eschweilenol B

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: eschweilenol B
• 英文别名: 2,3,8,9,10-Pentahydroxy-4,7,12,13-tetraoxa-naphtho[2,1,8-qra]naphthacene-5,14-dione；6,7,8,17,18-Pentahydroxy-3,10,15,22-tetraoxahexacyclo[14.6.2.02,11.04,9.013,23.020,24]tetracosa-1(23),2(11),4(9),5,7,12,16(24),17,19-nonaene-14,21-dione
• 化学式: C₂₀H₈O₁₁
• 分子量: 424.277
• InChiKey: WJVRFNZACTZZTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  31
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  172
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 eschweilenol B 以 乙醚 、 乙醇 为溶剂， 反应 12.0h， 以1 mg的产率得到2,3,8,9,10-Pentamethoxy-4,7,12,13-tetraoxa-naphtho[2,1,8-qra]naphthacene-5,14-dione
  参考文献：
  名称：

  Three New Ellagic Acid Derivatives from the Bark of Eschweilera coriacea from the Suriname Rainforest

  摘要：

  Bioassay-guided fractionation of Eschweilera coriacea collected in the lowland wet forest of Suriname yielded the new but only weakly active ellagic acid derivative eschweilenol A (1) and the two new but inactive ellagic acid derivatives eschweilenol B (2) and eschweilenol C (3). The four known compounds, sucrose, ellagic acid, 3-O-galloylepigallocatechin, and epigallocatechin, were also isolated. The structures of the three new compounds were determined by spectrometric methods, primarily from the HMQC, HMBC, NOESY, and ROESY NMR techniques, and chemical methods, including methylation and triethylsilylation. The location of a hydroxyl group in one ellagic acid derivative was determined by a new technique involving an NOE correlation of the protons of a triethylsilyl derivative with a proton on a neighboring aromatic ring.

  DOI：

  10.1021/np980046u

文献信息

• Three New Ellagic Acid Derivatives from the Bark of <i>Eschweilera coriacea</i> from the Suriname Rainforest
  作者：Shu-Wei Yang、Bing-Nan Zhou、Jan H. Wisse、Randy Evans、Hendrik van der Werff、James S. Miller、David G. I. Kingston

  DOI：10.1021/np980046u

  日期：1998.7.1

  Bioassay-guided fractionation of Eschweilera coriacea collected in the lowland wet forest of Suriname yielded the new but only weakly active ellagic acid derivative eschweilenol A (1) and the two new but inactive ellagic acid derivatives eschweilenol B (2) and eschweilenol C (3). The four known compounds, sucrose, ellagic acid, 3-O-galloylepigallocatechin, and epigallocatechin, were also isolated. The structures of the three new compounds were determined by spectrometric methods, primarily from the HMQC, HMBC, NOESY, and ROESY NMR techniques, and chemical methods, including methylation and triethylsilylation. The location of a hydroxyl group in one ellagic acid derivative was determined by a new technique involving an NOE correlation of the protons of a triethylsilyl derivative with a proton on a neighboring aromatic ring.