dechlorane-604 and dechlorane-603

Dechlorane Plus, dechlorane 602, dechlorane 603 and dechlorane 604 are flame retardants that have been used for a long time as a substitute for mirex, but they have not been noticed as environmental contaminants until recently (2006). Regardless of their large molecular size and very high lipophilicity (log K(OW) > 9), Dechlorane Plus and related compounds have been detected in different aquatic and terrestrial species, supporting their bioaccumulation and biomagnification. Moreover, some studies showed different behaviour of the syn-Dechlorane Plus and anti-Dechlorane Plus isomers in the environment and different biomagnification factors in biota. This review describes the different analytical approaches applied to the determination of Dechlorane Plus and related compounds. Moreover, a summary of their levels in aquatic and terrestrial biota, as well as in humans, is presented, showing also current research results on their bioaccumulation and biomagnification potential. Finally, isomer-specific bioaccumulation of Dechlorane Plus is also discussed.

Topics: Animals; Biota; Chromatography, Gas; Environmental Monitoring; Environmental Pollutants; Flame Retardants; Humans; Hydrocarbons, Chlorinated; Mass Spectrometry; Polycyclic Compounds

Dechloranes, a type of additive polychlorinated flame retardant, which include Dechlorane (Dec) Plus (DP), Dec 602, Dec 603, and Dec 604, were detected in surficial water and sediment from the Jiulong River Estuary (JRE). The total concentration of dechloranes in the water and sediments ranged from 1.4 to 4.1 ng/L and 9.3 to 36.2 ng/g dry weight, respectively. The distribution patterns of dechloranes in the water and sediments were both dominated by DP. The average values of the anti-DP fractional abundances (f

Topics: Adult; China; Environment; Environmental Exposure; Environmental Monitoring; Estuaries; Flame Retardants; Geologic Sediments; Humans; Hydrocarbons, Chlorinated; Polycyclic Compounds; Risk Assessment; Rivers; Water; Water Pollutants, Chemical

We measured the concentrations of 60 flame retardants (and related compounds) in fish samples collected in the Great Lakes basin. These analytes include dechlorane-related compounds (Decs), organophosphate esters (OPEs), and brominated flame retardants (BFRs). Composite lake trout (Salvelinus namaycush) or walleye (Sander vitreus, from Lake Erie) samples were collected (N=3 for each lake) in 2010 from each of the five Great Lakes (a total of 15 samples). Among the dechlorane-related compounds, Dechlorane, Dechlorane Plus, Dechlorane-602, Dechlorane-603, and Dechlorane-604 (with zero to three bromines and with four chlorines) were detected in >73% of the fish samples. The concentrations of some of these dechlorane-related compounds were 3-10 times higher in Lake Ontario trout than in fish from the other four lakes. Tris(1-chloroisopropyl) phosphate, tri-n-butylphosphate, tris(2-chloroethyl)phosphate, and triphenyl phosphate were found in >50% of the fish samples. Polybrominated diphenyl ethers (PBDEs) were the most abundant of the flame retardants in fish, with a mean concentration of 250ng/g lipid. Our findings suggest that the Decs and BFRs with 3-6 bromines are more bioaccumulative in the fish than the OPEs and high molecular weight BFRs.

Topics: Animals; Environmental Monitoring; Esters; Fishes; Flame Retardants; Halogenated Diphenyl Ethers; Hydrocarbons, Chlorinated; Lakes; Ontario; Organophosphates; Perches; Polycyclic Compounds; Trout; Water Pollutants, Chemical

