CN106132390A - 由d‑泛醇构成的黑色素生成抑制剂、及含有该黑色素生成抑制剂的美白化妆品 - Google Patents
由d‑泛醇构成的黑色素生成抑制剂、及含有该黑色素生成抑制剂的美白化妆品 Download PDFInfo
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- CN106132390A CN106132390A CN201580016779.9A CN201580016779A CN106132390A CN 106132390 A CN106132390 A CN 106132390A CN 201580016779 A CN201580016779 A CN 201580016779A CN 106132390 A CN106132390 A CN 106132390A
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Abstract
本发明提供一种D‑泛醇的新用途。并且提供一种由D‑泛醇构成的黑色素生成抑制剂。
Description
技术领域
本发明涉及一种由D-泛醇构成的黑色素生成抑制剂。另外,涉及一种含有该黑色素生成抑制剂的美白化妆品。
背景技术
D-泛醇是一种泛酸的醇型衍生物,是能在体内转换为维生素B5(泛酸)的物质。另外,一直以来被用作皮肤外用剂的材料,已经提出有多种含有D-泛醇的皮肤外用剂。
例如,在专利文献1中,记载了一种改善皮肤粗糙度,尤其改善皮肤干燥性,从而调整肤质的含有D-泛醇的皮肤化妆品。
另外,在专利文献2中,记载了一种使毛发具有良好的弹性、韧性、顺滑性的含有D-泛醇的毛发化妆品。
现有技术文献
专利文献
专利文献1:日本特开2012-41302号公报
专利文献2:日本特开2012-167042号公报
发明内容
本发明要解决的问题
本发明提供一种上述D-泛醇的新用途。
用于解决问题的手段
本发明人等通过实验发现,D-泛醇具有黑色素生成抑制作用,从而完成本发明。
即,本发明的第一方式是由D-泛醇构成的黑色素生成抑制剂。
另外,本发明的另一方式是含有上述黑色素生成抑制剂的美白化妆品。
发明的效果
根据本发明,提供一种新的黑色素生成抑制剂。另外,根据本发明的另一方式,提供一种美白效果显著的美白化妆品。
附图说明
图1是表示实验例中D-泛醇的黑色素生成抑制作用的图表。
图2是表示实验例中D-泛醇的角化细胞的细胞生长作用的图表。
具体实施方式
以下,针对本发明进行详细地说明,但本发明不限于具体实施方式。
D-泛醇是由以下结构式(1)表示的化合物。
D-泛醇被用作化妆品等皮肤外用剂的材料,可容易地获取,能够适当使用市售品。
本发明人等进行如下所述的实验,根据其结果,发现D-泛醇不仅具有角化细胞的细胞生长作用,而且具有黑色素生成抑制作用。
<实验1:黑色素生成抑制实验>
按照以下记载的方法,在细胞内黑色素合成过程中,采用特异地被黑色素获取的2-硫脲嘧啶(在本试验中使用14C标记的2-硫脲嘧啶),对黑色素生成抑制作用进行评价。使用24孔板,采用黑色素细胞培养用完全培养基(Invitrogen Corporation),分别向各孔以6.0×104cells/well/0.5mL浓度播种正常人类黑色素细胞(Kurabo Industries Ltd.)。在5%二氧化碳气氛下,以37℃培养24小时。之后,分别以各浓度3孔,更换至0.5mL含有0mM、1mM的D-泛醇的培养基,进一步向该9孔中添加0.5μCi/well的2-[2-14C]硫脲嘧啶(Daiichiclarity Co.,LTD)。然后,以与上述培养条件相同的条件再培养3天。培养结束之后,从各孔中去除培养液,使用PBS(磷酸盐缓冲生理盐水)清洗之后,使用WST-8试剂(株式会社同仁化学研究所)测定细胞数。去除WST-8试剂,用PBS清洗之后,使用100(w/v)%三氯乙酸(和光纯药工业株式会社)从孔的底面剥离细胞之后,加水稀释使三氯乙酸浓度成为10(w/v)%,在冰箱中静置30分钟。利用离心分离回收细胞之后,使用液体闪烁计数器(Aloka Co.,LTD.)测定从各孔回收的细胞中14C-硫脲嘧啶量。
分别求出由含有1mM的D-泛醇的培养基培养得到的细胞的辐射剂量相对于由含有0mM的D-泛醇的培养基培养得到的细胞的辐射剂量(对照)的百分率,作为黑色素量(%)。即,能够判断各细胞内获取的辐射剂量性越小,黑色素量越小,因此,能够判断所添加的成分的黑色素抑制力值越大。结果在图1中示出。
<实验2:角化细胞的细胞生长实验>
按照以下记载的方法,评价细胞生长促进作用。使用24孔板,采用角化细胞培养用完全培养基(Kurabo Industries Ltd.),分别向各孔以1.0×104cells/well/1mL浓度播种正常人类角化细胞(Kurabo Industries Ltd.)。在5%二氧化碳气氛下,以37℃培养24小时。之后,分别以各浓度3孔,更换至1mL含有0μM、15μM、150μM的D-泛醇的培养基。然后,以与上述培养条件相同的条件再培养2天。培养结束之后,各孔分别添加20μL的WST-8试剂(株式会社同仁化学研究所),在37℃下,进行3小时显色反应。反应之后,利用酶标仪BenchmarkPlus(Bio-Rad Laboratories)测定450nm和650nm的吸光度,将450nm吸光度测定值-650nm吸光度测定值计算出的值作为细胞生长测定值。
