3,4-ベンゾピレン 化学特性,用途語,生産方法
外観
うすい黄色〜黄緑色, 結晶性粉末〜粉末
溶解性
水、メタノール又はエタノールにほとんど溶けない。
解説
ベンゾピレン，3,4-benzopyrene．C20H12(252.32)．発がん性物質．石炭タール中に約1.5％ 存在するほか，自動車の排気ガス，タバコの煙，くん製食品などにもごく微量に含まれる．ピレンに無水コハク酸をフリーデル-クラフツ閉環させて合成される．黄色の結晶．融点179.9～180.3 ℃，沸点310～312 ℃(1.33 kPa)．水に不溶，ベンゼン，トルエン，キシレンに可溶，エタノールに微溶，水に不溶．がんの研究に広く使われており，その分析には，エアサンプラーや，そのほかのばいじん捕集器で集められたばいじんをベンゼンで抽出し，抽出液を減圧濃縮したうえ，クロマトグラフィーで単離し，365～403 nm の光吸収，または蛍光を測定して定量する．それ自体には反応性はないが，酵素反応によって生成する7,8-ジオールや9,10-エポキシドがDNA中のグアニン塩基と付加体を形成することが確かめられている．
用途
環境(大気)分析用標準品。
用途
本物質は非意図的生成物のため、用途の情報は無い
用途
接着剤、塗料、防水剤、シーリング剤、結合剤、炭素・黒鉛製品、冶金精錬製品
説明
Benzo(a)pyrene (BaP) is bioactivated to its carcinogenic form
by phase 1 and phase 2 metabolism. As with other polycyclic
aromatic hydrocarbons (PAHs), the presence of the ‘bay
region’ contributes greatly to the carcinogenicity of BaP. This
region is sterically constrained, allowing the formation of
diol epoxides, which subsequently react with intracellular
molecules such as DNA. Human exposure to BaP and other
PAHs occurs primarily from smoking or from secondhand
smoke, air polluted with combustion products, or food and
water polluted with combustion products, such as those
cooked over charcoal or broiled.
BaP has been extensively studied for its toxicities in children
and during pregnancy. A study of pregnant active smokers
showed that BaP crossed the human placenta and was bound
to fetal hemoglobin at levels significantly higher than in pregnant
nonsmokers.
化学的特性
B(a)P, is yellowish needles, crystals or powder.
Odorless. PAHs are compounds containing multiple benzene
rings and are also called polynuclear aromatic
hydrocarbons.
物理的性質
Odorless, yellow, orthorhombic or monoclinic crystals from ethanol. Solution in concentrated
sulfuric acid is orange-red and fluoresces green under exposure to UV light (quoted, Keith and
Walters, 1992).
使用
Benzopyrene is a polyaromatic hydrocarbon (PAH) found in coal tar. Benzopyrene is a known carcinogen. The metbolism of Benzopyrene results in diol epoxides that react and bind to DNA forming adducts which in turns leads to mutations and eventually cancer.
定義
ChEBI: An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings.
一般的な説明
A liquid. Presents a threat to the environment. Immediate steps should be taken to limits its spread to the environment. Easily penetrates the soil and contaminates groundwater or nearby waterways.
空気と水の反応
Insoluble in water.
反応プロフィール
BENZO[A]PYRENE undergoes photo-oxidation after irradiation in indoor sunlight or by fluorescent light in organic solvents. Incompatible with strong oxidizing agents including various electrophiles, peroxides, nitrogen oxides and sulfur oxides. Oxidized by ozone, chromic acid and chlorinating agents. Readily undergoes nitration and halogenation. Hydrogenation occurs with platinum oxide .
危険性
Highly toxic, confirmed carcinogen by inhalation.
健康ハザード
The acute oral toxicity of benzo[a]pyrene islow. This may be due to the poor absorption of this compound by the gastrointestinal tract.The lethal dose in mice from intraperitonealadministration is reported as 500 mg/kg(NIOSH 1986).
Animal studies show sufficient evidence ofits carcinogenicity by all routes of exposureaffecting a variety of tissues, which includethe lungs, skin, liver, kidney, and blood.
Dasenbrock et al. (1996) have investigatedthe carcinogenic potency of carbon particles,diesel soot and benzo[a]pyrene in rats fromrepeated intracheal administration in a 16-week study. A total dose of 15 mg purebenzo[a]pyrene caused lung tumor in theexperimental animals at a rate similar tothat caused by diesel soot and carbon blackparticles.
Lodovici et al. (1998) measured the levelsof PAHs and benzo[a]pyrenediol epoxideDNA adduct in autoptic lung samples ofsmokers and non-smokers. Benzo[a]pyrenediol epoxide resulting from metabolic activation of benzo[a]pyrene binds to DNA to forman adduct, the levels of which can be used as abiomarker to evaluate the exposure of humansto benzo(a)pyrene.
Benz[a]pyrene exhibited teratogeniceffects in test species. It is a mutagen.It showed positive in a histidine rever-sion–Ames test, cell transform mouse embryotest, and in in vitro sister chromatid exchange(SCE)–human lymphocytes..
