(-)-epicatechin 4'-O-glucuronide | 1146696-35-6

• 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: (-)-epicatechin 4'-O-glucuronide
• 英文别名: epicatechin 4'-O-β-D-glucuronide；(2R,3R)-epicatechin-4'-O-β-D-glucuronic acid；(-)-epicatechin-4'-β-D-glucuronide；Epicatechin-4'-glucuronide；(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-hydroxy-4-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]phenoxy]oxane-2-carboxylic acid
• CAS: 1146696-35-6
• 化学式: C₂₁H₂₂O₁₂
• 分子量: 466.398
• InChiKey: FXAMKGHSKXKNHR-CVPXIJHMSA-N

物化性质

• 沸点：
  878.2±65.0 °C(Predicted)
• 密度：
  1.763±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  207
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  3,4,6-三邻乙酰基-alpha-D-吡喃葡萄糖 1,2-(原酸甲酯) 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 (-)-epicatechin 4'-O-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

• Epicatechin B-Ring Conjugates: First Enantioselective Synthesis and Evidence for Their Occurrence in Human Biological Fluids
  作者：Fedor Romanov-Michailidis、Florian Viton、René Fumeaux、Antoine Lévèques、Lucas Actis-Goretta、Maarit Rein、Gary Williamson、Denis Barron

  DOI：10.1021/ol3016463

  日期：2012.8.3

  Herein, the first enantioselective total synthesis of a number of biologically relevant (−)-epicatechin conjugates is described. The success of this synthesis relied on (i) optimized conditions for the stereospecific cyclization step leading to the catechin C ring; on (ii) efficient conjugation reactions; and on (iii) optimized deprotection sequences. These standard compounds have been subsequently

  在此，描述了许多生物学上相关的（-）-表儿茶素结合物的第一对映选择性全合成。该合成的成功取决于（i）导致儿茶素C环的立体有择环化步骤的最佳条件；（ii）有效的共轭反应；（iii）优化的脱保护序列。随后，这些标准化合物首次用于阐明在（-）-表儿茶素吸收后存在于四种不同人类生物液中的（-）-表儿茶素结合物的模式。
• Preparation and Characterization of Catechin Sulfates, Glucuronides, and Methylethers with Metabolic Interest
  作者：Susana González-Manzano、Ana González-Paramás、Celestino Santos-Buelga、Montserrat Dueñas

  DOI：10.1021/jf803140h

  日期：2009.2.25

  for which sufficient amounts of them are required that cannot be obtained by isolation from biological fluids. This paper describes the preparation of the methyl, sulfate, and glucuronide derivatives of catechins using different chemical syntheses and their characterization by HPLC−DAD−ESI/MS. MS2 fragmentation of the compounds was also described that allowed the determination of the location of the different

  儿茶素是许多植物食品中与健康促进有关的主要多酚。在人类有机体中，它们主要代谢为不同的结合物（硫酸盐，葡糖醛酸苷和甲基醚），这些结合物在血浆中进一步发现，将有助于与母体化合物摄入相关的生物学效应。循环代谢物可能具有与原始化合物不同的生物学特性，因此，重要的是评估其活性，为此需要足够量的代谢物，而这些量不能通过从生物体液中分离获得。本文介绍了使用不同化学合成方法制备儿茶素的甲基，硫酸盐和葡萄糖醛酸衍生物，并通过HPLC-DAD-ESI / MS对其进行了表征。MS 2还描述了化合物的断裂，从而可以确定儿茶素糖苷配基上不同取代基的位置。优化的程序允许制备在3'和4'位置缀合的（epi）儿茶素硫酸盐，葡糖醛酸苷和甲基醚，以及在5和7位置缀合的硫酸盐，具有令人满意的收率，可以通过半制备型HPLC进一步分离，考虑到它们在体外/离体测定中的用途。
• Chemical Synthesis and Characterization of Epicatechin Glucuronides and Sulfates: Bioanalytical Standards for Epicatechin Metabolite Identification
  作者：Mingbao Zhang、G. Erik Jagdmann、Michael Van Zandt、Ryan Sheeler、Paul Beckett、Hagen Schroeter

  DOI：10.1021/np300568m

  日期：2013.2.22

  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.