(-)-(2R,3R)-5,7-dihydroxy-2-(3',4'-dihydroxy-phenyl)chroman-3-yl 3'',5''-dihydroxy-4''-methoxybenzoate | 108907-44-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (-)-(2R,3R)-5,7-dihydroxy-2-(3',4'-dihydroxy-phenyl)chroman-3-yl 3'',5''-dihydroxy-4''-methoxybenzoate
• 英文别名: (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-3-yl 3,5-dihydroxy-4-methoxybenzoate；4"-O-methyl-(-)-epicatechin gallate；(-)-epicatechin 3-O-(4'-O-methyl)-gallate；(-)-epicatechin 3-O-(4-O-methyl)-gallate；4''-O-methyl-(-)-epicatechin gallate；epicatechin-3-O-(4'-O-methyl)gallate；Epicatechin 3-O-(4-O-methylgallate)；[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,5-dihydroxy-4-methoxybenzoate
• CAS: 108907-44-4
• 化学式: C₂₃H₂₀O₁₀
• 分子量: 456.406
• InChiKey: BXDRTHBTGNNTEW-NHCUHLMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (-)-(2R,3R)-5,7-dihydroxy-2-(3',4'-dihydroxy-phenyl)chroman-3-yl 3'',5''-dihydroxy-4''-methoxybenzoate 以 水 为溶剂， 反应 0.17h， 以12 mg的产率得到表儿茶素
  参考文献：
  名称：

  Hashimoto, Fumio; Nonaka, Gen-Ichiro; Nishioka, Itsuo, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 2, p. 611 - 616

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-bis(benzyloxy)-4-methoxybenzoyl chloride 在 palladium dihydroxide 4-二甲氨基吡啶 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (-)-(2R,3R)-5,7-dihydroxy-2-(3',4'-dihydroxy-phenyl)chroman-3-yl 3'',5''-dihydroxy-4''-methoxybenzoate
  参考文献：
  名称：

  Regiospecific and enantioselective synthesis of methylated metabolites of tea catechins

  摘要：

  The regiospecific and enantioselective syntheses of various methylated regioisomers of epicatechin gallate (EGC) and epigallocatechin gallate (EGCG) have been achieved. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.010

文献信息

• Syntheses of methylated catechins and theaflavins using 2-nitrobenzenesulfonyl group to protect and deactivate phenol
  作者：Tomohiro Asakawa、Yusuke Kawabe、Atsushi Yoshida、Yoshiyuki Aihara、Tamiko Manabe、Yoshitsugu Hirose、Asuka Sakurada、Makoto Inai、Yoshitaka Hamashima、Takumi Furuta、Toshiyuki Wakimoto、Toshiyuki Kan

  DOI：10.1038/ja.2016.14

  日期：2016.4

  An efficient and versatile synthetic method for labile polyphenols was established using 2-nitrobenzenesulfonate (Ns) as a protecting group for phenol. This methodology provides regio- and stereoselective access to a range of methylated catechins, such as methylated epigallocatechin gallates, that are not readily available from natural sources. In addition, biomimetic synthesis of theaflavins from

  使用2-硝基苯磺酸盐（Ns）作为酚的保护基，建立了一种有效且通用的不稳定多酚合成方法。这种方法为区域和立体选择提供了一系列甲基化的儿茶素，例如甲基化的表没食子儿茶素没食子酸酯，而天然来源不易获得。此外，使用Ns保护可从儿茶素仿生合成茶黄素，从而最大程度地减少了氧化过程中富电子芳环的不良副反应，从而能够在一步氧化偶联反应中构建复杂的苯并马酚酮核。这些化合物的可用性将有助于儿茶素的详细结构生物学活性关系研究。
• Methylation of Tea Catechins by Rat Liver Homogenates
  作者：Kazuo OKUSHIO、Masayuki SUZUKI、Natsuki MATSUMOTO、Fumio NANJO、Yukihiko HARA

  DOI：10.1271/bbb.63.430

  日期：1999.1

  Methylation of (-)-epigallocatechin (EGC), (-)-epicatechin gallate (ECg), and (-)-epigallocatechin gallate (EGCg) was carried out with a rat liver homogenate and S-adenosyl-L-methionine. A structural analysis of the reaction products by MS and NMR showed that 4′-O-methyl EGC, 4″-O-methyl ECg, and 4″-O-methyl EGCg had been formed from EGC, ECg, and EGCg, respectively. These results suggest that methylation may be one of the metabolic pathways to the catechins.

  使用大鼠肝匀浆和 S-腺苷-L-蛋氨酸对 (-)-表儿茶素 (EGC)、(-)-表儿茶素没食子酸酯 (ECg) 和 (-)-表没食子儿茶素没食子酸酯 (EGCg) 进行甲基化。通过MS和NMR对反应产物进行结构分析表明，EGC、ECg和EGCg分别形成4'-O-甲基EGC、4"-O-甲基ECg和4"-O-甲基EGCg。这些结果表明甲基化可能是儿茶素的代谢途径之一。
• Regioselective synthesis of methylated epigallocatechin gallate via nitrobenzenesulfonyl (Ns) protecting group
  作者：Yoshiyuki Aihara、Atsusi Yoshida、Takumi Furuta、Toshiyuki Wakimoto、Toshifumi Akizawa、Motomi Konishi、Toshiyuki Kan

  DOI：10.1016/j.bmcl.2009.05.111

  日期：2009.8

  Regioselective synthesis of methylated epigallocatechin gallate from epigallocatechin was accomplished using a 2-nitrobenzenesulfonyl (Ns) group as a protecting group for phenols. This methodology provided several methylated catechins, which are naturally scarce catechin derivatives. (C) 2009 Elsevier Ltd. All rights reserved.
• Regiospecific and enantioselective synthesis of methylated metabolites of tea catechins
  作者：Sheng Biao Wan、Q. Ping Dou、Tak Hang Chan

  DOI：10.1016/j.tet.2006.04.010

  日期：2006.6

  The regiospecific and enantioselective syntheses of various methylated regioisomers of epicatechin gallate (EGC) and epigallocatechin gallate (EGCG) have been achieved. (c) 2006 Elsevier Ltd. All rights reserved.
• Hashimoto, Fumio; Nonaka, Gen-Ichiro; Nishioka, Itsuo, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 2, p. 611 - 616
  作者：Hashimoto, Fumio、Nonaka, Gen-Ichiro、Nishioka, Itsuo

  DOI：——

  日期：——