Bisphenol Aのソースを表示

{{Short description|Chemicals used in plastics manufacturing}}
{{cs1 config|name-list-style=vanc|display-authors=3}}
{{Good article}}
{{Use dmy dates|date=December 2020}}
{{Chembox
|Watchedfields = changed
|verifiedrevid = 477162965
|Name = Bisphenol&nbsp;A
|ImageFile1_Ref = {{chemboximage|correct|??}}
|ImageFile1 = Bisphenol-A-Skeletal.svg
|ImageSize1 = 240px
|ImageFile2 = Bisphenol A.png
|ImageSize2 = 180px
|ImageName = Bisphenol A
|PIN = 4,4′-(Propane-2,2-diyl)diphenol
|OtherNames = {{unbulleted list|Bisphenol acetone|BPA|Diphenylolpropane|''p'',''p''-Isopropylidenebisphenol|2,2-Bis(4-hydroxyphenyl)propane|2,2-Di(4-phenylol)propane}}
|Section1={{Chembox Identifiers
|IUPHAR_ligand = 7865
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI = 33216
|DrugBank_Ref = {{drugbankcite|correct|drugbank}}
|DrugBank = DB06973
|SMILES = Oc1ccc(cc1)C(c2ccc(O)cc2)(C)C
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = MLT3645I99
|KEGG_Ref = {{keggcite|correct|kegg}}
|KEGG = C13624
|InChI = 1/C15H16O2/c1-15(2,11-3-7-13(16)8-4-11)12-5-9-14(17)10-6-12/h3-10,16-17H,1-2H3
|InChIKey = IISBACLAFKSPIT-UHFFFAOYAI
|SMILES1 = CC(C)(c1ccc(cc1)O)c2ccc(cc2)O
|ChEMBL_Ref = {{ebicite|correct|EBI}}
|ChEMBL = 418971
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/C15H16O2/c1-15(2,11-3-7-13(16)8-4-11)12-5-9-14(17)10-6-12/h3-10,16-17H,1-2H3
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = IISBACLAFKSPIT-UHFFFAOYSA-N
|CASNo = 80-05-7
|CASNo_Ref = {{cascite|correct|CAS}}
|PubChem = 6623
|EINECS = 201-245-8
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 6371
|RTECS = SL6300000
|UNNumber = 2430
}}
|Section2={{Chembox Properties
|C=15 | H=16 | O=2
|Appearance = White solid
|Odour = Phenolic, medical
|Density = 1.217 g/cm<sup>3</sup><ref>{{cite journal |last1=Lim |first1=Caitlin F. |last2=Tanski |first2=Joseph M. |title=Structural Analysis of Bisphenol-A and its Methylene, Sulfur, and Oxygen Bridged Bisphenol Analogs |journal=Journal of Chemical Crystallography |date=3 August 2007 |volume=37 |issue=9 |pages=587–595 |doi=10.1007/s10870-007-9207-8|bibcode=2007JCCry..37..587L |s2cid=97284173 }}</ref>
|Solubility = 0.3 g/L (25&nbsp;°C)<ref name=water-solubility>{{cite journal |last1=Shareef |first1=Ali |last2=Angove |first2=Michael J. |last3=Wells |first3=John D. |last4=Johnson |first4=Bruce B. |title=Aqueous Solubilities of Estrone, 17β-Estradiol, 17α-Ethynylestradiol, and Bisphenol A |journal=Journal of Chemical & Engineering Data |date=11 May 2006 |volume=51 |issue=3 |pages=879–881 |doi=10.1021/je050318c}}</ref>
|MeltingPtC = 155
|MeltingPt_ref =<ref name=mbt-mpt>{{cite journal |last1=Mitrofanova |first1=S. E. |last2=Bakirova |first2=I. N. |last3=Zenitova |first3=L. A. |last4=Galimzyanova |first4=A. R. |last5=Nefed'ev |first5=E. S. |title=Polyurethane varnish materials based on diphenylolpropane |journal=Russian Journal of Applied Chemistry |date=September 2009 |volume=82 |issue=9 |pages=1630–1635 |doi=10.1134/S1070427209090225|s2cid=98036316 }}</ref>
|BoilingPtC = 250-252
|BoilingPt_notes = at {{convert|13|Torr|atm}}
|BoilingPt_ref =<ref name=mbt-mpt />
|LogP = 3.41<ref>{{cite journal |last1=Robinson |first1=Brian J. |last2=Hui |first2=Joseph P.M. |last3=Soo |first3=Evelyn C. |last4=Hellou |first4=Jocelyne |title=Estrogenic Compounds in Seawater and Sediment from Halifax Harbour, Nova Scotia, Canada |journal=Environmental Toxicology and Chemistry |date=2009 |volume=28 |issue=1 |pages=18–25 |doi=10.1897/08-203.1|pmid=18702564 |bibcode=2009EnvTC..28...18R |s2cid=13528747 }}</ref>
|VaporPressure = {{nowrap|5×10<sup>−6</sup> Pa}} (25&nbsp;°C)<ref>{{cite web|url=http://www.speclab.com/compound/c80057.htm|website=speclab.com|title=Chemical Fact Sheet – Cas #80057 CASRN 80-05-7|date=1 April 2012|access-date=14 June 2012|archive-url=https://web.archive.org/web/20120212033315/http://www.speclab.com/compound/c80057.htm|archive-date=12 February 2012|url-status=dead}}</ref>
}}
|Section3={{Chembox Hazards
|Hazards_ref = <ref name="Sigma">{{Sigma-Aldrich|id=239658|name=Bisphenol A|access-date=22-05-2022}}</ref>
|NFPA-H = 2
|NFPA-F = 1
|NFPA-R = 0
|GHSPictograms = {{GHS05}}{{GHS07}}{{GHS08}}{{GHS09}}
|GHSSignalWord = Danger
|HPhrases = {{H-phrases|317|318|335|360|H411}}<ref name="Sigma" />
|PPhrases = {{P-phrases|201|202|261|273|302+352|304+340|305+351+338|308+313|333+313|363|403+233}}<ref name="Sigma" />
|FlashPtC = 227 
|FlashPt_ref =<ref name="Sigma"/>
|AutoignitionPtC = 510 
|AutoignitionPt_ref=<ref name="Sigma"/>
}}
}}
'''Bisphenol A''' ('''BPA''') is a [[chemical compound]] primarily used in the manufacturing of various [[plastic]]s. It is a colourless solid which is [[Solubility|soluble]] in most common organic [[solvent]]s, but has very poor solubility in water.<ref name=water-solubility/><ref name="Fiege" /> BPA is produced on an industrial scale by the [[condensation reaction]] of [[phenol]] and [[acetone]]. Global production in 2022 was estimated to be in the region of 10 million tonnes.<ref name=production />

BPA's largest single application is as a [[co-monomer]] in the production of [[polycarbonate]]s, which accounts for 65–70% of all BPA production.<ref name=EU2008 /><ref name="Tom2021"/> The manufacturing of [[epoxy resin]]s and [[vinyl ester resin]]s account for 25–30% of BPA use.<ref name=EU2008/><ref name="Tom2021" /> The remaining 5% is used as a major component of several [[high-performance plastics]], and as a minor additive in [[PVC]], [[polyurethane]], [[thermal paper]], and several other materials. It is not a [[plasticizer]],<ref>{{cite book |doi=10.1002/14356007.a20_439|chapter=Plasticizers|title=Ullmann's Encyclopedia of Industrial Chemistry|year=2000| vauthors = Cadogan DF, Howick CJ |isbn=3527306730}}</ref> although it is often wrongly labelled as such.

The health effects of BPA have been the subject of prolonged public and scientific debate.<ref name=WHO /><ref name=German2011 /><ref name=GLP /> BPA is a [[xenoestrogen]], exhibiting hormone-like properties that mimic the effects of [[estrogen]] in the body.<ref>{{cite journal| vauthors = Egan M |title=Sarah A. Vogel. Is It Safe? BPA and the Struggle to Define the Safety of Chemicals|location=Berkeley|publisher=University of California Press |date=2013 |journal=Isis |volume=105 |issue=1 |pages=254 |doi=10.1086/676809 |issn=0021-1753}}</ref> Although the effect is very weak,<ref name=Xenochemicals /> the pervasiveness of BPA-containing materials raises concerns, as exposure is effectively lifelong.  Many BPA-containing materials are non-obvious but commonly encountered,<ref name="Covaci">{{cite journal | vauthors = Geens T, Aerts D, Berthot C, Bourguignon JP, Goeyens L, Lecomte P, Maghuin-Rogister G, Pironnet AM, Pussemier L, Scippo ML, Van Loco J, Covaci A | title = A review of dietary and non-dietary exposure to bisphenol-A | journal = Food and Chemical Toxicology | volume = 50 | issue = 10 | pages = 3725–3740 | date = October 2012 | pmid = 22889897 | doi = 10.1016/j.fct.2012.07.059 | url = https://dipot.ulb.ac.be/dspace/bitstream/2013/195906/1/Elsevier_179533.pdf }}</ref> and include coatings for the inside of [[food can]]s,<ref>{{cite journal | vauthors = Noonan GO, Ackerman LK, Begley TH | title = Concentration of bisphenol A in highly consumed canned foods on the U.S. market | journal = Journal of Agricultural and Food Chemistry | volume = 59 | issue = 13 | pages = 7178–7185 | date = July 2011 | pmid = 21598963 | doi = 10.1021/jf201076f | bibcode = 2011JAFC...59.7178N }}</ref> clothing designs,<ref name="ir.rcees.ac.cn">{{cite journal | vauthors = Xue J, Liu W, Kannan K | title = Bisphenols, Benzophenones, and Bisphenol A Diglycidyl Ethers in Textiles and Infant Clothing | journal = Environmental Science & Technology | volume = 51 | issue = 9 | pages = 5279–5286 | date = May 2017 | pmid = 28368574 | doi = 10.1021/acs.est.7b00701 | bibcode = 2017EnST...51.5279X | url = http://ir.rcees.ac.cn/handle/311016/39260 | access-date = 12 April 2022 | archive-date = 29 December 2022 | archive-url = https://web.archive.org/web/20221229150022/https://ir.rcees.ac.cn/handle/311016/39260 | url-status = dead }}</ref> shop receipts,<ref name=paper1/> and dental fillings.<ref name="teeth">{{cite journal | vauthors = Ahovuo-Saloranta A, Forss H, Walsh T, Nordblad A, Mäkelä M, Worthington HV | title = Pit and fissure sealants for preventing dental decay in permanent teeth | journal = The Cochrane Database of Systematic Reviews | volume = 2017 | pages = CD001830 | date = July 2017 | issue = 7 | pmid = 28759120 | pmc = 6483295 | doi = 10.1002/14651858.CD001830.pub5 }}</ref> BPA has been investigated by public health agencies in many countries, as well as by the [[World Health Organization]].<ref name=WHO /> 

