Document O1Vo56Z6GLnyaeQKOexVXr7me

M 3M Specialty Materials 3M Center St. Paul, MN 55144-1000 651 733 1110 May 11,2004 TSCA Non-Confidential Information Center (7407T) Office of Pollution Prevention and Toxics (OPPT) Docket AR-226 EPA West Building, Room B-146 1301 Constitution Ave., N.W. Washington, DC 20460 Phone: 202-566-0280 Attention: OPPT Docket No. AR-226 Re: Information on Perfluorooctane Sulfonate, Perfluorooctanoic Acid, and Related Compounds Dear Sir or Madam: This continues 3M's voluntary submissions of data on perfluorooctane sulfonate (PFOS), perfluorooctanoic acid (PFOA), and related compounds, as part of our ongoing dialogue with EPA regarding perfluorochemicals. We are enclosing for the docket paper copies of a number of studies, or in the case of a collection of bird studies, a CD of electronic copies. The studies are itemized on the enclosed index. As in our past submissions, we have organized the studies by chemical, and within the sections for each chemical, by endpoint or type of study. This submission includes studies related to PFOS, PFOA, and other compounds, and also includes studies that address multiple compounds. With respect to the environmental studies, please note that this submission includes revised reports on the Tennessee River study which should replace those we submitted in July 2003. In addition, we have included in this submission addenda to a number of PFOS ecotoxicological studies correcting reported values based on a new analysis of the purity of the sample material used in the tests. The more recent analysis identified additional impurities in the test material and thus revised the sample purity slightly downward. We have provided the AR226 docket reference for each of the studies to which these addenda pertain. We are also providing a table summarizing the changes to each study report. Docket Office May 2004 Page 2 o f 2 Consistent with our past practice, we have included a bibliography of recently published literature in 3M's possession. Given the amount of published literature and its ready availability to EPA, we intend to discontinue the bibliography listing in future submissions. We will also be providing under separate cover in the near future 3M's CD#6 of its AR226 submissions, containing copies of all submissions from February 2002 through this May, 2004 submission. We look forward to continuing our dialogue with the Agency. Please feel free to contact me with any questions. Very truly yours, cc: Dr. Charles Auer Dr. Oscar Hernandez (without enclosures) Michael A. Santoro Director of Environmental, Health, Safety and Regulatory Affairs 3M Building 236-1B-10 St. Paul, MN 55144 651-733-6374 (phone) 651-733-1958 (fax) E-mail: masantoro@mmm.com ATTACHMENT TO LETTER OF May 11,2004 3M FLUOROCHEMICAL SUBMISSION 3M FLUOROCHEMICAL SUBMISSION TOXICOLOGY, EPIDEMIOLOGY AND MEDICAL SURVEILLANCE Multiple Chemicals Human Sera/Medical Surveillance/Epidemiology 1. Final Report, Descriptive Analysis of Serum Perfluorooctanoate (PFOA) and Perfluorooctanesulfonate (PFOS) Concentrations of Antwerp Employee Participants from the 2003 Fluorochemical Medical Surveillance Program, 3M Medical Department, August 14, 2003. 2. Sample Analysis Report for Protocol EPI-0012, Quantitative Determination of PFOS and Related Compounds in Human Serum by LC/MS/MS, Northwest Bioanalytical Study No. NWBS00-091, November 21, 2001. 