1,3,7-三氯二苯并[b,e][1,4]二恶英 | 67028-17-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶英
• 中文名称: 1,3,7-三氯二苯并[b,e][1,4]二恶英
• 英文名称: 1,3,7-Trichlorodibenzo-p-dioxin
• CAS: 67028-17-5
• 化学式: C₁₂H₅Cl₃O₂
• 分子量: 287.5
• InChiKey: RPKWIXFZKMDPMH-UHFFFAOYSA-N

物化性质

• 保留指数：
  2133;2165;2166

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

ADMET

代谢

CDDs通过口服、吸入和皮肤暴露途径被吸收。CDDs通过血清脂质和脂蛋白在血浆中运输，主要分布到肝脏和脂肪组织。CDDs通过微粒体单加氧酶系统非常缓慢地被代谢为极性代谢物，这些代谢物可以与葡萄糖醛酸和谷胱甘肽发生结合反应。它们可能通过诱导I相和II相酶来增加自己的代谢速率。CDDs的主要排泄途径是胆汁和粪便，尽管也有少量通过尿液和哺乳排出。

CDDs are absorbed through oral, inhalation, and dermal routes of exposure. CDDs are carried in the plasma by serum lipids and lipoproteins, distributing mainly to the liver and adipose tissue. CDDs are very slowly metabolized by the microsomal monooxygenase system to polar metabolites that can undergo conjugation with glucuronic acid and glutathione. They may increase the rate of their own metabolism by inducing both phase I and phase II enzymes. The major routes of excretion of CDDs are the bile and the faeces, though smaller amounts are excreted in the urine and via lactation. (L177)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

CDDs通过结合芳基烃受体并随后改变某些基因的转录来产生其毒性作用。对Ah受体的亲和力取决于特定CDD的结构。基因表达的改变可能源于Ah受体及其异二聚体形成伙伴芳基烃受体核移位子与基因调控元素的直接相互作用，或者是由启动磷酸化/去磷酸化级联反应，随后激活其他转录因子。受影响的基因包括几个癌基因、生长因子、受体、激素和药物代谢酶。这些基因的转录/翻译改变被认为是CDD大多数毒性作用的原因。

CDDs cause their toxic effects by binding to the aryl hydrocarbon receptor and subsequently altering the trascription of certain genes. The affinity for the Ah receptor depends on the structure of the specific CDD. The change in gene expression may result from the direct interaction of the Ah receptor and its heterodimer-forming partner, the aryl hydrocarbon receptor nuclear translocator, with gene regulatory elements or the initiation of a phosphorylation/dephosphorylation cascade that subsequently activates other transcription factors. The affected genes include several oncogenes, growth factors, receptors, hormones, and drug-metabolizing enzymes. The change in transcription/translation of these genes is believed to be the cause of most of the toxic effects of CDDs. (L177)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

3, 其对人类致癌性无法分类。

3, not classifiable as to its carcinogenicity to humans. (L135)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

暴露于大量氯代二苯并二噁烷（CDDs）会引起氯痤疮，这是一种严重的皮肤疾病，其症状类似于粉刺，主要发生在面部和上半身。CDDs还可能引起肝损伤，并导致长期的葡萄糖代谢改变和激素水平的微妙变化。此外，研究表明CDDs可能会破坏内分泌系统，削弱免疫系统，以及造成生殖损害和出生缺陷、中枢和周围神经系统病理变化、甲状腺疾病、子宫内膜异位症和糖尿病。(L177, L178)

Exposure to large amounts of CDDs causes chloracne, a severe skin disease with acne-like lesions that occur mainly on the face and upper body. CDDs may also cause liver damage and induce long-term alterations in glucose metabolism and subtle changes in hormonal levels. In addition, studies have shown that CDDs may disrupt the endocrine system and weaken the immune system, as well as cause reproductive damage and birth defects, central and peripheral nervous system pathology, thyroid disorders, endometriosis, and diabetes. (L177, L178)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口服（L177）；吸入（L177）；皮肤（L177）

Oral (L177) ; inhalation(L177) ; dermal (L177)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

除了氯痤疮，二噁烷暴露还会导致皮肤皮疹、色素沉着和体毛过度生长。

In addition to chloracne, CDD exposure causes skin rashes, discoloration, and excessive body hair. (L177)

来源:Toxin and Toxin Target Database (T3DB)

文献信息

• Method for reducing formation of polychlorinated aromatic compounds during air oxychlorination of c1-c3 hydrocarbons
  申请人：The Geon Company

  公开号：EP0781746A1

  公开（公告）日：1997-07-02

  An improved process is disclosed for manufacturing chlorinated hydrocarbon by way of a once-through air-based oxychlorination process which yields reduced levels of environmental toxins such as chlorobenzenes, polychlorinated biphenyls, polychlorinated dibenzodioxins and polychlorinated dibenzofurans. The process involves fixed bed or fluid bed catalyzed oxychlorination of a hydrocarbon reactant containing from 1 to 3 carbon atoms. The oxychlorination process consists of contacting the hydrocarbon reactant with air or oxygen enriched air and hydrogen chloride in the presence of the oxychlorination catalyst in a heated reaction zone operated at from 150°C to 600°C and recovering chlorinated hydrocarbon from the effluents of the reaction zone. The improvement consists of the use of air which is pretreated before use in the operated oxychlorination process by a means for removal of the aromatic hydrocarbons.

  本发明公开了一种改进的工艺，通过一次通过式空气氧氯化工艺生产氯化碳氢化合物，该工艺可减少氯苯、多氯联苯、多氯二苯并二噁英和多氯二苯并呋喃等环境毒素的含量。该工艺涉及固定床或流化床催化含 1 至 3 个碳原子的碳氢化合物反应物的氧氯化。 氧氯化工艺包括在 150°C 至 600°C 的加热反应区中，在氧氯化催化剂存在下，使碳氢化合物反应物与空气或富氧空 气和氯化氢接触，并从反应区的流出物中回收氯化碳氢化合物。改进之处在于使用空气，这种空气在用于运行中的氧氯化工艺之前，已通过去除芳香烃的方法进行了预处理。
• Method for reducing formation of polychlorinated aromatic compounds during oxychlorination of C1-C3 hydrocarbons
  申请人：The Geon Company

  公开号：EP0774450B1

  公开（公告）日：2000-02-09
• US5750812A
  申请人：——

  公开号：US5750812A

  公开（公告）日：1998-05-12
• US6177599B1
  申请人：——

  公开号：US6177599B1

  公开（公告）日：2001-01-23