JP2014031347A - Composition containing cyclic hydroxy acid or derivative thereof, and sterol ester - Google Patents
Composition containing cyclic hydroxy acid or derivative thereof, and sterol ester Download PDFInfo
- Publication number
- JP2014031347A JP2014031347A JP2012174091A JP2012174091A JP2014031347A JP 2014031347 A JP2014031347 A JP 2014031347A JP 2012174091 A JP2012174091 A JP 2012174091A JP 2012174091 A JP2012174091 A JP 2012174091A JP 2014031347 A JP2014031347 A JP 2014031347A
- Authority
- JP
- Japan
- Prior art keywords
- phytosteryl
- acid
- gallate
- composition
- formula
- 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
- -1 cyclic hydroxy acid Chemical class 0.000 title claims abstract description 139
- 239000000203 mixture Substances 0.000 title claims abstract description 79
- 229930182558 Sterol Natural products 0.000 title claims abstract description 55
- 235000003702 sterols Nutrition 0.000 title claims abstract description 55
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 claims abstract description 14
- VFPFQHQNJCMNBZ-UHFFFAOYSA-N ethyl gallate Chemical compound CCOC(=O)C1=CC(O)=C(O)C(O)=C1 VFPFQHQNJCMNBZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- JXOHGGNKMLTUBP-HSUXUTPPSA-N shikimic acid Chemical compound O[C@@H]1CC(C(O)=O)=C[C@@H](O)[C@H]1O JXOHGGNKMLTUBP-HSUXUTPPSA-N 0.000 claims abstract description 10
- JXOHGGNKMLTUBP-JKUQZMGJSA-N shikimic acid Natural products O[C@@H]1CC(C(O)=O)=C[C@H](O)[C@@H]1O JXOHGGNKMLTUBP-JKUQZMGJSA-N 0.000 claims abstract description 10
- 239000004262 Ethyl gallate Substances 0.000 claims abstract description 7
- 235000019277 ethyl gallate Nutrition 0.000 claims abstract description 7
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000000473 propyl gallate Substances 0.000 claims abstract description 7
- 235000010388 propyl gallate Nutrition 0.000 claims abstract description 7
- 229940075579 propyl gallate Drugs 0.000 claims abstract description 7
- RPWFJAMTCNSJKK-UHFFFAOYSA-N Dodecyl gallate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC(O)=C(O)C(O)=C1 RPWFJAMTCNSJKK-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000555 dodecyl gallate Substances 0.000 claims abstract description 6
- 235000010386 dodecyl gallate Nutrition 0.000 claims abstract description 6
- 229940080643 dodecyl gallate Drugs 0.000 claims abstract description 6
- WMBWREPUVVBILR-WIYYLYMNSA-N (-)-Epigallocatechin-3-o-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-WIYYLYMNSA-N 0.000 claims abstract description 5
- MTPIQEWGULCIPM-UHFFFAOYSA-N 2-ethylhexyl 3,4,5-trihydroxybenzoate Chemical compound CCCCC(CC)COC(=O)C1=CC(O)=C(O)C(O)=C1 MTPIQEWGULCIPM-UHFFFAOYSA-N 0.000 claims abstract description 5
- WMBWREPUVVBILR-UHFFFAOYSA-N GCG Natural products C=1C(O)=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229940030275 epigallocatechin gallate Drugs 0.000 claims abstract description 5
- 229940080646 ethylhexyl gallate Drugs 0.000 claims abstract description 5
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims abstract description 5
- BRNPAEUKZMBRLQ-UHFFFAOYSA-N octadecyl 3,4,5-trihydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1=CC(O)=C(O)C(O)=C1 BRNPAEUKZMBRLQ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000194 fatty acid Substances 0.000 claims description 67
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 66
- 229930195729 fatty acid Natural products 0.000 claims description 66
- 150000004665 fatty acids Chemical class 0.000 claims description 59
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 24
- 150000003432 sterols Chemical class 0.000 claims description 24
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol group Chemical group [C@@H]1(CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@H](C)CCCC(C)C HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 18
- 229920006395 saturated elastomer Polymers 0.000 claims description 17
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 239000000539 dimer Substances 0.000 claims description 16
- 235000018330 Macadamia integrifolia Nutrition 0.000 claims description 12
- 240000000912 Macadamia tetraphylla Species 0.000 claims description 12
- 235000003800 Macadamia tetraphylla Nutrition 0.000 claims description 12
- 239000010466 nut oil Substances 0.000 claims description 12
- AVBJHQDHVYGQLS-UHFFFAOYSA-N 2-(dodecanoylamino)pentanedioic acid Chemical compound CCCCCCCCCCCC(=O)NC(C(O)=O)CCC(O)=O AVBJHQDHVYGQLS-UHFFFAOYSA-N 0.000 claims description 11
- 239000003921 oil Substances 0.000 claims description 11
- 235000019198 oils Nutrition 0.000 claims description 11
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 229940024606 amino acid Drugs 0.000 claims description 10
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 10
- 235000020778 linoleic acid Nutrition 0.000 claims description 10
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims description 10
- 239000002537 cosmetic Substances 0.000 claims description 9
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 claims description 7
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 230000037303 wrinkles Effects 0.000 claims description 7
- 241001483078 Phyto Species 0.000 claims description 6
- 230000001076 estrogenic effect Effects 0.000 claims description 6
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 235000019774 Rice Bran oil Nutrition 0.000 claims description 5
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 239000008165 rice bran oil Substances 0.000 claims description 5
- 235000020238 sunflower seed Nutrition 0.000 claims description 5
- 230000003712 anti-aging effect Effects 0.000 claims description 4
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 3
- DCVMAYAWOPBYKB-UHFFFAOYSA-N 3-[methyl(tetradecanoyl)amino]propanoic acid Chemical compound CCCCCCCCCCCCCC(=O)N(C)CCC(O)=O DCVMAYAWOPBYKB-UHFFFAOYSA-N 0.000 claims description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 3
- SHBUUTHKGIVMJT-UHFFFAOYSA-N Hydroxystearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OO SHBUUTHKGIVMJT-UHFFFAOYSA-N 0.000 claims description 3
- FNZSVEHJZREFPF-ZETCQYMHSA-N Nonate Chemical compound CCCCC[C@H](C(O)=O)CC(O)=O FNZSVEHJZREFPF-ZETCQYMHSA-N 0.000 claims description 3
- RJECHNNFRHZQKU-UHFFFAOYSA-N Oelsaeurecholesterylester Natural products C12CCC3(C)C(C(C)CCCC(C)C)CCC3C2CC=C2C1(C)CCC(OC(=O)CCCCCCCC=CCCCCCCCC)C2 RJECHNNFRHZQKU-UHFFFAOYSA-N 0.000 claims description 3
- 239000005642 Oleic acid Substances 0.000 claims description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 3
- XKMYWNHZAQUEPY-YZGJEOKZSA-N [(3s,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl] 12-hydroxyoctadecanoate Chemical compound C([C@@H]12)C[C@]3(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)CCCCCCCCCCC(O)CCCCCC)C1 XKMYWNHZAQUEPY-YZGJEOKZSA-N 0.000 claims description 3
- JBBRZDLNVILTDL-XNTGVSEISA-N [(3s,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl] 16-methylheptadecanoate Chemical compound C([C@@H]12)C[C@]3(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)CCCCCCCCCCCCCCC(C)C)C1 JBBRZDLNVILTDL-XNTGVSEISA-N 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- XHRPOTDGOASDJS-UHFFFAOYSA-N cholesterol n-octadecanoate Natural products C12CCC3(C)C(C(C)CCCC(C)C)CCC3C2CC=C2C1(C)CCC(OC(=O)CCCCCCCCCCCCCCCCC)C2 XHRPOTDGOASDJS-UHFFFAOYSA-N 0.000 claims description 3
- 229940072104 cholesteryl hydroxystearate Drugs 0.000 claims description 3
- 229940073724 cholesteryl isostearate Drugs 0.000 claims description 3
- RJECHNNFRHZQKU-RMUVNZEASA-N cholesteryl oleate Chemical compound C([C@@H]12)C[C@]3(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)C1 RJECHNNFRHZQKU-RMUVNZEASA-N 0.000 claims description 3
- XHRPOTDGOASDJS-XNTGVSEISA-N cholesteryl stearate Chemical compound C([C@@H]12)C[C@]3(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)CCCCCCCCCCCCCCCCC)C1 XHRPOTDGOASDJS-XNTGVSEISA-N 0.000 claims description 3
- 229940074391 gallic acid Drugs 0.000 claims description 3
- 235000004515 gallic acid Nutrition 0.000 claims description 3
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 claims description 3
- 229940072106 hydroxystearate Drugs 0.000 claims description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 3
- 229940049964 oleate Drugs 0.000 claims description 3
- WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 claims description 3
- 229940066675 ricinoleate Drugs 0.000 claims description 3
- GHVNFZFCNZKVNT-UHFFFAOYSA-M decanoate Chemical compound CCCCCCCCCC([O-])=O GHVNFZFCNZKVNT-UHFFFAOYSA-M 0.000 claims 1
- 230000037330 wrinkle prevention Effects 0.000 claims 1
- 239000003974 emollient agent Substances 0.000 abstract description 12
- 230000007794 irritation Effects 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 8
- 150000003254 radicals Chemical class 0.000 abstract description 8
- 238000004040 coloring Methods 0.000 abstract description 7
- 239000000839 emulsion Substances 0.000 abstract 1
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 description 15
- 238000011156 evaluation Methods 0.000 description 14
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 10
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 description 9
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 description 9
- 235000001014 amino acid Nutrition 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 230000007760 free radical scavenging Effects 0.000 description 9
- BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- HZYXFRGVBOPPNZ-UHFFFAOYSA-N UNPD88870 Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)=CCC(CC)C(C)C)C1(C)CC2 HZYXFRGVBOPPNZ-UHFFFAOYSA-N 0.000 description 8
- NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- NLQLSVXGSXCXFE-UHFFFAOYSA-N sitosterol Natural products CC=C(/CCC(C)C1CC2C3=CCC4C(C)C(O)CCC4(C)C3CCC2(C)C1)C(C)C NLQLSVXGSXCXFE-UHFFFAOYSA-N 0.000 description 8
