Dibenzothiophene

Very soluble in ethanol and benzene. Soluble in chloroform, and methanol

In water, 1.47 mg/L water at 25 °C

0.000205 [mmHg]

2.05X10-4 mm Hg at 25 °C /extrapolated/

130.2 Ų [M]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID0047741]

153.42 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

This chemical does not meet GHS hazard criteria for 4.3% (3 of 69) of reports.

Danger

H302 (92.8%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P262, P264, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P316, P317, P321, P330, P332+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 69 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

Chemical: Dibenzothiophene

Dibenzothiophene: Does not have an individual approval but may be used under an appropriate group standard

There is no data available on cancer in humans. There is inadequate evidence of carcinogenicity in experimental animals. Dibenzothiophene is not classifiable as to its carcinogenicity in humans. [IARC, Vol. 103, 2013] Classified as a heterocyclic aromatic compound; [HSDB] Effects in lethal-dose animal studies include general anesthesia, coma, and fatty liver degeneration; [RTECS] See POLYCYCLIC AROMATIC HYDROCARBONS.

Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: dibenzothiophene is included in topical acne drug products.

Thiophenes, a class of polycyclic aromatic compound (PAC), which contain a sulfur in one of the rings, are components of petroleum. The Erika oil spill (December 1999) impacted 400 km of Atlantic French coast. The Erika fuel is an heavy fuel containing 3-4% sulfur and sulfur compounds such as thiophenes. It has been reported that water and sediments were contaminated by dibenzothiophene (DBT). Analysis of DNA adducts in fish liver and mussel digestive gland, living in sites impacted by Erika oil spill, has revealed DNA adduct pattern different from a classical PAH contamination. Few studies report biological activities of thiophenes in the environment .

... The Exxon Valdez spilled over 77 metric tons of dibenzothiophene and methyldibenzothiophenes into the environment.

Acute Tox. 4 (92.8%)

Acute toxicity (Oral) - Category 4

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. 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 soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Heterocyclic derivatives of polycyclic aromatic hydrocarbons (PAHs) are often significant components of environmental contaminant mixtures; however, their contribution to the toxicity of these mixtures is not well characterized. These heterocycles commonly co-occur in PAH mixtures, which contain agonists for the aryl hydrocarbon receptor (AHR). /The/ goal for these studies was to explore the effects of two PAH heterocycles, carbazole (CB) and dibenzothiophene (DBT), alone and in combination with a PAH-type agonist for the AHR (beta-naphthoflavone [BNF]) on AHR-mediated cytochrome P4501A (CYP1A) activity and on fish embryotoxicity. Embryos of Fundulus heteroclitus were exposed to CB or DBT, with and without coexposure to BNE Carbazole alone slightly induced, whereas DBT alone slightly reduced, in ovo CYP1A-mediated ethoxyresorufin-O-deethylase (EROD) activity compared to control values. However, exposure to CB or DBT reduced in ovo EROD activity in embryos coexposed to BNE Carbazole and DBT were characterized in vitro as noncompetitive CYP1A inhibitors. Carbazole and DBT enhanced the embryotoxicity of BNF, although neither compound was embryotoxic by itself. The co-occurrence of CB and DBT with PAH-type AHR inducers in contaminated ecosystems may increase the toxicity of PAH-type AHR agonists in these settings and may need to be considered when estimating the embryotoxicity of PAH mixtures.

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values in the range of 5,273 to 18,937(2), indicate that dibenzothiophene is expected to be immobile in soil(SRC). Volatilization of dibenzothiophene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.4X10-5 atm-cu m/mole(SRC), derived from its vapor pressure of 2.05X10-4 mm Hg(3) and water solubility of 1.47 mg/L(4); however, adsorption may attenuate this process(SRC). Volatilization from dry soil surfaces is not expected(SRC), based on the vapor pressure(3). Dibenzothiophene is expected to undergo biodegradation in acclimated soils(SRC). The biodegradation half-life of dibenzothiophene in an aerobic groundwater/soil slurry obtained from the American Creosote Works site in Pensacola, FL was approximately 8.2 days(5).

AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 11,584 to 20,535 using marine sediment obtained from the South China Sea(2), indicates that dibenzothiophene 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 3.4X10-5 atm-cu m/mole(SRC), derived from its vapor pressure of 2.05X10-4 mm Hg(4) and water solubility of 1.47 mg/L(5). However, adsorption to suspended solids and sediment may attenuate this process(SRC). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 24 hours and 16 days, respectively when adsorption is neglected. The volatilization half-life from a model pond is estimated as 217 days when adsorption is considered(6). According to a classification scheme(7), BCF values of 1,220-2,410 measured in fish(8), suggest bioconcentration in aquatic organisms is very high(SRC). Biodegradation is expected to occur in acclimated aqueous environments(SRC). Dibenzothiophene was slowly degraded (lag periods of 19-118 days) in three different microcosms using groundwater from a creosote contaminated site(9) and had a half-life of 10 days following a 7 day acclimation period in groundwater from a gasoline contaminated aquifer(10). The photolysis half-lives for dibenzothiophene in a river, eutrophic pond, and oligotrophic pond were estimated as 16, 39, and 8 days, respectively(11).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dibenzothiophene, which has a vapor pressure of 2.05X10-4 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase dibenzothiophene 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 2 days(SRC), calculated from its rate constant of 8.1X10-12 cu cm/molecule-sec at 25 °C(3). Particulate-phase dibenzothiophene may be removed from the air by wet and dry deposition(SRC). Dibenzothiophene absorbs UV light greater than 290 nm(4) and is susceptible to direct photolysis in the environment(5); however, the rate of this reaction in the atmosphere is not known(SRC).

Dibenzothiophene was detected in samples of margarine, butter, and vegetable oils at 0.03-0.46 ug/kg(1). Dibenzothiophene was detected in samples of cereal products at 0.50-4.3 ug/kg(2). Dibenzothiophene was detected in samples of leaf lettuce at levels of 0.08-0.60 ug/kg(3).

/AQUATIC SPECIES/ Fish embryos exposed to complex mixtures of polycyclic aromatic hydrocarbons (PAHs) from petrogenic sources show a characteristic suite of abnormalities, including cardiac dysfunction, edema, spinal curvature, and reduction in the size of the jaw and other craniofacial structures. To elucidate the toxic mechanisms underlying these different defects, ... zebrafish (Danio rerio) embryos /were exposed/ to seven non-alkylated PAHs, including five two- to four-ring compounds that are abundant in crude oil and two compounds less abundant in oil but informative for structure-activity relationships. /The authors/ also analyzed two PAH mixtures that approximate the composition of crude oil at different stages of weathering. Exposure to the three-ring PAHs dibenzothiophene and phenanthrene alone was sufficient to induce the characteristic suite of defects, as was genetic ablation of cardiac function using a cardiac troponin T antisense morpholino oligonucleotide. The primary etiology of defects induced by dibenzothiophene or phenanthrene appears to be direct effects on cardiac conduction, which have secondary consequences for late stages of cardiac morphogenesis, kidney development, neural tube structure, and formation of the craniofacial skeleton. The relative toxicity of the different mixtures was directly proportional to the amount of phenanthrene, or the dibenzothiophene-phenanthrene total in the mixture. Pyrene, a four-ring PAH, induced a different syndrome of anemia, peripheral vascular defects, and neuronal cell death, similar to the effects previously described for potent aryl hydrocarbon receptor ligands. Therefore, different PAH compounds have distinct and specific effects on fish at early life history stages.

/OTHER TERRESTRIAL SPECIES/ The effects of eight polycyclic aromatic compounds on the survival and reproduction of the collembolan Folsomia fimetaria L. were investigated in a well-characterized Danish agricultural soil. With the exception of acridine, polycyclic aromatic hydrocarbons (PAHs) and neutral N-, S-, and O-monosubstituted analogues showed similar toxicities to soil collembolans when the results were expressed in relation to total soil concentrations (mg/kg). The estimated concentrations resulting in a 10% reduction of reproductive output (EC10 values) were based on measured initial concentrations and were for acridine 290 mg/kg, carbazole 10 mg/kg, dibenzofuran 19 mg/kg, dibenzothiophene 7.8 mg/kg, fluoranthene 37 mg/kg, fluorene 7.7 mg/kg, phenantrene 23 mg/kg, and pyrene 10 mg/kg. When the EC10 values were converted to soil pore-water concentrations, they showed a highly significant correlation (r2 = 0.71, p < 0.01) to no-observed-effect concentrations for the freshwater crustacean Daphnia magna, as estimated by a quantitative structure activity relation (QSAR) for baseline toxicity (nonpolar narcosis). Only carbazole and acridine were more than two times more toxic (4.9 and 3.1, respectively) than expected from the Daphnia QSAR data. ...

/OTHER TERRESTRIAL SPECIES/ The effect of eight polycyclic aromatic compounds (PACs) on the seed emergence and early life-stage growth of three terrestrial plants (Sinapsis alba, Trifolium pratense and Lolium perenne) were studied in a greenhouse, using a Danish agricultural soil with an organic carbon content of 1.6%. After three weeks of exposure, seed emergence and seedling weight (fresh weight and dry weight) were determined. Exposure concentrations were verified with chemical analysis. The substances tested were four polycyclic aromatic hydrocarbons (fluoranthene, pyrene, phenanthrene and fluorene), the N-, S-, and O-substituted analogues of fluorene (carbazole, dibenzothiophene and dibenzofuran, respectively), and the quinoline representative acridine. Seedling growth was a far more sensitive endpoint than seed emergence for all substances. Concentrations estimated to give a 20% reduction of seedling fresh weight (EC20-values) ranged from 36 to 290 mg/kg for carbazole, 43 to 93 mg/kg for dibenzofuran, 37 to 110 mg/kg for dibenzothiophene, 140 to 650 mg/kg for fluoranthene, 55 to 380 mg/kg for fluorene, 37 to 300 mg/kg for phenanthrene, and 49 to 1300 mg/kg for pyrene. For acridine, no toxicity was observed within the concentration range tested (1-1000 mg/kg). As illustrated by the EC20-values, there was a rather large difference in sensitivity between the species, and T. pratense was the most sensitive of the species tested.

/AQUATIC SPECIES/ A series of polycyclic aromatic S heterocycles (PASH) were compared to their sterically and structurally similar polycyclic aromatic hydrocarbons (PAH) for toxicity, bioconcentration, and elimination in D. magna. The PASH were generally more toxic than their analogous PAH. Benzo(b)thiophene and benzo(b)naphtho(2,1-d)-thiophene were biconcentrated to a greater extent than naphthalene and chrysene, respectively. Dibenzothiophene and phenanthrene exhibited similar uptake curves. No clear trend was observed for elimination differences between PASH and PAH.

For more Ecotoxicity Excerpts (Complete) data for DIBENZOTHIOPHENE (8 total), please visit the HSDB record page.

Particulate-phase dibenzothiophene was emitted from a lawn mower using two different fuels at rates of 0.8 and 1.0 ug/hour(1). Using the same fuels and equipping the lawn mower engine with a catalytic converter, the particulate-phase emissions dropped to 0.1 ug/hour(1). Vapor-phase emissions of dibenzothiophene were 16.9 and 17.5 ug/hour without a catalytic converter and 7.4 and 8.2 ug/hour, when a catalytic converter was used(1). Dibenzothiophene was identified as a volatile emission product of hot asphalt roofing tar(2). Dibenzothiophene was emitted from light and heavy duty vehicles at a mean rate of 0.15 ug/km(3). Dibenzothiophene was emitted from vehicles near a tunnel in Los Angeles, CA at rates of 55.3 ug/L (vapor-phase) and 8.8 ug/L (particulate-phase)(4). Dibenzothiophene was identified, not quantified, as a combustion product of pulverized coal and tires(5). Dibenzothiophene was detected in storm water runoff from Philadelphia, PA at 44-62 ng/L(6). It was estimated that the Exxon Valdez spilled over 77 metric tons of dibenzothiophene and methyldibenzothiophenes into the environment of the Prince William Sound, AK(7).

