Skip to main content

Analysis of Endocrine Disrupting Chemicals in Food Samples

  • Chapter
Electrokinetics Across Disciplines and Continents

Abstract

Endocrine disrupting compounds are organic compounds that are present in low concentrations in food and environmental samples. These compounds are suspected to cause dysfunction of the endocrine system in humans and animals. This chapter briefly presents an overview on some important endocrine disrupting compounds as well as matrices, where their determination is pertinent. Advanced sample preparation methods, using low solvent amounts, together with new multidimensional analytical methods to perform the analysis of endocrine disrupting compounds are also discussed. Comprehensive two-dimensional gas chromatography has been successfully applied to the analysis of some endocrine disrupting compounds. Dibutylphthalate, benzylbutylphthalate, nonylphenol, and octylphenol were quantified using comprehensive two-dimensional gas chromatography with a flame ionization detector. The merit parameters of the analytical method were determined. The compounds were evaluated throughout a concentration range of 0.2–6.0 μg L−1. LOD ranging from 0.07 to 0.32 μg L−1 and LOQ ranging from 0.17 to 0.55 μg L−1 were obtained for these four compounds.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 149.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 109.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  • Amorim LCA, Dimandja J-M, Cardeal ZL (2009) Analysis of hydroxylated polycyclic aromatic hydrocarbons in urine using comprehensive two-dimensional gas chromatography with a flame ionization detector. J Chromatogr A 1216(14):2900–2904

    Article  CAS  Google Scholar 

  • Andrews R, Paterson S (2012) A validated method for the analysis of cannabinoids in post-mortem blood using liquid–liquid extraction and two-dimensional gas chromatography-mass spectrometry. Forensic Sci Int 222(1–3):111–117

    Article  CAS  Google Scholar 

  • Batlle R, Nerín C (2004) Application of single-drop microextraction to the determination of dialkyl phthalate esters in food simulants. J Chromatogr A 1045(1–2):29–35

    Article  CAS  Google Scholar 

  • Brix RS, Hvidt S, Carlsen L (2001) Solubility of nonylphenol and nonylphenol ethoxylates. On the possible role of micelles. Chemosphere 44(4):759–763

    Article  CAS  Google Scholar 

  • Bruckner CA, Prazen BJ, Synovec RE (1998) Comprehensive two dimensional high-speed gas chromatography with chemometric analysis. Anal Chem 70(14):2796–2804

    Article  CAS  Google Scholar 

  • Cacho JI, Campillo N, Viñas P, Hernández-Córdoba M (2012) Determination of alkylphenols and phthalate esters in vegetables and migration studies from their packages by means of stir bar sorptive extraction coupled to gas chromatography-mass spectrometry. J Chromatogr A 1241:21–27

    Article  CAS  Google Scholar 

  • Cardeal ZL, Gomes da Silva MD, Marriott PJ (2006) Comprehensive two-dimensional gas chromatography/mass spectrometric analysis of pepper volatiles. Rapid Commun Mass Spectrom 20:2823–2836

    Article  CAS  Google Scholar 

  • Cardeal ZL, Patricio P, Gomes da Silva MDR, Marriott PJ (2008) Comprehensive two-dimensional gas chromatography for fingerprint pattern recognition in cachaça production. Talanta 74:793–799

    Article  CAS  Google Scholar 

  • Cavaliere B, Macchione B, Sindona G, Tagarelli A (2008) Tandem mass spectrometry in food safety assessment: the determination of phthalates in olive oil. J Chromatogr A 1205(1–2):137–143

    Article  CAS  Google Scholar 

  • Cirillo T, Fasano E, Castaldi E, Montuori P, Cocchieri RA (2011) Children’s exposure to di(2-ethylhexyl)phthalate and dibutylphthalate plasticizers from school meals. J Agric Food Chem 59(19):10532–10538

    Article  CAS  Google Scholar 

  • Dallüge J, Beens J, Brinkman UAT (2003) Comprehensive two-dimensional gas chromatography: a powerful and versatile analytical tool. J Chromatogr A 1000(1–2):69–108

