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Elucidating the Pathways of Poly- and Perfluorinated Acid Formation in Rainbow Trout

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Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada, and Environment Canada, Water Science & Technology Directorate, 867 Lakeshore Road, Burlington, Ontario L7R 4A6, Canada
* Corresponding author e-mail: [email protected]; phone: 416-978-1780.
†University of Toronto.
‡Environment Canada.
Cite this: Environ. Sci. Technol. 2010, 44, 13, 4973–4980
Publication Date (Web):June 2, 2010
Copyright © 2010 American Chemical Society

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Several studies have shown that fluorotelomer-based compounds can be metabolized to poly- and perfluorinated carboxylates, such as perfluorooctanoate (PFOA). Research has predominately focused on the 8:2 fluorotelomer alcohol (8:2 FTOH), however, the biotransformation pathway is not well understood. Specifically, there is uncertainty regarding the biological fate of the 8:2 fluorotelomer unsaturated carboxylate (FTUCA) and 7:3 fluorotelomer saturated carboxylate (FTCA). The objective of this study was to further elucidate the pathway for 8:2 FTOH biotransformation through dosing rainbow trout with three 8:2 FTOH metabolism intermediates: the 7:3 FTCA (CF3(CF2)6CH2CH2COO), 8:2 FTCA (CF3(CF2)7CH2COO), and 8:2 FTUCA (CF3(CF2)6CF═CHCOO). This study represents the first investigation of these three labile intermediate metabolites in an in vivo system. The parent compounds were dosed via the diet and the parent compounds and intermediates were monitored in the blood and liver during the 7-day uptake phase and 10-day elimination phase. Exposure to the 7:3 FTCA did not result in the formation and accumulation of PFOA, but resulted in low levels of the 7:3 FTUCA and perfluoroheptanoate, a novel finding. PFOA was formed in the 8:2 FTCA and 8:2 FTUCA dosing. In addition, the 7:3 FTCA was formed during exposure to both the 8:2 FTCA and 8:2 FTUCA. Elimination half-lives were 5.1 d (95% confidence interval: 3.1−14 d) for 7:3 FTCA, 1.2 d (1.1−1.3 d) for 8:2 FTCA, and 0.39 d (0.31−0.53 d) for 8:2 FTUCA. The observed differences in the elimination half-life may be the result of differences in either the depuration or metabolism rate. Based on the findings of this study, and reported analogous literature pathways, we proposed a “beta-like-oxidation” pathway for PFOA formation proceeding from the 8:2 FTUCA > 7:3 β-keto acid > 7:2 ketone > PFOA. Alternatively PFOA could be formed directly through the β-oxidation of the 7:3 β-keto acid.

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Detailed information on the synthesis of 8:2 FTCA and 8:2 FTUCA, food preparation and analysis, fish care and sampling, instrumental analysis, and statistical analyses and data treatment; figures of blood and liver trends from the 7:3 FTCA treatment; tables of liver somatic index values, elimination half-lives, and mean and standard error values for blood and liver from the 7:3 FTCA, 8:2 FTCA, and 8:2 FTUCA treatments. This information is available free of charge via the Internet at

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