- 229940032091 stigmasterol Drugs 0.000 description 8
- HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 description 8
- 235000016831 stigmasterol Nutrition 0.000 description 8
- KZJWDPNRJALLNS-VPUBHVLGSA-N (-)-beta-Sitosterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@@H](C(C)C)CC)C)CC4)CC3)CC=2)CC1 KZJWDPNRJALLNS-VPUBHVLGSA-N 0.000 description 7
- CSVWWLUMXNHWSU-UHFFFAOYSA-N (22E)-(24xi)-24-ethyl-5alpha-cholest-22-en-3beta-ol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(CC)C(C)C)C1(C)CC2 CSVWWLUMXNHWSU-UHFFFAOYSA-N 0.000 description 7
- KLEXDBGYSOIREE-UHFFFAOYSA-N 24xi-n-propylcholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CCC)C(C)C)C1(C)CC2 KLEXDBGYSOIREE-UHFFFAOYSA-N 0.000 description 7
- SGNBVLSWZMBQTH-FGAXOLDCSA-N Campesterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@H](C(C)C)C)C)CC4)CC3)CC=2)CC1 SGNBVLSWZMBQTH-FGAXOLDCSA-N 0.000 description 7
- LPZCCMIISIBREI-MTFRKTCUSA-N Citrostadienol Natural products CC=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C LPZCCMIISIBREI-MTFRKTCUSA-N 0.000 description 7
- ARVGMISWLZPBCH-UHFFFAOYSA-N Dehydro-beta-sitosterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)CCC(CC)C(C)C)CCC33)C)C3=CC=C21 ARVGMISWLZPBCH-UHFFFAOYSA-N 0.000 description 7
- BTEISVKTSQLKST-UHFFFAOYSA-N Haliclonasterol Natural products CC(C=CC(C)C(C)(C)C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC12C BTEISVKTSQLKST-UHFFFAOYSA-N 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- MJVXAPPOFPTTCA-UHFFFAOYSA-N beta-Sistosterol Natural products CCC(CCC(C)C1CCC2C3CC=C4C(C)C(O)CCC4(C)C3CCC12C)C(C)C MJVXAPPOFPTTCA-UHFFFAOYSA-N 0.000 description 7
- SGNBVLSWZMBQTH-PODYLUTMSA-N campesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](C)C(C)C)[C@@]1(C)CC2 SGNBVLSWZMBQTH-PODYLUTMSA-N 0.000 description 7
- 235000000431 campesterol Nutrition 0.000 description 7
- 210000004209 hair Anatomy 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 description 7
- 229950005143 sitosterol Drugs 0.000 description 7
- 235000015500 sitosterol Nutrition 0.000 description 7
- QYIXCDOBOSTCEI-UHFFFAOYSA-N alpha-cholestanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 QYIXCDOBOSTCEI-UHFFFAOYSA-N 0.000 description 6
- 238000004945 emulsification Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
- 230000002195 synergetic effect Effects 0.000 description 6
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 5
- 230000032683 aging Effects 0.000 description 5
- 235000012000 cholesterol Nutrition 0.000 description 5
- 229960000735 docosanol Drugs 0.000 description 5
- QYIXCDOBOSTCEI-QCYZZNICSA-N (5alpha)-cholestan-3beta-ol Chemical compound C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCCC(C)C)[C@@]2(C)CC1 QYIXCDOBOSTCEI-QCYZZNICSA-N 0.000 description 4
- WCBPJVKVIMMEQC-UHFFFAOYSA-N 1,1-diphenyl-2-(2,4,6-trinitrophenyl)hydrazine Chemical group [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NN(C=1C=CC=CC=1)C1=CC=CC=C1 WCBPJVKVIMMEQC-UHFFFAOYSA-N 0.000 description 4
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 4
- 201000004384 Alopecia Diseases 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
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- 239000003112 inhibitor Substances 0.000 description 1
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- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
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- 125000001802 myricyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940043348 myristyl alcohol Drugs 0.000 description 1
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- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 125000001402 nonanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960002969 oleic acid Drugs 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
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- 239000000312 peanut oil Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 239000010773 plant oil Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 230000037394 skin elasticity Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- GHIZCSMTYWOBQA-BZSCQJQFSA-N spinasterol Natural products CC[C@H](C=C[C@@H](C)[C@@H]1CC[C@@]2(C)C3=CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C)C(C)C GHIZCSMTYWOBQA-BZSCQJQFSA-N 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- 230000005068 transpiration Effects 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 125000000297 undecanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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- 229930003231 vitamin Natural products 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000010497 wheat germ oil Substances 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
- A61K8/18—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
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
Abstract
Description
本発明は、特定の環状ヒドロキシ酸またはその誘導体と、ステロールエステルを含有する組成物に関し、さらに詳細には、シワの生成、皮膚弾力の消失、脱毛といった老化現象を防止または改善する組成物に関し、シワ防止剤、シワ改善剤、およびアンチエージング剤に関する。 The present invention relates to a composition containing a specific cyclic hydroxy acid or a derivative thereof and a sterol ester. More specifically, the present invention relates to a composition for preventing or improving the aging phenomenon such as generation of wrinkles, loss of skin elasticity, hair loss, The present invention relates to an anti-wrinkle agent, an anti-wrinkle agent, and an anti-aging agent.
近年、老化現象の原因として、フリーラジカルの発生が考えられている。必要以上のフリーラジカルは、脂肪酸の酸化、コラーゲン線維の架橋、ヒアルロン酸の断片化、ＤＮＡ螺旋の部分開裂、連鎖的ラジカルの発生による組織の損傷等の悪影響を及ぼし、その結果として、シワの生成、皮膚弾力の消失、脱毛といった老化現象を引き起こす。 In recent years, generation of free radicals is considered as a cause of the aging phenomenon. Unnecessary free radicals adversely affect fatty acid oxidation, collagen fiber cross-linking, hyaluronic acid fragmentation, DNA helix partial cleavage, tissue damage due to the generation of chain radicals, and as a result, wrinkles are generated. Cause aging phenomenon such as loss of skin elasticity and hair loss.
したがって、フリーラジカルを消去する作用のある物質の探索が広く行われてきた。このような作用を有する物質として、フェノール性水酸基を有する化合物などの環状炭化水素に直接水酸基が結合した化合物等が挙げられる（例えば非特許文献１）。しかしながら、これらの化合物であっても、活性が弱く十分に機能しないものも多く、さらに刺激性、使用感、臭い、保存安定性を考慮した場合、少量しか使用できない場合があった。 Therefore, a search for a substance having an action of eliminating free radicals has been widely performed. Examples of the substance having such an action include compounds in which a hydroxyl group is directly bonded to a cyclic hydrocarbon such as a compound having a phenolic hydroxyl group (for example, Non-Patent Document 1). However, even though these compounds are weak in activity and do not function sufficiently, there are cases where only a small amount can be used in consideration of irritation, feeling of use, smell, and storage stability.
本発明の目的は、優れたフリーラジカル消去効果を有し、刺激性、使用感、臭い、保存安定性においても優れた組成物を提供することにある。 An object of the present invention is to provide a composition having an excellent free radical scavenging effect and excellent in irritation, feeling in use, odor, and storage stability.
本発明者らは、上記課題を解決すべく、鋭意検討した結果、特定の環状ヒドロキシ酸またはその誘導体とステロールエステルを併用した場合には、相乗的にフリーラジカルを消去する効果を有することを見出した。また、特定の環状ヒドロキシ酸およびその誘導体とステロールエステルを配合した組成物は、刺激性、使用感（べたつき、エモリエント性、延展性）、臭い、保存安定性（乳化安定性、着色安定性）においても優れた組成物を提供することを見出し、本発明を完成させた。 As a result of intensive studies to solve the above problems, the present inventors have found that when a specific cyclic hydroxy acid or a derivative thereof and a sterol ester are used in combination, they have an effect of synergistically eliminating free radicals. It was. In addition, a composition containing a specific cyclic hydroxy acid or derivative thereof and a sterol ester is irritating, feeling of use (stickiness, emollient, spreadability), odor, storage stability (emulsification stability, color stability). Has found that the present invention provides an excellent composition, and has completed the present invention.
すなわち、本発明は、以下の通りである。
［１］（Ａ）式（１）で示される環状ヒドロキシ酸またはその誘導体、
式（１）：
式（２）：
式（３）：
ただし、没食子酸を除く。）
ならびに、
（Ｂ）ステロールエステル
を含む組成物。
［２］（Ａ）が、シキミ酸、エチルガレート、プロピルガレート、エチルヘキシルガレート、ドデシルガレート、ステアリルガレート、リノレイルガレート、エピガロカテキンガレートおよびグルコシルペンタガレートから選択される、上記［１］に記載の組成物。
［３］（Ａ）の濃度が０．００１重量％〜３０重量％である、上記［１］または［２］に記載の組成物。
［４］（Ａ）の濃度が０．００１重量％〜１０重量％である、上記［１］〜［３］の何れか１項に記載の組成物。
［５］（Ｂ）が、Ｎ−アシルアミノ酸ステロールエステルである、上記［１］〜［４］の何れか１項に記載の組成物。
［６］（Ｂ）が、式（４）：
Ｘは、水素原子、Ｃ８−３８脂肪族アルコールのエステル生成残基、またはステロールのエステル生成残基を示し、
ＣＯＲ１０は、Ｃ８−２２アシル基を示し、
Ｒ１１は、水素原子、または−ＣＯＯＹ（式中、Ｙは、水素原子、Ｃ８−３８脂肪族アルコールのエステル生成残基、またはステロールのエステル生成残基を示す。）で示される基を示し、
Ｒ１２は、水素原子またはＣ１−６アルキル基を示し、
ｎは１または２を示す。
但し、Ｒ１１が水素原子のとき、Ｘはステロールのエステル生成残基であり、Ｒ１１が−ＣＯＯＹで示される基のとき、ＸまたはＹの少なくとも一方がステロールのエステル生成残基である。）
で示されるＮ−アシルアミノ酸ステロールエステルである、上記［１］〜［５］の何れか１項に記載の組成物。
［７］ステロールのエステル生成残基がフィトステロールのエステル生成残基であり、ＣＯＲ１０がラウロイル基であり、かつｎが２である、上記［６］記載の組成物。
［８］（Ｂ）が、Ｎ−ミリストイル−Ｎ−メチル−β−アラニン（フィトステリル／デシルテトラデシル）、Ｎ−ラウロイル−Ｌ−グルタミン酸ジ（コレステリル／ベヘニル／２−オクチルドデシル）、Ｎ−ラウロイル−Ｌ−グルタミン酸ジ（フィトステリル／ベヘニル／２−オクチルドデシル）、Ｎ−ラウロイル−Ｌ−グルタミン酸ジ（コレステリル／２−オクチルドデシル）、Ｎ−ラウロイル−Ｌ−グルタミン酸ジ（フィトステリル／２−オクチルドデシル）またはＮ−ラウロイル−Ｌ−グルタミン酸ジ（フィトステリル／ベヘニル／２−オクチルドデシル／イソステアリル）である、上記［１］〜［６］の何れか１項に記載の組成物。
［９］（Ｂ）が、脂肪酸ステロールエステルである、上記［１］〜［４］の何れか１項に記載の組成物。
［１０］（Ｂ）が、酪酸フィトステリル、ノナン酸フィトステリル、ステアリン酸コレステリル、イソステアリン酸コレステリル、イソステアリン酸フィトステリル、ヒドロキシステアリン酸コレステリル、ヒドロキシステアリン酸フィトステリル、カプリル／カプリン酸フィトステリル、リシノール酸フィトステリル、オレイン酸コレステリル、オレイン酸フィトステリル、オレイン酸ジヒドロコレステリル、分岐脂肪酸（Ｃ１２−３１）フィトステリル、フィトステリルカノラ油脂肪酸グリセリズ、フィトステリルナタネグリセリズ、マカデミアナッツ油脂肪酸フィトステリル、マカデミアナッツ油脂肪酸コレステリル、マカデミアナッツ油脂肪酸ジヒドロコレステリル、ヒマワリ種子油脂肪酸フィトステリル、コメヌカ油脂肪酸フィトステリル、ダイマージリノール酸（フィトステリル／イソステアリル／セチル／ステアリル／ベヘニル）、ダイマージリノール酸ダイマージリノレイルビス（ベヘニル／イソステアリル／フィトステリル）、ダイマージリノール酸（フィトステリル／ベヘニル）およびダイマージリノール酸ジ（イソステアリル／フィトステリル）から選択される、上記［１］〜［４］または［９］の何れか１項に記載の組成物。
［１１］（Ｂ）の濃度が０．００１重量％〜４０重量％である、上記［１］〜［１０］の何れか１項に記載の組成物。
［１２］（Ａ）の重量／（Ｂ）の重量が０．０１〜１００である、上記［１］〜［１１］の何れか１項に記載の組成物。
［１３］（Ａ）の重量／（Ｂ）の重量が０．１〜４０である、上記［１］〜［１２］の何れか１項に記載の組成物。
［１４］上記［１］〜［１３］の何れか１項に記載の組成物を含有する化粧料。
［１５］皮膚用であることを特徴とする上記［１４］に記載の化粧料。
［１６］上記［１］〜［１３］の何れか１項に記載の組成物を含有するシワ防止剤、シワ改善剤、またはアンチエージング剤。
That is, the present invention is as follows.
