(3S,5S,9R,10S,13R,14R,17R)-17-[(2R,5R)-5-乙基-7-甲基-6-亚甲基辛烷-2-基]-10,13-二甲基-2,3,4,5,6,9,11,12,14,15,16,17-十二氢-1H-环戊二烯并[a]菲-3-醇 | 129620-23-1

• 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
• 中文名称: (3S,5S,9R,10S,13R,14R,17R)-17-[(2R,5R)-5-乙基-7-甲基-6-亚甲基辛烷-2-基]-10,13-二甲基-2,3,4,5,6,9,11,12,14,15,16,17-十二氢-1H-环戊二烯并[a]菲-3-醇
• 英文名称: Sutinasterol
• 英文别名: (3S,5S,9R,10S,13R,14R,17R)-17-[(2R,5R)-5-ethyl-7-methyl-6-methylideneoctan-2-yl]-10,13-dimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 129620-23-1
• 化学式: C₃₁H₅₂O
• 分子量: 440.753
• InChiKey: ALRMQDKADQHRGT-BARFHZGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-溴苯甲酸酐 、 (3S,5S,9R,10S,13R,14R,17R)-17-[(2R,5R)-5-乙基-7-甲基-6-亚甲基辛烷-2-基]-10,13-二甲基-2,3,4,5,6,9,11,12,14,15,16,17-十二氢-1H-环戊二烯并[a]菲-3-醇 在 4-二甲氨基吡啶 作用下， 以 苯 为溶剂， 反应 5.0h， 生成 Sutinasterol p-bromobenzoate
  参考文献：
  名称：

  Sterols of marine invertebrates. 63. Isolation and structure elucidation of sutinasterol, the major sterol of the marine sponge Xestospongia sp

  摘要：

  A new sterol, sutinasterol ((24R)-24-ethyl-26,26-dimethyl-3-beta-hydroxycholesta-7,25(27)-diene) with a side chain arising from quadruple biomethylation has been isolated from the marine sponge Xestospongia sp. Since it represents the bulk (94%) of the sterol fraction, it presumably plays a biological role in membrane function. Four minor sterols were also characterized, one of which appears to be a biosynthetic intermediate of sutinasterol. A second trace sterol contains a side chain that is the result of five biomethylations and is the largest sterol isolated from natural sources to date. The structures of these sterols were deduced from spectral data (H-1 and C-13 NMR and MS). A crystal structure study of sutinasterol was performed to determine the stereochemistry of the C24 ethyl group.

  DOI：

  10.1021/jo00001a013

文献信息

• Sterols of marine invertebrates. 63. Isolation and structure elucidation of sutinasterol, the major sterol of the marine sponge Xestospongia sp
  作者：Russell G. Kerr、Sutinah L. Kerr、George R. Pettit、Delbert L. Herald、Thomas L. Groy、Carl Djerassi

  DOI：10.1021/jo00001a013

  日期：1991.1

  A new sterol, sutinasterol ((24R)-24-ethyl-26,26-dimethyl-3-beta-hydroxycholesta-7,25(27)-diene) with a side chain arising from quadruple biomethylation has been isolated from the marine sponge Xestospongia sp. Since it represents the bulk (94%) of the sterol fraction, it presumably plays a biological role in membrane function. Four minor sterols were also characterized, one of which appears to be a biosynthetic intermediate of sutinasterol. A second trace sterol contains a side chain that is the result of five biomethylations and is the largest sterol isolated from natural sources to date. The structures of these sterols were deduced from spectral data (H-1 and C-13 NMR and MS). A crystal structure study of sutinasterol was performed to determine the stereochemistry of the C24 ethyl group.