Benzo(J)Fluoranthene

Yellow plates from alcohol, needles from acetic acid

Orange needles from benzene and alcohol

Yellow plates (recrystallized from ethanol); needles (recrystallized from acetic acid).

Solubility in water: 2.5X10-9 mg/L, temperature not specified

Soluble in hydrogen sulfide on heating

Slightly soluble in ethanol and acetic acid.

Benzo[j]fluoranthene appears as yellow crystals. Insoluble in water.

Yellow to orange solid; [HSDB] White powder; [MSDSonline]

Danger

H350: May cause cancer [Danger Carcinogenicity]

P203, P273, P280, P318, P391, P405, and P501 (click each P-code to see the statement)

Danger

H350 (100%): May cause cancer [Danger Carcinogenicity]

P203, P273, P280, P318, P391, P405, and P501 (click each P-code to see the statement)

Hazard Traits - Bioaccumulation; Carcinogenicity; Environmental Persistence; Environmental tox

Regulation (EC) No 178/2002 (amended)

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Danger of cutaneous absorption; [MAK] See POLYCYCLIC AROMATIC HYDROCARBONS.

The major hazards encountered in the use and handling of benzo(j)fluoranthene stem from its toxicologic properties. Exposure to this orange to yellow, crystalline substance may occur from its use as an experimental carcinogen in biochemical research, or from its ubiquitous presence in the products of incomplete combustion from such activities as coal tar distillation, petroleum refining, and the combustion of wood, coal, oil, and gasoline. Ventilation should be employed to prevent exposure. However, in activities and situations where over-exposure may occur, wear a respirator and protective suit (preferably one piece, disposable, closely fitting at the ankles and wrists), including gloves, hair covering, and overshoes. Smoking, eating, and drinking should be prohibited in benzo(j)fluoranthene work areas. Transport of this substance should be in a securely sealed container which is placed in a second unbreakable, leakproof container. Before implementing land disposal of benzo(j)fluoranthene, consult with environmental regulatory agencies for guidance.

National Toxicology Program. Fourteenth Report on Carcinogens (2016). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. Benzo(j)fluoranthene (205-82-3) is listed as reasonably anticipated to be a human carcinogen. /Polycyclic Aromatic Hydrocarbons/[Available from, as of July 31, 2009: https://ntp.niehs.nih.gov/pubhealth/roc/index-1.html]

U.S. Dept Health & Human Services/Agency for Toxic Substances Disease Registry; Toxicological Profile for Polycyclic Aromatic Hydrocarbons (Update) (1995) NTIS# PB/95/264370

Vigorous reactions, sometimes amounting to explosions, can result from the contact between aromatic hydrocarbons, such as BENZO[J]FLUORANTHENE, and strong oxidizing agents. They can react exothermically with bases and with diazo compounds. Substitution at the benzene nucleus occurs by halogenation (acid catalyst), nitration, sulfonation, and the Friedel-Crafts reaction.

Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 0.1 mg/cu m (cyclohexane-extractable fraction). /Coal tar pitch volatiles/

NIOSH considers coal tar pitch volatiles to be potential occupational carcinogens. NIOSH usually recommends that occupational exposures to carcinogens be limited to the lowest feasible concentration. /Coal tar pitch volatiles/

Toxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations. /Polynuclear aromatic hydrocarbons (including benzanthracenes, benzopyrenes, benzofluoranthene, chrysenes, dibenz-anthracenes, and indenopyrenes)/

For the maximum protection of human health from the potential carcinogenic effects of exposure to polynuclear aromatic hydrocarbons through ingestion of contaminated water and contaminated aquatic organisms, the ambient water concentration should be zero, based on the nonthreshold assumption for this chemical. However, zero level may not be attainable at the present time. Therefore, the levels which may result in incremental increase of cancer risk over the lifetime are estimated at 1X10-5, 1X10-6, and 1X10-7. The corresponding recommended criteria are 28.0 ng/L, 2.8 ng/L, and 0.28 ng/L, respectively. If these estimates are made for consumption of aquatic organisms only, excluding consumption of water, the levels are 311.0 ng/L, 31.1 ng/L, and 3.11 ng/L, respectively. /Polynuclear aromatic hydrocarbons/.

PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practicable to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": A high efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 600,000(SRC), determined from a structure estimation method(2), indicates that benzo(j)fluoranthene is expected to be immobile in soil(SRC). Volatilization of benzo(j)fluoranthene from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.0X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Benzo(j)fluoranthene is not expected to volatilize from dry soil surfaces based on an estimated vapor pressure of 2.7X10-8 mm Hg(SRC), determined from a fragment constant method(2). PAHs with four or more rings, such as benzo(j)fluoranthene, are generally expected to be resistant to biodegradation(3). Benzo(j)fluoranthene absorbs strongly at wavelengths >290 nm(4), and therefore is expected to be susceptible to direct photolysis on surfaces exposed to sunlight(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 600,000(SRC), determined from a structure estimation method(2), indicates that benzo(j)fluoranthene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.0X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). According to a classification scheme(4), an estimated BCF of 4990(SRC), from an estimated log Kow of 6.11(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is very high, provided the compound is not metabolized by the organism(SRC). However, benzo(j)fluoranthene may not bioconcentrate in aquatic organisms which contain microsomal oxidase, such as fish, as this enzyme enables the rapid metabolism of certain polycyclic aromatic hydrocarbons(5). PAHs with four or more rings, such as benzo(j)fluoranthene, are generally expected to be resistant to biodegradation(6). Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions(3). Benzo(j)fluoranthene absorbs strongly at wavelengths >290 nm(7), and therefore is expected to be susceptible to direct photolysis at water surfaces exposed to sunlight(SRC).

Toxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations. /Polynuclear aromatic hydrocarbons (including benzanthracenes, benzopyrenes, benzofluoranthene, chrysenes, dibenz-anthracenes, and indenopyrenes)/

For the maximum protection of human health from the potential carcinogenic effects of exposure to polynuclear aromatic hydrocarbons through ingestion of contaminated water and contaminated aquatic organisms, the ambient water concentration should be zero, based on the nonthreshold assumption for this chemical. However, zero level may not be attainable at the present time. Therefore, the levels which may result in incremental increase of cancer risk over the lifetime are estimated at 1X10-5, 1X10-6, and 1X10-7. The corresponding recommended criteria are 28.0 ng/L, 2.8 ng/L, and 0.28 ng/L, respectively. If these estimates are made for consumption of aquatic organisms only, excluding consumption of water, the levels are 311.0 ng/L, 31.1 ng/L, and 3.11 ng/L, respectively. /Polynuclear aromatic hydrocarbons/.

The 9,10-dihydrodiol has been detected as a metabolite of benzo(j)fluoranthene in rat liver preparations.

The metabolites of benzo(j)fluoranthene (BjF) as formed in vitro using the 9000 from Aroclor-pretreated rats have been identified. Two dihydrodiols, trans-4,5- dihydroxybenzo(j)fluoranthene and trans-9,10-dihydro-9,10-dihydroxybenzo(j)fluoranthene have been identified as major metabolites by comparison of their spectral and chromatographic properties with those of pure synthetic standards. There was no evidence that any of the isomeric 2,3-dihydrodiol was formed as a metabolite of benzo(j)fluoranthene under these conditions. Neither of the metabolic dihydrodiols of benzo(j)fluoranthene were formed with a high degree of steroselectivity. The enantiomeric purity of te 4,5-dihydrodiol was 20% while that of the 9,10-dihydrodiol was 46%. At least four phenols were detected among the metabolites of benzo(j)fluoranthene These were identified as 3-,4-,6- and 10-hydroxybenzo(j)fluoranthene based upon comparison of their UV spectra and HPLC retention times with those of synthetic reference standards. Benzo(j)fluoranthene-4,5-dione was also identified as a metabolite under these incubation conditions.

The metabolism of benzo(j)fluoranthene (BjF) in vivo in mouse skin was investigated, trans-4,5-dihydro-4,5-dihydroxybenzo(j)fluoranthene (BjF-4,5-diol) and trans-9,10-dihydro-9,10-dihydroxybenzo(j)fluoranthene (BjF-9,10-diol) have been identified as major metabolites. In addition, 4- and 0-hydroxybenzol(j) fluoranthene and benzo(j)fluoranthene-4,5-dione have been tentatively identified among the metabolites formed in vivo in mouse skin. The enantiomeric purity of the metabolic dihydrodiols of benzo(j)fluoranthene as formed in vivo in mouse skin was determined. The major enantiomeric of benzo(j)fluoranthene-4,5-diol was present in 57-62% enantiomeric excess while that of benzo(j)fluoranthene-9,10-diol was present in 66-71% enantiomeric excess. In each case the later-eluting enantiomer on chiral stationary-phase high performance liquid chromatography predominated. The tumor-initiating activity of trans-2,3-dihydro-2,3-dihydroxybenzol(j) fluoranthene (BjF-2,3-diol), trans-4,5-Dihydro-4,5-dihydroxybenzol(j) fluoranthene, trans-9,10-dihydro-9,10-dihydroxybenzol(j)fluoranthene, and benzo(j)fluoranthene was evaluated on the skin of female CD-1 mice. As a total initiation dose of 3 umol/mouse trans-4,5-Dihydro-4,5-dihydroxybenzo(j)fluoranthene resulted in a 100% incidence of tumor-bearing mice with 5.0 tumors/mouse. In comparison, benzo(j)fluoranthene-9,10-diol elicited a 60% incidence of tumor-bearing mice with 1.7 tumors/mouse, while benzo(j)fluoranthene-2,3-diol was inactive. At the same dose, benzo(j)fluoranthene gave rise to a 90% incidence of tumor-bearing mice with 7.8 tumors/mouse. At a 1 mumol dose, trans-4,5-Dihydro-4,5-dihydroxybenzo(j) fluoranthene induced a 78% incidence of tumor-bearing mice with 4.5 tumors/mouse while benzo(j)fluoranthene gave rise to a 70% tumor incidence with 3.4 tumors/mouse. These studies indicate that while trans-9,10-dihydro-9,10-dihydroxybenzo(j) fluoranthene could contribute to the overall tumorigenic activity of benzo(j)fluoranthene in mouse skin, trans-4,5-Dihydro-4,5-dihydroxybenzol(j)fluoranthene is a more potent tumor initiator in the target tissue.

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)

Used as a cancer research chemical; Not commercially used or produced; [HSDB]

BIOCHEMICAL RESEARCH

Substance listed with specific concentration in tattoo ink and/or permanent make up according to EU Commission Regulation 2020/2081. The concentration limit (by weight) is 0.00005%.

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 vocanic eruptions. PAHs from these sources may contaminate nearly water systems. They are also found in coal tar and charbroiled food. (L10)