JP5350656B2 - Antioxidant or active oxygen scavenger, and perfume composition and cosmetics containing the same - Google Patents
Antioxidant or active oxygen scavenger, and perfume composition and cosmetics containing the same Download PDFInfo
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Abstract
Description
本発明は、優れた抗酸化能または活性酸素消去能を有する天然物由来の新規化合物について、当該新規化合物を有効成分とする抗酸化剤または活性酸素消去剤、およびそれらが配合された香粧品用香料組成物、化粧料に関する。 The present invention relates to a novel compound derived from a natural product having an excellent antioxidant ability or active oxygen scavenging ability, an antioxidant or an active oxygen scavenger containing the novel compound as an active ingredient, and a cosmetic containing the same. The present invention relates to a fragrance composition and a cosmetic.
老化した皮膚では過酸化脂質が増大し、柔軟性、弾力性を失い、皮膚のしわが増大し、乾燥して滑らかさのない荒れ肌症状が認められている。これらの皮膚症状が現れる原因物質の一つとして、大気中の酸素が紫外線や酵素等の影響を受けて生成するいわゆる活性酸素が考えられている。この活性酸素は、呼吸によって体内に入る酸素によっても、さらには喫煙、ストレス、怒り、不安、恐怖などの激しい感情、暴飲・暴食などでも発生すると言われている。 In aged skin, lipid peroxide increases, softness and elasticity are lost, wrinkles of the skin increase, and dry and rough skin symptoms are not smooth. As one of the causative substances in which these skin symptoms appear, so-called active oxygen is considered that oxygen in the atmosphere is generated under the influence of ultraviolet rays or enzymes. This active oxygen is said to be generated not only by oxygen entering the body by breathing, but also by intense emotions such as smoking, stress, anger, anxiety and fear, violent drinking and eating.
活性酸素には、フリーラジカルであるスーパーオキシドやヒドロキシラジカルといったものと、非ラジカルである一重項酸素や過酸化水素といったものがある。この活性酸素は、必要以上に体内外に存在すると、正常な細胞、細胞膜そしてＤＮＡにも作用し破壊する。また脂質をも酸化するため過酸化脂質を生成する。これにより、アトピー症状の悪化、白内障、中風、心筋梗塞、発ガンなど様々な疾病をも誘発する。生体に対しては、コラーゲン線維の架橋、ヒアルロン酸の断片化、ＤＮＡ螺旋の部分開裂、連鎖的ラジカルの発生による組織の損傷等の悪影響を及ぼし、その結果として皮膚のしわや弾力消失、脱毛といった生体の老化を促進するといわれている。 Active oxygen includes free radicals such as superoxide and hydroxy radicals, and non-radicals such as singlet oxygen and hydrogen peroxide. If this active oxygen is present inside and outside the body more than necessary, it also acts on normal cells, cell membranes, and DNA to destroy them. It also produces lipid peroxides because it oxidizes lipids. This also induces various diseases such as worsening atopic symptoms, cataracts, middle winds, myocardial infarction, and carcinogenesis. For the living body, it has adverse effects such as cross-linking of collagen fibers, fragmentation of hyaluronic acid, partial cleavage of DNA helix, tissue damage due to generation of chain radicals, resulting in skin wrinkles, loss of elasticity, hair loss, etc. It is said to promote aging of the living body.
従って活性酸素の生成を抑制することは、皮膚の老化を改善したり予防したりする点で、皮膚や生体内の組織等を正常に保つためにも非常に重要なことである。これは老化防止皮膚化粧料に求められる重要な要素である。そのため、従来生体内に発生した活性酸素を消去する作用のある物質の探索が広く行われてきた。 Therefore, suppressing the production of active oxygen is very important in order to improve or prevent skin aging and to keep the skin and tissues in the living body normal. This is an important factor required for anti-aging skin cosmetics. Therefore, the search of the substance which has the effect | action which erase | eliminates the active oxygen conventionally generated in the living body has been performed widely.
