ContaminantDB: Bisphenol A

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (43)XML

Record Information

Version

1.0

Creation Date

2009-03-19 21:46:58 UTC

Update Date

2026-05-14 18:29:24 UTC

Accession Number

CHEM000566

Identification

Common Name

Bisphenol A

Class

Small Molecule

Description

Bisphenol 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.

Contaminant Sources

Clean Air Act Chemicals
FooDB Chemicals
HMDB Contaminants - Urine
HPV EPA Chemicals
My Exposome Chemicals
OECD HPV Chemicals
STOFF IDENT Compounds
Suspected Compounds – Schymanski Project
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Aromatic Hydrocarbon
Food Toxin
Household Toxin
Human Neurotoxin
Industrial/Workplace Toxin
Metabolite
Organic Compound
PMT
Pesticide
Phenolic Antioxidant
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2, 2-Bis(4-hydroxyphenyl)propane	ChEBI
2,2-Bis(4'-hydroxyphenyl)propane	ChEBI
2,2-Bis(4-hydroxyphenyl)propane	ChEBI
2,2-Bis(p-hydroxyphenyl)propane	ChEBI
2,2-Di(4-hydroxyphenyl)propane	ChEBI
2,2-Di(4-phenylol)propane	ChEBI
4,4'-(1-Methylethane-1,1-diyl)diphenol	ChEBI
4,4'-(1-Methylethylidene)bisphenol	ChEBI
4,4'-(Propane-2,2-diyl)diphenol	ChEBI
4,4'-Bisphenol a	ChEBI
4,4'-Isopropylidenediphenol	ChEBI
Bisphenol-a	ChEBI
BPA	ChEBI
Dianin's compound	ChEBI
(1-Methylethylidene)bis-phenol	HMDB
1,1'-(1-Methylethylidene)bisphenylol, 9ci	HMDB
2, 2-Bis(hydroxyphenyl)propane	HMDB
2, 2-Di(4-phenylol)propane	HMDB
2,2'-Bis(4-hydroxyphenyl)propane	HMDB
2,2-(4,4'-Dihydroxydiphenyl)propane	HMDB
2,2-(4,4-Dihydroxydiphenyl)propane	HMDB
2,2-Bis (4-hydroxyphenol) propane	HMDB
2,2-Bis(4,4'-hydroxyphenyl)propane	HMDB
2,2-Bis(hydroxyphenyl)propane	HMDB
2,2-Bis(p-hydroxyphenyl)-propane	HMDB
2,2-Bis-4'-hydroxyfenylpropan	HMDB
2,2-Bis[4-hydroxyphenyl]propane	HMDB
2,2-Di-(4'-hydroxyphenyl)-propane	HMDB
4, 4'-Bisphenol a	HMDB
4, 4'-Dihydroxydiphenyl-2,2-propane	HMDB
4, 4'-Dihydroxydiphenyldimethylmethane	HMDB
4, 4'-Dihydroxydiphenylpropane	HMDB
4,4' Isopropylidinediphenol	HMDB
4,4'-(1-Methylethylidene)bis-phenol	HMDB
