title: Biotransformation pathways of fluorotelomer-based polyfluoroalkyl substances: a review.
abstract: The study reviews the current state of knowledge regarding the biotransformation of fluorotelomer-based compounds, with a focus on compounds that ultimately degrade to form perfluoroalkyl carboxylates (PFCAs). Most metabolism studies have been performed with either microbial systems or rats and mice, and comparatively few studies have used fish models. Furthermore, biotransformation studies thus far have predominately used the 8:2 fluorotelomer alcohol (FTOH) as the substrate. However, there have been an increasing number of studies investigating 6:2 FTOH biotransformation as a result of industry's transition to shorter-chain fluorotelomer chemistry. Studies with the 8:2 FTOH metabolism universally show the formation of perfluorooctanoate (PFOA) and, to a smaller fraction, perfluorononanoate (PFNA) and lower-chain-length PFCAs. In general, the overall yield of PFOA is low, presumably because of the multiple branches in the biotransformation pathways, including conjugation reactions in animal systems. There have been a few studies of non-FTOH biotransformation, which include polyfluoroalkyl phosphates (PAPs), 8:2 fluorotelomer acrylate (8:2 FTAC), and fluorotelomer carboxylates (FTCAs, FTUCAs). The PAPs compounds and 8:2 FTAC were shown to be direct precursors to FTOHs and thus follow similar degradation pathways.
authors.affiliation: Department of Chemistry, University of Toronto, Ontario, Canada.
authors.forename: Craig M
authors.initials: CM
authors.lastname: Butt
authors.forename: Derek C G
authors.initials: DC
authors.lastname: Muir
authors.forename: Scott A
authors.initials: SA
authors.lastname: Mabury
mesh_terms: D000818:Animals; D001419:Bacteria / Q000378:metabolism; D001711:Biotransformation; D002264:Carboxylic Acids / Q000493:pharmacokinetics*; D006801:Humans; D006845:Hydrocarbons, Fluorinated / Q000493:pharmacokinetics*
chemical_list: D002264:Carboxylic Acids; D006845:Hydrocarbons, Fluorinated
keywords: Biotransformation; Fluorochemicals; Fluorotelomer compounds; Perfluoroalkyl carboxylates; Perfluoroalkyl substance