Soluble in ethanol, ether, acetone, benzene (U.S. EPA, 1985), toluene, xylenes, and other
monoaromatic hydrocarbons.
物理描述：
Benz[a]anthracene appears as colorless leaflets or plates or coarse gold powder with a greenish-yellow fluorescence. May reasonably be expected to be a carcinogen.
颜色/状态：
Plates from glacial acetic acid or alcohol
蒸汽压力：
2.1X10-7 mm Hg at 25 °C
亨利常数：
1.20e-05 atm-m3/mole
稳定性/保质期：
<p><b>这是一个段落的标题。</b></p>
分解：
Hazardous decomposition products formed under fire conditions - Carbon oxides.[Sigma-Aldrich; Safety Data Sheet for Benz
相对蒸发率：
Evaporative half-life of benzo(a)anthracene in a rapidly-stirred aqueous solution is 89 hours.
The cytochrome P450 isoforms responsible for the regio-selective metabolism of benz[a]anthracene (BA) are poorly defined but as with other polycyclic aromatic hydrocarbons (PAHs) may include members of the CYP2C sub-family. Since the expression of some of these is regulated in a gender-specific manner and may be altered by age, rat strain or by phenobarbital treatment, the effects of these variables on metabolism of BA to diols was investigated. These studies used hepatic, microsomal membranes from immature and adult Long-Evans rats and adult Hooded Lister rats. BA-diols were resolved by normal phase HPLC into three discrete peaks identified as benz[a]anthracene-5,6-diol (BA-5,6-diol), benz[a]anthracene-10, 11-diol (BA-10,11-diol) and a mixture of benz[a]anthracene-3,4- and -8,9-diols (BA-3,4-diol and BA-8,9-diol and termed Peak(3/8)). Significant gender-related differences were found in the rates of diol formation in adults of both the Long-Evans and Hooded Lister rat strains. Formation of BA-10,11-diol and to a lesser extent the components of Peak(3/8) were greater in the male compared to female animals by factors of at least 14 and two, respectively. An age-dependent effect is also observed in the Long-Evans rat since these differences are still apparent in prepubertal animals but to a lesser extent (gender ratio male:female BA-10,11-diol 9X; Peak(3/8) 1.4X). In contrast BA-5,6-diol was formed at similar rates by membranes from female and male rats whether mature (Long-Evans and Hooded Lister) or immature (Long-Evans). Phenobarbital treatment of the adult Long-Evans rats resulted in a moderate increase in the formation of each diol other than at the 10,11-position and the induction was not gender specific. The rate of formation of BA-10, 11-diol was decreased in phenobarbital-treated male rats suggesting modulation of a male specific isoform. Measurement of microsomal epoxide hydrolase revealed no gender or age differences and suggests that this enzyme is not rate limiting in BA-diol formation and thus is not responsible for the differences in BA-diol formation observed. The results suggest that CYP2C11 along with a male-specific isoenzyme not regulated by age are important in the formation of BA-10,11-diol and a component(s) of Peak(3/8) in males. CYPs 2B2 and/or 2C6 appear to be involved in formation of BA-5,6-diol in male and female. ...
Benz[a]anthracene (BA) is one of the most abundant polycyclic aromatic hydrocarbons (PAHs) that are ubiquitous environmental pollutants. PAH carcinogenesis is explained by DNA adduct formation by PAH diol epoxide and oxidative DNA damage by PAH o-quinone. Benz[a]anthracene-trans-3,4-dihydrodiol (BA-3,4-dihydrodiol) is a minor metabolite but shows higher mutagenicity and tumorigenicity than parent BA. We confirmed that a BA o-quinone type metabolite, benz[a]anthracene-3,4-dione (BA-3,4-dione), induced oxidative DNA damage in the presence of cytochrome P450 reductase. ... We found that BA-3,4-dihydrodiol nonenzymatically caused Cu(II)-mediated DNA damage including 8-oxo-7,8-dihydro-2'-deoxyguanosine formation and the addition of NADH enhanced DNA damage. BA-3,4-dihydrodiol induced a double-base lesion of C and G at the 5'-ACG-3' sequence complementary to codon 273 of the human p53 tumor suppressor gene, which is known as a hotspot. The DNA damage was inhibited by catalase and bathocuproine, indicating the involvement of H(2)O(2) and Cu(I). Time-of-flight mass spectroscopic study suggested that BA-3,4-dihydrodiol undergoes Cu(II)-mediated autoxidation leading to the formation of its hydroxylated form of BA-3,4-dihydrodiol, capable of causing oxidative DNA damage. It is noteworthy that BA-3,4-dihydrodiol can nonenzymatically induce DNA damage more efficiently than BA-3,4-dione with metabolic activation. In conclusion, oxidative DNA damage induced by BA-3,4-dihydrodiol not only via quinone-type redox cycle but also via a new type of redox cycle participates in the expression of carcinogenicity of BA and BA-3,4-dihydrodiol.
