CHEBI:33216 - bisphenol A

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ChEBI Name bisphenol A
ChEBI ID CHEBI:33216
Definition A bisphenol that is 4,4'-methanediyldiphenol in which the methylene hydrogens are replaced by two methyl groups.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:47094, CHEBI:22900, CHEBI:31295
Supplier Information No supplier information found for this compound.
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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 scale by the condensation reaction of phenol and acetone. Global production in 2022 was estimated to be in the region of 10 million tonnes. BPA's largest single application is as a co-monomer in the production of polycarbonates, which accounts for 65–70% of all BPA production. The manufacturing of epoxy resins and vinyl ester resins account for 25–30% of BPA use. The remaining 5% is used as a major component of several high-performance plastics, and as a minor additive in PVC, polyurethane, thermal paper, and several other materials. It is not a plasticizer, although it is often wrongly labelled as such. The health effects of BPA have been the subject of prolonged public and scientific debate. BPA is a xenoestrogen, exhibiting hormone-like properties that mimic the effects of estrogen in the body. Although the effect is very weak, the pervasiveness of BPA-containing materials raises concerns, as exposure is effectively lifelong. Many BPA-containing materials are non-obvious but commonly encountered, and include coatings for the inside of food cans, clothing designs, shop receipts, and dental fillings. BPA has been investigated by public health agencies in many countries, as well as by the World Health Organization. While normal exposure is below the level currently associated with risk, several jurisdictions have taken steps to reduce exposure on a precautionary basis, in particular by banning BPA from baby bottles. There is some evidence that BPA exposure in infants has decreased as a result of this. BPA-free plastics have also been introduced, which are manufactured using alternative bisphenols such as bisphenol S and bisphenol F, but there is also controversy around whether these are actually safer.
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Formulae C15H16O2
C15H16O2
Net Charge 0
Average Mass 228.291
Monoisotopic Mass 228.11503
InChI InChI=1S/C15H16O2/c1-15(2,11-3-7-13(16)8-4-11)12-5-9-14(17)10-6-12/h3-10,16-17H,1-2H3
InChIKey IISBACLAFKSPIT-UHFFFAOYSA-N
SMILES CC(C)(C1=CC=C(O)C=C1)C1=CC=C(O)C=C1
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): xenoestrogen
A synthetic or semi-synthetic compound that has oestrogenic activity.
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
Application(s): endocrine disruptor
Any compound that can disrupt the functions of the endocrine (hormone) system
xenoestrogen
A synthetic or semi-synthetic compound that has oestrogenic activity.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing bisphenol A (CHEBI:33216) has role endocrine disruptor (CHEBI:138015)
bisphenol A (CHEBI:33216) has role environmental contaminant (CHEBI:78298)
bisphenol A (CHEBI:33216) has role xenobiotic (CHEBI:35703)
bisphenol A (CHEBI:33216) has role xenoestrogen (CHEBI:76988)
bisphenol A (CHEBI:33216) is a bisphenol (CHEBI:22901)
Incoming 3,3',5,5'-tetrabromobisphenol A (CHEBI:33217) has functional parent bisphenol A (CHEBI:33216)
4-[2-(4-methoxyphenyl)propan-2-yl]phenol (CHEBI:131346) has functional parent bisphenol A (CHEBI:33216)
5-hydroxybisphenol A (CHEBI:31133) has functional parent bisphenol A (CHEBI:33216)
bisphenol A (3-chloro-2-hydroxypropyl) (2,3-dihydroxypropyl) ether (CHEBI:59642) has functional parent bisphenol A (CHEBI:33216)
bisphenol A dimethacrylate (CHEBI:34579) has functional parent bisphenol A (CHEBI:33216)
bisphenol A sulfate (CHEBI:167305) has functional parent bisphenol A (CHEBI:33216)
bisphenol AF (CHEBI:72754) has functional parent bisphenol A (CHEBI:33216)
IUPAC Name
4,4'-(propane-2,2-diyl)diphenol
Synonyms Sources
2, 2-Bis(4-hydroxyphenyl)propane HMDB
2,2-Bis(4'-hydroxyphenyl)propane HMDB
2,2-Bis(4-Hydroxyphenyl)propane KEGG COMPOUND
2,2-Bis(p-hydroxyphenyl)propane ChemIDplus
2,2-Di(4-hydroxyphenyl)propane ChemIDplus
2,2-Di(4-phenylol)propane ChemIDplus
4,4'-(1-Methylethane-1,1-diyl)diphenol HMDB
4,4'-(1-Methylethylidene)bisphenol ChemIDplus
4,4'-(Propane-2,2-diyl)diphenol HMDB
4,4'-Bisphenol A ChemIDplus
4,4'-Isopropylidenediphenol ChemIDplus
Bisphenol A KEGG COMPOUND
bisphenol A UniProt
bisphenol-A ChEBI
BPA HMDB
Dianin's compound ChEBI
Manual Xrefs Databases
2OH PDBeChem
Bisphenol_A Wikipedia
c0764 UM-BBD
C13624 KEGG COMPOUND
DB06973 DrugBank
HMDB0032133 HMDB
LSM-37080 LINCS
View more database links
Registry Numbers Types Sources
1107700 Reaxys Registry Number Reaxys
80-05-7 CAS Registry Number KEGG COMPOUND
80-05-7 CAS Registry Number NIST Chemistry WebBook
80-05-7 CAS Registry Number ChemIDplus
Citations
Resnik DB, Elliott KC (2015)
Bisphenol A and risk management ethics.
