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Benzo[e]pyren

Benzo(E)Pyrene

HCID 9128
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TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

CAS
192-97-2
Standard-SMILES
c1ccc2c(c1)c1cccc3ccc4cccc2c4c31
InChIKey
TXVHTIQJNYSSKO-UHFFFAOYSA-N
Summenformel
C20H12
Durchschnittliche Molmasse
252,3 g/mol
Monoisotopische Masse
252,09390038

Überblick

Benzo[e]pyrene appears as colorless crystals or white crystalline solid. (NTP, 1992)

Namen und Bezeichner

Bevorzugter Name
Benzo(E)Pyrene
IUPAC
benzo[e]pyrene
Lokaler Name
Benzo[e]pyren
Englischer Name
Benzo[e]pyrene
Summenformel
C20H12
Molmasse
252.31

Namen und Synonyme

Benzo[e]pyrene192-97-2BENZO(E)PYRENE1,2-Benzpyrene4,5-Benzpyrene4,5-BenzopyreneBenzo(l)pyrene9,10-Benzpyrene1,2-BenzopyreneBenz(e)pyreneBenz[e]pyreneDTXSID3023764
Weitere Namen anzeigen
Benzo[e]pyrene 98%
NSC 89273CHEBI:3456763APT6398RNSC-89273DTXCID103764Benzo[l]pyrene1,2-benzo(e)pyreneRefChem:916916

Datenbank-Bezeichner

CAS
192-97-2、73467-76-2
PubChem CID
9128
DTXSID
DTXSID3023764
ChEMBL
CHEMBL1371125
ChEBI
CHEBI:34567
UNII
63APT6398R
EC Number
205-892-7
Nikkaji
J2.971H

Eigenschaften

Berechnete Struktureigenschaften

XLogP
6,4
Polarare Oberfläche (TPSA)
0 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
0
Frei drehbare Bindungen
0
Schwere Atome
20
Formalladung
0
Komplexität
336

Experimentelle und physikochemische Eigenschaften

Polymers · 3 Einträge

Other Classes -> Polycyclic Aromatic Hydrocarbons

Other Classes -> Polycyclic Aromatic Hydrocarbons

Polycyclic aromatic hydrocarbon

SpringerMaterials PropertiesAngular frequency
LogP · 2 Einträge

log Kow = 6.44

6.44

Color/Form · 3 Einträge

Prisms or plates from benzene

Pale yellow needles (from benzene or methanol)

Colorless crystals or white crystalline solid

Solubility · 4 Einträge

less than 1 mg/mL at 73 °F (NTP, 1992)

In water 0.0063 mg/L at 25 °C

2.9X10-8 mol/L dissolve in water at 25 °C

Soluble in acetone

Boiling Point · 3 Einträge

918 °F at 760 mmHg (NTP, 1992)

492 °C at 76- mm Hg

BP: 250 °C at 3-4 mm Hg (sublimes)

Decomposition · 2 Einträge

Hazardous decomposition products formed under fire conditions - Carbon oxides.[Sigma-Aldrich; Safety Data Sheet for Benzo

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H350: May cause cancer [Danger Carcinogenicity]

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

Danger

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

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

Gefahrenhinweise

Regulatory InformationHazard Traits - Carcinogenicity
DOT LabelClass 9
Fire HazardsFlash point data for this compound are not available. It is probably combustible. (NTP, 1992)
Health HazardsSYMPTOMS: This compound may cause irritation of the skin on contact.
Hazards Summary · 2 Einträge

May cause irritation; [MSDSonline] See POLYCYCLIC AROMATIC HYDROCARBONS.

See POLYCYCLIC AROMATIC HYDROCARBONS.