分别求出由含有D-泛醇的培养基培养得到的孔的细胞生长测定值相对于由含有0μM的D-泛醇的培养基培养得到的孔的细胞生长测定值(对照)的百分率,作为细胞生长率(%)。即,能够判断吸光度值越大,细胞生长率越高,因此,能够判断所添加的成分的细胞生长促进力值越大。结果在图2中示出。
根据上述实验1,可知D-泛醇具有黑色素生成抑制作用,为具有美白效果的材料。
另外,根据上述实验2,还可知D-泛醇具有角化细胞的细胞生长作用,可以认为通过使角化细胞的细胞生长,促进角化细胞的代谢,从而促进黑色素排出。
根据以上实验,可知D-泛醇不仅能抑制黑色素的生成,而且能促进黑色素的排出,利用这两种作用的机理所产生的美白作用,D-泛醇具有显著的美白效果。进而,利用具有两种作用机理,尤其具有角化细胞的代谢促进作用,能够期待比以往的美白剂更迅速地获得美白效果(美白速度快)。另外,由于具有不同于以往美白剂的作用机理,因此通过组合使用其他美白剂,能够期待美白效果的持续性、更显著的美白效果。
这样,由于D-泛醇具有显著的美白效果,优选配混于美白化妆品。另外,还优选作为有效成分配混于美白化妆品。当D-泛醇配混于美白化妆品时,配混量通常为0.0001质量%以上、优选为0.001质量%以上、更优选为0.01质量%以上、进一步优选为0.1质量%以上。另外上限通常为20质量%以下、优选为10质量%以下、更优选为5质量%以下。
作为D-泛醇应用于皮肤的一种方式,例如可列举出与具有黑色素生成抑制作用的植物提取物组合应用的方法。通过与具有黑色素生成抑制作用的植物提取物组合,能够显著地提高D-泛醇的美白效果。作为该植物提取物,可优选例示出茜草科钩藤提取物、毛叶香茶菜提取物、狭叶松果菊叶提取物、紫草根提取液、红花提取液、鳄梨提取液、秋葵提取液、猕猴桃提取液、艳山姜叶提取物、肥皂草提取物、金银花提取物、茶提取物、冬瓜子提取物、大蒜提取物、青柠果汁提取物、纳豆提取物、橙提取物、缬草提取物、黄瓜提取物、杏仁提取物、山栀子提取物、葡萄柚提取物、牛蒡提取物、红茶提取物、杉菜提取物、锦葵提取物、大枣提取物、番茄提取物、人参提取物、茯苓提取物、白花百合鳞茎提取物、灵芝提取物、莴苣叶提取物、柠檬提取物或者蜂王浆提取物等。这些植物提取物可以仅使用一种,也可以两种以上组合使用。
在将具有黑色素生成抑制作用的植物提取物和D-泛醇应用于皮肤时,优选同时或者大致同时使用。在此所述“大致同时”是指,例如一天以内的意思,更优选12小时以内、进一步优选6小时以内、尤其优选1小时以内。
具体而言,可优选例示出将双方配混于皮肤外用剂,作为该皮肤外用剂的有效成分应用于皮肤的方法。
所述应用方法也可应用于将植物提取物以外的美白成分和D-泛醇组合的美白方法。
将具有黑色素生成抑制作用的植物提取物配混于美白化妆品时,配混量通常为0.0001质量%以上、优选为0.001质量%以上、更优选为0.01质量%以上、进一步优选为0.1质量%以上。另外,上限通常为20质量%以下、优选为10质量%以下、更优选为5质量%以下。
所述植物提取物的提取方法并未特别限定,但优选利用溶剂的提取法。在进行提取时,上述原材料可以直接使用,但将其粉碎/切碎呈粉末状用于提取,能以平稳条件短时间且高提取效率地进行有效成分的提取。
提取温度并未特别限定,可以根据原材料粉碎物大小、溶剂种类等适当设定。通常设定在室温至溶剂沸点的范围内。另外,提取时间也未特别限定,可以根据原材料粉碎物的大小、溶剂种类、提取温度等适当设定。另外,在提取时,可以进行搅拌,也可以不搅拌静置,还可以施加超声波。
例如,对于上述植物提取物,可以将原材料浸渍于溶剂中,在室温或者80℃~100℃下进行提取。对通过提取处理得到的提取液进行过滤之后,可以将其直接地或者根据需要浓缩或干燥以后,用作活性成分。需要说明的是,在该提取处理时,可以使用切碎或者粉碎后的原材料。另外,也可以使用生的原材料或者干燥后的原材料,或者也可以使用焙烤后的原材料。焙烤方法并未特别限定,可列举出在80℃~120℃下焙烤0.5小时~2小时的方法。
用于提取的溶剂种类并未特别限定,优选水(包括热水等)、醇(例如甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、2-丁醇)、二醇(例如1,3-丁二醇、丙二醇)、丙三醇、酮(例如丙酮、甲基乙基酮)、醚(例如二乙醚、二恶烷、四氢呋喃、丙醚)、乙腈、酯(例如乙酸乙酯、乙酸丁酯)、脂肪族烃(例如己烷、庚烷、液体石蜡)、芳香族烃(例如甲苯、二甲苯)、卤代烃(例如三氯甲烷)、或者它们中两种以上的混合溶剂。