この様な作用を有する物質として従来用いられてきたものとしては、天然由来のものでは脂溶性のトコフェロール（ビタミンＥ）、水溶性のアスコルビン酸（ビタミンＣ）、合成化合物ではＢＨＴ（ブチルヒドロキシトルエン）、ＢＨＡ（ブチルヒドロキシアニソール）等が挙げられる。また、植物抽出物の中にも抗酸化効果を有するものがあり、化粧料に配合して皮膚の老化を防止しようとする試みがなされてきた。（例えば、特許文献１〜４参照。）
しかしながら、各種の植物抽出物は安全性の面において懸念されるものもあり、また活性酸素消去能が十分ではなかったり、化粧料等の皮膚外用剤の基剤中に配合した場合、有効な効果を得るにはかなりの高濃度を配合しなければならず、製剤に好ましくない臭いを付与してしまったりする場合があるなど、作用効果や安定性の面ですべてを満足できるものが少ないのが現状であった。 However, there are some plant extracts that are concerned about safety, and the active oxygen scavenging ability is not sufficient, or when it is formulated in a base for external preparations such as cosmetics, it has an effective effect. There are few things that can satisfy all in terms of action effect and stability, such as adding a rather bad odor to the preparation, so that a high concentration must be blended to obtain It was the current situation.
上記事情において、安全性が高く、また抗酸化作用が高く、さらに生体内に発生する活性酸素を消去する作用を十分に有し、化粧料への適用性の良好な新規抗酸化剤、活性酸素消去剤が求められていた。 In the above circumstances, a novel antioxidant, active oxygen, which has high safety, high antioxidant action, has sufficient action to eliminate active oxygen generated in the living body, and has good applicability to cosmetics There was a need for an eraser.
そこで、本発明の目的とするところは、抗酸化効果または活性酸素消去効果に優れた新規抗酸化剤または新規活性酸素消去剤、あるいはそれらが配合された香粧品用香料組成物、化粧料を提供することにある。 Accordingly, the object of the present invention is to provide a novel antioxidant or novel active oxygen scavenger excellent in antioxidant effect or active oxygen scavenging effect, or a perfume composition for cosmetics and cosmetics containing them. There is to do.
そこで、本発明者等は上記事情に鑑み鋭意研究した結果、下記化学式で表される化合物が優れた抗酸化効果または活性酸素消去効果を有することを見出し、本発明を完成したものである。
即ち、本発明は、下記化学式
Thus, as a result of intensive studies in view of the above circumstances, the present inventors have found that a compound represented by the following chemical formula has an excellent antioxidant effect or active oxygen scavenging effect, and completed the present invention.
That is, the present invention has the following chemical formula:
本発明の化合物は優れた抗酸化効果、活性酸素消去効果を有する。本発明の抗酸化剤または活性酸素消去剤は植物抽出物から単離されたものであって安全性が高く、非常に優れた抗酸化効果・活性酸素消去効果を発揮する。従って、酸化や活性酸素が関与する生体の各種問題を予防または低減するのに有用である。また、前記抗酸化剤または活性酸素消去剤を配合した本発明の香粧品用香料組成物は、安全性や抗酸化効果、活性酸素消去効果などに加え、バラエティの広い魅力的な香りを発現できる優れたものである。更に、前記抗酸化剤、活性酸素消去剤または香粧品用香料組成物を配合した本発明の化粧料は、従来の抗酸化剤の使用量を大幅に削減できる。また各種原料の酸化を防止して品質の劣化を抑制すると共に、優れた活性酸素消去効果を有する。従って、肌に適用した場合には肌荒れを防止し、肌のつや、はり、明るさを保ち、しわを改善する等、いわゆる皮膚老化防止効果に優れている。 The compound of the present invention has an excellent antioxidant effect and active oxygen scavenging effect. The antioxidant or active oxygen scavenger of the present invention is isolated from a plant extract, has high safety, and exhibits a very excellent antioxidant effect / active oxygen scavenging effect. Therefore, it is useful for preventing or reducing various problems of living bodies involving oxidation and active oxygen. Moreover, the fragrance composition for cosmetics of the present invention containing the antioxidant or active oxygen scavenger can exhibit a wide variety of attractive fragrances in addition to safety, antioxidant effect, active oxygen scavenging effect, etc. It is excellent. Furthermore, the cosmetic of the present invention containing the antioxidant, active oxygen scavenger or cosmetic fragrance composition can greatly reduce the amount of conventional antioxidant used. In addition, it prevents oxidation of various raw materials to suppress deterioration of quality and has an excellent active oxygen scavenging effect. Therefore, when applied to the skin, it is excellent in so-called skin aging preventing effects such as preventing rough skin, maintaining skin gloss, elasticity, brightness and improving wrinkles.