Reactive GroupHydrocarbons, Aromatic
Special Reports · 1 Eintrag

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 October 31, 2016: https://www.atsdr.cdc.gov/toxprofiles/tp.asp?id=122&tid=25]

OSHA StandardsPermissible 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/

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 2 Einträge

... Previous studies from /the author's/ laboratory reported that benzo(a)pyrene (Bap) influenced efflux transport of rhodamine 123 (Rho-123) by induction of P-glycoprotein (P-gp) in Caco-2 cells. The present study investigated whether induction of P-gp and the enhanced efflux transport of Rho-123 were caused by benzo(e)pyrene (Bep), which has a structure similar to Bap, but is not a carcinogenic compound. In Caco-2 monolayer exposed to 50 uM Bep for 72 hr, the ratio of the apparent permeability coefficient (P(app)) of Rho-123 efflux increased significantly compared to that of the control monolayer. Similarly, a significant increase in expression of MDR1 mRNA and of P-gp at the protein level were detected by RT-PCR and by Western blot analysis, respectively, in Caco-2 cells exposed to Bep, compared to that of the control. Caco-2 cells exposed to Bep showed oxidative stress that was detected by fluorescence microscopy using aminophenyl fluorescein. However, the oxidative stress was weaker compared with that of Bap. The cellular GSH content was decreased to 80% or 59% of control cells, respectively, in Caco-2 cells exposed to either Bep or Bap. Our results further show that Bep or Bap-induced P-gp in Caco-2 cells might have been the result of oxidative stress rather than DNA damage.

The mechanism of the co-carcinogenic activity of benzo[e]pyrene (BeP) was investigated by determining the effects of benzo[e]pyrene on the binding of the carcinogen benzo[a]pyrene (BaP) to DNA in Sencar mouse epidermis. The dose of benzo[a]pyrene used was 20 nmol/mouse a dose which is not carcinogenic in a single application but is carcinogenic after multiple treatments such as those in the benzo[a]pyrene-benzo[e]pyrene co-carcinogenesis experiments described by Van Duuren and Goldschmidt. After 3 hr of exposure to [(3)H]benzo[a]pyrene and benzo[e]pyrene at benzo[a]pyrene:benzo[e]pyrene dose ratios of 1:3 and 1:10, [(3)H]benzo[a]pyrene-DNA adducts in both benzo[e]pyrene-treated groups were lower than in an acetone-benzo[a]pyrene control group. After 12 and 24 hr of exposure the benzo[a]pyrene-benzo[e]pyrene (1:10) group contained 19% and 33% higher [(3)H]benzo[a]pyrene-DNA adduct levels than the control. In the benzo[a]pyrene-benzo[e]pyrene 11:3) group the amount of [(3)H]benzo[a]pyrene-DNA adduct levels was higher than the control after 12 hr. Benzo[e]pyrene cotreatment with either [(3)H]benzo[a]pyrene-7 8-dihydrodiol or anti-[(3)H]benzo[a]pyrene had no effect on the amount of benzo[a]pyrene DE-DNA adducts present. These results demonstrate that the cocarcinogen benzo[e]pyrene increases the amount of a low dose of benzo[a]pyrene that binds to mouse epidermal DNA and indicate that the increase in benzo[a]pyrene-DNA adducts results from increased metabolism of benzo[a]pyrene to the proximate carcinogen benzo[a]pyrene-7 8-dihydrodiol.

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

Melting Point · 2 Einträge

352 to 354 °F (NTP, 1992)

178-179 °C

Vapor Pressure · 2 Einträge

0.00000001 [mmHg]

5.7X10-9 mm Hg at 25 °C /extrapolated/

Physical Description · 2 Einträge

Benzo[e]pyrene appears as colorless crystals or white crystalline solid. (NTP, 1992)

Insoluble in water (0.0063 mg/L at 25 deg C; [ChemIDplus] Fine, slightly yellow crystals; Insoluble in water; [MSDSonline]

Stability/Shelf Life · 2 Einträge

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

Benzo(e)pyrene may be sensitive to prolonged exposure to light.

