CN112135599B - 美白剂 - Google Patents
美白剂 Download PDFInfo
- Publication number
- CN112135599B CN112135599B CN201980033386.7A CN201980033386A CN112135599B CN 112135599 B CN112135599 B CN 112135599B CN 201980033386 A CN201980033386 A CN 201980033386A CN 112135599 B CN112135599 B CN 112135599B
- Authority
- CN
- China
- Prior art keywords
- acid
- skin
- aminomethylcyclohexylcarbonyl
- phenyl
- whitening
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000007854 depigmenting agent Substances 0.000 title description 2
- 230000002087 whitening effect Effects 0.000 claims abstract description 64
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 239000002253 acid Substances 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- 125000002252 acyl group Chemical group 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 26
- 239000002537 cosmetic Substances 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 abstract description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 7
- 125000002947 alkylene group Chemical group 0.000 abstract description 4
- 239000004480 active ingredient Substances 0.000 abstract description 3
- 210000003491 skin Anatomy 0.000 description 44
- -1 propioyl group Chemical group 0.000 description 38
- 238000003756 stirring Methods 0.000 description 20
- 208000012641 Pigmentation disease Diseases 0.000 description 18
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 17
- 230000019612 pigmentation Effects 0.000 description 16
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 14
- 150000003839 salts Chemical class 0.000 description 14
- 239000006071 cream Substances 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 13
- 238000009472 formulation Methods 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 11
- 238000001816 cooling Methods 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- 229930195729 fatty acid Natural products 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 235000011187 glycerol Nutrition 0.000 description 8
