Bisphenol F
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Bisphenol F (BPF; 4,4′-dihydroxydiphenylmethane) is an
organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
with the chemical formula . It is structurally related to
bisphenol A Bisphenol A (BPA) is a chemical compound primarily used in the manufacturing of various plastics. It is a colourless solid which is soluble in most common organic solvents, but has very poor solubility in water. BPA is produced on an industrial s ...
(BPA), a popular precursor for forming
plastic Plastics are a wide range of synthetic or semi-synthetic materials that use polymers as a main ingredient. Their plasticity makes it possible for plastics to be moulded, extruded or pressed into solid objects of various shapes. This adaptab ...
s, as both belong to the category of molecules known as
bisphenol The bisphenols () are a group of chemical compounds related to diphenylmethane. 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 lett ...
s, 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.


Uses

BPF is used in the manufacture of
plastic Plastics are a wide range of synthetic or semi-synthetic materials that use polymers as a main ingredient. Their plasticity makes it possible for plastics to be moulded, extruded or pressed into solid objects of various shapes. This adaptab ...
s and epoxy resins. 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. 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.


Biological effects


Pharmacokinetics

BPF undergoes two primary phase II biotransformations to form the corresponding
glucuronide A glucuronide, also known as glucuronoside, is any substance produced by linking glucuronic acid to another substance via a glycosidic bond. The glucuronides belong to the glycosides. Glucuronidation, the conversion of chemical compounds to glucu ...
and
sulfate The sulfate or sulphate ion is a polyatomic anion with the empirical formula . Salts, acid derivatives, and peroxides of sulfate are widely used in industry. Sulfates occur widely in everyday life. Sulfates are salts of sulfuric acid and many ...
.


Hormonal Effects

BPF has
estrogen Estrogen or oestrogen is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three major endogenous estrogens that have estrogenic hormonal acti ...
ic,
progesteron Progesterone (P4) is a medication and naturally occurring steroid hormone. It is a progestogen and is used in combination with estrogens mainly in hormone therapy for menopausal symptoms and low sex hormone levels in women. It is also used i ...
ic, and anti-
androgen An androgen (from Greek ''andr-'', the stem of the word meaning "man") is any natural or synthetic steroid hormone that regulates the development and maintenance of male characteristics in vertebrates by binding to androgen receptors. This in ...
ic effects. The overarching implications of these hormonal changes for humans are decreases in
testosterone Testosterone is the primary sex hormone and anabolic steroid in males. In humans, testosterone plays a key role in the development of Male reproductive system, male reproductive tissues such as testes and prostate, as well as promoting secondar ...
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 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. It is important to note that 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 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.


Environmental contamination

BPF is pervasive in the environment. Four out of five studies yielded results that BPF is estrogenic,
androgenic An androgen (from Greek ''andr-'', the stem of the word meaning "man") is any natural or synthetic steroid hormone that regulates the development and maintenance of male characteristics in vertebrates by binding to androgen receptors. This incl ...
and
thyroidogenic File:Thyroid_system.svg, upright=1.5, The thyroid system of the thyroid hormones T3 and T4 rect 376 268 820 433 Thyroid-stimulating hormone rect 411 200 849 266 Thyrotropin-releasing hormone rect 297 168 502 200 Hypothalamus rect 66 216 386 25 ...
. The greatest effect of BPF to be liver toxicity. ''In vitro'' studies of BPF showed effects of cytotoxicity,
cellular dysfunction Cellular may refer to: *Cellular automaton, a model in discrete mathematics * Cell biology, the evaluation of cells work and more * ''Cellular'' (film), a 2004 movie *Cellular frequencies, assigned to networks operating in cellular RF bands *Cell ...
,
DNA damage DNA repair is a collection of processes by which a cell identifies and corrects damage to the DNA molecules that encode its genome. In human cells, both normal metabolic activities and environmental factors such as radiation can cause DNA da ...
and
chromosomal aberration A chromosomal abnormality, chromosomal anomaly, chromosomal aberration, chromosomal mutation, or chromosomal disorder, is a missing, extra, or irregular portion of chromosomal DNA. These can occur in the form of numerical abnormalities, where ther ...
s.


References

{{Estrogen receptor modulators Bisphenols Endocrine disruptors Estrogens Nonsteroidal antiandrogens Bis(4-hydroxyphenyl)methanes