Collision Cross Section149.7 Ų [M]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID3023764]

Physikochemische Eigenschaften

Schmelzpunkt
177 · 177-180 °C(lit.)
Siedepunkt
495.49 °C · 495.49°C (rough estimate)
Dichte
1.286 · 1.286
Dampfdruck
644 at · 644 at 25 °C (subcooled liquid vapor pressure calculated from GC retention time data, Hinckley etal., 1990)
Brechungsindex
1.853 · 1.8530 (estimate)
Flammpunkt
-18 °C · -18 °C
storage temp.
2 · 2-8°C
Löslichkeit
Slightly soluble in methanol (Patnaik, 1992)
Aggregatzustand
crystals
pka
14 · >14 (Schwarzenbach et al., 1993)
Farbe
6 H6 · Prisms from C6H6
Wasserlöslichkeit
0.984 ug/L · 0.984ug/L(25 ºC)
Merck
13 · 13,1105
BRN
1911334 · 1911334
Henry's Law Constant
(x 10-7 atmm3/mol): 4.84 at 25 °C (approximate - calculated from water solubility and vapor pressure)
Major Application
environmental
InChI
1S/C20H12/c1-2-8-16-15(7-1)17-9-3-5-13-11-12-14-6-4-10-18(16)20(14)19(13)17/h1-12H
InChIKey
TXVHTIQJNYSSKO-UHFFFAOYSA-N
SMILES
c1ccc2c(c1)c3cccc4ccc5cccc2c5c34
CAS Datenbank
192 · 192-97-2(CAS DataBase Reference)
EPA chemische Informationen
Benzo[e]pyrene (192-97-2)
Reactivity ProfileBENZO[E]PYRENE may be sensitive to prolonged exposure to light.
Air and Water ReactionsInsoluble in water.
NIOSH Recommendations · 2 Einträge

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/

Clean Water Act Requirements · 2 Einträge

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/.

Sicherheit und Schutzausrüstung

Fire FightingFires involving this chemical can be controlled with a dry chemical, carbon dioxide, or Halon extinguisher. (NTP, 1992)
First Aid · 1 Eintrag

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Fire Fighting Procedures · 3 Einträge

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

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

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.

Storage Conditions · 2 Einträge

Keep container tightly closed in a dry and well-ventilated place.[Sigma-Aldrich; Safety Data Sheet for Benzo

You should protect this material from exposure to light, and store it in a refrigerator.

Cleanup Methods · 3 Einträge

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 Benzo

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.

Small Spills and Leakage: If you spill this chemical, first remove all sources of ignition, then dampen the solid spill material with toluene, then transfer the dampened material to a suitable container. Use absorbent paper dampened with toluene to pick up any remaining material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash all contaminated surfaces with toluene followed by washing with a soap and water solution. Do not reenter the contaminated area until the safety officer (or other responsible person) has verified that the area has been properly cleaned.

Nonfire Spill Response · 1 Eintrag

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then dampen the solid spill material with toluene, then transfer the dampened material to a suitable container. Use absorbent paper dampened with toluene to pick up any remaining material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash all contaminated surfaces with toluene followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 3 Einträge

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 Benzo

Preventive Measures · 5 Einträge

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 Benzo

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

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 Benzo

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 Benzo

For more Preventive Measures (Complete) data for BENZO(E)PYRENE (8 total), please visit the HSDB record page.

Isolation and EvacuationExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Threshold Limit Values (TLV) · 5 Einträge

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 BENZO(E)PYRENE (6 total), please visit the HSDB record page.

Personal Protective Equipment (PPE) · 6 Einträge

MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves.

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

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

Body Protection: Impervious clothing. 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 Benzo

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 Benzo

For more Personal Protective Equipment (PPE) (Complete) data for BENZO(E)PYRENE (10 total), please visit the HSDB record page.