3. Sample Analysis Report for Protocol EPI-PEuro, Quantitative Determination of PFOS, PFOSA, PFOSAA, PFHS, POAA, M556 and M570 in Human Serum by LC/MS/MS, Northwest Bioanalytical Study No. NWBS99-117, December 9,1999. 4. Sample Analysis Report for Protocol EPI-Swed, Quantitative Determination of PFOS, PFOSA, PFOSAA, PFHS, POAA, M556 and M570 in Human Serum by LC/MS/MS, Northwest Bioanalytical Study No. NWBS99-116, December 9, 1999. Pharmacokinetic Study 1. Final Report, Xenochemical Receptor trans-Activation by Perfluorooctane-based Chemicals, Boston University Department of Biology, 3M Reference No. T-6295.35, September 12, 2001. PFOS Perfluorooctane sulfonate Pharmacokinetic. Mechanism and Other Studies 1. Final Report, An Investigation of the Mechanism of Toxicity in Adult Rats Exposed to High Levels of Perfluorooctanesulfonate (PFOS), 3M Project No. T-6295.31, April 23, 2004. 2. Final Report, Analysis of Liver Enzymes, Glycogen, and Perfluorooctane Sulfonate (PFOS) Concentration in Samples from T-6295.25: One-Generation Reproduction Study of PFOS - Mevalonic Acid/Cholesterol Challenge and NOEL Investigation in Rats, 3M Project No. T-6295.28, April 23, 2004. ATTACHMENT TO LETTER OF May 11,2004 3M FLUOROCHEMICAL SUBMISSION 3. Final Report, Determination of Possible Interference of Perfluorooctane Sulfonic Acid Potassium Salt with Rat Cholesterol, 3M Project No. 6329.263, August 17, 1999. PFOA Perfluorooctanoate 1. "Genotoxicity, Carcinogenicity, Developmental Effects and Reproductive Effects of Perfluorooctanoate: A Perspective from Available Animal and Human Studies," Association of Plastics Manufacturers of Europe and The Society of the Plastics Industry, December 12, 2002. [previously submitted to EPA but we have not been able to locate in the docket] POSF Perfluorooctanesulfonyl fluoride Repeat Dose 1. Final Report, Oral Toxicity Rangefinder for Perfluorooctane Sulfonyl Fluoride (POSF) in Rats, 3M Study No. T-7098.2, May 11, 2001. Pharmacokinetic Study 1. Final Report, Acute Inhalation Toxicokinetic Study of Perfluorooctanesulfonyl Fluoride (POSF), 3M Study No. T7098.4, November 9, 2001. PFHS Perfluorohexane sulfonate Repeat-Dose 1. Final Report, Oral (Gavage) Combined Repeated Dose Toxicity Study of T-7706 with the Reproduction/Developmental Toxicity Screening Test, Argus Research Protocol No. 418 028, 3M Reference No. T-7706, July 31, 2003. FOSA Perfluorooctanesulfonamide Pharmacokinetics and Mechanism Studies 1. Final Report, Comparative Molecular Biology of Perfluorooctanesulfonamide (FOSA, T7132) in Rats Following Four Consecutive Days of Dosing, Study No. DTI 5, 3M Reference No. T-7132, February 18, 2004. ATTACHMENT TO LETTER OF May 11, 2004 3M FLUOROCHEMICAL SUBMISSION ENVIRONMENTAL STUDIES Multiple Chemicals Environmental Monitoring 1. Revised Tennessee River Study (replaces versions submitted July 2003) a. Revised Report, A Survey of Selected Fluorochemicals in the Decatur Alabama Area - 2002 Sampling, Entrix, Inc. Project No. 178401, November 2003. (replaces the previously submitted Docket No. AR226-1364) b. Revised Analytical Laboratory Report, Tennessee River Valley Samples, 3M Environmental Laboratory Study # E02-0443, September 12, 2003. (replaces the previously submitted Docket No. AR226-1365) PFOS Perfluorooctane sulfonate Ecotoxicitv Studies 1. Avian In-life Studies a. Mallard Duck Acute Study i. Toxicological Summary, PFOS - Dietary Acute Mallard Study, May 5, 2004. ii. Final Report, PFOS: A Dietary LC50 Study with the Mallard, Wildlife International, Ltd. Project No. 454-102, March 24, 2004. iii. Analytical Report, Laboratory Report Revision 1: Analytical Report of Data for PFOS Dietary LC50 Study with Mallards (Sera and Liver), 3M Environmental Laboratory No. FACT-TOX-130, March 23,2001. b. Mallard Duck Pilot Study i. Toxicological Summary, PFOS - Dietary Chronic Pilot Reproductive Study: Mallard, May 5, 2004. ii. Final Report, PFOS: A Pilot Reproduction Study with the Mallard, Wildlife International, Ltd. Project No. 454-105, March 24, 2004. ATTACHMENT TO LETTER OF May 11,2004 3M FLUOROCHEMICAL SUBMISSION iii. Analytical Report, Extraction of Potassium Perfluorooctanesulfonate from Mallard Serum and Mallard Liver for Analysis Using HPLCElectrospray/Mass Spectrometry (Mallard Pilot Study Samples), Centre Study No. 023-042, September 10, 2001. iv. Analytical Report, Extraction of Potassium Perfluorooctanesulfonate from Egg Membrane, Albumen, and Yolk for Analysis Using HPLCElectrospray/Mass Spectrometry (Quail and Mallard Pilot Studies samples), Centre Study No. 023-063, September 10, 2001. c. Mallard Duck Definitive Study i. Toxicological Summary, PFOS - Dietary Chronic Definitive Reproductive Study: Mallard, May 5, 2004. ii. Final Report, PFOS: A Reproduction Study with the Mallard, Wildlife International, Ltd. Project No. 454-109, March 24, 2004. iii. Analytical Report, Analytical Phase Report for PFOS: A Reproduction Study with the Mallard (Mallard Definitive Study Sera and Liver Analyses), 3M Environmental Laboratory Study # E01-1256, January 22, 2003. iv. Analytical Report, Extraction of Potassium Perfluorooctanesulfonate from Red Blood Cells and Serum for Analysis Using HPLC-Electrospray/Mass Spectrometry (Samples from Definitive Mallard and Quail Reproduction Studies), Exygen Study No. 023-066, June 12, 2003. v. Analytical Report, Analysis of Perfluorooctanesulfonate in Mallard and Quail Egg Yolk (Mallard and Quail Definitive Reproduction Study Eggs), Exygen Study No. 023-070, July 5, 2002. d. Northern Bobwhite Quail Acute Study i. Toxicological Summary, PFOS - Dietary Acute Northern Bobwhite Study, May 5, 2004. ii. Final Report, PFOS: A Dietary LC50 Study with the Northern Bobwhite, Wildlife International, Ltd. Project No. 454-103, March 24,2004. iii. Analytical Report, Laboratory Report Revision 1: Analytical Report of Data for PFOS Dietary LC50 Study in Northern Bobwhite (Sera and Liver), 3M Environmental Laboratory No. FACT-TOX-129, March 23, 2001. ATTACHMENT TO LETTER OF May 11, 2004 3M FLUOROCHEMICAL SUBMISSION e. Northern Bobwhite Quail Pilot Study i. Toxicological Summary, PFOS - Dietary Chronic Pilot Reproductive Study: Northern Bobwhite, May 5, 2004. ii. Final Report, PFOS: A Pilot Reproduction Study with the Northern Bobwhite, Wildlife International, Ltd. Project No. 454-104, March 24, 2004. iii. Analytical Report, Extraction of Potassium Perfluorooctanesulfonate from Quail Serum and Quail Liver for Analysis Using HPLCElectrospray/Mass Spectrometry (Quail Pilot Study Samples), Centre Study