JP2006117580A - Melanin formation inhibitor - Google Patents
Melanin formation inhibitor Download PDFInfo
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- JP2006117580A JP2006117580A JP2004306844A JP2004306844A JP2006117580A JP 2006117580 A JP2006117580 A JP 2006117580A JP 2004306844 A JP2004306844 A JP 2004306844A JP 2004306844 A JP2004306844 A JP 2004306844A JP 2006117580 A JP2006117580 A JP 2006117580A
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Abstract
Description
本発明は、優れたメラニン生成抑制剤、およびそれらを含有する香粧品に関するものである。 The present invention relates to excellent melanin production inhibitors and cosmetics containing them.
従来、メラニンの生成を抑制するものとしては、メラノサイトに対する細胞毒性によるもの、メラノサイト内でのチロシナーゼの活性を抑制するものや、チロシナーゼの発現を抑制するもの、チロシナーゼ活性により生成したドーパキノンから、自動酸化によりメラニンに至る経路で、酸化を防止する方法が知られている。そして、細胞毒性によるメラニン生成抑制作用を示すものとしては、ハイドロキノン等が知られている。これらは、皮膚の色素沈着を軽減する目的で、色素沈着症の治療に使用されてきたが、安全性に問題がある。その誘導体として一般的に知られているアルブチン(非特許文献1)は、メラニンの生成を可逆的に抑制する物質として、一般に化粧品等に使用されている。 Conventionally, the suppression of melanin production is due to cytotoxicity against melanocytes, the suppression of tyrosinase activity in melanocytes, the suppression of tyrosinase expression, the autooxidation from dopaquinone generated by tyrosinase activity There is known a method for preventing oxidation through a route leading to melanin. And hydroquinone etc. are known as what shows the melanin production suppression effect by cytotoxicity. They have been used to treat pigmentation for the purpose of reducing skin pigmentation, but have safety issues. Arbutin (Non-patent Document 1), which is generally known as a derivative thereof, is generally used in cosmetics and the like as a substance that reversibly suppresses the production of melanin.
その他メラニン生成抑制剤としては、例えば、システイン、グルタチオン、ビタミンC(非特許文献2)、コウジ酸(非特許文献3)、トリコデルマ属に属する微生物の産生物(特許文献1)、乳蛋白質のアルカリ分解物(特許文献2)、乳蛋白質の加水分解物(特許文献3)、コウジ酸のアミノ酸誘導体とペプチド誘導体(特許文献4)、メラニン生成抑制機能を有する香料化合物群(特許文献5)、チロシナーゼ活性阻害機能を有する香料化合物群(特許文献6、特許文献7)、各種植物抽出物等が知られている。 Other melanin production inhibitors include, for example, cysteine, glutathione, vitamin C (non-patent document 2), kojic acid (non-patent document 3), products of microorganisms belonging to the genus Trichoderma (patent document 1), and alkalis of milk proteins. Decomposed product (Patent Document 2), hydrolyzate of milk protein (Patent Document 3), amino acid derivative and peptide derivative of kojic acid (Patent Document 4), fragrance compound group having melanin production inhibitory function (Patent Document 5), tyrosinase A group of perfume compounds having an activity-inhibiting function (Patent Documents 6 and 7), various plant extracts, and the like are known.
しかしながら、これら従来のメラニン生成抑制剤は、ハイドロキノンの様に安全性に問題のあるものや、効果が実用上において満足できないものであり、真に満足できるものとはいえなかった。
本発明の目的は、安全で、かつ香粧品中に香粧品の品質を損なうことなく、任意の量を配合することができる新規なメラニン生成抑制剤を提供することにある。 An object of the present invention is to provide a novel melanin production inhibitor that is safe and can be incorporated in an arbitrary amount in a cosmetic product without impairing the quality of the cosmetic product.
