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Dechlorane Plus

Dechlorane Plus structure

Dechlorane Plus 

structure
  • CAS No:

    13560-89-9

  • Formula:

    C18H12Cl12

  • Chemical Name:

    Dechlorane Plus

  • Synonyms:

    1,4:7,10-Dimethanodibenzo[a,e]cyclooctene,1,2,3,4,7,8,9,10,13,13,14,14-dodecachloro-1,4,4a,5,6,6a,7,10,10a,11,12,12a-dodecahydro-;1,2,3,4,7,8,9,10,13,13,14,14-Dodecachloro-1,4,4a,5,6,6a,7,10,10a,11,12,12a-dodecahydro-1,4:7,10-dimethanodibenzo[a,e]cyclooctene;Dodecachlorodimethanodibenzocyclooctane;Dechlorane Plus 25;Bis(hexachlorocyclopentadieno)cyclooctane;Dechlorane Plus;Dechlorane Plus 515;Dodecachlorododecahydrodimethanodibenzocyclooctene;Dechlorane Plus 2520;Dechloran A;1,2,3,4,7,8,9,10,13,13,14,14-Dodecachloro-1,4,4a,5,6,6a,7,10,10a,11,12,12a-dodecahydro-1,4:7,10-dimethanodibenzo[a,e]cyclooctane;Dechlorane Plus 1000;Dechlorane Plus 35;Dodecachlorododecahydrodimethanodibenzocyclooctane;11114-14-0;39386-10-2;40372-58-5;59459-11-9;60880-74-2;1195618-74-6

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

Off-White Solid


DryPowder

Dechlorane Plus Basic Attributes

653.729

653.72

236-948-9

DTXSID7027750

Colorless crystals|White crystalline powder

29038900

Characteristics

0

9.51

DryPowder

1.8

>325 °C

675.3°C (rough estimate)

311.3±27.5 °C

1.6000 (estimate)

Insoluble

Store and handle in accordance with all current regulations and standards. Keep container tightly closed and properly labeled. Keep dry. Keep separated from incompatible substances ... .

7.1X10-10 mm Hg at 25 deg C (est)

Odorless

Henry's Law constant = 7.44X10-6 atm-cu m/mole at 25 °C (est)

Safety Information

II

6.1

UN 2922 8/PG 2

3

R25:Toxic if swallowed. R34:Causes burns.

24/25

AI3575000

T

Stable in water.

P261, P271, P304+P312, P304+P340, P312

H332

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.|Waste from material: Reuse or reprocess, if possible. Dispose in accordance with all applicable regulations. Container Management: Dispose of container in accordance with applicable local, regional, national, and/or international regulations. Container rinsate must be disposed of in compliance with applicable regulations.

Incompatibilities: Materials to Avoid: Incompatible with oxidizing agents.

|Warning|H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]|P261, P271, P304+P312, P304+P340, and P312|Aggregated GHS information provided by 286 companies from 3 notifications to the ECHA C&L Inventory.

Eye Protection: Safety glasses or goggles are recommended when there is a potential for eye contact.|Skin and Body Protection: Wear protective clothing to minimize skin contact. Use high-efficiency particulate filter vacuum to remove dust from clothing.|Hand Protection: Wear appropriate chemical resistant gloves. Consult a glove supplier for assistance in selecting an appropriate chemical resistant glove. Protective Material Types: Tyvek, Rubber, Nitrile, Neoprene.|Respiratory Protection: A NIOSH approved respirator with high efficiency particulate air (HEPA) cartridges may be permissible under certain circumstances where airborne concentrations are expected to exceed exposure limits, or when symptoms have been observed that are indicative of overexposure. When an air purifying respirator is not adequate for spills and/or emergencies of unknown concentrations, an approved self-contained breathing apparatus operated in the pressure demand mode is required. A respiratory protection program that meets 29 CFR 1910.134 must be followed whenever workplace conditions warrant use of a respirator.

Negligible fire hazard.

Extinguishing Media: Use extinguishing agents appropriate for surrounding fire. Fire Fighting: Move container from fire area if it can be done without risk. Avoid inhalation of material or combustion by-products. Wear an approved positive-pressure self-contained breathing apparatus operated in pressure demand mode.

ACCIDENTAL RELEASE MEASURES: Personal Precautions: Avoid breathing dust. Minimize generation of dust. Wear appropriate personal protective equipment ... . Methods and Materials for Containment and Cleaning Up: Shovel dry material into suitable container. Clean up residue with a high-efficiency particulate filter vacuum. Use methods to minimize generation of dust. Environmental Precautions: Keep out of water supplies and sewers. Releases should be reported, if required, to appropriate agencies.

