Pyren

Other Classes -> Polycyclic Aromatic Hydrocarbons

Polycyclic aromatic hydrocarbon

log Kow = 4.88

4.88

4.88

1.27 at 73.4 °F (EPA, 1998) - Denser than water; will sink

1.271 g/cu cm at 23 °C

1.27 g/cm³

1.27 at 73.4 °F

1.271 @ 23°C

Monoclinic prismatic tablets from alcohol or by sublimation; pure pyrene is colorless

Pale yellow plates (from toluene, sublimes)

Colorless solid (tetracene impurities give yellow color)

less than 1 mg/mL at 72 °F (NTP, 1992)

In water, 0.135 mg/L at 25 °C

In water, median of 19 measured values from literature: 0.135 mg/L at 24-25 °C (average: 0.128 mg/L)

Soluble in ethanol, ethyl ether, benzene, toluene; slightly soluble in carbon tetrachloride

Soluble in carbon disulfide, ligroin

Partially soluble in organic solvents

759 °F at 760 mmHg (EPA, 1998)

394 °C

404.00 °C. @ 760.00 mm Hg

404 °C

759 °F

404 °C @760 [mm Hg]

Hazardous decomposition products formed under fire conditions - Carbon oxides.

When heated to decomposition it emits acrid smoke and irritating fumes.

Poisonous gases are produced in fire.

313 °F (EPA, 1998)

150.62 °C

151.2 °C

151 °C

313 °F

150.62 °C

This chemical does not meet GHS hazard criteria for 13.4% (22 of 164) of reports.

Warning

H315 (63.4%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 164 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

Chemical: Pyrene

Hazard Traits - Bioaccumulation; Environmental Persistence; Nephrotoxicity and Other Toxicity to the Urinary System

Pyrene is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Pyrene are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 17-11-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/12145

Restricted substance: Pyrene

Substance: Pyrene

When heated to decomposition, it emits acrid smoke and fumes. (EPA, 1998)

Gives off irritating or toxic fumes (or gases) in a fire.

Pyrene is a carcinogenic agent and is absorbed by the skin. It is a skin irritant, a suspected mutagen, and an equivocal tumor-causing agent. Workers exposed to 3 to 5 mg/m3 of pyrene exhibited some teratogenic effects. Pyrene is a polycyclic aromatic hydrocarbon (PAH). The acute toxicity of pure PAHs appears low when administered orally or dermally to rats or mice. Human exposure to PAHs is almost exclusively via the gastrointestinal and respiratory tracts, and approximately 99 percent is ingested in the diet. Despite the high concentrations of pyrene to which humans may be exposed through food, there is currently little information available to implicate diet-derived PAHs as the cause of serious health effects. (EPA, 1998)

Health & Welfare Canada; Polycyclic Aromatic Hydrocarbons (1979) Report No. 80-EHD-50

Pyrene is found in an EPA document entitled Chemical Emergency Preparedness Program: Interim Guidance (Nov, 1985). This voluntary program provides two goals: to increase community awareness of chemical hazards and to develop state and local emergency response plans for dealing with chemical accidents.[Roytech/SOCMA Suspect Chemicals Source Book. 4th ed. Burlingame, CA: Roytech Publications, 1985., p. IV-234]

U.S. Dept Health & Human Services/Agency for Toxic Substances Disease Registry; Toxicological Profile for Polycyclic Aromatic Hydrocarbons (Update) (1995) NTIS# PB/95/264370[Available from, as of February 14, 2017: https://www.atsdr.cdc.gov/toxprofiles/tp.asp?id=122&tid=25]

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Pyrene is included on this list. Effective date 6/1/87; Sunset date: 6/1/97.

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use water spray, carbon dioxide, dry powder, alcohol-resistant foam, polymer foam.

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Do NOT induce vomiting. Give one or two glasses of water to drink. Refer for medical attention .

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

Use dry chemical, carbon dioxide, water spray, or alcohol foam extinguishers. ... If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position. ... The only respirators recommended for firefighting are self-contained breathing apparatuses that have full face-pieces and are operated in a pressure-demand or other positive-pressure mode.

Keep container tightly closed in a dry and well-ventilated place.

Store in a flammanle materials storage area. ... Store in a cool, dry place.

Separated from strong oxidants. Keep in a well-ventilated room.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. 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.

