JP2011219463A - Composition for external use for cosmetic or medicine with vitamin d stabilized - Google Patents
Composition for external use for cosmetic or medicine with vitamin d stabilized Download PDFInfo
- Publication number
- JP2011219463A JP2011219463A JP2011057522A JP2011057522A JP2011219463A JP 2011219463 A JP2011219463 A JP 2011219463A JP 2011057522 A JP2011057522 A JP 2011057522A JP 2011057522 A JP2011057522 A JP 2011057522A JP 2011219463 A JP2011219463 A JP 2011219463A
- Authority
- JP
- Japan
- Prior art keywords
- vitamin
- fatty acid
- cosmetic
- vitamins
- acid ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 37
- 239000002537 cosmetic Substances 0.000 title claims abstract description 29
- 229940046008 vitamin d Drugs 0.000 title claims abstract description 18
- 239000003814 drug Substances 0.000 title abstract description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims abstract description 53
- -1 fatty acid ester Chemical class 0.000 claims abstract description 45
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 claims abstract description 42
- 239000000194 fatty acid Substances 0.000 claims abstract description 34
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims abstract description 31
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 28
- 229930195729 fatty acid Natural products 0.000 claims abstract description 28
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims abstract description 27
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 claims abstract description 23
- 235000019155 vitamin A Nutrition 0.000 claims abstract description 22
- 239000011719 vitamin A Substances 0.000 claims abstract description 22
- 235000019156 vitamin B Nutrition 0.000 claims abstract description 22
- 239000011720 vitamin B Substances 0.000 claims abstract description 22
- 229940088594 vitamin Drugs 0.000 claims abstract description 21
- 229930003231 vitamin Natural products 0.000 claims abstract description 21
- 235000013343 vitamin Nutrition 0.000 claims abstract description 21
- 239000011782 vitamin Substances 0.000 claims abstract description 21
- 235000019166 vitamin D Nutrition 0.000 claims abstract description 21
- 239000011710 vitamin D Substances 0.000 claims abstract description 21
- 235000019165 vitamin E Nutrition 0.000 claims abstract description 21
- 239000011709 vitamin E Substances 0.000 claims abstract description 21
- 235000019154 vitamin C Nutrition 0.000 claims abstract description 18
- 239000011718 vitamin C Substances 0.000 claims abstract description 18
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 claims abstract description 17
- 229930003270 Vitamin B Natural products 0.000 claims abstract description 17
- 229930003316 Vitamin D Natural products 0.000 claims abstract description 17
- 150000003710 vitamin D derivatives Chemical class 0.000 claims abstract description 17
- 229940045997 vitamin a Drugs 0.000 claims abstract description 17
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229930003427 Vitamin E Natural products 0.000 claims abstract description 14
- 229940046009 vitamin E Drugs 0.000 claims abstract description 14
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229930003268 Vitamin C Natural products 0.000 claims abstract description 13
- LXNHXLLTXMVWPM-UHFFFAOYSA-N Vitamin B6 Natural products CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 claims description 33
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 claims description 27
- 235000005282 vitamin D3 Nutrition 0.000 claims description 25
- 239000011647 vitamin D3 Substances 0.000 claims description 25
- 229940021056 vitamin d3 Drugs 0.000 claims description 25
- 229940011671 vitamin b6 Drugs 0.000 claims description 18
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical group CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 claims description 15
- 229940042585 tocopherol acetate Drugs 0.000 claims description 15
- 229960005070 ascorbic acid Drugs 0.000 claims description 14
- BGRXBNZMPMGLQI-UHFFFAOYSA-N 2-octyldodecyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OCC(CCCCCCCC)CCCCCCCCCC BGRXBNZMPMGLQI-UHFFFAOYSA-N 0.000 claims description 11
- 229940073665 octyldodecyl myristate Drugs 0.000 claims description 11
- 150000003722 vitamin derivatives Chemical class 0.000 claims description 10
- 239000002211 L-ascorbic acid Substances 0.000 claims description 9
- 235000000069 L-ascorbic acid Nutrition 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- RADKZDMFGJYCBB-UHFFFAOYSA-N pyridoxal hydrochloride Natural products CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 claims description 8
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims description 7
- 235000019158 vitamin B6 Nutrition 0.000 claims description 6
- 239000011726 vitamin B6 Substances 0.000 claims description 6
- 235000010323 ascorbic acid Nutrition 0.000 claims description 5
- 239000011668 ascorbic acid Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 229960003471 retinol Drugs 0.000 claims description 5
- 235000020944 retinol Nutrition 0.000 claims description 5
- 239000011607 retinol Substances 0.000 claims description 5
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical group CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 claims description 3
- 230000032683 aging Effects 0.000 claims description 2
- 150000004667 medium chain fatty acids Chemical class 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims description 2
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- 229940079593 drug Drugs 0.000 abstract description 3
- VYGQUTWHTHXGQB-FFHKNEKCSA-N Retinol Palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C VYGQUTWHTHXGQB-FFHKNEKCSA-N 0.000 description 26
- 229940108325 retinyl palmitate Drugs 0.000 description 13
