JP2014227393A - Skin-whitening agent - Google Patents
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- JP2014227393A JP2014227393A JP2013109639A JP2013109639A JP2014227393A JP 2014227393 A JP2014227393 A JP 2014227393A JP 2013109639 A JP2013109639 A JP 2013109639A JP 2013109639 A JP2013109639 A JP 2013109639A JP 2014227393 A JP2014227393 A JP 2014227393A
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- 0 CC(*)[C@@](CC(*)([C@]1*C1)C(O)=O)OC(C=Cc1ccc(*)c(*)c1)=O Chemical compound CC(*)[C@@](CC(*)([C@]1*C1)C(O)=O)OC(C=Cc1ccc(*)c(*)c1)=O 0.000 description 1
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Abstract
Description
本発明は、美白剤に関する。 The present invention relates to a whitening agent.
シミ・ソバカスや日焼けによって生じる色素沈着症状は、紫外線、女性ホルモン、遺伝的要因などによって惹き起こされると考えられているが、その要因は個々人によって様々である。そのため、色素沈着症状を改善する方法としては、色素沈着の原因となるメラニンの産生を抑制する方法や酵素チロシナーゼの活性を抑制する方法などが検討されており、これまでにも様々な美白剤が報告されている。これまでに報告されている美白剤としては、ヒノキチオールの誘導体（特許文献１参照），エルゴステロール誘導体（特許文献２参照），フェノキシ酢酸誘導体（特許文献３参照），α−Ｄ−グルコピラノシルグリセロール（特許文献４）等が挙げられる。しかし、これまでに報告されている美白剤は、その美白効果が必ずしも十分でなかったり、安全性で問題があるために使用制限がなされていたり、製剤に好ましくない色や臭いを付与してしまう場合があるなど、効果、副作用、安定性などの点から未だ十分なものが得られていないのが現状である。 Pigmentation symptoms caused by spots, sunbacus and sunburn are thought to be caused by ultraviolet rays, female hormones, genetic factors, etc., but the factors vary from person to person. Therefore, as a method for improving pigmentation symptoms, a method for suppressing the production of melanin that causes pigmentation and a method for suppressing the activity of the enzyme tyrosinase have been studied. It has been reported. Examples of whitening agents reported so far include derivatives of hinokitiol (see Patent Document 1), ergosterol derivatives (see Patent Document 2), phenoxyacetic acid derivatives (see Patent Document 3), and α-D-glucopyranosyl. Examples include glycerol (Patent Document 4). However, the whitening agents that have been reported so far do not necessarily have a sufficient whitening effect, are restricted in use due to safety issues, and give undesirable color and odor to the preparation. In some cases, there are cases where sufficient products have not yet been obtained in terms of effects, side effects, and stability.
また、クロロゲン酸の誘導体としては、クロロゲン酸のエチルエステルが抗インフルエンザウィルス効果を発揮することが知られている（特許文献５参照）。 As derivatives of chlorogenic acid, it is known that ethyl ester of chlorogenic acid exerts an anti-influenza virus effect (see Patent Document 5).
本発明は、高い美白作用を発揮する、美白剤を提供する。 The present invention provides a whitening agent that exhibits a high whitening effect.
本発明は、下記化学式（１）で示される化合物 The present invention relates to a compound represented by the following chemical formula (1)
（式１中Ｒ１は、Ｈ若しくは炭素数１〜１２の直鎖若しくは分岐鎖を有する、飽和若しくは不飽和のアルキル基を示し、Ｒ２〜Ｒ6は同一若しくは異なってもよくＨ若しくは炭素数２〜１２の直鎖若しくは分岐鎖を有する、飽和若しくは不飽和のアシル基を示し、Ｒ１〜Ｒ６が全てＨであることはない）を有効成分とする美白剤である。 (In Formula 1, R 1 represents H or a saturated or unsaturated alkyl group having a straight chain or branched chain having 1 to 12 carbon atoms, and R 2 to R 6 may be the same or different, and H or carbon number. A whitening agent having 2 to 12 straight or branched chain saturated or unsaturated acyl groups, and R 1 to R 6 are not all H).
