189-55-9c1ccc2c(c1)cc1ccc3cc4ccccc4c4ccc2c1c34TUGYIJVAYAHHHM-UHFFFAOYSA-NDibenzo[a,i]pyrene can cause cancer according to an independent committee of scientific and health experts.
189-55-9DTXSID9059751CHEBI:82314Dibenz[a,i]pyrene is a colorless solid. Water insoluble.
Greenish-yellow solid; [HSDB]
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Danger
H341: Suspected of causing genetic defects [Warning Germ cell mutagenicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
This chemical does not meet GHS hazard criteria for 6.1% (3 of 49) of reports.
Danger
H350 (16.3%): May cause cancer [Danger Carcinogenicity]
Hazard Traits - Bioaccumulation; Carcinogenicity; Environmental Persistence
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.)
Eight tires were analyzed for 15 high molecular weight (HMW) polycyclic aromatic hydrocarbons (PAH), using pressurized fluid extraction. The variability of the PAH concentrations determined between different tires was large; a factor of 22.6 between the lowest and the highest. The relative abundance of the analytes was quite similar regardless of tire. Almost all (92.3%) of the total extractable PAH content was attributed to five PAHs: benzo[ghi]perylene, coronene, indeno[1,2,3-cd]pyrene, benzo[e]pyrene, and benzo[a]pyrene. The difference in the measured PAH content between summer and winter tires varied substantially across manufacturers, making estimates of total vehicle fleet emissions very uncertain. However, when comparing different types of tires from the same manufacturer they had significantly (p = 0.05) different PAH content. Previously, there have been no data available for carcinogenic dibenzopyrene isomers in automobile tires. In this study, the four dibenzopyrene isomers dibenzo[a,l]pyrene, dibenzo[a,e]pyrene, dibenzo[a,i]pyrene, and dibenzo[a,h]pyrene constituted <2% of the sum of the 15 analyzed HMW PAHs. These findings show that automobile tires may be a potential previously unknown source of carcinogenic dibenzopyrenes to the environment.[Sadiktsis I et al; Environ Sci Technol 46 (6): 3326-34 (2012)]
Dibenzo[a,i]pyrene (10 umol) was metabolized to partially characterized phenols and dihydrodiols by mixed-function oxidases in liver homogenates and microsomes from 3-methylcholanthrene pretreated rats.
1,2 & 3,4-dihydrodiols have been reported to be metabolites of dibenzo[a,i]pyrene following incubation of this compound with rat-liver preparations. The 3,4-dihydrodiol has been reported to be mutagenic to bacteria in the presence of an exogenous metabolic system; it is a tumor initiator on mouse skin and tumorigenic in newborn mice.
... C57BL/6 Jax mice /were injected/ sc with 500 ug (14)C-labelled DB(a,i)P in peanut oil. Distribution of radioactivity between injection sites and organs was determined ... 85% of carcinogen is removed from injection site and ... removal was nearly complete in 10 wk.
Used as a research chemical; [HSDB] Present in fossil fuels, cigarette smoke, and coal tar; [CHEMINFO]
Smoking cigarettes [Category: Food & Drugs]
There is no ... known use of this compound.
/SRP/: Experimental carcinogen
PAHs are generally not produced commercially in the United States except as research chemicals. /Polycyclic aromatic hydrocarbons/
(1978) Not produced commercially in USA
(1982) Not produced commercially in USA
There is no commercial production ... of this compound.
Keine Reaktionsaufzeichnungen unter den aktuellen Filterkriterien.
Wird geladen…
Ionization potential: 6.95-7.30 eV (range of 4 values)
Enthalpy of fusion: 27.87 kJ/mol at 556.8 K
Attacked by nitric acid & by other reagents, mainly at 5- & 8-positions; slowly oxidized by sulfuric acid to a quinone; oxidized by lead tetraacetate to the 5,8-diacetoxy derivative and by chromic oxide or selenium dioxide to the 5,8-quinone
Concentrated sulfuric acid solutions of dibenzo(a,i)pyrene are blue with red fluorescence; it is almost insoluble in alcohol and ether. Db(a,i)p can be sublimed unchanged.
