Light induced degradation of testosterone in waters

Science of the Total Environment

Volumn 408, Issue 17, 2010, Pages 3554-3559

  Vulliet, Emmanuelle ^a   Falletta, Marine ^b   Marote, Pedro ^b   Lomberget, Thierry ^c   Païssé, Jean Olivier ^a   Grenier Loustalot, Marie Florence ^a  

^a CNRS USR59   (France)

^b UNIVERSITÉ LYON 1   (France)

^c Univ Lyon   (France)

Author keywords

Kinetics; Photodegradation products; Photolysis; Testosterone

Indexed keywords

ENZYME KINETICS; IRRADIATION; PHOTOLYSIS;

EXCITATION WAVELENGTH; LIGHT-INDUCED DEGRADATION; PHOSPHATE BUFFERS; PHOTODEGRADATION PATHWAY; PHOTODEGRADATION PRODUCTS; PHOTOTRANSFORMATIONS; SPECTROMETRIC DATA; TESTOSTERONE;

PHOTODEGRADATION;

(1,5,10) CYCLOPROPYL 17BETA HYDROXYANDROSTANE 2 ONE; ANDROSTANE DERIVATIVE; PHOSPHATE BUFFERED SALINE; TESTOSTERONE; UNCLASSIFIED DRUG; WATER; WATER POLLUTANT;

IRRADIATION; KINETICS; PH; PHOSPHATE; PHOTODEGRADATION; PHOTOLYSIS; TESTOSTERONE;

ARTICLE; EXCITATION; IRRADIATION; PH; PHOTODEGRADATION; PHOTOLYSIS; PRIORITY JOURNAL; SPECTROMETRY; SPECTROSCOPY; ANALYSIS; CHEMISTRY; ECOSYSTEM RESTORATION; RADIATION RESPONSE; WATER POLLUTANT;

ENVIRONMENTAL RESTORATION AND REMEDIATION; PHOTOLYSIS; TESTOSTERONE; WATER; WATER POLLUTANTS, CHEMICAL;

EID: 77953812402     PISSN: 00489697     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.scitotenv.2010.05.002     Document Type: Article

References (31)

1. Bandelj E., van den Heuvel M.R., Leush F.D.L., Shannon N., Taylor S., McCarthy L.H. Determination of the androgenic potency of whole effluents using mosquitofish and trout bioassays. Aquat Toxicol 2006, 80:237-248.
2. Barel-Cohen K., Shore S., Shemesh M., Wenzel A., Mueller J., Kronfeld-Schor N. Monitoring of natural and synthetic hormones in a polluted river. J Environ Manage 2006, 78:16-23.
3. Casey F.X.M., Hakk H., Simunek J., Larsen G.L. Fate and transport of testosterone in agricultural soils. Environ Sci Technol 2004, 38:790-798.
4. Chapman O.L., Rettig T.A., Griswold A.A., Dutton A.I., Fitton P. Photochemical rearrangements of 2-cyclohexenones. Tetrahedron Lett 1963, 29:2049-2055.
5. Choudhry G.G., Webster G.R.B. Environmental photochemistry of PCDDs. Quantum yields of the direct phototransformation of 1, 2, 3, 7-Tetra-, 1, 3, 6, 8-Tetra-, 1, 2, 3, 4, 6, 7, 8-Hepta-, and 1, 2, 3, 4, 6, 7, 8, 9-Octachlorodibenzo-p-dioxin in aqueous acetonitrile and their sunlight half-lives. J Agric Food Chem 1989, 37:254-261.
6. Cooper G.F. Synthesis of 5, 17-dihydroxy-5α, 17α-norpregn-20-yn-3-one, a major photodegradation product of norethindrone. Steroids 1988, 51:459-464.
7. Cooper W.J., Zika R.G., Pestane R.G., Fisher A.M. Sunlight-induced photochemistry of humic substances in natural waters: major reactive species. ACS Symp Ser 1989, 219:333-362.
8. Cornell D.G., Avram E., Filipescu N. Photohydratation of testosterone and 4-androstene-3, 17-dione in aqueous solution. Steroids 1979, 33:485-494.
9. Eastman R.H. Conjugative effects of cyclopropane rings. I. Synthesis and properties of 1-methyl-4-isopropyltricyclo[4, 1, 01, 6, 02, 4]heptanon-5. JACS 1954, 76:4115-4117.
10. Finlay-Moore O., Hartel P.G., Cabrera M.L. 17ß-Estradiol and testosterone in soil and runoff from grasslands amended with broiler litter. J Environ Qual 2000, 29:1604-1611.
11. 4-steroids. J Chem Soc (C) 1967, 2459-2465.
12. Jacobsen A.M., Lorenzen A., Chapman R., Topp E. Persistence of testosterone and 17β-estradiol in soils receiving swine manure or municipal biosolids. J Environ Qual 2005, 34:861-871.
13. Jankowska R., Mhehe G.L., Hsing-Jang L. Lithium naphtalenide induced reductive cleavage of α, β-epoxy ketones: an efficient procedure for the preparation of β-hydroxy ketones. Chem Commun 1999, 16:1581-1582.
14. Kim S.D., Cho J., Kim I.S., Vanderford B.J., Snyder S.A. Occurrence and removal of pharmaceuticals and endocrine disruptors in South Korean surface, drinking, and waste waters. Water Res 2007, 41:1013-1021.
15. Kolodziej E.P., Harter T., Sedlak D.L. Dairy wastewater, aquaculture, and spawning fish as sources of steroid hormones in the aquatic environment. Environ Sci Technol 2004, 38:6377-6384.
16. Kolpin D.W., Furlong E.T., Meyer M.T., Thurman E.M., Zaugg S.D., Barber L.B., et al. Pharmaceutical, hormones, and other organics wastewater contaminants in U.S. streams, 1999-2000: a national reconnaissance. Environ Sci Technol 2002, 36:1202-1211.
17. Kuhn H.J., Braslavsky S.E., Schmidt R. Chemical actinometry. Pure Appl Chem 2004, 76:2105-2146.
18. Kwie W.W., Shoulders B.A., Gardner P.D. Photoisomerization of Δ4-cholesten-3-one. J Am Chem Soc 1962, 84:2268-2269.
19. Lorenzen A., Chapman R., Hendel J.G., Topp Persistence and pathways of testosterone dissipation in agricultural soil. J Environ Qual 2005, 34:854-860.
20. Mills L.J., Chichester C. Review of evidence: are endocrine-disrupting chemicals in the aquatic environment impacting fish populations?. Sci Total Environ 2005, 343:1-34.
21. Shoulders B.A., Kwie W.W., Klyne W., Gardner P.D. The structure of lumi-4-cholesten-3-one. Tetrahedron 1965, 21:2973-2981.
22. Solomon G.M., Schettler T. Environment and health: 6. Endocrine disruption and potential human health implications. Can Med Assoc J 2000, 163:1471-1476.
23. Su M.D. The role of spin-orbit coupling and symmetry in photochemical rearrangements of α, β-unsaturated cyclic ketones. Chem Phys 1996, 205:277-308.
24. Trenholm R.A., Vanderford B.J., Holady J.C., Rexing D.J., Snyder S.A. Broad range of endocrine disruptors and pharmaceuticals using gas chromatography and liquid chromatography tandem mass spectrometry. Chemosphere 2006, 65:1990-1998.
25. Vulliet E., Baugros J.B., Flament-Waton M.M., Grenier-Loustalot M.F. Analytical methods for the determination of selected steroid sex hormones and corticosteriods in wastewater. Anal Bioanal Chem 2007, 387:2143-2151.
26. Vulliet E., Wiest L., Baudot R., Grenier-Loustalot M.F. Multi-residue analysis of steroids at sub ng/L levels in surface and ground-waters using liquid chromatography coupled to mass tandem spectrometry. J Chromatogr A 2008, 1210:84-91.
27. Wan H.B., Wong M.K., Mok Y. Comparative study on the quantum yields of direct photolysis of organophosphorus pesticides in aqueous solution. J Agric Food Chem 1994, 42:2625-2630.
28. Waters J.A., Kondo Y., Witkop B. Photochemistry of steroids. J Pharm Sci 1972, 61:321-334.
29. Williams J.R., Moore R.H., Li R., Weeks C.M. Photochemistry of 11α- and 11β-hydroxy steroidal 1, 4-dien-3-ones and 11α- and 11β-hydroxy steroidal bicycle[3.1.0]hex-3-en-2-ones in neutral and acidic media. J Org Chem 1980, 45:2324-2331.
30. Zepp R.G., Cline D.M. Rates of direct photolysis in aquatic environment. Environ Sci Technol 1977, 11:359-366.
31. Zimmerman H.E., Lewis R.G., McCullough J.J., Padwa A., Staley S., Semmelhack M. The relation of cyclohexenone to cyclohaxadienone rearrangements. Mechanistic organic photochemistry. JACS 1966, 88:159-161.