- 230000002401 inhibitory effect Effects 0.000 description 8
- 229920001296 polysiloxane Polymers 0.000 description 8
- GYDJEQRTZSCIOI-LJGSYFOKSA-N tranexamic acid Chemical compound NC[C@H]1CC[C@H](C(O)=O)CC1 GYDJEQRTZSCIOI-LJGSYFOKSA-N 0.000 description 8
- 239000004359 castor oil Substances 0.000 description 7
- 235000019438 castor oil Nutrition 0.000 description 7
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 6
- 102000003425 Tyrosinase Human genes 0.000 description 6
- 108060008724 Tyrosinase Proteins 0.000 description 6
- 239000006096 absorbing agent Substances 0.000 description 6
- 239000007844 bleaching agent Substances 0.000 description 6
- 230000000475 sunscreen effect Effects 0.000 description 6
- 239000000516 sunscreening agent Substances 0.000 description 6
- 229960000401 tranexamic acid Drugs 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- 239000004166 Lanolin Substances 0.000 description 4
- 208000003351 Melanosis Diseases 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 235000019388 lanolin Nutrition 0.000 description 4
- 229940039717 lanolin Drugs 0.000 description 4
- 239000006210 lotion Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000002265 prevention Effects 0.000 description 4
- 208000024891 symptom Diseases 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 3
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 3
- 235000010323 ascorbic acid Nutrition 0.000 description 3
- 229960005070 ascorbic acid Drugs 0.000 description 3
- 239000011668 ascorbic acid Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 210000002752 melanocyte Anatomy 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 210000004694 pigment cell Anatomy 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229940075554 sorbate Drugs 0.000 description 3
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 3
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 2
