JP2015067568A - Whitening agent and anti-photoaging agent comprising benzylideneazolidine derivative or salt thereof - Google Patents
Whitening agent and anti-photoaging agent comprising benzylideneazolidine derivative or salt thereof Download PDFInfo
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- JP2015067568A JP2015067568A JP2013202410A JP2013202410A JP2015067568A JP 2015067568 A JP2015067568 A JP 2015067568A JP 2013202410 A JP2013202410 A JP 2013202410A JP 2013202410 A JP2013202410 A JP 2013202410A JP 2015067568 A JP2015067568 A JP 2015067568A
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- 150000003839 salts Chemical class 0.000 title claims abstract description 51
- AGIBHTHSMHAQEM-UHFFFAOYSA-N 2-benzylidenepyrrolidine Chemical class C1CNC(C1)=Cc1ccccc1 AGIBHTHSMHAQEM-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 230000002087 whitening effect Effects 0.000 title claims abstract description 27
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- 125000000524 functional group Chemical group 0.000 claims description 96
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Abstract
Description
本発明は、ベンジリデンアゾリジン誘導体またはその塩を含む美白剤、抗光老化剤、チロシナーゼ阻害剤、メラニン産生抑制剤、活性酸素種生成抑制剤、SOD様活性剤、および、カタラーゼ様活性剤に関する。 The present invention relates to a whitening agent, an anti-photoaging agent, a tyrosinase inhibitor, a melanin production inhibitor, a reactive oxygen species production inhibitor, an SOD-like active agent, and a catalase-like active agent containing a benzylidene azolidine derivative or a salt thereof.
シミ、ソバカス、日焼け後の色素沈着、肝斑や雀卵斑、ソーラー・レンティゴ(日光黒子)等の皮膚症状等に代表される皮膚色の不均一化、しわ、たるみ、および、皮膚の菲薄化、肌荒れ等は、紫外線や炎症などの様々な刺激によって引き起こされる、光老化反応の一種と考えられている。従来考えられてきた主要な作用経路は、紫外線や活性酸素種(一重項酸素、スーパーオキシドアニオン、過酸化水素等)などがメラノサイトに直接作用することによりチロシナーゼの活性が増加し、その結果として、メラニン合成が促進されて色素沈着を惹起するというものであった。また、近年、紫外線や活性酸素種などにより引き起こされる炎症反応の結果として、しわ、たるみ等のような肌の老化現象が促進されることも報告されている。 Non-uniform skin color, wrinkles, sagging, and thinning of skin, such as skin spots such as spots, buckwheat, pigmentation after sunburn, liver spots and sparrow eggs, and solar lentigo (Nikko Kuroko) The rough skin is considered to be a kind of photoaging reaction caused by various stimuli such as ultraviolet rays and inflammation. The main route of action that has been considered in the past is that the activity of tyrosinase is increased by the direct action of ultraviolet rays and reactive oxygen species (singlet oxygen, superoxide anion, hydrogen peroxide, etc.) on melanocytes, Melanin synthesis was promoted to induce pigmentation. In recent years, it has also been reported that skin aging such as wrinkles and sagging is promoted as a result of an inflammatory reaction caused by ultraviolet rays or reactive oxygen species.
このような光老化反応を抑制する方法として、メラニン生成プロセスにおけるチロシナーゼ活性の阻害、メラニン生成の抑制、紫外線暴露により生成する活性酸素種の抑制および消去、ターンオーバ促進に基づくメラニン排出を促進させるために、皮膚の基底細胞の細胞分裂の活性化等を目的とするものが考えられる。 In order to suppress such photoaging reaction, to inhibit tyrosinase activity in the melanin production process, to suppress melanin production, to suppress and eliminate reactive oxygen species generated by UV exposure, and to promote melanin excretion based on accelerated turnover In addition, those intended for activation of cell division of the basal cells of the skin can be considered.
また、上記抑制作用を有する美白剤および抗光老化剤としては、これまでに、アスコルビン酸またはその誘導体、アルブチン、微生物抽出物、発酵生産物や植物抽出物が知られている。また、近年、たとえば、ヒヨドリラクトンA(特許文献1参照)、ヘスペリジン(特許文献2参照)、クリプトメリジオール(特許文献3参照)、チャフロサイドA(特許文献4参照)、ポゴズトン誘導体(特許文献5参照)等が報告されている。 Moreover, ascorbic acid or a derivative thereof, arbutin, a microbial extract, a fermentation product, and a plant extract are known as a whitening agent and an anti-photoaging agent having the above-described inhibitory action. In recent years, for example, hydridolactone A (see Patent Document 1), hesperidin (see Patent Document 2), cryptomellidiol (see Patent Document 3), chafuroside A (see Patent Document 4), pogozton derivative (see Patent Document 5) ) Etc. have been reported.
本発明は、新たな薬剤(美白剤、抗光老化剤、チロシナーゼ阻害剤、メラニン産生抑制剤、活性酸素種生成抑制剤、SOD(スーパーオキシドディスムターゼ)様活性剤、および、カタラーゼ様活性剤)を提供することを目的とする。 The present invention provides new drugs (whitening agents, anti-photoaging agents, tyrosinase inhibitors, melanin production inhibitors, reactive oxygen species production inhibitors, SOD (superoxide dismutase) -like activators, and catalase-like activators). The purpose is to provide.
本発明者らは、上記課題を解決するため鋭意検討した結果、以下に示す新規ベンジリデンアゾリジン誘導体またはその塩により上記目的を達成できることを見出して、本発明を完成するに至った。 As a result of intensive studies to solve the above problems, the present inventors have found that the above object can be achieved by the following novel benzylidene azolidine derivatives or salts thereof, and have completed the present invention.
すなわち、本発明の美白剤は、一般式(I)で表されるベンジリデンアゾリジン誘導体またはその塩を含むことを特徴とする。 That is, the whitening agent of the present invention is characterized by containing a benzylidene azolidine derivative represented by the general formula (I) or a salt thereof.
なお、本発明における美白剤とは、肌のくすみやしみ、肝斑等に特に関係しているメラニン色素等による皮膚の色素沈着を改善、抑制・低減・防止、予防、または、遅延させるものをいう。上記美白剤は、肌を白く保つ美白作用を有している。 The whitening agent in the present invention is an agent that improves, suppresses / reduces / prevents, prevents or delays skin pigmentation due to melanin pigments particularly related to dullness and itching of the skin and liver spots. Say. The whitening agent has a whitening effect that keeps the skin white.
また、本発明の抗光老化剤は、上記一般式(I)で表されるベンジリデンアゾリジン誘導体またはその塩を含むことを特徴とする。 The anti-photoaging agent of the present invention is characterized by containing a benzylidene azolidine derivative represented by the above general formula (I) or a salt thereof.
なお、本発明における抗光老化剤とは、紫外線や活性酸素種による、皮膚のしわ、たるみ、くすみ、しみ、くまなどの老化現象を改善、抑制・低減・防止、予防、または遅延をさせるものをいう。上記抗光老化剤は、紫外線による肌へのダメージを抑制する作用を有しており、皮膚の弾力性の低下、皮膚の黒化、黄ばみの増加、皮膚の糖化、角質水分量の減少等の光老化現象の抑制に優れたものである。 In addition, the anti-photoaging agent in the present invention is an agent that improves, suppresses, reduces, prevents, prevents or delays aging phenomena such as wrinkles, sagging, dullness, blotches, and bears caused by ultraviolet rays and reactive oxygen species. Say. The anti-photoaging agent has an action of suppressing damage to the skin by ultraviolet rays, such as skin elasticity reduction, skin blackening, yellowing increase, skin glycation, keratin water content reduction, etc. It is excellent in suppressing photoaging.
また、本発明のチロシナーゼ阻害剤は、上記一般式(I)で表されるベンジリデンアゾリジン誘導体またはその塩を含むことを特徴とする。 In addition, the tyrosinase inhibitor of the present invention is characterized by containing a benzylidene azolidine derivative represented by the above general formula (I) or a salt thereof.
なお、本発明におけるチロシナーゼ阻害剤とは、メラニン合成に関与するチロシナーゼの活性を阻害または低下させるものをいう。 The tyrosinase inhibitor in the present invention refers to an agent that inhibits or reduces the activity of tyrosinase involved in melanin synthesis.
また、本発明のメラニン産生抑制剤は、上記一般式(I)で表されるベンジリデンアゾリジン誘導体またはその塩を含むことを特徴とする。 Moreover, the melanin production inhibitor of this invention is characterized by including the benzylidene azolidine derivative represented by the said general formula (I), or its salt.
なお、本発明におけるメラニン産生抑制剤とは、メラニン産生を阻害または低下させるものをいう。 In addition, the melanin production inhibitor in this invention means what inhibits or reduces melanin production.
また、本発明の活性酸素種生成抑制剤は、上記一般式(I)で表されるベンジリデンアゾリジン誘導体またはその塩を含むことを特徴とする。 Moreover, the reactive oxygen species production inhibitor of the present invention is characterized by containing a benzylidene azolidine derivative represented by the above general formula (I) or a salt thereof.
なお、本発明における活性酸素種生成抑制剤とは、紫外線暴露等により生じる活性酸素種の生成を阻害または低下させるものをいう。また、紫外線暴露等により生じた活性酸素種を消去する機能も持ち合わせる。 In addition, the reactive oxygen species production inhibitor in the present invention refers to an agent that inhibits or reduces the production of reactive oxygen species caused by exposure to ultraviolet rays or the like. It also has a function to erase active oxygen species generated by UV exposure.
また、本発明のSOD様活性剤は、上記一般式(I)で表されるベンジリデンアゾリジン誘導体またはその塩を含むことを特徴とする。 The SOD-like activator of the present invention is characterized by containing a benzylidene azolidine derivative represented by the above general formula (I) or a salt thereof.
なお、本発明におけるSOD様活性剤とは、紫外線暴露などにより生じたスーパーオキシドアニオンの生成を阻害または低下させるものをいう。 The SOD-like active agent in the present invention refers to an agent that inhibits or reduces the production of superoxide anion caused by exposure to ultraviolet rays.
また、本発明のカタラーゼ様活性剤は、上記一般式(I)で表されるベンジリデンアゾリジン誘導体またはその塩を含むことを特徴とする。 The catalase-like active agent of the present invention is characterized by containing a benzylidene azolidine derivative represented by the above general formula (I) or a salt thereof.
なお、本発明におけるカタラーゼ様活性剤とは、紫外線暴露などにより生じた過酸化水素の生成を阻害または低下させるものをいう。 The catalase-like active agent in the present invention refers to an agent that inhibits or reduces the production of hydrogen peroxide generated by exposure to ultraviolet rays.
本発明の美白剤、抗光老化剤、チロシナーゼ阻害剤、メラニン産生抑制剤、活性酸素種生成抑制剤、SOD様活性剤、および、カタラーゼ様活性剤において、前記構造式(I)中、A2、A3およびA4のうち、少なくとも1つは、前記官能基(1)、前記官能基(2)、または前記官能基(3)とすることができる。 In the whitening agent, anti-photoaging agent, tyrosinase inhibitor, melanin production inhibitor, reactive oxygen species production inhibitor, SOD-like activator, and catalase-like activator of the present invention, A 2 in the structural formula (I) , A 3 and A 4 may be the functional group (1), the functional group (2), or the functional group (3).
本発明の美白剤、抗光老化剤、チロシナーゼ阻害剤、メラニン産生抑制剤、活性酸素種生成抑制剤、SOD様活性剤、および、カタラーゼ様活性剤において、前記構造式(I)中、A2および/またはA3が、水素原子、ヒドロキシル基で置換された炭素数1〜8のアルキル基、前記官能基(1)、前記官能基(2)、または前記官能基(3)とすることができる。 In the whitening agent, anti-photoaging agent, tyrosinase inhibitor, melanin production inhibitor, reactive oxygen species production inhibitor, SOD-like activator, and catalase-like activator of the present invention, A 2 in the structural formula (I) And / or A 3 may be a hydrogen atom, an alkyl group having 1 to 8 carbon atoms substituted with a hydroxyl group, the functional group (1), the functional group (2), or the functional group (3). it can.
本発明の美白剤、抗光老化剤、チロシナーゼ阻害剤、メラニン産生抑制剤、活性酸素種生成抑制剤、SOD様活性剤、および、カタラーゼ様活性剤において、前記構造式(I)が、下記構造式(II)で表わされるベンジリデンアゾリジン誘導体またはその塩とすることができる。
本発明の美白剤、抗光老化剤、チロシナーゼ阻害剤、メラニン産生抑制剤、活性酸素種生成抑制剤、SOD様活性剤、および、カタラーゼ様活性剤において、前記構造式(I)が、下記構造式(III)で表わされるベンジリデンヒダントイン誘導体またはその塩とすることができる。
本発明により、上記ベンジリデンアゾリジン誘導体またはその塩を有効成分とする、新規の薬剤(美白剤、抗光老化剤、チロシナーゼ阻害剤、メラニン産生抑制剤、活性酸素種生成抑制剤、SOD様活性剤、および、カタラーゼ様活性剤)が提供される。また、上記ベンジリデンアゾリジン誘導体またはその塩は、基剤への溶解性(特に親水性)に優れ、製剤化(水溶性剤))が容易である。 According to the present invention, a novel drug (whitening agent, anti-photoaging agent, tyrosinase inhibitor, melanin production inhibitor, reactive oxygen species production inhibitor, SOD-like activator, comprising the benzylidene azolidine derivative or a salt thereof as an active ingredient. And catalase-like activators). The benzylidene azolidine derivative or a salt thereof is excellent in solubility (particularly hydrophilic) in the base and easy to formulate (water-soluble agent).
また、本発明の上記ベンジリデンアゾリジン誘導体またはその塩を有効成分とする、美白剤、抗光老化剤、チロシナーゼ阻害剤、メラニン産生抑制剤、活性酸素種生成抑制剤、SOD様活性剤、および、カタラーゼ様活性剤は、後述するように外用組成物(皮膚外用剤、化粧料等)、内服剤および飲食品など、様々な剤形および形態をとりうる。なかでも紫外線によりダメージを受けた部位に直接適用できる、外用組成物、特に皮膚外用剤、化粧料として有用である。 Further, a whitening agent, an anti-photoaging agent, a tyrosinase inhibitor, a melanin production inhibitor, a reactive oxygen species production inhibitor, an SOD-like active agent, comprising the benzylidene azolidine derivative of the present invention or a salt thereof as an active ingredient, The catalase-like active agent can take various dosage forms and forms such as external compositions (external preparations for skin, cosmetics, etc.), internal preparations and foods and drinks as described later. In particular, it is useful as an external composition, particularly a skin external preparation, and a cosmetic, which can be directly applied to a site damaged by ultraviolet rays.
以下、本発明の実施の形態について詳細に説明する。 Hereinafter, embodiments of the present invention will be described in detail.
[ベンジリデンアゾリジン誘導体およびその塩]
本発明におけるベンジリデンアゾリジン誘導体は、下記構造式(I)で表わされる。
The benzylidene azolidine derivative in the present invention is represented by the following structural formula (I).
なお、上記構造式(I)中、下記構造式(i)で表わされる部分および下記構造式(ii)で表わされる部分を、それぞれ、「ベンゼン環部分(i)」および「アゾリジン部分(ii)」と称する。
上記構造式(I)に示されるように、アゾリジン部分(ii)には、「N−A2」が、さらにはA1が「N−A4」である場合、「N−A4」が含まれている。「N−A2」や「N−A4」の窒素原子は、塩基性の窒素原子であり、このN原子に、無機酸や有機酸が付加して、酸付加塩が形成されうる。ここで、無機酸としては、塩酸、硫酸、硝酸、燐酸、臭化水素酸等をあげることができる。また、有機酸としては、酢酸、クエン酸、グルコン酸、酒石酸、フマル酸、マレイン酸、乳酸、メタンスルホン酸、およびパラトルエンスルホン酸等をあげることができる。 As shown in the above structural formula (I), the azolidine moiety (ii) includes “NA 2 ”, and when A 1 is “NA 4 ”, “NA 4 ” is include. The nitrogen atom of “NA 2 ” or “NA 4 ” is a basic nitrogen atom, and an inorganic acid or an organic acid can be added to the N atom to form an acid addition salt. Here, examples of the inorganic acid include hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, hydrobromic acid, and the like. Examples of organic acids include acetic acid, citric acid, gluconic acid, tartaric acid, fumaric acid, maleic acid, lactic acid, methanesulfonic acid, and paratoluenesulfonic acid.
また、本発明におけるベンジリデンアゾリジン誘導体の塩は、本発明におけるベンジリデンアゾリジン誘導体に比べて、親水性が向上したり、固形になりやすいために取り扱いが容易になったりするなどの点で好ましい。 Further, the salt of the benzylidene azolidine derivative in the present invention is preferable in that the hydrophilicity is improved and the handling becomes easy because it tends to be solid, compared to the benzylidene azolidine derivative in the present invention.