Immediately Dangerous to Life or Health (IDLH)NIOSH considers coal tar pitch volatiles to be potential occupational carcinogens. /Coal tar pitch volatiles/

Toxikologische Informationen

Body BurdenAnalysis of urine taken from workers in an aluminum plant found benzo(e)pyrene concentrations of 0.08-0.095 ug/mmole creatinine(1).
TreatmentThere is no known antidote for PAHs. Exposure is usually handled with symptomatic treatment. (L10)
Interactions · 5 Einträge

... In this research, we studied the photoirradiation of isomeric methylbenzo[a]pyrene (MBaP) and methylbenzo[e]pyrene (MBeP) by UVA light in the presence of a lipid, methyl linoleate, and evaluated the potential of these compounds to induce lipid peroxidation. The compounds chosen for study included BaP, 3-MBaP, 4-MBaP, 6-MBaP, 7-MBaP, 10-MBaP, BeP, 4-MBeP, and 9-MBeP. The results indicate that upon photoirradiation by UVA at 7 and 21 J/sq cm, these compounds induced lipid peroxidation. The levels of the induced lipid peroxidation were similar among BaP and the isomeric MBaPs, and among the BeP and MBePs, with the BaP group higher than the BeP group. There was also a co-relation between the UV A light dose and the level of lipid peroxidation induced. Lipid peroxide formation was inhibited by NaN3 (singlet oxygen and free radical scavenger) and was enhanced by the presence of deuterium oxide (D2O) (extends singlet oxygen lifetime). These results suggest that photoirradiation of MBaPs and MBePs by UVA light generates reactive oxygen species (ROS), which induce lipid peroxidation.

Benzo[e]pyrene (B[e]P) inhibited 7,12-dimethylbenz[a]anthracene (DMBA) skin tumor-initiation in mice by 84%, whereas pyrene and fluoranthene inhibited DMBA initiation by 50 and 34%, respectively. ...

Benzo(e)pyrene, when administered to mice by skin application together with 7,12-dimethylbenz(a)anthracene or benzo(a)pyrene, resulted in fewer skin tumors than with 7,12-dimethylbenz(a)anthracene alone and in more skin tumors than with benzo(a)pyrene alone.

Groups of 20 female Fischer 344 rats (aged unspecified) received implants of beeswax pellets containing either 1 mg benzo(a)pyrene, 0.5 mg benzo(a)pyrene, 1 mg benzo(e)pyrene (purity unspecified), 0.5 mg benzo(a)pyrene + 1 mg benzo(e)pyrene, or 1 mg benzo(a)pyrene + 1 mg benzo(e)pyrene in tracheas from isogenic donors transplanted subcutaneously in the retroscapular region (two tracheas/animal). All surviving animals were killed 28 months after the start of exposure. Benzo(e)pyrene did not induce tumors in tracheal explants, while 1 mg benzo(a)pyrene induced carcinomas in 65% of the grafts. Benzo(e)pyrene appeared to reduce the incidence of carcinomas from 65% (benzo(a)pyrene alone) to 40% (benzo(a)pyrene plus benzo(e)pyrene). However, the incidence of sarcoma in tracheal and peritracheal explants was enhanced two- to three-fold by benzo(e)pyrene given with benzo(a)pyrene compared with benzo(a)pyrene alone.

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

Health EffectsPAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system. (L10)
Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), a measured soil Koc value of 6.9X10+5(2), indicates that benzo(e)pyrene is expected to be essentially immobile in soil(SRC). Volatilization of benzo(e)pyrene from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.0X10-7 atm-cu m/mole(SRC), derived from its extrapolated vapor pressure, 5.7X10-9 mm Hg(3), and water solubility, 0.0063 mg/L(4). Benzo(e)pyrene is not expected to volatilize from dry soil surfaces(SRC) based upon its extrapolated vapor pressure(3). Limited biodegradation data, specific to benzo(e)pyrene, suggest that biodegradation is slow(5,6); 87% of the initial benzo(e)pyrene remained after 1280 days of incubation(6); soil degradation studies conducted over 4 weeks found that all higher ring PAHs were only slightly or not biodegraded(6). In general, PAHs with five or more benzene rings do not biodegrade readily(7). Benzo(e)pyrene is susceptible to direct photolysis(8,9) on soil surfaces exposed to sunlight.

