコニウム、塩化ミリスチルジメチルベンジルアンモニウム、塩化ラウリルジメチル(エチルベンジル)アンモニウム、塩化ステアリルジメチルベンジルアンモニウム、塩化ラウリルピリジニウム、塩化セチルピリジニウム、塩化ラウロイルコラミノホルミルメチルピリジニウム、塩化ステアロイルコラミノホルミルメチルピリジニウム、臭化アルキルイソキノリウム、塩化メチルベンゼトニウム、塩化ベンゼトニウム等の陽イオン界面活性剤;
シエチレンジノニルフェニルエーテル、ポリオキシエチレン(1)ポリオキシプロピレン(1,2,4,8)セチルエーテル、ポリオキシエチレン(5)ポリオキシプロピレン(1,2,4,8)セチルエーテル、ポリオキシエチレン(10)ポリオキシプロピレン(1,2,4,8)セチルエーテル、ポリオキシエチレン(20)ポリオキシプロピレン(1,2,4,8)セチルエーテル、ポリオキシエチレンポリオキシプロピレンラウリルエーテル、ポリオキシエチレン(3)ポリオキシプロピレン(34)ステアリルエーテル、
イン酸ジグリセリル、ジイソステアリン酸ポリ(2〜10)グリセリル、ジステアリン酸ポリ(6〜10)グリセリル、トリイソステアリン酸ジグリセリル、
アルミニウム、炭酸カルシウム、チタン酸リチウムコバルト、マンガンバイオレット、パール顔料等の粉体類および色材類;
ヒアルロン酸、ヒアルロン酸ナトリウム、コンドロイチン硫酸ナトリウム、乳酸ナトリウム、ピロリドンカルボン酸ナトリウム、ベタイン、乳酸菌培養液、酵母エキス、セラミド等の保湿剤;
水酸化ナトリウム、水酸化カリウム、トリエタノールアミン等のpH調整剤;
塩化ナトリウム、塩化カリウム、塩化マグネシウム、硫酸ナトリウム等の塩類;
クエン酸、グリコール酸、酒石酸、乳酸等のα−ヒドロキシ酸類;
アンゼリカ油、イランイラン油、エレミ油、カミツレ油、ローマカミツレ油、カルダモン油、カラムス油、ガルバナム油、カンファー油、キャロットシード油、クラリーセージ油、チョウジ油、ケイヒ油、コリアンダー油、サイプレス油、サンダルウッド油、シダーウッド油、シトロネラ油、シナモンリーフ油、ジャスミンアブソリュート、ジュニパーベリー油、ジンジャーエクストラクト、スペアミント油、セージ油、セダー油、ゼラニウム油、タイム油、ティーツリー油、ナツメグ油、ニアウリ油、ネロリ油、パイン油、バジル油、ハッカ油、パチュリー油、パルマローザ油、フェンネル油、プチグレン油、ブラックペッパー油、フランキンセンス油、ベチバ油、ペパーミント油、ベルガモット油、ベンゾイン油、ボアドローズ油、マジョラム油、ミルラ油、メリッサ油、ユーカリ油、ラベンサラ油、ラバンジン油、ラベンダー油、リンデン油、ローズ油、ローズウッド油、ローズマリー油、ロベージ油等の精油類;
ピネン、テルピネン、テルピノーレン、ミルセン、ロンギフィーレン等のテルペン類;
香料;水などが挙げられる。
本発明の皮膚外用剤および化粧料は、上述した成分を、所定の含有量となるように用いて、その態様に応じ常法に従い、溶解、混合あるいは分散等することにより製造することができる。また、本発明の皮膚外用剤および化粧料の形状としては、固体、液体、半固体、気体のほか、粉体、顆粒、錠形、ゲル状、泡状など多数の形態が挙げられるが、特にこれに限定されるものではない。
液体クロマトグラフ装置 :Agilent 1100シリーズ
カラム :Shodex OHpak SB-802.5 HQ
カラム温度:40℃
溶離液 :0.02M 酢酸アンモニウム水溶液/アセトニトリル=75/25(V/V)
溶離液流速:0.8ml/min
試料注入量:100μl(オートサンプラー使用)
質量分析装置 :Thermoquest LCQ Advantage
イオン化法:エレクトロスプレーイオン化法(ESI)
測定モード:選択的イオンモニタリング(SIM)
モニタリングイオン例:m/z207(for ヒドロキシクエン酸),m/z445(for ヒドロキシクエ
ン酸−2−パルミテート)
ヒドロキシクエン酸−2−パルミテート ナトリウム塩の合成
(1)ヒドロキシクエン酸トリベンジルエステルの合成
200mLナスフラスコにヒドロキシクエン酸カルシウム塩2.96g(10.1mmol)、トルエンスルホン酸一水和物5.86g(30.8mmol)、ベンジルアルコール10g(92.5mmol)、トルエン20mLを仕込み、共沸する水を除きながら4時間還流下で攪拌した。放冷した後、酢酸エチルを50mL加え、良く攪拌した。
これを5質量%炭酸水素ナトリウム水溶液100mLの入った500mLビーカー中に少しずつ攪拌しながら加えた。不溶物を除き、水層を分離した後、有機層を水で洗浄し、さらに無水硫酸ナトリウム上で乾燥させた。溶媒とベンジルアルコールを減圧留去して得られた残渣をシリカゲルカラムクロマトグラフィーにかけ、ヘキサン:酢酸エチル(5:1)で溶出して目的物1.96g(収率40%)を白色固体として得た。
50mLナスフラスコに、上記(1)で合成したヒドロキシクエン酸トリベンジルエステル239mg(0.50mmol)、THF5mL、パルミチン酸クロライド165mg(0.60mmol)を仕込み、氷冷下トリエチルアミン61mg(0.60mmol)をTHF2mLに溶かした溶液を加え、同温で30分、室温で2時間攪拌した。
反応液に酢酸エチル100mLと水50mLを加え、常法に従って有機層を洗浄した後、無水硫酸ナトリウム上で乾燥させた。溶媒を減圧留去して得られた残渣をシリカゲルカラムクロマトグラフィーにかけ、ヘキサン:酢酸エチル(10:1)で溶出して目的物330mg(収率92%)を白色固体として得た。
50mLナスフラスコに上記(2)で合成したヒドロキシクエン酸トリベンジルエステル−2−パルミテート300mg(0.42mmol)を仕込み、エタノール5mL、DMF5mLを加えた。触媒として10質量%パラジウム活性炭を40mg加えて接触還元を2時間行った。触媒をろ別し、溶媒を減圧留去して得られた残渣にヘキサンを加え、析出した固体をろ取し、目的物175mg(収率84%)を白色固体として得た。
1H−NMR (270 MHz, DMSO−D6, ppm): 5.0 (s, 1H, CH),3.2-3.8 (br, 4H, OH, COOH),2.7-3.0 (dd, 2H, -CH2COOH),2.0-2.2 (m, 2H, -CH2COOC-),1.0-1.5 (m, 26H, -(CH2)13-),0.8-0.9 (t, 3H, CH3-).