Evacuate persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Remove all sources of ignition and dampen spilled material with toluene to avoid airborne dust, then transfer material to a suitable container. Ventilate the spill area and use absorbent dampened with toluene to pick up remaining material. Wash surfaces well with soap and water. Seal all wastes in vapor-tight plastic bags for eventual disposal. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. Ventilate area after cleanup is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters.

Personal protection: Particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder.

Bioaccumulation of this chemical may occur in crustacea, in fish, in milk, in algae and in molluscs. It is strongly advised that this substance does not enter the environment.

... In surface waters, one-third of the total polycyclic aromatic hydrocarbons (PAH) is bound to larger suspended particles, one-third is bound to finely dispersed particles, and the last third is present in dissolved form. The particle-bound portion of 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/

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; Contaminated packaging: Dispose of as unused product.

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.

For more Disposal Methods (Complete) data for Pyrene (14 total), please visit the HSDB record page.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder.

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

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.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. 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.

For more Preventive Measures (Complete) data for Pyrene (10 total), please visit the HSDB record page.

Adipose tissue collected from Korean women during 2007/2008 contained a mean pyrene conentration of 2.1 ng/g lipid wt (98% detection frequency, range of <1.0-5.1 ng/g)(1). Blood plasma collected from 51 healthy females and 60 healthy males in Hong Kong during 2008 contained mean pyrene concentrations (ng/g lipid) of 184 (range 99-305) in females and 212 (range 75.8-312) in males(2). In an analysis of 33 human placenta samples collected from non-smoking women in Beijing, China during 2005-2006, pyrene was detected at mean, median, minimum and maximum concentrations of 2.71, 2.61, not-detected and 5.42 ng/g fresh weight, respectively(3). In an analysis of 7 human umbilical blood samples collected from non-smoking women in Beijing, China during 2005-2006, pyrene was detected at mean, median, minimum and maximum concentrations of 0.491, 0.474, 0.096 and 1.18 ng/g fresh weight, respectively(3). In an analysis of 21 human milk samples collected from non-smoking women in Beijing, China during 2005-2006, pyrene was detected at mean, median, minimum and maximum concentrations of 0.97, 0.861, 0.232 and 4.71 ng/g fresh weight, respectively(3).

Benzo(a)pyrene (B(a)P) is able to inhibit the mutagenicity of l-nitropyrene (l-NP) through the reduction of nitroreductase activity and formation of adducts with DNA. The relationships between the chemical structure of 9 polycyclic aromatic hydrocarbons (PAHs) and antagonistic effects on the l-nitropyrene-induced mutation were evaluated by the binary mixtures of l-nitropyrene and PAHs with Salmonella typhimurium TA98 in the absence of S9 mix. Remarkably different antagonistic effects of 9 polycyclic aromatic hydrocarbons on the mutagenicity of l-nitropyrene were observed. Among the tested polycyclic aromatic hydrocarbons, coronene demonstrates the most antagonistic potential followed by benzo(g,h,i)perylene (B(g,h,i)P), benzo(e)pyrene (B(e)P), dibenzo(a,h)pyrene (DB(a,h)P), benzo(a)pyrene benzo(a)pyrene and pyrene. Naphthalene, anthracene, and chrysene had only minor inhibitory activity on the l-nitropyrene mutagenicity. The modifying effects of polycyclic aromatic hydrocarbons on the nitroreductase activity of TA98 strains in the presence of l-nitropyrene were further examined from the production of l-AP. The statistical analytical data showed that the inhibitory effect of polycyclic aromatic hydrocarbons on the mutagenicity of l-nitropyrene significantly correlated with their effects on the nitroreductase activity (r = - 0.69, p < 0.05). In addition, the formation of l-nitropyrene-DNA adducts of the binary mixtures of l-nitropyrene and polycyclic aromatic hydrocarbon was determined by the 32P-postlabeling method. The results indicated that the modulatory effects of polycyclic aromatic hydrocarbons on the formation of l-nitropyrene-DNA adducts were correlated well with their antagonistic activity (r= -0.91, P < 0.011. From the above results, the relationships between the chemical structure of polycyclic aromatic hydrocarbons and the antagonistic effects on the l-nitropyrene mutagenicity were revealed by the surface area and electronic parameters of PAHs. The planar molecular area of PAHs was more convicingly correlated with the antagonistic effect on the mutagenicity of l-nitropyrene (r= - 0.81, p < 0.01) than that with the difference in energy, DELTAE, between EHOMO and ELUMO (r = 0.69, p < 0.05). According to the above, two possible mechanisms are involved in the interactive effect of the binary mixtures: (1) a higher binding affinity with nitroreductase for PAHs having a large planar surface area; and (2) a high energy of interaction between l-nitropyrene and polycyclic aromatic hydrocarbons with a low DELTAE might decrease the nitroreductive capability.

