(3R,5S,7R,8R,9S,10S,12S,13R,14S)-17-[(2R)-6-羟基-6-甲基庚烷-2-基]-10,13-二甲基-2,3,4,5,6,7,8,9,11,12,14,15,16,17-十四氢-1H-环戊二烯并[a]菲-3,7,12-三醇 | 18866-87-0

• 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
• 中文名称: (3R,5S,7R,8R,9S,10S,12S,13R,14S)-17-[(2R)-6-羟基-6-甲基庚烷-2-基]-10,13-二甲基-2,3,4,5,6,7,8,9,11,12,14,15,16,17-十四氢-1H-环戊二烯并[a]菲-3,7,12-三醇
• 中文别名: (3R,5S,7R,8R,9S,10S,12S,13R,14S)-17-[(2R)-6-羟基-6-甲基庚烷-2-基]-10,13-二甲基-2,3,4,5,6,7,8,9,11,12,14,15,16,17-十四氢-1H-环戊二烯并[a]菲-3,7,12-三酚
• 英文名称: 5β-Cholestane-3α,7α,12α,25-tetrol
• 英文别名: 5β-cholestanetetrol-(3α,7α,12α,25)；3α,7α,12α-Trihydroxy-10,13-dimethyl-17β-((R)-5-hydroxy-1,5-dimethyl-hexyl)-5β-gonan；5β-Cholestantetrol-(3α,7α,12α,25)；(10S)-3t,7t,12t-Trihydroxy-10r,13c-dimethyl-17c-((R)-5-hydroxy-1,5-dimethyl-hexyl)-(5cH,8cH,9tH,14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol；(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-17-[(2R)-6-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7,12-triol
• CAS: 18866-87-0
• 化学式: C₂₇H₄₈O₄
• 分子量: 436.676
• InChiKey: NTIXPPFPXLYJCT-RNUSRIHUSA-N

物化性质

• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 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：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,5S,7R,8R,9S,10S,12S,13R,14S)-17-[(2R)-6-羟基-6-甲基庚烷-2-基]-10,13-二甲基-2,3,4,5,6,7,8,9,11,12,14,15,16,17-十四氢-1H-环戊二烯并[a]菲-3,7,12-三醇 在 silver carbonate 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 7α,12α,25-trihydroxy-5β-cholestan-3-one
  参考文献：
  名称：

  Bile acids. LXXIII. Synthesis of analogs of 7α-hydroxy-4-cholesten-3-one as substrates for hepatic steroid 12α-hydroxylase

  摘要：

  Analogs of 7 alpha-hydroxy-4-cholesten-3-one were prepared to ascertain structural features necessary for maximal activity of hepatic microsomal 12 alpha-steroid hydroxylase. Methyl 3 alpha,7 alpha-dihydroxy-5 beta-cholane-24-carboxylate derived from chenodeoxycholic acid was oxidized at C-3 with silver carbonate/Celite. The product was hydrolyzed and dehydrogenated with SeO2 to provide 3-oxo-7 alpha-hydroxy-4-cholene-24-carboxylic acid. 5 beta-Cholestane-3 alpha,7 alpha,25-triol and 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol were similarly oxidized at C-3 and dehydrogenated to provide 7 alpha,25-dihydroxy-4-cholesten-3-one and 7 alpha,12 alpha,25-trihydroxy-4-cholesten-3-one, respectively. The products were characterized by thin-layer and gas chromatography, ultraviolet, infrared, proton resonance and mass spectrometry.

  DOI：

  10.1016/s0039-128x(84)80020-3
• 作为产物：
  描述：

  cholic acid triformate 在 草酰氯 、 甲烷磺酸 、 silver nitrate 作用下， 以 甲醇 、 乙醚 、 苯 为溶剂， 反应 6.01h， 生成 (3R,5S,7R,8R,9S,10S,12S,13R,14S)-17-[(2R)-6-羟基-6-甲基庚烷-2-基]-10,13-二甲基-2,3,4,5,6,7,8,9,11,12,14,15,16,17-十四氢-1H-环戊二烯并[a]菲-3,7,12-三醇
  参考文献：
  名称：

  7β-hydroxy bile alcohols: Facile synthesis and 2D 1H NMR studies of 5β-cholestane-3α,7β,12α,25-tetrol