AQUATIC FATE: Based on a classification scheme(1), a measured Koc value of 6.9X10+5(2), indicates that benzo(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 3.0X10-7 atm-cu m/mole(SRC), derived from its extrapolated vapor pressure, 5.7X10-9 mm Hg(4), and water solubility, 0.0063 mg/L(5). According to a classification scheme(6), an estimated BCF of 8200(SRC), from its log Kow of 6.44(7) and a regression-derived equation(8), 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(9). A measured fish biotransformation half-life of 1.1 days has been reported for the analogous compound benzo(a)pyrene(10). Benzo(e)pyrene absorbs strongly at wavelengths >290 nm(14) and, therefore, is expected to be susceptible to direct photolysis on water surfaces exposed to sunlight(SRC). Benzo(e)pyrene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Limited biodegradation data, specific to benzo(e)pyrene, suggest that biodegradation is slow(11,12). In general, PAHs with five or more benzene rings do not biodegrade readily(13).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), benzo(e)pyrene, which has an extrapolated vapor pressure of 5.7X10-9 mm Hg at 25 °C(2), is expected to exist primarily in the particulate phase in the ambient atmosphere. Based on an estimated super-cooled vapor pressure of 1.8X10-7 mm Hg at 25 °C(3), a small percentage of benzo(e)pyrene is expected to exist in the vapor phase in the ambient atmosphere(1). Similar PAHs have been detected in the vapor phase in ambient air(4,5). Vapor-phase benzo(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(3). Particulate-phase benzo(e)pyrene is also degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is also estimated to be 7.7 hours(SRC), calculated from a measured rate constant of 5.0X10-11 cu cm/molecule-sec at 25 °C(6). Particulate-phase benzo(e)pyrene may be removed from the air by wet and dry deposition(SRC). Benzo(e)pyrene absorbs strongly at wavelengths >290 nm(7,8) and, therefore, is expected to be susceptible to direct photolysis by sunlight(SRC).

Food Survey Values · 2 Einträge

In meat the amount of benzo(e)pyrene present depends on the method of cooking: time of exposure, distance of the heat source and whether or not the melted fat is allowed to drip into the heat source. Charcoal broiled or barbecued meat contained 1.7 to 7.5 ug/kg; up to 17.5 ug/kg were found in charcoal broiled T bone steak. In smoked ham, up to 5.2 ug/kg benzo(e)pyrene were found; heavy smoking increased the content to 17.9 ug/kg. Benzo(e)pyrene was detected in tomatoes at a concentration of 0.2 ug/kg. 1 out of 15 brands of whisky contained benzo(e)pyrene at a concentration of 0.3 ug/L; black tea extract contained 1.9 to 22.3 ug/kg benzo(e)pyrene; baker's dry yeast contained 3.1 to 55 ug/kg; roasted peanuts contained up to 0.4 ug/kg benzo(e)pyrene; and roasted coffee contained 0.3 to 7.2 ug/kg benzo(e)pyrene. The compound has laso been detected not qunatified in salad, tomatoes, spinach, kale, cereals, vegetables, roasted coffee, black tea, roasted peanuts and yeast(1).