本願第２の発明は、化学式（１）において、Ｒ１がエチル基、２−エチルヘキシル基から選択される１種又は２種であり、Ｒ２〜Ｒ6がＨである化合物を有効成分とする美白剤である。 In the second invention of the present application, in the chemical formula (1), R 1 is one or two selected from an ethyl group and a 2-ethylhexyl group, and a compound in which R 2 to R 6 are H is an active ingredient. It is a whitening agent.
本願発明は、高い美白効果を有する美白剤に関する。 The present invention relates to a whitening agent having a high whitening effect.
以下本発明を実施するための形態を説明する。 Hereinafter, modes for carrying out the present invention will be described.
本発明は、下記化学式（１）で示される化合物 The present invention relates to a compound represented by the following chemical formula (1)
（式１中Ｒ１は、Ｈ若しくは炭素数１〜１２の直鎖若しくは分岐鎖を有する、飽和若しくは不飽和のアルキル基を示し、Ｒ２〜Ｒ6は同一若しくは異なってもよくＨ若しくは炭素数２〜１２の直鎖若しくは分岐鎖を有する、飽和若しくは不飽和のアシル基を示し、Ｒ１〜Ｒ６が全てＨであることはない）を有効成分とする美白剤である。 (In Formula 1, R 1 represents H or a saturated or unsaturated alkyl group having a straight chain or branched chain having 1 to 12 carbon atoms, and R 2 to R 6 may be the same or different, and H or carbon number. A whitening agent having 2 to 12 straight or branched chain saturated or unsaturated acyl groups, and R 1 to R 6 are not all H).
本願発明の効果の点から、化学式（１）において、Ｒ１がエチル基であり、Ｒ２〜Ｒ6がＨである化合物が好ましく用いられる。 From the viewpoint of the effect of the present invention, a compound in which R 1 is an ethyl group and R 2 to R 6 are H in chemical formula (1) is preferably used.
本願発明の化合物は、下記化学式（２）で示される化合物であるクロロゲン酸を出発物質として合成することができる。 The compound of the present invention can be synthesized using chlorogenic acid, which is a compound represented by the following chemical formula (2), as a starting material.
Ｒ１にアルキル基をエステル結合させる際には、化学式（２）の化合物と炭素数１から１２のアルコールを希酸水溶液中で混合し、常温若しくは６０℃以下の温度条件下で適時反応させることにより合成することができる。 When an alkyl group is bonded to R 1 by ester bonding, the compound of formula (2) and an alcohol having 1 to 12 carbon atoms are mixed in a dilute aqueous acid solution and reacted at room temperature or under a temperature condition of 60 ° C. or less. Can be synthesized.
Ｒ２〜Ｒ6にアシル基を結合させる際には、化学式（２）の化合物と無水カルボン酸−ピリミジン混液を混合し、常温若しくは６０℃以下の温度条件下で適時反応させることにより合成することができる。この際、アシル基を結合させない部位については、予め他の化合物でマスキングを行ってから、反応後マスキングを取り外すこともできる。 When an acyl group is bonded to R 2 to R 6 , synthesis is performed by mixing the compound of the chemical formula (2) and a carboxylic anhydride-pyrimidine mixed solution and reacting them at room temperature or at a temperature of 60 ° C. or less in a timely manner. Can do. At this time, the portion where the acyl group is not bonded can be masked with another compound in advance, and then the masking can be removed after the reaction.
本発明の美白剤は、化学式（１）に示した化合物のみからなるものでもよいし、製剤化したものでもよい。 The whitening agent of the present invention may be composed of only the compound represented by the chemical formula (1) or may be formulated.
本発明の美白剤は、デキストリン、シクロデキストリン等の薬学的に許容し得るキャリアーその他任意の助剤を用いて、定法に従い、粉末状、顆粒状、錠剤状、液状等の任意の剤型に製剤化することができる。この際、助剤としては、例えば、賦形剤、結合剤、崩壊剤、潤沢剤、安定剤、矯味・矯臭剤等を用いることができる。美白剤は、他の組成物（例えば、皮膚外用剤、美容用飲食品等）に配合して使用することができる他、軟膏剤、外用液剤、貼付剤として使用することができる。 The whitening agent of the present invention is formulated into any dosage form such as powder, granule, tablet, liquid, etc. according to a conventional method using a pharmaceutically acceptable carrier such as dextrin and cyclodextrin and other optional auxiliaries. Can be In this case, as an auxiliary agent, for example, an excipient, a binder, a disintegrant, a lubricant, a stabilizer, a flavoring / flavoring agent, and the like can be used. The whitening agent can be used by blending with other compositions (for example, external preparations for skin, cosmetic foods and drinks), and can also be used as an ointment, a liquid for external use, and a patch.
