9,10-Dimethylanthracene

log Kow = 5.69

5.25

In water, 5.60X10-2 mg/L at 25 °C

Insoluble in water

360 °C

BP: 140-142 °C at 0.5-1 mm Hg

Questionable carcinogen with experimental carcinogenic and tumorigenic data

UV: 6579 (Sadtler Research Laboratories Spectral Collection) /1,3-Dimethylanthracene/

UV: 6574 (Sadtler Research Laboratories Spectral Collection) /2,3-Dimethylanthracene/

Danger

H312 (83%): Harmful in contact with skin [Warning Acute toxicity, dermal]

P203, P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P317, P318, P321, P333+P317, P342+P316, P362+P364, P403, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 47 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H312: Harmful in contact with skin [Warning Acute toxicity, dermal]

USEPA; Ambient Water Quality Criteria Doc: Polynuclear Aromatic Hydrocarbons (Draft) (1980)

Health and Welfare Canada; Polycyclic Aromatic Hydrocarbons Rept No 80-EHD-50 (1979)

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/

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/.

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

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

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: Do not let product enter drains. 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.

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contaminated packaging: Dispose of as unused product.

The worker should wash daily at the end of each work shift, and prior to eating, drinking, smoking, etc. /Coal tar pitch volatiles/

Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises. /Coal tar pitch volatiles/

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Do not let product enter drains.

Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fire protection.

For more Preventive Measures (Complete) data for 9,10-Dimethylanthracene (8 total), please visit the HSDB record page.

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 9,10-Dimethylanthracene (6 total), please visit the HSDB record page.

Respirator Recommendations: At concentrations above the NIOSH REL, or where there is no REL, at any detectable concentration: /Coal tar pitch volatiles/[Table#4917]

Respirator Recommendations: Escape conditions: /Coal tar pitch volatiles/[Table#4918]

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).

Skin protection: Handle with gloves.

For more Personal Protective Equipment (PPE) (Complete) data for 9,10-Dimethylanthracene (6 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4.6X10+4(SRC), determined from a structure estimation method(2), indicates that 9,10-dimethylanthracene is expected to be immobile in soil(SRC). Volatilization of 9,10-dimethylanthracene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.9X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption to soil is expected to attenuate volatilization(SRC). 9,10-dimethylanthracene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.0X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). 9,10-Dimethylanthracene reached 1.6 and 19.5% of its theoretical oxygen demand after 144 hours incubation in activated sludge from two different waste treatment facilities(4), suggesting that biodegradation may be a slow environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4.6X10+4(SRC), determined from a structure estimation method(2), indicates that 9,10-dimethylanthracene 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 2.9X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2 and 19 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 80 years if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 2600(SRC), from its log Kow of 5.69(7) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). 9,10-Dimethylanthracene reached 1.6 and 19.5% of its theoretical oxygen demand after 144 hours incubation in activated sludge from two different waste treatment facilities(8), suggesting that biodegradation may be a slow environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 9,10-dimethylanthracene, which has an estimated vapor pressure of 3.0X10-6 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 9,10-dimethylanthracene 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 0.1 days(SRC), calculated from its rate constant of 1.3X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 9,10-dimethylanthracene may be removed from the air by wet and dry deposition(SRC). Analogous anthracene contains chromophores that absorb at wavelengths >290 nm(4), suggesting that 9,10-dimethylanthracene may be susceptible to direct photolysis by sunlight(SRC).

9,10-Dimethylanthracene has reportedly been found in mineral oil(1). This compound was analyzed for but not found in samples of margarines, butters, and vegetable oils from Finland, detection limit 0.02 ug/kg(2), and samples of leaf lettuce from Finland, detection limit 0.05 ug/kg(3).

IDENTIFICATION AND USE: 9-10-Dimethylanthracene (9,10-DMA) is a solid polycyclic hydrocarbon. HUMAN EXPOSURE AND TOXICITY: There are no data available. ANIMAL STUDIES: 9,10-DMA was not mutagenic in the recessive lethal assay. 9,10-Dimethylanthracene showed a rather weak genotoxicity in Drosophila melanogaster studies. The fraction of all genotoxic events which are due to mitotic recombination was 83%. ECOTOXICITY STUDIES: 9,10-DMA suppressed cell proliferation of the freshwater species of fish, Lepomis macrochirus (bluegill).

/AQUATIC SPECIES/ Polycyclic aromatic hydrocarbons (PAH) have been demonstrated to affect immune system modulation. The freshwater species of fish, Lepomis macrochirus (bluegill), was employed to investigate the effects of a 14-day dietary exposure to PAH including 2-aminoanthracene (2-AA), 2-methylnaphthalene (2-MN), and 9,10-dimethylanthracene (9,10-DMA) and a mixture of these 3 compounds at a total dose of 3.1 +/- 0.01 mg on lymphocyte proliferation stimulated with 3 mitogens (concanavalin A [Con A], phorbol ester, and calcium ionophore). 2-Aminoanthracene was mitogenic itself and with added mitogens. 2-Methylnaphthalene induced some stimulatory and some inhibitory effects upon cell proliferation by Con A. 9,10-DMA and the mixture each suppressed cell proliferation. The mixture was highly suppressive to lymphocytes. Intracellular baseline calcium levels were reduced, possibly as a step prior to cell death. All PAH compounds tested were immunomodulatory to bluegill lymphocytes. Bluegill were demonstrated to have utility as a biomarker species for investigation of immunotoxicity.

