Advances in environmental research

  • 제2권3호
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  • Pages.179-202
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  • 2013
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  • 2234-1722(pISSN)
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  • 2234-1730(eISSN)
테크노프레스 (Techno-Press)
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DOI QR코드

DOI QR Code

Bisphenol A and other alkylphenols in the environment - occurrence, fate, health effects and analytical techniques

  • Zhu, Zhuo (Department of Chemistry and Biochemistry, University of Massachusetts Dartmouth, University of Massachusetts Graduate School of Marine Sciences and Technology) ;
  • Zuo, Yuegang (Department of Chemistry and Biochemistry, University of Massachusetts Dartmouth, University of Massachusetts Graduate School of Marine Sciences and Technology)
  • 투고 : 2013.05.24
  • 심사 : 2013.09.05
  • 발행 : 2013.09.25
⟨ 이전 논문 다음 논문 ⟩

초록

Bisphenol A and other alkylphenols are widely used in plastic and other industrial consumer products. Release of these compounds into the aquatic environment during their manufacture, use and disposal has been a great scientific and public concern due to their toxicity at high concentrations and endocrine disrupting effects at low concentration on aquatic wildlife and human beings. This paper reviews the published data and researches on the environmental occurrence, distribution, health effects and analytical techniques of bisphenol A and alkylphenols. The aim is to provide an overview of the current understanding about bisphenol A and alkylphenols in the environment and the difficulties faced today in order to establish standard and systematic environmental analysis and assessment process for these endocrine disruptor compounds.

키워드

참고문헌

  1. Ahel, M. and Giger, W. (1993), "Partitioning of alkylphenols and alkylphenol polyethoxylates between water and organic solvents", Chemosphere, 26(8), 1471-1478. https://doi.org/10.1016/0045-6535(93)90214-P
  2. Ahel, M., Giger, W. and Schaffner, C. (1994), "Behaviour of alkylphenol polyethoxylate surfactants in the aquatic environment, II. Occurrence and transformation in rivers", Water Res., 28(5), 1143-1152. https://doi.org/10.1016/0043-1354(94)90201-1
  3. Ahel, M., Schaffner, C. and Giger, W. (1996), "Behaviour of alkylphenol polyethoxylate surfactants in the aquatic environment, III. Occurrence and elimination of their persistent metabolites during infiltration of river water to groundwater", Water Res., 30(1), 37-46. https://doi.org/10.1016/0043-1354(95)00123-3
  4. Ahel, M., Molnar, E., Ibric, S. and Giger, W. (2000), "Estrogenic metabolites of alkylphenol olyethoxylates in secondary sewage effluents and rivers", Water Sci. Technol., 42(7-8), 15-22.
  5. Alonso-Magdalena, P., Laribi, O., Ropero, A.B., Fuentes, E., Ripoll, C., Soria, B. and Nadal, A. (2005), "Low doses of bisphenol A and diethylstilbestrol impair $Ca^{2+}$ signals in pancreatic alpha-cells through a nonclassical membrane estrogen receptor within intact islets of Langerhans", Environ. Health Perspect., 113(8), 969-977. https://doi.org/10.1289/ehp.8002
  6. Alonso-Magdalena, P., Ropero, A.B., Carrera, M.P., Cederroth, C.R., Baquie, M., Gauthier, B.R., Nef, S., Stefani, E. and Nadal, A. (2008), "Pancreatic insulin content regulation by the estrogen receptor ER alpha", PLoS ONE, 3, e2069. https://doi.org/10.1371/journal.pone.0002069
  7. Andreu, V., Ferrer, E., Rubio, J.L., Font, G. and Pico, Y. (2007), "Quantitative determination of octylphenol, nonylphenol, alkylphenol ethoxylates and alcohol ethoxylates by pressurized liquid extraction and liquid chromatography-mass spectrometry in soils treated with sewage sludges", Sci. Total Enviro., 378(1-2),124-129. https://doi.org/10.1016/j.scitotenv.2007.01.024
  8. Ballesteros, O., Zafra, A., Navalon, A. and Vilchez, J.L. (2006), "Sensitive gas chromatographic-mass spectrometric method for the determination of phthalate esters, alkylphenols, bisphenol A and their chlorinated derivatives in wastewater samples", J. Chromatogr. A, 1121(2), 154-162. https://doi.org/10.1016/j.chroma.2006.04.014
  9. Ballesteros-Gomez, A., Rubio, S. and Perez-Bendito, D. (2009), "Analytical methods for the determination of bisphenol A in food", J. Chromatogr. A, 1216(3), 449-469. https://doi.org/10.1016/j.chroma.2008.06.037
  10. Baltussen, E., Sandra, P., David, F. and Cramers, C. (1999), "Stir bar sorptive extraction (SBSE), a novel extraction technique for aqueous samples: Theory and principles", J. Microcolumn Sep., 11(10), 737-747. https://doi.org/10.1002/(SICI)1520-667X(1999)11:10<737::AID-MCS7>3.0.CO;2-4
  11. Barber, L.B., Lee, K.E., Swackhamer, D.L. and Schoenfuss, H.L. (2007), "Reproductive responses of male fathead minnows exposed to wastewater treatment plant effluent, effluent treated with XAD8 resin, and an environmentally relevant mixture of alkylphenol compounds", Aquat. Toxicol., 82(1), 36-46. https://doi.org/10.1016/j.aquatox.2007.01.003
  12. Bennett, E.R. and Metcalfe, C.D. (1998), "Distribution of alkylphenol compounds in Great Lakes sediments, United States and Canada", Environ. Toxicol. Chem., 17(7), 1230-1235. https://doi.org/10.1002/etc.5620170706
  13. Bennie, D.T., Sullivan, C.A., Lee, H.B., Peart, T.E. and Maguire, R.J. (1997), "Occurance of alkylphenols and alkylphenol mono- and diethoxylates in natural waters of the laurentian Great Lakes basin and the upper St. Lawrence River", Sci. Total Environ., 193(3), 263-275. https://doi.org/10.1016/S0048-9697(96)05386-7
  14. Bergman, A., Heindel, J.J., Jobling, S., Kidd, K.A. and Zoeller, R.T. (2012), State of the Science of Endocrine Disrupting Chemicals-2012, WHO, UNEP.