No. 023-041, September 10, 2001. f. Northern Bobwhite Quail Definitive Study i. Toxicological Summary, PFOS - Dietary Chronic Definitive Reproductive Study: Northern Bobwhite, May 5, 2004. ii. Final Report, PFOS: A Reproduction Study with the Northern Bobwhite, Wildlife International, Ltd. Project No. 454-108, March 24, 2004. iii. Analytical Report, Analytical Phase Report for PFOS: A Reproduction Study with the Northern Bobwhite (Quail Definitive Study Sera and Liver Analyses), 3M Environmental Laboratory Study # E01-1245, April 18, 2003. 2. Bluegill Study a. Robust Summary, Acute Toxicity to Bluegill Sunfish, 3M, April 14, 2004. b. Analytical Report, 96-Hour Static Bluegill Toxicity Test: Aquatic Toxicity Data Sheet (FC-95), 3M, May 27,1978. Analytical Purity Revisions to Ecotox Studies 1. Summary Table, PFOS Ecotoxicological Testing Results Comparison of Effect Concentrations Calculated Using Different Sample Purity, May 2004 2. Addenda to Previously Submitted Reports Revised to Reflect the Most Recent PFOS Purity Analyses a. Addendum, PFOS: A 96-Hour Static Acute Toxicity Test with the Saltwater Mysid (Mysidopsis bahia), Wildlife International, Ltd. Project No. 454A-101, September 27, 2000 [Addendum to AR226-0095], ATTACHMENT TO LETTER OF May 11, 2004 3M FLUOROCHEMICAL SUBMISSION b. Addendum, PFOS: A 96-Hour Static Acute Toxicity Test with the Fathead Minnow (Pimephales promelas), Wildlife International, Ltd. Project No. 454A-102, September 27, 2000 [Addendum to AR226-0083]. c. Addendum, PFOS: A 96-Hour Toxicity Test with the Freshwater Alga {Selenastrum capricornutum), Wildlife International, Ltd. Project No. 454A-103A, September 27, 2000 [Addendum to AR226-0085], d. Addendum, PFOS: A 48-Hour Static Acute Toxicity Test with the Cladoceran (Daphnia magna), Wildlife International, Ltd. Project No. 454A-104, September 27, 2000 [Addendum to AR226-0087], e. Addendum, PFOS: A 96-Hour Static Acute Toxicity Test with the Freshwater Mussel (Unio complamatus), Wildlife International, Ltd. Project No. 454A-105, September 27, 2000 [Addendum to AR226-0091], f. Addendum, PFOS: A 96-Hour Shell Deposition Test with the Eastern Oyster (Crassostrea virginica), Wildlife International, Ltd. Project No. 454A-106, September 27, 2000 [Addendum to AR226-0089]. g. Addendum, PFOS, A Flow-Through Life-Cycle Toxicity Test with the Saltwater Mysid (Mysidopsis bahia), Wildlife International, Ltd. Project No. 454A-107, September 27, 2000 [Addendum to AR226-0101]. h. Addendum, PFOS: An Early Life-Stage Toxicity Test with the Fathead Minnow (.Pimephales promelas), Wildlife International, Ltd. Project No. 454A-108, September 27, 2000 [Addendum to AR226-0097]. i. Addendum, PFOS: A Semi-Static Life-Cycle Toxicity Test with the Cladoceran (Daphnia magna), Wildlife International, Ltd. Project No. 454A-109, September 27, 2000 [Addendum to AR226-0099]. j. Addendum, Non-GLP Study: Determination of the Solubility of PFOS in Wildlife International, Ltd. Freshwater, Freshwater Algal Medium, and Saltwater, Wildlife International, Ltd. Project No. 454C-101-1, November 27, 2000 [Not previously submitted to the AR226 docket]. k. Addendum, Determination of the Water Solubility of PFOS by the Shake Flask Method, Wildlife International, Ltd. Project No. 454C-107, November 27,2000 [Addendum to AR226-0052]. l. Addendum, PFOS: An Activated Sludge, Respiration Inhibition Test, Wildlife International, Ltd. Project No. 454E-101, December 1, 2000 [Addendum to AR2260093], ATTACHMENT TO LETTER OF May 11, 2004 3M FLUOROCHEMICAL SUBMISSION BIBLIOGRAPHY OF PUBLISHED LITERATURE Alexander BH, Olsen GW, Burris JM, Mandel JH, and Mandel JS (2003). Mortality of Employees of a Perfluorooctanesulphonyl Fluoride Manufacturing Facility. Occup. Environ. Med. 60:722-729. Aslam, M. K. Khalil, Reinhold A. Rasmussen, John A. Culbertson, John M. Prins, Eric P. Grimsrud, and Martha J. Shearer (2003). Atmospheric Perfluorocarbons. Environmental Science and Technology 37: 4358-4361. Austin ME, Kasturi BS, Barber M, Kanna K, MohanKumar PS, and MohanKumar SMJ (2003). Neuroendocrine Effects of Perfluorooctane Sulfonate in Rats. Environ. Health Perspect. 11(12): 1485-1489. Butenhoff JL, Gaylor DW, Moore JA, Olsen GW, Rodricks J, Mandel JH, and Zobel LR (2004). Characterization of Risk for General Population Exposure to Perfluorooctanoate. Reg. Toxicol, and Pharmacol, xx (2004) (in press). Butenhoff JL, Kennedy GL, Frame SR, O'Connor JC, and York RG (2004). The Reproductive Toxicology of Ammonium Perfluorooctanoate (APFO) in the Rat. Toxicol. 196: 95-116. Cai Y, Nelson BD, Li R, Luciakova K, and DePierre JW (1996). Thyromimetic Action of the Peroxisome Proliferators Clofibrate, Perfluorooctanoic Acid and Acetylsalicyclic Acid Includes Changes in mRNA Levels for Certain Genes Involved in Mitochondrial Biogenesis. Archives of Biochem. And Biophysics 325:107-112. Carlini, Filippo M (2002). Fluorinated Surfactants: An Illustrative Example of High Performance Applications of Fluorochemicals in Demanding Environments. CHIMICA OGGI/Chemistry Today March/April, 21-24. Chen, L., S. Kutsuna, K. Tokuhashi, A. Sekiya, K. Takeuchi, T. Ibusuki (2003). Kinetics for the Gas-Phase Reactions of OH Radicals With the Hydrofluoroethers CH2FCF20CHF2, CHF2CF20CH2CF3, CF3CHFCF20CH2CF3, and CF3CHFCF20CH2CF2CHF2 at 268-308 K. International Journal of Chemical Kinetics 35 (6): 239-245. DePierre, Joseph W (2002). Effects on Rodents of Perfluorofatty Acids. The Handbook of Environmental Chemistry Vol. 3: 203-248. Grasty RC, Grey BE, Lau CS, and Rogers JM (2003). Prenatal Window of Susceptibility to Perfluorooctane Sulfonate-Induced Neonatal Mortality in the Sprague-Dawley Rat. Birth Defects Research (Part B) 68: 465-471. Hack, Walter, M. Hold, K. Hoyermann, 1.1. Morozov, and E. S. Vasiliev (2002). Fluorinated Radical Reactions of Atmospheric Importance. Global Atmospheric Change and its Impact on Regional Air Quality, 103-108. Han X, Snow TA, Kemper RA, and Jepson GW (2003). Binding of Perfluorooctanoic Acid to Rat and Human Plasma Proteins. Chem. Res. Toxicology 16 (6): 775-781. ATTACHMENT TO LETTER OF May 11,2004 3M FLUOROCHEMICAL SUBMISSION Hansen, Kristen J., L. A. Clemen, M.E. Ellefson, H. O. Johnson (2001). Compound-Specific, Quantitative Characterization of Organic Fluorochemicals in Biological Matrices. Environmental Science & Technology 35, No. 4: 766-770. Hoff PT, Scheirs J, Van de Vijver K, Van Donge W, Esmans EL, Blust R, and De Coen W (2004). Biochemical effect evaluation of perfluorooctane sulfonic acid polluted wood mice. Environ. Health Perspect., doi:10.1289/ehp.6479, online at http://dx.doi.org, January 