ACCIDENTAL RELEASE MEASURES: Personal Precautions: Avoid breathing dust. Minimize generation of dust. Wear appropriate personal protective equipment ... . Environmental Precautions: Keep out of water supplies and sewers. Releases should be reported, if required, to appropriate agencies.|Precautions for Safe Handling: During processing use only with adequate ventilation. Avoid breathing dust. Wash thoroughly after handling. Do not reuse containers. Use methods to minimize dust.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.|Provide local exhaust ventilation where dust or mist may be generated. Ensure compliance with applicable exposure limits.

Dechlorane plus was detected at 2.45-93.8 ng/g dry weight in sewage sludge samples collected Apr-Jun 2006 from 31 urban Spanish wastewater treatment plants with 0.903-19.2 and 1.55- 75.1 ng/g dry weight for the syn- and anti-isomer, respectively(1).

SEDIMENT: During a monitoring study of dechlorane plus in the Great Lakes region, the highest concentration of dechlorane plus measured in Lake Erie sediment was 40 ng/g compared to the highest Lake Michigan sediment concentration of 4-6 ng/g(1). Surface sediment samples collected 1997-1998 and 1998 from Lake Erie and Lake Ontario had respective dechlorane plus concentrations of 0.061-8.62 and 2.23-586 ng/g dry weight; reported archived (1980-2002) suspended sediment sample results from the Niagara River showed a maximum concentration of 89 ng/g in 1980 and a minimum concentration of 7 ng/g in 1999(2). The mean concentration of dechlorane plus syn- and anti-isomers in sediment samples collected in 2002 from Lake Winnipeg, Canada were 11.7 and 18.3 pg/g dry weight and from Lake Ontario were 29.6 and 176.4 pg/g dry weight, respectively(3). Sediment core sample collected Jul 2004 from Lake Ontario contained 150 ng/g dry weight of dechlorane plus at the surface and 310 ng/g dry weight at 2-3 cm depth (representing 1994 concentration)(4).|SEDIMENT: Dechlorane plus was not detected 53 sediment samples collected during a monitoring study of Japanese industrial zones along the Pacific coast and the Japan Sea coast from 1974 to 1976(1). Sediment samples collected in 2003 from Pohang and Busan Bay, Korea, contained 10-936 and 8-196 pg/g dry weight, respectively(2). Dechlorane plus isomers (syn- and anti-) were detected at 21,820 and 55,320 ng/g organic carbon in surface sediment samples and at 13,130 and 65,660 ng/g organic carbon in suspended sediment samples collected in 2006 from a reservoir near the e-waste recycling plants, South China(3). Dechlorane Plus was detected in sediment samples from 14 of 15 locations in Bohai and Huanghai Sea, China, at a mean concentration of 2.9 ng/g dry weight; samples were collected from Oct to Dec 2008(4). Dechlorane plus concentrations in sediment were reported as 1.86-8.00 ng/g wet weight in samples collected Oct 2009 in the Beijing-Hangzhou Grand Canal, China(5). Surface sediment samples collected May 18 to Jul 11, 2011 from the Qiantang River, China contained dechlorane plus at 0.081-1.1, <0.01-0.54 and 0.55 ng/g dry weight in all 9 urban, 9 of 12 rural and 1 reservoir sample, respectively(6). Sediment samples collected the summer of 2011 from the Lingjiang, Oujiang and Qiantang Rivers, located in the Yangtze River Delta contained 0.591-7.00 ng/g dry weight of dechlorane plus; it was not detected (detection limit 0.330 ng/g dry weight) in samples from the East China Sea(7). Dechlorane plus was detected at 0.3-4.7 ng/g in 20 surface sediment samples collected in 2011 from River Ravi, Pakistan with a mean of 1.9 ng/g(8).|SOIL: In soil samples collected Oct 2009 from 21 locations in Huai'an, China, dechlorane plus was detected at 0.83-1200 ng/g(1). Dechlorane plus concentrations in soil were reported as 5.11-13,400 ng/g dry weight in samples collected Oct 2009 in the city of Huai'an, China(2). Dechlorane plus was detected at 0.1-15 ng/g in 50 surface soil samples collected in 2011 from 10 sampling sites located along the River Ravi, Pakistan with a mean of 0.8 ng/g(3).

