JP5405902B2 - Whitening agent, whitening cosmetic, and method for producing whitening agent - Google Patents
Whitening agent, whitening cosmetic, and method for producing whitening agent Download PDFInfo
- Publication number
- JP5405902B2 JP5405902B2 JP2009128799A JP2009128799A JP5405902B2 JP 5405902 B2 JP5405902 B2 JP 5405902B2 JP 2009128799 A JP2009128799 A JP 2009128799A JP 2009128799 A JP2009128799 A JP 2009128799A JP 5405902 B2 JP5405902 B2 JP 5405902B2
- Authority
- JP
- Japan
- Prior art keywords
- whitening
- compound
- formula
- whitening agent
- cosmetic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Landscapes
- Cosmetics (AREA)
Description
本発明は、美白剤、美白用化粧料及び美白剤の製造方法に関する。 The present invention relates to a whitening agent, a whitening cosmetic, and a method for producing a whitening agent.
従来、種々の植物の抽出物が美白剤として用いられている。例えば、ヨモギの抽出物には、美白作用があることが知られている（特許文献１等）。
また、ヨモギをはじめとする種々の植物の抽出物中に、フラボノイド類が含まれることが知られ、及び所定のフラボノイド類及びその配糖体については、メラニン産生を促進するＡＤＦ（成人Ｔ細胞白血病由来因子）の産生を抑制することが報告されている（特許文献２）。一方で、所定のフラボノイド類については、メラニンの産生を促進する作用があることも報告されている（例えば、特許文献３及び４）。
Conventionally, various plant extracts have been used as whitening agents. For example, a mugwort extract is known to have a whitening effect (Patent Document 1, etc.).
In addition, flavonoids are known to be contained in extracts of various plants including mugwort, and for certain flavonoids and glycosides thereof, ADF (adult T cell leukemia) that promotes melanin production is known. It has been reported that production of (derived factor) is suppressed (Patent Document 2). On the other hand, it has also been reported that certain flavonoids have an action of promoting melanin production (for example, Patent Documents 3 and 4).
植物の抽出物は、一般的には、複数の化合物の混合物である。より高い美白効果を得るためには、又は美白効果のない化合物によるアレルギーの発症等の可能性をより低減するためには、美白効果のある化合物を特定することが重要である。
本発明は、新規な美白剤、美白用化粧料、及び美白剤の製造方法を提供することを課題とする。
A plant extract is generally a mixture of a plurality of compounds. In order to obtain a higher whitening effect, or in order to further reduce the possibility of the development of allergy due to a compound having no whitening effect, it is important to specify a compound having a whitening effect.
This invention makes it a subject to provide the manufacturing method of a novel whitening agent, cosmetics for whitening, and a whitening agent.
本発明は、下記式：（I）
また、本発明によって、前記化合物を有効成分として含有する美白用化粧料；及び植物（例えばヨモギ）の抽出物を処理して、抽出物中の前記化合物の含有比率を高める工程を含む美白剤の製造方法；が提供される。 Further, according to the present invention, there is provided a whitening cosmetic comprising: a whitening cosmetic comprising the compound as an active ingredient; and a step of treating a plant (eg mugwort) extract to increase the content ratio of the compound in the extract. A manufacturing method is provided.
本発明によれば、新規な美白剤、美白用化粧料、及び美白剤の製造方法を提供することができる。 ADVANTAGE OF THE INVENTION According to this invention, the manufacturing method of a novel whitening agent, cosmetics for whitening, and a whitening agent can be provided.
以下、本発明について詳細に説明する。なお、本明細書において「〜」とはその前後に記載される数値を下限値及び上限値として含む意味で使用される。
本発明は、下記式（Ｉ）で表される化合物からなる美白剤に関する。
The present invention relates to a whitening agent comprising a compound represented by the following formula (I).