The following benzo(e)pyrene concentrations have been reported for various foods, ug/kg: smoked herring and salmon, 0.4 to 1.2; barbecued beef, 1.7; canned smoked oysters, 16.0; canned non smoked oysters, 1.0; smoked sausage, hams, pork and bacon, 0.2 to 2.0; charbroiled steak, chicken, hamburger and frankfurters, 2.0 to 20; vegetable oils, 0.4 to 2.6; spinach, 6.9; salads, 3.7 to 14.7; kale, 1.1 to 76.2; soybeans, 4.3; cereals, 0.3 to 4.9; various char broiled steaks and ribs, 5.5 to 7.5(1). Based upon a total diet study conducted in the United Kingdom, the contribution of benzo(e)pyrene from individual food groups to the total dietary load are as follows: cereals, 31%; meat, 3%; fish, 1%; oils/fats, 53%; fruit/sugar, 3%; vegetables, 9%; and beverages and milk, 0%(2); benzo(e)pyrene concentrations in the individual food groups were as follows, ug/kg: cereals, 0.17 to 0.29 (0.22 average); meat, <0.08 to 0.13 (0.03 average); fish, 0.09 to 0.34 (0.12 average); oils/fats, <0.08 to 3.20 (1.10 average); fruits and sugars, <0.08 to 0.08 (0.03 average); root vegetables, <0.08 to 0.15 (0.02 average); other vegetables, <0.08 to 0.40 (0.10 average); beverages and milk, <0.08 (the detection limit)(2). Benzo(e)pyrene levels of 0.05 to 23 ug/kg were detected in fat samples taken from 26 food products on the Finish market(3); the highest levels were in margarine(3). Benzo(e)pyrene concentrations of 1.29-89.94 ug/kg were detected in Spanish olive pomace oil(4).

Exposure RoutesOral (L10) ; inhalation (L10)
Milk ConcentrationsAs part of a total diet study conducted in the United Kingdom, no detectable levels of benzo(e)pyrene (detection limit of 0.08 ug/kg) were found in various milk samples(1).
Toxicity Summary · 2 Einträge

IDENTIFICATION AND USE: Benzo(e)pyrene (B(e)P) is a constituent of coal tar. It is used in experimental research. Polycyclic aromatic hydrocarbons 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. HUMAN EXPOSURE AND TOXICITY: B(e)P is a toxic element in cigarette smoke. It is a toxicant to human retinal pigment epithelial cells in vitro. It causes cell death and induces apoptosis by the involvement of multiple caspase pathways. Human microvascular endothelial cells exposed to B(e)P showed a decrease in cell viability. It induced unscheduled DNA synthesis in HeLa cells in the presence of an exogenous metabolic system. The agent is not classifiable as to its carcinogenicity to humans. ANIMAL STUDIES: It has been observed to cause violent uveitis when injected intraocularly in animal eyes. One study showed that B(e)P is a very weak tumor initiator, a weak complete carcinogen, a moderate tumor promoter, possibly a weak co-tumor-initiator when given with benzo(a)pyrene, and a potent anit-tumor-initiator when given with 7,12-dimethylbenz[a]anthracene. In another study, a group of 20 female mice received applications of a 0.1% solution of benzo(e)pyrene by skin painting for life. Of five animals that survived 13 months after the start of treatment, two had skin papillomas and three had carcinomas. In other experiment, 30 female mice received 100 ug benzo(e)pyrene by skin application for 30 weeks. At 30 weeks, 68% of the mice had papillomas (2.1 papillomas/mouse); and at 40 weeks, 24% of mice had carcinomas. Benzo(e)pyrene was mutagenic to Salmonella typhimurium in the presence of an exogenous metabolic system. It did not induce mitotic recombination in yeast. It did not induce mutations or sister chromatid exchange in cultured mammalian cells and was negative in assays for morphological transformation. In the one available report, it did not induce chromosomal aberrations in vitro. In the one available in-vivo study, it induced sister chromatid exchange, but not chromosomal aberrations in hamster bone marrow.

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)

Average Daily Intake · 1 Eintrag

FOOD: Based upon a total diet study conducted in the United Kingdom, the total dietary load of benzo(e)pyrene is 0.17 ug/person/day assuming a total diet consumption of 1.46 kg food and beverages(1). Based upon a survey of Dutch foods, the mean intake of benzo(e)pyrene was reported to be 0.14 ug/person/day(2). AIR: Based upon an ambient air monitoring study conducted in Osaka, Japan in 1981-1982, the avg daily respiratory intake was determined to be 22 ng/day/man(3).

