cholic acid | 7170-94-7

• 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: cholic acid
• 英文别名: 3α,7α,12α-trihydroxy-5β-cholane-24-carboxylic acid；3α,7α,12α-Trihydroxy-5β-cholan-24-carbonsaeure；3α,7α,12α-Trihydroxy-26.27-dinor-5β-cholestansaeure-(25)；Homocholic acid；(5R)-5-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]hexanoic acid
• CAS: 7170-94-7
• 化学式: C₂₅H₄₂O₅
• 分子量: 422.605
• InChiKey: XOUBHVKCXRSUEN-SRNOMOOLSA-N

物化性质

• 熔点：
  219.5-220 °C
• 沸点：
  593.3±50.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cholic acid 在 N-溴代丁二酰亚胺(NBS) 、 碳酸氢钠 作用下， 生成 3α,12α-dihydroxy-7-oxo-25-homo-5β-cholan-25-oic acid
  参考文献：
  名称：

  胆汁酸衍生的 PET 基阳离子传感器：其灵敏度的分子结构依赖性

  摘要：

  敏感传感器：讨论了使用胆汁酸作为支架设计 PET 阳离子传感器的一般策略。保持基本分子结构相同，制备了不同的基于胆汁酸的氟离子载体，以实现对金属离子的最高灵敏度。已经研究了灵敏度对分子结构的依赖性。

  DOI：

  10.1002/asia.200900026
• 作为产物：
  描述：

  cholic acid triformate 在 草酰氯 、 silver nitrate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 cholic acid
  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

• Synthesis of homoursodeoxycholic acid and [11,12-3H]homoursodeoxycholic acid
  作者：Tai iu Kuramoto、Keiko Kawamoto、Shigeru Moriwaki、Takahiko Hoshita

  DOI：10.1016/s0039-128x(84)80036-7

  日期：1984.12

  Homoursodeoxycholic acid and [11,12-3H]homoursodeoxycholic acid were synthesized from ursodeoxycholic acid and homocholic acid, respectively. Ursodeoxycholic acid (Ia) was converted to 3 alpha, 7 beta-diformoxy-5 beta-cholan-24-oic acid (Ib) using formic acid. Reaction of the diformoxy derivative (Ib) with thionyl chloride yielded the acid chloride (II) which was treated with diazomethane to produce 3 alpha, 7 bet

  熊去氧胆酸和[11,12-3H]去氧胆酸分别由熊去氧胆酸和高胆酸合成。使用甲酸将熊去氧胆酸（Ia）转化为3α，7β-二甲氧基-5β-胆碱-24-oic酸（Ib）。二甲氧基衍生物（Ib）与亚硫酰氯反应生成酰氯（II），将其用重氮甲烷处理以生成3α，7β-diformoxy-25-diazo-25-homo-5beta-cholan-24-one（ III）。由重氮酮（III）通过Arndt-Eistert合成的Wolff重排形成纯去氧胆酸（IV）。由胆酸通过上述相同的方法制备的高胆酸（V）的N-溴代琥珀酰亚胺氧化得到3α，12α-dihydroxy-7-oxo-25-homo-5β-cholan-25-oicacid （VI）。用1-丙醇中的钠还原7-酮基脱氧胆酸（VI），得到3α，7β，12α-三羟基-25-homo-5β-胆烷-25-酸（VII）。使用乙酸的混合物将7-表甲胆酸（VII）
• Bridgwater, Biochemical Journal, 1956, vol. 64, p. 593,597
  作者：Bridgwater

  DOI：——

  日期：——
• The Preparation of C-27 Steroids from Bile Acids. I. Coprostanetetrol-3(α), 7(α),12(α),25
  作者：W. H. Pearlman

  DOI：10.1021/ja01198a066

  日期：1947.6
• METHOD FOR DETERMINING IN VITRO BIOEQUIVALENCE OF A SUCRALFATE SUSPENSION SAMPLE TO A SUCRALFATE SUSPENSION REFERENCE LISTED DRUG (RLD)
  申请人：Clayton Pharmaceuticals LLC

  公开号：EP3423829B1

  公开（公告）日：2020-10-28
• 7β-hydroxy bile alcohols: Facile synthesis and 2D 1H NMR studies of 5β-cholestane-3α,7β,12α,25-tetrol
  作者：B. Dayal、N.H. Ertel、J. Padia、K.R. Rapole、G. Salen

  DOI：10.1016/s0039-128x(97)00007-x

  日期：1997.5

  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.