Cited by 150Per- and polyfluoroalkyl substances researchEnvironmental Toxicology and EcotoxicologyToxic Organic Pollutants Impact

Fluorotelomer Acids are More Toxic than Perfluorinated Acids

Open access
Phillips, Michelle M. (MacDonald), Dinglasan-Panlilio, Mary Joyce A., Mabury, Scott A., Solomon, Keith R., Sibley, Paul K.·2007·Environmental Science & Technology

Abstract

Saturated and unsaturated fluorotelomer carboxylic acids have been identified as intermediates in the degradation of fluorotelomer alcohols to perfluorinated carboxylic acids (PFCAs). Although surface waters are the likely environmental sink for telomer acids, no fate or toxicity data exist for this matrix. We assessed the acute toxicity of the 4:2, 6:2, 8:2, and 10:2 saturated (FTCA) and unsaturated (FTUCA) fluorotelomer carboxylic acids to Daphnia magna, Chironomus tentans, and Lemna gibba. In general, toxicity increased with increasing fluorocarbon (FC) chain length, particularly for telomer acids of > or =8 FCs. In addition, the FTCAs were generally more toxic than the corresponding FTUCAs. Acute EC50s ranged from 0.025 mg/L (0.04 micromol/L) for D. magna (10:2 FTCA, immobility) to 63 mg/L (167 micromol/L) for C. tentans (6:2 FTCA, growth). While chain-length trends observed in the current study agree with those previously reported for PFCAs, the toxicity thresholds generated here are up to 10,000 times smaller. Our data provide the first evidence that PFCA precursors are more toxic than the PFCAs themselves.

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

A few free checks a day · papers already verified open instantly · results are public

Integrity signals

Registry

Crossref · 10.1021/es070734c

Cites

2 of 2 references verified0 citation errors · 0 not checkable

Statistics

Claims the paper makes

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

A few free checks a day · papers already verified open instantly · results are public

Claims other papers make about this one

Each is checked against this paper’s own text: does it say what the citing paper says it does?

Self-check

Percentages, sums and reported differences re-computed from the paper’s own numbers.

The self-check needs the paper’s full text.