通过这样的提取操作,从原材料提取出有效成分溶入溶剂。含有提取物的溶剂可以直接使用,也可以静置数日使其熟化后使用。可以进一步实施灭菌、清洗、过滤、脱色、除臭等惯用的纯化处理后使用。另外,也可以根据需要进行浓缩或者稀释后使用。另外,可以使溶剂完全挥发,成为固体状(干燥物)后使用,也可以将该干燥物再次溶解于任意溶剂中使用。
作为将D-泛醇应用于皮肤的另一方式,可列举出将D-泛醇和美白化合物组合的应用方法。作为美白化合物的例子,优选可列举出4-烷基间苯二酚、由下述通式(1)表示的化合物、由下述通式(2)表示的化合物、由下述通式(3)表示的化合物、乌索酸磷酸酯及其盐等。需要说明的是,只要没有特别记载,针对存在光学异构体的化合物而言,L体、D体以及外消旋体(DL体)的任一种均包括于本发明。
对于在此所述的盐,只要是用于皮肤外用剂,就可以没有特别限定地使用。例如优选例示出钠、钾等碱金属盐;钙、镁等碱土金属盐;铵盐、三乙胺、三乙醇胺等有机胺盐;赖氨酸、精氨酸等碱性氨基酸盐等。这些盐中,尤其优选碱金属,其中尤其优选钠盐。
对于4-烷基间苯二酚,参照WO2007/148472。4-烷基间苯二酚的烷基优选具有3~10个碳原子的烷基,其中优选具有3~6个碳原子的烷基。具体而言,可例示出正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、戊基、正己基、环己基、辛基、异辛基等。在本发明的方法中,尤其优选使用4-正丁基间苯二酚。
所述通式(1)中,A1、A2、A3独立地表示可具有取代基的苯基。所述取代基选自羟基、具有1~4个碳原子的烷基以及具有1~4碳原子的烷氧基。X为氮原子或者氧原子。
所述通式(1)中,-X-R1由下述通式(4)表示。
所述通式(4)中,X1为氮原子。R2和R3相互键合,与X1一起形成具有2~8个碳原子且可具有取代基的杂环或者烃环。需要说明的是,在此碳原子数被定义为实际的碳原子数。在杂环或者烃环具有取代基的情况下,该取代基优选选自具有1~4个碳原子的烷基、具有1~4个碳原子的烷氧基、羟基、氨基以及氧代。在此,所述杂环包括芳香族杂环、非芳香族不饱和杂环、饱和杂环中的任一种。杂环优选为饱和杂环。另外,杂环的碳原子数优选为3~5、更优选为4~5。
另外,烃环包括芳香族烃环、非芳香族不饱和烃环以及环烷基环中的任一种。
更详细而言,对于所述通式(1)中的-X-R1由所述通式(4)表示的化合物,参照WO2010/074052。作为优选例,列举出下述的化合物1~12。
另外,所述通式(1)中,-X-R1由下述通式(5)表示。
通式(5)中,X2为氮原子或者氧原子。
n为1~5的整数。n优选为1~3的整数。
Y为羟基或者氨基。
当Y为氨基时,X2优选为氧原子。
通式(5)中,当X2为氮原子时,R4存在且表示氢原子。当X2为氧原子时,R4不存在。
更详细而言,对于所述通式(1)中的-X-R1由所述通式(5)表示的化合物,参照WO2010/074052。
作为优选例,列举出以下的化合物13~22。
另外,所述通式(1)中,-X-R1由下述通式(6)表示。
——X3-Hp (6)
通式(6)中,X3为氧原子或者氮原子。
通式(6)中,p的数量与X3相对应。
更详细而言,对于通式(1)中的-X-R1由通式(6)表示的化合物,参照WO2010/074052。
作为优选化合物的例子,可列举出以下的化合物23~29。
所述通式(2)中,R’1表示未取代的或者具有取代基的芳香族基团,该取代基为具有1~4个碳原子的直链或支链的烷基、具有1~4个碳原子的直链或支链的烷氧基、卤素原子或者具有1~4个碳原子的卤代烷基,该芳香族基团为苯基、萘基或者联苯基。
R’2表示氢原子、具有1~4个碳原子的直链或支链的烷基、或者具有1~3个碳原子的直链或支链的烷酰基。
R’3表示氢原子或者具有1~4碳原子的直链或支链的烷基。
更详细而言,对于由所述通式(2)表示的化合物,参照WO2011/074643。
作为优选化合物的例子,可列举出以下的化合物30~44。
在所述通式(3)中,R”1表示-SH、-SO3H、-S-S-X1、-S-X2、-SO-X3或者-SO2-X4,所述X1~X4独立地表示氢原子或者具有1~8个碳原子的脂肪族烃基。R”2表示具有5~12个碳原子且未取代或者可具有取代基的芳香族基团,所述芳香族基团优选为苯基。n表示1或者2的整数。所述取代基优选为具有1~4碳原子的烷基、具有1~4个碳原子的烷氧基或者苯基。
更详细而言,对于由所述通式(3)表示的化合物,参照WO2010/058730。
优选具体例为以下的化合物45~52。
乌索酸磷酸酯由下述式表示。详细参照WO2006/132033。
以美白效果作为目的,在将所述4-烷基间苯二酚、由通式(1)、(2)或(3)表示的化合物及其盐配混于皮肤外用剂的情况下,所述4-烷基间苯二酚、由通式(1)、(2)或(3)表示的化合物、乌索酸磷酸酯及其盐可以仅包含一种,也可以包含两种以上。
皮肤外用剂中所含的所述4-烷基间苯二酚、由通式(1)、(2)或(3)表示的化合物及其盐的含量,优选为相对于皮肤外用剂总量的0.001~10质量%,进一步优选为0.01~5质量%,更优选为0.1~3质量%。
