Fluorinated organics in the biosphere
Abstract
The use of organofluorine compounds has increased throughout this century, and they are now ubiquitous environmental contaminants. Although generally viewed as recalcitrant because of their lack of chemical reactivity, many fluorinated organics are biologically active. Several questions surround their distribution, fate, and effects. Of particular interest is the fate of perfluoroalkyl substituents, such as the trifluoromethyl group. Most evidence to date suggest that such groups resist defluorination, yet they can confer significant biological activity. Certain volatile fluorinated compounds can be oxidized in the troposphere yielding nonvolatile compounds, such as trifluoroacetic acid. In addition, certain nonvolatile fluorinated compounds can be transformed in the biosphere to volatile compounds. Research is needed to assess the fate and effects of nonvolatile fluorinated organics, the fluorinated impurities present in commercial formulations, and the transformation products generated by biochemical processes and/or oxidation in the troposphere.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
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?
Pseudomonas sp. Strain D2 partially defluorinated 6:2 FTSA under aerobic conditions.
“Key et al. (1997) found isolated Pseudomonas sp. Strain D2 partially defluorinated 6:2 FTSA under aerobic conditions.”
From Biotransformation of perfluoroalkyl acid precursors from various environmental systems: advances and perspectives (2021) · cites this paper as Key et al. (1997)
Cites
Stratospheric sink for chlorofluoromethanes: chlorine atom-catalysed destruction of ozone
Molina, M. J., & Rowland, F. S. (1974) · Nature · doi:10.1038/249810a0 · Cited by 4,332 · see citing works
Fluoride Metabolites After Prolonged Exposure of Volunteers and Patients to Desflurane
Sutton, T. S., Koblin, D. D., Gruenke, L. D., Weiskopf, R. B., Rampil, I. J., Waskell, L., & Eger, E. I. (1991) · Anesthesia & Analgesia · doi:10.1213/00000539-199108000-00011 · Cited by 122 · see citing works
Flagged first, then by citations
Cited by
Sorted by citations
Compound-specific, quantitative characterization of organic fluorochemicals in biological matrices
Hansen, K. J., Clemen, L. A., Ellefson, M. E., & Johnson, H. O. (2001) · Environmental Science & Technology · doi:10.1021/es001489z · Cited by 923 · see citing works
The Developmental Toxicity of Perfluoroalkyl Acids and Their Derivatives
Lau, C., Butenhoff, J. L., & Rogers, J. M. (2004) · Toxicology and Applied Pharmacology · doi:10.1016/j.taap.2003.11.031 · Cited by 867 · see citing works
Trojanowicz, M., Bojanowska-Czajka, A., Bartosiewicz, I., & Kulisa, K. (2018) · Chemical Engineering Journal · doi:10.1016/j.cej.2017.10.153 · Cited by 550 · see citing works
Microbial degradation of polyfluoroalkyl chemicals in the environment: A review
Liu, J., & Mejia Avendaño, S. (2013) · Environment International · doi:10.1016/j.envint.2013.08.022 · Cited by 525 · see citing works
Johansson, N., Fredriksson, A., & Eriksson, P. (2008) · NeuroToxicology · doi:10.1016/j.neuro.2007.10.008 · Cited by 463 · see citing works
Cui, L., Zhou, Q.-F., Liao, C.-Y., Fu, J.-J., & Jiang, G.-B. (2009) · Archives of Environmental Contamination and Toxicology · doi:10.1007/s00244-008-9194-6 · Cited by 368 · see citing works
Mamsen, L. S., Björvang, R. D., Mucs, D., Vinnars, M.-T., Papadogiannakis, N., Lindh, C. H., Andersen, C. Y., & Damdimopoulou, P. (2019) · Environment International · doi:10.1016/j.envint.2019.01.010 · Cited by 338 · see citing works
Trophic Magnification of Poly- and Perfluorinated Compounds in a Subtropical Food Web
Loi, E. I. H., Yeung, L. W. Y., Taniyasu, S., Lam, P. K. S., Kannan, K., & Yamashita, N. (2011) · Environmental Science & Technology · doi:10.1021/es200432n · Cited by 335 · see citing works
Effect of solution chemistry on the adsorption of perfluorooctane sulfonate onto mineral surfaces
Tang, C. Y., Shiang Fu, Q., Gao, D., Criddle, C. S., & Leckie, J. O. (2010) · Water Research · doi:10.1016/j.watres.2010.01.038 · Cited by 284 · see citing works