- 235000019172 retinyl palmitate Nutrition 0.000 description 13
- 239000011769 retinyl palmitate Substances 0.000 description 13
- OEWBEINAQKIQLZ-CMRBMDBWSA-N [(2s)-2-[(2r)-3,4-bis(2-hexyldecanoyloxy)-5-oxo-2h-furan-2-yl]-2-(2-hexyldecanoyloxy)ethyl] 2-hexyldecanoate Chemical compound CCCCCCCCC(CCCCCC)C(=O)OC[C@H](OC(=O)C(CCCCCC)CCCCCCCC)[C@H]1OC(=O)C(OC(=O)C(CCCCCC)CCCCCCCC)=C1OC(=O)C(CCCCCC)CCCCCCCC OEWBEINAQKIQLZ-CMRBMDBWSA-N 0.000 description 12
- 238000002156 mixing Methods 0.000 description 12
- 235000008160 pyridoxine Nutrition 0.000 description 12
- 239000011677 pyridoxine Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 239000006210 lotion Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000006071 cream Substances 0.000 description 4
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 3
- BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 3
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- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 2
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- 125000004432 carbon atom Chemical group C* 0.000 description 2
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- TUYRNAGGIJZRNM-LBHUVFDKSA-N [(2s)-2-[(2r)-4-hexadecanoyloxy-3-hydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethyl] hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(OC(=O)CCCCCCCCCCCCCCC)=C1O TUYRNAGGIJZRNM-LBHUVFDKSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940100609 all-trans-retinol Drugs 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 229940072065 ascorbic acid 2-sulfate Drugs 0.000 description 1
- 229940066595 beta tocopherol Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229960002685 biotin Drugs 0.000 description 1
- 235000020958 biotin Nutrition 0.000 description 1
- 239000011616 biotin Substances 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- FDJOLVPMNUYSCM-WZHZPDAFSA-L cobalt(3+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(1r,2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2 Chemical compound [Co+3].N#[C-].N([C@@H]([C@]1(C)[N-]\C([C@H]([C@@]1(CC(N)=O)C)CCC(N)=O)=C(\C)/C1=N/C([C@H]([C@@]1(CC(N)=O)C)CCC(N)=O)=C\C1=N\C([C@H](C1(C)C)CCC(N)=O)=C/1C)[C@@H]2CC(N)=O)=C\1[C@]2(C)CCC(=O)NC[C@@H](C)OP([O-])(=O)O[C@H]1[C@@H](O)[C@@H](N2C3=CC(C)=C(C)C=C3N=C2)O[C@@H]1CO FDJOLVPMNUYSCM-WZHZPDAFSA-L 0.000 description 1
- CAEMOCUMMOVWCN-UHFFFAOYSA-N diphosphono hydrogen phosphate phosphoric acid Chemical class OP(O)(O)=O.OP(O)(=O)OP(O)(=O)OP(O)(O)=O CAEMOCUMMOVWCN-UHFFFAOYSA-N 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- 229960000304 folic acid Drugs 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 235000010382 gamma-tocopherol Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008269 hand cream Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- JMOLZNNXZPAGBH-UHFFFAOYSA-N hexyldecanoic acid Chemical compound CCCCCCCCC(C(O)=O)CCCCCC JMOLZNNXZPAGBH-UHFFFAOYSA-N 0.000 description 1
- 229950004531 hexyldecanoic acid Drugs 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 150000003903 lactic acid esters Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N n-hexadecanoic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 229960003966 nicotinamide Drugs 0.000 description 1
- 235000005152 nicotinamide Nutrition 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229940055726 pantothenic acid Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 229960003581 pyridoxal Drugs 0.000 description 1
- 235000008164 pyridoxal Nutrition 0.000 description 1
- 239000011674 pyridoxal Substances 0.000 description 1
- 235000008151 pyridoxamine Nutrition 0.000 description 1
- 239000011699 pyridoxamine Substances 0.000 description 1
- 125000002181 pyridoxine group Chemical group 0.000 description 1
- ZUFQODAHGAHPFQ-UHFFFAOYSA-N pyridoxine hydrochloride Chemical compound Cl.CC1=NC=C(CO)C(CO)=C1O ZUFQODAHGAHPFQ-UHFFFAOYSA-N 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 229960002477 riboflavin Drugs 0.000 description 1
- 230000008591 skin barrier function Effects 0.000 description 1
- 229940010747 sodium hyaluronate Drugs 0.000 description 1
- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960003495 thiamine Drugs 0.000 description 1
- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229960001727 tretinoin Drugs 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
- 150000003697 vitamin B6 derivatives Chemical class 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
- DIPPFEXMRDPFBK-JPWDPSJFSA-N vitamin D4 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CC[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C DIPPFEXMRDPFBK-JPWDPSJFSA-N 0.000 description 1
- RMDJVOZETBHEAR-LQYWTLTGSA-N vitamin D5 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CC[C@@H](CC)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C RMDJVOZETBHEAR-LQYWTLTGSA-N 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 239000002076 α-tocopherol Substances 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
Landscapes
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Abstract
Description
本発明は、ビタミンＤ類が安定化された化粧用又は医薬用外用組成物に関する。 The present invention relates to a cosmetic or pharmaceutical composition for external use in which vitamin D is stabilized.
ビタミン類を含有する化粧用又は医薬用外用組成物としては以下に示すような例が知られている。例えば、ビタミンＣ（特許文献２参照）、ビタミンＥ（特許文献３参照）が皮膚ヒアルロン酸の産生促進作用を有することが知られている。
また、ビタミンＤ３が皮膚の弾性およびしわの改善効果を有することが知られている（特許文献１参照）。
The following examples are known as cosmetic or pharmaceutical external compositions containing vitamins. For example, it is known that vitamin C (see Patent Document 2) and vitamin E (see Patent Document 3) have a skin hyaluronic acid production promoting action.
It is also known that vitamin D3 has an effect of improving skin elasticity and wrinkles (see Patent Document 1).
