JP5292281B2 - 酸化防止剤 - Google Patents
酸化防止剤 Download PDFInfo
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- JP5292281B2 JP5292281B2 JP2009506940A JP2009506940A JP5292281B2 JP 5292281 B2 JP5292281 B2 JP 5292281B2 JP 2009506940 A JP2009506940 A JP 2009506940A JP 2009506940 A JP2009506940 A JP 2009506940A JP 5292281 B2 JP5292281 B2 JP 5292281B2
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- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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Description
Z1は、CR7R8または単結合を表し、
X1からX4は、それぞれ相互に独立に、C−R1、O、NまたはSから選択され、X1からX4からの2つの隣接基はまた一緒になって、非置換、または一置換もしくは多置換の環、またはC原子6〜18個を有する縮合環系を表し、該縮合環系の少なくとも1つの環は、好ましくは芳香族性を有し、さらに、環当り1つまたは2つのCH基は、C=O、N、OまたはSによって置き換えられていてもよく、縮合環系では、さらに、1つまたは2つのCH2基は、C=OまたはC=CH2によって置き換えられていてもよく、
R1は、H、直鎖もしくは分枝のC1〜C20アルコキシ基から選択され、アルキル鎖はまた、それぞれ、酸素または窒素、直鎖もしくは分枝のC1〜C20アルキル基によって割り込まれていてもよく、アルキル鎖はまた、それぞれ、酸素または窒素、直鎖もしくは分枝のC3〜C20アルケニル基、直鎖もしくは分枝のC1〜C20ヒドロキシアルキル基によって割り込まれていてもよく、ヒドロキシル基は、鎖の第一級または第二級炭素原子に結合していてもよく、さらに、アルキル鎖はまた、それぞれ、酸素または窒素、直鎖もしくは分枝のC1〜C20ヒドロキシアルコキシ基によって割り込まれていてもよく、ヒドロキシル基(複数可)は、鎖の第一級または第二級炭素原子に結合していてもよく、さらに、アルキル鎖はまた、酸素、直鎖もしくは分枝のC1〜C20アルキルアミノ基、直鎖もしくは分枝のC1〜C20ジアルキルアミノ基によって割り込まれていてもよく、
あるいは、R1は、カルボン酸、リン酸、スルホン酸、硫酸、またはスルホン官能基を表し、それらが、直鎖もしくは分枝のC1〜C20アルキル基、または直鎖もしくは分枝のC3〜C20アルケニル基によって任意選択でエステル化またはアルキル化されていてもよく、
R7およびR8は、それぞれ相互に独立に、H、OH、直鎖もしくは分枝のC1〜C20アルコキシ基、直鎖もしくは分枝のC1〜C20アルキル基、直鎖もしくは分枝のC3〜C20アルケニル基、直鎖もしくは分枝のC1〜C20ヒドロキシアルキル基から選択され、ヒドロキシル基は、鎖の第一級または第二級炭素原子に結合していてもよく、さらに、アルキル鎖はまた、酸素、直鎖もしくは分枝のC1〜C20ヒドロキシアルコキシ基によって割り込まれていてもよく、ヒドロキシル基(複数可)は、鎖の第一級または第二級炭素原子に結合していてもよく、さらに、アルキル鎖はまた、酸素によって割り込まれていてもよい]
の化合物、または式Iの化合物の塩の酸化防止剤としての使用に関する。
あるいは、R2〜R6およびR9〜R13は、それぞれ相互に独立に、カルボン酸、リン酸、スルホン酸、硫酸、またはスルホン官能基を表し、それらが、直鎖もしくは分枝のC1〜C20アルキル基、または直鎖もしくは分枝のC3〜C20アルケニル基によって任意選択でエステル化またはアルキル化されていてもよい]
または式Ia〜Idの化合物の塩であることが好ましい。
R11が、直鎖もしくは分枝のC1〜C6アルキル基、C1〜C4ジアルキルアミノ基、またはC1〜C4アルコキシ基から選択されることを特徴とする式Iまたは式Ia〜Idの少なくとも1つの化合物の使用が特に好ましい場合がある。