上記構造式(I)、および上記構造式(I)を除く本明細書中の構造式において、「n」、「A1」および「A2」、「A3」は、以下のように規定される。 In the structural formulas in the present specification excluding the structural formula (I) and the structural formula (I), “n”, “A 1 ”, “A 2 ”, and “A 3 ” are defined as follows: Is done.
(1)「n」
nは、1〜5の整数であり、1〜3の整数とすることができる。
(1) “n”
n is an integer of 1 to 5, and can be an integer of 1 to 3.
(2)「A1」
A1は、O、S、またはN−A4であり、好ましくは、N−A4である。
(2) “A 1 ”
A 1 is O, S, or N—A 4 , and preferably N—A 4 .
(3)「A2」、「A3」および「A4」
A2、A3およびA4は、それぞれ独立に、水素原子、ヒドロキシル基で置換されていてもよい炭素数1〜8のアルキル基、下記構造式(1)で表わされる官能基(官能基(1))、下記構造式(2)で表わされる官能基(官能基(2))、または下記構造式(3)で表わされる官能基(官能基(3))である。ただし、少なくともA2、A3およびA4のいずれかに1つ以上のヒドロキシル基を含むものとする。
(3) “A 2 ”, “A 3 ” and “A 4 ”
A 2 , A 3 and A 4 are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms which may be substituted with a hydroxyl group, or a functional group represented by the following structural formula (1) (functional group ( 1)), a functional group represented by the following structural formula (2) (functional group (2)), or a functional group represented by the following structural formula (3) (functional group (3)). However, at least one of A 2 , A 3, and A 4 includes one or more hydroxyl groups.
また、A2、A3およびA4のうち、少なくとも1つは、前記官能基(1)、前記官能基(2)、または前記官能基(3)であることが好ましく、A2、A3およびA4のうち、少なくとも2つは、前記官能基(1)、前記官能基(2)、または前記官能基(3)であることが好ましい。
なお、nが2〜5の整数である場合、複数存在するA3−O−は、同一でも異なっていてもよい。 In addition, when n is an integer of 2 to 5, a plurality of A 3 —O— may be the same or different.
また、高い水溶性を発揮できるという観点からは、A1、A2および「A3−O−」のうち、少なくとも1つは、ヒドロキシル基を有する官能基であることが好ましい。 Further, from the viewpoint of exhibiting high water solubility, at least one of A 1 , A 2 and “A 3 —O—” is preferably a functional group having a hydroxyl group.
(3―1)「ヒドロキシル基で置換されていてもよい炭素数1〜8のアルキル基」
「ヒドロキシル基で置換されていてもよい炭素数1〜8のアルキル基」は、炭素数1〜8のアルキル基である限り、直鎖状であっても分岐状であってもよく、ヒドロキシル基で置換されているもの(ヒドロキシアルキル基)であっても、ヒドロキシル基で置換されていないアルキル基であってもよい。そのなかでも、水溶親水性が向上するという観点からは、直鎖状または分岐状の、炭素数1〜8のヒドロキシアルキル基であることが好ましい。
(3-1) "C1-C8 alkyl group optionally substituted with a hydroxyl group"
The “alkyl group having 1 to 8 carbon atoms which may be substituted with a hydroxyl group” may be linear or branched as long as it is an alkyl group having 1 to 8 carbon atoms. Even if it is substituted with (hydroxyalkyl group), it may be an alkyl group not substituted with a hydroxyl group. Among these, from the viewpoint of improving water-solubility, a linear or branched hydroxyalkyl group having 1 to 8 carbon atoms is preferable.
また、上記アルキル基の炭素数は、1〜8とすることができ、1〜4とすることができる。 Moreover, carbon number of the said alkyl group can be set to 1-8, and can be set to 1-4.
(3―2)「官能基(1)」
官能基(1)は、上記構造式(1)で表わされる官能基である。ここで、X1は、炭素数2〜4のアルキレン基であり、上記アルキレン基は、直鎖であっても、分岐していてもよい。X1において、アルキレン基の炭素数は1〜2であること(たとえば、アルキレン基がメチレン基(―CH2―)またはエチレン基(―CH2CH2―))が好ましい。
(3-2) "Functional group (1)"
The functional group (1) is a functional group represented by the structural formula (1). Here, X 1 is an alkylene group having 2 to 4 carbon atoms, and the alkylene group may be linear or branched. In X 1 , the alkylene group preferably has 1 to 2 carbon atoms (for example, the alkylene group is a methylene group (—CH 2 —) or an ethylene group (—CH 2 CH 2 —)).
R1は、炭素数2〜4のヒドロキシアルキル基(少なくとも1つのヒドロキシル基で置換されたアルキル基)であり、、炭素数2のヒドロキシアルキル基とすることができ、ヒドロキシエチル基(―CH2CH2OH)とすることができる。 R 1 is a hydroxyalkyl group having 2 to 4 carbon atoms (an alkyl group substituted with at least one hydroxyl group), can be a hydroxyalkyl group having 2 carbon atoms, and is a hydroxyethyl group (—CH 2 CH 2 OH).
mは、1〜4の整数であり、1〜2の整数とすることができる。 m is an integer of 1-4, and can be an integer of 1-2.
なお、mは2〜4の整数である場合、複数存在するX1は、同一であっても、異なっていてもよい。この場合、複数存在するX1は、メチレン基(―CH2―)またはエチレン基(―CH2CH2―)であることが好ましい。 In addition, when m is an integer of 2 to 4, a plurality of X 1 may be the same or different. In this case, it is preferable that a plurality of X 1 are a methylene group (—CH 2 —) or an ethylene group (—CH 2 CH 2 —).
(3―3)「官能基(2)」
官能基(2)は、上記構造式(2)で表わされる官能基である。ここで、X2は、炭素数2〜4のアルキレン基であり、上記アルキレン基は、直鎖であっても、分岐していてもよい。X2において、アルキレン基の炭素数は、1〜2であること(たとえば、アルキレン基がメチレン基(―CH2―)またはエチレン基(―CH2CH2―))であることが好ましい。
(3-3) "Functional group (2)"
The functional group (2) is a functional group represented by the structural formula (2). Here, X 2 is an alkylene group having 2 to 4 carbon atoms, and the alkylene group may be linear or branched. In X 2 , the alkylene group preferably has 1 to 2 carbon atoms (for example, the alkylene group is a methylene group (—CH 2 —) or an ethylene group (—CH 2 CH 2 —)).
R2は、炭素数2〜4のヒドロキシアルキル基(少なくとも1つのヒドロキシル基で置換されたアルキル基)であり、炭素数2のヒドロキシアルキル基とすることができ、ヒドロキシエチル基(―CH2CH2OH)とすることができる。 R 2 is a hydroxyalkyl group having 2 to 4 carbon atoms (an alkyl group substituted with at least one hydroxyl group), can be a hydroxyalkyl group having 2 carbon atoms, and can be a hydroxyethyl group (—CH 2 CH 2 OH).
pは、1または2である。 p is 1 or 2.
qは、0〜4の整数であり、1〜2の整数とすることができる。 q is an integer of 0 to 4, and can be an integer of 1 to 2.
なお、qは2〜4の整数である場合、複数存在するX1は、同一であっても、異なっていてもよい。この場合、汎用な試薬原料より製造しうるという観点からは、複数存在するX1は、メチレン基(―CH2―)またはエチレン基(―CH2CH2―)であることが好ましい。 In addition, when q is an integer of 2 to 4, a plurality of X 1 may be the same or different. In this case, from the viewpoint that it can be produced from a general-purpose reagent raw material, a plurality of X 1 are preferably a methylene group (—CH 2 —) or an ethylene group (—CH 2 CH 2 —).
(3―4)「官能基(3)」
官能基(3)は、上記構造式(3)で表わされる官能基である。ここで、X3aおよびX3bは、それぞれ独立に、2〜4のアルキレン基であり、上記アルキレン基は、直鎖であっても、分岐していてもよい。X3aおよびX3bは、それぞれ独立に、炭素数2〜4のアルキレン基(たとえば、アルキレン基がメチレン基(―CH2―)またはエチレン基(―CH2CH2―)であることが好ましい。
(3-4) "Functional group (3)"
The functional group (3) is a functional group represented by the structural formula (3). Here, X 3a and X 3b are each independently 2 to 4 alkylene groups, and the alkylene groups may be linear or branched. X 3a and X 3b are each independently preferably an alkylene group having 2 to 4 carbon atoms (for example, the alkylene group is a methylene group (—CH 2 —) or an ethylene group (—CH 2 CH 2 —).
R3aおよびR3bは、それぞれ独立に、炭素数2〜4のヒドロキシアルキル基(少なくともヒドロキシル基で置換されたアルキル基)であり、汎用な試薬原料より製造しうるという観点からは、炭素数2のヒドロキシアルキル基であることが好ましく、ヒドロキシエチル基(―CH2CH2OH)であることがより好ましい。 R 3a and R 3b are each independently a hydroxyalkyl group having 2 to 4 carbon atoms (an alkyl group substituted with at least a hydroxyl group), and from the viewpoint that it can be produced from a general-purpose reagent raw material, the number of carbon atoms is 2 The hydroxyalkyl group is preferably a hydroxyethyl group (—CH 2 CH 2 OH).
rは、1または2である。 r is 1 or 2;
sおよびtは、それぞれ独立に、0〜4の整数であり、汎用な試薬原料より製造しうるという観点からは、1〜2の整数であることが好ましい。 s and t are each independently an integer of 0 to 4, and are preferably an integer of 1 to 2 from the viewpoint that they can be produced from general-purpose reagent raw materials.
なお、sが2〜4の整数である場合、複数存在するX3aは、同一でも異なっていてもよいし、tが2〜4の整数である場合、複数存在するX3bは、同一でも異なっていてもよい。この場合、汎用な試薬原料より製造しうるという観点からは、複数存在するX3aおよびX3bは、メチレン基(―CH2―)またはエチレン基(―CH2CH2―)であることが好ましい。 In addition, when s is an integer of 2 to 4, a plurality of X 3a may be the same or different, and when t is an integer of 2 to 4, a plurality of X 3b is the same or different. It may be. In this case, from the viewpoint of being able to produce from general-purpose reagent raw materials, it is preferable that a plurality of X 3a and X 3b are methylene groups (—CH 2 —) or ethylene groups (—CH 2 CH 2 —). .
(3―5)「A2」
親水性をより向上できるという観点からは、A2は、水素原子、ヒドロキシル基で置換された炭素数1〜8のヒドロキシルアルキル基、官能基(1)、官能基(2)または官能基(3)であることが好ましく、ヒドロキシル基で置換された炭素数1〜8のヒドロキシルアルキル基、官能基(1)、官能基(2)または官能基(3)であることがより好ましく、官能基(1)または官能基(3)であることがさらに好ましい。
(3-5) “A 2 ”
From the viewpoint of further improving hydrophilicity, A 2 is a hydrogen atom, a hydroxyl alkyl group having 1 to 8 carbon atoms substituted with a hydroxyl group, a functional group (1), a functional group (2) or a functional group (3 It is preferably a hydroxylalkyl group having 1 to 8 carbon atoms substituted with a hydroxyl group, more preferably a functional group (1), a functional group (2) or a functional group (3). More preferably, it is 1) or functional group (3).
(3―6)「A3」
上述のように、A3は、水素原子、ヒドロキシル基で置換されていてもよい炭素数1〜8のアルキル基、官能基(1)〜(3)のいずれかであるために、ベンゼン環部分(i)に結合している「A3−O−」は、電子供与性の基である。
(3-6) “A 3 ”
As described above, A 3 is any one of a hydrogen atom, an alkyl group having 1 to 8 carbon atoms which may be substituted with a hydroxyl group, and functional groups (1) to (3). “A 3 —O—” bonded to (i) is an electron donating group.
A3は、水素原子、炭素数1〜8のヒドロキシアルキル基、官能基(1)、官能基(2)または官能基(3)であることが好ましく、官能基(1)または官能基(3)であることがより好ましい。 A 3 is preferably a hydrogen atom, a hydroxyalkyl group having 1 to 8 carbon atoms, a functional group (1), a functional group (2) or a functional group (3). The functional group (1) or the functional group (3 ) Is more preferable.
さらに、「A3―O―」は、「アゾリジン部分(ii)」に対して、ベンゼン環部分(i)のパラ位に結合していることが好ましい。このようなベンジリデンアゾリジン誘導体は、下記構造式(II)で表わされる。
ここで、より親水性を向上できるという観点から、上記構造式(II)中のn´は、0であり、かつA1はN−A4であること、すなわち、本発明におけるベンジリデンアゾリジン誘導体下記化学構造式(III)で表わされることが好ましい。
また、合成しやすさ(合成工程の短縮化)を考慮すると、A2とA3とは同一の官能基であることがより好ましい。 In consideration of ease of synthesis (shortening of the synthesis process), A 2 and A 3 are more preferably the same functional group.
(3―7)「A4」
A4は、より親水性を向上できるという観点からは、水素原子または官能基(3)であることが好ましく、水素原子であることがより好ましい。
(3-7) “A 4 ”
A 4 is preferably a hydrogen atom or a functional group (3), more preferably a hydrogen atom, from the viewpoint that the hydrophilicity can be further improved.
(4)分子量
本発明におけるベンジリデンヒダントイン誘導体の分子量は、通常250〜1000であり、好ましくは300〜500である。なお、上記分子量は、皮膚を透過して体内に吸収されて刺激性や毒性を示すといった悪影響を及ぼすリスクを低減するためには、300以上であることが好ましい。
(4) Molecular weight The molecular weight of the benzylidenehydantoin derivative in the present invention is usually 250 to 1000, preferably 300 to 500. The molecular weight is preferably 300 or more in order to reduce the risk of adverse effects such as irritation and toxicity through the skin and absorbed into the body.
[ベンジリデンアゾリジン誘導体およびその塩の製造方法]
たとえば、化学反応式(1)に示されるように、下記式(a)で表される化合物(a)と、下記式(b)で表される化合物(b)を、塩基の存在下で反応させて、下記式(c)で表される化合物(c)を合成する。次いで、化学反応式(2)に示されるように、下記式(c)で表される化合物を、下記式(d)で表される化合物(d)を、塩基の存在下に反応させることにより、本発明におけるベンジリデンアゾリジン誘導体を合成することができる。
For example, as shown in the chemical reaction formula (1), the compound (a) represented by the following formula (a) and the compound (b) represented by the following formula (b) are reacted in the presence of a base. To synthesize a compound (c) represented by the following formula (c). Next, as shown in the chemical reaction formula (2), the compound represented by the following formula (c) is reacted with the compound (d) represented by the following formula (d) in the presence of a base. The benzylidene azolidine derivative in the present invention can be synthesized.
ここで、上記化合物(b)として、市販品をそのまま用いることもできる。また、A3として水素原子を除く官能基を有する化合物(b)は、下記構造式(b´)で表わされる、A3として水素原子を有する化合物(b´)と、下記構造式(e)で表わされる化合物(e)と、塩基の存在下で、反応式(3)で示されるように、反応させることによって得られたものを用いることができる。
また、上記化合物(a)として、市販品をそのまま用いることもできる。 Moreover, a commercial item can also be used as it is as the said compound (a).
また、下記式(4−1)で示されるように、上記化合物(a)と上記化合物(d)とを、塩基の存在下で反応させて、下記構造式(f)で表される化合物(f)を合成できる。あるいは、下記反応式(4−2)で示されるように、下記化合物(g)と下記化合物(h)とを、塩基の存在下または非存在下にて、縮合剤を用い(このとき、イソシアナートを経由する)、さらに酸の存在下で環化させることにより、下記構造式(f)で表される化合物(f)を合成することもできる。ここで、上記化合物(a)のA1が「NH」である場合、反応式(5)で示されるように、化合物(f)と下記構造式(e´)とを、塩基の存在下で反応させて、A1が「NA4」である化合物(f)を合成できる。次いで、下記反応式(6)で示されるように、化合物(f)と上記化合物(b)とを、塩基の存在下で、反応させて、本発明におけるベンジリデンアゾリジン誘導体を合成することもできる。
(式(g)のA1は、式(I)のA1と同一である。
Zは、ヒドロキシル基またはアルコキシル基である。)
(A 1 of formula (g) is the same as A 1 of formula (I).