Cites

Flagged first, then by citations

Research works printed but not linked: 33

  1. Ellis, D. A.; Martin, J. W.; De Silva, A. O.; Mabury, S. A.; Hurley, M. D.; Sulbaek Andersen, M. P.; Wallington, T. J. Degradation of fluorotelomer alcohols: A likely atmospheric source of perfluorinated carboxylic acids. Environ. Sci. Technol. 2004, 38, 3316-3321.
  2. Dinglasan, M. J.; Ye, Y.; Edwards, E. A.; Mabury, S. A. Fluo- rotelomer alcohol biodegradation yields poly-and perfluori- nated aids. Environ. Sci. Technol. 2004, 38, 2857-2864.
  3. Wang, N.; Szostek, B.; Folsom, P. W.; Sulecki, L. M.; Capka, V.; Buck, R. C.; Berti, W. R.; Gannon, J. T. Aerobic biotransformation of 14 C-labeled 8-2 telomer B alcohol by activated sludge from a domestic sewage treatment plant. Environ. Sci. Technol. 2005, 39, 531-538.
  4. Kubwabo, C.; Vais, N.; Benoit, F. M. A pilot study on the determination of perfluorooctanesulfonate and other perflu- orinated compounds in blood of Canadians. J. Environ. Monit. 2004, 6, 540-545.
  5. Moody, C. A.; Martin, J. W.; Kwan, W. C.; Muir, D. C. G.; Mabury, S. A. Monitoring perfluorinated surfactants in biota and surface water samples following an accidental release of fire-fighting foam into Etobicoke Creek. Environ. Sci. Technol. 2002, 36, 545- 551.
  6. Martin, J. W.; Whittle, M. D.; Muir, D. C. G.; Mabury, S. A. Perfluoroalkyl contaminants in a food web from Lake Ontario. Environ. Sci. Technol. 2004, 38, 5379-5385.
  7. Martin, J. W.; Smithwick, M. M.; Braune, B. M.; Hoekstra, P. F.; Muir, D. C. G.; Mabury, S. A. Identification of long-chain perfluorinated acids in biota from the Canadian Arctic. Environ. Sci. Technol. 2004, 38, 373-380.
  8. Kannan, K.; Tao, L.; Sinclair, E.; Pastva, S. D.; Jude, D. J.; Giesy, J. P. Perfluorinated compounds in aquatic organisms at various trophic levels in a Great Lakes food chain. Arch. Environ. Contam. Toxicol. 2005, 48, 559-566.
  9. So, M. K.; Taniyasu, S.; Yamashita, N.; Giesy, J. P.; Zheng, J.; Fang, Z.; Im, S. H.; Lam, P. K. S. Perfluorinated compounds in coastal waters of Hong Kong, South China, and Korea. Environ. Sci. Technol. 2004, 38, 4056-4063.
  10. Kissa, E. Fluorinated Surfactants and Repellents, 2nd ed.; Marcel Dekker, Inc.: New York, 2001; Vol. 97.
  11. Ellis, D. A.; Martin, J. W.; Hurley, M. D.; Sulbaek Andersen, M. P.; Wallington, T. J. Atmospheric lifetime of fluorotelomer alcohols. Environ. Sci. Technol. 2003, 37, 3816-3820.
  12. Stock, N. L.; Lau, F. K.; Ellis, D. A.; Martin, J. W.; Muir, D. C. G.; Mabury, S. A. Polyfluorinated telomer alcohols and sulfonamides in the North American troposphere. Environ. Sci. Technol. 2004, 38, 991-996.
  13. Dinglasan-Panlilio, M. J. A.; Mabury, S. A. Significant residual fluorinated alcohols are present in fluorinated polymers. Environ. Sci. Technol. 2005, In Press.
  14. Hurley, M. D.; Ball, J. C.; Wallington, T. J.; Sulbaek Andersen, M. P.; Ellis, D. A.; Martin, J. W.; Mabury, S. A. Atmospheric chemistry of 4:2 fluorotelomer alcohol (CF 3(CF2)3CH2CH2OH): Products and mechanism of Cl atom initiated oxidation. J. Phys. Chem. A 2004, 108, 5635-5642.
  15. Loewen, M.; Halldorson, T.; Wang, F.; Tomy, G. Fluorotelomer carboxylic acids and PFOS in rainwater from an urban center in Canada. Environ. Sci. Technol. 2005, 39, 2944-2951.
  16. Houde, M.; Martin, J. W.; Letcher, R. J.; Solomon, K.; Muir, D. C. G. Biological monitoring of polyfluoroalkyl substances: A review. Environ. Sci. Technol. 2006, 40, 3463-3473.
  17. Butt, C.; Muir, D. C. G.; Stirling, I.; Kwan, M.; Mabury, S. A. Rapid response of arctic ringed seals to changes in perfluoroalkyl production. Environ. Sci. Technol. 2007, 41, 42-49.
  18. Gauthier, S. A.; Mabury, S. A. Aqueous photolysis of 8:2 fluorotelomer alcohol. Environ. Toxicol. Chem. 2005, 24, 1837- 1846.
  19. Achilefu, S.; Mansuy, L.; Selve, C.; Thiebaut, S. Synthesis of 2H,- 2H-perfluoroalkyl and 2H-perfluoroalkenyl carboxylic acids and amides. J. Fluorine Chem. 1995, 70, 19-26.
  20. MacDonald, M. M.; Warne, A. L.; Stock, N. L.; Mabury, S. A.; Solomon, K. R.; Sibley, P. K. Toxicity of perfluorooctane sulfonic acid and perfluorooctanoic acid to Chironomus tentans. Environ. Toxicol. Chem. 2004, 23, 2116-2123.
  21. Greenberg, B. M.; Huang, X.; Dixon, D. G. Applications of the aquatic higher plant Lemna gibba for ecotoxicological assess- ment. J. Aquat. Ecosyst. Health 1992, 1, 147-155.
  22. ASTM. Standard guide for conducting static toxicity tests with Lemna gibba G3. Designation: E 1415 -91. In Annual Book of ASTM Standards, 11 ed.; ASTM: West Conshohocken, PA, 2001; Vol. 11.05, pp 753-762.
  23. ASTM. Standard guide for conducting acute toxicity tests on test materials with fishes, macroinvertebrates, and amphibians. Designation: E729-96. In Annual Book of ASTM Standards, 11 ed.; ASTM: West Conshohocken, PA, 2001; Vol. 11.05, pp 175- 196.
  24. ASTM. Test method for measuring the toxicity of sediment- associated contaminants with freshwater invertebrates. Des- ignation: E 1706-00. In Annual Book of ASTM Standards: Water and environmental technology, 11 ed.; ASTM: West Consho- hocken, PA, 2001; Vol. 11.05, pp 1109-1225.
  25. Stephenson, G.; Koper, N.; Atkinson, G.; KR, S.; Scroggins, R. Use of nonlinear regression techniques for describing concen- tration-response relationships of plant species exposed to contaminated soils. Environ. Toxicol. Chem. 2000, 19, 2968- 2981.
  26. Boudreau, T. M.; Sibley, P.; Mabury, S. A.; Muir, D. C. G.; Solomon, K. Toxicity of Perfluoroalkyl Carboxylic Acids of Different Chain Length to Selected Freshwater Organisms. In Department of Environmental Biology, Master's Thesis; University of Guelph: Guelph, ON, 2002; p 134.
  27. Upham, B. L.; Deocampo, N. D.; Wurl, B.; Trosko, J. E. Inhibition of gap junction intercellular communication by perfluorinated fatty acids is dependent on the chain length of the fluorinated tail. Int. J. Cancer 1998, 78, 491-495.
  28. Goecke, C. M.; Jarnot, B. M.; Reo, N. V. A comparative toxicological investigation of perfluorocarboxylic acids in rats by fluorine-19 NMR spectroscopy. Chem. Res. Toxicol. 1992, 5, 512-519.
  29. Goecke-Flora, C. M.; Reo, N. V. Influence of carbon chain length on the hepatic effects of perfluorinated fatty acids. A 19 F-and 31 P-NMR investigation. Chem. Res. Toxicol. 1996, 9, 689-695.
  30. Intrasuksri, U.; Feller, D. R. Comparison of the effects of selected monocarboxylic, dicarboxylic and perfluorinated fatty acids on peroxisome proliferation in primary cultured rat hepatocytes. Biochem. Pharm. 1991, 42, 184-188.
  31. MacDonald, M. M. Fluorotelomer Acid Toxicity to Aquatic Organisms. M.Sc. Thesis. University of Guelph, Guelph, Ontario, Canada, 2005
  32. Martin, J. W.; Mabury, S. A.; O'Brien, P. J. Metabolic products and pathways of fluorotelomer alcohols in isolated rat hepa- tocytes. Chem.-Biol. Interact. 2005, 155, 165-180.
  33. Hagen, D. F.; Belisle, J.; Johnson, J. D.; Venkateswarlu, P. Characterization of fluorinated metabolites by a gas chromato- graphic helium microwave plasma detectorsThe biotransfor- mation of 1H, 1H, 2H, 2H-perfluorodecanol to perfluorooc- tanoate. Anal. Biochem. 1981, 118, 336-343.

