239
Views
50
CrossRef citations to date
0
Altmetric
Research Article

O-Phenylphenol and its Sodium and Potassium Salts: A Toxicological Assessment

, , , , &
Pages 551-626 | Published online: 29 Sep 2008

References

  • Adams, R.M. Allergic contact dermatitis due to o- phenylphenol. Cont. Derm. 7, 332, 1981.
  • Andersen, K.E. and Hamann, K. The sensitizing potential of metalworking fluid biocides (phenolic and thiazolic compounds) in the guinea-pig maximization test in relation to patch-test reactivity in eczema patients. Food Chem. Toxicol. 22, 655–660, 1984.
  • Appel, K.E. The carcinogenicity of the biocide ortho- phenylphenol. Arch. Toxicol. 74, 61–71, 2000.
  • Bajaj, K.L., Miller, I.R., Bhatia, L.S. Metabolism of 2– hydroxybiphenyl and 4–hydroxybiphenyl in albino mice. Indian J. Exp. Biol. 14, 329–331, 1976.
  • Balakrishnan, S., Uppala, P.T., Rupa, D.S., Hasegawa, L., Eastmond, D.A. Detection of micronuclei, cell prolif- eration and hyperploidy in bladder epithelial cells of rats treated with o-phenylphenol. Mutagenesis 17, 89–93, 2002.
  • Bartels, M.J. and McNett, D.A. Qantitation of ortho- phenylphenol metabolites in rat urine samples from a p-postlabeling study. Dow Chemical, Report No. K-001024–062, 1996.
  • Bartels, M.J., Brzak, K.A., McNett, D.A., Shabrang, S.N. Ortho-phenylphenol (OPP): limited metabolism study in human. Dow Chemical, Report No. K-0011024– 059, 1997.
  • Bartels, M.J., McNett, D.A., Timchalk, C., Mendrala, A.L., Christenson, W.R., Sangha, G.K., Brzak, K.A., Shabrang, S.N. Comparative metabolism of ortho- phenylphenol in mouse, rat and man. Xenobiotica 28, 579–594, 1998.
  • Berdasco, N.M. Orthophenylphenol: dermal sensitization potential in the Hartley albino guinea pig. Dow Chemi- cal, Report No. K-001204–048, 1991.
  • Blair, R.M., Fang, H., Branham, W.S., Hass, B.S., Dial, S.L., Moland, C.L., Tong, W., Shi, L., Perkins, R., Sheehan, D.M. The estrogen receptor relative binding activities of 188 natural and xenochemicals: structural diversity of ligands. Toxicol. Sci. 54, 138–153, 2000.
  • Bomhard, E. O-Phenylphenol Kaliumsalz - Untersuchungen zur akuten oralen Toxizitaet an maennlichen und weiblichen Wistar-Ratten. BayerAG, Report No. 17260, 1988.
  • Bomhard, E. Preventol O extra (Schuppen) - Untersuchungen zur akuten dermalen Toxizitaet an maennlichen und weiblichen Wistar-Ratten. Bayer AG, Report No. 19831, 1991a.
  • Bomhard, E. O-Phenylphenol Kaliumsalz - Untersuchungen zur akuten dermalen Toxizitaet an maennlichen und weiblichen Wistar-Ratten. BayerAG, Report No. 20817, 1991b.
  • Boutwell, R.K. and Bosch, D.K. The tumor-promoting ac- tion of phenol and related compounds for mouse skin. Cancer Res. 19, 413–424, 1959.
  • Brasch, J., Henseler, T., Frosch, P. Patch test reactions to a preliminary preservative series. Dermatosen 41, 71–76, 1993.
  • Brendler, S.Y. Preventol O extra: mutagenicity study for the detection of induced forward mutations in the CHO- HGPRT assay in vitro. Bayer AG, Report No. 21278, 1992.
  • Brendler-Schwaab, S.Y. Preventol O extra: comet assay in vivo in mouse liver and kidney. BayerAG, Report No. 30130, 2000.
  • Burke, M.D. and Bridges, W. Biphenyl hydroxylations and spectrally apparent interactions with liver microsomes from hamsters pre-treated with phenobarbitone and 3–methyl-cholanthrene. Xenobiotica 5, 357–376, 1975.
  • Carreon, R.E. and New, M.A. Dowicide 1: acute percutane- ous absorption potential. Dow Chemical, Report No. K-1024–(37), 1981.
  • Christenson, W.R., Wahle, B.S., Bartels, M.J., Cohen, S.M. Technical grade ortho-phenylphenol: a 32–P- postlabeling study to examine the potential for the formation of DNA adducts in the urinary bladder of the male rat. Bayer Corp., Report No. 94–972–AV, 1996b.
  • Cline, J.C., and Mcmahon, R.E. Detection of chemical mu- tagens. Use of concentration gradient plates in a high capacity screen. Res. Comm. Chem. Pathol. Pharmacol. 16, 523–533, 1977.
  • Cnubben, N.H.P., Elliott, G.R., Hakkert, B.C., Meuling, W.J.A., van de Sandt, J.J.M. Comparative in vitro-in vivo percutaneous penetration of the fungicide ortho- phenylphenol. Regul. Toxicol. Pharmacol. 35, 198–208, 2002.
  • Cohen, S.M., Cano, M., Earl, R.A., Carson, S.D., Garland, E.M. A proposed role for silicates and protein in the proliferative effects of saccharin on the male rat urothelium. Carcinogenesis 12, 1551–1555, 1991.
  • Cohen, S.M. Role of urinary physiology and chemistry in bladder carcinogenesis. Food Chem. Toxicol. 33, 715– 730, 1995.
  • Cohen, S.M., Cano, M., Anderson, T., Garland, E.M. Exten- sive handling of rats leads to mild urinary bladder hyperplasia. Toxicol. Pathol. 24, 251–257, 1996.
  • Cohen, S.M. Urinary bladder carcinogenesis. Toxicol. Pathol. 26, 121–127, 1998.
  • Cosse, P.F., Stebbins, K.E., Stott, W.T., Johnson, K.A., Atkin, L. Ortho-phenylphenol: palatability/probe, four-week and one-year oral toxicity studies in beagle dogs. Dow Chemical, Report No. K-001024–039, 1990.
  • Eastmond, D.A. Induction of micronuclei and aneuploidy by the quinone-forming agents benzene and o-phenylphenol. Toxicol. Letters 67, 105–118, 1993.
  • Eastmond, D.A. Personal communication, March 2002.
  • Eigenberg, D.A. Two-generation dietary reproduction study in rats using ortho-phenylphenol. Mobay Corp., Re- port No. 85–671–02, 1990.
  • Eigenberg, D.A. and Lake, S.G. A two-generation dietary reproduction study in Sprague-Dawley rats using tech- nical grade ortho-phenylphenol. Bayer Corp., File No. 7788, 1995.
  • Eigenberg, D.A., Lake, S.G., Sangha, G.K., Thyssen, J.H. Evaluation of the reproductive toxicity of o- phenylphenol (OPP) in a two-generation rat reproductive toxicity study. Fundam. Appl. Toxicol. 36, 356, 1997 (abstract).
  • Ernst, W. Umwandlung und Ausscheidung von 2– Hydroxydiphenyl bei der Ratte. Arzneim. Forsch. 15, 632–636, 1965.
  • EPA – Environmental Protection Agency. Special report on environmental endocrine disruption: an effects assess- ment and analysis. Washington D.C., 1997.
  • EPA – Environmental Protection Agency. Notice: endocrine disruptor screening program [OPPTS-42206; FRL- 6021–3]. Federal Register: August 11, 63, No. 154, 42852–42855, 1998.
  • EU – MRC Institute for Environment and Health. European workshop on the impact of endocrine disrupters on human health and wildlife. Reports of Proceedings, Weybrigde, U.K.; EUR 17549, 1996.
  • EU – European Commission DG Env. Towards the estab- lishment of a priority list of substances for further evaluation of their role in endocrine disruption. June 21, 2000.
  • FAO/WHO - Plant Production and Protection Paper, No. 68, 37, 1985.
  • FAO/WHO - Plant Production and Protection Paper, No. 102, 49, 1990.
  • FAO/WHO - Plant Production and Protection Paper, No. 153, 169, 1999.
  • Freyberger, A. O-phenylphenol - interactions of o- phenylphenol (OPP) and its metabolites with microso- mal prostaglandin-H-synthase: possible implications for OPP-induced tumor formation in the rat urinary bladder. Bayer AG, Report No. 22788, 1994.
  • Freyberger, A. and Degen, S.A. Inhibition of prostaglandin- H-synthase by o-phenylphenol and its metabolites. Arch. Toxicol. 72, 637–644, 1998.
  • Fujii, T. and Hiraga, K. Carcinogenicity testing of sodium orthophenylphenate in F344 rats. J. Saitana Med. School 12, 277–287, 1985.
  • Fujii, T., Mikuriya, H., Kamiya, N., Hiraga, K. Enhancing effect of thiabendazole on urinary bladder carcino- genesis induced by sodium o-phenylphenate in F344 rats. Food Chem. Toxicol. 24, 207–211, 1986a.