本発明の美白剤を製剤化した場合、化学式（１）に示した化合物の含有量は、特に限定されるものではなく、目的に応じて適宜設定することができる。 When the whitening agent of the present invention is formulated, the content of the compound represented by the chemical formula (1) is not particularly limited and can be appropriately set depending on the purpose.
本発明の美白剤は、必要に応じて美白作用を有する他の成分を、化学式（１）に示した化合物とともに配合して用いることができる。 The whitening agent of this invention can mix | blend and use the other component which has a whitening effect with the compound shown in Chemical formula (1) as needed.
本発明の美白剤の投与方法としては、経皮投与、経口投与等が挙げられるが、目的に応じてその予防・改善等に公的な方法を適宜選択すればよい。 Examples of the administration method of the whitening agent of the present invention include transdermal administration, oral administration, and the like, and a public method may be appropriately selected for its prevention and improvement depending on the purpose.
また本発明の美白剤の投与量も、目的、適用方法、適用期間等によって適宜増減すればよい。 Further, the dosage of the whitening agent of the present invention may be appropriately increased or decreased depending on the purpose, application method, application period and the like.
本発明の美白剤は、化学式（１）に示した化合物が有する美白作用を通じて、メラニンの産生を抑制する。 The whitening agent of the present invention suppresses the production of melanin through the whitening action of the compound represented by the chemical formula (1).
本発明の美白剤は、優れた美白作用を有するとともに、皮膚に適用した場合の使用感と安全性に優れているため、例えば、皮膚外用剤に配合するのに好適である。この場合に、化学式（１）に示した化合物をそのまま配合してもよいし、化学式（１）に示した化合物から製剤化した美白剤を配合してもよい。 The whitening agent of the present invention has an excellent whitening action and is excellent in the feeling of use and safety when applied to the skin, and is therefore suitable for blending into, for example, a skin external preparation. In this case, the compound represented by the chemical formula (1) may be blended as it is, or a whitening agent formulated from the compound represented by the chemical formula (1) may be blended.
化学式（１）に示した化合物を配合する皮膚外用剤の剤型は任意であり、例えば、ローションなどの可溶化系、クリームや乳液などの乳化系、カラミンローション等の分散系として提供することができる。さらに、噴射剤と共に充填したエアゾール、軟膏剤、粉末、顆粒などの種々の剤型で提供することもできる。 The dosage form of the external preparation for skin containing the compound represented by the chemical formula (1) is arbitrary. For example, it can be provided as a solubilizing system such as lotion, an emulsifying system such as cream or emulsion, or a dispersing system such as calamine lotion. it can. Furthermore, it can also be provided in various dosage forms such as aerosols, ointments, powders and granules filled with a propellant.
なお、化学式（１）に示した化合物を配合する皮膚外用剤には、化学式（１）に示した化合物の他に、必要に応じて、通常医薬品、医薬部外品、皮膚化粧料、毛髪用化粧料及び洗浄料に配合される、油性成分、保湿剤、粉体、色素、乳化剤、可溶化剤、洗浄剤、紫外線吸収剤、増粘剤、薬剤、香料、樹脂、防菌防黴剤、アルコール類等を適宜配合することができる。また、本発明の効果を損なわない範囲において、他の保湿剤、細胞賦活剤、あるいは抗酸化剤等との併用も可能である。 In addition to the compound represented by the chemical formula (1), the skin external preparation containing the compound represented by the chemical formula (1) is usually used for pharmaceuticals, quasi-drugs, skin cosmetics and hair as needed. Oily ingredients, moisturizers, powders, pigments, emulsifiers, solubilizers, detergents, UV absorbers, thickeners, drugs, perfumes, resins, antibacterial and antifungal agents, blended in cosmetics and detergents, Alcohols etc. can be mix | blended suitably. Moreover, in the range which does not impair the effect of this invention, combined use with another moisturizer, a cell activator, an antioxidant, etc. is also possible.