なお、ビタミンＢについては、ヒアルロン酸産生、皮膚弾性又はシワに対する作用は不明であるが、ニコチン酸アミド化合物を含有する皮膚外用組成物に皮膚バリアー機能を有すること（特許文献４参照）、ビタミンＡ酸（レチノイン酸）と水溶性のビタミンＢ６塩酸塩を含有する美白用皮膚外用剤（特許文献５参照）が知られている。 As for vitamin B, the effects on hyaluronic acid production, skin elasticity or wrinkles are unknown, but the skin external composition containing a nicotinamide compound has a skin barrier function (see Patent Document 4), vitamin A A whitening skin external preparation (see Patent Document 5) containing an acid (retinoic acid) and water-soluble vitamin B6 hydrochloride is known.
しかしながら、ビタミンＡ、Ｂ、Ｃ、Ｄ及びＥのすべてを配合した外用組成物は知られていない。また、ビタミンＡ、Ｂ、Ｃ及びＥがビタミンＤを安定化することも知られていない。 However, an external composition containing all of vitamins A, B, C, D and E is not known. It is also not known that vitamins A, B, C and E stabilize vitamin D.
本発明者らは、ビタミン類の安定性に優れた半固形の化粧用又は医薬用外用組成物を開発すべく長年に渡って鋭意研究を継続してきた。その研究の途中、通常の半固形の化粧用又は医薬用外用組成物中でビタミンＤ類を安定に存在させることが困難であることを見出した。 The present inventors have continued intensive research for many years in order to develop a semi-solid cosmetic or pharmaceutical composition with excellent stability of vitamins. During the research, it was found that it was difficult to make vitamin Ds stably present in ordinary semisolid cosmetic or pharmaceutical external compositions.
本発明者らは、上述の課題を解決するために鋭意研究を継続して行った結果、本発明を完成させた。すなわち、本発明は、以下に記すとおりである。
［１］
（１）ビタミンＡ類、ビタミンＢ類、ビタミンＣ類、ビタミンＥ類からなる群より選択される１種又は２種以上のビタミンと（２）高級脂肪酸エステルとを添加することによりビタミンＤ類が安定化された、（１）ビタミンＡ類、ビタミンＢ類、ビタミンＣ類、ビタミンＥ類からなる群より選択される１種又は２種以上のビタミン；（２）高級脂肪酸エステル；及びビタミンＤ類を含有する化粧用又は医薬用外用組成物。
The inventors of the present invention have completed the present invention as a result of continuing intensive studies to solve the above-described problems. That is, the present invention is as described below.
[1]
(1) By adding one or more vitamins selected from the group consisting of vitamins A, vitamins B, vitamins C and vitamins E, and (2) higher fatty acid esters, vitamins D are added. Stabilized (1) one or more vitamins selected from the group consisting of vitamin A, vitamin B, vitamin C, vitamin E; (2) higher fatty acid esters; and vitamin D A cosmetic or pharmaceutical composition for external use.
さらに、本発明として好適には以下に示す発明が挙げられる。
［２］
（１）ビタミンＡ類、ビタミンＢ類、ビタミンＣ類及びビタミンＥ類と（２）高級脂肪酸エステルとを添加することによりビタミンＤ類が安定化された、（１）ビタミンＡ類、ビタミンＢ類、ビタミンＣ類及びビタミンＥ類；（２）高級脂肪酸エステル；及びビタミンＤ類を含有する化粧用又は医薬用外用組成物。
［３］
ビタミンＡ類がレチノール脂肪酸エステルである、［１］又は［２］に記載の化粧用又は医薬用外用組成物。
［４］
ビタミンＢ類がビタミンＢ６脂肪酸エステルである、［１］−［３］から選択されるいずれか１項に記載の化粧用又は医薬用外用組成物。
［５］
ビタミンＣ類がアスコルビン酸モノ脂肪酸エステル、Ｌ−アスコルビン酸ジ脂肪酸エステル又はＬ−アスコルビン酸テトラ脂肪酸エステルである、［１］−［４］から選択されるいずれか１項に記載の化粧用又は医薬用外用組成物。
［６］
ビタミンＤ類がコレカルシフェロールである、［１］−［５］から選択されるいずれか１項に記載の化粧用又は医薬用外用組成物。
［７］
ビタミンＥ類が酢酸トコフェロールである、［１］−［６］から選択されるいずれか１項に記載の化粧用又は医薬用外用組成物。
［８］
高級脂肪酸エステル類がパルミチン酸イソプロピル、ミリスチン酸イソプロピル、ミリスチン酸オクチルドデシル又は中鎖脂肪酸トリグリセリドである、［１］−［７］から選択されるいずれか１項に記載の化粧用又は医薬用外用組成物。
［９］
老化防止用である、［１］−［８］から選択されるいずれか１項に記載の化粧用又は医薬用外用組成物。
［１０］
（１）ビタミンＡ類、ビタミンＢ類、ビタミンＣ類、ビタミンＥ類からなる群より選択される１種又は２種以上のビタミンと（２）高級脂肪酸エステルとを添加することによりビタミンＤ類を安定化する方法。
［１１］
（１）ビタミンＡ類、ビタミンＢ類、ビタミンＣ類及びビタミンＥ類と（２）高級脂肪酸エステルとを添加することによりビタミンＤ類を安定化する方法。
Further, the present invention preferably includes the following inventions.