  15. Berkner, S., Streck, G. and Herrmann, R. (2004), "Development and validation of a method for determination of trace levels of alkylphenols and bisphenol A in atmospheric samples", Chemosphere, 54(4), 575-584. https://doi.org/10.1016/S0045-6535(03)00759-8
  16. Biggers, W. and Laufer, H. (2004), "Identifications of juvenile hormone-activate alkylphenols in the lobster Hormarus americanus and in marine sediments", Biol. Bull., 206(1), 13-24. https://doi.org/10.2307/1543194
  17. Blackburn, M.A. and Waldock, M.J. (1995), "Concentrations of alkylphenols in rivers and estuaries in England and Wales", Water Res., 29(7), 1623-1629. https://doi.org/10.1016/0043-1354(94)00340-D
  18. Blackburn, M.A., Kirby, S.J. and Waldock, M.J. (1999), "Concentrations of alkylphenol polyethoxylates entering UK estuaries", Mar. Pollut. Bull., 38, 109-118. https://doi.org/10.1016/S0025-326X(98)00104-0
  19. Bobsein, R.L., Hauger, B.E., Coutant, W.R. and Rathman, J. (2007), "Phosphite additives in polyolefins", US Patent 7, 157, 511.
  20. Boitsov, S., Meier, S., Klungsoyr, J. and Svardal, A. (2004), "Gas chromatography-mass spectrometry analysis of alkylphenols in produced water from offshore oil installations as pentafluorobenzoate derivatives", J. Chromatogr. A, 1059(1-2), 131-141. https://doi.org/10.1016/j.chroma.2004.09.084
  21. Boitsov, S., Mjos, S. and Meier, S. (2007), "Identification of estrogen-like alkylphenols in produced water from offshore oil installations", Mar. Environ. Res., 64(5), 651-665. https://doi.org/10.1016/j.marenvres.2007.07.001
  22. Cantero, M., Rubio, S. and Perez-Bendito, D. (2006), "Determination of alkylphenols and alkylphenol carboxylates in wastewater and river samples by hemimicelle-based extraction and liquid chromatography-ion trap mass spectrometry", J. Chromatogr. A, 1120(1-2), 260-267. https://doi.org/10.1016/j.chroma.2005.12.048
  23. Cash, G. (1995), "Correlation of physicochemical properties of alkylphenols with their graph-theoretical epsilon parameter", Chemosphere, 31(10), 4307-4315. https://doi.org/10.1016/0045-6535(95)00295-J
  24. Cespedes, R., Lacorte, S., Ginebreda, A. and Barcelo, D. (2008), "Occurrence and fate of alkylphenols and alkylphenol ethoxylates in sewage treatment plants and impact on receiving waters along the Ter River (Catalonia, NE Spain)", Environ. Pollut., 153(2), 384-392. https://doi.org/10.1016/j.envpol.2007.08.026
  25. Chen, B., Duan, J., Maia, B., Luo, X., Yang, Q., Sheng, G. and Fu, J. (2006), "Distribution of alkylphenols in the Pearl River Delta and adjacent northern South China Sea, China", Chemosphere, 63(4), 652-661. https://doi.org/10.1016/j.chemosphere.2005.08.004
  26. Chen, Y., Zhang, K. and Zuo, Y. (2013), "Direct and indirect photodegradation of estriol in the presence of humic acid, nitrate and iron complexes in water solutions", Sci. Total Environ. 463-464, 802-809. https://doi.org/10.1016/j.scitotenv.2013.06.026
  27. Chiha, M., Hamdaoui, O., Baup, S. and Gondrexon, N. (2011), "Sonolytic degradation of endocrine disrupting chemical 4-cumylphenol in water", Ultrason. Sonochem., 18(5), 943-950. https://doi.org/10.1016/j.ultsonch.2010.12.014
  28. Cousins, I.T., Staples, C.A., Klecka, G.M. and Mackay, D. (2002), "A Multimedia assessment of the environmental fate of bisphenol A", Hum. Ecol. Risk Assess. , 8(5), 1107-1135 https://doi.org/10.1080/1080-700291905846
