3β-hydroxycholesta-5,8-dien-7-one | 96974-03-7

• 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
• 英文名称: 3β-hydroxycholesta-5,8-dien-7-one
• 英文别名: 7-keto-cholesta-5,8-dien-3β-ol；7-ketodehydrocholesterol；7-kDHC；3β-Hydroxy-cholesta-5.8(9)-dien-7-on；3beta-Hydroxycholesta-5,8-dien-7-one；(3S,10S,13R,14R,17R)-3-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-7-one
• CAS: 96974-03-7
• 化学式: C₂₇H₄₂O₂
• 分子量: 398.629
• InChiKey: FZSPKLBNBCBSLR-NYFDNNRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3β-hydroxycholesta-5,8-dien-7-one 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 cholesta-3,5,8-trien-7-one
  参考文献：
  名称：

  Untersuchungen uber Steroide. XXXII. 3β-Acetoxycholesta-5, 8 (9)-dien-7-on und 3β-Acetoxycholesta-5, 8(14)-dien-7-on.

  摘要：

  描述了 7-脱氢胆固醇乙酸酯的光氧化反应。得到的新反应产物是 3β-乙酰氧基胆甾-5，8 (9)-二烯-7-酮。除已知产物外，3β-乙酰氧基胆甾烷-6-烯-5，8α-环氧乙烷的热重排还产生了一种新化合物，即 5，6α-环氧胆甾烷-8 (14)-烯-3β，7α-二醇-3-乙酸酯，该化合物可通过常规方法转化为 3β-乙酰氧基胆甾烷-5，8 (14)-二烯-7-酮。

  DOI：

  10.1248/cpb.11.1028
• 作为产物：
  描述：

  7-脱氢醋酸胆固醇 在 氢氧化钾 、 臭氧 作用下， 以 乙醇 为溶剂， 生成 3β-hydroxycholesta-5,8-dien-7-one
  参考文献：
  名称：

  Untersuchungen uber Steroide. XXXII. 3β-Acetoxycholesta-5, 8 (9)-dien-7-on und 3β-Acetoxycholesta-5, 8(14)-dien-7-on.

  摘要：

  描述了 7-脱氢胆固醇乙酸酯的光氧化反应。得到的新反应产物是 3β-乙酰氧基胆甾-5，8 (9)-二烯-7-酮。除已知产物外，3β-乙酰氧基胆甾烷-6-烯-5，8α-环氧乙烷的热重排还产生了一种新化合物，即 5，6α-环氧胆甾烷-8 (14)-烯-3β，7α-二醇-3-乙酸酯，该化合物可通过常规方法转化为 3β-乙酰氧基胆甾烷-5，8 (14)-二烯-7-酮。

  DOI：

  10.1248/cpb.11.1028

文献信息

• Reactivities and Products of Free Radical Oxidation of Cholestadienols
  作者：Libin Xu、Ned A. Porter

  DOI：10.1021/ja5011674

  日期：2014.4.9

  them, dienols leading to the formation of the pentadienyl radical in ring B (termed endo-B) of the sterol are more reactive than those leading to the pentadienyl radical spanning rings B and C (termed exo-B). By comparing the oxysterol profile formed from 7-DHC and those formed from 8-DHC and 5,8(14)-dienol, products formed from abstraction of the hydrogen atoms at C-9 and C-14 (H-9 or H-14 mechanism)

  7-脱氢胆固醇 (7-DHC) 是迄今为止报道的最易氧化的脂质分子，自由基过氧化的传播速率常数是胆固醇的 200 倍。为了更好地理解 7-DHC 的高反应性并阐明反应机理，我们合成了共轭和跳过的非共轭胆甾二烯醇，它们会产生 7-DHC 过氧化形成的两种假定的戊二烯基自由基中间体之一。额外的二烯醇包括 6,8(9)-二烯醇、5,8(14)-二烯醇、6,8(14)-二烯醇和生物学上重要的 8-脱氢胆固醇 (8-DHC; 5,8(9)-二烯醇）。我们发现所有二烯醇的反应性都明显（至少是胆固醇的 40 倍）。他们之中，导致在甾醇的环 B 中形成戊二烯基（称为内型 B）的二烯醇比导致跨越环 B 和 C 的戊二烯基（称为外型 B）的那些更具反应性。通过比较 7-DHC 和 8-DHC 和 5,8(14)-二烯醇形成的氧甾醇谱，从 C-9 和 C-14（H-9 或 H- 14 机制) 有明显区别。当在良好的氢原子供体
• Metabolism of oxysterols derived from nonenzymatic oxidation of 7-dehydrocholesterol in cells
  作者：Libin Xu、Zeljka Korade、Dale A. Rosado、Karoly Mirnics、Ned A. Porter

  DOI：10.1194/jlr.m035733

  日期：2013.4

  Recent studies suggest that 7-dehydrocholesterol (7-DHC)-derived oxysterols play important roles in the pathophysiology of Smith-Lemli-Opitz syndrome (SLOS), a metabolic disorder that is caused by defective 3 beta-hydroxysterol-Delta(7)-reductase (DHCR7). Although 14 oxysterols have been identified as the primary products of 7-DHC autoxidation in organic solution, the metabolic fate of these oxysterols in a biological environment has not yet been elucidated. Therefore, we incubated these primary 7-DHC oxysterols in control Neuro2a and control human fibroblast cells and identified metabolites of these oxysterols by HPLC-MS. We also incubated Dhcr7-deficient Neuro2a cells and fibroblasts from SLOS patients with isotopically labeled 7-DHC (d(7)-7-DHC). The observation of matching d(0)- and d(7) peaks in HPLC-MS confirmed the presence of true metabolites of 7-DHC after excluding the possibility of ex vivo oxidation. The metabolites of primary 7-DHC oxysterols were found to contribute to the majority of the metabolic profile of 7-DHC in cells. Furthermore, based on this new data, we identified three new 7-DHC-derived metabolites in the brain of Dhcr7-KO mice. Our studies suggest that 7-DHC peroxidation is a major source of oxysterols observed in cells and in vivo and that the stable metabolites of primary 7-DHC oxysterols can be used as markers of 7-DHC peroxidation in these biological systems.-Xu, L., Z. Korade, D. A. Rosado, Jr., K. Mirnics, and N. A. Porter. Metabolism of oxysterols derived from nonenzymatic oxidation of 7-dehydrocholesterol in cells. J. Lipid Res. 2013. 54: 1135-1143.