本発明の化合物は、アヤメ属植物であるサフランの花全体もしくは雌しべの抽出物から分離・精製することにより単離することができる。また、合成品としても入手することができる。本発明の化合物の抽出方法は、例えばサフランの花全体の抽出物を各種の溶媒、即ち液化ガス（液体炭酸、液化プロパン、液化ブタン等）、水、炭素数１〜５の低級アルコール類（メチルアルコール、エチルアルコール、プロピルアルコール等）、含水低級ア
ルコール類、炭素数１〜５の低級アルコールと炭素数１〜５の脂肪酸とのエステル類（酢酸メチル、酢酸エチル、酢酸ブチル等）、ケトン類（アセトン、メチルエチルケトン等）、前記エステル類およびケトン類の含水物、ハロゲン化炭化水素類（クロロホルム、ジクロロメタン、ジクロロエタン、トリクロロエタン等）、エーテル類（メチルエーテル、エチルエーテル、テトラヒドロフラン、ジオキサン等）、炭化水素類（石油エーテル、ヘキサン等）あるいは前記溶媒の混合物で抽出して得た抽出液を、酸、アルカリ処理、カラムクロマトグラフィー、蒸留、濃縮等により得ることができる。
The compound of the present invention can be isolated by separating and purifying from the whole saffron flower or pistil extract which is a genus plant. It can also be obtained as a synthetic product. The method for extracting a compound of the present invention includes, for example, extracting an entire saffron flower extract with various solvents, that is, liquefied gas (liquid carbonic acid, liquefied propane, liquefied butane etc.), water, lower alcohols having 1 to 5 carbon atoms (methyl Alcohol, ethyl alcohol, propyl alcohol, etc.), hydrous lower alcohols, esters of lower alcohols having 1 to 5 carbon atoms and fatty acids having 1 to 5 carbon atoms (methyl acetate, ethyl acetate, butyl acetate, etc.), ketones ( Acetone, methyl ethyl ketone, etc.), hydrates of the esters and ketones, halogenated hydrocarbons (chloroform, dichloromethane, dichloroethane, trichloroethane, etc.), ethers (methyl ether, ethyl ether, tetrahydrofuran, dioxane, etc.), hydrocarbons (Petroleum ether, hexane, etc.) or a mixture of the above solvents The extract obtained out, acid, alkali treatment, column chromatography, distillation, can be obtained by concentration or the like.
本発明の化合物を含有するＣｒｏｃｕｓ ｓａｔｉｖｕｓ Ｌ．は、サフランと俗称され、その抽出物は独特のメディシナル（薬品的）な臭気を有する。そのため、Ｃｒｏｃｕｓ ｓａｔｉｖｕｓ Ｌ．の抽出物等の使用に際しては、そのメディシナル臭が原因となり最終製品に好ましくない臭気特徴を与えるため、化粧料等においてもその使用が不可能であるか、もしくは大きな阻害要因となっていた。従って配合するにも少量とする必要があったり、そもそもＣｒｏｃｕｓ ｓａｔｉｖｕｓ Ｌ．の抽出物は、本発明の化合物に比較してその効果が高くないことから、期待する抗酸化能や活性酸素消去能は得られなかった。 Crocus sativus L. containing the compounds of the present invention. Is commonly referred to as saffron, and its extract has a unique medicinal odor. Therefore, Crocus sativus L. In the use of the extract or the like, the medicinal odor causes unpleasant odor characteristics to the final product, so that it cannot be used in cosmetics or the like, or has been a major hindrance factor. Therefore, it is necessary to use a small amount for blending, and in the first place Crocus sativus L. This extract was not effective as compared with the compound of the present invention, and thus the expected antioxidant ability and active oxygen scavenging ability were not obtained.
それに対し、本発明の化合物はほとんど香りを有しておらず、かつ抗酸化効果や活性酸素消去効果が著しく高いため、上記問題を全く生じなく、本発明の目的を達成することが可能となる。 On the other hand, since the compound of the present invention has almost no fragrance and has an extremely high antioxidant effect and active oxygen scavenging effect, the above-mentioned problems do not occur at all and the object of the present invention can be achieved. .
本発明の化合物を産業上利用するためには、必ずしも不純物が全く含まれない状態に精製する必要はなく、本発明の抗酸化剤中または活性酸素消去剤中において本発明化合物を０．００００１質量％（以下、単に％と表現する）以上含有されていればよい。 In order to use the compound of the present invention industrially, it is not always necessary to purify the compound to be completely free of impurities, and 0.00001 mass of the compound of the present invention is contained in the antioxidant or active oxygen scavenger of the present invention. % (Hereinafter simply expressed as%) may be contained.
