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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 17:48:03 UTC
Update Date2020-10-09 21:09:19 UTC
HMDB IDHMDB0032133
Secondary Accession Numbers
  • HMDB32133
Metabolite Identification
Common NameBisphenol A
DescriptionBisphenol A, also known as 4,4'-bisphenol a or BPA, belongs to the class of organic compounds known as bisphenols. These are methylenediphenols, HOC6H4CH2C6H4OH, commonly p,p-methylenediphenol, and their substitution products (generally derived from condensation of two equivalent amounts of a phenol with an aldehyde or ketone). Bisphenol A is an extremely weak basic (essentially neutral) compound (based on its pKa). Bisphenol A exists in all living organisms, ranging from bacteria to humans. Bisphenol A is a potentially toxic compound. Bisphenol A, commonly abbreviated as BPA, is an organic compound with two phenol functional groups. With an annual production of 2-3 million metric tonnes, it is an important monomer in the production of polycarbonate. Bisphenol A has low acute toxicity, with an oral LD50 of 3250 mg/kg in rats, but it is an endocrine disruptor. In case of inhalation, move patient to fresh air and monitor for respiratory distress.
Structure
Data?1563862224
Synonyms
ValueSource
2, 2-Bis(4-hydroxyphenyl)propaneChEBI
2,2-Bis(4'-hydroxyphenyl)propaneChEBI
2,2-Bis(4-hydroxyphenyl)propaneChEBI
2,2-Bis(p-hydroxyphenyl)propaneChEBI
2,2-Di(4-hydroxyphenyl)propaneChEBI
2,2-Di(4-phenylol)propaneChEBI
4,4'-(1-Methylethane-1,1-diyl)diphenolChEBI
4,4'-(1-Methylethylidene)bisphenolChEBI
4,4'-(Propane-2,2-diyl)diphenolChEBI
4,4'-Bisphenol aChEBI
4,4'-IsopropylidenediphenolChEBI
Bisphenol-aChEBI
BPAChEBI
Dianin's compoundChEBI
(1-Methylethylidene)bis-phenolHMDB
1,1'-(1-Methylethylidene)bisphenylol, 9ciHMDB
2, 2-Bis(hydroxyphenyl)propaneHMDB
2, 2-Di(4-phenylol)propaneHMDB
2,2'-Bis(4-hydroxyphenyl)propaneHMDB
2,2-(4,4'-Dihydroxydiphenyl)propaneHMDB
2,2-(4,4-Dihydroxydiphenyl)propaneHMDB
2,2-Bis (4-hydroxyphenol) propaneHMDB
2,2-Bis(4,4'-hydroxyphenyl)propaneHMDB
2,2-Bis(hydroxyphenyl)propaneHMDB
2,2-Bis(p-hydroxyphenyl)-propaneHMDB
2,2-Bis-4'-hydroxyfenylpropanHMDB
2,2-Bis[4-hydroxyphenyl]propaneHMDB
2,2-Di-(4'-hydroxyphenyl)-propaneHMDB
4, 4'-Bisphenol aHMDB
4, 4'-Dihydroxydiphenyl-2,2-propaneHMDB
4, 4'-DihydroxydiphenyldimethylmethaneHMDB
4, 4'-DihydroxydiphenylpropaneHMDB
4,4' IsopropylidinediphenolHMDB
4,4'-(1-Methylethylidene)bis-phenolHMDB
4,4'-(1-Methylethylidene)bisphenol, 9ciHMDB
4,4'-DihydroxdiphenylpropaneHMDB
4,4'-Dihydroxy-2,2-diphenylpropaneHMDB
4,4'-Dihydroxydiphenyl-2,2-propaneHMDB
4,4'-DihydroxydiphenyldimethylmethaneHMDB
4,4'-DihydroxydiphenylpropaneHMDB
4,4'-Dimethylmethylenedi-phenolHMDB
4,4'-DimethylmethylenediphenolHMDB
4,4'-Isopropylidene diphenolHMDB
4,4'-ISOPROPYLIDENE-diphenolHMDB
4,4'-IsopropylidenebisphenolHMDB
4,4'-Isopropylidenebis[phenol]HMDB
4,4'-Isopropylidenedi-phenolHMDB
4,4'-ISOPROPYLIDENEDIPHENOL (bisphenol a)HMDB
4,4'-Isopropylidenediphenol bHMDB
4,4'-Isopropylidenediphenol, 8ciHMDB
4,4'-Propane-2,2-diyldiphenolHMDB
4,4-IsopropylidenediphenolHMDB
4,4[-IsopropylidenediphenolHMDB
4-[1-(4-Hydroxyphenyl)-1-methylethyl]phenolHMDB
beta, Beta'-bis(p-hydroxyphenyl)propaneHMDB
beta,Beta'-bis(p-hydroxyphenyl)propaneHMDB
beta,beta-Di-(p-hydroxyphenyl)propaneHMDB
beta-Di-(p-hydroxyphenyl)propaneHMDB
beta-Di-p-hydroxyphenylpropaneHMDB
Biphenol aHMDB
Bis(4-hyd roxyphenyl) dimethylmethaneHMDB
Bis(4-hydroxyphenyl) dimethylmethaneHMDB
Bis(4-hydroxyphenyl) propaneHMDB
Bis(4-hydroxyphenyl)dimethylmethaneHMDB
Bis(4-hydroxyphenyl)propaneHMDB
Bis(p-hydroxyphenyl)propaneHMDB
Bisferol aHMDB
BisphenolHMDB
Bisphenol a (bpa)HMDB
Bisphenol a, disodium saltHMDB
Bisphenol a, sodium saltHMDB
Bisphenol a.HMDB
Di-2,2-(4-hydroxyphenyl)propaneHMDB
DianHMDB
DianoHMDB
Dimethyl bis(p-hydroxyphenyl)methaneHMDB
Dimethylbis(p-hydroxyphenyl)methaneHMDB
Dimethylmethylene-p,p'-diphenolHMDB
DiphenylolpropaneHMDB
Hydrogenated bisphenol aHMDB
Ipognox 88HMDB
Isopropylidenebis(4-hydroxybenzene)HMDB
Millad hbpaHMDB
NonameHMDB
p, P'-dihydroxydiphenyldimethylmethaneHMDB
p, P'-dihydroxydiphenylpropaneHMDB
p, P'-isopropylidenediphenolHMDB
p,P'-bisphenol aHMDB
p,P'-dihydroxydiphenyldimethylmethaneHMDB
p,P'-dihydroxydiphenylpropaneHMDB
p,P'-isopropylidenebisphenolHMDB
p,P'-isopropylidenediphenolHMDB
ParabisHMDB
Parabis aHMDB
Poly(bisphenol a carbonate)HMDB