Concentrations (pg/cu m) of particulate dechlorane plus measured in the air at six locations in the Great Lakes region(1).[Table#7116]|Concentrations (pg/cu m) of vapor and particulate dechlorane plus measured in the air samples collected 2005 to 2009 from five locations in the Great Lakes region(1).[Table#7117]|URBAN/SUBURBAN: In atmospheric samples collected in the spring, summer and autumn 2004 and the winter 2005 from Taihu Lake basin, China, the annual average concentration of dechlorane plus was 3.5 pg/cu m(1). The mean concentration of dechlorane plus was 15.6 pg/cu m in 24 of 32 air samples collected Jul-Oct 2005 from urban sites in China(2). The annual deposition flux of dechlorane plus is 2410 ng/sq m/year, calculated from data collected Oct 2007 to Sep 2008 at an urban site (Guangzhou City) in China(3). Dechlorane plus concentrations in the gas and particulate phase were reported as 393-434 and 7330-26300 pg/cu m, respectively in atmospheric samples collected Oct 10-13, 2009 in the city of Huai'an, China(4). Air samples collected Oct 25-31, 2011 from south coast of Laizhou Bay, China, contained dechlorane plus at 0.85-2.1 pg/cu m in the particulate phase, it was not detected in the gas phase(5). Dechlorane plus was detected at 1.5-530 pg/cu m with a mean of 88 pg/cu m in samples collected Jan 22-Mar 19, 2011 from 10 sampling stations (5 industrial, 5 agricultural) near the River Ravi, Pakistan(6). Atmospheric samples collected Nov-Dec 2012 and Feb-Mar 2013 from Osaka City, Japan contained 7.1-15.4 pb/cu m of dechlorane plus(7).|RURAL/REMOTE: The mean concentration of dechlorane plus was 3.5 pg/cu m in 27 of 70 air samples collected Jul-Oct 2005 from rural sites in China(1). The annual deposition flux of dechlorane plus is 872 ng/sq m/year, calculate from data collected Oct 2007 to Sep 2008 at a rural site in China(2). Dechlorane plus was detected at 0.05-4.2 pg/cu m in atmospheric samples collected Nov-Dec 2008 and Aug-Sep 2009 over the East Atlantic Ocean and East Greenland Sea, respectively(3).|SOURCE DOMINATED: The annual deposition flux of dechlorane plus is 27,900 ng/sq m/year, calculate from data collected Oct 2007 to Sep 2008 at an e-waste recycling site in China(1).

Dechlorane plus concentrations in indoor dust collected Nov 2002-Mar 2003 from 69 homes in Ottawa, Canada were 2.3-182 ng/g dust except one sample that contained 5683 ng/g dust; seven samples collected the spring of 2007 in Ottawa contained 14-61 ng/g dust(1). Dust samples collected from residence in occupationally exposed and non-occupationally exposed e-waste recycling site, a rural and an urban area of China contained dechlorane plus levels of 343-4197, 45.2-1798, 32.6-118 and 2.78-70.4 ng/g dry weight, respectively(2). Dog food samples collected from dog owners in Bloomington, IN, contained dechlorane plus at 0.005-0.089 ng/g wet weight; the average concentration of dechlorane plus in dry cat food was reported as 0.086 ng/g wet weight(3).

Toxicity

IDENTIFICATION AND USE: Dechlorane plus (DP) is a solid. It is used as fire retardant for plastics. Flame retardants such as DP were introduced as replacements and produced in high volumes. HUMAN STUDIES: DP is detected human milk, and human serum. Although human exposure to DP is evident, little is known about its potential effects on human health. The effects of DP on adipogenesis was investigated using human primary subcutaneous and omental preadipocytes. The results of the study showed that DP can induce adipogenesis and while DP can directly activate PPARgamma, its adipogenic effects may be mediated via other pathways. ANIMAL STUDIES: In rabbits DP produced no corneal, iridal, or conjunctival effects. In male mice, DP exposure increased the level of superoxide dismutase (SOD) and 8-hydroxy-2-deoxyguanosine (8-OHdG). The microarray-based transcriptomic results demonstrated that DP exposure led to significant alteration of gene expression involved in carbohydrate, lipid, nucleotide, and energy metabolism, as well as signal transduction processes. After dermal application in rabbits the only treatment-related clinical sign observed was minimal erythema at the dose site after 18-20 applications. DP did not have developmental and reproductive effects in rats. DP was not mutagenic in Salmonella typhimurium,strains TA98, TA100, TA1535, TA1537, TA1538 with or without metabolic activation. ECOTOXICITY STUDIES: In male common quails (Coturnix coturnix) DP exposure altered hepatic alkoxyresorufin O-dealkylase (AROD) activity. Juvenile Chinese sturgeon (Acipenser sinensis) were treated with DP at doses of 1, 10, and 100 mg/kg wet weight for 14 days. DP had effects on the generalized stress response, small G-protein signal cascades, Ca(2+) signaling pathway, and metabolic process, and induced apoptosis in the liver. In zebrafish, DP disrupted thyroid hormone balance by altering regulatory pathways in the brain. In blue mussels, toxicity of DP occured primarily via oxidative stress, and gills represented the most responsive tissue. Earthworms (Eisenia fetida) were exposed to DP at 0.1, 0.5, 6.25 and 12.5 mg/kg for 28 days. Results showed that the direct toxicity of DP was very low. However, death rate, as well as SOD activity, together with changes in activities of CAT, GSH-Px, and GSH levels, indicated that oxidative stress had a significant role in DP exposure. In addition, DP also changed the AChE and cellulase activity of earthworms even under low DP concentration after long-term exposure. Moreover, comet assay results showed that DP exposure increased the levels of tDNA significantly even in the lowest treatment. Another study indicated that DP toxicity on the earthworm is primarily through oxidative damage and neurotoxicity.