Z is a hydroxyl group or an alkoxyl group. )
また、本発明におけるベンジリデンアゾリジン誘導体が、構造式(I)のA2、A3およびA4として、官能基(2)または官能基(3)を有する場合、それぞれ、前記化合物(d)、前記化合物(e)、前記化合物(e´)の代わりに、下記構造式(i)で表される化合物(i)、また、前記化合物(h)の代わりに、下記構造式(j)で表される化合物(j)を用いることを除いては、反応式(1)〜(6)と同様にして、構造式(I)中、A2、A3またはA4として、下記構造式(k)で表される官能基(k)を有する化合物(k)を合成することができる。次いで、前記化合物(k)を一般的な官能基変換反応(カルボン酸のエステル化、カルボン酸のアミド化、エステル交換、エステルのアミド化など)により、本発明におけるベンジリデンアゾリジン誘導体に導くこともできる。
上述したような、本発明におけるベンジリデンアゾリジン誘導体の製造法で用いる塩基としては、たとえば、炭酸ナトリウム、炭酸カリウム、水素化ナトリウム、ナトリウムメトキシド、ナトリウムt−ブトキシド、カリウムt−ブトキシド、ピリジン、トリエチルアミン、トリイソプロピルアミン、ジイソプロピルエチルアミン、ピロリジン、ピペリジン、酢酸ナトリウム、アンモニア水、ジアザビシクロウンデセン、ジアザビシクロノネンをあげることができる。 Examples of the base used in the method for producing the benzylidene azolidine derivative in the present invention as described above include sodium carbonate, potassium carbonate, sodium hydride, sodium methoxide, sodium t-butoxide, potassium t-butoxide, pyridine, and triethylamine. , Triisopropylamine, diisopropylethylamine, pyrrolidine, piperidine, sodium acetate, aqueous ammonia, diazabicycloundecene and diazabicyclononene.
また、本発明におけるベンジリデンアゾリジン誘導体の製造方法で用いる縮合剤としては、たとえば、ホスゲン、トリホスゲン、カルボニルジイミダゾール、クロロ蟻酸トリクロロメチル、クロロ蟻酸パラニトロフェニルあるいはクロロ蟻酸パラシアノフェニルをあげることができる。 Examples of the condensing agent used in the method for producing a benzylidene azolidine derivative in the present invention include phosgene, triphosgene, carbonyldiimidazole, trichloromethyl chloroformate, paranitrophenyl chloroformate, and paracyanophenyl chloroformate. .
また、本発明におけるベンジリデンアゾリジン誘導体の製造方法で用いる酸としては、たとえば、塩酸、硫酸、硝酸、燐酸、臭化水素酸などの無機酸、または、酢酸、クエン酸、グルコン酸、酒石酸、フマル酸、マレイン酸、乳酸、メタンスルホン酸、パラトルエンスルホン酸などの有機酸をあげることができる。 Examples of the acid used in the method for producing a benzylidene azolidine derivative in the present invention include inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, hydrobromic acid, or acetic acid, citric acid, gluconic acid, tartaric acid, fumaric acid. Examples thereof include organic acids such as acid, maleic acid, lactic acid, methanesulfonic acid, and paratoluenesulfonic acid.
さらに、上述のようにして得られたベンジリデンアゾリジン誘導体は、シリカゲル、アルミナ、ゼオライト、活性炭、イオン交換樹脂、多孔性合成樹脂などの吸着剤での処理、溶媒の留去、および/または再結晶により精製することで高純度のものをうることができる。 Further, the benzylidene azolidine derivative obtained as described above can be treated with an adsorbent such as silica gel, alumina, zeolite, activated carbon, ion exchange resin, porous synthetic resin, evaporation of the solvent, and / or recrystallization. A highly purified product can be obtained by purifying by the above.
また、本発明におけるベンジリデンアゾリジン誘導体の塩は、上述のようにして得られたベンジリデンアゾリジン誘導体に塩酸、硫酸、硝酸、燐酸、臭化水素酸などの無機酸、または、酢酸、クエン酸、グルコン酸、酒石酸、フマル酸、マレイン酸、乳酸、メタンスルホン酸、パラトルエンスルホン酸などの有機酸を加えて中和、留去、精製することで導くことが可能である。 The salt of the benzylidene azolidine derivative in the present invention is an inorganic acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, hydrobromic acid, acetic acid, citric acid, benzylidene azolidine derivative obtained as described above. It can be derived by adding an organic acid such as gluconic acid, tartaric acid, fumaric acid, maleic acid, lactic acid, methanesulfonic acid or paratoluenesulfonic acid, neutralizing, distilling, and purifying.
[ベンジリデンアゾリジン誘導体またはその塩を含む薬剤]
(薬剤)
本発明の薬剤(美白剤、抗光老化剤、チロシナーゼ阻害剤、メラニン産生抑制剤、活性酸素種生成抑制剤、SOD様活性剤、および、カタラーゼ様活性剤)は、上記ベンジリデンアゾリジン誘導体またはその塩を含むことを特徴とする。
[Drugs containing benzylidene azolidine derivatives or salts thereof]
(Drug)
The agent of the present invention (whitening agent, anti-photoaging agent, tyrosinase inhibitor, melanin production inhibitor, reactive oxygen species production inhibitor, SOD-like activator, and catalase-like activator) is the benzylidene azolidine derivative or its It contains a salt.
本発明の美白剤は、上記ベンジリデンアゾリジン誘導体またはその塩を有効成分とすることにより、優れた美白作用を有するものである。 The whitening agent of the present invention has an excellent whitening action by using the benzylidene azolidine derivative or a salt thereof as an active ingredient.
上記美白作用は、肌のくすみやしみ等に特に関係しているメラニン色素等による皮膚の着色現象を予防または遅延させることにより発現しているものと推測されるが、これに限定されるものではない。 The above-mentioned whitening effect is presumed to be manifested by preventing or delaying the skin coloring phenomenon caused by melanin pigments particularly related to dullness and itching of the skin, but is not limited to this. Absent.
また、本発明の抗光老化剤は、上記ベンジリデンアゾリジン誘導体またはその塩を有効成分とすることにより、優れた抗光老化作用を有するものである。 The anti-photoaging agent of the present invention has an excellent anti-photoaging effect by using the benzylidene azolidine derivative or a salt thereof as an active ingredient.
上記抗光老化作用は、紫外線暴露による活性酸素種の増加により引き起こされる、皮膚のしわ、たるみ、くすみ、色素沈着(しみ等)、くま、菲薄化などの肌の老化現象を予防または防止または遅延させることにより発現しているものと推測されるが、これに限定されるものではない。 The above-mentioned anti-photoaging action prevents, prevents or delays skin aging such as wrinkles, sagging, dullness, pigmentation (stains, etc.), bears and thinning caused by the increase of reactive oxygen species due to UV exposure. However, the present invention is not limited to this.
また、本発明のチロシナーゼ阻害剤は、上記ベンジリデンアゾリジン誘導体またはその塩を有効成分とすることにより、優れたチロシナーゼ活性の阻害作用を有するものである。 The tyrosinase inhibitor of the present invention has an excellent inhibitory effect on tyrosinase activity by using the benzylidene azolidine derivative or a salt thereof as an active ingredient.
上記チロシナーゼ活性の阻害作用は、メラニン合成に関与するチロシナーゼの活性を阻害または低下させることにより発現しているものと推測される。 The inhibitory effect on the tyrosinase activity is presumed to be expressed by inhibiting or reducing the activity of tyrosinase involved in melanin synthesis.
また、本発明のメラニン産生抑制剤は、上記ベンジリデンアゾリジン誘導体またはその塩を有効成分とすることにより、優れたメラニン産生抑制作用を有するものである。 Moreover, the melanin production inhibitor of this invention has the outstanding melanin production inhibitory effect by using the said benzylidene azolidine derivative or its salt as an active ingredient.
上記メラニン産生抑制作用は、メラニン産生を阻害または低下させることにより発現しているものと推測される。 The melanin production-suppressing effect is presumed to be expressed by inhibiting or reducing melanin production.
また、本発明の活性酸素種抑制剤は、上記一般式(I)で表されるベンジリデンアゾリジン誘導体またはその塩を含むことを特徴とする。 In addition, the reactive oxygen species inhibitor of the present invention is characterized by containing a benzylidene azolidine derivative represented by the above general formula (I) or a salt thereof.
上記活性酸素種生成抑制剤とは、紫外線暴露等により生じる活性酸素種の生成を阻害または低下させるものをいう。また、紫外線暴露等により生じた活性酸素種を消去する機能も持ち合わせる。 The active oxygen species production inhibitor refers to an agent that inhibits or reduces the production of active oxygen species caused by exposure to ultraviolet rays or the like. It also has a function to erase active oxygen species generated by UV exposure.
また、本発明のSOD様活性剤は、上記一般式(I)で表されるベンジリデンアゾリジン誘導体またはその塩を含むことを特徴とする。 The SOD-like activator of the present invention is characterized by containing a benzylidene azolidine derivative represented by the above general formula (I) or a salt thereof.
上記SOD様活性剤とは、紫外線暴露などにより生じたスーパーオキシドアニオンの生成を阻害または低下させるものをいう。 The SOD-like active agent refers to an agent that inhibits or reduces the production of superoxide anion generated by ultraviolet exposure or the like.
また、本発明のカタラーゼ様活性剤は、上記一般式(I)で表されるベンジリデンアゾリジン誘導体またはその塩を含むことを特徴とする。 The catalase-like active agent of the present invention is characterized by containing a benzylidene azolidine derivative represented by the above general formula (I) or a salt thereof.
上記カタラーゼ様活性剤とは、紫外線暴露などにより生じた過酸化水素水の生成を阻害または低下させるものをいう。 The catalase-like active agent refers to an agent that inhibits or reduces the production of hydrogen peroxide generated by exposure to ultraviolet rays.
本発明における美白剤、抗光老化剤、チロシナーゼ阻害剤、メラニン産生抑制剤、活性酸素種生成抑制剤、SOD様活性剤、および、カタラーゼ様活性剤を適用することで、上記のくすみやシミ、そばかす、肝斑等の肌の着色現象、シワ、たるみ、くすみ、皮膚の菲薄化等の肌の老化現象、皮膚の糖化現象を防止、予防、進行を遅延させることにより、たとえば、肌の透明感やハリ、ツヤを増加させることができ、肌を若々しく保つ効果も期待できる。前記肌に対する効果は、外皮用組成物として適用した場合に特に優れており、また、既知の美白成分(チロシナーゼ阻害成分、メラニン産生抑制成分)、抗光老化成分(活性酸素種生成抑制成分、SOD様活性成分、カタラーゼ様活性成分)、抗糖化成分、抗炎症成分、抗シワ成分、細胞賦活化成分等の1種または2種以上を組み合わせることで、各作用を増強させた組成物をうることができる。 By applying the whitening agent, anti-photoaging agent, tyrosinase inhibitor, melanin production inhibitor, reactive oxygen species production inhibitor, SOD-like activator, and catalase-like activator in the present invention, Prevent skin coloration such as freckles, liver spots, wrinkles, sagging, dullness, skin aging such as thinning of skin, glycation of skin, prevent, prevent, delay progress, for example, skin transparency It can increase skin, firmness and luster, and can also be expected to keep youthful. The effect on the skin is particularly excellent when applied as an outer skin composition, and is also known as a whitening component (tyrosinase inhibiting component, melanin production inhibiting component), anti-photoaging component (reactive oxygen species production inhibiting component, SOD). Like active ingredient, catalase-like active ingredient), anti-glycation component, anti-inflammatory component, anti-wrinkle component, cell activation component, etc. Can do.
より具体的には、たとえば、アルブチン、アスコルビン酸またはその誘導体、ビタミンEまたはその誘導体(δ−トコフェロール類等)、ハイドロキノン、コウジ酸、ルシノール、グリチルリチン酸またはその誘導体、グリチルレチン酸またはその誘導体、加水分解大豆タンパク、レチノイド類(レチノール及びその誘導体、レチノイン酸、レチナール等)、カイネチン、ピロロキノリンキノン(PQQ)およびそれらの塩類、ヒアルロン酸及びその誘導体およびそれらの塩類などと組み合わせて外用組成物(皮膚外用剤、化粧品等)とすることができる。 More specifically, for example, arbutin, ascorbic acid or a derivative thereof, vitamin E or a derivative thereof (δ-tocopherols, etc.), hydroquinone, kojic acid, lucinol, glycyrrhizic acid or a derivative thereof, glycyrrhetinic acid or a derivative thereof, hydrolysis Composition for external use in combination with soy protein, retinoids (retinol and its derivatives, retinoic acid, retinal, etc.), kinetin, pyrroloquinoline quinone (PQQ) and their salts, hyaluronic acid and its derivatives and their salts, etc. Agents, cosmetics, etc.).
(基剤または担体)
本発明において、薬剤(美白剤、抗光老化剤、チロシナーゼ阻害剤、メラニン産生抑制剤、活性酸素種生成抑制剤、SOD様活性剤、および、カタラーゼ様活性剤)は、本発明の効果を損なわない範囲で、化粧品や医薬部外品に使用されるその他の公知の基剤または担体を含むことができる。基剤または担体は、1種を単独で、または2種以上を組み合わせて使用できる。
(Base or carrier)
In the present invention, drugs (whitening agents, anti-photoaging agents, tyrosinase inhibitors, melanin production inhibitors, reactive oxygen species production inhibitors, SOD-like activators, and catalase-like activators) impair the effects of the present invention. In other words, other known bases or carriers used in cosmetics and quasi drugs can be included. A base or a carrier can be used singly or in combination of two or more.
基剤または担体としては、パラフィン、流動パラフィン、スクワラン、白ロウ、ゲル化炭化水素(プラスチベースなど)、オゾケライト、セレシン、ワセリン、ハードファット、マイクロクリスタリンワックス、α−オレフィンオリゴマー、軽質流動パラフィンのような炭化水素;ラウリン酸、ミリスチン酸、パルミチン酸、ステアリン酸、ベヘニン酸、イソステアリン酸のような脂肪酸;トリ2−エチルヘキサン酸グリセリル(トリオクタノイン)、トリ(カプリル酸/カプリン酸)グリセリルのようなトリ脂肪酸グリセリド;セタノール、ステアリルアルコール、ベヘニルアルコールのような高級アルコール;メチルポリシロキサン、高重合メチルポリシロキサン、ジメチルシロキサン・メチル(ポリオキシエチレン)シロキサン・メチル(ポリオキシプロピレン)シロキサン共重合体、ジメチルシロキサン・メチル(ポリオキシエチレン)シロキサン共重合体、ジメチルシロキサン・メチル(ポリオキシプロピレン)シロキサン共重合体、ポリオキシエチレン・メチルポリシロキサン共重合体、ポリ(オキシエチレン・オキシプロピレン)・メチルポリシロキサン共重合体、ジメチルシロキサン・メチルセチルオキシシロキサン共重合体、ジメチルシロキサン・メチルステアロキシシロキサン共重合体、アクリル酸アルキル共重合体メチルポリシロキサンエステル、架橋型メチルポリシロキサン、架橋型メチルフェニルポリシロキサン、架橋型ポリエーテル変性シリコーン、架橋型アルキルポリエーテル変性シリコーン、架橋型アルキル変性シリコーン、デカメチルシクロペンタシロキサン、エチルトリシロキサン、メチルトリメチコン、メチルシロキサン網状重合体、ポリオキシエチレン・メチルポリシロキサン共重合体、メチルハイドロジェンポリシロキサン、トリエトキシシリルエチルポリジメチルシロキシエチルヘキシルジメチコン、ジメチルポリシロキサンのようなシリコーン油;エチレングリコールモノアセタート、エチレングリコールジアセタート、トリエチレングリコールジアセタート、ヘキシレングリコールジアセタート、および2−メチル−2−プロペン−1,1−ジオールジアセタートのようなグリコールアセタート;トリエチレングリコールジバレラート、2,2,4−トリメチル−1,3−ペンタンジオールモノイソブチラート、2,2,4−トリメチル−1,3−ペンタンジオールジイソブチラートのようなグリコールエステル;エチレングリコールジアクリラート、ジエチレングリコールジアクリラート、プロピレングリコールモノアクリラート、2,2−ジメチル−トリメチレングリコールジアクリラート、および1,3−ブチレングリコールジアクリラートのようなグリコールアクリラート;エチレングリコールジニトラート、ジエチレングリコールジニトラート、トリエチレングリコールジニトラート、およびプロピレングリコールジニトラートのようなグリコールジニトラート;2,2′−[1,4−フェニレンジオキシ]ジエタノール;エチルセルロース、ヒドロキシプロピルセルロース、ヒドロキシプロピルメチルセルロースのようなセルロース誘導体;ポリビニルピロリドン;カラギーナン;ポリビニルブチラート;ポリエチレングリコール;ジオキサン;ブチレングリコールアジピン酸ポリエステル;ミリスチン酸イソプロピル、ミリスチン酸オクチルドデシル、パルミチン酸イソプロピル、パルミチン酸セチル、イソノナン酸イソノニル、テトラ2−エチルヘキサン酸ペンタエリスエリットのようなエステル類;デキストリン、マルトデキストリンのような多糖類;エタノール、イソプロパノールのような低級アルコール;エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノプロピルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノプロピルエーテル、ジエチレングリコールモノブチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノプロピルエーテル、ジプロピレングリコールモノエチルエーテル、ジプロピレングリコールモノプロピルエーテルのようなグリコールエーテル;水などの水系基剤などをあげることができる。 Bases or carriers include paraffin, liquid paraffin, squalane, white wax, gelled hydrocarbons (plastibase, etc.), ozokerite, ceresin, petrolatum, hard fat, microcrystalline wax, α-olefin oligomer, light liquid paraffin, etc. Hydrocarbons; fatty acids such as lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, isostearic acid; such as glyceryl tri-2-ethylhexanoate (trioctanoin), tri (caprylic acid / capric acid) glyceryl Tri-fatty acid glycerides; higher alcohols such as cetanol, stearyl alcohol, behenyl alcohol; methyl polysiloxanes, highly polymerized methyl polysiloxanes, dimethyl siloxane methyl (polyoxyethylene) siloxane methyl (Polyoxypropylene) siloxane copolymer, dimethylsiloxane methyl (polyoxyethylene) siloxane copolymer, dimethylsiloxane methyl (polyoxypropylene) siloxane copolymer, polyoxyethylene methyl polysiloxane copolymer, poly (Oxyethylene / oxypropylene) / methylpolysiloxane copolymer, dimethylsiloxane / methylcetyloxysiloxane copolymer, dimethylsiloxane / methylstearoxysiloxane copolymer, alkyl acrylate copolymer methylpolysiloxane ester, cross-linked type Methylpolysiloxane, crosslinked methylphenylpolysiloxane, crosslinked polyether-modified silicone, crosslinked alkylpolyether-modified silicone, crosslinked alkyl-modified silicone, decamethylcyclopen Such as polysiloxane, ethyltrisiloxane, methyltrimethicone, methylsiloxane network polymer, polyoxyethylene-methylpolysiloxane copolymer, methylhydrogenpolysiloxane, triethoxysilylethylpolydimethylsiloxyethylhexyldimethicone, dimethylpolysiloxane Silicone oils; glycols such as ethylene glycol monoacetate, ethylene glycol diacetate, triethylene glycol diacetate, hexylene glycol diacetate, and 2-methyl-2-propene-1,1-diol diacetate Acetate; triethylene glycol divalerate, 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate, 2,2,4-trimethyl-1,3-pentanediol dii Glycol esters such as butyrate; such as ethylene glycol diacrylate, diethylene glycol diacrylate, propylene glycol monoacrylate, 2,2-dimethyl-trimethylene glycol diacrylate, and 1,3-butylene glycol diacrylate Glycol acrylates; glycol dinitrates such as ethylene glycol dinitrate, diethylene glycol dinitrate, triethylene glycol dinitrate, and propylene glycol dinitrate; 2,2 '-[1,4-phenylenedioxy] diethanol; ethylcellulose, hydroxy Cellulose derivatives such as propylcellulose, hydroxypropylmethylcellulose; polyvinylpyrrolidone; carrageenan; polyvinylbuty Polyethylene glycol; dioxane; butylene glycol adipic acid polyester; esters such as isopropyl myristate, octyldodecyl myristate, isopropyl palmitate, cetyl palmitate, isononyl isononanoate, pentaerythrite tetra-2-ethylhexanoate; Polysaccharides such as dextrin and maltodextrin; lower alcohols such as ethanol and isopropanol; ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, Diethylene glycol monobutyl ether, propylene glycol Examples thereof include glycol ethers such as recall monoethyl ether, propylene glycol monopropyl ether, dipropylene glycol monoethyl ether and dipropylene glycol monopropyl ether; aqueous bases such as water.