针对以美白效果为目的,将所述4-烷基间苯二酚、由通式(1)、(2)或(3)表示的化合物、乌索酸磷酸酯及其盐与D-泛醇组合,应用于皮肤的方法,依据将前述具有黑色素生成抑制作用的植物提取物与D-泛醇应用于皮肤的情况。
<实验3:具有黑色素生成抑制作用的植物提取物或现有美白化合物与D-泛醇的组合产生的协同效果的确认>
为了确认D-泛醇与上述具有黑色素生成抑制作用的植物提取物组合产生的协同效果,以及为了确认D-泛醇与美白化合物的组合产生的协同效果,进行与所述<实验1:黑色素生成抑制实验>和<实验2:角化细胞的细胞生长实验>相同的实验。另外,将0mM和0μM的D-泛醇同样地用于对照,但是将<实验1>的1mM的D-泛醇分别替换为以下的试样(1)~(3)实施。
试样(1):1mM的D-泛醇
试样(2):选自表1记载的植物提取物(提取物1~50)的一种的1%,或选自现有美白化合物的一种的0.1μg/mL
试样(3):所述试样(1)和试样(2)的各组合。
另外,<实验2>的15μM和150μM的D-泛醇分别替换为上述试样(1)~(3)实施。结果在表2中示出。需要说明的是,表2中黑色素量(%)和细胞生长率(%)与实验1和实验2记载的相同,均为相对于对照的比率。
需要说明的是,在此使用的现有美白化合物为“4-正丁基间苯二酚”、“乌索酸磷酸酯”、所述化合物1、31和45。
需要说明的是,在本实验中,化合物1使用通过WO2010/074052记载的方法合成的1-(三苯基甲基)咪唑。化合物31使用通过WO2011/074643记载的方法合成的N-苯甲酰基-L-丝氨酸。化合物45使用通过WO2010/058730记载的方法制成的N-(甲苯甲酰基)甲硫氨酸。后述<美白速度>也相同。
[表1]
表1
[表2]
表2
根据上述结果可知,通过将植物提取物1~35、化合物1、31、45、4-正丁基间苯二酚、或乌索酸磷酸酯与D-泛醇组合使用,能得到黑色素生成抑制和角化细胞的细胞生长作用的协同效果。另外,可知通过将D-泛醇与植物提取物36~40组合使用,能得到角化细胞的细胞生长作用的协同效果,通过将D-泛醇与植物提取物41~45组合使用,能得到黑色素生成抑制的协同效果。
尤其,在实现黑色素生成抑制和角化细胞的细胞生长作用的协同效果的情况下,认为可以进一步增进D-泛醇的代谢促进功能,即黑色素排出促进功能,可以期待进一步加速色素沉积皮肤的美白速度。
对于配混有D-泛醇的美白化妆品,在进行化妆品的制备时,可以使其含有通常化妆品使用的成分。另外,对于其剂型并没有任何限定。以下,针对用于美白化妆品时,可以使美白化妆品中含有的成分进行说明。
作为有效成分,可列举出D-泛醇以外的美白成分、抗皱成分、泛醇以外的消炎成分、源自动植物的提取物等。在D-泛醇用于有效成分的情况下,可以含有两种以上的有效成分。
作为美白成分,只要是通常用于化妆品的成分,就没有特别限定。例如,可列举出4-正丁基间苯二酚、抗坏血酸葡萄糖苷、维生素C乙基醚、凝血酸、熊果苷、1-三苯基甲基哌啶、1-三苯基甲基吡咯烷、2-(三苯基甲基氧)乙醇、2-(三苯基甲基氨基)乙醇、2-(三苯基甲基氧)乙胺、三苯基甲胺、三苯基甲醇、三苯基甲烷以及氨基二苯基甲烷、N-(对甲苯甲酰基)半胱氨酸、N-(对甲氧基苯甲酰)半胱氨酸等。另外,作为其他美白成分,可列举出N-苯甲酰-丝氨酸、N-(对甲基苯甲酰)丝氨酸、N-(对乙基苯甲酰)丝氨酸、N-(对甲氧基苯甲酰)丝氨酸、N-(对氟苯甲酰)丝氨酸、N-(对三氟甲基苯甲酰)丝氨酸、N-(2-萘甲酰基)丝氨酸、N-(4-苯基苯甲酰)丝氨酸、N-(对甲基苯甲酰)丝氨酸甲基酯、N-(对甲基苯甲酰)丝氨酸乙基酯、N-(2-萘甲酰基)丝氨酸甲基酯、N-苯甲酰-O-甲基丝氨酸、N-(对甲基苯甲酰)-O-甲基丝氨酸、N-(对甲基苯甲酰)-O-乙酰丝氨酸、N-(2-萘甲酰基)-O-甲基丝氨酸等。
这些美白成分既可以为市售品,也可以通过合成得到。
美白化妆品的美白成分的含量通常为0.01~30质量%,优选为0.1~10质量%,更优选为1~5质量%。
作为抗皱成分,只要是通常用于化妆品的成分,就没有特别限定。例如可列举出,作为维生素A或其衍生物的视黄醇、视黄醛、视黄酸、维甲酸、异维甲酸、生育酚视黄酸酯、视黄醇棕榈酸酯、视黄醇乙酸酯、乌索酸苄基酯、乌索酸磷酸酯、桦木酸苄基酯、苄基酸磷酸酯。化妆品中抗皱成分的含量通常为0.01~30质量%,优选为0.1~10质量%,更优选为1~5质量%。
