TWI548422B - Anti-inflammatory agents and melanin production inhibitors - Google Patents
Anti-inflammatory agents and melanin production inhibitors Download PDFInfo
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- TWI548422B TWI548422B TW103140197A TW103140197A TWI548422B TW I548422 B TWI548422 B TW I548422B TW 103140197 A TW103140197 A TW 103140197A TW 103140197 A TW103140197 A TW 103140197A TW I548422 B TWI548422 B TW I548422B
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- pentaerythritol
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- general formula
- alkyl
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Description
本發明係關於消炎劑、黑色素生成抑制劑及含有其之皮膚外用劑組成物。
若將皮膚暴露於紫外線下,則因此皮膚受到各種影響。此時皮膚內所生成之各種化學介質等引發炎症,對皮膚組織造成相當大之損傷,成為肌膚粗糙或色素沉澱、斑點、雀斑等症狀。又,代表性之化學介質有屬於花生油酸代謝物之前列腺素類或白三烯類、屬於細胞介素之一種的介白素類或腫瘤壞死因子-α等,其中,前列腺素E2(PGE2)已周知為代表性之炎症性介質。
以由紫外線等所引發之炎症的預防‧症狀改善為目的,已提案有例如,磷脂醯肌醇(L-α-glycero-phospho-D-myo-inositol)(專利文獻1)、百合科萱草屬植物或其之醱酵物(專利文獻2)等之消炎劑,此等調配而成之皮膚外用劑已上市。
另一方面,斑點、雀斑係黑生素之生成與排泄的平衡失調,於表皮過剩蓄積黑色素所致者。此等之原因有炎症、荷爾蒙之平衡、遺傳性要因等各種原因,但因為紫外線之影響而被助長。用於緩和已增加之色素沉澱者為美白劑。其中,作為應用於防止皮膚黑化或斑點、雀斑,並保持原本白色肌膚之美白化妝料者,已知有麴酸或抗壞血酸衍生物等。然而,由美白效果之程度或於製劑中之穩定性方面
而言,此等未必可滿足。
季戊四醇為糖醇之一種,工業上被利用作為松香酯原料或醇酸樹脂原料、合成潤滑劑原料等。迄今,已提案有含有季戊四醇之液狀化妝料(專利文獻3),且已知季戊四醇作為副溶劑或保濕劑的利用。
[專利文獻1]日本專利特開2009-269851號公報
[專利文獻2]日本專利特開2008-50326號公報
[專利文獻3]日本專利特開平6-48914號公報
本發明提供一種消炎劑組成物、PGE2產生抑制劑組成物、黑色素生成抑制劑組成物或美白劑組成物,其含有選自包含季戊四醇、下述一般式(1)所示之季戊四醇之烷基縮醛衍生物、及一般式(2)所示之季戊四醇之烷基縮醛衍生物之群組之1種或2種以上。