なかでも、炭化水素(特に、α−オレフィンオリゴマー、スクワラン、軽質流動パラフィン、流動パラフィン)、トリ脂肪酸グリセリド(特に、トリ2−エチルヘキサン酸グリセリル、トリ(カプリル酸/カプリン酸)グリセリル)、高級アルコール(特に、セタノール、ステアリルアルコール、ベヘニルアルコール)、シリコーン油(特に、メチルポリシロキサン、アクリル酸アルキル共重合体メチルポリシロキサンエステル、架橋型メチルポリシロキサン、デカメチルシクロペンタシロキサン、エチルトリシロキサン、メチルトリメチコン、メチルシロキサン網状重合体、ポリオキシエチレン・メチルポリシロキサン共重合体、メチルハイドロジェンポリシロキサン、トリエトキシシリルエチルポリジメチルシロキシエチルヘキシルジメチコン、ジメチルポリシロキサン)、エステル類(特に、イソノナン酸イソノニル、テトラ2−エチルヘキサン酸ペンタエリスリット)、多糖類(特に、デキストリン、マルトデキストリン)、グリコールエーテル(特に、ジエチレングリコールモノエチルエーテル)、水が好ましい。 Among them, hydrocarbons (especially α-olefin oligomers, squalane, light liquid paraffin, liquid paraffin), trifatty acid glycerides (particularly glyceryl tri-2-ethylhexanoate, tri (caprylic acid / capric acid) glyceryl), higher alcohols (Especially cetanol, stearyl alcohol, behenyl alcohol), silicone oil (especially methylpolysiloxane, alkyl acrylate copolymer methylpolysiloxane ester, cross-linked methylpolysiloxane, decamethylcyclopentasiloxane, ethyltrisiloxane, methyltrimethicone , Methylsiloxane network polymer, polyoxyethylene / methylpolysiloxane copolymer, methylhydrogenpolysiloxane, triethoxysilylethylpolydimethylsiloxyethylhexyl dimethyl ester Con, dimethylpolysiloxane), esters (especially isononyl isononanoate, pentaerythritol tetra-2-ethylhexanoate), polysaccharides (especially dextrin, maltodextrin), glycol ethers (especially diethylene glycol monoethyl ether), water Is preferred.
(添加剤)
本発明において、皮膚外用組成物には、本発明の効果を損なわない範囲で、化粧品や医薬部外品に添加される公知の添加剤、たとえば、増粘剤、界面活性剤、保存剤、pH調整剤、キレート剤、安定化剤、刺激軽減剤、防腐剤、着色剤、分散剤、香料、パール光沢付与剤等を添加することができる。添加剤は、1種を単独で、または2種以上を組み合わせて使用できる。
(Additive)
In the present invention, the composition for external use for skin is a known additive added to cosmetics and quasi-drugs, for example, thickeners, surfactants, preservatives, pH, within the range not impairing the effects of the present invention A regulator, a chelating agent, a stabilizer, an irritation reducing agent, an antiseptic, a colorant, a dispersant, a fragrance, a pearl luster imparting agent, and the like can be added. An additive can be used individually by 1 type or in combination of 2 or more types.
増粘剤としては、たとえば、メチルセルロース、エチルセルロース、ヒドロキシエチルセルロース、ヒドロキシメチルセルロース、ヒドロキシプロピルセルロース、ヒドロキシプロピルメチルセルロース、カルボキシメチルセルロース、カルボキシエチルセルロースのようなセルロース系増粘剤、グアーガム、ローカストビーンガム、カラギーナン、キサンタンガムのような増粘多糖類、デキストラン、ポリビニルアルコール、ポリビニルピロリドン、ポリビニルメチルエーテル、カルボキシビニルポリマー、アクリル酸メタクリル酸アルキル共重合体、デキストリン脂肪酸エステル、ペクチン、(アクリル酸ヒドロキシエチル/アクリロイルジメチルタウリンNa)コポリマー、ジメチルジステアリルアンモニウムヘクトライト、(アクリロイルジメチルタウリンアンモニウム/ビニルピロリドン)コポリマー、ジステアリン酸ポリエチレングリコール、トリイソステアリン酸エチレングリコール、トリイソステアリン酸ポリオキシエチレン(20)メチルグルコシド、ポリエチレングリコール、ベントナイト、アルギン酸、アルギン酸ナトリウム、アルギン酸プロピレングリコールエステル、マクロゴール、コンドロイチン硫酸ナトリウム、ヒアルロン酸およびこれらの塩、ヒアルロン酸誘導体およびこれらの塩などの水溶性高分子をあげることができる。 Examples of the thickener include cellulose-based thickeners such as methylcellulose, ethylcellulose, hydroxyethylcellulose, hydroxymethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, carboxymethylcellulose, carboxyethylcellulose, guar gum, locust bean gum, carrageenan, and xanthan gum. Such as polysaccharide thickener, dextran, polyvinyl alcohol, polyvinyl pyrrolidone, polyvinyl methyl ether, carboxyvinyl polymer, alkyl methacrylate copolymer, dextrin fatty acid ester, pectin, (hydroxyethyl acrylate / acryloyldimethyltaurine Na) copolymer , Dimethyl distearyl ammonium hectorite, (acrylic Yldimethyltaurate ammonium / vinyl pyrrolidone) copolymer, polyethylene glycol distearate, ethylene glycol triisostearate, polyoxyethylene (20) methyl glucoside triisostearate, polyethylene glycol, bentonite, alginic acid, sodium alginate, propylene glycol alginate, macrogol And water-soluble polymers such as sodium chondroitin sulfate, hyaluronic acid and salts thereof, hyaluronic acid derivatives and salts thereof.
なかでも、特に使用感が良くなる点で、メチルセルロース、エチルセルロース、ヒドロキシエチルセルロース、ヒドロキシメチルセルロース、ヒドロキシプロピルセルロース、ヒドロキシプロピルメチルセルロース、カルボキシメチルセルロース、カルボキシエチルセルロースのようなセルロース系増粘剤、グアーガム、ローカストビーンガム、カラギーナン、キサンタンガムのような増粘多糖類、デキストラン、ポリビニルアルコール、ポリビニルピロリドン、ポリビニルメチルエーテル、カルボキシビニルポリマー、アクリル酸メタクリル酸アルキル共重合体、デキストリン脂肪酸エステル、ペクチン、(アクリル酸ヒドロキシエチル/アクリロイルジメチルタウリンNa)コポリマー、ジメチルジステアリルアンモニウムヘクトライト、(アクリロイルジメチルタウリンアンモニウム/ビニルピロリドン)コポリマーが好ましく、メチルセルロース、エチルセルロース、ヒドロキシエチルセルロース、ヒドロキシメチルセルロース、ヒドロキシプロピルセルロース、ヒドロキシプロピルメチルセルロース、カルボキシメチルセルロース、カルボキシエチルセルロース、キサンタンガム、アクリル酸メタクリル酸アルキル共重合体、(アクリル酸ヒドロキシエチル/アクリロイルジメチルタウリンNa)コポリマー、(アクリロイルジメチルタウリンアンモニウム/ビニルピロリドン)コポリマーがより好ましい。 Among these, in terms of particularly good usability, methyl cellulose, ethyl cellulose, hydroxyethyl cellulose, hydroxymethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose, carboxymethyl cellulose, cellulose thickeners such as carboxyethyl cellulose, guar gum, locust bean gum, Carrageenan, thickening polysaccharides such as xanthan gum, dextran, polyvinyl alcohol, polyvinyl pyrrolidone, polyvinyl methyl ether, carboxyvinyl polymer, alkyl methacrylate copolymer, dextrin fatty acid ester, pectin, (hydroxyethyl acrylate / acryloyldimethyl) Taurine Na) copolymer, dimethyl distearyl ammonium hectorite (Acryloyldimethyltauronium ammonium / vinylpyrrolidone) copolymer is preferred, methylcellulose, ethylcellulose, hydroxyethylcellulose, hydroxymethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, carboxymethylcellulose, carboxyethylcellulose, xanthan gum, alkyl methacrylate methacrylate (acrylic) An acid hydroxyethyl / acryloyldimethyltaurine Na) copolymer and an (acryloyldimethyltaurine ammonium / vinylpyrrolidone) copolymer are more preferred.
界面活性剤としては、たとえば、ソルビタンモノイソステアレート、ソルビタンモノラウレート、ソルビタンモノパルミテート、ソルビタンモノステアレート、ペンタ−2−エチルヘキシル酸ジグリセロールソルビタン、テトラ−2−エチルヘキシル酸ジグリセロールソルビタンのようなソルビタン脂肪酸エステル類;モノステアリン酸グリセリル、モノステアリン酸グリセリンリンゴ酸のようなグリセリン脂肪酸類;モノステアリン酸ポリグリセリル、モノイソステアリン酸ポリグリセリル、ジイソステアリン酸ポリグリセリルのようなポリグリセリン脂肪酸類;モノステアリン酸プロピレングリコールのようなプロピレングリコール脂肪酸エステル類;ポリオキシエチレン硬化ヒマシ油40(HCO−40)、ポリオキシエチレン硬化ヒマシ油50(HCO−50)、ポリオキシエチレン硬化ヒマシ油60(HCO−60)、ポリオキシエチレン硬化ヒマシ油80などの硬化ヒマシ油誘導体;モノラウリル酸ポリオキシエチレン(20)ソルビタン(ポリソルベート20)、モノステアリン酸ポリオキシエチレン(20)ソルビタン(ポリソルベート60)、モノオレイン酸ポリオキシエチレン(20)ソルビタン(ポリソルベート80)、イソステアリン酸ポリオキシエチレン(20)ソルビタンのようなポリオキシエチレンソルビタン脂肪酸エステル類;ポリオキシエチレンモノヤシ油脂肪酸グリセリル;グリセリンアルキルエーテル;アルキルグルコシド;ポリオキシエチレンセチルエーテルのようなポリオキシアルキレンアルキルエーテル;ステアリルアミン、オレイルアミンのようなアミン類;ポリオキシエチレン・メチルポリシロキサン共重合体、ラウリルPEG−9ポリジメチルシロキシエチルジメチコン、PEG−9ポリジメチルシロキシエチルジメチコンのようなシリコーン系界面活性剤などをあげることができる。 Examples of the surfactant include sorbitan monoisostearate, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, diglycerol sorbitan penta-2-ethylhexylate, and diglycerol sorbitan tetra-2-ethylhexylate. Sorbitan fatty acid esters; glyceryl fatty acids such as glyceryl monostearate and glyceryl monostearate; polyglyceryl fatty acids such as polyglyceryl monostearate, polyglyceryl monoisostearate and polyglyceryl diisostearate; propylene glycol monostearate Propylene glycol fatty acid esters such as: polyoxyethylene hydrogenated castor oil 40 (HCO-40), polyoxyethylene hydrogenated castor oil Cured castor oil derivatives such as deca oil 50 (HCO-50), polyoxyethylene hydrogenated castor oil 60 (HCO-60), polyoxyethylene hydrogenated castor oil 80; polyoxyethylene (20) sorbitan monolaurate (polysorbate 20) , Polyoxyethylene sorbitan fatty acid esters such as polyoxyethylene (20) sorbitan monostearate (polysorbate 60), polyoxyethylene monooxylate (20) sorbitan (polysorbate 80), polyoxyethylene (20) sorbitan isostearate Polyoxyethylene mono coconut oil fatty acid glyceryl; glycerin alkyl ether; alkyl glucoside; polyoxyalkylene alkyl ether such as polyoxyethylene cetyl ether; stearylamine, olei Examples include amines such as amines; polyoxyethylene / methylpolysiloxane copolymers, silicone surfactants such as lauryl PEG-9 polydimethylsiloxyethyl dimethicone, and PEG-9 polydimethylsiloxyethyl dimethicone. .
なかでも、グリセリン脂肪酸類(特に、モノステアリン酸グリセリル)、ポリグリセリン脂肪酸類(特に、モノステアリン酸ポリグリセリル)、硬化ヒマシ油誘導体(特に、ポリオキシエチレン硬化ヒマシ油50(HCO−50)、ポリオキシエチレン硬化ヒマシ油60(HCO−60))、ポリオキシエチレンソルビタン脂肪酸エステル類(特に、イソステアリン酸ポリオキシエチレン(20)ソルビタン、モノステアリン酸ポリオキシエチレン(20)ソルビタン(ポリソルベート60))、ポリオキシアルキレンアルキルエーテル(特に、ポリオキシエチレンセチルエーテル)、シリコーン系界面活性剤(特に、ポリオキシエチレン・メチルポリシロキサン共重合体、ラウリルPEG−9ポリジメチルシロキシエチルジメチコン、PEG−9ポリジメチルシロキシエチルジメチコン)が好ましい。 Among them, glycerin fatty acids (particularly glyceryl monostearate), polyglycerin fatty acids (particularly polyglyceryl monostearate), hydrogenated castor oil derivative (particularly polyoxyethylene hydrogenated castor oil 50 (HCO-50), polyoxy) Ethylene hydrogenated castor oil 60 (HCO-60)), polyoxyethylene sorbitan fatty acid esters (particularly polyoxyethylene (20) sorbitan isostearate, polyoxyethylene (20) sorbitan monostearate (polysorbate 60)), polyoxy Alkylene alkyl ether (especially polyoxyethylene cetyl ether), silicone surfactant (especially polyoxyethylene methylpolysiloxane copolymer, lauryl PEG-9 polydimethylsiloxyethyl dimethicone, PE -9 polydimethylsiloxyethyl dimethicone) is preferred.