作为源自动植物的提取物,只要是通常用于医药品、化妆品、食品等的提取物,就没有特别限定。例如,优选可列举出:木通茎提取物、罗汉柏提取物、石刁柏茎提取物、鳄梨提取液、土常山提取物、巴旦杏提取物、山金车花提取物、芦荟提取物、野樱梅提取物、杏子提取物、銀杏提取物、印度吉纳树提取物、茴香提取物、土当归提取物、野蔷薇果提取物、刺五加提取物、延命草提取物、黄芩提取物、黄蘗提取物、黄莲提取物、御种人参提取物、贯叶连翘提取物、野芝麻提取物、橙提取物、火棘提取物、葛根提取物、洋甘菊提取物、胡萝卜提取物、茵陈蒿花提取物、甘草提取物、猕猴桃提取液、黄瓜提取物、番石榴提取物、苦参根提取物、山栀子提取物、山白竹提取物、苦参提取物、胡桃提取物、葡萄柚提取物、黑米提取物、小球藻提取物、桑白皮提取物、白花油麻藤茎提取物、月桃叶提取物、龙胆根提取物、牻牛儿苗提取物、红茶提取物、牛蒡提取物、稻米提取物、稻米发酵提取物、米糠发酵提取物、稻米胚芽油、越橘提取物、洋苏提取物、肥皂草提取物、细竹提取物、山楂提取物、芫荽提取物、山椒提取物、香菇提取物、地黄提取物、紫草根提取液、紫苏提取物、椴树提取物、榆绣线菊花提取物、芍药提取物、姜根提取物,菖蒲根提取物、白桦提取物、杉菜提取物、甜叶菊提取物、甜叶菊发酵物、洋常春藤提取物、西洋山楂提取物、西洋接骨木提取物、欧蓍草提取物、西洋薄荷提取物、鼠尾草提取物、锦葵提取物、川芎提取物、当药提取物、桑根皮提取物、大黄提取物、大豆提取物、大枣提取物,欧百里香提取物、蒲公英提取物、茶提取物、丁香提取物、温州蜜桔果皮提取物、甜茶提取物、辣椒提取物、当归提取物、金盏花提取物、桃仁提取物、橙皮提取物、蕺菜提取物、番茄提取物、纳豆提取物、人参提取物、大蒜提取物、野蔷薇提取物、朱槿提取物、麦门冬提取物、莲提取物、荷兰芹提取物、桦树提取物、北美金缕梅提取物、毛叶香茶菜提取物、丝柏提取物、枇杷提取物、款冬提取物、蜂斗菜提取物、茯苓提取物、假叶树提取物、葡萄提取物、葡萄种子提取物、丝瓜提取物、红花提取液、薄荷提取物、阔叶椴提取物,牡丹根提取物、忽布提取物、松提取物、马郁兰提取物、欧洲七叶树提取物、观音莲提取物、无患子提取物、香蜂花提取物、海蕴提取物、桃提取物、蓝芙蓉提取物、有加利树提取物、虎耳草提取物、柚子提取物、白花百合鳞茎提取物、薏苡仁提取物、艾蒿提取物、薰衣草提取物、绿茶提取物、苹果提取物、路易波士茶提取物、灵芝提取物、莴苣叶提取物、柠檬提取物、连翘提取物、紫云英提取物、蔷薇提取物、迷迭香提取物、白花春黄菊花提取物、蜂王浆提取物、地榆提取物等提取物。
化妆品中源自动植物的提取物的含量通常为0.01~30质量%,优选为0.1~10质量%,更优选为1~5质量%。
作为消炎成分,可列举出苦参黄素、光甘草定、甘草酸、甘草次酸等,优选为甘草酸及其盐、甘草次酸烷基及其盐以及甘草次酸及其盐。
化妆品中的消炎成分的含量通常为0.01~30质量%,优选为0.1~10质量%,更优选为1~5质量%。
作为油性成分,可列举出极性油、挥发性烃油等。
作为极性油,可列举出作为合成酯油的肉豆蔻酸异丙酯、辛酸十六烷基酯、肉豆蔻酸辛基十二烷基酯、棕榈酸异丙酯、硬脂酸丁酯、月桂酸己酯、肉豆蔻酸肉豆蔻酯、油酸癸酯、二甲基辛酸己基癸酯、乳酸十六烷酯、乳酸肉豆蔻酯、乙酸羊毛脂酯、硬脂酸异十六烷基酯、异硬脂酸异十六烷基酯、12-羟基硬脂酸胆固醇酯、二-2-乙基己酸乙二醇酯、二季戊四醇脂肪酸酯、单异硬脂酸N-烷基乙二醇酯、二癸酸新戊二醇酯、苹果酸二异硬脂基酯、二-2-庚基十一烷酸甘油酯、三羟甲基丙烷三(2-乙基己酸)酯、三羟甲基丙烷三异硬脂酸酯、四-2-乙基己酸季戊四醇酯、三-2-乙基己酸甘油酯、三羟甲基丙烷三异硬脂酸酯。
另外,还可以列举出:十六烷基-2-乙基己酸酯、2-乙基己基椋榈酸酯、三肉豆蔻酸甘油酯、三-2-庚基十一烷酸甘油酯、蓖麻油脂肪酸甲酯、油酸油酯、十八十六醇、乙酰甘油酯、棕榈酸2-庚基十一烷酯、己二酸二异丁酯、N-月桂酰基-L-谷氨酸-2-辛基十二烷酯、己二酸二-2-庚基十一烷酯、月桂酸乙酯、癸二酸二-2-乙基己酯、肉豆蔻酸2-己基癸酯、棕榈酸2-己基癸酯、己二酸2-己基癸酯、癸二酸二异丙酯,琥珀酸2-乙基己酯、乙酸乙酯、乙酸丁酯、乙酸戊酯、柠檬酸三乙酯、甲氧基肉桂酸乙基己酯等。
另外,可列举出作为天然油的鳄梨油、山茶油、海龟油、夏威夷果油、玉米油、貂油、橄榄油、菜籽油、蛋黄油、芝麻油、杏仁油、小麦胚芽油、山茶花油、蓖麻油、亚麻子油、红花油、棉籽油、紫苏子油、大豆油、花生油、茶籽油、椰子油、米糠油、中国桐油,日本桐油、霍霍巴油、胚芽油、三甘油、三辛酸甘油酯、三异棕榈酸甘油酯等。
作为挥发性烃油,可列举出异十二烷、异十六烷等。
作为表面活性剂,可列举出:脂肪酸皂(月桂酸钠、棕榈酸钠等)、月桂基硫酸钾、烷基醚硫酸三乙醇胺等阴离子表面活性剂类;氯化硬脂基三曱基铵、苯扎氯铵、月桂基氧化胺等阳离子表面活性剂类;
甜菜碱系表面活性剂(烷基甜菜碱、酰氨基甜菜碱、磺基甜菜碱等)、咪唑啉系两性表面活性剂(2-椰油基-2-氢氧化咪唑啉鎓-1-羧基乙氧基2钠盐等)、酰基甲基牛磺酸等两性表面活性剂类;
脱水山梨糖醇脂肪酸酯类(脱水山梨糖醇单硬脂酸酯、脱水山梨糖醇倍半油酸酯等)、甘油脂肪酸类(单硬脂酸甘油等)、丙二醇脂肪酸酯类(单硬脂酸丙二醇等)、氢化蓖麻油衍生物、甘油烷基醚、POE脱水山梨糖醇脂肪酸酯类(POE脱水山梨糖醇单油酸酯、聚氧乙烯脱水山梨糖醇单硬脂酸酯等)、POE山梨糖醇脂肪酸酯类(POE-山梨糖醇单月桂酸酯等)、POE甘油脂肪酸酯类(POE-甘油单异硬脂酸酯等)、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),PLURONIC型类、POE·POP烷基醚类(POE·POP2-癸基十四烷基醚等)、TETRONIC类、POE蓖麻油/氢化蓖麻油衍生物(POE蓖麻油、POE氢化蓖麻油等)、蔗糖脂肪酸酯、烷基葡糖苷等非离子表面活性剂类等。
