{{Short description|Class of chemical compounds}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{distinguish|biphenol}} The '''bisphenols''' ({{IPAc-en|ˈ|b|ɪ|s|f|ᵻ|n|ɒ|l}}) are a group of industrial chemical compounds related to diphenylmethane; commonly used in the production of plastics and epoxy resins. They feature two hydroxyphenyl groups linked by a methylene bridge. Also included are bisphenol S, P, and M. "Bisphenol" is a common 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".<ref name=Ullmann>{{cite encyclopedia | vauthors = Fiege H, Voges HW, Hamamoto T, Umemura S, Iwata T, Miki H, Fujita Y, Buysch HJ, Garbe D, Paulus W |title=Phenol Derivatives |encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2002|publisher=Wiley-VCH|location=Weinheim|doi=10.1002/14356007.a19_313|isbn=978-3-527-30673-2 |entry=Phenol Derivatives }}.</ref>
Bisphenols have attracted controversy because of their role as endocrine disruptors. Their estrogenic properties are weak, but the scale of their production is considerable.<ref name = "Almeida_2018" /><ref>{{cite journal | vauthors = Vandenberg LN, Maffini MV, Sonnenschein C, Rubin BS, Soto AM | title = Bisphenol-A and the great divide: a review of controversies in the field of endocrine disruption | journal = Endocrine Reviews | volume = 30 | issue = 1 | pages = 75–95 | date = February 2009 | pmid = 19074586 | pmc = 2647705 | doi = 10.1210/er.2008-0021 }}</ref>
==Partial inventory of bisphenols== {| class="wikitable" ! Structural formula ! Name ! CAS ! colspan="2" | Reactants |- |150px|Bisphenol A||Bisphenol A || 80-05-7 || Phenol || Acetone |- |150px|Bisphenol AP||Bisphenol AP || 1571-75-1 ||Phenol || Acetophenone |- |150px|Bisphenol AF||Bisphenol AF || 1478-61-1 || Phenol || Hexafluoroacetone |- |150px|Bisphenol B||Bisphenol B || 77-40-7 || Phenol || Butanone |- |150px|Bisphenol BP||Bisphenol BP || 1844-01-5 || Phenol || Benzophenone |- |150px|Bisphenol C||Bisphenol C || 79-97-0 || ''o''-cresol || Acetone |- |150px|Bisphenol CII||Bisphenol C 2 || 14868-03-2 || Phenol || Chloral |- |150px|Bisphenol E||Bisphenol E || 2081-08-5 || Phenol ||Ethanal |- |150px|Bisphenol F||Bisphenol F || 620-92-8 || Phenol || Formaldehyde |- |150px|Bisphenol G||Bisphenol G || 127-54-8 || 2-Isopropylphenol || Acetone |- |150px|Bisphenol M||Bisphenol M || 13595-25-0 || || |- |150px|Bisphenol S||Bisphenol S || 80-09-1 || Phenol || Sulfur trioxide |- |150px|Bisphenol P||Bisphenol P || 2167-51-3 || || |- |150px|Bisphenol PH||Bisphenol PH || 24038-68-4 || 2-Phenylphenol || Acetone |- |150px|Bisphenol TMC||Bisphenol TMC || 129188-99-4 || Phenol || 3,3,5-Trimethylcyclohexanone |- |150px|Bisphenol Z||Bisphenol Z || 843-55-0 || Phenol || Cyclohexanone |- |150px|Dinitrobisphenol A||Dinitrobisphenol A || 5329-21-5 || Bisphenol A || Nitric acid |- |150px|Tetrabromobisphenol A||Tetrabromobisphenol A || 79-94-7 || Bisphenol A || Bromine |- |150px|Tetramethylbisphenol F||Tetramethyl bisphenol F || 5384-21-4 || 2,6-Xylenol || Formaldehyde |}
==Health effects== Many bisphenols, including Bisphenols A (BPA), F (BPF) and S (BPS), have been shown to be endocrine disruptors, potentially relating to adverse health effects.<ref name = "Almeida_2018" /><ref>{{cite web|title=BPA-Free Plastic Containers May Be Just as Hazardous|url=http://www.scientificamerican.com/article/bpa-free-plastic-containers-may-be-just-as-hazardous/|magazine=Scientific American|date=11 August 2014| vauthors = Bilbrey J |access-date=8 August 2015}}</ref> Other implicated health effects include obesity and metabolic disorders.<ref name="Akash2023">{{cite journal |last1=Akash |first1=M. S. H. |last2=Alshahrani |first2=S. |last3=Alzahrani |first3=A. |year=2023 |title=Toxicological evaluation of bisphenol analogues: Preventive measures and therapeutic interventions |journal=Environmental Toxicology and Pharmacology |volume=83 |article-number=103545 |doi =10.1016/j.etap.2023.103545 |doi-broken-date=17 November 2025 }}</ref> The threat is of interest because the chemical is pervasive in everyday life, including food<ref name = "Almeida_2018">{{cite journal | vauthors = Almeida S, Raposo A, Almeida-González M, Carrascosa C | title = Bisphenol A: Food Exposure and Impact on Human Health | journal = Comprehensive Reviews in Food Science and Food Safety | volume = 17 | issue = 6 | pages = 1503–1517 | date = November 2018 | pmid = 33350146 | doi = 10.1111/1541-4337.12388 }}</ref> and through the use of thermal paper.<ref name= Heinälä/>
===Occurrence in humans=== Bisphenols have monitored in humans through analysis of serum and urine.<ref name="Hines2017">{{Cite journal |last1=Hines |first1=Cynthia J. |last2=Jackson |first2=Matthew V. |last3=Deddens |first3=James A. |last4=Clark |first4=John C. |last5=Ye |first5=Xiaoyun |last6=Christianson |first6=Annette L. |last7=Meadows |first7=Juliana W. |last8=Calafat |first8=Antonia M. |date=2017-03-01 |title=Urinary Bisphenol A (BPA) Concentrations among Workers in Industries that Manufacture and Use BPA in the USA |url=https://academic.oup.com/annweh/article/61/2/164/2769471 |journal=Annals of Work Exposures and Health |language=en |volume=61 |issue=2 |pages=164–182 |doi=10.1093/annweh/wxw021 |issn=2398-7308 |pmc=5577557 |pmid=28395354}}</ref><ref name="Ribeiro2017">{{cite journal|last1=Ribeiro|first1=E.|last2=Ladeira|first2=C.|last3=Viegas|first3=S.|year=2017|title=Occupational Exposure to Bisphenol A (BPA): A Reality That Still Needs to Be Unveiled|journal=Toxics |volume=5 |issue=3 |page=22 |doi=10.3390/toxics5030022 |doi-access=free }}</ref> Workers who manufacture BPA-based thermal paper have high BPA levels.<ref name= Heinälä>{{cite journal |last1=Heinälä |first1=M. |last2=Ylinen |first2=K. |last3=Tuomi |first3=T. |last4=Santonen |first4=T. |last5=Porras |first5=S. P. |year=2017 |title=Assessment of occupational exposure to bisphenol A in five different production companies in Finland |journal=Annals of Work Exposures and Health |volume=61 |issue=1 |pages=44–55 |doi=10.1093/annweh/wxw006 |pmid=28395312 }}</ref> BPS and BPF levels are elevated among workers dismantling e-waste in China.<ref>{{cite web |title=Bisphenols |website=European Chemicals Agency |url=https://echa.europa.eu/hot-topics/bisphenols |access-date=2025-11-10}}</ref> 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.<ref>{{cite journal |last1=Rifa |first1=R. A. |last2=Lavado |first2=R. |year=2024 |title=Unveiling the next generation of bisphenol analogs and their impact on human health using in vitro methods |journal=Emerging Contaminants |volume=10 |issue=2 |article-number=100296 |doi=10.1016/j.emcon.2023.100296}}</ref><ref name="Akash2023" /><ref>{{Cite book | vauthors = Pelch KE, Wignall JA, Goldstone AE, Ross PK, Blain RB, Shapiro AJ, Holmgren SD, Hsieh JH, Svoboda D |url=https://www.ncbi.nlm.nih.gov/books/NBK538922/ |title=NTP Research Report on Biological Activity of Bisphenol A (BPA) Structural Analogues and Functional Alternatives: Research Report 4 |date=2017 |publisher=National Toxicology Program |series=NTP Research Reports |location=Research Triangle Park (NC) |pmid=31944638}}</ref><ref>{{cite journal | vauthors = Fishburn JL, Larson HL, Nguyen A, Welch CJ, Moore T, Penn A, Newman J, Mangino A, Widman E, Ghobashy R, Witherspoon J, Lee W, Mulligan KA | title = Bisphenol F affects neurodevelopmental gene expression, mushroom body development, and behavior in Drosophila melanogaster | journal = Neurotoxicology and Teratology | volume = 102 | article-number = 107331 | date = 2024-03-01 | pmid = 38301979 | doi = 10.1016/j.ntt.2024.107331 | bibcode = 2024NTxT..10207331F | doi-access = free }}</ref>