20, 2004. Hori, Hisao, Y. Takano, K. Koike, K. Takeuchi, and H. Einaga (2003). Decomposition of Environmentally Persistent Trifluoroacetic Acid to Fluoride Ions by a Homogeneous Photocatalyst in Water. Environmental Science & Technology 37 (2): 418-422. Inoue K, Okada F, Ito R, Kato S, Sasaki S, Nakajima S, Uno A, Saijo Y, Sata F, Yoshimura Y, Kishi R, and Nakazawa H (2004). Perfluorooctane Sulfonate (PFOS) and Related Perfluorinated Compounds in Human Maternal and Cord Blood Samples: Assessment of PFOS Exposure in Susceptible Population during Pregnancy, Environ. Health Perspect. Doi:10.1289/ehp.6864, online at http://dx.doi.org, April 13, 2004. Khalil, M.A.K., and R.A. Rasmussen (1989) The Potential Of Soils As A Sink Of Chlorofluorocarbons And Other Man-Made Chlorocarbons. Geophysical Research Letters, Vol. 16, No. 7, pp. 679-682. Kozlov, Sergey N., V. Orkin, M. Kurylo (2003). An Investigation of the Reactivity of OH with Fluoroethanes: CH3CH2F(HFC-161), CH2FCH2F(HFC-152), and CH3CHF2 (HFC-152a). Journal of Physical Chemistry 107: 2239-2246. Kurunthachalam, K., C. Simonetta, J. Falandysz, G. Oehme, S. Focardi, and J. P. Giesy (2002). Perfluorooctanesulfonate and Related Fluorinated Hydrocarbons in Marine Mammals, Fish, and Birds from Coasts of the Baltic and the Mediterranean Seas. Environmental Science and Technology 36 NO.15, pp. 3210-3216. Lau C, Butenhoff J, and Rogers J (2004). The developmental toxicity of perfluoroalkyl acids and their derivatives. Toxicol, and Applied Pharmacol, xx (2004) (in press). Lau C, Thibodeaux JR, Hanson RG, Rogers JM, Grey BE, Stanton, ME, Butenhoff JL, and Stevenson LA (2003). Exposure to Perfluorooctane Sulfonate During Pregnancy in Rat and Mouse. II: Postnatal Evaluation. Toxicol. Sci. 74(2):382-392. Mabury, Scott A., Redefining Persistence ~ Fluorinated Pollutants in the Environment. Martin JW, Smithwick MM, Braune BM, Hoekstra PF, Muir DCG, and Mabury SA (2003). Identification of Long-Chain Perfluorinated Acids in Biota from the Canadian Arctic. Environ. Sci. Technol. 38(2):373-380. Martin, Jonathan W., S. A. Mabury, K. R. Solomon, and D. C. G. Muir (2003). Dietary Accumulation of Perfluorinated Acids in Juvenile Rainbow Trout (oncorhynchus Mykiss). Environmental Toxicology and Chemistry 22 (1): 189-195. ATTACHMENT TO LETTER OF May 11,2004 3M FLUOROCHEMICAL SUBMISSION Olsen GW, Church TR, Hansen KJ, Butenhoff, JL, Mandel JH, and Zobel LR (2004). Quantitative Evaluation of Perfluorooctanesulfonate (PFOS) and other FCs in the Serum of Children. J. Children's Health 2:1-24. Olsen GW, Church TR, Larson EB, Van Belle G, Lundberg JK, Hansen KJ, Burris JM, Mandel JH, and Zobel LR (2004) Serum Concentrations of Perfluorooctanesulfonate and Other Fluorochemicals in an Elderly Population from Seattle, Washington. Chemosphere 54:1599 1611. Olsen GW, Church TR, Miller JP, Burris JM, Hansen KJ, Lundberg JK, Armitage JB, Herron RM, Medhdizadehkashi Z, Nobiletti JB, O'Neill EM, Mandel JH, and Zobel LR (2003). Perfluorooctanesulfonate and Other Fluorochemicals in the Serum of American Red Cross Adult Blood Donors. Environ. Health Perspect. I l l (16): 1892-1901. Olsen GW, Logan PW, Hansen KJ, Simpson CA, Burris JM, Burlew, MM, Vorarath PP, Venkateswarlu P, Schumpert JC, and Mandel JH (2003). An Occupational Exposure Assessment of a Perfluorooctanesulfonyl Fluoride Production Site: Biomonitoring. AIHA Journal 64:651-659. Olsson U, Sundberg C, Andersson K, and DePierre JW (1993). Further Studies on the Involvement of Selenium in Peroxisome Proliferation in Rat Liver: Comparison of Effects with Clofibric Acid and Perfluorooctanoic Acid and the Pharmacokinetics of [l4]Clofibrate. Biochem. Pharmacol. 