Artigo Acesso aberto Revisado por pares

Toxicity and Health Threats of Phthalate Esters: Review of the Literature

1973; National Institute of Environmental Health Sciences; Volume: 4; Linguagem: Inglês

10.2307/3428178

ISSN

1552-9924

Autores

John Autian,

Tópico(s)

3D Printing in Biomedical Research

Resumo

Research ArticleOpen AccessToxicity and health threats of phthalate esters: review of the literature. J Autian J Autian Search for more papers by this author Published:1 June 1973https://doi.org/10.1289/ehp.73043Cited by:165AboutSectionsPDF ToolsDownload CitationsTrack Citations ShareShare onFacebookTwitterLinked InReddit FiguresReferencesRelatedDetailsCited bySui Y, Meng Z, Chen J, Liu J, Hernandez R, Gonzales M, Gwag T, Morris A and Zhou C (2021) Effects of Dicyclohexyl Phthalate Exposure on PXR Activation and Lipid Homeostasis in Mice, Environmental Health Perspectives, 129:12, Online publication date: 1-Dec-2021. Deshpande T, Quadir A, Obara S, Ibrahim A and Hoag S (2018) Developing a stable aqueous enteric coating formulation with hydroxypropyl methylcellulose acetate succinate (HPMCAS-MF) and colloidal silicon dioxide as anti-tacking agent, International Journal of Pharmaceutics, 10.1016/j.ijpharm.2018.02.025, 542:1-2, (108-116), Online publication date: 1-May-2018. Qin X, Ma Q, Yuan J, Hu X, Tan Q, Zhang Z, Wang L and Xu X (2018) The effects of di-2-ethylhexyl phthalate on testicular ultrastructure and hormone-regulated gene expression in male rats, Toxicology Research, 10.1039/C7TX00257B, 7:3, (408-414) Lin X, Ma Y, Wan J and Wang Y (2017) LiCoPO 4 (LCP) as an effective peroxymonosulfate activator for degradation of diethyl phthalate in aqueous solution without controlling pH: Efficiency, stability and mechanism, Chemical Engineering Journal, 10.1016/j.cej.2017.01.036, 315, (304-314), Online publication date: 1-May-2017. Walsh J, Lenes J, Weisberg R, Zheng L, Hu C, Fanning K, Snyder R and Smith J (2017) More surprises in the global greenhouse: Human health impacts from recent toxic marine aerosol formations, due to centennial alterations of world-wide coastal food webs, Marine Pollution Bulletin, 10.1016/j.marpolbul.2016.12.053, 116:1-2, (9-40), Online publication date: 1-Mar-2017. Han Y, Diao D, Lu Z, Li X, Guo Q, Huo Y, Xu Q, Li Y, Cao S, Wang J, Wang Y, Zhao J, Li Z, He M, Luo Z and Lou X (2017) Selection of Group-Specific Phthalic Acid Esters Binding DNA Aptamers via Rationally Designed Target Immobilization and Applications for Ultrasensitive and Highly Selective Detection of Phthalic Acid Esters, Analytical Chemistry, 10.1021/acs.analchem.6b04808, 89:10, (5270-5277), Online publication date: 16-May-2017. Zhu X, Li F, Qiu Z and Huang J (2017) Migration of DEHP from plastic to food simulants under microwave heating, IOP Conference Series: Earth and Environmental Science, 10.1088/1755-1315/64/1/012050, 64, (012050), Online publication date: 1-May-2017. Morgenstern R, Whyatt R, Insel B, Calafat A, Liu X, Rauh V, Herbstman J, Bradwin G and Factor-Litvak P (2017) Phthalates and thyroid function in preschool age children: Sex specific associations, Environment International, 10.1016/j.envint.2017.05.007, 106, (11-18), Online publication date: 1-Sep-2017. Phan-Vu D and Tan C (2017) Synthesis of phthalate-free plasticizers by hydrogenation in water using RhNi bimetallic catalyst on aluminated SBA-15, RSC Advances, 10.1039/C7RA02227A, 7:30, (18178-18188) Cheng Z, Li H, Wang H, Zhu X, Sthiannopkao S, Kim K, Yasin M, Hashim J and Wong M (2016) Dietary exposure and human risk assessment of phthalate esters based on total diet study in Cambodia, Environmental Research, 10.1016/j.envres.2016.06.011, 150, (423-430), Online publication date: 1-Oct-2016. Shoombuatong W, Nabu S, Simeon S, Prachayasittikul V, Lapins M, Wikberg J and Nantasenamat C (2016) Extending proteochemometric modeling for unraveling the sorption behavior of compound–soil interaction, Chemometrics and Intelligent Laboratory Systems, 10.1016/j.chemolab.2016.01.002, 151, (219-227), Online publication date: 1-Feb-2016. Russo M, Avino P, Perugini L and Notardonato I (2015) Extraction and GC-MS analysis of phthalate esters in food matrices: a review, RSC Advances, 10.1039/C5RA01916H, 5:46, (37023-37043) Wang Y, Zhang G and Wang L (2014) Potential Toxicity of Phthalic Acid Esters Plasticizer: Interaction of Dimethyl Phthalate with Trypsin in Vitro, Journal of Agricultural and Food Chemistry, 10.1021/jf5046359, 63:1, (75-84), Online publication date: 14-Jan-2015. Chang L, Bi P, Li X and Wei Y (2015) Study of solvent sublation for concentration of trace phthalate esters in plastic beverage packaging and analysis by gas chromatography–mass spectrometry, Food Chemistry, 10.1016/j.foodchem.2015.01.013, 177, (127-133), Online publication date: 1-Jun-2015. Zhang L, Liu J, Liu H, Wan G and Zhang S (2015) The occurrence and ecological risk assessment of phthalate esters (PAEs) in urban aquatic environments of China, Ecotoxicology, 10.1007/s10646-015-1446-4, 24:5, (967-984), Online publication date: 1-Jul-2015. Kwack S and Lee B (2015) Comparative Cytotoxicity and Sperm Motility Using a Computer-Aided Sperm Analysis System (CASA) for Isomers of Phthalic Acid, a Common Final Metabolite of Phthalates, Journal of Toxicology and Environmental Health, Part A, 10.1080/15287394.2015.1067503, 78:16, (1038-1050), Online publication date: 18-Aug-2015. Al Salloum H, Saunier J, Aymes-Chodur C, Barakat H and Yagoubi N (2015) Impact of the nature and concentration of plasticizers on the ability of PVC to sorb drug, International Journal of Pharmaceutics, 10.1016/j.ijpharm.2015.11.004, 496:2, (664-675), Online publication date: 1-Dec-2015. (2015) Case Histories and Problem Resolution Biomaterials, Medical Devices, and Combination Products, 10.1201/b19086-23, (517-546), Online publication date: 10-Dec-2015. Karandikar R, Badri A and Phale P (2015) Biochemical Characterization of Inducible ‘Reductase’ Component of Benzoate Dioxygenase and Phthalate Isomer Dioxygenases from Pseudomonas aeruginosa strain PP4, Applied Biochemistry and Biotechnology, 10.1007/s12010-015-1744-6, 177:2, (318-333), Online publication date: 1-Sep-2015. Starling A, Engel L, Calafat A, Koutros S, Satagopan J, Yang G, Matthews C, Cai Q, Buckley J, Ji B, Cai H, Chow W, Zheng W, Gao Y, Rothman N, Xiang Y and Shu X (2015) Predictors and long-term reproducibility of urinary phthalate metabolites in middle-aged men and women living in urban Shanghai, Environment International, 10.1016/j.envint.2015.07.003, 84, (94-106), Online publication date: 1-Nov-2015. Bhatia H, Kumar A, Chapman J and McLaughlin M (2014) Long-term exposures to di-n-butyl phthalate inhibit body growth and impair gonad development in juvenile Murray rainbowfish ( Melanotaenia fluviatilis ) , Journal of Applied Toxicology, 10.1002/jat.3076, 35:7, (806-816), Online publication date: 1-Jul-2015. Al-Natsheh M, Alawi M, Fayyad M and Tarawneh I (2015) Simultaneous GC–MS determination of eight phthalates in total and migrated portions of plasticized polymeric toys and childcare articles, Journal of Chromatography B, 10.1016/j.jchromb.2015.01.010, 985, (103-109), Online publication date: 1-Mar-2015. Guo Y, Wang L and Kannan K (2013) Phthalates and Parabens in Personal Care Products From China: Concentrations and Human Exposure, Archives of Environmental Contamination and Toxicology, 10.1007/s00244-013-9937-x, 66:1, (113-119), Online publication date: 1-Jan-2014. Zhang X and Chen Z (2014) Observing Phthalate Leaching from Plasticized Polymer Films at the Molecular Level, Langmuir, 10.1021/la500476u, 30:17, (4933-4944), Online publication date: 6-May-2014. Gad S (2014) Phthalic Anhydride Encyclopedia of Toxicology, 10.1016/B978-0-12-386454-3.01201-X, (934-936), . Sun R and Zhuang H (2014) A sensitive heterogeneous biotin–streptavidin enzyme-linked immunosorbent assay for the determination of di-(2-ethylhexyl)phthalate (DEHP) in beverages using a specific polyclonal antibody, Anal. Methods, 10.1039/C4AY02088J, 6:24, (9807-9815) Bhatia H, Kumar A, Ogino Y, Gregg A, Chapman J, McLaughlin M and Iguchi T (2014) Di-n-butyl phthalate causes estrogenic effects in adult male Murray rainbowfish (Melanotaenia fluviatilis), Aquatic Toxicology, 10.1016/j.aquatox.2014.01.025, 149, (103-115), Online publication date: 1-Apr-2014. Fan Y, Liu S and Xie Q (2014) Rapid determination of phthalate esters in alcoholic beverages by conventional ionic liquid dispersive liquid–liquid microextraction coupled with high performance liquid chromatography, Talanta, 10.1016/j.talanta.2013.11.023, 119, (291-298), Online publication date: 1-Feb-2014. Watkins D, Téllez-Rojo M, Ferguson K, Lee J, Solano-Gonzalez M, Blank-Goldenberg C, Peterson K and Meeker J (2014) In utero and peripubertal exposure to phthalates and BPA in relation to female sexual maturation, Environmental Research, 10.1016/j.envres.2014.08.010, 134, (233-241), Online publication date: 1-Oct-2014. Chen B and Zhang L (2013) An easy and sensitive analytical method of determination of phthalate esters in children's toys by UPLCMS/MS, Polymer Testing, 10.1016/j.polymertesting.2013.02.011, 32:4, (681-685), Online publication date: 1-Jun-2013. 蔡 伊 (2013) Development of Ecotoxicogenomic Biomarkers on the Freshwater Shrimp (Neocaridina denticulate) Following Short-Term Exposure to Dipropyl Phthalate, International Journal of Ecology, 10.12677/IJE.2013.24007, 02:04, (38-49), . Braun J, Sathyanarayana S and Hauser R (2013) Phthalate exposure and childrenʼs health, Current Opinion in Pediatrics, 10.1097/MOP.0b013e32835e1eb6, 25:2, (247-254), Online publication date: 1-Apr-2013. Abdel daiem M, Rivera-Utrilla J, Ocampo-Pérez R, Méndez-Díaz J and Sánchez-Polo M (2012) Environmental impact of phthalic acid esters and their removal from water and sediments by different technologies – A review, Journal of Environmental Management, 10.1016/j.jenvman.2012.05.014, 109, (164-178), Online publication date: 1-Oct-2012. Guo Y and Kannan K (2012) Challenges encountered in the analysis of phthalate esters in foodstuffs and other biological matrices, Analytical and Bioanalytical Chemistry, 10.1007/s00216-012-5999-2, 404:9, (2539-2554), Online publication date: 1-Nov-2012. Zhou J, Cai Z and Xing K (2011) Potential mechanisms of phthalate ester embryotoxicity in the abalone Haliotis diversicolor supertexta, Environmental Pollution, 10.1016/j.envpol.2011.02.016, 159:5, (1114-1122), Online publication date: 1-May-2011. Aoki K, Harris C, Katsiadaki I and Sumpter J (2011) Evidence suggesting that di-n-butyl phthalate has antiandrogenic effects in fish, Environmental Toxicology and Chemistry, 10.1002/etc.502, 30:6, (1338-1345), Online publication date: 1-Jun-2011. Dulazi A and Liu H (2011) Removal of phthalate esters from water using immobilized lipase on chitosan beads, Environmental Technology, 10.1080/09593330.2010.538932, 32:13, (1443-1451), Online publication date: 1-Oct-2011. Molenberghs G and Verbeke G (2011) A note on a hierarchical interpretation for negative variance components, Statistical Modelling: An International Journal, 10.1177/1471082X1001100501, 11:5, (389-408), Online publication date: 1-Oct-2011. Alam M, Andrina B, Tay T, Tsunekawa N, Kanai