(式中,R1及R2可彼此相異,表示碳數1~4之烷基。)
(式中,R3~R6可彼此相異,表示碳數1~4之烷基。)
又,本發明提供一種消炎用、防止肌膚粗糙用、防日曬
用、美白用或膚色改善用的皮膚外用劑組成物,其含有選自包含季戊四醇、上述一般式(1)所示之季戊四醇之烷基縮醛衍生物、及一般式(2)所示之季戊四醇之烷基縮醛衍生物之群組之1種或2種以上。
又,本發明提供一種用於炎症之預防或治療、PGE2產生抑制或黑色素生成抑制的選自包含季戊四醇、上述一般式(1)所示之季戊四醇之烷基縮醛衍生物、及上述一般式(2)所示之季戊四醇之烷基縮醛衍生物之群組之1種或2種以上。
又,本發明提供一種選自包含季戊四醇、上述一般式(1)所示之季戊四醇之烷基縮醛衍生物、及上述一般式(2)所示之季戊四醇之烷基縮醛衍生物之群組之1種或2種以上作為消炎用、防止肌膚粗糙用、防日曬用、美白用或膚色改善用的皮膚外用劑組成物的使用。
又,本發明提供一種選自包含季戊四醇、上述一般式(1)所示之季戊四醇之烷基縮醛衍生物、及上述一般式(2)所示之季戊四醇之烷基縮醛衍生物之群組之1種或2種以上的化合物之使用,其係用於製造消炎劑組成物、PGE2產生抑制劑組成物、黑色素生成抑制劑組成物或美白劑組成物。
又,本發明提供一種選自包含季戊四醇、上述一般式(1)所示之季戊四醇之烷基縮醛衍生物、及上述一般式(2)所示之季戊四醇之烷基縮醛衍生物之群組之1種或2種以上的化合物用於製造消炎用、防止肌膚粗糙用、防日曬用、美白用或膚色改善用的皮膚外用劑組成物的使用。
又,本發明提供一種炎症之預防或治療、PGE2之產生抑制或黑色素之生成抑制的方法,其特徵為,投予選自包含季戊四醇、上述一般式(1)所示之季戊四醇之烷基縮醛衍生物、及上述一般式(2)所
示之季戊四醇之烷基縮醛衍生物之群組之1種或2種以上的有效量。
又,本發明提供一種防止肌膚粗糙、防日曬、美白或膚色改善用的方法,其特徵為,將選自包含季戊四醇、上述一般式(1)所示之季戊四醇之烷基縮醛衍生物、及上述一般式(2)所示之季戊四醇之烷基縮醛衍生物之群組之1種或2種以上的有效量應用於皮膚。
上述消炎劑之現狀為在長時間應用於肌膚時之安全性、或製劑安定性方面存在問題,且尚未出現於安全性、製劑安全性、及消炎效果之所有方面均獲得滿足者。又,亦期望有更加優越的黑色素生成抑制劑。
從而,本發明提供一種皮膚外用劑組成物,其可抑制因紫外線等之刺激所造成的炎症,預防因紫外線等所造成之肌膚粗糙、色素沉澱、斑點、雀斑等,且具有黑色素生成抑制作用。
本發明者等人有鑑於上述情況,經潛心研究之結果發現,季戊四醇及季戊四醇之烷基縮醛衍生物係對因紫外線等刺激所造成之表皮細胞中之PGE2產生增加具有優越的抑制效果,進而具有優越之黑色素生成抑制效果;又,發現此等調配而成之皮膚外用劑組成物可抑制因紫外線所造成之炎症,並發揮肌膚粗糙之預防或改善效果、色素沉澱‧斑點‧雀斑等之預防效果、進而黑色素生成抑制效果及美白效果,遂完成本發明。
本發明之季戊四醇及季戊四醇之烷基縮醛衍生物,係具有優越之PGE2產生抑制能力的優越之消炎劑,且為具有優越之黑色素
生成抑制作用的優越之白美劑。從而,季戊四醇及季戊四醇之烷基縮醛衍生物調配而成的皮膚外用劑組成物,係肌膚粗糙或因紫外線所造成之色素沉澱‧斑點‧雀斑等之預防或改善效果、美白效果、膚色改善效果優越者。