Dechloranes (Decs) have been recently found to occur widely in the environment even in the remote polar regions. However, the understanding of their environmental fate is rather limited. The Tibetan Plateau (TP) may be an important indicator region to study the long-range atmospheric transport and their fates of these emerging contaminants since it has very limited local sources. In the present study, Dechlorane plus (DP), Dechlorane 602 (Dec 602), Dechlorane 603 (Dec 603) and Dechlorane 604 (Dec 604) were analyzed in lichen samples from the southeast TP. The results showed that only DP and Dec 602 were detected, with a detection frequency of 89% and 100%, respectively. The average concentrations (dry weight) of ΣDP and Dec 602 were 318 pg g(-1) (20-1132 pg g(-1)) and 167 pg g(-1) (27-843 pg g(-1)), respectively. The DP concentration in this study was much higher than those in moss from the remote Ny-Ålesund, Arctic. The concentrations of Dec 602 were found to generally increase with increasing altitude, while DP concentrations seemingly showed an opposite altitudinal trend along the mountain slopes. No stereoselective accumulation or transformation of anti-DP and syn-DP was observed in lichens and the altitudinal behavior of the two isomers was similar. This research documented that Decs are prone to undergo LRAT and cold-trapping by the mountains in the southeast TP.

Topics: Air Movements; Air Pollutants; Altitude; Arctic Regions; Bryophyta; Environmental Monitoring; Flame Retardants; Hydrocarbons, Chlorinated; Lichens; Polycyclic Compounds; Tibet

Dechlorane Plus (DP) is a flame retardant used as a substitute of Mirex since 1970s, but it was not detected in the environment until 2006. Since then, this compound and its main relatives, Dechlorane 602, 603 and 604, have been mainly studied in environmental matrices for monitoring purposes, but the dietary exposure to them has been hardly investigated so far. In the present study, we determined this family of compounds in fish and vegetable oil samples from Catalonia (Spain), most of them used as health supplements. Determination was carried out by gas chromatography-high resolution mass spectrometry (GC-HRMS), after a clean up in a multilayer silica column and preparative high performance liquid chromatography (HPLC) equipped with a pyrenyl(ethyl) column. Concentrations of Dechlorane compounds were between below the limit of detection and 384.2 pg g(-1). Although there are only few studies about the presence of these pollutants in food or feed, concentrations obtained indicated that these compounds are in the same order in fish and vegetable oil health supplements as the few other food and feed studies.

Topics: Chromatography, High Pressure Liquid; Environmental Monitoring; Environmental Pollutants; Fish Oils; Flame Retardants; Gas Chromatography-Mass Spectrometry; Hydrocarbons, Chlorinated; Limit of Detection; Plant Oils; Polycyclic Compounds; Spain

Dechlorane 602 (Dec 602), Dechlorane 603 (Dec 603), Dechlorane 604 (Dec 604), Dechlorane 604 component B (Dec 604 CB) and Dechlorane Plus (DP) were analyzed in soil and fish collected across e-waste recycling sites in Guiyu. The results indicate that soil and fish are contaminated with dechlorane compounds especially Dec 602 and DP which show high concentrations in the samples near recycling sites. Dec 604 and Dec 604 CB are not detected. The photo-degradation experiment indicates that Dec 604 and Dec 604 CB have much faster degradation rates compared to other dechloranes, suggesting they might be more vulnerable to degradation during recycling processes and further studies are needed for assessing the environmental fate and persistence of their degradation products. Dec 602 has not been manufactured in China, the detection of Dec 602 in soil and fish implies that it might be from imports of recyclable materials from developed countries.

Topics: Animals; China; Electronic Waste; Environmental Monitoring; Fishes; Flame Retardants; Hydrocarbons, Chlorinated; Muscles; Polycyclic Compounds; Recycling; Rivers; Soil Pollutants; Water Pollutants, Chemical

Dechloranes, including Dechlorane Plus (syn- and anti-isomers), Dechlorane 602, Dechlorane 603, Dechlorane 604, Chlordene Plus, and Mirex are used as flame-retardants and were recently found in human serum of the European population. In order to investigate if food consumption would possibly be a significant route of exposure, we developed a method for the measurement of Dechloranes in food and feed. We showed that it was possible to extend the scope of the regular polychlorinated dibenzo-p-dioxins (PCDDs), polychlorinated dibenzofurans (PCDFs), dioxin like (DL-), and non-dioxin like (NDL-) regulated PCBs clean-up and fractionation procedure to Dechloranes and that no compound degradation occurred during the strong acidic treatments used for lipid digestion. Dechloranes were measured by gas chromatography coupled to triple quadrupole mass spectrometry (GC-QQQMS/MS). We optimized injection parameters by face centered experimental design (FCD). The electron ionization fragmentation was investigated to set appropriate multiple reaction monitoring (MRM) transitions. Instrumental and method limits of quantitation (iLOQs and mLOQs) were determined following EU guidelines for dioxin analyses in food. A total of 88 samples were analyzed to assess the prevalence of this route of exposure to humans. Average levels of the sum of Dechloranes ranged from 10 to 31pg/g fat, with the exception of fish, feed additives, and corn that were reported in pg/g wet weight at average levels of 9, 12, and 2pg/g ww. Based on Belgian food habits, a dietary intake was estimated to be 136pg/day. The relatively low reported levels indicate that other routes of human exposure should be considered.