保存剤、防腐剤としては、安息香酸、安息香酸ナトリウム、デヒドロ酢酸、デヒドロ酢酸ナトリウム、パラオキシ安息香酸イソブチル、パラオキシ安息香酸イソプロピル、パラオキシ安息香酸ブチル、パラオキシ安息香酸エチル、パラオキシ安息香酸プロピル、パラオキシ安息香酸ベンジル、パラオキシ安息香酸メチル、フェノキシエタノールなどをあげることができる。なかでも、パラオキシ安息香酸メチル、パラオキシ安息香酸プロピル、フェノキシエタノールが好ましい。 Preservatives and preservatives include benzoic acid, sodium benzoate, dehydroacetic acid, sodium dehydroacetate, isobutyl paraoxybenzoate, isopropyl paraoxybenzoate, butyl paraoxybenzoate, ethyl paraoxybenzoate, propyl paraoxybenzoate, paraoxybenzoic acid Examples thereof include benzyl, methyl paraoxybenzoate, and phenoxyethanol. Of these, methyl paraoxybenzoate, propyl paraoxybenzoate, and phenoxyethanol are preferable.
pH調整剤としては、無機酸(塩酸、硫酸、リン酸、ポリリン酸、ホウ酸など)、有機酸(乳酸、酢酸、クエン酸、クエン酸ナトリウム、酒石酸、リンゴ酸、コハク酸、コハク酸ナトリウム、シュウ酸、グルコン酸、フマル酸、プロピオン酸、酢酸、アスパラギン酸、ε−アミノカプロン酸、グルタミン酸、アミノエチルスルホン酸など)、グルコノラクトン、酢酸アンモニウム、無機塩基(炭酸水素ナトリウム、炭酸ナトリウム、水酸化カリウム、水酸化ナトリウム、水酸化カルシウム、水酸化マグネシウムなど)、有機塩基(モノエタノールアミン、トリエタノールアミン、ジイソプロパノールアミン、トリイソプロパノールアミン、リジンなど)などをあげることができる。なかでも、コハク酸、コハク酸ナトリウム、クエン酸、クエン酸ナトリウム、トリエタノールアミン、水酸化カリウム、水酸化ナトリウムが好ましい。 Examples of pH adjusters include inorganic acids (hydrochloric acid, sulfuric acid, phosphoric acid, polyphosphoric acid, boric acid, etc.), organic acids (lactic acid, acetic acid, citric acid, sodium citrate, tartaric acid, malic acid, succinic acid, sodium succinate, Oxalic acid, gluconic acid, fumaric acid, propionic acid, acetic acid, aspartic acid, ε-aminocaproic acid, glutamic acid, aminoethylsulfonic acid, etc.), gluconolactone, ammonium acetate, inorganic base (sodium bicarbonate, sodium carbonate, hydroxylation) And potassium (sodium hydroxide, calcium hydroxide, magnesium hydroxide, etc.), organic bases (monoethanolamine, triethanolamine, diisopropanolamine, triisopropanolamine, lysine, etc.). Of these, succinic acid, sodium succinate, citric acid, sodium citrate, triethanolamine, potassium hydroxide, and sodium hydroxide are preferable.
キレート剤としては、エチレンジアミン4酢酸(エデト酸)、エチレンジアミン4酢酸塩(ナトリウム塩(エデト酸ナトリウム:日本薬局方、EDTA−2Naなど)、カリウム塩など)、フィチン酸、グルコン酸、ポリリン酸、メタリン酸などをあげることができる。なかでも、エデト酸ナトリウムが好ましい。 Chelating agents include ethylenediaminetetraacetic acid (edetic acid), ethylenediaminetetraacetic acid salt (sodium salt (sodium edetate: Japanese Pharmacopoeia, EDTA-2Na, etc.), potassium salt, etc.), phytic acid, gluconic acid, polyphosphoric acid, metalin Acids can be raised. Of these, sodium edetate is preferred.
安定化剤としては、ポリアクリル酸ナトリウム、ジブチルヒドロキシトルエン、ブチルヒドロキシアニソールなどをあげることができる。 Examples of the stabilizer include sodium polyacrylate, dibutylhydroxytoluene, butylhydroxyanisole and the like.
刺激低減剤としては、甘草エキス、アルギン酸ナトリウム、2−メタクリロイルオキシエチルホスホリルコリンなどをあげることができる。 Examples of the irritation reducing agent include licorice extract, sodium alginate, 2-methacryloyloxyethyl phosphorylcholine and the like.
着色剤としては、無機顔料、天然色素などをあげることができる。 Examples of the colorant include inorganic pigments and natural pigments.
パール光沢付与剤としては、ジステアリン酸エチレングリコール、モノステアリン酸エチレングリコール、ジステアリン酸トリエチレングリコールなどをあげることができる。なかでも、ジステアリン酸エチレングリコールが好ましい。 Examples of the pearl luster imparting agent include ethylene glycol distearate, ethylene glycol monostearate, and triethylene glycol distearate. Of these, ethylene glycol distearate is preferred.
(その他の活性成分)
本発明において、薬剤には、本発明の効果を妨げない範囲で、抗酸化成分、老化防止成分、抗炎症成分、他の美白成分、角質柔軟成分、細胞賦活化成分、ビタミン類、血行促進成分、保湿成分、DNAの損傷の予防および/または修復作用を有する成分、紫外線吸収成分、紫外線散乱成分、洗浄成分、抗菌成分、収斂成分などの、化粧品や医薬部外品に添加しうる他の活性成分を配合することができる。他の活性成分は、1種を単独で、または2種以上を組み合わせて使用できる。
(Other active ingredients)
In the present invention, the drug includes an antioxidant component, an anti-aging component, an anti-inflammatory component, other whitening component, a keratin soft component, a cell activation component, vitamins, and a blood circulation promoting component, as long as the effects of the present invention are not hindered. Other activities that can be added to cosmetics and quasi-drugs, such as moisturizing ingredients, ingredients that prevent and / or repair DNA damage, UV-absorbing ingredients, UV-scattering ingredients, cleaning ingredients, antibacterial ingredients, and astringent ingredients Ingredients can be blended. Other active ingredients can be used singly or in combination of two or more.
抗酸化成分としては、植物(たとえば、ブドウ、オタネニンジン、コンフリー等)に由来する成分;プロアントシアニジン、トコフェロールおよびその誘導体、アスコルビン酸およびその誘導体、へスペリジン、グルコシルヘスペリジン、エルゴチオネイン、亜硫酸水素ナトリウム、エリソルビン酸およびその塩、フラボノイド、グルタチオン、グルタチオンペルオキシダーゼ、グルタチオン−S−トランスフェラーゼ、カタラーゼ、スーパーオキサイドジスムターゼ、チオレドキシン、タウリン、チオタウリン、ヒポタウリンなどをあげることができる。なかでも、ブドウ種子エキス、ブドウ葉エキス、オタネニンジンエキス、コンフリー葉エキス、プロアントシアニジン、トコフェロールおよびその誘導体(特に、δ−トコフェロール、α−トコフェロール)、アスコルビン酸およびその誘導体(特に、アスコルビン酸、アスコルビン酸リン酸エステルナトリウム、アスコルビン酸リン酸エステルマグネシウム、テトライソパルミチン酸アスコルビル(テトラ2−ヘキシルデカン酸アスコルビル))、へスペリジン、グルコシルヘスペリジン、エルゴチオネインが好ましい。 Antioxidant components include components derived from plants (eg, grapes, ginseng, comfrey, etc.); proanthocyanidins, tocopherols and derivatives thereof, ascorbic acid and derivatives thereof, hesperidin, glucosyl hesperidin, ergothioneine, sodium bisulfite, erythorbine Examples thereof include acids and salts thereof, flavonoids, glutathione, glutathione peroxidase, glutathione-S-transferase, catalase, superoxide dismutase, thioredoxin, taurine, thiotaurine, and hypotaurine. Among them, grape seed extract, grape leaf extract, ginseng extract, comfrey leaf extract, proanthocyanidins, tocopherol and its derivatives (particularly δ-tocopherol, α-tocopherol), ascorbic acid and its derivatives (particularly ascorbic acid, ascorbine) Sodium acid phosphate sodium, magnesium ascorbate phosphate, ascorbyl tetraisopalmitate (ascorbyl tetra-2-hexyldecanoate), hesperidin, glucosyl hesperidin and ergothioneine are preferred.
抗シワ、老化防止成分としては、加水分解大豆タンパク、レチノイド(レチノールおよびその誘導体、レチノイン酸、レチナール等)、パンガミン酸、カイネチン、ウルソール酸、ウコンエキス、スフィンゴシン誘導体、ケイ素、ケイ酸、N−メチル−L−セリン、メバロノラクトン等をあげることができる。なかでも、アルテミアエキス、加水分解大豆タンパク、レチノール、酢酸レチノール、パルミチン酸レチノールが好ましい。 Anti-wrinkle and anti-aging components include hydrolyzed soy protein, retinoids (retinol and its derivatives, retinoic acid, retinal, etc.), pangamic acid, kinetin, ursolic acid, turmeric extract, sphingosine derivatives, silicon, silicic acid, N-methyl -L-serine, mevalonolactone and the like can be mentioned. Of these, artemia extract, hydrolyzed soy protein, retinol, retinol acetate, and retinol palmitate are preferred.
抗炎症成分としては、植物(たとえば、コンフリー)に由来する成分;アラントイン、カラミン、グリチルリチン酸またはその誘導体、グリチルレチン酸またはその誘導体、酸化亜鉛、グアイアズレン、塩酸ピリドキシン、メントール、カンフル、テレピン油、インドメタシン、サリチル酸またはその誘導体などをあげることができる。なかでも、コンフリー葉エキス、アラントイン、グリチルリチン酸ジカリウム、グリチルレチン酸ステアリルが好ましい。 Anti-inflammatory components include components derived from plants (eg Comfrey); allantoin, calamine, glycyrrhizic acid or derivatives thereof, glycyrrhetinic acid or derivatives thereof, zinc oxide, guaiazulene, pyridoxine hydrochloride, menthol, camphor, turpentine oil, indomethacin And salicylic acid or a derivative thereof. Of these, Comfrey leaf extract, allantoin, dipotassium glycyrrhizinate, and stearyl glycyrrhetinate are preferable.
他の美白成分としては、たとえば、アルブチン;ハイドロキノン;コウジ酸;エラグ酸;フィチン酸;ルシノール;カモミラET;アスコルビン酸またはその誘導体;ビタミンEまたはその誘導体;パントテン酸またはその誘導体;トラネキサム酸などや、美白作用を有する植物成分(たとえば、植物エキスや精油)をあげることができる。なかでも、アルブチン、ハイドロキノン、コウジ酸、アスコルビン酸、アスコルビン酸リン酸エステルナトリウム、アスコルビン酸リン酸エステルマグネシウム、テトライソパルミチン酸アスコルビル(テトラ2−ヘキシルデカン酸アスコルビル)、2−O−エチルアスコルビン酸、3−O−エチルアスコルビン酸、トラネキサム酸が好ましい。 Other whitening components include, for example, arbutin; hydroquinone; kojic acid; ellagic acid; phytic acid; lucinol; chamomile ET; ascorbic acid or a derivative thereof; vitamin E or a derivative thereof; pantothenic acid or a derivative thereof; The plant component (for example, a plant extract and essential oil) which has a whitening effect can be mention | raise | lifted. Among them, arbutin, hydroquinone, kojic acid, ascorbic acid, sodium ascorbate phosphate, magnesium ascorbate phosphate, ascorbyl tetraisopalmitate (ascorbyl tetra-2-hexyldecanoate), 2-O-ethylascorbic acid, 3 -O-ethylascorbic acid and tranexamic acid are preferable.
角質柔軟成分としては、ラノリン、尿素、α−ヒドロキシ酸(フィチン酸、乳酸、乳酸塩、グリコール酸、サリチル酸、リンゴ酸等)、クエン酸などをあげることができる。なかでも、乳酸、乳酸ナトリウム、グリコール酸、サリチル酸、フィチン酸が好ましい。 Examples of the keratin soft component include lanolin, urea, α-hydroxy acid (phytic acid, lactic acid, lactate, glycolic acid, salicylic acid, malic acid, etc.), citric acid, and the like. Of these, lactic acid, sodium lactate, glycolic acid, salicylic acid, and phytic acid are preferable.
細胞賦活化成分としては、植物(たとえば、ビルベリー)に由来する成分;γ−アミノ酪酸、ε−アミノプロン酸などのアミノ酸類;レチノールおよびその誘導体、チアミン、リボフラビン、塩酸ピリドキシン、パントテン酸類などのビタミン類;グリコール酸、乳酸などのα−ヒドロキシ酸類;タンニン、フラボノイド、サポニン、アラントイン、感光素301号などをあげることができる。なかでも、ビルベリー葉エキス、レチノール、酢酸レチノール、パルミチン酸レチノールが好ましい。 Cell activation components include components derived from plants (eg, bilberry); amino acids such as γ-aminobutyric acid and ε-aminoproic acid; vitamins such as retinol and its derivatives, thiamine, riboflavin, pyridoxine hydrochloride, and pantothenic acids And α-hydroxy acids such as glycolic acid and lactic acid; tannins, flavonoids, saponins, allantoins, and photosensitizer 301. Of these, bilberry leaf extract, retinol, retinol acetate, and retinol palmitate are preferred.
ビタミン類としては、レチノール、酢酸レチノール、パルミチン酸レチノール等のレチノール誘導体、レチナール、レチノイン酸、レチノイン酸メチル、レチノイン酸エチル、レチノイン酸レチノール、d−δ−トコフェリルレチノエート、α−トコフェリルレチノエート、β−トコフェリルレチノエート等のビタミンA類;β−カロチン、α−カロチン、γ−カロチン、δ−カロチン、リコピン、ゼアキサンチン、クリプトキサンチン、エキネノン等のプロビタミンA類;δ−トコフェロール、α−トコフェロール、β−トコフェロール、コハク酸dl−α−トコフェロール、コハク酸dl−α−トコフェロールカルシウム、δ−トコフェロール、ニコチン酸トコフェロール等のビタミンE類;リボフラビン、フラビンモノヌクレオチド、フラビンアデニンジヌクレオチド、リボフラビン酪酸エステル、リボフラビンテトラ酪酸エステル、リボフラビン5’−リン酸エステルナトリウム、リボフラビンテトラニコチン酸エステル等のビタミンB2類;ニコチン酸メチル、ニコチン酸、ニコチン酸アミドなどのニコチン酸類;ステアリン酸アスコルビル、ジパルミチン酸L−アスコルビル、テトライソパルミチン酸アスコルビル(テトラ2−ヘキシルデカン酸アスコルビル)、アスコルビン酸、アスコルビン酸ナトリウム、デヒドロアスコルビン酸、アスコルビン酸リン酸エステルナトリウム、アスコルビン酸リン酸エステルマグネシウム、アスコルビン酸グルコシド、2−O−エチルアスコルビン酸、3−O−エチルアスコルビン酸などのビタミンC類;メチルヘスペリジン、エルゴカルシフェロール、コレカルシフェロールなどのビタミンD類;フィロキノン、ファルノキノン等のビタミンK類;ジベンゾイルチアミン、ジベンゾイルチアミン塩酸塩、チアミン塩酸塩、チアミンセチル塩酸塩、チアミンチオシアン酸塩、チアミンラウリル塩酸塩、チアミン硝酸塩、チアミンモノリン酸塩、チアミンリジン塩、チアミントリリン酸塩、チアミンモノリン酸エステルリン酸塩、チアミンモノリン酸エステル、チアミンジリン酸エステル、チアミンジリン酸エステル塩酸塩、チアミントリリン酸エステル、チアミントリリン酸エステルモノリン酸塩等のビタミンB1類;塩酸ピリドキシン、酢酸ピリドキシン、塩酸ピリドキサール、5’−リン酸ピリドキサール、塩酸ピリドキサミン等のビタミンB6類、シアノコバラミン、ヒドロキソコバラミン、デオキシアデノシルコバラミン等のビタミンB12類;葉酸、プテロイルグルタミン酸等の葉酸類;パントテン酸、パントテン酸カルシウム、パントテニルアルコール(パンテノール)、D−パンテテイン、D−パンテチン、補酵素A、パントテニルエチルエーテル等のパントテン酸類;ビオチン、ビオシチン等のビオチン類;そのほか、カルニチン、フェルラ酸、α−リポ酸、オロット酸、γ−オリザノール等のビタミン様作用因子などをあげることができる。 Vitamins include retinol, retinol acetate, retinol palmitate, etc., retinal, retinoic acid, methyl retinoic acid, ethyl retinoic acid, retinol retinoic acid, d-δ-tocopheryl retinoate, α-tocopheryl retinoate Vitamins such as β-tocopheryl retinoate; provitamins A such as β-carotene, α-carotene, γ-carotene, δ-carotene, lycopene, zeaxanthin, cryptoxanthine, echinone; δ-tocopherol, α- Vitamin Es such as tocopherol, β-tocopherol, dl-α-tocopherol succinate, dl-α-tocopherol calcium succinate, δ-tocopherol, tocopherol nicotinate; riboflavin, flavin mononucleotide, flavin Vitamin B2 such as denine dinucleotide, riboflavin butyrate, riboflavin tetrabutyrate, riboflavin 5'-phosphate sodium, riboflavin tetranicotinate; nicotinic acids such as methyl nicotinate, nicotinic acid, nicotinamide; stearic acid Ascorbyl, L-ascorbyl dipalmitate, ascorbyl tetraisopalmitate (ascorbyl tetra-2-hexyldecanoate), ascorbic acid, sodium ascorbate, dehydroascorbic acid, sodium ascorbate phosphate, magnesium ascorbate phosphate, ascorbic acid Vitamin Cs such as glucoside, 2-O-ethylascorbic acid, 3-O-ethylascorbic acid; methyl hesperidin, ergocalci Vitamin Ds such as ferrol and cholecalciferol; vitamin Ks such as phylloquinone and farnoquinone; dibenzoyl thiamine, dibenzoyl thiamine hydrochloride, thiamine hydrochloride, thiamine cetyl hydrochloride, thiamine thiocyanate, thiamine lauryl hydrochloride, thiamine Nitrate, thiamine monophosphate, thiamine lysine salt, thiamine triphosphate, thiamine monophosphate phosphate, thiamine monophosphate, thiamine diphosphate, thiamine diphosphate hydrochloride, thiamine triphosphate, thiamine triphosphate Vitamin B1 such as monophosphate; Vitamin B6 such as pyridoxine hydrochloride, pyridoxine acetate, pyridoxal hydrochloride, 5'-pyridoxal phosphate, pyridoxamine hydrochloride, cyanocobalamin, hydro Vitamin B12 such as socobalamin and deoxyadenosylcobalamin; folic acid such as folic acid and pteroylglutamic acid; pantothenic acid, calcium pantothenate, pantothenyl alcohol (panthenol), D-pantethein, D-panthetin, coenzyme A, pant Examples thereof include pantothenic acids such as tenenyl ethyl ether; biotins such as biotin and biocytin; and vitamin-like agents such as carnitine, ferulic acid, α-lipoic acid, orotic acid, and γ-oryzanol.