前記式（Ｉ）の化合物の製造方法については特に制限されない。化学合成したものを使用しても、天然物由来の材料から精製したものを使用してもよい。前記式（Ｉ）の化合物は、例えば、Artemisia princeps Pampanini（ガイヨウヨモギ）、Artemisia Mongolia Fischer（モウコヨモギ）、Artemisia Stelleriana(シロヨモギ)、 Artemisia iwayomogi(イワヨモギ)、Artemisia deserti等のヨモギ抽出物から単離することができる。前記式（Ｉ）の化合物はヨモギに限らず、種々の植物抽出物から同定されており、具体的には、グレープフルーツ（“Bitterness and immature flavor in grapefruit: analyses and improvement of quality.", Journal of Food Science (1986), 51(5), 1368-9, Berry, R. E.; Tatum, J. H.参照）、ハッカ属ヌマハッカ（“Isolation and identification of flavonoid compounds of Mentha aquatica L. herb”， Roczniki Chemii (1977), 51(4), 701-9., Berry, R. E.; Tatum, J. H. Burzanska-Hermann, Zdzislawa; Rzadkowska-Bodalska, Halina; Olechnowicz-Stepien, Waleria.参照）、オオヒレアザミ（“On the phytochemistry of the flowers of Onopordon acanthium L. (cotton thistle)”. Deutsche Apotheker Zeitung (1976), 116(3), 57-9, Karl, Christian; Mueller, Gerhard; Pedersen, Peter A.参照）、カオリカズラ及びルエリア・ツベローサ（“Apigenin glycosides from Thunbergia fragrans and Ruellia tuberosa.”, Current Science (1974), 43(15), 480., Nair, A. G. Ramachandran; Subramanian, S. Sankara.参照）、並びに柑橘類（“Flavonoids in citrus and related genera. VI. Isolation and synthesis of ・ -form of isorhoifolin from citrus.", Agricultural and Biological Chemistry (1974), 38(2), 339-41, Kamiya, Shintaro; Esaki, Sachiko; Konishi, Fukuko.;及び“Flavonoids in citrus and related genera. II. Isolation and identification of isonaringin and neoeriocitrin from Citrus.”, Agricultural and Biological Chemistry (1971), 35(11), Kamiya, Shintaro; Esaki, Sachiko; Konishi, Fukuko.参照）等が報告されている。上記式（Ｉ）の化合物は、上記列挙したいずれの植物の抽出物から単離されたものであってもよい。 The method for producing the compound of the formula (I) is not particularly limited. A chemically synthesized product or a product purified from a natural product-derived material may be used. The compound of the formula (I) can be isolated from Artemisia princeps Pampanini, Artemisia Mongolia Fischer, Artemisia Stelleriana, Artemisia iwayomogi, Artemisia deserti, etc. Artemisia deserti it can. The compound of the formula (I) is not limited to mugwort but has been identified from various plant extracts, and specifically, grapefruit (“Bitterness and immature flavor in grapefruit: analyzes and improvement of quality.”, Journal of Food Science (1986), 51 (5), 1368-9, Berry, RE; see Tatum, JH), mint genus (“Isolation and identification of flavonoid compounds of Mentha aquatica L. herb”, Roczniki Chemii (1977), 51 (4), 701-9., Berry, RE; Tatum, JH Burzanska-Hermann, Zdzislawa; Rzadkowska-Bodalska, Halina; Olechnowicz-Stepien, Waleria.), Great White Thistle (“On the phytochemistry of the flowers of Onopordon acanthium L (cotton thistle) ”. See Deutsche Apotheker Zeitung (1976), 116 (3), 57-9, Karl, Christian; Mueller, Gerhard; Pedersen, Peter A.), Kaorikazura and Lueria Tuberosa (“ Apigenin glycosides from Thunbergia fragrans and Ruellia tuberosa. ”, Current Science (1974), 43 ( 15), 480., Nair, AG Ramachandran; Subramanian, S. Sankara.), And citrus (“Flavonoids in citrus and related genera. VI. Isolation and synthesis of ・ -form of isorhoifolin from citrus.”, Agricultural and Biological Chemistry (1974), 38 (2), 339-41, Kamiya, Shintaro; Esaki, Sachiko; Konishi, Fukuko .; and “Flavonoids in citrus and related genera. II. Isolation and identification of isonaringin and neoeriocitrin from Citrus.”, Agricultural and Biological Chemistry (1971), 35 (11), Kamiya, Shintaro; Esaki, Sachiko; Konishi, Fukuko. The compound of the above formula (I) may be isolated from any of the plant extracts listed above.
