2-[3′-metoxy-4′-(methyl-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)phenyl]ethyl acetate | 1445865-08-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[3′-metoxy-4′-(methyl-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)phenyl]ethyl acetate
• CAS: 1445865-08-6
• 化学式: C₂₄H₃₀O₁₃
• 分子量: 526.494
• InChiKey: QTMIQZLBGLERDZ-VZGLXOSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.87
• 重原子数：
  37.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  159.19
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  homovanillyl alcohol acetate 、 3,4,6-三邻乙酰基-alpha-D-吡喃葡萄糖 1,2-(原酸甲酯) 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以32%的产率得到2-[3′-metoxy-4′-(methyl-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)phenyl]ethyl acetate
  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