[2]
(1) Vitamin A, Vitamin B, Vitamin C and Vitamin E and (2) Vitamin D is stabilized by adding higher fatty acid esters. (1) Vitamin A and Vitamin B Vitamin Cs and vitamins E; (2) higher fatty acid esters; and vitamin Ds for cosmetic or pharmaceutical use.
[3]
The cosmetic or pharmaceutical composition for external use according to [1] or [2], wherein the vitamin A is a retinol fatty acid ester.
[4]
The cosmetic or pharmaceutical composition for external use according to any one of [1] to [3], wherein the vitamin B is a vitamin B6 fatty acid ester.
[5]
The cosmetic or pharmaceutical according to any one of [1] to [4], wherein the vitamin C is ascorbic acid mono-fatty acid ester, L-ascorbic acid di-fatty acid ester, or L-ascorbic acid tetra-fatty acid ester. Composition for external use.
[6]
The cosmetic or pharmaceutical external composition according to any one of [1] to [5], wherein the vitamin D is cholecalciferol.
[7]
The cosmetic or pharmaceutical composition for external use according to any one of [1] to [6], wherein the vitamin E is tocopherol acetate.
[8]
The cosmetic or pharmaceutical external composition according to any one of [1] to [7], wherein the higher fatty acid ester is isopropyl palmitate, isopropyl myristate, octyldodecyl myristate, or medium-chain fatty acid triglyceride. object.
[9]
The cosmetic or pharmaceutical external composition according to any one of [1] to [8], which is used for preventing aging.
[10]
(1) Vitamin D by adding one or more vitamins selected from the group consisting of vitamin A, vitamin B, vitamin C, and vitamin E and (2) a higher fatty acid ester How to stabilize.
[11]
(1) A method of stabilizing vitamin D by adding vitamin A, vitamin B, vitamin C and vitamin E and (2) a higher fatty acid ester.
本発明により、ビタミンＤ類を安定に存在させた半固形の化粧用又は医薬用外用組成物を提供することができる。 According to the present invention, it is possible to provide a semisolid cosmetic or pharmaceutical composition for external use in which vitamin D is stably present.
本発明の「半固形」の組成物は、ローション剤、乳剤、ゲル剤、クリーム剤、軟膏剤等の医薬用組成物を包含する。また、化粧水、乳液、クリーム、美容液、パック、ファンデーション、ハンドクリーム、ボディローション等の化粧用組成物も包含する。 The “semi-solid” composition of the present invention includes pharmaceutical compositions such as lotions, emulsions, gels, creams, ointments and the like. In addition, cosmetic compositions such as lotion, milky lotion, cream, cosmetic liquid, pack, foundation, hand cream, body lotion and the like are also included.
本発明の「ビタミンＡ類」は、例えば、レチノール；レチノールのパルミチン酸エステル、ステアリン酸エステル、酢酸エステル等の各種脂肪酸エステル；レチノールの乳酸エステル、グリコール酸エステル等の各種有機酸エステル；レチノールのリン酸、ピロリン酸、硫酸等の各種無機酸ジエステル複合体等が挙げられる。好適には、オール−ｔｒａｎｓ−レチノールおよびその異性体、オール−ｔｒａｎｓ―レチノイン酸およびその異性体、オール−ｔｒａｎｓ―レチナールおよびその異性体、それらの３デヒドロ体、３，４ジデヒドロ体、さらには、広く市販されており、安定性が比較的良好なパルミチン酸レチノールが挙げられる。特に好適には、パルミチン酸レチノールである。これらのビタミンＡは、合成によって得られたものであっても、天然抽出物より得られたものであっても、それを精製したものであっても良い。
本発明の「ビタミンＢ類」は、例えば、ビタミンＢ１、ビタミンＢ２、ナイアシン、パントテン酸、ビタミンＢ６、ビタミンＢ１２、葉酸、ビオチン等を挙げることができる。ビタミンＢ類として、好適には、ピリドキシン、ピリドキサール、ピリドキサミン等のビタミンＢ６であり、さらに好適には、脂溶性ビタミンＢ６（ビタミンＢ６の脂肪酸エステル）であり、特に好適には、トリス２−ヘキシルデカン酸ピリドキシン（脂溶性ビタミンＢ６誘導体の一種、以下、ＶＢ６−ＩＰと称することがある。）である。
本発明の「ビタミンＣ類」は、例えば、Ｌ−アスコルビン酸モノステアレート、Ｌ−アスコルビン酸モノパルミテート、Ｌ−アスコルビン酸モノオレエート等のアスコルビン酸モノ脂肪酸エステル；Ｌ−アスコルビン酸モノリン酸エステル、Ｌ−アスコルビン酸−２−硫酸エステル等のアスコルビン酸モノリン酸エステル；Ｌ−アスコルビン酸ジステアレート、Ｌ−アスコルビン酸ジパルミテート、Ｌ−アスコルビン酸ジオレエート等のＬ−アスコルビン酸ジ脂肪酸エステル；Ｌ−アスコルビン酸トリステアレート、Ｌ−アスコルビン酸トリパルミテート、Ｌ−アスコルビン酸トリオレエート等のＬ−アスコルビン酸トリ脂肪酸エステル；アスコルビン酸テトライソパルミテート等のＬ−アスコルビン酸テトラ脂肪酸エステル；Ｌ−アスコルビン酸トリリン酸エステル等のＬ−アスコルビン酸トリリン酸エステル等を挙げることができる。これらのビタミンＣ類として、好適には、アスコルビン酸モノ脂肪酸エステル、Ｌ−アスコルビン酸ジ脂肪酸エステル又はＬ−アスコルビン酸テトラ脂肪酸エステルであり、更に好適には、Ｌ−アスコルビン酸−６−モノステアレート、Ｌ−アスコルビン酸−６−モノパルミテート、Ｌ−アスコルビン酸−２，６−ジパルミテート、テトラ２−ヘキシルデカン酸アスコルビル（以下、ＶＣ−ＩＰと称することがある。）等である。
本発明の「ビタミンＤ類」は、例えば、ビタミンＤ２（エルゴカルシフェロール）、ビタミンＤ３（コレカルシフェロール）、ビタミンＤ４、ビタミンＤ５、ビタミンＤ６、ビタミンＤ７、１，２５−ジヒドロキシコレカルシフェロール等が挙げられる。これらのビタミンＤ類の中でも、好適には、ビタミンＤ３（コレカルシフェロール）を用いることが好ましい。