本発明の香粧品用香料組成物中への抗酸化剤または活性酸素消去剤の配合量は、香粧品用香料組成物の使用目的、種類などにより異なるが、本発明化合物の含有量として香粧品用香料組成物中に０．０００１〜２０％であり、好ましくは０．００１〜５％である。この範囲であれば、期待する抗酸化効果や活性酸素消去効果を得るとことができ、また臭いや安全性の面でも好ましい。 The blending amount of the antioxidant or active oxygen scavenger in the fragrance composition for cosmetics of the present invention varies depending on the purpose and type of use of the fragrance composition for cosmetics, but the content of the compound of the present invention is a cosmetic product. It is 0.0001 to 20% in a fragrance composition for use, preferably 0.001 to 5%. Within this range, the expected antioxidant effect and active oxygen scavenging effect can be obtained, and it is also preferable in terms of odor and safety.
本発明の香粧品用香料組成物は、有効な抗酸化効果を有すると共に、バラエティの広い魅力的な香りを発現することが可能となる。本発明の香粧品用香料組成物中へは、本発明の抗酸化剤、活性酸素消去剤以外に、公知の香料素材や溶剤が用いられる。例えばリモネン、カリオフィレン、ピネンなどの各種炭化水素類；アセトアルデヒド、α−シンナミックアルデヒド、シトラ−ルなどの各種アルデヒド類；マルト−ル、ベンジルアセトン、ダマセノンなどの各種ケトン類；ブタノ−ル、ベンジルアルコ−ル、リナロ−ルなどの各種アルコ−ル類；ゲラニルエチルエ−テル、ロ−ズオキサイド、フルフラ−ルなどの各種エ−テル・オキサイド類；エチルアセテ−ト、ベンジルアセテ−ト、リナリルアセテ−トなどの各種エステル類；γ−デカラクトン、クマリン、スクラレオライドなどの各種ラクトン類；インド−ル、２−イソプロピル−４−メチルチアゾ−ル、フェニルアセトニトリルなどの各種ヘテロ化合物類；ジャスミンアブソリュ−ト、シダ−ウッドオイル、オリスコンクリ−トなどの各種天然素材類が挙げられる。使用する溶剤としては、例えばエタノ−ル、ジプロピレングリコ−ル（ＤＰＧともいう）、ベンジルベンゾエ−ト、水、トリアセチン、トリエチルシトレ−トなどが挙げられる。 The fragrance composition for cosmetics of the present invention has an effective antioxidant effect and can express a wide variety of attractive fragrances. In addition to the antioxidant and active oxygen scavenger of the present invention, known fragrance materials and solvents are used in the fragrance composition for cosmetics of the present invention. For example, various hydrocarbons such as limonene, caryophyllene, and pinene; various aldehydes such as acetaldehyde, α-cinnamic aldehyde, citral; various ketones such as maltol, benzylacetone, and damasenone; butanol, benzylalcohol Various alcohols such as quinol and linalol; various ether oxides such as geranyl ethyl ether, rose oxide and furfural; ethyl acetate, benzyl acetate and linalyl acetate Various esters such as γ-decalactone, coumarin and sclareolide; various hetero compounds such as indol, 2-isopropyl-4-methylthiazol and phenylacetonitrile; jasmine absolute, fern -Wood oil, Oris concrete, etc. Various natural materials are listed. Examples of the solvent to be used include ethanol, dipropylene glycol (also referred to as DPG), benzyl benzoate, water, triacetin, triethyl citrate and the like.
本発明の抗酸化剤または活性酸素消去剤、あるいは本発明の香粧品用香料組成物を化粧料へ配合する場合、その配合量は、化粧料の使用目的、種類などにより異なるが、本発明化合物の含有量として０．００００１〜２０％、更には０．０００１〜５％が好ましい。この範囲であれば、期待する抗酸化効果や活性酸素消去効果を得るとことができ、また臭
いや安全性の面でも好ましい。
When the antioxidant or active oxygen scavenger of the present invention or the perfume composition for cosmetics of the present invention is blended in cosmetics, the blending amount varies depending on the purpose and type of cosmetics used, but the compound of the present invention The content of is preferably 0.00001 to 20%, more preferably 0.0001 to 5%. Within this range, the expected antioxidant effect and active oxygen scavenging effect can be obtained, and it is also preferable in terms of odor and safety.
