Izvorni kod stranice Bisfenol A

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|   IUPACName = 4,4'-(propan-2,2-diil)difenol
|   OtherNames = BPA; 4,4'-dihidroksi-2,2-difenilpropan; ''p'',''p'''-izopropilidenbisfenol; 2,2-bis(4-hidroksifenil)propan; 4,4'-(propan-2-iliden)difenol; 4,4´-izopropilidenedifenol; 
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| SMILES = Oc1ccc(cc1)C(c2ccc(O)cc2)(C)C
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| UNII = MLT3645I99
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| 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
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|   EINECS = 201-245-8
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|   RTECS = SL6300000
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| Section2 = {{Chembox Properties-lat
|   C=15|H=16|O=2
|   Appearance = Bela čvrsta materija
|   Density = 1.20 g/cm³
|   Solubility = 120–300 ppm (21.5&nbsp;°C)
|   MeltingPtC = 158
|   MeltingPtCH = 159
|   BoilingPtC = 220
|    Boiling_notes = 4 mmHg
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|   FlashPtC = 227
|   AutoignitionPtC = 600
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| Section8 = {{Chembox Related-lat
|   Function =
|   OtherFunctn =
|   OtherCpds = [[fenol]]i<br />[[Bisfenol S]]
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}}

'''Bisfenol A''' je [[hemijsko jedinjenje|kemijski spoj]] sa dvije [[funkcionalna grupa|funkcionalne skupine]] [[fenol]]a koji se uglavnom koristi sa proizvodnju [[polikarbonat]]ne [[plastika|plastike]] i [[poliepoksid]]a.

Pošto je dokazano da ima [[estrogeni|estrogena]] svojstva još od [[1930-e|1930-ih]], mnogi su izrazili zabrinutost oko upotrebe Bisfenola A u potrošačkim proizvodima. U nekim državama, razni proizvodi sa sadržajem te tvari su više puta povučeni sa polica. 2010., [[Administracija za hranu i lijekove]] (FDA) je objavila izvještaj u kojem izražava zabrinutost oko izlaganja fetusa, beba i mlade djece toj tvari jer uzrokuje negativne posljedice za razvoj.<ref name="U.S. Food and Drug Administration">{{cite web|url=http://www.fda.gov/NewsEvents/PublicHealthFocus/ucm197739.htm|title=Update on Bisphenol A for Use in Food Contact Applications: January 2010|date=15 January 2010|publisher=U.S. Food and Drug Administration|accessdate=15 January 2010}}</ref>
== Dobivanje ==
[[A.P. Diannin]] je prvi sastavio bisfenol A [[1891]]. godine.<ref name=dianin>{{cite journal | author = Dianin | title = Zhurnal russkogo fiziko-khimicheskogo obshchestva | volume = 23 | year = 1891 | pages = &nbsp;492&ndash;}}</ref><ref>{{cite journal | first = Theodor | last = 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> Dobiva se od dva ekvivalenta fenola i jednog ekvivalenta [[aceton]]a. Reakcija se katalizira [[hlorovodonična kiselina|kolorovodičnom kiselinom]] (HCl):
:[[Datoteka:Synthesis Bisphenol A.svg|frameless|upright=2.5]]<!--:<math>\mathrm{(CH_3)_2CO + 2 \ C_6H_5OH \longrightarrow (CH_3)_2C(C_6H_4OH)_2 + H_2O}</math>-->