LD50 Rat oral 25 g/kg|LC50 Rat inhalation >2.25 mg/L/4 hr|LC50 Rat inhalation >300 mg/L/1 hr|LD50 Rat (male Sprague-Dawley) oral >3160 mg/kg bw|LD50 Rabbit dermal >8000 mg/kg bw

/BIRDS and MAMMALS/ While a number of studies have addressed bioaccumulation of the flame retardant Dechlorane Plus (DP), little information is available regarding the adverse effects of DP on animals, especially on bird species. In the present study, male common quails (Coturnix coturnix) were consecutively exposed to commercial DP-25 by gavage for 90 days at 1-mg/kg/day, 10-mg/kg/day, and 100-mg/kg/day dosages. Concentrations of DP isomers in liver, muscle, and serum were determined after exposure. Liver enzyme activity involved in xenobiotic biotransformation processes and oxidative stress was measured, as well as glutathione and maleic dialdehyde content. The results showed that DP was more prone to accumulate in the liver than in muscle and serum in all exposed groups. In tested tissues, syn-DP dominated in the high-exposure groups (10 and 100 mg/kg/day), whereas anti-DP tended to accumulate in the low-exposure group (1 mg/kg/day). The concentration ratios of anti-DP to total DP (f(anti) values) in the tissues examined were close to commercial DP in the low-exposure group; however, the f(anti) values were significantly decreased in the high-exposure groups. Enzyme activity of 7-pentoxyresorufin-O-demethylase (PROD) decreased significantly in all exposed groups compared with the control group, whereas activity of erythromycin N-demethylase (ERND) and the antioxidant enzyme catalase significantly increased in high-exposure groups. The results implied that DP exposure levels influenced isomeric compositions in organs and that DP exposure altered hepatic alkoxyresorufin O-dealkylase (AROD) activity and contributed to the biological effects of DP.|/BIRDS and MAMMALS/ Japanese quails (Coturnix japonica) were exposed in ovo to tris(1,3-dichloro-2-propyl) phosphate (TDCIPP; 500 ng/uL), Dechlorane Plus (DP; 500 ng/uL), or a 1:1 mixture of these two to investigate the effects on liver and thyroid gland morphology. Histological examination of 14-day-old quails showed that exposure to TDCIPP or the mixture induced hepatic sinusoidal dilatation. No marked effects were seen for DP alone. In addition, the mixture produced divergence of thyroid gland follicles and proliferation of follicular cells. /This/ study is the first demonstrating histopathological alterations as a result of exposure during early development to the flame retardants TDCIPP or a TDCIPP-DP mixture suggesting the need for further research efforts to investigate potential adverse health effects associated with exposure to these environmental chemicals in wild birds.|/BIRDS and MAMMALS/ Dechlorane Plus (DP) is an additive chlorinated flame retardant comprising two major isomers, syn- and anti-DP, that is used in a variety of commercial/industrial products. It has been detected in biotic and abiotic matrices including the eggs of herring gulls collected from the Laurentian Great Lakes. However, data on potential toxicological and molecular responses to exposure are lacking, especially for avian species. A combined in vitro/in ovo approach was used to determine concentration-dependent effects of DP in chicken embryonic hepatocytes (CEH) and chicken embryos following injection of DP into the air cell of eggs prior to incubation. Overt toxicity (i.e. cytotoxicity and pipping success) and mRNA expression levels of transcripts previously determined to be responsive to a brominated flame retardant were assessed in CEH and hepatic tissue. DP was not cytotoxic up to a maximum concentration of 3 uM in CEH, and no effects on pipping success were observed up to the highest nominal dose group of 500 ng/g egg. A significant shift in isomeric content of syn- and anti-DP was detected between stock solutions of the commercial mixture and hepatic tissue; the proportion of the syn-DP isomer increased from 0.34 to 0.65 with a concomitant decrease of anti-DP from 0.66 to 0.35. None of the mRNA transcripts changed as a result of in vitro or in ovo exposure to DP indicating that, although there was concordance between the two approaches, DP may evoke its toxicity through other modes of action. At current environmental exposure levels, no adverse effects of DP on embryonic viability or pathways associated with the genes assessed are predicted.|/AQUATIC SPECIES/ Dechlorane Plus (DP), a chlorinated flame retardant, is increasingly reported in aquatic ecosystems worldwide. But little information is available regarding the toxicity of DP in marine organisms, especially in macroalgae. The objective of this study was to investigate effects of DP exposure on photosynthesis, oxidative stress and its enrichment in juvenile marine macroalgae (Ulva pertusa). Following 21- day uptake and 21- day depuration (10-8 mol/L), algae accumulated 1.18 times of DP compared to the initial concentration. Anti-DP was prone to accumulate in juvenile macroalgae. The enrichment of DP affected the physiological responses in algae. After 1, 7 and 14 days DP exposure (10-8, 10-7 and 10-6 mol/L), antioxidant enzymes (SOD and CAT) activities and MDA content changed in a dose and time depended manner. Chlorophyll fluorescence parameters, including Fv/Fm, FPSII and ETR decreased with the increasing DP concentration. It indicated that DP leads to a low rate of light energy utilization in algae which may ascribe to the oxidative damage induced by DP enrichment. Present study provides insight into the toxicological effects of DP on marine macroalgae, which is useful for risk assessment of DP in intertidal zone ecosystems.|For more Ecotoxicity Excerpts (Complete) data for Dechlorane plus (11 total), please visit the HSDB record page.