Cultures of Mycobacterium vanbaalenii strain PYR-1 grown in mineral salts medium and nutrients in the presence of benz[a]anthracene metabolized 15% of the added benz[a]anthracene after 12 days of incubation. Neutral and acidic ethyl acetate extractable metabolites were isolated and characterized by high performance liquid chromatography (HPLC) and uv-visible absorption, gas chromatography/mass (GC/MS) and nuclear magnetic resonance (NMR) spectral analysis. Trimethylsilylation of the metabolites followed by GC/MS analysis facilitated identification of metabolites. The characterization of metabolites indicated that M. vanbaalenii initiated attack of benz[a]anthracene at the C-1,2-, C-5,6-, C-7,12- and C-10,11-positions to form dihydroxylated and methoxylated intermediates. The major site of enzymatic attack was in the C-10, C-11 positions. Subsequent ortho- and meta-cleavage of each of the aromatic rings led to the accumulation of novel ring-fission metabolites in the medium. The major metabolites identified were 3-hydrobenzo[f]isobenzofuran-1-one (3.2%), 6-hydrofuran[3,4-g]chromene-2,8-dione (1.3%), benzo[g]chromene-2-one (1.7%), naphtho[2,1-g]chromen-10-one (48.1%), 10-hydroxy-11-methoxybenz[a]anthracene (9.3%), and 10,11-dimethoxybenz[a]anthracene (36.4%). Enzymatic attack at the C-7 and C-12 positions resulted in the formation of benz[a]anthracene-7,12-dione, 1-(2-hydroxybenzoyl)-2-naphthoic acid, and 1-benzoyl-2-naphthoic acid. A phenyl-naphthyl metabolite, 3-(2-carboxylphenyl)-2-naphthoic acid, was formed when M. vanbaalenii was incubated with benz[a]anthracene cis-5,6-dihydrodiol, indicating ortho-cleavage of 5,6-dihydroxybenz[a]anthracene. A minor amount of 5,6-dimethoxybenz[a]anthracene was also formed. The data extend and propose novel pathways for the bacterial metabolism of benz[a]anthracene.
Cultures of the ligninolytic fungus Irpex lacteus incubated in a nutrient liquid medium degraded more than 70% of the initially applied benz[a]anthracene within 14 days. At the first step of metabolization, benz[a]anthracene was transformed via a typical pathway of ligninolytic fungi to benz[a]anthracene-7,12-dione (BaAQ). The product was further transformed by at least two ways, whereas one is complied with the anthracene metabolic pathway of I. lacteus. Benz[a]anthracene-7,12-dione was degraded to 1,2-naphthalenedicarboxylic acid and phthalic acid that was followed with production of 2-hydroxymethyl benzoic acid or monomethyl and dimethylesters of phthalic acid. Another degradation product of BaAQ was identified as 1-tetralone. Its transformation via 1,4-naphthalenedione, 1,4-naphthalenediol and 1,2,3,4-tetrahydro-1-hydroxynaphthalene resulted again in phthalic acid. None of the intermediates were identified as dead-end metabolites. ...