以下、ヨモギを例に挙げて、植物抽出物から、上記式（Ｉ）の化合物を単離する方法を説明するが、以下の方法に限定されるものでもない。
ヨモギ抽出物は、ヨモギの全草をそのまま、あるいは乾燥粉砕したものを溶媒等により抽出して得ることができる。又、ヨモギ抽出物は、溶媒に溶解した状態でも、あるいは凍結粉砕等により粉末化した状態のものでも用いることができる。ヨモギ抽出物を調製する際に用いる溶媒としては、例えば水、低級１価アルコール（メタノール、エタノール、１−プロパノール、２−プロパノール、１−ブタノール、２−ブタノール等）、液状多価アルコール（グリセリン、プロピレングリコール、１，３−ブチレングリコール等）、低級エステル（酢酸エチル等）、炭化水素（ベンゼン、ヘキサン、ペンタン等）、ケトン類（アセトン、メチルエチルケトン等）、エーテル類（ジエチルエーテル、テトラヒドロフラン、ジプロピルエーテル等）、アセトニトリル等が挙げられ、それらの一種又は二種以上を用いることができる。中でも、水、又は水と親水性の高い有機溶媒との混合溶媒を用いるのが好ましく、そのような有機溶媒としてはエタノールが特に好ましい。
Hereinafter, a method for isolating the compound of the above formula (I) from a plant extract will be described by taking a mugwort as an example, but it is not limited to the following method.
The mugwort extract can be obtained by extracting the whole mugwort plant as it is or by drying and grinding it with a solvent or the like. The mugwort extract can be used either in a state dissolved in a solvent or in a powdered state by freeze pulverization or the like. Examples of the solvent used when preparing the mugwort extract include water, lower monohydric alcohols (methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, etc.), liquid polyhydric alcohols (glycerin, Propylene glycol, 1,3-butylene glycol, etc.), lower esters (ethyl acetate, etc.), hydrocarbons (benzene, hexane, pentane, etc.), ketones (acetone, methyl ethyl ketone, etc.), ethers (diethyl ether, tetrahydrofuran, dipropyl, etc.) Ether), acetonitrile, etc., and one or more of them can be used. Among these, water or a mixed solvent of water and a highly hydrophilic organic solvent is preferably used, and ethanol is particularly preferable as such an organic solvent.
好ましい抽出方法の一例としては、濃度０〜１００ｖｏｌ％の水を含むエタノールを用い、室温でもしくは加温して、３日間抽出を行った後ろ過し、得られた濾液を濃縮（所望により減圧濃縮）して、溶媒を除去して、抽出物を得る。所望により複数回抽出を行い、そのろ液を混合してもよい。また、所望により所定の期間熟成等をさせた後、濃縮してもよい。 As an example of a preferable extraction method, ethanol containing water having a concentration of 0 to 100 vol% is used, extracted at room temperature or heated for 3 days, filtered, and the obtained filtrate is concentrated (concentrated under reduced pressure if desired). ) To remove the solvent and obtain an extract. If desired, extraction may be performed a plurality of times, and the filtrate may be mixed. Further, it may be concentrated after aging for a predetermined period if desired.
得られたヨモギ抽出物をカラムに吸着させた後、極性の異なる複数種の溶媒で溶出させて分画し、所定の画分を採取し精製した後、また同様に分画・精製を繰り返すことで、前記式（Ｉ）の化合物の比率を高めることができる。最終的にＴＬＣ上で単一スポットになるまで、分画・精製操作を繰り返せば、前記式（Ｉ）の化合物を単離することができる。 Adsorb the obtained mugwort extract to the column, elute with multiple solvents with different polarities, fractionate, collect and purify the specified fraction, and repeat fractionation and purification in the same way The ratio of the compound of the formula (I) can be increased. The compound of formula (I) can be isolated by repeating the fractionation / purification operation until it finally becomes a single spot on TLC.
ヨモギ抽出物等、前記式（Ｉ）の化合物を含有する植物等の天然物抽出物に、該化合物の含有比率を高める処理を施した後、該処理物を美白剤として用いても、処理前の天然物抽出物と比較して、より高い美白効果が得られる。前記式（Ｉ）の化合物の含有比率を高める処理としては、溶媒抽出、限外ろ過、カラム精製等が挙げられる。 A natural product extract such as a mugwort extract or the like containing a compound of the above formula (I) is subjected to a treatment for increasing the content ratio of the compound, and the treated product may be used as a whitening agent. Compared with natural product extracts of the above, a higher whitening effect can be obtained. Examples of the treatment for increasing the content ratio of the compound of the formula (I) include solvent extraction, ultrafiltration, column purification and the like.
