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Details

Stereochemistry ACHIRAL
Molecular Formula C15H16O2
Molecular Weight 228.2863
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BISPHENOL A

SMILES

CC(C)(C1=CC=C(O)C=C1)C2=CC=C(O)C=C2

InChI

InChIKey=IISBACLAFKSPIT-UHFFFAOYSA-N
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

HIDE SMILES / InChI
Molecular Formula C15H16O2
Molecular Weight 228.2863
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Bisphenol A is a small estrogenic monomer that is polymerized to produce polycarbonate plastic and resins used to line metal cans. It is also used to make some dental sealants. Bisphenol A had been considered to be a very weak environmental estrogen. It is able to interact with human estrogen receptors. In addition, it binds strongly to the estrogen-related receptor gamma. Bisphenol A inhibited androgen-induced androgen receptor transcriptional activity. Prenatal exposure to maternal Bisphenol A concentrations were related to higher levels of anxiety, depression, aggression, and hyperactivity in children. Bisphenol A exposure in childhood was associated with higher levels of anxiety, depression, hyperactivity, inattention, and conduct problems. It never found use as a drug.

CNS Activity

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
 5.5 nM [Kd]
Modulator
846
 11.7 µM [IC50]
Antagonist
2849
 80.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Male-specific suppression of hepatic microsomal UDP-glucuronosyl transferase activities toward sex hormones in the adult male rat administered bisphenol A.
2002-12-15
Choriogenin mRNA induction in male medaka, Oryzias latipes as a biomarker of endocrine disruption.
2002-12-03
Oxidative degradation of bisphenol a by crude enzyme prepared from potato.
2002-10-23
The nuclear pregnane X receptor: a key regulator of xenobiotic metabolism.
2002-10
Acute toxicity, mutagenicity, and estrogenicity of biodegradation products of bisphenol-A.
2002-10
Low doses of the endocrine disruptor bisphenol-A and the native hormone 17beta-estradiol rapidly activate transcription factor CREB.
2002-10
Sulfation of bisphenol A abolished its estrogenicity based on proliferation and gene expression in human breast cancer MCF-7 cells.
2002-10
No androgenic/anti-androgenic effects of bisphenol-A in Hershberger assay using immature castrated rats.
2002-09-05
Development of a fish reporter gene system for the assessment of estrogenic compounds and sewage treatment plant effluents.
2002-09
The activity of bisphenol A depends on both the estrogen receptor subtype and the cell type.
2002-08
DNA microarray analysis of differentially expressed genes responsive to bisphenol A, an alkylphenol derivative, in an in vitro mouse Sertoli cell model.
2002-08
[Extraction of bisphenol-A from a cardiopulmonary bypass circuit].
2002-08
Effects on extrahepatic UDP-glucuronosyltransferases in hypophysectomized rat.
2002-08
Phenylphenols, biphenols, bisphenol-A and 4-tert-octylphenol exhibit alpha and beta estrogen activities and antiandrogen activity in reporter cell lines.
2002-07-31
Determination of bisphenol-type contaminants from food packaging materials in aqueous foods by solid-phase microextraction-high-performance liquid chromatography.
2002-07-19
Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids.
2002-07
Gene expression profile induced by 17alpha-ethynyl estradiol, bisphenol A, and genistein in the developing female reproductive system of the rat.
2002-07
Stimulation of calbindin-D(9k) mRNA expression in the rat uterus by octyl-phenol, nonylphenol and bisphenol.
2002-06-14
Early cerebral activities of the environmental estrogen bisphenol A appear to act via the somatostatin receptor subtype sst(2).
2002-06
Endocrine disrupter bisphenol a induces orphan nuclear receptor Nur77 gene expression and steroidogenesis in mouse testicular Leydig cells.
2002-06
Validation of HPLC and GC-MS systems for bisphenol-A leached from hemodialyzers on the basis of FUMI theory.
2002-05-15
Effect of an endocrine disruptor on mammalian fertility. Application of monoclonal antibodies against sperm proteins as markers for testing sperm damage.
2002-05
Estrogen receptor binding assay of chemicals with a surface plasmon resonance biosensor.
2002-05
Low dose effect of in utero exposure to bisphenol A and diethylstilbestrol on female mouse reproduction.
2002-04-17
Developmental effects of perinatal exposure to bisphenol-A and diethylstilbestrol on reproductive organs in female mice.
2002-04-17
Detecting endocrine-disrupting compounds by fast impedance measurements.
2002-04-01
Fish test for endocrine-disruption and estimation of water quality of Japanese rivers.
2002-04
Bisphenol A affects endocrine physiology and biotransformation enzyme activities of the field vole (Microtus agrestis).
2002-04
Dietary bisphenol A prevents ovarian degeneration and bone loss in female mice lacking the aromatase gene (Cyp19 ).
2002-04
Endocrine disruptors and dental materials: health implications associated with their use in Brazil.
2002-03-30
Bisphenol A induces apoptosis and G2-to-M arrest of ovarian granulosa cells.
2002-03-29
Effect of endocrine disrupters on immune responses in vitro.
2002-03-01
Metabolism of 2-hydroxy-4-methoxybenzophenone in isolated rat hepatocytes and xenoestrogenic effects of its metabolites on MCF-7 human breast cancer cells.
2002-02-20
Investigation of the stability of a mixture of single-based propellants and resins or polymers.
2002-02-14
Acute toxicity, mutagenicity, and estrogenicity of bisphenol-A and other bisphenols.
2002-02
Developmental increases in rat hepatic microsomal UDP-glucuronosyltransferase activities toward xenoestrogens and decreases during pregnancy.
2002-02
Interaction of estrogen mimics, singly and in combination, with plasma sex steroid-binding proteins in rainbow trout (Oncorhynchus mykiss).
2002-02
Comparison of reporter gene assay and immature rat uterotrophic assay of twenty-three chemicals.
2002-01-15
Degradation of bisphenol-A (BPA) in the presence of reactive oxygen species and its acceleration by lipids and sodium chloride.
2002-01
Mutagenicity of bisphenol A (4,4'-isopropylidenediphenol) in vitro: effects of nitrosylation.
2002
Water sorption and solubility of dental composites and identification of monomers released in an aqueous environment.
2001-12
Sulfonic acid functionalized mesoporous MCM-41 silica as a convenient catalyst for Bisphenol-A synthesis.
2001-11-07
Modulation by estrogens and xenoestrogens of recombinant human neuronal nicotinic receptors.
2001-11-02
Morphological effects of Bisphenol-A on the early life stages of medaka (Oryzias latipes).
2001-11
Decomposition of bisphenol-A (BPA) by radical oxygen.
2001-10
Bisphenol A enhances cadmium toxicity through estrogen receptor.
2001-09
Effects of bisphenol A and its derivatives on the response of GABA(A) receptors expressed in Xenopus oocytes.
2001-09
In utero exposure to low doses of bisphenol A lead to long-term deleterious effects in the vagina.
2001-08-16
Levels of persistent organic pollutants in several child day care centers.
2001-08-13
Estrogen-like properties of brominated analogs of bisphenol A in the MCF-7 human breast cancer cell line.
2001
Patents

Patents

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JP2000273276A
2
JP2000281747A
2
JP2000290617A
3
JP2000297137A
4
JP2000303362A
2
JP2000319619A
3
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JP2001011197A
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JP2001011366A
2

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
In mouse pancreatic cells, phosphorylation of the transcription factor cAMP response element-binding protein associated with rapid induction of calcium influx was reported at a bisphenol A (BPA) dose of 1 nm, which was equal in magnitude to the response caused by the same dose of estradiol. In addition, rapid (within 1.5 min) influx of calcium was observed in human MCF-7 breast cancer cells in response to estradiol and BPA that was significant at the lowest dose tested, which was 0.1 nm BPA; for estradiol, the EC50 was 0.11 nm, and for BPA the EC50 was 0.15 nm.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:50:24 GMT 2025
Edited
by admin
on Mon Mar 31 18:50:24 GMT 2025
Record UNII
MLT3645I99
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
4,4'-ISOPROPYLIDENEDIPHENOL
INCI  
INCI  
Preferred Name English
BISPHENOL A
HSDB   MI  
Systematic Name English
NSC-1767
Code English
BISPHENOL A [HSDB]
Common Name English
BISPHENOL A [USP-RS]
Common Name English
4,4'-(1-METHYLETHYLIDENE)BISPHENOL
Systematic Name English
BISPHENOL A [MI]
Common Name English
2,2-BIS(4-HYDROXYPHENYL)PROPANE
Systematic Name English
Code System Code Type Description
RXCUI
1433347
Created by admin on Mon Mar 31 18:50:24 GMT 2025 , Edited by admin on Mon Mar 31 18:50:24 GMT 2025
PRIMARY RxNorm
MESH
C006780
Created by admin on Mon Mar 31 18:50:24 GMT 2025 , Edited by admin on Mon Mar 31 18:50:24 GMT 2025
PRIMARY
NSC
1767
Created by admin on Mon Mar 31 18:50:24 GMT 2025 , Edited by admin on Mon Mar 31 18:50:24 GMT 2025
PRIMARY
NCI_THESAURUS
C152071
Created by admin on Mon Mar 31 18:50:24 GMT 2025 , Edited by admin on Mon Mar 31 18:50:24 GMT 2025
PRIMARY
FDA UNII
MLT3645I99
Created by admin on Mon Mar 31 18:50:24 GMT 2025 , Edited by admin on Mon Mar 31 18:50:24 GMT 2025
PRIMARY
MERCK INDEX
m2568
Created by admin on Mon Mar 31 18:50:24 GMT 2025 , Edited by admin on Mon Mar 31 18:50:24 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID7020182
Created by admin on Mon Mar 31 18:50:24 GMT 2025 , Edited by admin on Mon Mar 31 18:50:24 GMT 2025
PRIMARY
RS_ITEM_NUM
1075892
Created by admin on Mon Mar 31 18:50:24 GMT 2025 , Edited by admin on Mon Mar 31 18:50:24 GMT 2025
PRIMARY
HSDB
513
Created by admin on Mon Mar 31 18:50:24 GMT 2025 , Edited by admin on Mon Mar 31 18:50:24 GMT 2025
PRIMARY
SMS_ID
100000159488
Created by admin on Mon Mar 31 18:50:24 GMT 2025 , Edited by admin on Mon Mar 31 18:50:24 GMT 2025
PRIMARY
CHEBI
33216
Created by admin on Mon Mar 31 18:50:24 GMT 2025 , Edited by admin on Mon Mar 31 18:50:24 GMT 2025
PRIMARY
EVMPD
SUB169668
Created by admin on Mon Mar 31 18:50:24 GMT 2025 , Edited by admin on Mon Mar 31 18:50:24 GMT 2025
PRIMARY
DAILYMED
MLT3645I99
Created by admin on Mon Mar 31 18:50:24 GMT 2025 , Edited by admin on Mon Mar 31 18:50:24 GMT 2025
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Mon Mar 31 18:50:24 GMT 2025 , Edited by admin on Mon Mar 31 18:50:24 GMT 2025
CONCEPT Industrial Aid
WIKIPEDIA
BISPHENOL A
Created by admin on Mon Mar 31 18:50:24 GMT 2025 , Edited by admin on Mon Mar 31 18:50:24 GMT 2025
PRIMARY
DRUG BANK
DB06973
Created by admin on Mon Mar 31 18:50:24 GMT 2025 , Edited by admin on Mon Mar 31 18:50:24 GMT 2025
PRIMARY
CAS
80-05-7
Created by admin on Mon Mar 31 18:50:24 GMT 2025 , Edited by admin on Mon Mar 31 18:50:24 GMT 2025
PRIMARY
PUBCHEM
6623
Created by admin on Mon Mar 31 18:50:24 GMT 2025 , Edited by admin on Mon Mar 31 18:50:24 GMT 2025
PRIMARY
ECHA (EC/EINECS)
201-245-8
Created by admin on Mon Mar 31 18:50:24 GMT 2025 , Edited by admin on Mon Mar 31 18:50:24 GMT 2025
PRIMARY
Related Record Type Details
Structure of DISODIUM BISPHENOL A
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of BISPHENOL A
ACTIVE MOIETY
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