Bioethics 29, 182-189 [PubMed:24471646]
[show Abstract]
Ferreira LL, Couto R, Oliveira PJ (2015)
Bisphenol A as epigenetic modulator: setting the stage for carcinogenesis?
European journal of clinical investigation 45 Suppl 1, 32-36 [PubMed:25524584]
[show Abstract]
Niu Y, Zhang J, Duan H, Wu Y, Shao B (2015)
Bisphenol A and nonylphenol in foodstuffs: Chinese dietary exposure from the 2007 total diet study and infant health risk from formulas.
Food chemistry 167, 320-325 [PubMed:25148994]
[show Abstract]
Fang F, Chen D, Yu P, Qian W, Zhou J, Liu J, Gao R, Wang J, Xiao H (2015)
Effects of Bisphenol A on glucose homeostasis and brain insulin signaling pathways in male mice.
General and comparative endocrinology 212, 44-50 [PubMed:25637671]
[show Abstract]
Vojdani A, Kharrazian D, Mukherjee PS (2015)
Elevated levels of antibodies against xenobiotics in a subgroup of healthy subjects.
Journal of applied toxicology : JAT 35, 383-397 [PubMed:25042713]
[show Abstract]
Liu J, Jin X, Zhao N, Ye X, Ying C (2015)
Bisphenol A promotes X-linked inhibitor of apoptosis protein-dependent angiogenesis via G protein-coupled estrogen receptor pathway.
Journal of applied toxicology : JAT 35, 1309-1317 [PubMed:25663485]
[show Abstract]
Gao H, Yang BJ, Li N, Feng LM, Shi XY, Zhao WH, Liu SJ (2015)
Bisphenol A and hormone-associated cancers: current progress and perspectives.
Medicine 94, e211 [PubMed:25569640]
[show Abstract]
Kuruto-Niwa R, Tateoka Y, Usuki Y, Nozawa R (2007)
Measurement of bisphenol A concentrations in human colostrum.
Chemosphere 66, 1160-1164 [PubMed:16904728]
[show Abstract]
Masuda S, Terashima Y, Sano A, Kuruto R, Sugiyama Y, Shimoi K, Tanji K, Yoshioka H, Terao Y, Kinae N (2005)
Changes in the mutagenic and estrogenic activities of bisphenol A upon treatment with nitrite.
Mutation research 585, 137-146 [PubMed:15936980]
[show Abstract]
Kim JY, Jeong HG (2003)
Down-regulation of inducible nitric oxide synthase and tumor necrosis factor-alpha expression by bisphenol A via nuclear factor-kappaB inactivation in macrophages.
Cancer letters 196, 69-76 [PubMed:12860292]
[show Abstract]
Tohei A, Suda S, Taya K, Hashimoto T, Kogo H (2001)
Bisphenol A inhibits testicular functions and increases luteinizing hormone secretion in adult male rats.
Experimental biology and medicine (Maywood, N.J.) 226, 216-221 [PubMed:11361040]
[show Abstract]
Farabollini F, Porrini S, Dessì-Fulgherit F (1999)
Perinatal exposure to the estrogenic pollutant bisphenol A affects behavior in male and female rats.
Pharmacology, biochemistry, and behavior 64, 687-694 [PubMed:10593191]
[show Abstract]
Last Modified
22 January 2021
General Comment
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag