# Bisphenol

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{{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](/source/diphenylmethane); commonly used in the production of plastics and epoxy resins. They feature two [hydroxyphenyl](/source/phenols) groups linked by a [methylene bridge](/source/methylene_bridge). Also included are bisphenol S, P, and M. "Bisphenol" is a [common name](/source/Trivial_name); the letter following denotes the variant, which depends on the additional substituents. [Bisphenol A](/source/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](/source/endocrine_disruptors).  Their [estrogen](/source/estrogen)ic 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](/source/CAS_registry_number) 
! colspan="2" | [Reactant](/source/Reactant)s 
|-
|150px|Bisphenol A||[Bisphenol A](/source/Bisphenol_A) || 80-05-7 || [Phenol](/source/Phenol) || [Acetone](/source/Acetone)
|-
|150px|Bisphenol AP||[Bisphenol AP](/source/Bisphenol_AP) || 1571-75-1 ||[Phenol](/source/Phenol) || [Acetophenone](/source/Acetophenone)
|-
|150px|Bisphenol AF||[Bisphenol AF](/source/Bisphenol_AF) || 1478-61-1 || [Phenol](/source/Phenol) || [Hexafluoroacetone](/source/Hexafluoroacetone)
|-
|150px|Bisphenol B||[Bisphenol B](/source/Bisphenol_B) || 77-40-7 || [Phenol](/source/Phenol) || [Butanone](/source/Butanone)
|-
|150px|Bisphenol BP||[Bisphenol BP](/source/Bisphenol_BP) || 1844-01-5 || [Phenol](/source/Phenol) || [Benzophenone](/source/Benzophenone)
|-
|150px|Bisphenol C||[Bisphenol C](/source/Bisphenol_C) || 79-97-0 || [''o''-cresol](/source/o-Cresol) || [Acetone](/source/Acetone)
|-
|150px|Bisphenol CII||[Bisphenol C 2](/source/Bisphenol_C_2)  || 14868-03-2 || [Phenol](/source/Phenol) || [Chloral](/source/Chloral)
|-
|150px|Bisphenol E||[Bisphenol E](/source/Bisphenol_E) || 2081-08-5
|| [Phenol](/source/Phenol) ||[Ethanal](/source/Acetaldehyde)
|-
|150px|Bisphenol F||[Bisphenol F](/source/Bisphenol_F) || 620-92-8 || [Phenol](/source/Phenol) || [Formaldehyde](/source/Formaldehyde)
|-
|150px|Bisphenol G||[Bisphenol G](/source/Bisphenol_G) || 127-54-8 || 2-Isopropylphenol || [Acetone](/source/Acetone)
|-
|150px|Bisphenol M||[Bisphenol M](/source/Bisphenol_M) || 13595-25-0 ||  ||
|-
|150px|Bisphenol S||[Bisphenol S](/source/Bisphenol_S) || 80-09-1 || [Phenol](/source/Phenol) || [Sulfur trioxide](/source/Sulfur_trioxide)
|-
|150px|Bisphenol P||[Bisphenol P](/source/Bisphenol_P) || 2167-51-3 ||  ||
|-
|150px|Bisphenol PH||[Bisphenol PH](/source/Bisphenol_PH) || 24038-68-4 || [2-Phenylphenol](/source/2-Phenylphenol) || [Acetone](/source/Acetone)
|-
|150px|Bisphenol TMC||[Bisphenol TMC](/source/Bisphenol_TMC) || 129188-99-4 || [Phenol](/source/Phenol) || 3,3,5-Trimethylcyclohexanone
|-
|150px|Bisphenol Z||[Bisphenol Z](/source/Bisphenol_Z) || 843-55-0 || [Phenol](/source/Phenol) || [Cyclohexanone](/source/Cyclohexanone)
|-
|150px|Dinitrobisphenol A||[Dinitrobisphenol A](/source/Dinitrobisphenol_A) || 5329-21-5 || [Bisphenol A](/source/Bisphenol_A) || [Nitric acid](/source/Nitric_acid)
|-
|150px|Tetrabromobisphenol A||[Tetrabromobisphenol A](/source/Tetrabromobisphenol_A) || 79-94-7 || [Bisphenol A](/source/Bisphenol_A) || [Bromine](/source/Bromine)
|-
|150px|Tetramethylbisphenol F||[Tetramethyl bisphenol F](/source/Tetramethyl_bisphenol_F) || 5384-21-4 || [2,6-Xylenol](/source/2%2C6-Xylenol) || [Formaldehyde](/source/Formaldehyde)
|}

==Health effects==
Many bisphenols, including Bisphenols A (BPA), F (BPF) and S (BPS), have been shown to be [endocrine disruptor](/source/endocrine_disruptor)s, 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](/source/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](/source/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](/source/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](/source/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](/source/Coating) of packages, inner lining of food containers, and [thermal paper](/source/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](/source/ingestion) of food that is contaminated with bisphenol. Bisphenol can [leach](/source/Leaching_(chemistry)) 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](/source/Absorption_(skin)) and can result in skin [irritation](/source/irritation) or [allergic reactions](/source/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](/source/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](/source/Volatility_(chemistry)), bisphenol do not easily evaporate into the air at [room temperature](/source/room_temperature) according to their chemical properties.<ref name="NIEHS_BPA" /><ref name="NIOSH2011" /> However, bisphenol can attach to dust and small [particles](/source/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

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Adapted from the Wikipedia article [Bisphenol](https://en.wikipedia.org/wiki/Bisphenol) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Bisphenol?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.