Cited by

Sorted by citations

Authors
Phillips, M. M. (., Dinglasan-Panlilio, M. J. A., Mabury, S. A., Solomon, K. R., & Sibley, P. K.
Affiliations
University of Toronto (CA)
Corresponding author
Sibley, Paul K.
Venue
Environmental Science & Technology
Published
2007-09-19
Volume
41
Issue
20
Pages
7159-7163
ISSN
  • 0013-936X (ISSN-L)
  • 1520-5851
OpenAlex
W2010936035
Cited by
150
References
2
Citations by year
2026: 11 · 2025: 9 · 2024: 9 · 2023: 12 · 2022: 13 · 2021: 10 · 2020: 9 · 2019: 5 · 2018: 4 · 2017: 7 · 2016: 7 · 2015: 6 · 2014: 7 · 2013: 8 · 2012: 10
FWCI
3.70
Type
journal article
Language
en
Open access
Locations
  • Environmental Science & Technology (publishedVersion)
  • PubMed (publishedVersion)
  • University of Washington Tacoma Digital Commons (University of Washington Tacoma) (submittedVersion)
  • The Atrium (University of Guelph) (submittedVersion)
Funders
Natural Sciences and Engineering Research Council of Canada
Topics
  • Physical Sciences › Environmental Science › Environmental Chemistry › Per- and polyfluoroalkyl substances research
  • Physical Sciences › Environmental Science › Health, Toxicology and Mutagenesis › Environmental Toxicology and Ecotoxicology
  • Physical Sciences › Environmental Science › Health, Toxicology and Mutagenesis › Toxic Organic Pollutants Impact
Keywords
fluorotelomer carboxylic acids, fluorotelomer alcohols, perfluorinated carboxylic acids, acute toxicity, Daphnia magna, Chironomus tentans, Lemna gibba, chain length dependence, surface water toxicity
MeSH terms
Animals, Carboxylic Acids, Chironomidae, Daphnia, Fluorine, Fluorocarbons

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review