- WSWCOQWTEOXDQX-MQQKCMAXSA-M (E,E)-sorbate Chemical compound C\C=C\C=C\C([O-])=O WSWCOQWTEOXDQX-MQQKCMAXSA-M 0.000 description 2
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 2
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 2
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- 206010014970 Ephelides Diseases 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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- 229930003270 Vitamin B Natural products 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 description 2
- 239000002280 amphoteric surfactant Substances 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
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- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- FUWUEFKEXZQKKA-UHFFFAOYSA-N beta-thujaplicin Chemical compound CC(C)C=1C=CC=C(O)C(=O)C=1 FUWUEFKEXZQKKA-UHFFFAOYSA-N 0.000 description 2
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Abstract
本发明涉及一种具有优异的美白作用的美白剂。将下述通式(1)表示的化合物或其酸加成物作为美白剂的有效成分。式中，X表示氢原子可被甲基取代的碳数为1～2的亚烷基，Y表示COOR1或CH2OR2，R1表示氢原子或可具有支链的碳数为1～6的烷基，R2表示氢原子或可具有支链的碳数为1～6的酰基。
Description
技术领域
本发明涉及具有优异的美白作用的美白剂。
背景技术
已知除了紫外线曝露造成晒黑以外，色斑、雀斑、肝斑、因药剂引起的皮肤的黑化症等色素沉积带来的皮肤症状是由于在色素细胞(黑色素细胞)的黑色素产生进入亢进状态后，所产生的黑色素因周转(turnover)异常等而沉积在皮肤上造成的。
从外观上容易确认到与这样的色素沉积相关联的皮肤症状，因此对脸的印象有较大影响。因此，以具有想要美观的皮肤的愿望的人为中心的群体对皮肤的色素沉积的预防与改善的关心程度较高，美白剂与美白用化妆品的需求近年来也变得较大。
作为以预防或改善皮肤的色素沉积为目的的美白剂，以往已知有抗坏血酸或对苯二酚等，掺混了这些的皮肤外用剂广泛用于皮肤的色素沉积的预防或改善。另外，近年来，通过对发生色素沉积的作用机理的剖解，黑素产生抑制剂、酪氨酸酶阻化剂、酪氨酸酶基因表达抑制剂、α-MSH抑制剂、抗氧化剂、黑素细胞的树突伸长抑制剂、色素细胞向角化细胞传递黑色素的阻化剂等具有与现有的美白剂不同的作用机理的美白剂的开发如火如荼。
但是，在现有的美白剂中，虽然确认了具有一定的美白效果，但是有时不能充分满足需求，或在发挥美白作用的浓度下，有时会产生不被期望的其他作用(副反应)。因此，需要安全性高且发挥优异的美白作用的新成分，人们正在对此进行研究开发。
西曲酸酯或其盐也是近年来开发的美白剂的有效成分之一，是通过代谢而分解为氨甲环酸的化合物(专利文献1)。已知氨甲环酸具有对活化黑素细胞的前列腺素E2的产生抑制作用与酪氨酸酶抑制作用，起到美白效果。还报告了西曲酸酯除了作为其代谢物的氨甲环酸的美白作用之外，还具有化合物本身的活性带来的美白作用。
专利文献2中记载的氨基羧酸衍生物，已确认其具有抗溃疡作用，并且提出其作为医疗用品的用途。另外，该化合物的结构与氨甲环酸部分一致。
现有技术文献
专利文献
专利文献1:日本特开2008-110967号公报
专利文献2:日本特公昭64-4508号公报
发明内容
发明要解决的技术问题
