다이벤조[a,e]플루오란텐

Dibenzo(a,e)fluoranthene appears as yellow crystals. Water insoluble.

Yellow solid; [HSDB]

Warning

H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]

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

Aggregated GHS information provided per 51 reports by companies from 2 notifications to the ECHA C&L Inventory.

Warning

H351: Suspected of causing cancer [Warning Carcinogenicity]

Vigorous reactions, sometimes amounting to explosions, can result from the contact between aromatic hydrocarbons, such as DIBENZO(A,E)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/.

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.[Sigma-Aldrich; Safety Data Sheet for Dibenzo

Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.[Sigma-Aldrich; Safety Data Sheet for Dibenzo

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.[Sigma-Aldrich; Safety Data Sheet for Dibenzo

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.

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber; Contaminated packaging: Dispose of as unused product.[Sigma-Aldrich; Safety Data Sheet for Dibenzo

The worker should wash daily at the end of each work shift, and prior to eating, drinking, smoking, etc. /Coal tar pitch volatiles/

Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises. /Coal tar pitch volatiles/

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.[Sigma-Aldrich; Safety Data Sheet for Dibenzo

Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.[Sigma-Aldrich; Safety Data Sheet for Dibenzo

For more Preventive Measures (Complete) data for Dibenzo(a,e)fluoranthene (8 total), please visit the HSDB record page.

8 Hr Time Weighted Avg (TWA): 0.2 mg/cu m. /Coal tar pitch volatiles, as benzene soluble aerosol/

Peak Exposure Recommendation: Transient increases in workers' exposure levels may exceed 3 times the value of the TLV-TWA level for no more than 15 minutes at a time, on no more than 4 occasions spaced 1 hour apart during a workday, and under no circumstances should they exceed 5 times the value of the TLV-TWA level. In addition, the 8-hour TWA is not to be exceeded for an 8-hour work period. /Coal tar pitch volatiles, as benzene soluble aerosol/

A1; Confirmed human carcinogen. /Coal tar pitch volatiles, as benzene soluble aerosol/

Biological Exposure Index (BEI): Determinant: 1-Hydroxypyrene (1-HP) in urine (with hydrolysis); Sampling Time: end of shift at end of workweek. BEI: None.; Biological monitoring should be considered for this compound based on the review; however, a specific BEI could not be determined due to insufficient data. /Polycyclic aromatic hydrocarbons/

For more Threshold Limit Values (TLV) (Complete) data for Dibenzo(a,e)fluoranthene (6 total), please visit the HSDB record page.

Respirator Recommendations: At concentrations above the NIOSH REL, or where there is no REL, at any detectable concentration: /Coal tar pitch volatiles/[Table#6566]

Respirator Recommendations: Escape conditions: /Coal tar pitch volatiles/[Table#6567]

Eye/face protection: Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).[Sigma-Aldrich; Safety Data Sheet for Dibenzo

Skin protection: Handle with gloves.[Sigma-Aldrich; Safety Data Sheet for Dibenzo

For more Personal Protective Equipment (PPE) (Complete) data for Dibenzo(a,e)fluoranthene (6 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 6.5X10+6(SRC), determined from a structure estimation method(2), indicates that dibenzo(a,e)fluoranthene is expected to be immobile in soil(SRC). Volatilization of dibenzo(a,e)fluoranthene from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.9X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Dibenzo(a,e)fluoranthene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.3X10-11 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Biodegradation data in soil were not available(SRC, 2017). However, polycyclic aromatic hydrocarobons with four or more rings are generally expected to be resistant to biodegradation(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 6.5X10+6(SRC), determined from a structure estimation method(2), indicates that dibenzo(a,e)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 7.9X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(6), an estimated BCF of 9600(SRC), from an estimated log Kow of 7.28(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). PAHs may not bioconcentrate in aquatic organisms which contain microsomal oxidase, such as some fish, as this enzyme enables the rapid metabolism of certain polycyclic aromatic hydrocarbons(6). Biodegradation data in water were not available(SRC, 2017). However, polycyclic aromatic hydrocarobons with four or more rings are generally expected to be resistant to biodegradation(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dibenzo(a,e)fluoranthene, which has an estimated vapor pressure of 7.3X10-11 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase dibenzo(a,e)fluoranthene may be removed from the air by wet and dry deposition(SRC). Dibenzo(a,e)fluoranthene absorbs UV light at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

IDENTIFICATION AND USE: Dibenzo(a,e)fluoranthene (DB(a,e)F) is a solid polycyclic aromatic hydrocarbon (PAH). There is no commercial production or known use of this compound. HUMAN EXPOSURE AND TOXICITY: There are no data available. ANIMAL STUDIES: There is limited evidence in experimental animals for the carcinogenicity of DB(a,e)F. Dibenzofluoranthene-12,13-dihydrodiol is six times more mutagenic in Salmonella TA100 than dibenzofluoranthene-3,4-dihydrodiol. However, these two major DB(a,e)F proximate metabolites, which are immediate precursors of the corresponding diolepoxides, showed on an equimolar basis nearly identical initiation activities on mouse skin; they induced three times more papillomas than the parent hydrocarbon. On the other hand the epithelioma initiation capacities, i.e. the number of papillomas progressing to malignant tumors, of DB(a,e)F or the two dibenzofluoranthene dihydrodiols were equivalent. These data indicate that activation of DB(a,e)F to bacterial mutagens may occur predominantly through a vicinal, non-bay-region 12,13-dihydrodiol epoxide.

