JP4169278B2 - Melanin production inhibitor - Google Patents
Melanin production inhibitor Download PDFInfo
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- JP4169278B2 JP4169278B2 JP2004306845A JP2004306845A JP4169278B2 JP 4169278 B2 JP4169278 B2 JP 4169278B2 JP 2004306845 A JP2004306845 A JP 2004306845A JP 2004306845 A JP2004306845 A JP 2004306845A JP 4169278 B2 JP4169278 B2 JP 4169278B2
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- melanin production
- production inhibitor
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Description
本発明は、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 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), milk protein hydrolyzate (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 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、破線部はいずれか１箇所が二重結合であることを示し、R1、R2はともに水素原子であるか、またはR1、R2のいずれか１方がメチル基で、他方が水素原子であることを示す）で表される化合物群よりばれる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。
(In the formula, either one of the broken lines indicates a double bond, and R1 and R2 are both hydrogen atoms, or one of R1 and R2 is a methyl group and the other is a hydrogen atom. A melanin production inhibitor comprising one or more compounds selected from the group of compounds represented by (2) as an active ingredient.
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。 Since the melanin production inhibitor of the present invention has a high melanin production inhibitory effect, is safe, and can combine a plurality of compounds, any amount can be blended in 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、破線部はいずれか１箇所が二重結合であることを示し、R1、R2はともに水素原子であるか、またはR1、R2のいずれか１方がメチル基で、他方が水素原子であることを示す）で表される化合物群よりばれる１種以上の化合物を有効成分とする。
(In the formula, either one of the broken lines indicates a double bond, and R1 and R2 are both hydrogen atoms, or one of R1 and R2 is a methyl group and the other is a hydrogen atom. 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、破線部はいずれか１箇所が二重結合であることを示し、R1、R2はともに水素原子であるか、またはR1、R2のいずれか１方がメチル基で、他方が水素原子であることを示す）で表される化合物としては、具体的には４−（２，６，６−トリメチル−１−シクロヘキセン−１−イル）−ブタン−２−オール、４−（２，６，６−トリメチル−２−シクロヘキセン−１−イル）−ブタン−２−オール、４−（２，２−ジメチル−６−メチレンシクロヘキシル）−ブタン−２−オール、５-(２，６，６-トリメチル-２-シクロヘキセン-1-イル)-ペンタン-３-オール、５-(２，６，６-トリメチル-１-シクロヘキセン-1-イル)-ペンタン-３-オール、５-(２-メチレン-６，６-ジメチルシクロヘキシル)-ペンタン-３-オール、４-(２，６，６-トリメチル-２-シクロヘキセン-1-イル)-３-メチルブタン-２-オール、４-(２，６，６-トリメチル-1-シクロヘキセン-1-イル)-３-メチルブタン-２-オール、4-(２-メチレン-６，６-ジメチルシクロヘキシル) ３-メチルブタン-２-オールが挙げられる。
(In the formula, either one of the broken lines indicates a double bond, and R1 and R2 are both hydrogen atoms, or one of R1 and R2 is a methyl group and the other is a hydrogen atom. Specifically, the compound represented by 4- (2,6,6-trimethyl-1-cyclohexen-1-yl) -butan-2-ol, 4- (2,6 , 6-Trimethyl-2-cyclohexen-1-yl) -butan-2-ol, 4- (2,2-dimethyl-6-methylenecyclohexyl) -butan-2-ol, 5- (2,6,6- Trimethyl-2-cyclohexen-1-yl) -pentan-3-ol, 5- (2,6,6-trimethyl-1-cyclohexen-1-yl) -pentan-3-ol, 5- (2-methylene- 6,6-Dimethylcyclohexyl) -pentan-3-ol, 4- (2,6,6-trimethyl-2-cyclo Hexen-1-yl) -3-methylbutan-2-ol, 4- (2,6,6-trimethyl-1-cyclohexen-1-yl) -3-methylbutan-2-ol, 4- (2-methylene- 6,6-dimethylcyclohexyl) 3-methylbutan-2-ol.
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、４−（２，６，６−トリメチル−１−シクロヘキセン−１−イル）−ブタン−２−オール、４−（２，６，６−トリメチル−２−シクロヘキセン−１−イル）−ブタン−２−オール、４−（２，２−ジメチル−６−メチレンシクロヘキシル）−ブタン−２−オールがより好ましい。 As an active ingredient of the melanin production inhibitor of the present invention, 4- (2,6,6-trimethyl-1-cyclohexen-1-yl) -butan-2-ol, 4- (2, More preferred are 6,6-trimethyl-2-cyclohexen-1-yl) -butan-2-ol and 4- (2,2-dimethyl-6-methylenecyclohexyl) -butan-2-ol.
