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Benzo(ghi)perylene

HCID 9117
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Grundinformationen

CAS
191-24-2
Standard-SMILES
c1cc2ccc3ccc4ccc5cccc6c(c1)c2c3c4c56
InChIKey
GYFAGKUZYNFMBN-UHFFFAOYSA-N
Summenformel
C22H12
Durchschnittliche Molmasse
276,3 g/mol
Monoisotopische Masse
276,09390038

Überblick

Benzo[ghi]perylene is a colorless to white crystalline solid. Water insoluble.

Namen und Bezeichner

Bevorzugter Name
Benzo(ghi)perylene
IUPAC
hexacyclo[12.8.0.02,11.03,8.04,21.017,22]docosa-1(14),2(11),3(8),4,6,9,12,15,17(22),18,20-undecaene
Englischer Name
Benzo[ghi]perylene
Summenformel
C22H12
Molmasse
276.33

Namen und Synonyme

Benzo[ghi]perylene191-24-21,12-Benzoperylene1,12-BenzperyleneBenzo[g,h,i]peryleneBENZO(GHI)PERYLENEBenzo(g,h,i)peryleneBenzo(ghi)pyrileneDTXSID50239085ZME2E2Q9Lbenzo(ghi)-peryleneNSC-89275
Weitere Namen anzeigen
hexacyclo[12.8.0.02,11.03,8.04,21.017,22]docosa-1(14),2(11),3(8),4,6,9,12,15,17(22),18,20-undecaeneDTXCID303908hexacyclo(12.8.0.02,11.03,8.04,21.017,22)docosa-1(14),2(11),3(8),4,6,9,12,15,17(22),18,20-undecaeneRefChem:118246205-883-8CCRIS 784C22H12MFCD00004135

Datenbank-Bezeichner

CAS
191-24-2
PubChem CID
9117
DTXSID
DTXSID5023908
ChEMBL
CHEMBL1880376
ChEBI
CHEBI:34568
UNII
5ZME2E2Q9L
EC Number
205-883-8
Nikkaji
J5.878E

Eigenschaften

Berechnete Struktureigenschaften

XLogP
6,6
Polarare Oberfläche (TPSA)
0 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
0
Frei drehbare Bindungen
0
Schwere Atome
22
Formalladung
0
Komplexität
411

Experimentelle und physikochemische Eigenschaften

Chemical ClassesSemi-Volatile Organic Compound (SVOC)
Polymers · 2 Einträge

Other Classes -> Polycyclic Aromatic Hydrocarbons

Polycyclic aromatic hydrocarbon

SpringerMaterials PropertiesAngular frequency
PesticidesPesticide -> EPA IRIS
LogP · 3 Einträge

log Kow = 6.63

6.58

7.04

Density · 2 Einträge

1.3 g/cu cm

1.3 g/cm³

Color/Form · 2 Einträge

Yellow-green fluorescent leaflets from benzene

Large, pale yellow-green plates (recrystallized from xylene)

Solubility · 3 Einträge

In water, 2.6X10-4 mg/L at 25 °C

Soluble in 1,4-dioxane, dichloromethane, benzene, and acetone

Solubility in water: none

Boiling Point

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

This chemical does not meet GHS hazard criteria for 2.4% (1 of 41) of reports.

Warning

H400 (97.6%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

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

Aggregated GHS information provided per 41 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

Gefahrenhinweise

Regulatory Information · 5 Einträge

Hazard Traits - Bioaccumulation; Environmental Persistence; Environmental tox

Restricted substance: Benzo[ghi]perylene

Substance: Benzo[ghi]perylene

Benzo[ghi]perylene: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelClass 9
Fire Hazards · 2 Einträge

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Combustible under specific conditions.

Fire PotentialCombustible under specific conditions.
Health HazardsExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Hazards SummaryMay cause irritation; [MSDSonline] See POLYCYCLIC AROMATIC HYDROCARBONS.

