Dibenzo[a,h]anthracene
描述
Dibenzo(a,h)anthracene is one of over 100 different polycyclic aromatic hydrocarbons (PAHs). PAHs are chemicals that are formed during the incomplete burning organic substances, such as fossil fuels. They are usually found as a mixture containing two or more of these compounds. It is one ingredient of cigarette. (L10)
类别
"Cigarette Toxin", "Industrial/Workplace Toxin", "Pollutant", "Food Toxin", "Natural Toxin"
同义词
"1,2,5,6-Dibenzanthracene", "1,2:5, 6-Dibenzanthracene", "1,2:5,6-Benzanthracene", "1,2:5,6-Dibenz(a)anthracene", "1,2:5,6-Dibenzanthracene", "1,2:5,6-Dibenzoanthracene", "Benzo[k]tetraphene", "Benz[a,h]anthracene", "DBA", "Dibenz(a,h)anthracene", "Dibenz(a,h)antracene", "Dibenzathracene", "Dibenza[a,h]-anthracene", "Dibenzo(a,h)anthracene", "Dibenzo[a,H]anthracene", "Dibenz[a,H]anthracene"
IUPAC 名称
pentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-1,3,5,7,9,11,13,15,17,19,21-undecaene
传统名称
pentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-1,3,5,7,9,11,13,15,17,19,21-undecaene
简化分子线性输入规范
C1=CC=C2C(C=CC3=CC4=C(C=CC5=CC=CC=C45)C=C23)=C1
InChI 标识符
InChI=1S/C22H14/c1-3-7-19-15(5-1)9-11-17-14-22-18(13-21(17)19)12-10-16-6-2-4-8-20(16)22/h1-14H
键
InChIKey=LHRCREOYAASXPZ-UHFFFAOYSA-N
类型
Phenanthrenes and derivatives
直接大类
Phenanthrenes and derivatives
另外分类
"Anthracenes", "Aromatic hydrocarbons", "Polycyclic hydrocarbons", "Unsaturated hydrocarbons"
取代基
"Anthracene", "Aromatic homopolycyclic compound", "Aromatic hydrocarbon", "Hydrocarbon", "Phenanthrene", "Polycyclic hydrocarbon", "Unsaturated hydrocarbon"
分子框架
Aromatic homopolycyclic compounds
外部描述符
"ortho-fused polycyclic arene"
地位
Detected and Not Quantified
熔点/沸点/溶解度
269.5°C//2.49e-06 mg/mL at 25 °C [HASSETT,JJ et al. (1980)]
暴露途径
Oral (L10) ; inhalation (L10)
毒性机制
The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. The main carcinogenic metabolite of benzo(a)pyrene is the diol-epoxide trans-9,10-epoxy-7,8-dihydrodiol. (L10, L23, A27, A32)
代谢
PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. (L10)
致癌性
2A, probably carcinogenic to humans. (L135)
用途/来源
PAHs are released into the environment via the combustion of fossil fuels, coke oven emissions and vehicle exhausts, as well as naturally from forest fires and volcanic eruptions. PAHs from these sources may contaminate nearly water systems. They are also found in coal tar and charbroiled food. (L10)
健康影响
PAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system. (L10)
症状
Acute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. (A10)
治疗
There is no known antidote for PAHs. Exposure is usually handled with symptomatic treatment. (L10)
创建于
2009-03-06 18:57:55 UTC
更新于
2014-12-24 20:20:52 UTC