5α-cholestane-3β,4β-diol | 20834-99-5

• 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: 5α-cholestane-3β,4β-diol
• 英文别名: 5α-Cholestan-3β,4β-diol；(10R)-3c.4c-Dihydroxy-10r.13c-dimethyl-17c-((R)-1.5-dimethyl-hexyl)-(5tH.8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；3β.4β-Dihydroxy-10.13-dimethyl-17β-((R)-1.5-dimethyl-hexyl)-5α-gonan；5α-Cholestandiol-(3β.4β)；(3S,4R,5R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,4-diol
• CAS: 20834-99-5
• 化学式: C₂₇H₄₈O₂
• 分子量: 404.677
• InChiKey: YIGWOKYLCVPSEG-ZFALSOKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  29
• 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：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5α-cholestane-3β,4β-diol 在 lead(IV) acetate 、 溶剂黄146 作用下， 生成 3.4-seco-5α-cholestanedioic acid-(3.4)
  参考文献：
  名称：

  79.二氧化硒对固醇和胆汁酸的作用。第三部分 胆固醇

  摘要：

  DOI：

  10.1039/jr9370000377
• 作为产物：
  描述：

  cholesterol 在 selenium(IV) oxide 、 溶剂黄146 、 铂 、 苯 作用下， 生成 5α-cholestane-3β,4β-diol
  参考文献：
  名称：

  79.二氧化硒对固醇和胆汁酸的作用。第三部分 胆固醇

  摘要：

  DOI：

  10.1039/jr9370000377

文献信息

• Hydroxy-steroids. Part XI. The preparation and infrared spectra of vicinal cholestanediols
  作者：C. W. Davey、E. L. McGinnis、J. M. McKeown (née Chancellor)、G. D. Meakins、M. W. Pemberton、R. N. Young

  DOI：10.1039/j39680002674

  日期：——

  Twenty-eight vicinal cholestanediols (positions 1,2; 2,3; 3,4; 4,5; 5,6; 6,7; and 7,8) have been prepared by unambiguous routes starting from the corresponding olefins. The O–H stretching bands of dilute solutions of these diols and of seven reference compounds have been examined under high dispersion. Characteristic differences between ax,ax, ax,eq, and eq,eq compounds were observed. It was concluded

  已经通过从相应的烯烃开始的明确途径制备了二十八个邻位胆固醇二醇（1,2,2,3; 3,4; 4,5; 5,6; 6,7和7,8位）。这些二醇和七种参考化合物的稀溶液的O–H伸缩带已在高分散度下进行了检测。观察到ax，ax，ax，eq和eq，eq化合物之间的特性差异。结论是，不能通过游离和键合羟基的吸收之间的频率差来获得羟基之间的二面角的精确值。
• �ber Steroide und Sexualhormone. 155. Mitteilung. �ber 3?, 5-Dioxy-koprostan und zwei epimere 3,4-Dioxy-cholestane
  作者：Pl. A. Plattner、H. Heusser、A. B. Kulkarni

  DOI：10.1002/hlca.19480310647

  日期：——

  Durch katalytische Reduktion des Cholestenon-epoxyds ist es gelungen, auf partialsynthetischem Weg 3α, 5-Dioxy-koprostan zu bereiten, das in der räumlichen Anordnung des Asymmetriezentrums 5 der Konfiguration des Strophanthidins und verwandter Aglykone entspricht.

  通过胆甾醇环氧化物的催化还原，可以以部分合成的方式制备3α，5-二氧-共前列腺素，其在不对称中心5的空间排列上对应于司他啡啶和相关糖苷配基的构型。
• Stereospecific hydrogen transfer from C-4 to C-6 during enzymatic transformation of cholesterol into cholestenone.
  作者：TOSHIO NAMBARA、SHIGEO IKEGAWA、TOSHIKO HIRAYAMA、HIROSHI HOSODA

  DOI：10.1248/cpb.26.757

  日期：——

  In order to clarify the steric mechanism for biotransformation of ⊿5-3β-hydroxysteroid into ⊿4-3-ketosteroid the metabolic fate of hydrogen at C-4 during conversion of cholesterol into cholestenone by 3β-hydroxysteroid oxidase has been investigated. Of three substrates required for this purpose 4α-d1-cholesterol was prepared through 4-d1-cholest-4-en-3β-ol tert-butyldimethylsilyl ether as a key intermediate. The substrate was incubated with the enzyme, and the content and locality of deuterium in resulting cholestenone were determined by inspection of the mass, nuclear magnetic resonance, and infrared spectra. The transformation products formed from 4α-and 6-deuterated cholesterols retained the label almost intact, while that derived from 4β-d1-cholesterol showed ca. 50% retention of the heavy isotope at 6β. Incubation studies using 6β-d1-cholestenone as a substrate implied that a 50% loss of the label would be ascribable in part to the exchange with the incubation medium under the enzymatic control. These results led to a definite conclusion that 4β-hydrogen was transferred stereospecifically to the 6β-position during biotransformation of cholesterol into cholestenone.

  为了弄清将 ⊿5-3β-羟基类固醇生物转化为 ⊿4-3-酮类固醇的立体机制，研究了 3β-羟基类固醇氧化酶将胆固醇转化为胆甾烯酮过程中 C-4 位氢的代谢去向。在为此目的所需的三种底物中，4α-d1-胆固醇是通过 4-d1-cholest-4-en-3β-ol 叔丁基二甲基硅醚作为关键中间体制备的。将底物与酶孵育，通过检测质量、核磁共振和红外光谱来确定生成的胆甾烯酮中氘的含量和位置。由 4α 和 6-氘化胆固醇形成的转化产物几乎完整地保留了标签，而由 4β-d1- 胆固醇形成的转化产物在 6β 处保留了约 50%的重同位素。使用 6β-d1-cholestenone 作为底物进行的孵育研究表明，50% 的标签损失部分归因于在酶控制下与孵育介质的交换。这些结果得出了明确的结论，即在胆固醇向胆甾烯酮的生物转化过程中，4β-氢被立体定向转移到了 6β 位。
• Sterols. XXXI. Oxidation of Sitosterol by Selenium Oxide
  作者：Russell E. Marker、Oliver Kamm、Eugene L. Wittle

  DOI：10.1021/ja01272a024

  日期：1938.5
• METHODS, COMPOSITIONS, AND KITS FOR THE TREATMENT OF CANCER
  申请人：Haggerty Timothy J.

  公开号：US20140335050A1

  公开（公告）日：2014-11-13

  The invention features methods, compositions, and kits for the administration of an HSP90 inhibitor, OBAA, flunarizine, aphidicolin, damnacanthal, dantrolene, or an analog thereof, alone, or in combination with, e.g., a TAA, an antigen-binding scaffold (e.g., an antibody, a soluble T cell receptor, or a chimeric receptor) specific for a TAA, a cell (e.g., a white blood cell that targets a cancer cell), and/or an IFN-β receptor agonist or an IFN-γ receptor agonist, for the treatment of cancer.