While normal exposure is below the level currently associated with risk, several jurisdictions have taken steps to reduce exposure on a precautionary basis, in particular by banning BPA from baby bottles. There is some evidence that BPA exposure in infants has decreased as a result of this.<ref name="auto"/> BPA-free plastics have also been introduced, which are manufactured using alternative bisphenols such as [[bisphenol S]] and [[bisphenol F]], but there is also controversy around whether these are actually safer.<ref>{{cite journal | vauthors = Thoene M, Dzika E, Gonkowski S, Wojtkiewicz J | title = Bisphenol S in Food Causes Hormonal and Obesogenic Effects Comparable to or Worse than Bisphenol A: A Literature Review | journal = Nutrients | volume = 12 | issue = 2 | pages = 532 | date = February 2020 | pmid = 32092919 | pmc = 7071457 | doi = 10.3390/nu12020532 | doi-access = free }}</ref><ref name=Other>{{cite journal |last1=Chen |first1=Da |last2=Kannan |first2=Kurunthachalam |last3=Tan |first3=Hongli |last4=Zheng |first4=Zhengui |last5=Feng |first5=Yong-Lai |last6=Wu |first6=Yan |last7=Widelka |first7=Margaret |title=Bisphenol Analogues Other Than BPA: Environmental Occurrence, Human Exposure, and Toxicity—A Review |journal=Environmental Science & Technology |date=7 June 2016 |volume=50 |issue=11 |pages=5438–5453 |doi=10.1021/acs.est.5b05387|pmid=27143250 |bibcode=2016EnST...50.5438C}}</ref><ref>{{cite journal |last1=Eladak |first1=Soria |last2=Grisin |first2=Tiphany |last3=Moison |first3=Delphine |last4=Guerquin |first4=Marie-Justine |last5=N'Tumba-Byn |first5=Thierry |last6=Pozzi-Gaudin |first6=Stéphanie |last7=Benachi |first7=Alexandra |last8=Livera |first8=Gabriel |last9=Rouiller-Fabre |first9=Virginie |last10=Habert |first10=René |date=2015 |title=A new chapter in the bisphenol A story: bisphenol S and bisphenol F are not safe alternatives to this compound |journal=Fertility and Sterility |language=en |volume=103 |issue=1 |pages=11–21 |doi=10.1016/j.fertnstert.2014.11.005|pmid=25475787 |doi-access=free }}</ref>

== History ==
Bisphenol A was first reported in 1891 by the Russian [[chemist]] [[Aleksandr Dianin]].<ref>See:

* А. Дианина (1891) [https://books.google.com/books?id=VHYMAQAAIAAJ&pg=PA488 "О продуктахъ конденсацiи кетоновъ съ фенолами"] (On condensation products of ketones with phenols), ''Журнал Русского физико-химического общества'' (Journal of the Russian Physical Chemistry Society), '''23''' :  488-517, 523–546, 601–611; see especially pages 491-493 ("Диметилдифенолметань" (dimethyldiphenolmethane)).
* Reprinted in condensed form in:  A. Dianin (1892) [https://books.google.com/books?id=cx9LAAAAYAAJ&pg=PA334 "Condensationsproducte aus Ketonen und Phenolen"] (Condensation products of ketones and phenols), ''Berichte der Deutschen chemischen Gesellschaft zu Berlin'', '''25''', part 3 :  334-337. {{doi|10.1002/cber.18920250333}}</ref>

In 1934, workers at [[I.G. Farbenindustrie]] reported the coupling of BPA and [[epichlorohydrin]].  Over the following decade, coatings and resins derived from similar materials were described by workers at the companies of DeTrey Freres in [[Switzerland]] and DeVoe and Raynolds in the US. This early work underpinned the development of [[epoxy resins]], which in turn motivated production of BPA.<ref name="UllmannEpox">{{Ullmann| vauthors = Pham HQ, Marks MJ |chapter=Epoxy Resins|year=2012|doi=10.1002/14356007.a09_547.pub2|isbn=978-3527306732}}</ref> The utilization of BPA further expanded with discoveries at [[Bayer]] and [[General Electric]] on [[polycarbonate]] [[plastic]]s.  These plastics first appeared in 1958, being produced by [[Mobay]], General Electric, and Bayer.<ref name=Ullmann>{{Ullmann|first = Volker | last = Serini |chapter=Polycarbonates|year=2000|doi=10.1002/14356007.a21_207}}</ref>

The British biochemist Edward [[Charles Dodds]] tested BPA as an artificial [[estrogen]] in the early 1930s.<ref name="Vogel2009">{{cite journal | vauthors = Vogel SA | title = The politics of plastics: the making and unmaking of bisphenol a "safety" | journal = American Journal of Public Health | volume = 99 | issue = Suppl 3 | pages = S559–S566 | date = November 2009 | pmid = 19890158 | pmc = 2774166 | doi = 10.2105/AJPH.2008.159228 }}</ref><ref>{{cite journal|vauthors=Dodds EC, Lawson W | year = 1936| title = Synthetic Œstrogenic Agents without the Phenanthrene Nucleus| journal=Nature| volume = 137| issue =3476| page = 996|bibcode=1936Natur.137..996D| doi=10.1038/137996a0| s2cid = 4171635| doi-access =free}}</ref><ref name="W. Lawson, 1938 pp. 222">{{cite journal | vauthors = Dodds EC, Lawson W | year = 1938| title =  Molecular Structure in Relation to Oestrogenic Activity. Compounds without a Phenanthrene Nucleus| journal = Proceedings of the Royal Society of London B: Biological Sciences | volume = 125 | issue = 839| pages = 222–232 | doi=10.1098/rspb.1938.0023| bibcode=1938RSPSB.125..222D| doi-access = free}}</ref> Subsequent work found that it bound to [[estrogen receptors]] tens of thousands of times more weakly than [[estradiol]], the major natural female sex hormone.<ref>{{cite journal |last1=Kwon |first1=Jung-Hwan |last2=Katz |first2=Lynn E. |last3=Liljestrand |first3=Howard M. |title=Modeling binding equilibrium in a competitive estrogen receptor binding assay |journal=Chemosphere |date=October 2007 |volume=69 |issue=7 |pages=1025–1031 |doi=10.1016/j.chemosphere.2007.04.047|pmid=17559906 |bibcode=2007Chmsp..69.1025K }}</ref><ref name=Xenochemicals>{{cite journal |last1=Blair |first1=R. M. |title=The Estrogen Receptor Relative Binding Affinities of 188 Natural and Xenochemicals: Structural Diversity of Ligands |journal=Toxicological Sciences |date=1 March 2000 |volume=54 |issue=1 |pages=138–153 |doi=10.1093/toxsci/54.1.138|pmid=10746941 | doi-access = free}}</ref> Dodds eventually developed a structurally similar compound, [[diethylstilbestrol]] (DES), which was used as a synthetic estrogen drug in women and animals until it was banned due to its risk of causing cancer; the ban on use of DES in humans came in 1971 and in animals, in 1979.<ref name=Vogel2009 /> BPA was never used as a drug.<ref name="Vogel2009" />

== Production ==
The synthesis of BPA  still follows Dianin's general method, with the fundamentals changing little in 130 years. The [[condensation reaction|condensation]] of [[acetone]] (hence the suffix 'A' in the name)<ref>{{cite book | vauthors = Uglea CV, Negulescu II | title=Synthesis and Characterization of Oligomers | year=1991 | publisher=[[CRC Press]] | page=103 | isbn=978-0-8493-4954-6}}</ref> with two [[equivalent (chemistry)|equivalents]] of [[phenol]] is [[catalyzed]] by a strong acid, such as concentrated [[hydrochloric acid]], [[sulfuric acid]], or a solid acid [[Ion-exchange resin|resin]] such as the [[sulfonic acid]] form of [[polystyrene sulfonate]].<ref>{{cite journal | vauthors = De Angelis A, Ingallina P, Perego C |title=Solid Acid Catalysts for Industrial Condensations of Ketones and Aldehydes with Aromatics |journal=Industrial & Engineering Chemistry Research |date=March 2004 |volume=43 |issue=5 |pages=1169–1178 |doi=10.1021/ie030429+}}</ref> An excess of phenol is used to ensure full condensation and to limit the formation of byproducts, such as [[Dianin's compound]]. BPA is fairly cheap to produce, as the synthesis benefits from a high [[atom economy]] and large amounts of both starting materials are available from the [[cumene process]].<ref name="Fiege" /> As the only [[by-product]] is water, it may be considered an industrial example of [[green chemistry]]. Global production in 2022 was estimated to be in the region of 10 million tonnes.<ref name=production>{{cite journal | vauthors = Abraham A, Chakraborty P | title = A review on sources and health impacts of bisphenol A | journal = Reviews on Environmental Health | volume = 35 | issue = 2 | pages = 201–210 | date = June 2020 | pmid = 31743105 | doi = 10.1515/reveh-2019-0034 | s2cid = 208186123}}</ref>

:[[File:Synthesis Bisphenol A.svg|frameless|upright=2.4|Synthesis of bisphenol A from phenol and acetone]]

Usually, the addition of acetone takes place at the [[Arene substitution pattern|para position]] on both phenols, however minor amounts of the ortho-para (up to 3%) and ortho-ortho isomers are also produced, along with several other minor by‑products.<ref name=terasaki>{{cite journal | vauthors = Terasaki M, Nomachi M, Edmonds JS, Morita M | title = Impurities in industrial grade 4,4'-isopropylidene diphenol (bisphenol A): possible implications for estrogenic activity | journal = Chemosphere | volume = 55 | issue = 6 | pages = 927–931 | date = May 2004 | pmid = 15041297 | doi = 10.1016/j.chemosphere.2003.11.063 | bibcode = 2004Chmsp..55..927T }}</ref> These are not always removed and are known impurities in commercial samples of BPA.<ref>{{cite journal | vauthors = Pahigian JM, Zuo Y | title = Occurrence, endocrine-related bioeffects and fate of bisphenol A chemical degradation intermediates and impurities: A review | journal = Chemosphere | volume = 207 | pages = 469–480 | date = September 2018 | pmid = 29807346 | doi = 10.1016/j.chemosphere.2018.05.117 | s2cid = 44172964 | bibcode = 2018Chmsp.207..469P | doi-access = free }}</ref><ref name=terasaki/>

==Properties==
BPA has a fairly high melting point but can be easily dissolved in a broad range of organic solvents including [[toluene]], [[ethanol]] and [[ethyl acetate]].<ref>{{cite book |title=CRC handbook of chemistry and physics : a ready-reference book of chemical and physical data. |date=2017 |publisher=CRC Press, Inc.|location=Boca Raton, Florida |isbn=9781498754293 |pages=3–56 |edition=2016-2017, 97th |url=https://books.google.com/books?id=VVezDAAAQBAJ&dq=crc+handbook+of+chemistry+and+physics+%2280-05-7%22&pg=SA3-PA56|last1=Haynes |first1=William M. }}</ref> It may be purified by [[Recrystallization (chemistry)|recrystallisation]] from acetic acid with water.<ref>{{cite book |last1=Perrin |first1=Douglas Dalzell Perrin |last2=Armarego |first2=W. L. F. |title=Purification of laboratory chemicals |year=1988 |publisher=Butterworth-Heinemann |isbn=9780080347141 |page=208 |url=https://books.google.com/books?id=vLFXAAAAMAAJ}}</ref> Crystals form in the [[monoclinic]] [[space group]] P 2<sub>1</sub>/n (where n indicates the glide plane); within this individual molecules of BPA are arraigned with a 91.5° [[torsion angle]] between the phenol rings.<ref>{{cite web |title=2,2-bis(4-Hydroxyphenyl)propane |url=https://www.ccdc.cam.ac.uk/structures/Search?Ccdcid=1122458&DatabaseToSearch=Published |website=www.ccdc.cam.ac.uk |publisher=The Cambridge Crystallographic Data Centre |access-date=29 June 2022}}</ref><ref>{{cite journal |last1=Okada |first1=Kenji |title=X-ray crystal structure analyses and atomic charges of color former and developer. I. Color developers |journal=Journal of Molecular Structure |date=July 1996 |volume=380 |issue=3 |pages=223–233 |doi=10.1016/0022-2860(95)09168-8|bibcode=1996JMoSt.380..223O }}</ref><ref>{{cite journal |last1=Wolak |first1=J. E. |last2=Knutson |first2=J. |last3=Martin |first3=J. D. |last4=Boyle |first4=P. |last5=Sargent |first5=Andrew L. |last6=White |first6=Jeffery L. |title=Dynamic Disorder and Conformer Exchange in the Crystalline Monomer of Polycarbonate |journal=The Journal of Physical Chemistry B |date=1 December 2003 |volume=107 |issue=48 |pages=13293–13299 |doi=10.1021/jp036527q}}</ref> [[Spectroscopic]] data is available from [[National Institute of Advanced Industrial Science and Technology|AIST]].<ref>{{cite web |title=4,4'-isopropylidenediphenol |url=https://sdbs.db.aist.go.jp/CompoundView.aspx?sdbsno=1716 |website=sdbs.db.aist.go.jp |publisher=Spectral Database for Organic Compounds (SDBS) |access-date=8 August 2024}}</ref>

== Uses and applications ==
[[File:Polycarbonate water bottle.JPG|thumb|right|upright|Bisphenol&nbsp;A is primarily used to make plastics, such as this [[polycarbonate]] water bottle.]]

===Main uses===
==== Polycarbonates ====
{{main|Polycarbonate}}

About 65–70% of all bisphenol A is used to make [[polycarbonate]] plastics,<ref name="EU2008">{{cite book |author1=European Commission. Joint Research Centre. Institute for Health Consumer Protection |title=Updated European Union risk assessment report : 4,4'-isopropylidenediphenol (bisphenol-A) : environment addendum of February 2008 |date=2010 |publisher=Publications Office |isbn=9789279175428 |page=6 |doi=10.2788/40195 |doi-access=free}}</ref><ref name="Tom2021">{{cite journal | vauthors = Vasiljevic T, Harner T | title = Bisphenol A and its analogues in outdoor and indoor air: Properties, sources and global levels | journal = The Science of the Total Environment | volume = 789 | pages = 148013 | date = May 2021 | pmid = 34323825 | doi = 10.1016/j.scitotenv.2021.148013 | bibcode = 2021ScTEn.78948013V | doi-access = free}}</ref> which can consist of nearly 90% BPA by mass. [[Polymerisation]] is achieved by a reaction with [[phosgene]], conducted under biphasic conditions; the hydrochloric acid is scavenged with aqueous base.<ref name="UllmannPolyC">{{Ullmann|first=Volker|last1=Serini |title=Polycarbonates|year=2000|doi=10.1002/14356007.a21_207}}</ref> This process converts the individual molecules of BPA into large polymer chains, effectively trapping them.

:[[File:Polycarbonatsynthese.svg|500px]]

==== Epoxy and vinyl ester resins ====
About 25–30% of all BPA is used in the manufacture of [[epoxy resin]]s and [[vinyl ester resin]]s.<ref name="EU2008" /><ref name="Tom2021" /> For epoxy resin, it is first converted to its [[Bisphenol A diglycidyl ether|diglycidyl ether]] (usually abbreviated BADGE or DGEBA).<ref>{{cite journal | vauthors = Ng F, Couture G, Philippe C, Boutevin B, Caillol S | title = Bio-Based Aromatic Epoxy Monomers for Thermoset Materials | journal = Molecules | volume = 22 | issue = 1 | pages = 149 | date = January 2017 | pmid = 28106795 | pmc = 6155700 | doi = 10.3390/molecules22010149 | doi-access = free}}</ref><ref>{{cite book| vauthors = Kroschwitz JI |title=Kirk-Othmer Encyclopedia of Chemical Technology|year=1998|edition=5|volume=5|page=8|publisher=Wiley |isbn=978-0-471-52695-7}}</ref> This is achieved by a reaction with [[epichlorohydrin]] under basic conditions.

:[[File:Diglycidether.svg|350px]]

Some of this is further reacted with [[methacrylic acid]] to form [[bis-GMA]], which is used to make vinyl ester resins. Alternatively, and to a much lesser extent, BPA may be [[ethoxylated]] and then converted to its di[[acrylate]] and di[[methacrylate]] derivatives (bis-EMA, or EBPADMA). These may be incorporated at low levels in vinyl ester resins to change their physical properties<ref>{{cite journal | vauthors = Gonçalves F, Kawano Y, Pfeifer C, Stansbury JW, Braga RR | title = Influence of BisGMA, TEGDMA, and BisEMA contents on viscosity, conversion, and flexural strength of experimental resins and composites | journal = European Journal of Oral Sciences | volume = 117 | issue = 4 | pages = 442–446 | date = August 2009 | pmid = 19627357 | doi = 10.1111/j.1600-0722.2009.00636.x }}</ref> and see common use in [[dental composite]]s and [[Dental sealant|sealants]].<ref>{{cite journal |last1=Sideridou |first1=I. |last2=Tserki |first2=V. |last3=Papanastasiou |first3=G. |title=Effect of chemical structure on degree of conversion in light-cured dimethacrylate-based dental resins |journal=Biomaterials |date=April 2002 |volume=23 |issue=8 |pages=1819–1829 |doi=10.1016/S0142-9612(01)00308-8|pmid=11950052 }}</ref><ref>{{cite journal |last1=Sideridou |first1=Irini D. |last2=Achilias |first2=Dimitris S. |title=Elution study of unreacted Bis-GMA, TEGDMA, UDMA, and Bis-EMA from light-cured dental resins and resin composites using HPLC |journal=Journal of Biomedical Materials Research Part B: Applied Biomaterials |date=July 2005 |volume=74B |issue=1 |pages=617–626 |doi=10.1002/jbm.b.30252|pmid=15889433}}</ref>

===Minor uses===
The remaining 5% of BPA is used in a wide range of applications, many of which involve plastic.<ref name=potential>{{cite journal | vauthors = Geens T, Goeyens L, Covaci A | title = Are potential sources for human exposure to bisphenol-A overlooked? | journal = International Journal of Hygiene and Environmental Health | volume = 214 | issue = 5 | pages = 339–347 | date = September 2011 | pmid = 21570349 | doi = 10.1016/j.ijheh.2011.04.005 | bibcode = 2011IJHEH.214..339G }}</ref> BPA is a major component of several [[high-performance plastics]], the production of these is low compared to other plastics but still equals several thousand tons a year. Comparatively minor amounts of BPA are also used as additives or modifiers in some [[commodity plastics]]. These materials are much more common but their BPA content will be low.

====Plastics====
;As a major component 
* Polycyanurates can be produced from BPA by way of its di[[cyanate ester]] (BADCy).<ref name=potential /> This is formed by a reaction between BPA and [[cyanogen bromide]].<ref>{{cite book |last1=Hamerton |first1=Ian |title=Chemistry and technology of cyanate ester resins |date=1994 |publisher=Blackie Academic & Professional |location=London |isbn=978-0-7514-0044-1 |edition=1st}}</ref> Examples include [[BT-Epoxy]], which is one of a number of resins used in the production of [[printed circuit boards]].
* [[Polyetherimide]]s such as Ultem can be produced from BPA via a nitro-displacement of appropriate bisnitroimides.<ref>{{cite journal | vauthors = Takekoshi T, Kochanowski JE, Manello JS, Webber MJ |title=Polyetherimides. I. Preparation of dianhydrides containing aromatic ether groups |journal=Journal of Polymer Science: Polymer Chemistry Edition |date=June 1985 |volume=23 |issue=6 |pages=1759–1769 |doi=10.1002/pol.1985.170230616|bibcode=1985JPoSA..23.1759T}}</ref><ref>{{cite book |last1=Lau |first1=Kreisler S.Y. |title=Handbook of thermoset plastics |date=2014 |publisher=William Andrew |location=San Diego |isbn=978-1-4557-3107-7 |pages=319–323 |edition=3rd |chapter=10 - High-Performance Polyimides and High Temperature Resistant Polymers}}</ref> These [[thermoplastic]] [[polyimide]] plastics have exceptional resistance to mechanical, thermal and chemical damage. They are used in medical devices and other high performance instrumentation.
* [[Polybenzoxazine]]s may be produced from a number of biphenols, including BPA.<ref>{{cite journal | vauthors = Vijayakumar CT, Shamim Rishwana S, Surender R, David Mathan N, Vinayagamoorthi S, Alam S |title=Structurally diverse benzoxazines: synthesis, polymerization, and thermal stability |journal=Designed Monomers and Polymers |date=2 January 2014 |volume=17 |issue=1 |pages=47–57 |doi=10.1080/15685551.2013.797216|s2cid=94255723 |doi-access=free }}</ref><ref>{{cite journal | vauthors = Ghosh NN, Kiskan B, Yagci Y |title=Polybenzoxazines—New high performance thermosetting resins: Synthesis and properties |journal=Progress in Polymer Science |date=November 2007 |volume=32 |issue=11 |pages=1344–1391 |doi=10.1016/j.progpolymsci.2007.07.002}}</ref>
* [[Polysulfone]]s can be produced from BPA and [[bis(4-chlorophenyl) sulfone]] forming poly(bisphenol-A sulfone) (PSF). It is used as a high performance alternative to polycarbonate.<ref name=potential /><ref name="q156">{{cite book | title=Kirk-Othmer Encyclopedia of Chemical Technology | publisher=Wiley | date=2001-01-26 | isbn=978-0-471-48494-3 | doi=10.1002/0471238961.0118151323080920.a01 | page=}}</ref>
*Bisphenol-A formaldehyde resins are a subset of [[phenol formaldehyde resin]]s. They are used in the production of [[high-pressure laminate]]s<ref name=potential />

;As a minor component 
* [[Polyurethane]] can incorporate BPA and its derivatives as hard segment chain extenders, particularly in [[memory foam]]s.<ref>{{cite journal | vauthors = Laza JM, Veloso A, Vilas JL |title=Tailoring new bisphenol a ethoxylated shape memory polyurethanes |journal=Journal of Applied Polymer Science |date=10 January 2021 |volume=138 |issue=2 |pages=49660 |doi=10.1002/app.49660|s2cid=224955435 }}</ref><ref>{{cite book |last1=Król |first1=Piotr |title=Linear polyurethanes : synthesis methods, chemical structures, properties and applications |date=2008 |publisher=VSP |location=Leiden |isbn=9789004161245 |pages=11–14}}</ref>
* [[PVC]] can contain BPA and its derivatives through multiple routes. BPA is sometimes used as an antioxidant in [[phthalates]],<ref>{{cite web |title=European Union Summary Risk Assessment Report - Bis (2-ethylhexyl) Phthalate (DEHP) |url=https://publications.jrc.ec.europa.eu/repository/handle/JRC45844 |website=Joint Research Centre (JRC) Publications Repository |date=16 July 2008 |publisher=European Commission |issn=1018-5593|access-date=24 November 2021}}{{open access}}</ref> which are extensively used as [[plasticizer]]s for PVC. BPA has also been used as an antioxidant to protect sensitive PVC [[heat stabilizer]]s. Historically 5–10% by weight of BPA was included in barium-cadmium types, although these have largely been phased out due health concerns surrounding the [[cadmium]]. BPA diglycidyl ether (BADGE) is used as an acid scavenger, particularly in PVC [[Dispersion (chemistry)|dispersion]]s, such as organosols or [[plastisol]]s,<ref>{{cite journal | vauthors = Shah AC, Poledna DJ |title=Review of PVC dispersion and blending resin products |journal=Journal of Vinyl and Additive Technology |date=September 2003 |volume=9 |issue=3 |pages=146–154 |doi=10.1002/vnl.10076|s2cid=98016356 }}</ref><ref>{{cite journal | vauthors = Shah AC, Poledna DJ |title=Review of specialty PVC resins |journal=Journal of Vinyl and Additive Technology |date=September 2002 |volume=8 |issue=3 |pages=214–221 |doi=10.1002/vnl.10365|s2cid=97146596 }}</ref> which are used as coatings for the inside of food cans, as well as embossed clothes designs produced using [[heat transfer vinyl]] or [[screen printing]] machines.<ref name="ir.rcees.ac.cn"/>

;Derivatives used as flame retardants
BPA is used to form a number of [[flame retardant]]s used in plastics.<ref name=UllmannBr>{{ Ullmann | vauthors = Dagani MJ, Barda HJ, Benya TJ, Sanders DC | title = Bromine Compounds | doi = 10.1002/14356007.a04_405 }}</ref><ref>{{cite journal |last1=Bergman |first1=Åke |last2=Rydén |first2=Andreas |last3=Law |first3=Robin J. |last4=de Boer |first4=Jacob |last5=Covaci |first5=Adrian |last6=Alaee |first6=Mehran |last7=Birnbaum |first7=Linda |last8=Petreas |first8=Myrto |last9=Rose |first9=Martin |last10=Sakai |first10=Shinichi |last11=Van den Eede |first11=Nele |last12=van der Veen |first12=Ike |title=A novel abbreviation standard for organobromine, organochlorine and organophosphorus flame retardants and some characteristics of the chemicals |journal=Environment International |date=November 2012 |volume=49 |pages=57–82 |doi=10.1016/j.envint.2012.08.003|pmid=22982223 |pmc=3483428 |bibcode=2012EnInt..49...57B |hdl=2433/193940 |hdl-access=free }}</ref>

{{multiple image
| direction = Horizontal 
| align = center
| total_width = 750
| image1 = Tetrabromobisphenol A.svg
| caption1 = [[Tetrabromobisphenol A]] (TBBPA)
| image2 = Tetrabromobisphenol A bis(2,3-dibromopropyl) ether (TBBPA-DBPE).png
| caption2 = Tetrabromobisphenol A bis(2,3-dibromopropyl) ether (TBBPA-DBPE)
| image3 = Bisphenol_A_diphenyl_phosphate.svg
| caption3 = [[Bisphenol A diphenyl phosphate]] (BADP)
}}

Bromination of BPA forms [[tetrabromobisphenol A]] (TBBPA), which is mainly used as a reactive component of polymers, meaning that it is incorporated into the polymer backbone.  It is used to prepare fire-resistant [[polycarbonate]]s by replacing some bisphenol A. A lower grade of TBBPA is used to prepare [[epoxy resin]]s, used in [[printed circuit board]]s. TBBPA is also converted to TBBPA-BDBPE which can be used as a flame retardant in [[polypropylene]]. TBBPA-BDBPE is not chemically bonded to the polymer and can leach out into the environment.<ref>{{cite journal |last1=Gauthier |first1=Lewis T. |last2=Laurich |first2=Bruce |last3=Hebert |first3=Craig E. |last4=Drake |first4=Christine |last5=Letcher |first5=Robert J. |title=Tetrabromobisphenol-A-Bis(dibromopropyl ether) Flame Retardant in Eggs, Regurgitates, and Feces of Herring Gulls from Multiple North American Great Lakes Locations |journal=Environmental Science & Technology |date=20 August 2019 |volume=53 |issue=16 |pages=9564–9571 |doi=10.1021/acs.est.9b02472|pmid=31364365 |bibcode=2019EnST...53.9564G |s2cid=198998658 }}</ref> The use of these compounds is diminishing due to restrictions on [[brominated flame retardant]]s. The reaction of BPA with [[phosphorus oxychloride]] and [[phenol]] forms BADP, which is used as a liquid flame retarder in some high performance [[polymer blend]]s such as polycarbonate/[[Acrylonitrile butadiene styrene|ABS]] mixtures that are used to form the casings for household electronics.<ref>{{cite journal |last1=Pawlowski |first1=Kristin H |last2=Schartel |first2=Bernhard |title=Flame retardancy mechanisms of triphenyl phosphate, resorcinol bis(diphenyl phosphate) and bisphenol A bis(diphenyl phosphate) in polycarbonate/acrylonitrile–butadiene–styrene blends |journal=Polymer International |date=November 2007 |volume=56 |issue=11 |pages=1404–1414 |doi=10.1002/pi.2290}}</ref>

====Other applications====
* BPA is used as an antioxidant in several fields, particularly in [[brake fluid]]s.<ref>{{cite journal | vauthors = Lamprea K, Bressy A, Mirande-Bret C, Caupos E, Gromaire MC | title = Alkylphenol and bisphenol A contamination of urban runoff: an evaluation of the emission potentials of various construction materials and automotive supplies | journal = Environmental Science and Pollution Research International | volume = 25 | issue = 22 | pages = 21887–21900 | date = August 2018 | pmid = 29796891 | doi = 10.1007/s11356-018-2272-z | bibcode = 2018ESPR...2521887L | s2cid = 44140721 | url = https://hal.science/hal-01813100/file/Lamprea2018_ESPR.pdf }}</ref>
*BPA is used as a developing agent in [[thermal paper]] (shop receipts).<ref name=paper1>{{cite journal | vauthors = Björnsdotter MK, de Boer J, Ballesteros-Gómez A | title = Bisphenol A and replacements in thermal paper: A review | journal = Chemosphere | volume = 182 | pages = 691–706 | date = September 2017 | pmid = 28528315 | doi = 10.1016/j.chemosphere.2017.05.070 | bibcode = 2017Chmsp.182..691B | hdl = 1871.1/0c9480c5-48ce-4955-8d53-39b8b246802f | url = https://research.vu.nl/en/publications/0c9480c5-48ce-4955-8d53-39b8b246802f | hdl-access = free }}</ref> Recycled paper products can also contain BPA,<ref>{{cite journal | vauthors = Liao C, Kannan K | title = Widespread occurrence of bisphenol A in paper and paper products: implications for human exposure | journal = Environmental Science & Technology | volume = 45 | issue = 21 | pages = 9372–9379 | date = November 2011 | pmid = 21939283 | doi = 10.1021/es202507f | bibcode = 2011EnST...45.9372L }}</ref> although this can depend strongly on how it is recycled. [[Deinking]] can remove 95% of BPA,<ref name=EU2008 /> with the pulp produced used to make newsprint, toilet paper and facial tissues. If deinking is not performed then the BPA remains in the fibers, paper recycled this way is usually made into [[corrugated fiberboard]].<ref name=EU2008 />
* [[Ethoxylated]] BPA finds minor use as a 'levelling agent' in tin [[electroplating]]. 
* Several drug candidates have also been developed from bisphenol A, including [[ralaniten]], [[ralaniten acetate]], and [[EPI-001]].

==BPA substitutes==
{{see also|Bisphenol}}
Concerns about the health effects of BPA have led some manufacturers replacing it with other bisphenols, such as [[bisphenol S]] and [[bisphenol F]]. These are produced in a similar manner to BPA, by replacing acetone with other compounds, which undergo analogous condensation reactions.<ref name="Fiege">{{Ullmann| vauthors = Fiege H, Voges HW, Hamamoto T, Umemura S, Iwata T, Miki H, Fujita Y, Buysch HJ, Garbe D, Paulus W |year=2000 |doi=10.1002/14356007.a19_313|title=Phenol Derivatives |isbn=978-3527306732}}</ref> Thus, in [[bisphenol F]], the F signifies [[formaldehyde]].
Health concerns have also been raised about these substitutes.<ref>{{cite journal | vauthors = Rochester JR, Bolden AL | title = Bisphenol S and F: A Systematic Review and Comparison of the Hormonal Activity of Bisphenol A Substitutes | journal = Environmental Health Perspectives | volume = 123 | issue = 7 | pages = 643–650 | date = July 2015 | pmid = 25775505 | pmc = 4492270 | doi = 10.1289/ehp.1408989| bibcode = 2015EnvHP.123..643R }}</ref><ref name=Other /> Alternative polymers, such as [[tritan copolyester]] have been developed to give the same properties as polycarbonate (durable, clear) without using BPA or its analogues. 

{| class="wikitable" 
! Structural formula
! Name
! [[CAS registry number|CAS]] 
! colspan="2" | [[Reactant]]s 
|-
|[[File:Bisphenol AF.svg|150px|Bisphenol AF]]||[[Bisphenol AF]] || 1478-61-1 || [[Phenol]] || [[Hexafluoroacetone]]
|-
|[[File:Bisphenol F.svg|150px|Bisphenol F]]||[[Bisphenol F]] || 620-92-8 || [[Phenol]] || [[Formaldehyde]]
|-
|[[File:Bisphenol S.svg|150px|Bisphenol S]]||[[Bisphenol S]] || 80-09-1 || [[Phenol]] || [[Sulfur trioxide]]
|-
|[[File:Bisphenol Z.svg|150px|Bisphenol Z]]||[[Bisphenol Z]] || 843-55-0 || [[Phenol]] || [[Cyclohexanone]]
|-
|[[File:Tetramethyl bisphenol F.png|150px|]]||[[Tetramethyl bisphenol F]] || 5384-21-4 || [[2,6-xylenol]] || [[Formaldehyde]]
|}

==Human safety==
===Exposure===
[[File:Import canned foods in Kobe.jpg|thumb|upright|The largest exposure humans have had to BPA is from food packaging, particularly the [[epoxy]] lining of metal food, beverage cans and [[plastic bottle]]s.]]

As a result of the presence of BPA in plastics and other commonplace materials, most people are frequently exposed to trace levels of BPA.<ref>{{cite journal | vauthors = 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 = Environmental Health Perspectives | volume = 116 | issue = 1 | pages = 39–44 | date = January 2008 | pmid = 18197297 | pmc = 2199288 | doi = 10.1289/ehp.10753 | bibcode = 2008EnvHP.116...39C }}</ref><ref>{{cite journal | vauthors = Thoene M, Rytel L, Nowicka N, Wojtkiewicz J | title = The state of bisphenol research in the lesser developed countries of the EU: a mini-review | journal = Toxicology Research | volume = 7 | issue = 3 | pages = 371–380 | date = May 2018 | pmid = 30090587 | pmc = 6062254 | doi = 10.1039/c8tx00064f }}</ref><ref>{{cite journal | vauthors = Vandenberg LN, Hauser R, Marcus M, Olea N, Welshons WV | title = Human exposure to bisphenol A (BPA) | journal = Reproductive Toxicology | volume = 24 | issue = 2 | pages = 139–177 | date = August 2007 | pmid = 17825522 | doi = 10.1016/j.reprotox.2007.07.010 | bibcode = 2007RepTx..24..139V }}</ref> The primary source of human exposure is via food, as epoxy and PVC are used to line the inside of food cans to prevent corrosion of the metal by acidic foodstuffs. Polycarbonate drink containers are also a source of exposure, although most disposable drinks bottles are actually made of [[Polyethylene terephthalate|PET]], which contains no BPA. Among the non-food sources, exposure routes include through dust,<ref name="Tom2021"/> thermal paper,<ref name="paper1"/> clothing,<ref name="ir.rcees.ac.cn"/> dental materials,<ref>{{cite journal |last1=Van Landuyt |first1=K.L. |last2=Nawrot |first2=Tim |last3=Geebelen |first3=B. |last4=De Munck |first4=J. |last5=Snauwaert |first5=J. |last6=Yoshihara |first6=K. |last7=Scheers |first7=Hans |last8=Godderis |first8=Lode |last9=Hoet |first9=P. |last10=Van Meerbeek |first10=B. |title=How much do resin-based dental materials release? A meta-analytical approach |journal=Dental Materials |date=August 2011 |volume=27 |issue=8 |pages=723–747 |doi=10.1016/j.dental.2011.05.001|pmid=21664675 }}</ref> and medical devices.<ref name="Covaci"/> Although BPA exposure is common, it does not accumulate within the body, with [[toxicokinetic]] studies showing the [[biological half-life]] of BPA in adult humans to be around two<ref>{{cite journal |vauthors=Tsukioka T, Terasawa JI, Sato S, Hatayama Y, Makino T, Nakazawa H |date=2004 |title=Development of Analytical Method for Determining Trace Amounts of BPA in Urine Samples and Estimation of Exposure to BPA. |journal=Journal of Environmental Chemistry |volume=14 |issue=1 |pages=57–63 |doi=10.5985/jec.14.57 |doi-access=free}}</ref><ref>{{cite journal |vauthors=Shin BS, Kim CH, Jun YS, Kim DH, Lee BM, Yoon CH, Park EH, Lee KC, Han SY, Park KL, Kim HS, Yoo SD |date=December 2004 |title=Physiologically based pharmacokinetics of bisphenol A |journal=Journal of Toxicology and Environmental Health. Part A |volume=67 |issue=23–24 |pages=1971–1985 |bibcode=2004JTEHA..67.1971S |doi=10.1080/15287390490514615 |pmid=15513896 |s2cid=24467830}}</ref> to five hours.<ref>{{Cite journal |last1=Stahlhut |first1=Richard W. |last2=Welshons |first2=Wade V. |last3=Swan |first3=Shanna H. |date=May 2009 |title=Bisphenol A data in NHANES suggest longer than expected half-life, substantial nonfood exposure, or both |journal=Environmental Health Perspectives |volume=117 |issue=5 |pages=784–789 |doi=10.1289/ehp.0800376 |issn=1552-9924 |pmc=2685842 |pmid=19479022|bibcode=2009EnvHP.117..784S }}</ref> During its elimination, the body first converts BPA into more water-soluble compounds via [[glucuronidation]] or [[sulfation]], which are then removed from the body through urine. This allows exposure to be easily determined by urine testing, facilitating convenient [[biomonitoring]] of populations.<ref name="auto">{{cite journal | vauthors = Huang RP, Liu ZH, Yin H, Dang Z, Wu PX, Zhu NW, Lin Z | title = Bisphenol A concentrations in human urine, human intakes across six continents, and annual trends of average intakes in adult and child populations worldwide: A thorough literature review | journal = The Science of the Total Environment | volume = 626 | pages = 971–981 | date = June 2018 | pmid = 29898562 | doi = 10.1016/j.scitotenv.2018.01.144 | s2cid = 49194096 | bibcode = 2018ScTEn.626..971H }}</ref><ref name=Covaci /><ref>{{cite journal |last1=Bousoumah |first1=Radia |last2=Leso |first2=Veruscka |last3=Iavicoli |first3=Ivo |last4=Huuskonen |first4=Pasi |last5=Viegas |first5=Susana |last6=Porras |first6=Simo P. |last7=Santonen |first7=Tiina |last8=Frery |first8=Nadine |last9=Robert |first9=Alain |last10=Ndaw |first10=Sophie |title=Biomonitoring of occupational exposure to bisphenol A, bisphenol S and bisphenol F: A systematic review |journal=Science of the Total Environment |date=August 2021 |volume=783 |pages=146905 |doi=10.1016/j.scitotenv.2021.146905|pmid=33865140 |bibcode=2021ScTEn.78346905B |s2cid=233290894 |doi-access=free|hdl=10400.21/13242 |hdl-access=free }}</ref> Food and drink containers made from Bisphenol A-containing plastics do not contaminate the content to cause any increased cancer risk.<ref name=cruk>{{cite web |publisher=[[Cancer Research UK]] |url=https://www.cancerresearchuk.org/about-cancer/causes-of-cancer/cancer-myths/does-using-plastic-bottles-and-containers-cause-cancer |title=Does using plastic bottles and containers cause cancer? |date=23 December 2021}}</ref>

===Health effects and regulation===
{{main|Health effects of Bisphenol A}}
The health effects of BPA have been the subject of prolonged public and scientific discourse,<ref name=WHO /><ref name=German2011>{{cite journal | vauthors = Hengstler JG, Foth H, Gebel T, Kramer PJ, Lilienblum W, Schweinfurth H, Völkel W, Wollin KM, Gundert-Remy U | title = Critical evaluation of key evidence on the human health hazards of exposure to bisphenol A | journal = Critical Reviews in Toxicology | volume = 41 | issue = 4 | pages = 263–291 | date = April 2011 | pmid = 21438738 | pmc = 3135059 | doi = 10.3109/10408444.2011.558487}}</ref><ref name=GLP>{{cite journal | vauthors = Myers JP, vom Saal FS, Akingbemi BT, Arizono K, Belcher S, Colborn T, Chahoud I, Crain DA, Farabollini F, Guillette LJ, Hassold T, Ho SM, Hunt PA, Iguchi T, Jobling S, Kanno J, Laufer H, Marcus M, McLachlan JA, Nadal A, Oehlmann J, Olea N, Palanza P, Parmigiani S, Rubin BS, Schoenfelder G, Sonnenschein C, Soto AM, Talsness CE, Taylor JA, Vandenberg LN, Vandenbergh JG, Vogel S, Watson CS, Welshons WV, Zoeller RT | display-authors = 6 | title = Why public health agencies cannot depend on good laboratory practices as a criterion for selecting data: the case of bisphenol A | journal = Environmental Health Perspectives | volume = 117 | issue = 3 | pages = 309–315 | date = March 2009 | pmid = 19337501 | pmc = 2661896 | doi = 10.1289/ehp.0800173 | bibcode = 2009EnvHP.117..309M }}</ref> with [[PubMed]] listing more than 18,000 publishings related to the subject as of 2024.<ref>{{cite web |title=bisphenol a - Search Results - PubMed |url=https://pubmed.ncbi.nlm.nih.gov/?term=bisphenol+a |website=PubMed |access-date=26 January 2024 |language=en}}</ref> Concern is mostly related to its [[estrogen]]-like activity, although it can interact with other receptor systems as an [[Endocrine disruptor|endocrine-disrupting chemical]].<ref name="receptors">{{cite journal |last1=MacKay |first1=Harry |last2=Abizaid |first2=Alfonso |title=A plurality of molecular targets: The receptor ecosystem for bisphenol-A (BPA) |journal=Hormones and Behavior |date=May 2018 |volume=101 |pages=59–67 |doi=10.1016/j.yhbeh.2017.11.001|pmid=29104009 |s2cid=23088708 }}</ref> These interactions are all very weak, but exposure to BPA is effectively lifelong, leading to concern over possible cumulative effects. Studying this sort of long‑term, low‑dose interaction is difficult, and although there have been numerous studies, there are considerable discrepancies in their conclusions regarding the nature of the effects observed as well as the levels at which they occur.<ref name=WHO /> A common criticism is that industry-sponsored trials tend to show BPA as being safer than studies performed by academic or government laboratories,<ref name=GLP/><ref>{{cite journal |vauthors=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 |pmc=1280330 |doi=10.1289/ehp.7713|bibcode=2005EnvHP.113..926V }}</ref> although this has also been explained in terms of industry studies being better designed.<ref name=German2011 /><ref>{{cite journal |last1=Teeguarden |first1=Justin G. |last2=Hanson-Drury |first2=Sesha |title=A systematic review of Bisphenol A "low dose" studies in the context of human exposure: A case for establishing standards for reporting "low-dose" effects of chemicals |journal=Food and Chemical Toxicology |date=December 2013 |volume=62 |pages=935–948 |doi=10.1016/j.fct.2013.07.007|pmid=23867546}}</ref>

In the 2010s public health agencies in the EU,<ref>{{cite web |title=Bisphenol A - ECHA |url=https://echa.europa.eu/hot-topics/bisphenol-a |website=echa.europa.eu |access-date=28 March 2022 |archive-date=8 June 2022 |archive-url=https://web.archive.org/web/20220608014918/https://echa.europa.eu/hot-topics/bisphenol-a |url-status=dead }}</ref><ref>{{cite book |title=EFSA explains the Safety of Bisphenol A: scientific opinion on bisphenol A (2015). |publisher=European Food Safety Authority  |date=2015 |doi=10.2805/075460|author1=European Food Safety Authority |isbn=9789291996421 }}</ref><ref>{{cite journal |title=Scientific Opinion on the risks to public health related to the presence of bisphenol A (BPA) in foodstuffs |journal=EFSA Journal |date=21 January 2015 |volume=13 |issue=1 |page=3978 |doi=10.2903/j.efsa.2015.3978|hdl=2164/12119 |hdl-access=free }}</ref> US,<ref>{{cite web | author = OCSPP US EPA |title=Risk Management for Bisphenol A (BPA) |url=https://www.epa.gov/assessing-and-managing-chemicals-under-tsca/risk-management-bisphenol-bpa |website=www.epa.gov |access-date=28 March 2022 |language=en |date=21 September 2015}}</ref><ref>{{cite book | title = NTP Research Report on the Consortium Linking Academic and Regulatory Insights on Bisphenol A Toxicity (CLARITY-BPA): A Compendium of Published Findings | pages = 18 | date = October 2021 | pmid = 34910417 | doi = 10.22427/NTP-RR-18 | s2cid = 240266384 | author1 = CLARITY-BPA Research Program }}</ref> Canada,<ref>{{cite web |last=Health Canada |date=16 April 2013 |title=Bisphenol A (BPA) |url=https://www.canada.ca/en/health-canada/services/home-garden-safety/bisphenol-bpa.html |access-date=28 March 2022 |website=www.canada.ca ([[Health Canada]]) |publisher=Government of Canada}}</ref> Australia<ref>{{cite web |title=Bisphenol A (BPA) |url=https://www.foodstandards.gov.au/consumer/chemicals/bpa/Pages/default.aspx |access-date=28 March 2022 |website=Food Standards Australia New Zealand ([[FSANZ]]) |publisher=Department of Health (Australia) |archive-date=24 March 2022 |archive-url=https://web.archive.org/web/20220324044358/https://www.foodstandards.gov.au/consumer/chemicals/bpa/Pages/default.aspx |url-status=dead }}</ref> and Japan as well as the [[WHO]]<ref name=WHO>{{cite book |title=Joint FAO/WHO expert meeting to review toxicological and health aspects of bisphenol A : final report, including report of stakeholder meeting on bisphenol A, 1-5 November 2010, Ottawa, Canada |date=2011 |publisher=World Health Organization |hdl=10665/44624 |isbn=978-92-4-156427-4 |url=https://apps.who.int/iris/handle/10665/44624 |access-date=23 March 2022 |language=en}}</ref> all reviewed the health risks of BPA, and found normal exposure to be below the level currently associated with risk. Regardless, due to the scientific uncertainty, many jurisdictions continued to take steps to reduce exposure on a precautionary basis. In particular, infants were considered to be at greater risk,<ref>{{cite book | vauthors = Aschberger K, Castello P, Hoekstra E |title=Bisphenol A and baby bottles : challenges and perspectives |publisher=The Publications Office of the European Union |date=2010 |doi=10.2788/97553 |isbn=9789279158698 |doi-access=free}}</ref> leading to bans on the use of BPA in [[baby bottle]]s and related products by the US,<ref>{{cite web |title=Indirect Food Additives: Polymers |url=https://www.federalregister.gov/documents/2012/07/17/2012-17366/indirect-food-additives-polymers |website=Federal Register |date=17 July 2012 |publisher=U.S. Government Publishing Office}}{{Federal Register|77|41899}}</ref> Canada,<ref>{{cite web | author = Legislative Services Branch|title=Consolidated federal laws of canada, Canada Consumer Product Safety Act |url=https://laws-lois.justice.gc.ca/eng/acts/C-1.68/index.html |website=laws-lois.justice.gc.ca |date=1 July 2020}}</ref> and EU<ref>{{cite web |title=EUR-Lex - 32011L0008 - EN - EUR-Lex |url=https://eur-lex.europa.eu/eli/dir/2011/8/oj |website=EUR-Lex |publisher=European Union |language=en |quote=COMMISSION DIRECTIVE 2011/8/EU of 28 January 2011 amending Directive 2002/72/EC as regards the restriction of use of Bisphenol A in plastic infant feeding bottles}}</ref> amongst others. Bottle producers largely switched from polycarbonate to [[polypropylene]] and there is some evidence that BPA exposure in infants has decreased as a result of this.<ref name="auto"/> The [[European Food Safety Authority]] completed a re-evaluation into the risks of BPA in 2023, concluding that its [[tolerable daily intake]] should be greatly reduced.<ref>{{cite journal |last1=Lambré |first1=Claude |last2=Barat Baviera |first2=José Manuel |last3=Bolognesi |first3=Claudia |last4=Chesson |first4=Andrew |last5=Cocconcelli |first5=Pier Sandro |last6=Crebelli |first6=Riccardo |last7=Gott |first7=David Michael |last8=Grob |first8=Konrad |last9=Lampi |first9=Evgenia |last10=Mengelers |first10=Marcel |last11=Mortensen |first11=Alicja |last12=Rivière |first12=Gilles |last13=Silano (until December †) |first13=Vittorio |last14=Steffensen |first14=Inger-Lise |last15=Tlustos |first15=Christina |last16=Vernis |first16=Laurence |last17=Zorn |first17=Holger |last18=Batke |first18=Monika |last19=Bignami |first19=Margherita |last20=Corsini |first20=Emanuela |last21=FitzGerald |first21=Rex |last22=Gundert-Remy |first22=Ursula |last23=Halldorsson |first23=Thorhallur |last24=Hart |first24=Andrew |last25=Ntzani |first25=Evangelia |last26=Scanziani |first26=Eugenio |last27=Schroeder |first27=Henri |last28=Ulbrich |first28=Beate |last29=Waalkens-Berendsen |first29=Dina |last30=Woelfle |first30=Detlef |last31=Al Harraq |first31=Zainab |last32=Baert |first32=Katleen |last33=Carfì |first33=Maria |last34=Castoldi |first34=Anna F |last35=Croera |first35=Cristina |last36=Van Loveren |first36=Henk |title=Re-evaluation of the risks to public health related to the presence of bisphenol A (BPA) in foodstuffs |journal=EFSA Journal |date=April 2023 |volume=21 |issue=4 |pages=e06857 |doi=10.2903/j.efsa.2023.6857|pmid=37089179 |pmc=10113887 |hdl=20.500.11815/4370 |hdl-access=free }}</ref> This led the European Union to ban BPA in all the food contact materials, including plastic and coated packaging, in December of 2024.<ref>{{cite web |title=Regulation - EU - 2024/3190 - EN - EUR-Lex |url=https://eur-lex.europa.eu/eli/reg/2024/3190/oj/eng |access-date=14 January 2025 |website=eur-lex.europa.eu |language=en}}</ref> The ban will come into force after an implementation period of up to three years.

BPA exhibits very low [[acute toxicity]] (i.e. from a single large dose) as indicated by its [[LD50|LD<sub>50</sub>]] of 4&nbsp;g/kg (mouse). Reports indicate that it is a minor skin irritant as well, although less so than [[phenol]].<ref name="Fiege" />

=== Pharmacology ===
[[File:BPAvEstdiol.svg|thumb|Overlay of [[estradiol]], the major female sex hormone in humans (green) and BPA (purple). This displays the [[structure–activity relationship]] which allows BPA to mimic the effects of estradiol and other estrogens.]]

BPA has been found to interact with a diverse range of [[hormone receptor]]s, in both humans and animals.<ref name="receptors" /> It binds to both of the [[nuclear receptor|nuclear]] [[estrogen receptor]]s (ERs), [[estrogen receptor alpha|ERα]] and [[estrogen receptor beta|ERβ]]. BPA is a [[selective estrogen receptor modulator]] (SERM), or [[partial agonist]] of the ER, so it can serve as both an [[estrogen]] [[agonist]] and [[receptor antagonist|antagonist]]. However, it is 1000- to 2000-fold less potent than [[estradiol]], the major female sex hormone in humans. At high concentrations, BPA also binds to and acts as an antagonist of the [[androgen receptor]] (AR). In addition to receptor binding, the compound has been found to affect [[Leydig cell]] [[steroidogenesis]], including affecting [[CYP17A1|17α-hydroxylase/17,20 lyase]] and [[aromatase]] expression and interfering with [[LH receptor]]-ligand binding.<ref>{{cite journal |last1=Akingbemi |first1=Benson T. |last2=Sottas |first2=Chantal M. |last3=Koulova |first3=Anna I. |last4=Klinefelter |first4=Gary R. |last5=Hardy |first5=Matthew P. |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 |date=1 February 2004 |volume=145 |issue=2 |pages=592–603 |doi=10.1210/en.2003-1174|pmid=14605012 |doi-access=free}}</ref>

Bisphenol&nbsp;A's interacts with the [[estrogen-related receptor gamma|estrogen-related receptor γ]] (ERR-γ). This [[orphan receptor]] (endogenous ligand unknown) behaves as a constitutive activator of transcription. BPA seems to bind strongly to ERR-γ ([[dissociation constant]] = 5.5 nM), but only weakly to the ER.<ref name="matsushima">{{cite journal | vauthors = Matsushima A, Kakuta Y, Teramoto T, Koshiba T, Liu X, Okada H, Tokunaga T, Kawabata S, Kimura M, Shimohigashi Y | title = Structural evidence for endocrine disruptor bisphenol A binding to human nuclear receptor ERR gamma | journal = Journal of Biochemistry | volume = 142 | issue = 4 | pages = 517–524 | date = October 2007 | pmid = 17761695 | doi = 10.1093/jb/mvm158 }}</ref> BPA binding to ERR-γ preserves its basal constitutive activity.<ref name="matsushima" /> It can also protect it from deactivation from the SERM [[4-hydroxytamoxifen]] (afimoxifene).<ref name="matsushima" /> This may be the mechanism by which BPA acts as a [[xenoestrogen]].<ref name="matsushima" /> Different expression of ERR-γ in different parts of the body may account for variations in bisphenol&nbsp;A effects.  BPA has also been found to act as an [[agonist]] of the [[GPER]] (GPR30).<ref name="ProssnitzBarton2014">{{cite journal | vauthors = Prossnitz ER, Barton M | title = Estrogen biology: new insights into GPER function and clinical opportunities | journal = Molecular and Cellular Endocrinology | volume = 389 | issue = 1–2 | pages = 71–83 | date = May 2014 | pmid = 24530924 | pmc = 4040308 | doi = 10.1016/j.mce.2014.02.002}}</ref>

== Environmental safety ==
===Distribution and degradation===
BPA has been detectable in the natural environment since the 1990s and is now widely distributed.<ref name="auto1">{{cite journal |last1=Staples |first1=Charles A. |last2=Dome |first2=Philip B. |last3=Klecka |first3=Gary M. |last4=Oblock |first4=Sondra T. |last5=Harris |first5=Lynne R. |title=A review of the environmental fate, effects, and exposures of bisphenol A |journal=Chemosphere |date=April 1998 |volume=36 |issue=10 |pages=2149–2173 |doi=10.1016/S0045-6535(97)10133-3|pmid=9566294 |bibcode=1998Chmsp..36.2149S }}</ref> It is primarily a river pollutant,<ref name=":1">{{cite journal | vauthors = Corrales J, Kristofco LA, Steele WB, Yates BS, Breed CS, Williams ES, Brooks BW | title = Global Assessment of Bisphenol A in the Environment: Review and Analysis of Its Occurrence and Bioaccumulation | journal = Dose-Response | volume = 13 | issue = 3 | pages = 1559325815598308 | date = 2015-07-29 | pmid = 26674671 | pmc = 4674187 | doi = 10.1177/1559325815598308 }}</ref> but has also been observed in the marine environment,<ref name=Turkey>{{cite journal |last1=Ozhan |first1=Koray |last2=Kocaman |first2=Emel |title=Temporal and Spatial Distributions of Bisphenol A in Marine and Freshwaters in Turkey |journal=Archives of Environmental Contamination and Toxicology |date=February 2019 |volume=76 |issue=2 |pages=246–254 |doi=10.1007/s00244-018-00594-6|pmid=30610254 |bibcode=2019ArECT..76..246O |s2cid=58536418 }}</ref> in soils,<ref name=multi /> and lower levels can also be detected in air.<ref>{{cite journal |last1=Vasiljevic |first1=Tijana |last2=Harner |first2=Tom |title=Bisphenol A and its analogues in outdoor and indoor air: Properties, sources and global levels |journal=Science of the Total Environment |date=October 2021 |volume=789 |pages=148013 |doi=10.1016/j.scitotenv.2021.148013|pmid=34323825 |bibcode= 2021ScTEn.78948013V|doi-access=free }}</ref> The solubility of BPA in water is low (~300&nbsp;g per ton of water)<ref name=water-solubility /> but this is still sufficient to make it a significant means of distribution into the environment.<ref name=multi>{{cite journal |last1=Cousins |first1=I.T. |last2=Staples |first2=C.A. |last3=Kleĉka |first3=G.M. |last4=Mackay |first4=D. |title=A Multimedia Assessment of the Environmental Fate of Bisphenol A |journal=Human and Ecological Risk Assessment|date=July 2002 |volume=8 |issue=5 |pages=1107–1135 |doi=10.1080/1080-700291905846|bibcode=2002HERA....8.1107C |s2cid=43509780 }}</ref> Many of the largest sources of BPA pollution are water-based, particularly wastewater from industrial facilities using BPA.
[[Paper recycling]] can be a major source of release when this includes [[thermal paper]],<ref name=EU2008 /><ref>{{cite journal |last1=Fürhacker |first1=M |last2=Scharf |first2=S |last3=Weber |first3=H |title=Bisphenol A: emissions from point sources |journal=Chemosphere |date=September 2000 |volume=41 |issue=5 |pages=751–756 |doi=10.1016/S0045-6535(99)00466-X|pmid=10834378 |bibcode=2000Chmsp..41..751F }}</ref> [[leaching (chemistry)|leaching]] from PVC items may also be a significant source,<ref name=":1"/> as can landfill [[leachate]].<ref name="CEC">{{cite journal |last1=Qi |first1=Chengdu |last2=Huang |first2=Jun |last3=Wang |first3=Bin |last4=Deng |first4=Shubo |last5=Wang |first5=Yujue |last6=Yu |first6=Gang |title=Contaminants of emerging concern in landfill leachate in China: A review |journal=Emerging Contaminants |date=2018 |volume=4 |issue=1 |pages=1–10 |doi=10.1016/j.emcon.2018.06.001|doi-access=free}}</ref>

In all cases, [[wastewater treatment]] can be highly effective at removing BPA, giving reductions of 91–98%.<ref name="pmid15765931">{{cite journal | vauthors = Drewes JE, Hemming J, Ladenburger SJ, Schauer J, Sonzogni W | title = An assessment of endocrine disrupting activity changes during wastewater treatment through the use of bioassays and chemical measurements | journal = Water Environment Research  | volume = 77 | issue = 1 | pages = 12–23 | date = 2005 | pmid = 15765931 | doi = 10.2175/106143005x41573 | bibcode = 2005WaEnR..77...12D | s2cid = 12283834 }}</ref> Regardless, the remaining 2–9% of BPA will continue through to the environment, with low levels of BPA commonly observed in surface water and sediment in the U.S. and Europe.<ref>{{cite journal | vauthors = Klecka GM, Staples CA, Clark KE, Van der Hoeven N, Thomas DE, Hentges SG | title = Exposure analysis of bisphenol A in surface water systems in North America and Europe | journal = Environmental Science & Technology | volume = 43 | issue = 16 | pages = 6145–50 | date = August 2009 | pmid = 19746705 | doi = 10.1021/es900598e | bibcode = 2009EnST...43.6145K}}</ref>

Once in the environment BPA is aerobically biodegraded by a wide a variety of organisms.<ref name="auto1"/><ref>{{cite journal |last1=Kang |first1=J |last2=Katayama |first2=Y |last3=Kondo |first3=F |title=Biodegradation or metabolism of bisphenol A: From microorganisms to mammals |journal=Toxicology |date=16 January 2006 |volume=217 |issue=2–3 |pages=81–90 |doi=10.1016/j.tox.2005.10.001|pmid=16288945 |bibcode=2006Toxgy.217...81K }}</ref><ref>{{cite journal |last1=Zhang |first1=Chi |last2=Li |first2=Yi |last3=Wang |first3=Chao |last4=Niu |first4=Lihua |last5=Cai |first5=Wei |title=Occurrence of endocrine disrupting compounds in aqueous environment and their bacterial degradation: A review |journal=Critical Reviews in Environmental Science and Technology |date=2 January 2016 |volume=46 |issue=1 |pages=1–59 |doi=10.1080/10643389.2015.1061881|bibcode=2016CREST..46....1Z |s2cid=94353391}}</ref> Its [[half life]] in water has been estimated at between 4.5 and 15 days, degradation in the air is faster than this, while soil samples degrade more slowly.<ref name=multi /> BPA in sediment degrades most slowly of all, particularly where this is anaerobic. [[Abiotic]] degradation has been reported, but is generally slower than biodegradation. Pathways include [[Photodegradation|photo-oxidation]], or reactions with minerals such as [[goethite]] which may be present in soils and sediments.<ref>{{cite journal |last1=Im |first1=Jeongdae |last2=Löffler |first2=Frank E. |title=Fate of Bisphenol A in Terrestrial and Aquatic Environments |journal=Environmental Science & Technology |date=16 August 2016 |volume=50 |issue=16 |pages=8403–8416 |doi=10.1021/acs.est.6b00877|pmid=27401879 |bibcode=2016EnST...50.8403I |osti=1470902}}</ref>

===Environmental effects===
BPA is an environmental [[Contaminants of emerging concern|contaminant of emerging concern]].<ref name="CEC" /> Despite its short half-life and non-[[bioaccumulating]] character, the continuous release of BPA into the environment causes continuous exposure to both plant<ref name=meta2>{{cite journal |last1=Xiao |first1=Changyun |last2=Wang |first2=Lihong |last3=Zhou |first3=Qing |last4=Huang |first4=Xiaohua |title=Hazards of bisphenol A (BPA) exposure: A systematic review of plant toxicology studies |journal=Journal of Hazardous Materials |date=February 2020 |volume=384 |pages=121488 |doi=10.1016/j.jhazmat.2019.121488|pmid=31699483 |bibcode=2020JHzM..38421488X |s2cid=207939269}}</ref> and animal life. Although many studies have been performed, these often focus on a limited range of [[model organism]]s and can use BPA concentrations well beyond environmental levels.<ref name=meta3>{{cite journal |last1=Rubin |first1=Alexander M. |last2=Seebacher |first2=Frank |title=Bisphenols impact hormone levels in animals: A meta-analysis |journal=Science of the Total Environment |date=July 2022 |volume=828 |pages=154533 |doi=10.1016/j.scitotenv.2022.154533|pmid=35288143 |bibcode=2022ScTEn.82854533R |s2cid=247423338 }}</ref> As such, the precise effects of BPA on the growth, reproduction, and development of aquatic organism are not fully understood.<ref name=meta3 /> Regardless, the existing data shows the effects of BPA on wildlife to be generally negative.<ref name=meta1>{{cite journal |last1=Wu |first1=Nicholas C. |last2=Seebacher |first2=Frank |title=Effect of the plastic pollutant bisphenol A on the biology of aquatic organisms: A meta-analysis |journal=Global Change Biology |date=July 2020 |volume=26 |issue=7 |pages=3821–3833 |doi=10.1111/gcb.15127|pmid=32436328 |bibcode=2020GCBio..26.3821W |s2cid=218765595 }}</ref><ref name=RSC>{{cite journal |vauthors=Oehlmann J, Schulte-Oehlmann U, Kloas W, Jagnytsch O, Lutz I, Kusk KO, Wollenberger L, Santos EM, Paull GC, Van Look KJ, Tyler CR | title = A critical analysis of the biological impacts of plasticizers on wildlife | journal = Philosophical Transactions of the Royal Society B: Biological Sciences | volume = 364 | issue = 1526 | pages = 2047–62 | year = 2009 | pmid = 19528055 | doi = 10.1098/rstb.2008.0242 | pmc=2873012}}</ref> BPA appears able to affect development and reproduction in a wide range of wildlife,<ref name=RSC /><ref>{{Cite journal |last1=Wu |first1=Nicholas C. |last2=Rubin |first2=Alexander M. |last3=Seebacher |first3=Frank |date=2022-01-26 |title=Endocrine disruption from plastic pollution and warming interact to increase the energetic cost of growth in a fish |journal=Proceedings of the Royal Society B: Biological Sciences |language=en |volume=289 |issue=1967 |doi=10.1098/rspb.2021.2077 |issn=0962-8452 |pmc=8790379 |pmid=35078359}}</ref> with certain species being particularly sensitive, such as [[invertebrate]]s and [[amphibian]]s.<ref name=meta1 />

== See also ==
; Structurally related
* [[4,4'-Dihydroxybenzophenone]] - used as a UV stabilizer in cosmetics and plastics
* [[Dinitrobisphenol A]] - a proposed metabolite of BPA, which may show increased endocrine disrupting character 
* [[HPTE]] - a metabolite of the synthetic insecticide [[methoxychlor]]

; Others
* [[2,2,4,4-Tetramethyl-1,3-cyclobutanediol]] - next generation BPA replacement 
* [[4-tert-Butylphenol]] - used as a chain-length regulator in the production of polycarbonates and epoxy resins, it has also been studied as a potential endocrine disruptor

== References ==
{{Reflist}}

{{Androgen receptor modulators}}
{{Estrogen receptor modulators}}
{{Estrogen-related receptor modulators}}
{{Authority control}}

[[Category:2,2-Bis(4-hydroxyphenyl)propanes]]
[[Category:Bis(4-hydroxyphenyl)methanes]]
[[Category:Commodity chemicals]]
[[Category:Endocrine disruptors]]
[[Category:GPER agonists]]
[[Category:Medical controversies]]
[[Category:Monomers]]
[[Category:Nonsteroidal antiandrogens]]
[[Category:Russian inventions]]
[[Category:Selective estrogen receptor modulators]]
[[Category:Xenoestrogens]]