Bisphenol A and Template:Foreign relations of the European Union: Difference between pages

From Wikipedia, the free encyclopedia
(Difference between pages)
Content deleted Content added
VisualWikitext
→‎Synthesis: Explain why "A"
 
No edit summary
 
Line 1: Line 1:
{| class="infobox" width="150" style="width:20%; text-align: center; font-size:90%"
{{Chembox new <!-- infobox -->
! colspan="2"| [[European Union]]
| Name = Bisphenol A
| ImageFile = Bisphenol A.svg
| ImageSize = 275px
| ImageName = Bisphenol A
| IUPACName = 4,4'-dihydroxy-2,2-diphenylpropane
| OtherNames = BPA, 4,4'-(propan-2-ylidene)diphenol,<br />p, p'-isopropylidenebisphenol,<br> 4,4´-isopropylidenediphenol.
| Section1 = {{Chembox Identifiers
| SMILES = CC(c2ccc(O)cc2)(C)c1ccc(O)cc1
| CASNo = 80-05-7
| RTECS = SL6300000
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>15</sub>H<sub>16</sub>O<sub>2</sub>
| MolarMass = 228.29 g/mol
| Appearance = White to light brown flakes or powder
| Density = 1.20 g/cm³, solid
| Solubility = 120–300 ppm (at 21.5 °C)
| MeltingPt = 158 to 159 °C (430 K)
| BoilingPt = 220 °C (493 K) / 4 mmHg
| Viscosity =
}}
| Section3 = {{Chembox Structure
| CrystalStruct =
| Dipole =
}}
| Section7 = {{Chembox Hazards
| MainHazards =<!--Please add the following - Potential to reduce sperm production, increase prostate weight, increase risk of onset of endometriosis, can affect estrogen's natural actions (I could not add because my computer was attempting to wreck the template) -->
| ExternalMSDS =
| NFPA-H = 3
| NFPA-F = 0
| NFPA-R = 0
| FlashPt = 227 °C, autoignition: 600 °C
| RSPhrases = R: 36, 37, 38, 43 S: 24, 26, 37
}}
| Section8 = {{Chembox Related
| Function = [[?]]
| OtherFunctn =
| OtherCpds = [[phenols]]<br>[[Bisphenol S]]
}}
}}

'''Bisphenol A''', commonly abbreviated as '''BPA''', is an [[organic compound]] with two [[phenol]] [[functional group]]s. It is a difunctional building block of several important polymers and polymer additives. With an annual production of approximately 3 million tonnes, it is a important [[monomer]] in the production of [[polycarbonate]].

Suspect of being hazardous to humans already in the 1930s, in 2007 Bisphenol A has become controversial because it mimics [[estrogen]] and thus could induce hormonal responses.

==Synthesis==
Bisphenol A was first reported by [[A.P. Dianin]] in 1891.<ref name=dianin>{{cite journal | author = Dianin | title = Zhurnal russkogo fiziko-khimicheskogo obshchestva | volume = 23 | year = 1891 | pages = pp.&nbsp;492&ndash;}}</ref><ref>{{cite journal | first = Theodor | last = Zincke | authorlink = Theodor Zincke | title = Ueber die Einwirkung von Brom und von Chlor auf Phenole: Substitutionsprodukte, Pseudobromide und Pseudochloride | journal = [[Justus Liebigs Annalen der Chemie]] | year = 1905 | pages = 75–99 | doi = 10.1002/jlac.19053430106 | volume = 343}}</ref>
It is prepared by the [[condensation reaction|condensation]] of [[acetone]] (hence the suffix A in the name<ref>{{cite book | last=Uglea | first=Constantin V. Uglea | coauthors=Ioan I. Negulescu | title=Synthesis and Characterization of Oligomers | date=1991 | publisher=[[CRC Press]] | pages=page 103}}</ref>) with two [[Equivalent (chemistry)|equivalents]] of [[phenol]]. The reaction is [[catalysis|catalyzed]] by an acid, such as [[hydrochloric acid]] (HCl) or a [[Sodium polystyrene sulfonate|sulfonated polystyrene resin]]. Typically, a large excess of phenol is used to ensure full condensation:
: (CH<sub>3</sub>)<sub>2</sub>CO + 2 C<sub>6</sub>H<sub>5</sub>OH → (CH<sub>3</sub>)<sub>2</sub>C(C<sub>6</sub>H<sub>4</sub>OH)<sub>2</sub> + H<sub>2</sub>O
A large number of ketones undergo analogous condensation reactions. The method is efficient and the only by-product is water.<ref name=Fiege>{{citation | first = Helmut | last = Fiege | coauthors = Heinz-Werner Voges, Toshikazu Hamamoto, Sumio Umemura, Tadao Iwata, Hisaya Miki, Yasuhiro Fujita, Hans-Josef Buysch, Dorothea Garbe, Wilfried Paulus | title = Phenol Derivatives | series = Ullmann's Encyclopedia of Industrial Chemistry | publisher = Wiley-VCH | location = Weinheim | year = 2002 | doi = 10.1002/14356007.a19_313}}</ref>

==Use==
{{further|[[Polycarbonate]]}}
Products containing or made from Bisphenol A have been in commerce for more than 50 years, and its current uses are numerous. It is used in the synthesis of [[polyester]]s, [[polysulfone]]s, and [[polyether]] [[ketones]], as an [[antioxidant]] in some [[plasticizer]]s, and as a [[polymerization]] inhibitor in [[Polyvinyl chloride|PVC]]. It is a key [[monomer]] in production of [[polycarbonate]] [[plastic]] and [[epoxy]] resins.<ref name=Fiege/> Polycarbonate plastic, which is clear and nearly shatter-proof, is used to make a variety of common products including baby and water bottles, sports equipment, medical devices, CDs, and household electronics.<ref name="CERHR">{{cite news | title = CERHR Expert Panel Report for Bisphenol A | url = http://cerhr.niehs.nih.gov/chemicals/bisphenol/BPAFinalEPVF112607.pdf | accessdate = [[2008-04-18]] |date=[[2007-11-26]]| author=National Toxicology Program, U.S. Department of Health and Human Services}}</ref> Epoxy resins are used as coatings on the inside of almost all food and beverage cans.<ref name="C&ENews">{{cite journal|last=Erickson|first=Britt E.|date=June 2, 2008|title=Bisphenol A under scrutiny|journal=Chemical and Engineering News|publisher=American Chemical Society|volume=86|issue=22|pages=36-39}}</ref><!--For what reason is it used in cans?--> It is also a precursor to the [[flame retardant]] [[tetrabromobisphenol A]], and was formerly used as a [[fungicide]].<ref>[http://pesticideinfo.org/Detail_Chemical.jsp?Rec_Id=PC33756 Pesticideinfo.org: Bisphenol A]</ref>

Global production of bisphenol A in 2003 was estimated to be about 3 million [[metric tonnes|metric tonnes (t)]].<ref>[http://www.ec.gc.ca/substances/ese/eng/challenge/batch2/batch2_80-05-7.cfm Draft Screening Assessment for The Challenge Phenol, 4,4' -(1-methylethylidene)bis- (Bisphenol A) Chemical Abstracts Service Registry Number 80-05-7], Environment Canada.</ref> In the U.S., it is manufactured by [[Bayer MaterialScience]], [[Dow Chemical Company]], [[General Electric]], [[Hexion Specialty Chemicals]], and [[Sunoco|Sunoco Chemicals]]. In 2004, these companies produced just over 1 million t of bisphenol A, up from just 7,260 t in 1991. In 2003, annual U.S. consumption was 856,000 t, 72% of which was used to make polycarbonate plastic and 21% going into epoxy resins.<ref name="CERHR"/>

==Health effects==
Bisphenol A has a low [[acute toxicity]], with an oral [[LD50|LD<sub>50</sub>]] of 3250 mg/kg in rats.<ref>[http://www.glue.umd.edu/~choi/MSDS/Sigma-Aldrich/BISPHENOL%20A.pdf MSDS: Bisphenol A 99+%]</ref> However, bisphenol A is an [[endocrine disruptor]]: it is an [[estrogen receptor]] [[agonist]],<ref>{{Citation | last = Okada | first = H | last2 = ''et al.'' | first2 = | title = Direct evidence revealing structural elements essential for the high binding ability of bisphenol A to human estrogen-related receptor-gamma. | journal = Environ. Health Perspect. | volume = 116 | issue = 1 | pages = 32-38 | date = 2008 | year = 2008 | url = http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pubmed&pubmedid=18197296 | pmid = : 18197296}}</ref> and such agonists can act like the body's own [[hormones]], leading to similar physiological effects on the body.<ref>{{cite journal | last =O’Connor, Chapin | title = Critical evaluation of observed adverse effects of endocrine active substances on reproduction and development, the immune system, and the nervous system | journal = Pure Appl. Chem | volume = 75 | issue = 11–12 | pages = 2099–2123 |date=2003 | url = http://www.iupac.org/publications/pac/2003/pdf/7511x2099.pdf | format = Full Article | accessdate = 2007-02-28}}</ref> There is thus concern that long term low dose exposure to bisphenol A may induce [[chronic toxicity]] in humans.<ref>{{cite journal |author=vom Saal FS, Hughes C |title=An extensive new literature concerning low-dose effects of bisphenol A shows the need for a new risk assessment |journal=Environ. Health Perspect. |volume=113 |issue=8 |pages=926–33 |year=2005 |pmid=16079060 |doi= |url=http://ehpnet1.niehs.nih.gov/members/2005/7713/7713.html}}</ref><ref>[http://www.physorg.com/news120894078.html Hot liquids release potentially harmful chemicals in polycarbonate plastic bottles]</ref><ref name=pmid_18155859>{{cite journal |author=Le HH, Carlson EM, Chua JP, Belcher SM |title=Bisphenol A is released from polycarbonate drinking bottles and mimics the neurotoxic actions of estrogen in developing cerebellar neurons |journal=Toxicol. Lett. |volume=176 |issue=2 |pages=149–56 |year=2008 |pmid=18155859 |doi=10.1016/j.toxlet.2007.11.001}}</ref>