本発明の「ビタミンＥ類」は、例えば、α−トコフェロール、β−トコフェロール、γ−トコフェロール、ｄ−トコフェロール、酢酸トコフェロール、ニコチン酸ＤＬ−α−トコフェロール、コハク酸ＤＬ−α−トコフェロール等が挙げられ、好適には、酢酸トコフェロールが挙げられる。
“Vitamin A” of the present invention includes, for example, retinol; various fatty acid esters such as palmitic acid ester, stearic acid ester, and acetic acid ester of retinol; various organic acid esters such as lactic acid ester and glycolic acid ester of retinol; Examples thereof include various inorganic acid diester complexes such as acid, pyrophosphoric acid, and sulfuric acid. Preferably, all-trans-retinol and its isomers, all-trans-retinoic acid and its isomers, all-trans-retinal and its isomers, their 3 dehydro, 3,4 didehydro, Examples thereof include retinol palmitate, which is widely marketed and has relatively good stability. Particularly preferred is retinol palmitate. These vitamin A may be obtained by synthesis, may be obtained from a natural extract, or may be obtained by purifying it.
Examples of the “vitamin B” of the present invention include vitamin B1, vitamin B2, niacin, pantothenic acid, vitamin B6, vitamin B12, folic acid, biotin and the like. Vitamin B is preferably vitamin B6 such as pyridoxine, pyridoxal, pyridoxamine, more preferably fat-soluble vitamin B6 (fatty acid ester of vitamin B6), particularly preferably tris 2-hexyldecanoic acid. It is pyridoxine (a kind of fat-soluble vitamin B6 derivative, hereinafter sometimes referred to as VB6-IP).
“Vitamin Cs” of the present invention include, for example, ascorbic acid monofatty acid esters such as L-ascorbic acid monostearate, L-ascorbic acid monopalmitate, L-ascorbic acid monooleate; L-ascorbic acid monophosphate, L Ascorbic acid monophosphates such as ascorbic acid-2-sulfate; L-ascorbic acid difatty acid esters such as L-ascorbic acid distearate, L-ascorbic acid dipalmitate, L-ascorbic acid dioleate; L-ascorbic acid tristearate L-ascorbic acid trifatty acid esters such as L-ascorbic acid tripalmitate and L-ascorbic acid trioleate; L-ascorbic acid tetrafatty acid esters such as ascorbic acid tetraisopalmitate; Like phosphate triphosphate esters of L- ascorbic acid triphosphate ester, and the like. These vitamin Cs are preferably ascorbic acid monofatty acid ester, L-ascorbic acid difatty acid ester or L-ascorbic acid tetrafatty acid ester, and more preferably L-ascorbic acid-6-monostearate. L-ascorbic acid-6-monopalmitate, L-ascorbic acid-2,6-dipalmitate, ascorbyl tetra-2-hexyldecanoate (hereinafter sometimes referred to as VC-IP), and the like.
Examples of the “vitamin D” of the present invention include vitamin D2 (ergocalciferol), vitamin D3 (cholecalciferol), vitamin D4, vitamin D5, vitamin D6, vitamin D7, 1,25-dihydroxycholecalciferol and the like. Can be mentioned. Among these vitamin Ds, vitamin D3 (cholecalciferol) is preferably used.
Examples of the “vitamin E” of the present invention include α-tocopherol, β-tocopherol, γ-tocopherol, d-tocopherol, tocopherol acetate, DL-α-tocopherol nicotinate, DL-α-tocopherol succinate and the like. Preferably, tocopherol acetate is used.
本発明の「高級脂肪酸エステル」は、炭素数１０−３０の脂肪酸と炭素数２−３０のアルコール類からなるエステルであり、好適には、パルミチン酸イソプロピル、ミリスチン酸イソプロピル、ミリスチン酸オクチルドデシル、中鎖脂肪酸トリグリセリド等が挙げられる。
本発明の組成物には、ビタミンＡ類；ビタミンＢ類；ビタミンＣ類；ビタミンＤ類；ビタミンＥ類及び高級脂肪酸エステル以外に、通常、医薬品、医薬部外品、化粧品などの外用組成物に用いられる成分、例えば、水性成分、油性成分、粉末成分、アルコール類、保湿剤、増粘剤、紫外線吸収剤、美白剤、防腐剤、酸化防止剤、界面活性剤、香料、色素などを適宜必要に応じて配合することができる。そのような配合の方法は、日局製剤総則等に記載の方法に従って行うことができる。
The “higher fatty acid ester” of the present invention is an ester comprising a fatty acid having 10 to 30 carbon atoms and an alcohol having 2 to 30 carbon atoms, preferably isopropyl palmitate, isopropyl myristate, octyldodecyl myristate, And chain fatty acid triglycerides.
