ethyl 4-β-D-glucopyranosyloxy-3-methoxybenzoate | 1131878-62-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: ethyl 4-β-D-glucopyranosyloxy-3-methoxybenzoate
• CAS: 1131878-62-0
• 化学式: C₁₆H₂₂O₉
• 分子量: 358.345
• InChiKey: NEXROKCHSRMTOS-XYFZXANASA-N

物化性质

• 沸点：
  574.1±50.0 °C(predicted)
• 密度：
  1.405±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.95
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  134.91
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  3-methoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-benzoic acid ethyl ester 在 甲醇 、 sodium methylate 作用下， 生成 ethyl 4-β-D-glucopyranosyloxy-3-methoxybenzoate
  参考文献：
  名称：

  Molecular Interactions between Barley and Oat β-Glucans and Phenolic Derivatives

  摘要：

  Equilibrium dialysis, molecular modeling, and multivariate data analysis were used to investigate the nature of the molecular interactions between 21 vanillin-inspired phenolic derivatives, 4 bile salts, and 2 commercially available beta-glucan preparations, Glucagel and PromOat, from barley and oats. The two beta-glucan products showed very similar binding properties. It was demonstrated that the two beta-glucan products are able to absorb most phenolic derivatives at a level corresponding to the absorption of bile salts. Glucosides of the phenolic compounds showed poor or no absorption. The four phenolic derivatives that showed strongest retention in the dialysis assay shared the presence of a hydroxyl group in para-position to a CHO group. However, other compounds with the same structural feature but possessing a different set of additional functional groups showed less retention. Principal component analysis (PCA) and partial least-squares regression (PLS) calculations using a multitude of diverse descriptors related to electronic, geometrical, constitutional, hybrid, and topological features of the phenolic compounds showed a marked distinction between aglycon, glucosides, and bile salt retention. These analyses did not offer additional information with respect to the mode of interaction of the individual phenolics with the beta-glucans. When the barley beta-glucan was subjected to enzyme degradation, the ability to bind some but not all of the phenolic derivatives was lost. It is concluded that the binding must be dependent on multiple characteristics that are not captured by a single molecular descriptor.

  DOI：

  10.1021/jf802057v