3'-O-methyl (-)-epicatechin 5-O-β-glucuronide | 603133-94-4

• 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: 3'-O-methyl (-)-epicatechin 5-O-β-glucuronide
• 英文别名: Me-EC-GlcUA；3'-O-methyl-(-)-epicatechin-7-O-β-D-glucuronide；3'-O-Methyl-(-)-epicatechin 7-O-glucuronide；(2S,3S,4S,5R,6S)-6-[[(2R,3R)-3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-chromen-7-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 603133-94-4
• 化学式: C₂₂H₂₄O₁₂
• 分子量: 480.425
• InChiKey: MZJSKSYVZZIYPF-ZRRVXMDUSA-N

物化性质

• 沸点：
  834.1±65.0 °C(Predicted)
• 密度：
  1.656±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  196
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  (2R,3R)-3,5-bis(benzyloxy)-2-(4-(benzyloxy)-3-methoxyphenyl)chroman-7-ol 在 20% palladium hydroxide-activated charcoal 、 氢气 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 5.25h， 生成 3'-O-methyl (-)-epicatechin 5-O-β-glucuronide
  参考文献：
  名称：

  Chemical Synthesis and Characterization of Epicatechin Glucuronides and Sulfates: Bioanalytical Standards for Epicatechin Metabolite Identification

  摘要：

  The monoglucuronides and sulfates of epicatechin, 3'-O-methylepicatechin, and 4'-O-methylepicatechin, respectively, were synthesized as authentic bioanalytical standards. Reversed-phase HPLC methods capable of baseline separation of the glucuronides and sulfates have been developed. Both the epicatechin glucuronides and sulfates were stable in the solid state when stored under ambient conditions and in aqueous solution when stored refrigerated. These results should prove invaluable to the research community as analytical standards as well as in future studies of the biological and pharmacological effects of epicatechin in humans.

  DOI：

  10.1021/np300568m

文献信息

• A versatile approach to the regioselective synthesis of diverse (−)-epicatechin-β-d-glucuronides
  作者：Eric S. Mull、Michael Van Zandt、Adam Golebiowski、R. Paul Beckett、Pradeep K. Sharma、Hagen Schroeter

  DOI：10.1016/j.tetlet.2012.01.054

  日期：2012.3

  A versatile new approach is reported for the total synthesis of five glucuronide metabolites of epicatechin, using selective protection/deprotection techniques. (C) 2012 Elsevier Ltd. All rights reserved.