本発明は、一般式 The present invention provides a general formula
(式中R1〜R6は水素原子または炭素数1〜10のアルコシキル基或いはビニル基のいずれかを示し、アルコキシル基とビニル基は、それぞれが式中R1〜R6のいずれか一つ以上を占める)で表される化合物群より選ばれる1種以上の化合物を有効成分とするメラニン生成抑制剤にある。
(Wherein R 1 to R 6 represent either a hydrogen atom, an alkoxyl group having 1 to 10 carbon atoms or a vinyl group, and each of the alkoxyl group and the vinyl group represents any one of R 1 to R 6 in the formula. In the melanin production inhibitor containing one or more compounds selected from the group of compounds represented by
本発明のメラニン生成抑制剤は、メラニン生成抑制効果が高く、安全で、複数の化合物を組み合わせることができるため、香粧品中に香粧品の品質を損なうことなく、任意の量を配合することができる。 The melanin production inhibitor of the present invention has a high melanin production inhibitory effect, is safe, and can combine a plurality of compounds. Therefore, any amount can be added to the cosmetic product without impairing the quality of the cosmetic product. it can.
本発明のメラニン生成抑制剤は、一般式 The melanin production inhibitor of the present invention has the general formula
(式中R1〜R6は水素原子または炭素数1〜10のアルコシキル基或いはビニル基のいずれかを示し、アルコキシル基とビニル基は、それぞれが式中R1〜R6のいずれか一つ以上を占める)で表される化合物群より選ばれる1種以上の化合物を有効成分とする。
(Wherein R 1 to R 6 represent either a hydrogen atom, an alkoxyl group having 1 to 10 carbon atoms or a vinyl group, and each of the alkoxyl group and the vinyl group represents any one of R 1 to R 6 in the formula. One or more compounds selected from the group of compounds represented by:
本発明の一般式 General formula of the present invention
(式中R1〜R6は水素原子または炭素数1〜10のアルコシキル基或いはビニル基のいずれかを示し、アルコキシル基とビニル基は、それぞれが式中R1〜R6のいずれか一つ以上を占める)で表される化合物群とは、具体的には、2−メトキシスチレン、3−メトキシスチレン、4−メトキシスチレン、2−エトキシスチレン、3−エトキシスチレン、4−エトキシスチレン、2−プロポキシスチレン、3−プロポキシスチレン、4−プロポキシスチレン、2−ブトキシスチレン、3−ブトキシスチレン、4−ブトキシスチレン、4−ビニルフェニル ペンチルエーテル、4−ビニルフェニル ヘキシルエーテル、4−ビニルフェニル ヘプチルエーテル、4−ビニルフェニル オクチルエーテル、4−ビニルフェニル ノニルエーテル、4−ビニルフェニル デシルエーテル、2,3−ジメトキシスチレン、2,4−ジメトキシスチレン、2,5−ジメトキシスチレン、2,6−ジメトキシスチレン、3,4−ジメトキトルエン、3,5−ジメトキトルエン、2,3−ジエトキシスチレン、2,4−ジエトキシスチレン、2,5−ジエトキシスチレン、2,6−ジエトキシスチレン、3,4−ジエトキシスチレン、3,5−ジエトキシスチレン、2−エトキシ−3−メトキシスチレン、2−エトキシ−4−メトキシスチレン、2−エトキシ−5−メトキシスチレン、2−エトキシ−6−メトキシスチレン、3−エトキシ−2−メトキシスチレン、3−エトキシ−4−メトキシスチレン、3−エトキシ−5−メトキシスチレン、3−エトキシ−6−メトキシスチレン、4−エトキシ−2−メトキシスチレン、4−エトキシ−3−メトキシスチレンが挙げられる。
(Wherein R 1 to R 6 represent either a hydrogen atom, an alkoxyl group having 1 to 10 carbon atoms or a vinyl group, and each of the alkoxyl group and the vinyl group represents any one of R 1 to R 6 in the formula. Specifically, the compound group represented by 2-methoxystyrene, 3-methoxystyrene, 4-methoxystyrene, 2-ethoxystyrene, 3-ethoxystyrene, 4-ethoxystyrene, 2-methoxystyrene, Propoxystyrene, 3-propoxystyrene, 4-propoxystyrene, 2-butoxystyrene, 3-butoxystyrene, 4-butoxystyrene, 4-vinylphenyl pentyl ether, 4-vinylphenyl hexyl ether, 4-vinylphenyl heptyl ether, 4 -Vinylphenyl octyl ether, 4-vinylphenyl nonyl ether, 4- Nylphenyl decyl ether, 2,3-dimethoxystyrene, 2,4-dimethoxystyrene, 2,5-dimethoxystyrene, 2,6-dimethoxystyrene, 3,4-dimethoxytoluene, 3,5-dimethoxytoluene, 2, 3-diethoxystyrene, 2,4-diethoxystyrene, 2,5-diethoxystyrene, 2,6-diethoxystyrene, 3,4-diethoxystyrene, 3,5-diethoxystyrene, 2-ethoxy- 3-methoxystyrene, 2-ethoxy-4-methoxystyrene, 2-ethoxy-5-methoxystyrene, 2-ethoxy-6-methoxystyrene, 3-ethoxy-2-methoxystyrene, 3-ethoxy-4-methoxystyrene, 3-ethoxy-5-methoxystyrene, 3-ethoxy-6-methoxystyrene, 4-ethoxy-2- Tokishisuchiren, and a 4-ethoxy-3-methoxy styrene.
本発明のメラニン生成抑制剤の有効成分としては、前記化合物群のうち、2−メトキシスチレン、3−メトキシスチレン、4−メトキシスチレン、2−エトキシスチレン、3−エトキシスチレン、4−エトキシスチレンが好ましく、2−メトキシスチレン、3−メトキシスチレン、4−メトキシスチレンがより好ましい。 As the active ingredient of the melanin production inhibitor of the present invention, 2-methoxystyrene, 3-methoxystyrene, 4-methoxystyrene, 2-ethoxystyrene, 3-ethoxystyrene and 4-ethoxystyrene are preferable among the above compound group. 2-methoxystyrene, 3-methoxystyrene, and 4-methoxystyrene are more preferable.
これら化合物は、単独で使用してもよく、また、任意の組合せで併用してもよい。 These compounds may be used alone or in any combination.
これら化合物は、市販または一般的な合成により容易に入手することができる。 These compounds can be easily obtained commercially or by general synthesis.
本発明のメラニン生成抑制剤は、アルブチン、コウジ酸、アスコルビン酸など、公知のメラニン生成抑制剤と組み合わせて使用することもできる。 The melanin production inhibitor of the present invention can be used in combination with known melanin production inhibitors such as arbutin, kojic acid, and ascorbic acid.
本発明のメラニン生成抑制剤は、ビタミン、抗酸化剤、抗炎症剤、紫外線吸収剤、冷感剤など、その他の有効成分と組み合わせて使用することもできる。 The melanin production inhibitor of the present invention can be used in combination with other active ingredients such as vitamins, antioxidants, anti-inflammatory agents, ultraviolet absorbers, cooling agents and the like.
本発明のメラニン生成抑制剤は、例えば、乳液、ローション、クリーム、パウダー、パック剤、皮膚洗浄剤、ペースト剤、ファンデーション、化粧水、ゲル剤、シャンプー、リンス、ボディーソープ、洗顔料等の化粧品や石鹸、洗剤その他皮膚外用剤などの香粧品に好適に用いることができる。さらには、繊維に塗布または付着させて使用することもできる。 The melanin production inhibitor of the present invention includes, for example, cosmetics such as emulsion, lotion, cream, powder, pack, skin cleanser, paste, foundation, lotion, gel, shampoo, rinse, body soap, face wash, It can be suitably used for cosmetics such as soaps, detergents and other external preparations for skin. Furthermore, it can also be used by applying or adhering to fibers.
本発明のメラニン生成抑制剤の香粧品類への添加量は特に限定されないが、一般に0.00001〜10質量%とすることが好ましく、0.0001〜5質量%とすることがさらに好ましい。 Although the addition amount to the cosmetics of the melanin production inhibitor of this invention is not specifically limited, Generally it is preferable to set it as 0.00001-10 mass%, and it is more preferable to set it as 0.0001-5 mass%.
