(22S,25S)-(5α)-spirosolane-3β,7α-diol | 107423-40-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (22S,25S)-(5α)-spirosolane-3β,7α-diol
• 英文别名: tomatidane-3β,7α-diol；(1R,2S,4S,5'S,6S,7S,8R,9S,12S,13S,16S,18R,20R)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-piperidine]-16,20-diol
• CAS: 107423-40-5
• 化学式: C₂₇H₄₅NO₃
• 分子量: 431.659
• InChiKey: GAEKNUMQYPAKIY-LFSDXSMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  61.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (22S,25S)-(5α)-spirosolane-3β,7α-diol 在 吡啶 作用下， 生成 (22S,25S)-3β,7α-diacetoxy-28-acetyl-(5α)-spirosolane
  参考文献：
  名称：

  The Microbial Hydroxylation of Tomatidine^1a,b

  摘要：

  DOI：

  10.1021/jo01024a046
• 作为产物：
  描述：

  番茄碱 以 乙醇 为溶剂， 生成 (22S,25S)-(5α)-spirosolane-3β,9-diol 、 (22S,25S)-(5α)-spirosolane-3β,7α-diol
  参考文献：
  名称：

  The Microbial Hydroxylation of Tomatidine^1a,b

  摘要：

  DOI：

  10.1021/jo01024a046

文献信息

• Metabolism of the tomato saponin α-tomatine by Gibberella pulicaris
  作者：Klaus-Michael Weltring、Judith Wessels、Guido F. Pauli

  DOI：10.1016/s0031-9422(97)00847-9

  日期：1998.8

  The ascomycete Gibberella pulicaris is able to metabolize the saponin alpha-tomatine within 2 h by first removing the complete lycotetraose moiety leading to the aglycone tomatidine. This product is further converted into 7 alpha-hydroxy-tomatidine and the corresponding Delta(5)-dehydro product 7 alpha-hydroxy-tomatidenol. Structural evidence for the hydroxylated main metabolite as well as the unsaturated minor product is based on MS and NMR measurements. The latter include the application of modern soft pulse H-1 NMR techniques allowing the definitive localization of the position of hydroxylation even for the few milligram quantities that could be obtained. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.