aleurinin A | 131158-59-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: aleurinin A
• 英文别名: 2-[[(1R,7R,8S,26R,28R,29R,38R)-1,13,14,15,18,19,20,34,35,39,39-undecahydroxy-2,5,10,23,31-pentaoxo-6,9,24,27,30,40-hexaoxaoctacyclo[34.3.1.04,38.07,26.08,29.011,16.017,22.032,37]tetraconta-3,11,13,15,17,19,21,32,34,36-decaen-28-yl]oxymethyl]prop-2-enenitrile
• CAS: 131158-59-3
• 化学式: C₃₈H₂₇NO₂₃
• 分子量: 865.625
• InChiKey: CCIHZFMRYZSRTN-TWWAIRJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  62
• 可旋转键数：
  3
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  396
• 氢给体数：
  11
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  aleurinin A 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 3-[[(1R,3R,4R,21R,22S)-9,10,11,14,15,16,27,28,29,32,33,34-dodecahydroxy-6,19,24,37-tetraoxo-2,5,20,23,38-pentaoxaheptacyclo[19.18.0.04,22.07,12.013,18.025,30.031,36]nonatriaconta-7,9,11,13,15,17,25,27,29,31,33,35-dodecaen-3-yl]oxy]-2-methylpropanenitrile
  参考文献：
  名称：

  Tannins and related compounds. XCII. Isolation and characterization of cyanogenic ellagitannins, aleurinins A and B, and a related O-glycosidic ellagitannin, aleurinin C, from Aleurites fordii Hemsley.

  摘要：

  A chemical examination of the tannin ingredients in the leaves of the wood oil tree, Aleurites fordii HEMSLEY (Euphorbiaceae), has led to the isolation of three new ellagitannins named aleurinins A (4), B(5) and C(6), together with corilagin (1), geraniin (2) and chebulagic acid (3). on the basis of chemical and spectroscpic evidence, the structures of aleurinins A (4) and B (5) have been established as ellagitannins possessing a novel cyanopropylene alcohol glucoside core, while aleurinin C (6) has been characterized as an ellagitannin based on a hydroxyacetone glucoside core.

  DOI：

  10.1248/cpb.38.861