5β-cholane-3α,6α,24-triol | 7750-84-7

• 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: 5β-cholane-3α,6α,24-triol
• 英文别名: 5β-Cholan-3α,6α,24-triol；5beta-Cholane-3alpha,6alpha,24-triol；(3R,5R,6S,8S,9S,10R,13R,14S,17R)-17-[(2R)-5-hydroxypentan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,6-diol
• CAS: 7750-84-7
• 化学式: C₂₄H₄₂O₃
• 分子量: 378.596
• InChiKey: QURUUUBBQMXRPI-KUEYJUPNSA-N

物化性质

• 沸点：
  509.5±25.0 °C(Predicted)
• 密度：
  1.079±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5β-cholane-3α,6α,24-triol 在 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 生成 24-iodo-5β-cholane-3α,6α-diol
  参考文献：
  名称：

  Synthesis of sulfonate analogs of bile acids

  摘要：

  Sulfonate analogs of C23 and C24 bile acids were synthesized from norcholic, norchenodeoxycholic, norursodeoxycholic, nordeoxycholic, norhyodeoxycholic, cholic, deoxycholic, hyodeoxycholic, and lithocholic acids. The principal reactions used were (1) reduction of the bile acids with NaBH4 to the corresponding bile alcohols, (2) selective tosylation of the terminal hydroxyl group, (3) iodination of the tosyl esters with NaI, and (4) treatment of the iodides with Na2SO3 to form the sulfonate analogs of the bile acids. The sulfonate analogs showed polarity similar to that of taurine-conjugated bile acids on thin-layer chromatography. The carbon 13 nuclear magnetic resonance spectral data for the sulfonate analogs were tabulated.

  DOI：

  10.1016/0039-128x(92)90008-w
• 作为产物：
  描述：

  猪去氧胆酸 在 sodium tetrahydroborate 、 氯甲酸乙酯 、 三乙胺 作用下， 生成 5β-cholane-3α,6α,24-triol
  参考文献：
  名称：

  Synthesis of sulfonate analogs of bile acids

  摘要：

  Sulfonate analogs of C23 and C24 bile acids were synthesized from norcholic, norchenodeoxycholic, norursodeoxycholic, nordeoxycholic, norhyodeoxycholic, cholic, deoxycholic, hyodeoxycholic, and lithocholic acids. The principal reactions used were (1) reduction of the bile acids with NaBH4 to the corresponding bile alcohols, (2) selective tosylation of the terminal hydroxyl group, (3) iodination of the tosyl esters with NaI, and (4) treatment of the iodides with Na2SO3 to form the sulfonate analogs of the bile acids. The sulfonate analogs showed polarity similar to that of taurine-conjugated bile acids on thin-layer chromatography. The carbon 13 nuclear magnetic resonance spectral data for the sulfonate analogs were tabulated.

  DOI：

  10.1016/0039-128x(92)90008-w

文献信息

• Matumoto, Journal of Biochemistry, 1955, vol. 42, p. 207,213
  作者：Matumoto

  DOI：——

  日期：——
• Haslewood, Biochemical Journal, 1956, vol. 62, p. 637,641
  作者：Haslewood

  DOI：——

  日期：——
• A hyodeoxycholic acid-based molecular tweezer: a highly selective fluoride anion receptor
  作者：Ki Soo Kim、Hong-Seok Kim

  DOI：10.1016/j.tet.2005.09.082

  日期：2005.12

  A new molecular tweezer receptor Hc1 based on hyodeoxycholic acid has been synthesized and its binding properties were accessed by H-1 NMR and isothermal titration calorimetry experiments. Molecular tweezer Hc1 shows a high selectivity toward F- over Cl Br-, I-, and H2PO4-. (c) 2005 Elsevier Ltd. All rights reserved.