===Endocrine disruption===
The first evidence of the estrogenicity of bisphenol A came from experiments in the 1930s in which it was fed to ovariectomized rats,<ref>E. C. Dodds and Wilfrid Lawson, "Synthetic Œstrogenic Agents without the Phenanthrene Nucleus", ''Nature'', 137 (1936), 996.</ref><ref>E. C. Dodds and W. Lawson, ''Proceedings of the Royal Society of London, Series B, Biological Sciences'', 125, #839 (27-IV-1938), pp. 222–232.</ref> but it was not until 1997 that adverse effects of low-dose exposure on laboratory animals were first reported.<ref name=C&ENews/> Since then, its endocrine disrupting properties have been extensively investigated, and more than 100 studies have been published "rais[ing] health concerns" about the chemical.<ref name="WaPo">{{Citation | last = Layton | first = Lyndsey | title = Studies on Chemical In Plastics Questioned Congress Examines Role Of Industry in Regulation | newspaper = Washington Post | pages = A1 | year = 2008 | date = April 27, 2008 | url = http://www.washingtonpost.com/wp-dyn/content/article/2008/04/26/AR2008042602126.html}}.</ref> Early development appears to be the period of greatest sensitivity to its effects,<ref name=HealthCanada>[http://www.ec.gc.ca/substances/ese/eng/challenge/batch2/batch2_80-05-7.cfm Draft Screening Assessment for The Challenge Phenol, 4,4' -(1-methylethylidene)bis- (Bisphenol A)Chemical Abstracts Service Registry Number 80-05-7.] [[Health Canada]], 2008.</ref> and studies have demonstrated developmental toxicity, carcinogenic effects, and possible neurotoxicity at low doses in animal models (see [[#Selected studies on low dose bisphenol A exposure in animals|table]] below).<ref>{{cite journal | last =Lee Ym, et al. | title = Estrogen receptor independent neurotoxic mechanism of bisphenol A, an environmental estrogen. | journal = J Vet Sci. | volume = 8 | issue = 1 | pages = 27–38 |date=2007 | url = http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=pubmed&cmd=Retrieve&dopt=AbstractPlus&list_uids=17322771&query_hl=2&itool=pubmed_docsum | format = Abstract | accessdate = 2007-02-28}}</ref><ref>{{cite journal | last =Zsarnovszky A, Le HH, Wang HS, Belcher SM. | title = Ontogeny of rapid estrogen-mediated extracellular signal-regulated kinase signaling in the rat cerebellar cortex: potent nongenomic agonist and endocrine disrupting activity of the xenoestrogen bisphenol A | journal = Endocrinology. | volume = 146 | issue = 12 | pages = 5388–96 |date=2005 | url = http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=16123166 | format = Abstract | accessdate = 2007-02-28}}</ref> Recent studies suggest it may also be linked to obesity<ref>{{cite news |title=Bisphenol A linked to obesity in mice, study says |url=http://www.ctv.ca/servlet/ArticleNews/story/CTVNews/20080515/BPA_obesity_080515/20080515?hub=Health |work=CTV News |date=2008-05-15 |accessdate=2008-05-16 }}</ref> by triggering fat-cell activity<ref>{{cite journal | last =Grossman, Elizabeth. | title = Chemicals May Play Role in Rise in Obesity. | journal = Washington Post. |date=March 12, 2007 | url = http://www.washingtonpost.com/wp-dyn/content/article/2007/03/11/AR2007031100918.html?referrer%3Demailarticlepg&sub=AR}}</ref> and have confirmed that bisphenol A exposure during development has [[carcinogenic]] effects and produce precursors of [[breast cancer]].<ref>{{cite journal | last =Murray TJ | title = Induction of mammary gland ductal hyperplasias and carcinoma in situ following fetal bisphenol A exposure.| journal = Reproductive Toxicology |date=2007 | url = http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=17123778 | format = Abstract | accessdate = 2007-02-28}}</ref><ref name=pmid_18226065>{{cite journal |author=Soto AM, Vandenberg LN, Maffini MV, Sonnenschein C |title=Does breast cancer start in the womb? |journal=Basic Clin. Pharmacol. Toxicol. |volume=102 |issue=2 |pages=125–33 |year=2008 |pmid=18226065 |doi=10.1111/j.1742-7843.2007.00165.x}}</ref> However, neither the U.S. [[Environmental Protection Agency]]<ref>[http://www.epa.gov/iris/subst/0356.htm U.S.EPA, IRIS: Bisphenol A]</ref> nor the [[International Agency for Research on Cancer]]<ref>[http://monographs.iarc.fr/ENG/Classification/ListagentsCASnos.pdf AGENTS REVIEWED BY THE IARC MONOGRAPHS Volumes 1-99]</ref> have evaluated Bisphenol A for possible carcinogenic activity.
In 2007, a consensus statement by 38 experts on bisphenol A concluded that average levels in people are above those that cause harm to animals in laboratory experiments,<ref>{{cite journal | last =vom Saal, Fred. | title = Chapel Hill bisphenol A expert panel consensus statement: integration of mechanisms, effects in animals and potential to impact human health at current levels of exposure. | journal = Reprod Toxicol. |date=July 27, 2007 | url = http://www.ncbi.nlm.nih.gov/sites/entrez?Db=pubmed&Cmd=ShowDetailView&TermToSearch=17768031&ordinalpos=2&itool=EntrezSystem2.PEntrez.Pubmed.Pubmed_ResultsPanel.Pubmed_RVDocSum}}</ref> and a panel convened by the U.S. [[National Institutes of Health]] determined that there was "some concern" about BPA's effects on fetal and infant brain development and behavior.<ref name="CERHR"/> A 2008 draft report by the U.S. [[National Toxicology Program]] (NTP) agreed with the panel, concluding that "there is some concern for neural and behavioral effects in fetuses, infants, and children at current human exposures," and that there is "some concern for bisphenol A exposure in these populations based on effects in the prostate gland, mammary gland, and an earlier age for puberty in females." The NPT also concluded that there is negligible concern that "exposure of pregnant women to bisphenol A will result in fetal or neonatal mortality, birth defects or reduced birth weight and growth in their offspring" or that it causes adverse effects in exposed adults.<ref>[http://www.niehs.nih.gov/news/media/questions/sya-bpa.cfm Since you asked - Bisphenol A: Questions and Answers about the Draft National Toxicology Program Brief on Bisphenol A], National Institute of Environmental Health Sciences website.</ref>

In April 2008, the [[Health Canada]] released its Draft Screening Assessment for bisphenol A, which concluded that the chemical may pose some risk to infants<ref name='C&EN'>{{Citation | last = Morrissey | first = Susan R. | title = Banning Bisphenol A In Baby Bottles: Canada moves toward restricting the chemical; Congress proposes similar legislation | newspaper = Chemical and Engineering News | pages = | year = 2008 | date = April 23, 2008 | url = http://pubs.acs.org/cen/news/86/i17/8617news4.html}}.</ref> and proposed classifying the chemical as "'toxic' to human health and the environment."<ref>[http://www.chemicalsubstanceschimiques.gc.ca/challenge-defi/bisphenol-a_e.html Government of Canada Takes Action on Another Chemical of Concern: Bisphenol A], Chemical Substances, Health Canada. Accessed April 19, 2008.</ref> This action follows Canadian regulators selection of bisphenol A in 2006 as one of 200 substances deserving of thorough safety assessments after preliminary studies had found it to be "inherently toxic"; the chemical had not previously been studied by them in depth, having been accepted under [[grandfather clause]]s when stricter regulations were passed in the 1980s.<ref name="globemittelstaedt">{{cite news | last=Mittelstaedt | first=Martin | title='Inherently toxic' chemical faces its future | date=[[2007-04-07]] | url=http://www.theglobeandmail.com/servlet/story/RTGAM.20070406.wbisphenolA0407/BNStory/National/ | accessdate=2007-04-07 | publisher=Globe & Mail}}</ref>

In contrast to the recent actions in North America, in January 2006 the [[Germany|German]] Federal Institute for Risk Assessment announced that polycarbonate baby bottles are safe and stated that published research on the health effects of Bisphenol A is "difficult to interpret and [is] occasionally contradictory".<ref>[http://www.bfr.bund.de/cd/7294 Selected questions and answers relating to bisphenol A in baby bottles]- Federal Institute for Risk Assessment</ref> An assessment released later that year by the [[European Union]]’s Food Safety Authority reached a similar conclusion, expressing "considerable reservations" about the biological significance and robustness of the low-dose exposure studies on rodents.<ref>[http://www.efsa.europa.eu/EFSA/efsa_locale-1178620753812_1178620772817.htm Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to 2,2-BIS(4-HYDROXYPHENYL)PROPANE], European Food Safety Authority, November 29, 2006. Accessed April 19, 2008</ref> In 2007 [[Japan]] also concluded that "the current exposure levels of BPA will not pose any unacceptable risk to human health that a ban is not needed."<ref>[http://unit.aist.go.jp/crm/mainmenu/BPA_Summary_English.pdf Bisphenol A Risk Assessment Document (AIST Risk Assessment Document Series No. 4) Summary], New Energy and Industrial Technology Development Organization, Research Center for Chemical Risk Management, National Institute of Advanced Industrial Science and Technology, November 2007.</ref>