(4)ヒドロキシクエン酸−2−パルミテート ナトリウム塩の合成
500mLのナスフラスコに上記(3)と同様にして合成したヒドロキシクエン酸−2−パルミテート10g(22.4mmol)を入れ、蒸留水200mLを加えて懸濁した。懸濁液に水酸化ナトリウム2.15g(53.8mmol)を加え、透明になるまで撹拌した。この溶液をエバポレーターで濃縮乾燥し、目的物12.1g(収率99%)を得た。
ヒドロキシクエン酸−2−ミリステート ナトリウム塩の合成
(1)ヒドロキシクエン酸トリベンジルエステル−2−ミリステートの合成
実施例1(1)と同様にして合成したヒドロキシクエン酸トリベンジルエステル330mg(0.69mmol)、THF5mL、ミリスチン酸クロライド340mg(1.38mmol)、トリエチルアミン203mg(2.00mmol)を用いて実施例1(2)と同様に行い、目的物350mg(収率74%)を白色固体として得た。
50mLナスフラスコに上記(1)で合成したヒドロキシクエン酸トリベンジルエステル−2−ミリステート300mg(0.43mmol)、THF5mL、エタノール5mLを用いて実施例1(3)と同様に行い、目的物180mg(収率99%)を白色固体として得た。
なお、この目的物の構造は下記の1H−NMRスペクトルから確認した。
1H−NMR (500 MHz, DMSO−D6, ppm): 5.0 (s, 1H, CH),3.2-3.8 (br, 4H, OH, COOH),2.9 (s, 2H, -CH2COOH),2.2-2.3 (m, 2H, -CH2COOC-),1.1-1.5 (m, 22H, -(CH2)11-),0.8-0.9 (t, 3H, CH3-).
ヒドロキシクエン酸−2−パルミテート10gに替えて上記(2)と同様にして合成したヒドロキシクエン酸−2−ミリステート9.4gを用いた以外は実施例1(4)と同様にして目的物11.4g(収率99%)を得た。
ヒドロキシクエン酸−2−ラウレート ナトリウム塩の合成
(1)ヒドロキシクエン酸トリベンジルエステル−2−ラウレートの合成
実施例1(1)と同様にして合成したヒドロキシクエン酸トリベンジルエステル479mg(1.00mmol)、THF5mL、ラウリル酸クロライド438mg(2.00mmol)、トリエチルアミン203mg(2.00mmol)を用いて実施例1(2)と同様に行い、目的物610mg(収率92%)を白色固体として得た。
50mLナスフラスコに上記(1)で合成したヒドロキシクエン酸トリベンジルエステル−2−ラウレート580mg(0.88mmol)、THF5mL、エタノール5mLを用いて実施例1(3)と同様に行い、目的物342mg(収率88%)を白色固体として得た。
なお、この目的物の構造は下記の1H−NMRスペクトルから確認した。
1H−NMR (500 MHz, DMSO−D6, ppm): 5.0 (s, 1H, CH),3.2-4.2 (br, 4H, OH, COOH),2.9 (s, 2H, -CH2COOH),2.2-2.3 (m, 2H, -CH2COOC-),1.1-1.5 (m, 18H, -(CH2)9-)
,0.8-0.9 (t, 3H, CH3-).
ヒドロキシクエン酸−2−パルミテート10gに替えて上記(2)と同様にして合成したヒドロキシクエン酸−2−ラウレート8.7gを用いた以外は実施例1(4)と同様に
して目的物10.7g(収率99%)を得た。
ヒドロキシクエン酸−2−カプレート ナトリウム塩の合成
(1)ヒドロキシクエン酸トリベンジルエステル−2−カプレートの合成
実施例1(1)と同様にして合成したヒドロキシクエン酸トリベンジルエステル479mg(1.00mmol)、THF5mL、カプリン酸クロライド382mg(2.00mmol)、トリエチルアミン203mg(2.00mmol)を用いて実施例1(2)と同様に行い、目的物570mg(収率90%)を白色固体として得た。
50mLナスフラスコに上記(1)で合成したヒドロキシクエン酸トリベンジルエステル−2−カプレート520mg(0.82mmol)、THF5mL、エタノール5mLを用いて実施例1(3)と同様に行い、目的物240mg(収率81%)を白色固体として得た。
なお、この目的物の構造は下記の1H−NMRスペクトルから確認した。
1H−NMR (500 MHz, DMSO−D6, ppm): 5.0 (s, 1H, CH),3.2-4.2 (br, 4H, OH, COOH),2.9 (s, 2H, -CH2COOH),2.2-2.3 (m, 2H, -CH2COOC-),1.1-1.5 (m, 14H, -(CH2)7-)
,0.8-0.9 (t, 3H, CH3-).