Y and Kurohmaru M (2010) Single administration of di(n-butyl) phthalate delays spermatogenesis in prepubertal rats, Tissue and Cell, 10.1016/j.tice.2010.02.004, 42:2, (129-135), Online publication date: 1-Apr-2010. Verbeke G and Molenberghs G (2010) Arbitrariness of models for augmented and coarse data, with emphasis on incomplete data and random effects models, Statistical Modelling: An International Journal, 10.1177/1471082X0901000403, 10:4, (391-419), Online publication date: 1-Dec-2010. Molenberghs G and Kenward M (2010) Semi-parametric marginal models for hierarchical data and their corresponding full models, Computational Statistics & Data Analysis, 10.1016/j.csda.2009.09.040, 54:2, (585-597), Online publication date: 1-Feb-2010. Gu J, Han B, Duan S, Zhao Z and Wang Y (2009) Degradation of the endocrine-disrupting dimethyl phthalate carboxylic ester by Sphingomonas yanoikuyae DOS01 isolated from the South China Sea and the biochemical pathway, International Biodeterioration & Biodegradation, 10.1016/j.ibiod.2008.12.004, 63:4, (450-455), Online publication date: 1-Jun-2009. Matsumoto M, Hirata-Koizumi M and Ema M (2008) Potential adverse effects of phthalic acid esters on human health: A review of recent studies on reproduction, Regulatory Toxicology and Pharmacology, 10.1016/j.yrtph.2007.09.004, 50:1, (37-49), Online publication date: 1-Feb-2008. Tanaka N, Nomura Y, Nishikiori R, Shibata S, Shirai K and Fujitani M (2005) Temporary restorative resins using non-phthalate ester plasticizers, Journal of Dentistry, 10.1016/j.jdent.2004.12.004, 33:7, (577-583), Online publication date: 1-Aug-2005. Salazar V, Castillo C, Ariznavarreta C, Campón R and Tresguerres J (2004) Effect of oral intake of dibutyl phthalate on reproductive parameters of Long Evans rats and pre-pubertal development of their offspring, Toxicology, 10.1016/j.tox.2004.06.045, 205:1-2, (131-137), Online publication date: 1-Dec-2004. Silva M, Barr D, Reidy J, Kato K, Malek N, Hodge C, Hurtz D, Calafat A, Needham L and Brock J (2003) Glucuronidation patterns of common urinary and serum monoester phthalate metabolites, Archives of Toxicology, 10.1007/s00204-003-0486-3, 77:10, (561-567), Online publication date: 1-Oct-2003. Ema M, Miyawaki E, Hirose A and Kamata E (2003) Decreased anogenital distance and increased incidence of undescended testes in fetuses of rats given monobenzyl phthalate, a major metabolite of butyl benzyl phthalate, Reproductive Toxicology, 10.1016/S0890-6238(03)00037-6, 17:4, (407-412), Online publication date: 1-Jul-2003. Pietrogrande M, Rossi D and Paganetto G (2003) Gas chromatographic–mass spectrometric analysis of di(2-ethylhexyl) phthalate and its metabolites in hepatic microsomal incubations, Analytica Chimica Acta, 10.1016/S0003-2670(02)01652-5, 480:1, (1-10), Online publication date: 1-Mar-2003. Ema M and Miyawaki E (2002) Effects on development of the reproductive system in male offspring of rats given butyl benzyl phthalate during late pregnancy, Reproductive Toxicology, 10.1016/S0890-6238(01)00200-3, 16:1, (71-76), Online publication date: 1-Jan-2002. Rozati R, Reddy P, Reddanna P and Mujtaba R (2002) Role of environmental estrogens in the deterioration of male factor fertility, Fertility and Sterility, 10.1016/S0015-0282(02)04389-3, 78:6, (1187-1194), Online publication date: 1-Dec-2002. Koo J, Parham F, Kohn M, Masten S, Brock J, Needham L and Portier C (2018) The association between biomarker-based exposure estimates for phthalates and demographic factors in a human reference population., Environmental Health Perspectives, 110:4, (405-410), Online publication date: 1-Apr-2002. Ema M and Miyawaki E (2001) Effects of monobutyl phthalate on reproductive function in pregnant and