[1] (A) a cyclic hydroxy acid represented by the formula (1) or a derivative thereof,
Formula (1):
Formula (2):
Formula (3):
However, gallic acid is excluded. )
And
(B) A composition comprising a sterol ester.
[2] The above [1], wherein (A) is selected from shikimic acid, ethyl gallate, propyl gallate, ethylhexyl gallate, dodecyl gallate, stearyl gallate, linoleyl gallate, epigallocatechin gallate and glucosyl pentagallate. Composition.
[3] The composition according to [1] or [2] above, wherein the concentration of (A) is 0.001 to 30% by weight.
[4] The composition according to any one of [1] to [3] above, wherein the concentration of (A) is 0.001 to 10% by weight.
[5] The composition according to any one of [1] to [4], wherein (B) is an N-acylamino acid sterol ester.
[6] (B) is represented by formula (4):
X represents a hydrogen atom, an esterogenic residue of a C 8-38 aliphatic alcohol, or an esterogenic residue of a sterol;
COR 10 represents a C 8-22 acyl group,
R 11 represents a hydrogen atom or a group represented by —COOY (wherein Y represents a hydrogen atom, an ester-forming residue of a C 8-38 aliphatic alcohol, or an ester-forming residue of a sterol). ,
R 12 represents a hydrogen atom or a C 1-6 alkyl group,
n represents 1 or 2.
However, when R 11 is a hydrogen atom, X is an ester-forming residue of sterol, and when R 11 is a group represented by —COOY, at least one of X or Y is an ester-forming residue of sterol. )
The composition according to any one of [1] to [5] above, which is an N-acylamino acid sterol ester represented by:
[7] The composition according to [6] above, wherein the ester-generating residue of sterol is an ester-generating residue of phytosterol, COR 10 is a lauroyl group, and n is 2.
[8] (B) is N-myristoyl-N-methyl-β-alanine (phytosteryl / decyltetradecyl), N-lauroyl-L-glutamate di (cholesteryl / behenyl / 2-octyldodecyl), N-lauroyl- L-glutamate di (phytosteryl / behenyl / 2-octyldodecyl), N-lauroyl-L-glutamate di (cholesteryl / 2-octyldodecyl), N-lauroyl-L-glutamate di (phytosteryl / 2-octyldodecyl) or N -The composition according to any one of [1] to [6] above, which is dilauroyl-L-glutamate (phytosteryl / behenyl / 2-octyldodecyl / isostearyl).
[9] The composition according to any one of [1] to [4], wherein (B) is a fatty acid sterol ester.
[10] (B) is phytosteryl butyrate, phytosteryl nonate, cholesteryl stearate, cholesteryl isostearate, phytosteryl isostearate, cholesteryl hydroxystearate, phytosteryl hydroxystearate, phytosteryl caprylate / phytosteryl ricinoleate, cholesteryl oleate , phytosteryl oleate, dihydrocholesteryl, branched fatty acid (C 12-31) phytosteryl, Phyto stearyl Riruka Nora oil fatty Guriserizu, Phyto Steri Luna seed glyceryl's, macadamia nut oil fatty acid phytosteryl, macadamia nut oil fatty acid cholesteryl, macadamia nut oil fatty acid dihydrocholesteryl , Sunflower seed oil fatty acid phytosteryl, rice bran oil fatty acid Steryl, dimer linoleic acid (phytosteryl / isostearyl / cetyl / stearyl / behenyl), dimer linoleic acid dimer linoleyl bis (behenyl / isostearyl / phytosteryl), dimer linoleic acid (phytosteryl / behenyl) and dimer linol 10. The composition according to any one of [1] to [4] or [9] above, which is selected from acid di (isostearyl / phytosteryl).
[11] The composition according to any one of [1] to [10], wherein the concentration of (B) is 0.001 to 40% by weight.
[12] The composition according to any one of [1] to [11] above, wherein the weight of (A) / (B) is 0.01 to 100.
[13] The composition according to any one of [1] to [12] above, wherein the weight of (A) / (B) is 0.1 to 40.
[14] A cosmetic comprising the composition according to any one of [1] to [13].
[15] The cosmetic according to [14], which is for skin.
[16] An anti-wrinkle agent, an anti-wrinkle agent, or an anti-aging agent containing the composition according to any one of [1] to [13].
本発明により、優れたフリーラジカル消去効果を有し、刺激性、使用感、臭い、保存安定性においても優れた組成物を提供することができる。これにより、シワの生成、皮膚弾力の消失、脱毛といった老化現象を防止または改善することができる。 According to the present invention, it is possible to provide a composition having an excellent free radical scavenging effect and excellent in irritation, feeling in use, smell, and storage stability. Thereby, the aging phenomenon such as generation of wrinkles, disappearance of skin elasticity, and hair loss can be prevented or improved.
本発明は、（Ａ）特定の環状ヒドロキシ酸またはその誘導体、および（Ｂ）ステロールエステルを含む。 The present invention includes (A) a specific cyclic hydroxy acid or derivative thereof, and (B) a sterol ester.
［（Ａ）環状ヒドロキシ酸またはその誘導体］
本発明の特定の環状ヒドロキシ酸またはその誘導体は、式（１）で表される。
式（１）：
[(A) Cyclic hydroxy acid or derivative thereof]
The specific cyclic hydroxy acid or derivative thereof of the present invention is represented by the formula (1).
Formula (1):
式中、Ｒ１は水素原子、直鎖または分岐鎖状の飽和または不飽和のＣ１−２４炭化水素基、式（２）、あるいは、式（３）を示す。Ｒ２、Ｒ３およびＲ４はそれぞれ独立に水素原子、直鎖または分岐鎖状の飽和または不飽和のＣ１−２４炭化水素基、あるいはＣ１−２４アルキル−カルボニル基を示す。 In the formula, R 1 represents a hydrogen atom, a linear or branched saturated or unsaturated C 1-24 hydrocarbon group, formula (2), or formula (3). R 2 , R 3 and R 4 each independently represent a hydrogen atom, a linear or branched saturated or unsaturated C 1-24 hydrocarbon group, or a C 1-24 alkyl-carbonyl group.
式（２）：
式（２）中、＊はＯＲ１における酸素原子との結合点を示す。 In the formula (2), * represents a bonding point with an oxygen atom in OR 1 .
式（３）：
式（３）中、＊はＯＲ１における酸素原子との結合点を示し、Ｒ５、Ｒ６、Ｒ７、およびＲ８はそれぞれ独立に水素原子またはガロイル基を示す。
Ｒ５、Ｒ６、Ｒ７、およびＲ８の１以上がガロイル基であることが好ましく、２以上がガロイル基であることがより好ましく、３以上がガロイル基であることがより好ましく、すべてがガロイル基であることが好ましい。
In formula (3), * represents a bonding point with an oxygen atom in OR 1 , and R 5 , R 6 , R 7 , and R 8 each independently represent a hydrogen atom or a galloyl group.
One or more of R 5 , R 6 , R 7 , and R 8 are preferably galloyl groups, more preferably 2 or more are galloyl groups, more preferably 3 or more are galloyl groups, A galloyl group is preferred.
ただし、本発明においては、（Ａ）環状ヒドロキシ酸またはその誘導体から没食子酸を除く。 However, in the present invention, gallic acid is excluded from (A) cyclic hydroxy acid or a derivative thereof.
本発明において、直鎖または分岐鎖状の飽和または不飽和のＣ１−２４炭化水素基とは、炭素数１〜２４個の直鎖または分枝鎖状の炭化水素基を意味する。たとえば、Ｃ１−２４アルキル基またはＣ１−２４アルケニル基が挙げられる。
Ｃ１−２４アルキル基としては、例えば、メチル、エチル、プロピル、イソプロピル、ブチル、イソブチル、ｓｅｃ−ブチル、ｔｅｒｔ−ブチル、ペンチル、イソペンチル、ｓｅｃ−ペンチル、ネオペンチル、ｔｅｒｔ−ペンチル、ヘキシル、ｓｅｃ−ヘキシル、ヘプチル、ｓｅｃ−ヘプチル、オクチル、２−エチルヘキシル、ｓｅｃ−オクチル、ノニル、ｓｅｃ−ノニル、デシル、ｓｅｃ−デシル、ウンデシル、ｓｅｃ−ウンデシル、ドデシル、ｓｅｃ−ドデシル、トリデシル、イソトリデシル、ｓｅｃ−トリデシル、テトラデシル、ｓｅｃ−テトラデシル、ヘキサデシル、ｓｅｃ−ヘキサデシル、ステアリル、モノメチル分枝−イソステアリル、イコシル、ドコシル、テトラコシル、トリアコンチル、２−ブチルオクチル、２−ヘキシルオクチル、２−ブチルデシル、２−ヘキシルデシル、２−オクチルデシル、２−ヘキシルドデシル、２−オクチルドデシル、２−デシルドデシル、２−オクチルテトラデシル、２−デシルテトラデシル、２−ドデシルテトラデシル、２−デシルヘキサデシル、２−ドデシルヘキサデシル、２−テトラデシルヘキサデシル、２−ドデシルオクタデシル、２−テトラデシルオクタデシル、２−ヘキサデシルオクタデシル、２−テトラデシルイコシル、２−ヘキサデシルイコシル、および２−オクタデシルイコシル等が挙げられる。
特に、Ｃ１−６アルキル基としては、メチル、エチル、イソプロピル、プロピル、ブチル、イソブチル、ｓｅｃ−ブチル、ｔｅｒｔ−ブチル、ペンチル、ｓｅｃ−ペンチル、ｔｅｒｔ−ペンチル、イソペンチル、およびヘキシルが挙げられる。
Ｃ１−２４アルケニル基としては例えば、ビニル、アリル、プロペニル、イソプロペニル、ブテニル、イソブテニル、ペンテニル、イソペンテニル、ヘキセニル、ヘプテニル、オクテニル、ノネニル、デセニル、ウンデセニル、ドデセニル、テトラデセニル、オレイル、およびリノレイル等が挙げられる。
In the present invention, the linear or branched saturated or unsaturated C 1-24 hydrocarbon group means a linear or branched hydrocarbon group having 1 to 24 carbon atoms. For example, a C1-24 alkyl group or a C1-24 alkenyl group is mentioned.
