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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 17:48:03 UTC
Update Date2021-10-13 06:22:07 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
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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point156 - 157 °CNot Available
Boiling Point292.00 to 293.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.12 mg/mL at 25 °CNot Available
LogP3.32Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available147.126http://allccs.zhulab.cn/database/detail?ID=AllCCS00000915
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.086 g/LALOGPS
logP10(3.81) g/LALOGPS
logP10(4.04) g/LChemAxon
logS10(-3.4) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+153.28131661259
DarkChem[M-H]-153.71531661259
DeepCCS[M+H]+160.70930932474
DeepCCS[M-H]-158.35130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Bisphenol ACC(C)(C1=CC=C(O)C=C1)C1=CC=C(O)C=C13617.7Standard polar33892256
Bisphenol ACC(C)(C1=CC=C(O)C=C1)C1=CC=C(O)C=C12142.8Standard non polar33892256
Bisphenol ACC(C)(C1=CC=C(O)C=C1)C1=CC=C(O)C=C12158.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Bisphenol A,1TMS,isomer #1CC(C)(C1=CC=C(O)C=C1)C1=CC=C(O[Si](C)(C)C)C=C12216.5Semi standard non polar33892256
Bisphenol A,2TMS,isomer #1CC(C)(C1=CC=C(O[Si](C)(C)C)C=C1)C1=CC=C(O[Si](C)(C)C)C=C12197.8Semi standard non polar33892256
Bisphenol A,1TBDMS,isomer #1CC(C)(C1=CC=C(O)C=C1)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C12491.4Semi standard non polar33892256
Bisphenol A,2TBDMS,isomer #1CC(C)(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C12713.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Bisphenol A EI-B (Non-derivatized)splash10-03di-2290000000-5a53b16778a578ff5d0d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Bisphenol A EI-B (Non-derivatized)splash10-03di-2290000000-5a53b16778a578ff5d0d2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bisphenol A GC-MS (Non-derivatized) - 70eV, Positivesplash10-03g0-1790000000-7521406d051aed77fe2f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bisphenol A GC-MS (2 TMS) - 70eV, Positivesplash10-0ab9-6289000000-59b1fac0d668364456292017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bisphenol A GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bisphenol A GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-03di-3590000000-0cd99fd08fc2fad698f32014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Bisphenol A LC-ESI-ITFT , positive-QTOFsplash10-0zfs-4960000000-b4ebb7f1ff08fbb41adb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bisphenol A LC-ESI-ITFT , positive-QTOFsplash10-004i-1090000000-80a2709d727e93053cd12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bisphenol A LC-ESI-ITFT , positive-QTOFsplash10-004i-0090000000-c33246c7d9d8b300c90c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bisphenol A LC-ESI-ITFT , positive-QTOFsplash10-004i-0090000000-e5f7d4cb43ef56a850562017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bisphenol A LC-ESI-ITFT , positive-QTOFsplash10-0532-9340000000-c3298310f84ad87b13102017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bisphenol A LC-ESI-ITFT , positive-QTOFsplash10-000t-9000000000-75784b9156574d6f17622017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bisphenol A LC-ESI-ITFT , positive-QTOFsplash10-0a4j-1900000000-1316f0a328865698ba142017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bisphenol A 75V, Positive-QTOFsplash10-000t-9000000000-75784b9156574d6f17622021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bisphenol A 35V, Positive-QTOFsplash10-0zfs-4960000000-b4ebb7f1ff08fbb41adb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bisphenol A 15V, Positive-QTOFsplash10-004i-0090000000-c33246c7d9d8b300c90c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bisphenol A 30V, Positive-QTOFsplash10-004i-1090000000-80a2709d727e93053cd12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bisphenol A 30V, Positive-QTOFsplash10-004i-0090000000-e5f7d4cb43ef56a850562021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bisphenol A 45V, Positive-QTOFsplash10-0532-9340000000-c3298310f84ad87b13102021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bisphenol A 35V, Positive-QTOFsplash10-0a4j-1900000000-1316f0a328865698ba142021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bisphenol A 10V, Positive-QTOFsplash10-004i-0090000000-8791a2cf0310bf33a81e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bisphenol A 20V, Positive-QTOFsplash10-004i-0190000000-ee807d7dec5640d38d182016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bisphenol A 40V, Positive-QTOFsplash10-01rb-2920000000-e15c6a1d966dd429fe3f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bisphenol A 10V, Negative-QTOFsplash10-004i-0090000000-0494eb6f9068e16e1d992016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bisphenol A 20V, Negative-QTOFsplash10-004i-0090000000-e9b5452c25e607f299502016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bisphenol A 40V, Negative-QTOFsplash10-002f-9470000000-9d3d569c0a3f755f123f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bisphenol A 10V, Positive-QTOFsplash10-002r-1960000000-42e45d340eea8ee9e3db2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bisphenol A 20V, Positive-QTOFsplash10-0a4i-3900000000-8ef860db11d71a8b2f2e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bisphenol A 40V, Positive-QTOFsplash10-0a4i-2900000000-61ebc2c60a263652b43e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bisphenol A 10V, Negative-QTOFsplash10-004i-3090000000-27243d7aedeaef4a196c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bisphenol A 20V, Negative-QTOFsplash10-0095-3940000000-3863b01420a8ec7c47d32021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
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
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal 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
Good Scents IDrw1450961
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.. .