CAS: 94105-90-5; 3-(4-Hydroxyphenyl)Chroman-7-Ol

该化合物是一种苯丙醚,该化合物具有苯丙基核心结构,其特征为一个有引信的苯和苯环;其分子结构包括一个附于一个苯环的氢氧基组(-OH),有助于其潜在的抗氧化特性;其结构中存在多个氢氧基组,常常增强其在极溶剂中的再活性和溶性;该化合物可能展示生物活动,包括抗炎和抗氧化效应,使其在药理学研究中引起兴趣;此外,其结构特征表明在开发天然产品或功能食品方面的潜在应用;然而,为了充分理解其特性,行动机制和潜在治疗用途,必须进行详细研究.

结构式图片

相似化合物

531-95-3 65998-44-9 3722-56-3

物理性质

MSDS等安全信息

上下游产品

daidzein 3,4-dihydro-7-hydroxy-3-(4-methoxyphenyl)-2H-1-benzopyran 7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on 7-acetoxy-3-(4-acetoxy-phenyl)-chroman 4',7-dimethoxyisoflavan 7-acetoxy-3-(4-acetoxy-phenyl)-chroman equol6,8,3',5'-2H4equol (+)-Equol

合成工艺路线路线简述

  • 1029608-32-9 = 94105-90-5
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethyl Acetate; 24 H
    标题:O-Quinone Methide Based Approach To Isoflavans: Application To The Total Syntheses Of Equol,3'-Hydroxyequol And Vestitol
    作者:Gharpure,Santosh J.; Sathiyanarayanan,A. M.; Jonnalagadda,Prasad
    参考文献:Tetrahedron Letters 日期:2008 卷标:49(18) 页码:2974-2978]

    69618-79-7 = 94105-90-5
    反应条件:1.1 Reagents: Imidazole Solvents: Ethanol; 45 Min,Reflux
    标题:Preparation Of Isoflavone Derivatives
    参考文献:World Intellectual Property Organization]

    175089-66-4 = 94105-90-5
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Dimethylformamide; 8 H,0.1 Mpa,25 °C
    标题:Preparation Method Of Equol
    参考文献:China]

    81267-65-4 = 94105-90-5
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol; 6 H,2 Atm,Rt
    标题:Methods For Synthesizing Glycinols,Glyceollins I And Ii And Isoflavenes And Chromanes Using A Wittig Reaction,And Compositions Made Therewith
    参考文献:United States]

    2229767-32-0 = 94105-90-5
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Methanol,Tetrahydrofuran,Water; 20 Min,60 °C
    标题:Enantioselective Total Synthesis Of Natural Isoflavans: Asymmetric Transfer Hydrogenation/deoxygenation Of Isoflavanones With Dynamic Kinetic Resolution
    作者:Kessberg,Anton; Luebken,Tilo; Metz,Peter
    参考文献:Organic Letters 日期:2018 卷标:20(10) 页码:3006-3009]

    486-66-8 = 94105-90-5
    反应条件:1.1 Reagents: Acetic Acid,Oxygen Catalysts: Palladium; 3 D,Rt1.2 Reagents: Hydrogen Solvents: Diglyme; 30 Min,Rt
    标题:Preparation Of Flavone,Isoflavone,And Flavanone Sulfamates As Estrone Sulfatase And/or Aromatase Inhibitors For Treatment Of Breast And Endometrial Cancers
    参考文献:United States]

    = 94105-90-5 [标题:Reaction Conditions
    标题:Synthesis Of Isoflavanes And Intermediates Thereof Via Chiral Intermediates
    参考文献:World Intellectual Property Organization]

    = 94105-90-5 [标题:Reaction Conditions
    标题:Use Of Equol For Ameliorating Or Preventing Neuropsychiatric And Neurodegenerative Diseases Or Disorders
    参考文献:World Intellectual Property Organization]

    = 94105-90-5 [标题:Reaction Conditions
    标题:Catalytic Hydrogenation Of Isoflavones. The Preparation Of (+/-)-Equol And Related Isoflavans
    作者:Lamberton,John A.; Suares,Hector; Watson,Keith G.
    参考文献:Australian Journal Of Chemistry 日期:1978 卷标:31(2) 页码:455-7]

    486-66-8 = 94105-90-5
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium,Water Solvents: Ethanol,Acetic Acid; 10 H,Rt
    标题:Synthesis Of Various Kinds Of Isoflavones,Isoflavanes,And Biphenyl-Ketones And Their 1,1-Diphenyl-2-Picrylhydrazyl Radical-Scavenging Activities
    作者:Goto,Hideyuki; Terao,Yoshiyasu; Akai,Shuji
    参考文献:Chemical & Pharmaceutical Bulletin 日期:2009 卷标:57(4) 页码:346-360]

    10499-17-9 = 94105-90-5
    反应条件:1.1 Reagents: Tetrabutylammonium Iodide Solvents: Dichloromethane; Rt -> -78 °C1.2 Reagents: Boron Trichloride; -78 °C; 2 H,-78 °C -> 0 °C1.3 Reagents: Sodium Bicarbonate Solvents: Water; Neutralized
    标题:Synthesis Of Haginin E,Equol,Daidzein,And Formononetin From Resorcinol Via An Isoflavene Intermediate
    作者:Li,Sie-Rong; Chen,Po-Yuan; Chen,Liang-Yeu; Lo,Yi-Fang; Tsai,Ian-Lih; Et Al
    参考文献:Tetrahedron Letters 日期:2009 卷标:50(18) 页码:2121-2123]

    3682-01-7 = 94105-90-5
    反应条件:1.1 Reagents: Ammonium Formate Catalysts: Palladium Dihydroxide Solvents: Acetic Acid; 1.4 H,Reflux
    标题:Preparation Of Isoflavonoid Compounds
    参考文献:United States]

    81267-65-4 = 94105-90-5
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Dichloromethane; 10 H,15 Atm,20 °C
    标题:Method For Synthesizing Equol
    参考文献:China]

    1118431-82-5 = 94105-90-5
    反应条件:1.1 Reagents: Pyridinium Chloride; 1.5 H,220 °C1.2 Solvents: Water; Cooled
    标题:Simple And Efficient Synthesis Of (+/-)-Equol And Related Derivatives
    作者:Gupta,Atul; Ray,Suprabhat
    参考文献:Synthesis 日期:2008 卷标:(23) 页码:3783-3786]

    486-66-8 = 94105-90-5
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Tetrahydrofuran; 4 - 8 H,Rt
    标题:Synthesis,Structure-Activity Relationship Analysis And Kinetics Study Of Reductive Derivatives Of Flavonoids As Helicobacter Pylori Urease Inhibitors
    作者:Xiao,Zhu-Ping; Peng,Zhi-Yun; Dong,Jing-Jun; He,Juan; Ouyang,Hui; Et Al
    参考文献:European Journal Of Medicinal Chemistry 日期:2013 卷标:63 页码:685-695]

    = 94105-90-5 [标题:Reaction Conditions
    标题:Equol,A Natural Estrogenic Metabolite From Soy Isoflavones Convenient Preparation And Resolution Of R- And S-Equols And Their Differing Binding And Biological Activity Through Estrogen Receptors Alpha And Beta
    作者:Muthyala,Rajeev S.; Ju,Young H.; Sheng,Shubin; Williams,Lee D.; Doerge,Daniel R.; Et Al
    参考文献:Bioorganic & Medicinal Chemistry 日期:2004 卷标:12(6) 页码:1559-1567]

    = 94105-90-5 [标题:Reaction Conditions
    标题:Estrogen Receptor-β Ligands For Therapy
    参考文献:World Intellectual Property Organization]

    = 94105-90-5 [标题:Reaction Conditions
    标题:Therapeutic Methods And Compositions Involving Isoflavones
    参考文献:World Intellectual Property Organization]

    = 94105-90-5 [标题:Reaction Conditions
    标题:Metabolites Of Daidzein And Genistein And Their Biological Activities
    作者:Chang,Yu-Chen; Nair,Muraleedharan G.; Nitiss,John L.
    参考文献:Journal Of Natural Products 日期:1995 卷标:58(12) 页码:1901-5]

    486-66-8 = 94105-90-5 + 17238-05-0
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol,Acetic Acid; 8 H,Rt
    标题:Structure-Activity Relationship Of Phytoestrogen Analogs As Erα/β Agonists With Neuroprotective Activities
    作者:Cho,Hye Won; Gim,Hyo Jin; Li,Hua; Subedi,Lalita; Kim,Sun Yeou; Et Al
    参考文献:Chemical & Pharmaceutical Bulletin 日期:2021 卷标:69(1) 页码:99-105
脑益嗪置于氢气体系中,用 N,N-二甲基甲酰胺 作为反应溶剂,25.0 °C,100.0 Kpa 条件下,反应 8.0H,反应生成 雌马酚
参考文献:一种雌马酚的制备方法
标题:一种雌马酚的制备方法
摘要:本发明涉及一种雌马酚的制备方法,步骤为:S1:苯并氢化吡喃的合成:称取大豆甙元原料,溶于dmf中,在加氢釜中加入钯碳,在恒温恒压下同速反应;将催化剂过滤,滤液加入冰水,搅拌析出白色固体,过滤,水洗,烘干,得到中间体a;s2:缩合物的合成:取中间体a,二氯乙烷,多聚磷酸加到三口瓶,回流反应,降温,冷却,加到冰水中;分层取有机相,硫酸钠干燥,浓缩二氯乙烷,得黄色油状物,用90%乙醇水重结晶,得中间体b;s3:雌马酚的合成:取中间体b,Dmf,催化剂,加入加氢釜中,在恒温恒压下反应后滤出催化剂,滤液加入冰水中,搅拌析出灰色固体,过滤,滤饼用70%甲醇水重结晶,得到雌马酚.本发明的优点是,步骤简单,总收率高,环保易操作.

海关参考信息

专利信息


专利号:US-7816544-B2
优先权日:2004-03-23
标 题:Synthesis of rocaglamide natural products via photochemical generation of oxidopyrylium species
发明人：JONES II GUILFORD; GERARD BAUDOUIN; PORCO JR JOHN A
权利人:UNIV BOSTON
摘要:The present invention provides new strategies for the synthesis of compounds of the rocaglamide family and related natural products. In particular, the new biomimetic synthetic approach involves photochemical generation of an oxidopyrylium species from a 3-hydroxychromone derivative followed by 1,3-dipolar cycloaddition of the oxidopyrylium species to a dipolarophile. This approach can be used for the formation of adducts containing an aglain core structure. Methods for the conversion of aglain core structures to aglain, rocaglamide and forbaglin ring systems are also provided. The present invention also relates to the use of rocaglamide/aglain/forbaglin derivatives for the manufacture of medicaments for use in the treatment of cancer or cancerous conditions, disorders associated with cellular hyperproliferation, or NF-κB-dependent conditions.

专利号:US-7129357-B2
优先权日:2003-09-15
标题:Synthesis of quinoline 5-carboxamides useful for the preparation of PDE IV inhibitors
发明人：ANDREWS DAVID R; TANG SUHAN; WU WENXUE; KALLINEY SAMI Y; SUDHAKAR ANANTHA; NIELSEN CHRISTOPHER
权利人:SCHERING CORP
摘要:In one embodiment, the present application discloses a process for making the compound of the formula:

专利号:US-5639785-A
优先权日:1995-06-07
标 题 :Methods for the treatment of baldness and gray hair using isoflavonoid derivatives
发明人：KUNG PATRICK C
权利人:GLOBAL PHARMA LTD
摘要:The present invention relates to novel pharmaceutical compositions of isoflavanoid derivatives useful for the treatment of male pattern baldness and alopecia areata, and their use in promoting the conversion of gray hair to the original pigment in hair follicles. Also described herein are methods for the synthesis of isoflavanoid derivatives.

专利号:US-10030003-B2
优先权日:2014-09-10
标 题:Synthesis of isoflavanes and intermediates thereof
发明人：BELIAEV NIKOLAI; SHAFRAN YURI
权利人:SYSTEM BIOLOGIE AG
摘要:Subject of the invention is a method for enantioselective production of an isoflavane from an isoflavone, comprising the steps: (a) selectively reducing the isoflavone, such that the 4-keto group of the isoflavone is converted to a 4-hydroxy group, and the 2,3-double bond of the isoflavone is converted to a 2,3-single bond, thereby obtaining a 4-hydroxy intermediate, and (b) reacting the 4-hydroxy intermediate with a chiral reagent, such that a chiral group is covalently attached to the C4-position of the 4-hydroxy intermediate, thereby obtaining a chiral intermediate. The invention also relates to intermediates of formulae (IV), (V), (VI) and (VII) obtainable in the inventive process.