本発明の化粧料には、油脂、ロウ類、炭化水素、高級脂肪酸、高級アルコール、エステル類、その他の油性原料、グリセリン等の多価アルコール、界面活性剤、増粘剤等の通常用いられている成分が使用され、これら公知の化粧料用素材と本発明の抗酸化剤、活性酸素消去剤または香粧品用香料組成物を用いて通常の製造法で得ることが出来る。また、必要に応じて公知の酸化防止剤（ビタミンＣ、ビタミンＥ等）、活性酸素消去剤等を併用してもよい。 In the cosmetics of the present invention, oils, waxes, hydrocarbons, higher fatty acids, higher alcohols, esters, other oily raw materials, polyhydric alcohols such as glycerin, surfactants, thickeners and the like are usually used. The known ingredients for cosmetics and the antioxidants, active oxygen scavengers or fragrance compositions for cosmetics of the present invention can be used to obtain them by ordinary production methods. Moreover, you may use together well-known antioxidant (vitamin C, vitamin E, etc.), an active oxygen scavenger, etc. as needed.
また化粧料の剤型も任意であり、例えば溶液系、可溶化系、乳化系、エアゾール等がある。更に、化粧料の用途も任意であり、例えば化粧水、乳液、クリーム、パック等のフェイシャル化粧料やファンデーション、口紅、アイシャドウ等のメイクアップ化粧料、芳香化粧料、シャンプー等の洗髪用化粧料、毛髪仕上げ用化粧料、ボディー化粧料、口腔用化粧料、入浴化粧料等がある。本発明の化粧料は抗酸化性が高いので、従来の化粧料に添加されていた抗酸化剤の添加を大幅に削減することが出来る。従って、敏感肌の一部の化粧料使用者における合成抗酸化剤の配合に起因する刺激感の低減も可能である。また、本発明のスキンローションや入浴剤は、肌荒れを防止し、肌のつや、はり、明るさを保ち、しわを改善する効果に優れるので、皮膚老化防止用の化粧料として用いるとより良い効果が期待できる。 The dosage form of the cosmetic is also arbitrary, and examples include a solution system, a solubilization system, an emulsification system, and an aerosol. Furthermore, the use of cosmetics is also optional, for example, facial cosmetics such as lotions, emulsions, creams and packs, makeup cosmetics such as foundations, lipsticks and eye shadows, cosmetics for hair washing such as aromatic cosmetics and shampoos. , Hair finishing cosmetics, body cosmetics, oral cosmetics, bath cosmetics, and the like. Since the cosmetics of the present invention have high antioxidant properties, the addition of antioxidants that have been added to conventional cosmetics can be greatly reduced. Accordingly, it is possible to reduce the irritation caused by the blending of the synthetic antioxidants in some cosmetic users who have sensitive skin. In addition, the skin lotion and bathing agent of the present invention have excellent effects of preventing rough skin, maintaining skin gloss, elasticity, brightness, and improving wrinkles. Can be expected.
以下、本発明の化合物等について、単離例、試験例および実施例に基づいて説明するが、本発明はこれらに限定されるものではない。 Hereinafter, although the compound etc. of this invention are demonstrated based on an isolation example, a test example, and an Example, this invention is not limited to these.
（単離）
Ｃｒｏｃｕｓ ｓａｔｉｖｕｓ Ｌ．の乾燥した雌しべ１００グラムをエチルアルコール１リットルに室温で浸漬して花香成分および抗酸化成分を移行させた後、雌しべを除いた。次に、溶媒を留去して抽出物１０グラムを得た。この抽出物はメディシナル臭を有していた。
次に上記抽出物１０グラムを、ｎ−ヘキサン／酢酸エチル＝１：１（Ｖ／Ｖ）〜酢酸エチル／メタノール＝１：１（Ｖ／Ｖ）の移動相を用いて常法に従いシリカゲルカラムクロマトグラフィーを行い、精製することにより、当該化合物２−ｈｙｄｒｏｘｙ−３，５，５−ｔｒｉｍｅｔｈｙｌ−２−ｃｙｃｌｏｈｅｘｅｎｏｎｅを得た。この臭いは、仄かに甘く弱いスパイシー調の香りを有していた。
ＭＳスペクトルデータは以下である。
(Isolation)
Crocus sativus L. 100 grams of dried pistil was soaked in 1 liter of ethyl alcohol at room temperature to transfer the fragrance component and antioxidant component, and then the pistil was removed. Next, the solvent was distilled off to obtain 10 grams of an extract. This extract had a medicinal odor.
Next, 10 grams of the above extract was subjected to silica gel column chromatography using a mobile phase of n-hexane / ethyl acetate = 1: 1 (V / V) to ethyl acetate / methanol = 1: 1 (V / V) according to a conventional method. The compound 2-hydroxy-3,5,5-trimethyl-2-cyclohexenone was obtained by performing chromatography and purification. This smell had a much sweeter and weaker spicy scent.