  • Fujii, T., Mikuriya, H., Hayashida, S., Hiraga, K. Enhancing effects of thiabendazole on urinary bladder carcino- genesis in rats fed diet containing low-dose of sodium o-phenylphenate for 13 week. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 37, 411–414, 1986b.
  • Fujii, T., Nakamura, K., Hiraga, K. Effects of PH on the carcinogenicity of o-phenylphenol and sodium o- phenylphenate in the rat urinary bladder. Food Chem. Toxicol. 25, 359–362, 1987.
  • Fujii, T., Mikuriya, H., Yoneyama, M., Yano, N., Yuzawa, K., Nagasawa, A., Sasaki, M. Dietary toxicity test of o-phenylphenol and sodium hydrogencarbonate by simultaneous administration to mice for 52 weeks. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 40, 298–306, 1989a.
  • Fujii, T., Mikuriya, H., Yoneyama, M., Yano, N., Yuzawa, K., Nagasawa, A., Sasaki, M. Dietary toxicity of o-phenylphenol, thiabendazole, and sodium hydrogencarbonate by simultaneous administration to mice for 52 weeks. Ann. Rep. To- kyo Metr. Res. Lab. P.H. 40, 307–315, 1989b.
  • Fujii, T., Mikuriya, H., Yano, N., Yuzawa, K., Nagasawa, A., Fukumori, N., Tada, Y., Sasaki, M. Subacute tox- icity test of ceramics by gavage to rats and influence of ceramics on urinary bladder carcinogenesis induced by o-phenylphenol. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 41, 233–244, 1990.
  • Fujii, T., Mikuriya, H., Sasaki, M. Chronic oral toxicity and carcinogenicity study of thiobendazole in rats. Food Chem. Toxicol. 29, 771–775, 1991.
  • Fujita, H., Kojima, A., Sasaki, M., Hiraga, K. Assay of host- mediated mutagenicity by S. typhimurium and E. coli in rats fed sodium o-phenylphenate (OPP-Na). Ann. Rep. Tokyo Metr. Res. Lab. P.H. 35, 431–435, 1984.
  • Fujita, h., Kojima, A., Sasaki, M., Hiraga, K. Mutagenicity test of antioxidants and fungicides with Salmonella typhimurium TA97a and TA102. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 36, 413–417, 1985.
  • Fukumori, N. and Sasaki, M. Comparison of ultrastructural changes between o-phenylphenol (OPP) – kidney damage and sucrose-nephrosis in the rat proximal tubules. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 37, 399–406, 1986.
  • Fukumori, N., Sasaki, M., Hiraga, K. Ultrastructural alter- ations of hepatocytes in male rats fed with sodium o- phenylphenate (OPP-Na). Ann. Rep. Tokyo Metr. Res. Lab. P.H. 34, 329–336, 1983.
  • Fukumori, N., Sasaki, M., Hiraga, K. Effects of sodium o- phenylphenate (OPP-Na) on ultra-structure of bladder epithelium in rats. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 35, 416–424, 1984.
  • Fukumori, N. and Sasaki, M. Ultrastructural alterations of the proximal tubules induced by o-phenylphenol (OPP) in the rat kidney. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 36, 400–408, 1985.
  • Fukushima, S., Hasegawa, R., Kurata, Y., Okuda, M., Hatano, A., Ito, N. Histopathological and ultrastructural analy- sis of urinary bladder lesions in animals induced by sodium o-phenylphenate. Proc. Jap. Cancer Ass., 41 Ann. Mtg. 314, 1982 (abstract).
  • Fukushima, S., Kurata, Y., Shibata, M.A., Ikawa, E., Ito, N. Promoting effect of sodium o-phenylphenate and o- phenyl-phenol on two-stage urinary bladder carcino- genesis in rats. Jpn. J. Cancer Res. (Gann) 74, 625– 632, 1983.
  • Fukushima, S., Kurata, Y., Ogiso, T., Okuda, M., Miyata, Y., Ito, N. Pathological analysis of the carcinogenicity of sodium o-phenylphenate and o-phenylphenol. Oncol- ogy 42, 304–311, 1985.
  • Fukushima, S., Shibata, M.A., Kurata, Y., Tamano, S., Masui, T. Changes in the urine and scanning electron micro- scopically observed appearance of the rat bladder fol- lowing treatment with tumor promoters. Jpn. J. Can- cer Res. (Gann) 77, 1074–1082, 1986.
  • Fukushima, S., Inoue, T., Uwagawa, S., Shibata, M.A., Ito, N. Co-carcinogenic effects of NaHCO3 on o- phenylphenol-induced rat bladder carcinogenesis. Carcinogenesis 10, 1635–1640, 1989.
  • Funahashi, M., Arai, M., Takahashi, H., Hibino, T. Morpho- logical characteristics of rabbit urinary bladder tu- mors induced by BBN and OPP-Na. Fujita Gakuen Hoken Eisei Daigaku, Toyoaki 11, 187–189, 1987.
  • Gaches, C.G. Woodworm and the bladder. Proc. R. Soc. Med. 68, 525–527, 1975.
  • Gbodi, T.A. and Oehme, F.W. The fate of phenol, o- phenylphenol and disophenol in rats. Toxicol. Appl. Pharmacol. 45, 223, 1978 (abstract).
  • Geier, J., Kleinhans, D., Peters, K.-P. Kontaktallergien durch industriell verwendete Biozide. Dermatosen/Occup. Environ. 44, 154–159, 1996.
  • Gilbert, K.S. Dowicidetm1 antimicrobial; primary dermal ir- ritation study in New Zealand White rabbits. Dow Chemical, Report No. K-001024–057b, 1994a.
  • Gilbert, K.S. Dowicidetm1 antimicrobial; dermal sensitiza- tion potential in the Hartley albino guinea pig. Dow Chemical, Report No. K-001024–057e, 1994b.
  • Gilbert; K.S. Dowicide A antimicrobial: dermal sensitiza- tion potential in Hartley albino guinea pigs. Dow Chemical, Report No. K-0011025–014e, 1994c.
  • Gilbert, K.S. and Crissman, J.W. Dowicidetm1 antimicrobial; acute oral toxicity study in Fischer 344 rats. Dow Chemical, Report No. K-001024–057a, 1994.
  • Gilbert, K.S. and Stebbins, K.E. Dowicide A antimicrobial: acute oral toxicity study in Fischer 344 rats. Dow Chemical, Report No. K-001025–014a, 1994.
  • Goh, C.L. and Yuen, R. A study of occupational skin disease in the metal industry (1986–1990). Ann. Acad. Med. Singapore 23, 639–644, 1994.
  • Grattan, C.E.H., English, J.S.C., Foulds, I.S., Rycroft, R.J.G. Cutting fluid dermatitis. Cont. Derm. 20, 372–376, 1989.
  • Grether, T., Brunn, H., Laib, R.J. 32P-postlabelling method as a sensitive indicator for analysis of genotoxicity of biphenyl derivatives. Arch. Toxicol. 63, 423–424, 1989a.
  • Grether, T., Rogiers, V., Laib, R.J. Analysis of genotoxicity of hydroxylated and chlorinated biphenyl derivatives in vitro and in vivo. Naunyn-Schmiedeberg’s Arch. Pharmacol. Suppl. to Vol. 339, r 23, 1989b (abstract).
  • Groot, A.P. de, Feron, V.J., Immel, H., Rats R. Induction of hyperplasia in the bladder epithelium of rats by a dietary excess of acid or base: implications for toxic- ity/carcinogenicity testing. Food Chem. Toxicol. 26, 425–434, 1988.
  • Gucklhorn, I.R. Antimicrobials in cosmetics. Manufacturing Chemist Aerosol News 40, 23–30, 1969.
  • Halpaap-Wood, K., Horning, E.C., Horning, M.G. The ef- fect of 3–methylcholanthrene, Aroclor 1254, and phe- nobarbital induction on the metabolism of biphenyl by rat and mouse 9000g supernatant liver fractions. Drug Metab. Disp. 9, 103–107, 1981.
  • Hagedorn-Leweke, U. and Lippold, B.C. Absorption of sun- screens and other compounds through human skin in vivo: derivation of a method to predict maximum fluxes. Pharm. Res. 12, 1354–1360, 1995.
  • Hagiwara, A., Shibata, M., Hirose, M., Fukushima, S., Ito, N. Long-term toxicity and carcinogenicity study of sodium o-phenylphenate in B6C3F1 mice. Food Chem. Toxicol. 22, 809–814, 1984.
  • Hanada, S. Studies on food additives diphenyl and o- phenylphenol from standpoint of public health. II. Toxicological studies of diphenyl and o-phenylphenol. J. Nagoya City Univ. Med. Ass. 28, 983–995,1977.
  • Harbell, J.W. O-phenylphenol - mouse lymphoma assay (L5178Y TK +/-). Microbiological Associates Inc., (Lab. Study No. ML-NCI #246), 1989a.
  • Harbell, J.W. O-phenylphenol, sodium salt tetrahydrate - mouse lymphoma assay (L5178Y TK +/-). Microbio- logical Associates Inc., (Lab. Study No. ML-NCI #247), 1989b.
  • Harke, H.-P. and Klein, H. Zur Frage der Resorption von 2–Phenylphenol aus waschenden Haende- Desinfektionsmitteln. Zbl. Bakt. Hyg., I. Abt. Orig. B 174, 274–278, 1981.
  • Hasegawa, R. and Cohen, S.M. The effect of different salts of saccharin on the rat urinary bladder. Cancer Letters 30, 261–268, 1986.
  • Hasegawa, R., Kaji, N., Furukawa, F., Fukuoka, M., Kuzunishi, K., Takahashi, M., Hayashi, Y. Investiga- tion of bladder cancer initiation effects of OPP-Na metabolites in rat urine. Proc. J. Cancer Assoc. 91, 1988, 235 (abstract).
  • Hasegawa, R., Furukawa, F., Toyoda, K., Sato, H., Shimoji, N., Takahashi, M., Hayashi, Y. In situ freezing of the urinary bladder: a trigger of rapid development of sodium-o-phenyl-phenate-induced urinary bladder tumors in the rat. Carcinogenesis 10, 571–575, 1989a. Hasegawa, R., Nakaji, Y., Kurokawa, Y., Tobe, M. Acute toxicity tests on 113 environmental chemicals. Sci. Rep. Inst. Tohuku Univ. 36, 1–4, 1989b.
  • Hasegawa, R., Furukawa, F., Toyoda, K., Sato, H., Takahashi, M., Hayashi, Y. Urothelial damage and tumor initia- tion by urinary metabolites of sodium-o-phenylphenate in the urinary bladder of female rats. Jpn. J. Cancer Res. 81, 483–488, 1990a.
  • Hasegawa, R., Takahashi, S., Asamoto, M., Shirai, T., Fukushima, S. Species differences in sodium o- phenylphenate induction of urinary bladder lesions. Cancer Letters 50, 87–91, 1990b.
  • Hasegawa, R., Fukuoka, M., Takahashi, T., Yamamoto, A., Yamaguchi, S., Shibata, M.A., Tanaka, A., Fukushima, S. Sex differences in o-phenylphenol and sodium o- phenylphenate rat urinary bladder carcinogenesis: uri- nary metabolites and electrolytes under conditions of aciduria and alkalinuria. Jpn. J. Cancer Res. 82, 657– 664, 1991.
  • Haworth, S., Lawlor, T., Mortelmans, K., Speck, W., Zeiger, E. Salmonella mutagenicity test results for 250 chemi- cals. Environ. Mutagen. 5 (Suppl 1), 3–142, 1983.
  • Henschke, P., Almstadt, E., Lüttgert, S., Appel, K.E. Me- tabolites of the biocide o-phenyl-phenol generate oxi- dative DNA lesions in V79 cells. Arch. Toxicol. 73, 607–610, 2000.
  • Hiraga, K. and Fujii, T. Induction of tumours of the urinary system in F344 rats by dietary administration of so- dium o-phenylphenate. Food Cosmet. Toxicol. 19, 303–310, 1981.
  • Hiraga, K. and Fujii, T. Induction of tumours of the urinary bladder in F344 rats by dietary administration of o- phenylphenol. Food Chem. Toxicol. 22, 865–870, 1984.
  • Hirayama, T., Nohara, M., Shindo, H., Fukui, S. Mutagenic- ity assays of photochemical reaction products of bi- phenyl (BP) and o-phenylphenol (OPP) with NOx. Chemosphere 10, 223–228, 1981.
  • Hodge, H.C., Maynard, E.A., Blanchet, H.J., Spencer, H.C., Rowe, V.K. Toxicological studies of orthophenylphenol (Dowicide 1). J. Pharmacol. Exp. Ther. 104, 202–210, 1952.
  • Honma, Y., Kakizoe, T., Komatsu, H., Niijima, T., Sugimura, T. Increased agglutinability of bladder epithelial cells by concanavalin A in rats fed several biphenyl deriva- tives. J. Cancer Res. Clin. Oncol. 106, 176–178, 1983.
  • Horvath, E., Levay, G., Pongracz, K., Bodell, W.J. Peroxidative activation of ortho-phenylhydroquinone leads to the formation of DNA adducts in HL-60 cells. Carcinogenesis 13, 1937–1939, 1992.
  • IARC: Sex hormones (II). Monographs on the evaluation of carcinogenic risks of chemicals to humans. 21, 1979. IARC: Ortho-phenylphenol and its sodium salt. Monographs on the evaluation of carcinogenic risks of chemicals to humans, miscellaneous pesticides. 30, 329–344, 1983.
  • IARC: Ortho-phenylphenol and its sodium salt. Monographs on the evaluation of carcinogenic risks to humans. 73, 451–480, 1999.
  • Iguchi, S., Tayama, K., Hiraga, K. Subacute toxicity of sodium o-phenylphenate by food administration to rats. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 30, 67–79, 1979.
  • Iguchi, S., Takahashi H., Fugii, T., Fukumori, N., Mikuriya, H., Tada, Y., Yuzawa, K., Hiraga, K. Subchronic toxicity of o-phenylphenol (OPP) by food administra- tion to rats. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 35, 407–415, 1984.
  • Innes, J.R.M., Ulland, B.M., Valerio, M.G., Petrucelli, L., Fishbein, L., Hart, E.R., Palotta, A.J., Bates, R.R., Falk, H.L., Gart, J.J., Klein, M., Mitchell, I., Peters, J. Bioassay of pesticides and industrial chemicals for tumorigenicity in mice: a preliminary note. J. Natl. Cancer Inst. 42, 1101–1114, 1969.
  • Inoue, T., Shibata, M., Uwa, K., Asamoto, S., Osaki, T., Fukushima, A. Synergistic effect of NaHCO3 on rat bladder carcinogenesis by OPP. Proc. J. Cancer Assoc., p. 91, 1988 (abstract).
  • Inoue, S., Yamamoto, K., Kawanishi, S. DNA damage in- duced by metabolites of o-phenylphenol in the pres- ence of copper(II) ions. Chem. Res. Toxicol. 3, 144– 149, 1990.
  • Inoue, T. Pathological studies on urinary bladder carcino- genesis of o-phenylphenol and its sodium salt in male rats. J. Nagoya City Univ. Med. Assoc. 44, 463–478, 1993.
  • Inui, N., Nishi, Y., Iwata, K. Dose-response relationships for mutations induced in embryo cells after treatment of pregnant hamsters. In: Problems of Threshold in Chemical Mutagenesis. Eds.: Tazima, Y. et al., 35– 39, 1984.
  • Ishidate, M., Yoshikawa, K., Sofuni, T., Mutagenicity tests on OPP, OPP-sodium salt, and their possible metabo- lites. Unpublished report from the Division of Mu- tagenesis, Biological Safety Research Center, National Institute of Hygienic Sciences, Tokyo, Japan, 1983. Submitted to WHO by Dow Chemical Co., Midland, MT., USA. Cited according to: FAO/ WHO - Evalu- ations 1985, II – Toxicology.
  • Ishidate, M., Sofuni, T., Yoshikawa, K., Hayashi, M., Nohmi, T., Sawada, M., Matsuoka, A. Primary mutagenicity screening of food additives currently used in Japan. Food Chem. Toxic. 22, 623–636, 1984.
  • Ishidate, M. (ed.) Chromosomal aberration test in vitro. L.I.C., Inc., Tokyo, 1987.
  • Ishidate, M., Harnois, M.C., Sofuni, T. A comparative analy- sis of data on the clastogenicity of 951 chemical sub- stances tested in mammalian cell cultures. Mutat. Res. 195, 151–213, 1988.
  • Ito, K., Nishitani, K., Hara, I. A study of cases of leucomelanodermatosis due to phenyl-phenol com- pounds. Bull. Pharm. Res. Institute 76, 5–13, 1968.
  • Ito, N., Fukushima, S., Shirai, T., Hagiwara, A., Imaida, K. Drugs, food additives and natural products as promot- ers in rat urinary bladder carcinogenesis. IARC Sci. Publ. 56, 399–407, 1984.
  • Ito, N., Hasegawa, R., Imaida, K., Takahashi, S., Shirai, T. Medium-term rat liver bioassay for rapid detection of carcinogens and modifiers of hepatocarcinogenesis. Drug Metab. Rev. 26, 431–442, 1994.
  • Itoh, S., Ueda, H., Naasaka, T., Sumitomo, H. Evaluating variation of estrogenic effect by drinking water chlo- rination with the MVLN assay. Water Sci. Technol. 42, 61–69, 2000.
  • JEFCA (Joint FAO/WHO Expert Committee on Food Addi- tives) Fifty-fifth Meeting, Geneva, 6–15 June 2000. JMPR, Pesticide Residues in Food – 1985 Report on the joint meeting of the FAO panel of experts on pesticide residues in food and the environment and a WHO expert group on pesticide residues. Geneva, 37, 1985.