===Biodegradation=== {{See also|Bisphenol A#Environmental effects}} Due to its high production volumes, BPA has been characterised as "pseudo-persistent",<ref>{{cite journal | vauthors = Pivnenko K, Pedersen GA, Eriksson E, Astrup TF | title = Bisphenol A and its structural analogues in household waste paper | journal = Waste Management | volume = 44 | pages = 39–47 | date = October 2015 | pmid = 26194879 | doi = 10.1016/j.wasman.2015.07.017 | s2cid = 217938141 | bibcode = 2015WaMan..44...39P | url = https://backend.orbit.dtu.dk/ws/files/118749778/PostPrint_Davidsen_JoH_1_.pdf }}</ref> leading to its spreading and potential accumulation in a variety of environmental matrices. BPA has a fairly short half-life. A number of aerobic organisms degrade BPA.<ref>{{cite journal |last1=Im |first1=Jeongdae |last2=Löffler |first2=Frank E. |title=Fate of Bisphenol a in Terrestrial and Aquatic Environments |journal=Environmental Science & Technology |date=2016 |volume=50 |issue=16 |pages=8403–8416 |doi=10.1021/acs.est.6b00877 |pmid=27401879 |osti=1470902 }}</ref>
===Precautions to reduce occupational exposures=== Engineering controls to reduce exposure in the workplace 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.<ref>{{cite web |title=Occupational Exposure to Bisphenol A (BPA) in U.S. Manufacturing Companies |website=NIOSH Science Blog |publisher=Centers for Disease Control and Prevention (CDC) |date=2017-01-05 |url=https://www.cdc.gov/niosh/blogs/2017/bpa.html |access-date=2025-11-10}}</ref><ref>{{cite web |title=Occupational Exposure to BPA |website=CBIA |date=2017-01-18 |url=https://www.cbia.com/news/hr-safety/occupational-exposure-bpa/ |access-date=2025-11-10}}</ref>
=== Exposure to bisphenol=== Because bisphenol is 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 (skin absorption, ingestion and inhalation).<ref name="Hines2017" />
== Exposure pathways == === Dietary exposure=== The main pathway of exposure is through ingestion of food that is contaminated with bisphenol. Bisphenol can leach slowly into the food from surfaces such as the inside lining of cans, plastic containers, packages, disposable tableware, and through wear and tear.<ref name="Lee2022" /> This means that eating foods or drinking beverages that came in contact with products made from bisphenol could result in exposure.<ref name="Benhamada2016" /><ref name="Agarwal2022" /> Studies have found bisphenol residue in foods and beverages even when using containers that claimed to be "bisphenol free".<ref name="Ali2019" />
=== Dermal (skin) exposure === Bisphenol can also enter the body through the skin via absorption and can result in skin irritation or allergic reactions in some individuals.<ref name="Lee2022" /><ref name="NIOSH2011" /> 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 in ingestion of the chemical.<ref name="Ehrlich2014" /> Workers who handle receipts regularly, like cashiers and retail employees, may face higher dermal exposure.<ref name="Lee2022" /><ref name="NIEHS_BPA" />