作为多元醇,可列举出:聚乙二醇、丙三醇、1,3-丁二醇、赤藻糖醇、山梨糖醇、木糖醇、麦芽糖醇、丙二醇、二丙二醇、二丙三醇、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。
作为增稠剂,可列举出:瓜尔豆胶、榅桲籽、卡拉胶,半乳聚糖、阿拉伯胶、果胶、甘露聚糖、淀粉、黄原胶、凝胶多糖、甲基纤维素、羟乙基纤维素、羧甲基纤维素、甲基羟基丙基纤维素、硫酸软骨素、硫酸皮肤素、糖原、硫酸乙酰肝素、透明质酸、透明质酸钠、黄蓍胶、硫酸角质素、软骨素、硫酸粘多糖、羟基乙基瓜尔豆胶、羧基甲基瓜尔豆胶、葡聚糖、硫酸角质、刺槐豆胶、琥珀酰聚糖、卡洛宁酸、甲壳质、几丁聚糖、羧基甲基甲壳质、琼脂、聚乙烯醇、聚乙烯吡咯烷酮、羧基乙烯基聚合物、烷基改性羧基乙烯基聚合物、聚丙烯酸钠、聚乙二醇、膨润土等。
作为粉体类,可列举出:能实施表面处理的云母、滑石、高岭土、合成云母、碳酸钙、碳酸镁、硅酸酐(二氧化硅)、氧化铝、硫酸钡等粉体类;能实施表面处理的氧化铁红、铁的黄色氧化物、铁的黑色氧化物、氧化钴、群青、普鲁士蓝、氧化钛、氧化锌的无机颜料类;能实施表面处理的云母钛、鱼鳞箔、氯氧化铋等珠光剂类;能被色淀的红色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。
作为紫外线吸收剂,可列举出:对氨基苯甲酸系紫外线吸收剂、邻氨基苯甲酸系紫外线吸收剂、水杨酸系紫外线吸收剂、肉桂酸系紫外线吸收剂、二苯甲酮系紫外线吸收剂、糖系紫外线吸收剂、2-(2’-羟基-5-叔辛基苯基)苯并三唑、4-甲氧基-4’-叔丁基二苯甲酰基甲烷等紫外线吸收剂类等。
另外,美白化妆品的制造方法并未特别限定,可以根据所应用的美白化妆品的剂型,适当使用已知方法进行制造。用于美白化妆品时的剂型,可以使用如通常已知的化妆水剂型、乳液剂型、精华液剂型、霜剂型、粉末剂型的任一种。
实施例
以下,列举具体的实验例,进一步详细地说明本发明,但本发明不仅限于以下的方式。
<实施例1至4>
制备以下表3至6所示配方的美白化妆品1至4。
[表3]
表3:实施例1(化妆水)(质量份)
(制备方法)配合(A)的各成分,在室温下溶解。另外,使(B)的各成分也在室温下溶解,并添加至(A)配方中使其可溶,得到美白化妆品1。
[表4]
表4:实施例2(乳液)(质量份)
(制备方法)配合(A)的各成分,加热混合至70℃。配合(B)的各成分,加热混合至70℃,并添加至(A)配方中使其乳化,边冷却边添加(C),得到美白化妆品2。
[表5]
表5:实施例3(护手霜)(质量份)
(制备方法)利用与实施例2同样的方法,得到美白化妆品3。
[表6]
表6:实施例4(霜)(质量份)
(制备方法)配合(A)的各成分,加热至80℃。配合(B)的各成分,加热至80℃。边搅拌(A)的混合物,边添加(B)的混合物,进行搅拌使其乳化,之后进行冷却,由此得到美白化妆品4。
<美白评价>
将实施例1的配方中的“D-泛醇”分别置换成“水”、置换成配混浓度达到1%的作为现有美白成分的“2-羟基-2’-羟基-5,5’-二丙基-1,1’-联苯”、以及置换成配混浓度达到2%的“腺苷一磷酸二钠”,分别作为比较化妆品1至3,使用与实施例1记载的方法相同的方法,制造比较化妆品1至3。针对美白化妆品1以及比较化妆品1至3,按以下步骤对色素沉积抑制作用进行评价。
在自愿参加的受试者的上臂内侧部设置1.5cm×1.5cm的部位共四处。向所设置的部位照射最小红斑量(1MED)的紫外线1天1次,连续3天照射3次。从试验第1天的紫外线照射结束时(第1天照射结束后)开始,1天2次且连续21天日涂抹50μL美白化妆品1、比较化妆品1至3。第21天的涂抹结束24小时后,使用色差计(CR-300、柯尼卡美能达株式会社)对各试验部位的皮肤亮度(L*值)进行测定,计算出比较化妆品1(对照)的涂抹部位的L*值与美白化妆品1、比较化妆品2或3的涂抹部位的L*值之差(ΔL*值=美白化妆品1(比较化妆品2或3)涂抹部位的L*值-比较化妆品1涂抹部位L*值)。L*值在色素沉积的程度越强时值越低。因此,可以判断为ΔL*值越大,越改善色素沉积。计算出的ΔL*值为0.4以上则判定为A,不足0.4则判定为B。结果在表7中示出。
[表7]
表7
根据表7的结果,可知本发明的美白化妆品1具有强于比较化妆品2和比较化妆品3的色素沉积抑制作用,这样本发明的美白化妆品1示出优异的美白效果(色素沉积改善效果)。这是由本发明的美白化妆品1中含有的黑色素生成抑制剂(D-泛醇)所产生的美白效果。另外,本发明的黑色素生成抑制剂除了黑色素生成抑制作用以外,还具有角化细胞的细胞生长作用,因此可以理解为与现有的美白剂相比,能实现更高的美白效果。
<参考例1至64(美白化妆品5至68)>