Topics: Animals; Eating; Environmental Pollutants; Feeding Behavior; Food; Food Contamination; Gas Chromatography-Mass Spectrometry; Humans; Hydrocarbons, Chlorinated; Polycyclic Compounds; Tandem Mass Spectrometry

A total of 175 samples, composed of 35 different foodstuffs, were obtained from retail markets in Korea and analyzed to investigate the contamination status and dietary intake of Dechlorane compounds. The concentrations of Dechlorane Plus (DP), mirex, Dechlorane (Dec) 602 and 603 ranged from ND to 169.85 pg/g wet weight (ww), 107.30 pg/g ww, 20.81 pg/g ww, 0.41 pg/g ww, respectively, while Dechlorane (Dec) 604 was not detected in any samples. Strong correlations between anti- and syn-DP and between mirex and Dec 602 were observed. The average anti-isomer fractional abundance (fanti) was 0.78±0.11 which was larger than the technical DP value (fanti=0.75). The estimated dietary daily intake of DP, 11.2×10(3) pg/day, was one to three orders of magnitude higher than other Dechloranes. Grain was the most contributed food group to dietary daily intake of DP for Korean population.

Topics: Diet; Environmental Monitoring; Environmental Pollutants; Flame Retardants; Food Contamination; Humans; Hydrocarbons, Chlorinated; Mirex; Polycyclic Compounds; Republic of Korea

A method for the determination of chlorinated flame retardants: Dechlorane Plus, Dechlorane (Dec) 602, Dec 603 and Dec 604, in marketed fish is described. The method involves the use of matrix solid-phase dispersion (MSPD) prior to their determination by gas chromatography-electron-capture negative-ion chemical-ionisation mass spectrometry (GC-ECNICI-MS). Parameters that affect the extraction efficiency of the target analytes from fish samples were optimised using a Box-Behnken design method. MSPD integrated the extraction and clean-up procedures into a single step, which provides the benefits of being simple and convenient. The optimal extraction conditions involved dispersing a freeze-dried fish (1-g) in 2-g of silica gel, and packed with 1-g of Florisil, and then the target analytes were eluted with 20 mL of n-hexane. The limits of quantification were 9-15 pg/g-lipid weight. Preliminary results showed that the total concentrations of the target analytes ranged from 0.15 to 1.3 ng/g-lipid weight.

Topics: Animals; Fishes; Flame Retardants; Food Contamination; Gas Chromatography-Mass Spectrometry; Hydrocarbons, Chlorinated; Molecular Structure; Polycyclic Compounds; Reproducibility of Results; Seafood; Sensitivity and Specificity; Solid Phase Extraction; Water Pollutants, Chemical

A new methodology for the analysis of Dechlorane Plus and related compounds (DPMA, Dec 602, Dec 603 and Dec 604) by gas chromatography coupled to negative chemical ionization tandem mass spectrometry (GC-NCI-MS-MS) was developed for three different matrices, including environmental (sediment and sludge) and biota (fish) samples. Analytical parameters such as linearity, repeatability and reproducibility, recoveries, limits of detection and limits of quantification were evaluated, showing satisfactory values for the developed methodology. Moreover, a comparison with the analysis by GC-NCI-MS was carried out. Method limits of detection (MDLs), ranging between 0.12 and 1.26 pg/g dw, 1.16-2.90 pg/g dw and 2.30-21.1 pg/g lw for sediment, sludge and fish respectively, were much better than those obtained by GC-MS, with improvement factor up to 320. The applicability of the developed methodology was demonstrated by the analysis of real samples collected in a non-producing area, the Ebro river basin (Spain). DP values were up to 1.61 ng/g dw, 18.8 ng/g dw and 2.24 ng/g lw for sediment, sludge and fish samples, respectively.

