Benzo[ghi]fluoranthene
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Benzo[ghi]fluoranthene
structure -
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CAS No:
203-12-3
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Formula:
C18H10
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Chemical Name:
Benzo[ghi]fluoranthene
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Synonyms:
Benzo[ghi]fluoranthene;7,10-Benzofluoranthene;Benzo[mno]fluoranthene;2,13-Benzofluoranthene;NSC 89272
- Categories:
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CAS No:
Description
Yellow needles with greenish-yellow fluorescence (recrystallized from petroleum ether); blue fluorescence in solution.
YELLOW CRYSTALS.
Benzo[ghi]fluoranthene is a member of phenanthrenes.
Benzo[ghi]fluoranthene Basic Attributes
226.27
226.27
205-903-5
92XNX26268
0527
89272
DTXSID4075455
Yellow crystals|Yellow needles with greenish-yellow fluorescence (recrystallzed from petroleum ether (a mixture of low-boiling hydrocarbons)); blue fluorescence in solution
2902909090
Characteristics
0
7.23
YELLOW CRYSTALS.
1.1624 (estimate)
149 °C
170-180 °C @ Press: 0.2 Torr
189.9±13.7 °C
1.997
Solubility in water: none
2-8°C
Vapour pressure, Pa at 20°C:
Relative vapour density (air = 1): 7.8
mma-sat 10 mg/plate MUREAV 174,247,86
Flammable; burning produces irritating fumes
Henry's Law constant = 1.3X10-6 atm-cu m/mole at 25 °C (est)
Decomposes on heating producing toxic fumes|Hydroxyl radical reaction rate constant = 6.2X10-11 cu-cm/molc sec at 25 °C (est)
Safety Information
III
6.1(b)
2811
DF6140000
Ventilated, low temperature and dry
P260, P264, P270, P309+P311, P405, P501
H371
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.
Combustible.
Use water spray, powder.
Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.
Well closed.
NO open flames.
PREVENT DISPERSION OF DUST!
Use local exhaust or breathing protection.
Protective gloves. Protective clothing.
Wear safety goggles, face shield or eye protection in combination with breathing protection if powder.
Benzo(ghi)fluoranthene was identified in gasoline engine exhaust at concentrations of 112-244 ug/L fuel(1). Gaseous emissions from gasoline-powered chain saws had combined benzofluoranthene isomer concentrations ranging from 1.2-2.0 ug/cu m(2). Two turbine engine exhaust had combined benzofluoranthene isomer levels of 33.17 and 67.17 ng/cu m(3). Lawn mower engines were found to emit benzo(ghi)fluoranthene levels of 7.9-13.5 ug/hr with catalyst controls and 20.3-51.9 ug/hr without catalyst controls(4). Monitoring conducted in Los Angeles, CA in 1993 near traffic tunnels identified benzo(ghi)fluoranthene emission rates of 70.9 and 19.7 ug/L fuel in the vapor-phase and particulate phase respectively(5). Benzo(ghi)fluoranthene was detected in particle emissions from industrial boiler burning of No. 2 distillate fuel(6). Coke oven emission were found to contain benzo(ghi)fluoranthene(7). The mean emission factor of benzo(ghi)fluoranthene detected from light and heavy duty vehicles in a California roadway tunnel ranged from 0.44-89.99 ug/kg fuel burned(8). Benzo(ghi)fluoranthene emissions from catalyst-equipped gasoline-powered vehicles was 0.276 and 0.063 ug/km in the gas and particle phases respectively(9); emissions from non-catalyst-equipped gasoline-powered vehicles was 10.7 and 46.8 ug/km in the gas and particle phases respectively(9).|Benzo(ghi)fluoranthene was identified in wastewater effluents from an aluminum factory in Sweden(1). Aerosol emission rate of benzo(ghi)fluoranthene from hot asphalt roofing tar pot fumes was 4.3 ug/g(2).
SEDIMENT: Analysis of sediment cores taken from a creek near an industrial site of Bitterfeld, Germany detected a benzo(ghi)fluoranthene concentration of 5000 ug/kg(1). Sediment samples collected between 2002-2006 from the Hamilton Harbor, Ontario, Canada and surrounding creeks were found to contain benzo(ghi)fluoranthene (concentration not reported)(2). Sediments collected from the Black Sea during 1988 and 1990 cruises contained benzo(ghi)fluoranthene concentrations of 0.5-275 ng/g dry wt(3).