Plant Concentrations · 1 Eintrag

Lettuce and rye that were grown at a site near a highway had benzo(e)pyrene concentrations of 0.1 to 3.5 ug/kg fresh wt(1). Since the 1840s, crops have been harvested and stored for long term agricultural studies at a site in the UK(2); benzo(e)pyrene levels in grass samples were found to vary from 28 ug/kg in 1860 to 1862 to 93 ug/kg in 1879 to 1881 and then fall gradually to 5 ug/kg in 1985 to 1986(2); between 1877 and 1984, levels in wheat grain ranged from 0.29 to 2.50 ug/kg with the lowest levels occurring most recently(2).

Animal Concentrations · 1 Eintrag

Benzo(e)pyrene concentrations of 66-89 ng/g dry wt were detected in seston blue mussel (Mytilus edulis L.) taken from the coastal area of the northern Baltic(1). Gallbladders of common eider ducks (Somateria mollissima), which feed on the mussels, had a mean concentration of 2.1 ng/g dry wt(1). Benthic organisms (worms and midges) taken from the Raison River and Lake Erie near a Detroit power plant had benzo(e)pyrene levels of 20 to 110 ppb(2). Slugs, beetles, millipedes, earthworms and Casuarina littorina collected near a roadside in Brisbane, Australia contained 7, 2.5, 1, 13, and 4 ng/g wet weight benzo(e)pyrene, respectively(3).

Regulatorische Informationen

Clean Water Act Requirements · 2 Einträge

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/.

Sicherheitsdaten

wgk
3
ridadr
UN 3077 9/PG 3
hs_code
29029000
RTECS-Nr.
DJ4200000
risk_code
45-50/53-67-65-38-11-20
Toxizität
mmo-sat 1 nmol/plate CNREA8 40,1985,80
hazard_code
T,N,Xn,F
safety_code
53-45-60-61-62-33-25-16-9
hazard_class
6.1(b)
packing_group
III
Speicherklasse
3 - Flammable liquids
Giftige Stoffe Daten
192-97-2(Hazardous Substances Data)
Hazard Classifications
Aquatic Acute 1Aquatic Chronic 1Asp. Tox. 1Flam. Liq. 2Skin Irrit. 2STOT SE 3
Metabolism/Metabolites · 5 Einträge

The 4,5-dihydrodiol is the major metabolite of benzo(e)pyrene, but the 9,10-dihydrodiol has also been detected as a minor product following incubation of benzo(e)pyrene with rat liver preparations. Glucuronic acid conjugates of 3-hydroxy-benzo(e)pyrene and of the 4,5-dihydrodiol have been reported in hamster embryo cells. The formation of the 4,5,9,10-tetraol and the 9,10,11,12-tetraol as well as unidentified phenols from the precursor 9,10-dihydrodiol have also been reported using hepatic microsomal preparations from various species including humans.

The potential biological activity of benzo(e)pyrene was investigated by a determination of the mutagenic activity of the polycyclic hydrocarbon and six of its derivatives in the absence and presence of a cytochrome P-450-dependent monooxygenase system. In the presence of hepatic microsomes from Aroclor 1254-pretreated rats or the cytochrome P-450-dependent monooxygenase system purified to near homogeneity from these microsomes, benzo(e)pyrene, trans-9,10-dihydroxy-9,10-dihydrobenzo(e)pyrene (bay region dihydrodiol), and trans-9,10-dihydroxy-9,10,11,12-tetrahydrobenzo(e)pyrene were metabolized to products which had little or no mutagenic activity toward strains TA 98 and TA 100 of Salmonella typhimurium. Under the same assay conditions, the products formed from trans-4,5-dihydroxy-4,5-dihydrobenzo(e)pyrene (K-region dihydrodiol) had modest mutagenic activity. In contrast with these results, 9,10-dihydrobenzo(e)pyrene was metabolically activated to potent mutagenic products which were 10- to 25-fold more active than the products formed from benzo(e)pyrene. The high intrinsic mutagenic activity of the chemically synthesized benzo ring tetrahydroepoxide of 9,10-dihydrobenzo(e)pyrene in both strains of bacteria and in cultured Chinese hamster V79 cells suggested that the high mutagenicity of 9,10-dihydrobenzo(e)pyrene after metabolism was mediated by this bay region tetrahydroepoxide. Liver microsomal metabolites of several of the benzo(e)pyrene derivatives were analyzed by high pressure liquid chromatography. Incubation of 9,10-dihydrobenzo(e)pyrene with hepatic microsomes from untreated or Aroclor 1254-pretreated rats confirmed the metabolic formation of the benzo ring epoxide of 9,10-dihydrobenzo(e)pyrene and established the formation of several other metabolites. In contrast to these results, trans-9,10-dihydroxy-9,10-dihydrobenzo(e)pyrene was not metabolized to benzo ring diol epoxides but rather was converted to 4,5,9,10-tetrahydroxy-4,5,9,10-tetrahydrobenzo(e)pyrene along with three phenolic derivatives of the dihydrodiol. Thus, lack of formation of a benzo ring epoxide provides a rationale for the inability of 9,10-dihydroxy-9,10-dihydrobenzo(e)pyrene to be metabolically activated by rat liver enzymes to mutagenic products and may contribute to the low carcinogenic activity of benzo(e)pyrene in rodents.