In addition to vitamins A, vitamins B, vitamins C, vitamins D, vitamins E and higher fatty acid esters, the composition of the present invention is usually used for external compositions such as pharmaceuticals, quasi drugs and cosmetics. Necessary components such as aqueous components, oily components, powder components, alcohols, humectants, thickeners, UV absorbers, whitening agents, preservatives, antioxidants, surfactants, fragrances, pigments, etc. It can be blended according to. Such a blending method can be performed according to the method described in the Japanese Pharmacopoeia General Rules and the like.
本発明の組成物において含有されるビタミン類等の含有量は、各ビタミン類の種類により異なるが、パルミチン酸レチノール、トリ２−ヘキシルデカン酸ピリドキシン、テトラ２−ヘキシルデカン酸アスコルビル、コレカルシフェロール及び酢酸トコフェロールを含有する場合には、その重量％は、それぞれ以下のようになる。
好適には、０．０１〜１％（１万〜１００万ＩＵ／１００ｇ）、０．０１〜１０％、０．０１〜１０％、０．００００１〜１％及び０．０１〜５％であり、より好適には、０．０５〜０．５％（５万〜５０万ＩＵ／１００ｇ）、０．１〜５％、０．１〜５％、０．０００１〜０．１％及び０．１〜２％である。
The content of vitamins and the like contained in the composition of the present invention varies depending on the type of each vitamin, but retinol palmitate, pyridoxine tri-2-hexyldecanoate, ascorbyl tetra-2-hexyldecanoate, cholecalciferol and tocopherol acetate When it contains, the weight% is as follows, respectively.
Preferably, 0.01-1% (10,000-1 million IU / 100g), 0.01-10%, 0.01-10%, 0.00001-1% and 0.01-5% More preferably, 0.05 to 0.5% (50,000 to 500,000 IU / 100 g), 0.1 to 5%, 0.1 to 5%, 0.0001 to 0.1%, and 0. 1-2%.
（製剤例１）クリーム
パルミチン酸レチノール０．２３ｇ、トリ２−ヘキシルデカン酸ピリドキシン３．０ｇ、テトラ２−ヘキシルデカン酸アスコルビル３．０ｇ、コレカルシフェロール０．０００２ｇ、酢酸トコフェロール１．０ｇ、自己乳化型モノステアリン酸グリセリン５．０ｇ、ポリオキシエチレンセチルエーテル１．５ｇ、セタノール５．０ｇ、スクワラン８．０ｇおよびミリスチン酸イソプロピル８．０ｇを混合し、８０℃に加温して均一に溶解し、混合物（A）を調製した。
別に、1,3-ブチレングリコール５．０ｇおよび精製水５０．３ｇを混合し、８０℃に加温し均一にし、混合物（B）を調製した。
さらに、キサンタンガム０．０２ｇを水１０．０ｇに溶解し、８０℃に加温し、混合物（C）を調製した。
次に、（A）を８０℃で加温撹拌しながら、（B）を徐々に添加し、撹拌を続けながら、５０℃まで冷却し、（C）を添加し、混合した。さらに撹拌を続け、３５℃で調製を終了し、クリームを得た。
(Formulation Example 1) Cream 0.23 g of retinol palmitate, 3.0 g of pyridoxine tri-2-hexyldecanoate, 3.0 g of ascorbyl tetra-2-hexyldecanoate, 0.0002 g of cholecalciferol, 1.0 g of tocopherol acetate, self-emulsifying mono Glycerol stearate 5.0 g, polyoxyethylene cetyl ether 1.5 g, cetanol 5.0 g, squalane 8.0 g and isopropyl myristate 8.0 g were mixed and heated to 80 ° C. to dissolve evenly. A) was prepared.
Separately, 5.0 g of 1,3-butylene glycol and 50.3 g of purified water were mixed and heated to 80 ° C. to make a uniform mixture (B).
Furthermore, 0.02 g of xanthan gum was dissolved in 10.0 g of water and heated to 80 ° C. to prepare a mixture (C).
Next, while (A) was heated and stirred at 80 ° C., (B) was gradually added. While continuing stirring, the mixture was cooled to 50 ° C., and (C) was added and mixed. Stirring was continued and the preparation was completed at 35 ° C. to obtain a cream.
（製剤例２）ローション
パルミチン酸レチノール０．２３ｇ、トリ２−ヘキシルデカン酸ピリドキシン３．０ｇ、テトラ２−ヘキシルデカン酸アスコルビル３．０ｇ、コレカルシフェロール０．０００２ｇ、酢酸トコフェロール１．０ｇ、ポリオキシエチレンポリオキシプロピレンセチルエーテル０．６ｇ、ミリスチン酸オクチルドデシル２．０ｇを混合し、７０℃に加温して均一に溶解し、混合物（A）を調製した。
別に、1.3-ブチレングリコール５．０ｇ、ジプロピレングリコール５．０ｇ、メチルパラベン０．３ｇおよび精製水２０．０ｇを混合し、均一に溶解し、混合物（B）を調製した。
さらに、ヒアルロン酸ナトリウム０．００５ｇを水１５．０ｇに均一に溶解し、混合物（C）を調製した。
次に、（A）を７０℃で加温撹拌しながら、７０℃に加温した精製水４８．０ｇを徐々に添加し、撹拌を続けながら、５０℃まで冷却し、（B）および（C）を添加し、混合した。さらに撹拌を続け、３５℃で調製を終了し、ローションを得た。
(Formulation Example 2) Lotion 0.23 g of retinol palmitate, 3.0 g of pyridoxine tri-2-hexyldecanoate, 3.0 g of ascorbyl tetra-2-hexyldecanoate, 0.0002 g of cholecalciferol, 1.0 g of tocopherol acetate, polyoxyethylene poly 0.6 g of oxypropylene cetyl ether and 2.0 g of octyldodecyl myristate were mixed, heated to 70 ° C. and uniformly dissolved to prepare a mixture (A).