Some toxicologists and regulatory agencies have criticized low-dose toxicity studies, especially those that involved injecting bisphenol A directly into animals, since human exposures typically involve ingestion and subsequent metabolization in the liver, and the experimental design of some of these studies has also been questioned.<ref name="pmid16954066">{{cite journal |author=Goodman JE, McConnell EE, Sipes IG, ''et al'' |title=An updated weight of the evidence evaluation of reproductive and developmental effects of low doses of bisphenol A |journal=[[Crit. Rev. Toxicol.]] |volume=36 |issue=5 |pages=387–457 |year=2006 |pmid=16954066 |doi=10.1080/10408440600758317 |url=http://www.informaworld.com/openurl?genre=article&doi=10.1080/10408440600758317&magic=pubmed||1B69BA326FFE69C3F0A8F227DF8201D0}}</ref><ref>[http://www.bisphenol-a.org/pdf/Gray-HERA-2004.pdf Weight of the Evidence Evaluation of Low-Dose Reproductive and Developmental Effects of Bisphenol A], George M. Gray, Joshua T. Cohen, Gerald Cunha, Claude Hughes, Ernest E. McConnell, Lorenz Rhomberg, I. Glenn Sipes, and Donald Mattison7Human and Ecological Risk Assessment, 10: 875–921, 2004.</ref> Studies have also appeared pointing out flaws in chemical industry funded studies that found no evidence of adverse effects from low dose exposure,<ref>{{cite journal | last =Frederick S. vom Saal | title = Large effects from small exposures. II. The importance of positive controls in low-dose research on bisphenol A. | journal = Environmental Research | volume = 100 | issue = 1 | pages = 50–76 |date=2006 | url = http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=16256977&dopt=Abstract | format = Abstract | accessdate = 2007-02-28}}</ref> and a study from 2008 concluded that blood levels of bisphenol A in neonatal mice are the same whether it is injected or ingested.<ref name="pmid18295446">{{cite journal |author=Taylor JA, Welshons WV, Vom Saal FS |title=No effect of route of exposure (oral; subcutaneous injection) on plasma bisphenol A throughout 24h after administration in neonatal female mice |journal=Reprod. Toxicol. |volume=25 |issue=2 |pages=169–76 |year=2008 |month=February |pmid=18295446 |doi=10.1016/j.reprotox.2008.01.001 |url=http://linkinghub.elsevier.com/retrieve/pii/S0890-6238(08)00002-6 |accessdate=2008-05-05}}</ref>