Dechlorane plus' production and use as a flame retardant for plastics(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4.8X10+7(SRC), determined from a structure estimation method(2), indicates that dechlorane plus is expected to be immobile in soil(SRC). Volatilization of dechlorane plus from moist soil surfaces may be expected(SRC) given an estimated Henry's Law constant of 7.4X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). However, adsorption to soil is expected to attenuate volatilization(SRC). Dechlorane plus is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.4X10-11 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Based on 0-0.6% biodegradation after 2-3 weeks in screening tests using sewage sludge inocula(3-4), biodegradation of dechlorane plus in soil is not expected.|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4.8X10+7(SRC), determined from a structure estimation method(2), indicates that dechlorane plus 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 7.4X10-6 atm-cu m/mole(SRC), 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 13 and 100 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 9.5X10+7 years if adsorption is considered(4). Dechlorane plus is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). According to a classification scheme(5), BCFs of 14-121(6), measured in fish, suggest the potential for bioconcentration in aquatic organisms is low to high. Reported log bioaccumulation factors (BAF) of 2.13-4.40 in aquatic organisms indicate that dechlorane plus will bioaccumulate in the environment(7). Limited biodegradation data indicate little or no degradation occurred under aerobic and anaerobic conditions(6,8).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dechlorane plus, which has an estimated vapor pressure of 2.4X10-11 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase dechlorane plus may be removed from the air by wet or dry deposition(SRC). Dechlorane plus does not contain chromophores that absorb at wavelengths >290 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Dechlorane plus is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1). Dechlorane plus does not contain chromophores that absorb at wavelengths >290 nm and, therefore, is not expected to be susceptible to direct photolysis by sunlight(1).

BCF ranges of 14-96 and 23-121 were measured in fish using carp (Cyprinus carpio), which were exposed over an 8-week period to 0.27 and 2.65 ppb of dechlorane plus, respectively(1). According to a classification scheme(2), BCF values of zero to 30 are low and from 100 to 1000 are high. The average biomagnification factor for anti- and syn-dechlorane plus measured in juvenile rainbow trout (Onchorynchus mykiss) exposed for 49 days was 1.9 and 5.2 respectively(3). The trophic magnification factors of 2.5 and <1 were calculated for anti- and syn-isomers of dechlorane plus in the food web of Lake Winnipeg, Canada from biota sampled Jun-Sep 2002(4). Log bioaccumulation factors (BAF) for dechlorane plus were reported as 2.13-4.40 in aquatic organisms sampled in a reservoir near the e-waste recycling plants, South China, the trophic magnification factor was 10.2(5). Chemicals are considered to be bioaccumulative if the log BAF is greater than 3.70. All species except two were greater than this value, the Chinese mystery snail (Cipangopaludina chinensis) (lowest trophic level) and the northern snakehead (Ophicephalus argus) (highest tropic level), indicating that dechlorane plus is metabolized in some higher level species(5).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of dechlorane plus can be estimated to be 4.8X10+7(SRC). According to a classification scheme(2), this estimated Koc value suggests that dechlorane plus is expected to be immobile in soil.

