title: Compounds structurally related to Dechlorane Plus in sediment and biota from Lake Ontario (Canada).
abstract: The historical occurrence of Dechlorane Plus (DP) and detection of novel compounds structurally related to DP is described in a dated Lake Ontario sediment core. Our core was collected near the mouth of the Niagara River, which is known to be a major source of DP to the lake. Maximum DP concentrations (920 ng g(-1), dry weight) were observed between 1976 and 1980, the highest reported to date. Following that time, we observed a dramatic decrease in DP concentration which coincided with the enactment of United States federal and state laws to mitigate free release of chemicals into the Niagara River and installation of an industrial wastewater treatment facility. During the course of our research, four new substances structurally related to DP were also identified. These compounds were thought to arise from the Diels-Alder reactions resulting from impurities present in 1,5-cyclooctadiene, a feedstock used in production of DP. To confirm our hypothesis, Diels-Alder reactions were performed on the individual impurities. Using different stationary-phase capillary gas chromatography columns and high-resolution mass spectrometry, we were able to positively identify some of these novel compounds in the core. Interestingly, we also were able to identify a monoadduct compound, formed by addition of 1 mol of hexachlorocyclopentadiene to 2 mol of 1,3-cyclooctadiene, in lake trout. The concentration of this monoadduct was approximately 2 orders of magnitude greater than that of DP, suggesting that it is more bioaccumulative.
authors.affiliation: Department of Chemistry, McMaster University, Hamilton, Ontario L8S 4M1, Canada. ed.sverko@ec.gc.ca
authors.forename: Ed
authors.initials: E
authors.lastname: Sverko
authors.forename: Eric J
authors.initials: EJ
authors.lastname: Reiner
authors.forename: Gregg T
authors.initials: GT
authors.lastname: Tomy
authors.forename: Robert
authors.initials: R
authors.lastname: McCrindle
authors.forename: Li
authors.initials: L
authors.lastname: Shen
authors.forename: Gilles
authors.initials: G
authors.lastname: Arsenault
authors.forename: Donna
authors.initials: D
authors.lastname: Zaruk
authors.forename: Karen A
authors.initials: KA
authors.lastname: MacPherson
authors.forename: Chris H
authors.initials: CH
authors.lastname: Marvin
authors.forename: Paul A
authors.initials: PA
authors.lastname: Helm
authors.forename: Brian E
authors.initials: BE
authors.lastname: McCarry
mesh_terms: D000818:Animals; D002170:Canada; D004784:Environmental Monitoring; D005411:Flame Retardants / Q000032:analysis*; D005618:Fresh Water / Q000737:chemistry*; D019015:Geologic Sediments / Q000737:chemistry*; D006114:Great Lakes Region; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000737:chemistry*; D014337:Trout; D014874:Water Pollutants, Chemical / Q000737:chemistry*
chemical_list: D005411:Flame Retardants; D006843:Hydrocarbons, Chlorinated; D011083:Polycyclic Compounds; D014874:Water Pollutants, Chemical; C526360:dechlorane plus