    Article  Google Scholar 

  • Del Carlo M, Pepe A, Sacchetti G, Compagnone D, Mastrocola D, Cichelli A (2008) Determination of phthalate esters in wine using solid-phase extraction and gas chromatography-mass spectrometry. Food Chem 111(3):771–777

    Article  Google Scholar 

  • Djokic MR, Dijkmans T, Yildiz G, Prins W, Van Geem KM (2012) Quantitative analysis of crude and stabilized bio-oils by comprehensive two-dimensional gas-chromatography. J Chromatogr A 1257:131–140

    Article  CAS  Google Scholar 

  • EC (2000) European Commission DG ENV-towards the establishment of a priority list of substances for further evaluation of their role in endocrine disruption. http://ec.europa.eu/environment/archives/docum/pdf/bkh_main.pdf. Accessed November 2013

  • EC (2001) European Commission Environment—communication from the commission to the council and the European parliament. http://ec.europa.eu/environment/archives/docum/01262_en.htm#bkh. Accessed November 2013

  • EFSA (2005a) Opinion of the scientific panel on food additives, flavouring, processing aids and material in contact with food on a request from the Commission related to bis(2-ethylhexyl) phthalate (DEHP) for use in food contact materials—European Food Safety Authority. EFSA J 243:1–20

    Google Scholar 

  • EFSA (2005b) Opinion of the scientific panel on food additives, flavouring, processing aids and material in contact with food on a request from the commission related to butylbenzyl phthalate (BBP) for use in food contact materials—European Food Safety Authority. EFSA J 241:1–14

    Google Scholar 

  • EFSA (2005c) Opinion of the scientific panel on food additives, flavouring, processing aids and material in contact with food on a request from the Commission related to di-butyl phthalate (DBP) for use in food contact materials—European Food Safety Authority. EFSA J 242:1–17

    Google Scholar 

  • Farajzadeh MA, Mogaddam MRA (2012) Air-assisted liquid–liquid microextraction method as a novel microextraction technique; Application in extraction and preconcentration of phthalate esters in aqueous sample followed by gas chromatography-flame ionization detection. Anal Chim Acta 728:31–38

    Article  CAS  Google Scholar 

  • Feng CH, Jiang SR (2012) Micro-scale quantitation of ten phthalate esters in water samples and cosmetics using capillary liquid chromatography coupled to UV detection: effective strategies to reduce the production of organic waste. Microchim Acta 177(1–2):167–175

    Article  CAS  Google Scholar 

  • Feng YL, Zhu JP, Sensenstein R (2005) Development of a headspace solid-phase microextraction method combined with gas chromatography mass spectrometry for the determination of phthalate esters in cow milk. Anal Chim Acta 538(1–2):41–48

    Article  CAS  Google Scholar 

  • Ferguson KK, Cantonwine DE, Rivera-Gonzalez LO, Loch-Caruso R, Mukherjee B, Del Toro LVA, Jimenez-Velez B, Calafat AM, Ye X, Alshawabkeh AN, Cordero JF, Meeker JD (2014) Urinary phthalate metabolite associations with biomarkers of inflammation and oxidative stress across pregnancy in Puerto Rico. Environ Sci Technol 48:7018–7025

    Article  CAS  Google Scholar 

  • Fromme H, Kuchler T, Otto T, Pilz K, Müller J, Wenzel A (2002) Occurrence of phthalates and bisphenol A and F in the environment. Water Res 36(6):1429–1438

    Article  CAS  Google Scholar 

  • Gonzalez-Castro MI, Olea-Serrano MF, Rivas-Velasco AM, Medina-Riviero E, Ordoñez-Acevedo LG, De León-Rodríguez A (2011) Phthalates and bisphenols migration in mexican food cans and plastic food containers. Bull Environ Contam Toxicol 86(6):627–631

    Article  CAS  Google Scholar 

  • Gu YY, Yu XJ, Peng JF, Chen SB, Zhong YY, Yin DQ, Hu XL (2014) Simultaneous solid phase extraction coupled with liquid chromatography tandem mass spectrometry and gas chromatography tandem mass spectrometry for the highly sensitive determination of 15 endocrine disrupting chemicals in seafood. J Chromatogr B 965:164–172