Self-citationHuang, H., Huang, C., Wang, L., Ye, X., Bai, C., Simonich, M. T., Tanguay, R. L., & Dong, Q. (2010) · Aquatic Toxicology · doi:10.1016/j.aquatox.2010.02.003 · Cited by 283 · see citing works
Zhang, W., Pang, S., Lin, Z., Mishra, S., Bhatt, P., & Chen, S. (2021) · Environmental Pollution · doi:10.1016/j.envpol.2020.115908 · Cited by 280 · see citing works
McGuire, M. E., Schaefer, C., Richards, T., Backe, W. J., Field, J. A., Houtz, E., Sedlak, D. L., Guelfo, J. L., Wunsch, A., & Higgins, C. P. (2014) · Environmental Science & Technology · doi:10.1021/es5006187 · Cited by 269 · see citing works
Renal elimination of perfluorocarboxylates (PFCAs)
Han, X., Nabb, D. L., Russell, M. H., Kennedy, G. L., & Rickard, R. W. (2012) · Chemical Research in Toxicology · doi:10.1021/tx200363w · Cited by 250 · see citing works
Shaw, D. M. J., Munoz, G., Bottos, E. M., Duy, S. V., Sauvé, S., Liu, J., & Van Hamme, J. D. (2019) · Science of The Total Environment · doi:10.1016/j.scitotenv.2018.08.012 · Cited by 232 · see citing works
Investigating the biodegradability of perfluorooctanoic acid
Liou, J. S.-C., Szostek, B., DeRito, C. M., & Madsen, E. L. (2010) · Chemosphere · doi:10.1016/j.chemosphere.2010.03.009 · Cited by 191 · see citing works
Ji, K., Kim, Y., Oh, S., Ahn, B., Jo, H., & Choi, K. (2008) · Environmental Toxicology and Chemistry · doi:10.1897/07-523.1 · Cited by 191 · see citing works
Li, F., Zhang, C., Qu, Y., Chen, J., Chen, L., Liu, Y., & Zhou, Q. (2010) · Science of The Total Environment · doi:10.1016/j.scitotenv.2009.10.032 · Cited by 191 · see citing works
Masoner, J. R., Kolpin, D. W., Cozzarelli, I. M., Smalling, K. L., Bolyard, S. C., Field, J. A., Furlong, E. T., Gray, J. L., Lozinski, D., Reinhart, D., et al. (2020) · Environmental Science: Water Research & Technology · doi:10.1039/d0ew00045k · Cited by 188 · see citing works
Davis, K. L., Aucoin, M. D., Larsen, B. S., Kaiser, M. A., & Hartten, A. S. (2007) · Chemosphere · doi:10.1016/j.chemosphere.2006.11.049 · Cited by 187 · see citing works
Sorption of short- and long-chain perfluoroalkyl surfactants on sewage sludges
Zhang, C., Yan, H., Li, F., Hu, X., & Zhou, Q. (2013) · Journal of Hazardous Materials · doi:10.1016/j.jhazmat.2013.06.022 · Cited by 182 · see citing works
Wackett, L. P. (2022) · Microbial Biotechnology · doi:10.1111/1751-7915.13928 · Cited by 165 · see citing works
Yu, Y., Che, S., Ren, C., Jin, B., Tian, Z., Liu, J., & Men, Y. (2022) · Environmental Science & Technology · doi:10.1021/acs.est.1c05509 · Cited by 143 · see citing works
Pan, C.-G., Ying, G.-G., Zhao, J.-L., Liu, Y.-S., Jiang, Y.-X., & Zhang, Q.-Q. (2014) · Science of The Total Environment · doi:10.1016/j.scitotenv.2014.06.033 · Cited by 143 · see citing works
Perfluoroalkyl acids (PFAAs) in riverine and coastal sediments of Laizhou Bay, North China
Zhao, Z., Tang, J., Xie, Z., Chen, Y., Pan, X., Zhong, G., Sturm, R., Zhang, G., & Ebinghaus, R. (2013) · Science of The Total Environment · doi:10.1016/j.scitotenv.2012.12.095 · Cited by 106 · see citing works
Biodegradation and biotransformation of organofluorine compounds
Murphy, C. D. (2010) · Biotechnology Letters · doi:10.1007/s10529-009-0174-3 · Cited by 93 · see citing works
Case–control study on perfluorinated alkyl acids (PFAAs) and the risk of prostate cancer
Hardell, E., Kärrman, A., van Bavel, B., Bao, J., Carlberg, M., & Hardell, L. (2014) · Environment International · doi:10.1016/j.envint.2013.10.005 · Cited by 80 · see citing works
Borg, D., Bogdanska, J., Sundström, M., Nobel, S., Håkansson, H., Bergman, Å., DePierre, J. W., Halldin, K., & Bergström, U. (2010) · Reproductive Toxicology · doi:10.1016/j.reprotox.2010.07.004 · Cited by 76 · see citing works
Neutral polyfluoroalkyl substances in the global Atmosphere
Gawor, A., Shunthirasingham, C., Hayward, S. J., Lei, Y. D., Gouin, T., Mmereki, B. T., Masamba, W., Ruepert, C., Castillo, L. E., Shoeib, M., et al. (2014) · Environ. Sci.: Processes Impacts · doi:10.1039/c3em00499f · Cited by 75 · see citing works
Liao, C., Wang, T., Cui, L., Zhou, Q., Duan, S., & Jiang, G. (2009) · Environmental Science & Technology · doi:10.1021/es802985e · Cited by 74 · see citing works
Willach, S., Brauch, H.-J., & Lange, F. T. (2016) · Chemosphere · doi:10.1016/j.chemosphere.2015.11.113 · Cited by 71 · see citing works
Chen, J., Das, S. R., La Du, J., Corvi, M. M., Bai, C., Chen, Y., Liu, X., Zhu, G., Tanguay, R. L., Dong, Q., et al. (2013) · Environmental Toxicology and Chemistry · doi:10.1002/etc.2031 · Cited by 70 · see citing works
Ellis, D. A., & Mabury, S. A. (2000) · Environmental Science & Technology · doi:10.1021/es990422c · Cited by 68 · see citing works
Sun, H., Zhang, X., Wang, L., Zhang, T., Li, F., He, N., & Alder, A. C. (2012) · Environmental Science and Pollution Research · doi:10.1007/s11356-011-0727-6 · Cited by 62 · see citing works
Perfluorododecanoic Acid Exposure Induced Developmental Neurotoxicity in Zebrafish Embryos
Guo, X., Zhang, S., Lu, S., Zheng, B., Xie, P., Chen, J., Li, G., Liu, C., Wu, Q., Cheng, H., et al. (2018) · Environmental Pollution · doi:10.1016/j.envpol.2018.06.013 · Cited by 58 · see citing works
Kali, S. E., Österlund, H., Viklander, M., & Blecken, G.-T. (2025) · Water Research · doi:10.1016/j.watres.2024.122973 · Cited by 62 · see citing works
“F) bonds in PFAS provide high thermal and chemical stability (Key et al., 1997).”
Xie, G., Cui, J., Zhai, Z., & Zhang, J. (2020) · Environmental Science and Pollution Research · doi:10.1007/s11356-019-06689-4 · Cited by 38 · see citing works
Perfluorododecanoic Acid Induces Cognitive Deficit in Adult Rats
Kawabata, K., Matsuzaki, H., Nukui, S., Okazaki, M., Sakai, A., Kawashima, Y., & Kudo, N. (2017) · Toxicological Sciences · doi:10.1093/toxsci/kfx058 · Cited by 37 · see citing works
Contaminant Exposure and Transport from Three Potential Reuse Waters within a Single Watershed
Masoner, J. R., Kolpin, D. W., Cozzarelli, I. M., Bradley, P. M., Arnall, B. B., Forshay, K. J., Gray, J. L., Groves, J. F., Hladik, M. L., Hubbard, L. E., et al. (2023) · Environmental Science & Technology · doi:10.1021/acs.est.2c07372 · Cited by 36 · see citing works
Nolen, R. M., Faulkner, P., Ross, A. D., Kaiser, K., Quigg, A., & Hala, D. (2022) · Science of The Total Environment · doi:10.1016/j.scitotenv.2021.150361 · Cited by 29 · see citing works
Asakawa, A., Toyoshima, M., Harada, K., Fujimiya, M., Inoue, K., & Koizumi, A. (2008) · International Journal of Molecular Medicine · doi:10.3892/ijmm.21.4.439 · Cited by 26 · see citing works
Contamination of per- and poly-fluoroalkyl substances in agricultural soils: A review
Biswas, B., Joseph, A., Parveen, N., Ranjan, V. P., Goel, S., Mandal, J., & Srivastava, P. (2025) · Journal of Environmental Management · doi:10.1016/j.jenvman.2025.124993 · Cited by 27 · see citing works
- Authors
- Key, B. D., Howell, R. D., & Criddle, C. S.
- Affiliations
- Michigan State University (US)
- ORCID
- Criddle, Craig S.
- Venue
- Environmental Science & Technology
- Publisher
- American Chemical Society (ACS)
- Published
- 1997-08-28
- Volume
- 31
- Issue
- 9
- Pages
- 2445-2454
- ISSN
- 0013-936X (ISSN-L)
- 1520-5851
- OpenAlex
- W2004024071
- Cited by
- 729
- References
- 2
- Citations by year
- 2026: 17 · 2025: 19 · 2024: 26 · 2023: 20 · 2022: 29 · 2021: 32 · 2020: 39 · 2019: 29 · 2018: 24 · 2017: 28 · 2016: 33 · 2015: 30 · 2014: 44 · 2013: 38 · 2012: 38
- FWCI
- 4.92
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Environmental Science & Technology (publishedVersion)
- Funders
- National Science Foundation
- Topics
- Physical Sciences › Environmental Science › Environmental Chemistry › Per- and polyfluoroalkyl substances research
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmaceutical Science › Fluorine in Organic Chemistry
- Physical Sciences › Environmental Science › Health, Toxicology and Mutagenesis › Toxic Organic Pollutants Impact
- Keywords
- organofluorine compounds, environmental pollutants, perfluorinated compounds, trifluoromethyl group, biological activity, tropospheric oxidation, trifluoroacetic acid, degradation intermediates, commercial formulations, bioaccumulation
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