=== Inhalation exposure === Due to its volatility, bisphenol do not easily evaporate into the air at room temperature according to their chemical properties.<ref name="NIEHS_BPA" /><ref name="NIOSH2011" /> However, bisphenol can attach to dust and small particles in the environment and be inhaled. Usually, inhalation exposure of bisphenol are more common under industrial and manufacture settings.<ref name="ECHA2023" /><ref name="Hines2017" /><ref name="Konieczna2015" /> == References == {{Reflist|refs= <ref name="Lee2022">{{cite journal | last1=Lee | first1=S. S. | last2=Ryu | first2=H. Y. | last3=Ahn | first3=K. S. | last4=Lee | first4=S. | last5=Lee | first5=J. | last6=Lee | first6=J. W. | last7=Ko | first7=S. M. | last8=Son | first8=W. C. | year=2022 | title=Toxicological profile of bisphenol F | journal=Journal of Toxicology and Environmental Health Part A | volume=85 | issue=4 | pages=163–174 | doi=10.1080/15287394.2021.1997843}}</ref> <ref name="Benhamada2016">{{cite journal | last1=Benhamada | first1=M. | last2=Bouzid | first2=D. | last3=Boyron | first3=O. | last4=Taam | first4=M. | year=2016 | title=The relationship between the aging of polycarbonate characterized by SEC and the release of bisphenol A quantified by HPLC-UV | journal=European Food Research and Technology | volume=242 | issue=2 | pages=227–232 |doi=10.1007/s00217-015-2534-7}}</ref> <ref name="Agarwal2022">{{cite journal | last1=Agarwal | first1=A. | last2=Gandhi | first2=S. | last3=Tripathi | first3=A. D. | last4=Iammarino | first4=M. | last5=Homroy | first5=S. | year=2022 | title=Analysis of Bisphenol A migration from microwaveable polycarbonate cups into coffee during microwave heating | journal=International Journal of Food Science & Technology | volume=57 | pages=7477–7485 |doi=10.1111/ijfs.16103}}</ref> <ref name="Ali2019">{{cite journal | last1=Ali | first1=M. | last2=Jaghbir | first2=M. | last3=Salam | first3=M. | last4=Al-Kadamany | first4=G. | last5=Damsees | first5=R. | last6=Al-Rawashdeh | first6=N. | year=2019 | title=Testing baby bottles for the presence of residual and migrated bisphenol A | journal=Environmental Monitoring and Assessment | volume=191 | issue=1 | pages=1–11 |doi=10.1007/s10661-018-7126-0}}</ref> <ref name="NIOSH2011">{{cite report | author=National Institute for Occupational Safety and Health | title=NIOSH Skin Notation Profiles: Bisphenol A (BPA) | year=2011 | publisher=U.S. Department of Health and Human Services }}</ref> <ref name="NIEHS_BPA">{{cite web | author=National Institute of Environmental Health Sciences | title=Bisphenol A (BPA) | url=https://www.niehs.nih.gov/health/topics/agents/sya-bpa }}</ref> <ref name="ECHA2023">{{cite report | author=European Chemicals Agency | title=Scientific report for evaluation of limit values for Bisphenol A at the workplace | year=2023 | url=https://echa.europa.eu/documents/10162/23ca2397-4387-e040-8070-b1fd27423fda }}</ref> <ref name="Ehrlich2014">{{cite journal | last1=Ehrlich | first1=S. | last2=Calafat | first2=A. M. | last3=Humblet | first3=O. | last4=Smith | first4=T. | last5=Hauser | first5=R. | year=2014 | title=Handling of thermal receipts as a source of exposure to bisphenol A | journal=JAMA | volume=311 | issue=8 | pages=859–860 | doi=10.1001/jama.2013.283735 }}</ref> <ref name="Konieczna2015">{{cite journal | last1=Konieczna | first1=A. | last2=Rutkowska | first2=A. | last3=Rachoń | first3=D. | year=2015 | title=Health risk of exposure to bisphenol A | journal=Roczniki Państwowego Zakładu Higieny | volume=66 | issue=1 |url=https://roczniki.pzh.gov.pl/Health-risk-of-exposure-to-Bisphenol-A-BPA-,182345,0,2.html}}</ref> }}
== Further reading == * For additional examples and alternate names, see: {{cite book |title= Polymer Science Dictionary | vauthors = Alger M |publisher= Springer |year= 2017 |isbn= 978-94-024-0893-5 |page= 77 }}
Category:Bisphenols Category:Endocrine disruptors Category:Environmental chemistry Category:Occupational hazards