Bisphenol

The bisphenols (/ˈbɪsfɪnɒl/) are a group of industrial chemical compounds related to diphenylmethane; commonly used in the creation of plastics and epoxy resins.[1][2][3] 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".[3][4][5]

Not to be confused with biphenol.

List
Structural formula Name CAS Reactants
Bisphenol A80-05-7PhenolAcetone
Bisphenol AP1571-75-1PhenolAcetophenone
Bisphenol AF1478-61-1PhenolHexafluoroacetone
Bisphenol B77-40-7PhenolButanone
Bisphenol BP1844-01-5PhenolBenzophenone
Bisphenol C79-97-0o-cresolAcetone
Bisphenol C 214868-03-2PhenolChloral
Bisphenol E2081-08-5 PhenolEthanal
Bisphenol F620-92-8PhenolFormaldehyde
Bisphenol G127-54-82-IsopropylphenolAcetone
Bisphenol M13595-25-0
Bisphenol S80-09-1PhenolSulfur trioxide
Bisphenol P2167-51-3
Bisphenol PH24038-68-42-PhenylphenolAcetone
Bisphenol TMC129188-99-4Phenol3,3,5-Trimethylcyclohexanone
Bisphenol Z843-55-0PhenolCyclohexanone
Dinitrobisphenol A5329-21-5Bisphenol ANitric acid
Tetrabromobisphenol A79-94-7Bisphenol ABromine

Health effects

Bisphenols A (BPA), F (BPF) and S (BPS) have been shown to be endocrine disruptors, potentially relating to adverse health effects.[3][6] Due to its high production volumes, BPA has been characterised as a "pseudo-persistent" chemical,[7] leading to its spreading and potential accumulation in a variety of environmental matrices, even though it has a fairly short half-life.[8]

References
  1. Pelch KE, Wignall JA, Goldstone AE, Ross PK, Blain RB, Shapiro AJ, et al. (2017). NTP Research Report on Biological Activity of Bisphenol A (BPA) Structural Analogues and Functional Alternatives: Research Report 4. NTP Research Reports. Research Triangle Park (NC): National Toxicology Program. PMID 31944638.
  2. Fishburn JL, Larson HL, Nguyen A, Welch CJ, Moore T, Penn A, et al. (2024-03-01). "Bisphenol F affects neurodevelopmental gene expression, mushroom body development, and behavior in Drosophila melanogaster". Neurotoxicology and Teratology. 102: 107331. Bibcode:2024NTxT..10207331F. doi:10.1016/j.ntt.2024.107331. PMID 38301979.
  3. Almeida S, Raposo A, Almeida-González M, Carrascosa C (November 2018). "Bisphenol A: Food Exposure and Impact on Human Health". Comprehensive Reviews in Food Science and Food Safety. 17 (6): 1503–1517. doi:10.1111/1541-4337.12388. PMID 33350146.
  4. Vandenberg LN, Maffini MV, Sonnenschein C, Rubin BS, Soto AM (February 2009). "Bisphenol-A and the great divide: a review of controversies in the field of endocrine disruption". Endocrine Reviews. 30 (1): 75–95. doi:10.1210/er.2008-0021. PMC 2647705. PMID 19074586.
  5. Fiege H, Voges HW, Hamamoto T, Umemura S, Iwata T, Miki H, et al. (2002). "Phenol Derivatives". Phenol Derivatives. Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN 978-3-527-30673-2..
  6. Bilbrey J (11 August 2014). "BPA-Free Plastic Containers May Be Just as Hazardous". Scientific American. Retrieved 8 August 2015.
  7. Pivnenko K, Pedersen GA, Eriksson E, Astrup TF (October 2015). "Bisphenol A and its structural analogues in household waste paper" (PDF). Waste Management. 44: 39–47. Bibcode:2015WaMan..44...39P. doi:10.1016/j.wasman.2015.07.017. PMID 26194879. S2CID 217938141.
  8. See Bisphenol A#Environmental effects for extensive discussion

Further reading
  • For additional examples and alternate names, see: Alger M (2017). Polymer Science Dictionary. Springer. p. 77. ISBN 978-94-024-0893-5.
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