R6は、H、またはカルボン酸、リン酸、スルホン酸、硫酸、またはスルホン官能基を表し、それらが、直鎖もしくは分枝のC1〜C20アルキル基、または直鎖もしくは分枝のC3〜C20アルケニル基によってエステル化またはアルキル化されていてもよく、
R2、R3、R5、R9、R10、R12、およびR13は、Hを表す]。
−例えば、超酸化物遊離ラジカルアニオンもしくはNO遊離ラジカルに対抗して、または例えば一重項酸素および過酸化物に対抗してなどの反応性酸素種に対抗してなどの、UV光、もしくは喫煙などの熱分解プロセスによって誘起される遊離ラジカルに対抗する酸化防止作用、
−好ましい化合物は、強力な酸化防止活性を高分子の安定性と合せる、
−化粧用、医薬用、特に皮膚用製品、または家事用製品、または食品もしくは食品添加物、特に、染料、コンシステンシー用物質または臭気物質を含むものに対する製品安定化作用、
−式Iの好ましい化合物は、組成物中の油成分として適切である、
−式Iの好ましい化合物は、例えば、皮膚感覚などの組成物の医薬特性を改良するために適切である、
−式Iの好ましい化合物は、好ましくは、例えば、結晶性成分用の溶媒として、良好な溶解性および溶媒特性を示す、
−本発明による好ましい群の化合物はまた、皮膚のタンニングを引き起こし得るか、またはジヒドロキシアセトンなどの皮膚タンニング物質の作用を改良する、
−皮膚耐性が十分ある、
−顔料および表面コーティングに及ぼす製品安定化作用、
−式Iの好ましい化合物は、LSF、SPF、PPD、もしくはIPDなどの光保護因子、または遊離ラジカル保護因子の産生または喚起のために適している、
−特に、本用途において以下に記載のPEGまたはPG含有乳化剤などの自動酸化可能なポリエチレングリコール(PEG)またはポリグリセリン(PG)に及ぼす安定化作用、あるいは、自動酸化可能なポリエチレングリコール(PEG)またはポリグリセリン(PG)誘導体の劣化生成物のダメージ作用の低減、
−特に、化粧用、医薬用、特に皮膚用製品、または家事用製品、または食品および食品添加物中の、染料、コンシステンシー物質もしくは臭気物質、または酸化防止剤もしくはビタミン、およびUVフィルタ、ならびに二酸化チタン含有顔料に及ぼす安定化作用、
−大抵の酸化防止剤が遊離ラジカルとの反応後無効になるが、式Iの好ましい化合物は、この反応後UVろ過作用を示し、したがってそれらの保護機能を継続する、
−酸化防止特性を有する本発明による好ましい化合物がまた、色素沈着制御用に用い得るのは、それらが、皮膚領域に対する美白作用を有し得るからである。加えて、ここで記載の好ましい化合物は、無色またはわずかしか着色していないので、したがって、組成物を変色させないか、またはわずかに変色させるのみである。
R1は、基−C(O)CH3、−CO2R3、−C(O)NH2および−C(O)N(R4)2から選択することができ、
Xは、OまたはNHを表し、
R2は、C原子1〜30個を有する直鎖もしくは分枝のアルキルを表し、
R3は、C原子1〜20個を有する直鎖もしくは分枝のアルキルを表し、
R4はそれぞれの場合、相互に独立に、H、またはC原子1〜8個を有する直鎖もしくは分枝のアルキルを表し、
R5は、C原子1〜8個を有する直鎖もしくは分枝のアルキル、またはC原子1〜8個を有する直鎖もしくは分枝のアルコキシを表し、
R6は、C原子1〜8個を有する直鎖もしくは分枝のアルキル、好ましくは、2−(4−ヒドロキシ−3,5−ジメトキシベンジリデン)マロン酸および/または2−(4−ヒドロキシ−3,5−ジメトキシベンジル)マロン酸、特に好ましくは、2−(4−ヒドロキシ−3,5−ジメトキシベンジリデン)マロン酸ビス(2−エチルヘキシル)(例えば、Oxynex(登録商標)ST Liquid)および/または2−(4−ヒドロキシ−3,5−ジメトキシベンジル)マロン酸ビス(2−エチルヘキシル)(例えば、RonaCare(登録商標)AP)の誘導体を表す]。
−直鎖もしくは分枝のC1〜C20アルコキシ基、特に、エチルヘキシルオキシ基などの長鎖アルコキシ官能基は、化合物の油溶解性を向上させる
−一部の場合では、この型の化合物は、油成分の形態であり、組成物内に容易に組み込み得るか、または他の製剤成分用の溶媒として機能し得る。