以下,針對本發明之構成進行詳述。
本發明之消炎劑、PGE2產生抑制劑、黑色素生成抑制劑、美白劑、及消炎用、防止肌膚粗糙用、防日曬用、美白用或膚色改善用的皮膚外用劑組成物(以下亦稱為本發明組成物),係含有選自包含季戊四醇及季戊四醇之烷基縮醛衍生物之群組之1種或2種以上者。
季戊四醇為由C(CH2OH)4之式所示的糖醇的1種。
季戊四醇之烷基縮醛衍生物係由下述一般式(1)或(2)所示者。
(式中,R1及R2可彼此相異,表示碳數1~4之烷基。)
(式中,R3~R6可彼此相異,表示碳數1~4之烷基。)
上述一般式(1)或(2)中,作為R1~R6所示之烷基,較佳為碳數1~3之烷基、更佳碳數1~2之烷基。具體而言,可列舉甲基、乙基、正丙基、異丙基,更佳為甲基、乙基、正丙基,進而更佳為甲基、
乙基。
作為式(1)所示之季戊四醇之烷基縮醛衍生物,可列舉單異亞丙基季戊四醇、單(1-甲基亞丙基)季戊四醇、單(1-甲基亞丁基)季戊四醇、單(1-乙基亞丙基)季戊四醇、單(1-乙基亞丁基)季戊四醇、單(1-丙基亞丁基)季戊四醇等。
作為式(2)所示之季戊四醇之烷基縮醛衍生物,可列舉二異亞丙基季戊四醇、二(1-甲基亞丙基)季戊四醇、二(1-甲基亞丁基)季戊四醇、二(1-乙基亞丙基)季戊四醇、二(1-乙基亞丁基)季戊四醇、二(1-丙基亞丁基)季戊四醇等。
本發明之一般式(1)、(2)所示之季戊四醇之烷基縮醛衍生物,可藉由公知方法由季戊四醇與烷基酮化合物所合成。
季戊四醇、一般式(1)所示之季戊四醇之烷基縮醛衍生物、及一般式(2)所示之季戊四醇之烷基縮醛衍生物(以下亦稱為季戊四醇類),係如後述實施例所示般,抑制表皮細胞之因花生油酸所造成之PGE2產生,亦抑制因紫外線照射所造成之PGE2產生。又,季戊四醇類係藉由應用至皮膚,而顯著抑制紫外線照射所產生之紅斑。再者,季戊四醇類具有優越之黑色素生成抑制作用及美白作用。
從而,季戊四醇、一般式(1)或(2)所示之季戊四醇之烷基縮醛衍生物係作為PGE2產生抑制劑組成物、消炎劑組成物、黑色素生成抑制劑組成物、美白劑組成物,進而消炎用、防止肌膚粗糙用、防日曬用、美白用或膚色改善用的皮膚外用劑組成物而有用。
本發明之皮膚外用劑組成物之消炎、防止肌膚粗糙及防日曬效果,主要為根據消炎效果,進而根據抑制起因於紫外線之炎症者。
從而,本發明之皮膚外用劑組成物對於因紫外線照射所產生之炎症、因日曬所造成之紅斑及起因於紫外線照射之色素沉澱、斑點、雀斑、肌膚粗糙之預防、改善效果優越。
又,本發明之皮膚外用劑組成物之美白效果及膚色改善效果,主要為根據黑色素生成抑制作用及美白作用。
於膚色改善,包括色斑及肌膚亮度之改善。
又,上述皮膚外用劑組成物係包括醫藥用外用劑組成物、醫藥部外品用外用劑組成物、及化妝料組成物。特佳係作為化妝料組成物而使用。
本發明之季戊四醇類的含量,係以上述組成物之總量為基準,較佳為0.001質量%以上、更佳為0.01質量%以上、進而較佳為0.1質量%以上、進而更佳為0.5質量%以上;且,較佳為20質量%以下、更佳為10質量%以下、進而較佳為8質量%以下、進而更佳為5質量%以下。季戊四醇類之含量的具體範圍,較佳為0.001~20質量%、更佳為0.01~15質量%、進而較佳為0.1~10質量%、進而更佳為0.1~8質量%、特佳為0.5~8質量%、最佳為0.5~5質量%。若為此範圍內,則可充分發揮PGE2產生抑制能力,得到優越的消炎效果、黑色素生成抑制作用、美白作用。