Separately, 5.0 g of 1.3-butylene glycol, 5.0 g of dipropylene glycol, 0.3 g of methylparaben and 20.0 g of purified water were mixed and dissolved uniformly to prepare a mixture (B).
Furthermore, 0.005 g of sodium hyaluronate was uniformly dissolved in 15.0 g of water to prepare a mixture (C).
Next, while heating and stirring (A) at 70 ° C., 48.0 g of purified water heated to 70 ° C. was gradually added, and the mixture was cooled to 50 ° C. while continuing to stir. ) Was added and mixed. Stirring was continued and the preparation was completed at 35 ° C. to obtain a lotion.
（実施例１）
パルミチン酸レチノール０．１１５ｇ、トリ２−ヘキシルデカン酸ピリドキシン１．５ｇ、テトラ２−ヘキシルデカン酸アスコルビル１．５ｇ、コレカルシフェロール０．０５ｇおよび酢酸トコフェロール０．５ｇを量り、全量が５０ｇとなるようミリスチン酸イソプロピルを加えた後、混合し調製した。
(Example 1)
Retinol palmitate 0.115 g, pyridoxine tri-2-hexyldecanoate 1.5 g, ascorbyl tetra-2-hexyldecanoate 1.5 g, cholecalciferol 0.05 g, and tocopherol acetate 0.5 g were measured to give a total amount of myristic acid to 50 g. After adding isopropyl, it was prepared by mixing.
（実施例２）
パルミチン酸レチノール０．１１５ｇ、トリ２−ヘキシルデカン酸ピリドキシン１．５ｇ、テトラ２−ヘキシルデカン酸アスコルビル１．５ｇ、コレカルシフェロール０．０５ｇおよび酢酸トコフェロール０．５ｇを量り、全量が５０ｇとなるようミリスチン酸オクチルドデシルを加えた後、混合し調製した。
(Example 2)
Retinol palmitate 0.115 g, pyridoxine tri-2-hexyldecanoate 1.5 g, ascorbyl tetra-2-hexyldecanoate 1.5 g, cholecalciferol 0.05 g, and tocopherol acetate 0.5 g were measured to give a total amount of myristic acid to 50 g. After adding octyldodecyl, it was prepared by mixing.
（実施例３）
パルミチン酸レチノール０．１１５ｇおよびコレカルシフェロール０．０５ｇを量り、全量が５０ｇとなるようミリスチン酸オクチルドデシルを加えた後、混合し調製した。
（実施例４）
トリ２−ヘキシルデカン酸ピリドキシン１．５ｇおよびコレカルシフェロール０．０５ｇを量り、全量が５０ｇとなるようミリスチン酸オクチルドデシルを加えた後、混合し調製した。
(Example 3)
0.115 g of retinol palmitate and 0.05 g of cholecalciferol were weighed, octyldodecyl myristate was added to a total amount of 50 g, and then mixed to prepare.
Example 4
1.5 g of pyridoxine tri-2-hexyldecanoate and 0.05 g of cholecalciferol were weighed and octyldodecyl myristate was added to a total amount of 50 g, followed by mixing.
（実施例５）
パルミチン酸レチノール０．１１５ｇ、テトラ２−ヘキシルデカン酸アスコルビル１．５ｇ、コレカルシフェロール０．０５ｇおよび酢酸トコフェロール０．５ｇを量り、全量が５０ｇとなるようミリスチン酸オクチルドデシルを加えた後、混合し調製した。
(Example 5)
Prepared by mixing 0.115 g of retinol palmitate, 1.5 g of ascorbyl tetra-2-hexyldecanoate, 0.05 g of cholecalciferol and 0.5 g of tocopherol acetate, adding octyldodecyl myristate to a total amount of 50 g, and mixing did.
（実施例６）
コレカルシフェロール０．０５ｇおよび酢酸トコフェロール０．５ｇを量り、全量が５０ｇとなるようミリスチン酸オクチルドデシルを加えた後、混合し調製した。
（比較例１）
パルミチン酸レチノール０．１１５ｇ、トリ２−ヘキシルデカン酸ピリドキシン１．５ｇ、テトラ２−ヘキシルデカン酸アスコルビル１．５ｇ、コレカルシフェロール０．０５ｇおよび酢酸トコフェロール０．５ｇを量り、全量が５０ｇとなるよう流動パラフィンを加えた後、混合し調製した。
(Example 6)
0.05 g of cholecalciferol and 0.5 g of tocopherol acetate were weighed and octyldodecyl myristate was added to a total amount of 50 g, followed by mixing.
(Comparative Example 1)
Weigh 0.115 g of retinol palmitate, 1.5 g of pyridoxine tri-2-hexyldecanoate, 1.5 g of ascorbyl tetra-2-hexyldecanoate, 0.05 g of cholecalciferol and 0.5 g of tocopherol acetate so that the total amount is 50 g. Was added and mixed to prepare.