また、本発明の美白剤は、経口的に摂取することも可能であり、例えば美容用運食品に配合することができる。ここで、美容用飲食品としては、その区分に制限はなく、経口的に摂取される一般食品、健康食品、保健機能食品、医薬部外品、医薬品等を幅広く含むものである。 In addition, the whitening agent of the present invention can be taken orally, and can be blended in, for example, a cosmetic food. Here, there is no restriction | limiting in the classification | category as food / beverage products for beauty, and it includes a wide range of foods such as general foods, health foods, health functional foods, quasi drugs, and pharmaceuticals that are taken orally.
この場合に、化学式（１）に示した化合物をそのまま配合してもよいし、化学式（１）に示した化合物から製剤化した美白剤を配合してもよい。 In this case, the compound represented by the chemical formula (1) may be blended as it is, or a whitening agent formulated from the compound represented by the chemical formula (1) may be blended.
化学式（１）に示した化合物、化学式（１）に示した化合物から製剤化した美白剤を美容用飲食品に配合する場合、それらにおける有効成分の配合量は、使用目的、症状、性別等を考慮して適宜変更することができるが、添加対象となる美容用飲食品の一般的な摂取量を考慮して、成人１日あたり０．０１〜１００ｍｇに成るようにするのが好ましい。 When a whitening agent formulated from the compound represented by the chemical formula (1) or the compound represented by the chemical formula (1) is blended in a cosmetic food or drink, the blending amount of the active ingredient in the formula is intended for use, symptoms, sex, etc. Although it can be appropriately changed in consideration, it is preferable that the daily intake is 0.01 to 100 mg for an adult in consideration of a general intake amount of the beauty food or drink to be added.
本発明の美白剤を配合した美容用飲食品は、化学式（１）に示した化合物をその活性を妨げないような任意の美容用飲食品に配合したものであってもよいし、化学式（１）に示した化合物を主成分とする栄養補助食品であってもよい。 The cosmetic food / beverage products containing the whitening agent of the present invention may be formulated with any cosmetic food / beverage product that does not interfere with the activity of the compound represented by the chemical formula (1). It may be a dietary supplement containing as a main component the compound shown in (1).
本発明の美白剤を配合した美容用飲食品を製造する際には、例えば、デキストリン、デンプン等の糖類；ゼラチン、大豆タンパク、トウモロコシタンパク、コラーゲン等のタンパク質；大豆ペプチド、ゼラチンなどのペプチド；アラニン、グルタミン、イソロイシン等のアミノ酸類；セルロース、アラビアゴム、キサンタンガム、ジェランガム、カラゲニン等の多糖類；大豆油、ナタネ油、コメ油、中鎖脂肪酸トリグリセリド、高級不飽和脂肪酸トリグリセリド等の油脂類等の任意の助剤を添加して、任意の形状の美容用飲食品にすることができる。 When manufacturing a food and drink for cosmetics containing the whitening agent of the present invention, for example, sugars such as dextrin and starch; proteins such as gelatin, soy protein, corn protein and collagen; peptides such as soy peptide and gelatin; alanine Amino acids such as cellulose, gum arabic, xanthan gum, gellan gum, carrageenan, etc .; oils such as soybean oil, rapeseed oil, rice oil, medium-chain fatty acid triglycerides, higher unsaturated fatty acid triglycerides, etc. The auxiliary agent can be added to make a food or drink for beauty of any shape.
化学式（１）に示した化合物を配合し得る美容用飲食品は特に限定されないが、清涼飲料、炭酸飲料、栄養飲料、果実飲料、乳酸飲料等の飲料（これらの飲料の濃縮原液、調整用粉末、ゼリーを含む）；種々の形態の健康・栄養補助食品；錠剤、カプセル剤、顆粒剤、ドリンク剤等が挙げられ、これらの美容用飲食品に化学式（１）に示した化合物を配合するときに、通常用いられる補助的な原料や添加剤を併用することができる。 Beauty foods and drinks that can be blended with the compound represented by the chemical formula (1) are not particularly limited, but beverages such as soft drinks, carbonated drinks, nutrition drinks, fruit drinks, lactic acid drinks (concentrated concentrates of these drinks, powders for adjustment) , Including jelly); various forms of health and nutritional supplements; tablets, capsules, granules, drinks, and the like. When these compounds for cosmetics are blended with the compound represented by chemical formula (1) In addition, commonly used auxiliary raw materials and additives can be used in combination.