The Koc of dibenzothiophene was measured in 14 soil and sediment samples collected from the Ohio, Missouri, Mississippi, and Illinois Rivers and their watersheds(1). The adsorption isotherms were determined to be linear over the entire concentration range and adsorption was shown to be strongly correlated with the percentage of organic carbon in the soil and sediment. The Koc values ranged from 5,273 to 18,937 with an average value of 11,120(1). Koc values in the range of 11,584 to 20,535 were calculated for dibenzothiophene from adsorption isotherms using marine sediment obtained from the South China Sea(2). According to a classification scheme(3), these Koc values suggest that dibenzothiophene is expected to be immobile in soil(SRC).

URBAN/SUBURBAN: Dibenzothiophene was detected at a concn of 9.08 ng/cu m in the atmosphere of Lanzhou, China(1). Dibenzothiophene was detected in atmospheric samples collected in Galveston Bay, TX. Particulate-phase levels were 0.002-0.021 ng/cu m(mean concn 0.007 ng/cu m), and vapor-phase levels were 0.074-2.580 ng/cu m (mean concn 0.888 ng/cu m)(2). Dibenzothiophene was detected in air samples collected in Corpus Christi, TX at a max concn of 0.010 ng/cu m(3). Atmospheric levels of dibenzothiophene in the air of lower Manhattan, NY from September to October 2001 ranged from 0-14 ng/cu m, with an average concn of 6 ng/cu m(4). Dibenzothiophene was detected in air samples collected in Birmingham, England at a concn range of 0.02-0.05 ng/cu m(5). The vapor-phase daytime concn of dibenzothiophene in the atmosphere of Masnou Harbor, Spain ranged from 1.42-3.73 ng/cu m, and the nighttime range was 0.91-1.59 ng/cu m(6). The aerosol-phase daytime concn of dibenzothiophene in the atmosphere of Masnou Harbor, Spain ranged from 0.021-0.095 ng/cu m, and the nighttime range was 0.039-0.098 ng/cu m(6).

INDOOR AIR: Dibenzothiophene was detected in the air of a paste plant in Norway at concns of 3.9 and 5.7 ug/cu m(1) and in the workplace air of a coke plant in Norway at levels of 15-76 ug/cu m (particulate) and 1.2-49 ug/cu m(vapor)(2). Dibenzothiophene was detected in the workplace air of an aluminum factory at 2.09 ug/cu m(3). Vapor-phase dibenzothiophene was measured in the workplace air of a creosote plant at levels of 0.1-2.8 ug/cu m(4).

Dibenzothiophene was detected in mussel samples collected from the Baltic Sea at levels of 27.8-292 ng/g (March 1995), 26.3-54.9 ng/g (October 1995), and 9.6-161 ng/g(August 1996)(1). Dibenzothiophene was identified, not quantified, in American pliace and yellowtail flounder collected in the Northwest Atlantic(2).

Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: dibenzothiophene is included in topical acne drug products.

Beijerinckia B8/36 when grown with succinate in the presence of dibenzothiophene, accumulated (+)-cis-1,2-dihydroxy-1,2-dihydrodibenzothiophene and dibenzothiophene-5-oxide in the culture medium. Each metabolite was isolated in crystalline form and characterized by a variety of chemical techniques, cis-Naphthalene dihydrodiol dehydrogenase, isolated from Pseudomonas putida, oxidized (+)-cis-1,2-dihydroxy-1,2-dihydrodibenzothiophene to a compound that was tentatively identified as 1,2-dihydroxydibenzothiophene. ...