Topics: Animals; Environmental Monitoring; Fishes; Flame Retardants; Gas Chromatography-Mass Spectrometry; Geologic Sediments; Hydrocarbons, Chlorinated; Limit of Detection; Polycyclic Compounds; Reproducibility of Results; Sewage; Spain; Tandem Mass Spectrometry; Water Pollutants, Chemical

Dechloranes (Decs), including Dechlorane Plus (DP) and Dechlorane (Dec) 602, 603, 604, are used as flame retardants. Fifty four samples were collected in a river in northeastern China and analyzed for Decs by gas chromatography/mass spectrometry. The average concentrations of total DP (syn- and anti-) in water, sediment, air, reed (Phragmites australis), and fish (E. elongatus) were 0.30±0.24 (mean±SD) ng L(-1), 1.3±0.69 ng g(-1) dry weight (dw), 0.25±0.18 ng m(-3), 0.63±0.18 ng g(-1) wet weight (ww), and 29±20 ng g(-1) lipid weight (lw), respectively. While Dec 602 and Dec 603 were detected in most of sediment and fish samples, no Dec 604 was found in any of the investigated environmental matrices. The mean ratio of syn-DP to total DP (fsyn) in water, sediment, reed, and fish were 0.28, 0.25, 0.27 and 0.47, suggesting depletion in abiota and enrichment in biota for syn-DP. It was found that biota-sediment accumulation factor (BSAF) was 4.7 for Dec 602, 0.88 for syn-DP, and 0.33 for anti-DP.

Topics: Air; Animals; China; Environmental Monitoring; Fishes; Flame Retardants; Gas Chromatography-Mass Spectrometry; Geologic Sediments; Hydrocarbons, Chlorinated; Polycyclic Compounds; Rivers; Water Pollutants, Chemical

A chlorinated compound (Chlordene Plus, CP), structurally related to Dechloranes (Dec) 602, 603, 604, and Dechlorane Plus (DP), was identified, and concentrations and spatial trends of Dec 602, 603, 604, CP, and DP in tributary sediments of the Laurentian Great Lakes are reported. The dechloranes were widely detected with their concentrations varying considerably across the Great Lakes basin. Spatial trends of Dec 602, 604, and DP in Canadian tributary sediments were similar to that of BDE 209, which suggested these flame retardant chemicals in tributaries were associated with industrial and urban areas. The highest concentrations of Dec 602, 604, and DP observed in tributaries of the Niagara River confirmed that past or ongoing manufacturing of these compounds at plants along the river were important sources to Lake Ontario. Dec 603 was detected in technical products of aldrin and dieldrin, and its spatial trend was consistent with historic pesticide usage. Similarly, CP was detected in technical products of chlordene and chlordane, and it was found in higher concentrations in sediments near urban areas, possibly related to past chlordane use in home termite control.

Topics: Chlordan; Environmental Monitoring; Flame Retardants; Fresh Water; Geologic Sediments; Great Lakes Region; Hydrocarbons, Chlorinated; Insecticides; Polycyclic Compounds; Water Pollutants, Chemical

Concentrations of Mirex, Dechlorane (Dec) Plus (DP), Dec 602, Dec 603, and Dec 604 were significantly higher in peregrine falcon (Falco peregrinus) eggs from Canada than Spain, with the former having the only measurable concentrations of the dechlorinated DP products, decachloropentacyclooctadecadiene (aCl10DP) and undecachloropentacyclooctadecadiene (aCl11DP). Large variations also occurred in the in ovo concentrations of the DP monoadduct, DPMA. This is the first study to report the accumulation and metabolism of DP by peregrines, both DP and dechloranes in European biota, as well as dechloranes in a terrestrial organism and one at the top of the food web. The geographical differences in the measured in ovo concentrations reflect local exposure of the adult peregrines on their breeding grounds, likely differences in diet of the adults, the production of DP on the Niagara River, and the greater use of Mirex and dechloranes as flame retardants in North America than Europe.