URBAN/SUBURBAN: Air samples collected in Antwerp, Belgium in 1974-1975 contained combined benzofluoranthene isomer concentrations of 15.68 ng/cu m in the summer and 114.46 ng/cu m in the winter(1). Aerosol collected from six sites in Hong Kong and China in 1993 contained benzo(ghi)fluoranthene concentrations of 24-1621 pg/cu m(2). Aerosols collected from Kenmore Sqaure in Boston, MA during June-July 1994 had a benzo(ghi)fluoranthene concentration of 0.90 ng/cu cm(3). Air particulate sampling conducted in Sacramento, Modesto and Bakersfield, CA during Dec 2000-Jan 2001 detected benzo(ghi)fluoranthene concentration ranges of 0-1380, 4-1130 and 0.72-618 pg/cu m respectively(4).|INDOOR AIR: Air monitoring conducted in the basement room of a home in Boulder, CO burning natural gas in a fireplace between 1997 and 2000 detected benzo(ghi)fluoranthene (concentration not reported)(1). In a 2003 study conducted in Sweden, the indoor air of 13 homes using wood-burning appliances contained a median benzo(ghi)fluoranthene concentration of 0.19 ng/cu m (mean 0.39 ng/cu m) while 10 homes without wood-burning appliances contained a median benzo(ghi)fluoranthene concentration below the limit of quantification (0.05-0.15 ng/cu m)(2).|RURAL/REMOTE: Air samples collected in Botrange, Belgium in 1974-1975 contained combined benzofluoranthene isomer concentrations of 2.06 ng/cu m in the summer and 6.53 ng/cu m in the winter(1). Samples of sea air collected near Ostend, Belgium in 1974-1975 contained benzofluoranthene concentrations of 65.51 ng/cu m in the winter(1). PM2.5 aerosol collected from sites in the southeastern US in 1999 and 2000 had benzo(ghi)fluoranthene concentrations of 0.01-0.04 ng/cu m(2). Aerosols collected from Quabbin Summit, MA during July 1994 had a benzo(ghi)fluoranthene concentration of 0.078 ng/cu cm(3). Benzo(ghi)fluoranthene was identified in air samples collected from high mountain regions of Europe during 1996-1998 monitoring in the Alps, the Pyrenees and Norway(4).
Benzo(ghi)fluoranthene has been identified in mainstream cigarette smoke (0.1 ug/100 cigarettes, 0.1 mg/kg cigarette smoke condensate), mainstream smoke of marijuana cigarettes, emissions from the burning of various types of coals (0.01-8.9 mg/kg burned fuel)and from oil-fired stoves (0.15-0.47 mg/kg)(1). Smoke emitted from the charcoal grilling of meat patties contained benzo(ghi)fluoranthene levels of 0.96 ug/kg meat(2). Analysis of fine particles emissions from the burning of six Northeastern US woods identified benzo(ghi)fluoranthene concentrations of 0.059-0.198 mg/g(3). Combustion of Kaft lignin had a benzo(ghi)fluoranthene emission factor of 3-150 mg/kg(4). Benzo(ghi)fluoranthene was detected in emissions from the combustion of scrap tires(5). Combustion of pulverized coal emitted benzo(ghi)fluoranthene levels of 16.4-260 ug/g coal(6). The emission rate of benzo(ghi)fluoranthene from the burning of pine wood, oak wood and synthetic log was 0.11-0.27 mg/kg of log burned(7). The emission rate of benzo(ghi)fluoranthene from the burning of 6 southern US wood species was 0.077-0.151 mg/g wood(8). The average emission of benzo(ghi)fluoranthene concentration detected during the prescribed burning of forest areas in Georgia in 2004 was 0.0972 mg/g organic content(9). The benzo(ghi)fluoranthene emission factor from the burning of various coals ranged from 0.001-58 mg/kg of coal burned(10).
Toxicity
IDENTIFICATION AND USE: Benzo(ghi)fluoranthene is a polycyclic aromatic hydrocarbon (PAH). There is no commercial production or known use of this compound. HUMAN STUDIES: Human exposure to benzo(ghi)fluoranthene occurs primarily through the smoking of tobacco, inhalation of polluted air and by ingestion of food and water contaminated by combustion effluents. ANIMAL STUDIES: Benzo(ghi)fluoranthene was tested for carcinogenicity in one study in female mice by skin painting; no skin tumor was observed. Benzo(ghi)fluoranthene was mutagenic to Salmonella typhimurium in the presence of an exogenous metabolic system.
Benzo(ghi)fluoranthene occurs in fossil fuels(1). Polyaromatic hydrocarbons (PAHs) also occur in volcanic eruptions(2,3).