The MS spectrum data is as follows.
（精製品）
ＭＳ（ｍ／ｚ）：１５４（Ｍ＋）、１５４,７０，９８，１３９，５５，１１１，４１，８３
(Fine products)
MS (m / z): 154 (M +), 154, 70, 98, 139, 55, 111, 41, 83
（試験例１：活性酸素消去効果試験（ＤＰＰＨ法））
活性酸素を消去する効果を測定する方法は各種あるが、今回は有機ラジカルである１，１−ジフェニル−２−ピクリルヒドラジル（ＤＰＰＨ）消去能を測定した。方法は以下に示す通りである。即ち、９６ウェルマイクロプレートに１００ｍｍｏｌ／Ｌトリス緩衝液（ｐＨ７．５、和光純薬）を８０μｌ、９９．５％メタノール（純正化学）にて濃度調製した各試料溶液を２０μｌ、９９．５％メタノール（純正化学）にて濃度調製した０．５ｍｍｏｌ／Ｌ ＤＰＰＨ(和光純薬)を１００μｌ加えた後攪拌し、遮光の状態で室温で２０分間インキュベートした。その後、分光光度計（Ｍｕｌｔｉ−Ｓｐｅｃｔｒｏｐｈｔｏｍｅｔｅｒ Ｖｉｅｎｔ ＸＳ／大日本住友ファーマ）にて５１７ｎｍの吸光度Ａを測定した。一方、ＤＰＰＨを加えないもの（ブランク）とサンプルを加えないもの（コントロ
ール）で同様の操作を行い、得られた吸光度（それぞれＢとＣ）を測定し、活性酸素消去率（％）を得た。
(Test Example 1: Active oxygen scavenging effect test (DPPH method))
There are various methods for measuring the effect of scavenging active oxygen, but this time, the ability to scavenge 1,1-diphenyl-2-picrylhydrazyl (DPPH), an organic radical, was measured. The method is as follows. That is, 20 μl, 99.5% methanol of each sample solution prepared by concentrating 100 mmol / L Tris buffer solution (pH 7.5, Wako Pure Chemical Industries) with 80 μl, 99.5% methanol (Pure Chemical) on a 96-well microplate. After adding 100 μl of 0.5 mmol / L DPPH (Wako Pure Chemical Industries), whose concentration was adjusted by (Pure Chemical), the mixture was stirred and incubated at room temperature for 20 minutes in the dark. Then, the absorbance A at 517 nm was measured with a spectrophotometer (Multi-Spectrophotometer Vient XS / Dainippon Sumitomo Pharma). On the other hand, the same operation was performed with the sample without DPPH (blank) and the sample without control (control), and the obtained absorbance (B and C, respectively) was measured to obtain the active oxygen elimination rate (%). .
（ＩＣ５０計算式）
活性酸素消去率（％）＝｛１−（Ａ−Ｂ）／Ｃ｝×１００
（但し、Ａ：サンプルの吸光度、Ｂ：ブランクの吸光度、Ｃ：コントロールの吸光度）
(IC 50 calculation formula)
Active oxygen elimination rate (%) = {1− (A−B) / C} × 100
(However, A: Absorbance of sample, B: Absorbance of blank, C: Absorbance of control)
同様に表１に示す各試料を用い試験を行った。横軸に濃度、縦軸に活性酸素消去率をプロットしたグラフを作成し、このグラフから活性酸素を５０％抑制する濃度(以後、ＩＣ５０と表す。)を求めた。 Similarly, each sample shown in Table 1 was tested. A graph was prepared by plotting the concentration on the horizontal axis and the active oxygen elimination rate on the vertical axis, and from this graph, the concentration at which active oxygen was suppressed by 50% (hereinafter referred to as IC 50 ) was determined.
結果を表１に示す。
活性酸素消去効果試験（ＤＰＰＨ法）とＩＣ５０の結果
The results are shown in Table 1.
Active oxygen scavenging effect test (DPPH method) and IC 50 results
上記の結果から、本発明の抗酸化剤または活性酸素消去剤は、汎用されている天然系抗酸化剤であるＤＬ−α−トコフェロールや香料の中でも高い抗酸化性を有すると言われているローズマリーオイルアブソリュートと同程度の優れた抗酸化能を有することがわかる。 From the above results, the antioxidant or active oxygen scavenger of the present invention is said to have a high antioxidant property among DL-α-tocopherol and fragrance, which are natural antioxidants that are widely used. It can be seen that it has an excellent antioxidant ability comparable to that of Marie Oil Absolute.