本發明之含有季戊四醇類的組成物,可依通常方法製造,例如可應用於乳液、乳霜、化妝水、精華液、面膜、洗臉劑等之基礎化妝料,口紅、粉底、粉底液、彩妝粉餅等之彩妝化妝料,洗髮精、潤髮乳、護髮乳、調理劑、染髮料、整髮料等之頭髮化妝料,洗臉劑、沐浴乳、肥皂等之清潔用化妝料,進而入浴劑等任一種形態,但當然亦不限定於此等。特佳係作為化妝水、乳液、乳霜、美溶液等
皮膚外用劑而應用於化妝料。
本發明之組成物係除了上述必須成分之外,視需要可依不損及本發明之效果之範圍使用一般所使用之任意成分。
在將季戊四醇類根據其黑色素生成抑制作用而調配於美白化妝料等之美白用外用劑的情況,由其黑色素生成抑制作用之強化或輔助的觀點而言,可將氫醌、熊果素、土耳其鞣酸、麴酸、維他命C及其衍生物(例如抗壞血酸葡萄糖苷、抗壞血酸磷酸酯鈉、抗壞血酸硫酸2鈉、抗壞血酸磷酸酯鎂、抗壞血酸異軟脂酸酯、抗壞血酸乙酯等)、及聯苯衍生物(例如去氫二甲酚、2,2'-二羥基-5,5'-二丙基聯苯等之黑色素生成抑制劑)、火棘萃取物、菊葉薯蕷(dioscorea composita)萃取物、接骨木萃取物、岩白菜萃取物、洋甘菊提取物、腺苷5'-1-磷酸或其鹽、亞麻油酸衍生物、維生素B3及其衍生物、傳明酸及傳明酸鹽、傳明酸衍生物、4-甲氧基水楊酸及其鹽等美白劑適當組合而使用。
於本發明之組成物中,除上述成分以外,亦可於不損害本發明目的之範圍內適當調配如下者:玻尿酸、多元醇、糖醇等保濕劑;焦油系色素、氧化鐵等著色顏料;對羥基苯甲酸酯等防腐劑;脂肪酸皂、鯨蠟基硫酸鈉等陰離子性界面活性劑;聚氧乙烯烷基醚、聚氧乙烯脂肪酸酯、聚氧乙烯多元醇脂肪酸酯、聚氧乙烯氫化蓖麻油、多元醇脂肪酸酯、聚甘油脂肪酸酯等非離子性界面活性劑;四烷基銨鹽等陽離子性界面活性劑;甜菜鹼型、磺基甜菜鹼型、磺基胺基酸型、N-硬脂醯基-L-麩胺酸鈉等雙離子性界面活性劑;卵磷脂、溶血磷脂醯膽鹼等天然系界面活性劑;明膠、酪蛋白、澱粉、阿拉伯膠、刺梧桐樹膠、瓜爾膠、刺槐豆膠、黃蓍膠、榲桲籽膠、果膠、鹿角菜膠、海藻酸鈉等天然高分子;甲基纖維素、羥乙基纖維素、羥丙基纖維素、
羧甲基纖維素鈉、乙基纖維素等半合成高分子;聚乙烯醇、聚乙烯甲醚及其共聚物、聚乙烯吡咯啶酮、聚丙烯酸鈉、羧乙烯聚合物、聚環氧乙烷聚合物等合成高分子;三仙膠等增黏劑;氧化鈦等顏料;二丁基羥基甲苯等抗氧化劑等。
關於上述實施形態,本發明進一步揭示以下實施態樣。
<1>一種消炎劑組成物、PGE2產生抑制劑組成物、黑色素生成抑制劑組成物或美白劑組成物,其含有選自包含季戊四醇、下述一般式(1)所示之季戊四醇之烷基縮醛衍生物、及下述一般式(2)所示之季戊四醇之烷基縮醛衍生物之群組之1種或2種以上。
(式中,R1及R2可彼此相異,表示碳數1~4之烷基。)
(式中,R3~R6可彼此相異,表示碳數1~4之烷基。)
<2>一種消炎用、防止肌膚粗糙用、防日曬用、美白用或膚色改善用的皮膚外用劑組成物,其含有選自包含季戊四醇、下述一般式(1)所示之季戊四醇之烷基縮醛衍生物、及下述一般式(2)所示之季戊四醇之
烷基縮醛衍生物之群組之1種或2種以上。
(式中,R1及R2可彼此相異,表示碳數1~4之烷基。)
(式中,R3~R6可彼此相異,表示碳數1~4之烷基。)
