(3alpha,5beta,7alpha,8xi,9xi,14xi,17xi)-3,7-二羟基胆甾烷-26-酸 | 17974-66-2

• 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: (3alpha,5beta,7alpha,8xi,9xi,14xi,17xi)-3,7-二羟基胆甾烷-26-酸
• 英文名称: (25RS)-3α,7α-dihydroxy-5β-cholestan-26-oic acid
• 英文别名: 3α,7α-dihydroxy-5β-cholestan-26-oic acid；dihydroxycholestanoic acid；3alpha,7alpha-Dihydroxy-5beta-cholestan-26-oic acid；(6R)-6-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylheptanoic acid
• CAS: 17974-66-2
• 化学式: C₂₇H₄₆O₄
• 分子量: 434.66
• InChiKey: ITZYGDKGRKKBSN-HKFUITGCSA-N

物化性质

• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

制备方法与用途

生物活性的3α,7α-二羟基/coprostanic 酸是一种内源性代谢物，也是一种胆汁酸，并且是鹅去氧胆酸的前体。

反应信息

• 作为反应物：
  描述：

  (3alpha,5beta,7alpha,8xi,9xi,14xi,17xi)-3,7-二羟基胆甾烷-26-酸 生成 鹅去氧胆酸
  参考文献：
  名称：

  Non-stereospecific Formation of 3.ALPHA.,7.ALPHA.,24-Trihydroxy-5.BETA.-cholestan-26-oic Acid during Chenodeoxycholic Acid Biosynthesis.

  摘要：

  将 3α，7α-二羟基-5β-胆甾烷-26-酸及其 Δ24- 类似物与大鼠肝匀浆孵育，可产生 3α，7α，24-三羟基-5β-胆甾烷-26-酸的 C-24、25 非对映异构体混合物，而 3α，7α，24-三羟基-5β-胆甾烷-26-酸是去氧胆酸生物合成的关键中间体。

  DOI：

  10.1248/cpb.42.1536
• 作为产物：
  描述：

  3α,7α-diformyloxy-5β-24-hydroxy-cholane 在 咪唑 、 氢氧化钾 、 碘 、 sodium hydride 、 三苯基膦 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 二甲基亚砜 为溶剂， 反应 11.0h， 生成 (3alpha,5beta,7alpha,8xi,9xi,14xi,17xi)-3,7-二羟基胆甾烷-26-酸
  参考文献：
  名称：

  A convenient synthesis of 5β-cholestan-26-oic and 5β-cholestan-26,27-dioic acids

  摘要：

  A new method for the preparation of 5 beta-cholestan-26-oic acids 7 and their analogs is described. The key steps in the synthesis are: iodination of bis- and tris-formyloxy-5 beta-cholan-24-ols 3; nucleophilic substitution of iodides 4 with diethyl sodiomalonate; complete alkaline hydrolysis of esters 5; and subsequent decarboxylation of geminal diacids 6 in DMSO. (C) 2000 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(99)00099-9

文献信息

• Synthesis of 3α,7α-dihydroxy-5β-cholestan-26-oic acid from 3α,7α,12α-trihydroxy-5β-cholestan-26-oic acid: configuration in the bile of Alligator mississippiensis
  作者：Ashok K. Batta、Renu Mirchandani、Gerald Salen、Sarah Shefer

  DOI：10.1016/0039-128x(92)90002-q

  日期：1992.4

  product. Purification via column chromatography yielded the pure diastereoisomers in approximately 25% overall yield. The two diastereoisomers were resolved on thin-layer chromatography and high-performance liquid chromatography. When the bile of A mississippiensis was hydrolyzed with rat fecal bacteria, the 3 alpha,7 alpha-dihydroxy-5 beta-cholestan-26-oic acid isolated via chromatographic purification

  描述了由3α，7α，12α-三羟基-5β-胆甾醇-26-酸合成3α，7α-二羟基-5β-胆甾醇-26-酸的25R-和25S-非对映异构体。通过剧烈地水解密西西比短吻鳄的胆汁，然后反复结晶水解物，获得3α，7α，12α-三羟基-5β-胆甾烷-26-oo酸的25S-非对映异构体，且25R-非对映异构体为通过水解密西西比河胆汁中的胆汁盐与大鼠粪便分离。在控制条件下，甲基3α，7α，12α-三羟基-5β-胆甾烷-26-油酸的25R-或25S-非对映异构体的乙酰化产生相应的3α，7α-二乙酸酯。将二乙酸酯定量氧化为甲基3α，7α-二乙酰氧基-12-氧代-5β-胆甾烷-26-酸酯，其以约58％的产率转化为12-甲苯磺酰zone。用硼氢化钠在乙酸中还原甲苯磺酰zone，得到3α，7α-二羟基-5β-胆甾烷-26-油酸的25R-或25S-非对映异构体作为主要产物。通过柱色谱法纯化得到纯的非对映异构体，总产
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  申请人：Esperion Therapeutics, Inc.

  公开号：EP1495034A2

  公开（公告）日：2005-01-12
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  公开号：EP1497247A2

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  公开号：EP3773919A1

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  公开号：US20110246081A1

  公开（公告）日：2011-10-06

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