前記式（Ｉ）の化合物を単独で美白剤として使用することにより、又は該化合物の含有比率がより高い天然物由来の抽出物を用いることにより、美白効果のない化合物が皮膚に適用されることのマイナス効果（例えば、アレルギーの発症等）が生じる可能性をより低減することができる。また、天然物由来の抽出物をそのまま化粧料に配合する場合より、着色や変臭・沈殿などの変化を低減させる安定な化粧料を調製することができる。 A compound having no whitening effect is applied to the skin by using the compound of formula (I) alone as a whitening agent, or by using an extract derived from a natural product having a higher content ratio of the compound. The possibility that negative effects (for example, the development of allergies) will occur can be further reduced. In addition, it is possible to prepare a stable cosmetic that reduces changes in coloration, odor, precipitation, and the like, as compared with the case where an extract derived from a natural product is directly added to the cosmetic.
本発明は、前記式（Ｉ）の化合物を有効成分として含有する美白用化粧料にも関する。本発明の美白用化粧料中、前記式（Ｉ）の化合物の含有量は、固形分で０．００００１〜０．１質量％（以下、単に「％」と記載する）であるのが好ましく、０．０００１〜０．０１％であるのがより好ましい。前記範囲であると、高い美白効果が得られるとともに、化粧料中に安定的に配合することができる。 The present invention also relates to a whitening cosmetic containing the compound of formula (I) as an active ingredient. In the whitening cosmetic composition of the present invention, the content of the compound of the formula (I) is preferably 0.00001 to 0.1% by mass (hereinafter simply referred to as “%”) in terms of solid content, It is more preferably 0.0001 to 0.01%. Within the above range, a high whitening effect can be obtained and can be stably blended in cosmetics.
本発明の美白用化粧料は、化粧料に通常使用される各種の成分、即ち、水、アルコール、油剤、界面活性剤、増粘剤、粉体、キレート剤、ｐＨ調整剤、紫外線吸収剤、植物・微生物由来の抽出物、保湿剤・抗炎症剤・細胞賦活剤等の各種薬効剤、香料等を、本発明の効果を損なわない範囲で適宜加えることができる。 The whitening cosmetic composition of the present invention comprises various components usually used in cosmetics, that is, water, alcohol, oil agent, surfactant, thickener, powder, chelating agent, pH adjuster, ultraviolet absorber, Various medicinal agents such as extracts derived from plants and microorganisms, moisturizers, anti-inflammatory agents, cell activators, fragrances, and the like can be appropriately added within a range not impairing the effects of the present invention.
本発明の美白用化粧料の形態については特に制限はなく、乳液、クリーム、化粧水、美容液、パック、洗顔料、メーキャップ化粧料等、いずれの形態の化粧料として調製されたものであってもよい。 The form of the whitening cosmetic of the present invention is not particularly limited, and is prepared as a cosmetic of any form, such as a milky lotion, cream, lotion, cosmetic liquid, pack, face wash, makeup cosmetics, etc. Also good.
以下、実施例により本発明をさらに具体的に説明するが、本発明の範囲は下記の実施例に限定されることはない。
［実施例１］
（製造例１）
ガイヨウヨモギ（Artemisiaprinceps Pampanini）又はモウコヨモギ（Artemisia Mongolia Fischer）の葉１ｋｇを細切りし、水−エタノール混合溶媒（水／エタノール＝１０／９０ｖｏｌ％）５Ｌで３回抽出した。３回の抽出によって得られたろ液を混合して、減圧濃縮を行い、エタノールを留去し、ヨモギ抽出物を得た。次に、このヨモギ抽出物を、カラム（ＨＰ−２０：三菱化学社製）に吸着させた後、含水アルコールで溶出し、シリカゲルオープンカラムにより、クロロホルム、メタノール、水の混合溶媒を用いて、ＴＬＣ上単一スポットになるまで分画・精製を繰り返し、式（Ｉ）の化合物を得た。
EXAMPLES Hereinafter, although an Example demonstrates this invention further more concretely, the scope of the present invention is not limited to the following Example.
[Example 1]
(Production Example 1)
1 kg of leaves of Artemisiaprinceps Pampanini or Artemisia Mongolia Fischer were cut into small pieces and extracted three times with 5 L of a water-ethanol mixed solvent (water / ethanol = 10/90 vol%). The filtrates obtained by the extraction three times were mixed and concentrated under reduced pressure, and ethanol was distilled off to obtain a mugwort extract. Next, this mugwort extract was adsorbed on a column (HP-20: manufactured by Mitsubishi Chemical Corporation), and then eluted with hydrous alcohol, and a TLC using a mixed solvent of chloroform, methanol and water with a silica gel open column. Fractionation and purification were repeated until the upper single spot was obtained to obtain a compound of formula (I).
