4,4-dimethyl-5α-cholest-7-en-3-one | 2604-90-2

• 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: 4,4-dimethyl-5α-cholest-7-en-3-one
• 英文别名: 4,4-Dimethyl-5α-cholesten-(7)-on-(3)；4,4-Dimethyl-3-oxo-5α-cholesten-7；5alpha-Cholest-7-en-3-one, 4,4-dimethyl-；(5R,9R,10R,13R,14R,17R)-4,4,10,13-tetramethyl-17-[(2R)-6-methylheptan-2-yl]-2,5,6,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 2604-90-2
• 化学式: C₂₉H₄₈O
• 分子量: 412.7
• InChiKey: XVNFRBRLEKVOLX-DNOGYWRBSA-N

物化性质

• 沸点：
  490.0±44.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  烯胆固烷酮 、 碘甲烷 在 potassium tert-butylate 作用下， 生成 4,4-dimethyl-5α-cholest-7-en-3-one 、 4α-methylcholest-7-en-3-one 、 4β-methyl-5α-cholest-7-en-3-one
  参考文献：
  名称：

  Novel nuclear methylation of sterols by the nematode caenorhabditis elegans

  摘要：

  Caenorhabditis elegans possesses a unique sterol methylation pathway not reported to occur in any other organism and also removes the C-24 ethyl group of sitosterol (a plant sterol). This nematode produced substantial quantities of 4 alpha-methyl-5 alpha-cholest-8(14)-en-3 beta-ol and smaller amounts of lophenol from dietary cholesterol, desmosterol or sitosterol. When C. elegans was propagated in media containing sitosterol plus 25-azacoprostane hydrochloride (25-aza-5 beta-cholestane hydrochloride), an inhibitor of delta 24-sterol reductase in insects, its 4 alpha-methylsterol fraction largely consisted of equal amounts of 4 alpha-methyl-5 alpha-cholesta-7,24-dien-3 beta-ol and 4 alpha-methyl-5 alpha-cholesta-8(14),24-dien-3 beta-ol. Thus 25-azacoprostane hydrochloride inhibited both a delta 24-sterol reductase and a delta 7-sterol isomerase in C. elegans.

  DOI：

  10.1016/0039-128x(83)90042-9

文献信息

• Novel nuclear methylation of sterols by the nematode caenorhabditis elegans
  作者：David J. Chitwood、William R. Lusby、Ruben Lozano、Malcolm J. Thompson、James A. Svoboda

  DOI：10.1016/0039-128x(83)90042-9

  日期：1983.9

  Caenorhabditis elegans possesses a unique sterol methylation pathway not reported to occur in any other organism and also removes the C-24 ethyl group of sitosterol (a plant sterol). This nematode produced substantial quantities of 4 alpha-methyl-5 alpha-cholest-8(14)-en-3 beta-ol and smaller amounts of lophenol from dietary cholesterol, desmosterol or sitosterol. When C. elegans was propagated in media containing sitosterol plus 25-azacoprostane hydrochloride (25-aza-5 beta-cholestane hydrochloride), an inhibitor of delta 24-sterol reductase in insects, its 4 alpha-methylsterol fraction largely consisted of equal amounts of 4 alpha-methyl-5 alpha-cholesta-7,24-dien-3 beta-ol and 4 alpha-methyl-5 alpha-cholesta-8(14),24-dien-3 beta-ol. Thus 25-azacoprostane hydrochloride inhibited both a delta 24-sterol reductase and a delta 7-sterol isomerase in C. elegans.