  29. Dachs, J., Van Ry, D. and Eisenreich, S. (1999), "Occurrence of estrogenic nonylphenols in the urban and costal atmosphere of the lower Hudson River estuary", Environ. Sci. Technol., 33(15), 2676-2679. https://doi.org/10.1021/es990253w
  30. de Voogt, P., de Beer, K. and van der Wielen, F. (1997), "Determination of alkylphenol ethoxylates in industrial and environmental samples", Trends Anal. Chem., 16(10), 584-595. https://doi.org/10.1016/S0165-9936(97)00100-3
  31. Devier, M., Le Menach, K., Viglino, L., Di Gioia, L., Lachassagne, P. and Budzinski, H. (2013), "Ultra-trace analysis of hormones, pharmaceutical substances, alkylphenols and phthalates in two French natural mineral waters", Sci. Total Environ., 443(15), 621-632. https://doi.org/10.1016/j.scitotenv.2012.10.015
  32. Ding, W., Tzing, S. and Lo, J. (1999), "Occurrence and concentrations of aromatic surfactants and their degradation products in river waters of Taiwan", Chemosphere, 38(11), 2597-2606. https://doi.org/10.1016/S0045-6535(98)00467-6
  33. Diana, A. and Dimitra, V. (2011), "Alkylphenols and phthalates in bottled waters", J. Hazard. Mater., 185(1), 281-286. https://doi.org/10.1016/j.jhazmat.2010.09.031
  34. Dodds, E.C., Goldberg, L., Lawson, W. and Robinson, R. (1938), "Oestrogenic activity of certain synthetic compounds", Nature, 141, 247-248.
  35. Dorn, P.B., Chou, C.S. and Getempo, J.J. (1987), "Degradation of Bisphenol A in natural waters", Chemosphere, 16(7), 1501-1507. https://doi.org/10.1016/0045-6535(87)90090-7
  36. Espejo, R., Valter, K., Simon, M., Janin, Y. and Arrizabalag, P. (2002), "Determination of nineteen 4-alkylphenol endocrine disrupters in Geneva municipal sewage wastewater", J. Chromatogr. A, 976(1-2), 335-343. https://doi.org/10.1016/S0021-9673(02)01229-3
  37. Ferrara, F., Fabietti, F., Delise, M. and Funari, E. (2005), "Alkylphenols and alkylphenol ethoxylates contamination of crustaceans and fishes from the Adriatic Sea (Italy)", Chemosphere, 59(8), 1145-1150. https://doi.org/10.1016/j.chemosphere.2004.11.085
  38. Ferrara, F., Ademollo, N., Delise, M., Fabietti, F. and Funari, E. (2008), "Alkylphenols and their ethoxylates in seafood from the Tyrrhenian Sea", Chemosphere, 72(9), 1279-1285. https://doi.org/10.1016/j.chemosphere.2008.04.060
  39. Fiedler, S., Foerster, M., Glaser, B. and Zech, W. (2007), "Alkylphenols in sediments of the Atlantic Rainforest south-west of Sao Paulo, Brazil", Chemosphere, 66(2), 212-218. https://doi.org/10.1016/j.chemosphere.2006.05.064
  40. Fiege, H., Voges, H., Hamamoto, H., Umemura, S., Iwata, T., Miki, H., Fujita, Y., Buysch, H., Garbe, D. and Paulus, W. (2002), Phenol Derivatives, Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim.
  41. Geyer, H., Viswanathan, R., Freitag, D. and Korte, F. (1981), "Relationship between water solubility of organic chemicals and their bioaccumulation by the alga Chlorella", Chemosphere, 10(11-12), 1307-1313. https://doi.org/10.1016/0045-6535(81)90048-5
  42. Guo, Y., Wang, L. and Kannan, K. (2013), "Effects of storage time and temperature on levels of phthalate metabolites and bisphenol A in urine", Adv. Environ. Res., Int. J., 2(1), 9-17. https://doi.org/10.12989/aer.2013.2.1.009
  43. Hansch, C. and Leo, A. (1995), "The hydrophobic parameter: measurement and calculation S.R. Heller (Ed.), Exploring QSAR, Fundamentals and Applications in Chemistry and Biology", American Chemical Society, Washington, D.C., USA.