制备以下表8所示配方的美白化妆品5。另外,使该配方中(A)中进一步含有相对于化妆品总量浓度为1.0质量%的表1所示的植物提取物,制备美白化妆品5至55。另外,制备将该植物提取物置换为“4-正丁基间苯二酚”、“乌索酸磷酸酯”、“2-羟基-2’-羟基-5,5’-二丙基-1,1’-联苯”、“腺苷一磷酸二钠”、所述化合物1、2、13、30、31、33、45、47或49的美白化妆品56至68。需要说明的是,“4-正丁基间苯二酚”、“乌索酸磷酸酯”、所述化合物1、2、13、30、31、33、45、47和49的浓度相对于化妆品总量为0.1质量%,“2-羟基-2’-羟基-5,5’-二丙基-1,1’-联苯”、“腺苷一磷酸二钠”的浓度相对于化妆品总量为1.0质量%。
需要说明的是,在本实验中,化合物2使用通过WO2010/074052记载的方法合成的1-(三苯基甲基)哌啶,化合物13使用通过同一文献记载的方法合成的2-(三苯基甲氧基)乙醇。化合物30使用通过WO2011/074643记载的方法合成的N-(对甲基苯甲酰基)-L-丝氨酸,化合物33使用通过同一文献记载的方法合成的N-(对甲氧基苯甲酰基)-L-丝氨酸。化合物47使用通过WO2010/058730记载的方法合成的N-(甲苯甲酰基)半胱氨酸,化合物49使用通过同一文献记载的方法合成的N-(4-甲氧基苯甲酰)-L-半胱氨酸。化合物1、31和45与所述<实验3>相同。
美白化妆品5至68均使用与化妆品1相同的制备法得到,即配合(A)的各成分,在室温下溶解,另外,使(B)的各成分也在室温下溶解,并添加至(A)配方中使其可溶。
[表8]
表8:美白化妆品5(化妆水)(质量份)
<美白速度的评价>
针对上述美白化妆品5至68,按以下步骤对美白速度进行评价。将上述化妆品5的配方中的D-泛醇置换成水,与化妆品5同样地制备比较化妆品4。
在自愿参加的受试者的左右上臂内侧部设置1.0cm×1.0cm的部位共八处。向所设置的部位照射最少红斑量(1MED)的紫外线1天1次,连续3天照射3次。从试验第1天的紫外线照射结束时(第一天照射结束后)开始,1天2次且连续21天涂抹50μL美白化妆品5至68、以及比较化妆品4。每天涂抹第2次结束24小时后,使用色差计(CR-300、柯尼卡美能达株式会社)对各试验部位的皮肤明度(L*值)进行测定,计算出比较化妆品4的涂抹部位的L*值与美白化妆品5至68的涂抹部位的L*值之差(ΔL*值=美白化妆品5(美白化妆品6至68)涂抹部位的L*值-比较化妆品4涂抹部位L*值)。L*值在色素沉积的程度越强时值越低。因此,可以判断为ΔL*值越大,越改善色素沉积。在表9至19中示出计算出的ΔL*值为0.4时所需的天数、以及第21天的涂抹结束24小时后测定计算出的ΔL*值。
另外,以计算出将所述化妆品6至68中的美白成分D-泛醇除去、即美白成分只为所述各植物提取物或现有美白化合物时的ΔL*值和ΔL*值为0.4时所需的天数为目的,使用与化妆品5相同的方法分别制备将所述化妆品6至68的配方中的D-泛醇置换为水的化妆品6’至68’。接着,利用与所述<美白速度的变化>相同的方法,将比较化妆品4用作对照,求出ΔL*值为0.4时所需的天数,以及第21天的涂抹结束24小时后测定的L*值和ΔL*值。在表9至19中以“无D-泛醇的ΔL*值”作为第21天的涂抹结束24小时后测定计算出的ΔL*值示出。另外,ΔL*值为0.4时所需的天数均超过21天。
[表9]
表9
[表10]
表10
[表11]
表11
[表12]
表12
[表13]
表13
[表14]
表14
[表15]
表15
[表16]
表16
[表17]
表17
[表18]
表18
[表19]
表19
根据表9至19的结果,可以理解为通过将D-泛醇与特定的植物提取物或者特定的现有美白化合物组合,并且适用于皮肤,能够更迅速地获得美白效果。可以认为这是由于D-泛醇具有的不仅能够抑制黑色素的生成,而且能够促进黑色素的排出的这两种作用机理所产生的美白作用的原因。
Claims (7)
1.一种由D-泛醇构成的黑色素生成抑制剂。
2.一种美白化妆品,其含有权利要求1所述的黑色素生成抑制剂、以及选自以下美白剂(A)~(G)的1种以上,
(A)选自由茜草科钩藤提取物、毛叶香茶菜提取物、狭叶松果菊叶提取物、紫草根提取液、红花提取液、鳄梨提取液、秋葵提取液、猕猴桃提取液、艳山姜叶提取物、肥皂草提取物、金银花提取物、茶提取物、冬瓜子提取物、大蒜提取物、青柠果汁提取物、纳豆提取物、橙提取物、缬草提取物、黄瓜提取物、杏仁提取物、山栀子提取物、葡萄柚提取物、牛蒡提取物、红茶提取物、杉菜提取物、锦葵提取物、大枣提取物、番茄提取物、人参提取物、茯苓提取物、白花百合鳞茎提取物、灵芝提取物、莴苣叶提取物、柠檬提取物及蜂王浆提取物构成的组的1种或者2种以上的具有黑色素生成抑制作用的植物提取物
(B)4-烷基间苯二酚
(C)由下述通式(1)表示的化合物
(D)由下述通式(2)表示的化合物
(E)由下述通式(3)表示的化合物
(F)乌索酸磷酸酯
(G)所述(B)~(F)的盐,
其中,
通式(1)中,A1、A2、A3独立地表示可具有取代基的苯基,所述取代基选自羟基、具有1~4个碳原子的烷基以及具有1~4碳原子的烷氧基,X为氮原子或者氧原子,
