Perfluoroalkyl Carboxylates and Sulfonates

These considerations apply also to the fluorotelomer alcohol CF3(CF2)7-CH2CH20H that was degraded in a mixed cnltnre obtained by enrichment with ethanol. Terminal dehydrogenation followed by elimination of flnoride, hydration and further loss of fluoride produced perfluorooctanoate (Dinglasan et al. 2004). 

CF3(CF2)7CH2-CH20H CF3(CF2)7CH2C02H CF3(CF2)6-CF=CHC02H CF3(CF2)6C0CH2C02H CF3(CF2)6C02H 

CT Walsh (1984) Stereochemical studies on a plasmid-coded fluoroacetate halohydrolase. Bioorg Chem 12 197-295. 

Berends AG, JC Bouttonet, CG de Rooij, RS Thompson (1999) Toxicity of trifluoroacetate to aquatic organisms. Environ Toxicol Chem 18 1053-1059. 

Boutonnet JC et al. (1999) Environmental risk assessment of trifinoroacetic acid. Human Ecol Risk Assess 5 59-124. 

---

For many organic compounds that accumulate in lipids, bio accumulation potential can be estimated from the Kow. Since perfluoroalkyl compounds are inherently oleophobic, and do not partition preferentially to lipid rich tissues [67], the K0w is not a useful predictor of bioaccumulation and direct evidence derived from the laboratory or field is required. Additionally, tissue concentrations of perfluoroalkyl substances should never be lipid normalized. The dietary accumulation, bioconcentration, and biomagnification potential of various perfluoroalkyl carboxylates and sulfonates have been assessed in the laboratory and in the Great Lakes food web (Table 4). 

Arsenault G, McAlees A, McCrindle R et al (2007) Analysis of perfluoroalkyl anion fragmentation pathways for perfluoroalkyl carboxylates and sulfonates during liquid chromatog-raphy/tandem mass spectrometry evidence for fluorine migration prior to secondary and tertiary fragmentation. Rapid Commun Mass Spec 21 3803-3814... 

---