The microbial transformation of dibenzothiophene (DBT) is of interest in the potential desulfurization of oil. /The authors/ isolated three soil Pseudomonas species which oxidized DBT to characteristic water-soluble, sulfur-containing products. Two of /the/ isolates harbored a 55-megadalton plasmid; growth in the presence of novobiocin resulted in both loss of the plasmid and loss of the ability to oxidize DBT. Reintroduction of the plasmid restored the ability to oxidize DBT to water-soluble products. The products resulting from the oxidation of DBT were characterized and included 3-hydroxy-2-formyl benzothiophene, 3-oxo-[3'-hydroxy-thionaphthenyl-(2)-methylene]-dihydrothionaph thene, and the hemiacetal and trans forms of 4-[2-(3-hydroxy)-thianaphthenyl]-2-oxo-3-butenoic acid. The products of DBT oxidation were inhibitory to cell growth and further DBT oxidation. DBT oxidation in our soil isolates was induced by naphthalene or salicylate and to a much lesser extent by DBT and was repressed by succinate.

Various microorganisms were screened for their ability to desulfurize dibenzothiophene (DBT) via a sulfur-specific pathway. Based on the desulfurization activity, strain G3 was selected as the best strain. From taxonomical studies, the strain was shown to belong to the genus Mycobacterium. Dibenzothiophene was degraded by both growing and resting cells of this strain, and 2-hydroxybiphenyl was detected as a dead-end product. Strain G3 could also desulfurize 4,6-dimethylDBT. Sulfate ion repressed the expression of the DBT desulfurizing enzyme(s). Accumulation of 2-hydroxybiphenyl produced severe inhibitory effects on both cell growth and DBT desulfurization. Resting cells of this strain could desulfurize about 250 ppm of DBT or 4,6-dimethylDBT within 12 hr.

The microbial degradation of organic sulfur compounds was studied in the anaerobic conditions using Desulfovibrio desulfuricans M6, a sulfate-reducing bacterium isolated from soil. Biphenyl was the major dibenzothiophene degradation product.

The metabolic pathway of the PAH fluorene and the cometabolic pathway of the PAHs phenanthrene, fluoranthene, anthracene and dibenzothiophene in Sphingomonas sp. LB126 were examined. ...For dibenzothiophene the metabolites dibenzothiophene-5-oxide and dibenzothiophene-5,5-dioxide were identified; these compounds appeared to be the products of a dead-end pathway. Since apart from dibenzothiophene no metabolites were found in very high concentrations for any of the other substrates, complete degradation is suggested, even for the cometabolic degradation of phenanthrene, fluoranthene and anthracene.

Large rainbow trout (400 g) were exposed to food pellets spiked with four polycyclic aromatic compounds (PACs). Muscle, liver, internal organs, fatty tissue, and blood were analyzed after 5, 10, 15, and 19 weeks for PAC, lipid, and moisture content. At all collection times, concentrations expressed on a per gram basis were higher in fatty tissue and internal organs, followed by liver and muscle, and lowest levels were observed in blood. When examining the tissue burden, the highest bioaccumulations of carbazole, dibenzofuran, dibenzothiophene, and fluorene were in muscle and internal organs, intermediate in fatty tissue, and lowest in blood and liver. Carbazole with the lowest log K(OW) showed the lowest concentration within any tissue. Levels in tissues were significantly correlated to log K(OW) (> 5% level of significance), especially with longer exposure, and were more highly correlated when examining muscle, fatty tissue, and internal organs (> 0.05%). Different tissues displayed different time trends, and ratios between organs help determine the length of exposure. The most striking change in levels observed with time was in internal organs relative to other tissues, particularly when compared to daily exposure. The elimination of contaminants in feces and gallbladder bile was also compared, because they represent additional tools to assess recent exposure.

Used in cosmetics and pharmaceuticals; [Hawley]

... Dibenzothiophene is included in topical acne drug products.

Cosmetics and pharmaceuticals, intermediate

Dibenzothiophene: ACTIVE

Drug category - acne