Using a structure estimation method based on molecular connectivity indices(1), the Koc of dibenzo(a,e)fluoranthene can be estimated to be 6.5X10+6(SRC). According to a classification scheme(2), this estimated Koc value suggests that dibenzo(a,e)fluoranthene is expected to be immobile in soil.

Dibenzo(a,e)fluoranthene is one of many polycyclic aromatic hydrocarbons (PAH), a group of chemicals that are formed during the incomplete burning of coal, oil, gas, wood, garbage, or other organic substances. PAHs generally occur as complex mixtures, for example as part of combustion products such as soot, not as single compounds. PAHs occur naturally in volcanoes and forest fires. They can also be found in substances such as crude oil and coal. They are found throughout the environment in the air, water, and soil(1). /Polycyclic aromatic hydrocarbons/

URBAN/SUBURBAN: Unspecified dibenzofluoranthene was identified in air samples collected from several locations at Christchurch, New Zealand. July concentrations ranged from 2 to 80 ng/cu m; year not specified(1). The mean concentration of dibenzo(a,e)fluoranthene/dibenzo(b,k)fluoranthene in Beijing, China during the 2008 Olympic games was 352.0 pg/cu m during source control periods and 483.0 pg/cu m during non-source control periods(2).

/GENOTOXICITY/ Relatively little is known about the mutagenicity of C24H14 PAH, a diverse group of five- and six-ring PAH, some of which are present at trace levels in the environment. To better understand the mutagenicity of this class of compounds, 11 C24H14 PAH, including benzo[a]perylene, benzo[b]perylene, dibenzo[a,e]fluoranthene, dibenzo[a,f]fluoranthene, dibenzo[j,l]fluoranthene, dibenzo[a,h]pyrene, dibenzo[a,i]pyrene, dibenzo[e,l]pyrene, naphtho[1,2-b]fluoranthene, naphtho[2,3-a]pyrene, and naphtho[2,3-e]pyrene, were tested in a mutagenicity assay based on human h1A1v2 cells. h1A1v2 cells are a line of human B-lymphoblastoid cells that have been engineered to express cytochrome P4501A1 (CYP1A1), an enzyme capable of metabolizing promutagenic PAH. Mutagenicity was measured at the thymidine kinase (tk) locus following a 72-hr exposure period. Our results show that nine of the compounds were mutagenic. Benzo[a]perylene, dibenzo[a,e]fluoranthene, dibenzo[a,i]pyrene, and naphtho[2,3-a]pyrene were the most potent mutagens, having minimum mutagenic concentrations (MMC) (i.e., the dose at which the induced response was twice that of the negative controls) in the 1-5 ng/mL range. Benzo[b]perylene, dibenzo[a,h]pyrene, dibenzo[a,f]fluoranthene, and naphtho[2,3-e]pyrene were somewhat less potent mutagens, having MMC in the 10-30 ng/mL range. Dibenzo[e,l]pyrene, which had an MMC of 280 ng/mL, was the least potent mutagen. Dibenzo[j,l]fluoranthene and naphtho[1,2-b]fluoranthene were not mutagenic at the doses tested (1-3000 ng/ml). The most mutagenic compounds were also quite toxic. At the highest doses tested, benzo[a]perylene, dibenzo[a,e]fluoranthene, dibenzo[a,i]pyrene, dibenzo[a,h]pyrene, and dibenzo[a,f]fluoranthene induced > 60% killing, and naphtho[2,3-a]pyrene and naphtho[2,3-e]pyrene induced > 50% killing. Benzo[b]perylene, dibenzo[e,l]pyrene, dibenzo[j,l]fluoranthene, and naphtho[1,2-b]fluoranthene induced < 50% killing at the highest doses tested. Comparing these results to a previous study in which nine other C24H14 PAH were tested for mutagenicity in this same assay, it was found that dibenzo[a]pyrene isomers were generally more mutagenic than the other groups of C24H14 PAH tested. These observations are discussed with emphasis given to identifying C24H14 PAH that may be important environmental mutagens.

Dibenzo(a,e)fluoranthene is a member of a group of chemicals called polycyclic aromatic hydrocarbons (PAHs). Dibenzo(a,e)fluoranthene occurs primarily in products of incomplete combustion(1), which may result in its release to the environment through various waste streams(SRC). There is no commercial production of this compound(1).

AEROBIC: Polycyclic aromatic hydrocarobons (PAHs) with four or more rings, such as dibenzo(a.e)fluoranthene, are generally expected to be resistant to biodegradation(1). Previous studies have shown that PAHs with 2 or 3 rings can be biodegraded(2).