9,10-Dimethylanthracene was tested for but not detected in air samples influenced by aircraft exhaust from C-130H aircraft at the Savannah Air National Guard base, Savannah GA(1). 9,10-Dimethylanthracene emissions of 0.119 and 0.289 mg/g polystyrene were reported in particulate and gaseous emissions, respectively, from polystyrene combustion(2).

Using a bench scale reactor, 9,10-dimethylanthracene was identified as a pyrolysis product of shredded and ground Dunlop scrap tires burned in a furnace at 850 °C. The yield of 9,10-dimethylanthracene decreased as the bulk air ratio increased(1).[Table#4916]

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 9,10-dimethylanthracene can be estimated to be 4.6X10+4(SRC). According to a classification scheme(2), this estimated Koc value suggests that 9,10-dimethylanthracene is expected to be immobile in soil.

Summary information indicates that 9,10-dimethylanthracene (CAS # 781-43-1) was evaluated for carcinogenicity in a group of 32 female Swiss CD-1 albino mice by application of a single dose of the test substance (in 100 uL of acetone) followed by tri-weekly dosing with the promoter phorbul myristate acetate (in 100 uL of acetone). Treatment with the promoter began 2 weeks following application of the test substance and continued for 180 days. Tumors were found in 8 of 32 of the mice. There was a total of 8 tumors in the group. The first observable tumor was seen at 140 days.

9,10-Dimethylanthracene is one of many polycyclic aromatic hydrocarbons (PAH), a group of chemicals that are formed during the incomplete burning of coal, oil, gas, wood, garbage, or other organic substances(1,2). PAHs generally occur as complex mixtures, for example as part of combustion products such as soot, not as single compounds. PAHs occur naturally in volcanoes and forest fires. They can also be found in substances such as crude oil and coal. They are found throughout the environment in the air, water, and soil(1). Many PAHs found in the environment are formed during pyrolysis and incomplete combustion of organic matter at high temperatures(2). /Polycyclic aromatic hydrocarbons/

URBAN/SUBURBAN: 9,10-Dimethylanthracene was present at 0.7, 0.16 and 0.03 ng/cu m in air samples taken at Baltimore (urban), Hart Miller Island (rural; 18km NE) and from the USCG Station at Stillpond (over water; 23km further NE), respectively, on the northern Chesapeake Bay, sampled in June, 1996(1). 9,10-Dimethylanthracene mean concentrations were 0.01 and <0.012 ng/cu m in summer 2000 and winter 2001, respectively, outside of homes tested in Shimizu, Japan(2).

INDOOR: 9,10-Dimethylanthracene mean concentrations were 0.01 and 0.0082 ng/cu m in summer 2000 and winter 2001, respectively, inside of homes tested in Shimizu, Japan(1).

SOURCE DOMINATED: Air samples collected from Kokkola, Finland, a small industrial town, were analyzed for 9,10-dimethylanthracene. The air samples contained a number of different polycyclic aromatic hydrocarbons, but not 9,10-dimethylanthracene, detection limit 0.1 ng/cu m(1). 9,10-Dimethylanthracene was tested for but not detected in air particulate matter from over the lower Back River estuary in the Baltimore Harbor area on the Chesapeake Bay, sampled in June 1996(2).

9,10-Dimethylanthracene mean concentrations were reported as 218.7 (Las Caletillas), 24.11 (El Poris) and 70.0 (El Medano) ng/g dry wt in the Canary Islands Intertidal limpet (Patella ulyssiponensis aspera) collected at mid-tide throughout 1991-1993 on the southeast coast of Tenerife. The last oil spills near the Canary Islands were on Dec 19, 1989 and Dec 30-31, 1989(1). 9,10-dimethylanthracene concentrations were 591.1, 526.5 and 108.7 ng/g dry wt, respectively, in the intertidal limpet P. crenata from the same area(2).

Polycyclic aromatic hydrocarbons (PAHs), such as 9,10-dimethylanthracene, are found in the environment and are formed during pyrolysis and incomplete combustion of organic matter at high temperatures(1). 9,10-Dimethylanthracene occurs primarily in cigarette smoke(2) which will result in its direct release to the environment(SRC).