なかでも、レチノール、酢酸レチノール、パルミチン酸レチノールなどのビタミンA類;アスコルビン酸、アスコルビン酸リン酸エステルナトリウム、アスコルビン酸リン酸エステルマグネシウム、テトライソパルミチン酸アスコルビル(テトラ2−ヘキシルデカン酸アスコルビル)、2−O−エチルアスコルビン酸、3−O−エチルアスコルビン酸などのビタミンC類;δ−トコフェロール、ニコチン酸トコフェロール等のビタミンE類;ニコチン酸アミドなどのニコチン酸類が好ましい。 Among them, vitamin A such as retinol, retinol acetate, retinol palmitate, etc .; ascorbic acid, sodium ascorbate phosphate, magnesium ascorbate phosphate, ascorbyl tetraisopalmitate (ascorbyl tetra-2-hexyldecanoate), 2- Vitamin Cs such as O-ethylascorbic acid and 3-O-ethylascorbic acid; Vitamin Es such as δ-tocopherol and tocopherol nicotinate; and nicotinic acids such as nicotinamide are preferable.
血行促進作用成分としては、植物(たとえば、オタネニンジン、アシタバ、アルニカ、イチョウ、ウイキョウ、エンメイソウ、オランダカシ、カミツレ、ローマカミツレ、カロット、ゲンチアナ、ゴボウ、コメ、サンザシ、シイタケ、セイヨウサンザシ、セイヨウネズ、センキュウ、センブリ、タイム、チョウジ、チンピ、トウキ、トウニン、トウヒ、ニンジン、ニンニク、ブッチャーブルーム、ブドウ、ボタン、マロニエ、メリッサ、ユズ、ヨクイニン、ローズマリー、ローズヒップ、チンピ、トウキ、トウヒ、モモ、アンズ、クルミ、トウモロコシ)に由来する成分;ニコチン酸トコフェロール、グルコシルヘスペリジン、ヘスペリジンをあげることができる。なかでも、オタネニンジンエキス、ニコチン酸トコフェロール、グルコシルヘスペリジン、ヘスペリジンが好ましい。 Examples of the blood circulation promoting component include plants (for example, ginseng, ashitaba, arnica, ginkgo, fennel, enmelio, dutch oak, chamomile, roman chamomile, carrot, gentian, burdock, rice, hawthorn, shiitake, hawthorn, prunus, nematode, Assembly, thyme, clove, chimney, spruce, spruce, spruce, carrot, garlic, butcher bloom, grape, button, maronier, melissa, yuzu, yokuinin, rosemary, rosehip, chimpy, touki, spruce, peach, apricot, walnut Ingredients derived from corn); tocopherol nicotinate, glucosyl hesperidin, hesperidin. Of these, ginseng extract, tocopherol nicotinate, glucosyl hesperidin, and hesperidin are preferable.
保湿成分としては、植物(たとえば、チガヤ)に由来する成分;アラニン、セリン、ロイシン、イソロイシン、スレオニン、グリシン、プロリン、ヒドロキシプロリン、グルコサミン、テアニンのようなアミノ酸およびその誘導体;コラーゲン、ゼラチン、エラスチンのようなタンパク質やペプチド、その加水分解物;グリセリン、1,3−ブチレングリコール、プロピレングリコール、ポリエチレングリコール、ジプロピレングリコール、ジグリセリンなどの多価アルコール;ソルビトールのような糖アルコール;レシチン、水素添加レシチンのようなリン脂質;ヒアルロン酸、ヒアルロン酸ナトリウム、アセチルヒアルロン酸、アセチルヒアルロン酸ナトリウム、ヘパリン、コンドロイチンのようなムコ多糖;乳酸、ピロリドンカルボン酸ナトリウム、尿素のようなNMF由来成分;ポリグルタミン酸;MPCポリマー(たとえば、LIPIDURE(商標)等)等のリン脂質極性基を有する高分子;ポリオキシプロピレンメチルグルコシド;トリメチルグリシン(ベタイン);ヒドロキシエチルウレア;アクリル酸・アクリルアミド・塩化ジメチルジアリルアンモニウム共重合体;ソルビトールなどをあげることができる。なかでも、チガヤ根エキス、加水分解コラーゲン、加水分解エラスチン、MPCポリマーグリセリン、1,3−ブチレングリコール、ポリエチレングリコール、ジプロピレングリコール、ジグリセリン、ポリオキシプロピレンメチルグルコシド、トリメチルグリシン(ベタイン)、ヒドロキシエチルウレア、アクリル酸・アクリルアミド・塩化ジメチルジアリルアンモニウム共重合体、水素添加レシチン、ヒアルロン酸、ヒアルロン酸ナトリウム、アセチルヒアルロン酸、アセチルヒアルロン酸ナトリウム、ソルビトールが好ましい。 Moisturizing ingredients include ingredients derived from plants (eg, Tigaya); amino acids such as alanine, serine, leucine, isoleucine, threonine, glycine, proline, hydroxyproline, glucosamine, theanine and derivatives thereof; collagen, gelatin, elastin Such proteins and peptides, hydrolysates thereof; polyhydric alcohols such as glycerin, 1,3-butylene glycol, propylene glycol, polyethylene glycol, dipropylene glycol, diglycerin; sugar alcohols such as sorbitol; lecithin, hydrogenated lecithin Phospholipids such as: hyaluronic acid, sodium hyaluronate, acetyl hyaluronic acid, sodium acetyl hyaluronate, heparin, chondroitin mucopolysaccharides; lactic acid, pyrrolidone carvone NMF-derived components such as sodium and urea; polyglutamic acid; polymers having a phospholipid polar group such as MPC polymer (for example, LIPIDURE ™); polyoxypropylene methylglucoside; trimethylglycine (betaine); hydroxyethylurea Acrylic acid / acrylamide / dimethyldiallylammonium chloride copolymer; sorbitol and the like. Among them, chigaya root extract, hydrolyzed collagen, hydrolyzed elastin, MPC polymer glycerin, 1,3-butylene glycol, polyethylene glycol, dipropylene glycol, diglycerin, polyoxypropylene methylglucoside, trimethylglycine (betaine), hydroxyethyl Urea, acrylic acid / acrylamide / dimethyldiallylammonium chloride copolymer, hydrogenated lecithin, hyaluronic acid, sodium hyaluronate, acetyl hyaluronic acid, sodium acetyl hyaluronate and sorbitol are preferred.
DNAの損傷の予防および/または修復作用を有する成分としては、動物(たとえば、アルテミア)に由来する成分;植物(たとえば、キャッツクロー)に由来する成分;DNA、DNA塩、RNA、RNA塩等の核酸成分をあげることができる。なかでも、アルテミアエキス、DNA−Naが好ましい。 Examples of the component having an action of preventing and / or repairing DNA damage include components derived from animals (eg, Artemia); components derived from plants (eg, cat's claw); DNA, DNA salts, RNA, RNA salts, etc. Nucleic acid components can be mentioned. Of these, artemia extract and DNA-Na are preferable.
紫外線吸収成分としては、パラメトキシケイ皮酸2−エチルヘキシル、2−[4−(ジエチルアミノ)−2−ヒドロキシベンゾイル]安息香酸ヘキシルエステル、2,4,6−トリス[4−(2−エチルヘキシルオキシカルボニル)アニリノ]−1,3,5−トリアジン、ジメトキシベンジリデンオキソイミダゾリジンプロピオン酸2−エチルヘキシル、2,4−ビス−[{4−(2−エチルヘキシルオキシ)−2−ヒドロキシ}−フェニル]−6−(4−メトキシフェニル)−1,3,5−トリアジンなどをあげることができる。なかでも、パラメトキシケイ皮酸2−エチルヘキシル、2−[4−(ジエチルアミノ)−2−ヒドロキシベンゾイル]安息香酸ヘキシルエステル、2,4,6−トリス[4−(2−エチルヘキシルオキシカルボニル)アニリノ]−1,3,5−トリアジンが好ましい。 Examples of ultraviolet ray absorbing components include 2-methoxyhexyl paramethoxycinnamate, 2- [4- (diethylamino) -2-hydroxybenzoyl] benzoic acid hexyl ester, 2,4,6-tris [4- (2-ethylhexyloxycarbonyl) ) Anilino] -1,3,5-triazine, dimethoxybenzylideneoxoimidazolidinepropionate 2-ethylhexyl, 2,4-bis-[{4- (2-ethylhexyloxy) -2-hydroxy} -phenyl] -6 (4-methoxyphenyl) -1,3,5-triazine and the like can be mentioned. Among them, 2-methoxyhexyl paramethoxycinnamate, 2- [4- (diethylamino) -2-hydroxybenzoyl] benzoic acid hexyl ester, 2,4,6-tris [4- (2-ethylhexyloxycarbonyl) anilino] -1,3,5-triazine is preferred.
紫外線散乱成分としては、酸化亜鉛、酸化チタン、酸化鉄、酸化セリウム、酸化ジルコニウム、ケイ酸チタン、ケイ酸亜鉛、無水ケイ酸、ケイ酸セリウム、含水ケイ酸等の無機化合物や、それらの無機化合物を含水ケイ酸、水酸化アルミニウムで被覆したもの、マイカやタルク等の無機粉体に被覆したもの、ポリアミド、ポリエチレン、ポリエステル、ポリスチレン、ナイロン等の樹脂粉体に複合化したもの、さらにシリコン油や脂肪酸アルミニウム塩等で処理したものなどをあげることができる。なかでも、酸化亜鉛、酸化チタン、酸化鉄等の無機化合物や、これらの無機化合物を水酸化アルミニウム、含水ケイ酸、マイカやタルク等の無機粉体やシリコン油で被覆したものが好ましい。 Ultraviolet scattering components include inorganic compounds such as zinc oxide, titanium oxide, iron oxide, cerium oxide, zirconium oxide, titanium silicate, zinc silicate, anhydrous silicic acid, cerium silicate, hydrous silicic acid, and those inorganic compounds Coated with water-containing silicic acid, aluminum hydroxide, coated with inorganic powder such as mica and talc, compounded with resin powder such as polyamide, polyethylene, polyester, polystyrene, nylon, etc. The thing processed with fatty acid aluminum salt etc. can be mention | raise | lifted. Of these, inorganic compounds such as zinc oxide, titanium oxide and iron oxide, and those inorganic compounds coated with inorganic powder such as aluminum hydroxide, hydrous silicic acid, mica and talc, and silicon oil are preferable.
洗浄成分としては、ポリオキシアルキレンアルキル(またはアルケニル)エーテル硫酸塩、アルキル(またはアルケニル)硫酸塩、高級脂肪酸塩、エーテルカルボン酸塩、アミドエーテルカルボン酸塩、アルキルリン酸エステル塩、N−アシルアミノ酸塩、ポリオキシアルキレン脂肪酸アミドエーテル硫酸塩、アシル化イセチオン酸塩、アシル化タウレート等のアニオン界面活性剤;アミンオキサイド、グリセリン脂肪酸エステル、ソルビタン脂肪酸エステル、アルキルサッカライド、ポリオキシアルキレンアルキルエーテル、脂肪酸アルカノールアミド、ポリオキシアルキレン硬化ヒマシ油等の非イオン界面活性剤;アルキレンオキサイドが付加していてもよい、直鎖または分岐鎖の長鎖アルキル基を有するモノまたはジ長鎖アルキル第4級アンモニウム塩等のカチオン界面活性剤;カルボベタイン、スルホベタイン、イミダゾリニウムベタイン、アミドベタイン等の両性界面活性剤をあげることができる。 Cleaning components include polyoxyalkylene alkyl (or alkenyl) ether sulfates, alkyl (or alkenyl) sulfates, higher fatty acid salts, ether carboxylates, amide ether carboxylates, alkyl phosphate esters, N-acyl amino acids Anionic surfactants such as salts, polyoxyalkylene fatty acid amide ether sulfates, acylated isethionates, acylated taurates; amine oxides, glycerin fatty acid esters, sorbitan fatty acid esters, alkyl saccharides, polyoxyalkylene alkyl ethers, fatty acid alkanolamides , Nonionic surfactants such as polyoxyalkylene hydrogenated castor oil; mono- or di-long-chain alkyl having a linear or branched long-chain alkyl group, to which alkylene oxide may be added Cationic surfactants such as ammonium salts; carboxymethyl betaine, sulfobetaine, imidazolinium betaine, may be mentioned amphoteric surfactants such as betaines.
なかでも、アニオン界面活性剤、非イオン界面活性剤、両性界面活性剤が好ましい。アニオン界面活性剤では、高級脂肪酸塩(特に、パルミチン酸、ラウリン酸、ミリスチン酸、ステアリン酸等の高級脂肪酸の塩)、N−アシルアミノ酸塩(特に、N−ラウロイルアスパラギン酸ナトリウム、水酸化カリウム/N−ヤシ油脂肪酸アシルグルタミン酸カリウム、ヤシ油脂肪酸アシルグリシンナトリウム、ミリストイルグルタミン酸)が好ましい。非イオン界面活性剤では、脂肪酸アルカノールアミド(特に、ヤシ油脂肪酸ジエタノールアミド、ヤシ油脂肪酸モノエタノールアミド)、アミンオキサイド(特に、ヤシ油アルキルジメチルアミンオキシド、ラウリルジメチルアミンオキシド)が好ましい。両性界面活性剤では、イミダゾリニウムベタイン(特に、2−アルキル−N−カルボキシメチル−N−ヒドロキシエチルイミダゾリウムベタイン、N−ヤシ油脂肪酸アシル−N−カルボキシメトキシエチル−N−カルボキシメチルエチレンジアミン二ナトリウム)が好ましい。 Of these, anionic surfactants, nonionic surfactants, and amphoteric surfactants are preferred. Anionic surfactants include higher fatty acid salts (particularly salts of higher fatty acids such as palmitic acid, lauric acid, myristic acid and stearic acid), N-acyl amino acid salts (particularly sodium N-lauroyl aspartate, potassium hydroxide / N-coconut oil fatty acid potassium acylglutamate, coconut oil fatty acid acylglycine sodium, myristoyl glutamic acid) are preferred. Among the nonionic surfactants, fatty acid alkanolamides (especially coconut oil fatty acid diethanolamide, coconut oil fatty acid monoethanolamide) and amine oxides (especially coconut oil alkyldimethylamine oxide, lauryldimethylamine oxide) are preferable. Amphoteric surfactants include imidazolinium betaines (especially 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolium betaine, N-coconut oil fatty acid acyl-N-carboxymethoxyethyl-N-carboxymethylethylenediamine disodium. ) Is preferred.