(試験方法)
チロシナーゼ活性阻害試験
マックルベイン緩衝液(pH6.8)1mlに、0.3mg/ml濃度のチロシン溶液と各濃度の試料溶液を加え、37℃にて10分間の予備保温を行う。これに1mg/mlのチロシナーゼ(シグマ社製)0.1mlを加え37℃にて15分間加温した後、分光光度計を用いて、波長475nmにて吸光度(A)を測定した。各試料は50%エタノールにて、0.006%〜0.03%(最終濃度0.002%〜0.01%となる)に希釈したものを試験に用い、対照に対する阻害率を指標とした。尚、対照として、グラブリジンを0.00025%(最終濃度は0.000083%となる)に希釈して用いた。
一方、チロシナーゼの代わりに緩衝液0.1mlを加えたものの吸光度(B)、試料溶液の代わりに緩衝液0.1mlを加えたものの吸光度(C)、更に試料溶液とチロシナーゼの代わりに緩衝液0.2mlを加えたものの吸光度(D)をそれぞれ測定して、下式に従い阻害率(%)を算出した。
(計算式)
阻害率(%)=(A−B)/(C−D)×100
(Test method)
Tyrosinase activity inhibition test To 1 ml of Macclebain buffer (pH 6.8), a 0.3 mg / ml tyrosine solution and a sample solution of each concentration are added, and preliminary incubation is performed at 37 ° C. for 10 minutes. 0.1 mg of 1 mg / ml tyrosinase (manufactured by Sigma) was added thereto and heated at 37 ° C. for 15 minutes, and then the absorbance (A) was measured at a wavelength of 475 nm using a spectrophotometer. Each sample was diluted with 0.006% to 0.03% (final concentration 0.002% to 0.01%) with 50% ethanol for the test, and the inhibition rate relative to the control was used as an index. . As a control, grabridine was diluted to 0.00025% (the final concentration was 0.000083%) and used.
On the other hand, the absorbance (B) when 0.1 ml of buffer solution was added instead of tyrosinase, the absorbance (C) when 0.1 ml of buffer solution was added instead of the sample solution, and the buffer solution 0 instead of the sample solution and tyrosinase. The absorbance (D) of each sample with 2 ml added was measured, and the inhibition rate (%) was calculated according to the following formula.
(a formula)
Inhibition rate (%) = (A−B) / (C−D) × 100
横軸に最終濃度、縦軸にチロシナーゼ活性阻害率をプロットしたグラフを作成し、このグラフからチロシナーゼ活性を50%阻害する濃度(以後、IC50と表す。)を求めた。 A graph was prepared by plotting the final concentration on the horizontal axis and the tyrosinase activity inhibition rate on the vertical axis, and the concentration at which tyrosinase activity was inhibited by 50% (hereinafter referred to as IC50) was determined from this graph.
結果を表1に示す。 The results are shown in Table 1.
チロシナーゼ活性阻害試験結果
表1の結果から明らかなように、本発明のメラニン生成抑制剤は、チロシナーゼ活性阻害試験に対して、優れた阻害効果を示した。 As is clear from the results in Table 1, the melanin production inhibitor of the present invention showed an excellent inhibitory effect on the tyrosinase activity inhibition test.
本発明のメラニン生成抑制剤は、安全で、かつ香粧品の品質を損なうことなく、任意の量を配合することができるため、香粧品類に好適に使用される。 Since the melanin production inhibitor of the present invention is safe and can be added in any amount without impairing the quality of the cosmetic product, it is suitably used for cosmetic products.
Claims (5)
上記一般式(式中R1〜R6は水素原子または炭素数1〜10のアルコシキル基或いはビニル基のいずれかを示し、アルコキシル基とビニル基は、それぞれが式中R1〜R6のいずれか一つ以上を占める)で表される化合物群より選ばれる1種以上の化合物を有効成分とするメラニン生成抑制剤。
In the above general formula (wherein R 1 to R 6 represent either a hydrogen atom, an alkoxyl group having 1 to 10 carbon atoms or a vinyl group, and each of the alkoxyl group and the vinyl group represents any of R 1 to R 6 in the formula. A melanin production inhibitor comprising as an active ingredient at least one compound selected from the group of compounds represented by:
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