処方例１（香料処方例１、香料比較例１）
本発明の抗酸化剤（活性酸素消去剤でもある）を配合して、下記処方のハーブ系調合香料を作製した。
Formulation Example 1 (Fragrance Formulation Example 1, Fragrance Comparison Example 1)
An antioxidant (which is also an active oxygen scavenger) of the present invention was blended to prepare a herbal blended fragrance having the following formulation.
処方例２（香料処方例２、香料比較例２）
本発明の抗酸化剤（活性酸素消去剤でもある）を配合して、下記処方のフローラル系調合香料を作製した。
Formulation Example 2 (Fragrance Formulation Example 2, Fragrance Comparison Example 2)
The antioxidant of the present invention (which is also an active oxygen scavenger) was blended to produce a floral blended fragrance having the following formulation.
実施例３〜５及び比較例３〜５（スキンローション）
表４記載の組成のスキンローションを、下記方法に従い調製した。
（スキンローションの調製法）
水相、アルコール相を各々均一に溶解し、そして水相とアルコール相とを混合攪拌分散し可溶化を行い、次いで容器に充填する。使用時には内容物を均一に振盪分散して使用する。
Examples 3-5 and Comparative Examples 3-5 (Skin Lotion)
Skin lotions having the compositions described in Table 4 were prepared according to the following method.
(Skin lotion preparation method)
The aqueous phase and the alcohol phase are uniformly dissolved, and the aqueous phase and the alcohol phase are mixed, stirred and dispersed to effect solubilization, and then filled into a container. In use, the contents are uniformly shaken and dispersed.
上記で調製したスキンローションを用いて使用試験を行い、皮膚老化防止効果を調べた。試験方法は下記に示す通りである。 A use test was conducted using the skin lotion prepared above, and the anti-skin aging effect was examined. The test method is as shown below.
（試験方法）
６０名の女性被験者の顔面を左右に分け、一方に上記の実施例３〜５、他方に実施例３に対しては比較例３のスキンローション、実施例４に対しては比較例４のスキンローション、そして実施例５に対しては比較例５のスキンローションを毎日２回以上塗布してもらい、２ヵ月後それぞれの比較例を基準として下記の判定基準により各評価項目について評点を出してもらい、評点の合計値により評価した。被験者を１群２０名の３群に分け、実施例３〜５の各スキンローション３種を各群に割り当て試験を行った。その結果を表５に示す。
(Test method)
The face of 60 female subjects is divided into left and right, one of the above examples 3 to 5, the other is the skin lotion of comparative example 3 for example 3, and the skin of comparative example 4 for example 4. For the lotion and Example 5, the skin lotion of Comparative Example 5 was applied at least twice daily, and after 2 months, each comparative item was scored for each evaluation item based on the following criteria. The evaluation was based on the total score. The test subjects were divided into 3 groups of 20 people per group, and each skin lotion of Examples 3 to 5 was assigned to each group for testing. The results are shown in Table 5.
（判定基準）
＋３：比較例３〜５よりも実施例３〜５の方が非常によい
＋２：比較例３〜５よりも実施例３〜５の方がかなりよい
＋１：比較例３〜５よりも実施例３〜５の方がややよい
０：差がない
−１：比較例３〜５の方が実施例３〜５よりもややよい
−２：比較例３〜５の方が実施例３〜５よりもかなりよい
−３：比較例３〜５の方が実施例３〜５よりも非常によい
(Criteria)
+3: Examples 3-5 are much better than Comparative Examples 3-5 +2: Examples 3-5 are much better than Comparative Examples 3-5 +1: Examples over Comparative Examples 3-5 3-5 is slightly better 0: No difference -1: Comparative Examples 3-5 are slightly better than Examples 3-5 -2: Comparative Examples 3-5 are better than Examples 3-5 -3: Comparative Examples 3 to 5 are much better than Examples 3 to 5
表５より明らかなように、本発明の抗酸化剤、活性酸素消去剤または香粧品用香料組成物を有効成分として含有するスキンローションは、肌荒れを防止し、肌のつや、はり、明るさを保ち、しわを改善する効果に優れ、皮膚老化防止用化粧料として用いることができる。 As is apparent from Table 5, skin lotion containing the antioxidant, active oxygen scavenger or cosmetic fragrance composition of the present invention as an active ingredient prevents rough skin, and improves skin gloss, elasticity and brightness. It is excellent in the effect of keeping and improving wrinkles, and can be used as a cosmetic for preventing skin aging.