本发明的技术问题在于，提供一种安全性较高且具有优异的美白作用的美白剂。
用于解决上述技术问题的方案
本发明人等追求具有美白作用的化合物而进行了深入研究，结果发现具有特定结构的氨基羧酸衍生物及其酸加成盐发挥优异的美白作用，从而完成了本发明。
即，本发明的一方案是含有以下述通式(1)表示的化合物或其酸加成盐的美白剂。
[化1]
(式中，X表示氢原子可被甲基取代的碳数为1～2的亚烷基，Y表示COOR1或CH2OR2，R1表示氢原子或可具有支链的碳数为1～6的烷基，R2表示氢原子或可具有支链的碳数为1～6的酰基。)
此外，本发明的另一方案是含有上述美白剂的美白用的皮肤外用组合物。所述皮肤外用组合物优选为化妆品。
发明效果
通过本发明，提供了具有优异的美白作用的美白剂。此外，还提供了含有该美白剂的美白用皮肤外用组合物，该美白用皮肤外用组合物适合作为化妆品。
具体实施方式
本发明的美白剂含有以下述通式(1)表示的化合物或其酸加成盐。
[化2]
通式(1)中，X表示氢原子可被甲基取代的碳数为1～2的亚烷基。作为碳数为1～2的亚烷基，为亚甲基及亚乙基。X优选为-CH2-CH(CH3)-或-CH2-CH2-。
通式(1)中，Y表示COOR1或CH2OR2，R1表示氢原子或可具有支链的碳数为1～6的烷基，R2表示氢原子或具有支链的碳数为1～6的酰基。
即，在Y为COOR1的情况下，R1为氢原子时Y为羧基，R1为可具有支链的碳数为1～6的烷基时Y为酯基。作为可以具有支链的碳数为1～6的烷基，例如可以例举：甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、正己基等。从美白作用的观点来看，R1特别优选为氢原子，或R1为烷基时其碳数越小越优选。
此外，Y为CH2OR2的情况下，R2为氢原子时Y为羟甲基，R2为可具有支链的碳数为1～6的酰基时Y为酯基。作为可具有支链的碳数为1～6的酰基，例如可以例举甲酰基、乙酰基、丙烯酰基、丙酰基、丙炔酰基、丁酰基、异丁酰基、甲基丙烯酰基、戊酰基、己酰基等。从美白作用的观点来看，R2特别优选为氢原子，或R2为酰基时其碳数越小越优选。
在通式(1)中，1,4-亚环己基可以是椅型或船型的任一种形态。此外，两个键也可以是顺式异构或反式异构的任一种关系。优选为椅型形态下的反式异构关系的1,4-亚环己基。
作为下述通式(1)表示的化合物的酸加成盐，可以例举无机酸、有机羧酸或有机磺酸的盐。作为无机酸，可以例举盐酸、氢溴酸、硫酸、硝酸、磷酸等，作为有机羧酸，可以例举乙酸、丙酸、马来酸、富马酸、草酸、柠檬酸、丁酸、乳酸、酒石酸等，作为有机磺酸，可以例举甲磺酸、乙磺酸、苯磺酸、对甲苯磺酸等。其中，优选无机酸盐，更优选盐酸盐。
作为本发明的美白剂的有效成分，可以是以通式(1)表示的化合物或其酸加成盐的任一种，更优选酸加成盐。
以下例举以通式(1)表示的化合物的具体例，但显然并不限定于这些。
2-[对-(4-氨基甲基环己基羰基)苯基]乙酸、2-[对-(4-氨基甲基环己基羰基)苯基]乙酸甲酯、2-[对-(4-氨基甲基环己基羰基)苯基]乙酸乙酯、2-[对-(4-氨基甲基环己基羰基)苯基]乙酸丙酯、2-[对-(4-氨基甲基环己基羰基)苯基]乙酸丁酯、2-[对-(4-氨基甲基环己基羰基)苯基]乙酸戊酯、2-[对-(4-氨基甲基环己基羰基)苯基]乙酸己酯；
2-[对-(4-氨基甲基环己基羰基)苯基]乙醇、2-[对-(4-氨基甲基环己基羰基)苯基]甲酸乙酯、2-[对-(4-氨基甲基环己基羰基)苯基]乙酸乙酯、2-[对-(4-氨基甲基环己基羰基)苯基]丙酸乙酯、2-[对-(4-氨基甲基环己基羰基)苯基]丁酸乙酯、2-[对-(4)-[氨基甲基环己基羰基]苯基]戊酸乙酯、2-[对-(4-氨基甲基环己基羰基)苯基]己酸乙酯；
2-[对-(4-氨基甲基环己基羰基)苯基]丙酸、2-[对-(4-氨基甲基环己基羰基)苯基]丙酸甲酯、2-[对-(4-氨基甲基环己基羰基)苯基]丙酸乙酯、2-[对-(4-氨基甲基环己基羰基)苯基]丙酸丙酯、2-[对-(4-氨基甲基环己基羰基)苯基]丙酸丁酯、2-[对-(4-氨基甲基环己基羰基)苯基]丙酸戊酯、2-[对-(4-氨基甲基环己基羰基)苯基]丙酸己酯；
2-[对-(4-氨基甲基环己基羰基)苯基]丙醇、2-[对-(4-氨基甲基环己基羰基)苯基]丙基甲酸酯、2-[对-(4-氨基甲基环己基羰基)苯基]丙基乙酸酯、2-[对-(4-氨基甲基环己基羰基)苯基]丙基丙酸酯、2-[对-(4-氨基甲基环己基羰基)苯基]丙基丁酸酯、2-[对-(4-氨基甲基环己基羰基)苯基]丙基戊酸酯、2-[对-(4-氨基甲基环己基羰基)苯基]丙基己酸酯；
