2,3,7,8-Tetrachlorodibenzofuran
描述
Chlorinated dibenzofurans (CDFs) are a family of chemical that contain one to eight chlorine atoms attached to the carbon atoms of the parent chemical, dibenzofuran. The CDF family contains 135 individual compounds with varying damaging health and environmental effects; those 2,3,7,8-substitued being particularly harmful. Most CDFs are produced in very small amounts as unwanted impurities after use of chlorinated compounds. Only a few of these 135 compounds have been produced and their properties (color, smell, taste, and toxicity) studied. (L952)
类别
"Pesticide", "Industrial/Workplace Toxin", "Pollutant", "Synthetic Toxin"
同义词
"2,3,7,8-TCDF", "2,3,7,8-Tetrachloro-dibenzofuran", "2,3,7,8-Tetrachlorodibenzo[b,d]furan", "2,3,7,8-Tetrapolychlorinated dibenzofuran", "PCDF 83"
IUPAC 名称
4,5,11,12-tetrachloro-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),2,4,6,9,11-hexaene
传统名称
4,5,11,12-tetrachloro-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),2,4,6,9,11-hexaene
简化分子线性输入规范
ClC1=C(Cl)C=C2C(OC3=CC(Cl)=C(Cl)C=C23)=C1
InChI 标识符
InChI=1S/C12H4Cl4O/c13-7-1-5-6-2-8(14)10(16)4-12(6)17-11(5)3-9(7)15/h1-4H
键
InChIKey=KSMVNVHUTQZITP-UHFFFAOYSA-N
大分类
Organoheterocyclic compounds
直接大类
Polychlorinated dibenzofurans
另外分类
"Aryl chlorides", "Benzenoids", "Furans", "Heteroaromatic compounds", "Hydrocarbon derivatives", "Organochlorides", "Organooxygen compounds", "Oxacyclic compounds"
取代基
"Aromatic heteropolycyclic compound", "Aryl chloride", "Aryl halide", "Benzenoid", "Furan", "Heteroaromatic compound", "Hydrocarbon derivative", "Organic oxygen compound", "Organochloride", "Organohalogen compound", "Organooxygen compound", "Oxacycle", "Polychlorinated dibenzofuran"
分子框架
Aromatic heteropolycyclic compounds
外部描述符
"PCDFs", "chlorins"
地位
Detected and Not Quantified
熔点/沸点/溶解度
227°C//6.92e-07 mg/mL at 26 °C [FRIESEN,KJ & WEBSTER,GRB (1990)]
暴露途径
Inhalation (L952) ; dermal (L952) ; oral (L952)
毒性机制
Halogenated dibenzofurans (PCDFs and PBDFs) bind the aryl hydrocarbon receptor (AhR), which increases its ability to activate transcription in the XRE (xenobiotic resoponse element) promoter region. Specifically AhR binds to the PCDF, translocates it to the nucleus and together with hydrocarbon nuclear translocator (ARNT) and xenobiotic responsive element (XRE) increases the expression of CYP1A1 and aryl hydrocarbon hydroxylase (CYP1B1). AhR signaling also increseases conversion of arachidonic acid to prostanoids via cyclooxygenase-2, alters Wnt/beta-catenin signaling downregulating Sox9 and alters signaling by receptors for inflammatory cytokines. AhR signalling also alters proteasomal degradation of steroid hormone receptors, alters cellular UVB stress response and changes the differentiation of certain T-cell subsets. The resulting AhR mediated activation and alteration leads to body weight loss, cancer and thymic atrophy (characteristic of immune and endocrine disruption) which are common toxic responses to PCDFs and related toxic halogenated aryl hydrocarbons.
代谢
No information on the metabolism of dibenzofuran in mammalian organisms was found in the available literature. The bacteria Sphingomonas, Brevibacterium, Terrabacter, and Staphylococcus auricularis degrade dibenzofuran to 2,2',3-trihydroxybiphenyl via dibenzofuran 4,4a-dioxygenase. (L952)
致癌性
3, not classifiable as to its carcinogenicity to humans. (L135)
用途/来源
CDFs are created from production of coal tar and during incineration. They are used as insecticides, in the production of PVC, and in industrial bleaching. (L952)
健康影响
CDFs cause vomiting and diarrhea, anemia, more frequent lung infections, numbness and other effects on the nervous system, and mild changes in the liver. However, there were no permanent liver changes or definite liver damage found in people who ingested CDFs. (L952)
症状
Skin and eye irritations, especially severe acne, darkened skin color, and swollen eyelids with discharge are the most obvious health effects of the CDF poisoning. (L952)
创建于
2009-03-06 18:58:17 UTC
更新于
2014-12-24 20:21:19 UTC