得られた化合物の質量マススペクトルと1Ｈ−ＮＭＲ及び13Ｃ−ＮＭＲ（５００及び１２５ＭＨｚ、Ｃ5Ｄ5Ｎ、温度３００Ｋ）を測定した。結果を下記に示す。 The mass spectrum and 1 H-NMR and 13 C-NMR (500 and 125 MHz, C 5 D 5 N, temperature 300 K) of the obtained compound were measured. The results are shown below.
この測定結果は、“The antioxidative compounds of Similax riparia leaves (in Korean).", Yakhak Hoechi (2003), 47, 300-306, Cho E, Kim J, Kim H, Chon I, Ham I, Whang Wに報告されている、式（Ｉ）の化合物のＮＭＲデータと整合していた。 The measurement results are shown in “The antioxidative compounds of Similax riparia leaves (in Korean).”, Yakhak Hoechi (2003), 47, 300-306, Cho E, Kim J, Kim H, Chon I, Ham I, Whang W. It was consistent with the reported NMR data of the compound of formula (I).
（美白作用の評価１）
マウス由来のＢ１６メラノーマ培養細胞を使用し、製造例１で得られた式（Ｉ）の化合物のメラニン生成抑制効果を調べた。具体的には、６穴プレートに１０％ＦＢＳ含有ＭＥＭ培地を適量とりＢ１６メラノーマ細胞を播種し、３７℃、二酸化炭素濃度５％中にて静置した。翌日、製造例１で得られた化合物を、含水エタノール（水／エタノール＝５０／５０（ｖｏｌ比））に溶解して添加した。培養５日目に培地を交換し、再度検体調製液を添加した。翌日、培地を除き、１枚のプレートについて、細胞をリン酸緩衝液にて洗浄した後回収し、Ｂ１６メラノーマ培養細胞の白色化度を以下の基準にて評価した。対照には検体を添加しないものを用意した。また、比較例として、製造例１で化合物の単離に用いたヨモギ抽出物、及びメラニン生成抑制作用のあることが知られているコウジ酸についても同様の試験を行った。
なお、式（Ｉ）の化合物、ヨモギ抽出物、及びコウジ酸のそれぞれについて、固形分濃度が１００μｇ／ｍＬである各試料をそれぞれ調製し、試験を行なった。
（判定基準）
＋＋：対照に対してあきらかに白色である。
＋ ：対照に対して白色である。
− ：対照と同じ黒色である。
結果を下記表２に示す。
(Evaluation of whitening effect 1)
Using mouse-derived B16 melanoma cultured cells, the melanin production inhibitory effect of the compound of formula (I) obtained in Production Example 1 was examined. Specifically, an appropriate amount of 10% FBS-containing MEM medium was taken in a 6-well plate, seeded with B16 melanoma cells, and allowed to stand at 37 ° C. in a carbon dioxide concentration of 5%. On the next day, the compound obtained in Production Example 1 was dissolved in water-containing ethanol (water / ethanol = 50/50 (vol ratio)) and added. On day 5 of the culture, the medium was changed, and the sample preparation solution was added again. On the next day, the medium was removed and the cells were collected after washing with phosphate buffer on one plate, and the degree of whiteness of the cultured B16 melanoma cells was evaluated according to the following criteria. As a control, a sample to which no specimen was added was prepared. In addition, as a comparative example, the same test was performed on mugwort extract used for the isolation of the compound in Production Example 1 and kojic acid known to have a melanin production inhibitory action.
In addition, about each of the compound of a formula (I), a mugwort extract, and kojic acid, each sample whose solid content concentration is 100 microgram / mL was prepared, respectively, and the test was done.
(Criteria)
++: Clearly white relative to the control.
+: White with respect to the control.
-: The same black color as the control.
The results are shown in Table 2 below.
上記結果から、本発明の前記式（Ｉ）の化合物は、従来の美白剤であるコウジ酸と比較して、より高い美白効果を示すことが理解できる。また、その効果はヨモギ抽出物と同程度であったが、美白活性成分だけを精製して得られた式（Ｉ）の化合物は、その着色の程度が濃褐色であるヨモギ抽出物よりも低かった。そのため、ヨモギ抽出物を配合する場合より安定性や安全性に優れた化粧料を製造することができる。 From the above results, it can be understood that the compound of the formula (I) of the present invention exhibits a higher whitening effect as compared with kojic acid which is a conventional whitening agent. The effect was similar to that of mugwort extract, but the compound of formula (I) obtained by purifying only the whitening active ingredient was lower in coloration than mugwort extract. It was. Therefore, it is possible to produce a cosmetic material that is more stable and safer than when a mugwort extract is blended.
