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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 17:48:03 UTC
Update Date2017-12-07 03:17:18 UTC
HMDB IDHMDB0032133
Secondary Accession Numbers
  • HMDB32133
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
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 KeyIISBACLAFKSPIT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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).
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
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

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Route of exposure:

  Parenteral:

  Enteral:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

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 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-2290000000-5a53b16778a578ff5d0dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03g0-1790000000-7521406d051aed77fe2fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0ab9-6289000000-59b1fac0d66836445629View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0zfs-4960000000-b4ebb7f1ff08fbb41adbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-1090000000-80a2709d727e93053cd1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0090000000-c33246c7d9d8b300c90cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0090000000-e5f7d4cb43ef56a85056View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0532-9340000000-c3298310f84ad87b1310View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000t-9000000000-75784b9156574d6f1762View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4j-1900000000-1316f0a328865698ba14View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-8791a2cf0310bf33a81eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0190000000-ee807d7dec5640d38d18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01rb-2920000000-e15c6a1d966dd429fe3fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-0494eb6f9068e16e1d99View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-e9b5452c25e607f29950View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9470000000-9d3d569c0a3f755f123fView in MoNA
MSMass Spectrum (Electron Ionization)splash10-03di-3590000000-0cd99fd08fc2fad698f3View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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
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. [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.. .