また本発明の美白剤は、優れた美白作用を有するので、メラニン色素の産生機構に関連する研究のための試薬としても好適に利用することができる。 Further, since the whitening agent of the present invention has an excellent whitening action, it can be suitably used as a reagent for research related to the production mechanism of melanin pigment.
以下、実施例を示し、本発明を具体的に説明するが、本発明は下記の各例に何ら制限されるものではない。 EXAMPLES Hereinafter, although an Example is shown and this invention is demonstrated concretely, this invention is not restrict | limited to each following example at all.
「実施例１」クロロゲン酸エチルエステルの合成
エタノール５０ｍＬと試薬級クロロゲン酸０．１ｇ、希硫酸１ｍＬを混合し、暗中条件下、４０℃で３時間加熱、反応させた。酢酸エチル５０ｍＬと精製水５０ｍＬを添加して攪拌後酢酸エチル層を採取した。酢酸エチル層を精製水を用いて３回洗浄し、得られた酢酸エチル層の溶媒を留去し、濃縮物を凍結乾燥することにより、化学式（１）においてＲ１位にエチル基を導入したクロロゲン酸エチルエステルを合成した。収率は４８．６％であった。
クロロゲン酸エチルエステルの確認
ＬＣ／ＭＳ 直接ＭＳに注入して
ＥＳＩ＋ 水素付加イオンである383.1を確認
ＥＳＩ− 水素脱離イオンである381.1を確認
ＮＭＲ （１００ＭＨｚ、ＣＤ３ＯＤ）
13.0, 36.4, 36.6, 36.6, 61.3, 69.0, 70.8, 71.2, 74.4, 113.7, 113.7, 115.2, 121.7, 126.3, 145.5, 145.9, 148.4, 167.0, 173.6
Example 1 Synthesis of Chlorogenic Acid Ethyl Ester 50 mL of ethanol, 0.1 g of reagent grade chlorogenic acid, and 1 mL of dilute sulfuric acid were mixed and heated and reacted at 40 ° C. for 3 hours under dark conditions. 50 mL of ethyl acetate and 50 mL of purified water were added and stirred, and the ethyl acetate layer was collected. The ethyl acetate layer was washed three times with purified water, the solvent of the obtained ethyl acetate layer was distilled off, and the concentrate was freeze-dried to introduce an ethyl group at the R 1 position in the chemical formula (1). Chlorogenic acid ethyl ester was synthesized. The yield was 48.6%.
Confirmation of chlorogenic acid ethyl ester LC / MS Direct injection into MS confirms ESI + hydrogen addition ion 383.1 ESI- confirms hydrogen desorption ion 381.1 NMR (100 MHz, CD3OD)
13.0, 36.4, 36.6, 36.6, 61.3, 69.0, 70.8, 71.2, 74.4, 113.7, 113.7, 115.2, 121.7, 126.3, 145.5, 145.9, 148.4, 167.0, 173.6
［試験例１］ メラニン産生抑制作用
Ｂ１６マウスメラノーマ細胞を９０ｍｍディッシュ１ディッシュ当り１．８×１０４個となるように播種し、５質量％のウシ胎児血清（ＦＢＳ）を添加したダルベッコ改変イーグル培地（ＤＭＥＭ）を用いて培養した。２４時間後に５質量％ＦＢＳ添加ＤＭＥＭ培地に実施例１若しくはクロロゲン酸を添加して０．１ｍM濃度に調整したサンプル培養液に交換した。さらに５日間培養し、培養終了後にトリプシンにより細胞を剥離して回収した。回収した細胞を遠心し、細胞沈殿物を得た。得られた沈殿物に組織溶解剤（商品名Ｓｏｌｖａｂｌｅ[パーキンエルマー製]）を添加して煮沸し、室温に戻して分光光度計（日立社製分光光度計Ｕ−３０１０）により５００ｎｍの吸光度を測定した。
評価では、実施例１若しくはクロロゲン酸を添加せず５質量％ＦＢＳ添加ＤＭＥＭ培地のみで培養したものを、ネガティブコントロールとした。また５０ｍＭ乳酸ナトリウムを添加して培養したものを、ポジティブコントロールとした。
[Test Example 1] Melanin production inhibitory action Dulbecco's modified Eagle medium supplemented with 5 mass% fetal bovine serum (FBS) seeded with B16 mouse melanoma cells at 1.8 × 10 4 per 90 mm dish (DMEM) was used for culture. After 24 hours, Example 1 or a sample culture solution adjusted to a concentration of 0.1 mM by adding chlorogenic acid to 5% by mass FBS-added DMEM medium was replaced. After further culturing for 5 days, the cells were detached and collected with trypsin after completion of the culture. The collected cells were centrifuged to obtain a cell precipitate. Tissue solubilizer (trade name Solvable [manufactured by Perkin Elmer]) is added to the resulting precipitate, boiled, returned to room temperature, and the absorbance at 500 nm is measured with a spectrophotometer (Hitachi spectrophotometer U-3010). did.
