6-Hydroxy-3,3',3,4'-tetrachlorobiphenyl

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-Hydroxy-3,3',3,4'-tetrachlorobiphenyl
• 英文别名: 2-Hydroxy-4,5,3',4'-tetrachloro biphenyl；4,5-dichloro-2-(3,4-dichlorophenyl)phenol
• 化学式: C₁₂H₆Cl₄O
• 分子量: 307.991
• InChiKey: GPHKIEYWDKDZEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3,3,4,4-四氯联苯 在 rat β-NF hepatic microsomes 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 水 为溶剂， 反应 0.08h， 生成 2,6-二氯-4-(3,4-二氯苯基)苯酚 、 6-Hydroxy-3,3',3,4'-tetrachlorobiphenyl 、 5-Hydroxy-3,3',3,4'-tetrachlorobiphenyl
  参考文献：
  名称：

  β-Naphthoflavone- and self-induced metabolism of 3,3′,4,4′-tetrachlorobiphenyl in hepatic microsomes of the male, pregnant female and foetal rat

  摘要：

  1. The in vitro metabolism of 3,3',4,4'-tetrachloro-[C-14]-biphenyl ([C-14]-TCB) by hepatic microsomes from the Wistar rat was investigated with liver microsomes from the male, pregnant female and foetus.2. Three hydroxylated metabolites (4-OH-3,3',4,5'-tetrachlorobiphenyl, 5-OH-3,3',4,4'-tetrachlorobiphenyl, and 6-OH-3,3',4,4'-tetrachlorobiphenyl) were identified by hplc and gc-ms after incubations of liver microsomes from the beta-naphthoflavone-pretreated male rat and TCB-treated pregnant rat. No metabolites of [C-14]-TCB were found after incubation with foetal liver microsomes from dams pretreated with [C-14]-TCB. The results indicate that the in vivo accumulation of 4-OH-tetraCB in the foetal compartment is probably due to transplacental transport rather than the formation of this metabolite in the foetus.3. Pretreatment of the male rat with beta-naphthoflavone substantially induced the formation of hydroxylated metabolites, but pretreatment with phenobarbital and dexamethasone was without effect. Based on in vitro incubations of liver microsomes from the beta-naphthoflavone pretreated male rat, an apparent K-m and V-max of 4.5 mu M and 240 pmol/mg protein/min respectively was determined for the metabolism of [C-14]-TCB. The formation of phenolic metabolites of [C-14]-TCB was most likely dependent on P4501A induction.

  DOI：

  10.3109/00498259509061849

文献信息

• β-Naphthoflavone- and self-induced metabolism of 3,3′,4,4′-tetrachlorobiphenyl in hepatic microsomes of the male, pregnant female and foetal rat
  作者：D. C. Morse、P. J. Van Bladeren、E. Klasson Wehler、A. Brouwer

  DOI：10.3109/00498259509061849

  日期：1995.1

  1. The in vitro metabolism of 3,3',4,4'-tetrachloro-[C-14]-biphenyl ([C-14]-TCB) by hepatic microsomes from the Wistar rat was investigated with liver microsomes from the male, pregnant female and foetus.2. Three hydroxylated metabolites (4-OH-3,3',4,5'-tetrachlorobiphenyl, 5-OH-3,3',4,4'-tetrachlorobiphenyl, and 6-OH-3,3',4,4'-tetrachlorobiphenyl) were identified by hplc and gc-ms after incubations of liver microsomes from the beta-naphthoflavone-pretreated male rat and TCB-treated pregnant rat. No metabolites of [C-14]-TCB were found after incubation with foetal liver microsomes from dams pretreated with [C-14]-TCB. The results indicate that the in vivo accumulation of 4-OH-tetraCB in the foetal compartment is probably due to transplacental transport rather than the formation of this metabolite in the foetus.3. Pretreatment of the male rat with beta-naphthoflavone substantially induced the formation of hydroxylated metabolites, but pretreatment with phenobarbital and dexamethasone was without effect. Based on in vitro incubations of liver microsomes from the beta-naphthoflavone pretreated male rat, an apparent K-m and V-max of 4.5 mu M and 240 pmol/mg protein/min respectively was determined for the metabolism of [C-14]-TCB. The formation of phenolic metabolites of [C-14]-TCB was most likely dependent on P4501A induction.