1,4,6,9-四氯二苯并(b,e)(1,4)二恶英 | 40581-93-9

• 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: 1,4,6,9-四氯二苯并(b,e)(1,4)二恶英
• 英文名称: 1,4,6,9-tetrachloro-dibenzo[1,4]dioxine
• 英文别名: 1,4,6,9-tetrachlorodibenzo-p-dioxin；1,4,6,9-tetrachlorodibenzodioxin；1,4,6,9-tetrachlordibenzodioxin；1,4,6,9-tetrachlorodioxine
• CAS: 40581-93-9
• 化学式: C₁₂H₄Cl₄O₂
• 分子量: 321.975
• InChiKey: QTIIAIRUSSSOHT-UHFFFAOYSA-N

物化性质

• 保留指数：
  2341;2341;2341;2308;2309;2341

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  18
• 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携带，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。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。(L177)

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是由于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件的直接相互作用，或者启动磷酸化/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, 无法归类其对人类致癌性的类别。(L135)

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

接触大量氯丹类化合物（CDDs）会导致氯痤疮，这是一种严重的皮肤疾病，其特点是在面部和上半身出现类似粉刺的损伤。CDDs还可能引起肝脏损伤，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，研究还表明CDDs可能会干扰内分泌系统，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的病理变化、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

除了氯痤疮外，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)

反应信息

• 作为产物：
  描述：

  乙炔 在 氧气 、 copper dichloride 作用下， 生成 1,4,6,9-四氯二苯并(b,e)(1,4)二恶英 、 1,2,6,9-四氯二苯并(b,e)(1,4)二恶英 、 1,2,7,8-四氯二苯并-对-二恶英 、 1,2,3,9-四氯二苯并[1,4]二恶英
  参考文献：
  名称：

  铜催化的乙炔和二氯乙炔的氯化和缩合。

  摘要：

  使用氯化铜作为模拟硼硅酸盐表面的氯化剂，证明了乙炔在低温下的氯化和缩合。在有和没有氯源和硼硅酸盐表面的情况下进行的实验表明，没有气相和气相表面反应。氯化和缩合仅在铜催化剂存在下发生。在废水中观察到C2至C8有机产物。仅从提取硼硅酸盐表面观察到PCDD / F。提出了与观察到的产物分布一致的全局反应模型。用二氯乙炔进行的类似实验表明，在不存在铜催化剂的情况下，反应性更高。在低温下在气相中和在存在硼硅酸盐表面的情况下观察到反应。仅在铜催化剂存在下观察到六氯苯的形成。仅从提取硼硅酸盐表面观察到PCDD / F。提出了一种由二氯乙炔形成六氯苯的整体反应模型。

  DOI：

  10.1016/s0045-6535(99)00272-6

文献信息

• Congeneric, Chlorinated, Brominated And/Or Iodised, Fluorinated Aromatic Compounds Comprising Two Benzol Rings In Their Basic Structure, Method For Their Production And Use Thereof
  申请人：Liu Huiling

  公开号：US20070298501A1

  公开（公告）日：2007-12-27

  Congeneric, halogenated, fluorinated aromatic compounds where A and B are each phenyl radicals, L=oxygen atom, sulfur atom or alkylene radical and p=0 or 1; processes for their preparation and their use.

  同系的，卤代，氟代的芳香化合物，其中A和B分别是苯基，L=氧原子，硫原子或烷基，p=0或1;它们的制备过程和用途。
• CONGENERIC, CHLORINATED, BROMINATED AND/OR IODISED, FLUORINATED AROMATIC COMPOUNDS COMPRISING TWO BENZOL RINGS IN THEIR BASIC STRUCTURE, METHOD FOR THEIR PRODUCTION AND USE THEREOF
  申请人：LIU Huiling

  公开号：US20110229973A1

  公开（公告）日：2011-09-22

  Congeneric, halogenated, fluorinated aromatic compounds where A and B are each phenyl radicals, L=oxygen atom, sulfur atom or alkylene radical and p=0 or 1; processes for their preparation and their use.

  同系、卤代、氟代芳香化合物，其中A和B分别是苯基，L=氧原子、硫原子或烷基，p=0或1；它们的制备方法及其用途。
• Isomer Distributions of Polychlorinated Dibenzo-<i>p</i>-dioxins/Dibenzofurans Formed during De Novo Synthesis on Incinerator Fly Ash
  作者：Ruud Addink、Harrie A. J. Govers、Kees Olie

  DOI：10.1021/es971077z

  日期：1998.7.1

  Polychlorinated dibenzo-p-dioxins (PCDD) and dibenzofurans (PCDF) emitted from municipal waste incinerators appear to have a chlorination pattern that is quite constant across various samples and conditions. This suggested that these patterns may he controlled by thermodynamic properties of the individual PCDD/F congeners, such as the free Gibbs energy of formation (Delta G degrees(f,T)) This would make prediction of the isomer composition of a particular sample (and hence its TEQ value) possible, based on values of Delta G degrees(f.T). A laboratory scale study was carried out with activated carbon on fly ash as the source of PCDD/F formation. Although it was found that the isomer distributions within homologues were independent of the reaction time (proof of thermodynamic control), other observations (lack of equilibrium/isomerization between isomers and lack of similarity between isomer distributions measured and predicted by Delta G degrees(f,T)) contradicted the possibility of thermodynamic control. Hence, this study could not confirm that de novo formation of PCDD/F could explain thermodynamically controlled isomer distributions in incinerators. Some recommendations for further work-time-based studies with precursors, isomerization studies with single congeners, and more data on Delta G degrees(f,T) values of PCDD/F-were made.
• Isomer-specific separation of 2,3,7,8-substituted polychlorinated dibenzo-p-dioxins by high-resolution gas chromatography/mass spectrometry
  作者：Hans Rudolf. Buser、Christoffer. Rappe

  DOI：10.1021/ac00267a034

  日期：1984.3.1
• High-resolution gas chromatography of the 22 tetrachlorodibenzo-p-dioxin isomers
  作者：Hans Rudolf. Buser、Christoffer. Rappe

  DOI：10.1021/ac50064a006

  日期：1980.12.1