    Article  CAS  Google Scholar 

  • Guenther K, Heinke V, Thiele B, Kleist E, Prast H, Raecker T (2002) Endocrine disrupting nonylphenols are ubiquitous in food. Environ Sci Technol 36(8):1676–1680

    Article  CAS  Google Scholar 

  • Guenther K, Kleist E, Thiele B (2006) Estrogen-active nonylphenols from an isomer-specific viewpoint: a systematic numbering system and future trends. Anal Bioanal Chem 384(2):542–546

    Article  CAS  Google Scholar 

  • Hauser R, Meeker JD, Singh NP, Silva MJ, Ryan L, Duty S, Calafat AM (2007) DNA damage in human sperm is related to urinary levels of phthalate monoester and oxidative metabolites. Hum Reprod 22(3):688–695

    Article  CAS  Google Scholar 

  • Huang L-P, Lee C-C, Hsu PC, Shih TS (2011) The association between semen quality in workers and the concentration of di(2-ethylhexyl) phthalate in polyvinyl chloride pellet plant air. Fertil Steril 96(1):90–94

    Article  CAS  Google Scholar 

  • Ibrahim N, Osman R, Abdullah A, Saim N (2014) Determination of phthalate plasticisers in palm oil using online solid phase extraction-liquid chromatography (SPE-LC). J Chem. Article ID 682975, 9 pp., doi:10.1155/2014/682975

    Google Scholar 

  • IPCS/WHO (2002) International Programme on Chemical Safety-Global assessment of the state of the science of endocrine disruptors. http://www.who.int/ipcs/publications/new_issues/endocrine_disruptors/en/

  • Klosterhaus SL, Grace R, Hamilton MC, Yee D (2013) Method validation and reconnaissance of pharmaceuticals, personal care products, and alkylphenols in surface waters, sediments, and mussels in an urban estuary. Environ Int 54:92–99

    Article  CAS  Google Scholar 

  • Kueseng P, Thavarungkul P, Kanatharana P (2007) Trace phthalate and adipate esters contaminated in packaged food. J Environ Sci Health B 42(5):569–576

    Article  CAS  Google Scholar 

  • Li Y, Zhang S, Song C, You J (2013) Determination of bisphenol a and alkylphenols in soft drinks by high-performance liquid chromatography with fluorescence detection. Food Anal Methods 6(5):1284–1290

    Article  Google Scholar 

  • Marriott P, Shellie R (2002) Principles and applications of comprehensive two-dimensional gas chromatography. TrAC Trends Anal Chem 21(9–10):573–583

    Article  CAS  Google Scholar 

  • Mateus EP, Gomes da Silva MDR, Ribeiro AB, Marriott PJ (2008) Qualitative mass spectrometric analysis of the volatile fraction of creosote treated railway wood sleepers by using comprehensive two-dimensional gas chromatography. J Chromatogr A 1178:215–222

    Article  CAS  Google Scholar 

  • Mateus EP, Barata RC, Zrostlíková J, Gomes da Silva MDR, Paiva MR (2010) Characterization of the volatile fraction emitted by Pinus spp by one and two dimensional chromatographic techniques with mass spectrometric detection. J Chromatogr A 1217:1845–1855

    Article  CAS  Google Scholar 

  • Meeker JD, Ferguson KK (2011) Relationship between urinary phthalate and bisphenol A concentrations and serum thyroid measures in US Adults and Adolescents from the National Health and Nutrition Examination Survey (NHANES) 2007–2008. Environ Health Perspect 119(10):1396–1402

    Article  CAS  Google Scholar 

  • Menezes HC, Cardeal ZL (2011) Determination of polycyclic aromatic hydrocarbons from ambient air particulate matter using a cold fiber solid phase microextraction gas chromatography–mass spectrometry method. J Chromatogr A 1218:3300–3305

