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Bisphenol F

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Bisphenol F
Names
Preferred IUPAC name
4,4′-Methylenediphenol
Other names
BPF; 4,4′-Dihydroxydiphenylmethane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.691 Edit this at Wikidata
UNII
  • InChI=1S/C13H12O2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h1-8,14-15H,9H2
    Key: PXKLMJQFEQBVLD-UHFFFAOYSA-N
  • InChI=1/C13H12O2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h1-8,14-15H,9H2
    Key: PXKLMJQFEQBVLD-UHFFFAOYAW
  • c1cc(ccc1Cc2ccc(cc2)O)O
Properties
C13H12O2
Molar mass 200.237 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Bisphenol F (BPF; 4,4′-dihydroxydiphenylmethane) is an organic compound with the chemical formula (HOC
6H
4)
2CH
2. It is structurally related to bisphenol A (BPA), a popular precursor for forming plastics, as both belong to the category of molecules known as bisphenols, which feature two phenol groups connected via a linking group. In BPF, the two aromatic rings are linked by a methylene connecting group. In response to concern about the health effects of BPA, BPF is increasingly used as a substitute for BPA.[1]

Uses

BPF is used in the manufacture of plastics and epoxy resins.[2] It is used in the production of tank and pipe linings, industrial flooring, road and bridge deck toppings, structural adhesives, grouts, coatings and electrical varnishes.[3] BPF is also utilized in liners, lacquers, adhesives, plastics, and the coating of drinks and food cans.[2] BPF is found in dental materials, such as restorative materials, liners, adhesives, oral prosthetic devices and tissue substitutes.[2][4][5]

Biological effects

Pharmacokinetics

BPF undergoes two primary phase II biotransformations to form the corresponding glucuronide and sulfate.[6][7][8]

Hormonal effects

BPF has estrogenic, progesteronic, and anti-androgenic effects. The overarching implications of these hormonal changes for humans are decreases in testosterone secretions, especially in male testes, and increases in the activity of estrogen. The effects are greatest in the fetal testis, which is primed to be more easily affected due to its plasticity and massive period of growth. One study[9] found that BPF had the same effect in lowering testosterone secretions as BPA, increasing over 80% compared to the control in the human fetal testes. This research is done using an in vitro method of fetal testis assay (FeTA), and does not necessarily reflect the mechanisms BPF would undergo if ingested by humans. For example, the ability for BPF to activate oestrogen in the receptors is lower than that of BPA, (one study[9] suggests 5- to 10-fold lower) and the actions of these bisphenols are likely not directly through these receptors, but rather more indirect. As such, most research done on this topic has been using human cell line cultures, rather than studies on mammalian in vivo exposure. Several other reviews have all shown that BPF demonstrates similar endocrine and physiological disruptions as BPA, both in vitro and in vivo primary organoid cell cultures, especially demonstrating its estrogenic and anti-androgenic actions.[10][11]

Environmental contamination

BPF is pervasive in the environment, appearing in river water, drinking water, and agricultural soil samples[12][13][14].[6][15] Four out of five studies yielded results that BPF is estrogenic, androgenic and thyroidogenic.[2] The greatest effect of BPF to be liver toxicity.[16] In vitro studies of BPF showed effects of cytotoxicity, cellular dysfunction, DNA damage and chromosomal aberrations.[2]