There is no commercial production or known use for benzo(ghi)fluoranthene(1). Benzo(ghi)fluoranthene occurs ubiquitously as a product of incomplete combustion(1). It has been identified in mainstream cigarette smoke and mainstream smoke of marijuana cigarettes(1). Emissions from gasoline/diesel engines and highway vehicles(2,3) release benzo(ghi)fluoranthene to the environment. Benzo(ghi)fluoranthene occurs in emissions from the combustion of wood(4), coal(5), distillate fuel(6) and scrap tires(7).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.8X10+5(SRC), determined from a structure estimation method(2), indicates that benzo(ghi)fluoranthene is expected to be immobile in soil(SRC). Volatilization of benzo(ghi)fluoranthene from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.3X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). In addition, adsorption to soil is expected to attenuate potential volatilization(SRC). Benzo(ghi)fluoranthene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.9X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Polycyclic aromatic hydrocarbons (PAHs), such as benzo(ghi)fluoranthene, with more than 3 rings appear to be extremely stable to biodegradation(3). Breakdown in soil generally takes weeks to months for PAHs with 3 rings, primarily by action of microorganisms; PAHs with 4 or more rings are generally resistant to biodegradation(4,5). Soil microbes adapted specifically to PAHs are capable of biodegrading benzo(ghi)fluoranthene(6). Benzo(ghi)fluoranthene absorbs light strongly at wavelengths >290 nm(7) 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), an estimated Koc value of 1.8X10+5(SRC), determined from a structure estimation method(2), indicates that benzo(ghi)fluoranthene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.3X10-6 atm-cu m/moleSRC), developed using a fragment constant estimation method(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 41 and 305 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 >10 years if adsorption is considered(4). According to a classification scheme(5), an estimated BCF of 2040(SRC), from an estimated log Kow of 5.52(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is very high, provided the compound is not metabolized by the organism(SRC). However, benzo(ghi)fluoranthene may not bioconcentrate in aquatic organisms which contain microsomal oxidase, such as fish, as this enzyme enables the rapid metabolism of certain polycyclic aromatic hydrocarbons(6). Polycyclic aromatic hydrocarbons (PAHs) with four or more rings, such as benzo(ghi)fluoranthene, are generally expected to be resistant to biodegradation(7). Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions(3). Benzo(ghi)fluoranthene absorbs strongly at wavelengths >290 nm(8), and therefore is expected to be susceptible to direct photolysis at water surfaces exposed to sunlight(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), benzo(ghi)fluoranthene, which has an estimated vapor pressure of 1.9X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase benzo(ghi)fluoranthene 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 6.2 hours(SRC), calculated from its rate constant of 6.2X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Particulate-phase benzo(ghi)fluoranthene may be removed from the air by wet and dry deposition(SRC). Benzo(ghi)fluoranthene absorbs strongly at wavelengths >290 nm(3) and, therefore, is expected to be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of benzo(ghi)fluoranthene with photochemically-produced hydroxyl radicals has been estimated as 6.2X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 6.2 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Benzo(ghi)fluoranthene is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups that hydrolyze under environmental conditions(2). Benzo(ghi)fluoranthene absorbs light strongly at wavelengths >290 nm(3) and, therefore, is expected to be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 2040 was calculated in fish for benzo(ghi)fluoranthene(SRC), using an estimated log Kow of 5.52(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC), provided the compound is not metabolized by the organism(SRC). However, benzo(ghi)fluoranthene may not bioconcentrate in aquatic organisms which contain microsomal oxidase, such as fish, as this enzyme enables the rapid metabolism of certain polycyclic aromatic hydrocarbons(3). Using a database of measured fish biotransformation half-lives of PAHs(4), a fish biotransformation half-life of 0.8 days has been estimated for benzo(ghi)fluoranthene(1).|In the food chain important to humans, bioaccumulation takes place, specifically in oils and fats(1). Caged mussels (Mytilus galloprovincialis) exposed for 30 days in three sites of a coastal lagoon (in Italy) contaminated by PAHs had benzo(ghi)fluoranthene concentrations rise from undetectable levels at day zero (<3 ng/g dry wt) to 15.1-30 ng/g after 30 days of exposure(2).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of benzo(ghi)fluoranthene can be estimated to be 1.8X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that benzo(ghi)fluoranthene is expected to be immobile in soil. Based on monitoring of water and sediment layers conducted in the Baltic Sea, benzo(ghi)fluoranthene had an apparent log Koc of 5.0-6.7(3).
The Henry's Law constant for benzo(ghi)fluoranthene is estimated as 1.3X10-6 atm-cu m/mole(SRC) developed using a fragment constant estimation method(1). This Henry's Law constant indicates that benzo(ghi)fluoranthene is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 41 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 305 days(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 >10 years if adsorption is considered(3). Benzo(ghi)fluoranthene's estimated Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to be an important fate process(SRC). In addition, adsorption to soil is expected to attenuate potential volatilization(SRC). Benzo(ghi)fluoranthene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.9X10-7 mm Hg(SRC), determined from a fragment constant method(1).