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 5 Einträge

... Using recently developed metabolic toxicity screening arrays and a biocolloid reactor-LC-MS/MS approach, both featuring films of DNA and human metabolic enzymes, we demonstrated the relatively low reactivity of metabolically activated benzo[ghi]perylene (B[ghi]P) toward DNA. Electro-optical toxicity screening arrays showed that B[ghi]P metabolites damage DNA at a 3-fold lower rate than benzo[a]pyrene (B[a]P), whose metabolites have a strong and well-understood propensity for DNA damage. Metabolic studies using magnetic bead biocolloid reactors coated with microsomal enzymes in 96-well plates showed that cyt P450s 1A1 and 1B1 provide high activity for B[ghi]P and B[a]P conversion. Consistent with published results, the major metabolism of B[ghi]P involved oxidations at 3,4 and 11,12 positions, leading to the formation of B[ghi]P 3,4-oxide and B[ghi]P 3,4,11,12-bisoxide. B[ghi]P 3,4-oxide was synthesized and reacted with deoxyadenosine at N6 and N7 positions and with deoxyguanosine at the N2 position. B[ghi]P 3,4-oxide is hydrolytically unstable and transforms into the 3,4-diol or converts to 3- or 4-hydroxy B[ghi]P. LC-MS/MS of reaction products from the magnetic biocolloid reactor particles coated with DNA and human enzymes revealed for the first time that a major DNA adduct results from the reaction between B[ghi]P 3,4,11,12-bisoxide and deoxyguanosine. Results also demonstrated 5-fold lower formation rates of the major DNA adduct for B[ghi]P metabolites compared to B[a]P. Overall, results from both the electro-optical array and biocolloid reactor-LC-MS/MS consistently suggest a lower human genotoxicity profile of B[ghi]P than B[a]P.

Carcinogenic polycyclic aromatic hydrocarbons (PAH), e.g., benzo[a]pyrene (BaP), possess a bay region comprising an ortho-fused benzene ring. Benzo[ghi]perylene (BghiP) represents the group of PAHs lacking such a "classic" bay region and hence cannot be metabolically converted like BaP to bay region dihydrodiol epoxides considered as ultimate mutagenic and carcinogenic metabolites of PAH. BghiP exhibits bacterial mutagenicity in strains TA98 (1.3 his(+)-revertant colonies/nmol) and TA100 (4.3 his(+)-revertant colonies/nmol) of Salmonella typhimurium after metabolic activation by the postmitochondrial hepatic fraction of CD rats treated with 3-methylcholanthrene. Inhibition of microsomal epoxide hydrolase (mEH) with 1,1,1-trichloro-2-propene oxide raised the bacterial mutagenicity of BghiP in TA98 almost 4-fold indicating arene oxides as ultimate mutagens. To confirm this assumption, the biotransformation of BghiP was elucidated. Incubation of BghiP with liver microsomes of CD rats treated with Aroclor 1254 yielded 17 ethyl acetate extractable metabolic products. Twelve metabolites were identified by a combination of chromatographic, spectroscopic, and biochemical methods. The microsomal biotransformation of BghiP proceeds by two pathways: Pathway I starts with the monooxygenase attack at the 7-position leading to the 7-phenol, which is transformed to the 7,8- and 7,10-diphenols followed by oxidation to the 7,8- and 7,10-quinones. On pathway II, the K regions of BghiP are successively converted to arene oxides yielding the indirectly identified 3,4-oxide and the 3,4,11,12-bisoxides. Enzymatic hydrolysis of the 3,4-oxide leads to the trans-3,4-dihydrodiol, which is oxidized to the 3,4-quinone. Similarly, the trans-3,4-trans-11,12-bisdihydrodiols and the trans-3,4-dihydrodiol 11,12-quinone are generated from the 3,4,11,12-bisoxides. The trans-3,4-dihydrodiol and the trans-3,4-trans-11,12-bisdihydrodiols are preferentially formed as R,R and R,R,R,R enantiomers, respectively. The intrinsic bacterial mutagenicity of the 3,4,11,12-bisoxides is rather low and hardly explains the strong increase in bacterial mutagenicity of BghiP after inhibition of mEH. Thus, we believe that the 3,4-oxide plays a more important role as the ultimate mutagenic metabolite of BghiP.

