3β-acetoxycholest-5-en-4-one | 56533-66-5

• 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-acetoxycholest-5-en-4-one
• 英文别名: 4-ketocholesteryl acetate；3β-Acetoxy-cholest-5-en-4-on；4-Oxocholest-5-en-3-yl acetate；[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-4-oxo-1,2,3,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 56533-66-5
• 化学式: C₂₉H₄₆O₃
• 分子量: 442.682
• InChiKey: CAGXAMRCJUHQSK-CWLZQRTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-acetoxycholest-5-en-4-one 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Improved synthesis and in vitro evaluation of the cytotoxic profile of oxysterols oxidized at C4 (4α- and 4β-hydroxycholesterol) and C7 (7-ketocholesterol, 7α- and 7β-hydroxycholesterol) on cells of the central nervous system

  摘要：

  Whereas the biological activities of oxysterols oxidized at C7 (7-ketocholesterol (71(C), 76-hydroxycholesterol (7 6-0HC), 7 alpha-hydroxycholesterol (7 alpha-OHC)) are well documented, those of oxysterols oxidized at C4 (4 beta-hydroxycholesterol (4 beta-OHC), 4 alpha-hydroxycholesterol (4 alpha-OHC)) are not well known, especially on the cells of the central nervous system. Therefore, an improved methodology has been validated for 4 beta-OHC and 4 alpha-OHC synthesis, and the effects on cell viability and cell growth of these molecules were studied on immortalized, tumoral and normal brain cells (158N, C6 and SK-N-BE cells, and mixed primary cultures of astrocytes and oligodendrocytes). Whereas inhibition of cell growth with 7KC, 7 6-OHC, and 7 alpha-OHC is associated with a decrease of cell viability (cytotoxic activities), our data establish that 4 beta-OHC and 4a-OHC have no effect on cell viability, and no or minor effect on cell growth evocating cytostatic properties. Thus, comparatively to oxysterols oxidized at C7, the toxicity of oxysterols oxidized at C4 is in the following range of order: 7KC > 76-OHC > 7 alpha-OHC > (4 alpha-OHC > 4 alpha-OHC). Interestingly, to date, 4 beta-0HC and 4a-OHC are the only oxysterols identified with cytostatic properties suggesting that these molecules, whereas not cytotoxic, may have some interests to counteract cell proliferation. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.028
• 作为产物：
  描述：

  4-Beta-羟基胆固醇 在 吡啶 、 chromium(VI) oxide 、 氯仿 、 溴 、 溶剂黄146 、 苯 作用下， 生成 3β-acetoxycholest-5-en-4-one
  参考文献：
  名称：

  10.类固醇和相关化合物。第五部分类固醇二酚

  摘要：

  DOI：

  10.1039/jr9400000060

文献信息

• H-Atom Abstraction vs Addition: Accounting for the Diverse Product Distribution in the Autoxidation of Cholesterol and Its Esters
  作者：Zosia A. M. Zielinski、Derek A. Pratt

  DOI：10.1021/jacs.8b11524

  日期：2019.2.20

  serious implications for how these oxysterols are used as biomarkers. The resolution and quantification of all autoxidation products by LC-MS/MS was greatly enabled by the synthesis of a new isotopically labeled cholesterol standard and corresponding selected autoxidation products. The autoxidation of cholesteryl acetate was also investigated as a model for the cholesterol esters which abound in vivo. Although

  我们最近表示，胆固醇的自由基介导的氧化（自氧化）会产生比以前认为的更复杂的氢过氧化物产物混合物。除了主要产物胆固醇 7-氢过氧化物的差向异构体之外，在良好的 H 原子供体存在下，还形成了区域异构 4-和 6-氢过氧化物中的每一种的差向异构体，就像 5α-氢过氧化物一样。在此，我们通过报告竞争性过氧自由基加成到胆固醇产生的产物来完成这个故事，立体异构的胆固醇-5,6-环氧化物占氧化产物的 12%，以及胆固醇氢过氧化物的亲电脱水产物， 4-、6- 和 7- 酮胆固醇。而且，我们询问了在良好的 H 原子供体存在的情况下，它们的分布和相对于 H 原子提取产物的丰度如何变化，这对如何将这些氧甾醇用作生物标志物具有重要意义。LC-MS/MS 对所有自氧化产物的分辨率和定量在很大程度上得益于合成新的同位素标记胆固醇标准品和相应的选定自氧化产物。还研究了胆固醇乙酸酯的自氧化作为体内大量胆固醇酯的模型。尽管
• Cholesterol and Companions. IX. Oxidation of Δ⁵-Cholestene-3-one with Lead Tetraacetate
  作者：Louis F. Fieser、Robert Stevenson

  DOI：10.1021/ja01636a004

  日期：1954.4