Cocarcinogenic studies on mouse skin (50 female ICR/HA mice per group) were conducted. Simultaneous dermal application of 5 ug benzo(a)pyrene in same soln with pyrene (0.004 and 0.012 mg) 3 times weekly in 0.1 mL acetone per application resulted in 6/50 and 20/50 mice with squamous carcinomas, respectively. No neoplasms were observed in mice treated with pyrene alone. /From table/

Exposure to sun may provoke an irritating effect of pyrene on skin and lead to chronic skin discoloration.

Chemical pollution of the aquatic environment is almost always the result of multiple rather than single toxic compounds. The possibility of separating the effects of key risk chemicals from those of others, including their joint effects, is of clear theoretical interest and high technical importance. ... This goal /was addressed/ using multiple gene expression profiling in the liver of juvenile brown trout (Salmo trutta lacustris) exposed to three model chemicals (cadmium, carbon tetrachloride, and pyrene) administered singly, in binary and trinary combinations at low acutely sublethal concentrations, and in the partial dose-response manner. Differentially expressed genes were grouped by correlation of profiles, and the dependence on dose was analyzed with multiple regression. Responses to cadmium and CCl4 were largely similar, and no sign of interaction was observed (i.e., in binary combinations, the effects were equal to those produced by the more potent compound, cadmium). Joint effects became apparent in the presence of pyrene, which caused markedly different alterations in gene expression. Using the results of 118 experiments conducted earlier for comparison, ... a group of 23 genes responding to chemical toxicity (cadmium, CCl4, pyrene, and resin acids) with significantly higher probability than that of responding to other stressors (handling or viral and bacterial infections) /was found/. This group included genes implicated in the immune and stress responses that were markedly enriched in extracellular proteins. In conclusion, /it was/ demonstrated that chemical-characteristic genomic endpoints often remain when the chemical is present as part of a binary or a trinary mixture. Despite dissimilar chemistry and different cellular targets, the degree of responses to the combination of cadmium and CCl4 appeared to be less than additive. Chemical interactions or nonadditive effects manifested when a compound with a markedly different mode of action (pyrene) was included into the mixture.

For more Interactions (Complete) data for Pyrene (6 total), please visit the HSDB record page.

EC50; Species: Pseudokirchneriella subcapitata (Green algae, age <24 hr); Conditions: freshwater, static; Concentration: 894000 ug/L for 72 hr; Effect: increased intoxication, immobilization /98% purity/

EC50; Species: Daphnia magna (Water flea); Conditions: freshwater, renewal; Concentration: 72.7 ug/L for 7 days; Effect: growth rate />99% purity/

EC50; Species: Daphnia magna (Water flea, age <24 hr, neonate); Conditions: freshwater, static; Concentration: 67000 ug/L for 48 hr; Effect: intoxication, immobilization /98% purity/

EC50; Species: Daphnia magna (Water flea, age 4-6 days); Conditions: freshwater, static, 23 °C; Concentration: 0.45 mmol/cu m for 48 hr; Effect: intoxication, immobilization /> or =97% purity/

For more Ecotoxicity Values (Complete) data for Pyrene (13 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 61,936-90,000(2-3), indicate that pyrene is expected be immobile in soil(SRC). Volatilization of pyrene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.19X10-5 atm-cu m/mole(4). However, adsorption to soil is expected to attenuate volatilization(SRC). Pyrene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 4.5X10-6 mm Hg at 25 °C(5). Photolytic degradation of pyrene is expected to occur on soil surfaces as indicated by numerous photolysis studies performed on a variety of substrates(6-7). PAHs with four or more rings, such as pyrene, are generally expected to be resistant to biodegradation(8). Biodegradation is expected to occur slowly in soils, with estimated half-lives ranging from several weeks to years(9-10). Faster biodegradation rates occur with exposure to acclimated microbes(11). Soil microcosm studies using three industrial soils from Austria found pronounced biodegradation of pyrene in one soil (about 65-75% over 65 days of incubation), but only slight biodegradation in the other two soils(12).

AQUATIC FATE: Based on a classification scheme(1), Koc values of 61,936-90,000(2-3), indicate that pyrene is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon a Henry's Law constant of 1.19X10-5 atm-cu m/mole(5). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 4.5 and 37 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 29 years if adsorption is considered(6). According to a classification scheme(7), BCFs of 72-4800(8-11) in fish suggest bioconcentration in aquatic organisms is moderate to very high, provided the compound is not metabolized by the organism(SRC). However, pyrene 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(12). A measured fish biotransformation half-life of 2.08 days has been reported for pyrene(13). The near surface half-life for direct photolysis of pyrene in water by sunlight was measured as 0.68 hours(14) and 0.85 hours(15). PAHs with four or more rings, such as pyrene, are generally expected to be resistant to biodegradation(16). Biodegradation is expected to occur slowly, with estimated half-lives ranging from several weeks to years(17-18). Faster biodegradation rates occur with exposure to acclimated microbes(19). Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions(4).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), pyrene, which has a vapor pressure of 4.5X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Pyrene has been detected in ambient air samples in both vapor and particulate phases(3). Vapor-phase 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 5X10-11 cu cm/molecule-sec at 25 °C(4). The atmospheric lifetime of vapor-phase pyrene due to reaction with nitrate radicals has been calculated as approximately 30 days(5). Particulate-phase pyrene may be removed from the air by wet or dry deposition(SRC). Monitoring studies have detected pyrene in both precipitation(6) and dry deposition samples(7). Pyrene absorbs strongly at wavelengths >290 nm(8,9) and, therefore, is expected to be susceptible to direct photolysis by sunlight(SRC). [

Pyrene was detected in smoked ham (0.2-11.2 ppb), pork roll (2.5 ppb), frankfurters (3.8 ppb), gouda cheese (2.6 ppb), hot sausage (1.5 ppb), barbecued beef (3.2 ppb), mutton (8 ppb), salami (5.2 ppb), mortadella (15 ppb), heavily smoked bacon (27 ppb), and heavily smoked ham (35-161 ppb)(1). Pyrene was detected in milled wheat and cereals at concentrations of 1.5-28.0 ppb and 2.2-21.0 ppb respectively(2). Pyrene was detected in freeze dried carrots at a concentration of 0.82 ug/kg(3). Pyrene was detected in wheat flour (5.5 ug/kg), rye flour (2.6 ug/kg), rolled oats (5.4 ug/kg), milled oats (1.6 ug/kg), milled wheat (1.6 ug/kg) and bran (47 ug/kg)(4). Pyrene was detected in beet greens (0.692 ug/kg), lettuce (0.433 ug/kg), tomatoes (0.395 ug/kg), potatoes (0.417 ug/kg), apples (3.461 ug/kg), beef (1.269 ug/kg), pork (5.288 ug/kg), butter (1.769 ug/kg) and pizza (0.584 ug/kg)(5). Pyrene was detected in bread (0.5 ug/kg) and margarine (4.5 and 4.7 ug/kg) produced in the Netherlands(6). Pyrene was detected in olive oil (9 ug/kg), sunflower seeds (2.2 ug/kg), Sesame oil (1.2 ug/kg), linseed oil (6.3 ug/kg) and wheat germ oil 13.2 ug/kg)(7). Pyrene was detected in smoke from chicken fried in soybean, canola and sunflower oils(8). Pyrene was detected in 99% of the food samples in Minnesota Children's Pesticide Exposure Study at a mean concentration of 0.4 ug/kg (102 children, ages 3-12)(9). Five olive pomace oils contained pyrene at 5.21-211.76 ug/kg(10).

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

Oral (L10) ; inhalation (L10)

ENVIRONMENTAL: Pyrene was detected in dried milk at a concentration of 2.1 ppb(1). Pyrene was detected at an average concentration of 0.04 ppb in UK milk products(2). Pyrene was detected in milk at 14 farms in samples tested March 2000 at concentrations of 1.8-3.7 ng/g milk fat(3). In an analysis of 21 human milk samples collected from non-smoking women in Beijing, China during 2005-2006, pyrene was detected at mean, median, minimum and maximum concentrations of 0.97, 0.861, 0.232 and 4.71 ng/g fresh weight, respectively(4).