Examples of the C 1-24 alkyl group include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, sec-pentyl, neopentyl, tert-pentyl, hexyl, sec-hexyl. , Heptyl, sec-heptyl, octyl, 2-ethylhexyl, sec-octyl, nonyl, sec-nonyl, decyl, sec-decyl, undecyl, sec-undecyl, dodecyl, sec-dodecyl, tridecyl, isotridecyl, sec-tridecyl, tetradecyl , Sec-tetradecyl, hexadecyl, sec-hexadecyl, stearyl, monomethyl branched-isostearyl, icosyl, docosyl, tetracosyl, triacontyl, 2-butyloctyl, 2-hexyl Octyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, 2-hexyldecyl, 2-octyldodecyl, 2-decyldodecyl, 2-octyltetradecyl, 2-decyltetradecyl, 2-dodecyltetradecyl, 2 -Decylhexadecyl, 2-dodecylhexadecyl, 2-tetradecylhexadecyl, 2-dodecyloctadecyl, 2-tetradecyloctadecyl, 2-hexadecyloctadecyl, 2-tetradecylicosyl, 2-hexadecylicosyl, and Examples include 2-octadecylicosyl.
In particular, C 1-6 alkyl groups include methyl, ethyl, isopropyl, propyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, sec-pentyl, tert-pentyl, isopentyl, and hexyl.
C 1-24 alkenyl groups include, for example, vinyl, allyl, propenyl, isopropenyl, butenyl, isobutenyl, pentenyl, isopentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tetradecenyl, oleyl, linoleyl and the like Can be mentioned.
Ｒ１における直鎖または分岐鎖状の飽和または不飽和のＣ１−２４炭化水素基としては、エチル基、プロピル基、エチルヘキシル基、ドデシル基、ステアリル基、またはリノレイル基が好ましい。Ｃ１−２４アルキル基がより好ましく、Ｃ１−６アルキル基がより好ましい。
Ｒ２、Ｒ３およびＲ４における直鎖または分岐鎖状の飽和または不飽和のＣ１−２４炭化水素基としては、Ｃ１−２４アルキル基が好ましく、Ｃ１−６アルキル基がより好ましい。
As the linear or branched saturated or unsaturated C 1-24 hydrocarbon group for R 1 , an ethyl group, a propyl group, an ethylhexyl group, a dodecyl group, a stearyl group, or a linoleyl group is preferable. More preferably C 1-24 alkyl group, C 1-6 alkyl group is more preferable.
The linear or branched saturated or unsaturated C 1-24 hydrocarbon group for R 2 , R 3 and R 4 is preferably a C 1-24 alkyl group, and more preferably a C 1-6 alkyl group.
Ｒ１は好ましくは、水素原子、エチル基、プロピル基、エチルヘキシル基、ドデシル基、ステアリル基、リノレイル基、式（２）または式（３）である。より好ましくは、水素原子、エチル基、プロピル基、またはエチルヘキシル基であり、最も好ましくは水素原子である。 R 1 is preferably a hydrogen atom, an ethyl group, a propyl group, an ethylhexyl group, a dodecyl group, a stearyl group, a linoleyl group, formula (2) or formula (3). A hydrogen atom, an ethyl group, a propyl group, or an ethylhexyl group is more preferable, and a hydrogen atom is most preferable.
Ｒ２は好ましくは、水素原子またはＣ１−６アルキル基である。より好ましくは、水素原子メチル基、エチル基、プロピル基であり、最も好ましくは水素原子である。 R 2 is preferably a hydrogen atom or a C 1-6 alkyl group. More preferably, they are a hydrogen atom methyl group, an ethyl group, and a propyl group, Most preferably, it is a hydrogen atom.
上記一般式（１）で示される化合物としては、例えば、以下の化合物が挙げられる。 Examples of the compound represented by the general formula (1) include the following compounds.
本発明の組成物中の（Ａ）としては、シキミ酸、エチルガレート、プロピルガレート
エチルヘキシルガレート、ドデシルガレート、ステアリルガレート、リノレイルガレート、エピガロカテキンガレートまたはグルコシルペンタガレートから選ばれる化合物が好ましく、これらは単独または組み合わせて使用することができる。シキミ酸、エチルガレート、プロピルガレート、エチルヘキシルガレート、ドデシルガレート、ステアリルガレート、リノレイルガレートがより好ましく、シキミ酸、エチルガレート、プロピルガレートがより好ましく、シキミ酸がより好ましい。
(A) in the composition of the present invention is preferably a compound selected from shikimic acid, ethyl gallate, propyl gallate ethylhexyl gallate, dodecyl gallate, stearyl gallate, linoleyl gallate, epigallocatechin gallate or glucosyl pentagallate. Can be used alone or in combination. Shikimic acid, ethyl gallate, propyl gallate, ethyl hexyl gallate, dodecyl gallate, stearyl gallate and linoleyl gallate are more preferable, shikimic acid, ethyl gallate and propyl gallate are more preferable, and shikimic acid is more preferable.
本発明の組成物中の（Ａ）の濃度は、０．００１重量％〜３０重量％が好ましい。（Ａ）の効能を発揮する組成物が得られるという観点で、下限値は、０．００５重量％がより好ましく、０．０１重量％がより好ましく、０．０５重量％がより好ましく、０．１重量％がより好ましい。一方、得られる組成物の使用感の観点から、上限値は、２０重量％がより好ましく、１５重量％がより好ましく、１０重量％がより好ましく、５重量％がより好ましく、３重量％がより好ましい。 The concentration of (A) in the composition of the present invention is preferably 0.001 to 30% by weight. In view of obtaining a composition exhibiting the effect of (A), the lower limit is more preferably 0.005% by weight, more preferably 0.01% by weight, more preferably 0.05% by weight. 1% by weight is more preferred. On the other hand, from the viewpoint of the feeling of use of the resulting composition, the upper limit is more preferably 20% by weight, more preferably 15% by weight, more preferably 10% by weight, more preferably 5% by weight, and more preferably 3% by weight. preferable.
［Ｂ成分：ステロールエステル］
ステロールエステルとしては、ステロールをアシルアミノ酸でエステル化して得られるＮ−アシルアミノ酸ステロールエステル、またはステロールを脂肪酸でエステル化して得られる脂肪酸ステロールエステル等が挙げられる。
[B component: sterol ester]
Examples of the sterol esters include N-acyl amino acid sterol esters obtained by esterifying sterols with acyl amino acids, or fatty acid sterol esters obtained by esterifying sterols with fatty acids.
ステロールとしては、カンペステロール、カンペスタノール、ブラシカステロール、２２−デヒドロカンペステロール、スティグマステロール、スチグマスタノール、２２−ジヒドロスピナステロール、２２−デヒドロスチグマスタノール、７−デヒドロスチグマステロール、シトステロール、チルカロール、オイホール、フコステロール、イソフコステロール、コジステロール、クリオナステロール、ポリフェラステロール、クレロステロール、２２−デヒドロクレロステロール、フンギステロール、コンドリラステロール、アベナステロール、ベルノステロール、ポリナスタノール等のフィトステロール；コレステロール、ジヒドロコレステロール、コレスタノール、コプロスタノール、エピコプロステロール、エピコプロスタノール、２２−デヒドロコレステロール、デスモステロール、２４−メチレンコレステロール、ラノステロール、２４，２５−ジヒドロラノステロ−ル、ノルラノステロ−ル、スピナステロール、ジヒドロアグノステロール、アグノステロール、ロフェノール、ラトステロール等の動物性ステロール；デヒドロエルゴステロール、２２，２３−ジヒドロエルゴステロール、エピステロール、アスコステロール、フェコステロール等の菌類性ステロール等、ならびにこれらの水添物およびこれらの配合物等が挙げられる。植物から抽出等によって得られるステロールの混合物を用いても良い。
ステロールとしては、フィトステロール、ラノステロール、コレステロールまたはジヒドロコレステロールが好ましく、フィトステロールまたはコレステロールがより好ましく、フィトステロールが特に好ましい。シトステロール、スティグマステロールおよびカンペステロールを含むフィトステロールを用いることがより好ましい。
シトステロール、スティグマステロールおよびカンペステロールの比、シトステロール：スティグマステロール：カンペステロールが３５〜６５：１０〜４０：１０〜４０であることが好ましく、５５〜６５：２０〜３０：１０〜２０であることがより好ましい。
Examples of sterols include campesterol, campestanol, brassicasterol, 22-dehydrocampesterol, stigmasterol, stigmasterol, 22-dihydrospinasterol, 22-dehydrostigmasterol, 7-dehydrostigmasterol, sitosterol, tilcarol, Phytosterols such as euphor, fucostosterol, isofucosterol, kodisosterol, cryoasterol, polyferasterol, clerolosterol, 22-dehydrocrerolosterol, fungisterol, chondirasterol, abasterosterol, vernosterol, polynastanol; cholesterol, Dihydrocholesterol, cholestanol, coprostanol, epicoprosterol, epicoprostanol, Animal sterols such as 2-dehydrocholesterol, desmosterol, 24-methylenecholesterol, lanosterol, 24,25-dihydrolanosterol, norlanosterol, spinasterol, dihydroagnosterol, agnosterol, rophenol, latosterol; Examples include dehydroergosterol, 22,23-dihydroergosterol, fungal sterols such as episterol, ascosterol, fecosterol, and the like, hydrogenated products thereof, and combinations thereof. You may use the mixture of the sterol obtained by extraction etc. from a plant.
As the sterol, phytosterol, lanosterol, cholesterol or dihydrocholesterol is preferable, phytosterol or cholesterol is more preferable, and phytosterol is particularly preferable. More preferably, phytosterols including sitosterol, stigmasterol and campesterol are used.
The ratio of sitosterol, stigmasterol and campesterol, sitosterol: stigmasterol: campesterol is preferably 35 to 65:10 to 40:10 to 40, and preferably 55 to 65:20 to 30:10 to 20. More preferred.
アシルアミノ酸のアミノ酸としては、グリシン、Ｎ−メチルグリシン、アラニン、β−アラニン、Ｎ−メチル−β−アラニン、バリン、ロイシン、イソロイシン、セリン、トレオニン、フェニルアラニン、チロシン、トリプトファン、シスチン、システイン、メチオニン、プロリン、ヒドロキシプロリン、アスパラギン、アスパラギン酸、グルタミン、グルタミン酸、アルギニン、ヒスチジン、リシン等が挙げられる。 As amino acids of acylamino acids, glycine, N-methylglycine, alanine, β-alanine, N-methyl-β-alanine, valine, leucine, isoleucine, serine, threonine, phenylalanine, tyrosine, tryptophan, cystine, cysteine, methionine, Examples include proline, hydroxyproline, asparagine, aspartic acid, glutamine, glutamic acid, arginine, histidine, and lysine.
ステロールエステルは、好ましくは、Ｎ−アシルアミノ酸ステロールエステルであり、中でも、式（４）で示されるＮ−アシルアミノ酸ステロールエステルが特に好ましい。 The sterol ester is preferably an N-acyl amino acid sterol ester, and among them, the N-acyl amino acid sterol ester represented by the formula (4) is particularly preferable.
式中、Ｘは、水素原子、Ｃ８−３８脂肪族アルコールのエステル生成残基、またはステロールのエステル生成残基を示し、
ＣＯＲ１０は、Ｃ８−２２アシル基を示し、
Ｒ１１は、水素原子、または−ＣＯＯＹ（式中、Ｙは、水素原子、Ｃ８−３８脂肪族アルコールのエステル生成残基、またはステロールのエステル生成残基を示す。）で示される基を示し、
Ｒ１２は、水素原子またはＣ１−６アルキル基を示し、
ｎは１または２を示す。
但し、Ｒ１１が水素原子のとき、Ｘはステロールのエステル生成残基であり、Ｒ１１が−ＣＯＯＹで示される基のとき、ＸまたはＹの少なくとも一方がステロールのエステル生成残基である。）
In the formula, X represents a hydrogen atom, an ester-forming residue of a C 8-38 aliphatic alcohol, or an ester-forming residue of a sterol;
COR 10 represents a C 8-22 acyl group,
R 11 represents a hydrogen atom or a group represented by —COOY (wherein Y represents a hydrogen atom, an ester-forming residue of a C 8-38 aliphatic alcohol, or an ester-forming residue of a sterol). ,
R 12 represents a hydrogen atom or a C 1-6 alkyl group,
n represents 1 or 2.