抗菌成分としては、クロルヘキシジン、サリチル酸、塩化ベンザルコニウム、アクリノール、エタノール、塩化ベンゼトニウム、クレゾール、グルコン酸およびその誘導体、ポピドンヨード、ヨウ化カリウム、ヨウ素、イソプロピルメチルフェノール、トリクロカルバン、トリクロサン、感光素101号、感光素201号、パラベン、フェノキシエタノール、1,2−ペンタンジオール、塩酸アルキルジアミノグリシンなどをあげることができる。なかでも、塩化ベンザルコニウム、塩化ベンゼトニウム、グルコン酸およびその誘導体、イソプロピルメチルフェノール、トリクロカルバン、トリクロサン、感光素101号、感光素201号、パラベン、フェノキシエタノール、1,2−ペンタンジオール、塩酸アルキルジアミノグリシンが好ましく、塩化ベンザルコニウム、グルコン酸およびその誘導体、塩化ベンゼトニウム、イソプロピルメチルフェノールがより好ましい。 Antibacterial components include chlorhexidine, salicylic acid, benzalkonium chloride, acrinol, ethanol, benzethonium chloride, cresol, gluconic acid and its derivatives, popidone iodine, potassium iodide, iodine, isopropylmethylphenol, triclocarban, triclosan, photosensitizer 101 Photosensitive element 201, paraben, phenoxyethanol, 1,2-pentanediol, alkyldiaminoglycine hydrochloride, and the like. Among them, benzalkonium chloride, benzethonium chloride, gluconic acid and derivatives thereof, isopropylmethylphenol, triclocarban, triclosan, photosensitizer 101, photosensitizer 201, paraben, phenoxyethanol, 1,2-pentanediol, alkyldiamino hydrochloride Glycine is preferred, and benzalkonium chloride, gluconic acid and its derivatives, benzethonium chloride, and isopropylmethylphenol are more preferred.
収斂成分としては、ミョウバン、クロロヒドロキシアルミニウム、塩化アルミニウム、アラントインアルミニウム塩、硫酸亜鉛、硫酸アルミニウムカリウム等の金属塩;タンニン酸、クエン酸、乳酸、コハク酸などの有機酸をあげることができる。なかでも、ミョウバン、クロロヒドロキシアルミニウム、塩化アルミニウム、アラントインアルミニウム塩、硫酸アルミニウムカリウム、タンニン酸が好ましい。 Examples of the astringent component include metal salts such as alum, chlorohydroxyaluminum, aluminum chloride, allantoin aluminum salt, zinc sulfate, and potassium aluminum sulfate; organic acids such as tannic acid, citric acid, lactic acid, and succinic acid. Of these, alum, chlorohydroxyaluminum, aluminum chloride, allantoin aluminum salt, potassium aluminum sulfate, and tannic acid are preferable.
(製剤形態)
また、本発明における薬剤は、各成分を常法に従って、たとえば、混合撹拌することにより調製できる。
(Formulation)
Moreover, the chemical | medical agent in this invention can be prepared by mixing and stirring each component in accordance with a conventional method, for example.
本発明において、薬剤の形態は特に限定されず、化粧品または医薬部外品の形態として公知の形態を採ることができる。このような公知の形態として、たとえば、液剤、懸濁剤、乳剤、クリーム剤、軟膏剤、ゲル剤、リニメント剤、ローション剤、エアゾール剤、パウダー剤、パップ剤、不織布等のシートに薬液を含浸させたシート剤、リップスティックのようなスティック剤などをあげることができる。なかでも、使用感が良い点で、液剤、懸濁剤、乳剤、クリーム剤、軟膏剤、ゲル剤、ローション剤が好ましく、液剤、乳剤、クリーム剤、ゲル剤、ローション剤がより好ましい。また、特に上記ベンジリデンアゾリジン誘導体またはその塩は、基剤への溶解性(特に親水性)に優れ、製剤化(水溶性剤))が容易であることから、水溶液、水系懸濁液、水系乳液、水性ジェル、水系ローションの製剤形態が好適である。また、製剤に応じて水中油型(O/W)、油中水型(W/O)等、使用目的や所望の使用感に応じて、適宜選択できる。 In this invention, the form of a chemical | medical agent is not specifically limited, A well-known form can be taken as a form of cosmetics or a quasi-drug. As such known forms, for example, liquids, suspensions, emulsions, creams, ointments, gels, liniments, lotions, aerosols, powders, poultices, non-woven fabrics and the like are impregnated with chemicals. And a stick agent such as a lipstick. Of these, liquids, suspensions, emulsions, creams, ointments, gels, and lotions are preferred, and liquids, emulsions, creams, gels, and lotions are more preferred in terms of good usability. In particular, the benzylidene azolidine derivative or salt thereof is excellent in solubility in the base (particularly hydrophilic) and easy to formulate (water-soluble agent). Formulation forms of emulsions, aqueous gels and aqueous lotions are preferred. Further, depending on the formulation, an oil-in-water type (O / W), a water-in-oil type (W / O) or the like can be appropriately selected according to the purpose of use and the desired feeling of use.
また、化粧品組成物の具体的な用途は特に限定されず、化粧水、乳液、クリーム、美容液、日焼け止め用化粧品、パック、ハンドクリーム、ボディローション、ボディークリームのような基礎化粧品;洗顔料、メイク落とし、ボディーシャンプー、シャンプー、リンスのような洗浄用化粧品;ファンデーション、コンシーラー、化粧下地、リップクリーム、口紅、チークカラーのようなメークアップ化粧品;入浴剤などをあげることができる。 In addition, the specific use of the cosmetic composition is not particularly limited, and basic cosmetics such as lotion, milky lotion, cream, cosmetic liquid, sunscreen cosmetics, packs, hand creams, body lotions, body creams; Cosmetics for cleaning such as makeup removers, body shampoos, shampoos and rinses; makeup cosmetics such as foundations, concealers, makeup bases, lip balms, lipsticks and teak colors; bathing agents and the like.
本発明におけるベンジリデンアゾリジン誘導体またはその塩を有効成分とする薬剤(美白剤、抗光老化剤、チロシナーゼ阻害剤、メラニン産生抑制剤、活性酸素種生成抑制剤、SOD様活性剤、および、カタラーゼ様活性剤)が、上記いずれの形態を取る場合でも、ベンジリデンアゾリジン誘導体またはその塩の含有量は、0.00001重量%以上50重量%以下の含有量とすることができ、0.00001重量%以上20重量%以下であってもよく、0.0001重量%以上10重量%以下であってもよく、0.001重量%以上5重量%以下であってもよく、0.01重量%以上3重量%以下であってもよく、0.1重量%以上1重量%以下であってもよい。 Drugs containing benzylidene azolidine derivative or a salt thereof as an active ingredient in the present invention (whitening agent, anti-photoaging agent, tyrosinase inhibitor, melanin production inhibitor, reactive oxygen species production inhibitor, SOD-like activator, and catalase-like agent In the case where the activator) takes any of the above forms, the content of the benzylidene azolidine derivative or a salt thereof can be 0.00001 wt% or more and 50 wt% or less, and 0.00001 wt% 20 wt% or less, 0.0001 wt% or more and 10 wt% or less, 0.001 wt% or more and 5 wt% or less, 0.01 wt% or more 3 % By weight or less, or 0.1% by weight or more and 1% by weight or less may be used.
以下、本発明の構成と効果を具体的に示す実施例等について説明する。なお、実施例等における評価項目は下記のようにして測定を行った。 Examples and the like specifically showing the configuration and effects of the present invention will be described below. In addition, the evaluation item in an Example etc. measured as follows.
<1H−NMRスペクトルの測定>
1H−NMRスペクトルの測定は、核磁気共鳴装置(日本電子社製、JNM−ECP500)を用いて行った。より詳細には、1H−NMRスペクトルの測定は、溶媒としてDMSO−d6を用い、内部標準としてテトラメチルシランを用いて行った。
<Measurement of 1 H-NMR spectrum>
1 H-NMR spectrum was measured using a nuclear magnetic resonance apparatus (JNM-ECP500, manufactured by JEOL Ltd.). More specifically, the 1 H-NMR spectrum was measured using DMSO-d 6 as a solvent and tetramethylsilane as an internal standard.
<UVスペクトルの測定>
UVスペクトルの測定は、分光光度計(島津製作所社製、UV−4250)を用いて行った。より詳細には、UVスペクトルの測定は、溶媒としてエタノールを用い、試料溶液の濃度5ppmで、光路長1cmの石英セルを用いて行った。なお、吸光度は、Lambert−beerの法則に従って、Ioを空のセルの透過光強度、Iが試料セルの透過光強度とした場合、吸光度=−log10(I/I0)で算出した。また、得られたUVスペクトルにおける吸光度が最大となる波長をλmax(nm)とした。
<Measurement of UV spectrum>
The UV spectrum was measured using a spectrophotometer (manufactured by Shimadzu Corporation, UV-4250). More specifically, the UV spectrum was measured using a quartz cell with ethanol as a solvent, a sample solution concentration of 5 ppm, and an optical path length of 1 cm. The absorbance was calculated according to Lambert-Beer's law, where Io was the transmitted light intensity of the empty cell and I was the transmitted light intensity of the sample cell, with absorbance = −log 10 (I / I 0 ). Further, the wavelength at which the absorbance in the obtained UV spectrum becomes maximum was defined as λmax (nm).
<親水性評価>
得られた化合物(1)を、以下に示す試験溶媒に溶解させ、性状確認を行うとともに、試験溶媒100g対する25℃における溶解度(g/100g試験溶媒)を測定した。
・試験溶媒:ジプロピレングリコール、エタノール、および精製水を、それぞれ10質量%、10質量%および80質量%の量で含む混合溶媒(ただし、ジプロピレングリコール、エタノール、および精製水の合計量を100質量%とする。)
<Hydrophilicity evaluation>
The obtained compound (1) was dissolved in the test solvent shown below, the properties were confirmed, and the solubility (g / 100 g test solvent) at 25 ° C. with respect to 100 g of the test solvent was measured.
Test solvent: A mixed solvent containing dipropylene glycol, ethanol, and purified water in amounts of 10% by mass, 10% by mass, and 80% by mass, respectively (however, the total amount of dipropylene glycol, ethanol, and purified water is 100 (Mass%)
なお、溶解度の違いによって以下のように親水性評価を行った。
・1.0以上(g/100g試験溶媒)の場合:親水性が特に高い
・0.2以上〜1.0未満(g/100g試験溶媒)の場合:親水性が高い
・0.1以上〜0.2未満(g/100g試験溶媒)の場合:親水性が乏しい
・0.1未満(g/100g試験溶媒)の場合、固体浮遊物のある場合:親水性がない
In addition, hydrophilicity evaluation was performed as follows by the difference in solubility.
When 1.0 or more (g / 100 g test solvent): particularly high hydrophilicity When 0.2 or more and less than 1.0 (g / 100 g test solvent): high hydrophilicity 0.1 or more If less than 0.2 (g / 100 g test solvent): poor hydrophilicity. If less than 0.1 (g / 100 g test solvent), if there is a solid suspension: not hydrophilic
〔実施例1〕
(化合物(1)の合成)
300mLナス型フラスコ中で、4−ヒドロキシベンズアルデヒド14.7g(120mmol)に、2−(2−クロロエトキシ)エタノール16.4g(132mmol)、炭酸カリウム33.2g(240mmol)、アセトニトリル150mLを加えて、105℃で14時間撹拌しながら加熱した。さらに、2−(2−クロロエトキシ)エタノール1.49g(12.0mmol)を加えて、105℃で30時間撹拌しながら加熱した。反応混合液が室温まで冷えた後、セライト濾過によって固形物を除去した。溶剤を減圧下にて留去し、白い固形物の混ざった黄色粘性物質を34.6g得た。
[Example 1]
(Synthesis of Compound (1))
In a 300 mL eggplant-shaped flask, 16.4 g (132 mmol) of 2- (2-chloroethoxy) ethanol, 33.2 g (240 mmol) of potassium carbonate, and 150 mL of acetonitrile were added to 14.7 g (120 mmol) of 4-hydroxybenzaldehyde. Heated at 105 ° C. with stirring for 14 hours. Furthermore, 1.49 g (12.0 mmol) of 2- (2-chloroethoxy) ethanol was added and heated at 105 ° C. with stirring for 30 hours. After the reaction mixture cooled to room temperature, the solid was removed by celite filtration. The solvent was distilled off under reduced pressure to obtain 34.6 g of a yellow viscous substance mixed with a white solid.
これに水を80mL加えて、別に用意した200mLナス型フラスコ中に移し替え、ヒダントイン15.6g(156mmol)、28%アンモニア水14.4gを加えて、90℃で12時間撹拌しながら加熱した。反応混合液が室温まで冷えた後、濾過によって析出した結晶を回収した。その後、水で2回、エタノールで2回、結晶の洗浄を行った。乾燥後、5−[4−[2−(2−ヒドロキシエトキシ)エトキシ]ベンジリデン]ヒダントインを29.6g得た。 80 mL of water was added thereto, transferred to a separately prepared 200 mL eggplant-shaped flask, 15.6 g (156 mmol) of hydantoin and 14.4 g of 28% aqueous ammonia were added, and the mixture was heated at 90 ° C. with stirring for 12 hours. After the reaction mixture had cooled to room temperature, the precipitated crystals were collected by filtration. Thereafter, the crystals were washed twice with water and twice with ethanol. After drying, 29.6 g of 5- [4- [2- (2-hydroxyethoxy) ethoxy] benzylidene] hydantoin was obtained.
続いて、得られたうちの17.5g(60.0mmol)に、200mLナス型フラスコ中で、2−(2−クロロエトキシ)エタノール7.47g(60mmol)、炭酸カリウム20.0g(145mmol)、N,N−ジメチルホルムアミド80mLを加えて、110℃で3時間撹拌しながら加熱した。反応混合液が室温まで冷えた後、セライト濾過によって固形物を除去した。溶剤を減圧下にて留去し、白い固形物の混ざった黄色粘性物質を30.5g得た。これをシリカゲルカラムクロマトグラフィー(展開溶媒;イソプロパノール:トルエン=1:3)によって精製し、黄色の結晶を9.21g得た。これをエタノールで活性炭処理し、再結晶させることで、下記化合物(1)を6.56g得た(収率;25%)。
(化合物(1)のスペクトルデータ等)
UVスペクトル:λmax;335nm、吸光度;0.43(エタノール)。
1H−NMRスペクトル:δ〔ppm、DMSO−d6〕=3.41−3.46(m,4H),3.48−3.53(m,4H),3.60(m,2H),3.64(m,2H),3.75(t,2H),4.15(t,2H),4.61(t,1H),4.67(t,1H),6.52(s,1H),6.99(d,2H),7.62(d,2H),10.71(s,1H)。
溶解度:2.0(g/100g試験溶媒)、親水性が特に高い。
(Spectral data of compound (1), etc.)
UV spectrum: [lambda] max; 335 nm, absorbance; 0.43 (ethanol).
1 H-NMR spectrum: δ [ppm, DMSO-d 6 ] = 3.41-3.46 (m, 4H), 3.48-3.53 (m, 4H), 3.60 (m, 2H) , 3.64 (m, 2H), 3.75 (t, 2H), 4.15 (t, 2H), 4.61 (t, 1H), 4.67 (t, 1H), 6.52 ( s, 1H), 6.99 (d, 2H), 7.62 (d, 2H), 10.71 (s, 1H).
Solubility: 2.0 (g / 100 g test solvent), especially hydrophilic.
〔実施例2〕
(化合物(2)の合成)
200mLナス型フラスコ中で、4−ヒドロキシベンズアルデヒド14.7g(120mmol)に、ヒダントイン15.6g(156mmol)、水80mL、28%アンモニア水14.4gを加えて、90℃で12時間撹拌しながら加熱した。反応混合液が室温まで冷えた後、濾過によって析出した結晶を回収した。その後、水で2回、エタノールで2回、結晶の洗浄を行った。乾燥後、5−(4−ヒドロキシベンジリデン)ヒダントインを20.3g得た。
[Example 2]
(Synthesis of Compound (2))
In a 200 mL eggplant type flask, 15.6 g (156 mmol) of hydantoin, 80 mL of water, and 14.4 g of 28% aqueous ammonia are added to 14.7 g (120 mmol) of 4-hydroxybenzaldehyde and heated at 90 ° C. with stirring for 12 hours. did. After the reaction mixture had cooled to room temperature, the precipitated crystals were collected by filtration. Thereafter, the crystals were washed twice with water and twice with ethanol. After drying, 20.3 g of 5- (4-hydroxybenzylidene) hydantoin was obtained.