  摘要：

  A rapid and easily performed procedure for the synthesis of 5 beta-cholestane-3 alpha, 7 beta, 12 alpha, 25-tetrol by means of an efficient homologation sequence of the intermediate, 3 alpha, 7 beta, 12 alpha-triformyloxy-24-oxo-25-diazo-25-homo-5 beta-cholane is described. The reaction sequence involved treating the intermediate, alpha-diazoketone in methanol with 3% AgNO3 or Ag2O, anhydrous Na2CO3, Na2S2O3/H2O resulting in the formation of homoursocholic acid in high yield. Esterification of the homoursocholic acid in methanol containing a catalytic amount of methanesulfonic acid under microwave irradiation conditions gave methyl homoursocholate. The subsequent treatment of methyl homoursocholate with methyl magnesium iodide provided 5 beta-cholestane-3 alpha,7 beta,12 alpha,25-tetrol in 88% yield The products and synthetic intermediates prepared in these studies were fully characterized by the results of 1D and 2D NMR, and high-resolution mass spectral studies. These studies will help in further investigation of the defect of cholic acid biosynthesis in patients with cerebrotendinous xanthomatosis (CTX) as well as other inborn errors of bile acid metabolism. (C) 1997 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(97)00007-x

文献信息

• Bile alcohol glucuronides: regioselective O-glucuronidation of 5β-cholestane-3α,7α,12α,25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol
  作者：Bishambar Dayal、Gerald Salen、Janak Padia、Sarah Shefer、George S. Tint、Gino Sasso、Tomas H. Williams

  DOI：10.1016/0008-6215(93)84178-9

  日期：1993.2

  procedure for the preparation of 5-beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol-3-O-beta-D-glucuronide and its corresponding C-26 analogue is described. The method involves direct coupling of bile alcohols, namely, 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol and 24-nor-5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol to methyl (tetra-O-acetyl-beta-D-glucopyranuronate) in the presence

  描述了制备5-β-胆甾烷-3α，7α，12α，25-四环-3-3-β-D-葡糖醛酸苷及其相应的C-26类似物的简便且受区域控制的方法。该方法涉及胆汁醇的直接偶联，即5β-胆甾烷3α，7α，12α，25-四醇和24-nor-5β-胆甾烷3α，7α，12α，25-四醇。在二氯甲烷中，在路易斯酸，氯化锡（IV）的存在下，生成甲基（四-O-乙酰基-β-D-吡喃葡萄糖醛酸酯）。通过分析和制备型薄层色谱分离得到的四元醇的1,2-反式和1,2-顺式-葡糖醛酸异头物对，并通过高分辨率1H NMR光谱，化学电离和质谱确定它们的身份。快速原子轰击质谱。所描述的方法相对于涉及溴化物的传统两步合成法具有实际优势，因为它更有效且使用廉价且毒性较小的材料。提示这些化合物可用于研究脑腱黄瘤病（CTX）中血脑屏障的通透性。
• Meiosis regulating compounds
  申请人：——

  公开号：US20010005757A1

  公开（公告）日：2001-06-28

  Certain compounds, structurally related to natural compounds which can be extracted i.a. from bull testes and from human follicular fluid, can be used for regulating the meiosis in oocytes and in male germ cells. Some of these compounds are useful in the treatment of infertility, whereas other compounds are useful as contraceptives. These compounds have the structural formula 1 wherein the substituents are as defined in the specification.

  某些化合物在结构上与可以从公牛睾丸和人类卵泡液中提取的天然化合物相关，可用于调节卵母细胞和男性生殖细胞中的减数分裂。其中一些化合物对治疗不孕症有用，而其他化合物则可用作避孕药。这些化合物具有结构式，其中取代基如规范中定义。
• Identification of 5 β-cholestane-3 α, 7 α, 12 α, 25, 26-pentol in cerebrotendinous xanthomatosis
  作者：B. Dayal、G.S. Tint、D.N. Greeley、T.H. Williams、G. Salen

  DOI：10.1016/0039-128x(83)90142-3

  日期：1983.10

  Abstract An unrecognized pentahydroxy bile alcohol has been isolated from the bile and feces of patients with cerebrotendinous xanthomatosis (CTX). Its structure, 5 β-cholestane-3 α, 7 α, 12 α, 25, 26-pentol has been deduced by spectroscopic methods and confirmed by comparison with a synthetic analog.