IDENTIFICATION AND USE: Pyrene is a solid. It can be used as an additive in electro-insulating oils as well as in epoxy resins for electrical insulation. Optical brighteners can be synthesized by reaction of pyrene with a complex of cyanuric chloride and aluminum chloride. Pyrene itself can serve as an electron donor to enhance the blackness in pencil leads. It is also used in biochemical research. HUMAN EXPOSURE AND TOXICITY: Exposure to the sun may provoke an irritating effect of pyrene on skin and lead to chronic skin discoloration. Pyrene, but not related polyaromatic hydrocarbons, enhanced basal transcription of the human and mouse IL-4 promoter. ANIMAL STUDIES: Dermal exposure to 10 g/kg was not lethal in mice. Inhalation caused pathological changes in hepatic, pulmonary, and intragastric tissue and a decrease in the number of neutrophils, leukocytes, and erythrocytes. No blastomogenic or carcinogenic effects were noted, except for an occasional papilloma. Some teratogenic effects were noted. Pyrene induced mutations and unscheduled DNA synthesis in some in vitro assays in mammalian cells. There is limited evidence that pyrene is active in short-term assays. ECOTOXICITY STUDIES: There was an interaction between pyrene and the thyroid system in fish. In rockfish, pyrene exposure impaired skeleton development via disrupting the proliferation of the chondrocytes. Embryonic exposure of zebrafish to low-level environmental pyrene disrupted normal cardiac development and altered expression of defective cardiac differentiation related genes. Pyrene might be a contributor to the behavioral and neuro-developmental toxicity in pufferfish. in the earthworm Lumbricus rubellus pyrene was found to cause a dose dependant decrease in lactate and the concentrations of the saturated fatty acids tetradecanoic, hexadecanoic and octadecanoic acid and an increase in production of the amino acids alanine, leucine, valine, isoleucine, lysine, tyrosine and methionine. It is proposed that this indicates impaired glucose metabolism, with an associated increase in fatty acid metabolism and changes in TCA cycle intermediates.

The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (L10, L23, A27, A32)

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Pyrene is included on this list. Effective date 6/1/87; Sunset date: 6/1/97.

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 5000 lb or 2270 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).

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Pyrene is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 1,000 or 10,000 lbs. Extremely hazardous substances that are solids are subject to either of two threshold planning quantities ... The lower quantity applies only if the solid exists in powdered form and has a particle size less than 100 microns; or is handled in solution or in molten form; or meets the criteria for a National Fire Protection Association (NFPA) rating of 2, 3 or 4 for reactivity. If the solid does not meet any of these criteria, it is subject to the upper ... threshold planning quantity ... .

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/.

(FL) FLORIDA 210 ug/L

(MN) MINNESOTA 200 ug/L

(WI) WISCONSIN 250 ug/L

... The apparent elimination rate of (14)C-pyrene (23 hr) contained in the skin after an exposure of 4.5 hr was similar to the apparent urinary excretion half life of 1-OHPy (21 hr). These values are threefold higher than the urinary excretion half life of 1-OHPy after an intravenous administration of pyrene (0.5 mg/kg). ...

Two well-informed human volunteers were exposed to 500 ug pyrene by ingestion and by dermal application, in two separate experiments. Urinary measurements of 1-hydroxypyrene (1-OHP) were performed on all micturitions taken at intervals of 0.5-4 hr for a total period of 48 hr after dosing. Following the absorption phase, 1-OHP was excreted with a first order apparent half-life of approximately 12 hr for both volunteers and both exposure routes. ...

The urinary excretion profiles following exposure to pyrene were established in one psoriasic patient under treatment with a coal tar-based shampoo and in two other volunteers exposed to a single dose of 100 uL creosote and, in a separate experiment, to five consecutive daily dermal applications of 500 ug pyrene on 200 sq cm of the inner face of the forearms. Timed micturitions were collected for up to 48 hr following exposure. Both in the psoriasic patient and in the volunteers exposed to creosote, the excretion peaks between 10 and 15 hr after application and first-order apparent half lives of 11.5-15 hr can be calculated for the elimination phase. ...

Five experiments were conducted in male Sprague-Dawley rats regarding the kinetic of urinary excretion of 1-hydroxypyrene (1-OHP) following i.v., oral and dermal exposure to 0.5-50 umol/kg pyrene either as a single substance or as mixture of various polycyclic aromatic hydrocarbons (PAH). ... Half-lives of both pyrene and 1-OHP in all measured tissues were all comprised between 3.1 and 5.4 hr, and 5.2-6.7 hr, respectively, so that no long term accumulation would be predicted from these values for any tissue. ...