3−(4’−メチルベンジリデン)−dl−ショウノウなどのベンジリデンショウノウ誘導体(例えば、Eusolex(登録商標)6300)、3−ベンジリデンショウノウ(例えば、Mexoryl(登録商標)SD)、N−{(2および4)−[(2−オキソボルン−3−イリデン)メチル]−ベンジル}アクリルアミドのポリマー(例えば、Mexoryl(登録商標)SW)、メチル硫酸N,N,N−トリメチル−4−(2−オキソボルン−3−イリデンメチル)アニリニウム(例えば、Mexoryl(登録商標)SK)、または(2−オキソボルン−3−イリデン)トルエン−4−スルホン酸(例えば、Mexoryl(登録商標)SL)、
1−(4−tert−ブチルフェニル)−3−(4−メトキシフェニル)プロパン−1,3−ジオン(例えば、Eusolex(登録商標)9020)または4−イソプロピルジベンゾイルメタン(例えば、Eusolex(登録商標)8020)などのベンゾイルまたはジベンゾイルメタン、
2−ヒドロキシ−4−メトキシベンゾフェノン(例えば、Eusolex(登録商標)4360)または2−ヒドロキシ−4−メトキシベンゾフェノン−5−スルホン酸およびそのナトリウム塩(例えば、Uvinul(登録商標)MS−40)などのベンゾフェノン、
メトキシケイ皮酸オクチル(例えば、Eusolex(登録商標)2292)、例えば、異性体の混合物としての4−メトキシケイ皮酸イソペンチル(例えば、Neo Heliopan(登録商標)E 1000)などのメトキシケイ皮酸エステル、
サリチル酸2−エチルヘキシル(例えば、Eusolex(登録商標)OS)、サリチル酸4−イソプロピルベンジル(例えば、Megasol(登録商標))またはサリチル酸3,3,5−トリメチルシクロヘキシル(例えば、Eusolex(登録商標)HMS)などのサリチル酸誘導体、
4−アミノ安息香酸、4−(ジメチルアミノ)安息香酸2−エチルヘキシル(例えば、Eusolex(登録商標)6007)、4−アミノ安息香酸エトキシル化エチル(例えば、Uvinul(登録商標)P25)などの4−アミノ安息香酸および誘導体、
2−フェニルベンゾイミダゾール−5−スルホン酸およびそのカリウム、ナトリウム、およびトリエタノールアミン塩(例えば、Eusolex(登録商標)232)、2,2−(1,4−フェニレン)ビスベンゾイミダゾール−4,6−ジスルホン酸およびその塩(例えば、Neoheliopan(登録商標)AP)、または2,2−(1,4−フェニレン)ビスベンゾイミダゾール−6−スルホン酸などのフェニルベンゾイミダゾールスルホン酸;
および、
−2−シアノ−3,3−ジフェニルアクリル酸2−エチルヘキシル(例えば、Eusolex(登録商標)OCR)、
−3,3’−(1,4−フェニレンジメチレン)ビス(7,7−ジメチル−2−オキソビシクロ[2.2.1]ヘプト−1−イルメタンスルホン酸およびその塩(例えば、Mexoryl(登録商標)SX)および
−2,4,6−トリアニリノ−(p−カルボ−2’−エチルヘキシル−1’−オキシ)−1,3,5−トリアジン(例えば、Uvinul(登録商標)T150)
−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(例えば、Uvinul(登録商標)UVA Plus、BASF)などのさらなる物質が存在する。
−2−(2H−ベンゾトリアゾール−2−イル)−4−メチル−6−(2−メチル−3−(1,3,3,3−テトラメチル−1−(トリメチルシリルオキシ)ジシロキサニル)プロピル)フェノール(例えば、Silatrizole(登録商標))、
−4,4’−[(6−[4−((1,1−ジメチルエチル)アミノカルボニル)フェニルアミノ]−1,3,5−トリアジン−2,4−ジイル)ジイミリオ]ビス(安息香酸)2−エチルヘキシル(例えば、Uvasorb(登録商標)HEB)、
−α−(トリメチルシリル)−ω−[トリメチルシリル)オキシ]ポリ[オキシ(ジメチル[および約6%のメチル[2−[p−[2,2−ビス(エトキシカルボニル]ビニル]フェノキシ]−1−メチレンエチル]および約1.5%のメチル[3−[p−[2,2−ビス(エトキシカルボニル)ビニル)フェノキシ)プロペニル)および0.1〜0.4%の(メチル水素]−シリレン]](n≒60)(CAS No. 207 574−74−1)、
−2,2’−メチレンビス(6−(2H−ベンゾトリアゾール−2−イル)−4−(1,1,3,3−テトラメチルブチル)−フェノール)(CAS No.103 597−45−1)、
−2,2’−(1,4−フェニレン)ビス(1H−ベンゾイミダゾール−4,6−ジスルホン酸、モノナトリウム塩)(CAS No.180 898−37−7)および
−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(CAS No.103 597−45−、187 393−00−6)、
−4,4’−[(6−[4−((1,1−ジメチルエチル)アミノカルボニル)フェニルアミノ]−1,3,5−トリアジン−2,4−ジイル)ジイミノ]ビス(安息香酸)2−エチルヘキシル(例えば、Uvasorb(登録商標)HEB)である。
−カプセル壁の親水性は、UVフィルタまたは式Iの化合物の溶解性と独立に設定し得る。したがって、例えば、疎水性UVフィルタまたは本発明による化合物を純粋に水性である組成物中に組み込むことも可能である。加えて、不快であると見なされる場合が多い、疎水性UVフィルタを含む組成物を施用した場合の油っぽい感じも抑制される。
−ある種のUVフィルタ、特に、ジベンゾイルメタン誘導体は、化粧用組成物中で低い光安定性しか示さない。例えば、ケイ皮酸誘導体などの、これらのフィルタの光安定性を低下させるこれらのフィルタまたは化合物をカプセル化することによって、組成物全体の光安定性を増加させることが可能になる。
−有機UVフィルタの皮膚への浸透、およびヒトの皮膚への直接施用におけるそれに伴う刺激の可能性は、文献で繰返し議論されている。ここで提案されている対応物質のカプセル化によってこの影響が抑制される。
−一般に、個々のUVフィルタまたは本発明による化合物または他の成分をカプセル化することによって、結晶化プロセス、沈殿および凝集物の形成などの、個々の組成物成分相互の相互作用により引き起こされる組成物問題は、相互作用が抑制されるので、回避することが可能になる。
のピリミジンカルボン酸の使用がここでは好ましい。R2が、メチルまたはエチル基であり、R1またはR5およびR6が、Hであるピリミジンカルボン酸の使用が好ましい。ピリミジンカルボン酸エクトイン((S)−1,4,5,6−テトラヒドロ−2−メチル−4−ピリミジンカルボン酸)およびヒドロキシエクトイン((S,S)−1,4,5,6−テトラヒドロ−5−ヒドロキシ−2−メチル−4−ピリミジンカルボン酸)の使用が特に好ましい。本発明による組成物は、好ましくは、最高15重量%の量でこの種のピリミジンカルボン酸を含む。ここでは、ピリミジンカルボン酸は、好ましくは、本発明による化合物と100:1〜1:100の比で用いられ、1:10〜10:1の範囲の比が特に好ましい。
−鉱油、鉱物性油;
−カプリンまたはカプリル酸のトリグリセリドなどの油、さらには、例えば、ヒマシ油などの天然油;
−脂肪、ロウ、および他の天然および合成脂質、好ましくは、脂肪酸と低炭素数を有するアルコール、例えば、イソプロパノールとのエステル、プロピレングリコールまたはグリセリン、または脂肪族アルコールと低炭素数を有するアルカン酸または脂肪酸のエステル;
−ジメチルポリシロキサン、ジエチルポリシロキサン、ジフェニルポリシロキサン、およびそれらの混合形態などのシリコーン油。
によって区別されるアルキルグルコシドの群から選択される。
として定義される。グルコシル化度が1〜2、特に有利には1.1〜1.5、非常に特に有利に1.2〜1.4、特に1.3である生成物を選択することが本発明に従って有利である。
によって区別される物質群から選択される。
によって区別される物質群から選択される。
の少なくとも1つの化合物を水素化することによって調製される。
が、水素化されていることを特徴とする、式IbまたはIcの化合物を調製するための方法にさらに関する
R6は、H、またはカルボン酸、リン酸、スルホン酸、硫酸、またはスルホン官能基を表し、それらが、直鎖もしくは分枝のC1〜C20アルキル基、または直鎖もしくは分枝のC3〜C20アルケニル基によってエステル化またはアルキル化されていてもよく、
R2、R3、R5、R9、R10、R12、およびR13は、Hを表す]。
実施例1:2−(ヒドロキシフェニルメチル)−5−メトキシフェノールの調製
2−(ヒドロキシフェニルメチル)−5−ジエチルアミノフェノール
2−(ヒドロキシフェニルメチル)フェノール
2−(ヒドロキシフェニルメチル)−5−スルホフェノール
2−(ヒドロキシフェニルメチル)−5−メトキシ−4−スルホフェノール
2−[(4−ジエチルアミノ−2−ヒドロキシフェニル)ヒドロキシメチル]安息香酸エチル
2−[(4−ジエチルアミノ−2−ヒドロキシフェニル)ヒドロキシメチル]安息香酸エチルヘキシル
2−[(2−ヒドロキシフェニル)ヒドロキシメチル]安息香酸エチルヘキシル
3−ヒドロキシ−1,3−ジフェニルプロパン−1−オン
1−(4−tert−ブチルフェニル)−3−ヒドロキシ−3−フェニルプロパン−1−オン
1−(4−tert−ブチルフェニル)−3−ヒドロキシ−3−(4−メトキシフェニル)プロパン−1−オン
3−(4−tert−ブチルフェニル)−3−ヒドロキシ−1−フェニルプロパン−1−オン
3−(4−tert−ブチルフェニル)−3−ヒドロキシ−1−(4−メトキシフェニル)プロパン−1−オン
実施例3:3−(4−メトキシフェニル)−3−ヒドロキシ−1−(4−tert−ブチルフェニル)プロパン−1−オンの合成
UV光を照射すると、実施例1または2に記載の本発明による化合物のUVスペクトルが変化する。ここでの照射は、UV用特殊ガラスフィルタを備えたAtlas Sun Test CPS、キセノンランプによって、出力95.69W/m2で290〜400nmの範囲で実施することができる。わずか約60分後、化合物によるUV吸収の有意な増加が明白であり、この吸収は、照射を続けるとさらに増加する。
UV光を照射すると、実施例1または2に記載の化合物と、β−カロテンとを含むエマルジョンは、本発明による試料中のβ−カロテンによる吸収(440〜480nmの範囲のEmax)が、β−カロテンのみを含む試料より有意に大きいことを示す。したがって、本発明によるエマルジョン中のβ−カロテンの劣化が減少し;本発明による化合物がβ−カロテンを安定化させる。
本発明による化合物の遊離ラジカル低減作用は、例えば、2,2−ジフェニル−1−ピクリルヒドラジル(DPPH)アッセイによって実際に示すことができる。2,2−ジフェニル−1−ピクリルヒドラジルは、溶液中で安定である遊離ラジカルである。不対電子によって、515nmでの強い吸収帯がもたらされ、溶液は濃紫色である。遊離ラジカルスカベンジャの存在下、電子は、対を形成し、吸収は消滅し、脱色は、取り込まれた電子数を勘定しながら化学量論的に進行する。吸収は光度計で測定される。試験される物質の抗遊離ラジカル特性は、用いられた2,2−ジフェニル−1−ピクリルヒドラジルの50%が遊離ラジカルスカベンジャと反応した点での濃度を測定することによって求められる。この濃度は、所与の測定条件下での物質特性と見なすことができる値であるEC50として表される。調査された物質は、標準(例えば、トコフェロール)と比較される。ここでのEC50値は、それぞれの化合物が遊離ラジカルをスカベンジする能力の指標である。EC50値が小さいほど、遊離ラジカルをスカベンジする能力は大きい。
2,2−ジフェニル−1−ピクリルヒドラジル(DPPH)をエタノールに溶解した原液を調製する(0.025g/lのDPPH遊離ラジカル)。試験すべき化合物の多様な濃度の液をこの溶液の一定分量に加える。吸収は、それぞれの場合、515nm、25℃、および厚さ1cmで測定される。求められるEC50は、元のDPPH遊離ラジカル濃度の50%が依然として存在する点での値である。この値が小さいほど、対応する遊離ラジカルを低減する活性は大きい。この値を実現するのに要する反応時間は、TEC50値(分で)で示される。
脂質アッセイ:8%(やはり、際立つものでない)
TEACアッセイ:50%(この値は良好である)。
実施例6a:
化合物(9)=(4−メトキシフェニル)−フェニルメタノールに対する光転換試験:
該物質の4%ミリスチン酸イソプロピル溶液を2μ/cm−2の速度で粗面Perspex支持体に施用する。試料を太陽試験器中で1時間50分、太陽光をシミュレートした照射にかける。照射後、試料をイソプロパノール40mlで抽出し、体積が正確に50mlになるように補給する。非照射試料と比較して、285nmでの物質の最大吸収の増加は0.77吸収単位である。
実施例6b:実施例1からの化合物(5)=2−(ヒドロキシフェニルメチル)−5−メトキシフェノールに対する光転換試験
該物質を粗面化Perspexプレートに施用し(0.75mg/cm−2)、シミュレートされた太陽下で照射する。照射量は、非重み付けの全UV絶対照射量として理解すべきである。各照射段階後、試料のUV吸収は、placebo(placebo=グリセリンを含むPerspexプレート)に対して測定される。物質は、照射によって吸収力が増加し、開始時の値は、吸収が全くない(図1を参照されたい)ことが分かる。