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)
IDENTIFICATION AND USE: Benz(a)anthracene (BA) is a solid. There is no commercial production of this compound. Polycyclic aromatic hydrocarbons are a group of chemicals that are formed during the incomplete burning of coal, oil, gas, wood, garbage, or other organic substances, such as tobacco and charbroiled meat. HUMAN EXPOSURE AND TOXICITY: It is reasonably anticipated to be a human carcinogen. Benz(a)anthracene induced arylhydrocarbon hydroxylase in two human hepatoma cell lines. The percent of lymphoblasts was higher in benz(a)anthracene-treated cultures of peripheral blood mononuclear cells than in control cultures. ANIMAL STUDIES: 2 mg BA induced 17 carcinomas and 1 papilloma in the bladders of 52 mice surviving 40 or more weeks. The incidence of tumors in the controls was 3.8%. Single administration of 0.5 mg BA by stomach tube produced no tumors among 13 mice observed for 16 months. Eight or 16 administrations at three- to seven-day intervals produced a papilloma of the forestomach in 2/27 mice, whereas no tumors appeared among 16 controls. Benz(a)anthracene was mutagenic in an in vitro L5178Y mouse lymphoma assay with metabolic activation. Benz(a)anthracene showed unequivocal mutagenic activity with metabolic activation in Salmonella typhimurium TA98 and TA100 as determined by Ames assay. Postnatal exposure to BA altered ovarian ERbeta expression, disturbed morphological development of the ovaries and caused ovarian dysfunction in immature rats. ECOTOXICITY STUDIES: BA induced alterations in metabolic enzyme activity in northern bobwhite quail. An increase in mixed-function oxygenase and cytochrome p450 was found in intestinal homogenates from Nereis virens fed food contaminated with benz(a)anthracene. The lowest tested and observed effect concentration (LOEC) for Japanese medaka early life stages was equivalent to 0.92 ug/g dryw of BA. weight
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. (L10, L23, A27, A32)
CLASSIFICATION: B2; probable human carcinogen. BASIS FOR CLASSIFICATION: Based on no human data and sufficient data from animal bioassays. Benz[a]anthracene produced tumors in mice exposed by gavage; intraperitoneal, subcutaneous or intramuscular injection; and topical application. Benz[a]anthracene produced mutations in bacteria and in mammalian cells and transformed mammalian cells in culture. HUMAN CARCINOGENICITY DATA: None. ANIMAL CARCINOGENICITY DATA: Sufficient.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
致癌性证据
整体评估：2B组：该剂对人类可能是致癌的。
OVERALL EVALUATION: Group 2B: The agent is possibly carcinogenic to humans.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
致癌性证据
A2；疑似人类致癌物。
A2; Suspected human carcinogen.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
苯并(a)蒽通过被动扩散进行肠道传输。
Benz(a)anthracene undergoes intestinal transport by passive diffusion.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
苯并(a)蒽在人类肝脏中未被检测到，但在脂肪组织中存在。
... Benz(a)anthracene was not detected in /human/ liver, but was present in fatty tissues.
Benzo(a)pyrene and benz(a)anthracene levels were 0.528 and 0.546 ug/L respectively in the urine in 451 and 437 samples collected in the northwest of the Ruhr area, whereas 35 and 34 urine samples collected in an uncontaminated area contained 0.395 and 0.416 ug/L of benzo(a)pyrene and benz(a)anthracene. Smoking did not affect the urinary ... levels.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
在拟镖水蚤（Daphnia pulex）中，苯并(a)蒽的吸收和代谢时间大约为24小时。
The time for uptake and metabolism of benz(a)anthracene is approximately 24 hours in Daphnia pulex.
1.周国泰，化学危险品安全技术全书，化学工业出版社，1997 2.国家环保局有毒化学品管理办公室、北京化工研究院合编，化学品毒性法规环境数据手册，中国环境科学出版社.1992 3.Canadian Centre for Occupational Health and Safety,CHEMINFO Database.1998 4.Canadian Centre for Occupational Health and Safety, RTECS Database, 1989
Carbon acidity. 77. Ion pair carbon acidities of some silanes in tetrahydrofuran
摘要：
The relative solvent-separated ion pair (SSIP) lithium acidity (PK(Li)/THF) and contact ion pair (CIP) cesium acidity (pK(Cs/THF)) were obtained for 9-fluorenyltrimethylsilane (1) (21.3, 21.6, respectively) and 9-fluorenyl-tert-butyldimethylsilane (2) (20.3, 20.6, respectively) in THF. Values for pK(Cs/THF) were determined at 25-degrees-C for (p-biphenylylmethyl)-tert-butyldimethylsilane (3), 35.4, benzyltrimethylsilane (4), 37.5, alpha,alpha-bis(trimethylsilyl)toluene (5), 34.1, 2-(trimethylsilyl)-1,3-dithiane (6), 33.5, (trimethylsilyl)acetonitrile (7), 28.8, and tris(trimethylsilyl)methane (8), 36.8. Some thermodynamic parameters were determined by measurements at other temperatures, and some ionic acidities (pK(FI)) were determined by conductivity studies. Carbanion stabilization by these silyl substituents varies from about 1 to over 3 pK units in different systems. 9,9-Bis(trimethylsilyl)fluorene (9) was found to undergo silyl transfer on treatment with various carbanions, but this reaction is slower than proton transfer.