In the evaluation, the negative control was obtained by culturing only Example 1 or 5% by mass FBS-added DMEM medium without adding chlorogenic acid. Moreover, what was cultured by adding 50 mM sodium lactate was used as a positive control.
表１より明らかなように、実施例１を添加した培地では、有意なメラニン生成抑制効果が認められた。これに対し、対照であるクロロゲン酸においては、試料無添加のネガティブコントロールと同程度の吸光度を示しており、メラニン生成抑制効果は認められなかった。 As is clear from Table 1, in the medium to which Example 1 was added, a significant melanin production inhibitory effect was observed. On the other hand, chlorogenic acid as a control showed the same level of absorbance as the negative control without addition of the sample, and no melanin production inhibitory effect was observed.
Claims (2)
（式１中Ｒ１は、Ｈ若しくは炭素数１〜１２の直鎖若しくは分岐鎖を有する、飽和若しくは不飽和のアルキル基を示し、Ｒ２〜Ｒ6は同一若しくは異なってもよくＨ若しくは炭素数２〜１２の直鎖若しくは分岐鎖を有する、飽和若しくは不飽和のアシル基を示し、Ｒ１〜Ｒ６が全てＨであることはない）を有効成分とする美白剤。 Compound represented by the following chemical formula (1)
(In Formula 1, R 1 represents H or a saturated or unsaturated alkyl group having a straight chain or branched chain having 1 to 12 carbon atoms, and R 2 to R 6 may be the same or different, and H or carbon number. A whitening agent comprising 2 to 12 straight or branched chain saturated or unsaturated acyl groups, wherein R 1 to R 6 are not all H).
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| JP2013109639A JP2014227393A (en) | 2013-05-24 | 2013-05-24 | Skin-whitening agent |
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| JP2013109639A JP2014227393A (en) | 2013-05-24 | 2013-05-24 | Skin-whitening agent |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016183130A (en) * | 2015-03-26 | 2016-10-20 | 株式会社コーセー | Agent for improving or preventing pigmentation |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0826967A (en) * | 1994-07-13 | 1996-01-30 | Ichimaru Pharcos Co Ltd | Cosmetic containing chlorogenic acid or its derivative |
| JPH0930953A (en) * | 1995-07-21 | 1997-02-04 | Noevir Co Ltd | Dermal preparation for external use |
| JPH1029908A (en) * | 1996-07-12 | 1998-02-03 | Noevir Co Ltd | External preparation for skin |
| JPH1059839A (en) * | 1996-08-21 | 1998-03-03 | Noevir Co Ltd | Preparation for external use for skin |
-
2013
- 2013-05-24 JP JP2013109639A patent/JP2014227393A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0826967A (en) * | 1994-07-13 | 1996-01-30 | Ichimaru Pharcos Co Ltd | Cosmetic containing chlorogenic acid or its derivative |
| JPH0930953A (en) * | 1995-07-21 | 1997-02-04 | Noevir Co Ltd | Dermal preparation for external use |
| JPH1029908A (en) * | 1996-07-12 | 1998-02-03 | Noevir Co Ltd | External preparation for skin |
| JPH1059839A (en) * | 1996-08-21 | 1998-03-03 | Noevir Co Ltd | Preparation for external use for skin |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016183130A (en) * | 2015-03-26 | 2016-10-20 | 株式会社コーセー | Agent for improving or preventing pigmentation |
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