（美白作用の評価２）
上記特許文献２には、式（Ｉ）の化合物のアグリコンであるアピゲニンやその糖誘導体にメラニン産生を促進するＡＤＦの産生を抑制する効果があることが示唆されている。そこで、アピゲニン及びアピゲニン−７−グルコシドについても美白効果を調べ、その結果を、式（Ｉ）の化合物の美白効果と比較した。
なお、式（Ｉ）の化合物、アピゲニン、及びアピゲニン−７−グルコシドのそれぞれについて、１６０ｍｏｌ／Ｌの試料を調製し、この３種の試料について、上記と同様にして試験し、及び上記と同一の判定基準で評価した。結果を下記表に示す。
(Evaluation of whitening effect 2)
Patent Document 2 suggests that apigenin, which is an aglycon of the compound of formula (I), or a sugar derivative thereof has an effect of suppressing ADF production that promotes melanin production. Thus, the whitening effect was also examined for apigenin and apigenin-7-glucoside, and the results were compared with the whitening effect of the compound of formula (I).
In addition, a 160 mol / L sample was prepared for each of the compound of formula (I), apigenin, and apigenin-7-glucoside, and these three samples were tested in the same manner as described above, and the same as above. Evaluation was based on criteria. The results are shown in the table below.
上記表に示す結果から、式（Ｉ）の化合物の試料には高い美白効果が認められたが、アピゲニン及びアピゲニン−７−グルコシドの同一濃度の各試料には、美白効果は認められなかった。 From the results shown in the above table, a high whitening effect was observed in the sample of the compound of formula (I), but no whitening effect was observed in each sample of the same concentration of apigenin and apigenin-7-glucoside.
（美白作用の評価３）
また、フラボノイドの配糖体として、式（Ｉ）の化合物に含まれる糖と同一の糖を含むフラボノイド誘導体である、ナリンギン及びナリンゲニンのそれぞれについて、濃度１００μｍｏｌ／Ｌ及び３００μｍｏｌ／Ｌの試料を準備し、上記と同様に試験を行い、上記と同一の判定基準で評価した。結果を下記表に示す。
(Evaluation of whitening effect 3)
In addition, as flavonoid glycosides, samples having a concentration of 100 μmol / L and 300 μmol / L are prepared for naringin and naringenin, which are flavonoid derivatives containing the same sugar as that contained in the compound of formula (I). The test was performed in the same manner as described above, and the evaluation was performed according to the same criteria as described above. The results are shown in the table below.
上記表に示す結果から、ナリンギン及びナリンゲニンには、美白効果が認められなかった。 From the results shown in the above table, no whitening effect was observed for naringin and naringenin.
上記評価結果から、式（Ｉ）の化合物のアグリコンであるアピゲニンでは美白効果は得られず、またアピゲニンの配糖体であっても、式（Ｉ）の化合物とは異なる糖を含むアピゲニン−７−グルコシドによっても美白効果は得られないことがわかった。さらに、式（Ｉ）の化合物と同一の糖を含む配糖体であっても、アグリコンが他のフラボノイド類である、ナリンゲニンやナリンギンでも、美白効果は得られなかった。即ち、式（Ｉ）の化合物は、他のフラボノイド類及びその配糖体と比較して、格段に高い美白効果を示すことが理解できる。 From the above evaluation results, apigenin, which is an aglycon of the compound of formula (I), does not provide a whitening effect, and even apigenin glycosides include apigenin-7 containing a sugar different from the compound of formula (I). -It was found that no whitening effect was obtained even with glucoside. Furthermore, even if it was a glycoside containing the same sugar as the compound of formula (I), no whitening effect was obtained even with naringenin or naringin in which aglycone is another flavonoid. That is, it can be understood that the compound of the formula (I) shows a markedly higher whitening effect than other flavonoids and glycosides thereof.