4,4'-(1-Methylethylidene)bisphenol, 9ci	HMDB
4,4'-Dihydroxdiphenylpropane	HMDB
4,4'-Dihydroxy-2,2-diphenylpropane	HMDB
4,4'-Dihydroxydiphenyl-2,2-propane	HMDB
4,4'-Dihydroxydiphenyldimethylmethane	HMDB
4,4'-Dihydroxydiphenylpropane	HMDB
4,4'-Dimethylmethylenedi-phenol	HMDB
4,4'-Dimethylmethylenediphenol	HMDB
4,4'-Isopropylidene diphenol	HMDB
4,4'-ISOPROPYLIDENE-diphenol	HMDB
4,4'-Isopropylidenebisphenol	HMDB
4,4'-Isopropylidenebis[phenol]	HMDB
4,4'-Isopropylidenedi-phenol	HMDB
4,4'-ISOPROPYLIDENEDIPHENOL (bisphenol a)	HMDB
4,4'-Isopropylidenediphenol b	HMDB
4,4'-Isopropylidenediphenol, 8ci	HMDB
4,4'-Propane-2,2-diyldiphenol	HMDB
4,4-Isopropylidenediphenol	HMDB
4,4[-Isopropylidenediphenol	HMDB
4-[1-(4-Hydroxyphenyl)-1-methylethyl]phenol	HMDB
beta, Beta'-bis(p-hydroxyphenyl)propane	HMDB
beta,Beta'-bis(p-hydroxyphenyl)propane	HMDB
beta,beta-Di-(p-hydroxyphenyl)propane	HMDB
beta-Di-(p-hydroxyphenyl)propane	HMDB
beta-Di-p-hydroxyphenylpropane	HMDB
Biphenol a	HMDB
Bis(4-hyd roxyphenyl) dimethylmethane	HMDB
Bis(4-hydroxyphenyl) dimethylmethane	HMDB
Bis(4-hydroxyphenyl) propane	HMDB
Bis(4-hydroxyphenyl)dimethylmethane	HMDB
Bis(4-hydroxyphenyl)propane	HMDB
Bis(p-hydroxyphenyl)propane	HMDB
Bisferol a	HMDB
Bisphenol	HMDB
Bisphenol a (bpa)	HMDB
Bisphenol a, disodium salt	HMDB
Bisphenol a, sodium salt	HMDB
Bisphenol a.	HMDB
Di-2,2-(4-hydroxyphenyl)propane	HMDB
Dian	HMDB
Diano	HMDB
Dimethyl bis(p-hydroxyphenyl)methane	HMDB
Dimethylbis(p-hydroxyphenyl)methane	HMDB
Dimethylmethylene-p,p'-diphenol	HMDB
Diphenylolpropane	HMDB
Hydrogenated bisphenol a	HMDB
Ipognox 88	HMDB
Isopropylidenebis(4-hydroxybenzene)	HMDB
Millad hbpa	HMDB
Noname	HMDB
p, P'-dihydroxydiphenyldimethylmethane	HMDB
p, P'-dihydroxydiphenylpropane	HMDB
p, P'-isopropylidenediphenol	HMDB
p,P'-bisphenol a	HMDB
p,P'-dihydroxydiphenyldimethylmethane	HMDB
p,P'-dihydroxydiphenylpropane	HMDB
p,P'-isopropylidenebisphenol	HMDB
p,P'-isopropylidenediphenol	HMDB
Parabis	HMDB
Parabis a	HMDB
Poly(bisphenol a carbonate)	HMDB
Rikabanol	HMDB
Ucar bisphenol a	HMDB
Ucar bisphenol HP	HMDB