The Henry's Law constant for dechlorane plus is estimated as 7.4X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that dechlorane plus may 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 13 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 100 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 9.5X10+7 years if adsorption is considered(3). Dechlorane plus' Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Dechlorane plus is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.4X10-11 mm Hg(SRC), determined from a fragment constant method(1).

SURFACE WATER: The mean concentration of dechlorane plus was reported as 3.5, 1.0, 1.8, 13.9 and 6.2 pg/L in aqueous samples collected Apr-May 2011 and Apr-Jun 2012 from Lakes Erie, Huron, Michigan, Ontario and Superior, respectively(1). Dechlorane plus was detected in 6.7% of 60 water samples collected during a monitoring study of Japanese industrial zones along the Pacific coast and the Japan Sea coast from 1974 to 1976 with an average concentration of 0.6 ppb(2). Dechlorane plus isomers (syn- and anti-) were detected at 0.27 and 0.53 ng/L in surface water samples collected in 2006 from a reservoir near the e-waste recycling plants, South China(3). Dechlorane Plus was detected in seawater samples from 12 of 15 locations in Bohai and Huanghai Sea, China, at a mean concentration of 1.8 ng/L; samples were collected from Oct to Dec 2008(4). Dechlorane plus was detected at <0.02-1.3 pg/L in seawater samples collected Nov-Dec 2008 and Aug-Sep 2009 from the East Atlantic and East Greenland seas, respectively(5).|RAIN/SNOW/FOG: Dechlorane plus was detected in precipitation samples collected 2005-2009 from Eagle Harbor, Chicago, Sleeping Bear Dunes, Cleveland and Sturgeon Point in the Great Lakes region at 0.05, 0.76, 0.05, 0.49 and 0.89 ng/L, respectively(1).

Dechlorane plus was detected in 7 of 12 formulas, 9 of 15 cereal and 4 of 8 puree baby food samples collected in 2013 in the US at 21, 57 and 9.8 pg/g fresh weight, respectively(1). In China, dechlorane plus was detected in 6 of 9 formula, 2 of 12 cereal and 2 of 6 puree baby food samples at 680, 5.9 and 5.8 pg/g fresh weight, respectively(1).|In a market basket study conducted in 2012 in Osaka, Japan, 123 food samples were purchased and formed 13 food group composites(1). Dechlorane plus was not detected (detection limit 0.4 pg/g wet weight) in nine of the food groups containing rice, grains, seeds, tubers, oils, fats, fruits vegetables, mushrooms, seaweeds, beverages, milk, dairy products, seasonings and other processed foods. Detection of dechlorane plus in the remaining food groups were as follows(1):[Table#7124]

In a market basket study conducted in 2012 in Osaka, Japan, dechlorane plus was not detected (detection limit 0.4 pg/g wet weight) in milk or dairy products(1).

According to the 2016 TSCA Inventory Update Reporting data, 2 reporting facilities estimate the number of persons reasonably likely to be exposed during the manufacturing, processing, or use of dechlorane plus in the United States may be as low as 25 workers and as high as 50 workers per plant; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 10,762 workers (6911 of these are female) were potentially exposed to dechlorane plus in the US(1). Occupational exposure to dechlorane plus may occur through dermal contact with this compound at workplaces where dechlorane plus is produced or used. Monitoring data indicate that the general population may be exposed to dechlorane plus via inhalation of contaminated ambient air and ingestion of some foods(SRC).

Dechlorane plus was detected in serum samples collected from 20 residence each in Guiyu and Haojiang, China at 7.8-465 and 0.93-50.5 ng/g lipid, respectively(1). Pooled serum samples collected from 305 volunteers living in Laizhou Bay, China had dechlorane plus concentrations of 1.4-11 ng/g lipid(2).|Dechlorane plus levels were measured in hair samples from occupationally exposed (OE e-waste) and non-occupationally exposed (NOE e-waste) residence of an e-waste recycling site, a rural and an urban area of China(1).[Table#7118]|Hair and blood samples were collected Nov 2011 from 24 workers (group A) directly engaged in dechlorane plus manufacturing and processing; 12 workers (group B) from the same plant but not directly exposed; and 12 people (group C) that did not work at the plant but resided about 3 km from the plant(1). Reported syn-, anti- and total dechlorane plus concentrations in ng/g lipid weight for blood and ng/g dry weight for hair were(1):[Table#7119]|Matched maternal blood, placenta and cord blood samples were collected Jul 2010 to Jul 2011, from mothers in the Wenling, Taizhou region, China, an e-waste recycling region(1). Forty-eight samples were collected from mothers who had lived in Wenling for more than 20 years (R20) and were living in villages where e-waste recycling activities were undertaken but did not directly participate. Twenty-four mothers lived in the region for less than 3 years (R3) and did not previously live in a region that contained e-waste recycling and did not participate in recycling activities. Reported syn-, anti- and total dechlorane plus concentrations were(1):[Table#7120]

Drug Information

It has been reported that breastfeeding can expose newborns to dechlorane plus (DP), but transplacental transfer of DP has not been documented. We measured DP and its dechlorinated analogs in matched maternal blood-placenta-cord blood samples from 72 residents of the e-waste recycling area of Wenling, China. DP was detected in cord sera, indicating the occurrence of prenatal DP exposure and the transfer of DP across the placenta. The concentration ratio in the cord serum and maternal serum was estimated to be 0.45 for syn-DP and 0.35 for anti-DP, indicating the placenta partially limited DP transfer with a greater extent for anti-DP. The DP concentrations in the maternal serum, placenta, and cord serum strongly correlated, indicating that DP could transfer between the tissues. The DP concentrations in the matched samples could be predicted from each other. The anti-DP/total DP concentration ratios in the placentas and cord sera were significantly different from those in the maternal sera, suggesting that DP stereoselectively bioaccumulates in human tissues. When the congener concentrations of polybrominated diphenyl ethers (PBDEs) were used as control variables, DP and total triiodothyronine concentrations were associated in the sera from mothers who had lived in Wenling for over 20 years.|Brominated flame retardants (BFRs) and Dechlorane Plus (DP) were measured in both human hair and paired serum samples from a cohort of university students in South China. Segmental analysis was conducted to explore gender difference and the relationships between the hair and serum. The concentrations of total PBDEs in the hair and serum samples were in a range of 0.28-34.1 ng/g dry weight (dw) and 0.16-156 ng/g lipid weight (lw), respectively. Concentrations of sum DPs (sum of the syn-DP and anti-DP isomers) in all hair samples ranged from nd-5.45 ng/g dry weight. Concentrations of most PBDEs and decabromodiphenylethane (DBDPE) in distal segments (5-10 cm from the scalp) were higher than those in the proximal segments (0-5 cm from the scalp) (t-test, p < 0.05), which could be due to the longer exposure time of distal segments. The proximal segments exhibited a unique congener profile, more close to that in the serum rather than the distal segments of hair. An obvious gender difference was found in the levels of sum of PBDEs using integrated hair samples, while the difference disappeared when considering alone the proximal segments of hair (0-5 cm from scalp) for both genders. This paper provides supplement to the current knowledge on sources of BFRs and DPs in hair and declares the importance of segmental analysis.|Dechlorane Plus (DP) and a dechlorinated product of DP were measured in 34 matched human hair and serum samples (19 males and 15 females) collected from e-waste recycling workers in South China. The DP (sum of syn- and anti-DP) concentrations in hair and serum samples ranged from 6.3 to 1100 ng/g dry weight and from 22 to 1400 ng/g lipid weight (lw). The levels of anti-Cl11-DP ranged from 0.02 to 1.8 ng/g in hair and from not detected to 7.9 ng/g lw in serum. Significant positive correlations for both DP and anti-Cl11-DP concentrations between hair and serum samples were found (p<0.05), indicating hair to be a suitable matrix for human DP exposure. However, a significant difference was found in the DP isomer composition between hair and serum, suggesting stereoselective bioaccumulation during the absorption of DP into hair. A sharp gender difference was found in the levels of DP in hair. Moreover, syn-DP, anti-DP and anti-Cl11-DP in hair significantly correlated with those in serum for male samples, but not for female samples. The observed gender differences in the present study may be, in part, ascribed to the much longer hair exposure time for females than males due to the difference in sampling distance from the scalp.|The tissue concentrations of dechlorane plus and its analogues were determined in ducks collected from several e-waste recycling villages of Taizhou, China. Compared with the published literature, the relatively high concentrations of these compounds were detected in ducks, indicating serious DP contamination. Since both the duck meat and eggs were important components for diet, this result reminded us of keeping a watchful eye on human dietary exposure to DP and its analogues in this study area. The wet-weight concentrations of DP and its analogues were significantly related to tissue lipid content (p < 0.05), indicating that the lipid pools predominantly impacted the distribution of DPs in ducks. On the basis of lipid adjustment, the significantly lower levels in brain than those in liver and blood, displayed the occurrence of liver sequestration and blood-brain barrier to DP and its analogues in the duck (p < 0.05). The maternal transfer of DP and Mirex was not obviously limited, and the transferring extent of Dec 602 was over one. The stereo-selected accumulation of two DP isomers occurred among tissues with preference to syn-DP in blood, and to anti-DP in brain. The values of lipid-adjusted monodechlorinated products mainly originated from the exterior environment in ducks.|For more Absorption, Distribution and Excretion (Complete) data for Dechlorane plus (7 total), please visit the HSDB record page.

/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 as 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. /Chlordane 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. Anticipate seizures, minimize external stimuli, 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 ... . /Chlordane and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for air way control in the patient who is unconscious or is in severe respiratory distress. 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 or lorazepam ... . Proparacaine hydrochloride should be used to assist eye irrigation ... . /Chlordane and related compounds/

/ALTERNATIVE and IN VITRO TESTS/ Polybrominated diphenyl ethers (PBDEs) are chemicals that were added to consumer products to reduce flammability but were deemed toxic and bioaccumulative and were phased out of commerce. Flame retardants (FRs) such as Dechlorane Plus (DP) were introduced as replacements. DP is being produced in high volumes and is detected in the environment, human milk, and human serum. Although human exposure to DP is evident, little is known about its potential effects on human health. We and others have shown that some FRs are potential obesogens, i.e., promote adipogenesis. However, the effects of DP on adipogenesis are not known. METHODS: Murine 3T3-L1 and human primary subcutaneous (Sc) and omental (Om) preadipocytes were differentiated in the presence of DP (0.001-10 uM) and adipogenic effects were measured. Further, the ability of DP to activate the adipogenic transcription factor peroxisome proliferator-activated receptor gamma (PPARgamma) was also assessed. RESULTS: We show that treatment of murine preadipocytes with DP significantly (p<0.05) increased lipid accumulation (2.5-fold) and the mRNA expression of adipogenic markers: fatty acid binding protein 4 (Fabp4), lipoprotein lipase (Lpl), perilipin (Plin), adipsin, and adiponectin. DP also significantly (p<0.05) increased the protein levels of selected mature adipocyte markers. We further show using luciferase reporter assays that DP increased PPARgamma transcriptional activity by threefold (p<0.05). When the PPARgamma agonist was replaced by DP in the human preadipocyte differentiation cocktail, DP significantly (p<0.05) increased the mRNA levels of adipogenic markers, PPARgamma, FABP4, and PLIN in human Sc as well as Om cultures. Finally, PPARgamma antagonist studies revealed that DP-mediated upregulation of adipogenic markers Fabp4 and Lpl did not occur via PPARgamma activation. The current study shows that DP can induce adipogenesis of murine and human preadipocytes. We show that, although DP can directly activate PPARgamma, its adipogenic effects may be mediated via other pathways.

dechlorane plus

Dechlorane Plus Use and Manufacturing

Methods of Manufacturing

Prepared by Diels-Alder reaction between cyclooctadiene and hexachlorocyclopentadiene.

Uses

Fire retardant for plastics.


Flame retardants


Building/construction materials not covered elsewhere

Production

This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).|(1986) >1 million-10 million pounds|(1990) >1 million-10 million pounds|(1994) >1 million-10 million pounds|For more U.S. Production (Complete) data for Dechlorane plus (7 total), please visit the HSDB record page.

Miscellaneous manufacturing|1,4:7,10-Dimethanodibenzo[a,e]cyclooctene, 1,2,3,4,7,8,9,10,13,13,14,14-dodecachloro-1,4,4a,5,6,6a,7,10,10a,11,12,12a-dodecahydro-: ACTIVE

A highly chlorinated flame retardant, Dechlorane Plus (DP), was detected and identified in ambient air, fish, and sediment samples from the Great Lakes region. The identity of this compound was confirmed by comparing its gas chromatographic retention times and mass spectra with those of authentic material. This compound exists as two gas chromatographically separable stereoisomers (syn and anti), the structures of which were characterized by one- and two-dimensional proton nuclear magnetic resonance.

Computed Properties

Molecular Weight:653.7
XLogP3:8
Exact Mass:653.711282
Monoisotopic Mass:647.720133
Heavy Atom Count:30
Complexity:782
Undefined Atom Stereocenter Count:8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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