Flash vacuum pyrolysis of 1,6-diphenyl-1,5-hexadien-3-ynes: tandem diaryldienyne cyclizations to form chrysene
作者：Motohiro Sonoda、Kayo Itahashi、Yoshito Tobe
DOI：10.1016/s0040-4039(02)01062-6
日期：2002.7
Flashvacuumpyrolysis of 1,6-diphenyl-1,5-hexadien-3-yne at 1000°C and its bromo derivative at 800°C yielded chrysene as the major product through tandem diaryldienyne cyclizations.
BF<sub>3</sub>·2CF<sub>3</sub>CH<sub>2</sub>OH (BF<sub>3</sub>·2TFE), an Efficient Superacidic Catalyst for Some Organic Synthetic Transformations
作者：G. K. Surya Prakash、Thomas Mathew、Eric R. Marinez、Pierre M. Esteves、Golam Rasul、George A. Olah
DOI：10.1021/jo0604181
日期：2006.5.1
acid strength to at least that of 100% anhydrous sulfuric acid for various acid-catalyzed organic transformations such as isomerizations, rearrangements, ionic hydrogenation of various ketones, and aromatics with triethylsilane and nitration of aromatics with metal nitrate. Studies of the pivalaldehyde−methyl isopropyl ketone rearrangement and the benzopinacol to phenanthrene transformation suggest
1:2-Benzanthracene and the 3′-methyl derivative have been prepared by Raney nickel reduction of the sulphuric esters of the leuco derivatives of 1:2-benzanthraquinone and 4′-chloro-3′-methyl-1:2-benzanthraquinone, followed by dehydrogenation. 3-Hydroxy-1:2-benzanthraquinone was methylated in the 4-position by formaldehyde, sodium hydrosulphite and sodium hydroxide solution (the Marschalk reaction)
Pd, Ir, Ru, and Rh with inexpensive earth-abundant metals like cobalt (Co) is attracting wider research interest in catalysis. Cobalt catalysts are now undergoing a renaissance in hydrogenation reactions. Herein, we describe a hydrogenation method for polycyclic aromatic hydrocarbons (PAHs) and olefins with a magnesium-activated earth-abundant Co catalyst. When diketimine was used as a ligand, simple
用廉价的地球丰富的金属如钴 (Co) 代替昂贵的贵金属如 Pt、Pd、Ir、Ru 和 Rh，正在吸引更广泛的催化研究兴趣。钴催化剂现在正经历加氢反应的复兴。在此，我们描述了一种使用镁活化的富含地球的 Co 催化剂对多环芳烃 (PAHs) 和烯烃进行加氢的方法。当二酮亚胺用作配体时，CoBr 2的简单且廉价的金属盐与镁结合在温和条件下对具有挑战性的多环芳烃进行位点选择性加氢显示出高催化活性。共催化氢化能够减少多环芳烃的两侧芳烃。多种多环芳烃可以以位点选择性方式进行氢化，这为制备部分还原的多环烃基序提供了一种经济、清洁和选择性的策略，而这些多环烃基序很难通过常规方法制备。还证明了使用定义明确的二酮亚胺配体 Co 配合物作为多环芳烃和烯烃选择性加氢的预催化剂。
Ultrasound assisted Bradsher reaction in aqueous and non-aqueous media: First use of ultrasounds in electrophilic aromatic cyclisation leading to polyacenes
作者：Emilia Kowalska、Piotr Bałczewski
DOI：10.1016/j.ultsonch.2016.07.010
日期：2017.1
ortho-formyl diarylmethanes. This reaction is also the first example of electrophilic, aromatic cyclisation assisted by ultrasounds which leads to pure polycyclic, fused aromatic hydrocarbons containing 3 and 4 fused rings in excellent yields. The reaction proceeds not only in aqueous but also in non-aqueous media at milder conditions (room temperature) and in much shorter reaction times than in conventional
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