However, when R 11 is a hydrogen atom, X is an ester-forming residue of sterol, and when R 11 is a group represented by —COOY, at least one of X or Y is an ester-forming residue of sterol. )
ＸまたはＹで示される「Ｃ８−３８脂肪族アルコールのエステル生成残基」における「Ｃ８−３８脂肪族アルコール」としては、天然または合成の、直鎖または分岐鎖状の、飽和または不飽和の、一価のＣ８−３８脂肪族アルコールであり、カプリルアルコール、ラウリルアルコール、ミリスチルアルコール、セチルアルコール、ステアリルアルコール、アラギジニルアルコール、ベヘニルアルコール等の直鎖飽和アルコール；２−ヘキシルデシルアルコール、２−オクチルドデシルアルコール、イソステアリルアルコール、デシルテトラデシルアルコール等の分岐鎖飽和アルコール；オレイルアルコール、リノレイルアルコール等の直鎖不飽和アルコール；等が挙げられる。
ＸまたはＹで示される「Ｃ８−３８脂肪族アルコールのエステル生成残基」における「Ｃ８−３８脂肪族アルコール」は、好ましくは、Ｃ８−３０脂肪族アルコール（好ましくはＣ１２−２４脂肪族アルコール、より好ましくはＣ１６−２０脂肪族アルコール）でかつ融点が２５℃以上のものであり、好適な具体例としては、例えば、２−ヘキシルデシルアルコール、２−オクチルドデシルアルコール、イソステアリルアルコール、デシルテトラデシルアルコール等の分岐鎖飽和アルコール；オレイルアルコール、リノレイルアルコール等の直鎖不飽和アルコールが挙げられる。中でも、２−ヘキシルデシルアルコール、２−オクチルドデシルアルコールまたはデシルテトラデシルアルコールが好ましく、２−オクチルドデシルアルコールがより好ましい。
別の態様として、ＸまたはＹで示される「Ｃ８−３８脂肪族アルコールのエステル生成残基」における「Ｃ８−３８脂肪族アルコール」は、好ましくは、飽和Ｃ１２−３８脂肪族アルコール（好ましくはＣ１２−２４脂肪族アルコール、より好ましくはＣ１６−２２脂肪族アルコール）でかつ融点が２５℃未満のものであり、好適な具体例としては例えば、セチルアルコール、ステアリルアルコール、ベヘニルアルコール等が挙げられる。中でも、ステアリルアルコールまたはベヘニルアルコールが好ましく、ベヘニルアルコールがより好ましい。
The “C 8-38 aliphatic alcohol” in the “ester generating residue of C 8-38 aliphatic alcohol” represented by X or Y is a natural or synthetic, linear or branched, saturated or unsaturated Monohydric C 8-38 aliphatic alcohols, linear saturated alcohols such as capryl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, aragidinyl alcohol, behenyl alcohol; 2-hexyldecyl alcohol, 2 -Branched chain saturated alcohols such as octyldodecyl alcohol, isostearyl alcohol, decyltetradecyl alcohol; linear unsaturated alcohols such as oleyl alcohol and linoleyl alcohol; and the like.
The “C 8-38 aliphatic alcohol” in the “ester generating residue of C 8-38 aliphatic alcohol” represented by X or Y is preferably a C 8-30 aliphatic alcohol (preferably a C 12-24 fatty acid). Aliphatic alcohols, more preferably C 16-20 aliphatic alcohols), and those having a melting point of 25 ° C. or higher. Preferred examples include 2-hexyldecyl alcohol, 2-octyldodecyl alcohol, and isostearyl alcohol. Branched chain saturated alcohols such as decyltetradecyl alcohol; linear unsaturated alcohols such as oleyl alcohol and linoleyl alcohol. Among them, 2-hexyldecyl alcohol, 2-octyldodecyl alcohol or decyltetradecyl alcohol is preferable, and 2-octyldodecyl alcohol is more preferable.
In another embodiment, the “C 8-38 aliphatic alcohol” in the “ester generating residue of C 8-38 aliphatic alcohol” represented by X or Y is preferably a saturated C 12-38 aliphatic alcohol (preferably Is a C 12-24 aliphatic alcohol, more preferably a C 16-22 aliphatic alcohol) and has a melting point of less than 25 ° C. Suitable examples include cetyl alcohol, stearyl alcohol, behenyl alcohol and the like. It is done. Among these, stearyl alcohol or behenyl alcohol is preferable, and behenyl alcohol is more preferable.
ＸまたはＹで示される「ステロールのエステル生成残基」における「ステロール」としては、前述のステロールが挙げられる。中でも、フィトステロール、ラノステロール、コレステロールまたはジヒドロコレステロールが好ましく、フィトステロールまたはコレステロールがより好ましく、フィトステロールが特に好ましい。シトステロール、スティグマステロールおよびカンペステロールを含むフィトステロールを用いることがより好ましい。
シトステロール、スティグマステロールおよびカンペステロールの比、シトステロール：スティグマステロール：カンペステロールが３５〜６５：１０〜４０：１０〜４０であることが好ましく、５５〜６５：２０〜３０：１０〜２０であることがより好ましい。
Examples of the “sterol” in the “ester-forming ester residue of sterol” represented by X or Y include the aforementioned sterols. Among them, phytosterol, lanosterol, cholesterol or dihydrocholesterol is preferable, phytosterol or cholesterol is more preferable, and phytosterol is particularly preferable. More preferably, phytosterols including sitosterol, stigmasterol and campesterol are used.
The ratio of sitosterol, stigmasterol and campesterol, sitosterol: stigmasterol: campesterol is preferably 35 to 65:10 to 40:10 to 40, and preferably 55 to 65:20 to 30:10 to 20. More preferred.
Ｒ１１としては、−ＣＯＯＹで示される基が好ましい。 R 11 is preferably a group represented by —COOY.
ＣＯＲ１０で示される「Ｃ８−２２アシル基」としては、例えば、直鎖または分岐鎖状の、飽和または不飽和のＣ８−２２脂肪酸より誘導されるアシル基が挙げられ、オクタノイル、ノナノイル、デカノイル、ウンデカノイル、ラウロイル、ミリストイル、パルミトイル、ステアロイル、オレオイル、リノレイル等が挙げられる。単一組成の脂肪酸より誘導されるアシル基のほか、ヤシ油脂肪酸、ヒマシ油脂肪酸、オリーブ油脂肪酸、パーム油脂肪酸等の天然より得られる混合脂肪酸、あるいは合成により得られる脂肪酸（分岐脂肪酸を含む）より誘導されるアシル基であっても良い。中でも、ラウロイル、ミリストイル、パルミトイルまたはステアロイルが好ましく、ラウロイルがより好ましい。 Examples of the “C 8-22 acyl group” represented by COR 10 include an acyl group derived from a linear or branched, saturated or unsaturated C8-22 fatty acid, and octanoyl, nonanoyl, decanoyl. , Undecanoyl, lauroyl, myristoyl, palmitoyl, stearoyl, oleoyl, linoleyl and the like. In addition to acyl groups derived from fatty acids of a single composition, natural fatty acids such as coconut oil fatty acid, castor oil fatty acid, olive oil fatty acid, palm oil fatty acid, or synthetic fatty acids (including branched fatty acids) It may be a derived acyl group. Among these, lauroyl, myristoyl, palmitoyl or stearoyl is preferable, and lauroyl is more preferable.
Ｒ１２で示される「Ｃ１−６アルキル基」としては、例えば、メチル、エチル、プロピル、イソプロピル、ブチル、イソブチル、ｓｅｃ−ブチル、ｔｅｒｔ−ブチル、ペンチル、イソペンチル、ネオペンチル、１−エチルプロピル、ヘキシル、イソヘキシル、１，１−ジメチルブチル、２，２−ジメチルブチル、３，３−ジメチルブチル、２−エチルブチル等が挙げられる。中でも、メチル、エチルが好ましい。
Ｒ１２としては、水素原子が好ましい。
Examples of the “C 1-6 alkyl group” represented by R 12 include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, 1-ethylpropyl, hexyl. , Isohexyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 2-ethylbutyl and the like. Of these, methyl and ethyl are preferable.
R 12 is preferably a hydrogen atom.
ｎは１または２を示す。ｎが１の場合、Ｎ−アシルアミノ酸ステロールエステルは、Ｎ−アシルアスパラギン酸ステロールエステルになり、ｎが２の場合、Ｎ−アシルグルタミン酸ステロールエステルとなる。ｎが２の場合、すなわちＮ−アシルグルタミン酸ステロールエステルが好ましい。なお、アミノ酸は光学活性体又はラセミ体のいずれであってもよい。 n represents 1 or 2. When n is 1, the N-acyl amino acid sterol ester is N-acyl aspartic acid sterol ester, and when n is 2, it is N-acyl glutamic acid sterol ester. When n is 2, that is, N-acylglutamic acid sterol ester is preferable. The amino acid may be optically active or racemic.
なお、本発明において、Ｎ−アシルアミノ酸ステロールエステルは、２種以上の混合物であってもよい。 In the present invention, the N-acyl amino acid sterol ester may be a mixture of two or more.
Ｎ−アシルアミノ酸ステロールエステルとしては、Ｎ−ミリストイル−Ｎ−メチル−β−アラニン（フィトステリル／デシルテトラデシル）、Ｎ−ラウロイル−Ｌ−グルタミン酸ジ（コレステリル／ベヘニル／２−オクチルドデシル）、Ｎ−ラウロイル−Ｌ−グルタミン酸ジ（フィトステリル／ベヘニル／２−オクチルドデシル）、Ｎ−ラウロイル−Ｌ−グルタミン酸ジ（コレステリル／２−オクチルドデシル）、Ｎ−ラウロイル−Ｌ−グルタミン酸ジ（フィトステリル／２−オクチルドデシル）またはＮ−ラウロイル−Ｌ−グルタミン酸ジ（フィトステリル／ベヘニル／２−オクチルドデシル／イソステアリル）が好ましく、Ｎ−ラウロイル−Ｌ−グルタミン酸ジ（コレステリル／ベヘニル／２−オクチルドデシル）、Ｎ−ラウロイル−Ｌ−グルタミン酸ジ（フィトステリル／ベヘニル／２−オクチルドデシル）、Ｎ−ラウロイル−Ｌ−グルタミン酸ジ（コレステリル／２−オクチルドデシル）またはＮ−ラウロイル−Ｌ−グルタミン酸ジ（フィトステリル／２−オクチルドデシル）がより好ましく、Ｎ−ラウロイル−Ｌ−グルタミン酸ジ（フィトステリル／ベヘニル／２−オクチルドデシル）またはＮ−ラウロイル−Ｌ−グルタミン酸ジ（フィトステリル／２−オクチルドデシル）が好ましく、Ｎ−ラウロイル−Ｌ−グルタミン酸ジ（フィトステリル／２−オクチルドデシル）がより好ましい。 Examples of N-acyl amino acid sterol esters include N-myristoyl-N-methyl-β-alanine (phytosteryl / decyltetradecyl), N-lauroyl-L-glutamate di (cholesteryl / behenyl / 2-octyldodecyl), N-lauroyl. -L-glutamate di (phytosteryl / behenyl / 2-octyldodecyl), N-lauroyl-L-glutamate di (cholesteryl / 2-octyldodecyl), N-lauroyl-L-glutamate di (phytosteryl / 2-octyldodecyl) or N-lauroyl-L-glutamate di (phytosteryl / behenyl / 2-octyldodecyl / isostearyl) is preferred, N-lauroyl-L-glutamate di (cholesteryl / behenyl / 2-octyldodecyl), N-lauroyl-L More preferred are di-glutamate (phytosteryl / behenyl / 2-octyldodecyl), N-lauroyl-L-glutamate di (cholesteryl / 2-octyldodecyl) or N-lauroyl-L-glutamate di (phytosteryl / 2-octyldodecyl), N-lauroyl-L-glutamate di (phytosteryl / behenyl / 2-octyldodecyl) or N-lauroyl-L-glutamate di (phytosteryl / 2-octyldodecyl) is preferred, N-lauroyl-L-glutamate di (phytosteryl / 2) -Octyldodecyl) is more preferred.