ヒドロキシクエン酸−2−パルミテート10gに替えて上記(2)と同様にして合成したヒドロキシクエン酸−2−カプレート8.1gを用いた以外は実施例1(4)と同様にして目的物10.1g(収率99%)を得た。
ヒドロキシクエン酸−2−オクタノエート ナトリウム塩の合成
(1)ヒドロキシクエン酸トリベンジルエステル−2−オクタノエートの合成
実施例1(1)と同様にして合成したヒドロキシクエン酸トリベンジルエステル479mg(1.00mmol)、THF5mL、カプリル酸クロライド325mg(2.00mmol)、トリエチルアミン203mg(2.00mmol)を用いて実施例1(2)と同様に行い、目的物600mg(収率94%)を白色固体として得た。
50mLナスフラスコに上記(1)で合成したヒドロキシクエン酸トリベンジルエステル−2−オクタノエート490mg(0.81mmol)、THF5mL、エタノール5mLを用いて実施例1(3)と同様に行い、目的物240mg(収率89%)を白色固体として得た。
なお、この目的物の構造は下記の1H−NMRスペクトルから確認した。
1H−NMR (500 MHz, DMSO−D6, ppm): 5.0 (s, 1H, CH),3.2-4.2 (br, 4H, OH, COOH),2.9 (s, 2H, -CH2COOH),2.2-2.3 (m, 2H, -CH2COOC-),1.1-1.6 (m, 10H, -(CH2)5-)
,0.8-0.9 (t, 3H, CH3-).
ヒドロキシクエン酸−2−パルミテート10gに替えて上記(2)と同様にして合成したヒドロキシクエン酸−2−オクタノエート7.5gを用いた以外は実施例1(4)と同様にして目的物9.6g(収率99%)を得た。
ヒドロキシクエン酸−2−ベヘノエート ナトリウム塩の合成
(1)ヒドロキシクエン酸トリベンジルエステル−2−ベヘノエートの合成
実施例1(1)と同様にして合成したヒドロキシクエン酸トリベンジルエステル479mg(1.00mmol)、THF5mL、ベヘノイルクロライド718mg(2.00mmol)、トリエチルアミン203mg(2.00mmol)を用いて実施例1(2)と同様に行い、目的物320mg(収率40%)を白色固体として得た。
50mLナスフラスコに上記(1)で合成したヒドロキシクエン酸トリベンジルエステル−2−ベヘノエート240mg(0.30mmol)、THF5mL、エタノール5mLを用いて実施例1(3)と同様に行い、目的物140mg(収率88%)を白色固体として得た。
なお、この目的物の構造は下記の1H−NMRスペクトルから確認した。
1H−NMR (500 MHz, DMSO−D6+CDCl3, ppm): 5.0 (s, 1H, CH),3.2-4.2 (br, 4H, OH,
COOH),2.9 (s, 2H, -CH2COOH),2.2-2.3 (m, 2H, -CH2COOC-),1.1-1.7 (m, 38H, -(CH2)19-),0.8-0.9 (t, 3H, CH3-).
ヒドロキシクエン酸−2−パルミテート10gに替えて上記(2)と同様にして合成したヒドロキシクエン酸−2−ベヘノエート11.3g及び蒸留水400mLを用いた以外は実施例1(4)と同様にして目的物13.3g(収率99%)を得た。
ヒドロキシクエン酸モノメチルエステル−2−パルミテート ナトリウム塩の合成
(1)ヒドロキシクエン酸ジベンジルエステルモノメチルエステル−2−パルミテートの合成
100mLナスフラスコに、実施例1(1)で合成したヒドロキシクエン酸トリベンジルエステル996mg(2.08mmol)、ジブチルチンオキシド518mg(2.08mmol)を仕込み、メタノール10mLを加え、還流下70分攪拌した。溶媒を減圧留去して得られた残渣にジオキサン10mL、パルミチン酸クロライド632mg(2.30mmol)、トリエチルアミン232mg(2.30mmol)を加え、室温で4時間攪拌した。
反応液に酢酸エチル150mLと水50mLを加え、有機層を常法に従って洗浄した後、無水硫酸ナトリウム上で乾燥させた。溶媒を減圧留去して得られた残渣をシリカゲルカラムクロマトグラフィーにかけ、ヘキサン:酢酸エチル(10:1)で溶出して目的物920mg(収率69%)を白色固体として得た。
50mLナスフラスコに上記(1)で合成したヒドロキシクエン酸ジベンジルエステルモノメチルエステル−2−パルミテート321mg(0.50mmol)を仕込み、エタノール5mL、DMF5mLを加えた。
触媒として10質量%パラジウム活性炭を40mg加えて接触還元を2時間行った。触媒をろ別し、溶媒を減圧留去して得られた残渣にヘキサンを加え、析出した固体をろ取し、目的物207mg(収率90%)を白色固体として得た。
なお、この目的物の構造は下記の1H−NMRスペクトルから確認した。
1H−NMR (270 MHz, DMSO−D6, ppm): 5.0 (s, 1H, CH),3.6 (s, 3H, -COOCH3),3.2-3.6 (br, 3H, OH, COOH),2.8-3.0 (m, 2H, -CH2COOH),2.0-2.2 (m, 2H, -CH2COOC-),1.1-1.6 (m, 26H, -(CH2)13-),0.8-0.9 (t, 3H, CH3-).
ヒドロキシクエン酸−2−パルミテート10gに替えて上記(2)と同様にして合成し
たヒドロキシクエン酸モノメチルエステル−2−パルミテート15.5g及び蒸留水400mLを用いた以外は実施例1(4)と同様にして目的物17.5g(収率99%)を得た。
皮膚浸透試験
被験物質として、
(a)ヒドロキシクエン酸 カルシウム塩(シグマアルドリッチジャパン株式会社)
(b)ヒドロキシクエン酸−2−パルミテート ナトリウム塩(実施例1)
を用い、その0.5質量%をそれぞれダルベッコPBS(−)に溶解した。
2cm角に切ったミニ豚皮膚(チャールスリバー社製(米国))をネットウェル(コーニング社製)に入れ、皮膚表皮側にシリコンシール剤を塗布したアッセイリング(中央に穴が開いたテフロン(R)リング)を押し付け、固定した。次に、マルチウェルプレートに皮膚培養用培地(TOYOBO社製)2mlを入れ、皮膚下部を浸すようにネットウェルをセットした。アッセイリングの穴に被検物質溶液0.1mlを静かに添加し、液漏れが無いことを確認し、マルチプレートシールで密閉し、37℃、二酸化炭素5%のインキュベーター中に静置した。
翌日トリプシン溶液を除去し、蒸留水1mlで3回洗浄し、皮膚片を37℃インキューベーターで5分間加温すると表皮が剥離した。剥離して浮いた表皮をピンセットで剥がし、表皮と真皮に分離した。分離した表皮と真皮をそれぞれ新しい1.5mlチューブに入れ、さらに30分間37℃インキュベーターで加温した。
抽出液中の被検物質はLC/MS法により定量した。抽出液のタンパク含量はLowry法によって定量分析した。
なお、Lowry法に用いる試薬は、新生化学実験講座1、タンパク質1、p85−107を参考にし以下のように調製した。
試薬1 2wt%炭酸ナトリウム含有0.1M水酸化ナトリウム溶液
試薬2 0.5wt%硫酸銅5水和物含有1wt%クエン酸ナトリウム溶液
試薬3 1Nフェノール試薬(Phenol-Reagent)
試薬4 試薬1と2の50:1混合液
標準試料:0.1〜1.5mgのアルブミン溶液
20μlのサンプル液または標準試料液を含むサンプルチューブに、試薬4を400μl加え、混合後、15分以上室温で放置した。次に試薬3を40μl加え、混合後、30分
以上室温で放置した。分光光度計を用いて、750nmの吸光度を測定し、標準試料で作成した検量線を用いて、サンプル液中のタンパク質濃度を決定した。
各分析試料毎のヒドロキシクエン酸量およびヒドロキシクエン酸−2−パルミテート量(単位:nmol/mg皮膚タンパク)を表1に示す。
トリグリセライド蓄積試験(1)
被験物質として、
(a)ヒドロキシクエン酸 カルシウム塩
(b)ヒドロキシクエン酸−2−パルミテート ナトリウム塩(実施例1)
(c)ヒドロキシクエン酸モノメチルエステル−2−パルミテート ナトリウム塩(参考例4)を用いて試験を行った。
マウス3T3−F442A細胞(大日本製薬製)を96ウェルマイクロプレートに播種し、37℃、5%CO2雰囲気下、10質量%FCSを含むDMEM培地(インビトロジェン株式会社製)にて2週間培養した。
各被験物質でのトリグリセライド蓄積量を、対照を100%としたときの相対比較値で表2に示す。
トリグリセライド蓄積試験(2)
被験物質として、
(a)ヒドロキシクエン酸 カルシウム塩
(b)ヒドロキシクエン酸−2−パルミテート ナトリウム塩(実施例1)
を用いた。
ヒト白色前駆脂肪細胞(Zen−Bio社製)を96ウェルマイクロプレートに播種し、37℃、5%CO2雰囲気下、白色脂肪前駆細胞用培地(PM−1、Zen−Bio社製)にて培養した。数日後、コンフルエントに達したことを顕鏡して確認し、ヒト白色前駆
脂肪細胞分化用培地(DM−1、Zen−Bio社製)に交換した。その3日後、分化用培地を白色脂肪細胞用培地(AM−1、Zen−Bio社製)に交換した。3日おきに培地の半量を新しい白色脂肪細胞用培地に交換しながら培養した。
4日間培養後、細胞をダルベッコPBS(−)で3回洗浄し、細胞内に蓄積されたトリグリセリド量をオイルレッド染色法により定量し、alamarBlue(Molecular Probe社製)試薬を用いた比色測定(570nm)により細胞生存率を測定した。
各被験物質でのトリグリセライド蓄積量と細胞生存率を、対照を100%としたときの相対比較値で表3に示した。
トリグリセリド蓄積試験(3)
被験物質として、
(a)ヒドロキシクエン酸 カルシウム塩
(b)ヒドロキシクエン酸−2−パルミテート ナトリウム塩(実施例1)
(d)ヒドロキシクエン酸−2−オクタノエート ナトリウム塩(参考例3)
(e)ヒドロキシクエン酸−2−カプレート ナトリウム塩(参考例2)
(f)ヒドロキシクエン酸−2−ラウレート ナトリウム塩(参考例1)
(g)ヒドロキシクエン酸−2−ミリステート ナトリウム塩(実施例2)
(h)ヒドロキシクエン酸−2−ベヘノエート ナトリウム塩(実施例3)
を用いた。
M培地(インビトロジェン株式会社製)にて2週間培養した。