3-[对-(4-氨基甲基环己基羰基)苯基]丙酸(化合物1)、3-[对-(4-氨基甲基环己基羰基)苯基]丙酸甲酯、3-[对-(4-氨基甲基环己基羰基)苯基]丙酸乙酯、3-[对-(4-氨基甲基环己基羰基)苯基]丙酸丙酯、3-[对-(4-氨基甲基环己基羰基)苯基]丙酸丁酯、3-[对-(4-氨基甲基环己基羰基)苯基]丙酸戊酯、3-[对-(4-氨基甲基环己基羰基)苯基]丙酸己酯(化合物2)；
3-[对-(4-氨基甲基环己基羰基)苯基]丙醇(化合物3)、3-[对-(4-氨基甲基环己基羰基)苯基]丙基甲酸酯、3-[对-(4-氨基甲基环己基羰基)苯基]丙基乙酸酯、3-[对-(4-氨基甲基环己基羰基)苯基]丙基丙酸酯、3-[对-(4-氨基甲基环己基羰基)苯基]丙基丁酸酯、3-[对-(4-氨基甲基环己基羰基)苯基]丙基戊酸酯、3-[对-(4-氨基甲基环己基羰基)苯基]丙基己酸酯(化合物4)；
2-甲基-3-[对-(4-氨基甲基环己基羰基)苯基]丙醇、2-甲基-3-[对-(4-氨基甲基环己基羰基)苯基]丙基甲酸酯、2-甲基-3-[对-(4-氨基甲基环己基羰基)苯基]丙基乙酸酯、2-甲基-3-[对-(4-氨基甲基环己基羰基)苯基]丙基丙酸酯、2-甲基-3-[对-(4-氨基甲基环己基羰基)苯基]丙基丁酸酯、2-甲基-3-[对-(4-氨基甲基环己基羰基)苯基]丙基戊酸酯、2-甲基-3-[对-(4-氨基甲基环己基羰基)苯基]丙基己酸酯(化合物5)。
[化3]
[化4]
[化5]
[化6]
[化7]
以通式(1)表示的化合物可以通过常规方法合成及提纯来获得。例如，可以通过专利文献2中记载的氨基羧酸卤化物的酸加成盐在路易斯酸存在下的酰化反应进行合成，并经过适当的分离及提纯方法来制造。
以通式(1)表示的化合物及其酸加成盐具有优异的美白作用，因此成为美白剂的有效成分。
另外，在本说明书中，美白是指色素沉积的预防及/或改善，更具体而言，是指色斑、暗沉、雀斑、晒黑、皮肤的炎症或刺激引起的黑头等的、由于黑色素产生亢进、过多蓄积、及沉积异常等而产生的色素沉积症状、及带来甾醇等药物引起的皮肤的黑化症等色素沉积的疾病等引起的色素沉积症状等的预防及/或改善。
虽然本发明的美白剂的作用机理的详细内容尚不明，但推测是通过酪氨酸酶抑制作用、酪氨酸酶基因表达抑制作用、酪氨酸酶蛋白表达抑制作用、酪氨酸酶关联蛋白分解作用等酪氨酸酶活性抑制作用、质子泵抑制作用、色素细胞向角化细胞传递黑色素的抑制作用或新的作用机理来预防及/或改善色素沉积。
本发明还可以从另一方面实现包括应用以通式(1)表示的化合物或其酸加成盐的美白方法或色素沉积的预防及/或改善方法。
本发明还可以从另一方面实现以通式(1)表示的化合物或其酸加成盐的用于美白或用于预防及/或改善色素沉积的用途。
本发明还可以从另一方面实现以通式(1)表示的化合物或其酸加成盐在美白剂的制造中的用途。
本发明还可以从另一方面实现用于美白或色素沉积的预防及/或改善的以通式(1)表示的化合物或其酸加成盐。
已知以通式(1)表示的化合物的结构与氨甲环酸部分一致，但在生物体内不会被代谢成氨甲环酸。即，可以认为以通式(1)表示的化合物的美白作用与氨甲环酸的机制不同，推测至少(4-氨基甲基环己基羰基)苯基的结构与该作用的发挥有关。
需要说明的是，专利文献1中记载的西曲酸酯是氨甲环酸的酯衍生物，通过其自身的结构及通过代谢切断酯键而成为氨甲环酸，由此发挥美白作用。
[化8]
[化9]
本发明的美白剂可以含有在美白用的组合物中，特别优选为制成可以期待经皮吸收的效果的皮肤外用组合物。作为皮肤外用组合物的形态，只要在皮肤外用中适用就没有特别限定，可优选例举化妆品(包括非正规药品)、医药品等。以通式(1)表示的化合物可确认较高的安全性，可以以日常使用的化妆品的形态连续施用。
作为皮肤外用组合物的剂型，没有特别的限定，例如可以例举:护肤液型、乳液或乳霜等乳化剂型、油剂型、凝胶剂型、涂敷剂、洗面奶等。
在美白用的皮肤外用组合物中含有本发明的美白剂的情况下，该美白剂的量的总量相对于组合物全量优选为0.01％～20质量％，更优选为0.1～10质量％，进一步优选为1～5质量％的含量，如此，容易得到所期望的效果，还能够确保处方设计的自由度。
本发明的美白用的皮肤外用组合物除了含有本发明的美白剂以外，还能够在不损害本发明的效果的提前下任意地含有在通常的皮肤外用组合物中掺混的成分。
作为这样的成分，例如可以例举：澳洲坚果油、鳄梨油、玉米油、橄榄油、菜籽油、芝麻油、蓖麻油、红花籽油、棉籽油、霍霍巴油、椰子油、棕榈油、液状羊毛脂、硬化椰子油、硬化油、木蜡、硬化蓖麻油、蜂蜡、小烛树蜡、棕榈蜡、白蜡、羊毛脂、还原羊毛脂、硬质羊毛脂、霍霍巴蜡等类油、蜡类；液体石蜡、角鲨烷、姥鲛烷、地蜡、石蜡、矿物蜡、凡士林、微晶蜡等烃类；油酸、异硬脂酸、月桂酸、肉豆蔻酸、棕榈酸、硬脂酸、山嵛酸、十一碳烯酸等高级脂肪酸类；鲸蜡醇、硬脂醇、异硬脂醇、山嵛醇、辛基十二烷醇、肉豆蔻醇、鲸蜡硬脂醇等高级醇等；异辛酸十六烷酯、肉豆蔻酸异丙酯、己基癸醇异硬脂酸酯、己二酸二异丙酯、癸二酸二-2-乙基己酯、乳酸十六烷基酯、苹果酸二异硬脂酯、二-2-乙基己酸乙二醇酯、新戊二醇二葵酸酯、二-2-庚基十一烷酸甘油酯、三-2-乙基己酸甘油酯、三-2-乙基己酸三羟甲基丙烷、三羟甲基丙烷三异硬脂酸酯、四-2-乙基己酸季戊四醇等合成酯油类；二甲基聚硅氧烷、甲基苯基聚硅氧烷、二苯基聚硅氧烷等链状聚硅氧烷；八甲基环四硅氧烷、十甲基环五硅氧烷、十二甲基环六硅氧烷等环状聚硅氧烷；氨基改性聚硅氧烷、聚醚改性聚硅氧烷、烷基改性聚硅氧烷、氟改性聚硅氧烷等改性聚硅氧烷等硅油等油剂类；
脂肪酸皂(月桂酸钠、棕榈酸钠等)、月桂基硫酸钾、烷基硫酸三乙醇胺醚等阴离子表面活性剂类；三甲基十八烷基氯化铵、苯扎氯铵、月桂基氧化胺等阳离子表面活性剂类；咪唑啉类两性表面活性剂(2-椰酰基-2-氢氧化咪唑啉鎓-1-羧乙氧基二钠盐等)、甜菜碱类表面活性剂(烷基甜菜碱、酰胺甜菜碱、磺基甜菜碱等)、酰基甲基牛磺酸等两性表面活性剂类；山梨酸酯脂肪酸酯类(山梨酸酯单硬脂酸酯、倍半油酸山梨酸酯等)、甘油脂肪酸类(单硬脂酸甘油等)、丙二醇脂肪酸酯类(单硬脂酸丙二醇酯等)、硬化蓖麻油衍生物、甘油烷基醚、POE山梨酸酯脂肪酸酯类(POE山梨酸酯单油酸酯、聚氧乙烯山梨酸酯单硬脂酸酯)、POE山梨糖醇脂肪酸酯类(POE-山梨糖醇单油酸酯)、POE甘油脂肪酸酯(POE-单异硬脂酸甘油等)、POE脂肪酸酯类(聚乙二醇单油酸酯、POE二硬脂酸酯等)、POE烷基醚类(POE2-辛基十二烷基醚等)、POE烷基苯基醚类(POE壬基苯基醚等)、普卢兰尼克(Pluronic)类型、POE·POP烷基醚类(POE·POP2-癸基十四烷基醚等)、TETRONICS类、POE蓖麻油·硬化蓖麻油衍生物(POE蓖麻油、POE硬化蓖麻油等)、蔗糖脂肪酸酯、烷基葡糖苷等非离子表面活性剂类；聚乙二醇、甘油、1，3-丁二醇、赤藓醇、山梨糖醇、木糖醇、麦芽糖醇、丙二醇、二丙二醇、双甘油、异戊二醇、1，2-戊二醇、2，4-己二醇、1，2-己二醇、1，2-辛二醇等多元醇类；
吡咯烷酮羧酸钠、乳酸、乳酸钠等保湿成分类；可被表面处理的：云母、滑石、高岭土、合成云母、碳酸钙、碳酸镁、无水硅酸(二氧化硅)、氧化铝、硫酸钡等粉体类；可被表面处理的：氧化铁、黄氧化铁、黑氧化铁、氧化钴、群青、普鲁士蓝、氧化钛、氧化锌的无机颜料类；可被表面处理的：云母钛、鱼磷箔、三氯氧化铋等珠光剂类；可被色淀(lake)化的：红色202号、红色228号、红色226号、黄色4号、蓝色404号、黄色5号、红色505号、红色230号、红色223号、橙色201号、红色213号、黄色204号、黄色203号、蓝色1号、绿色201号、紫色201号、红色204号等有机色素类；聚乙烯粉末、聚甲基丙烯酸甲酯、尼龙粉末、有机聚硅氧烷弹性体等有机粉体类；对氨基苯甲酸类紫外线吸收剂；邻氨基苯甲酸类紫外线吸收剂；水杨酸类紫外线吸收剂；肉桂酸系紫外线吸收剂；二苯甲酮系紫外线吸收剂；糖类紫外线吸收剂；2-(2’-羟基-5’-叔辛基苯基)苯并三唑、4-甲氧基-4’-叔丁基二苯甲酰甲烷等紫外线吸收剂类；
乙醇、异丙醇等低级醇类；维生素A或其衍生物、维生素B6盐酸盐、维生素B6三棕榈酸酯、维生素B6二辛酸酯、维生素B2或其衍生物、维生素B12、维生素B15或其衍生物等维生素B类；如α-生育酚、β-生育酚、γ-生育酚、维生素E乙酸酯等维生素E类、维生素D类、维生素H、泛酸、泛硫乙胺、吡咯并喹啉醌等维生素类等；对羟基苯甲酸甲酯、对羟基苯甲酸乙酯、对羟基苯甲酸丁酯、苯氧乙醇等抗菌剂(防腐剂)；甘草酸衍生物、甘草次酸衍生物、水杨酸衍生物、扁柏酚、氧化锌、尿囊素等消炎剂；视黄醇、抗坏血酸、生育酚、或法尼基乙酸酯等皱纹改善剂；各种提取物(例如黄檗、黄连、紫根、芍药、当药、白桦、鼠尾草、枇杷、人参、芦荟、锦葵、鸢尾、葡萄、薏苡仁、丝瓜络、百合、藏红花、川芎、生姜、小连翘、针苜蓿、大蒜、辣椒、陈皮、当归、海藻等)；蜂王浆、光敏剂、胆固醇衍生物等活化剂；壬酸香草酰胺、辣椒素、姜酮、单宁酸血液循环促进剂；硫磺、二甲噻蒽等抗脂漏剂；氨甲环酸、硫代牛磺酸、亚牛磺酸等抗炎症剂；胶原蛋白、透明质酸等水溶性高分子；等。
此外，也可以同时掺混本发明的美白剂以外的美白剂。例如烷基间苯二酚、抗坏血酸或其衍生物、胎盘提取物、虎耳草或薏苡等植物提取物、熊果素等。
实施例
以下，例举具体的实验例，更详细地说明本发明，但本发明并不仅限于以下的方式。
<美白效果的试验>
分别通过常规方法制备表1中记载的化妆品(实施例1～9、比较例及参考例)。
对于制备的各化妆品，通过以下的方法评价美白效果(色素沉积的改善效果)。即，在自愿参加的10名评定员的左右上臂内侧部合计设置8处0.5cm×0.5cm的试验部位。对设置的部位1天1次、连续3天照射3次照射最少红斑量(1MED)的紫外线照射。从试验第1天的紫外线照射结束时(第1次照射结束后)开始，在1天2次连续25天地在比较例与剩余的7处涂布实施例1～9及参考例中的任一种化妆品各50μL。在25天的涂布结束24小时后，用色彩色差计(CR-300、柯尼卡美能达株式会社)测量各试验部位的皮肤明亮度(L*值)，从实施例或参考例的化妆品的涂布部位的L*值减去比较例的化妆品的涂布部位的L*值，由此计算出皮肤明量度的差(ΔL*值)。L*值是色素沉积的程度越强则越低的值，因此能够判断ΔL*值越大色素沉积越得到改善。
[表1]
(质量％)
| POE(60)硬化蓖麻油 | 0.1 |
| 1,3-丁二醇 | 5 |
| 甘油 | 2 |
| 聚乙二醇400 | 3 |
| 1,2-戊二醇 | 3 |
| 氢氧化钾 | 0.005 |
| 羟苯甲酯 | 0.2 |
| 表2的化合物 | 表2的量 |
| 水 | 余量 |
[表2]
※2AA：ΔL＊≥0.5％以上、A：0.4＜ΔL＊＜0.5、B：ΔL＊≤0.4
<制造例1>
用表3所示的处方制备作为本发明的皮肤外用剂的化妆水。即，将A的成分在常温下、将B的成分在60℃下分别升温并混合，在搅拌下将B缓缓加入至A，搅拌冷却得到化妆水。
确认到该化妆水在适用于皮肤时可得到美白效果。
[表3]
<制造例2>
用表4所示的处方制备作为本发明的皮肤外用剂的化妆水。即，将A的成分在常温下、将B成分在60℃下分别升温并混合，在搅拌下将B缓缓加入至A，搅拌冷却得到化妆水。
确认到该化妆水在适用于皮肤时可得到美白效果。
[表4]
<制造例3>
用表5所示的处方制备作为本发明的皮肤外用剂的精华液。即，将A的成分及B的成分分别在80℃下进行升温并混合，在搅拌下将B缓缓加入至A，搅拌冷却得到精华液。
确认到该精华液在适用于皮肤时可得到美白效果。
[表5]
<制造例4>
用表6所示的处方制备作为本发明的皮肤外用剂的乳液。即，将A的成分及B的成分分别在80℃下进行升温并混合，在搅拌下将B缓缓加入至A，搅拌冷却得到乳液。
确认到该乳液在适用于皮肤时可得到美白效果。
[表6]
<制造例5>
用表7所示的处方制备作为本发明的皮肤外用剂的O/W乳膏。即，将A的成分及B的成分分别在80℃下进行升温并混合，在搅拌下将B缓缓加入至A，搅拌冷却得到O/W乳膏。
确认到该O/W乳膏在适用于皮肤时可得到美白效果。
[表7]
<制造例6>
用表8所示的处方制备作为本发明的皮肤外用剂的O/W乳膏。即，将A的成分及B的成分分别在80℃下进行升温并混合，在搅拌下将B缓缓加入至A，搅拌冷却得到O/W乳膏。
确认到该O/W乳膏在适用于皮肤时可得到美白效果。
[表8]
<制造例7>
用表9所示的处方制备作为本发明的皮肤外用剂的O/W粉底。即，将A的成分及B的成分分别在80℃下进行升温并混合，在搅拌下将B缓缓加入至A，搅拌冷却得到O/W粉底。
确认到该O/W粉底在适用于皮肤时可得到美白效果。
[表9-1]
[表9-2]
<制造例8>
用表10所示的处方制备作为本发明的皮肤外用剂的O/W粉底。即，将A的成分及B的成分分别在80℃下进行升温并混合，在搅拌下将B缓缓加入至A，搅拌冷却得到O/W粉底。
确认到该O/W粉底在适用于皮肤时可得到美白效果。
[表10-1]
[表10-2]
<制造例9>
用表11所示的处方制备作为本发明的皮肤外用剂的O/W防晒霜。即，将A的成分及B的成分分别在80℃下进行升温并混合，在搅拌下将B缓缓加入至A，搅拌冷却得到O/W防晒霜。
确认到该O/W防晒霜在适用于皮肤时可得到美白效果。
[表11-1]
[表11-2]
<制造例10>
用表12所示的处方制备作为本发明的皮肤外用剂的O/W防晒霜。即，将A的成分及B的成分分别在80℃下进行升温并混合，在搅拌下将B缓缓加入至A，搅拌冷却得到O/W防晒霜。
确认到该O/W防晒霜在适用于皮肤时可得到美白效果。
[表12-1]
[表12-2]
产业上的可利用性
本发明的美白剂起到优异的美白效果，因此可适宜地包含在美白用的皮肤外用组合物中，在产业上非常有用。
Claims (3)
1.通式(1)表示的化合物或其酸加成物在用于制备美白用的皮肤外用组合物中的用途：
式中，X表示-CH2-CH2-或-CH2-CH(CH3)-，Y表示COOR1或CH2OR2，R1表示氢原子或非支链的碳数为1～6的烷基，R2表示氢原子或非支链的碳数为1～6的酰基。
2.根据权利要求1的用途，其中通式(1)表示的化合物为
3.根据权利要求1或2的用途，其中所述皮肤外用组合物是化妆品。
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| JP2018-101963 | 2018-05-29 | ||
| PCT/JP2019/017350 WO2019230274A1 (ja) | 2018-05-29 | 2019-04-24 | 美白剤 |
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- 2019-04-24 EP EP19812513.0A patent/EP3804690A4/en active Pending
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5846049A (ja) * | 1981-09-11 | 1983-03-17 | Teijin Ltd | アミノカルボン酸誘導体およびその製造法 |
| JPH0383912A (ja) * | 1989-08-29 | 1991-04-09 | Dai Ichi Seiyaku Co Ltd | 日腔用組成物 |
| WO1995003818A1 (fr) * | 1993-07-30 | 1995-02-09 | Teijin Limited | Poudre permettant l'administration par voie nasale d'un medicament peptidique ou proteique |
| CN101378724A (zh) * | 2006-02-14 | 2009-03-04 | 宝丽化学工业有限公司 | 皮肤增白化妆品 |
| CN102711720A (zh) * | 2009-12-16 | 2012-10-03 | 宝丽化成工业有限公司 | 色素沉着预防或改善剂 |
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| BR112020023802B1 (pt) | 2023-10-31 |
| AU2019278251A1 (en) | 2020-12-10 |
| KR102513180B1 (ko) | 2023-03-23 |
| KR20210003827A (ko) | 2021-01-12 |
| JP7239573B2 (ja) | 2023-03-14 |
| NZ770176A (en) | 2024-02-23 |
| WO2019230274A1 (ja) | 2019-12-05 |
| SG11202011525WA (en) | 2020-12-30 |
| CN112135599A (zh) | 2020-12-25 |
| CA3101313A1 (en) | 2019-12-05 |
| EP3804690A1 (en) | 2021-04-14 |
| IL278816B2 (en) | 2023-11-01 |
| UA126100C2 (uk) | 2022-08-10 |
| AU2019278251B2 (en) | 2021-12-16 |
| RU2757906C1 (ru) | 2021-10-22 |
| TW202015653A (zh) | 2020-05-01 |
| IL278816B1 (en) | 2023-07-01 |
| EP3804690A4 (en) | 2022-06-08 |
| MX2020012483A (es) | 2021-02-15 |
| BR112020023802A2 (pt) | 2021-02-23 |
| CA3101313C (en) | 2023-01-24 |
| IL278816A (en) | 2021-01-31 |
| JPWO2019230274A1 (ja) | 2021-06-17 |
| US20210196599A1 (en) | 2021-07-01 |
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