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· 3 Einträge

550 °C at 760 mm Hg

550 °C

550 °C @760 [mm Hg]

Decomposition · 3 Einträge

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

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

Decomposes on heating. This produces toxic fumes.

Melting Point · 4 Einträge

531 to 534 °F (NTP, 1992)

278.3 °C

278 °C

277 °C

Vapor Pressure · 2 Einträge

1.0X10-10 mm Hg at 25 °C

0.000000001 [mm Hg] @25 °C

Physikochemische Eigenschaften

Schmelzpunkt
277 °C · 277 °C
Siedepunkt
550 °C · 550 °C
Dichte
1.3 g/cm3 · 1.3 g/cm3
Reactive GroupHydrocarbons, Aromatic
Special Reports · 5 Einträge

Junk GA, Ford CS; Chemosphere 9 (4): 187-230 (1980). A review of organic emissions from selected combustion processes.

Sterling TD et al; J Air Pollut Control Assoc 32 (3): 250-9 (1982). A critical review of the literature concerning indoor byproduct levels of tobacco smoke.

Hauser TR, Bromberg SM; Environ Monit Assess 2 (3): 249-72 (1982). An article concerning US EPA monitoring program at Love Canal, New York.

USEPA; Health and Environmental Effects Profile for Benzo(ghi)perylene (1987) EPA/600/X-87/395.

U.S. Dept Health & Human Services/Agency for Toxic Substances Disease Registry; Toxicological Profile for Polycyclic Aromatic Hydrocarbons (Update) (1995) NTIS# PB/95/264370

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/
Reactivity Profile · 1 Eintrag

Vigorous reactions, sometimes amounting to explosions, can result from the contact between aromatic hydrocarbons, such as BENZO[GHI]PERYLENE, 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.

Chemical DangersUpon heating, toxic fumes are formed. Decomposes on heating. This produces toxic fumes.
Air and Water ReactionsInsoluble in water.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

To extinguish a fire involving this chemical you may use a dry chemical, carbon dioxide, foam or halon extinguisher; a water spray may also be used. (NTP, 1992)

In case of fire in the surroundings, use appropriate extinguishing media.

First Aid Measures · 4 Einträge

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.

Rinse mouth. Refer for medical attention .

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.

Safe StorageWell closed.
Fire Fighting Procedures · 2 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

Storage ConditionsKeep container tightly closed in a dry and well-ventilated place.[Sigma-Aldrich; Safety Data Sheet for Benzo
Cleanup Methods · 1 Eintrag

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Avoid dust formation. Avoid breathing vapors, 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.[Sigma-Aldrich; Safety Data Sheet for Benzo

Nonfire Spill Response · 1 Eintrag

SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill 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 alcohol followed by washing with a strong 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 · 5 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

This research program was conducted to determine the capability of biological treatment and activated carbon desorption to remove chemical carcinogens and other hazardous organic cmpd (including benzo(ghi)perylene) from water and wastewater. All cmpd tested exhibited some degree of biological degradation. Carbon adsorption was also effective in removing the cmpd from aqueous solutions. Large polynuclear aromatic compounds exhibited reduced adsorption capacities due to exclusion from the small diameter pores of the carbon.

The following wastewater treatment technologies have been investigated for 1,12-Benzoperylene: Chemical precipitation.

Spillage DisposalSweep spilled substance into covered containers. Carefully collect remainder. Then store and dispose of according to local regulations. Do NOT let this chemical enter the environment.
Preventive Measures · 5 Einträge

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Avoid dust formation. Avoid breathing vapors, 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.[Sigma-Aldrich; Safety Data Sheet for Benzo

Precautions for safe handling: Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fire protection.[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(GHI)PERYLENE (8 total), please visit the HSDB record page.