-X-R1由下述通式(4)、(5)或者(6)表示,
通式(2)中,R’1表示未取代的或者具有取代基的芳香族基团,该取代基为具有1~4个碳原子的直链或支链的烷基、具有1~4个碳原子的直链或支链的烷氧基、卤素原子或者具有1~4个碳原子的卤代烷基,该芳香族基团为苯基、萘基或者联苯基,
R’2表示氢原子、具有1~4个碳原子的直链或支链的烷基、或者具有1~3个碳原子的直链或支链的烷酰基,
R’3表示氢原子或者具有1~4碳原子的直链或支链的烷基,
通式(3)中,R”1表示-SH、-SO3H、-S-S-X1、-S-X2、-SO-X3或者-SO2-X4,所述X1~X4独立地表示氢原子或者具有1~8个碳原子的脂肪族烃基R”2表示具有5~12个碳原子且未取代或者可具有取代基的芳香族基团,所述芳香族基团优选为苯基,n表示1或者2的整数,所述取代基为具有1~4碳原子的烷基、具有1~4个碳原子的烷氧基或者苯基,
通式(4)中,X1为氮原子,R2和R3相互键合,与X1一起形成具有2~8个碳原子且可具有取代基的杂环或者烃环,所述取代基选自具有1~4个碳原子的烷基、具有1~4个碳原子的烷氧基、羟基、氨基以及氧代,所述杂环的碳原子数为3~5,
通式(5)中,X2为氮原子或者氧原子,n为1~5的整数,n优选为1~3的整数,Y为羟基或者氨基,当X2为氮原子时,R4存在且表示氢原子,当X2为氧原子时,R4不存在,
-X3-Hp (6)
通式(6)中,X3为氧原子或者氮原子,在通式(6)中,p为与X3相应的数量。
3.根据权利要求2所述的方法,其特征在于,
所述植物提取物为选自茜草科钩藤提取物、毛叶香茶菜提取物、狭叶松果菊叶提取物、紫草根提取液及红花提取液的1种或者2种以上。
4.根据权利要求2所述的方法,其特征在于,
由所述通式(1)表示的化合物包含选自下述化合物1~29的1种以上。
5.根据权利要求2所述的方法,其特征在于,
由所述通式(2)表示的化合物包含选自下述化合物30~44的1种以上。
6.根据权利要求2所述的方法,其特征在于,
由所述通式(3)表示的化合物包含选自下述化合物45~52的1种以上。
7.一种美白方法,其包括使权利要求1所述的黑色素生成抑制剂与皮肤接触,对皮肤进行美白的工序;以及使选自以下美白剂(A)~(G)的1种以上与皮肤接触,对皮肤进行美白的工序。
(A)选自由茜草科钩藤提取物、毛叶香茶菜提取物、狭叶松果菊叶提取物、紫草根提取液、红花提取液、鳄梨提取液、秋葵提取液、猕猴桃提取液、艳山姜叶提取物、肥皂草提取物、金银花提取物、茶提取物、冬瓜子提取物、大蒜提取物、青柠果汁提取物、纳豆提取物、橙提取物、缬草提取物、黄瓜提取物、杏仁提取物、山栀子提取物、葡萄柚提取物、牛蒡提取物、红茶提取物、杉菜提取物、锦葵提取物、大枣提取物、番茄提取物、人参提取物、茯苓提取物、白花百合鳞茎提取物、灵芝提取物、莴苣叶提取物、柠檬提取物及蜂王浆提取物构成的组的1种或者2种以上的具有黑色素生成抑制作用的植物提取物
(B)4-烷基间苯二酚
(C)由下述通式(1)表示的化合物
(D)由下述通式(2)表示的化合物
(E)由下述通式(3)表示的化合物
(F)乌索酸磷酸酯
(G)所述(B)~(F)的盐,
其中,
通式(1)中,A1、A2、A3独立地表示可具有取代基的苯基,所述取代基选自羟基、具有1~4个碳原子的烷基以及具有1~4碳原子的烷氧基,X为氮原子或者氧原子,
-X-R1由下述通式(4)、(5)或者(6)表示,
通式(2)中,R’1表示未取代的或者具有取代基的芳香族基团,该取代基为具有1~4个碳原子的直链或支链的烷基、具有1~4个碳原子的直链或支链的烷氧基、卤素原子或者具有1~4个碳原子的卤代烷基,该芳香族基团为苯基、萘基或者联苯基,
R’2表示氢原子、具有1~4个碳原子的直链或支链的烷基、或者具有1~3个碳原子的直链或支链的烷酰基,
R’3表示氢原子或者具有1~4碳原子的直链或支链的烷基,
通式(3)中,R”1表示-SH、-SO3H、-S-S-X1、-S-X2、-SO-X3或者-SO2-X4,所述X1~X4独立地表示氢原子或者具有1~8个碳原子的脂肪族烃基R”2表示具有5~12个碳原子且未取代或者可具有取代基的芳香族基团,所述芳香族基团优选为苯基,n表示1或者2的整数,所述取代基为具有1~4碳原子的烷基、具有1~4个碳原子的烷氧基或者苯基,
通式(4)中,X1为氮原子,R2和R3相互键合,与X1一起形成具有2~8个碳原子且可具有取代基的杂环或者烃环,所述取代基选自具有1~4个碳原子的烷基、具有1~4个碳原子的烷氧基、羟基、氨基以及氧代,所述杂环的碳原子数为3~5,
通式(5)中,X2为氮原子或者氧原子,n为1~5的整数,n优选为1~3的整数,Y为羟基或者氨基,当X2为氮原子时,R4存在且表示氢原子,当X2为氧原子时,R4不存在,
-X3-Hp (6)
通式(6)中,X3为氧原子或者氮原子,在通式(6)中,p为与X3相应的数量。
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