実施例６〜８及び比較例６：入浴剤
下記組成の入浴剤を、常法に従い調製した。尚、この入浴剤は使用時に約３０００倍に希釈される。
Examples 6 to 8 and Comparative Example 6: Bathing agent Bathing agents having the following compositions were prepared according to a conventional method. In addition, this bath agent is diluted about 3000 times at the time of use.
上記入浴剤を６０名の被験者全員に三週間毎日の入浴時に比較例６の入浴剤を使用させた。その後、被験者を１群２０名の３群に分け、各群に実施例６〜８を割り当て、比較例６に引き続き実施例６〜８の各入浴剤を使用させた。そして、比較例６を基準として下記の判定基準により各評価項目について評点を出してもらい、評点の合計値により評価した。 All 60 subjects used the bathing agent of Comparative Example 6 when bathing every day for three weeks. Thereafter, the subjects were divided into 3 groups of 20 people per group, Examples 6 to 8 were assigned to each group, and each bath agent of Examples 6 to 8 was used following Comparative Example 6. Then, using Comparative Example 6 as a reference, each evaluation item was scored according to the following criteria, and the evaluation was made based on the total value of the scores.
（判定基準）
＋３：比較例６よりも実施例６〜８の方が改善され非常によい
＋２：比較例６よりも実施例６〜８の方がかなり改善された
＋１：比較例６よりも実施例６〜８の方がやや改善された
０：差がない
−１：比較例６の方が実施例６〜８よりもややよい
−２：比較例６の方が実施例６〜８よりもかなりよい
−３：比較例６の方が実施例６〜８よりも非常によい
(Criteria)
+3: Examples 6 to 8 were improved and much better than Comparative Example 6 +2: Examples 6 to 8 were significantly improved compared to Comparative Example 6 +1: Examples 6 to 6 than Comparative Example 6 8 is slightly improved 0: No difference -1: Comparative Example 6 is slightly better than Examples 6-8 -2: Comparative Example 6 is considerably better than Examples 6-8- 3: Comparative Example 6 is much better than Examples 6-8
表７より明らかなように、本発明の抗酸化剤、活性酸素消去剤または香粧品用香料組成物を有効成分として含有する入浴剤は、肌荒れを防止し、肌のつや、はり、明るさを保ち、しわを改善する効果に優れ、皮膚老化防止用入浴剤として用いることができる。尚、前記実施例に係るスキンローション及び入浴剤による発赤や乾燥等の異常は認められなかった。
As is clear from Table 7, the bath containing the antioxidant, active oxygen scavenger or cosmetic fragrance composition of the present invention as an active ingredient prevents rough skin, and gives the skin gloss, elasticity and brightness. It is excellent in the effect of keeping and improving wrinkles, and can be used as a bath agent for preventing skin aging. In addition, abnormalities such as redness and drying due to the skin lotion and bathing agent according to the above examples were not observed.
本発明の化合物は抗酸化剤、活性酸素消去剤の有効成分として有用である。また本発明の抗酸化剤、活性酸素消去剤は、植物抽出物から単離されたものであって安全性が高く、非常に優れた抗酸化効果、活性酸素消去効果を発揮する。従って酸化や活性酸素が関与するあらゆる分野、例えば化粧料等に好適に用いることが出来る。また、本発明の香粧品用香料組成物は安全性や抗酸化効果、活性酸素消去効果などに加え、バラエティの広い魅力的な香りを発現するような優れたものであるので、化粧料等に好適に用いることが出来る。 The compounds of the present invention are useful as active ingredients for antioxidants and active oxygen scavengers. Further, the antioxidant and active oxygen scavenger of the present invention are isolated from plant extracts and have high safety and exhibit very excellent antioxidant effect and active oxygen scavenging effect. Therefore, it can be suitably used in all fields involving oxidation and active oxygen, such as cosmetics. In addition to the safety, antioxidant effect, active oxygen scavenging effect, etc., the perfume composition for cosmetics of the present invention is excellent in expressing a wide variety of attractive fragrances. It can be suitably used.
Claims (4)
で表される化合物２−ｈｙｄｒｏｘｙ−３，５，５−ｔｒｉｍｅｔｈｙｌ−２−ｃｙｃｌｏｈｅｘｅｎｏｎｅからなる抗酸化剤または活性酸素消去剤。 The following chemical formula
The antioxidant or active-oxygen scavenger which consists of compound 2-hydroxy-3,5,5-trimethyl-2-cyclohexenone represented by these.
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