Speckled trout, Salvelinus fontinalis, were orally exposed to individual polycyclic aromatic compounds (PACs) represented by benzo[a]pyrene, carbazole, chrysene, dibenzofuran, dibenzothiophene, fluorene, phenanthrene, and pyrene. Fish were sacrificed 7 days after exposure and the gall bladder removed for bile analysis. High pressure liquid chromatography (HPLC) with fluorescence (F) and ultraviolet (UV) detection was used to determine the presence of PAC derivatives in the bile without pretreatment. Glucuronide conjugates were predominant in all exposures with variable amounts (0-53%) of phenols and starting material. Identification of compounds was confirmed by selective extraction of less polar nonconjugated PACs and enzymatic hydrolysis of water-soluble material. This was followed by HPLC and/or gas chromatography-mass spectrometry (GCMS) characterization of the produced phenols. Total metabolite levels varied widely among compounds.

Rat liver microsomal systems metabolize pyrene to 1-hydroxy and 4,5-dihydro-4,5-dihydroxypyrene, as well as to 1,6- and 1,8-pyrene quinone.

Yields trans-4,5-dihydro-4,5-dihydroxypyrene, s-(4,5-dihydro-4-hydroxypyren-5-yl)glutathione, 1,6-dihydroxypyrene, 1,8-dihydroxypyrene, and 1-hydroxypyrene in rats and rabbits.

For K-region of pyrene (4,5 bond), no evidence of phenol formation is found, 4,5-dihydrodiol is detected in relatively small amt, and no 4,5-dihydroxypyrene derivatives are found. Major metabolite appears to be mercapturic acid, n-acetyl-s-(4,5-dihydro-4-hydroxy-5-pyrenyl)l-cysteine.

For more Metabolism/Metabolites (Complete) data for Pyrene (19 total), please visit the HSDB record page.

PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. (L10)

Chemicals that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags.

... Rats were treated with Benzo(a)pyrene (BaP) (150 ug/kg) alone or with phenanthrene (PH) (4,300 ug/kg) and pyrene (PY) (2,700 ug/kg) (BPP group) by oral gavage once per day for 30 days. 7-ethoxyresorufin-O-deethylase activity in liver microsomal fraction was increased in only BaP groups. The highest concentration (34.5 ng/g) of BaP, was found in muscle of rats treated with BaP alone at 20 days of treatment; it was 23.6 ng/g in BPP treated rats at 30 days of treatment. The highest PH concentration was 47.1 ng/g in muscle and 118.8 ng/g in fat, and for PY it was 29.7 ng/g in muscle and 219.9 ng/g in fat, in BPP groups. In urine, 114-161 ng/mL 3-OH-PH was found, while PH was 41-69 ng/mL during treatment. 201-263 ng/mL 1-OH-PY was found, while PH was 9-17 ng/mL in urine. The level of PY, PH and their metabolites in urine was rapidly decreased after withdrawal of treatment ...

... This human control study examined the excretion kinetics of urinary 1-hydroxypyrene (1-OHP) after consuming barbecued meat. Two feeding experiments were conducted, with doses of 15 and 30 g of barbecued meat per kg of body weight for experiments 1 and 2, respectively. All voided urine was collected for 7 days and analyzed for 1-OHP. In both experiments, the amounts of urinary 1-OHP excreted was significantly increased (P < 0.05) at 12 hr post exposure but not at 12-24 hr post exposure. Mean percentages of administered pyrene doses excreted as urinary 1-OHP at 0-12 hr and 12-24 hr post exposure were 3.80 and 0.61% in experiment 1 and 1.66 and 0.38% in experiment 2. Excretion ratio was inversely related to dose. A pattern of diurnal fluctuation (P < 0.05) in 1-OHP excretions was also identified. That is, 1-OHP excretions were smaller in the first half of the day (~0:00-12:00) than in the last half of the day (~12:00-24:00). This study demonstrated that, even at large dietary doses, most of the total urinary excretion of 1-OHP occurs within 12 hr. Thus, subjects of occupational or environmental studies need only recall their diets for the current or previous day to diminish the influence from dietary pyrene.

