Effect of amines in the release of bisphenol A from polycarbonate baby bottles Joaquim Maia a , José Manuel Cruz b , Raquel Sendón a , Juana Bustos c , Maria Eugenia Cirugeda c , José Juan Sanchez c , Perfecto Paseiro a, * a Department of Analytical Chemistry, Nutrition and Bromatology, Faculty of Pharmacy, University of Santiago de Compostela, 15782-Santiago de Compostela, Spain b Chemical Engineering Department, University of Vigo, E.T.S.E.I., 36200 Vigo (Pontevedra), Spain c National Center for Food, Spanish Agency for Food Safety and Nutrition, 28.220 Majadahonda (Madrid), Spain article info Article history: Received 17 November 2009 Accepted 8 March 2010 Keywords: Bisphenol A Amines Polycarbonate Migration Depolymerization abstract The key block for the production of polycarbonate (PC) is bisphenol A (BPA). Recent studies have proven that this monomer is able to migrate from PC baby bottles into food simulants and, although this is a polemical subject, numerous investigations indicate that BPA may have an effect on the human health. For these reasons, BPA safety regarding human exposure has recently become an alarming issue. Amines are a class of chemicals which are present in foodstuffs, such as milk. For this reason PC baby bottles, while being used, are continuously in contact with several amines, some of which are able to cause PC aminolysis, resulting in the release of BPA. In this work, 16 substances (14 with amine groups and 2 with amide groups) were tested in order to verify if they were able to increase BPA release by increasing PC depolymerization. High-performance liquid chromatography (HPLC) with fluorescence detection (FLD) and gas chromatography coupled to mass spectrometry (GC–MS) were used to quantify and identify the BPA, respectively. Although most of the substances tested did not increase the release of BPA from PC, some of them had a significant effect and high levels of this monomer were measured in the solutions. Of all of the amines tested that origi- nating the worst case of BPA release was 1,4-diaminobutane. Also known as putrescine, 1,4-diaminobu- tane is a biogenic amine that results from protein degradation and it may be present in milk. In this case, BPA concentration in the solution was more than 5000 times the level found in the control sample. Ó 2010 Elsevier Ltd. All rights reserved. 1. Introduction Bisphenol A (BPA; 2,2’-bis(4-hydroxyphenyl)propane; CAS No. 80-05-7) (Fig. 1) is one of the highest production-volume chemi- cals in the world and it is present in several products that are use every day by the consumers. In 2003, more than two million metric tons were produced throughout the entire world and its de- mand increases up to 6–10% every year (Lang et al., 2008). This monomer is produced mostly to manufacture epoxy resins and, predominantly, PC (21% and 72%, respectively) (Fig. 1)(Chapin, 2007). Due PC characteristics (toughness, light weight, transpar- ency, high impact and temperature resistance), this material is very frequent in household and food contact products, such as food containers, baby bottles, kitchen appliances, plastic bottles, toys, mobile phones and countless other products (Nérin, Fernández, Domeño, & Salafranca, 2003; Wong, Leo, & Seah, 2005). BPA may also be found in PVC films, where it is used as an additive (López-Cervantes & Paseiro-Losada, 2003). It has already been demonstrated that BPA is released from PC baby bottles into food simulants (Biles, McNeal, Begley, & Holli- field, 1997; Brede, Fjeldal, Skjevrak, & Herikstad, 2003; Maragou, Makri, Lampi, Thomaidis, & Koupparis, 2007). This release is not primarily due to a migration process, because BPA diffusion from the PC to the beverage is very low. Rather than a diffusion process, most of the BPA leaching results from PC degradation (Bierder- mann-Brem & Grob, 2009). According to some authors, BPA may be harmful to human health. Data obtained from in vitro assays indicates that BPA has weak estrogenic activity and there is some apprehension about how it may affect the endocrine system by mimicking estradiol, even when very low doses are present (Krishnan, Stathis, Permuth, Tokes, & Feldman, 1993; Laws, Carey, Ferrell, Bodman, & Cooper, 2000; Simal-Gándara, Paz-Abuín, & Ahrné, 1998). There are also in vivo studies, made in mammals (mainly in mice and rats) that call attention to other adverse effects caused by BPA. Some exam- ples can be cited: increase in hormonally mediated cancers, such as prostate and breast cancer; abnormalities in reproductive organs; a decline in semen quality; early sexual maturation in females; met- abolic disorders including insulin resistant diabetes and obesity, and neurobehavioral problems such as autism and attention deficit 0963-9969/$ - see front matter Ó 2010 Elsevier Ltd. All rights reserved. doi:10.1016/j.foodres.2010.03.014 * Corresponding author. Tel.: +34 981 598450; fax: +34 981 594912. E-mail address: perfecto.paseiro@usc.es (P. Paseiro). Food Research International 43 (2010) 1283–1288 Contents lists available at ScienceDirect Food Research International journal homepage: www.elsevier.com/locate/foodres