bisphenol F
{{Chembox
| ImageFile = Bisphenol F skeletal.svg
| ImageSize = 200px
| ImageFile2 = Bisphenol F 3D BS.png
| ImageSize2 = 200px
| PIN = 4,4′-Methylenediphenol
| OtherNames = BPF; 4,4′-Dihydroxydiphenylmethane
| Section1 = {{Chembox Identifiers
| CASNo = 620-92-8
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = QD2C19044Z
| PubChem = 12111
| ChemSpiderID = 11614
| SMILES = c1cc(ccc1Cc2ccc(cc2)O)O
| 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
| InChIKey = PXKLMJQFEQBVLD-UHFFFAOYAW
| StdInChI = 1S/C13H12O2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h1-8,14-15H,9H2
| StdInChIKey = PXKLMJQFEQBVLD-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| C=13|H=12|O=2
| Appearance = colorless or white solid
| Density =
| MeltingPtC = 162.5
| BoilingPtC = 237-243
| BoilingPt_notes =12-13 Torr
| Solubility =
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| Autoignition =
}}
}}
Bisphenol F (BPF; 4,4′-dihydroxydiphenylmethane) is an organic compound with the chemical formula {{chem|(HOC|6|H|4|)|2|CH|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.{{Cite journal|last1=Usman|first1=Afia|last2=Ikhlas|first2=Shoeb|last3=Ahmad|first3=Masood|date=2019-09-15|title=Occurrence, toxicity and endocrine disrupting potential of Bisphenol-B and Bisphenol-F: A mini-review|url=https://www.sciencedirect.com/science/article/pii/S0378427419301559|journal=Toxicology Letters|language=en|volume=312|pages=222–227|doi=10.1016/j.toxlet.2019.05.018|pmid=31136786 |s2cid=169035866 |issn=0378-4274|url-access=subscription}}{{cite journal |doi=10.1016/j.chemosphere.2020.129273 |title=A targeted review on fate, occurrence, risk and health implications of bisphenol analogues |date=2021 |last1=Catenza |first1=Cyrene J. |last2=Farooq |first2=Amna |last3=Shubear |first3=Noor S. |last4=Donkor |first4=Kingsley K. |journal=Chemosphere |volume=268 |pmid=33352513 |bibcode=2021Chmsp.26829273C }}
Uses
BPF is used in the manufacture of plastics and epoxy resins.{{Cite journal|last1=Rochester|first1=Johanna Ruth|last2=Bolden|first2=Ashley Louise|title=Bisphenol S and F: A Systematic Review and Comparison of the Hormonal Activity of Bisphenol A Substitutes|url=http://ehp.niehs.nih.gov/1408989|journal=Environmental Health Perspectives|doi=10.1289/ehp.1408989|pmc=4492270|pmid=25775505|volume=123|issue=7|year=2015|pages=643–50|bibcode=2015EnvHP.123..643R }} 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.{{Cite journal|last1=Cabaton|first1=Nicolas|last2=Chagnon|first2=Marie-Christine|last3=Lhuguenot|first3=Jean-Claude|last4=Cravedi|first4=Jean-Pierre|last5=Zalko|first5=Daniel|date=2006-12-27|title=Disposition and metabolic profiling of bisphenol F in pregnant and nonpregnant rats|journal=Journal of Agricultural and Food Chemistry|volume=54|issue=26|pages=10307–10314|doi=10.1021/jf062250q|issn=0021-8561|pmid=17177575|bibcode=2006JAFC...5410307C }} BPF is also utilized in liners, lacquers, adhesives, plastics, and the coating of drinks and food cans. BPF is found in dental materials, such as restorative materials, liners, adhesives, oral prosthetic devices and tissue substitutes.{{Cite journal |last1=Fishburn |first1=Judith L. A. |last2=Larson |first2=Heather L. |last3=Nguyen |first3=An |last4=Welch |first4=Chloe J. |last5=Moore |first5=Taylor |last6=Penn |first6=Aliyah |last7=Newman |first7=Johnathan |last8=Mangino |first8=Anthony |last9=Widman |first9=Erin |last10=Ghobashy |first10=Rana |last11=Witherspoon |first11=Jocelyn |last12=Lee |first12=Wendy |last13=Mulligan |first13=Kimberly A. |date=2024-03-01 |title=Bisphenol F affects neurodevelopmental gene expression, mushroom body development, and behavior in Drosophila melanogaster |journal=Neurotoxicology and Teratology |volume=102 |pages=107331 |doi=10.1016/j.ntt.2024.107331 |issn=0892-0362|doi-access=free |pmid=38301979 |bibcode=2024NTxT..10207331F }}
Biological effects
= Pharmacokinetics =
BPF undergoes two primary phase II biotransformations to form the corresponding glucuronide and sulfate.{{Cite journal|last1=Audebert|first1=Marc|last2=Dolo|first2=L.|last3=Perdu|first3=E.|last4=Cravedi|first4=J.-P.|last5=Zalko|first5=D.|date=2011-06-09|title=Use of the γH2AX assay for assessing the genotoxicity of bisphenol A and bisphenol F in human cell lines|journal=Archives of Toxicology|language=en|volume=85|issue=11|pages=1463–1473|doi=10.1007/s00204-011-0721-2|pmid=21656223|bibcode=2011ArTox..85.1463A |s2cid=19978735|issn=0340-5761}}{{Cite journal|last1=Cabaton|first1=Nicolas|last2=Zalko|first2=Daniel|last3=Rathahao|first3=Estelle|last4=Canlet|first4=Cécile|last5=Delous|first5=Georges|last6=Chagnon|first6=Marie-Christine|last7=Cravedi|first7=Jean-Pierre|last8=Perdu|first8=Elisabeth|date=2008-10-01|title=Biotransformation of bisphenol F by human and rat liver subcellular fractions|journal=Toxicology in Vitro |volume=22|issue=7|pages=1697–1704|doi=10.1016/j.tiv.2008.07.004|issn=0887-2333|pmid=18672047|bibcode=2008ToxVi..22.1697C }}{{Cite journal|last1=Dumont|first1=Coralie|last2=Perdu|first2=Elisabeth|last3=Sousa|first3=Georges de|last4=Debrauwer|first4=Laurent|last5=Rahmani|first5=Roger|last6=Cravedi|first6=Jean-Pierre|last7=Chagnon|first7=Marie-Christine|date=2011-10-01|title=Bis(hydroxyphenyl)methane—bisphenol F—metabolism by the HepG2 human hepatoma cell line and cryopreserved human hepatocytes|journal=Drug and Chemical Toxicology|volume=34|issue=4|pages=445–453|doi=10.3109/01480545.2011.585651|issn=0148-0545|pmid=21770713|s2cid=25319579}}
= 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".{{cite journal |doi=10.1002/bdr2.1741 |title=Plastics derived endocrine-disrupting compounds and their effects on early development |date=2020 |last1=Basak |first1=Sanjay |last2=Das |first2=Mrinal K. |last3=Duttaroy |first3=Asim K. |journal=Birth Defects Research |volume=112 |issue=17 |pages=1308–1325 |pmid=32476245 |hdl=10852/82658 |hdl-access=free }}
Environmental contamination
BPF is pervasive in the environment, appearing in river water, drinking water, and agricultural soil samples.{{cite journal |doi=10.1016/j.ecoenv.2020.111481 |title=Occurrence, toxicity and ecological risk of Bisphenol a analogues in aquatic environment – A review |date=2021 |last1=Liu |first1=Jianchao |last2=Zhang |first2=Lingyu |last3=Lu |first3=Guanghua |last4=Jiang |first4=Runren |last5=Yan |first5=Zhenhua |last6=Li |first6=Yiping |journal=Ecotoxicology and Environmental Safety |volume=208 |pmid=33120264 |bibcode=2021EcoES.20811481L |doi-access=free }} Biodegradation appears to be the most promising route for removal of BPA and related bisphenols. One degradation process converts BPA to the corresponding benzophenone {{chem2|(HOC6H4)2CO}}, which is relatively labile.{{cite journal |doi=10.1016/j.chemosphere.2018.02.179 |title=Bisphenols: Application, occurrence, safety, and biodegradation mediated by bacterial communities in wastewater treatment plants and rivers |date=2018 |last1=Noszczyńska |first1=Magdalena |last2=Piotrowska-Seget |first2=Zofia |journal=Chemosphere |volume=201 |pages=214–223 |pmid=29524822 |bibcode=2018Chmsp.201..214N }}
References
{{Reflist}}
{{Xenoestrogens}}
{{Androgen receptor modulators}}
{{Estrogen receptor modulators}}