bisphenol

{{Short description|Class of chemical compounds}}

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{{distinguish|biphenol}}

The bisphenols ({{IPAc-en|ˈ|b|ɪ|s|f|ᵻ|n|ɒ|l}}) are a group of industrial chemical compounds related to diphenylmethane; commonly used in the creation of plastics and epoxy resins.{{Cite book | vauthors = Pelch KE, Wignall JA, Goldstone AE, Ross PK, Blain RB, Shapiro AJ, Holmgren SD, Hsieh JH, Svoboda D |url=http://www.ncbi.nlm.nih.gov/books/NBK538922/ |title=NTP Research Report on Biological Activity of Bisphenol A (BPA) Structural Analogues and Functional Alternatives: Research Report 4 |date=2017 |publisher=National Toxicology Program |series=NTP Research Reports |location=Research Triangle Park (NC) |pmid=31944638}}{{cite journal | vauthors = Fishburn JL, Larson HL, Nguyen A, Welch CJ, Moore T, Penn A, Newman J, Mangino A, Widman E, Ghobashy R, Witherspoon J, Lee W, Mulligan KA | title = Bisphenol F affects neurodevelopmental gene expression, mushroom body development, and behavior in Drosophila melanogaster | journal = Neurotoxicology and Teratology | volume = 102 | pages = 107331 | date = 2024-03-01 | pmid = 38301979 | doi = 10.1016/j.ntt.2024.107331 | bibcode = 2024NTxT..10207331F | doi-access = free }}{{cite journal | vauthors = Almeida S, Raposo A, Almeida-González M, Carrascosa C | title = Bisphenol A: Food Exposure and Impact on Human Health | journal = Comprehensive Reviews in Food Science and Food Safety | volume = 17 | issue = 6 | pages = 1503–1517 | date = November 2018 | pmid = 33350146 | doi = 10.1111/1541-4337.12388 }} Most are based on two hydroxyphenyl functional groups linked by a methylene bridge. Exceptions include bisphenol S, P, and M. "Bisphenol" is a common name; the letter following denotes the variant, which depends on the additional substituents. Bisphenol A is the most popular representative of the group, with millions of metric tons produced globally in the past decade, often simply called "bisphenol".{{cite journal | vauthors = Vandenberg LN, Maffini MV, Sonnenschein C, Rubin BS, Soto AM | title = Bisphenol-A and the great divide: a review of controversies in the field of endocrine disruption | journal = Endocrine Reviews | volume = 30 | issue = 1 | pages = 75–95 | date = February 2009 | pmid = 19074586 | pmc = 2647705 | doi = 10.1210/er.2008-0021 }}{{cite encyclopedia | vauthors = Fiege H, Voges HW, Hamamoto T, Umemura S, Iwata T, Miki H, Fujita Y, Buysch HJ, Garbe D, Paulus W |title=Phenol Derivatives |encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2002|publisher=Wiley-VCH|location=Weinheim|doi=10.1002/14356007.a19_313|isbn=978-3-527-30673-2 |entry=Phenol Derivatives }}.

List

Health effects

Bisphenols A (BPA), F (BPF) and S (BPS) have been shown to be endocrine disruptors, potentially relating to adverse health effects.{{cite web|title=BPA-Free Plastic Containers May Be Just as Hazardous|url=http://www.scientificamerican.com/article/bpa-free-plastic-containers-may-be-just-as-hazardous/|magazine=Scientific American|date=11 August 2014| vauthors = Bilbrey J |access-date=8 August 2015}} Due to its high production volumes, BPA has been characterised as a "pseudo-persistent" chemical,{{cite journal | vauthors = Pivnenko K, Pedersen GA, Eriksson E, Astrup TF | title = Bisphenol A and its structural analogues in household waste paper | journal = Waste Management | volume = 44 | pages = 39–47 | date = October 2015 | pmid = 26194879 | doi = 10.1016/j.wasman.2015.07.017 | s2cid = 217938141 | bibcode = 2015WaMan..44...39P | url = https://backend.orbit.dtu.dk/ws/files/118749778/PostPrint_Davidsen_JoH_1_.pdf }} leading to its spreading and potential accumulation in a variety of environmental matrices, even though it has a fairly short half-life.See Bisphenol A#Environmental effects for extensive discussion

References

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Further reading

  • For additional examples and alternate names, see: {{cite book |title= Polymer Science Dictionary | vauthors = Alger M |publisher= Springer |year= 2017 |isbn= 978-94-024-0893-5 |page= 77 }}

Category:Endocrine disruptors