<3>一種用於炎症之預防或治療、PGE2產生抑制、黑色素生成抑制的選自包含季戊四醇、下述一般式(1)所示之季戊四醇之烷基縮醛衍生物、及下述一般式(2)所示之季戊四醇之烷基縮醛衍生物之群組之1種或2種以上。
(式中,R1及R2可彼此相異,表示碳數1~4之烷基。)
(式中,R3~R6可彼此相異,表示碳數1~4之烷基。)
<4>一種選自包含季戊四醇、下述一般式(1)所示之季戊四醇之烷基縮醛衍生物、及下述一般式(2)所示之季戊四醇之烷基縮醛衍生物之群組之1種或2種以上作為消炎用、防止肌膚粗糙用、防日曬用、美白用或膚色改善用的皮膚外用劑組成物的使用。
(式中,R1及R2可彼此相異,表示碳數1~4之烷基。)
(式中,R3~R6可彼此相異,表示碳數1~4之烷基。)
<5>一種選自包含季戊四醇、下述一般式(1)所示之季戊四醇之烷基縮醛衍生物、及下述一般式(2)所示之季戊四醇之烷基縮醛衍生物之群組之1種或2種以上的使用,其係用於製造消炎劑組成物、PGE2產生抑制劑組成物、黑色素生成抑制劑組成物或美白劑組成物。
(式中,R1及R2可彼此相異,表示碳數1~4之烷基。)
[化14]
(式中,R3~R6可彼此相異,表示碳數1~4之烷基。)
<6>一種選自包含季戊四醇、下述一般式(1)所示之季戊四醇之烷基縮醛衍生物、及下述一般式(2)所示之季戊四醇之烷基縮醛衍生物之群組之1種或2種以上用於製造消炎用、防止肌膚粗糙用、防日曬用、美白用或膚色改善用的皮膚外用劑組成物的使用。
(式中,R1及R2可彼此相異,表示碳數1~4之烷基。)
(式中,R3~R6可彼此相異,表示碳數1~4之烷基。)
<7>一種炎症之預防或治療、PGE2產生抑制或黑色素生成抑制的方法,其特徵為,投予選自包含季戊四醇、下述一般式(1)所示之季戊四醇之烷基縮醛衍生物、及下述一般式(2)所示之季戊四醇之烷基縮醛衍生物之群組之1種或2種以上的有效量。
[化17]
(式中,R1及R2可彼此相異,表示碳數1~4之烷基。)
(式中,R3~R6可彼此相異,表示碳數1~4之烷基。)
<8>一種防止肌膚粗糙、防日曬、美白或膚色改善的方法,其特徵為,將選自包含季戊四醇、下述一般式(1)所示之季戊四醇之烷基縮醛衍生物、及下述一般式(2)所示之季戊四醇之烷基縮醛衍生物之群組之1種或2種以上的有效量應用於皮膚。
(式中,R1及R2可彼此相異,表示碳數1~4之烷基。)
(式中,R3~R6可彼此相異,表示碳數1~4之烷基。)
<9>如上述<1>~<8>中任一項之組成物、使用或方法,其中,一般式(1)中之R1及R2所示之烷基較佳為碳數1~3、更佳為碳數1或2。
<10>如上述<1>~<8>中任一項之組成物、使用或方法,其中,上述一般式(1)所示之季戊四醇之烷基縮醛衍生物為單異亞丙基季戊四醇、單(1-甲基亞丙基)季戊四醇、單(1-乙基亞丙基)季戊四醇。
<11>如上述<1>~<8>中任一項之組成物、使用或方法,其中,一般式(2)中之R3~R6所示之烷基較佳為碳數1~3、更佳為碳數1或2。
<12>如上述<1>~<8>中任一項之組成物、使用或方法,其中,一般式(2)所示之季戊四醇之烷基縮醛衍生物為二異亞丙基季戊四醇、二(1-甲基亞丙基)季戊四醇或二(1-乙基亞丙基)季戊四醇。
