Bisphenol

Not to be confused with biphenol.

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]

List

Structural formula Name CAS Reactants
Bisphenol A Bisphenol A 80-05-7 Phenol Acetone
Bisphenol AP Bisphenol AP 1571-75-1 Phenol Acetophenone
Bisphenol AF Bisphenol AF 1478-61-1 Phenol Hexafluoroacetone
Bisphenol B Bisphenol B 77-40-7 Phenol Butanone
Bisphenol BP Bisphenol BP 1844-01-5 Phenol Benzophenone
Bisphenol C Bisphenol C 79-97-0 o-cresol Acetone
Bisphenol CII Bisphenol C 2 14868-03-2 Phenol Chloral
Bisphenol E Bisphenol E 2081-08-5 Phenol Ethanal
Bisphenol F Bisphenol F 620-92-8 Phenol Formaldehyde
Bisphenol G Bisphenol G 127-54-8 2-Isopropylphenol Acetone
Bisphenol M Bisphenol M 13595-25-0
Bisphenol S Bisphenol S 80-09-1 Phenol Sulfur trioxide
Bisphenol P Bisphenol P 2167-51-3
Bisphenol PH Bisphenol PH 24038-68-4 2-Phenylphenol Acetone
Bisphenol TMC Bisphenol TMC 129188-99-4 Phenol 3,3,5-Trimethylcyclohexanone
Bisphenol Z Bisphenol Z 843-55-0 Phenol Cyclohexanone
Dinitrobisphenol A Dinitrobisphenol A 5329-21-5 Bisphenol A Nitric acid
Tetrabromobisphenol A Tetrabromobisphenol A 79-94-7 Bisphenol A Bromine

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. ^ a b c 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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