Chemical Formula

C₁₅H₁₆O₂

Average Molecular Mass

228.286 g/mol

Monoisotopic Mass

228.115 g/mol

CAS Registry Number

1980-05-07

IUPAC Name

4-[2-(4-hydroxyphenyl)propan-2-yl]phenol

Traditional Name

bisphenol-A

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 Key

IISBACLAFKSPIT-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).

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Bisphenols

Alternative Parents

Substituents

Bisphenol
Phenylpropane
1-hydroxy-2-unsubstituted benzenoid
Phenol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

bisphenol (CHEBI:33216 )
Bisphenols (C13624 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

xenoestrogen

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Crystallizes as prisms from dil acetic acid and as needles from water (3).

Experimental Properties

Property	Value
Melting Point	156 - 157°C
Boiling Point	Not Available
Solubility	0.12 mg/mL at 25°C

Predicted Properties

Property	Value	Source
Water Solubility	0.086 g/L	ALOGPS
logP	3.81	ALOGPS
logP	4.04	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.78	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.28 m³·mol⁻¹	ChemAxon
Polarizability	25.41 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-2290000000-5a53b16778a578ff5d0d	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-2290000000-5a53b16778a578ff5d0d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03g0-1790000000-7521406d051aed77fe2f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0ab9-6289000000-59b1fac0d66836445629	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0zfs-4960000000-b4ebb7f1ff08fbb41adb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-004i-1090000000-80a2709d727e93053cd1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-004i-0090000000-c33246c7d9d8b300c90c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-004i-0090000000-e5f7d4cb43ef56a85056	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0532-9340000000-c3298310f84ad87b1310	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000t-9000000000-75784b9156574d6f1762	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4j-1900000000-1316f0a328865698ba14	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-000t-9000000000-75784b9156574d6f1762	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0zfs-4960000000-b4ebb7f1ff08fbb41adb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-004i-0090000000-c33246c7d9d8b300c90c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-004i-1090000000-80a2709d727e93053cd1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-004i-0090000000-e5f7d4cb43ef56a85056	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0532-9340000000-c3298310f84ad87b1310	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0a4j-1900000000-1316f0a328865698ba14	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0090000000-8791a2cf0310bf33a81e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0190000000-ee807d7dec5640d38d18	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01rb-2920000000-e15c6a1d966dd429fe3f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-0494eb6f9068e16e1d99	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0090000000-e9b5452c25e607f29950	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002f-9470000000-9d3d569c0a3f755f123f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002r-1960000000-42e45d340eea8ee9e3db	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-3900000000-8ef860db11d71a8b2f2e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-2900000000-61ebc2c60a263652b43e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-3090000000-27243d7aedeaef4a196c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0095-3940000000-3863b01420a8ec7c47d3	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03di-3590000000-0cd99fd08fc2fad698f3	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (7) ; inhalation (7) ; dermal (7)

Mechanism of Toxicity

Bisphenol is an endocrine disruptor. Low doses of bisphenol A can mimic the body's own hormones, possibly causing negative health effects. There is thus concern that long term low dose exposure to bisphenol A may induce chronic toxicity in humans (6).

Metabolism

Bisphenol A (BPA) is rapidly absorbed from the gastrointestinal tract after ingestionand is then converted to a number of metabolites, mainly BPA glucuronide, in the liver . Metabloites of Bsiphenol A (BPA) include isopropyl-hydroxyphenol (produced by the cleavage of BPA), a bisphenol A glutathione conjugate, glutathionyl-phenol, glutathionyl 4-isopropylphenol, and BPA dimers. The monoglucuronide conjugate was the major urinary metabolite; unchanged BPA is the principal component excreted in feces (1, 2).

Toxicity Values

LD50: 2230 mg/kg (Oral, Rabbit) (10)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Bisphenol A is used primarily to make plastics, and products containing bisphenol A-based plastics have been in commerce for more than 50 years. It is used in the synthesis of polyesters, polysulfones, and polyether ketones, as an antioxidant in some plasticizers, and as a polymerization inhibitor in PVC. It is a key monomer in production of polycarbonate plastic and epoxy resins. Polycarbonate plastic, which is clear and nearly shatter-proof, is used to make a variety of common products including baby and water bottles, sports equipment, medical and dental devices, dental fillings and sealants, eyeglass lenses, CDs and DVDs, and household electronics.[6] Epoxy resins containing bisphenol A are used as coatings on the inside of almost all food and beverage cans. Bisphenol A is also a precursor to the flame retardant, tetrabromobisphenol A, and was formerly used as a fungicide. (7)

Minimum Risk Level

Not Available

Health Effects

Permanent changes to genital tract, changes in breast tissue that predispose cells to hormones and carcinogens, increased prostate weight 30%, lower bodyweight, increase of anogenital distance in both genders, signs of early puberty and longer estrus, decline in testicular testosterone, breast cells predisposed to cancer, prostate cells more sensitive to hormones and cancer, decreased maternal behaviors, reversed the normal sex differences in brain structure and behavior, U.S. human exposure limit (not a result from an animal study, but a guideline set by EPA). (7)

Symptoms

Bisphenol A has low acute toxicity, with an oral LD50 of 3250 mg/kg in rats, but it is an endocrine disruptor. Low doses of bisphenol A can mimic the body's own hormones, possibly causing negative health effects. There is thus concern that long term low dose exposure to bisphenol A may induce chronic toxicity in humans. (7)

Treatment

Consider dilution immediately after ingestion. Insertion of a specialized nasogastric tube after confirmation of a circumferential burn may prevent strictures. In case of inhalation, move patient to fresh air and monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. In case of eye contact, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. Decontaminate skin or mucous membranes immediately with water and a soft sponge. (8)

Concentrations