Isolation and EvacuationExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Toxikologische Informationen

Body Burden · 2 Einträge

In an analysis of 33 human placenta samples collected from non-smoking women in Beijing, China during 2005-2006, benzo(ghi)perylene was detected at mean, median, minimum and maximum concentrations of 0.098, 0.118, not detectable and 0.244 ng/g fresh weight respectively(1). In an analysis of 7 human umbilical blood samples collected from non-smoking women in Beijing, China during 2005-2006, benzo(ghi)perylene was detected at mean, median, minimum and maximum concentrations of 0.014, 0.036, not detectable and 0.170 ng/g fresh weight respectively(1).

Polycyclic aromatic hydrocarbons were detected in human fat and liver and their average concentrations were 1100 and 380 /parts per trillion/ (undefined), respectively. Benzo(ghi)perylene levels in liver were lower than those in fats.

TreatmentThere is no know antidote for PAHs. Exposure is usually handled with symptomatic treatment. (L10)
Interactions · 4 Einträge

In tests for cocarcinogenic activity, benzo(a)pyrene was tested as the carcinogen at 5 ug applied simultaneously in the same solution with the cocarcinogen benzo(ghi)perylene (0.007 or 0.021 mg/dose) 3 times weekly in 0.1 mL acetone to groups of 50 female ICR/HU mice. Lower dose group had first papilloma in 238 days, with papillomas in 19 mice and squamous carcinomas in 10 mice; the higher dose group had first papilloma in 222 days, with papillomas in 20 mice and squamous carcinomas in 18 mice. No effects were observed in benzo(ghi)perylene admin at 0.021 mg/dose without benzo(a)perylene. /From table/

... In this study, human hepatoma HepG2 cells cotreated with benzo[a]pyrene (BaP) and benzo[g,h,i]perylene (BghiP) were used as a model to investigate the cocarcinogenic mechanism of BghiP in BaP-induced carcinogenesis. DNA adduct formation is thought to initiate carcinogenesis, so the effect of BghiP on BaP-DNA adduct formation was evaluated using a (32)P-postlabeling assay. The BaP-DNA adduct levels increased following the addition of BghiP, in a dose-dependent manner. However, no adducts were formed with BghiP alone. /A/ previous report showed that cytochrome P450 1A1 (CYP1A1) is responsible for the metabolic activation of BaP and the formation of B[a]P adduct in HepG2 cells. Western blot and Northern blot analyses were used to evaluate whether BaP-induced CYP1A1 protein and mRNA levels increased following the addition of BghiP. Our data showed that BghiP enhanced BaP-induced CYP1A1 protein and its mRNA levels. To understand whether BghiP enhances BaP-induced CYP1A1 gene expression through the aryl hydrocarbon receptor (AhR) signaling pathway, a gel retardation assay was performed to elucidate the synergistic mechanism of BghiP in BaP-induced CYP1A1 gene expression. The results showed that BghiP causes an increase in the nuclear accumulation of AhR in cells and/or activation of AhR to a DNA-binding form. There was a concordant increase in the transcription activation of CYP1A1 gene and the induction of AhR signal pathway. Our findings demonstrated that BghiP enhances BaP-induced CYP1A1 transcription by AhR activation and suggested that the induction mechanism of CYP1A1 contributes to the cocarcinogenic potential of BghiP in BaP-induced carcinogenesis.

