(24S)-24-methyl-5α-cholestane-3β,5,6β-triol | 59048-79-2

• 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: (24S)-24-methyl-5α-cholestane-3β,5,6β-triol
• 英文别名: (24S)-24-methylcholestane-3β,5α,6β-triol；24α-methylcholest-3β,5α,6β-triol；24(S)-methylcholestane-3β,5α,6β-triol；(24S)-ergostane-3β,5α,6β-triol；ergostane-3β,5α,6β-triol；(3S,5R,6R,8S,9S,10R,13R,14S,17R)-17-[(2R,5S)-5,6-dimethylheptan-2-yl]-10,13-dimethyl-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,5,6-triol
• CAS: 59048-79-2；76036-11-8；62504-61-4
• 化学式: C₂₈H₅₀O₃
• 分子量: 434.703
• InChiKey: YUKGXGFQDRWBSF-KVLSEEKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (24S)-24-methyl-5α-cholestane-3β,5,6β-triol 在 氯化亚砜 、 jones' reagent 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 0.17h， 生成 24(S)-methylcholest-4-ene-3,6-dione
  参考文献：
  名称：

  Pruna, L. B.; Henriques, Ruth D.; Huneck, S., Pharmazie, 1984, vol. 39, # 2, p. 117 - 120

  摘要：

  DOI：
• 作为产物：
  描述：

  24-methylcholest-5-en-3β-yl acetate 在 氢氧化钾 、 甲酸 、 双氧水 作用下， 生成 (24S)-24-methyl-5α-cholestane-3β,5,6β-triol
  参考文献：
  名称：

  Kobayashi, Masaru; Hayashi, Takaaki; Hayashi, Koji, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 6, p. 1848 - 1855

  摘要：

  DOI：

文献信息

• Oxidized Derivatives of Dihydrobrassicasterol: Cytotoxic and Apoptotic Potential in U937 and HepG2 Cells
  作者：Olivia Kenny、Yvonne O’Callaghan、Niamh M. O’Connell、Florence O. McCarthy、Anita R. Maguire、Nora M. O’Brien

  DOI：10.1021/jf204737e

  日期：2012.6.13

  The ability of phytosterol compounds to reduce plasma serum cholesterol levels in humans is well investigated. However, phytosterols are structurally similar to cholesterol with a double bond at the C5-6 position and are therefore susceptible to oxidation. Much research has been carried out on the biological effects of cholesterol oxidation products (COPs) in vitro. In contrast, there is less known about phytosterol oxidation products (POPs). From previous studies, it is apparent that oxidized derivatives of the phytosterols, beta-sitosterol and stigmasterol, are cytotoxic in vitro but are less potent than their COP counterparts. In the present study, the cytotoxic and apoptotic potential of oxidized derivatives of dihydrobrassicasterol (DHB) including 5 alpha,6 alpha-epoxyergostan-3 beta-ol (alpha-epoxide), 5 beta,6 beta-epoxyergostan-3 beta-ol (beta-epoxide), ergost-5-en-7-on-3 beta-ol (7-keto), ergost-5-ene-3 beta,7 beta-diol (7-beta-OH), and ergostane-3 beta,5 alpha,6 beta-triol (triol) were evaluated in the U937 and HepG2 cell lines. In general, 7-keto, 7-beta-OH, and triol derivatives had a significant cytotoxic impact on U937 and HepG2 cells. The oxides appear to be more toxic toward U937 cells. In line with previous findings, the POPs investigated in this study were less potent than the equivalent COPs. The results add to the body of data on the toxicity of individual POPs.
• Anjaneyulu, V.; Rao, K. Nageswara; Kobayashi, M., Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995, vol. 34, # 1, p. 78 - 80
  作者：Anjaneyulu, V.、Rao, K. Nageswara、Kobayashi, M.

  DOI：——

  日期：——