Bisphenol F

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][2]

Bisphenol F

Names
Preferred IUPAC name 4,4′-Methylenediphenol
Other names BPF; 4,4′-Dihydroxydiphenylmethane
Identifiers
CAS Number	620-92-8 Y
3D model (JSmol)	Interactive image
ChemSpider	11614
ECHA InfoCard	100.009.691
PubChem CID	12111
UNII	QD2C19044Z Y
CompTox Dashboard (EPA)	DTXSID9022445
InChI 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
SMILES c1cc(ccc1Cc2ccc(cc2)O)O
Properties
Chemical formula	C13H12O2
Molar mass	200.237 g·mol−1
Appearance	colorless or white solid
Melting point	162.5 °C (324.5 °F; 435.6 K)
Boiling point	237–243 °C (459–469 °F; 510–516 K) 12-13 Torr
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Uses

BPF is used in the manufacture of plastics and epoxy resins.^[3] 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.^[4] BPF is also utilized in liners, lacquers, adhesives, plastics, and the coating of drinks and food cans.^[3] BPF is found in dental materials, such as restorative materials, liners, adhesives, oral prosthetic devices and tissue substitutes.^[3][1][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. "Exposure s in utero may program the diseases of the testis, prostate, kidney and abnormalities in the immune system, and cause tumors, uterine hemorrhage during pregnancy and polycystic ovary".^[9]

Environmental contamination

BPF is pervasive in the environment, appearing in river water, drinking water, and agricultural soil samples.^[10] Biodegradation appears to be the most promising route for removal of BPA and related bisphenols. One degradation process converts BPA to the corresponding benzophenone (HOC₆H₄)₂CO, which is relatively labile.^[11]

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. Catenza, Cyrene J.; Farooq, Amna; Shubear, Noor S.; Donkor, Kingsley K. (2021). "A targeted review on fate, occurrence, risk and health implications of bisphenol analogues". Chemosphere. 268. Bibcode:2021Chmsp.26829273C. doi:10.1016/j.chemosphere.2020.129273. PMID 33352513.
3. 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.
4. 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.
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. 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. Basak, Sanjay; Das, Mrinal K.; Duttaroy, Asim K. (2020). "Plastics derived endocrine-disrupting compounds and their effects on early development". Birth Defects Research. 112 (17): 1308–1325. doi:10.1002/bdr2.1741. PMID 32476245.
10. Liu, Jianchao; Zhang, Lingyu; Lu, Guanghua; Jiang, Runren; Yan, Zhenhua; Li, Yiping (2021). "Occurrence, toxicity and ecological risk of Bisphenol a analogues in aquatic environment – A review". Ecotoxicology and Environmental Safety. 208. Bibcode:2021EcoES.20811481L. doi:10.1016/j.ecoenv.2020.111481. PMID 33120264.
11. Noszczyńska, Magdalena; Piotrowska-Seget, Zofia (2018). "Bisphenols: Application, occurrence, safety, and biodegradation mediated by bacterial communities in wastewater treatment plants and rivers". Chemosphere. 201: 214–223. Bibcode:2018Chmsp.201..214N. doi:10.1016/j.chemosphere.2018.02.179.