SURFACE WATER: Benzo(ghi)fluoranthene was identified in Japanese seawater(1).|RAIN/SNOW: Benzo(ghi)fluoranthene has been identified in Japanese rainwater(1). Benzo(ghi)fluoranthene was detected snow core samples collected at remote areas of five mountain lakes in Europe (Alps, Pyrenees, Caledonia)(2).
Margarines, butter and vegetable oils collected from Finnish markets and the margarine industry were analyzed for PAHs(1); benzo(ghi)fluoranthene was detected in 18 of 22 samples at concentrations ranging from 0.05 to 2.4 ug/kg(1). Smoke from the charcoal grilling of meat patties contained benzo(ghi)fluoranthene levels of 0.96 ug/kg meat(2). Emissions of benzo(ghi)fluoranthene from Chinese cooking, as sampled from four restaurants in Guangzhou City, China, ranged from 13-160 ng/mg(3).
Occupational exposure to benzo(ghi)fluoranthene may occur through inhalation and dermal contact with this compound at workplaces where benzo(ghi)fluoranthene is generated as a product of incomplete combustion of organic fuels. Monitoring data indicate that the general population may be exposed to benzo(ghi)fluoranthene via inhalation of ambient air, inhalation of tobacco smoke, ingestion of food and dermal contact with particulate matter resulting from combustion(SRC). Since benzo(ghi)fluoranthene is a product of incomplete combustion(1), occupational situations involving heating organic material may result in exposure to this compound through inhalation of air particulate matter and dermal contact with combustion products(SRC).|The personal air of six workers in a plant producing carbon anodes for aluminum electrolysis were monitored for exposure to benzo(ghi)fluoranthene and other PAHS(1); the benzo(ghi)fluoranthene concentrations identified for the six workers were 0.06-0.21, 0.19-0.47, 0.02-0.06, 0.15-0.34, 0.02-0.28 and 0.05-0.92 ug/cu m respectively(1).
Drug Information
350.03 Days
Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention . Wear protective gloves when administering first aid.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aromatic hydrocarbons and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aromatic hydrocarbons and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... .Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aromatic hydrocarbons and related compounds/
/GENOTOXICITY/ A number of isomeric C18H10 polycyclic aromatic hydrocarbons (PAHs), thought to be primarily cyclopenta-fused PAHs, are produced during the combustion and pyrolysis of fossil fuels. To determine the importance of their contributions to the total mutagenic activity of combustion and pyrolysis samples in which they are found, we characterized reference quantities of four C18H10 CP-PAHs: benzo[ghi]fluoranthene (BF), cyclopenta[cd]pyrene (CPP), cyclopent[hi]acephenanthrylene (CPAP), and cyclopent[hi]aceanthrylene (CPAA). Synthesis of CPAA and CPAP is described. The availability of reference samples of these isomers also proved to be an essential aid in the identification of the C18H10 species often found in combustion and pyrolysis samples. Chemical analysis of selected combustion and pyrolysis samples showed that CPP was generally the most abundant C18H10 isomer, followed by CPAP and BF. CPAA was detected only in pyrolysis products from pure PAHs. We tested the four C18H10 PAHs for mutagenicity in a forward mutation assay using S. typhimurium. CPP, BF, and CPAA were roughly twice as mutagenic as benzo[a]pyrene (BaP), whereas CPAP was only slightly active. These PAHs were also tested for mutagenic activity in human cells. In this assay, CPP and CPAA were strongly mutagenic but less active than BaP, whereas CPAP and BF were inactive at the dose levels tested. Also, the bacterial and human cell mutagenicity of CPAA and CPAP were compared with the mutagenicity of their monocyclopenta-fused analogs, aceanthrylene and acephenanthyrlene. Although the mutagenicities of CPAP and acephenanthrylene are similar, the mutagenic activity of CPAA is an order of magnitude greater than that of aceanthyrlene.|/OTHER TOXICITY INFORMATION/ Benzo(ghi)fluoranthene is present as a component of the total content of polynuclear aromatic compounds in the environment. Human exposure to benzo(ghi)fluoranthene occurs primarily through the smoking of tobacco, inhalation of polluted air and by ingestion of food and water contaminated by combustion effluents.
7,10-benzofluoranthene
The substance can be absorbed into the body by inhalation of its aerosol and through the skin.
MAY BE ABSORBED!
Benzo[ghi]fluoranthene Use and Manufacturing
There is no commercial production or known use of this compound.
Computed Properties
Molecular Weight:226.3
XLogP3:5.4
Exact Mass:226.078250319
Monoisotopic Mass:226.078250319
Heavy Atom Count:18
Complexity:314
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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