The major organic solvent sol metabolite formed in extracellular medium after 24 hr of culture (hamster embryo cells) with B[e]P was K-region dihydrodiol 4,5-dihydro-4,5-dihydroxybenzo[e]pyrene and small amt monohydroxybenzo[e]pyrenes.

The genotoxicity of 15 polycyclic aromatic hydrocarbons was determined with the alkaline version of the comet assay employing V79 lung fibroblasts of the Chinese hamster as target cells. These cells lack the enzymes necessary to convert PAHs to DNA-binding metabolites. ... 11 PAHs, i.e., benzo[a]pyrene (BaP), benz[a]anthracene, 7,12-dimethylbenz[a]anthracene, 3-methylcholanthrene, fluoranthene, anthanthrene, 11H-benzo[b]fluorene, dibenz[a,h]anthracene, pyrene, benzo[ghi]perylene and benzo[e]pyrene caused DNA strand breaks even without external metabolic activation, while naphthalene, anthracene, phenanthrene and naphthacene were inactive. When the comet assay was performed in the dark or when yellow fluorescent lamps were used for illumination the DNA-damaging effect of the 11 PAHs disappeared. White fluorescent lamps exhibit emission maxima at 334.1, 365.0, 404.7, and 435.8 nm representing spectral lines of mercury. In the case of yellow fluorescent lamps these emissions were absent. Obviously, under standard laboratory illumination many PAHs are photo-activated, resulting in DNA-damaging species. This feature of PAHs should be taken into account when these compounds are employed for the initiation of skin cancer. ...

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)

Verwendung und Herstellung

Uses · 6 Einträge

A constituent of coal tar; [Merck Index] Used in biochemical research; [HSDB]

BIOCHEMICAL RESEARCH

... /Benzo(e)pyrene/ has been employed for experimental production of tumors of rat conjunctiva.

There is no ... known use of this compound.

PAHs are generally not produced commercially in the United States except as research chemicals. /Polycyclic aromatic hydrocarbons/

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

U.S. Production · 3 Einträge

(1975) NOT PRODUCED COMMERCIALLY IN US

(1977) NOT PRODUCED COMMERCIALLY IN US

There is no commercial production ... of this compound.

General Manufacturing Information · 3 Einträge

Benzo(e)pyrene occurs ubiquitously in products of incomplete combustion; it is also found in fossil fuels.

Constituent of coal tar.

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/

Anwendungen

VerwendenUsed for studies of immune suppressive activity of bezo[e]Pyrene on antibody response to DNP-Ficoll and sheep erythrocytes and "dispersive liquid -liquid micro extraction” technique by extracting organic compounds from water samples.

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Ergänzende Hinweise

DefinitionChEBI: An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings. It is listed as a Group 3 carcinogen by the IARC.