    Article  CAS  Google Scholar 

  • Moreira DS, Aquino SF, Afonso RJ, Santos EP, de Pádua VL (2009) Occurrence of endocrine disrupting compounds in water sources of Belo Horizonte Metropolitan Area, Brazil. Environ Technol 30(10):1041–1049

    Article  CAS  Google Scholar 

  • Moreira MA, André LC, Cardeal ZL (2014) Analysis of phthalate migration to food simulants in plastic containers during microwave operations. Int J Environ Res Public Health 11(1):507–526

    Article  Google Scholar 

  • Moreira MA, André LC, Ribeiro AB, Gomes da Silva MDR, Cardeal ZL (2015) Quantitative analysis of endocrine disruptors by comprehensive two-dimensional gas chromatography. J Braz Chem Soc 26(3):531–536

    CAS  Google Scholar 

  • Murray JA (2012) Qualitative and quantitative approaches in comprehensive two-dimensional gas chromatography. J Chromatogr A 1261:58–68

    Article  CAS  Google Scholar 

  • Nanni N, Fiselier K, Grob K, Di Pasquale M, Fabrizi L, Aureli P, Coni E (2011) Contamination of vegetable oils marketed in Italy by phthalic acid esters. Food Control 22(2):209–214

    Article  CAS  Google Scholar 

  • Ostrovsky I, Cabala R, Kubinec R, Górová R, Blaško J, Kubincová J, Řimnáčová L, Lorenz W (2011) Determination of phthalate sum in fatty food by gas chromatography. Food Chem 124(1):392–395

    Article  CAS  Google Scholar 

  • Ozaki A, Baba T (2003) Alkylphenol and bisphenol A levels in rubber products. Food Addit Contam 20(1):92–98

    Article  CAS  Google Scholar 

  • Pedroso MP, de Godoy LAF, Fidélis CHV, Ferreira EC, Poppi RJ, Augusto F (2009) Comprehensive two-dimensional gas chromatography (GC × GC). Quim Nova 32(2):421–430

    Article  CAS  Google Scholar 

  • Petrovic M, Eljarrat E, de Alda MJL, Barceló D (2002) Recent advances in the mass spectrometric analysis related to endocrine disrupting compounds in aquatic environmental samples. J Chromatogr A 974(1–2):23–51

    Article  CAS  Google Scholar 

  • Ribeiro LH, Costa Freitas AM, Gomes da Silva MDR (2008) The use of headspace solid phase microextraction for characterization of volatile compounds in olive oil matrices. Talanta 77:110–117

    Article  CAS  Google Scholar 

  • Romero-Franco M, Hernandez-Ramirez RU, Calafat AM, Cebrián ME, Needham LL, Teitelbaum S, Wolff MS, López-Carrillo L (2011) Personal care product use and urinary levels of phthalate metabolites in Mexican women. Environ Int 37(5):867–871

    Article  CAS  Google Scholar 

  • Schroder HF (2001) Tracing of surfactants in the biological wastewater treatment process and the identification of their metabolites by flow injection-mass spectrometry and liquid chromatography-mass spectrometry and -tandem mass spectrometry. J Chromatogr A 926(1):127–150

    Article  CAS  Google Scholar 

  • Shen Y, Ren ML, Feng X, Gao YX, Xu Q, Cai YL (2014) Does nonylphenol promote the growth of uterine fibroids? Eur J Obstet Gynecol Reprod Biol 178:134–137

    Article  CAS  Google Scholar 

  • USEPA (2001) U.S. Environmental Protection Agency. Report No. EPA/625/R-00/015, Washington, DC

    Google Scholar 

  • USEPA (2015) United States-Environmental Protection Agency—National Exposure Research Laboratory Environmental Sciences. http://www.epa.gov/esd/chemistry/org-anal/faq.htm. Accessed February 2015

  • Vallejo A, Olivares M, Fernández LA, Etxebarria N, Arrasate S, Anakabe E, Usobiaga A, Zuloaga O (2011) Optimization of comprehensive two dimensional gas chromatography-flame ionization detection-quadrupole mass spectrometry for the separation of octyl- and nonylphenol isomers. J Chromatogr A 1218(20):3064–3069

    Article  CAS  Google Scholar 

  • Vendeuvre C, Bertoncini F, Duval L, Duplan JL, Thiébaut D, Hennion MC (2004) Comparison of conventional gas chromatography and comprehensive two-dimensional gas chromatography for the detailed analysis of petrochemical samples. J Chromatogr A 1056(1–2):155–162

    Article  CAS  Google Scholar 

  • Villar-Navarro M, Ramos-Payan M, Fernández-Torres R, Callejón-Mochón M, Bello-López MA (2013) A novel application of three phase hollow fiber based liquid phase microextraction (HF-LPME) for the HPLC determination of two endocrine disrupting compounds (EDCs), n-octylphenol and n-nonylphenol, in environmental waters. Sci Total Environ 443:1–6

    Article  CAS  Google Scholar 

  • von Muhlen C, Zini CA, Caramão EB, Marriott PJ (2007) Nomenclature for comprehensive multidimensional chromatography in Portuguese language. Quim Nova 30(3):682–687

    Article  Google Scholar 

  • WHO/UNEP (2012) World Health Organization—United Nations Environment Programme. State of the science of endocrine disrupting chemicals-2012. http://unep.org/pdf/9789241505031_eng.pdf. Accessed 10 December 2013

  • Wu YP, Wang YC, Ding WH (2012) Rapid determination of alkylphenols in aqueous samples by in situ acetylation and microwave-assisted headspace solid-phase microextraction coupled with gas chromatography-mass spectrometry. J Sep Sci 35(16):2122–2130

    Article  CAS  Google Scholar 

  • Wu P-G, Pan X-D, Ma B-J, Wang L-Y, Zhang J (2014) Determination of phthalate esters in non-alcoholic beverages by GC-MS and optimization of the extraction conditions. Eur Food Res Technol 238(4):607–612

    Article  CAS  Google Scholar 

  • Xia H, Chi Y, Qi X, Su M, Cao Y, Song P, Li X, Chen T, Zhao A, Zhang Y, Cao Y, Ma X, Jia W (2011) Metabolomic evaluation of di-n-butyl phthalate-induced teratogenesis in mice. Metabolomics 7(4):559–571

    Article  CAS  Google Scholar 

  • Xie X, Lü W, Chen X (2013) Binding of the endocrine disruptors 4-tert-octylphenol and 4-nonylphenol to human serum albumin. J Hazard Mater 248–249:347–354

    Article  Google Scholar 

  • Yilmaz PK, Ertas A, Kolak U (2014) Simultaneous determination of seven phthalic acid esters in beverages using ultrasound and vortex-assisted dispersive liquid–liquid microextraction followed by high-performance liquid chromatography. J Sep Sci 37(16):2111–2117

    Article  CAS  Google Scholar 

  • Zhang C, Eganhouse RP, Pontolillo J, Cozzarelli IM, Wang Y (2012) Determination of nonylphenol isomers in landfill leachate and municipal wastewater using steam distillation extraction coupled with comprehensive two-dimensional gas chromatography/time-of-flight mass spectrometry. J Chromatogr A 1230:110–116

    Article  CAS  Google Scholar 

Download references

Acknowledgment

Financial support was provided by FP7-PEOPLE-2010-IRSES-269289-ELECTROACROSS—Electrokinetics across disciplines and continents: an integrated approach to finding new strategies for sustainable development and the Brazilian foundations CNPq.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Zenilda L. Cardeal .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2016 Springer International Publishing Switzerland

About this chapter

Cite this chapter

Moreira, M.A., André, L.C., da Silva, M.D.R.G., Cardeal, Z.L. (2016). Analysis of Endocrine Disrupting Chemicals in Food Samples. In: Ribeiro, A., Mateus, E., Couto, N. (eds) Electrokinetics Across Disciplines and Continents. Springer, Cham. https://doi.org/10.1007/978-3-319-20179-5_21

Download citation

Publish with us

Policies and ethics