== Upotreba ==

[[Datoteka:HK Central Lan Fong Yuen Dairy products Canned Corned beef n Condensed milk.JPG|lijevo|mini|250px|Konzerve sa hranom sadrže Bisfenol A]]
Bisfenol A se uglavnom koristi za dobivanje plastike. Ključan je [[monomeri|monomer]] za proizvodnju poliepoksida<ref>{{cite web|url=http://www.californiaprogressreport.com/2009/07/committee_succe.html|title=Lawmakers to press for BPA regulation|last=Replogle|first=Jill|date=2009-07-17|publisher=California Progress Report|accessdate=2009-08-02}}</ref><ref>{{cite web|url=http://www.thestar.com/article/415296|title=Ridding life of bisphenol A a challenge|last=Ubelacker  |first=Sheryl |date=2008-04-16|publisher=Toronto Star |accessdate=2009-08-02}}</ref> i polikarbonata.<ref>{{cite book|last=Kroschwitz|first=Jacqueline I.|title=Kirk-Othmer encyclopedia of chemical technology|edition=5|volume=5|pages=8}}</ref><ref>{{cite web|url=http://www.alliancepoly.com/polycarbonate.asp|title=Polycarbonate (PC) Polymer Resin|publisher=Alliance Polymers, Inc|accessdate=2009-08-02|archivedate=2009-09-21|archiveurl=https://web.archive.org/web/20090921084954/http://www.alliancepoly.com/polycarbonate.asp|deadurl=yes}}</ref> Plastika je uglavnom prozirna, elastična i ne može se razbiti a sadrže ju sljedeći proizvodi: boca za vodu, flašice ze bebe, sportska oprema, [[zubna plomba]], sredstvo za brtvljenje, [[leća]], [[CD]]-i i [[DVD]]-i te kućni elektronički uređaji.<ref name="CERHR">{{cite news | title = CERHR Expert Panel Report for Bisphenol A | url = http://cerhr.niehs.nih.gov/chemicals/bisphenol/BPAFinalEPVF112607.pdf | format = PDF | accessdate = 2008-04-18 | date = 2007-11-26 | author = National Toxicology Program, U.S. Department of Health and Human Services | archive-date = 2008-02-18 | archive-url = https://web.archive.org/web/20080218195117/http://cerhr.niehs.nih.gov/chemicals/bisphenol/BPAFinalEPVF112607.pdf | dead-url = yes }}</ref> Proizvodi od plastike sadrže tu tvar još od [[1950-e|1950-ih]].
Bisfenol A se također koristi za sintezu [[polisulfon]]a i [[keton]]a poli[[etar|etri]] i kao inhibitor polimerizacije u [[PVC]]-u. Bisfenol A se može naći i unutar konzervi [[hrana|hrane]] i [[piće|pića]],<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|url=http://pubs.acs.org/isubscribe/journals/cen/86/i22/html/8622gov1.html}}</ref> iako je u [[Japan]]u počela proizvodnja konzervi i limenki bez te tvari zbog sumnje na štetnost zdravlju.

Nalazi se i u termalnom [[papir]]u, papiru za kopiranje bez ugljika<ref name="ReferenceA">cite doi|10.1016/S0045-6535(00)00507-5</ref> a proizvodi sa tom tvari koriste se za lijevanje i za oblogu cjevovoda.<ref name="epa-action-plan">{{cite web|url=http://www.epa.gov/oppt/existingchemicals/pubs/actionplans/bpa_action_plan.pdf|title=Bisphenol A Action Plan |date=29 March 2010|publisher=U.S. Environmental Protection Agency|accessdate=12 April 2010}}</ref>
Zanimljivo, Bisfenol A se prije koristio kao [[fungicid]].<ref>[http://pesticideinfo.org/Detail_Chemical.jsp?Rec_Id=PC33756 Pesticideinfo.org: Bisphenol A]</ref>
Svjetska proizvodnja te tvari [[2003]]. je procijenjena na preko 2 milijuna [[tona]], te više od 2.2 milijuna tona šest godina kasnije..<ref>{{cite web|url=http://www.reuters.com/article/idUSTRE65L6JN20100622?loomia_ow=t0:s0:a49:g43:r3:c0.084942:b35124310:z0|title=Experts demand European action on plastics chemical|publisher=Reuters}}</ref>

