Thebisphenols (/ˈbɪsfɪnɒl/) are a group of industrial chemical compounds related todiphenylmethane; commonly used in the production of plastics and epoxy resins. They feature twohydroxyphenyl groups linked by amethylene bridge. Also included are bisphenol S, P, and M. "Bisphenol" is acommon name; the letter following denotes the variant, which depends on the additional substituents.Bisphenol A is the most common representative of the group, with millions of metric tons produced globally in the past decade, often simply called "bisphenol".[1]
Bisphenols have attracted controversy because of their role asendocrine disruptors. Theirestrogenic properties are weak, but the scale of their production is considerable.[2][3]
| Structural formula | Name | CAS | Reactants | |
|---|---|---|---|---|
 | Bisphenol A | 80-05-7 | Phenol | Acetone |
 | Bisphenol AP | 1571-75-1 | Phenol | Acetophenone |
 | Bisphenol AF | 1478-61-1 | Phenol | Hexafluoroacetone |
 | Bisphenol B | 77-40-7 | Phenol | Butanone |
 | Bisphenol BP | 1844-01-5 | Phenol | Benzophenone |
 | Bisphenol C | 79-97-0 | o-cresol | Acetone |
 | Bisphenol C 2 | 14868-03-2 | Phenol | Chloral |
 | Bisphenol E | 2081-08-5 | Phenol | Ethanal |
 | Bisphenol F | 620-92-8 | Phenol | Formaldehyde |
 | Bisphenol G | 127-54-8 | 2-Isopropylphenol | Acetone |
 | Bisphenol M | 13595-25-0 | ||
 | Bisphenol S | 80-09-1 | Phenol | Sulfur trioxide |
 | Bisphenol P | 2167-51-3 | ||
 | Bisphenol PH | 24038-68-4 | 2-Phenylphenol | Acetone |
 | Bisphenol TMC | 129188-99-4 | Phenol | 3,3,5-Trimethylcyclohexanone |
 | Bisphenol Z | 843-55-0 | Phenol | Cyclohexanone |
 | Dinitrobisphenol A | 5329-21-5 | Bisphenol A | Nitric acid |
 | Tetrabromobisphenol A | 79-94-7 | Bisphenol A | Bromine |
 | Tetramethyl bisphenol F | 5384-21-4 | 2,6-Xylenol | Formaldehyde |
Many bisphenols, including Bisphenols A (BPA), F (BPF) and S (BPS), have been shown to beendocrine disruptors, potentially relating to adverse health effects.[2][4] Other implicated health effects include obesity and metabolic disorders.[5]The threat is of interest because the chemical is pervasive in everyday life, inclluding food[2] andthermal paper.[6]
Bisphenols have monitored in humans through analysis of serum and urine.[7][8] Workers who manufacture BPA-based thermal paper have high BPA levels.[6]. BPS and BPF levels are elevated among workers dismantling e-waste in China.[9]
Many analogues of BPA, such as bisphenol F (BPF), bisphenol S (BPS), bisphenol AP (BPAP), bisphenol AF (BPAF), bisphenol FL (BPFL), and bisphenol C (BPC) are less studied with respect to their hormone-disrupting potential and other health effects.[10][5][11][12]
Due to its high production volumes, BPA has been characterised as "pseudo-persistent",[13] leading to its spreading and potential accumulation in a variety of environmental matrices. BPA has a fairly shorthalf-life. A number of aerobic organisms degrade BPA.[14][15]
Engineering controls have been applied such as process enclosure, local exhaust ventilation, and isolation of bisphenol-handling areas lower airborne and surface contamination in workplaces where bisphenols are used.[16][17].
Because bisphenol are largely used in everyday life such as in plastics, protective coating of packages, inner lining of food containers, and thermal paper of receipts, it can enter the body through multiple pathways.[18]
The main pathway of exposure is throughingestion of food that is contaminated with bisphenol. Bisphenol canleach slowly into the food from things like the inside lining of cans, plastic containers, packages, disposable tableware, and especially through wear and tear.[19]This means that even simply using or eating food that came in contact with product made from bisphenol could result in exposure.[20]Moreover, studies have found bisphenol residue in foods and beverages even when using containers that claimed to be "bisphenol free".[20][21][22]
Bisphenol can also enter the body through the skin viaabsorption, and can result in skinirritation orallergic reactions in some individuals.[19][23] One well-known example is the handling of store receipts, which are often coated with bisphenol, and can transfer from the skin of the hands to the mouth, resulting iningestion of the chemical.[24]Workers who handle receipts regularly, like cashiers and retail employees, may face higher dermal exposure.[19][25]
Due to itsvolatility, bisphenol do not easily evaporate into the air atroom temperature according to their chemical properties.[25][23] However, bisphenol can attach to dust an smallparticles in the environment and be inhaled. Usually, inhalation exposure of bisphenol are more common under industrial and manufacture settings.[26][18][27]
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