[4-2H]-cholesterol | 1973-68-8

• 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: [4-2H]-cholesterol
• 英文别名: 4-Deuterocholesterol；(3S,8S,9S,10R,13R,14S,17R)-4-deuterio-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 1973-68-8
• 化学式: C₂₇H₄₆O
• 分子量: 387.654
• InChiKey: HVYWMOMLDIMFJA-MVVYYWQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [4-2H]-cholesterol 在 pyridinium chlorochromate 、 calcium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以93%的产率得到[4-2H]-5-cholesten-3-one
  参考文献：
  名称：

  Mechanism of cholesterol reduction to coprostanol by Eubacterium coprostanoligenes ATCC 51222

  摘要：

  The mechanism of reduction of cholesterol to coprostanol by Eubacterium coprostanoligenes ATCC 51222 was studied by incubating the bacterium with a mixture of alpha- and beta-isomers of [4-H-3,4-C-14]cholesterol. Coprostanol, isolated after incubation of [4-H-3,4-C-14]cholesterol in a growth medium under anaerobic conditions, retained 97% of the tritium originally present in cholesterol. The majority of this tritium (64%), however was in the C-6 position in coprostanol, which showed that the conversion of cholesterol into coprostanol by E. coprostanoligenes involved the intermediate formation of 4-cholesten-3-one followed by the reduction of the latter to coprostanol. In resting cell assays in which washed bacterial cells were incubated with micellar cholesterol in phosphate buffer at 37 degrees C, both 4-cholesten-3-one and coprostanone were produced in addition to coprostanol. Furthermore, 5-cholesten-3-one, 4-cholesten-3-one, and coprostanone were converted efficiently to coprostanol by E. coprostanoligenes. These results support the hypothesis that the major pathway for reduction of cholesterol by E. coprostanoligenes involves the intermediate formation of 4-cholesten-3-one followed by reduction of the latter to coprostanol through coprostanone as an intermediate.

  DOI：

  10.1016/0039-128x(95)00173-n
• 作为产物：
  描述：

  [4-2H]-5-cholesten-3-one 在 sodium tetrahydroborate 作用下， 生成 [4-2H]-epicholesterol 、 [4-2H]-cholesterol
  参考文献：
  名称：

  Mechanism of cholesterol reduction to coprostanol by Eubacterium coprostanoligenes ATCC 51222

  摘要：

  The mechanism of reduction of cholesterol to coprostanol by Eubacterium coprostanoligenes ATCC 51222 was studied by incubating the bacterium with a mixture of alpha- and beta-isomers of [4-H-3,4-C-14]cholesterol. Coprostanol, isolated after incubation of [4-H-3,4-C-14]cholesterol in a growth medium under anaerobic conditions, retained 97% of the tritium originally present in cholesterol. The majority of this tritium (64%), however was in the C-6 position in coprostanol, which showed that the conversion of cholesterol into coprostanol by E. coprostanoligenes involved the intermediate formation of 4-cholesten-3-one followed by the reduction of the latter to coprostanol. In resting cell assays in which washed bacterial cells were incubated with micellar cholesterol in phosphate buffer at 37 degrees C, both 4-cholesten-3-one and coprostanone were produced in addition to coprostanol. Furthermore, 5-cholesten-3-one, 4-cholesten-3-one, and coprostanone were converted efficiently to coprostanol by E. coprostanoligenes. These results support the hypothesis that the major pathway for reduction of cholesterol by E. coprostanoligenes involves the intermediate formation of 4-cholesten-3-one followed by reduction of the latter to coprostanol through coprostanone as an intermediate.

  DOI：

  10.1016/0039-128x(95)00173-n