β-1,2,3-tri-O-galloyl-4,6-(S)-hexahydroxydiphenoyl-D-glucose pentadecamethyl ether | 73493-42-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: β-1,2,3-tri-O-galloyl-4,6-(S)-hexahydroxydiphenoyl-D-glucose pentadecamethyl ether
• 英文别名: [(10R,11S,12R,13S,15R)-3,4,5,21,22,23-hexamethoxy-8,18-dioxo-12,13-bis[(3,4,5-trimethoxybenzoyl)oxy]-9,14,17-trioxatetracyclo[17.4.0.02,7.010,15]tricosa-1(23),2,4,6,19,21-hexaen-11-yl] 3,4,5-trimethoxybenzoate
• CAS: 73493-42-2
• 化学式: C₅₆H₆₀O₂₆
• 分子量: 1149.08
• InChiKey: JVCWBKAQNINGIN-WKMXFBBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  82
• 可旋转键数：
  24
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  279
• 氢给体数：
  0
• 氢受体数：
  26

反应信息

• 作为产物：
  描述：

  可得然胶 在 4-二甲氨基吡啶 、 oxonium 、 4-(dimethylamino)pyridine hydrochloride 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 β-1,2,3-tri-O-galloyl-4,6-(S)-hexahydroxydiphenoyl-D-glucose pentadecamethyl ether
  参考文献：
  名称：

  Cyanocuprate-mediated intramolecular biaryl couplings applied to an ellagitannin. Synthesis of (+)-O-permethyltellimagrandin II

  摘要：

  Generation of an intramolecularly tethered, nonracemic diaryl cuprate followed by its oxidation with ground state oxygen at -78 degrees leads to a biaryl precursor to an ellagitannin. Subsequent attachment of the appropriate glucose unit completes the synthesis of the title compound.

  DOI：

  10.1016/s0040-4039(00)77248-0

文献信息

• Eugeniin, a new ellagitannin from cloves.
  作者：GEN-ICHIRO NONAKA、MISAKO HARADA、ITSUO NISHIOKA

  DOI：10.1248/cpb.28.685

  日期：——

  A new ellagitannin, eugeniin was isolated from cloves, the dried flower buds of Eugenia caryophyllata THUNB., and the structure was determined to be 1, 2, 3-trigalloyl 4, 6-hexahydroxydiphenoyl β-D-glucopyranose.

  一种新的椰子单宁——尤金宁（eugeniin）从丁香（Eugenia caryophyllata THUNB.）的干花苞中分离出来，其结构确定为1, 2, 3-三没食子酸基4, 6-六羟基二苯基β-D-葡萄糖吡喃糖。
• 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。