7α,12α,25-trihydroxy-5β-cholestan-3-one | 73407-66-6

• 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: 7α,12α,25-trihydroxy-5β-cholestan-3-one
• 英文别名: 7alpha,12alpha,25-Trihydroxy-5beta-cholestan-3-one；(5R,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-17-[(2R)-6-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• CAS: 73407-66-6
• 化学式: C₂₇H₄₆O₄
• 分子量: 434.66
• InChiKey: ZOZJTXMHMMUIAZ-NMJMBVPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  31
• 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：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7α,12α,25-trihydroxy-5β-cholestan-3-one 在 吡啶 、 甲醇 、 sodium hydroxide 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.5h， 生成 {2-[(5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-Dihydroxy-17-((R)-5-hydroxy-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-(3Z)-ylideneaminooxy]-acetylamino}-(4-hydroxy-phenyl)-acetic acid
  参考文献：
  名称：

  Radioimmunoassay of 5β-cholestane-3α,7α,12α,25-tetrol 3-glucuronide in serum of patients with cerebrotendinous xanthomatosis

  摘要：

  A rapid, convenient, and specific radioimmunoassay for 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol has been developed. Specific antiserum was obtained from rabbits immunized by the bile alcohol-bovine serum albumin conjugate, which was coupled by an (O-carboxymethyl)oxime bridge at the C-3 position. The assay produces values for serum concentrations of bile alcohol glucuronides in patients with cerebrotendinous xanthomatosis.

  DOI：

  10.1016/0039-128x(92)90093-o
• 作为产物：
  描述：

  3α,7α,12α-trihydroxy-5β-cholane-24-carboxylic acid methyl ester 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

文献信息

• Radioimmunoassay of 5β-cholestane-3α,7α,12α,25-tetrol 3-glucuronide in serum of patients with cerebrotendinous xanthomatosis
  作者：Une Mizuho、Kataoka Jun、Nakata Yoshihiro、Hoshita Takahiko

  DOI：10.1016/0039-128x(92)90093-o

  日期：1992.1

  A rapid, convenient, and specific radioimmunoassay for 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol has been developed. Specific antiserum was obtained from rabbits immunized by the bile alcohol-bovine serum albumin conjugate, which was coupled by an (O-carboxymethyl)oxime bridge at the C-3 position. The assay produces values for serum concentrations of bile alcohol glucuronides in patients with cerebrotendinous xanthomatosis.
• Bile acids. LXXIII. Synthesis of analogs of 7α-hydroxy-4-cholesten-3-one as substrates for hepatic steroid 12α-hydroxylase
  作者：M JOYCE、S HIREMATH、M MATTAMMAL、W ELLIOTT

  DOI：10.1016/s0039-128x(84)80020-3

  日期：1984.7

  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.