  • John, J.A., Murray, F.J., Rao, K.S., Schwetz, B.A. Terato- logical evaluation of orthophenylphenol in rats. Fundam. Appl. Toxicol. 1, 282–285, 1981.
  • Kabashima, J. and Nakao, T. Effect of sodium o- phenylphenate (OPP-Na) on acid phosphatase in rat urine. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 32, 61– 64, 1981.
  • Kabashima, J., Ichikawa, H., Nakao, T. Effect of sodium o- phenylphenol (OPP-Na) on acid phosphatase in rat urine. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 34, 309– 311, 1983.
  • Kahn, G. Depigmentation caused by phenolic detergent ger- micides. Arch. Dermatol. 102, 177–187, 1970.
  • Kaneda, M., Teramoto, S., Shingu, A., Shirasu, Y. Teratoge- nicity and dominant-lethal studies with o-phenylphenol. J. Pesticide Sci. 3, 365–370, 1978.
  • Kato, M. Reverse mutation assay of Preventol OF using Salmonella typhimurium and Escherichia coli. Re- search Lab., JBC. Inc., Test No. 1097, 1989.
  • Kawachi, T., Yahagi, T., Kada, T., Tazima, Y., Ishidate, M., Sasaki, M., Sugiyama, T. Cooperative programme on short-term assays for carcinogenicity in Japan. IARC Scientific Publ. 27, 323–330, 1981.
  • Keller, B.J., Marsman, D.S., Popp, J.A., Thursman, R.G. Several nongenotoxic carcinogens uncouple mitochon- drial oxidative phosphorilation. Biochim. Biophys. Acta 1102, 237–244, 1992.
  • Kobayashi, H., Kabashima, J., Nakao, T. Effect of sodium o- phenylphenate (OPP-Na) on alkaline phosphatase in rat urine. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 33, 467–469, 1982.
  • Kojima, A., Hiraga, K. Mutagenicity of citrus fungicides in microbial system. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 29, 83–85, 1978.
  • Kojima, A., Fujita, H., Hiraga, K. Mutagenicity of o- phenylphenol (OPP) in the microbial system. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 34, 319–324, 1983.
  • Kojima, K., Kanazawa, H.J.L., Ono, H. Long-term effects of parathion, o-phenylphenol and penicillin-g potassium on immunological properties and intestinal flora in BALB/C mice. The international congress of toxicol- ogy VII, July 2–6, 12, 1995 (abstract).
  • Kolachana, P., Subrahmanyam, V.V., Eastmond, D.A., Smith, M.T. Metabolism of phenylhydroquinone by prostag- landin (H) synthase: possible implications in o- phenylphenol carcinogenesis. Carcinogenesis 12, 145– 149, 1991.
  • Kwok, E.S.C., Eastmond, D.A. Effects of pH on nonenzy- matic oxidation of phenyl-hydroquinone: potential role in urinary bladder carcinogenesis induced by o- phenylphenol in Fischer 344 rats. Chem. Res. Toxicol. 10, 742–749, 1997.
  • Kwok, E.S.C., Buchholz, B.A., Vogel, J.S., Turteltaub, K.W., Eastmond, D.A. Dose-dependent binding of ortho- phenylphenol to protein but not DNA in the urinary bladder of male F344 rats. Toxicol. Appl. Pharmacol. 159, 18–24, 1999.
  • Lambert, A.C. Mechanisms of genotoxicity induced by the ortho-phenylphenol metabolites phenylhydroquinone and phenylbenzoquinone. Master Thesis, Univ. of California Riverside; 1992.
  • Lambert, A.C. and Eastmond, D.A. Genotoxic effects of the o-phenylphenol metabolites phenylhydroquinone and phenylbenzo-quinone in V79 cells. Mutat. Res. 322, 243–256, 1994.
  • Landry, T.D., Stebbins, K.E., Battjes, J.E. Ortho- phenylphenol: acute aerosol inhalation toxicity study in Fischer 344 rats. Dow Chemical, Report No. K- 001024–049, 1992.
  • La Via, M.F. and La Via, D.S. Phenol derivatives are immunodepressive in mice. Drug Chem. Toxicol. 2, 167–177, 1979.
  • La Via, M.F., Loose, L.D., La Via, D.S., Silberman, M.s. The immunodepressive effect of phenol derivatives. Adv. Exp. Med. Biol. 121, 523–538, 1979.
  • Loeser, E. Preventol O extra: Untersuchungen zur akuten oralen Toxizitaet an maennlichen Wistar-Ratten. Bayer AG, Report 1981.
  • Luster, M.I., Dean, J.H., Boorman, G.A., Archer, D.L., Lauer, L., Lawson, L.D., Moore, J.A., Wilson, R.E. The effects of orthophenylphenol, tris(2,3–dichloropropyl)-phosphate, and cyclophosphamide on the immune system and host susceptibility of mice following subchronic exposure. Toxicol. Appl. Pharmacol. 58, 252–261, 1981.
  • Luster, M.I., Portier, C., Pait, D.G., White, K.L., Gennings, C., Munson, A.E., Rosenthal, G.J. Risk assessment in immunotoxicology. I. Sensitivity and predictability of immune tests. Fund. Appl. Toxicol. 18, 200–210, 1992. Luster, M.I., Portier, C., Pait, D.G., Rosenthal, G.J., Germolec, D.R., Corsini, E., Blaylock, B.L., Pollock, P., Kouchi,
  • Y., Craig, W., White, K.L., Munson, A., Comment, C.E. Risk assessment in immunotoxicology. II. Rela- tionship between immune and host resistance tests. Fund. Appl. Toxicol. 21, 71–82, 1993.
  • MacIntosh, F.C. The toxicity of diphenyl and o-phenylphenol. Analyst 70, 334–335, 1945.
  • Maertins, T. Preventol ON: Untersuchungen zum Reiz-/ Aetzpotential an Haut und Auge (Kaninchen) nach OECD-Richtlinie No. 404 und 405. Bayer AG Report- No. 16951, 1988a.
  • Maertins, T. Bayer AG, letter report, 1988b.
  • McMahon, R.E., Cline, J.C., Thompson, C.Z. Assay of 855 test chemicals in ten tester strains using a new modi- fication of the Ames test for bacterial mutagens. Can- cer Res. 39, 682–693, 1979.
  • McNett, D.A., Timchalk, C., Mendrala, A.L. Ortho- phenylphenol: metabolism of 14C-labelled OPP in B6C3F1 mice and Fischer 344 rats. Dow Chemical, Report No. K-001024–060, 1997.
  • Meiss, R., Heinrich, U., Himmels, S., Themann, H. A mor- phometric study of o-phenylphenol induced alterations in the rat liver following oral or subcutaneous admin- istration. Wissenschaft und Umwelt, 4, 257–261, 1981.
  • Mihail, F., Kimmerle, G. Preventol O und Preventol ON: Bestimmung der Inhalations-toxizitaet. Bayer AG, Report 1977.
  • Mikuriya, H., Fujii, T., Hayashida, S., Kamiya, N., Hiraga, K. Examination of dose-related enhancing effects of thiabendazole on urinary bladder carcinogenesis by sodium o-phenylphenate in rats. Ann. Rep. Tokyo. Metr. Res. Lab. P.H. 37, 407–410, 1986.
  • Mikuriya, H., Fujii, T., Yoneyama, M., Yano, N., Yuzawa, K., Nagasawa, A., Sasaki, M. Toxicity of o- phenylphenol by dietary administration to mice for 52 weeks. Ann. Rep. Tokyo. Metr. Res. Lab. P.H. 40, 281–288, 1989a.
  • Mikuriya, H., Fujii, T., Yoneyama, M., Yano, N., Yuzawa, K., Nagasawa, A., Sasaki, M. Toxicity of thiabenda- zole and o-phenylphenol by simultaneous administra- tion to mice for 52 weeks. Ann. Rep. Tokyo. Metr. Res. Lab. P.H. 40, 289–297, 1989b.
  • Mikuriya, H., Fujii, T., Yoneyama, M., Shimada, T., Sasaki, M. Toxicity of thiabendazole and o-phenylphenol by simultaneous administration to rats for six weeks. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 41, 245–254, 1990.
  • Mikuriya, H., Fujii, T., Sasaki, M. Chronic toxicity test of o- phenylphenol and thiabendazole by simultaneous administraton to mice. Shokuhin Eiseigaku Zsasshi 33, 274–282, 1992.
  • Miller, D., Wheals, B.B., Beresford, N., Sumpter, J.P. Estro- genic activity of phenolic additives determined by an in vitro yeast bioassay. Environ. Health Perspect. 109, 133–138, 2001.
  • Miyata, Y., Fukushima, S., Hirose, M., Masui, T., Ito, N. Short-term screening of promoters of bladder carcino- genesis in n-butyl-n-(4–hydoxybutyl)nitrosamine-ini- tiated; unilaterally ureter-ligated rats. Jpn. J. Cancer Res. 76, 828–834, 1985.
  • Mori, S., Kurata, Y., Takeuchi, Y., Toyama, M., Makino, M., Fukushima, S. Influences of strain and diet on the promoting effects of sodium L-ascorbate in two-stage urinary bladder carcinogenesis in rats. Cancer Res. 47, 3492–3495, 1987.
  • Morimoto, K., Fukuoka, M., Hasegawa, R., Tanaka, A., Takahashi, A., Hayashi, Y. DNA damage in uri- nary bladder epithelium of male F344 rats treated with 2–phenyl-1,4–benzoquinone, one of the non- conjugated urinary metabolites of sodium o- phenylphenate. Jpn. J. Cancer Res. 78, 1027–1030, 1987.
  • Morimoto, K., Sato, M., Fukuoka, M., Hasegawa, R., Takahashi, T., Tsuchiya, T., Tanaka, A., Takahashi, A., Hayashi, Y. Correlation between the DNA dam- age in urinary bladder epithelium and the urinary 2– phenyl-1,4–benzoquinone levels from F344 rats fed sodium o-phenylphenate in the diet. Carcinogenesis 10, 1823–1827, 1989.
  • Moriya, M., Ohta, T., Watanabe, K., Miyazawa, T., Kato, K., Shirasu, Y. Further mutagenicity studies on pesticides in bacterial reversion assay systems. Mutat. Res. 116, 185–216, 1983.
  • Mortelmans, K., Haworth, S., Lawlor, T., Speck, W., Tainer, B., Zeiger, E. Salmonella mutagenicity testing: II. Results from the testing of 270 chemicals. Environ. Mutagen. 8 (Suppl. 7), 1–119, 1986.
  • Morpurgo, G., Bellincampi, D., Gualandi, G., Baldinelli, L., Crescenzi, O.S. Analysis of mitotic nondisjunction with Aspergillus nidulans. Environ. Health Perspect. 31, 81–95, 1979.
  • Murata, M., Moriya, K., Inoue, S., Kawanishi, S. Oxidative damage to cellular and isolated DNA by metabolites of a fungicide ortho-phenylphenol. Carcinogenesis 20, 851–857, 1999.
  • Nagai, F., Nakao, T. Effect of o-phenylphenol sodium salt (OPP-Na) on rats enzymes in vivo. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 32, 57–60, 1981.
  • Nagai, F., Nakao, T. Changes of enzyme activities in rat urine and tissues by administration of different con- centrations of o-phenylphenol sodium salt (OPP-Na) in diet. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 34, 305– 308, 1983.
  • Nagai, F., Nakao, T. Changes in enzyme activities in the urine and tissues of rats fed sodium o-phenylphenate. Food Chem. Toxic. 22, 361–364, 1984.
  • Nagai, F., Ushiyama, K., Satoh, K., Kano, I. Modification of DNA base by OPP and its metabolites. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 39, 292–294, 1988.
  • Nagai, F., Ushiyama, K., Satoh, K., Kano, I. DNA cleavage by phenylhydroquinone: the major metabolite of a fungicide o-phenylphenol. Chem.-Biol. Interactions 76, 163–179, 1990.
  • Nagai, F., Ushiyama, K., Satoh, K., Kasai, H., Kano, I. Formation of 8–hydroxydeoxyguanosine in calf thy- mus DNA treated in vitro with phenylhydroquinone, the major metabolite of o-phenylphenol. Carcinogen- esis 16, 837–840, 1995.
  • Nakagawa, A., Nakao, T., Nakao, M. Altered levels of cyclic nucleotides in F344 rats fed sodium o-phenylphenate. Food Chem. Toxic. 22, 217–221, 1984.
  • Nakagawa, Y., Tayama, S. Effect of buthionine sulfoximine on orthophenylphenol-induced hepato- and nephro- toxic potential in male rats. Arch. Toxicol. 62, 452– 457, 1988.
  • Nakagawa, Y., Tayama, S. Formation of ortho-phenylphenol glutathione conjugates in the rat liver. Xenobiotica 19, 499–507, 1989.
  • Nakagawa, Y., Moldéus, P., Moore, G.A. Cytotoxicity of ortho-phenylphenol in isolated rat hepatocytes. Biochem. Pharmacol. 43, 159–165, 1992a.
  • Nakagawa, Y., Tayama, S., Moldéus, P., Moore, G.A. Rela- tionship between metabolism and cytotoxicity of ortho- phenylphenol in isolated rat hepatocytes. Biochem. Pharmacol. 43, 1431–1437, 1992b.
  • Nakagawa, Y., Tayama, S., Moore, G., Moldéus, P. Cyto- toxic effects of biphenyl and hydroxybiphenyls on isolated rat hepatocytes. Biochem. Pharmacol. 45, 1959–1965, 1993.
  • Nakagawa, Y., Moore, G.A. Cytotoxic effects of postharvest fungicides, ortho-phenylphenol, thiabendazole and imazalil, on isolated rat hepatocytes. Life Sciences 57, 1433–1440, 1995.
  • Nakagawa, Y., Tayama, S. Induction of 8–hydroxy-2´- deoxyguanosine in CHO-KL cells exposed to phenyl- hydroquinone, a metabolite of ortho-phenylphenol. Cancer Lett. 101, 227–232, 1996.
  • Nakamura, K., Iguchi, S., Ikeada, T., Hiraga, K. Subacute toxicity of o-phenylphenol by food administration to male rats. Ann. Rep. Tokyo Metr. Lab. P.H. 32, 33–39, 1981.
  • Nakamura, K., Ikeda, T., Iguchi, S., Hiraga, K. Toxicity of 2–phenylphenol (OPP) by dietary administration to male rats for 91 weeks. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 33, 434–443, 1982.
  • Nakao, T., Ushiyama, K., Kabashima, J., Nagai, F., Nakagawa, A., Ohno, T., Ichikawa, H., Kobayashi, H., Hiraga, K. The metabolic profile of sodium o- phenylphenate after subchronic oral administration to rats. Food Chem. Toxic. 21, 325–329, 1983.
  • Narayan, S., Roy, D. Changes in protein and nonprotein thiol contents in bladder, kidney and liver of mice by the pesticide sodium-o-phenylphenol and their possible role in cellular toxicity. Biochem. Int. 26, 191–198, 1992.
  • Nawai, S., Yoshida, S., Nakao, T., Hiraga, K. Examination of mutagens by induced sister chromatid exchange (SCE): II. Test of two fungicides by induced SCE, in vitro. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 30, 51– 53, 1979.
  • Nawai, S., Yoshida, S., Nakao, T., Hiraga, K. Effect of o- phenylphenol incubated with S-9 mix induced by phenobarbital or 3–methylcholanthrene on chromo- somes in CHO-K1 cells. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 33, 480–483, 1982.
  • Neumann, H.-G., Bitsch, A., Kloehn, P.-C. The dual role of 2–acetylfluorene in hepatocarcinogenesis: specific targets for initiation and promotion. Mut. Res. 376, 169–176, 1997.
  • Nishioka, H. and Ogasawara, H. Mutagenicity testing for diphenyl derivatives in bacterial systems. Mutat. Res. 54, 248–249, 1979 (abstract).
  • Norris, J.M. Eye irritation test conducted on Dowicide 1 preservative.Dow Chemical, Report 1971.
  • NITS = National Technical Information Service. Evaluation of carcinogenic, teratogenic and mutagenic activities of selected pesticides and industrial chemicals. Vol. 1, Carcinogenic Study, Washington DC, US Department of Commerce, 87, 1968.
  • NTIS = National Technical Information Service. Environ- mental criteria and assessment office health and envi- ronmental effects profile for 2–phenylphenol. National Technical Information Service as NTIS-PB88–161989, 1988
  • NTP - National Toxicology Program. Public Health Service, NTP-85–055, 1985.
  • NTP Technical report on the toxicology and carcinogenesis studies of ortho-phenylphenol (CAS No. 90–43–7) alone and with 7,12–dimethylbenz(a)anthracene (CAS No. 57–97–6) in Swiss CD-1 mice dermal studies). NIH Publication No. 85–2557, NTP 84–099, US De- partment of Health and Human Services, NTP TR 301, 1986 (also cited as Luster, M., 1985 in FAO/ WHO - Evaluations 1985).
  • OECD Environmental health and safety publications. Ap- praisal of test methods for sex-hormone disrupting chemicals. Series on testing and assessment, Paris, May 2001.
  • Oehme, F.W. Comparative toxicity of o-phenylphenol and an o-phenylphenol-containing disinfectant. Toxicol. Appl. Pharmacol. 19, 412, 1971 (abstract).
  • Oehme, F.W. and Smith, T.H. The metabolism and urinary excretion of o-phenylphenol in dogs and cats. Toxicol. Appl. Pharmacol. 22, 292, 1972 (abstract).
  • Ogata, A., Yoshida, S., Nawai, S., Ando, H., Kubo, Y., Hiraga, K., Masubuchi, M. Dominant lethal tests of long-term administration with sodium o-phenylphenol (OPP-Na) in mice. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 29, 99–103, 1978a.