pseudopregnant rats, Reproductive Toxicology, 10.1016/S0890-6238(01)00131-9, 15:3, (261-267), Online publication date: 1-May-2001. Nakajin S, Shinoda S, Ohno S, Nakazawa H and Makino T (2001) Effect of phthalate esters and alkylphenols on steroidogenesis in human adrenocortical H295R cells, Environmental Toxicology and Pharmacology, 10.1016/S1382-6689(01)00089-8, 10:3, (103-110), Online publication date: 1-Jul-2001. Ema M and Miyawaki E (2001) Adverse effects on development of the reproductive system in male offspring of rats given monobutyl phthalate, a metabolite of dibutyl phthalate, during late pregnancy, Reproductive Toxicology, 10.1016/S0890-6238(01)00111-3, 15:2, (189-194), Online publication date: 1-Mar-2001. Ema M, Miyawaki E and Kawashima K (2000) Effects of dibutyl phthalate on reproductive function in pregnant and pseudopregnant rats, Reproductive Toxicology, 10.1016/S0890-6238(99)00066-0, 14:1, (13-19), Online publication date: 1-Jan-2000. Ema M, Miyawaki E and Kawashima K (2000) Critical period for adverse effects on development of reproductive system in male offspring of rats given di-n-butyl phthalate during late pregnancy, Toxicology Letters, 10.1016/S0378-4274(99)00192-7, 111:3, (271-278), Online publication date: 1-Jan-2000. Ema M, Miyawaki E and Kawashima K (1999) Developmental effects of plasticizer butyl benzyl phthalate after a single administration in rats, Journal of Applied Toxicology, 10.1002/(SICI)1099-1263(199909/10)19:5 3.0.CO;2-X, 19:5, (357-365), Online publication date: 1-Sep-1999. Jha A, Singh A and Bharti M (1998) Germ cell mutagenicity of phthalic acid in mice, Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis, 10.1016/S0027-5107(98)00151-1, 422:2, (207-212), Online publication date: 1-Dec-1998. Rothenbacher K, Kimmel R, Hildenbrand S, Schmahl F and Dartsch P (2016) Nephrotoxic effects of di-(2-ethylhexyl)phthalate (DEHP) hydrolysis products on cultured kidney epithelial cells, Human & Experimental Toxicology, 10.1177/096032719801700609, 17:6, (336-342), Online publication date: 1-Jun-1998. Deisinger P, Perry L and Guest D (1998) In Vivo Percutaneous Absorption of [14C]DEHP from [14C]DEHP-Plasticized Polyvinyl Chloride Film in Male Fischer 344 Rats, Food and Chemical Toxicology, 10.1016/S0278-6915(98)00015-5, 36:6, (521-527), Online publication date: 1-Jun-1998. Ema M, Miyawaki E and Kawashima K (1998) Further evaluation of developmental toxicity of di-n-butyl phthalate following administration during late pregnancy in rats, Toxicology Letters, 10.1016/S0378-4274(98)00107-6, 98:1-2, (87-93), Online publication date: 1-Sep-1998. Ema M, Miyawaki E and Kawashima K (1998) Reproductive effects of butyl benzyl phthalate in pregnant and pseudopregnant rats, Reproductive Toxicology, 10.1016/S0890-6238(97)00127-5, 12:2, (127-132), Online publication date: 1-Mar-1998. Ema M, Miyawaki E, Harazono A and Kawashima K (1997) Developmental toxicity evaluation of phthalic acid, one of the metabolites of phthalic acid esters, in rats, Toxicology Letters, 10.1016/S0378-4274(97)00078-7, 93:2-3, (109-115), Online publication date: 1-Dec-1997. Harris C, Henttu P, Parker M and Sumpter J (2018) The estrogenic activity of phthalate esters in vitro., Environmental Health Perspectives, 105:8, (802-811), Online publication date: 1-Aug-1997. Ema M, Harazono A, Miyawaki E and Ogawa Y (1996) Characterization of developmental toxicity of mono-n-benzyl phthalate in rats, Reproductive Toxicology, 10.1016/0890-6238(96)00082-2, 10:5, (365-372), Online publication date: 1-Sep-1996. Ema M, Kurosaka R, Amano H and Ogawa Y (1995) Developmental toxicity evaluation of mono-n-butyl phthalate in rats, Toxicology Letters, 10.1016/0378-4274(94)03241-X, 78:2, (101-106), Online publication