（比較例２）
パルミチン酸レチノール０．１１５ｇ、トリ２−ヘキシルデカン酸ピリドキシン１．５ｇ、テトラ２−ヘキシルデカン酸アスコルビル１．５ｇ、コレカルシフェロール０．０５ｇおよび酢酸トコフェロール０．５ｇを量り、全量が５０ｇとなるようオクチルドデカノールを加えた後、混合し調製した。
(Comparative Example 2)
Octyldodeca is measured so that 0.115 g of retinol palmitate, 1.5 g of pyridoxine tri-2-hexyldecanoate, 1.5 g of ascorbyl tetra-2-hexyldecanoate, 0.05 g of cholecalciferol and 0.5 g of tocopherol acetate are added so that the total amount becomes 50 g. After adding the knoll, it was prepared by mixing.
（比較例３）
コレカルシフェロール０．０５ｇを量り、全量が５０ｇとなるようミリスチン酸イソプロピルを加えた後、混合し調製した。
(Comparative Example 3)
0.05 g of cholecalciferol was weighed, and isopropyl myristate was added to a total amount of 50 g, followed by mixing.
（比較例４）
コレカルシフェロール０．０５ｇを量り、全量が５０ｇとなるようミリスチン酸オクチルドデシルを加えた後、混合し調製した。
(Comparative Example 4)
Cholecalciferol 0.05 g was weighed and octyldodecyl myristate was added to a total amount of 50 g, followed by mixing.
（比較例５）
コレカルシフェロール０．０５ｇを量り、全量が５０ｇとなるよう流動パラフィンを加えた後、混合し調製した。
(Comparative Example 5)
0.05 g of cholecalciferol was weighed, and liquid paraffin was added to a total amount of 50 g, followed by mixing.
（比較例６）
コレカルシフェロール０．０５ｇを量り、全量が５０ｇとなるようオクチルドデカノールを加えた後、混合し調製した。
(Comparative Example 6)
Cholecalciferol 0.05 g was weighed and octyldodecanol was added to a total amount of 50 g, followed by mixing.
（試験例）
実施例および比較例で調整した組成物を気密、遮光容器に充填した後、５０℃で１月間保存した。保存後の組成物中のコレカルシフェロールの含量を、ＨＰＬＣ法を用いて測定し、保存開始時の含量に対する１月間保存後の含量を算出した。結果は、以下の表１−２に示した。なお、表１−２中に記載の略号は以下の通りである。
Ｍ−ｉＰｒ：ミリスチン酸イソプロピル
Ｍ−Ｏｃｔ：ミリスチン酸オクチルドデシル
Ｐａｒａ：流動パラフィン
ＯｃｔＯＨ：オクチルドデカノール
ＶＡ：パルミチン酸レチノール
ＶＢ６：トリ２−ヘキシルデカン酸ピリドキシン
ＶＣ：テトラ２−ヘキシルデカン酸アスコルビル
ＶＤ３：コレカルシフェロール
ＶＥ：酢酸トコフェロール
(Test example)
The compositions prepared in Examples and Comparative Examples were airtight and filled in a light-shielding container, and then stored at 50 ° C. for 1 month. The content of cholecalciferol in the composition after storage was measured using the HPLC method, and the content after storage for 1 month relative to the content at the start of storage was calculated. The results are shown in Table 1-2 below. In addition, the symbol described in Table 1-2 is as follows.
M-iPr: isopropyl myristate M-Oct: octyldodecyl myristate Para: liquid paraffin OctOH: octyldodecanol VA: retinol palmitate VB6: pyridoxine tri-2-hexyldecanoate VC: ascorbyl tetra-2-hexyldecanoate VD3: cholecalciferol VE: Tocopherol acetate
表１−２の試験結果より、高級脂肪酸エステルによるコレカルシフェロールの安定化効果が確認できた。すなわち、ミリスチン酸イソプロピルやミリスチン酸オクチルドデシルのような高級脂肪酸エステルを用いた場合には、組成物中でコレカルシフェロールが安定に存在するが、流動パラフィンやオクチルドデカノールのような油性基剤の場合には、組成物中でコレカルシフェロールが安定に存在しないことがわかった。さらに、組成物中にコレカルシフェロールとともに、パルミチン酸レチノール、トリ２−ヘキシルデカン酸ピリドキシン、テトラ２−ヘキシルデカン酸アスコルビル及び酢酸トコフェロールから選ばれる１種以上を含有させるとコレカルシフェロールの安定性が高まることがわかった。 From the test result of Table 1-2, the stabilization effect of cholecalciferol by higher fatty acid ester has been confirmed. That is, when a higher fatty acid ester such as isopropyl myristate or octyldodecyl myristate is used, cholecalciferol is stably present in the composition, but an oily base such as liquid paraffin or octyldodecanol is used. In some cases, it was found that cholecalciferol was not stably present in the composition. Furthermore, the stability of cholecalciferol increases when the composition contains at least one selected from retinol palmitate, pyridoxine tri-2-hexyldecanoate, ascorbyl tetra-2-hexyldecanoate and tocopherol acetate together with cholecalciferol. I understood.
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| CN107530362A (en) * | 2015-04-15 | 2018-01-02 | 玛路弘株式会社 | The pharmaceutical composition of skin |
| JP2018123081A (en) * | 2017-01-31 | 2018-08-09 | 中外製薬株式会社 | Aqueous pharmaceutical composition containing vitamin d compound |
| US10335362B2 (en) | 2010-10-12 | 2019-07-02 | Shiseido Company, Ltd. | Water-in-oil type emulsion cosmetic |
| CN115697290A (en) * | 2020-05-29 | 2023-02-03 | 联合利华知识产权控股有限公司 | Cosmetic compositions with enhanced color stability against retinoic acid precursors |
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