46:1805-1810. Panaretakis A, Shabalina IG, Grander D, Shoshan MC, and DePierre JW (2001). Reactive Oxygen Species and Mitochondria Mediate the Induction of Apoptosis in Human Hepatoma HepG2 cells by the Rodent Peroxisome Proliferator and Hepatocarcinogen, Perfluorooctanoic Acid. Toxicol, and Applied Pharmacol. 173:56-64. Permadi H, Lundgren B, Anderson K, and DePierre JW (1992). Effects of Perfluoro Fatty Acids on Xenobiotic-Metabolizing Enzymes, Enzymes which Detoxify Reactive Forms of Oxygen and Lipid Peroxidation in Mouse Liver. Biochem. Pharmacol. 44:1183-1191. Permadi H, Lundgren B, Anderson K, and DePierre JW (1993). Effects of Perfluoro Fatty Acids on Peroxisome Proliferation and Mitochondrial Size in Mouse Liver: Dose and Time Factors and Effect on Chain-Length. Xenobiotica 23:761-770. Raley, Brain K., L. Lovejoy, W. K. Barbee, L.S. Beu (2002). Abstract: Perfluorooctyl Sulfonates (PFOS) Treatment Options and Sampling Methods. 201st Meeting of The Electrochemical Society, Philadelphia Meeting Abstracts Volume 2002-1. Schrder HF (2003). Determination of Fluorinated Surfactants and Their Metabolites in Sewage Sludge Samples by Liquid Chromatography with Mass Spectrometry and Tandem Mass Spectrometry after Pressurized Liquid Extraction and Separation on Fluorine-Modified Reversed-Phase Sorbents. J. of Chromatography A, 1020: 131-151 ATTACHMENT TO LETTER OF May 11, 2004 3M FLUOROCHEMICAL SUBMISSION Shabalina IG, Panaretakis T, Bergstrand A, and DePierre JW (1999). Effects of the Rodent Peroxisome Proliferator and Hepatocarcinogen Perfluorooctanoic Acid on Apoptosis in Human Hepatoma HepG2 Cells. Carcinogenesis 20:2237-2246. Shipley JM, Hurst CH, Tanaka SS, DeRoos FL, Butenhoff JL, Seacat AM, and Waxman DJ (2004). irans-Activation of PPARa Target Genes by Perfluorooctane-based Chemicals. Toxicological Sciences (in press). Sohlenius A-K, Andersson K, and DePierre JW (1992). The Effects of Perfluoro-octanoic Acid on Hepatic Peroxisome Proliferation and Related Parameters Show No Sex-Related Differences in Mice. Biochem. J. 285:779-783. Sohlenius A-K, Andersson K, Bergstrand A, Spydevold O, and DePierre JW (1994). Effects of Perfluorooctanoic Acid - A Potent Peroxisome Proliferator in Rat - on Morris Hepatoma 7800C1 cells, a rat cell line. Biochemica et Biophysica Acta 1213:63-74. Sohlenius A-K, Andersson K, Olsson J, and DePierre JW (1995). Peroxisome Proliferation and Associated Effects Caused by Perfluorooctanoic Acid in Vitamin A-Deficient Mice. ChemicoBiological Interactions 98:45-50. Sohlenius A-K, Lundgren B, and DePierre JW (1992). Perfluorooctanoic Acid Has Persistent Effects on Peroxisome Proliferation and Related Parameters in Mouse Liver. J. Biochem. Toxicol. 7:205-212. Sohlenius A-K, Messing Eriksson A, Hogstrom C, Kimland M, and DePierre JW (1993). Perfluorooctane Sulfonic Acid is a Potent Inducer of Peroxisomal Fatty Acid Beta-Oxidation and Other Activities Known to be Affected by Peroxisome Proliferators in Mouse Liver. Pharmacol, and Toxicol. 