(R)-4-((5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-Dihydroxy-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-pentanoic acid | 139437-34-6

• 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: (R)-4-((5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-Dihydroxy-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-pentanoic acid
• 英文别名: 7alpha,12alpha-Dihydroxy-5beta-chol-2-en-24-oic Acid；(4R)-4-[(5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 139437-34-6
• 化学式: C₂₄H₃₈O₄
• 分子量: 390.563
• InChiKey: KHTQKVWLBDPPPW-QLEQUTGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-mesylcholic acid 在 吡啶 、 乙二醇 作用下， 反应 2.0h， 生成 7α,12α-dihydroxy-5β-cholen-(3)-oic acid-(24) 、 (R)-4-((5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-Dihydroxy-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-pentanoic acid 、 (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-12-hydroxy-10,13-dimethylhexadecahydro-1H-3,7-epoxycyclopenta[a]phenanthren-17-yl)pentanoic acid
  参考文献：
  名称：

  Modified bile acids: preparation of 7α,12α-dihydroxy-3β- and 7α,12α-dihydroxy-3α-(2-hydroxyethoxy)-5β-cholanic acid and their biological activity

  摘要：

  Methodology for the preparation of 7-alpha,12-alpha-dihydroxy-3-beta- (2) and 7-alpha,12-alpha-dihydroxy-3-alpha-(2-hydroxyethoxy)-5-beta-cholanic acid (3) is described. Nucleophilic displacement of the 3-mesylate of unprotected cholic acid with ethylene glycol led to the 3-beta-isomer whereas the 3-alpha-isomer was synthesized via the 7,12-diacetyl protected 3-allyl ether of methyl cholate. Only the 3-alpha-isomer 3 is recognized by the ileal bile acid transport system with affinity comparable to cholic acid.

  DOI：

  10.1016/0040-4039(92)88048-a

文献信息

• Modified bile acids: preparation of 7α,12α-dihydroxy-3β- and 7α,12α-dihydroxy-3α-(2-hydroxyethoxy)-5β-cholanic acid and their biological activity
  作者：G. Wess、W. Kramer、W. Bartmann、A. Enhsen、H. Glombik、S. Müllner、K. Bock、A. Dries、H. Kleine、W. Schmitt

  DOI：10.1016/0040-4039(92)88048-a

  日期：1992.1

  Methodology for the preparation of 7-alpha,12-alpha-dihydroxy-3-beta- (2) and 7-alpha,12-alpha-dihydroxy-3-alpha-(2-hydroxyethoxy)-5-beta-cholanic acid (3) is described. Nucleophilic displacement of the 3-mesylate of unprotected cholic acid with ethylene glycol led to the 3-beta-isomer whereas the 3-alpha-isomer was synthesized via the 7,12-diacetyl protected 3-allyl ether of methyl cholate. Only the 3-alpha-isomer 3 is recognized by the ileal bile acid transport system with affinity comparable to cholic acid.