［実施例２：化粧水の調製］
下記の組成の化粧水を、以下の方法で調製した。
Ａ． 成分（３）、（４）及び（８）〜（１０）を混合溶解する。
Ｂ． 成分（１）、（２）、（５）〜（７）及び（１１）を混合溶解する。
Ｃ． ＡとＢを混合して均一にし、化粧水を得た。
（成分） （％）
（１）グリセリン ５．０
（２）１，３−ブチレングリコール ６．５
（３）ポリオキシエチレン（２０Ｅ．Ｏ．）ソルビタン １．２
モノラウリン酸エステル
（４）エタノール １２．０
（５）乳酸 ０．０５
（６）乳酸ナトリウム ０．１
（７）コラーゲン １．０
（８）式（Ｉ）の化合物*1 ０．０００１
（９）メチルパラベン ０．１
（１０）香料 適量
（１１）精製水 残量
＊１：製造例１で調製したもの
[Example 2: Preparation of lotion]
A lotion having the following composition was prepared by the following method.
A. Components (3), (4) and (8) to (10) are mixed and dissolved.
B. Components (1), (2), (5) to (7) and (11) are mixed and dissolved.
C. A and B were mixed and uniformed to obtain a skin lotion.
(Ingredient) (%)
(1) Glycerin 5.0
(2) 1,3-butylene glycol 6.5
(3) Polyoxyethylene (20E.O.) sorbitan 1.2
Monolaurate (4) Ethanol 12.0
(5) Lactic acid 0.05
(6) Sodium lactate 0.1
(7) Collagen 1.0
(8) Compound of formula (I) * 1 0.0001
(9) Methylparaben 0.1
(10) Fragrance appropriate amount (11) Purified water remaining amount * 1: prepared in Production Example 1
［実施例３：乳液の調製］
下記の組成の乳液を、以下の方法で調製した。
Ａ． 成分（９）を加熱混合し、７０℃に保つ。
Ｂ． 成分（１）〜（８）および（１０）を加熱混合し、７０℃に保つ。
Ｃ． ＢにＡを加えて混合し、均一に乳化する。
Ｄ． Ｃを冷却後（１１）〜（１４）を加え、均一に混合して乳液を得た。
[Example 3: Preparation of emulsion]
An emulsion having the following composition was prepared by the following method.
A. Ingredient (9) is heated and mixed and maintained at 70 ° C.
B. Ingredients (1) to (8) and (10) are heated and mixed and maintained at 70 ° C.
C. A is added to B, mixed and uniformly emulsified.
D. After cooling C, (11) to (14) were added and mixed uniformly to obtain an emulsion.
（成分） （％）
（１）ポリオキシエチレン（１０Ｅ．Ｏ．）ソルビタン １．０
モノステアレート
（２）ポリオキシエチレン（６０Ｅ．Ｏ．）ソルビット ０．５
テトラオレエート
（３）グリセリルモノステアレート １．０
（４）ステアリン酸 ０．５
（５）ベヘニルアルコール ０．５
（６）スクワラン ８．０
（７）エタノール ５．０
（８）式（Ｉ）の化合物（Ｉ）*1 ０．００１
（９）精製水 残量
（１０）メチルパラベン ０．１
（１１）カルボキシビニルポリマー ０．２
（１２）水酸化ナトリウム ０．１
（１３）ヒアルロン酸 ０．１
（１４）香料 適量
＊１：製造例１で調製したもの
(Ingredient) (%)
(1) Polyoxyethylene (10E.O.) sorbitan 1.0
Monostearate (2) Polyoxyethylene (60EO) Sorbit 0.5
Tetraoleate (3) Glyceryl monostearate 1.0
(4) Stearic acid 0.5
(5) Behenyl alcohol 0.5
(6) Squalane 8.0
(7) Ethanol 5.0
(8) Compound (I) of formula (I) * 1 0.001
(9) Purified water remaining amount (10) Methylparaben 0.1
(11) Carboxyvinyl polymer 0.2
(12) Sodium hydroxide 0.1
(13) Hyaluronic acid 0.1
(14) Perfume appropriate amount * 1: prepared in Production Example 1
実施例２で調製した化粧水、及び実施例３で調製した乳液は、いずれも皮膚に適用することにより美白効果があり、また、同量のヨモギエキスを配合した化粧水・乳液と比較して製造時の着色や経時での変臭、沈殿物等の発生もなく、安定性も良好であった。 Both the lotion prepared in Example 2 and the emulsion prepared in Example 3 have a whitening effect when applied to the skin, and compared with a lotion / milky emulsion containing the same amount of mugwort extract. There was no coloration during production, no odor change or precipitation with time, and the stability was good.
