2,2',3,4,4',5,5'-heptabromodiphenyl ether | 446255-26-1

• 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: 2,2',3,4,4',5,5'-heptabromodiphenyl ether
• 英文别名: 2,2',3,4,4',5,5'-Heptabromodiphenyl ether；1,2,3,4-tetrabromo-5-(2,4,5-tribromophenoxy)benzene
• CAS: 446255-26-1
• 化学式: C₁₂H₃Br₇O
• 分子量: 722.483
• InChiKey: STMBXVOJNOJRPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,3,4,5-tetrabromophenol 、 4-methoxyphenyl-2',4',5'-tribromophenyliodonium bromide 在 sodium hydroxide 作用下， 反应 2.0h， 以40%的产率得到2,2',3,4,4',5,5'-heptabromodiphenyl ether
  参考文献：
  名称：

  Synthesis of Polybrominated Diphenyl Ethers and Their Capacity to Induce CYP1A by the Ah Receptor Mediated Pathway

  摘要：

  Polybrominated diphenyl ethers (PBDEs) have become widely distributed as environmental contaminants due to their use as flame retardants. Their structural similarity to other halogenated aromatic pollutants has led to speculation that they might share toxicological properties such as hepatic enzyme induction. In this work we synthesized a number of PBDE congeners, studied their affinity for rat hepatic Ah receptor through competitive binding assays, and determined their ability to induce hepatic cytochrome P-450 enzymes by means of EROD (ethoxyresorufin-O-deethylase) assays in human, rat, chick, and rainbow trout cells. Both pure PBDE congeners and commercial PBDE mixtures had Ah receptor binding affinities 10(-2)-10(-5) times that of 2,3,7,8-tetrachlorodibenzo-p-dioxin. In contrast with polychlorinated biphenyls, Ah receptor binding affinities of PBDEs could not be related to the planarity of the molecule, possibly because the large size of the bromine atoms expands the Ah receptor's binding site. EROD activities of the PBDE congeners followed a similar rank order in all cells. Some congeners, notably PBDE 85, did not follow the usual trend in which strength of Ah receptor binding affinity paralleled P-450 induction potency. Use of the gel retardation assay with a synthetic oligonucleotide indicated that in these cases the liganded Ah receptor failed to bind to the DNA recognition Sequence.

  DOI：

  10.1021/es0107475

文献信息

• Synthesis of Polybrominated Diphenyl Ethers and Their Capacity to Induce CYP1A by the Ah Receptor Mediated Pathway
  作者：Guosheng Chen、Alexandre D. Konstantinov、Brock G. Chittim、Elizabeth M. Joyce、Niels C. Bols、Nigel J. Bunce

  DOI：10.1021/es0107475

  日期：2001.9.1

  Polybrominated diphenyl ethers (PBDEs) have become widely distributed as environmental contaminants due to their use as flame retardants. Their structural similarity to other halogenated aromatic pollutants has led to speculation that they might share toxicological properties such as hepatic enzyme induction. In this work we synthesized a number of PBDE congeners, studied their affinity for rat hepatic Ah receptor through competitive binding assays, and determined their ability to induce hepatic cytochrome P-450 enzymes by means of EROD (ethoxyresorufin-O-deethylase) assays in human, rat, chick, and rainbow trout cells. Both pure PBDE congeners and commercial PBDE mixtures had Ah receptor binding affinities 10(-2)-10(-5) times that of 2,3,7,8-tetrachlorodibenzo-p-dioxin. In contrast with polychlorinated biphenyls, Ah receptor binding affinities of PBDEs could not be related to the planarity of the molecule, possibly because the large size of the bromine atoms expands the Ah receptor's binding site. EROD activities of the PBDE congeners followed a similar rank order in all cells. Some congeners, notably PBDE 85, did not follow the usual trend in which strength of Ah receptor binding affinity paralleled P-450 induction potency. Use of the gel retardation assay with a synthetic oligonucleotide indicated that in these cases the liganded Ah receptor failed to bind to the DNA recognition Sequence.