... Two groups of Buccinum undatum were exposed to equimolar amounts of pyrene and 1-hydroxypyrene over 15 d through their diets. Tissue extracts from the muscle and visceral mass were analyzed by liquid chromatography with fluorescence and mass spectrometry detection. Nine biotransformation products were detected in animals from both exposures. These included 1-hydroxypyrene, pyrene-1-sulfate, pyrene-1-glucuronide, pyrene glucose sulfate, two isomers each of pyrenediol sulfate and pyrenediol disulfate, and one isomer of pyrenediol glucuronide sulfate. These compounds represent a more complex metabolic pathway for pyrene than is typically reported. Diconjugated metabolites were as important in animals exposed to pyrene as in those exposed to 1-hydroxypyrene. Biotransformation products represented >90% of the material detected in the animals and highlight the importance of analyzing metabolites when assessing exposure. A mean of only 2 to 3% of the body burden was present in muscle compared with the visceral mass of both groups. The analytical methods were sufficiently sensitive to detect biotransformation products both in laboratory control whelks and in those sampled offshore. The tissue distribution of [(14)C]pyrene was also studied by autoradiography. Radioactivity was present primarily in the digestive and excretory system of the whelks and not in the gonads or muscle tissue.

... Transfer of 10 polynuclear aromatic hydrocarbons (PAHs) (pyrene, 3,4-benzophenanthrene, triphenylene, chrysene, 1,2-benzanthracene, 1,1'-binaphthyl, 9-phenylanthracene, 2,2'-binaphthyl, m-tetraphenyl and 1,3,5-triphenylbenzene) out of phosphatidylcholine vesicles has been examined. Our results show that the molecular volume of the PAH is a rate-determining factor. Moreover, high performance liquid chromatography (HPLC) data confirms the hypothesis that the rate of transfer is correlated with the size of the molecule and with the partitioning of the molecule between a polar and hydrocarbon phase. The kinetics and characteristics of the spontaneous transfer of carcinogens are likely to have a major impact on the competitive processes of PAH metabolism within cells.

For more Absorption, Distribution and Excretion (Complete) data for Pyrene (13 total), please visit the HSDB record page.

Used in research; [Hawley] As a starting material in the production of optical brighteners and dyes; [HSDB] It is a by-product of the pyrolysis of organic matter and is present in coal tar distillates, diesel exhaust, automobile exhaust, tobacco smoke, barbecue smoke, wood smoke, lake sediments, waste oils, and sewage. [CHEMINFO]

Optical brighteners can be synthesized by reaction of pyrene with a complex of cyanuric chloride and aluminum chloride.

By analogy to fluoranthene, pyrene and alkylpyrenes can be used as additives in electro-insulating oils as well as in epoxy resins for electrical insulation.

Pyrene from coal-tar has been used as a starting material for the synthesis of benzo(a)pyrene.

Pyrene itself can serve as an electron donor to enhance the blackness in pencil leads.

Biochemical research.

(1978) 8.69X10+7 G

(1982) 7.88X10+7 G

(1985) 5.74X10+7 g

2023: 895,552 lb

(1978) Not produced commercially in USA

(1982) Not produced commercially in USA

(1983) Not produced commercially in USA

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#4714]

For more U.S. Production (Complete) data for Pyrene (6 total), please visit the HSDB record page.

Pyrene is found in products of incomplete combustion, fossil fuels, and high-temperature coal tar fractions, which on average contain ca. 2% pyrene. It is recovered from a fraction crystallizing above 110 °C, which is obtained by redistillation of the high-boiling anthracene oil II or pitch distillate. Pure pyrene is produced by recrystallization, e.g., from solvent naphtha or by fractional crystallization from the melt, followed by dephenolation and debasing, and by refining with 80% sulfuric acid. Alternatively, pyrene-accompanying brasane (2, 3-benzodiphenylene oxide) can be separated by recrystallization from xylene in the presence of iron(III) chloride. Traces of tetracene are removed by reaction with maleic anhydride.

... Obtained by the destructive hydrogenation of hard coal.

Pyrene can be synthesized via bromination of o,o'-ditolyl. The resulting intermediate is transformed into its corresponding dicarboxylic acid via dinitrile intermediates. Cyclization takes place in the presence of zinc dust. An alternative route to pyrene is the reaction of peri-trimethylenenapthalene with malonyl chloride and AlCl3. It is also accessible via the Reformatsky reaction of 4-keto-1,2,3,4-tetrahydrophenanthrene

From coal tar.

Wood Product Manufacturing

Pyrene: ACTIVE