なお、Ｎ−ラウロイル−Ｌ−グルタミン酸ジ（フィトステリル／２−オクチルドデシル）とは、Ｎ−ラウロイル−Ｌ−グルタミン酸の２つのカルボキシ基を、フィトスロールおよび２−オクチルドデシルアルコールでエステル形成して得られる化合物を示す。即ち、Ｎ−ラウロイル−Ｌ−グルタミン酸ジフィトステリルエステル、Ｎ−ラウロイル−Ｌ−グルタミン酸γ−フィトステリル−α−２−オクチルドデシルエステル、およびＮ−ラウロイル−Ｌ−グルタミン酸α−フィトステリル−γ−２−オクチルドデシルエステルを含む。
また、Ｎ−ラウロイル−Ｌ−グルタミン酸ジ（フィトステリル／ベヘニル／２−オクチルドデシル）とは、Ｎ−ラウロイル−Ｌ−グルタミン酸の２つのカルボキシ基を、フィトスロール、ベヘニルアルコールおよび２−オクチルドデシルアルコールでエステル形成して得られる化合物を示す。即ち、Ｎ−ラウロイル−Ｌ−グルタミン酸ジフィトステリルエステル、Ｎ−ラウロイル−Ｌ−グルタミン酸γ−フィトステリル−α−２−オクチルドデシルエステル、Ｎ−ラウロイル−Ｌ−グルタミン酸α−フィトステリル−γ−２−オクチルドデシルエステルおよびＮ−ラウロイル−Ｌ−グルタミン酸γ−フィトステリル−α−ベヘニルエステルおよびＮ−ラウロイル−Ｌ−グルタミン酸α−フィトステリル−γ−ベヘニルエステルを含む。
N-lauroyl-L-glutamic acid di (phytosteryl / 2-octyldodecyl) is obtained by ester-forming two carboxy groups of N-lauroyl-L-glutamic acid with phytosulol and 2-octyldodecyl alcohol. Compounds are shown. N-lauroyl-L-glutamic acid diphytosteryl ester, N-lauroyl-L-glutamic acid γ-phytosteryl-α-2-octyldodecyl ester, and N-lauroyl-L-glutamic acid α-phytosteryl-γ-2-octyl Contains dodecyl ester.
N-lauroyl-L-glutamate di (phytosteryl / behenyl / 2-octyldodecyl) is an ester formed of two carboxy groups of N-lauroyl-L-glutamate with phytosulol, behenyl alcohol and 2-octyldodecyl alcohol. The compound obtained is shown. N-lauroyl-L-glutamic acid diphytosteryl ester, N-lauroyl-L-glutamic acid γ-phytosteryl-α-2-octyldodecyl ester, N-lauroyl-L-glutamic acid α-phytosteryl-γ-2-octyldodecyl ester Esters and N-lauroyl-L-glutamic acid γ-phytosteryl-α-behenyl ester and N-lauroyl-L-glutamic acid α-phytosteryl-γ-behenyl ester.
ステロールエステルとしては、脂肪酸ステロールエステルを用いることもできる。ここで、脂肪酸としては、酪酸、吉草酸、カプロン酸、カプリル酸、ノナン酸、カプリン酸、ラウリン酸、ミリスチン酸、パルミチン酸、パルミトレイン酸、ステアリン酸、ヒドロキシステアリン酸、イソステアリン酸、アラキン酸、ベヘン酸、リグノセリン酸、セロチン酸、オレイン酸、リノール酸、リノレン酸、リシノール酸、アラキドン酸、エイコサペンタエン酸、ドコサペンタエン酸、ドコサヘキサエン酸、ネルボン酸等の、直鎖または分岐鎖状の、飽和または不飽和のＣ４−３１脂肪酸の１種または２種以上が挙げられる。これらは、天然の動植物油由来の脂肪酸でもよく、例えば、ヒマシ油脂肪酸、脱水ヒマシ油脂肪酸、マカデミアナッツ油脂肪酸、ヤシ油脂肪酸、ピーナッツ油脂肪酸、魚油脂肪酸、菜種油脂肪酸（カノラ油脂肪酸）、ハイブリッドヒマワリ油脂肪酸、ヒマワリ油脂肪酸、ヒマワリ種子油脂肪酸、パーム油脂肪酸、綿実油脂肪酸、大豆油脂肪酸、サンフラワー油脂肪酸、小麦胚芽油脂肪酸、コメヌカ油脂肪酸、ゴマ油脂肪酸、コーン油脂肪酸、月見草種子油脂肪酸、ラノリン脂肪酸、非ヒドロキシラノリン脂肪酸、ヒドロキシラノリン脂肪酸、乳脂肪脂肪酸等が挙げられる。これらの脂肪酸は、水素添加がされていてもよい。また、不飽和脂肪酸の分子間重合反応によって得られる二塩基酸であるダイマー酸（例えばダイマージリノール酸）であってもよい。この中でも、酪酸、ノナン酸、ステアリン酸、イソステアリン酸、ヒドロキシステアリン酸、カプリル酸、カプリン酸、リシノール酸、オレイン酸、マカデミアナッツ油脂肪酸、ヒマワリ種子油脂肪酸、コメヌカ油脂肪酸、またはダイマージリノール酸が好ましく、マカデミアナッツ油脂肪酸またはダイマージリノール酸がより好ましく、ダイマージリノール酸がより好ましい。 As the sterol ester, a fatty acid sterol ester can also be used. Here, the fatty acids include butyric acid, valeric acid, caproic acid, caprylic acid, nonanoic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, hydroxystearic acid, isostearic acid, arachidic acid, behenic acid. Acid, lignoceric acid, serotic acid, oleic acid, linoleic acid, linolenic acid, ricinoleic acid, arachidonic acid, eicosapentaenoic acid, docosapentaenoic acid, docosahexaenoic acid, nervonic acid, etc., saturated or saturated One type or two or more types of unsaturated C4-31 fatty acids may be mentioned. These may be fatty acids derived from natural animal and plant oils, such as castor oil fatty acid, dehydrated castor oil fatty acid, macadamia nut oil fatty acid, coconut oil fatty acid, peanut oil fatty acid, fish oil fatty acid, rapeseed oil fatty acid (canola oil fatty acid), hybrid sunflower oil Fatty acid, sunflower oil fatty acid, sunflower seed oil fatty acid, palm oil fatty acid, cottonseed oil fatty acid, soybean oil fatty acid, sunflower oil fatty acid, wheat germ oil fatty acid, rice bran oil fatty acid, sesame oil fatty acid, corn oil fatty acid, evening primrose seed oil fatty acid, lanolin fatty acid Non-hydroxylanolin fatty acid, hydroxylanolin fatty acid, milk fat fatty acid and the like. These fatty acids may be hydrogenated. Moreover, dimer acid (for example, dimer dilinoleic acid) which is a dibasic acid obtained by the intermolecular polymerization reaction of unsaturated fatty acid may be sufficient. Among these, butyric acid, nonanoic acid, stearic acid, isostearic acid, hydroxystearic acid, caprylic acid, capric acid, ricinoleic acid, oleic acid, macadamia nut oil fatty acid, sunflower seed oil fatty acid, rice bran oil fatty acid, or dimerlinoleic acid is preferable. Macadamia nut oil fatty acid or dimer linoleic acid is more preferable, and dimer linoleic acid is more preferable.
脂肪酸ステロールエステルとしては、例えば、酪酸フィトステリル、ノナン酸フィトステリル、ステアリン酸コレステリル、イソステアリン酸コレステリル、イソステアリン酸フィトステリル、ヒドロキシステアリン酸コレステリル、ヒドロキシステアリン酸フィトステリル、カプリル／カプリン酸フィトステリル、リシノール酸フィトステリル、オレイン酸コレステリル、オレイン酸フィトステリル、オレイン酸ジヒドロコレステリル、分岐脂肪酸（Ｃ１２−３１）フィトステリル、フィトステリルカノラ油脂肪酸グリセリズ、フィトステリルナタネグリセリズ、マカデミアナッツ油脂肪酸フィトステリル、マカデミアナッツ油脂肪酸コレステリル、マカデミアナッツ油脂肪酸ジヒドロコレステリル、ヒマワリ種子油脂肪酸フィトステリル、コメヌカ油脂肪酸フィトステリル、ダイマージリノール酸（フィトステリル／イソステアリル／セチル／ステアリル／ベヘニル）、ダイマージリノール酸ダイマージリノレイルビス（ベヘニル／イソステアリル／フィトステリル）、ダイマージリノール酸（フィトステリル／ベヘニル）およびダイマージリノール酸ジ（イソステアリル／フィトステリル）等が挙げられる。 Examples of fatty acid sterol esters include phytosteryl butyrate, phytosteryl nonate, cholesteryl stearate, cholesteryl isostearate, phytosteryl isostearate, cholesteryl hydroxystearate, phytosteryl hydroxystearate, phytosteryl caprylate, phytosteryl ricinoleate, cholesteryl oleate , phytosteryl oleate, dihydrocholesteryl, branched fatty acid (C 12-31) phytosteryl, Phyto stearyl Riruka Nora oil fatty Guriserizu, Phyto Steri Luna seed glyceryl's, macadamia nut oil fatty acid phytosteryl, macadamia nut oil fatty acid cholesteryl, macadamia nut oil fatty acid dihydrocholesteryl , Sunflower seed oil fatty acid phytostery , Rice bran oil fatty acid phytosteryl, dimer linoleic acid (phytosteryl / isostearyl / cetyl / stearyl / behenyl), dimer linoleic acid dimer linoleyl bis (behenyl / isostearyl / phytosteryl), dimer linoleic acid (phytosteryl / behenyl) And dimer linoleic acid di (isostearyl / phytosteryl).
本発明の組成物には、Ｂ成分としてステロールエステルを１種以上含有させることができる。 The composition of the present invention may contain one or more sterol esters as the B component.
本発明の組成物中、（Ｂ）の濃度は、０．００１〜４０重量％が好ましい。下限値は、０．００５重量％がより好ましく、０．０１重量％が更に好ましい。上限値は、３５重量％がより好ましく、３０重量％が更に好ましく、２５重量％が更により好ましく、２０重量％が更に一層好ましく、１０重量％が特に好ましい。 In the composition of the present invention, the concentration of (B) is preferably 0.001 to 40% by weight. The lower limit is more preferably 0.005% by weight, still more preferably 0.01% by weight. The upper limit is more preferably 35% by weight, still more preferably 30% by weight, still more preferably 25% by weight, still more preferably 20% by weight, and particularly preferably 10% by weight.
（Ｂ）の重量に対する（Ａ）の重量、すなわち、(Ａ）の重量／（Ｂ）の重量は、０．０１〜１００が好ましい。下限値は、０．０５がより好ましく、０．１がより好ましく、０．２がより好ましく、０．５がより好ましい。上限値は、５０がより好ましく、４０がより好ましく、２０がより好ましく、５がより好ましく、３がより好ましい。 The weight of (A) relative to the weight of (B), that is, the weight of (A) / (B) is preferably from 0.01 to 100. The lower limit is more preferably 0.05, more preferably 0.1, more preferably 0.2, and more preferably 0.5. 50 is more preferable, 40 is more preferable, 20 is more preferable, 5 is more preferable, and 3 is more preferable.
本発明の組成物の形態には特に制限はなく、液状、ペースト状、ゲル状、固体状、粉末状等の任意の形態をとることができる。 There is no restriction | limiting in particular in the form of the composition of this invention, Arbitrary forms, such as a liquid form, a paste form, a gel form, a solid form, and a powder form, can be taken.
本発明の組成物を使用して、化粧料とすることができる。具体的には、化粧水、ローション、クリーム、乳液、美容液、シャンプー、ヘアリンス、ヘアコンディショナー、ヘアムース、ヘアジェル、ヘアワックス、エナメル、ファンデーション、アイライナー、アイブロウペンシル、マスカラ、アイシャドウ、チーク、リップスティック、おしろい、パウダー、パック、パックマスク、香水、オーデコロン、洗顔フォーム、クレンジングフォーム、クレンジングオイル、クレンジングジェル、クレンジングミルク、マスカラ、歯磨、石鹸、エアゾル、浴用剤、養毛剤、日焼け防止剤の形態とすることができる。 The composition of the present invention can be used as a cosmetic. Specifically, lotion, lotion, cream, milky lotion, serum, shampoo, hair rinse, hair conditioner, hair mousse, hair gel, hair wax, enamel, foundation, eyeliner, eyebrow pencil, mascara, eye shadow, teak, lipstick , Funny, powder, pack, pack mask, perfume, cologne, facial cleansing foam, cleansing foam, cleansing oil, cleansing gel, cleansing milk, mascara, toothpaste, soap, aerosol, bath preparation, hair nourishing agent, sunscreen Can do.
本願発明の組成物は、シワの生成、皮膚弾力の消失、脱毛といった老化現象を防止または改善する組成物であるため、皮膚用の化粧料とするのが好ましい。 Since the composition of the present invention is a composition that prevents or improves the aging phenomenon such as generation of wrinkles, loss of skin elasticity, and hair loss, it is preferably a cosmetic for skin.
また、本発明の組成物を薬用の組成物（医薬部外品を含む）として使用することもでき、シワ防止剤、シワ改善剤、またはアンチエージング剤とすることもできる。 Further, the composition of the present invention can be used as a medicinal composition (including quasi-drugs), and can also be used as a wrinkle inhibitor, a wrinkle improving agent, or an anti-aging agent.
化粧料または薬用の組成物とする場合、本発明の成分に加え、化粧料または薬用の組成物に通常に使用し得る成分を、本発明の効果を阻害しない範囲で配合しても良い。例えば、油性成分、界面活性剤、アミノ酸類、アミノ酸誘導体類、低級アルコール、高級アルコール、多価アルコール、糖アルコールおよびそのアルキレンオキシド付加物、水溶性高分子、ゲル化剤、保湿剤、殺菌剤および抗菌剤、抗炎症剤、鎮痛剤、抗真菌剤、角質軟化剥離剤、皮膚着色剤、ホルモン剤、紫外線吸収剤、育毛剤、発汗防止剤および収斂活性成分、汗防臭剤、ビタミン剤、血管拡張剤、生薬、ｐＨ調整剤、金属イオン封鎖剤、粘度調整剤、パール化剤、天然香料、合成香料、色素、顔料、酸化防止剤、防腐剤、乳化剤、脂肪及びワックス、シリコーン化合物、香油等が挙げられる。 In the case of a cosmetic or medicinal composition, in addition to the components of the present invention, components that can be normally used in the cosmetic or medicinal composition may be blended within a range that does not impair the effects of the present invention. For example, oil components, surfactants, amino acids, amino acid derivatives, lower alcohols, higher alcohols, polyhydric alcohols, sugar alcohols and their alkylene oxide adducts, water-soluble polymers, gelling agents, moisturizers, bactericides, and Antibacterial agent, anti-inflammatory agent, analgesic agent, antifungal agent, keratin softening release agent, skin colorant, hormone agent, UV absorber, hair restorer, antiperspirant and astringent active ingredient, sweat deodorant, vitamin agent, vasodilator Agents, herbal medicines, pH adjusters, sequestering agents, viscosity modifiers, pearlizing agents, natural fragrances, synthetic fragrances, pigments, pigments, antioxidants, preservatives, emulsifiers, fats and waxes, silicone compounds, perfume oils, etc. Can be mentioned.
次に実施例によって本発明を更に詳細に説明するが、本発明はこれら実施例に限定されるものではない。 EXAMPLES Next, although an Example demonstrates this invention further in detail, this invention is not limited to these Examples.
［評価１：フリーラジカル消去効果］
安定な人工的ラジカルである、ジフェニルピクリルヒドラジル（ＤＰＰＨ）を用いて、以下のようにフリーラジカル消去能を測定した。
２００μＭのＤＰＰＨエタノール溶液１００μＬに、表２に記載の濃度の各試料溶液１００μＬを加え、直ちに容器を密栓して振り混ぜ２時間室温、暗所にて静置し、波長５１６ｎｍの吸光度をサーモフィッシャーサイエンティフィック社製吸光マイクロプレートリーダーにて測定した（Ｉ）。また、２００μＭのＤＰＰＨエタノール溶液１００μＬに前記試料溶液作成に使用した溶媒のみ１００μＬを加え、上記同様に吸光度を測定した（ＩＩ）。
なお、ブランク１として、ＤＰＰＨを含まないエタノール１００μＬに、表２に記載の濃度の試料溶液１００μＬを加えた溶液の吸光度（ＩＩＩ）、および、ブランク２として、ＤＰＰＨを含まないエタノール１００μＬに前記試料溶液作成に使用した溶媒のみ１００μＬを加えた溶液の吸光度（ＩＶ）を測定した。
次式よりフリーラジカル消去効果（％）を求めた。
フリーラジカル消去効果（％）＝｛１−（Ｉ−ＩＩＩ）／（ＩＩ−ＩＶ）｝×１００
[Evaluation 1: Free radical scavenging effect]
The free radical scavenging ability was measured using diphenylpicrylhydrazyl (DPPH), which is a stable artificial radical.
Add 100 μL of each sample solution of the concentration shown in Table 2 to 100 μL of 200 μM DPPH ethanol solution, immediately seal the container, shake and mix for 2 hours at room temperature in a dark place, and absorb the absorbance at a wavelength of 516 nm at Thermo Fisher Scientific. Measurement was performed with an absorption microplate reader manufactured by Tific (I). Further, 100 μL of only the solvent used in the preparation of the sample solution was added to 100 μL of 200 μM DPPH ethanol solution, and the absorbance was measured in the same manner as described above (II).
As blank 1, absorbance (III) of a solution obtained by adding 100 μL of the sample solution having the concentration shown in Table 2 to 100 μL of ethanol not containing DPPH, and as blank 2, the sample solution was added to 100 μL of ethanol not containing DPPH. The absorbance (IV) of the solution to which 100 μL of only the solvent used for the preparation was added was measured.
The free radical scavenging effect (%) was obtained from the following equation.
Free radical scavenging effect (%) = {1- (I-III) / (II-IV)} × 100
［評価２：相乗効果］
併用による相乗効果の有無は、上記のフリーラジカル消去効果（％）を用いて以下の式により評価した。
（併用した場合の消去効果／フリーラジカル消去効果の和）
相加的な効果の場合、理論値は１となり、１を超える結果となれば、相乗効果があると判断できる。１を超えた場合○、１以下の場合×とした。
[Evaluation 2: Synergistic effect]
The presence or absence of a synergistic effect by the combined use was evaluated by the following formula using the above-mentioned free radical scavenging effect (%).
(Sum of elimination effect when combined use / free radical elimination effect)
In the case of an additive effect, the theoretical value is 1, and if the result exceeds 1, it can be determined that there is a synergistic effect. When it exceeded 1, it was set as ○ when it was 1 or less.
［評価３：刺激性］
表３に記載の組成物を調製し、組成物を皮膚に塗布した際の刺激について、５人の専門パネラーが下記の評価基準により評価を行った。
３点：刺激がまったく感じられない
２点：刺激があまり感じられない
１点：刺激がやや感じられる
０点：刺激が感じられる
専門パネラーの合計点が１３以上を◎、１０以上１２未満を○、６以上１０未満を△、５以下を×とした。
[Evaluation 3: Irritation]
The compositions shown in Table 3 were prepared, and the five expert panelists evaluated the irritation when the composition was applied to the skin according to the following evaluation criteria.
3 points: Stimulation is not felt at all 2 points: Stimulation is not felt at all 1 point: Stimulation is felt a little 0 points: Stimulation is felt Total score of professional panelists is 13 or more ◎ 10 or more and less than 12 ○ , 6 or more and less than 10 is Δ, and 5 or less is X.
［評価４：べたつき］
表３に記載の組成物を調製し、組成物を皮膚に塗布した際のべたつきついて、５人の専門パネラーが下記の評価基準により評価を行った。
３点：べたつきがまったく感じられない
２点：べたつきがあまり感じられない
１点：べたつきがやや感じられる
０点：べたつきが感じられる
専門パネラーの合計点が１３以上を◎、１０以上１２未満を○、６以上１０未満を△、５以下を×とした。
[Evaluation 4: Stickiness]
The compositions shown in Table 3 were prepared, and the stickiness when the composition was applied to the skin was evaluated by five professional panelists according to the following evaluation criteria.
3 points: Stickiness is not felt at all 2 points: Stickiness is not felt at all 1 point: Stickiness is slightly felt 0 points: Stickiness is felt Total score of professional panelists is 13 or more ◎ 10 or more and less than 12 ○ , 6 or more and less than 10 is Δ, and 5 or less is X.
［評価５：エモリエント性］
表３に記載の組成物を調製し、組成物を皮膚に塗布した後のエモリエント性について、５分後に５人の専門パネラーが下記の評価基準により評価を行った。なお、エモリエント性については、「油性の膜の働きにより肌からの水分の蒸散がおさえられることにより、皮膚を柔軟にする作用を意味する」ことを事前にパネラーに説明した。
３点：エモリエント性が感じられる
２点：エモリエント性がやや感じられる
１点：エモリエント性があまり感じられない
０点：エモリエント性がまったく感じられない
専門パネラーの合計点が１３以上を◎、１０以上１２未満を○、６以上１０未満を△、５以下を×とした。
[Evaluation 5: Emollient]
The emollient property after preparing the composition shown in Table 3 and applying the composition to the skin was evaluated by the 5 expert panelists according to the following evaluation criteria after 5 minutes. As for emollient, it was explained to the panelists in advance that “it means the action of softening the skin by suppressing the transpiration of moisture from the skin by the action of the oily film”.