Topics: Animals; Canada; Eggs; Environmental Monitoring; Environmental Pollutants; Falconiformes; Flame Retardants; Food Chain; Hydrocarbons, Chlorinated; Mirex; Polycyclic Compounds; Spain

Dechloranes, including Dechlorane Plus (DP), Mirex (Dechlorane), Dechlorane 602 (Dec 602), Dechlorane 603 (Dec 603), and Dechlorane 604 (Dec 604), were determined using GC-MSD for water, sediment and oyster samples collected at 15 sampling sites near the Bohai and Huanghai Sea shore area of northern China in 2008. DP and Mirex were detected in most water, sediment, and oyster samples, which indicated widespread distribution of these two compounds. The mean concentrations in water, sediment and oyster samples, respectively, were 1.8 ng/L, 2.9 ng/g dry weight (dw) and 4.1 ng/g wet weight (ww) for total DP, and 0.29 ng/L, 0.90 ng/g dw, and 2.0 ng/g ww for Mirex. Dec 602 and Dec 603 were not detected in water but in small portions of the sediment and oyster samples, showing a low level of contamination by these two chemicals in the region. Strong and significant correlations were found between total DP and Mirex concentrations in water, sediment and oyster samples, probably suggesting similar local sources of these two chemicals. Dec 604 was not found in any samples. The biota-sediment accumulation factor (BSAF) of DP, Mirex, and Dec 602 declined along with the increase of their logarithm of octanol-water partition coefficients (log Kow), possibly indicating that compounds with lower log Kow (like Mirex and Dec 602) accumulated more readily in biota. The mean fractional abundance of syn-DP (fsyn) was 0.34 in water samples, a value lower than that in Chinese commercial mixture (0.41), while the mean fsyn for surface sediment (0.44) and oyster (0.45) samples were higher than technical values. Enrichment of syn-DP in oyster was in agreement with previously reported findings in Great Lakes fish. Enrichment of syn-DP in marine surface sediments, however, is contrary to data reported for fresh water sediments. To our knowledge this is the first report of Dec 602, Dec 603, and Dec 604 in a marine environment and also the first report of Dechloranes in marine biota.

Topics: Animals; China; Environmental Monitoring; Flame Retardants; Hydrocarbons, Chlorinated; Mirex; Ostreidae; Polycyclic Compounds; Regression Analysis; Seawater; Water Pollutants, Chemical

Temporal trends and seasonal variation of Dechloranes (Dec) 602, 603, 604, and Chlordene Plus (CP) in Niagara River suspended sediment, a Lake Ontario sediment core, and Lake Ontario lake trout were investigated, with Mirex and Dechlorane Plus (DP) included for comparison. Temporal concentration trends were generally consistent in each of the media for all compounds with the lowest concentrations observed in or after the late 1990s. In Niagara River suspended sediments, all compounds showed seasonal variation over a year with distinct profiles observed. The relative concentration patterns observed were total DP > Mirex > Dec 602 and Dec 604 > Dec 603 > CP in suspended sediments and sediment cores, whereas Mirex was highest in lake trout, followed by Dec 602 and DP. Dec 602 concentrations were 50 to 380 times greater than those of DP in lake trout, indicating Dec 602 has a greater bioaccumulation potential. The estimated biota-sediment accumulation factor (BSAF) for Dec 602 was much greater than for DP in Lake Ontario, and was greater than those calculated for PBDEs, indicating that assessment of some dechlorane compounds is merited if use is ongoing or planned.

Topics: Animals; Environmental Monitoring; Flame Retardants; Fresh Water; Geologic Sediments; Great Lakes Region; Hydrocarbons, Chlorinated; Norbornanes; Polycyclic Compounds; Trout; Water Pollutants, Chemical; Water Pollution, Chemical