  • Ogata, A., Ando, H., Kubo, Y., Hiraga, K. Teratological tests of o-phenylphenol (OPP) and sodium o-phenylphenol (OPP-Na) in mice. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 29, 89–96, 1978b.
  • Ogata, A., Ando, H., Kubo, Y., Hiraga, K. Acute oral toxic- ity of sodium o-phenylphenate (OPP-Na) in mice. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 30, 54–56, 1979.
  • Ogata, A., Ando, H., Kubo, Y., Hiraga, K. Dominant lethal tests of long-term administration with sodium o-phenylphenol (OPP-Na) in rats. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 31, 17–19, 1980.
  • Ohtsuki, K., Kabashima, J., Nakao, T. Urinary metabolites of o-phenylphenol sodium salt by oral administration. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 32, 51–52, 1981.
  • Okuda, M. Pathological analysis of the carcinogenic effect of sodium o-phenylphenol and o-phenylphenol in the urinary bladder of rats and mice. J. Nagoya City Univ. Med. Ass. 37, 157–184, 1986.
  • Otoshi, T., Iwata, H., Yamamoto, S., Murai, T., Yamaguchi, S., Matsui-Yuasa, I., Otani, S., Fukushima, S. Sever- ity of promotion by sodium salts of succinic acid in rat urinary bladder carcinogenesis correlates with sodium ion concentration under conditions of equal urinary pH. Carcinogenesis 14, 2277–2281, 1993.
  • Pagano, G., Cipollaro, M., Corsale, G., Della Morte, R., Esposito, A., Giordano, G.G., Micallo, G., Quinto, I., Staiano, N. Comparative toxicity of diphenyl, diphe- nyl ether, and some of their derivatives. Med. Biol. Environ. 16, 291–297, 1988.
  • Pathak, D.N. and Roy, D. Examination of microsomal cyto- chrome P450–catalyzed in vitro activation of o- phenylphenol to DNA binding metabolite(s) by 32P- postlabeling technique. Carcinogenesis 13, 1593–1597, 1992a.
  • Pathak, D.N. and Roy, D. Mechanism of genotoxicity of o- phenylphenol (OPP) in vivo. Proc. Am. Assoc. Can- cer Res. 33, 141, 1992b (abstract).
  • Pathak, D.N. and Roy, D. Mechanisms of genotoxicity of o- phenylphenol in vitro: covalent modification to DNA by phenyl-2,5´-p-quinone, a reactive metabolite of o- phenylphenol. Toxicologist 12, 252, 1992c (abstract).
  • Pathak, D.N. and Roy, D. In vivo genotoxicity of sodium ortho-phenylphenol: phenylbenzoquinone is one of the DNA-binding metabolite(s) of sodium ortho- phenylphenol. Mutat. Res. 286, 309–319, 1993.
  • Pauluhn, J. Preventol ON extra: Untersuchungen auf haut- und schleimhautreizende Wirkung. Bayer AG, Report 1983.
  • Probst, G.S., McMahon, R.E., Hill, L.E., Thompson, C.Z., Epp, J.K., Neal, S.B. Chemically induced unsched- uled DNA synthesis in primary rat hepatocyte cul- tures: a comparison with bacterial mutagenicity using 218 compounds. Environ. Mut. 3, 11–32, 1981.
  • Quast, J.F. and McGuirk, R.J. Ortho-phenylphenol: two- year dietary chronic toxicity/oncogenicity study in B6C3F1 mice. Dow Chemical Comp., Bayer-Miles, Report Code K-001024–047, 1995.
  • Quast, J.F., McGuirk, R.J., Kociba, R.J. Results of a two- year dietary toxicity/oncogenicity study of ortho- phenylphenol (OPP) in B6C3F1 mice. Fundam. Appl. Toxicol. 36, 1997, 341 (abstract).
  • Rachofsky, M.A. and Oehme, F.W. Distribution, kinetics, and tissue residues of o-phenylphenol in the dog. Trans. Kansas Acad. Sci. 78, 23–24, 1976a (abstract). Rachofsky, M.A. and Oehme, F.W. Comparative and age- related pharmocodynamics for single and multiple doses of o-phenylphenol. Toxicol. Appl. Pharmacol. 37, 93, 1976b (abstract).
  • Reed, H.W.B. Alkylphenols. In: Kirk-Othmer Encyclopedia of Chemical Technology, 3rd ed., Vol. 2, Grayson, m. and Eckroth, d., Eds., <i>John Wiley and Sons, Inc., Ny. Pp 87–89, 1978.
  • Rehmann, K, Schramm, K.-W., Kettrup, A.A. Applicability of a yeast oestrogen screen for the detection of oestro- gen-like activities in environmental samples. Chemo- sphere 38, 3303–3312, 1999.
  • Reitz, R.H., Fox, T.R., Quast, J.F., Hermann, E.A., Watanabe, P.G. Molecular mechanisms involved in the toxicity of orthophenylphenol and its sodium salt. Chem.-Biol. Interactions 43, 99–119, 1983.
  • Reitz, R.H., Fox, T.R., Quast, J.F., Hermann, E.A., Watanabe, P.G. Biochemical factors involved in the effects of orthophenylphenol (OPP) and sodium orthophenylphenate (SOPP) on the urinary tract of male F44 rats. Toxicol. Appl. Pharmacol. 73, 345–349, 1984.
  • Robenek, H., Meiss, R., Themann, H., Himmels, S. A corre- lated thin section and freeze-fracture study of o- phenylphenol-induced alterations in the rat liver. Expl. Cell Biol. 48, 404–420, 1980.
  • Rodent bladder carcinogenesis group. Urinary bladder car- cinogenesis: implications for risk assessment. Food Chem. Toxicol. 33, 797–802, 1995.
  • Romanoski, C.A. and Eastmond, D.A. Arachidonic acid- dependent induction of micronuclei in V79 cells by phenylhydroquinone, a metabolite of the fungicide o- phenylphenol. Toxicologist 12, 56, 1992 (abstract).
  • Routledge, E.J. and Sumpter, J.P. Structural features of alkylphenolic chemicals associated with estrogenic activity. J. Biol. Chem. 272, 3280–3288, 1997.
  • Roy, D. Cytochrome P-450 catalyzed redox cycling of orthophenylphenol. Biochem. Int. 22, 849–857, 1990. Sakai, A., Miyata, N., Takahashi, A. Initiating activity of quinones in the two-stage transformation of Balb/3T3 cells. Carcinogenesis 16, 477–481, 1995.
  • Salminen, E. and Salminen, S. Urinary excretion of orally administered oxalic acid in saccharin and o- phenylphenol-fed NMRI mice. Urol. Int. 41, 88–90, 1986.
  • San, H.C. and Springfield, K.A. O-phenylphenol - Salmo- nella/mammalian-microsome plate incorporation mu- tagenicity assay (Ames test). Microbiological Associ- ates Inc., (Lab. Study number C141.501017); 1989a.
  • San, H.C. and Springfield, K.A. O-phenylphenol, sodium salt tetrahydrate - Salmonella/mammalian-microsome plate incorporation mutagenicity assay (Ames test). Microbiological Associates Inc., (Lab. Study number C142.501017); 1989b.
  • Sasaki, M. and Nakao, T. The effects of o-phenylphenol on the immune response in vitro. Ann. Rep. Tokyo Metro. Res. Lab. P.H. 29, 109–111, 1978.
  • Sasaki, Y.F., Saga, A., Akasaka, M., Yoshida, K., Nishidate, E., Su, Y.Q., Matsusaka, N., Tsuda, S. In vivo genotoxicity of ortho-phenylphenol, biphenyl, and thiabendazole detected in multiple mouse organs by the alkaline single cell gel electrophoresis assay. Mutat. Res. 395, 189–198, 1997.
  • Sasaki, M., Ueno, S., Miyamae, Y., Ohta, T., Tsuda, S. Detection of organ specific genotoxicity by alkaline single cell gel electrophoresis assay with mouse mul- tiple organs. Environ. Mutagen. Res. 20, 51–62, 1998. Sasaki, Y.F., Kawaguchi, S., Kamaya, A., Ohsita, M., Kabasawa, K., Iwama, K., Taniguchi, K., Tsuda, M. The comet assay with 8 mouse organs: results with 39 currently used food additives. Mutation Research 519, 103–119, 2002.
  • Sato, M., Tanaka, A., Tsuchiya, T., Yamaha, T., Nakaura, S., Tanaka, T. Excretion, distribution and metabolic fate of sodium o-phenylphenate and o-phenylphenol in the rat. J. Food Hyg. Soc. Japan 29, 7–12, 1988.
  • Sato, H., Toyoda, K., Takamura, N., Furukawa, F., Hasegawa, R., Fukuoka, M., Imaida, K., Takahashi, M., Hayashi, Y. Effects of 2–phenyl-1,4–benzoquinone and 2,5– dihydroxybiphenyl on two-stage mouse skin carcino- genesis. Cancer Lett. 55, 233–238, 1990.
  • Savides, M.C. and Oehme, F.W. Urinary metabolism of orally administered ortho-phenyl-phenol in dogs and cats. Toxicology 17, 355–363, 1980.