実施例1または2による化合物を含む化粧用組成物の例示的な製剤を以下に示す。対応する組成物は、本発明による化合物すべてに関して同じ仕方で調製し得る。
Claims (19)
- フリーラジカルに対する酸化防止剤としての作用が紫外線照射(UV光照射)により導入される請求項1に記載の使用。
- 化粧用もしくは医薬用組成物、または食品もしくは食品添加物を調製する、または家事用製品を調製するための、請求項1に記載の使用。
- 皮膚用組成物を調製するための、請求項1に記載の使用。
- 皮膚領域を美白化する化粧品を調製するための、請求項1に記載の使用。
- R 4 およびR 11 の少なくとも一方は、tert-ブチル基である、請求項1から5のいずれか1項に記載の使用。
- 少なくとも1つの化合物が、
2−(ヒドロキシフェニルメチル)−5−ジエチルアミノフェノール、
2−(ヒドロキシフェニルメチル)フェノール、
2−(ヒドロキシフェニルメチル)−5−メトキシフェノール、
1−(4−tert−ブチルフェニル)−3−ヒドロキシ−3−フェニル−プロパン−1−オン、
1−(4−tert−ブチルフェニル)−3−ヒドロキシ−3−(4−メトキシフェニル)プロパン−1−オン、
3−(4−tert−ブチルフェニル)−3−ヒドロキシ−1−フェニルプロパン−1−オン、
3−(4−tert−ブチルフェニル)−3−ヒドロキシ−1−(4−メトキシフェニル)プロパン−1−オン、および
3−(4−メトキシフェニル)−3−ヒドロキシ−1−(4−メトキシフェニル)プロパン−1−オン
から選択されることを特徴とする、請求項1から5のいずれか1項に記載の使用。 - 化粧用もしくは医薬用、あるいは、食品もしくは食品添加物、または家事用製品に適している少なくとも1つのビヒクルと、
以下の式Ia、Ib及びIcの化合物から選択された少なくとも1種の化合物と、
を含む、化粧用もしくは医薬用、あるいは、食品もしくは食品添加物、または家事用製品用の組成物。
R 3 、R 5 、R 9 、R 10 及びR 12 はそれぞれHを表し、
R 4 およびR 11 は、それぞれ相互に独立に、H、直鎖もしくは分枝のC 1 〜C 20 アルコキシ基、直鎖もしくは分枝のC 1 〜C 20 アルキル基、または直鎖もしくは分枝のC 1 〜C 20 ジアルキルアミノ基を表す。] - 前記ビヒクルが、皮膚用組成物に適しているビヒクルである請求項10に記載の組成物。
- R 4 およびR 11 の少なくとも一方は、tert-ブチル基である、請求項10または11に記載の組成物。
- 少なくとも1つの化合物が、
2−(ヒドロキシフェニルメチル)−5−ジエチルアミノフェノール、
2−(ヒドロキシフェニルメチル)フェノール、
2−(ヒドロキシフェニルメチル)−5−メトキシフェノール、
1−(4−tert−ブチルフェニル)−3−ヒドロキシ−3−フェニル−プロパン−1−オン、
1−(4−tert−ブチルフェニル)−3−ヒドロキシ−3−(4−メトキシフェニル)プロパン−1−オン、
3−(4−tert−ブチルフェニル)−3−ヒドロキシ−1−フェニルプロパン−1−オン、
3−(4−tert−ブチルフェニル)−3−ヒドロキシ−1−(4−メトキシフェニル)プロパン−1−オン、及び
3−(4−メトキシフェニル)−3−ヒドロキシ−1−(4−メトキシフェニル)プロパン−1−オン
から選択されることを特徴とする、請求項10から12のいずれか1項に記載の組成物。 - 式Ia、Ib及びIcの化合物から選択された少なくとも1種の化合物を0.01から20重量%の量で含むことを特徴とする、請求項10から14のいずれか1項に記載の組成物。
- 1つまたは複数のさらなる酸化防止剤および/またはビタミンを含むことを特徴とする、体細胞を酸化性ストレスから保護するための、請求項10から15のいずれか1項に記載の組成物。
- 少なくとも1つのセルフタンニング剤を含むことを特徴とする、請求項10から16のいずれか1項に記載の組成物。
- 請求項10から17のいずれか1項に記載の組成物の調製方法であって、