大部分の細胞が脂肪細胞に分化したことを顕鏡して確認した後、上記被験物質(a)(b)(d)〜(h)をそれぞれ40、50、100、150、200、300、400、500μM、1000mM含む培地に交換し、さらに4日間培養した。対照としては被験物質を添加しない条件で培養したものを用いた。
4日間培養後、細胞をダルベッコPBS(−)で3回洗浄し、細胞内に蓄積されたトリグリセリド量と細胞生存率を試験例3と同様にして測定した。
各被験物質でのトリグリセライド蓄積量と細胞生存率の比が、対照を100としたときの相対値で80以下となる最低濃度を表4に示した。
カフェイン等併用試験(1)
被験物質として、
(b)ヒドロキシクエン酸−2−パルミテート ナトリウム塩(実施例1)
(i)カフェイン一水和物(和光純薬工業株式会社製)
を用いた。
試験例2と同様にしてマウス3T3−F442A細胞を培養し、脂肪細胞への分化を確認後、被験物質(b)0.05mMと被験物質(i)0.1mMを含む培地に交換し、さらに4日間培養した。対照としては被験物質(b)0.05mMを含む培地で培養したものを用いた。
4日間培養後、細胞内に蓄積されたトリグリセライド量を試験例2と同様にして定量した。
各被験物質でのトリグリセライド蓄積量を、対照を100%としたときの相対比較値で表5に示す。
カフェイン等併用試験(2)
被験物質として、
(b)ヒドロキシクエン酸−2−パルミテート ナトリウム塩(実施例1)
(i)カフェイン一水和物(和光純薬工業株式会社)
(j)L−カルニチン塩酸塩(シグマアルドリッチジャパン株式会社)
を用いた。
試験例3と同様にしてヒト白色前駆脂肪細胞(Zen−Bio社製)を培養し、脂肪細胞への分化を確認後、各被験物質を単独で(b)50μM、(i)100μM、(j)50μM、(b)50μMおよび(i)100μM、(b)50μMおよび(j)50μMをそれぞれ含む培地に交換し、さらに4日間培養した。対照としては被験物質を添加しない条件で培養したものを用いた。
4日間培養後、細胞内に蓄積されたトリグリセライド量と細胞生存率を試験例5と同様にして測定した。
各被験物質でのトリグリセライド蓄積量と細胞生存率を、対照を100%としたときの相対比較値で表6に示す。
ヒドロキシクエン酸誘導体の分解確認試験
被験物質として、
(a)ヒドロキシクエン酸 カルシウム塩
(b)ヒドロキシクエン酸−2−パルミテート ナトリウム塩(実施例1)
を用いた。
ヒト白色前駆脂肪細胞(Zen−Bio社製)をT−25フラスコ2枚に播種し、37℃、5%CO2雰囲気下、白色脂肪前駆細胞用培地(PM−1、Zen−Bio社製)にて
培養した。数日後、コンフルエントに達したことを顕鏡して確認し、ヒト白色前駆脂肪細胞分化用培地(DM−1、Zen−Bio社製)に交換した。その3日後、分化用培地を白色脂肪細胞用培地(AM−1、Zen−Bio社製)に交換した。3日おきに培地を新しい白色脂肪細胞用培地に交換しながら培養した。
5日間培養後、トリプシン処理して細胞を各フラスコ底面から剥がし、遠心(1,000rpm、5分間)して細胞を集め、ダルベッコPBS(−)で2回洗浄した。1.5mlチューブに細胞を集め、凍結融解後、蒸留水0.15mlを加えて1.5mlチューブ用マイクロホモジナイザーで破砕した。12,000rpmで5分間遠心して未破砕残渣を取り除き、細胞抽出液を得た。
抽出液中の被検物質はLC/MS法により定量した。抽出液のタンパク含量は試験例1と同様にしてLowry法によって定量分析した。
各分析試料毎のヒドロキシクエン酸量およびヒドロキシクエン酸−2−パルミテート量(単位:nmol/mg皮膚タンパク)を表7に示す。
[実施例4]
次の処方に従い、化粧水を製造した。
(処方例1)
A.
グリチルリチン酸ジカリウム 0.2%
ヒドロキシクエン酸−2−パルミテート ナトリウム塩 1.0%
クエン酸 0.1%
クエン酸ナトリウム 0.3%
精製水 残分
B.
テトラオレイン酸ポリオキシエチレンソルビトール 0.9%
モノオレイン酸ソルビタン 0.1%
オリーブ油 0.1%
ジプロピレングリコール 5.0%
メチルパラベン 0.1%
エタノール 10.0%
A.
クエン酸ナトリウム 0.1%
グリセリン 8.0%
ピロリドンカルボン酸ナトリウム 1.0%
トレハロース 0.03%
1,3―ブチレングリコール 5.0%
ヒドロキシクエン酸−2−パルミテート ナトリウム塩 1.0%
精製水 残分
B.
ポリオキシエチレンポリオキシプロピレンデシルテトラデシルエーテル
0.6%
メチルパラベン 0.1%
エタノール 10.0%
A.
ポリビニルアルコール 0.1%
カルボキシビニルポリマー 0.2%
グリセリン 3.0%
エデト酸三ナトリウム 0.1%
水酸化ナトリウム 0.05%
2−アミノ−2−メチル−1−プロパノール 0.06%
ヒドロキシクエン酸−2−パルミテート ナトリウム塩 1.0%
カフェイン 0.1%
精製水 残分
B.