12-O-Tetradecanoylphorbol 13-acetate (TPA), a known tumor promoter, enhances the morphologic transformation of Syrian hamster embryo cells induced by low transforming concentrations of N-methyl-N'-nitro-N-nitrosoguanidine (MNNG) (0.025-0.1 ug/mL) without potentiation of cell lethality or of changes in sister chromatid exchanges (SCEs) or chromosomal aberration frequencies. When MNNG was added to logarithmically growing cultures and TPA was added 2, 24, or 48 hr later, no changes in SCE frequency relative to MNNG alone occurred. Similar results were obtained with TPA in cells that had been exposed to MNNG in stationary growth phase. Whereas no transformation occurred with TPA alone and pretreatment with TPA did not affect MNNG transformation, its addition 2 hr after MNNG reduced transformation frequency but addition 24-72 hr after MNNG increased the transformation frequency up to 6-fold. TPA had a minimal effect on increasing the transformation frequency (2-fold) induced by MNNG at 0.25 ug/mL, a high concentration. Of three polycyclic hydrocarbons, perylene, benzo[g,h,i]perylene, and benz[a]anthracene, known as weak or noncarcinogens, only benz[a]anthracene induced a very low transformation frequency; however, after TPA, transformation occurred with all three. Because the number of cells whose transformation was initiated by low doses of carcinogen is much larger than the number of cells giving rise to transformed colonies in the absence of TPA, the frequency of the initial event is greater than can be expected from point mutations. Furthermore, the promotional aspect of transformation is not accompanied by a parallel increase in SCE.

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. ...

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)
Ecotoxicity Values · 2 Einträge

LC50; Species: Daphnia magna (Water Flea) age <24 hr neonate; Conditions: freshwater, static, 20 °C, simulated solar radiation; Concentration: 0.48 nM for 48 hr /98% purity/

LC50; Species: Daphnia magna (Water Flea) age <24 hr neonate; Conditions: freshwater, static, 20 °C, visible light plus UVA; Concentration: 3.77 nM for 48 hr /98% purity/

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), measured Koc value of 6.3X10+6(2) and 4.1X10+4(3), indicate that benzo(ghi)perylene is expected to be immobile in soil(SRC). Volatilization of benzo(ghi)perylene from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 3.31X10-7 atm-cu m/mole(4). Benzo(ghi)perylene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1X10-10 mm Hg at 25 °C(5). In general, PAHs with five or more benzene rings do not biodegrade readily(6). Biodegradation of PAHs having five or more rings, including benzo(ghi)perylene, was slight to non-existent in three soils under field conditions(7). Soil degradation studies have found that benzo(ghi)perylene degrades slowly with half-lives ranging from 173 to 863 days(8-10). Benzo(ghi)perylene absorbs strongly at wavelengths >290 nm(11) and, therefore, is expected to be susceptible to direct photolysis on soil surfaces exposed to sunlight(SRC).

AQUATIC FATE: Based on a classification scheme(1), measured Koc value of 6.3X10+6(2) and 4.1X10+4(3), indicates that benzo(ghi)perylene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon a Henry's Law constant of 3.31X10-7 atm-cu m/mole(5). According to a classification scheme(6), an estimated BCF of 11,000(SRC), from its log Kow of 6.63(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). In general, PAHs with five or more benzene rings do not biodegrade readily(11). Biodegradation of PAHs having five or more rings, including benzo(ghi)perylene, was slight to non-existent in three soils under field conditions(12). A laboratory study using acclimated water and sediment from the Yellow River found that water high in sediment content could biodegrade benzo(ghi)perylene(13).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), benzo(ghi)perylene, which has a vapor pressure of 1.0X10-10 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 3.2X10-8 mm Hg at 25 °C(3), a small percentage of benzo(ghi)perylene is expected to exist in the vapor phase in the ambient atmosphere(1). Ambient monitoring studies have detected benzo(ghi)perylene in both the particulate and vapor phases(4,5). Vapor-phase benzo(ghi)perylene 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 4.4 hours(SRC), calculated from its rate constant of 8.7X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase benzo(ghi)perylene is also degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 4.5 hours(SRC), calculated from a measured rate constant of 8.5X10-11 cu cm/molecule-sec at 25 °C(6). Particulate-phase benzo(ghi)perylene may be removed from the air by wet and dry deposition(SRC). Benzo(ghi)perylene absorbs strongly at wavelengths >290 nm(7) and, therefore, is expected to be susceptible to direct photolysis by sunlight(SRC).

Food Survey Values · 2 Einträge

Fruits and vegetables collected from 19 localities in southern Moravia (Czech Republic) in 2003 were found in contain the following concentrations of benzo(ghi)perylene (in ug/kg fresh weight): parsely (0.02-0.05), tomato (0.02-0.06), apple (0.02-0.08), apricot (0.03-0.46), cauliflower (0.01-0.21), grape (0.04-0.09), cabbage (0.02)(1). Benzo(ghi)perylene has been detected in food samples at levels >1.0 ug/kg in many food categories including fats and oils, vegetable oils, processed fruit, dried fruit, vegetables, cocoa, whole grains, flour, meat, molluscs, fish, herbs, spices, coffee and tea(2).

Nineteen of 23 samples of margarines, butter and vegetable oils contained benzo(ghi)perylene at concentrations ranging from 0.02 to 2.4 ug/kg with an avg of 0.59 ug/kg(1). Composite fish samples from the Great Lakes harbors and tributary mouths contained benzo(ghi)perylene(2). Smoked fish including dried herring, whitefish and Kippered cod showed benzo(ghi)perylene at concentrations of 1.0, 2.4 and 2.2 ppb, respectively(3). Japanese horse mackerel contained benzo(ghi)perylene for 3 different methods of preparation at concentrations of 2-10, 2 and 1 ppb(3). Broiled steaks, smoked ham and barbecued ribs and beef contained benzo(ghi)perylene at concentrations of 6.7, 1.2, 4.7 and 4.3 ppb, respectively(3). Smoked sausage and cooked bologna contained benzo(ghi)perylene at concentrations raging from 0.25 to 0.50 and 0.04 to 0.20 ppb, respectively(3). Coffee soots contained benzo(ghi)perylene at concentrations ranging from 100 to 140 ppb(3). Smoked cod liver oil, halibut liver oil and coconut oil each contained benzo(ghi)perylene at a concentration of 20 ppb(3). The minimum and maximum benzo(ghi)perylene concentration in lettuce grown 8, 15, 25, 35, 45 and 65 m from a major highway were 1.7, 2.7; 1.1, 1.6; 0.9, 1.3; 0.9, 1.3; 0.8, 1.3; and 0.7, 1.0; ug/kg, respectively(4). The concentration of benzo(ghi)perylene in the peel, inner peel, outer core, and core of carrot tissues was determined to be 4.5 ug/kg dry weight, below detection, 4.8 ug/kg dry weight, and below detection, respectively(5). The fine aerosol emission rate for benzo(ghi)perylene from a charbroiled hamburger (regular) was determined to be 0.24 mg/kg(6).

Exposure Routes · 2 Einträge

The substance can be absorbed into the body by inhalation of its aerosol and through the skin.

Oral (L10) ; inhalation (L10)

Milk Concentrations · 1 Eintrag

In an analysis of 21 human milk samples collected from non-smoking women in Beijing, China during 2005-2006, benzo(ghi)perylene was detected at mean, median, minimum and maximum concentrations of 0.030, 0.019, not detectable and 0.135 ng/g fresh weight respectively(1).