References

  1. ^ Usman, Afia; Ikhlas, Shoeb; Ahmad, Masood (2019-09-15). "Occurrence, toxicity and endocrine disrupting potential of Bisphenol-B and Bisphenol-F: A mini-review". Toxicology Letters. 312: 222–227. doi:10.1016/j.toxlet.2019.05.018. ISSN 0378-4274. PMID 31136786. S2CID 169035866.
  2. ^ a b c d e Rochester, Johanna Ruth; Bolden, Ashley Louise (2015). "Bisphenol S and F: A Systematic Review and Comparison of the Hormonal Activity of Bisphenol A Substitutes". Environmental Health Perspectives. 123 (7): 643–50. doi:10.1289/ehp.1408989. PMC 4492270. PMID 25775505.
  3. ^ Cabaton, Nicolas; Chagnon, Marie-Christine; Lhuguenot, Jean-Claude; Cravedi, Jean-Pierre; Zalko, Daniel (2006-12-27). "Disposition and metabolic profiling of bisphenol F in pregnant and nonpregnant rats". Journal of Agricultural and Food Chemistry. 54 (26): 10307–10314. doi:10.1021/jf062250q. ISSN 0021-8561. PMID 17177575.
  4. ^ Usman, Afia; Ikhlas, Shoeb; Ahmad, Masood (2019-09-15). "Occurrence, toxicity and endocrine disrupting potential of Bisphenol-B and Bisphenol-F: A mini-review". Toxicology Letters. 312: 222–227. doi:10.1016/j.toxlet.2019.05.018. ISSN 0378-4274. PMID 31136786.
  5. ^ Fishburn, Judith L. A.; Larson, Heather L.; Nguyen, An; Welch, Chloe J.; Moore, Taylor; Penn, Aliyah; Newman, Johnathan; Mangino, Anthony; Widman, Erin; Ghobashy, Rana; Witherspoon, Jocelyn; Lee, Wendy; Mulligan, Kimberly A. (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. ISSN 0892-0362. PMID 38301979.
  6. ^ a b Audebert, Marc; Dolo, L.; Perdu, E.; Cravedi, J.-P.; Zalko, D. (2011-06-09). "Use of the γH2AX assay for assessing the genotoxicity of bisphenol A and bisphenol F in human cell lines". Archives of Toxicology. 85 (11): 1463–1473. Bibcode:2011ArTox..85.1463A. doi:10.1007/s00204-011-0721-2. ISSN 0340-5761. PMID 21656223. S2CID 19978735.
  7. ^ Cabaton, Nicolas; Zalko, Daniel; Rathahao, Estelle; Canlet, Cécile; Delous, Georges; Chagnon, Marie-Christine; Cravedi, Jean-Pierre; Perdu, Elisabeth (2008-10-01). "Biotransformation of bisphenol F by human and rat liver subcellular fractions". Toxicology in Vitro. 22 (7): 1697–1704. Bibcode:2008ToxVi..22.1697C. doi:10.1016/j.tiv.2008.07.004. ISSN 0887-2333. PMID 18672047.
  8. ^ Dumont, Coralie; Perdu, Elisabeth; Sousa, Georges de; Debrauwer, Laurent; Rahmani, Roger; Cravedi, Jean-Pierre; Chagnon, Marie-Christine (2011-10-01). "Bis(hydroxyphenyl)methane—bisphenol F—metabolism by the HepG2 human hepatoma cell line and cryopreserved human hepatocytes". Drug and Chemical Toxicology. 34 (4): 445–453. doi:10.3109/01480545.2011.585651. ISSN 0148-0545. PMID 21770713. S2CID 25319579.
  9. ^ a b Eladak, Soria; Grisin, Tiphany; Moison, Delphine; Guerquin, Marie-Justine; N'Tumba-Byn, Thierry; Pozzi-Gaudin, Stéphanie; Benachi, Alexandra; Livera, Gabriel; Rouiller-Fabre, Virginie; Habert, René (January 2015). "A new chapter in the bisphenol A story: bisphenol S and bisphenol F are not safe alternatives to this compound". Fertility and Sterility. 103 (1): 11–21. doi:10.1016/j.fertnstert.2014.11.005. ISSN 0015-0282. PMID 25475787.
  10. ^ Rochester, Johanna R.; Bolden, Ashley L. (2015-07-01). "Bisphenol S and F: A Systematic Review and Comparison of the Hormonal Activity of Bisphenol A Substitutes". Environmental Health Perspectives. 123 (7): 643–650. doi:10.1289/ehp.1408989. PMC 4492270. PMID 25775505.
  11. ^ Chen, Da; Kannan, Kurunthachalam; Tan, Hongli; Zheng, Zhengui; Feng, Yong-Lai; Wu, Yan; Widelka, Margaret (2016-06-07). "Bisphenol Analogues Other Than BPA: Environmental Occurrence, Human Exposure, and Toxicity—A Review". Environmental Science & Technology. 50 (11): 5438–5453. Bibcode:2016EnST...50.5438C. doi:10.1021/acs.est.5b05387. ISSN 0013-936X. PMID 27143250.
  12. ^ Fishburn, Judith L. A.; Larson, Heather L.; Nguyen, An; Welch, Chloe J.; Moore, Taylor; Penn, Aliyah; Newman, Johnathan; Mangino, Anthony; Widman, Erin; Ghobashy, Rana; Witherspoon, Jocelyn; Lee, Wendy; Mulligan, Kimberly A. (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. ISSN 0892-0362. PMID 38301979.
  13. ^ Yang, Jichun; Wang, Xin; Zhang, Danfeng; Wang, Lingling; Li, Qi; Zhang, Lei (2014-12-01). "Simultaneous determination of endocrine disrupting compounds bisphenol F and bisphenol AF using carboxyl functionalized multi-walled carbon nanotubes modified electrode". Talanta. 130: 207–212. doi:10.1016/j.talanta.2014.06.056. ISSN 0039-9140. PMID 25159400.
  14. ^ Rajasärkkä, Johanna; Pernica, Marek; Kuta, Jan; Lašňák, Jonáš; Šimek, Zdenĕk; Bláha, Luděk (2016-10-15). "Drinking water contaminants from epoxy resin-coated pipes: A field study". Water Research. 103: 133–140. Bibcode:2016WatRe.103..133R. doi:10.1016/j.watres.2016.07.027. ISSN 0043-1354. PMID 27448038.
  15. ^ Cabaton, Nicolas; Dumont, Coralie; Severin, Isabelle; Perdu, Elisabeth; Zalko, Daniel; Cherkaoui-Malki, Mustapha; Chagnon, Marie-Christine (2009-01-08). "Genotoxic and endocrine activities of bis(hydroxyphenyl)methane (bisphenol F) and its derivatives in the HepG2 cell line". Toxicology. 255 (1–2): 15–24. Bibcode:2009Toxgy.255...15C. doi:10.1016/j.tox.2008.09.024. ISSN 0300-483X. PMID 18973785.
  16. ^ Higashihara, Nobuhiko; Shiraishi, Keiji; Miyata, Katusi; Oshima, Yutaka; Minobe, Yasushi; Yamasaki, Kanji (2007-12-01). "Subacute oral toxicity study of bisphenol F based on the draft protocol for the "Enhanced OECD Test Guideline no. 407"". Archives of Toxicology. 81 (12): 825–832. Bibcode:2007ArTox..81..825H. doi:10.1007/s00204-007-0223-4. ISSN 0340-5761. PMID 17628788. S2CID 20531873.
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