2,3,7,8-Tetrachlorodibenzo-p-dioxin
描述
2,3,7,8-Tetrachlorodibenzo-p-dioxin is the most toxic of 75 chlorinated dibenzo-p-dioxin (CDD) congeners. CDDs are a class of manufactured chemicals that consist of dioxin skeletel structures with chlorine substituents. They are also persistent organic pollutants (POPs), thus their production is regulated in most areas. Dioxins occur as by-products from the manufacture of organochlorides, the bleaching of paper, chlorination by waste and drinking water treatment plants, municipal solid waste and industrial incinerators, and natural sources such as volcanoes and forest fires. (L177, L178)
类别
"Industrial/Workplace Toxin", "Pollutant", "Airborne Pollutant", "Synthetic Toxin"
同义词
"2,3,6,7-Tetrachlorodibenzo-p-dioxin", "2,3,7,8-:tetrachlorodibenzo-p-dioxin", "2,3,7,8-Tetra polychlorinated dibenzo-p-dioxin", "2,3,7,8-Tetrachloro(b,e)dibenzodioxin", "2,3,7,8-Tetrachloro(b,f)dibenzodioxin", "2,3,7,8-Tetrachlorodibenzo(b,e)(1,4)dioxan", "2,3,7,8-Tetrachlorodibenzo(b,e)(1,4)dioxin", "2,3,7,8-Tetrachlorodibenzo-1,4-Dioxin", "2,3,7,8-Tetrachlorodibenzo-P-dioxin", "2,3,7,8-tetrachlorodibenzodioxin", "2,3,7,8-tetrachlorodibenzodioxine", "2,3,7,8-Tetrachlorodibenzo[b,e][1,4]dioxin", "2,3,7,8-Tetrachlorooxanthrene", "Dibenzo-dioxin, 2,3,7,8-tetrachlorinated", "Tetrachlorodibenzo-1,4-dioxin", "Tetrachlorodibenzo-p-dioxin", "Tetrachlorodibenzodioxin", "Tetradioxin"
IUPAC 名称
2,3,7,8-tetrachlorooxanthrene
简化分子线性输入规范
ClC1=CC2=C(OC3=C(O2)C=C(Cl)C(Cl)=C3)C=C1Cl
InChI 标识符
InChI=1S/C12H4Cl4O2/c13-5-1-9-10(2-6(5)14)18-12-4-8(16)7(15)3-11(12)17-9/h1-4H
键
InChIKey=HGUFODBRKLSHSI-UHFFFAOYSA-N
大分类
Organoheterocyclic compounds
直接大类
Chlorinated dibenzo-p-dioxins
另外分类
"Aryl chlorides", "Benzenoids", "Diarylethers", "Hydrocarbon derivatives", "Organochlorides", "Oxacyclic compounds"
取代基
"Aromatic heteropolycyclic compound", "Aryl chloride", "Aryl halide", "Benzenoid", "Chlorinated-dibenzo-p-dioxin", "Diaryl ether", "Ether", "Hydrocarbon derivative", "Organic oxygen compound", "Organochloride", "Organohalogen compound", "Organooxygen compound", "Oxacycle"
分子框架
Aromatic heteropolycyclic compounds
外部描述符
"PCDDs", "polychlorinated dibenzodioxine"
地位
Detected and Not Quantified
蜂窝位置
"Actin Filament", "Basolateral Membrane", "Cell junction", "Cell surface", "Centrosome", "Cytosol", "Extracellular", "Extracellular matrix", "Focal adhesion", "Lysosome", "Membrane", "Membrane Fraction", "Microsome", "Microtubule", "Mitochondrion", "Nuclear Matrix", "Nuclear Membrane", "Nucleolus", "Peroxisome", "Plasma Membrane", "Sarcoplasmic Reticulum", "Secretory Granule", "Tubulin"
途径
"Apoptosis", "Cell cycle", "Insulin secretion", "Arachidonic Acid Metabolism", "Wnt signaling pathway", "Fatty acid Metabolism", "Ovarian Steroidogenesis", "Insulin signaling pathway", "Proteasome", "Eicosanoids", "Rna polymerase", "Phenothiazines", "Oxidative phosphorylation", "Nitrogen Metabolism", "Long-term potentiation", "Inositol Phosphate Metabolism", "Endocytosis", "Circadian rhythm", "Axon guidance"
熔点/沸点/溶解度
305°C//2e-07 mg/mL at 25 °C [SHIU,WY et al. (1988)]
暴露途径
Oral (L177) ; inhalation (L177) ; dermal (L177)
毒性机制
CDDs bind to the aryl hydrocarbon (Ah) receptor and subsequently alter the transcription of several genes (oncogenes, growth factors, receptors, hormones, and drug-metabolizing enzymes). 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 change in transcription/translation of these genes is believed to be the cause of most of the toxic effects of CDDs. 2,3,7,8-tetrachlorodibenzo-p-dioxin's carcinogenicity is thought to be the result of its ability to alter the capacity of both exogenous and endogenous substances to damage the DNA by inducing CYP1A1- and CYP1A2-dependent drug-metabolizing enzymes. (L177)
代谢
CDDs are absorbed through oral, inhalation, and dermal routes of exposure. CDDs are carried in the plasma by serum lipids and lipoproteins, and mainly distributed in the liver and adipose tissue. CDDs are slowly metabolized to polar metabolites by the microsomal monooxygenase system. These metabolites 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)
毒性值
LD50: 201 ug/kg (Oral, Rat) (T26)
LD50: 120 ug/kg (Intraperitoneal, Mouse) (T14)
致癌性
1, carcinogenic to humans. (L135)
用途/来源
Dioxins occur as by-products from the manufacture of organochlorides, the bleaching of paper, chlorination by waste and drinking water treatment plants, municipal solid waste and industrial incinerators, and natural sources such as volcanoes and forest fires. (L177, L178)
最低风险等级
Acute Oral: 0.0002 ug/kg/day (L134)
Intermediate Oral: 0.00002 ug/kg/day (L134)
Chronic Oral: 0.000001 ug/kg/day (L134)
健康影响
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 pathologies, thyroid disorders, endometriosis, and diabetes. 2,3,7,8-Tetrachlorodibenzo-p-dioxin is also a known as a human carcinogen. (L177, L178)
症状
In addition to chloracne, CDD exposure causes skin rashes, discoloration, and excessive body hair. (L177)
治疗
Treatment of CDD exposure may include washing the area of contact, different methods of gastrointestinal decontamination, administration of intravenous fluids, or forced alkaline diuresis. (L346)
创建于
2009-03-06 18:58:02 UTC
更新于
2014-12-24 20:21:02 UTC