エタノール 20.0%
ポリオキシエチレンオレイルエーテル 0.3%
メチルパラベン 0.1%
メントール 0.1%
A.
1,3−ブチレングリコール 5.02%
ラウロイルグルタミン酸ジ(コレステリル/ベヘニル/オクチルドデシル)0.5%
トレハロース 0.03%
トリオクタノイン 0.03%
イソステアリン酸PEG−58水添ヒマシ油 1.5%
PEG−60水添ヒマシ油 0.5%
メチルパラベン 0.2%
プロピルパラベン 0.01%
トコフェロール 0.05%
B.
ヒドロキシクエン酸−2−パルミテート ナトリウム塩 1.0%
リンゴ酸ナトリウム 0.1%
リンゴ酸 適量
精製水 残分
次の処方に従い、乳液を製造した。
(処方例5)
A.
スクワラン 10.0%
イソステアリン酸ポリオキシエチレングリセリル 3.5%
トリイソステアリン酸ポリオキシエチレン硬化ヒマシ油 6.5%
ピログルタミン酸イソステアリン酸ポリオキシエチレン硬化ヒマシ油 12.0%
メチルパラベン 0.1%
B.
ヒドロキシクエン酸−2−パルミテート ナトリウム塩 2.0%
精製水 残分
A.
流動パラフィン 10.6%
ミリスチン酸イソプロピル 0.6%
オレイルアルコール 1.2%
ポリオキシエチレンステアリルエーテル 3.4%
ジステアリン酸PEG 1.9%
ポリオキシエチレンポリオキシプロピレンテトラデシルエーテル
0.4%
B.
ステアロイルグルタミン酸ナトリウム 0.1%
プロピレングリコール 1.4%
メチルパラベン 0.1%
PEG−400 0.2%
ヒドロキシクエン酸−2−パルミテート ナトリウム塩 2.0%
精製水 残分
A.
モノステアリン酸ポリオキシエチレンソルビタン 1.0%
テトラオレイン酸ポリオキシエチレンソルビトール 0.5%
モノステアリン酸ソルビタン 1.0%
ステアリン酸 0.5%
ベヘニルアルコール 0.5%
ミツロウ 0.5%
スクワラン 10.0%
トリ2−エチルヘキサン酸グリセリル 10.0%
デカオレイン酸デカグリセリル 3.0%
1,3−ブチレングリコール 7.0%
メチルパラベン 0.1%
B.
キサンタンガム 0.04%
カルボキシビニルポリマー 0.08%
ヒドロキシクエン酸−2−パルミテート ナトリウム塩 2.0%
精製水 残分
C.
トリエタノールアミン 0.05%
精製水 4.95%
次の処方に従い、半透明ジェルを製造した。
(処方例8)
A.
寒天 2.0%
キサンタンガム 0.2%
カフェイン 0.1%
精製水 50.0%
B.
グリセリン 7.0%
PEG−1500 8.0%
メチルパラベン 0.1%
ヒドロキシクエン酸−2−パルミテート ナトリウム塩 2.0%
精製水 残分
0℃以下に冷却してゲル化させた。充分に固まったところでディスパーを用いてゲルを破砕しミクロゲルとした後、脱気して均一ゲル(半透明ジェル)を得た。
A.
カルボキシビニルポリマー 0.35%
精製水 50.0%
B.
水酸化ナトリウム 0.1%
精製水 10.0%
C.
ヒアルロン酸ナトリウム(1%水溶液) 6.0%
ヒドロキシクエン酸−2−パルミテート ナトリウム塩 2.0%
精製水 残分
D.
ポリオキシエチレンポリオキシプロピレンテトラデシルエーテル
0.3%
エタノール 5.0%
メチルパラベン 0.1%
E.
パーフルオロポリエーテル 0.2%
A.
カルボキシビニルポリマー 0.5%
精製水 40.0%
B.
水酸化カリウム 0.1%
精製水 10.0%
C.
ジプロピレングリコール 10.0%
メチルパラベン 0.1%
グリチルリチン酸ジカリウム 0.05%
加水分解コラーゲン 0.05%
ヒドロキシクエン酸−2−パルミテート ナトリウム塩 2.0%
精製水 残分
A.
グリセリン 10.0%
1,3−ブチレングリコール 6.0%
ジメチコン 2.0%
PEG−60水添ヒマシ油 0.6%
ラウレス−2 0.1%
ラウレス−21 0.1%
メチルパラベン 0.26%
プロピルパラベン 0.1%
エチルパラベン 0.1%
フェノキシエタノール 0.1%
酢酸トコフェロール 0.1%
キトサンサクシナミド 0.01%
酵母エキス 0.1%
エタノール 0.01%
香料 0.01%
B.
ヒドロキシクエン酸−2−パルミテート ナトリウム塩 1.0%
カルボキシビニルポリマー 0.5%
尿素 0.02%
グルコサミン塩酸塩 0.01%
エデト酸二ナトリウム 0.01%
精製水 50.0%
C.
アルギニン 0.63%
精製水 残分
A.
グリセリン 50.0%
ヒドロキシクエン酸−2−パルミテート ナトリウム塩 1.0%
トルマリン 5.0%
オリーブ油 1.0%
PEG−12 28.0%
PEG−75 7.5%
ラウリン酸ポリグリセリル 1.0%
エタノール 0.49%
(アクリル酸/アクリル酸アルキル(C10−30))コポリマー 0.11%
メチルパラベン 0.1%
プロピルパラベン 適量
イチョウエキス 適量
チャエキス 適量
マロニエエキス 適量
褐藻エキス 適量
B.
カルボキシビニルポリマー 0.07%
精製水 3.0%
C.
水酸化Na 0.01%
精製水 残分
A.