RikabanolHMDB
Ucar bisphenol aHMDB
Ucar bisphenol HPHMDB
Chemical FormulaC15H16O2
Average Molecular Weight228.2863
Monoisotopic Molecular Weight228.115029756
IUPAC Name4-[2-(4-hydroxyphenyl)propan-2-yl]phenol
Traditional Namebisphenol-A
CAS Registry Number80-05-7
SMILES
CC(C)(C1=CC=C(O)C=C1)C1=CC=C(O)C=C1
InChI Identifier
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
InChI KeyIISBACLAFKSPIT-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as bisphenols. These are methylenediphenols, HOC6H4CH2C6H4OH, commonly p,p-methylenediphenol, and their substitution products (generally derived from condensation of two equivalent amounts of a phenol with an aldehyde or ketone).
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentBisphenols
Alternative Parents
Substituents
  • Bisphenol
  • Phenylpropane
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Environmental role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point156 - 157 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.12 mg/mL at 25 °CNot Available
LogP3.32Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.086 g/LALOGPS
logP3.81ALOGPS
logP4.04ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)9.78ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity79.28 m³·mol⁻¹ChemAxon
Polarizability25.41 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-2290000000-5a53b16778a578ff5d0dSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-2290000000-5a53b16778a578ff5d0dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03g0-1790000000-7521406d051aed77fe2fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0ab9-6289000000-59b1fac0d66836445629Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0zfs-4960000000-b4ebb7f1ff08fbb41adbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-1090000000-80a2709d727e93053cd1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0090000000-c33246c7d9d8b300c90cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0090000000-e5f7d4cb43ef56a85056Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0532-9340000000-c3298310f84ad87b1310Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000t-9000000000-75784b9156574d6f1762Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4j-1900000000-1316f0a328865698ba14Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-8791a2cf0310bf33a81eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0190000000-ee807d7dec5640d38d18Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01rb-2920000000-e15c6a1d966dd429fe3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-0494eb6f9068e16e1d99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-e9b5452c25e607f29950Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9470000000-9d3d569c0a3f755f123fSpectrum
MSMass Spectrum (Electron Ionization)splash10-03di-3590000000-0cd99fd08fc2fad698f3Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.00142(0.00095-0.00202) umol/mmol creatinineNot AvailableBothNormal
    • Report on Human B...
details
UrineDetected and Quantified0.00120(0.00095-0.00153) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Report on Human B...
details
UrineDetected and Quantified0.000941 (0.000872-0.00102) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
    • Report on Human B...
details
UrineDetected and Quantified0.00117 (0.00104-0.00131) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal
    • National Health a...
    • Report on Human B...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06973
Phenol Explorer Compound IDNot Available
FooDB IDFDB008856
KNApSAcK IDNot Available
Chemspider ID6371
KEGG Compound IDC13624
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBisphenol_A
METLIN IDNot Available
PubChem Compound6623
PDB ID2OH
ChEBI ID33216
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029800
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kim JY, Jeong HG: Down-regulation of inducible nitric oxide synthase and tumor necrosis factor-alpha expression by bisphenol A via nuclear factor-kappaB inactivation in macrophages. Cancer Lett. 2003 Jun 30;196(1):69-76. [PubMed:12860292 ]
  2. Masuda S, Terashima Y, Sano A, Kuruto R, Sugiyama Y, Shimoi K, Tanji K, Yoshioka H, Terao Y, Kinae N: Changes in the mutagenic and estrogenic activities of bisphenol A upon treatment with nitrite. Mutat Res. 2005 Aug 1;585(1-2):137-46. [PubMed:15936980 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .