2-(4-glucuronide-3-hydroxyphenyl)ethanol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-glucuronide-3-hydroxyphenyl)ethanol
• 英文别名: hydroxytyrosol 4'-O-β-D-glucuronide；2-[3-metoxy-4′-(β-D-glucopyranosyluronic acid)phenyl]ethanol；(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(2-hydroxy-4-(2-hydroxyethyl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid；2-[3'-hydroxy-4'-(β-D-glucopyranosyluronic acid)phenyl]ethanol；2-[4'-hydroxy-3'-(β-D-glucopyranosyluronic acid)phenyl]ethanol；Hydroxytyrosol 4'-glucuronide；(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-hydroxy-4-(2-hydroxyethyl)phenoxy]oxane-2-carboxylic acid
• 化学式: C₁₄H₁₈O₉
• 分子量: 330.292
• InChiKey: JMDNSUMWVYKARS-BYNIDDHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-[3′-metoxy-4′-(methyl-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)phenyl]ethyl acetate 在 水 、 sodium carbonate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以67%的产率得到2-(4-glucuronide-3-hydroxyphenyl)ethanol
  参考文献：
  名称：

  Protective Activity of Hydroxytyrosol Metabolites on Erythrocyte Oxidative-Induced Hemolysis

  摘要：

  The capacity of important hydroxytyrosol metabolites (homovanillyl alcohol, hydroxytyrosol acetate, homovanillyl alcohol acetate, hydroxytyrosol 3' and 4'-O-glucuronides, and homovanillyl alcohol 4'-O-glucuronide) to protect red blood cells (RBCs) from oxidative injury induced by the radical initiator 2,2'-azo-bis(2-amidinopropane) dihydrochloride (AAPH) or by the natural radical initiator H2O2 was evaluated. In the presence of AAPH, all compounds showed to protect RBCs from hemolysis in a dose-dependent manner, exccept for the homovanillyl alcohol glucuronide, with the order of activity being at 20 mu M hydroxytyrosol > hydroxytyrosol glucuronides = hydroxytyrosol acetate = homovanillyl alcohol = homovanillyl acetate > homovanillyl alcohol glucuronide. At 10 mu M, hydroxytyrosol, hydroxytyrosol acetate, and hydroxytyrosol glucuronides still protected hemoglobine from oxidation and from morphological RBC changes. In the presence of H2O2, hydroxytyrosol showed to significantly protect RBCs from oxidative hemolysis in a dose-dependent manner, but the hydroxytyrosol glucuronides showed only a limited protection that was independent of the concentration used.

  DOI：

  10.1021/jf4016202

文献信息

• Biocatalyzed Synthesis and Structural Characterization of Monoglucuronides of Hydroxytyrosol, Tyrosol, Homovanillic Alcohol, and 3-(4′-Hydroxyphenyl)propanol
  作者：Olha Khymenets、Jesús Joglar、Pere Clapés、Teodor Parella、María-Isabel Covas、Rafael de la Torre

  DOI：10.1002/adsc.200606221

  日期：2006.10

  The biocatalytic synthesis and purification of O-β-D-monoglucuronide conjugates of hydroxytyrosol, tyrosol, homovanillic alcohol, and 3-(4′-hydroxyphenyl)propanol, using porcine liver microsomes, are described here. The glucuronides were synthesized, analyzed and separated by HPLC-UV, identified by HPLC-MS, and their structures unequivocally established by NMR techniques. The outcome of the glucuronidation

  O的生物催化合成与纯化本文描述了使用猪肝微粒体的羟基酪醇，酪醇，高香草醇和3-（4'-羟基苯基）丙醇的-β-D-单葡糖醛酸苷共轭物。葡糖醛酸苷通过HPLC-UV合成，分析和分离，通过HPLC-MS鉴定，并且通过NMR技术明确地确定了它们的结构。葡糖醛酸糖化反应的结果取决于酚类化合物的结构。因此，用猪肝微粒体生物催化的羟基酪醇的葡糖醛酸化仅在酚羟基上进行。区域选择性类似于对人和大鼠肝微粒体观察到的区域选择性，其4'-羟基位置比3'-羟基位置更有利。对于酪醇，高香草醛醇和羟苯基丙醇，在微粒体葡萄糖醛酸化过程中形成了两种产物：O -β-D-葡糖醛酸化的衍生物，以及次要的O -β-D-葡糖醛酸化的脂族醇。
• A concise synthesis of glucuronide metabolites of urolithin-B, resveratrol, and hydroxytyrosol
  作者：Ricardo Lucas、David Alcantara、Juan Carlos Morales

  DOI：10.1016/j.carres.2009.05.016

  日期：2009.7

  A simple and direct strategy to chemically synthesize O-beta-D-glucuronides of urolithin-B 4, resveratrol 5, and the corresponding hydroxytyrosol derivatives 6, 7 (as a regioisomeric mixture), and 8 is described. The critical glycosylation step has been optimized using a structurally simple phenol, urolithin-B, by modification of several reaction parameters (solvent, promoter, and glucuronide donor). Very high yields have been obtained in the first synthesis of the O-beta-D-glucuronide of urolithin-B 4. Extension of these reaction conditions was used for the synthesis of resveratrol-3-O-glucuronide 5 where a higher yield than previously reported was obtained by using the much more common trichloroacetimidate glucuronide donor. Finally, three O-beta-D-glucuronides of hydroxytyrosol 6, 7, and 8 have been synthesized for the first time using chemical synthesis. (C) 2009 Elsevier Ltd. All rights reserved.