火災危険
Literature sources indicate that BENZO[A]PYRENE is nonflammable.
毒性学
benzo[a]pyrene (BP) is a reasonably potent contact carcinogen, and therefore has been subjected
to extensive carcinogenic testing. A diet containing 25 ppm of benzo[a]pyrene (BP) fed to
mice for 140 days produced leukemia and lung adenomas in addition to
stomach tumors. Skin tumors developed in over 60% of the rats treated topically
with approximately 10 mg of benzo[a]pyrene three times per week.
The incidence of skin tumors dropped to about 20% when treatment was
about 3 mg 3 per week. Above the 10 mg range, however, the incidence
of skin tumors increased dramatically to nearly 100%.
benzo[a]pyrene (BP) is also carcinogenic when administered orally. In one experiment,
weekly doses of greater than 10 mg administered for 10 weeks induced
stomach cancers, although no stomach cancers were produced at the dose
of 10 mg or less. At 100 mg doses, nearly 79% of the animals had developed
stomach tumors by the completion of the experiment.
When 15 ppm of benzo[a]pyrene (BP) in feed was orally administered to mice, production of
leukemia, lung adenomas, and stomach tumors were observed after 140 days.
安全性プロファイル
Confirmed carcinogen withexperimental carcinogenic, neoplastigenic, andtumorigenic data. A poison via subcutaneous,intraperitoneal, and intrarenal routes. Experimentalteratogenic and reproductive effects. Human mutation data reported. A skin irritant.
職業ばく露
Benzopyrene (BP) is a PAH that
has no commercial-scale production. B(a)P is produced in
the United States by one chemical company and distributed
by several specialty chemical companies in quantities from
100 mg to 5 g for research purposes. Although not manufactured
in great quantity, B(a)P is a by-product of
combustion. It is estimated that 1.8 million pounds per year
are released from stationary sources, with 96% coming
from: (1) coal refuse piles, outcrops, and abandoned coal
mines; (2) residential external combustion of bituminous
coal; (3) coke manufacture; and (4) residential external
combustion of anthracite coal. Human exposure to B(a)P
can occur from its presence as a by-product of chemical
production. The number of persons exposed is not known.
Persons working at airports in tarring operations; refuse
incinerator operations; power plants, and coke manufacturers,
may be exposed to higher B(a)P levels than the general
population. Scientists involved in cancer research or in
sampling toxic materials may also be occupationally
exposed. The general population may be exposed to B(a)P
from air pollution, cigarette smoke, and food sources. B(a)
P has been detected in cigarette smoke at levels ranging
from 0.2 to 12.2:g per 100 cigarettes. B(a)P has been
detected at low levels in foods ranging from 0.1 to 50 ppb.
環境運命予測
The main natural sources of Benzo[a]pyrene(BaP) are forest fires and erupting volcanoes. Anthropogenic sources include the combustion of fossil fuels, coke oven emis- sions, and vehicle exhausts. In surface waters, direct deposition from the atmosphere appears to be the major source of BaP. Benzo[a]pyrene is moderately persistent in the environment. It readily binds to soils and does not readily leach to groundwater, though it has been detected in some groundwater. If released to water, it sorbs very strongly to sediments and particulate matter. In most waters and sediments, it resists breakdown by microbes or reactive chemicals, but it may evaporate or be degraded by sunlight. In water supply systems, it tends to sorb to any particulate matter and be removed by filtration before reaching the tap. In tap water, its source is mainly from PAH-containing materials in water storage and distribution systems.
純化方法
A solution of 250mg of benzo[a]pyrene in 100mL of *benzene is diluted with an equal volume of hexane, then passed through a column of alumina, Ca(OH)2 and Celite (3:1:1). The adsorbed material is developed with a 2:3 *benzene/hexane mixture. (It showed as an intensely fluorescent zone.) The main zone is eluted with 3:1 acetone/EtOH, and is transferred into 1:1 *benzene-hexane by adding H2O. The solution is washed, dried with Na2SO4, evaporated and crystallised from *benzene by the addition of MeOH [Lijinsky & Zechmeister J Am Chem Soc 75 5495 1953]. Alternatively it can be chromatographed on activated alumina, eluted with a cyclohexane-*benzene mixture containing up to 8% *benzene, and the solvent evaporated under reduced pressure [Cahnmann Anal Chem 27 1235 1955], and crystallised from EtOH [Nithipatikom & McGown Anal Chem 58 3145 1986]. [Beilstein 5 III 2517, 5 IV 2687.] CARCINOGENIC.
不和合性
Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,
bromine, fluorine, etc.); contact may cause fires or explosions.
Keep away from alkaline materials, strong bases,
strong acids, oxoacids, epoxides, nitrogen dioxide and ozone.
廃棄物の処理
Incineration in admixture
with a flammable solvent.
3,4-ベンゾピレン 上流と下流の製品情報
原材料
準備製品