date: 1-Jul-1995. Piersma A, Verhoef A and Dortant P (1995) Evaluation of the OECD 421 reproductive toxicity screening test protocol using butyl benzyl phthalate, Toxicology, 10.1016/0300-483X(95)03029-F, 99:3, (191-197), Online publication date: 1-May-1995. Sharpe R, Fisher J, Millar M, Jobling S and Sumpter J (2018) Gestational and lactational exposure of rats to xenoestrogens results in reduced testicular size and sperm production., Environmental Health Perspectives, 103:12, (1136-1143), Online publication date: 1-Dec-1995.Jobling S, Reynolds T, White R, Parker M and Sumpter J (2018) A variety of environmentally persistent chemicals, including some phthalate plasticizers, are weakly estrogenic., Environmental Health Perspectives, 103:6, (582-587), Online publication date: 1-Jun-1995. Ema M, Amano H and Ogawa Y (1994) Characterization of the developmental toxicity of di-n-butyl phthalate in rats, Toxicology, 10.1016/0300-483X(94)90002-7, 86:3, (163-174), Online publication date: 1-Feb-1994. Ema M, Kurosaka R, Amano H and Ogawa Y (1994) Embryolethality of butyl benzyl phthalate during early pregnancy in rats, Reproductive Toxicology, 10.1016/0890-6238(94)90007-8, 8:3, (231-236), Online publication date: 1-May-1994. Karigar C, Banji S and Pujar B (2013) Degradation of homophthalic acid byAspergillus niger, Current Microbiology, 10.1007/BF01576017, 27:3, (177-180), Online publication date: 1-Sep-1993. Jenke D, Chess E, Zietlow D and Rabinow B (1992) Model for estimating the accumulation of solutes leaching from polymeric containers into parenteral solutions, International Journal of Pharmaceutics, 10.1016/0378-5173(92)90363-7, 78:1-3, (115-122), Online publication date: 1-Jan-1992. Nomura Y, Nakagawa M, Ogawa N, Harashima S and Oshima Y (1992) Genes in PHT plasmid encoding the initial degradation pathway of phthalate in Pseudomonas putida, Journal of Fermentation and Bioengineering, 10.1016/0922-338X(92)90028-S, 74:6, (333-344), Online publication date: 1-Jan-1992. Graham B, Jones D and Sutow E (2016) An in vivo and in vitro Study of the Loss of Plasticizer from Soft Polymer-gel Materials, Journal of Dental Research, 10.1177/00220345910700050101, 70:5, (870-873), Online publication date: 1-May-1991. Kamrin M and Mayor G (2013) Diethyl Phthalate: A Perspective, The Journal of Clinical Pharmacology, 10.1002/j.1552-4604.1991.tb01908.x, 31:5, (484-489), Online publication date: 1-May-1991. Phillips J, Gibson W, Yam J, Alden C and Hard G (1990) Survey of the QSAR and in vitro approaches for developing non-animal methods to supersede the in vivo LD50 test, Food and Chemical Toxicology, 10.1016/0278-6915(90)90112-Z, 28:5, (375-394), Online publication date: 1-Jan-1990. Górski T, Goehl T, Jameson C, Collins B, Bursey J and Moseman R (1990) Gas chromatographic determination of 2-ethylhexanol and 2-ethylhexanoic acid as derivatives suitable for electroncapture and nitrogen-phosphorus detection after single reaction with heptafluorobutyrylimidazole, Journal of Chromatography A, 10.1016/S0021-9673(01)93096-1, 509:2, (383-389), Online publication date: 1-Jan-1990. Kim-Kang H, Gilbert S, Malick A and Johnson J (1990) Methods for Predicting Migration to Packaged Pharmaceuticals, Journal of Pharmaceutical Sciences, 10.1002/jps.2600790209, 79:2, (120-123), Online publication date: 1-Feb-1990. Nomura Y, Takada N and Oshima Y (1989) Isolation and identification of phthalate-utilizing bacteria, Journal of Fermentation and Bioengineering, 10.1016/0922-338X(89)90235-3, 67:4, (297-299), Online publication date: 1-Jan-1989. Ganning A, Olsson M, Elhammer Å and Dallner G (1989) The influence of di(2-ethylhexyl)phthalate on protein turnover in rat liver, Toxicology Letters, 10.1016/0378-4274(89)90173-2, 48:2, (185-192), Online publication date: 1-Aug-1989. Nelson B, Vorhees C, Scott W and Hastings L (1989) Effects of 2-methoxyethanol on fetal development, postnatal behavior, and embryonic intracellular pH of rats, Neurotoxicology and Teratology, 10.1016/0892-0362(89)90070-6, 11:3, (273-284), Online publication date: 1-May-1989. Nomura Y, Harashima S and Oshima Y (1989) A simple method for detection of enzyme activities involved in the initial step of phthalate degradation in microorganisms, Journal of Fermentation and Bioengineering, 10.1016/0922-338X(89)90234-1, 67:4, (291-296), Online publication date: 1-Jan-1989. Cummings A and Gray L (1987) Dibutyl phthalate: Maternal effects versus fetotoxicity, Toxicology Letters, 10.1016/0378-4274(87)90255-4, 39:1, (43-50), Online publication date: 1-Nov-1987. Agarwal D, Eustis S, Lamb J, Jameson C and Kluwe W (1986) Influence of dietary zinc on di(2-ethylhexyl)phthalate-induced testicular atrophy and zinc depletion in adult rats, Toxicology and Applied Pharmacology, 10.1016/0041-008X(86)90412-6, 84:1, (12-24), Online publication date: 1-Jun-1986. Eigenberg D, Carter D, Schram K and Sipes I (1986) Examination of the differential hepatotoxicity of diallyl phthalate in rats and mice, Toxicology and Applied Pharmacology, 10.1016/0041-008X(86)90395-9, 86:1, (12-21), Online publication date: 1-Oct-1986. Preston M and Al-Omran L (1986) Dissolved and particulate phthalate esters in the River Mersey Estuary, Marine Pollution Bulletin, 10.1016/0025-326X(86)90568-0, 17:12, (548-553), Online publication date: 1-Dec-1986. DeAngelo A, Garrett C, Manolukas L and Yario T (1986) DI-n-Octyl phthalate (DOP), a relatively ineffective peroxisome inducing straight chain isomer of the environmental contaminant DI(2-ethylhexyl)phthalate (DEHP), enhances the development of putative preneoplastic lesions in rat liver, Toxicology, 10.1016/0300-483X(86)90182-4, 41:3, (279-288), Online publication date: 1-Nov-1986. Russell D and McDuffie B (1986) Chemodynamic properties of phthalate esters: Partitioning and soil migration, Chemosphere, 10.1016/0045-6535(86)90553-9, 15:8, (1003-1021), Online publication date: 1-Jan-1986. Kluwe W (2018) Carcinogenic potential of phthalic acid esters and related compounds: structure-activity relationships., Environmental Health Perspectives, 65, (271-278), Online publication date: 1-Mar-1986. (2016) 7 Final Report on the Safety Assessment of Dibutyl Phthalate, Dimethyl Phthalate, and Diethyl Phthalate, Journal of the American College of Toxicology, 10.3109/10915818509078674, 4:3, (267-303), Online publication date: 1-May-1985. Agarwal D, Maronpot R, Lamb J and Kluwe W (1985) Adverse effects of butyl benzyl phthalate on the reproductive and hematopoietic systems of male rats, Toxicology, 10.1016/0300-483X(85)90015-0, 35:3, (189-206), Online publication date: 1-Jun-1985. Agarwal D, Lawrence W and Autian J (2009) Antifertility and mutagenic effects in mice from parenteral administration of di‐2‐ethylhexyl phthalate (DEHP), Journal of Toxicology and Environmental Health, 10.1080/15287398509530720, 16:1, (71-84), Online publication date: 1-Jan-1985. Agarwal D, Lawrence W, Nunez L and Autian J (2009) Mutagenicity evaluation of phthalic acid esters and metabolites in salmonella typhimurium cultures , Journal of Toxicology and Environmental Health, 10.1080/15287398509530719, 16:1, (61-69), Online publication date: 1-Jan-1985. DeAngelo A, Queral A and Garrett C (2018) Concentration-dependent inhibition of development of GGT positive foci in rat liver by the environmental contaminant di(2-ethylhexyl) phthalate., Environmental Health Perspectives, 60, (381-385), Online publication date: 1-May-1985. DeAngelo A, Garrett C and Queral A (1984) Inhibition of phenobarbital and dietary choline deficiency promoted preneoplastic lesions in rat liver by environmental contaminant di(2-ethylhexyl)phthalate, Cancer Letters, 10.1016/0304-3835(84)90100-9, 23:3, (323-330), Online publication date: 1-Jul-1984. Jäckh R, Rhodes C, Grasso P and Carter J (1984) Genotoxicity studies on Di-(2-ethylhexyl) phthalate and adipate and toxicity studies on Di-(2-ethylhexyl) phthalate in the rat and marmoset, Food and Chemical Toxicology, 10.1016/0278-6915(84)90096-6, 22:2, (151-155), Online publication date: 1-Feb-1984. Oishi S (1984) Testicular atrophy of rats induced by di-2-ethylhexyl phthalate: effects of vitamin a and zinc concentrations in the testis, liver and serum, Toxicology Letters, 10.1016/0378-4274(84)90186-3, 20:1, (75-78), Online publication date: 1-Jan-1984. Thomas J, Thomas M and Gangolli S (2008) Biological Effects of DI-(2-Ethylhexyl) Phthalate and Other Phthalic Acid Esters, CRC Critical Reviews in Toxicology, 10.3109/10408448409023761, 13:4, (283-317), Online publication date: 1-Jan-1984. Fatiadi A (1984) Priority toxic pollutants in human urine: Their occurrence and analysis, Environment International, 10.1016/0160-4120(84)90094-1, 10:2, (175-205), Online publication date: 1-Jan-1984. Ganning A, Brunk U and Dallner G (1983) Effects of dietary di(2-ethylhexyl)phthalate on the structure and function of rat hepatocytes, Biochimica et Biophysica Acta (BBA) - Molecular Cell Research, 10.1016/0167-4889(83)90027-7, 763:1, (72-82), Online publication date: 1-Aug-1983. Ishikawa Y, Honda K, Sasakawa S, Halada K and Kobayashi H (1983) Prevention of Leakage of Di-(2-ethylhexyl)phthalate from Blood Bags by Glow Discharge Treatment and Its Effect on Aggregability of Stored Platelets, Vox Sanguinis, 10.1111/j.1423-0410.1983.tb04125.x, 45:1, (68-76), Online publication date: 1-Jul-1983. Deangelo A and Garrett C (1983) Inhibition of development of preneoplastic lesions in the livers of rats fed a weakly carcinogenic environmental contaminant, Cancer Letters, 10.1016/0304-3835(83)90049-6, 20:2, (199-205), Online publication date: 1-Sep-1983. Rathinam K, Fernandez A, Vedanarayanan P, Bhujle V and Srinivasan K (1983) The occurrence of phthalic acid esters in various samples of commercially available sodium chloride injections (Indian Pharmacopoeia), Toxicology Letters, 10.1016/0378-4274(83)90152-2, 15:4, (329-333), Online publication date: 1-Mar-1983. Phillips B, James T and Gangoli S (1982) Genotoxicity studies of di(2-ethylhexyl)phthalate and its metabolites in CHO cells, Mutation Research/Genetic Toxicology, 10.1016/0165-1218(82)90139-2, 102:3, (297-304), Online publication date: 1-Oct-1982. Kaul A, Souney P and Osathanondh R (2016) A Review of Possible Toxicity of DI-2-Ethylhexylphthalate (DEHP) in Plastic Intravenous Containers: Effects on Reproduction, Drug Intelligence & Clinical Pharmacy, 10.1177/106002808201600908, 16:9, (689-692), Online publication date: 1-Sep-1982. Ekwall B, Nordensten C and Albanus L (1982) Toxicity of 29 plasticizers to HeLa cells in the MIT-24 system, Toxicology, 10.1016/0300-483X(82)90002-6, 24:3-4, (199-210), Online publication date: 1-Jan-1982. Kluwe W, Haseman J, Douglas J and Huff J (2009) The carcinogenicity of dietary di(2‐ethylhexyl) phthalate (DEHP) in fischer 344 rats and B6C3F 1 mice , Journal of Toxicology and Environmental Health, 10.1080/15287398209530296, 10:4-5, (797-815), Online publication date: 1-Oct-1982. ARCOS J, WOO Y and ARGUS M (1982) Structure-Activity Relationships Aliphatic Carcinogens, 10.1016/B978-0-12-059303-3.50007-8, (1-681), . Eaton R and Ribbons D (1982) The transformation of phthalaldehydate by phthalate-grown Micrococcus strain 12B, Archives of Biochemistry and Biophysics,

Referência(s)