デカメチルシクロペンタシロキサン 20.0%
アスコルビン酸カリウム 3.0%
ヒドロキシクエン酸−2−パルミテート ナトリウム塩 1.0%
B.
スクワラン 50.0%
軽質流動イソパラフィン 残分
パルミチン酸デキストリン 8.0%
C.
パラメトキシケイ皮酸オクチル 1.0%
フェノキシエタノール 0.5%
α−トコフェロール 0.1%
次の処方に従い、美容液を製造した。
(処方例14)
A.
キサンタンガム 0.4%
ヒドロキシエチルセルロース 0.1%
カルボキシビニルポリマー 0.1%
1,3−ブチレングリコール 5.0%
精製水 50.0%
B.
水酸化カリウム(1%水溶液) 2.5%
精製水 10.0%
C.
ヒドロキシクエン酸−2−パルミテート ナトリウム塩 2.0%
カフェイン 1.0%
精製水 残分
D.
メチルパラベン 0.1%
エタノール 3.0%
A.
1,3−ブチレングリコール 10.0%
グリセリン 5.0%
ヒアルロン酸ナトリウム 0.2%
キサンタンガム 0.2%
グリチルリチン酸ジカリウム 0.02%
ヒドロキシクエン酸−2−パルミテート ナトリウム塩 1.0%
精製水 残分
B.
エタノール 3.0%
水添レシチン 0.5%
トリオクタノイン 0.3%
ジフェニルジメチコン 0.2%
メチルパラベン 0.22%
フェノキシエタノール 0.08%
PEG−50水添ヒマシ油 0.1%
PEG−60水添ヒマシ油 0.1%
α−トコフェロール 0.01%
ミリスチン酸ポリグリセリル−10 0.05%
A.
キサンタンガム 0.4%
ヒドロキシエチルセルロース 0.4%
1,3−ブチレングリコール 3.0%
グリセリン 3.0%
メチルパラベン 0.1%
精製水 残分
B.
ヒドロキシクエン酸−2−パルミテート ナトリウム塩 5.0%
1,2−ヘキサンジオール 4.0%
精製水 50.0%
C.
アスコルビン酸−2−リン酸マグネシウム 1.5%
アスコルビン酸−2−リン酸ナトリウム 1.5%
クエン酸ナトリウム 0.5%
エデト酸四ナトリウム 0.1%
精製水 9.4%
次の処方に従い、クリームを製造した。
(処方例17)
A.
硬化なたね油アルコール 4.2%
イソノナン酸イソノニル 6.0%
スクワラン 9.6%
ミリスチン酸オクチルドデシル 4.8%
モノステアリン酸ポリグリセリル 2.0%
ステアリン酸グリセリル 1.0%
プロピルパラベン 0.05%
キサンタンガム 0.1%
α−トコフェロール 0.5%
B.
1,3−ブチレングリコール 4.8%
グリセリン 4.8%
ヒドロキシクエン酸−2−パルミテート ナトリウム塩 1.0%
アスコルビン酸−2−リン酸−6−パルミチン酸ナトリウム 1.0%
メチルパラベン 0.1%
精製水 残分
次の処方に従い、シート状パックを製造した。
(処方例18)
A.
グリセリン 30.0%
水酸化アルミナマグネシウム 1.0%
B.
ジイソプロパノールアミン 1.0%
ポリアクリル酸ナトリウム 2.0%
アクリル酸/アクリル酸ナトリウム(50/50(モル比))共重合体 2.0%
ヒドロキシクエン酸−2−パルミテート ナトリウム塩 2.0%
アスコルビン酸−2−リン酸マグネシウム 3.0%
精製水 残分
A.
1.3−ブチレングリコール 30.0%
水酸化アルミニウムゲル・炭酸水素ナトリウム共沈物 0.05%
B.
アクリル酸ナトリウム/アクリル酸(70/30(モル比))共重合体 1.0%
ポリアクリル酸 1.0%
N−ビニルアセトアミド/アクリル酸ナトリウム(9/1(wt比))共重合体
3.0%
乳酸アルミニウム 0.05%
アンモニア10%水溶液 0.01%
ヒドロキシクエン酸−2−パルミテート ナトリウム塩 2.0%
アスコルビン酸−2−リン酸マグネシウム 0.01%
精製水 残分
次の処方に従い、ピールオフパックを製造した。
(処方例20)
A.
ポリビニルアルコール 13.0%
カラギーナン 0.5%
ヒドロキシクエン酸−2−パルミテート ナトリウム塩 1.0%
精製水 残分
B.
