3’-O-ethyl-(-)-epicatechin | 917219-91-1

• 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-ethyl-(-)-epicatechin
• 英文别名: 2-(3-ethoxy-4-hydroxyphenyl)chroman-3,5,7-triol；3'-O-ethyl-(-)-epicatechin；(2R,3R)-2-(3-ethoxy-4-hydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
• CAS: 917219-91-1
• 化学式: C₁₇H₁₈O₆
• 分子量: 318.326
• InChiKey: JWPMSOATDHFFLB-RHSMWYFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  碘乙烷 、 表儿茶素 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 4.5h， 生成 3’-O-ethyl-(-)-epicatechin
  参考文献：
  名称：

  Effects of (−)-epicatechin and derivatives on nitric oxide mediated induction of mitochondrial proteins

  摘要：

  Impaired mitochondrial function represents an early manifestation of endothelial dysfunction and likely contributes to the development of cardiovascular diseases (CVD). The stimulation of mitochondrial function and/or biogenesis is seen as a means to improve the bioenergetic and metabolic status of cells and thus, reduce CVD. In this study we examined the capacity of the flavanol (-)-epicatechin and two novel derivatives to enhance mitochondrial function and protein levels in cultured bovine coronary artery endothelial cells. As nitric oxide production by endothelial cells is suspected in mediating mitochondria effects (including biogenesis), we also examined the dependence of responses on this molecule using an inhibitor of nitric oxide synthase. Results indicate that the flavanol (-)-epicatechin and derivatives are capable of stimulating mitochondrial function as assessed by citrate synthase activity as well as induction of structural (porin, mitofilin) and oxidative phosporylation protein levels (complex I and II). Effects were blocked by the use of the chemical inhibitor of the synthase thus, evidencing a role for nitric oxide in mediating these effects. The results observed indicate that the three agents are effective in enhancing mitochondria function and protein content. The effects noted for (-)-epicatechin may serve to explain the healthy effects on cardiometabolic risk ascribed to the consumption of cocoa products. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.079

文献信息

• Compositions and methods of use of derivatized flavanols
  申请人：Kwik-Uribe L. Catherine

  公开号：US20060293259A1

  公开（公告）日：2006-12-28

  The invention relates to compositions containing derivatized flavanols such as methylated flavanols, and methods of use thereof for prophylactic or therapeutic treatment of a human or a veterinary animal for example as anti-platelet agents.

  本发明涉及含有衍生化黄烷醇的组合物，例如甲基化黄烷醇，以及其用于预防或治疗人类或兽医动物的方法，例如作为抗血小板剂的用途。
• COMPOSITIONS AND METHODS OF USE OF DERIVATIZED FLAVANOLS
  申请人：MARS, INCORPORATED

  公开号：EP1898902A2

  公开（公告）日：2008-03-19
• US20140256741A1
  申请人：——

  公开号：US20140256741A1

  公开（公告）日：2014-09-11
• US9187448B2
  申请人：——

  公开号：US9187448B2

  公开（公告）日：2015-11-17
• [EN] COMPOSITIONS AND METHODS OF USE OF DERIVATIZED FLAVANOLS<br/>[FR] COMPOSITIONS ET PROCEDES POUR UTILISER DES FLAVANOLS DERIVES
  申请人：MARS INC

  公开号：WO2007002881A2

  公开（公告）日：2007-01-04

  [EN] The invention relates to compositions containing derivatized flavanols such as methylated flavanols, and methods of use thereof for prophylactic or therapeutic treatment of a human or a veterinary animal for example as anti-platelet agents.
  [FR] La présente invention concerne des compositions contenant des flavanols dérivés tels que des flavanols méthylés, et des procédés pour les utiliser pour le traitement prophylactique ou thérapeutique d'un humain ou d'un animal, par exemple en tant qu'agents anti-plaquettes.