lup-20(29)-en-2α,3β,28-triol | 169134-54-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: lup-20(29)-en-2α,3β,28-triol
• 英文别名: 2α,3β,28-lup-20(29)-entriol；lup-20(29)-ene-3β,28-diol；betulin；(1R,3aS,5aR,5bR,7aR,9R,10R,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-9,10-diol
• CAS: 169134-54-7
• 化学式: C₃₀H₅₀O₃
• 分子量: 458.725
• InChiKey: YTLCVRQYWKFDSE-MYBCYQINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 lup-20(29)-en-2α,3β,28-triol 在 吡啶 作用下， 反应 12.0h， 生成 lup-20(29)-en-2α,3β,28-triol triacetate
  参考文献：
  名称：

  Brassinosteroids, sterols and lup-20(29)-en-2α,3β,28-triol from Rheum Rhabarbarum

  摘要：

  The new pentacyclic triterpene lup-20(29)-en-2 alpha,3 beta,28-triol and its 3,28-dipalmitoyl ester were identified from panicles of Rheum rhabarbarum on the basis of their spectral data (H-1 NMR,. C-13 NMR, MS, IR). Besides the brassinosteroids brassinolide, castasterone and 24-epicastasterone, the phytosterols campesterol, stigmasterol, sitosterol and isofucosterol were identified from the same plant material.

  DOI：

  10.1016/0031-9422(95)00297-k
• 作为产物：
  描述：

  28-O-trityl-2α,3β-dihydroxylup-20(29)-en-28-ol 在 4-甲基苯磺酸吡啶 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以99%的产率得到lup-20(29)-en-2α,3β,28-triol
  参考文献：
  名称：

  有效获得异构体2,3-二羟基Lupanes：首次合成磷酸

  摘要：

  环烷酸（3）是天然存在的戊烷型五环三萜，具有多种药理特性。3的有效合成已从10步中完成，从容易获得的二酮11开始，总产率为19％。还开发了关键中间体17的替代方法，基于该方法，可以从10开始以10步获得3，总产率为26％（从11开始）。此外，七其他异构-2,3-二羟基lupanes 4 - 10已被合成。合成的三萜3 – 10 评估了它们对兔肌肉GPa（RMGPa）的抑制活性，其中一些对RMGPa表现出中等的抑制活性。

  DOI：

  10.1016/j.tet.2009.07.047

文献信息

• Seven new triterpene glycosides from the pericarps of Stryphnodendron fissuratum
  作者：Akihito Yokosuka、Sachiko Kawakami、Mitsue Haraguchi、Yoshihiro Mimaki

  DOI：10.1016/j.phytol.2011.04.010

  日期：2011.9

  Seven new triterpene glycosides on the basis of the lupane skeleton (1-7) were isolated from the pericarps of Stryphnodendron fissuratum (Leguminosae). The structures of 1-7 were determined on the basis of extensive spectroscopic analysis, including two-dimensional NMR data, and the results of hydrolytic cleavage. (C) 2011 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.
• Efficient access to isomeric 2,3-dihydroxy lupanes: first synthesis of alphitolic acid
  作者：Jia Hao、Xueli Zhang、Pu Zhang、Jun Liu、Luyong Zhang、Hongbin Sun

  DOI：10.1016/j.tet.2009.07.047

  日期：2009.9

  Alphitolic acid (3) is a naturally occurring lupane type of pentacyclic triterpene, which possesses various pharmacological properties. Efficient synthesis of 3 has been accomplished in 10 steps with an overall yield of 19% starting from the readily available diketone 11. An alternative approach to the key intermediate 17 has also been developed, and based on this approach, 3 could be obtained in 10

  环烷酸（3）是天然存在的戊烷型五环三萜，具有多种药理特性。3的有效合成已从10步中完成，从容易获得的二酮11开始，总产率为19％。还开发了关键中间体17的替代方法，基于该方法，可以从10开始以10步获得3，总产率为26％（从11开始）。此外，七其他异构-2,3-二羟基lupanes 4 - 10已被合成。合成的三萜3 – 10 评估了它们对兔肌肉GPa（RMGPa）的抑制活性，其中一些对RMGPa表现出中等的抑制活性。
• Brassinosteroids, sterols and lup-20(29)-en-2α,3β,28-triol from Rheum Rhabarbarum
  作者：Jürgen Schmidt、Uwe Himmelreich、Günter Adam

  DOI：10.1016/0031-9422(95)00297-k

  日期：1995.9

  The new pentacyclic triterpene lup-20(29)-en-2 alpha,3 beta,28-triol and its 3,28-dipalmitoyl ester were identified from panicles of Rheum rhabarbarum on the basis of their spectral data (H-1 NMR,. C-13 NMR, MS, IR). Besides the brassinosteroids brassinolide, castasterone and 24-epicastasterone, the phytosterols campesterol, stigmasterol, sitosterol and isofucosterol were identified from the same plant material.