专利号:US-8969596-B2
优先权日:2008-08-14
标题:Synthesis of equol
发明人：STEFFAN BERT
权利人:STEFFAN BERT
摘要:Subject of the invention is a method for the production of isoflavanes from isoflavones, whereby in a first reaction step (a) the 4-keto group of the isoflavone is reduced in a enantioselective manner, whilst the 2,3-double bond is maintained, to the 4-hydroxy compound.

专利号:US-8993296-B2
优先权日:2007-12-27
标 题:Enzyme associated with equol synthesis
发明人：SHIMADA YOSHIKAZU; YASUDA SETSUKO; TAKAHASHI MASAYUKI; HAYASHI TAKASHI; MIYAZAWA NORIHIRO; ABIRU YASUHIRO; OHTANI TADAAKI; SATO IKUTARO
权利人:OTSUKA PHARMA CO LTD
摘要:An object of the present invention is to provide enzymes associated with equol synthesis, genes coding such enzymes, and a process for producing equol and its intermediates using the enzymes and genes. n The present invention provides a dihydrodaidzein synthesizing enzyme, tetrahydrodaidzein synthesizing enzyme, equol synthesizing enzyme, and genes coding these enzymes. The present invention also provides a process for synthesizing dihydrodaidzein, tetrahydrodaidzein, and/or equol using these enzymes.

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主要参考文献


1: Mahalingam S, Gao L, Gonnering M, Helferich W, Flaws JA. Equol inhibits growth, induces atresia, and inhibits steroidogenesis of mouse antral follicles in vitro. Toxicol Appl Pharmacol. 2016 Mar 15;295:47-55. doi: 10.1016/j.taap.2016.02.009.
2: Hazim S, Curtis PJ, Schär MY, Ostertag LM, Kay CD, Minihane AM, Cassidy A. Acute benefits of the microbial-derived isoflavone metabolite equol on arterial stiffness in men prospectively recruited according to equol producer phenotype: a double-blind randomized controlled trial. Am J Clin Nutr. 2016 Mar;103(3):694-702. doi: 10.3945/ajcn.115.125690.
3: Pawlowski JW, Martin BR, McCabe GP, McCabe L, Jackson GS, Peacock M, Barnes S, Weaver CM. Impact of equol-producing capacity and soy-isoflavone profiles of supplements on bone calcium retention in postmenopausal women: a randomized crossover trial. Am J Clin Nutr. 2015 Sep;102(3):695-703. doi: 10.3945/ajcn.114.093906.

合成参考文献


参考文献:10.1515/znc-2009-11-1215
摘要:Islam MT. Variation in chemotactic preferences of Aphanomyces cochlioides zoospores to flavonoids. Z Naturforsch C J Biosci. 2009 Nov;64(11-12):847–52. doi: 10.1515/znc-2009-11-1215.
参考文献:10.1139/w11-051
摘要:Isabelle M, Villemur R, Juteau P, Lépine F. Isolation of estrogen-degrading bacteria from an activated sludge bioreactor treating swine waste, including a strain that converts estrone to β-estradiol. Can J Microbiol. 2011 Jul;57(7):559–68. doi: 10.1139/w11-051.
参考文献:10.4103/0974-8490.81958
摘要:El-Halawany AM, El Dine RS, Chung MH, Nishihara T, Hattori M. Screening for estrogenic and antiestrogenic activities of plants growing in Egypt and Thailand. Pharmacognosy Res. 2011 Apr;3(2):107–13.
参考文献:10.1016/j.jnutbio.2011.03.002
摘要:Franke AA, Lai JF, Halm BM, Pagano I, Kono N, Mack WJ, Hodis HN. Equol production changes over time in postmenopausal women. The Journal of Nutritional Biochemistry. 2012 Jun;23(6):573–9. doi: 10.1016/j.jnutbio.2011.03.002.
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