3 points: Emollient is felt 2 points: Emollient is slightly felt 1 point: Emollient is not felt so much 0 points: Emollient is not felt at all Total score of professional panelists is 13 or more ◎ 10 or more Less than 12 was evaluated as ◯, 6 or more and less than 10 as Δ, and 5 or less as ×.
［評価６：延展性］
表３に記載の組成物を調製し、組成物の塗布時ののびについて、５人の専門パネラーが下記の評価基準により評価を行った。
３点：塗布時に非常にのびが感じられる
２点：塗布時にのびが感じられる
１点：塗布時にのびがあまり感じられない
０点：塗布時にのびがまったく感じられない
専門パネラーの合計点が１３以上を◎、１０以上１２未満を○、６以上１０未満を△、５以下を×とした。
[Evaluation 6: Spreadability]
The compositions listed in Table 3 were prepared, and five expert panelists evaluated the spread during application of the composition according to the following evaluation criteria.
3 points: feels very stretched when applied 2 points: feels extended when applied 1 point: feels less stretched when applied 0 points: feels less extended when applied The total number of professional panelists is 13 or more ◎: 10 or more and less than 12 was evaluated as ◯, 6 or more and less than 10 as Δ, and 5 or less as ×.
［評価７：臭い］
表３に記載の組成物を調製し、組成物の塗布時の臭いについて、５人の専門パネラーが下記の評価基準により評価を行った。
３点：塗布時にまったく臭わない
２点：塗布時に僅かに臭いを感じる
１点：塗布時にやや臭いを感じる
０点：塗布時に強く臭いを感じる
専門パネラーの合計点が１３以上を◎、１０以上１２未満を○、６以上１０未満を△、５以下を×とした。
[Evaluation 7: Smell]
The compositions shown in Table 3 were prepared, and the five panelists evaluated the odor when the composition was applied according to the following evaluation criteria.
3 points: No odor at the time of application 2 points: A slight odor at the time of application 1 point: A little odor at the time of application 0 point: A strong odor at the time of application A total of 13 or more points of professional panelists ◎ 10 or more 12 Less than (circle), 6 or more and less than 10 was made into (triangle | delta), and 5 or less was made into x.
［評価８：保存安定性１（乳化）］
表○○組成物を調製した後、４０℃で１週間保存し、その分離の様子を目視観察した。
◎：乳化が完全に維持されている
○：分離とまではいかないがわずかに変化がある
△：少し分離が認められる
×：完全に分離が認められる
[Evaluation 8: Storage stability 1 (emulsification)]
After preparing Table XX composition, it was stored at 40 ° C. for 1 week, and the state of separation was visually observed.
◎: Emulsification is completely maintained ○: Not completely separated, but slightly changed △: Some separation is observed ×: Complete separation is observed
［評価９：保存安定性２（着色）］
表○○の組成物を調製した後、４０℃で１週間保存し、その着色の様子を目視観察した。
◎：まったく着色が見られない
○：ほとんど着色が感じられない
△：やや着色が観察された
×：着色が見られた
[Evaluation 9: Storage stability 2 (colored)]
After preparing the composition of Table (circle) (circle), it preserve | saved for one week at 40 degreeC, and the state of the coloring was visually observed.
A: No coloring is observed. O: Little coloring is observed. Δ: A little coloring is observed. X: Coloring is observed.
結果を表２および表３に示す。 The results are shown in Table 2 and Table 3.
表２に示す通り、シキミ酸とラウロイルグルタミン酸ジ（フィトステリル／オクチルドデシル）を併用した場合、相乗効果の計算値は１．４６となり、シキミ酸およびラウロイルグルタミン酸ジ（フィトステリル／オクチルドデシル）が共存した場合の明らかな抗酸化活性の相乗効果が確認された。
一方、α‐トコフェロールとラウロイルグルタミン酸ジ（フィトステリル／オクチルドデシル）を併用した場合、相乗効果の計算値は１.００となり、α‐トコフェロールとラウロイルグルタミン酸ジ（フィトステリル／オクチルドデシル）の場合には、相乗効果はまったく認められなかった。
As shown in Table 2, when shikimic acid and lauroylglutamate di (phytosteryl / octyldodecyl) are used in combination, the calculated synergistic effect is 1.46. When shikimic acid and lauroylglutamate di (phytosteryl / octyldodecyl) coexist A clear synergistic effect of antioxidant activity was confirmed.
On the other hand, when α-tocopherol and dilauroylglutamate (phytosteryl / octyldodecyl) are used in combination, the calculated synergistic effect is 1.00, and in the case of α-tocopherol and dilauroylglutamate (phytosteryl / octyldodecyl) synergistically. No effect was observed.
実施例２から５の組成物は、刺激性、使用感（べたつき、エモリエント性、延展性）、臭い、保存安定性（乳化安定性、着色安定性）において優れた組成物であることがわかる。
全体的に評価すると、実施例５の組成物より、実施例２，３および４の組成物のほうが優れており、実施例２および４の組成物より実施例３の組成物のほうが優れているということができる。
It can be seen that the compositions of Examples 2 to 5 are excellent in irritation, feeling in use (stickiness, emollient, spreadability), odor, and storage stability (emulsification stability, color stability).
Overall, the compositions of Examples 2, 3 and 4 are superior to the composition of Example 5, and the composition of Example 3 is superior to the compositions of Examples 2 and 4. It can be said.
さらに以下の組成物を調製した。 Further, the following composition was prepared.
処方例１から９の組成物は、優れたフリーラジカル消去効果を有し、刺激性、使用感（べたつき、エモリエント性、延展性）、臭い、保存安定性（乳化安定性、着色安定性）において優れた組成物であった。 The compositions of Formulation Examples 1 to 9 have an excellent free radical scavenging effect, and in terms of irritation, feeling of use (stickiness, emollient, spreadability), odor, and storage stability (emulsification stability, color stability) It was an excellent composition.
なお、成分の詳細は以下の通りである。
（Ａ成分）
シキミ酸：Sigma社製
エチルガレート：Aldrich社製
エピガロカテキンガレート：Sigma社製
ドデシルガレート：Aldrich製
グルコシルペンタガレート：味の素オムニケム社製
プロピルガレート：Sigma社製
（Ｂ成分）
ラウロイルグルタミン酸ジ（フィトステリル／オクチルドデシル）：味の素社製「エルデュウ」PS-203
ラウロイルグルタミン酸ジ(オクチルドデシル/フィトステリル/ベヘニル）：味の素社製「エルデュウ」PS-306
（その他）
α‐トコフェロール：Ｓｉｇｍａ社製
PPG-6デシルテトラデセスー３０：「ＮＩＫＫＯＬ」ＰＥＮ−４６３０、Ｎｉｋｋｏｌ社製
（アクリレーツ／アクリル酸アルキル（Ｃ１０−３０））クロスポリマー：「ＰＥＭＵＬＥＮ」ＴＲ−１、日光ケミカルズ社製
メチルパラベン：和光純薬工業社製
The details of the components are as follows.
(A component)
Shikimic acid: Sigma ethyl gallate: Aldrich epigallocatechin gallate: Sigma dodecyl gallate: Aldrich glucosyl pentagallate: Ajinomoto Omnichem propyl gallate: Sigma (component B)
Lauroylglutamate di (phytosteryl / octyldodecyl): "Eldu" PS-203 manufactured by Ajinomoto Co., Inc.
Lauroyl glutamate di (octyldodecyl / phytosteryl / behenyl): Ajinomoto Co., Inc. “El Deu” PS-306
(Other)
α-Tocopherol: Sigma
PPG-6 decyltetradeceth-30: “NIKKOL” PEN-4630, manufactured by Nikkol (Acrylates / alkyl acrylate (C10-30)) crosspolymer: “PEMULEN” TR-1, methyl paraben manufactured by Nikko Chemicals: Jun Wako Made by Yakuhin
本発明により、優れたフリーラジカル消去効果を有し、刺激性、使用感（べたつき、エモリエント性、延展性）、臭い、保存安定性（乳化安定性、着色安定性）において優れた組成物を提供することができる。 The present invention provides a composition having an excellent free radical scavenging effect and excellent in irritation, feeling of use (stickiness, emollient, spreadability), odor, and storage stability (emulsification stability, coloring stability). can do.
Claims (16)
式（１）：
式（２）：
式（３）：
ただし、没食子酸を除く。）
ならびに、
（Ｂ）ステロールエステル
を含む組成物。 (A) a cyclic hydroxy acid represented by formula (1) or a derivative thereof,
Formula (1):
Formula (2):
Formula (3):
However, gallic acid is excluded. )
And
(B) A composition comprising a sterol ester.
Ｘは、水素原子、Ｃ８−３８脂肪族アルコールのエステル生成残基、またはステロールのエステル生成残基を示し、
ＣＯＲ１０は、Ｃ８−２２アシル基を示し、
Ｒ１１は、水素原子、または−ＣＯＯＹ（式中、Ｙは、水素原子、Ｃ８−３８脂肪族アルコールのエステル生成残基、またはステロールのエステル生成残基を示す。）で示される基を示し、
Ｒ１２は、水素原子またはＣ１−６アルキル基を示し、
ｎは１または２を示す。
但し、Ｒ１１が水素原子のとき、Ｘはステロールのエステル生成残基であり、Ｒ１１が−ＣＯＯＹで示される基のとき、ＸまたはＹの少なくとも一方がステロールのエステル生成残基である。）
で示されるＮ−アシルアミノ酸ステロールエステルである、請求項１〜５の何れか１項に記載の組成物。 (B) is the formula (4):
X represents a hydrogen atom, an esterogenic residue of a C 8-38 aliphatic alcohol, or an esterogenic residue of a sterol;
COR 10 represents a C 8-22 acyl group,
R 11 represents a hydrogen atom or a group represented by —COOY (wherein Y represents a hydrogen atom, an ester-forming residue of a C 8-38 aliphatic alcohol, or an ester-forming residue of a sterol). ,
R 12 represents a hydrogen atom or a C 1-6 alkyl group,
n represents 1 or 2.
However, when R 11 is a hydrogen atom, X is an ester-forming residue of sterol, and when R 11 is a group represented by —COOY, at least one of X or Y is an ester-forming residue of sterol. )
The composition of any one of Claims 1-5 which is N-acyl amino acid sterol ester shown by these.
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| JP2020007228A (en) * | 2018-07-02 | 2020-01-16 | 株式会社ノエビア | Skin external preparation |
| CN111529434A (en) * | 2020-05-11 | 2020-08-14 | 山东农业大学 | Lip prevention and health care product containing EGCG and application thereof |
| WO2020196424A1 (en) | 2019-03-28 | 2020-10-01 | 住友ベークライト株式会社 | Water-soluble additive composition |
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| JP2020007228A (en) * | 2018-07-02 | 2020-01-16 | 株式会社ノエビア | Skin external preparation |
| JP7126753B2 (en) | 2018-07-02 | 2022-08-29 | 株式会社ノエビア | Skin topical agent |
| WO2020196424A1 (en) | 2019-03-28 | 2020-10-01 | 住友ベークライト株式会社 | Water-soluble additive composition |
| CN111529434A (en) * | 2020-05-11 | 2020-08-14 | 山东农业大学 | Lip prevention and health care product containing EGCG and application thereof |
| CN111529434B (en) * | 2020-05-11 | 2021-09-03 | 山东农业大学 | Lip prevention and health care product containing EGCG and application thereof |
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