DHHS/National Toxicology Program; Report on Carcinogens, Fourteenth Edition: Polycyclic Aromatic Hydrocarbons (November 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. Dibenzo(a,i)pyrene (189-55-9) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of November 3, 2016: http://ntp.niehs.nih.gov/pubhealth/roc/index-1.html]
USEPA; Ambient Water Quality Criteria Doc: Polynuclear Aromatic Hydrocarbons (Draft) (1980)
Health & Welfare Canada; Polycyclic Aromatic Hydrocarbons (1979) Report No. 80-EHD-50
Dutch Expert Committee on Occupational Standards; Ministry of Social Affairs and Employment RA 2/95: 50-1 (1995). Scientific documentation on the Dutch list of occupational carcinogens (II) for dibenzo(a,i)pyrene.
U064; As stipulated in 40 CFR 261.33, when dibenzo(a,i)pyrene, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).
Vigorous reactions, sometimes amounting to explosions, can result from the contact between aromatic hydrocarbons, such as DIBENZ[A,I]PYRENE, 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.
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/
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.
... In surface waters, one-third of the total PAH is bound to larger suspended particles, a third is bound to finely dispersed particles, and the last third is present in dissolved form. The particle-bound portion of polycyclic aromatic hydrocarbons (PAH) can be removed by sedimentation, flocculation, and filtration processes. The remaining one-third dissolved PAH usually requires oxidation for partial removal/transformation. /Polynuclear aromatic hydrocarbons/
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/
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U064, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
IARC describes laboratory decontamination & destruction methods for polycyclic aromatic hydrocarbons in this publication (number 49). When dealing with compounds other than those listed, the efficiency of the method should first be verified. Dibenzo(a,i)pyrene is not listed, but the method may be applicable to its destruction. /Polycyclic aromatic hydrocarbons/
PRECAUTIONS FOR "CARCINOGENS": Total destruction ... by incineration may be only feasable method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable. ... Most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/
For more Disposal Methods (Complete) data for Dibenzo(a,i)pyrene (6 total), please visit the HSDB record page.
SRP: Contaminated protective clothing should be segregated in a manner such that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.
PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Vertical laminar-flow biological safety cabinets may be used for containment of in vitro procedures ... provided that the exhaust air flow is sufficient to provide an inward air flow at the face opening of the cabinet, & contaminated air plenums that are under positive pressure are leak-tight. Horizontal laminar-flow hoods or safety cabinets, where filtered air is blown across the working area towards the operator, should never be used ... Each cabinet or fume cupboard to be used ... should be tested before work is begun (eg, with fume bomb) & label fixed to it, giving date of test & avg air-flow measured. This test should be repeated periodically & after any structural changes. /Chemical Carcinogens/
For more Preventive Measures (Complete) data for Dibenzo(a,i)pyrene (11 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,i)pyrene (6 total), please visit the HSDB record page.
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
PRECAUTIONS FOR "CARCINOGENS": ... dispensers of liq detergent ... Safety pipettes ... for all pipetting. ... In animal laboratory ... protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators ... when working with particulates or gases, & disposable plastic aprons ... gowns ... /should be/ of distinctive color ... /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... Clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/
Respirator Recommendations: Emergency or planned entry into unknown concentrations or IDLH conditions: /Coal tar pitch volatiles/[Table#4716]
Respirator Recommendations: Escape: /Coal tar pitch volatiles/[Table#4717]
For more Personal Protective Equipment (PPE) (Complete) data for Dibenzo(a,i)pyrene (6 total), please visit the HSDB record page.
Several well-documented examples of human exposure to carcinogens involve complex mixtures of polycyclic aromatic hydrocarbons (PAHs). Although the biological properties of many pure polycyclic aromatic hydrocarbons have been investigated, less is known about their effects when present as components of mixtures. As the ability to form DNA adducts in vivo is generally indicative of carcinogenic activity of polycyclic aromatic hydrocarbons, ... DNA binding potencies of dibenzo[a,e]pyrene (DB(a,e)P), dibenzo[a,h]pyrene (DB(a,h)P), dibenzo[a,i]pyrene (DB(a,i)P), dibenzo[a,l]pyrene (DB(a,l)P) and benzo[a]pyrene (B(a)P) /were measured/ when /they were/ applied topically, either singly or in combination, to the skin of male Parkes mice. DNA isolated from the skin and lungs was analyzed by 32P-postlabelling. The adducts formed by each polycyclic aromatic hydrocarbon exhibited markedly different chromatographic mobilities on polyethyleneimine-cellulose TLC plates. The relative binding potencies of the compounds in both skin and lungs were: dibenzo[a,l]pyrene > dibenzo[a,i]pyrene > dibenzo[a,e]pyrene, in good agreement with their reported carcinogenicities in mouse skin. The majority of adducts were removed from DNA within 21 days of treatment, but low levels of adducts were found to persist for at least 3 months in both tissues. When dibenzo[a,l]pyrene, dibenzo[a,e]pyrene and benzo[a]pyrene were applied together to mouse skin, a total binding 31% lower than expected was detected, while with a mixture of dibenzo[a,e]pyrene and benzo[a]pyrene the binding to DNA in skin was 65% higher than expected from the binding levels of the carcinogenes when applied singly. Other binary combinations of these three polycyclic aromatic hydrocarbons gave adduct levels similar to the sum of the binding levels of the individual components when applied singly. The results demonstrate the usefulness of 32P-post-labelling for the assessment of the DNA binding potencies of polycyclic aromatic hydrocarbons in mouse tissues, and for the detection of interactions between components of mixtures of carcinogens.
Ferulic, caffeic, chlorogenic, and ellagic acids, four naturally occurring plant phenols, inhibit the mutagenicity and cytotoxicity of (+/-)-7beta,8alpha-dihydroxy-9alpha, 10alpha-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (B[a]P 7,8-diol-9,10-epoxide-2), the only known ultimate carcinogenic metabolite of benzo[a]pyrene. The mutagenicity of 0.05 nmol of B[a]P 7,8-diol-9,10-epoxide-2 in strain TA100 of Salmonella typhimurium is inhibited 50% by incubation of the bacteria and the diol epoxide with 150 nmol of ferulic acid, 75 nmol of caffeic acid, 50 nmol of chlorogenic acid or, most strikingly, 1 nmol of ellagic acid in the 0.5-ml incubation mixture. A 3-nmol dose of ellagic acid inhibits mutation induction by 90%. Ellagic acid is also a potent antagonist of B[a]P 7,8-diol-9,10-epoxide-2 in Chinese hamster V79 cells. Mutations to 8-azaguanine resistance induced by 0.2 uM diol epoxide are reduced by 50% when tissue culture media also contains 2 uM ellagic acid. Similar to results obtained with the bacteria, ferulic, caffeic, and chlorogenic acids are approximately two orders of magnitude less active than ellagic acid in the mammalian cell assay. The antimutagenic effects of the plant phenols result from their direct interaction with B[a]P 7,8-diol-9,10-epoxide-2, because a concentration-dependent increase in the rate of diol epoxide disappearance in cell-free solutions of 1:9 dioxane/water, pH 7.0, is observed with all four phenols. In parallel with the mutagenicity studies, ellagic acid is 80-300 times more effective than the other phenols in accelerating the disappearance of B[a]P 7,8-diol-9,10-epoxide-2. Ellagic acid at 10 uM increases the disappearance of B[a]P 7,8-diol-9,10-epoxide-2 by approximately 20-fold relative to the spontaneous and hydronium ion-catalyzed hydrolysis of the diol epoxide at pH 7.0. Ellagic acid is a highly potent inhibitor of the mutagenic activity of bay-region diol epoxides of benzo[a]pyrene, dibenzo[a,h]pyrene, and dibenzo[a,i]pyrene, but higher concentrations of ellagic acid are needed to inhibit the mutagenic activity of the chemically less reactive bay-region diol epoxides of benz[a]anthracene, chrysene, and benzo[c]phenanthrene. These studies demonstrate that ellagic acid is a potent antagonist of the adverse biological effects of the ultimate carcinogenic metabolites of several polycyclic aromatic hydrocarbons and suggest that this naturally occurring plant phenol, normally ingested by humans, may inhibit the carcinogenicity of polycyclic aromatic hydrocarbons.
LC50; Species: Daphnia magna (Water flea) age <24 hr neonate; Conditions: freshwater, aquatic, visible light plus UVA, 20 °C; Concentration: 17.2 nM for 48 hr /98% purity/
LC50; Species: Daphnia magna (Water flea) age <24 hr neonate; Conditions: freshwater, aquatic, simulated solar radiation, 20 °C; Concentration: 2.27 nM for 48 hr /98% purity/
TERRESTRIAL FATE: Based on a classification scheme(1), an experimental Koc value of 5.1X10+5(2) indicates that dibenzo(a,i)pyrene is expected to be immobile in soil(SRC). Volatilization of dibenzo(a,i)pyrene from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.4X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Dibenzo(a,i)pyrene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.8X10-11 mm Hg at 25 °C(SRC), determined from a fragment constant method(3). Dibenzo(a,i)pyrene had biological degradation half-lives of 371 days and 232 days in soil die-away tests using two sandy loam soils(4). In general, polynuclear aromatic hydrocarbons (PAHs) with five or more benzene rings may not biodegrade readily(5). PAHs with four or more rings, such as dibenzo(a,i)pyrene, are expected to be resistant to biodegradation(6). Dibenzo(a,i)pyrene absorbs strongly at wavelengths >290 nm(7) and, therefore, is expected to be susceptible to direct photolysis on soil surfaces exposed to sunlight(SRC). Photodegradation of dibenzo(a,i)pyrene was observed in a soil degradation test(4).
AQUATIC FATE: Based on a classification scheme(1), an experimental Koc value of 5.1X10+5(2), indicates that dibenzo(a,i)pyrene 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 1.4X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 9600(SRC), from an estimated log Kow of 7.28(4) and a regression-derived equation(4), suggests the potential for bioconcentration in aquatic organisms is very high, provided the compound is not metabolized by the organism(SRC). However, it 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(6). In general, polynuclear aromatic hydrocarbons (PAHs) with five or more benzene rings may not biodegrade readily(7). PAHs with four or more rings, such as dibenzo(a,i)pyrene, are expected to be resistant to biodegradation(8). Dibenzo(a,i)pyrene absorbs strongly at wavelengths >290 nm(9) and, therefore, is expected to be susceptible to direct photolysis on water surfaces exposed to sunlight(SRC). Dibenzo(a,i)pyrene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dibenzo(a,i)pyrene, which has an estimated vapor pressure of 1.8X10-11 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist almost entirely in the particulate phase in the ambient atmosphere. Based on an estimated super-cooled vapor pressure of 1.2X10-8 mm Hg at 25 °C(2), a small percentage of dibenzo(a,i)pyrene may exist in the vapor phase in the ambient atmosphere(1). Similar PAHs have been detected in the vapor phase in ambient air(3,4). Vapor-phase dibenzo(a,i)pyrene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 7.7 hours(SRC), calculated from its rate constant of 5.0X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Particulate-phase dibenzo(a,i)pyrene may be removed from the air by wet and dry deposition(SRC). Dibenzo(a,i)pyrene absorbs strongly at wavelengths >290 nm(5,6) and, therefore, is expected to be susceptible to direct photolysis by sunlight(SRC).
The average dibenzo(a,i)pyrene concentration in margarine, spinach, and kale was determined to be 0.2, <0.03, and <0.07 ug/kg, respectively(1). Dibenzo(a,i)pyrene was detected in smoked sausages at a level of 0.4 ppb(2). Trace levels of dibenzo(a,i)pyrene were identified in charbroiled hamburgers(3).
Eighteen nations in Europe submitted almost 10,000 results (9,714) for PAH levels in different food commodities. An evaluation of these data was performed in June 2007 and updated in June 2008. Dibenzo(a,i)pyrene was detected above detection limits (not reported) in 4.9% of 2,471 samples at lower and upper bound mean concentrations of 0.04 and 0.17 ug/kg. In a comparison of 1,375 food products for 15 priority PAHS, dibenzo(a,i)pyrene was detected above detection limits in 7.6% of all samples at lower and upper bound mean concentrations of 0.06 and 0.15 ug/kg(1).
IDENTIFICATION AND USE: Dibenzo(a,i)pyrene (DB(a,i)P) forms greenish-yellow needles, prisms or lamellae. It is used as an experimental carcinogen. HUMAN EXPOSURE AND TOXICITY: DB(a,i)P is reasonably anticipated to be a human carcinogen. DB(a,i)P was mutagenic in the Ames test, in the presence of hepatic post-mitochondrial preparations isolated from man. ANIMAL STUDIES Groups of 20 female mice received 10 dermal applications of DB(a,i)P (total doses, 100 ug and 500 ug). Ten days after initiation had been completed, all animals received applications of 2.5 ug 12-O-tetradecanoylphorbol-13-acetate (TPA) for 20 weeks. Mice treated with 100 ug DB(a,i)P had a 40% skin tumor incidence (average of 0.5 skin tumors/mouse), whereas the group treated with 500 ug DB(a,i)P had an 85% skin tumor incidence (average of 5.8 skin tumors/mouse). A group of 20 female rats received intramamillary injection of 4 umol (1.2 mg)/gland DB(a,i)P and another was untreated. At the end of the study, 18/19 rats in the DB(a,i)P-treated group had developed fibrosarcomas (2.4 tumors/tumor-bearing rat), 11/19 rats had mammary adenocarcinomas (1.4 tumors/tumor-bearing rat) and 1/19 had mammary adenofibromas (two tumors). In contrast, 2/20 rats in the untreated group had developed mammary epithelial tumors (one adenofibroma and one adenocarcinoma) but no fibrosarcomas. Dermal exposure to DB(a,i)P caused benign or malignant skin tumors (papilloma or epithelioma) in mice, and subcutaneous injection caused cancer at the injection site (sarcoma) in mice and hamsters. DB(a,i)P was mutagenic in the in the Ames test, in the presence of hepatic post-mitochondrial preparations isolated from the mouse, rat, hamster, and pig. It did not induce DNA damage in mammalian cells in vitro. ECOTOXICITY STUDIES: DB(a,i)P induced 7-ethoxyresorufin-o-deethylase activity in the rainbow trout liver cell line.
/AQUATIC SPECIES/ The relative CYP1A induction potencies, determined as ethoxyresorufin-O-deethylase (EROD) activity, and the cytotoxicities of 19 compounds with one to six benzene rings, mixtures of polycyclic aromatic hydrocarbons (PAHs), and contaminated landfill leachates have been determined in the permanent fish hepatoma cell line PLHC-1. No CYP1A induction was observed with benzene, naphthalene, anthracene, acenaphthene, benzo[g,h,i]perylene, and fluorene and low induction was found with fluoranthene and phenanthrene. All other PAHs with three and more benzene rings led to a concentration-related induction of CYP1A, with rebound decreases at high concentrations resulting in bell-shaped concentration-activity curves. Fish-related induction equivalency factors (IEFs) were estimated for all PAHs on the basis of EC50 values of their EROD activities and are reported here for the first time. The following order of decreasing IEFs was found: dibenz[a,h]anthracene > dibenzo[a,i]pyrene > benzo[k]fluoranthene > 3-methylcholanthrene > benzo[a]pyrene > benzo[e]pyrene > chrysene > 7,12-dimethylbenz[a]anthracene > perylene > benz[a]anthracene > pyrene. In contrast to the EROD activity, the immunodetectable protein content determined by ELISA showed a concentration-dependent increase. The interaction of PAHs in mixtures of up to eight individual compounds was additive based on their EROD activities. In landfill leachates, determined induction equivalents (IEQ) were significantly higher than calculated IEQs based on analytical measurements, which indicates additional unknown inducing compounds present in leachates. This study shows that the PLHC-1 cell in vitro system serves as an integrative bioanalytical tool in the ecotoxicological evaluation of aquatic environmental samples contaminated with CYP1A-inducing compounds.
/AQUATIC SPECIES/ Along with 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD), 24 unsubstituted polycyclic aromatic hydrocarbons (PAHs) were evaluated for their ability to induce 7-ethoxyresorufin-o-deethylase (EROD) activity in the rainbow trout liver cell line RTL-W1. When the duration and cell density of exposure were increased, the EC(50) for EROD induction was relatively constant for TCDD, but increased for PAHs. Regardless of exposure conditions, EROD activity was not induced by 9 PAHs: naphthalene, phenanthrene, anthracene, pyrene, perylene, acenaphthylene, acenaphthene, fluorene, and fluoranthene. Two PAHs, benzo[g,h,i]perylene and coronene, induced EROD activity inconsistently. The remaining 13 PAHs consistently induced EROD activity. The EC(50)s for induction exhibited approximately a 110-fold range. The order of potency, from most to least potent, was benzo[k]fluoranthene, dibenzo[a,i]pyrene, dibenzo [a,h]anthracene, benzo[a]pyrene, indeno[1,2,3-cd]pyrene, benzo[b]fluoranthene, pentacene, benzo[b]anthracene, benzo[b] fluorene, chrysene, benzo[a]anthracene, benzo[e]pyrene, and triphenylene. When the induction potency was expressed relative to TCDD, the toxic equivalency factors (TEFs) ranged from 0.001 to 0.000 01. When expressed relative to benzo[a]pyrene, the TEFs ranged from 3.44 to 0. 03.
Dibenzo(a,i)pyrene has been identified in coke oven emissions, with a concentration of 493.3 to 693.2 ug/g per sample(1). Dibenzo(a,i)pyrene was detected in stack emissions from industrial coal combustion facilities(2). Monitoring of indoor air for emissions from open-fire, unvented coal combustion detected dibenzo(a,i)pyrene in particulate collections (1.4 ug/cu m), but not in volatile gas collection(3). Mesquite wood smoke contained dibenzo(a,i)pyrene emitted at a rate of ug/kg wood burned(4). Dibenzo(a,i)pyrene was detected at trace amounts in automobile exhaust gas(5). Dibenzo(a,i)pyrene was detected in the exhaust of two diesel and two gasoline-fuelled light-duty vehicles(6).
PRECAUTIONS FOR "CARCINOGENS": ... In relation specifically to cancer hazards, there are at present no health monitoring methods that may ensure the early detection of preneoplastic lesions or lesions which may preclude them. Whenever medical surveillance is indicated, in particular when exposure to a carcinogen has occurred, ad hoc decisions should be taken concerning additional tests that might become useful or manditory. /Chemical Carcinogens/
Recommended medical surveillance: The following medical procedures should be made available to each employee who is exposed to coal tar pitch volatiles at potentially hazardous levels: Initial Medical Examination: A complete history and physical examination: The purpose is to detect existing conditions that might place the exposed employee at increased risk, and to establish a baseline for future health monitoring. Examination of the oral cavity, respiratory tract, bladder, and kidneys should be stressed. The skin should be examined for evidence of chronic disorders, for premalignant and malignant lesions, and evidence of hyperpigmentation or photosensitivity. /Coal tar pitch volatiles/
Initial Medical Examination: Urinalysis: Coal tar pitch volatiles are associated with an excess of kidney and bladder cancer. A urinalysis should be obtained to include at a minimum: specific gravity, albumin, glucose, and a microscopic /examination/ on centrifuged sediment, as well as a test for red blood cells. /Coal tar pitch volatiles/
Initial Medical Examination: Urinary cytology: Coal tar pitch volatiles are associated with an excess of kidney and bladder cancer. Employees having 5 or more years of exposure or who are 45 years of age or older should have a urinary cytology examination. /Coal tar pitch volatiles/
For more Medical Surveillance (Complete) data for Dibenzo(a,i)pyrene (10 total), please visit the HSDB record page.
U064; As stipulated in 40 CFR 261.33, when dibenzo(a,i)pyrene, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).
Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV.D.3.b).
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/.
PAHs 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. There are more than 100 different PAHs. PAHs generally occur as complex mixtures (for example, as part of combustion products such as soot), not as single compounds. PAHs usually occur naturally, but they can be manufactured as individual compounds for research purposes; however, not as the mixtures found in combustion products. ... Others are contained in asphalt used in road construction. They can also be found in substances such as crude oil, coal, coal tar pitch, creosote, and roofing tar. They are found throughout the environment in the air, water, and soil. They can occur in the air, either attached to dust particles or as solids in soil or sediment. /Polycyclic aromatic hydrocarbons/
Coal tar pitch volatiles are products of the distillation of bituminous coal and contain polynuclear aromatic hydrocarbons. /Coal tar pitch volatiles/
VerwendenDibenzo[a,i]pyrene is a polycyclic aromatic hydrocarbon (PAH) with potent carcinogenic activity. Dibenzo[a,i]pyrene was shown to induce DNA adduction, tumorigenicity as well as Ki-ras oncogene mutations in strain A/J mouse lung. Dibenzo[a,i]pyrene has been shown to be present in cigarette smoke condensate and in automobile exhaust gas in small quantities.