  • Schewe, T., Markgraf, K., Schewe, C., Fischer, S., Getter, R., Mayer, M. Stoffwechselschaedigung menschlicher Hautzellen durch Orthophenylphenol (OPP). Melliand Textilberichte 9, 631–632, 1997.
  • Schnuch, A., Geier, J., Uter, W., Frosch, P.J. Patch testing with preservatives, antimicrobials and industrial bio- cides. Results from a multicentre study. Brit. J. Dermatol. 138, 467–476, 1998.
  • Schreiber, G. Pruefung von Preventol O extra auf primaere Hautreizwirkung. Fraunhofer-Institut fuer Toxikologie und Aerosolforschung, 1981a.
  • Schreiber, G. Pruefung von Peventol O extra auf Schleimhautreizwirkung. Fraunhofer-Institut fuer Toxikologie und Aerosolforschung, 1981b.
  • Schumann, R. Tagung der Kommission fuer kosmetische Mittel des BgVV; Bericht über die 59. Sitzung am 7. Dezember in Berlin. Bundesgesundheitsbl. – Gesundheitsforsch. – Gesundheitsschutz 43, 386–387, 2000.
  • Sekihashi, K., Yamamoto, A., Matsumura, Y., Ueno, S., Watanabe-Akanuma, M., Kassie, F., Knasmüller, S., Tsuda, S., Sasaki, Y.F. Comparative investigation of multiple organs of mice and rats in the comet assay. Mutat. Res. 517, 53–74, 2002.
  • Selim, S. A single dose open label study to investigate the absorp- tion and excretion of 14C/13C-labeled orthophenylphenol formulation after dermal application to healthy volunteers. Pharma Bio-Research Clinics BV, Assen, Netherlands, Report No. P0995002, 1996.
  • Shibata, A., Hagiwara, A., Fukushima, S., Ito, N. Thirteen weeks subacute oral study with sodium ortho- phenylphenate (OPP-Na) in B6C3F1 mice. J. Toxic. Sci. 6, 257, 1981 (abstract).
  • Shibata, M.-A., Hagiwara, A., Tamano, S., Fukushima, S., Ito, N. Subchronic toxicity study of sodium o- phenylphenate in mice. Toxicol. Letters 25, 239–246, 1985.
  • Shibata, M.-A., Nakanishi, K., Shibata, M., Masui, T., Miyata, Y., Ito, N. Promoting effect of sodium chloride in 2– stage urinary bladder carcinogenesis in rats initiated by n-butyl-n-(4–hydroxybutyl)-nitrosamine. Urol. Res. 14, 201–206, 1986.
  • Shibata, M.-A., Tamano, S., Kurata, Y., Hagiwara, A., Fukushima, S. Participation of urinary Na+, K+, pH, and l-ascorbic acid in the proliferative response of the bladder epithelium after the oral administration of various salts and/or ascorbic acid to rats. Food Chem. Toxicol. 27, 403–413, 1989a.
  • Shibata, M.-A., Tanaka, H., Yamada, M., Tamano, S., Fukushima, S. Proliferative response of renal pelvic epithelium in rats to oral administration of ortho- phenylphenol, sodium ortho-phenylphenate and diphe- nyl. Cancer Lett. 48, 19–28, 1989b.
  • Shibata, M-A., Yamada, M., Tanaka, H., Kagawa, M., Fukushima, S. Changes in urine composition, bladder epithelial morphology, and DNA synthesis in male F344 rats in response to ingestion of bladder tumor promoters. Toxicol. Appl. Pharmacol. 99, 37–49, 1989c.
  • Shibata, M., Kagawa, M., Kawabe, M., Hagiwara, A., Fukushima, S. Comparative promoting activities of phosphate salts on rat two-stage bladder carcinogen- esis under conditions of equivalent urinary Na+ or K+ levels. Teratog. Carcinog. Mutag. 11, 305–316, 1991.
  • Shibata, M., Tamano, S., Shirai, T., Kawabe, M., Fukushima, S. Inorganic alkalizers and acidifiers under conditions of high urinary Na+ or K+ on cell proliferation and two-stage carcinogenesis in the rat bladder. Jpn. J. Cancer Res. 83, 821–829, 1992.
  • Shioya, S., Nagami-Oguihara, R., Oguihara, S., Kimura, T., Imaida, K. Roles of bladder distension, urinary pH and urinary sodium ion concentration in cell prolifera- tion of urinary bladder epithelium in rats ingesting sodium salts. Food Chem. Toxicol. 32, 165–171, 1994.
  • Shirasu, Y, Moriya, M., Kato, K., Tezuka, H., Henmi, R., Shingu, A., Kaneda, M., Teramoto, S. Mutagenicity testing on o- phenylphenol. Mutat. Res. 54, 227, 1978 (abstract).
  • Shirasu, Y., Moriya, M., Tezuka, H., Teramoto, S., Ohta, T., Inoue, T. Mutagenicity screening studies on pesti- cides. International Conference on Environmental Mutagens 3, 331–335, 1982.
  • Smith, R.A., Christenson, W.R., Bartels, M.J., Arnold, L.L., St. John, M.K., Cano, M., Garland, E.M., Lake, S.G., Wahle, B.S., McNett, D.A., Cohen, S.M. Urinary physiologic and chemical metabolic effects on the urothelial cytotoxicity and potential DNA adducts of o-phenylphenol in male rats. Toxicol. Appl. Pharmacol. 150, 402–413, 1998.
  • Soto, A.M., Fernandez, M.F., Luizzi, M.F., Karasko, A.S.O., Sonnenschein, C. Developing a marker of exposure to xenoestrogen mixtures in human serum. Environ. Health Perspect. 105, (Suppl 3), 647–654, 1997.
  • St.John, M.K., Arnold, L.L., Anderson, T., Cano, M., Johansson, S.L., Cohen, S.M. Dietary effects of ortho- phenylphenol and sodium ortho-phenylphenate on rat urothelium. Toxicol. Sci. 59, 346–351, 2001.
  • Storrs, F.J., Rosenthal, L.E., Adams, R.M., Clendenning, W., Emmett, E.A., Fisher, A.A., Larsen, W.G., Maibach, H.I., Rietschel, R.L., Schorr, W.F., Taylor, J.S. Prevalence and relevance of allergic reactions in patients patch tested in North America - 1984 to 1985. J. Am. Acad. Dermatol. 20, 1038–1045, 1989.
  • Stouten, H. Toxicological profile for o-phenylphenol and its sodium salt. J. Appl. Toxicol. 18, 261–270, 1998.
  • Suberg, H. Preventol O extra (OPP): Untersuchung auf primaere Reiz-/Aetzwirkung an der Kaninchenhaut. Bayer AG, Inst. f. Toxikologie, Report 1983.
  • Sugihara, N., Shimomichi, K., Furuno, K. Cytotoxicity of food preservatives in cultured rat hepatocytes loaded with linolenic acid. Toxicology 120, 29–36, 1997.
  • Suzuki, H., Nakao, T., Hiraga, K. Mutagenicity of orthophenylphenol (OPP) in a human clonal cell line. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 35, 399–400, 1984.
  • Suzuki, H., Suzuki, N., Sasaki, M., Hiraga, K. Orthophenylphenol mutagenicity in a human cell strain. Mutat. Res. 156, 123–127, 1985.
  • Tada, Y., Fujitani, T., Yano, N.Y., Yuzawa, K., Nagasawa, A., Aoki, N., Ogata, A., Yoneyama, M. Chronic tox- icity of thiabendazole (TBZ) in CD-1 mice. Toxicol- ogy 169, 163–176, 2001.
  • Tadi-Uppala., P., Hasegawa, L., Rupa, D.S., Eastmond, D.A. Detection of micronuclei and cell proliferation in the rat bladder induced by the fungicides o-phenylphenol and sodium ortho-phenylphenate. Carcinogenesis 37, 127–128, 1996 (abstract).
  • Takahashi, T., Sato, H., Toyoda, K., Furukawa, F., Imaida, K., Hasegawa, R., Hayashi, Y. Sodium o-phenlyphenate (OPP-Na) promotes skin carcinogenesis in CD-1 fe- male mice initiated with 7,12–dimethylbenz[a]-an- thracene. Carcinogenesis 10, 1163–1167, 1989.
  • Taniguchi, Y., Morimoto, J., Okada, K., Imai, S., Tsubura, Y. Toxicological study of o-phenylphenol (OPP) in mice: I. Acute oral toxicity in ddY mouse. J. Nara Med. Ass. 32, 425–429, 1981a. Taniguchi, Y., Morimoto, J., Okada, K., Imai, S., Tsubura, Y. Toxicological study of sodium orthophenylphenate (OPP-Na) in rats. II. Acute oral toxicity in Fischer 344 DuCrj rats. J. Nara. Med. Ass. 32, 709–714, 1981b. Tayama, K., Iguchi, S., Hiraga, K. Acute oral toxicity of sodium o-phenylphenol (OPP-Na) in rats. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 30, 57–65, 1979.
  • Tayama, K., Iguchi, S., Hiraga, K. Acute oral toxicity of o- phenylphenol in rats. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 31, 1–6, 1980.
  • Tayama, K., Iguchi, S., Sasaki, M., Hiraga, K. Acute oral toxicity of o-phenylphenol (OPP) in mice. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 34, 325–328, 1983a.
  • Tayama, S., Kamiya, N., Nakao, T., Hiraga, K. Detection of o-phenylphenol (OPP) and the activated metabolites with S-9 mix by HPLC and the effect of these on induction of SCE in CHO-K1 cells. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 34, 312–314, 1983b.
  • Tayama, K., Hiraga, K. Depigmentation caused by a single oral administration of o-phenylphenol (OPP) in ordi- nary and textile hair of C57BL/6N mice. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 35, 401–406, 1984.
  • Tayama, K, Nakamura, K., Kamiya, N., Hiraga, K. Urinaly- ses of male F344/DuCrj rats fed with sodium o-phenylphenate (OPP-Na). Ann. Rep. Tokyo Metr. Res. Lab. P.H. 35, 425–430, 1984.
  • Tayama, S. and Ichikawa, H. Effects of phenylphenols on chromosomes in CHO-K1 cells. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 38, 388–391, 1987.
  • Tayama, S., Kamiya, N., Nakagawa, Y. Genotoxic effects of o-phenylphenol metabolites in CHO-K1 cells. Mutat. Res. 223, 23–33, 1989.
  • Tayama, S. and Nakagawa, Y. Sulfhydryl compounds inhibit the cyto- and genotoxicity of o-phenylphenol metabo- lites in CHO-K1 cells. Mutat. Res. 259, 1–12, 1991.
  • Tayama, S, and Nakagawa, Y. Effect of scavangers of active oxygen species on cell damage caused in CHO-K1 cells by phenylhydroquinone, an o- phenylphenol metabolite. Mutat. Res. 324, 121–131, 1994.
  • Tayama-Nawai, S., Yoshida, S., Nakao, T., Hiraga, K. In- duction of chromosome aberrations and sister-chro- matid exchanges in CHO-K1 cells by o-phenylphenol. Mutat. Res. 141, 95–99, 1984.
  • Thyssen, J. Preventol O extra: Gewerbetoxikologische Untersuchungen. Bayer AG, Report No. 10541, 1982. Thalacker, F.W. Nature of the residue of 14C-orthophenylphenol in lactating goats. Covance Laboratories Inc., Laboratory Project Identification CHW 6578–105, 1997.
  • Timchalk, K. 14C-orthophenylphenol: pharmacokinetics fol- lowing dermal application in male human volunteers. Dow Chemical, Report No. K-001024–064, 1996.
  • Timchalk, C., Selim, S., Sangha, G., Bartels, M.J. The phar- macokinetics amd metabolism of 14C/13C-labeled ortho- phenylphenol formation following dermal application to human volunteers. Hum. Exp. Toxicol. 17, 411– 417, 1998.
  • Trotz, S.I., Pitts, J.J. Industrial antimicrobial agents. In: Kirk- Othmer Encyclopedia of Chemical Technology, 3rd ed., Vol. 13, Grayson, M., Eckroth, D., Eds., John Wiley and Sons, Inc., NY. pp 226–229, 1981.
  • Tuer, W.F., James, W.D., Summers, R.J. Contact urticaria to o-phenylphenate. Annals Allergy 56, 19–21, 1986.
  • Ushiyama, K., Kabashima, J., Nakao, T. Metabolism of 2– phenylphenol (OPP) in rats: metabolic profile of OPP in rats fed dietary for long period. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 33, 455–457, 1982.
  • Ushiyama, K., Kabashima, J., Nakao, T. Metabolism of o- phenylphenol sodium salt (OPP-Na) in rats: dose- response of metabolic profile of OPP. Ann. Rep. To- kyo Metr. Res. Lab. P.H. 34, 297–298, 1983.
  • Ushiyama, K., Sato, K., Nakagawa, A., Nagai, F., Kabashima, J., Kano, I., Nakao, T. The metabolism of o- phenylphenol sodium salt. Toxicol. Lett. 31 (Suppl.), 168, 1986 (abstract).
  • Ushiyama, K., Nagai, F., Nakagawa, A., Kano, I. DNA adduct formation by o-phenyphenol metabolite in vivo and in vitro. Carcinogenesis 13, 1469–1473, 1992.
  • Uter, W., Schaller, S., Bahmer, F.A., Brasch, J., Diepgen, T.L., Enders, F., Frosch, P.J., Fuchs, T., Henseler, T., Mueller, S., Peters, K.P., Przybilla, B., Schaller, J., Schnuch, A., Schulze-Dirks, A., Stary, A. Contact allergy in metal workers – a one-year analysis based on data collected by the “Information Network of Dermatological Clinics” (IVDK) in Germany. Dermatosen, 41, 320–327, 1993.
  • Uwagawa, S., Imaida, K., Tsuda, H., Masui, T., Ito, N. Marked enhancing potential of prior N-methyl-N- nitrosourea (MNU) treatment on rat tumorigenesis in various organs induced by 6 different carcinogens. Toxicologist 8, 165, 1988 (abstract).
  • Uwagawa, S., Tsuda, H., Inoue, T., Tagawa, Y., Aoki, T., Kagawa, M., Ogiso, T., Ito, N. Enhancing potential of 6 different carcinogens on multi-organ tumorigenesis after initial treatment with N-methyl-N-nitrosourea in rats. Jpn. J. Cancer Res. 82, 1397–1405, 1991.
  • Van Hecke, E. Contact dermatitis to o-phenylphenol in a coolant. Contact dermatitis 15, 46, 1986.
  • Wahle, B.S., Christenson, W.R. Technical grade ortho- phenylphenol: a combined chronic toxicity/oncoge- nicity testing study in the rat. Bayer Corp., Report No. 92–272–sc, 1996.
  • Wahle, B.S., Christenson, W.R., Lake, S.G., Elcock, L.E., Moore, K.D., Sangha, G.K., Thyssen, J.H. Technical grade ortho-phenylphenol: a combined chronic toxic- ity/oncogenicity testing study in the rat. Fundam. Appl. Toxicol. 36, 1997 (abstract).
  • Wiebkin, P., Fry, J.R., Jones, C.A., Lowing, R.K., Bridges, J.W. The metabolism of biphenyl by isolated viable rat hepatocytes. Xenobiotica 6, 725–743, 1976.
  • Wiebkin, P., Fry, J.R., Jones, C.A., Lowing, R.K., Bridges, J.W. Biphenyl metabolism in isolated rat hepatocytes: effect of induction and nature of the conjugates. Biochem. Pharmacol. 27, 1899–1907, 1978.
  • WHO, World Health Organization. Pesticide Residues in Food – 1999. Who/PCS/00.4, 201–237, 2000.
  • Woodruff, R.C., Mason, J.M., Valencia, R., Zimmering, S. Chemical mutagenesis testing in Drosophila. V. Re- sults of 53 coded compounds tested for the National Toxicology Program. Environ. Mut. 7, 677–702, 1985. Yamazaki, H., Yamaguchi, T., Yamauchi, A., Kakiuchi, Y. Food additives on acceptable daily intake (ADI) level affect the agonist induced platelet activation. I. Anti- oxidants and preservatives: Chemosphere 29, 1293–1299, 1994.
  • Yanagisawa, F., Ueda, Y., Tsuchida, M. Acute intoxication by o-phenylphenol. Jpn. J. Rural Med. 27, 632–633, 1978. Yoshida, S., Nawai, S., Hiraga, K. Cytogenetic studies of sodium o-phenylphenate (OPP-Na). Ann. Rep. Tokyo Metr. Res. Lab. P.H. 30, 44–47, 1979.
  • Yoshida, S., Sasaki, M., Nakao, T., Hiraga, K. Chromosome preparations from CHO-K1 cells used Nunc plate. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 32, 111–114, 1981.
  • Yoshida, S. and Hiraga, K. Cytogenetic studies on rats fed with o-phenylphenol (OPP) and sodium o-phenylphenate (OPP-Na) for long-term. Ann. Rep. Tokyo Metr. Res. Lab. P.H. 33, 489–491, 1982.
  • Zablotny, C.L., Breslin, W.J., Kociba, R.J. Ortho- phenylphenol (OPP): gavage teratology probe study in New Zealand White rabbits. Dow Chemical Report No. K-001024–044, 1991a.
  • Zablotny, C.L., Breslin, W.J., Kociba, R.J. Ortho- phenylphenol (OPP): gavage teratology study in New Zealand White rabbits. Dow Chemical Report No. K- 001024–045, 1991b.
  • Zablotny, C.L., Breslin, W.J., Kociba, R.J. Developmental toxicity of ortho-phenylphenol (OPP) in New Zealand White rabbits. Toxicologist 12, 103, 1992 (abstract). Zempel, J.A., Szabo, J.R. Ortho-phenylphenol: 21–day repeated dermal dose study of systemic toxicity in Fischer 344rats. Dow Chemical Report No. K-001024–056, 1993.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.