続いて、得られたうちの18.8g(92.2mmol)を、500mLナス型フラスコ中で、N,N−ジメチルホルムアミド180mLに溶かした後、クロロ酢酸エチル27.1g(221mmol)、炭酸カリウム30.5g(221mmol)を加えて、120℃で2時間撹拌しながら加熱した。反応混合液が室温まで冷えた後、溶剤を減圧下にて留去し、水を加えて、酢酸エチルで3回抽出を行った。有機層をあわせて、水で2回、飽和食塩水で1回洗浄した後、有機層を硫酸ナトリウムにて乾燥させた。その後、硫酸ナトリウムを濾過して除去し、溶剤を減圧下にて留去した後、得られた茶褐色の結晶を、酢酸エチルとへキサンの混合溶媒で再結晶を行い、乾燥後、5−[4−(2−エトキシ−2−オキソエトキシ)ベンジリデン]−3−(2−エトキシ−2−オキソエチル)ヒダントインを9.96g得た。 Subsequently, 18.8 g (92.2 mmol) of the obtained product was dissolved in 180 mL of N, N-dimethylformamide in a 500 mL eggplant type flask, and then 27.1 g (221 mmol) of ethyl chloroacetate, 30 of potassium carbonate. 0.5 g (221 mmol) was added and heated at 120 ° C. with stirring for 2 hours. After the reaction mixture was cooled to room temperature, the solvent was distilled off under reduced pressure, water was added, and extraction was performed three times with ethyl acetate. The organic layers were combined, washed twice with water and once with saturated brine, and then dried over sodium sulfate. Thereafter, sodium sulfate was removed by filtration, and the solvent was distilled off under reduced pressure. The obtained brown crystals were recrystallized with a mixed solvent of ethyl acetate and hexane, dried, and then 5- [ 9.96 g of 4- (2-ethoxy-2-oxoethoxy) benzylidene] -3- (2-ethoxy-2-oxoethyl) hydantoin was obtained.
続いて、得られたうちの4.50g(12.0mmol)に、50mLナス型フラスコ中で、ジエタノールアミン7.57g(72.0mmol)を加えて、120℃で1時間撹拌しながら加熱した。反応混合液が室温まで冷えた後、析出した黄色の結晶をエタノールと水の混合溶媒で再結晶を行い、乾燥後、下記化合物(2)を4.46g得た(収率;18%)。
(化合物(2)のスペクトルデータ等)
UVスペクトル:λmax;336nm、吸光度;0.30(エタノール)。
1H−NMRスペクトル:δ〔ppm、DMSO−d6〕=3.33−3.36(m,4H),3.42−3.51(m,8H),3.57−3.60(m,4H),4.49(s,2H),4.71−4.74(t,1H×2),4.97(s,2H),5.00(t,1H),5.05(t,1H),6.53(s,1H),6.94(d,2H),7.60(d,2H),10.72(s,1H)。
溶解度:1.2(g/100g試験溶媒)、親水性が特に高い。
(Spectral data of compound (2), etc.)
UV spectrum: [lambda] max; 336 nm, absorbance; 0.30 (ethanol).
1 H-NMR spectrum: δ [ppm, DMSO-d 6 ] = 3.33-3.36 (m, 4H), 3.42-3.51 (m, 8H), 3.57-3.60 ( m, 4H), 4.49 (s, 2H), 4.71-4.74 (t, 1H x 2), 4.97 (s, 2H), 5.00 (t, 1H), 5.05 (T, 1H), 6.53 (s, 1H), 6.94 (d, 2H), 7.60 (d, 2H), 10.72 (s, 1H).
Solubility: 1.2 (g / 100 g test solvent), especially hydrophilic.
〔実施例3〕
(化合物(3)の合成)
実施例1の過程で得られた、5−[4−[2−(2−ヒドロキシエトキシ)エトキシ]ベンジリデン]ヒダントイン5.84g(20.0mmol)に、200mLナス型フラスコ中で、アクリル酸エチル2.40g(24.0mmol)、水酸化カリウム0.112g(2.00mmol)、N,N−ジメチルホルムアミド45mLを加えて、110℃で6時間撹拌しながら加熱した。反応混合液が室温まで冷えた後、セライト濾過によって固形物を除去した。溶剤を減圧下にて留去し、黄色粘性物質を得た。
Example 3
(Synthesis of Compound (3))
In a 200 mL eggplant-shaped flask, ethyl acrylate 2 was added to 5.84 g (20.0 mmol) of 5- [4- [2- (2-hydroxyethoxy) ethoxy] benzylidene] hydantoin obtained in the process of Example 1. .40 g (24.0 mmol), potassium hydroxide 0.112 g (2.00 mmol) and N, N-dimethylformamide 45 mL were added and heated at 110 ° C. with stirring for 6 hours. After the reaction mixture cooled to room temperature, the solid was removed by celite filtration. The solvent was distilled off under reduced pressure to obtain a yellow viscous substance.
これに別の100mLナス型フラスコ中で、ジエタノールアミン6.31g(60.0mmol)を加えて、120℃で17時間撹拌しながら加熱した。反応混合液が室温まで冷却した後、得られた橙色粘性物質にアセトニトリル及びイソプロパノールを加えることで結晶が析出し、濾過によって析出した結晶を回収した。その後、イソプロパノールと水で活性炭処理し、再結晶させることで、下記化合物(3)を3.52g得た(収率;39%)。
(化合物(3)のスペクトルデータ等)
UVスペクトル:λmax;338nm、吸光度;0.34(エタノール)。
1H−NMRスペクトル:δ〔ppm、DMSO−d6〕=2.72(t,2H),3.32−3.38(m,4H),3.46−3.52(m,8H),3.66(t,2H),3.75(t,2H),4.14(t,2H),4.69(s,2H),4.85(s,1H),6.47(s,1H),6.98(d,2H),7.62(d,2H),10.60(s,1H)。
溶解度:1.5(g/100g試験溶媒)、親水性が特に高い。
(Spectral data of compound (3), etc.)
UV spectrum: [lambda] max; 338 nm, absorbance; 0.34 (ethanol).
1 H-NMR spectrum: δ [ppm, DMSO-d 6 ] = 2.72 (t, 2H), 3.32-3-38 (m, 4H), 3.46-3.52 (m, 8H) , 3.66 (t, 2H), 3.75 (t, 2H), 4.14 (t, 2H), 4.69 (s, 2H), 4.85 (s, 1H), 6.47 ( s, 1H), 6.98 (d, 2H), 7.62 (d, 2H), 10.60 (s, 1H).
Solubility: 1.5 (g / 100 g test solvent), especially hydrophilic.
〔実施例4〕
(チロシナーゼ阻害活性評価1)
チロシナーゼが有するドーパ酸活性を測定することにより、化合物(1)のチロシナーゼ阻害活性を評価した。
Example 4
(Tyrosinase inhibitory activity evaluation 1)
The tyrosinase inhibitory activity of the compound (1) was evaluated by measuring the dopaic acid activity of tyrosinase.
具体的には、まず96ウェルプレートの各ウェルに、被験試料としてDMSOに溶解させた化合物(1)、またはコントロールとしてDMSOをそれぞれ加えた。次に、これに400U/mlに調製したマッシュルームに由来するチロシナーゼ液(リン酸緩衝液(pH6.0)で調製)を20μl加え、さらに反応液(0.5mg/ml L−tyrosine液、63mM CuSO4・5H2O/リン酸緩衝液(pH6.0))を100μl加え、37℃で30分間インキューベートした。その後、640nmの吸光度を測定し、これらを測定値(被験試料測定値、コントロール測定値)とし、コントロール値に対するチロシナーゼ活性率として次式(式1)により求めた。
(式1)
チロシナーゼ活性率=[(被験物質の640nmにおける吸光度)/(コントロールの640nmにおける吸光度)]×100(%)
Specifically, compound (1) dissolved in DMSO as a test sample or DMSO as a control was first added to each well of a 96-well plate. Next, 20 μl of mushroom-derived tyrosinase solution (prepared with phosphate buffer (pH 6.0)) prepared to 400 U / ml was added thereto, and further the reaction solution (0.5 mg / ml L-tyrosine solution, 63 mM CuSO4). 4 · 5H 2 O / phosphate buffer (pH 6.0)) was added 100 [mu] l, and 30 minutes incubated at 37 ° C.. Thereafter, the absorbance at 640 nm was measured, and these were taken as measurement values (test sample measurement values, control measurement values), and the tyrosinase activity rate relative to the control value was determined by the following equation (Formula 1).
(Formula 1)
Tyrosinase activity rate = [(absorbance at 640 nm of test substance) / (absorbance at 640 nm of control)] × 100 (%)
得られた結果を図1に示す。化合物(1)を添加することにより、チロシナーゼ活性が抑制されることが確認された。 The obtained results are shown in FIG. It was confirmed that tyrosinase activity was suppressed by adding compound (1).
〔実施例5〕
(チロシナーゼ阻害活性評価2)
化合物(2)を用いて、実施例4と同様の方法で、チロシナーゼ阻害活性を評価した。
Example 5
(Tyrosinase inhibitory activity evaluation 2)
Using compound (2), the tyrosinase inhibitory activity was evaluated in the same manner as in Example 4.
得られた結果を図2に示す。化合物(2)を添加することにより、チロシナーゼ活性が抑制されることが確認された。 The obtained results are shown in FIG. It was confirmed that tyrosinase activity was suppressed by adding compound (2).
〔実施例6〕
(メラニン産生抑制評価)
化合物(1)を用いて、マウス由来メラノーマ細胞を用いたメラニン産生抑制試験を行った。
Example 6
(Melanin production inhibition evaluation)
Using compound (1), a melanin production inhibition test using mouse-derived melanoma cells was performed.
具体的には、マウス由来メラノーマ細胞を、10%FBS含有DMEM培地を用いて、1.5×104cell/wellの密度で6ウェルプレートに播種し、37℃、5%炭酸ガスおよび95%空気の環境下で1日間培養した。その後、培地交換を行うと共に、DMSOに溶解させた化合物(1)、またはコントロールとしてDMSOをそれぞれ加え、同条件下において3日間培養した。その後、上清を除去し、PBS(−)で1回洗浄した。その後、1N NaOHを300μl添加し、60℃で2時間加温して細胞を溶解させ、475nmの吸光度を測定することによりメラニン産生量を求めた。これを測定値(被験試料測定値、コントロール測定値)とし、コントロール値に対するメラニン産生率として次式(式2)により求めた。
(式2)
メラニン産生率=[(被験物質の475nmにおける吸光度)/(コントロールの475nmにおける吸光度)]×100(%)
Specifically, mouse-derived melanoma cells were seeded in a 6-well plate at a density of 1.5 × 10 4 cells / well using 10% FBS-containing DMEM medium, and were incubated at 37 ° C., 5% carbon dioxide and 95%. The cells were cultured for 1 day in an air environment. Thereafter, the medium was changed, and compound (1) dissolved in DMSO or DMSO as a control was added, respectively, and cultured under the same conditions for 3 days. Thereafter, the supernatant was removed and washed once with PBS (−). Thereafter, 300 μl of 1N NaOH was added, the cells were lysed by heating at 60 ° C. for 2 hours, and the melanin production amount was determined by measuring the absorbance at 475 nm. This was taken as the measured value (test sample measured value, control measured value), and the melanin production rate relative to the control value was determined by the following formula (Formula 2).
(Formula 2)
Melanin production rate = [(absorbance at 475 nm of test substance) / (absorbance at 475 nm of control)] × 100 (%)
得られた結果を図3に示す。化合物(1)を添加することにより、メラニン産生率が低下した。 The obtained results are shown in FIG. By adding the compound (1), the melanin production rate decreased.
〔実施例7〕
(SOD様活性評価試験)
化合物(1)を用いて、SOD様作用活性評価試験を行った。
Example 7
(SOD-like activity evaluation test)
Using compound (1), an SOD-like activity evaluation test was conducted.
活性酸素抑制効果は、SODAssayKit−WST(和光純薬社製)を用いて、標準操作法に従って測定した。具体的には、DMSOに溶解させた試料化合物(1)溶液、またはコントロールとしてDMSO 20μLをそれぞれ加え、さらに高水溶性テトラゾリウム塩含有発色試薬 180μL、続いて酵素懸濁液 20μLを添加し、37℃の恒温槽中で30分間反応させた。その後、450nmの吸光度を測定し、これらを測定値(被験試料測定値、コントロール測定値)とし、コントロール値に対するスーパーオキシドアニオン産生阻害率として次式(式3)により求めた。
(式3)
スーパーオキシドアニオン産生阻害率=[(被験物質の450nmにおける吸光度)/(コントロールの450nmにおける吸光度)]×100(%)
The active oxygen suppression effect was measured according to standard operating methods using SODA Assay Kit-WST (manufactured by Wako Pure Chemical Industries, Ltd.). Specifically, the sample compound (1) solution dissolved in DMSO or DMSO (20 μL) was added as a control, respectively, and a highly water-soluble tetrazolium salt-containing coloring reagent (180 μL) was added, followed by enzyme suspension (20 μL) at 37 ° C. For 30 minutes in a constant temperature bath. Thereafter, the absorbance at 450 nm was measured, and these were taken as measured values (test sample measured values, control measured values), and the superoxide anion production inhibition rate relative to the control values was determined by the following formula (Formula 3).
(Formula 3)
Superoxide anion production inhibition rate = [(absorbance of test substance at 450 nm) / (absorbance of control at 450 nm)] × 100 (%)
得られた結果を図4に示す。化合物(1)を添加することにより、スーパーオキシドアニオンの生成が抑制され、SOD様活性を示すことが確認された。 The obtained results are shown in FIG. By adding the compound (1), it was confirmed that the production of superoxide anion was suppressed and SOD-like activity was exhibited.
〔実施例8〕
(カタラーゼ様活性評価試験1)
化合物(1)を用いて、カタラーゼ様作用活性評価試験を行った。
Example 8
(Catalase-like activity evaluation test 1)
A catalase-like activity evaluation test was conducted using the compound (1).
活性酸素抑制効果は、Amplex Red(商標) Catalase Assay Kit(Invitrogen社製)を用いて、標準操作法に従って測定した。具体的には、DMSOに溶解させた試料化合物(1)溶液、またはコントロールとしてDMSO 25μLをそれぞれ加え、さらに反応基質として40μL 過酸化水素水を加えた。室温にて30分間第一相反応を行った後に、発色試薬を50μL加えた。その後、37℃の恒温槽中で30分間反応させた。その後、560nmの吸光度を測定し、これらを測定値(被験試料測定値、コントロール測定値)とし、コントロール値に対する過酸化水素発生阻害率として次式(式4)により求めた。
(式4)
過酸化水素発生阻害率=[(被験物質の560nmにおける吸光度)/(コントロールの560nmにおける吸光度)]×100(%)
The active oxygen inhibitory effect was measured according to a standard operation method using Amplex Red (trademark) Catalase Assay Kit (Invitrogen). Specifically, a sample compound (1) solution dissolved in DMSO or DMSO 25 μL was added as a control, and 40 μL hydrogen peroxide solution was further added as a reaction substrate. After performing the first phase reaction at room temperature for 30 minutes, 50 μL of a coloring reagent was added. Then, it was made to react for 30 minutes in a 37 degreeC thermostat. Thereafter, the absorbance at 560 nm was measured, and these were taken as measured values (test sample measured values, control measured values), and the hydrogen peroxide generation inhibition rate relative to the control values was determined by the following formula (Formula 4).
(Formula 4)
Hydrogen peroxide generation inhibition rate = [(absorbance at 560 nm of the test substance) / (absorbance at 560 nm of the control)] × 100 (%)
得られた結果を図5に示す。化合物(1)を添加することにより、過酸化水素の生成が抑制され、カタラーゼ様活性を示すことが確認された。 The obtained results are shown in FIG. It was confirmed that the addition of compound (1) suppressed the production of hydrogen peroxide and exhibited catalase-like activity.
〔実施例9〕
(カタラーゼ様活性評価試験2)
化合物(2)、(3)を用いて、実施例8と同様の方法で、カタラーゼ様作用活性評価試験を行った。
Example 9
(Catalase-like activity evaluation test 2)
Using the compounds (2) and (3), a catalase-like activity evaluation test was conducted in the same manner as in Example 8.
得られた結果を図6に示す。化合物(2)、(3)を添加することにより、過酸化水素の生成が抑制され、カタラーゼ様活性を示すことが確認された。 The obtained result is shown in FIG. By adding the compounds (2) and (3), it was confirmed that the production of hydrogen peroxide was suppressed and a catalase-like activity was exhibited.
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