(3S,8S,9S,10R,13R,14S,17R)-10,13-二甲基-17-丙-2-基-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊并[a]菲-3-醇 | 1042-59-7

• 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,8S,9S,10R,13R,14S,17R)-10,13-二甲基-17-丙-2-基-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊并[a]菲-3-醇
• 英文名称: 20-methylpregn-5-en-3β-ol
• 英文别名: guneribol；20-Methyl-5-pregnen-3β-ol；20-Methyl-5-pregnenol-3β；20-Methylpregn-5-en-3beta-ol；(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-propan-2-yl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 1042-59-7
• 化学式: C₂₂H₃₆O
• 分子量: 316.527
• InChiKey: COSKITFSCAETCX-BIBIXIOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  (3S,8S,9S,10R,13R,14S,17R)-10,13-二甲基-17-丙-2-基-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊并[a]菲-3-醇 在 氯化亚砜 作用下， 生成 3β-Chlor-20-methyl-5-pregnen
  参考文献：
  名称：

  20-Methylpregnane and Derivatives^1,2

  摘要：

  DOI：

  10.1021/jo01071a022
• 作为产物：
  描述：

  3β-Chlor-20-methyl-5-pregnen 在 氢氧化钾 作用下， 生成 (3S,8S,9S,10R,13R,14S,17R)-10,13-二甲基-17-丙-2-基-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊并[a]菲-3-醇
  参考文献：
  名称：

  The Synthesis of 20-Methyl-5-pregnen-3β-ol

  摘要：

  DOI：

  10.1021/ja01499a050

文献信息

• Steroids and Steroidases. XVI. An Evaluation of Synthetic Routes to Variously C-17-Substituted Δ⁵-3-Ketosteroids
  作者：J. Bryan Jones、Keith D. Gordon

  DOI：10.1139/v72-435

  日期：1972.8.15

  Several routes to variously C-17-substituted Δ5-3-ketosteroids have been surveyed. The most convenient method was found to be oxidation of Δ5-3β-alcohol precursors with the Collins reagent, dipyridine chromium trioxide in methylene chloride. The purities of the desired acid- and base-labile compounds obtained were ≥ 99% in each case.

  已经研究了几种不同的 C-17 取代的 Δ5-3-酮类固醇的途径。发现最方便的方法是用柯林斯试剂氧化 Δ5-3β-醇前体，二吡啶三氧化铬在二氯甲烷中。在每种情况下，所获得的所需酸和碱不稳定化合物的纯度均≥ 99%。
• 10.1016/j.foodchem.2024.140820
  作者：Zhu, Hanyue、Chen, Longjian、Chen, Zi-Xing、Lin, Huiqi、Liu, Jianhui、Kwek, Erika、Ma, Ka Ying、He, Wensen、Wang, Guoxin、Chen, Zhen-Yu

  DOI：10.1016/j.foodchem.2024.140820

  日期：——

  promising. We hypothesize that plant sterols can reduce blood cholesterol because they have a side chain of at least three branches. Three cholesterol analogues were synthesized: CA0 (no side chain), CA3 (a 3‑carbon chain with one branch), and CA14 (a 14‑carbon side chain with two branches), and then compared their effect on blood cholesterol with that of β-sitosterol. Structurally, β-sitosterol has a

  植物甾醇在治疗高胆固醇血症中的应用前景广阔。我们假设植物甾醇可以降低血液胆固醇，因为它们具有至少三个分支的侧链。合成了三种胆固醇类似物：CA0（无侧链）、CA3（具有一个分支的 3 碳链）和 CA14（具有两个分支的 14 碳侧链），然后将它们对血液胆固醇的影响与β-谷甾醇。在结构上，β-谷甾醇具有 10 个碳侧链和三个分支。结果表明，β-谷甾醇可有效降低高胆固醇血症仓鼠血浆总胆固醇（TC）20.3%，而CA0、CA3和CA14对血浆TC没有影响。血浆和肝脏中不存在β-谷甾醇，表明它没有被吸收。我们得出结论，具有三个分支的 β-谷甾醇具有降低血浆 TC 的活性。相反，具有两个或更少支链的侧链的胆固醇类似物不影响血浆胆固醇。
• Short side chain sterols from the tunicate Polizoa opuntia
  作者：Jorge A. Palermo、María F.Rodríguez Brasco、Enrique A. Hughes、Alicia M. Seldes、Vilma T. Balzaretti、Eduardo Cabezas

  DOI：10.1016/0039-128x(95)00167-o

  日期：1996.1

  The sterol composition of the Patagonian tunicate Polizoa opuntia was examined, and twenty-four compounds ,cere identified as having either a Delta(5), Delta(7), or Delta(0) nucleus. Two of them, the rare 20-methylpregn-5-en-3 beta-ol and 20-ethylpregn-5-en-3 beta-ol, were previously unreported as natural products from tunicates. These compounds were present only as trace components; therefore, their structures were confirmed by synthesis from suitnble precursors and by comparison of the spectral and chromatographic constants of the synthetic and natural compounds.
• Acid-catalyzed and photochemical isomerization of steroidal cyclopropenes
  作者：Toshihiro Itoh、Carl Djerassi

  DOI：10.1021/ja00351a047

  日期：1983.6
• GINER, JOSE-LUIS;MARGOT, CHRISTIAN;DJERASSI, CARL, J. ORG. CHEM., 54,(1989) N, C. 2117-2125
  作者：GINER, JOSE-LUIS、MARGOT, CHRISTIAN、DJERASSI, CARL

  DOI：——

  日期：——