本発明によれば、新規な美白剤、及び美白用化粧料を提供することができる。 According to the present invention, a novel whitening agent and a whitening cosmetic can be provided.
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009128799A JP5405902B2 (en) | 2009-05-28 | 2009-05-28 | Whitening agent, whitening cosmetic, and method for producing whitening agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009128799A JP5405902B2 (en) | 2009-05-28 | 2009-05-28 | Whitening agent, whitening cosmetic, and method for producing whitening agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010275227A JP2010275227A (en) | 2010-12-09 |
| JP5405902B2 true JP5405902B2 (en) | 2014-02-05 |
Family
ID=43422534
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009128799A Active JP5405902B2 (en) | 2009-05-28 | 2009-05-28 | Whitening agent, whitening cosmetic, and method for producing whitening agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP5405902B2 (en) |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3135943B2 (en) * | 1990-10-11 | 2001-02-19 | 株式会社コーセー | Whitening agent |
| JPH04300812A (en) * | 1991-03-29 | 1992-10-23 | Maruzen Pharmaceut Co Ltd | Costmetic |
| JPH07126149A (en) * | 1993-10-28 | 1995-05-16 | Suntory Ltd | Cosmetic composition for beautifying and whitening |
| JP3660692B2 (en) * | 1993-11-18 | 2005-06-15 | 株式会社ノエビア | Tyrosinase biosynthesis inhibitor and whitening agent comprising the same |
| JP3445110B2 (en) * | 1997-08-15 | 2003-09-08 | 高砂香料工業株式会社 | Melanin production inhibitor |
| JPH11228339A (en) * | 1998-02-13 | 1999-08-24 | Ichimaru Pharcos Co Ltd | Melanin generation suppresser and preparation for external use for skin |
| JP5307369B2 (en) * | 2007-08-21 | 2013-10-02 | 株式会社コーセー | Whitening agent, whitening cosmetic, and method for producing whitening agent |
-
2009
- 2009-05-28 JP JP2009128799A patent/JP5405902B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP2010275227A (en) | 2010-12-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5599090B2 (en) | Type I collagen production promoter | |
| JP5307369B2 (en) | Whitening agent, whitening cosmetic, and method for producing whitening agent | |
| JP5008168B2 (en) | Anti-aging agent and skin cosmetics | |
| JP4869469B2 (en) | Melanin production promoter and gray hair improving agent | |
| JP5405902B2 (en) | Whitening agent, whitening cosmetic, and method for producing whitening agent | |
| JP2012046457A (en) | Cosmetic containing extract derived from kudzu root | |
| JP2012031086A (en) | Antioxidant and cosmetic material | |
| JP2008214335A (en) | Sparassis crispa extract, biaryl compound and cosmetic | |
| JP2006316029A (en) | Endothelin-1 production inhibitor and melanin production inhibitor | |
| KR101794343B1 (en) | Method for culture product of adenium obesum callus, culture product of adenium obesum callus, and cosmetic composition comprising the same | |
| CN108348449B (en) | Anti-aging skin external composition containing extract of germinated semi-wild soybean as effective component | |
| CN113101253A (en) | Cosmetic composition for improving skin comprising mixed extract of edible flowers | |
| KR20210026550A (en) | Cosmetic materials with excellent anti inflammation, antioxidant and skin whitening, Manufacturing method thereof and cosmetics containing the same | |
| KR102565298B1 (en) | Extracts of plant Containing High-Content of Taxifolin and Method for Producing the same | |
| KR102371164B1 (en) | Skin external composition for anti-aging containing germinated Glycine gracilis extract | |
| JP5946698B2 (en) | Whitening agent and skin cosmetics | |
| JP7222560B2 (en) | Cosmetic composition, beauty composition, joint protection composition, composition | |
| JP2011148732A (en) | Aquaporin 3 production promoter | |
| JP4994684B2 (en) | Moisturizer, cell activator, and antioxidant | |
| JP4520349B2 (en) | Cell activator and skin external preparation using the same | |
| JP2018070524A (en) | Epidermal cell activator | |
| JP2010215535A (en) | Melanin production-inhibiting agent | |
| TWI754618B (en) | Skin external composition for anti-aging containing germinated glycine gracilis extract | |
| JP2001329290A (en) | Cosmetic preparation | |
| JP4261413B2 (en) | Melanin production inhibitor |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20120222 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20130527 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130702 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130902 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20131008 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20131031 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5405902 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |