Dibenzo[a,e]pyrene

302.37

302.37

205-891-1

SAC8PEK62H

2811

DTXSID3052690

C44369

Pale yellow needles from xylene|Yellow crystals

2902909090

0

7.28 (est)

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

1.3±0.1 g/cm3

233.5 °C

552.3±17.0 °C at 760 mmHg

282.0±15.1 °C

1.913

Slightly soluble in ethanol, acetone, benzene, acetic acid; soluble in toluene and concentrated sulfuric acid

2-8°C

5.2X10-11 mm Hg at 25 deg C (est)

Henry's Law constant = 1.4X10-8 atm-cu m/mole at 25 °C (est)

Oxidized by sodium dichromate in glacial acetic acid, first to dibenzo(a,e)pyrene-8,14-quinone and then to 9,14-dioxo-9,14-dihydro-dibenz(a,c)anthracene carboxylic acid. Reacts with bromine or acetyl chloride to give mono substitution products, 1-bromodibenzo(a,e)pyrene or 1-acetodibenzo(a,e)pyrene.|Enthalpy of sublimation: 146.4 kJ/mol (414-506 K); Enthalpy of fusion: 32.1 kJ/mol (517.9 K)

Dust/air mixtures may ignite and explode. Insoluble in water.

Hydrocarbons, Aromatic

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

III

6.1(b)

2811

40-41

26-39

QL0175000

Xn

Stable under recommended storage conditions.[Sigma-Aldrich; Safety Data Sheet for Dibenzo

P201-P202-P281-P308 + P313-P405-P501

H341-H350

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|PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/|For more Disposal Methods (Complete) data for DIBENZO(A,E)PYRENE (8 total), please visit the HSDB record page.

Oxidized by sodium dichromate in glacial acetic acid, first to dibenzo[a,e]pyrene-5,6-quinone and then to 9,14-dioxo-9,14-dihydrodibenz[a,c]anthrancene carboxylic acid. ... Reacts with bromine or acetyl chloride to give the mono substitution products, 7-bromodibenzo[a,e]pyrene or 7-acetodibenzo[a,e]pyrene|Strong oxidizers. /Coal tar pitch volatiles/

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,e)pyrene (192-65-4) 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]

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. For electric vehicles or equipment, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. (ERG, 2016)

|Danger|H318: Causes serious eye damage [Danger Serious eye damage/eye irritation]|P201, P202, P273, P280, P281, P305+P351+P338, P308+P313, P310, P405, and P501

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. (ERG, 2016)|Eye/face protection: Face shield and safety glasses. 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|Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.[Sigma-Aldrich; Safety Data Sheet for Dibenzo|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face particle respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).[Sigma-Aldrich; Safety Data Sheet for Dibenzo|For more Personal Protective Equipment (PPE) (Complete) data for DIBENZO(A,E)PYRENE (9 total), please visit the HSDB record page.

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 firefighting 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 vapors, 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|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/

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, 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|Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.[Sigma-Aldrich; Safety Data Sheet for Dibenzo|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.[Sigma-Aldrich; Safety Data Sheet for Dibenzo|For more Preventive Measures (Complete) data for DIBENZO(A,E)PYRENE (17 total), please visit the HSDB record page.

PRECAUTIONS FOR "CARCINOGENS": Procurement ... of unduly large amt ... should be avoided. To avoid spilling, carcinogens should be transported in securely sealed glass bottles or ampoules, which should themselves be placed inside strong screw-cap or snap-top container that will not open when dropped & will resist attack from the carcinogen. Both bottle & the outside container should be appropriately labelled. ... National post offices, railway companies, road haulage companies & airlines have regulations governing transport of hazardous materials. These authorities should be consulted before ... material is shipped. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": When no regulations exist, the following procedure must be adopted. The carcinogen should be enclosed in a securely sealed, watertight container (primary container), which should be enclosed in a second, unbreakable, leakproof container that will withstand chem attack from the carcinogen (secondary container). The space between primary & secondary container should be filled with absorbent material, which would withstand chem attack from the carcinogen & is sufficient to absorb the entire contents of the primary container in the event of breakage or leakage. Each secondary container should then be enclosed in a strong outer box. The space between the secondary container & the outer box should be filled with an appropriate quantity of shock-absorbent material. Sender should use fastest & most secure form of transport & notify recipient of its departure. If parcel is not received when expected, carrier should be informed so that immediate effort can be made to find it. Traffic schedules should be consulted to avoid ... arrival on weekend or holiday ... /Chemical Carcinogens/

Permissible Exposure Limit: Table Z-1 8-hr Time Weighted Avg: 0.2 mg/cu m. /Coal tar pitch volatiles (benzene soluble fraction), anthracene, BaP, phenanthrene, acridine, chrysene, pyrene/

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/

Dibenzo(a,e)pyrene was detected as a minor constituent of a coal tar sample (SM 1597) from a medium crude coke oven tar at unreported concentrations(1). Dibenzo(a,e)pyrene has been detected in tobacco smoke, gasoline exhaust, diesel exhaust, and curing smoke(2,3). Dibenzo(a,e)pyrene was detected in the stack emissions of waste incinerators and in coal combustion stack emissions at unreported concentrations(4). Monitoring of indoor air for emissions from open-fire, unvented coal combustion detected dibenzo(a,e)pyrene in particulate collections (4.0 ug/cu m), but not in volatile gas collection(5). Dibenzo(a,e)pyrene was detected in the exhaust of two diesel and two gasoline-fuelled light-duty vehicles(6).

SEDIMENT: Sediment was collected from the Black River near the outfall of coking ovens used for the production of steel (Lorain, Ohio); one of nine subfractions of an HPLC fractionation procedure indicated the presence of dibenzo(a,e)pyrene at unreported concentrations(1). Sediment from Dokai Bay in north Kyushu, Japan, collected September, 1990, contained dibenzo(a,e)pyrene at unreported concentrations(2). Sediment collected from Sagamore Lake in New York State's Adirondack Park in March 1978 contained dibenzo(a,e)pyrene at concentrations of 120 ng/g dry weight 0-4 cm from the surface of sediment to not detected at 12-17 cm depth(3). Sediment collected from Woods Lake in New York State's Adirondack Park in March 1978 contained dibenzo(a,e)pyrene at concentrations of 390 ng/g dry weight 0-4 cm from the surface of sediment to not detected at 8-11 cm depth(3). Dibenzo(a,e)pyrene was qualitatively detected in surface sediments collected in Niigata, Japan in Sept 1995(4).|SOIL: Dibenzo(a,e)pyrene was detected in a coal tar contaminated soil from New Jersey at a general concentration of 28 ug/g soil for dibenzofluoranthrene, naphtho(1,2-k)fluoranthrene, and dibenzo(a,e)pyrene(1). Soil samples collected at 30 sampling sites along roadsides in the city of Chiang-Mai, Thailand during Feb 1996 contained arithmetic and geometric mean dibenzo(a,e)pyrene concentrations of 30.6 and 27.7 ng/g respectively(2). Dibenzopyrene (isomers not specified)was detected in surface sediments collected at 12 of 14 sampling stations in the Black Sea at concentrations of 5 to 79 ng/g(3).

URBAN/SUBURBAN: Dibenzopyrene was detected in urban air samples from Kokkola, Finland in the particulate phase (concentration = not detected to 0.7 ng/cu m)(1). Dibenzo(a,e)pyrene was detected as a particulate phase pollutant, concentrations of ng/cu m air, in Camden, NJ (summer max=1.35, winter max = 6.84), Elizabeth, NJ (summer max = 27.1, winter max = 16.7), Newark, NJ (summer max = 2.27, winter max = 17.4), and Ringwood, NJ (summer max = 2.77, winter max = 0.52) from the summer of 1981 to the winter of 1983(2). Dibenzo(a,e)pyrene was reported in samples of airborne particulates from Hamilton, Ontario at concentrations of 683 to 4159 ng/1000 cu m(3). Dibenzo(a,e)pyrene was detected in an air filter sample taken from the Baltimore Harbor Tunnel (May 1975, concentration found in particulate matter = 7 ng/cu m)(4). Dibenzo(a,e)pyrene was detected in aerosol samples collected at Kenmore Square (Boston, MA) in 1994 at a concentration of 0.133 ng/cu m(5). Air particulate samples collected at three different locations in Stockholm, Sweden in 2003 and 2005 contained dibenzo(a,e)pyrene levels 9.3-57 pg/cu m(6). One airborn particulate sample collected Washington DC in the late 1970s (SRM 1649) contained a dibenzo(a,e)pyrene concentration of 0.37 ug/g(7). Dibenzo(a,e)pyrene was detected in atmospheric air particulates collected in Beijing, China before, during and after the 2008 Beijing Olympic Gamse(8).|INDOOR AIR: Dibenzo(a,e)pyrene was detected in indoor air samples taken from residential homes in Xuan Wei, China which used smokey coal (4.9-18 ug dibenzo(a,e)pyrene/cu m air), smokeless coal (0.17-5.8 ug dibenzo(a,e)pyrene/cu m air), or wood (<0.01-0.55 ug dibenzo(a,e)pyrene/cu m air)(1). The concentration of dibenzo(a,e)pyrene in indoor air samples collected in Shimizu, Japan in the summer of 2000 and winter of 2001 was 0.042 and 0.039 ng/cu m respectively(8).|RURAL/REMOTE: The measured integrated anthropogenic deposition of dibenzo(a,e)pyrene for Sagamore Lake and Woods Lake in New York State's Adirondack Park was measured as 80 and 160 ng/sq cm, respectively(1).|SOURCE DOMINATED: Dibenzo(a,e)pyrene was not detected in air collected in Bahrain during the burning of oil wells in Kuwait (1991), with a study detection limit of 0.05 ng/cu m(1). Air samples collected in highway toll station booths had a mean dibenzopyrene concentration of 39.8 ng/cu m(2).

Dibenzo(a,e)pyrene was detected in smoke particulates from 10 brands of US cigarettes at levels 1.5-2.6 ng/cigarette(1). House dust samples collected from the Research Triangle Park area of North Carolina in Nov 1996 contained dibenzo(a,e)pyrene concentrations ranging from <0.05 to 0.30 ug/g in various particle size fractions of the dust(2). Dibenzo(a,e)pyrene was detected in extracts of soot deposits from coal-burning stoves in several homes of Henan Province, China at levels of 0.021 to 236 ug/g soot(3).

IDENTIFICATION AND USE: Dibenzo(a,e)pyrene (DB(a,e)P) forms yellow crystals. It is used as experimental carcinogen. HUMAN EXPOSURE AND TOXICITY: DB(a,e)P tested positive for mutagenicity in a forward mutation assay based on human B-lymphoblastoid cells. ANIMAL STUDIES: A group of 21 female mice received a single dermal application of 800 nmol (242 ug) DB(a,e)P. At the end of the experiment, 5/21 mice had developed seven skin papillomas (0.3 papillomas/mouse) and 2/23 mice in the control group had developed one skin papilloma (0.1 papilloma/mouse). The first skin papillomas appeared after 15 weeks in the DB(a,e)P-treated group compared with 20 weeks in the control group. D(a,e)P was mutagenic to the Salmonella typhimurium strain TA100 (his-/his+) when added at a concentration of 100 ug/plate with metabolic activation.

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, we have compared the 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), when applied topically, either singly or in combination, to the skin of male Parkes mice. DNA isolated from the skin and lungs was analyzed by (32)P-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 (32)P-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.

Persons with existing skin disorders may be more susceptible to the effects of /coal tar pitch volatiles/. /Coal tar pitch volatiles/

Dibenzo(a,e)pyrene occurs in fossil fuels(1). Sources of PAH release (including dibenzo(a,e)pyrene) include forest fires and volcanoes(2,3).

There is no commercial production or known use for dibenzo(a,e)pyrene(1,2). Dibenzo(a,e)pyrene occurs ubiquitously in products of incomplete combustion(1). It is present as a component of the total content of PAHs in the environment(2). Dibenzo(a,e)pyrene occurs in tobacco smoke(1,3), gasoline and diesel engine exhaust(4), stack emissions of waste incinerators, in coal combustion stack emissions, and in curing smoke(5). Other sources of PAH release include heating with wood or other biomass fuels(6). Barbecued, grilled, broiled, roasted, baked, and fried cooking of foods releases PAHs(6). Dibenzo(a,e)pyrene occurs in emissions from open-fire coal combustion and in coal tar and soot(7,8).

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)pyrene is expected to be immobile in soil(SRC). Volatilization of dibenzo(a,e)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(2). Dibenzo(a,e)pyrene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.2X10-11 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Dibenzo(a,e)pyrene absorbs strongly at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis on soil surfaces exposed to sunlight(SRC). Biodegradation data in soil were not available(SRC, 2016). However, PAHs with five or more benzene rings may not biodegrade readily(3).|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)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(2). According to a classification scheme(4), an estimated BCF of 9700(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). 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(5). Dibenzo(a,e)pyrene absorbs strongly at wavelengths >290 nm(7) and, therefore, may be susceptible to direct photolysis on water surfaces exposed to sunlight(SRC). Dibenzo(a,e)pyrene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Biodegradation data in water were not available(SRC, 2016). However, PAHs with five or more benzene rings may not biodegrade readily(6).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dibenzo(a,e)pyrene, which has an estimated vapor pressure of 5.2X10-11 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 1.3X10-8 mm Hg at 25 °C(2), a small percentage of dibenzo(a,e)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,e)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,e)pyrene may be removed from the air by wet and dry deposition(SRC). Dibenzo(a,e)pyrene has been detected in dry atmospheric deposition(5). Dibenzo(a,e)pyrene absorbs strongly at wavelengths >290 nm(6,7) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of dibenzo(a,e)pyrene with photochemically-produced hydroxyl radicals has been estimated as 5.0X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 7.7 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Dibenzo(a,e)pyrene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Dibenzo(a,e)pyrene absorbs strongly at wavelengths >290 nm(3,4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 9700 was calculated in fish for dibenzo(a,e)pyrene(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). 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(3). A measured fish biotransformation half-life of 1.1 days has been reported for the analogous compound benzo(a)pyrene(4).

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

The Henry's Law constant for dibenzo(a,e)pyrene is estimated as 1.4X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that dibenzo(a,e)pyrene is expected to be essentially nonvolatile from water surfaces(2). Dibenzo(a,e)pyrene's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Dibenzo(a,e)pyrene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.2X10-11 mm Hg(SRC), determined from a fragment constant method(1).

Dibenzo(a,e)pyrene was detected in beef (70% lean) patties at 1 ug/kg cooked over mesquite. It was not detected in beef patties (80% and 90% lean beef) cooked over mequite or hardwood charcoal. It was detected in the smoke condensate at 4 ug/kg of mesquite but not in the charcoal smoke(1). Dibenzo(a,e)pyrene was detected in canola and/or soya cooking oil at trace levels; soya oil, 0.3 ug/kg; corn oil, 0.3 ug/kg(2). Dibenzo(a,e)pyrene was detected at concentrations of 1.84-2.50 mg/kg in 3 of 5 olive pomace oil collected in Spain prior to 2001 to 2002(3).|Sources of PAHs in the diet (which includes dibenzo(a,e)pyrene) include barbecued, grilled, broiled, and smoke-cured meats; roasted, baked, and fried foods (prepared by high-temperature processing); breads, cereals, and grains (at least in part from gas or flame drying of grains); and vegetables grown in contaminated soil or with surface contamination from atmospheric deposition of PAH(1). /Polyaromatic hydrocarbons/|Eighteen nations in Europe submitted almost 10,000 results (9,714) for PAH levels in different food commodities(1). An evaluation of these data was performed in June 2007 and updated in June 2008. Dibenzo(a,e)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(1). In a comparison of 1,375 food products for 15 priority PAHS, dibenzo(a,e)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).

Occupational exposure to dibenzo(a,e)pyrene may occur through inhalation and dermal contact with this compound at workplaces where dibenzo(a,e)pyrene is produced as a product of incomplete combustion of fossil fuels. Monitoring data indicate that the general population may be exposed to dibenzo(a,e)pyrene via inhalation of ambient air, inhalation of tobacco smoke, ingestion of food and dermal contact with particulate matter resulting from combustion(SRC). Occupational and general population exposure to PAHs, such as dibenzo(a,e)pyrene, generally occurs as a mixture(1). Sources of PAHs in the diet include barbecued, grilled, broiled, and smoke-cured meats; roasted, baked, and fried foods (prepared by high-temperature processing); breads, cereals, and grains (at least in part from gas or flame drying of grains); and vegetables grown in contaminated soil or with surface contamination from atmospheric deposition of PAH(2).|The primary routes of potential human exposure to PAHs are inhalation of polluted air, wood smoke, and tobacco smoke, as well as ingestion of contaminated water, foodstuffs, and foods normally containing ug quantities of PAHs. ... Potential human exposure to PAHs may also occur by dermal contact with PAH-containing products such as creosote-treated wood products, asphalt roads, or coal tar. Consumers may be exposed to PAHs that are present in dermatological preparations containing coal tar ... . /Polycyclic aromatic hydrocarbons/

... The NADPH-supported metabolism of dibenzo[a,e]pyrene (DB[a,e]P) and dibenzo[a,l]pyrene (DB[a,l]P) was conducted with uninduced and 3-methylcholanthrene-induced rat liver microsomes. ... The metabolites of dibenzo(a,e)pyrene with induced microsomes were dibenzo(a,e)pyrene 3,4-dihydrodiol, 3-hydroxydibenzo(a,e)pyrene, 7-hydroxydibenzo(a,e)pyrene, and 9-hydroxydibenzo(a,e)pyrene. Some of these metabolites are very useful in assessing possible pathways of activation in the initiation of cancer.

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)|Carcinogens

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)

Immediate First Aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aromatic hydrocarbons and related compounds/|Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary. ... For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 L of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aromatic hydrocarbons and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aromatics hydrocarbons and related compounds/

/GENOTOXICITY/ Polycyclic aromatic compounds (PAC) are ubiquitous pollutants in urban air that may pose risks to human health. In order to better assess the health risks associated with this class of compounds, a total of 67 polycyclic aromatic compounds that either have been identified (55) or are suspected to be present (12) in urban aerosol samples were tested for mutagenicity in a forward mutation assay based on human B-lymphoblastoid cells. The cell line used (designated hlAlv2) constitutively expresses the cytochrome p4501Al, which is known to be necessary for the metabolism of many promutagens. The polycyclic aromatic compounds tested included 39 polycyclic aromatic hydrocarbons (PAH), 19 oxygen-containing polycyclic aromatic hydrocarbons (oxy-PAH) and nine NO2-substituted polycyclic aromatic hydrocarbons (nitro-PAH). A total of 26 polycyclic aromatic hydrocarbons were mutagenic. In comparing the minimum mutagenic concentrations of the mutagenic polycyclic aromatic hydrocarbons with that of benzo(a)pyrene (B[a]P) it was found that dibenzo(a,l)pyrene (DB(al)P), cyclopenta(c,d))pyrene (CPP), naphtho(2,1-a)pyrene, dibenzo(a,e)pyrene (DB(ae)P) and l-methylbenzo(a)pyrene were 24 + or - 21, 6.9 + or - 4.2, 3.2 + or - 3.0, 2.9 + or - 2.9 and 1.6 + or - 1.4 times, respectively, more mutagenic than benzo(a)pyrene, and that dibenzo(a,k)fluoranthene and benzo(a)pyrene were approximately equally mutagenic. The 19 other mutagenic polycyclic aromatic hydrocarbons were between tested only phenalenone, 7H-benz(d,e)anthracen-7-one, 3-nitro-6H-dibenzo(b,d)pyran-6-one, cyclopenta(c,d)pyren-3(4H)-one, 6H-benzo(c,d)pyren-6-one (BPK) and anthanthrenequinone were mutagenic; however, with the exception of 6H-benzo(c,d)pyren-6-one, these were over 50 times less active than benzo(a)pyrene. 6H-benzo(c,d)pyren-6-one was benzo(a)pyrene. Seven of the nitro-polycyclic aromatic hydrocarbons were mutagenic including 9-nitroanthracene, l-nitrofluoranthene, 3-nitrofluoranthene, 1,3-dinitropyrene, 1,6-dinitropyrene (1,6-DNP) and 1,8-dinitropyrene. 1,6-dinitropyrene wasnic nitro-polycyclic aromatic hydrocarbons were between 20 and 380 times less active than benzo(a)pyrene. These results are discussed in terms of their relevance for determining the most important mutagens in ambient air. Based on reported concentrations of polycyclic aromatic compounds in ambient aerosols, it is possible that cyclopenta(c,d))pyrene, dibenzo(a,e)pyrene, dibenzo(a,l)pyrene and 6H-benzo(c,d)pyren-6-one could account for a greater proportion of the mutagenicity than benzo(a)pyrene in some aerosols.|/OTHER TOXICITY INFORMATION/ ... The primary objectives of this study are to investigate the risk of 22 combined atmospheric polycyclic aromatic hydrocarbons (PAHs) and to find major contributing compounds that can act as adequate indicators for estimating the risk. The average lifetime cancer risk for all 22 PAHs in winter was 1.7 x 10(-4) in the Yokohama residential area. Although benzo[a]pyrene has been considered to be a useful indicator in many countries, the present study also showed that benzo[a]pyrene contributed only ca. 40% of the total cancer risk for all 22 PAHs, as calculated by unit risk. Six PAHs (dibenzo[a,h]anthracene, benzo[b]fluoranthene, indeno[1,2,3-cd]perylene, dibenzo[a,h]pyrene, dibenzo[a,e]pyrene, and benzo[a]pyrene) contributed 93% of the overall risk. Therefore, these six PAHs, including the high molecular ones, would be better indicators of the risk than benzo[a]pyrene alone. The secondary objective of this study is to reveal the PAHs that are major contributors to the deposition that contribute to the total deposition of PAHs in the human respiratory tract. The results revealed that the same six PAHs identified using unit risk evaluation were large contributors in all five parts of the respiratory tracts in adult males in spite of deposition process. It was concluded that the reason for this was that these six PAHs had the same size distributions, of which the 0.43-1.1 um fraction was the largest, about 57-70% of the whole concentration.

1,2,4,5-dibenzopyrene

Dibenz(a,e)pyrene occurs ubiquitously in products of incomplete combustion; it also occurs in fossil fuels.|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/

Method: EPA-RCA 8270D; Procedure: gas chromatography/mass spectrometry; Analyte: dibenzo(a,e)pyrene; Matrix: solid waste matrices, soils, air sampling media and water; Detection Limit: 1 ug/L.|We present a unique method for the unambiguous determination of dibenzo[a,l]pyrene, dibenzo[a,e]pyrene, dibenzo[a,h]pyrene, dibenzo[a,i]pyrene, and dibenzo[e,l]pyrene in high-performance liquid chromatography (HPLC) fractions. Chemical analysis is performed via laser-excited time-resolved Shpol'skii spectroscopy with the aid of a cryogenic fiber-optic probe, pulsed tunable dye laser, spectrograph, and intensified charge-coupled device. Unambiguous identification is accomplished via wavelength time matrix formats, which give simultaneous access to spectral and lifetime information. Prior to spectroscopic analysis, HPLC fractions are pre-treated with liquid-liquid extraction or solid-liquid extraction at the tip of the fiber-optic probe. Solid-liquid extraction gives the best limits of detection, which vary from 40 pg/mL (dibenzo[a,l]pyrene) to 0.2 ng/mL (dibenzo[e,l]pyrene).|Dibenzo[a,l]pyrene is considered the most potent carcinogen of all polycyclic aromatic hydrocarbons ever tested. Its four isomers, which include dibenzo[a,e]pyrene, dibenzo[a,h]pyrene, dibenzo[a,i]pyrene, and dibenzo[e,l]pyrene, are also carcinogenic and, therefore, a potential threat to humans. The method presented here provides a direct way for their determination in water samples. The entire procedure--from water extraction to LETRSS analysis--takes less than 15 min/sample and it consumes only 100 uL of organic solvent. This fact makes our approach environmentally friendly and cost-effective. Unambiguous isomer determination is accomplished via multidimensional data formats, namely, wavelength time matrixes, excitation-emission matrixes, and time-resolved excitation-emission matrixes. The analytical figures of merit demonstrate precise and accurate analysis at the sub-parts-per-billion level. Limits of detection are at the parts-per-trillion level. The potential of this approach for real-world analysis is illustrated with a heavily contaminated water samples.|We present an accurate method for the determination of isomers of high-molecular weight polycyclic aromatic hydrocarbons co-eluted in HPLC fractions. The feasibility of this approach is demonstrated with two isomers of molecular weight 302 with identical mass fragmentation patterns, namely dibenzo[a,i]pyrene and naphtho[2,3-a]pyrene. Qualitative and quantitative analysis is carried out via laser-excited time-resolved Shpol'skii spectroscopy at liquid helium temperature. Unambiguous identification of co-eluted isomers is based on their characteristic 4.2 K line-narrowed spectra in n-octane as well as their fluorescence lifetimes. Pre-concentration of HPLC fractions prior to spectroscopic analysis is performed with the aid of gold nanoparticles via an environmentally friendly procedure. In addition to the two co-eluted isomers, the analytical figures of merit of the entire procedure were evaluated with dibenzo[a,l]pyrene, dibenzo[a,h]pyrene and dibenzo[a,e]pyrene. The analytical recoveries from drinking water samples varied between 98.2 +/- 5.5 (dibenzo[a,l]pyrene) and 102.7 +/- 3.2% (dibenzo[a,i]pyrene). The limits of detection ranged from 51.1 ng/L (naphtho[2,3-a]pyrene) to 154 ng/L (dibenzo[a,e]pyrene). The excellent analytical figures of merit associated to its HPLC compatibility makes this approach an attractive alternative for the analysis of co-eluted isomers with identical mass spectra.|For more Analytic Laboratory Methods (Complete) data for DIBENZO(A,E)PYRENE (12 total), please visit the HSDB record page.

Health Hazards -> Carcinogens