AEROBIC: Using Warburg respirometer tests, 9,10-dimethylanthracene, present at a concentration of 500 mg/L, was not biodegraded to any extent by activated sludge from three different treatment plants. 9,10-Dimethylanthracene reached 19.5% of its theoretical oxygen demand over a period 144 hours using activated sludge from a treatment plant receiving municipal waste. 9,10-Dimethylanthracene was not biodegraded by activated sludge obtained from a treatment plant receiving residential wastes only. 9,10-Dimethylanthracene reached 1.6% of its theoretical oxygen demand over a period of 144 hours using activated sludge from a treatment plant receiving combined domestic wastewater(1).

PURE CULTURE: Biodegradation of 9,10-dimethylanthracene, present at 10 mg/mL, was studied over 90 days at 20 and 7 °C, respectively. The enrichment culture included Acidovorax, Bordetella, Pseudomonas, Sphingomonas and Variovorax species. Under nitrate reducing conditions, 9,10-dimethylanthracene was not biodegraded using the same soils and temperatures, with the exception of 7% degradation in Alert soil at 7 °C(1).[Table#4915]

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/.

The metabolism of two polycyclic aromatic hydrocarbons i.e. anthracene and 9,10-dimethylanthracene by Micrococcus sp., Pseudomonas sp. and Bacillus macerans was examined. The above compounds were used as a sole carbon source for their growth. Using the reversed-phase thin layer chromatography techniques a number of anthracene and 9,10-dimethylanthracene metabolites were isolated and their structures identified spectroscopically. These included anthracene and 9,10-dimethylanthracene cis-dihydrodiols, hydroxy-methyl-derivatives and various phenolic compounds. Bacteria metabolize hydrocarbons using the dioxygenase enzyme system, which differs from the mammalian cytochrome P-450 monoxygenase. ...

In-vitro stereoselective metabolism of methylated anthracenes by rat liver microsomes, and the configurations and optical purity of the trans-dihydrodiol metabolites were investigated. Liver microsomes from untreated immature male Sprague-Dawley-rats and from rats pretreated with either 3-methylcholanthrene (3-MC) or phenobarbital (PB) were incubated with 9-methylanthracene (779022) (9-MA), 9-hydroxymethylanthracene (9-OHMA), or 9,10-dimethylanthracene (781431) (9,10-DMA) for 60 minutes. Metabolites were separated by reverse phase high performance liquid chromatography (HPLC). Results indicated that 9-MA, 9-OHMA and 9,10-DMA were metabolized by 3-MC, PB and control microsomes in a stereoselective manner. With the exception of the formation of 9-OHMA-trans-3,4 dihydrodiol by PB microsomes, all of the trans-dihydrodiol metabolites formed from the three microsomal enzyme systems were predominantly the R,R enantiomers. The 3-MC microsomes exhibited much higher stereoselectivity than the Pb or control microsomes in the formation of trans-dihydrodiols from anthracene, 9-MA, 9-OHMA and 9,10-DMA. Optical purities of the trans-dihydrodiol metabolites, determined by analysis of the chiral stationary phase HPLC profiles of the dihydrodiols or their corresponding tetrahydrodiol derivatives, ranged from 76 to 98 percent, 4 to 76 percent and 4 to 60 percent for 3-MC, PB and control microsomes, respectively. Methyl and hydroxymethyl substituents slightly decreased the stereoselectivity of the trans-dihydrodiol formation. The authors conclude that the lower optical purities of the trans-dihydrodiols formed by either PB or control microsomes are clearly due to the lower stereoselectivity of the cytochrome-P-450 enzymes or epoxidation of the polycyclic aromatic hydrocarbon substrates, but not due to the change of the stereoselectivity of the epoxide hydrolase enzymes.

The metabolism of the weakly-carcinogenic hydrocarbon, 9,10-dimethylanthracene (DMA) by rat-liver microsomal preparations has been examined. 9-Hydroxymethyl-10-methylanthracene (9-OHMeMA) and 9,10-dihydroxymethyl-anthracene (9,10-DiOHMeA) were identified as metabolites by comparing their chromatographic and spectral properties with those of the authentic compounds. The trans-1,2-dihydro-1,2-dihydroxy derivative of DMA (DMA 1,2-diol) was the major metabolite formed which was identified by its chromatographic, u.v., n.m.r. and mass spectral properties. The dihydrodiol was also formed in the oxidation of DMA in an ascorbic acid-ferrous sulphate-EDTA system. Two other dihydrodiols that were formed from DMA by metabolism appeared to be the trans-1,2- and 3,4-dihydrodiols of 9-OHMeMA (9-OHMeMA 1,2-diol and 9-OHMeMA 3,4-diol) and the further metabolism of DMA 1,2-diol yielded both of these dihydrodiols. When 9-OHMeMA was further metabolized, two main metabolites were formed; one was identified as 9,10-DiOHMeA and the other appeared to be 9-OHMeMA 3,4-diol. No metabolites were detected when 9,10-DiOHMeA was incubated with rat-liver microsomal fractions.

Not commercially produced in the US; [HSDB]

Laboratory chemicals, manufacture of substances.

(1977) NOT PRODUCED COMMERCIALLY IN USA

(1979) NOT PRODUCED COMMERCIALLY IN USA