2,3-di-O-galloyl-α-D-glucose | 96691-90-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3-di-O-galloyl-α-D-glucose
• 英文别名: 2,3-digalloyl-α-D-glucose；α-nilocitin；galloyl(-2)[galloyl(-3)]a-Glc；[(2S,3R,4S,5R,6R)-2,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyl)oxyoxan-4-yl] 3,4,5-trihydroxybenzoate
• CAS: 96691-90-6
• 化学式: C₂₀H₂₀O₁₄
• 分子量: 484.37
• InChiKey: LRRLFFLVWQTQGZ-IVABAYMNSA-N

物化性质

• 沸点：
  947.5±65.0 °C(Predicted)
• 密度：
  1.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  244
• 氢给体数：
  9
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 2,3-di-O-galloyl-β-D-glucopyranose 、 2,3-di-O-galloyl-α-D-glucose
  参考文献：
  名称：

  Hydrolyzable Tannins with the Hexahydroxydiphenoyl Unit and the m-Depsidic Link:  HPLC-DAD-MS Identification and Model Synthesis

  摘要：

  This study was designed to develop efficient analytical tools for the difficult HPLC-DAD-MS identification of hydrolyzable tannins in natural tissue extracts. Throughout the study of the spectroscopic characteristics of properly synthesized stereodefined standards, it was observed that the UV-vis spectra of compounds with the m-depsidic link showed a characteristic shoulder at 300 nm, consistent with the simple glucogalloyl esters, whereas compounds with the hexahydroxydiphenoyl (HHDP) unit gave a diagnostic fragmentation pattern, caused by a spontaneous lactonization in the mass spectrometer. These observations were confirmed by HPLC-DAD-MS analyses of tannic acid and raspberry extracts, which are rich in hydrolyzable tannins with the m-depsidic link and the HHDP unit, respectively.

  DOI：

  10.1021/jf0622329