===Selected studies on low dose bisphenol A exposure in animals===
{| class="wikitable"
|-
|-
|style="text-align: center;" colspan="2"|[[Image:EU Insigna.svg|120px]]<br />
! Dose (µg/kg/day)
<small>This article is part of the series:</small><br />
! Effects (measured in studies of mice or rats,<br>descriptions are from [[Environmental Working Group]])<ref name="EWG-BPA">This table is adapted from: EWG, 2007. "Many studies confirm BPA's low-dose toxicity across a diverse range of toxic effects," Environmental Working Group Report: A Survey of Bisphenol A in U.S. Canned Foods. Accessed November 4th, 2007 at http://www.ewg.org/node/20941. All studies included in this table where judged by the CEHRH panel to be at least of moderate usefulness for assessing the risk of BPA to human reproduction.</ref><ref name="globemittelstaedt"/>
'''[[Foreign relations of the European Union]]'''<small>
! Study Year
|-
|-
! style="background:#ccccff" | Policy
| 0.025
|- style="font-size:95%; text-align:left; line-height:80%"
| Permanent changes to genital tract
|
| 2005<ref name="pmid15689538">{{cite journal |author=Markey CM, Wadia PR, Rubin BS, Sonnenschein C, Soto AM |title=Long-term effects of fetal exposure to low doses of the xenoestrogen bisphenol-A in the female mouse genital tract |journal=[[Biol. Reprod.]] |volume=72 |issue=6 |pages=1344-51 |year=2005 |pmid=15689538 |doi=10.1095/biolreprod.104.036301 |url=http://www.biolreprod.org/cgi/pmidlookup?view=long&pmid=15689538}}</ref>
[[Common Foreign and Security Policy|CFSP]] [[High Representative for the Common Foreign and Security Policy|High Representative]]<br />
{{spaces|5}}[[Javier Solana]]<br />
[[European Commissioner for External Relations and European Neighbourhood Policy|ER Commissioner]]<br />
{{spaces|5}}[[Benita Ferrero-Waldner]]
|-
|-
|<div class="NavFrame" style="border:none; padding: 0px; margin:0px">
| 0.025
<div class="NavHead" style="background-color:#ccccff; padding: 2px; margin:0px; font-weight:normal;">[[Enlargement of the European Union|Candidates]]</div>
| Changes in breast tissue that predispose cells to hormones and carcinogens
<div class="NavContent" style="text-align:center; margin:8px; border:none; display:none; line-height:95%">
| 2005 <ref name="pmid15919749">{{cite journal |author=Muñoz-de-Toro M, Markey CM, Wadia PR, ''et al'' |title=Perinatal exposure to bisphenol-A alters peripubertal mammary gland development in mice |journal=[[Endocrinology]] |volume=146 |issue=9 |pages=4138-47 |year=2005 |pmid=15919749 |doi=10.1210/en.2005-0340 |url=http://endo.endojournals.org/cgi/pmidlookup?view=long&pmid=15919749}}</ref>
[[Accession of Croatia to the European Union|Croatia]]{{·}} [[Accession of the former Yugoslav Republic of Macedonia to the European Union|FYR Macedonia]]{{·}} [[Accession of Turkey to the European Union|Turkey]]{{·}} ''[[Netherlands Antilles and the European Union|Netherlands Antilles]]''</div></div>
|-
|-
|<div class="NavFrame" style="border:none; padding: 0px; margin:0px">
| 2
<div class="NavHead" style="background-color:#ccccff; padding: 2px; margin:0px; font-weight:normal;">[[Stabilisation and Association Process|SAA states]]</div>
| increased prostate weight 30%
<div class="NavContent" style="text-align:center; margin:8px; border:none; display:none; line-height:95%">
| 1997<ref name="pmid9074884">{{cite journal |author=Nagel SC, vom Saal FS, Thayer KA, Dhar MG, Boechler M, Welshons WV |title=Relative binding affinity-serum modified access (RBA-SMA) assay predicts the relative in vivo bioactivity of the xenoestrogens bisphenol A and octylphenol |journal=[[Environ. Health Perspect.]] |volume=105 |issue=1 |pages=70-6 |year=1997 |pmid=9074884 |doi=}}</ref>
[[Accession of Albania to the European Union|Albania]]{{·}} [[Accession of Bosnia and Herzegovina to the European Union|Bosnia and Herzegovina]]{{·}} [[Accession of Kosovo to the European Union|Kosovo]]{{·}} [[Accession of Montenegro to the European Union|Montenegro]]{{·}} [[Accession of Serbia to the European Union|Serbia]]</div></div>
|-
|-
|<div class="NavFrame" style="border:none; padding: 0px; margin:0px">
| 2<!-- abstract says says 2.0, EWG report says 2.4 -->
<div class="NavHead" style="background-color:#ccccff; padding: 2px; margin:0px; font-weight:normal;">[[European Free Trade Association|EFTA]]/[[European Economic Area|EEA]]</div>
| lower bodyweight, increase of anogenital distance in both genders, signs of early puberty and longer estrus.
<div class="NavContent" style="text-align:center; margin:8px; border:none; display:none; line-height:95%">
| 2002<ref name="pmid11955942">{{cite journal |author=Honma S, Suzuki A, Buchanan DL, Katsu Y, Watanabe H, Iguchi T |title=Low dose effect of in utero exposure to bisphenol A and diethylstilbestrol on female mouse reproduction |journal=[[Reprod. Toxicol.]] |volume=16 |issue=2 |pages=117-22 |year=2002 |pmid=11955942 |doi= |url=http://linkinghub.elsevier.com/retrieve/pii/S0890623802000060}}</ref>
[[Iceland and the European Union|Iceland]]{{·}} [[Liechtenstein and the European Union#Liechtenstein|Liechtenstein]]{{·}} [[Norway and the European Union|Norway]]{{·}} [[Switzerland and the European Union|Switzerland]]</div></div>
|-
|-
|<div class="NavFrame" style="border:none; padding: 0px; margin:0px">
| 2.4
<div class="NavHead" style="background-color:#ccccff; padding: 2px; margin:0px; font-weight:normal;">[[Eastern Partnership]]</div>
| Decline in testicular testosterone
<div class="NavContent" style="text-align:center; margin:8px; border:none; display:none; line-height:95%">
| 2004<ref name="pmid14605012">{{cite journal |author=Akingbemi BT, Sottas CM, Koulova AI, Klinefelter GR, Hardy MP |title=Inhibition of testicular steroidogenesis by the xenoestrogen bisphenol A is associated with reduced pituitary luteinizing hormone secretion and decreased steroidogenic enzyme gene expression in rat Leydig cells |journal=[[Endocrinology]] |volume=145 |issue=2 |pages=592–603 |year=2004 |pmid=14605012 |doi=10.1210/en.2003-1174 |url=http://endo.endojournals.org/cgi/pmidlookup?view=long&pmid=14605012}}</ref>
[[Armenia and the European Union|Armenia]]{{·}} [[Azerbaijan and the European Union|Azerbaijan]]{{·}} [[Georgia and the European Union|Georgia]]{{·}} [[Moldova and the European Union|Moldova]]{{·}} [[Ukraine and the European Union|Ukraine]]</div></div>
|-
|-
|<div class="NavFrame" style="border:none; padding: 0px; margin:0px">
| 2.5
<div class="NavHead" style="background-color:#ccccff; padding: 2px; margin:0px; font-weight:normal;">[[Union for the Mediterranean|Mediterranean Union]]</div>
| Breast cells predisposed to cancer
<div class="NavContent" style="text-align:center; margin:8px; border:none; display:none; line-height:95%">
| 2007<ref name="pmid17123778">{{cite journal |author=Murray TJ, Maffini MV, Ucci AA, Sonnenschein C, Soto AM |title=Induction of mammary gland ductal hyperplasias and carcinoma in situ following fetal bisphenol A exposure |journal=[[Reprod. Toxicol.]] |volume=23 |issue=3 |pages=383–90 |year=2007 |pmid=17123778 |doi=10.1016/j.reprotox.2006.10.002 |url=http://linkinghub.elsevier.com/retrieve/pii/S0890-6238(06)00263-2}}</ref>
[[Israel and the European Union|Israel]]{{·}} [[Morocco and the European Union|Morocco]]</div></div>
|-
|-
|<div class="NavFrame" style="border:none; padding: 0px; margin:0px">
| 10
<div class="NavHead" style="background-color:#ccccff; padding: 2px; margin:0px; font-weight:normal;">[[Third country relationships with the European Union|Other relations]]</div>
| Prostate cells more sensitive to hormones and cancer
<div class="NavContent" style="text-align:center; margin:8px; border:none; display:none; line-height:95%">
| 2006<ref name="pmid16740699">{{cite journal |author=Ho SM, Tang WY, Belmonte de Frausto J, Prins GS |title=Developmental exposure to estradiol and bisphenol A increases susceptibility to prostate carcinogenesis and epigenetically regulates phosphodiesterase type 4 variant 4 |journal=[[Cancer Res.]] |volume=66 |issue=11 |pages=5624–32 |year=2006 |pmid=16740699 |doi=10.1158/0008-5472.CAN-06-0516 |url=http://cancerres.aacrjournals.org/cgi/pmidlookup?view=long&pmid=16740699}}</ref>
[[European Union-Russia Common Spaces|Russia]]{{·}} [[Microstates and the European Union|Microstates]]{{·}} [[Cape Verde and the European Union|Cape Verde]]{{·}} [[Special member state territories and the European Union|Territories]]{{·}} [[Greenland and the European Union|Greenland]]{{·}} [[Canada and the European Union|Canada]]{{·}} [[European Union arms embargo on the People's Republic of China|PR China]]{{·}} [[Euro-American relations|USA]]</div></div>
|-
|-
| style="background:#ccccff; text.align:center" | See also
| 10
|- style="font-size:95%; text-align:center"
| Decreased maternal behaviors
|
| 2002<ref name="pmid12060838">{{cite journal |author=Palanza PL, Howdeshell KL, Parmigiani S, vom Saal FS |title=Exposure to a low dose of bisphenol A during fetal life or in adulthood alters maternal behavior in mice |journal=[[Environ. Health Perspect.]] |volume=110 Suppl 3 |issue= |pages=415–22 |year=2002 |pmid=12060838 |doi= |url=http://ehpnet1.niehs.nih.gov/docs/2002/suppl-3/415-422palanza/abstract.html}}</ref>
[[European Neighbourhood Policy|Neighbourhood Policy]]{{·}} [[ACP countries|ACP]]{{·}} [[Third country economic relationships with the European Union|Economic Relations]]{{·}} [[European Commission diplomatic missions|Diplomatic Missions]]{{·}} [[European Security and Defence Policy|Security]]{{·}} [[Military of the European Union|Military]]{{·}} [[Eurosphere]]{{·}} [[ESDP missions]]
|-
<!-- values in abstract (PMID: 15079872) don't agree with LOAEL listed in EWG report| 30
| Hyperactivity
| 2004
|- -->
| 30
| Reversed the normal sex differences in brain structure and behavior
| 2003<ref name="pmid12631470">{{cite journal |author=Kubo K, Arai O, Omura M, Watanabe R, Ogata R, Aou S |title=Low dose effects of bisphenol A on sexual differentiation of the brain and behavior in rats |journal=[[Neurosci. Res.]] |volume=45 |issue=3 |pages=345–56 |year=2003 |pmid=12631470 |doi= |url=http://linkinghub.elsevier.com/retrieve/pii/S0168010202002511}}</ref>
|-
| 50
| U.S. human exposure limit (not a result from an animal study, but a guideline set by EPA)
| 1998<ref>EPA (Environmental Protection Agency). 1988. [http://www.epa.gov/iris/subst/0356.htm Oral RfD Assessment: Bisphenol A. Integrated Risk Information System].</ref>
|-
|}