72:90-93. Sohlenius A-K, Reinfeldt M, Backstrom K, Bergstrand A, and DePierre JW (1996). Hepatic Peroxisome Proliferation in Vitamin A-Deficient Mice Without a Simultaneous Increase in Peroxisomal Acyl-CoA Oxidase Activity. Biochem. Pharmacol. 51:821-827. Stock NL, Lau FK, Ellis DA, Martin JW, Muir DCG, and Mabury SA (2004). Polyfluorinated Telomer Alcohols and Sulfonamides in the North American Troposphere. Environ. Sci. Technol. 38 (4): 991-996 Takino, M., S. Daishima, and T. Nakahara (2003). Determination of Perfluorooctane sulfonate in River Water by Liquid Chromatography/Atmospheric Pressure Photoionization, Mass Spectrometry by Automated On-line Extraction Using Turbulent Flow Chromatography. Rapid Communications in Mass Spectrometry 17: 383-390. Thibodeaux JR, Hanson RG, Rogers JM, Grey BE, Barbee BD, Richards JH, Butenhoff JL, Stevenson LA, and Lau C (2003). Exposure to Perfluorooctane Sulfonate During Pregnancy in Rat and Mouse. I: Maternal and Prenatal Evaluations. Toxicol. Sci. 74(2):369-381. ATTACHMENT TO LETTER OF May 11,2004 3M FLUOROCHEMICAL SUBMISSION Tomy GT, Tittlemier SA, Palace VP, Budakowski WR, Braekevelt E, Brinkworth L, and Friesen K (2004). Biotransformation of N-Ethyl Perfluorooctanesulfonamide by Rainbow Trout (Onchorhynchus mykiss) Liver Microsomes. Environ. Sci. Technol. 38(3):758-762. Urata, Shingo, T. Uchimaru, A. K. Chandra, A. Takada, and A. Sekiya. C-H Bond Dissociation Enthalpies of Fluorinated Formates and Estimation of Their Rate Constants for the Reactions with OH Radicals: A DFT Study. DOI Wiley Periodicals, Inc. 10.1002/kin. Van de Vijer KI, Hoff PT, Das K, Van Dongen W, Esmans EL, Jauniaux T, Bouquegneau JM, Blust R, and De Coen W (2003). Perfluorinated Chemicals Infiltrate Ocean Waters: Link between Exposure Levels and Stable Isotope Ratios in Marine Mammals. Environ. Sci. Technol. 37(24):5545-5550. Xie Y, Yang Q, Messing Eriksson A, Nelson BD, and DePierre JW (2002). Characterization of the Adipose Tissue Atrophy Induced by Peroxisome Proliferators In Mice. Lipids 37:139-146. Xie Y, Yang Q, Nelson DB, DePierre JW (2003). The Relationship Between Liver Peroxisome Proliferation and Adipose Tissue Atrophy Induced by Peroxisome Proliferator Exposure and Withdrawal in Mice. Biochemical Pharmacology 66(5):749-756. Yang Q, Abedi-Valugerdi M, Xie Y, Zhao X-Y, Mller G, Nelson BD, and DePierre JW (2002). Potent Suppression Of The Adaptive Immune Response In Mice Upon Dietary Exposure to the Potent Peroxisome Proliferator, Perfluorooctanoic Acid. International Immunopharmacology 2:389-397. Yang Q, Xie Y, and DePierre JW (2000). Effects Of Peroxisome Proliferators on the Thymus and Spleen of Mice. Clinical and Experimental Immunology 122:219-226. Yang Q, Xie Y, Messing Eriksson A, Nelson BD, and DePierre JW (2001). Further Evidence for the Involvement of Inhibition of Cell Proliferation and Development in the Thymic and Splenic Atrophy Induced by the Peroxisome Proliferator Perfluorooctanoic Acid in Mice. Biochem. Pharmacol. 62:1133-1140. Yang Q, Xie Y., Alexsson SEH, Nelson BD, and DePierre JW (2002). Involvement of the Peroxisome Proliferator-Activated Receptor Alpha in the Immunomodulation Caused by Peroxisome Proliferators in Mice. Biochem. Pharmacol. 63:1893-1900.