<13>如上述<1>~<12>中任一項之組成物、使用或方法,其中,季戊四醇或季戊四醇之烷基縮醛衍生物的含量,係以組成物之總量為基準,較佳為0.001質量%以上、更佳為0.01質量%以上、進而較佳為0.1質量%以上、進而更佳為0.5質量%以上;且,較佳為20質量%以下、更佳為15質量%以下、進而較佳為10質量%以下、進而更佳為8質量%以下、特佳為5質量%以下。
<14>如上述<1>~<14>中任一項之組成物、使用或方法,其中,季戊四醇或季戊四醇之烷基縮醛衍生物之含量,係以組成物之總量為基準,較佳為0.001~20質量%、更佳為0.01~15質量%、進而較佳為0.1~10質量%、進而更佳為0.1~8質量%、特佳0.5~8質量%、最佳0.5~5質量%。
<15>如上述<1>~<14>中任一項之組成物、使用或方法,其中,有效成分為季戊四醇。
<16>如上述<1>~<14>中任一項之組成物、使用或方法,其中,皮
膚外用劑組成物為化妝料組成物。
以下根據實施例及比較例詳細說明本發明,但本發明之技術範圍並不限定於此等。
將季戊四醇(關東化學公司製)5.0g懸浮於丙酮70mL中,加入硫酸0.1mL並加溫至50℃。反應一日夜後,加入碳酸鉀1g予以中和,於減壓下去除過剩之丙酮約50%後,加入醋酸乙酯以去除丙酮。加入水藉醋酸乙酯進行萃取,得到白色結晶之二異亞丙基季戊四醇4.5g。
表示二異亞丙基季戊四醇之1H NMR的結果。
1H NMR(400MHz,CDCl3)[δ:1.85(s,12H),3.72(s,8H)]
將季戊四醇(關東化學公司製)5.0g懸浮於丙酮50mL中,加入硫酸0.05mL並加溫至50℃。反應2小時後,加入碳酸鉀1g予以中和,於減壓下去除過剩之丙酮約50%後,加入醋酸乙酯以去除丙酮。加入水藉醋酸乙酯進行萃取,得到白色結晶之單異亞丙基季戊四醇3.0g。
表示單異亞丙基季戊四醇之1H NMR的結果。
1H NMR(400MHz,CDCl3)[δ:1.42(s,6H),2.61(br,2H),3.73(s,4H),3.75(s,4H)]
將正常人類表皮細胞依每孔2×105個播種於24孔盤,於MCDB153
培養基培養2日。交換為屬於PGE2基質之含有花生油酸(和光純藥公司製)、及季戊四醇(純正化學公司製)或季戊四醇之烷基縮醛衍生物2種(實施例1、2之化合物)的MCDB153培養基,再培養1日。作為控制組,係以添加精製水取代季戊四醇或季戊四醇之烷基縮醛衍生物。培養結束後,使用PGE2測定套組(Cayman Chemical公司製)定量釋出於培養基上清液中的PGE2量。又,設置與控制組同樣地添加精製水、未添加花生油酸的對照群。
將結果示於表1。本發明之季戊四醇及季戊四醇之烷基縮醛衍生物,係於所有濃度區域中使因花生油酸添加而增加之PGE2量減少,可知其PGE2產生抑制效果明顯優越。
將正常人類表皮細胞依每孔2×105個播種於24孔盤,於MCDB153培養基培養2日。將培養基置換為HEPES Buffer,使用UVB燈(TOREX FL20S‧E-30/DMR 20W東芝醫療用品公司製),照射UVB 30mJ/cm2。紫外線強度係利用數位式紫外線強度計(Ultra Violet公司製)測定。UVB
照射後,交換為含有季戊四醇(純正化學公司製)的MCDB153培養基,再培養1日。作為控制組,係以添加精製水取代季戊四醇。培養結束後,使用PGE2測定套組(Cayman Chemical公司製)定量釋出於培養基上清液中的PGE2量。又,設置與控制組同樣地添加精製水、未照射UVB的對照群。