Dibenzo[a,e]fluoranthene

Group 3: Not classifiable as to its carcinogenicity to humans

Volume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987; 440 pages; ISBN 92-832-1411-0 (out of print)

2010

2005

An estimated BCF of 9600 was calculated in fish for dibenzo(a,e)fluoranthene(SRC), using an estimated log Kow of 7.28(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC), provided the compound is not metabolized by the organism(SRC). PAHs 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(3). Some marine organisms have no detectable aryl hydrocarbons hydroxylase enzyme systems, namely: phytoplankton, certain zooplankton, mussels (Mytilus edulis), scallops (Placopecten sp), and snails (Litternia littorea)(4). Those organisms which lack a metabolic detoxification enzyme system, tend to accumulate polycyclic aromatic hydrocarbons(4).

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 production by dibenzo[a,e]fluoranthene (DBF) of DNA-protein cross-links in cultured mouse fibroblasts is probably mediated by the activation of proximate metabolites of DBF and not by the DBF molecule itself. In order to test this hypothesis, several agents that enhance or reduce production of the DBF metabolite putatively involved in cross-linking were tested. Increasing NADPH concentrations in the medium enhanced cross-link production; 1,2-epoxy-3,3,3-trichloropropane (TCPO), an inhibitor of epoxide hydrolases, slightly reduced DNA-protein cross-link formation at high concentrations; norharman (NH), an inhibitor of certain steps in the metabolism of DBF, totally blocked cross-linking. The possible involvement of DBF-bisdihydrodiol, a bifunctional metabolite identified in vitro, is discussed. Postincubation in DBF-free medium did not induce a significant reduction in cross-links, indicating that repair did not take place.

Dibenzo[a,e]fluoranthene, its 7-hydroxy, 3,4- and 12,13-dihydrodiol metabolic derivatives as well as three synthetic, structurally related hydrocarbons, were tested for mutagenicity towards Salmonella typhimurium TA100 strain in the presence of 3-methylcholanthrene-treated rat and mouse liver post-mitochondrial supernatants. Of these compounds, the 12,13-dihydrodiol showed the highest activity, being 6-10 times more mutagenic than the parent compound. Our data, in conjunction with those of previous studies on the liver microsomal metabolism and DNA binding of dibenzo[a,e]fluoranthene and its dihydrodiols, indicate that activation of dibenzo[a,e]fluoranthene to bacterial mutagens may occur predominantly through a vicinal, non-bay-region 12,13-dihydrodiol epoxide.

When dibenzo[a,e]fluoranthene (DBF) is incubated in vitro with mouse liver microsomes in the presence of calf thymus DNA, several metabolites bind covalently to DNA. The metabolite-nucleoside adducts were separated by h.p.l.c. after enzymatic hydrolysis. The elution profile of this chromatogram exhibits six main peaks, labeled from A to F in order of decreasing polarity. It was compared to those obtained by direct reaction of DNA with 3,4-dihydroxy-1,2-epoxy 1,2,3,4-tetrahydro DBF (the bay region diol-epoxide) or 12,13-dihydroxy 10,11-epoxy 10,11,12,13-tetrahydro DBF (the pseudo bay region diol-epoxide). In both cases the retention period of the peak of the adduct was identical to that of the main peak E. The fluorescence spectra of these two adducts were similar to those of the corresponding tetrols. When DNA is reacted in the presence of microsomes with 3,4-dihydrodihydroxy DBF, the elution profile of the adducts indicates that vicinal epoxidation of the dihydrodiol and direct reaction is dominant. The metabolic reaction with 12,13-dihydrodihydroxy DBF appears more complex as revealed by the observed number of adducts which correspond to vicinal epoxidation of dihydrodiol as well as further oxidation at other sites.

The effects of norharman (NH) (a putative vicinal diolepoxidation inhibitor in DBF metabolism) on the metabolism of dibenzo[a,e]-fluoranthene (DBF) and on its fixation on DNA, RNA and proteins have been studied in vitro by incubation with S-9 and microsomes from rats and mice. Norharman (a putative vicinal diolepoxidation inhibitor in DBF metabolism) causes a decrease of the activity of microsome monooxygenases proportionally to its concentration but has no effect on the activity of NADPH p450 reductase nor on that of epoxide hydrolase. Paradoxically, the amount of DBF hydrophobic metabolites and especially that of diols and phenols, increases in the incubation mixture in the presence of NH; this increase is independent of the presence of conjugation enzymes of cytosol. Norharman (a putative vicinal diolepoxidation inhibitor in DBF metabolism) does not modify the covalent binding of DBF on the microsome RNA, conversely it decreases the binding of DBF on the DNA and on the proteins of the incubation mixture. This could partly explain the increase of DBF diols and phenols by an accumulative effect. Two higher homologs of NH: benzo[g]-beta carboline and benzo[i]-beta carboline, tested under the same conditions, proved inhibitory.

For more Metabolism/Metabolites (Complete) data for Dibenzo(a,e)fluoranthene (6 total), please visit the HSDB record page.

Not commercially used or produced; [HSDB]

Laboratory chemicals. Synthesis of substances.[Sigma-Aldrich; Safety Data Sheet for Dibenzo