  摘要 从脑腱黄瘤病 (CTX) 患者的胆汁和粪便中分离出一种未被识别的五羟基胆汁醇。其结构 5 β-cholestane-3 α, 7 α, 12 α, 25, 26-pentol 已通过光谱方法推导出并通过与合成类似物的比较确认。
• Characterization of pig kidney microsomal cytochrome <i>P</i>-450 catalysing 25-hydroxylation of vitamin D3 and C27 steroids
  作者：T Bergman、H Postlind

  DOI：10.1042/bj2700345

  日期：1990.9.1

  The cytochrome P-450 enzyme which catalyses 25-hydroxylation of vitamin D3 (cytochrome P-450(25] from pig kidney microsomes [Postlind & Wikvall (1988) Biochem. J. 253, 549-552] has been further purified. The specific content of cytochrome P-450 was 15.0 nmol.mg of protein-1, and the protein showed a single spot with an apparent isoelectric point of 7.4 and an Mr of 50,500 upon two-dimensional isoelectric-focusing/SDS/PAGE. The 25-hydroxylase activity towards vitamin D3 was 124 pmol.min-1.nmol of cytochrome P-450-1 and towards 1 alpha-hydroxyvitamin D3 it was 1375 pmol.min-1.nmol-1. The preparation also catalysed the 25-hydroxylation of 5 beta-cholestane-3 alpha,7 alpha-diol at a rate of 1000 pmol.min-1.nmol of cytochrome P-450-1 and omega-1 hydroxylation of lauric acid at a rate of 200 pmol.min-1.nmol of cytochrome P-450-1. A monoclonal antibody raised against the 25-hydroxylating cytochrome P-450, designated mAb 25E5, was prepared. After coupling to Sepharose, the antibody was able to bind to cytochrome P-450(25) from kidney as well as from pig liver microsomes, and to immunoprecipitate the activity for 25-hydroxylation of vitamin D3 and 5 beta-cholestane-3 alpha,7 alpha-diol when assayed in a reconstituted system. The hydroxylase activity towards lauric acid was not inhibited by the antibody. By SDS/PAGE and immunoblotting with mAb 25E5, cytochrome P-450(25) was detected in both pig kidney and pig liver microsomes. These results indicate a similar or the same species of cytochrome P-450 in pig kidney and liver microsomes catalysing 25-hydroxylation of vitamin D3 and C27 steroids. The N-terminal amino acid sequence of the purified cytochrome P-450(25) from pig kidney microsomes differed from those of hitherto isolated mammalian cytochromes P-450.

  细胞色素P-450酶催化维生素D3的25-羟化（来自猪肾微粒体的细胞色素P-450（25）[Postlind＆Wikvall（1988）Biochem.J.253,549-552]已被进一步纯化。细胞色素P-450的特异含量为15.0 nmol.mg-1蛋白质，并且该蛋白质在二维等电聚焦/SDS/PAGE上显示出一个明显的等电点为7.4，分子量为50,500的单一斑点。对于维生素D3的25-羟化酶活性为124 pmol.min-1.nmol细胞色素P-450-1，对于1α-羟基维生素D3的酶活性为1375 pmol.min-1.nmol-1。该制剂还催化了5β-胆甾烷-3α,7α-二醇的25-羟化，速率为1000 pmol.min-1.nmol细胞色素P-450-1，以及月桂酸的ω-1羟化，速率为200 pmol.min-1.nmol细胞色素P-450-1。制备了一种针对25-羟化细胞色素P-450的单克隆抗体，称为mAb 25E5。将抗体偶联到Sepharose后，抗体能够结合到肾脏以及猪肝微粒体的细胞色素P-450（25），并在重构系统中免疫沉淀维生素D3和5β-胆甾烷-3α,7α-二醇的25-羟化活性。抗体未抑制对月桂酸的羟化活性。通过SDS/PAGE和mAb 25E5的免疫印迹，检测到细胞色素P-450（25）存在于猪肾和猪肝微粒体中。这些结果表明，在猪肾和肝微粒体中存在相似或相同的细胞色素P-450物种，可催化维生素D3和C27类固醇的25-羟化。从猪肾微粒体中纯化的细胞色素P-450（25）的N末端氨基酸序列与迄今为止分离的哺乳动物细胞色素P-450的氨基酸序列不同。
• A facile synthesis of 5?-cholestane-3?, 7?, 12?,25-tetrol*1
  作者：B DAYAL

  DOI：10.1016/0039-128x(80)90144-0

  日期：1980.4

  A convenient procedure for the synthesis of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol via a modified homologation sequence of the intermediate 3 alpha,7 alpha,12 alpha-triformyloxy-24-oxo-25-diazo-25-homo-5 beta-cholane involving a homogeneous medium is described. This involves treating the intermediate alpha-diazoketone in methanol with a solution of silver benzoate in triethylamine. Grignard reaction of the resulting triformyloxy methyl homocholate yielded 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol. Large amounts of this bile alcohol were needed to further investigate the defect of cholic acid biosynthesis in patients with cerebrotendinous xanthomatosis (CTX).