  44. Hawrelak, M., Bennett, E. and Metcalfe, C. (1999), "The environmental fate of the primary degradation products of alkylphenol ethoxylate surfactants in recycled paper sludge", Chemosphere, 39(5), 745-752. https://doi.org/10.1016/S0045-6535(99)00010-7
  45. Ho, S.M., Tang, W.Y., Belmonte, J. and Prins, G.S. (2006), "Developmental exposure to estradiol and bisphenol A increases susceptibility to prostate carcinogenesis and epigenetically regulates phosphodiesterase type 4 variant 4", Cancer Res., 66(11), 5624-5632. https://doi.org/10.1158/0008-5472.CAN-06-0516
  46. Isobe, T., Nishiyama, H., Nakashima, A. and Takada, H. (2001), "Distribution and behaviour of nonylphenol, octylphenol, and nonylphenol monoethoxylate in Tokyo metropolitan area: their association with aquatic particles and sedimentary distributions", Environ. Sci. Technol., 35(6), 1041-1049. https://doi.org/10.1021/es001250i
  47. Itokawa, H., Totsuka, N., Nakahara, K., Maezuru, M., Takeya, K., Kondo, M., Inamatsu, M. and Morita, H. (1989), "A quantitative structure activity relationship for antitumor-activity of long-chain phenols from Ginkgo-Biloba L", Chem. Pharm. Bull., 37(6), 1619-1621. https://doi.org/10.1248/cpb.37.1619
  48. Jakob, W.L. and Schoof, H.F. (1972), "Mosquito larvicide studies with MON 585, a juvenile hormone mimic", Mosq. News, 32, 6-10.
  49. Jahnke, A., Gandrass, J. and Ruck, W. (2004), "Simultaneous determination of alkylphenol ethoxylates and their biotransformation products by liquid chromatography/electrospray ionisation tandem mass spectrometry", J. Chromatogr. A., 1035(1), 115-122. https://doi.org/10.1016/j.chroma.2004.02.060
  50. Jiao, Y. and Zuo, Y. (2009), "Ultrasonic extraction and HPLC determination of anthraquinones, aloe-emodine, emodine, rheine, chrysophanol and physcione, in roots of Polygoni multiflori", Phytochem. Anal., 20(4), 272-278. https://doi.org/10.1002/pca.1124
  51. Jobling, S., Sumpter, J., Sheahan, D., Osborne, J. and Matthiessen, P. (1996), "Inhibition of testicular growth in rainbow trout (Oncorhynchus mykiss) exposed to estrogenic alkylphenolic chemicals", Environ. Toxicol. Chem., 15(2), 194-202. https://doi.org/10.1002/etc.5620150218
  52. Jonsson, G., Cavcic, A., Stokke, T., Beyer, J., Sundt, R. and Brede, C. (2008), "Solid-phase analytical derivatization of alkylphenols in fish bile for gas chromatography-mass spectrometry analysis", J. Chromatogr. A, 1183(1-2), 6-14. https://doi.org/10.1016/j.chroma.2007.12.047
  53. Kawaguchi, M., Sakuia, N., Okanouchi, N., Ito, R., Saito, K. and Nakazawa, H. (2005), "Stir bar sorptive extraction and trace analysis of alkylphenols in water samples by thermal desorption with in tube silylation and gas chromatography-mass spectrometry", J. Chromatogr. A, 1062(1), 23-29. https://doi.org/10.1016/j.chroma.2004.11.033
  54. Koh, K., Chiu, T., Boobis, A., Cartmell, E., Pollard, S., Scrimshawd, M. and Lester, J. (2008), "A sensitive and robust method for the determination of alkylphenol polyethoxylates and their carboxylic acids and their transformation in a trickling filter wastewater treatment plant", Chemosphere, 73(4), 551-556. https://doi.org/10.1016/j.chemosphere.2008.06.016
  55. Klosterhaus, S., Grace, R., Hamilton, M. and Donald, Y. (2013), "Method validation and reconnaissance of pharmaceuticals, personal care products, and alkylphenols in surface waters, sediment, and mussels in an urban estuary", Environ. Int., 54, 92-99. https://doi.org/10.1016/j.envint.2013.01.009
  56. Laufer, H., Pan, X., Biggers, W., Capulong, C., Stuart, J.D., Demir, N. and Koehn, U. (2005), "Lessons learned from inshore and deep-sea lobsters concerning alkylphenols", Inver. Rep. Dev., 48(1-3), 109-117. https://doi.org/10.1080/07924259.2005.9652177
  57. Lee, H.B., Peart, T.E., Bennie, D.T. and Maguire, R.J. (1997), "Determination of nonylphenol polyethoxylates and their carboxylic acid metabolites in sewage treatment plant sludge by supercritical carbon dioxide extraction", J. Chromatogri. A, 785(1-2), 385-394. https://doi.org/10.1016/S0021-9673(97)00384-1
  58. Lee, P.C. and Lee, W. (1996), "In vivo estrogenic action of nonylphenol in immature female rats", Bull. Environ. Contam. Toxicol., 57(3), 341-348. https://doi.org/10.1007/s001289900196
  59. Leranth, C., Hajszan, T., Szigeti-Buck, K., Bober, J. and MacLusky, N.J. (2008), "Bisphenol A prevents the synaptogenic response to estradiol in hippocampus and prefrontal cortex of ovariectomized nonhuman primates", Proc. Natl Acad. Sci. USA, 105(37), 14187-14191. https://doi.org/10.1073/pnas.0806139105
  60. Li, C., Cheng, C. and Ding, W. (2008), "Determination of alkylphenol residues in baby-food purees by steam distillation extraction and gas chromatography?mass spectrometry", Food Chem. Toxicol., 46(2), 803-807. https://doi.org/10.1016/j.fct.2007.09.089
  61. Lin, W., Wang, S., Cheng, C. and Ding, W. (2009), "Determination of alkylphenol residues in breast and commercial milk by solid-phase extraction and gas chromatography-mass spectrometry", Food Chem., 114(2), 753-757. https://doi.org/10.1016/j.foodchem.2008.10.059
  62. Lorenc, J.F., Lambeth, G. and Scheffer, W. (1992), Alkylphenols, Encyclopedia of Chemical Technology, ol.Vol. 2 (4th Edition), John Wiley and Sons, New York, USA.