將結果示於表2。本發明之季戊四醇,係使因UVB照射而增加之PGE2量減少,可知其PGE2產生抑制效果明顯優越。
依表3之組成,藉常法調製本發明之季戊四醇調配而成的凝膠,並實施下述紅斑抑制試驗。
對被試驗者3名之背部2處,使用太陽光模擬器(Solar Light公司製)照射相當1.56MED的紫外線。在此紫外線照射完後,立即對被試驗者背部之單側依成為25μL/cm2之方式塗佈季戊四醇調配而成的凝膠。進而在紫外線照射3小時後,再次與上述同樣地塗佈25μL/cm2之凝膠。然後在紫外線照射24小時後,進行目視之紅斑判定與將藉由
Mexameter MX16(Courage Khhazaka公司製)所得之紅斑指數(erythema index)判定為發紅。目視係比較季戊四醇調配製劑與未塗佈部位。將結果示於表4及表5。
[表5]
由上表4,相較於未塗佈群,判斷3名中之2名係本發明之季戊四醇調配製劑塗佈群組的發紅較弱,1名判斷為同等。
又,由上表5之Maxameter的結果可知,相較於未塗佈群,本發明之季戊四醇調配製劑塗佈群均顯示較低值之紅斑指數,其紅斑抑制效果優越。從而,可知本發明之皮膚外用劑及化妝料可抑制起因於紫外線之炎症,預防或改善肌膚粗糙、色素沉澱、斑點、雀斑等的效果優越。
再者,試驗期間中,並未出現於塗佈有製劑之部位觀察到皮膚刺激反應及皮膚過敏反應的被試驗者,可確認本發明品在製劑形態下亦安全。
針對季戊四醇,進行下述所示之黑色素生成抑制試驗。
將由正常人類表皮黑色素細胞與表皮角質細胞所構成之3維培養皮膚模式(MEL-300-A,MatTek公司製),使用添加有誘導黑色素生成之因子之附屬之培養基進行培養。將季戊四醇溶液(1或5mmol/L)25μL添加至皮膚模式角質層上。每2~3日交換培養基及被試驗物質溶液,
培養11日後,洗淨皮膚模式,使用Alamar Blue(invitrogen公司製)測定細胞生存率。又,藉由於SOLVABLE(Perkin Elmar公司製)中加熱以溶解皮膚模式,將同樣地以SOLVABLE所溶解之melanin(SIGMA公司製)作為標準組,測定吸光度(405nm)算出黑色素量。求得將控制組(H2O添加)設為100(%)時的黑色素量。
將結果示於表6。
由表6之結果,顯示季戊四醇係添加濃度依存性地抑制黑色素生成,具有良好的美白作用。又,於上述試驗添加濃度中,均未檢測出細胞毒性。
於實施例6中,由於顯示季戊四醇之黑色素生成抑制效果,故進行屬於類似物質之3種糖醇(丁四醇、甘露醇、甘露糖)之黑色素生成抑制試驗。試驗方法係與實施例6相同。
將結果示於表7。
由表7之結果,丁四醇、甘露醇、甘露糖並未觀察到黑色素生成抑制效果。又,上述試驗添加濃度中,均未檢測到細胞毒性。
使用調配有屬於本發明之黑色素生成抑制成分之季戊四醇的美容液,實施下述所示之半臉比較連用試驗,針對使用後之肌膚狀態進行評價。
以33~48歲(平均年齡38.1歲)之健康正常人女性22名作為被試驗者,藉由雙盲試驗法,依1日2次,於半臉塗佈季戊四醇調配美容液(實施例8),於另一半臉塗佈安慰劑美容液(未調配季戊四醇;比較例1),連用8周後進行評價。美容液配方係示於表8。
對被試驗者,針對連用8周後之左右之肌膚狀態(斑點、色不均、肌膚明亮度),與試驗開始前相比較,回答出現何種變化。針對各項目進行5階段評價(5:變佳;4:稍微變佳;3:無變化;2:稍微變差;1:變差),將由全體被試驗者中回答了5、4之任一者的被試驗者,視為「塗佈樣本為有效與實際感受到之群組」,算出其比例。
由表9之結果明顯可知,相較於比較例1,在塗佈有調配本發明之季戊四醇之實施例8的部位實際感受到斑點、色不均、肌膚明亮度變佳的被試驗者的比例較多,可知其較有效。又,此試驗期間中,並未出現發生肌膚之困擾、未能繼續試驗的被試驗者。
藉常法製造下述組成之本發明之皮膚外用劑組成物(實施例9~13)。任一者於調配特性等方面均未有問題。又,調配量均為質
量%。
[表18]
本發明之含有季戊四醇及季戊四醇之烷基縮醛衍生物的消炎劑、黑色素生成抑制劑、美白劑,係具有優越之PGE2產生抑制
效果、紅斑抑制效果、黑色素生成抑制效果、美白效果,且安全性或穩定性優越,可穩定地調配於以消炎、防止肌膚粗糙、防曬、美白、膚色改善等為目的的皮膚外用劑組成物。
Claims (8)
- 一種選自包含季戊四醇、下述一般式(1)所示之季戊四醇之烷基縮醛衍生物、及下述一般式(2)所示之季戊四醇之烷基縮醛衍生物之群組之1種或2種以上的化合物之使用,其係用於製造以該等化合物作為有效成分之消炎劑組成物;
- 一種選自包含季戊四醇、下述一般式(1)所示之季戊四醇之烷基縮醛衍生物、及下述一般式(2)所示之季戊四醇之烷基縮醛衍生物之群組之1種或2種以上的化合物之使用,其係用於製造以該等化合物作為有效成分之PGE2產生抑制劑組成物;
- 一種選自包含季戊四醇、下述一般式(1)所示之季戊四醇之烷基縮 醛衍生物、及下述一般式(2)所示之季戊四醇之烷基縮醛衍生物之群組之1種或2種以上的化合物之使用,其係用於製造黑色素生成抑制劑組成物;
- 一種選自包含季戊四醇、下述一般式(1)所示之季戊四醇之烷基縮醛衍生物、及下述一般式(2)所示之季戊四醇之烷基縮醛衍生物之群組之1種或2種以上的化合物之使用,其係用於製造美白劑組成物;
- 一種選自包含季戊四醇、下述一般式(1)所示之季戊四醇之烷基縮醛衍生物、及下述一般式(2)所示之季戊四醇之烷基縮醛衍生物之群組之1種或2種以上的化合物之使用,其係用於製造以該等化合物作為 有效成分之消炎用、防日曬用、美白用或膚色改善用的皮膚外用劑組成物;
- 如申請專利範圍第1至5項中任一項之使用,其中,一般式(1)中之R1及R2所示之烷基為碳數1或2。
- 如申請專利範圍第1至5項中任一項之使用,其中,一般式(2)中之R3~R6所示之烷基為碳數1或2。
- 如申請專利範圍第1至5項中任一項之使用,其中,選自包含季戊四醇、一般式(1)所示之季戊四醇之烷基縮醛衍生物、及一般式(2)所示之季戊四醇之烷基縮醛衍生物之群組之1種或2種以上的化合物之含量,以組成物之總量作為基準,為0.001~15質量%。
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---|---|---|---|---|
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JPH1149655A (ja) * | 1997-08-08 | 1999-02-23 | Shiseido Co Ltd | 皮膚外用剤 |
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