CAS: 3371-27-5; (2S,3R)-2-(3,4,5-Trihydroxyphenyl)Chromane-3,5,7-Triol

该化合物是一种自然形成的裂变,具体地说是一种种类的丙烯,主要存在于各种植物中,特别是绿色茶叶和某些水果中,其特点是多酚结构,有助于其抗氧化性特性;该化合物的分子式反映了其碳,氢和氧原子的复杂安排,典型的多氢氧基组,加强了其在水中的再活性和溶性;(-)-Gallatechin展示了各种生物活动,包括潜在的反炎,抗癌和心血管保护效应,使其对营养和药物研究感兴趣;其立体化学学,前缀 " (-) " 表示其具体的空间安排,这对生物活动至关重要;该化合物在人类健康中的作用及其潜在的治疗应用,特别是在与氧化性压力有关的慢性疾病方面;

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(2R,2''R,3S,3''R,4S)-[4,8]-2,3-trans-3,4-trans-(+)-catechin-(-)-epigall°C atechin (-)-epigall°C atechin 3,4'-di-O-gallate (-)-epigall°C atechin 3,3'-di-O-gallate (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl (E)-3-(3,4-dihydroxyphenyl)acrylate oolongtheanine theasinensin C LDN-0096693 LDN-0096568

合成工艺路线路线简述

    (-)-表没食子儿茶素 以 水 用作溶剂,化学反应 1.0H,以63%的收率获得(-)-倍儿茶酸
    参考文献:Epimerization Of Tea Catechins Under Weakly Acidic And Alkaline Conditions
    标题:Epimerization Of Tea Catechins Under Weakly Acidic And Alkaline Conditions
    摘要:在ph 7的缓冲溶液中,用n2代替o2,在80 oc下,茶叶儿茶素迅速发生差向异构化反应,氧化副反应不到10%,儿茶素差向异构体的收率为50-63%.具有三个羟基的儿茶素比具有两个羟基的儿茶素差向异构化反应更快,不含没食子酰基的儿茶素比含有没食子酰基酯的儿茶素差向异构化反应更快.
    Doi:10.1271/bbb.90884

    海关参考信息

    专利信息


    专利号:US-9556140-B2
    优先权日:2013-01-26
    标 题 :Approach for synthesis of catechins
    发明人:DUGAR SUNDEEP; MAHAJAN DINESH; RAI KUMAR SANTOSH; TRIPATHI VINAYAK; PATIL ISHWAR RAKESH
    权利人:SPHAERA PHARMA PRIVATE LTD
    摘要:A process for synthesis of enatiomerically pure or enatiomerically enriched or racemic mixture of (+ and/or −) epicatechin and its intermediates, comprising the steps of: (i) obtaining penta-protected quercetin; (ii) reducing the penta-protected quercetin obtained from step (i); (iii) optionally deprotecting the compound of step (ii); (iv) reducing the compound obtained from step (ii) or step (iii) in the presence of a chiral/achiral reducing agent to obtain a chiral intermediate; (v) deprotecting and/or hydrogenation of the chiral intermediate obtained from step (iv) to obtain (−)-epicatechin; (vi) optionally simultaneously deprotecting and by drogenation of the compound obtained from step (ii) to obtain racemic epicatechin.

    专利号:US-9428482-B2
    优先权日:2011-01-27
    标 题 :Process for synthesis of polyphenols
    发明人:DUGAR SUNDEEP; MAHAJAN DINESH; PANTELIS PETER GIANNOUSIS; SINGH VIJAY; KAPOOR KAMAL KISHORE
    权利人:DUGAR SUNDEEP; MAHAJAN DINESH; PANTELIS PETER GIANNOUSIS; SINGH VIJAY; KAPOOR KAMAL KISHORE; SPHAERA PHARMA PTE LTD
    摘要:The present invention provides synthetic processes for preparing racemic and/or optically pure epicatechin, epigallocatechin and related polyphenols as such or as their variously functionalized derivatives. A principle objective of the disclosure is to provide a new and useful method of synthesis to obtain polyphenols in isomerically pure and/or racemic forms.

    专利号:US-2016361291-A1
    优先权日:2013-12-18
    标 题:Methods for increasing skeletal muscle protein synthesis using green tea extract
    发明人:MEADOR BENJAMIN; PEREIRA SUZETTE; EDENS NEILE; TISDALE MICHAEL
    权利人:ABBOTT LAB
    摘要:Methods of increasing skeletal muscle protein synthesis in a subject are provided. Methods of increasing or maintaining mammalian target of rapamycin (mTOR) activation are also provided. Such methods include a step of administering at least one serving per day of a composition including 20 to 2,000 mg of a green tea extract per serving to the subject.

    专利号:JP-2020117531-A
    优先权日:2013-01-26
    标题 :Novel process for synthesis of catechins

    专利号:US-2009170928-A1
    优先权日:2005-04-28
    标题:Synthesis of oligo/poly(catechins) and methods of use

    专利号:US-2014031421-A1
    优先权日:2011-01-27
    标 题 :Novel process for synthesis of polyphenols
    南京非跃生物科技有限公司
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    主要参考文献


    1: Lin G, Chang L, Liu Y, Xiang Z, Chen J, Yang Z. Enantioselective total syntheses of (+)-gallocatechin, (-)-epigallocatechin, and 8-C-ascorbyl-(-)-epigallocatechin. Chem Asian J. 2013 Apr;8(4):700-4. doi: 10.1002/asia.201201168. Epub 2013 Jan 29. Epub 2007 Sep 20. doi: 10.1021/jf901545u. doi: 10.1248/bpb.b14-00646. doi: 10.3390/ijms14059779.
    9: Wong IL, Wang BC, Yuan J, Duan LX, Liu Z, Liu T, Li XM, Hu X, Zhang XY, Jiang T, Wan SB, Chow LM. Potent and Nontoxic Chemosensitizer of P-Glycoprotein-Mediated Multidrug Resistance in Cancer: Synthesis and Evaluation of Methylated Epigallocatechin, Gallocatechin, and Dihydromyricetin Derivatives. J Med Chem. 2015 Jun 11;58(11):4529-49. doi: 10.1021/acs.jmedchem.5b00085. Epub 2015 Jun 2. doi: 10.1021/jf2039789. Epub 2012 Feb 8.
    13: Sugita-Konishi Y, Hara-Kudo Y, Amano F, Okubo T, Aoi N, Iwaki M, Kumagai S. Epigallocatechin gallate and gallocatechin gallate in green tea catechins inhibit extracellular release of Vero toxin from enterohemorrhagic Escherichia coli O157:H7. Biochim Biophys Acta. 1999 Oct 18;1472(1-2):42-50. doi: 10.1021/jf204715q. Epub 2012 Mar 19. Undetermined Language. doi: 10.1093/chemse/bjv018. Epub 2015 May 1. doi: 10.1002/pca.2566. Epub 2015 May 15.

    合成参考文献


    参考文献:10.1007/s11745-008-3167-4
    摘要:Lee SM, Kim CW, Kim JK, Shin HJ, Baik JH. GCG-rich tea catechins are effective in lowering cholesterol and triglyceride concentrations in hyperlipidemic rats. Lipids. 2008 May;43(5):419–29. doi: 10.1007/s11745-008-3167-4.
    参考文献:10.1007/s00425-014-2094-2
    摘要:Zhu Y, Peng QZ, Li KG, Xie DY. Molecular cloning and functional characterization of the anthocyanidin reductase gene from Vitis bellula. Planta. 2014 Aug;240(2):381–98. doi: 10.1007/s00425-014-2094-2.
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