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 emulsions, lotions, creams, powders, packs, skin cleansers, pastes, foundations, lotions, gels, shampoos, rinses, body soaps, facial cleansers and the like. 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）
Ｂ１６メラノーマ細胞を播種し、２４時間後サンプルを含有したテオフィリン入り培地に交換し、７２時間後細胞を１０％ＴＣＡ処理した後エタノール：ジエチルエーテル＝１：１で処理し、さらに１０％ＤＭＳＯを含有する１ｍｏｌ／ＬＮａＯＨ液にメラニンを溶解させ、ＯＤ４７５を測定し、メラニン量とした。また、同時に細胞数も求め、細胞当たりのメラニン合成量を算出した。
(Test method)
B16 melanoma cells were seeded and replaced with theophylline-containing medium containing the sample after 24 hours. After 72 hours, the cells were treated with 10% TCA, treated with ethanol: diethyl ether = 1: 1, and further containing 10% DMSO. Melanin was dissolved in 1 mol / L NaOH solution, and OD475 was measured to obtain the amount of melanin. At the same time, the number of cells was determined, and the amount of melanin synthesis per cell was calculated.
（計算式）
抑制率（％）＝（Ａ−Ｂ）／Ａ×１００（但し、Ａ：サンプル無添加時の細胞当たりのメラニン合成量、Ｂ：サンプル添加時の細胞当たりのメラニン合成量）
(a formula)
Inhibition rate (%) = (A−B) / A × 100 (where A: amount of melanin synthesis per cell when no sample is added, B: amount of melanin synthesis per cell when sample is added)
結果を表１に示す。 The results are shown in Table 1.
Ｂ１６メラノーマ細胞を用いたメラニン生成抑制試験結果
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、メラニン生成抑制試験に対して、優れたメラニン生成抑制効果を示した。 As is clear from the results of Table 1, the melanin production inhibitor of the present invention showed an excellent melanin production inhibitory effect on the melanin production 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 (6)
（式中、破線部はいずれか１箇所が二重結合であることを示し、R1、R2はともに水素原子であるか、またはR1、R2のいずれか１方がメチル基で、他方が水素原子であることを示す）で表される化合物群よりばれる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。 The following general formula
(In the formula, either one of the broken lines indicates a double bond, and R1 and R2 are both hydrogen atoms, or one of R1 and R2 is a methyl group and the other is a hydrogen atom. The melanin production inhibitor which uses as an active ingredient 1 or more types of compounds chosen from the compound group represented by this.
で表される４−（２，６，６−トリメチル−シクロヘキセン−１−イル）−ブタン−２−オール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。 The following general formula
A melanin production inhibitor comprising as an active ingredient one or more compounds selected from the group of 4- (2,6,6-trimethyl-cyclohexen-1-yl) -butan-2-ol compounds represented by:
上記構造式で示される４−（２，６，６−トリメチル−１−シクロヘキセン−１−イル）−ブタン−２−オールを有効成分とするメラニン生成抑制剤。
A melanin production inhibitor containing 4- (2,6,6-trimethyl-1-cyclohexen-1-yl) -butan-2-ol represented by the above structural formula as an active ingredient.
上記構造式で示される４−（２，６，６−トリメチル−２−シクロヘキセン−１−イル）−ブタン−２−オールを有効成分とするメラニン生成抑制剤。
A melanin production inhibitor containing 4- (2,6,6-trimethyl-2-cyclohexen-1-yl) -butan-2-ol represented by the above structural formula as an active ingredient.
上記構造式で示される４−（２，２−ジメチル−６−メチレンシクロヘキシル）−ブタン−２−オールを有効成分とするメラニン生成抑制剤。
A melanin production inhibitor containing 4- (2,2-dimethyl-6-methylenecyclohexyl) -butan-2-ol represented by the above structural formula as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2004306845A JP4169278B2 (en) | 2004-10-21 | 2004-10-21 | Melanin production inhibitor |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2004306845A JP4169278B2 (en) | 2004-10-21 | 2004-10-21 | Melanin production inhibitor |
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| Publication Number | Publication Date |
|---|---|
| JP2006117581A JP2006117581A (en) | 2006-05-11 |
| JP4169278B2 true JP4169278B2 (en) | 2008-10-22 |
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| JP2004306845A Expired - Fee Related JP4169278B2 (en) | 2004-10-21 | 2004-10-21 | Melanin production inhibitor |
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| JP (1) | JP4169278B2 (en) |
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