U SAD-u, slijedeće tvrtke najviše proizvode Bisfenol A: [[Bayer MaterialScience]], [[Dow Chemical Company]], [[SABIC]] Innovative Plastics, [[Hexion Specialty Chemicals]] i [[Sunoco|Sunoco Chemicals]]. Zajedno su proizveli preko 1 milijun tona te tvari 2004. Godišnja američka potrošnja iste je bila 856.000 tona, od toga je 72 % iskorišteno za proizvodnju polikarbonatne plastike, 21 % % za poliepokside<ref name="CERHR"/> a manje od 5 % za sredstva koja dolaze u dodir sa hranom.
Općenito, plastika na kojoj piše '''Tip 7''' i '''Tip 3''' sadrže Bisfenol A. Tipovi 1, 2, 4, 5, i 6 ne koriste spomenutu tvar u procesu polimerizacije.

== Utjecaj na zdravlje ==
Bisfenol A uzrokuje poremećaje [[endokrini sistem|endokrinog sustava]] jer oponaša [[hormoni|hormone]] tijela te može negativno utjecati na zdravlje.<ref>{{cite book|last=Gore|first=Andrea C. |title=Endocrine-Disrupting Chemicals: From Basic Research to Clinical Practice|url=https://archive.org/details/endocrinedisrupt0000unse_g6a6|publisher=Humana Press|date=June 8, 2007|series=Contemporary Endocrinology|isbn=978-1588298300}}</ref><ref>{{cite journal |last=O’Connor |first1=JC |last2=Chapin |first2=RE | 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 |year=2003 | url = http://www.iupac.org/publications/pac/2003/pdf/7511x2099.pdf| format = Full Article | accessdate = 2007-02-28 | doi = 10.1351/pac200375112099}}</ref><ref>{{cite journal |author=Okada H, Tokunaga T, Liu X, Takayanagi S, Matsushima A, Shimohigashi Y |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=32–8 |year=2008 |month=January |pmid=18197296 |pmc=2199305 |doi=10.1289/ehp.10587 |url=https://archive.org/details/sim_environmental-health-perspectives_2008-01_116_1/page/32}}</ref><ref name=JAMAVS>{{cite journal |author=vom Saal FS, Myers JP |title=Bisphenol A and Risk of Metabolic Disorders |journal= Journal of the American Medical Association (JAMA) |volume= 300|issue=300 |pages= 1353|year=2008 |pmid= 18799451|doi=10.1001/jama.300.11.1353 |url=http://jama.ama-assn.org/cgi/content/full/300.11.1353}}</ref> Štetni utjecaj je najveći na najmlađim osobama.<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> Nadzorna tijela su utvrdila "sigurne količine" izloženosti ljudi Bisfenolu A, no te razine su osporene od raznih stručnjaka.<ref name=EHP>{{cite news |author=Ginsberg G, Rice DC |title=Does Rapid Metabolism Ensure Negligible Risk from Bisphenol A? |journal=[[Environmental Health Perspectives|EPH]] |volume=117 |issue=11 |pages=1639–1643 |year=2009 |doi=10.1289/ehp.0901010 |url=http://www.ehponline.org/members/2009/0901010/0901010.html }}{{Dead link|date=August 2021 |bot=InternetArchiveBot |fix-attempted=yes }}</ref>

2009., "Endokrino društvo" je objavilo znanstvenu izjavu koja izražava "zabrinutost izlaganju ljudi Bisfenolu A" Slijedi popis moguće opasnosti te tvari na ljudsko zdravlje.