Toxicity Summary · 2 Einträge

IDENTIFICATION AND USE: Benzo(ghi)perylene (BghiP) is a solid. It is used in small amounts for scientific research. Polycyclic aromatic hydrocarbons (PAHs) are a group of chemicals that are formed during the incomplete burning of coal, oil, gas, wood, garbage, or other organic substances, such as tobacco and charbroiled meat. HUMAN EXPOSURE AND TOXICITY: In human cells BghiP can activate the overexpression of aryl hydrocarbon receptor (AhR) and cytochrome CYP4B1, and the effects are abated by the AhR receptor antagonist. BghiP represents the group of PAHs lacking a "classic" bay region and hence it cannot be metabolically converted to bay region dihydrodiol epoxides considered as ultimate mutagenic and carcinogenic metabolites of PAH. Experimental results demonstrate lower human genotoxicity profile of B[ghi]P than for benzo[a]pyrene. ANIMAL STUDIES: Benzo(ghi)perylene showed no tumorigenic effect in the respiratory tracts of rats when given at doses of 5 mg. BghiP was analyzed for induction effect on skin and liver aryl hydrocarbon hydroxylase and 7-ethoxycoumarin o-deethylase activities in neonatal rats. A single topical application caused induction of liver enzymes without producing effects on skin enzymes. BghiP exhibits bacterial mutagenicity in strains TA98 and TA100 of Salmonella typhimurium after metabolic activation. ECOTOXICITY STUDIES: BghiP was responsible for retardation of growth and increases in adrenal and nasal gland weight in nestling herring gulls (Larus argentatus).

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

Based upon the average atmospheric concentration of benzo(ghi)perylene at a remote site of 0.25 ng/cu m(1) and the average daily inhalation for a human adult of 20 cu m of air, the average daily intake of benzo(ghi)perylene via air is 20 pg(SRC). Based upon the average concentration of benzo(ghi)perylene among various food groups of 1 ng/kg(2,3) and the average daily consumption for a human adult of 1600 g of food, the average daily intake of benzo(ghi)perylene via food is 1.6 ug(SRC).

Ecotoxicity Excerpts · 1 Eintrag

/BIRDS and MAMMALS/ The physiological effects of a single ingested dose of Prudhoe Bay Crude Oil (PBC), its aromatic fractions, and PBC Corexit 9527 emulsion were studied in nestling herring gulls (Larus argentatus). The high molecular weight aromatic compounds, including benzo(ghi)perylene, were responsible for retardation of growth and increases in adrenal and nasal gland weight.

Regulatorische Informationen

CERCLA Reportable Quantities · 1 Eintrag

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).

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/.

State Drinking Water Guidelines(FL) FLORIDA 210 ug/l

Sicherheitsdaten

Alarmwort
Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H410

After incubation with liver microsomes from nonpretreated rats, no metabolites were found from benzo(ghi)perylene.

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)

Absorption, Distribution and Excretion · 2 Einträge

An analytical procedure is described which includes extraction of polycyclic aromatic hydrocarbons (PAH), including benzo(ghi)perylene, and polycyclic aromatic hydrocarbons metabolites from urine, reduction of metabolites to the original polycyclic aromatic hydrocarbons and subsequent analysis by HPLC. The mean value of the sum of the 11 polycyclic aromatic hydrocarbons in non smoker's urine was 1.1 ug/mmol creatinine. The sum of polycyclic aromatic hydrocarbons in smoker's urine was significantly higher. Increased levels of PAH were found in the urine of aluminum reduction workers.

... Benzo(ghi)perylene is absorbed readily from the gastrointestinal tract and lung. In general, polycyclic aromatic hydrocarbons are highly lipid soluble and can pass across epithelial membranes.

Verwendung und Herstellung

Uses · 5 Einträge

Used for scientific research; Not commercially used or produced; [HSDB] Benzo(ghi)perylene is present as a component of polycyclic aromatic hydrocarbons (PAH) content in the environment usually resulting from the incomplete combustion or pyrolysis of organic matters, especially fossil fuels and tobacco. [ICSC]

Small amounts are used for scientific research.

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/

PAHs are released into the environment via the combustion of fossil fuels, coke oven emissions and vehicle exhausts, as well as naturally from forest fires and vocanic eruptions. PAHs from these sources may contaminate nearly water systems. They are also found in coal tar and charbroiled food. (L10)

U.S. ProductionThere is no commercial production ... of this compound.
General Manufacturing Information · 2 Einträge

Benzo(ghi)perylene occurs ubiquitously in products of incomplete combustion; it also occurs in considerable amounts in coal-tar and is an important component of gasoline engine exhaust.

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/

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