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Record Information
Version3.6
Creation Date2012-09-11 17:48:03 UTC
Update Date2016-02-11 02:03:49 UTC
HMDB IDHMDB32133
Secondary Accession NumbersNone
Metabolite Identification
Common NameBisphenol A
DescriptionBisphenol A, commonly abbreviated as BPA, is an organic compound with two phenol functional groups. It is a difunctional building block of several important plastics and plastic additives. With an annual production of 2–3 million metric tonnes, it is an important monomer in the production of polycarbonate. It is a potential food contaminant arising from its use in reusable polycarbonate food containers such as water carboys, baby bottles and kitchen utensils. Suspected of being hazardous to humans since the 1930s, concerns about the use of bisphenol A in consumer products were regularly reported in the news media in 2008 after several governments issued reports questioning its safety, and some retailers removed baby bottles and other children's products made from it from their shelves.
Structure
Thumb
Synonyms
ValueSource
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-Methylethylidene)bisphenolChEBI
4,4'-Bisphenol aChEBI
4,4'-IsopropylidenediphenolChEBI
Bisphenol-aChEBI
(1-Methylethylidene)bis-phenolHMDB
1,1'-(1-Methylethylidene)bisphenylol, 9ciHMDB
2, 2-Bis(4-hydroxyphenyl)propaneHMDB
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'-hydroxyphenyl)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-Methylethane-1,1-diyl)diphenolHMDB
4,4'-(1-Methylethylidene)bis-phenolHMDB
4,4'-(1-Methylethylidene)bisphenol, 9ciHMDB
4,4'-(Propane-2,2-diyl)diphenolHMDB
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
BPAHMDB
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 KeyInChIKey=IISBACLAFKSPIT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as bisphenols. These are organic compounds containing two hydroxyphenyl group based on a diphenylmethane backbone.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentBisphenols
Alternative Parents
Substituents
  • Bisphenol
  • Phenylpropane
  • Phenol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
BiofunctionNot Available
Application
  • Nutrient
Cellular locations
  • Membrane
Physical Properties
StateNot Available
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity79.28 m3·mol-1ChemAxon
Polarizability25.41 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-03di-3590000000-0cd99fd08fc2fad698f3View in MoNA
1D NMR1H NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
    • Report on Human B...
    • National Health a...
details
UrineDetected and Quantified0.00117 (0.00104-0.00131) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal
    • Report on Human B...
    • National Health a...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB008856
KNApSAcK IDNot Available
Chemspider ID6371
KEGG Compound IDC13624
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB32133
Metagene LinkHMDB32133
METLIN IDNot Available
PubChem Compound6623
PDB ID2OH
ChEBI ID33216
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. [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. [15936980 ]
  3. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.