Komisija koju je sastavio američki Državni institut za zdravlje je došla do zaključka da postoji "poneka zabrinutost" o učincima Bisfenola A na razvoj [[fetus]]a i [[mozak|mozga]] i ponašanja djece.<ref name="CERHR"/> Kasniji izvještaj američkog Državnog toksičnog programa se složio sa nalazima komisije, izažavajući "poneku zabrinutost oko učinaka na mozak, ponašanje i žlijezdu prostate kod fetusa, dojenčadi i djece kod trenutne ljudske izloženosti Bisfenolu A," te "minimalnu zabinutost oko učinaka na [[mliječna žlijezda|mliječne žlijezde]] i na rano razdoblje puberteta za žene u fetusa, dojenčadi i djece kod trenutne ljudske izloženosti Bisfenolu A." Učinak iste tvari u utjecaju na trudnice pri stvaranju urođenih mana ili smanjenja težina novorođenih je prema toj ustanovi bio "zanemariv".<ref name=NTP08>[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] {{Webarchive|url=https://web.archive.org/web/20100513030019/http://www.niehs.nih.gov/news/media/questions/sya-bpa.cfm |date=2010-05-13 }}, National Institute of Environmental Health Sciences website.</ref>
=== Pretilost ===
[[Datoteka:Plastic-recyc-07.svg|desno|mini|Plastika tipa 7 sadrži bisfenol A]]
Prema istraživanju iz 2008., utvrdilo se da su ljudi izloženi bisfenolu A podložniji pretilosti.<ref>cite doi|10.1097/MED.0b013e32830ce95c</ref>
=== Neurološke komplikacije ===
Komisija Državnog instiuta za zdravlje je utvrdila da postoje "neke opasnosti" o utjecaju spoja na razvoj i ponašanje mozga fetusa i dojenčadi.<ref name="CERHR"/> Izvještaj Državnog toksičkog programa se složio sa nalazom.<ref name=NTP08/> Bisfenol A, kao i drugi ksenoestrogeni, mogu regulirati ili izmijeniti funkcije u [[nervni sistem|živčanom sustavu]]. Eksperimenti su 2007. pokazali da je spoj utjecao na strukturu, funkciju i ponašanje [[miš]]eva i [[pacov|štakora]]. Istraga iz 2008. zaključuje da je izloženost okoćenih miševa utjecala na njihovu seksualno dimorfnu moždanu morfologiju i neurološke fenotipove pri odrastanju. Spoj je također umanjio i proces memoriranja.
Medicinska škola u [[Yale]]u je 2008. izlagala [[primati|primate]] dnevnim dozama bisfenola A za koje [[Američka agencija za zaštitu okoliša]] (EPA) tvrdi da je "prihvatljiva" kod ljudi. Prema njihovom kontroverznom zaključku, spoj je ometao spajanje moždanih stanica bitnih za memoriju, učenje i ponašanje.<ref name="pmid18768812">{{cite journal |author=Leranth C, Hajszan T, Szigeti-Buck K, Bober J, Maclusky NJ |title=Bisphenol A prevents the synaptogenic response to estradiol in hippocampus and prefrontal cortex of ovariectomized nonhuman primates |journal=Proc. Natl. Acad. Sci. U.S.A. |volume= 105|issue= 37|pages= 14187|year=2008 |month=September |pmid=18768812 |doi=10.1073/pnas.0806139105 |url= |pmc=2544599}}</ref><ref name="Layton2">{{cite news|url=http://www.washingtonpost.com/wp-dyn/content/article/2008/09/03/AR2008090303397.html?hpid=topnews|title=Chemical in Plastic Is Connected to Health Problems in Monkeys|last=Layton|first=Lindsey|date=September 4, 2008|publisher=Washington Post|pages=A02|accessdate=2008-09-06}}</ref> Prema njima, spoj može prouzrokovati poremećaj gubitka pažnje i [[hiperaktivnost]]i.

2010., istraživanje je pokazalo da je [[kortikosteron]] i njegovo djelovanje u mozgu osjetljivo na bisfenol A.
=== Dopamin ===
Istraživanje iz 2005. ukazuje da je izloženost spoju ubrzala sustav [[dopamin]]a kod miševa. 2008., utvrđeno je da je to dovelo do hiperaktivnosti, manjka pažnje i povećane osjetljivosti na [[zloupotreba droga|zloupotrebu droga]].<ref>cite pmid|18555207</ref>
=== Štitnjača ===
Istraživanje iz 2007. pokazalo je da se bisfenol A veže za receptore hormona [[štitnjača|štitnjače]] te vjerojatno djeluje na njenu funkciju. Dvije godine kasnije, otkriveni su dokazi koji ukazuju da spoj djeluje na poremećaj lučenja [[Trijodotironin|trijodtironina]].<ref>cite pmid|19625957</ref>

=== Rak ===
Istraživanje iz 2010. ukazuje da bisfenol A može povećati opasnost od stvaranja [[rak]]a.<ref>cite doi|10.1038/nrendo.2010.87</ref> Također, "izlaganje fetusa (...) malim količinama (...) bisfenola A, mijenja razvoj grudi i povećava opasnost od raka dojki."<ref>cite doi|10.2533/chimia.2008.406</ref>

Prema istraživanju iz 1997., izlaganje 2 μg/kg bisfanola A tek okoćenim miševima rezultiralo je u povećanju težine [[prostata|prostate]] te opasnosti od karcinoma.
=== Neuroblastom ===
Istraživanja su pokazala da bisfenol A potiče razvoj stanica [[neuroblastom]]a<ref>cite doi|10.1016/j.etap.2007.05.003</ref> te predstavlja moguću opasnost od [[metastaza]].
=== Reprodukcijski sustav ===
Istraživanje iz 2009. je pokazalo da [[jajnici]] fetusa miševa pri izlaganju od samo 1&nbsp;µg/kg bisfenola A pokazuju dugoročne reproduktivne i karcenogene učinke.<ref name="pmid19590677">Newbold, R.; Jefferson, N.; Padilla-Banks, E. (Jun 2009).[http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2702400/?tool=pmcentrez ''Prenatal Exposure to Bisphenol A at Environmentally Relevant Doses Adversely Affects the Murine Female Reproductive Tract Later in Life''] Environmental health perspectives 117 (6): 879–885. doi:10.1289/ehp.0800045. ISSN 0091-6765. {{PMID|19590677}}.</ref>

Pri izloženosti fetusa količinom od 50&nbsp;µg/kg bisfenola A, dolazi do poremećaja razvoja jajnika te trajno mijenja mehanizme u [[hipotalamus]]u ovisne o estrogenu koji su odgovorni za seksualno ponašanje ženke miša.
=== Srce ===
[[Iain Lang]] je 2008. napravio prvo veće istraživanje o utjecaju bisfenola A na zdravlje ljudi. Ispitano je 1.500 osoba. Otkriveno je da je spoj povezan sa bolestima [[srce|srca]], [[dijabetes]]om i visokim razinama određenih enzima jetre.<ref name="Lang et al.">{{cite journal |author=Lang IA, Galloway TS, Scarlett A, Henley WE, Depledge M, Wallace RB, Melzer D |title=Association of Urinary Bisphenol A Concentration With Medical Disorders and Laboratory Abnormalities in Adults |journal=[[Journal of the American Medical Association|JAMA]] |volume= 300|issue=300 |pages= 1303|year=2008 |pmid= 18799442|doi=10.1001/jama.300.11.1303 |url=http://jama.ama-assn.org/cgi/content/full/300.11.1303}}</ref><ref>[http://www.newscientist.com/channel/health/dn14739-plastic-bottle-chemical-linked-to-heart-disease.html Newscientist.com] ''Plastic bottle chemical linked to heart disease''</ref>
=== Učinci na izloženim životinjama ===
{| class="wikitable"
|-
! Količina (µg/kg/dan)
! Učinci (istraživanja na miševima, štakorima<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 | archiveurl=https://web.archive.org/web/20070930072411/http://www.theglobeandmail.com/servlet/story/RTGAM.20070406.wbisphenolA0407/BNStory/National/ | archivedate=2007-09-30 | deadurl=no }}</ref><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>
! Godina istraživanja
|-
| 0.025
| "Trajne promjene genitalnog trakta"
| 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 |access-date=2013-02-05 |archive-date=2012-12-09 |archive-url=https://archive.today/20121209053634/http://www.biolreprod.org/cgi/pmidlookup?view=long&pmid=15689538 |dead-url=yes }}</ref>
|-
| 0.025
| "Promjene u tkivu dojki koje preodređuju stanice hormonima i karcenogenim tvarima"
| 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 |access-date=2013-02-05 |archive-date=2017-09-30 |archive-url=https://web.archive.org/web/20170930140607/http://endo.endojournals.org/cgi/pmidlookup?view=long&pmid=15919749 |dead-url=yes }}</ref>
|-
| 1
| "dugotrajni nepovoljni reprodukcijski i kancerogeni učinci"
| 2009<ref name="pmid19590677"/>
|-
| 2
| "povećanje težine prostate za 30%"
| 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=10.2307/3433065 |pmc=1469837}}</ref>
|-
| 2
| "manja tjelesna težina, znakovi ranog [[pubertet]]a i dužeg [[estrus]]a."
| 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= 10.1016/S0890-6238(02)00006-0|url=http://linkinghub.elsevier.com/retrieve/pii/S0890623802000060}}</ref>
|-
| 2.4
| "Opadanje [[testosteron]]a u testisima"
| 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 |access-date=2013-02-05 |archive-date=2021-02-14 |archive-url=https://web.archive.org/web/20210214102657/http://endo.endojournals.org/cgi/pmidlookup?view=long&pmid=14605012 |dead-url=yes }}</ref>
|-
| 2.5
| "stanice dojke preodređene za rak"
| 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 |pmc=1987322}}</ref>
|-
| 10
| "stanice prostate osjetljivije na harmone i rak"
| 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 |pmc=2276876}}</ref>
|-
| 10
| "opadanje majčinskog ponašanja"
| 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 |pmc=1241192 |access-date=2013-02-05 |archive-date=2011-03-01 |archive-url=https://web.archive.org/web/20110301100008/http://ehpnet1.niehs.nih.gov/docs/2002/suppl-3/415-422palanza/abstract.html |dead-url=yes }}</ref>
|-
| 30
| "Hiperaktivnost"
| 2004
|-
| 30
| "poništenje normalne seksualne razlike u moždanoj strukturi i ponašanju"
| 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= 10.1016/S0168-0102(02)00251-1|url=http://linkinghub.elsevier.com/retrieve/pii/S0168010202002511}}</ref>
|-
| 50
| "nepovoljni neurološki učinci kod [[primati|primata]]"
| 2008<ref name="pmid18768812"/>
|-
| 50
| "Poremećaj razvoja jajnika"
| 2009
|-
|}
== Reference ==
{{reflist}}

== Literatura ==
{{refbegin}}
* {{Clayden1st}}
* {{March6th}}
* {{Katritzky2nd}}
{{refend}}

== Vanjske veze ==
{{Portal-lat|Hemija}}
{{Commonscat-lat|Bisphenol A}}
* [http://www.drugbank.ca/drugs/DB06973 Bisphenol A]
* [http://www.mass.gov/Eeohhs2/docs/dph/environmental/exposure/bisphenol_a_brochure.pdf Kako zaštiti vašu bebu od bisfenola A] {{Webarchive|url=https://web.archive.org/web/20110222034558/http://www.mass.gov/Eeohhs2/docs/dph/environmental/exposure/bisphenol_a_brochure.pdf |date=2011-02-22 }}
* [http://www.youtube.com/watch?v=8wXGrzDIcr8 Video o utjecaju bisfenola A] na [[YouTube]]

[[Kategorija:Bisfenoli]]