  63. MacLusky, N.J., Hajszan, T. and Leranth, C. (2005), "The environmental estrogen bisphenol A inhibits estrogen induced hippocampal synaptogenesis", Environ. Health Perspect., 113(6), 675-679. https://doi.org/10.1289/ehp.7633
  64. Mark, V. (1979), Polycarbonate composition having resistance to high heat distortion, US Patent 4, 180, 651.
  65. Mark, V. (1981), Process for obtaining halogenated diphenols, US Patent 4, 283, 566.
  66. Meier, S., Klungsøyr, J., Boitsov, S., Eide, T. and Svardal, A., (2005), "Gas chromatography-mass spectrometry analysis of alkylphenols in cod (Gadus morhua) tissues as pentafluorobenzoate derivatives", J. Chromatogr. A, 1062(2), 255-268. https://doi.org/10.1016/j.chroma.2004.11.041
  67. Meier, S., Klungsøyr, J., Boitsov, S., Eide, T. and Svardal, A. (2005), "Gas chromatography-mass spectrometry analysis of alkylphenols in cod (Gadus morhua) tissues as pentafluorobenzoate derivatives", J. Chromatogr. A, 1062(2), 255-268. https://doi.org/10.1016/j.chroma.2004.11.041
  68. Messina, G., Lorenoni, L. and Fadda, A. (1984), Phenolic antioxidant compositions fororganic polymers, US Patent 4, 439, 570.
  69. Mottaleb, M., Usenko, S., O'Donnell, J., Ramirez, A., Brooks, B. and Chambliss, K. (2009), "Gas chromatography-mass spectrometry screening methods for select UV filters, synthetic musks, alkylphenols, an antimicrobial agent, and an insect repellent in fish", J. Chromatogr. A, 1216(5), 815-823. https://doi.org/10.1016/j.chroma.2008.11.072
  70. Mueller, G. and Kim, U. (1978), "Displacement of estradiol from estrogen receptors by simple alkyl phenols", Endocrinology, 102(5), 1429-1435. https://doi.org/10.1210/endo-102-5-1429
  71. Nakamura, S. and Daishima, S. (2004), "Simultaneous determination of alkylphenols and bisphenol A in river water by stir bar sorptive extraction with in situ acetylation and thermal desorption-gas chromatography-mass spectrometry", J. Chromatogr. A, 1038(1-2), 291-294. https://doi.org/10.1016/j.chroma.2004.03.040
  72. Navarro, A., Tauler, R., Lacorte, S. and Barcelo, D. (2010), "Occurrence and transport of pesticides and alkylphenols in water samples along the Ebro River Basin", J. Hydrol., 383(1-2), 18-29. https://doi.org/10.1016/j.jhydrol.2009.06.039
  73. Navarro-Ortega, A., Tauler, R., Lacorte, S. and Barcelo, D. (2010), "Occurrence and transport of PAHs, pesticides and alkylphenols in sediment samples along the Ebro River Basin", J. Hydrol., 383(1-2), 5-17. https://doi.org/10.1016/j.jhydrol.2009.12.031
  74. Newbold, R., Jefferson, W.N. and Padilla-Banks, E. (2007), "Long-term adverse effects of neonatal exposure to bisphenol A on the murine female reproductive tract", Reprod. Toxicol., 24(2), 253-258. https://doi.org/10.1016/j.reprotox.2007.07.006
  75. Niu, Y., Zhang, J., Wu, Y. and Shao, B. (2012), "Analysis of bisphenol A and alkylphenols in cereals by automated on-line solid-phase extraction and liquid chromatography tandem mass spectrometry", J. Agr. Food Chem., 60(24), 6116-6122. https://doi.org/10.1021/jf301401k
  76. Palanza, P.L., Gioiosa, L., Parmigiani, S. and vom Saal, F.S. (2008), "Effects of developmental exposure to bisphenol A on brain and behavior in mice", Environ. Res., 108(2), 150-157. https://doi.org/10.1016/j.envres.2008.07.023
  77. Palanza, P., Howdeshell, K., Parmigiani, S. and vom Saal, F. (2002), "Exposure to a low dose of bisphenol A during fetal life or in adulthood alters maternal behavior in mice", Environ. Health Perspect., 110(3), 415-422. https://doi.org/10.1289/ehp.02110s3415
  78. Pan, Y. and Tsai, S. (2008), "Solid phase microextraction procedure for the determination of alkylphenols in water by on-fiber derivatization with N-tert-butyl-dimethylsilyl-N-methyltrifluoroacetamide", Anal. Chim. Acta, 624(2), 247-252. https://doi.org/10.1016/j.aca.2008.06.039
  79. Pedersen, S. and Lindholst, C. (1999), "Quantification of the xenoestrogens 4-tert.-octylphenol and bisphenol A in water and in fish tissue based on microwave assisted extraction, solid-phase extraction and liquid chromatography-mass spectrometry", J. Chromatogr. A, 864(1), 17-24. https://doi.org/10.1016/S0021-9673(99)01011-0
  80. Renner, R. (1997), "European bans on surfactant trigger transatlantic debate", Environ. Sci. Technol., 31(7), 316A-320A. https://doi.org/10.1021/es972366q
  81. Rhind, S.M., Kyle, C.E., Mackie, C. and Telfer, G. (2007), "Effects of exposure of ewes to sewage sludge-treated pasture on phthalate and alkyl phenol concentrations in their milk", Sci. Total Environ., 383(1-3), 70-80. https://doi.org/10.1016/j.scitotenv.2007.04.045
  82. Ritchter, C., Birnbaum, L., Farabollini, F., Newbold, R., Rubin, B., Talsness, C., Vandenbergh, J., Walser-Kuntz, D. and vom Saal, F. (2007), "In vivo effects of bisphenol A in laboratory rodent studies", Reprod. Toxicol., 24(2), 199-224. https://doi.org/10.1016/j.reprotox.2007.06.004
  83. Ropero, A.B., Alonso-Magdalena, P., Garcia-Garcia, E., Ripoll, C., Fuentes, E. and Nadal, A. (2008), "Bisphenol-A disruption of the endocrine pancreas and blood glucose homeostasis", Int. J. Androl., 31(2), 194-200. https://doi.org/10.1111/j.1365-2605.2007.00832.x
  84. Rudel, R.A., Camann, D.E., Spengler, J.D., Korn, L.R. and Brody, J.G. (2003), "Phthalates, alkylphenols, pesticides, polybrominated diphenyl ethers, and other endocrine-disrupting compounds in indoor air and dust", Environ. Sci. Technol., 37(20), 4543-4553. https://doi.org/10.1021/es0264596
  85. Russell, B.A., Miller, J.D., Cashman, J.R. and Weerawarna, S.A. (2002), "Naturally occurring compounds and their derivatives as cyclooxygenase 2 and/or 5-lipoxygenase inhibitors", United States Patent No. 6, 365, 634.
  86. Sakaue, M., Ohsako, S., Ishimurai, R., Kurosawa, S., Kurohmaru, M., Hayashi, Y., Aoki, Y., Yonemoto, J. and Tohyama, C. (2001), "Bisphenol A affects spermatogenesis in the adult rat even at a low dose", J. Occup. Health, 43(4), 185-190. https://doi.org/10.1539/joh.43.185
  87. Salgueiro-Gonzalez, N., Turnes-Carou, I., Muniategui-Lorenzo, S., Lopez-Mahia, P. and Prada-Rodriguez, D. (2013), "Membrane assisted solvent extraction coupled with liquid chromatography tandem mass spectrometry applied to the analysis of alkylphenols in water samples", J. Chromatogr. A, 1281, 46-53 https://doi.org/10.1016/j.chroma.2013.01.069
  88. Sanchez-Avila, J., Bonet, J., Velasco, G. and Lacorte, S. (2009), "Determination and occurrence of phthalates, alkylphenols, bisphenol A, PBDEs, PCBs and PAHs in an industrial sewage grid discharging to a Municipal Wastewater Treatment Plant", Sci. Total Environ., 407(13), 4157-4167. https://doi.org/10.1016/j.scitotenv.2009.03.016
  89. Sanchez-Avila, J., Jordi, B., Gemma, V. and Silvia, L. (2009), "Determination and occurrence of phthalates, alkylphenols, bisphenol A, PBDEs, PCBs and PAHs in an industrial sewage grid discharging to a Municipal Wastewater Treatment Plant", Sci. Total Environ., 407(13), 4157-4167. https://doi.org/10.1016/j.scitotenv.2009.03.016
  90. Shao, B., Han, H., Hu, J., Zhao, J., Wu, G., Xue, G., Ma, Y. and Zhang, S. (2005), "Determination of alkylphenol and bisphenol A in beverages using liquid chromatography/electrospray ionization tandem mass spectrometry", Anal. Chim. Acta, 530(2), 245-252. https://doi.org/10.1016/j.aca.2004.09.086
  91. Shao, B., Han, H., Li, D., Ma, Y., Tu, X. and Wu, Y. (2007), "Analysis of alkylphenol and bisphenol A in meat by accelerated solvent extraction and liquid chromatography with tandem mass spectrometry", Food Chem., 105(3), 1236-1241. https://doi.org/10.1016/j.foodchem.2007.02.040
  92. Shiu, W., Ma, K., Varhani?kova, D. and Mackay, D. (1994), "Chlorophenols and alkylphenols: a review and correlation of environmentally relevant properties and fate in an evaluative environment", Chemosphere, 29(6), 1155-1224. https://doi.org/10.1016/0045-6535(94)90252-6
  93. Staples, C., Dorn, P., Klecka, G., O'Block, S., Branson, D. and Harris, L. (2000), "Bisphenol A concentrations in receiving waters near US manufacturing and processing facilities", Chemosphere, 40(5), 521-525. https://doi.org/10.1016/S0045-6535(99)00288-X
  94. Staples, C.A., Dorn, P.B. and Klecka, G.M. (1998), "A review of the environmental fate, effects and exposures of bisphenol A", Chemosphere, 36(10), 2149-1273 https://doi.org/10.1016/S0045-6535(97)10133-3
  95. Stuart, J.D., Capulong, C.P., Launer, K.D. and Pan, X. (2005), "Analyses of phenolic endocrine disrupting chemicals in marine samples by both gas and liquid chromatography-mass spectrometry", J. Chromatogr. A, 1079(1-2), 136-145. https://doi.org/10.1016/j.chroma.2005.03.075
  96. Soares, A., Guieysse, B., Jefferson, B., Cartmell, E. and Lester, J.N. (2008), "Nonylphenol in the environment: A critical review on occurrence, fate, toxicity and treatment in wastewaters", Environ. Int., 34(7), 1033-1049. https://doi.org/10.1016/j.envint.2008.01.004
  97. Sole, M., de Alda, L., Castillo M., Porte C., Ladegaard-Pedersen, K. and Barcelo, D. (2000), "Estrogenicity determination in sewage treatment plants and surface waters from the Catalonian area (NE Spain)", Environ. Sci. Technol., 34(24), 5076-5083. https://doi.org/10.1021/es991335n
  98. Susiarjo, M., Hassold, T., Freeman, E. and Hunt, P. (2007), "Bisphenol A exposure in utero disrupts early oogenesis in the mouse", PLoS Genetics, 3(1), e5. https://doi.org/10.1371/journal.pgen.0030005
  99. Tabata, A., Kashiwa, S., Ohnishi, Y., Ishikawa, H., Miyamoto, N., Itoh, M. and Magara, Y. (2001), "Estrogenic influence of estradiol-17$\beta$, p-nonylphenol and bisphenol A on Japanese Medaka (Oryzias iatipes) at detected environmental concentrations", Water Sci. Technol., 43(2), 109-116.
  100. Talsnessl, C., Andrade, A., Kuriyama, S., Taylor, J. and vom Saal, F. (2009), "Components of plastic: experimental studies in animals and relevance for human health", Phil. Trans. R. Soc. B, 364(1526), 2079-2096. https://doi.org/10.1098/rstb.2008.0281
  101. Tan, B.L. and Mohd, M.A. (2002), "Analysis of selected pesticides and alkylphenols in human cord blood by gas chromatograph-mass spectrometer", Talanta, 61(3), 385-391.
  102. Thiele, B., Gunther, K. and Schwuger, M.J. (1997), "Alkylphenol ethoxylates: Trace analysis and environmental behavior", Chem. Rev., 97(8), 3247-3272. https://doi.org/10.1021/cr970323m
  103. Toxicology, http://web.bryant.edu/-dlm1/sc372/readings/toxicology/toxicology.htm.
  104. Tsuda, T., Takino, A., Kojima, M., Harada, H. and Muraki, K. (1999), "Gas chromatographic-mass spectromeric determination of 4-nonylphenols and 4-tert-octylphenol in biological samples", J. Chromatogr. B, 723(1-2), 273-279. https://doi.org/10.1016/S0378-4347(98)00524-6
  105. Tsuda, T., Takino, A., Kojima, M., Harada, H., Muraki, K. and Tsuji, M. (2000), "4-Nonylphenols and 4-tert-octylphenol in water and fish from rivers flowing into Lake Biwa", Chemosphere, 41(5), 757-762. https://doi.org/10.1016/S0045-6535(99)00465-8
  106. U.S. EPA (2009), Screening-Level Hazard Characterization, Alkylphenols Category, Hazard Characterization Document, September, Washington D.C.
  107. Van Ry, D.A., Dachs, J., Gigliotti, C.L., Bruciak, P.A., Nelson, E.D. and Eisenreich, S. J. (2000), "Atmospheric seasonal trends and environmental fate of alkylphenols in the Lower Hudson River Estuary", Environ. Sci. Technol., 34(12), 2410-2417. https://doi.org/10.1021/es9910715
  108. Vom Saal, F.S., Cooke, P.S., Buchanan, D.L., Palanza, P., Thayer, K.A., Nagel, S.C., Parmigiani, S. and Welshons, W.V. (1998), "A physiologically based approach to the study of bisphenol A and other estrogenic chemicals on the size of reproductive organs, daily sperm production and behavior", Toxicol.Ind. Health, 14(1-2), 239-260. https://doi.org/10.1177/074823379801400115
  109. Wang, J., Pan, H., Liu, Z. and Ge, F. (2009), "Ultra-high-pressure liquid chromatography-tandem mass spectrometry method for the determination of alkylphenols in soil", J. Chromatography A, 1216(12),2499-2503. https://doi.org/10.1016/j.chroma.2009.01.062
  110. Wang, L., Ying, G., Zhao, J., Liu, S., Yang, B., Zhou, L., Tao, R. and Su., H. (2009), "Assessing estrogenic activity in surface water and sediment of the Liao River system in northeast China using combined chemical and biological tools", Environ. Poll., 159(1), 148-156.
  111. Watanabe, M., Takano, T., Nakamura, K., Watanabe, S. and Seino, K. (2007), "Water quality and concentration of alkylphenols in rivers used as source of drinking water and flowing through urban areas", Environ. Health Prev. Med., 12(1), 17-24. https://doi.org/10.1007/BF02898188
  112. Xie, Z.Y., Selzera, J., Ebinghaus, R., Caba, A. and Ruck, W. (2006), "Development and validation of a method for the determination of trace alkylphenols and phthalates in the atmosphere", Anal. Chim. Acta, 565(2), 198-207. https://doi.org/10.1016/j.aca.2006.02.027
  113. Yang, C., Zhao, J., Wang, J., Yu, H., Piao, X. and Li, D. (2013), "Water-based gas purge microsyringe extraction coupled with liquid chromatography for determination of alkylphenols from sea food Laminaria japonica Aresh", J. Chromatogr. A, 1300, 38-42. https://doi.org/10.1016/j.chroma.2013.02.087
  114. Ying, G., Williams, B. and Kookana, R. (2002), "Environmental fate of alkylphenols and alkylphenol ethoxylates-a review", Environ. Int., 28(3), 215-226. https://doi.org/10.1016/S0160-4120(02)00017-X
  115. Zgola-Grzeskowiak, A. (2010), "Dispersive liquid-liquid microextraction applied to isolation and concentration of alkylphenols and their short-chained ethoxylates in water samples", J. Chromatogr. A, 1217(11), 1761-1766. https://doi.org/10.1016/j.chroma.2010.01.054
  116. Zhang, K. and Zuo, Y. (2005), "Pitfalls and solution for simultaneous determination of estrone and 17$\alpha$-ethinylestradiol by gas chromatography-mass spectrometry after derivatization with N,O-bis (trimethylsilyl) trifluoroacetamide", Anal. Chim. Acta., 554(1-2), 190-196. https://doi.org/10.1016/j.aca.2005.08.045
  117. Zhu, Z. and Zuo, Y. (2013), "Occurrence of 4-cumylphenol, 2,4-bis-(dimethylbenzyl)phenol and bisphenol A in prawn Macrobrachium rosenbergii", Chemosphere. [Submitted]
  118. Zuo, Y., Zhang, K. and Deng, Y. (2006), "Occurrence and photochemical degradation of 17$\alpha$-ethinylestradiol in Acushnet River Estuary", Chemosphere, 63(9), 1583-1590. https://doi.org/10.1016/j.chemosphere.2005.08.063
  119. Zuo, Y., Zhang, K. and Lin, Y. (2007), "Microwave-accelerated derivatization for the simultaneous gas chromatographic-mass spectrometric analysis of natural and synthetic estrogenic steroids", J. Chromatogr. A, 1148(2), 211-218. https://doi.org/10.1016/j.chroma.2007.03.037
  120. Zuo, Y., Zhang, L., Wu, J., Fritz, J., Medeiros, S. and Rego, C. (2004), "Ultrasonic extraction and capillary gas chromatography determination of nicotine in pharmaceutical formulations", Anal. Chim. Acta, 526(1),35-39. https://doi.org/10.1016/j.aca.2004.09.035
  121. Zuo, Y., Zhang, K. and Zhou, S. (2013), "Determination of estrogenic steroids and microbial and photochemical degradation of 17$\alpha$-ethinylestradiol (EE2) in lake surface water, a case study", Environ. Sci. Processes & Impacts, 15, 1529-1535. https://doi.org/10.1039/c3em00239j

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