1,3−ブチレングリコール 3.0%
メチルパラベン 0.1%
エタノール 8.0%
次の処方に従い、入浴剤を製造した。
(処方例21)
テトラオレイン酸ポリオキシエチレンソルビトール 14.0%
ポリオキシエチレンオレイルエーテル 3.0%
セスキオレイン酸ソルビタン 3.0%
スクワラン 10.0%
ホホバ油 20.0%
アボカド油 5.0%
プロピルパラベン 0.1%
ヒドロキシクエン酸−2−パルミテート ナトリウム塩 20.0%
流動パラフィン 残分
炭酸水素ナトリウム 35.5%
クエン酸 37.1%
ポリエチレングリコール 2.1%
酸化マグネシウム 1.1%
α−トコフェロール 1.2%
アスコルビン酸−2−リン酸ナトリウム 1.5%
アスコルビン酸−2−グルコシド 1.5%
ヒドロキシクエン酸−2−パルミテート ナトリウム塩 20.0%
Claims (8)
- ヒドロキシクエン酸及び/又はそのアルカリ金属塩及び/又はそのアルカリ土類金属塩と、長鎖カルボン酸、長鎖アシルクロライド、長鎖カルボン酸無水物、長鎖カルボン酸エステル又は長鎖アルキルニトリルとを溶媒中で反応させることを特徴とする請求項1に記載のヒドロキシクエン酸誘導体又はその塩を製造する方法。
- ヒドロキシクエン酸及び/又はそのアルカリ金属塩及び/又はそのアルカリ土類金属塩を溶媒中でアルコールと反応させ、ヒドロキシクエン酸(トリ)エステルを製造する第一工程と、
長鎖カルボン酸、長鎖アシルクロライド、長鎖カルボン酸無水物、長鎖カルボン酸エステル又は長鎖アルキルニトリルと前記第一工程で得られた化合物とを反応させ、前記第一工程で得られた化合物の水酸基をエステル化する第二工程と、
前記第二工程で得られた化合物のエステル結合部位のうち、第一工程で形成されたエステル結合部位の全部を切断する第三工程とを有することを特徴とする請求項1に記載のヒドロキシクエン酸誘導体又はその塩を製造する方法。 - 請求項1に記載のヒドロキシクエン酸誘導体及び/又はその塩を含有することを特徴とする皮膚外用剤。
- 前記ヒドロキシクエン酸誘導体及び/又はその塩を、0.01質量%〜20質量%の量で含有することを特徴とする請求項4に記載の皮膚外用剤。
- 前記ヒドロキシクエン酸誘導体及び/又はその塩に加えて、ホルモン感受性リパーゼ活性を高める作用を持つ物質を含有することを特徴とする請求項4又は5に記載の皮膚外用剤。
- さらに脂肪酸の分解を高める作用を持つ物質を含有することを特徴とする請求項4〜6のいずれかに記載の皮膚外用剤。
- 請求項4〜7のいずれかに記載の皮膚外用剤を含有してなることを特徴とする化粧料。
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JP5342102B2 (ja) * | 2006-07-04 | 2013-11-13 | 昭和電工株式会社 | エマルション組成物 |
US7985722B2 (en) * | 2006-07-27 | 2011-07-26 | Aurora Advanced Beauty Labs | Rhamnolipid-based formulations |
EP2022475A1 (en) * | 2007-08-07 | 2009-02-11 | KPSS-Kao Professional Salon Services GmbH | Composition for keratin fibres |
WO2010096610A2 (en) * | 2009-02-19 | 2010-08-26 | Elc Management Llc | Compositions and methods for increasing tightly bound water in hair |
CN102038635A (zh) * | 2009-10-23 | 2011-05-04 | 天津天士力集团有限公司 | 一种含有pH值调节剂的紫杉烷类药物溶液及其制备方法 |
JP5634731B2 (ja) * | 2010-03-31 | 2014-12-03 | 日本メナード化粧品株式会社 | 皮膚外用剤 |
JP6006162B2 (ja) * | 2013-05-01 | 2016-10-12 | 昭和電工株式会社 | ヒドロキシトリカルボン酸のベンジル化方法 |
WO2014196598A1 (ja) | 2013-06-07 | 2014-12-11 | 花王株式会社 | 水中油型乳化皮膚化粧料 |
JP2015127315A (ja) * | 2013-12-28 | 2015-07-09 | 日本メナード化粧品株式会社 | 痩身方法 |
JP6266426B2 (ja) * | 2014-04-25 | 2018-01-24 | 日本メナード化粧品株式会社 | 皮膚外用剤 |
JPWO2016067968A1 (ja) * | 2014-10-29 | 2017-04-27 | 昭和電工株式会社 | ミトコンドリア機能改善剤 |
JP6404096B2 (ja) * | 2014-11-19 | 2018-10-10 | 日本メナード化粧品株式会社 | ゲル組成物及び乳化組成物 |
KR20180058727A (ko) * | 2015-09-30 | 2018-06-01 | 가부시키가이샤 시세이도 | 수중유중 분체형 조성물 |
EP3401323B1 (en) * | 2015-12-21 | 2020-07-08 | Showa Denko K.K. | Nicotinamide mononucleotide derivative and salt thereof, method for producing the same, topical agent, cosmetic and food additive |
US11292759B2 (en) * | 2018-03-07 | 2022-04-05 | Nutrition Research Group, Limited | Hydroxycitric acid metal heterocyclic compounds with covalent characteristics |
CN110141526B (zh) * | 2019-07-08 | 2020-08-11 | 杭州悦萱堂化妆品有限公司 | 一种保湿抗皱乳液及其制备方法 |
CN112547313B (zh) * | 2020-11-18 | 2021-10-22 | 东北大学 | 一种羟基柠檬酸在锡石矿物浮选中的应用 |
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FR2716374B1 (fr) * | 1994-02-18 | 1996-04-19 | Sederma Sa | Nouvelles compositions cosmétiques ou dermopharmaceutiques contenant des extraits de plantes. |
GB9507415D0 (en) * | 1994-06-08 | 1995-05-31 | Zylepsis Ltd | Production and uses of caffeic acid and derivatives thereof |
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US20030119913A1 (en) * | 2001-12-20 | 2003-06-26 | Ohia Sunny E. | Method for increasing serotonin levels in a person by administration of a composition incorporating (-)-hydroxycitric acid, and related compositions thereof |
US7118760B2 (en) * | 2003-12-23 | 2006-10-10 | Avon Products, Inc. | Esters of aryl benzimidazole sulfonic acids and sunscreen compositions containing same |
CN1960698A (zh) * | 2004-05-31 | 2007-05-09 | 昭和电工株式会社 | 含肉碱衍生物的局部减肥制剂和化妆品 |
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