式Ia、Ib及びIcの化合物から選択された少なくとも1種の化合物が、化粧用にもしくは医薬用に、または食品もしくは食品添加物向けに、または家事用製品向けに適しているビヒクルと混合されることを特徴とする、組成物の調製方法。 - 前記ビヒクルが、皮膚用組成物に適しているビヒクルである請求項18に記載の組成物の調製方法。
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ES2907708T3 (es) | 2015-01-13 | 2022-04-26 | British Columbia Cancer Agency Branch | Compuestos heterocíclicos para obtención de imágenes y tratamiento del cáncer y métodos para su uso |
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JPS5147941A (en) * | 1974-10-22 | 1976-04-24 | Dainichi Nippon Cables Ltd | Karyusheru anteikakuroropurengomusoseibutsu |
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WO2002051779A2 (de) * | 2000-12-23 | 2002-07-04 | Degussa Ag | Verfahren zur herstellung von alkoholen durch hydrierung von carbonylverbindungen |
JP2004089769A (ja) * | 2002-08-29 | 2004-03-25 | Cosmo Oil Co Ltd | アルドール反応触媒およびアルドール反応方法 |
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AU2003291063A1 (en) * | 2002-11-19 | 2004-06-15 | Board Of Trustees Operating Michigan State University | Antioxidant and antimicrobial agents and methods of use thereof |
ITMI20031396A1 (it) | 2003-07-09 | 2005-01-10 | Giuliani Spa | Composizione per uso farmaceutico o dietetico o cosmetico dotata di attivita' antiossidante. |
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- 2007-04-05 JP JP2009506940A patent/JP5292281B2/ja not_active Expired - Fee Related
- 2007-04-05 US US12/298,137 patent/US7906684B2/en not_active Expired - Fee Related
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ES2564244T3 (es) | 2016-03-21 |
CN101437579B (zh) | 2012-11-21 |
EP2010294A1 (de) | 2009-01-07 |
RU2008146195A (ru) | 2010-05-27 |
JP2009534433A (ja) | 2009-09-24 |
EP2010294B1 (de) | 2015-12-02 |
RU2454394C2 (ru) | 2012-06-27 |
DE102006019044A1 (de) | 2007-10-31 |
WO2007121845A1 (de) | 2007-11-01 |
US7906684B2 (en) | 2011-03-15 |
CN101437579A (zh) | 2009-05-20 |
US20090246158A1 (en) | 2009-10-01 |
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