===Human exposure to bisphenol A===
Bisphenol A has been known to leach from the plastic lining of canned foods <ref>{{cite website | title = Environmental Working Group | url =http://www.ewg.org/reports/bisphenola | accessdate = 2007-03-07}}</ref> and, to a lesser degree, polycarbonate [[plastics]] that are cleaned with harsh detergents or used to contain acidic or high-temperature liquids. Studies by the [[Centers for Disease Control and Prevention|CDC]] found bisphenol A in the urine of 95% of adults sampled in 1988-1994<ref name="pmid15811827">{{cite journal |author=Calafat AM, Kuklenyik Z, Reidy JA, Caudill SP, Ekong J, Needham LL |title=Urinary concentrations of bisphenol A and 4-nonylphenol in a human reference population |journal=[[Environ. Health Perspect.]] |volume=113 |issue=4 |pages=391–5 |year=2005 |pmid=15811827 |doi= |url=http://ehpnet1.niehs.nih.gov/members/2004/7534/7534.html}}</ref> and in 93% of children and adults tested in 2003-04.<ref name="pmid18197297">{{cite journal |author=Calafat AM, Ye X, Wong LY, Reidy JA, Needham LL |title=Exposure of the U.S. population to bisphenol A and 4-tertiary-octylphenol: 2003-2004 |journal=[[Environ. Health Perspect.]] |volume=116 |issue=1 |pages=39–44 |year=2008 |pmid=18197297 |doi=10.1289/ehp.10753}}</ref> Almost all exposure is through diet, and infants fed with liquid formula are among the most exposed. Infants fed canned formula with polycarbonate bottles can consume quantities of bisphenol A up to 13 µg/kg/day (see table below),<ref>{{cite website | title = European Food Safety Authority Opinion | url =http://www.efsa.europa.eu/en/science/afc/afc_opinions/bisphenol_a.html | format = Abstract | accessdate = 2007-02-28}}</ref> while the most sensitive animal studies show effects at much lower concentrations. Debate continues on what is the safe limit of this compound. Within the [[United States]], an exposure of up to 50 µg/kg/day (50 ppb/day) is considered safe<ref name="globemittelstaedt"/> by the [[United States Environmental Protection Agency]].<ref>[http://www.epa.gov/iris/subst/0356.htm Bisphenol A] - [[United States Environmental Protection Agency]]</ref>

Dr. Maida Galvez, a pediatrician studying BPA, recommends parents stay away from bottles containing the chemical and says, "We know the animal studies raise concerns, but there aren't human studies showing effects yet ... so, when we don't have the evidence, what we recommend is that parents try to err on the side of caution."<ref name="ABC">[http://www.abcnews.go.com/WN/story?id=4259036&page=1 Parents Concerned Over Potentially Toxic Baby Bottles] ABC News, Feb. 7, 2008.</ref>

{| class="wikitable"
|-
! Population
! Estimated daily bisphenol A intake, μg/kg/day.<br>Table adapted from the National Toxicology Program Expert Panel Report.<ref name="CERHR"/>
|-
| Infant (0-6 months)<br>formula-fed
| <center>1-11</center>
|-
| Infant (0-6 months)<br>breast-fed
| <center>0.2-1 </center>
|-
| Infant (6-12 months)
| <center>1.65-13</center>
|-
| Child (1.5-6 years)
| <center>0.043-14.7</center>
|-
| Adult
| <center>0.008-1.5</center>
|-
|}

==Government and industry response==
On April 18, 2008 Canadian Health Minister [[Tony Clement]] announced that Canada intends to ban the import, sale, and advertising of polycarbonate baby bottles containing bisphenol A over concerns of the safety of bisphenol A. While Health Canada concluded that human exposures are less than the levels deemed to be potentially unsafe, the margin of safety was considered too low for formula-fed infants.<ref name=HealthCanada/><ref>The government has given the public 60 days to comment on the proposed ban starting April 19, 2008 and will evaluate whether the ban will become law in October 2008. {{cite news | title=Government of Canada Takes Action on Another Chemical of Concern: Bisphenol A | url=http://www.chemicalsubstanceschimiques.gc.ca/challenge-defi/bisphenol-a_e.html
|accessdate=2008-04-18}}</ref> Around the same time, [[Wal-Mart]] announced that it was immediately ceasing sales in all its Canadian stores of food containers, water and baby bottles, sippy cups, and pacifiers containing bisphenol A, and that it would phase out baby bottles made with it in U.S. stores by early 2009.<ref>[http://www.marketwatch.com/news/story/wal-mart-pull-baby-bottles-made/story.aspx?guid=%7BF360BF61-1D66-4559-A370-EA6CF49E1366%7D&dist=msr_4 Wal-Mart to pull baby bottles made with chemical BPA: Washington Post], Market Watch, April 18, 2008.</ref> [[Nalgene]] also announced it will stop using the chemical in its products,<ref>[http://www.nytimes.com/2008/04/18/business/18plastic.html?ref=business Bottle Maker to Stop Using Plastic Linked to Health Concerns], ''New York Times'', April 18, 2008.</ref> and [[Toys-R-Us]] said it too will cease selling baby bottles made from it.<ref>{{cite news | title = Toys 'R' Us to phase out bisphenol A baby bottles | publisher = CBC News | date = April 22, 2008 | url = http://www.cbc.ca/consumer/story/2008/04/22/bottles-bpa.html | accessdate = 2008-04-22}}</ref> Subsequent news reports showed many retailers removing polycarbonate drinking products from their shelves.<ref>[http://cnews.canoe.ca/CNEWS/Politics/2008/04/15/5293466-cp.html CANOE - CNEWS - Politics: Bisphenol A water-bottle removal expanding among Canadian retailers<!-- Bot generated title -->]</ref>

As of the release of NTP and Health Canada reports, 10 U.S. states, including [[California]], [[Maryland]],<ref name="WaPo"/> [[Connecticut]]<ref name='courant'>{{Citation | last = Weil | first = William | title = Debate In A Bottle | newspaper = Hartford Courant | year = 2008 | date = April 23, 2008 | url = http://www.courant.com/features/lifestyle/green/hc-bottled.art0apr23,0,5170837.story}}.</ref> and [[New Jersey]],<ref>{{Citation | title = Momentum Builds to End BPA in Plastics | newspaper = NewsInferno.com | date = April 22, 2008 | url = http://www.newsinferno.com/archives/2955}}.</ref> already had legislation pending that would affect the use of BPA, and in the wake of these reports, [[U.S. Senator]] [[Charles Schumer]] ([[Democratic Party (United States)|D]]–[[New York State|N.Y.]]) introduced legislation that would ban bisphenol A nationally from products for infants.<ref name="WaPo"/> In addition, the U.S. Congress is investigating the [[Weinberg Group]], a chemical industry consulting firm, for its role in downplaying the health effects of bisphenol A and other chemicals,<ref>[http://cspinet.org/integrity/watch/200802111.html#5 Congressional Probe Targets Consulting Group], ''Integrity in Science Watch'', [[Center for Science in the Public Interest]], 02/11/2008.</ref> and the [[Energy and Commerce Committee]] in the [[United States House of Representatives|House of Representatives]] is investigating its use in baby products as well as the FDA's approval of the chemical. In asking the FDA to reassess its approval of bisphenol A, committee chairman [[Bart Stupak]] ([[Democratic Party (United States)|D]]–[[Michigan|Mich.]]) said "We would expect the FDA to make decisions based on the best available science…Yet the FDA relied on only two industry-funded studies, while other respected authorities used all available data to reach vastly different conclusions." While the FDA has set up a task force to address these concerns, it maintains that bisphenol A is safe and is not recommending that people avoid using products made from it. The [[Consumer Product Safety Commission]] agrees, and its deputy director has stressed that use of bisphenol A based plastics have many practical benefits, and that "a ban could result in less effective protection of children from head, eye, or bodily injury."<ref name=C&ENews/>

In response to the recent events, an [[American Chemistry Council]] (ACC)/BPA Global Group spokesman said, “The weight of scientific evidence, as assessed by Health Canada and other agencies around the world, provides reassurance that consumers can continue to safely use products made from bisphenol A."<ref>[http://www.kansascity.com/news/nation/story/582740.html Canada bans BPA plastic from baby bottles], ''Kansas City Star'', Apr. 18, 2008 .</ref> The ACC says that bisphenol A does not pose a risk to consumers and has called on the [[Food and Drug Administration]] to review the chemical. The ACC also called the media coverage of the controversy "unnecessarily confusing and frightening the public."<ref name='courant'/> The [[Grocery Manufacturers Association]] also insists that bisphenol A is safe, and argues that "Data purporting to demonstrate 'low' dose effects on the male reproductive system by BPA have not been successfully replicated and, therefore, are not credible to estimate human health risks and safety in light of the weight of a large body of evidence to the contrary."<ref>{{cite news | title = Canada Could Ban Baby Bottles Containing Bisphenol A | publisher = Environment News Service | date = April 22, 2008 | url = http://www.ens-newswire.com/ens/apr2008/2008-04-22-05.asp | accessdate = 2008-04-24 }}</ref> A spokesman for the [[tin can]] industry has said that without lining cans with bisphenol A based resins, ''[[E. coli]]'' and botulism poisoning would be "rampant."<ref name=C&ENews/> An industry website [http://bisphenol-a.org/index.html Bisphenol-a.org] also carries a number of articles dated as recently as [[February 2008]] claiming the use of Polycarbonate water bottles is safe.

The chemical industry has been criticized over bisphenol A by Democrats and their allies. David Michaels, who served in the [[Presidency_of_Bill_Clinton|Clinton Adminstration]], told the ''Washington Post'' that "Tobacco figured this out, and essentially it's the same model … If you fight the science, you're able to postpone regulation and victim compensation, as well. As in this case, eventually the science becomes overwhelming. But if you can get five or 10 years of avoiding pollution control or production of chemicals, you've greatly increased your product."<ref name="WaPo"/>

In the U.S. retail sector, growing concern over bisphenol A exposure had already led a number of retailers to stop using bisphenol A, particularly chains promoting healthy food and lifestyles. In 2005, [[Patagonia Inc.]] ceased selling polycarbonate bottles, and in 2006, [[Whole Foods Markets]] ceased selling baby bottles as did [[Mountain Equipment Co-op]] in 2007.<ref>{{cite news | url=http://biz.yahoo.com/ap/071223/polycarbonate_worries.html | date=[[2007-12-23]] | publisher=[[Associated Press]] | title=Polycarbonate bottles raise questions}}</ref>

The city of [[San Francisco, California|San Francisco]], [[California]], banned the sale of baby bottles and other products for young children containing bisphenol A effective December 2006, and was, at the time, the only jurisdiction in the world to outright forbid the substance.<ref>{{cite news | url=http://www.sfgate.com/cgi-bin/article.cgi?file=/chronicle/archive/2006/11/22/EDG6ELJ46Q1.DTL | date=[[2006-11-22]] | publisher=San Francisco Chronicle | title=Anxieties about toxics }}</ref> The ban was never enforced, and in May 2007 the city repealed the ban.

==Environmental risk==

As an environmental contaminant this compound interferes with [[nitrogen fixation]] at the roots of [[leguminous]] plants associated with the [[bacterial]] [[symbiont]] ''[[Sinorhizobium meliloti]]''. Despite a [[half-life]] in the soil of only 1–10 days, its ubiquity makes it an important [[pollutant]].<ref name=fox>{{cite journal | author=Fox, J.E., J. Gulledge, E. Engelhaupt, M.E. Burrow & J.A. McLachlan | title=Pesticides reduce symbiotic efficiency of nitrogen-fixing rhizobia and host plants | journal=[[PNAS|Proc. Nat. Acad. Sci.]] | year=2007 | volume=104 | pages=10282–7}}</ref> According to [[Health Canada]], "initial assessment shows that at low levels, bisphenol A can harm fish and organisms over time. Studies also indicate that it can currently be found in municipal wastewater."<ref>[http://www.chemicalsubstanceschimiques.gc.ca/challenge-defi/bisphenol-a_fs-fr_e.html Bisphenol A Fact Sheet], Health Canada. Assessed April 19, 2008.</ref>

==Identification in plastics==
[[Image:Plastic-recyc-07.svg|thumb|100px|Some type 7 plastics may leach bisphenol A|left]]
[[Image:Plastic-recyc-03.svg|thumb|100px|Some type 3 plastics may leach bisphenol A|right]]

There are [[Plastic_identification_code#Plastic_Identification_Code|seven classes of plastics]] used in packaging applications. Type 7 is the catch-all "other" class, and some type 7 plastics, such as [[polycarbonate]] (sometimes identified with the letters "PC" near the [[recycling symbol]]) and epoxy resins, are made from bisphenol A monomer.<ref name=Fiege/> When such plastics are exposed to hot liquids, bisphenol A leaches out 55 times faster than it does under normal conditions, at up to 32&nbsp;[[nanogram|ng]]/hour.<ref name="sciam2008">{{cite journal|author=Biello D | title=Plastic (not) fantastic: Food containers leach a potentially harmful chemical | journal=Scientific American | volume=2 | date=2008-02-19 | url=http://www.sciam.com/article.cfm?id=plastic-not-fantastic-with-bisphenol-a | accessdate=2008-04-09}}</ref> Type 3 ([[PVC]]) can also contain bisphenol A as antioxidant in [[plasticizers]].<ref name=Fiege/> Types 1 ([[Polyethylene terephthalate|PET]]), 2 ([[HDPE]]), 4 ([[LDPE]]), 5 ([[polypropylene]]), and 6 ([[polystyrene]]) do not use bisphenol A during [[polymerization]] or package forming,<ref> ''http://www.ehponline.org/docs/2006/8804/letter.html'' Environmental Health Perspectives Volume 114, Number 2, February 2006 </ref> and thus will not leach bisphenol A into food or beverages.

==References==
<div class="references-small">
<references />
</div>


----
==External links==
* [http://www.fda.gov/oc/opacom/hottopics/bpa.html US FDA statement on bisphenol A]
* [http://pubs.acs.org/subscribe/journals/esthag-w/2006/jun/science/pt_plastics.html Plastics chemical alters female brains]
* [http://www.pbs.org/wgbh/pages/frontline/shows/nature/interviews/vomsaal.html Frontline Fooling With Nature], interview Fredrick Vom Saal, Ph.D.
* [http://www.foodnavigator.com/news/ng.asp?n=64328-bisphenol-chemical-bpa News report on effect through plastic bottles]
* [http://assets.panda.org/downloads/bisphenol.pdf ''Bisphenol A. A Known Endocrine Disruptor'' WWF publication]
* [http://www.bisphenol-a.org Plastics Industry Bisphenol A information site]
* [http://www.epa.gov/iris/subst/0356.htm United States Environmental Protection Agency page on Bisphenol A]
* [http://www.eeletter.com/bpareport.pdf An ''Endocrine/Estrogen Letter'' special Report on BPA]
* [http://www.environmentalhealthnews.org/archives.jsp?sm=fr4%3Btype6%3B5Story12%3BNews+Stories&tn=0text&tv=bisphenol&ss=1 News coverage of bisphenol A from EnvironmentalHealthNews.org]
* [http://biology.plosjournals.org/perlserv/?request=get-document&doi=10.1371%2Fjournal.pbio.0050193 ''The Toxic Origins of Disease''], Liza Gross, PLoS Biology - an essay examining some of the evidence and effects.
* [http://www.jsonline.com/story/index.aspx?id=692145 CHEMICAL FALLOUT: JOURNAL SENTINEL WATCHDOG REPORT''], Milwaukee Journal Star newspaper article examining effects of Bisphenol A on lab animals and humans.
* [http://www.ava.gov.sg/FoodSector/FoodSafetyEducation/Food+Facts/SafeUsePlasticContainers/index.htm ''Safe Use Of Plastic Food Packaging And Containers''], Agri-Food & Veterinary, Authority of Singapore
* [http://www.loe.org/images/070803/Vandenberg%20Exposure%20Rep%20Tox%20resubmission.pdf ''Human Exposure to Bisphenol A''], Vandenberg, L.N., ''et al.'' via [[Living on Earth]]


|- style="font-size:95%; text-align:right"
{{HealthIssuesOfPlastics}}
|{{Tnavbar|Foreign relations of the European Union|mini=1|nodiv=1}}
|}<noinclude>


[[Category:Phenols]]
[[Category:European Union templates|Foreign relations]]
[[Category:Plasticizers]]
[[Category:Foreign relations templates|European Union]]
[[Category:Russian inventions]]


[[pl:Szablon:Polityka zagraniczna UE]]
[[da:Bisfenol A]]
</noinclude>
[[de:Bisphenol A]]
[[fr:Bisphénol A]]
[[nl:Bisfenol A]]
[[ja:ビスフェノールA]]
[[pl:Bisfenol A]]
[[fi:Bisfenoli-A]]
[[sv:Bisfenol A]]
[[zh:酚甲烷]]

Revision as of 10:35, 11 October 2008

European Union

This article is part of the series:
Foreign relations of the European Union

Policy

CFSP High Representative
     Javier Solana
ER Commissioner
     Benita Ferrero-Waldner

Candidates
SAA states
EFTA/EEA
Eastern Partnership
Mediterranean Union
Other relations
See also

Neighbourhood Policy · ACP · Economic Relations · Diplomatic Missions · Security · Military · Eurosphere · ESDP missions

Retrieved from "https://en.wikipedia.org/w/index.php?title=Bisphenol_A&oldid=244546085"