2,3-O-4,4′,5,5′,6,6′-hexahydroxydiphenoyl-β-D-glucose | 83541-38-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 2,3-O-4,4′,5,5′,6,6′-hexahydroxydiphenoyl-β-D-glucose
• 英文别名: 2,3-O-(S)-hexahydroxydiphenoyl-β-D-glucopyranose；HHDP-β-D-glucopyranose；(10R,11R,13R,14R,15S)-3,4,5,11,14,20,21,22-octahydroxy-13-(hydroxymethyl)-9,12,16-trioxatetracyclo[16.4.0.02,7.010,15]docosa-1(22),2,4,6,18,20-hexaene-8,17-dione
• CAS: 83541-38-2
• 化学式: C₂₀H₁₈O₁₄
• 分子量: 482.355
• InChiKey: GEAGRKQCZVLNAU-FYHMHJJZSA-N

物化性质

• 沸点：
  1159.4±65.0 °C(Predicted)
• 密度：
  1.867±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  34
• 可旋转键数：
  1
• 环数：
  4.0
• 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：

  Pterocarinin C 生成 2,3-O-4,4′,5,5′,6,6′-hexahydroxydiphenoyl-β-D-glucose
  参考文献：
  名称：

  NONAKA, GEN-ICHIRO;ISHIMATSU, MAKOTO;AGETA, MASAYUKI;NISHIOKA, ITSUO, CHEM. AND PHARM. BULL., 37,(1989) N, C. 50-53

  摘要：

  DOI：

文献信息

• First and biomimetic total synthesis of a member of the C-glucosidic subclass of ellagitannins, 5-O-desgalloylepipunicacortein A
  作者：Denis Deffieux、Anna Natangelo、Gaëlle Malik、Laurent Pouységu、Jaime Charris、Stéphane Quideau

  DOI：10.1039/c0cc04007j

  日期：——

  The first total synthesis of a member of the C-glucosidic subclass of ellagitannins, 5-O-desgalloylepipunicacortein A, was accomplished by relying on a biomimetic aldol-type formation of its characteristic C-aryl glucosidic bond through the exploitation of the inherent chemical reactivity of a glucopyranosic hemiacetal precursor.

  成功完成了5-O-脱没食子酰普尼卡科尔藤素A的首次全合成，该化合物属于黄酮鞣花酸的C-葡糖苷亚类。此合成依赖于通过利用葡糖吡喃糖半缩醛前体的固有化学反应性，实现其特征性的C-芳基葡糖苷键的仿生醛缩醇型形成反应。
• The metabolism of gallic acid and hexahydroxydiphenic acid in plants. Part 2. Esters of (S)-hexahydroxydiphenic acid with D-glucopyranose (4 C 1)
  作者：Raj K. Gupta、Sabah M. K. Al-Shafi、Keith Layden、Edwin Haslam

  DOI：10.1039/p19820002525

  日期：——

  One form of further metabolism of β-penta-O-galloyl-D-glucose in higher plants is that in which intramolecular oxidative coupling takes place between adjacent galloyl ester groups (2,3, and 4,6). This route of biosynthesis is confined to certain plants and details of the structure elucidation of some of the principal metabolites are recorded.

  在高等植物中，β-五元-O - galloyl - D-葡萄糖进一步代谢的一种形式是其中在相邻的没食子酰基酯基团（2,3和4,6）之间发生分子内氧化偶联的形式。这种生物合成途径仅限于某些植物，并且记录了一些主要代谢产物的结构阐明细节。
• Nonaka, Gen-ichiro; Ishimatsu, Makoto; Ageta, Masayuki, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 1, p. 50 - 53
  作者：Nonaka, Gen-ichiro、Ishimatsu, Makoto、Ageta, Masayuki、Nishioka, Itsuo

  DOI：——

  日期：——
• Hydrolyzable Tannins with the Hexahydroxydiphenoyl Unit and the <i>m</i>-Depsidic Link:  HPLC-DAD-MS Identification and Model Synthesis
  作者：Panagiotis Arapitsas、Stefano Menichetti、Franco F. Vincieri、Annalisa Romani

  DOI：10.1021/jf0622329

  日期：2007.1.1

  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.