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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
Estrogen-like properties of brominated analogs of bisphenol A in the MCF-7 human breast cancer cell line.
2001
Water sorption and solubility of dental composites and identification of monomers released in an aqueous environment.
2001 Dec
Morphological effects of Bisphenol-A on the early life stages of medaka (Oryzias latipes).
2001 Nov
Modulation by estrogens and xenoestrogens of recombinant human neuronal nicotinic receptors.
2001 Nov 2
Sulfonic acid functionalized mesoporous MCM-41 silica as a convenient catalyst for Bisphenol-A synthesis.
2001 Nov 7
Levels of persistent organic pollutants in several child day care centers.
2001 Nov-Dec
Decomposition of bisphenol-A (BPA) by radical oxygen.
2001 Oct
Bisphenol A enhances cadmium toxicity through estrogen receptor.
2001 Sep
Effects of bisphenol A and its derivatives on the response of GABA(A) receptors expressed in Xenopus oocytes.
2001 Sep
Mutagenicity of bisphenol A (4,4'-isopropylidenediphenol) in vitro: effects of nitrosylation.
2002
Fish test for endocrine-disruption and estimation of water quality of Japanese rivers.
2002 Apr
Bisphenol A affects endocrine physiology and biotransformation enzyme activities of the field vole (Microtus agrestis).
2002 Apr
Dietary bisphenol A prevents ovarian degeneration and bone loss in female mice lacking the aromatase gene (Cyp19 ).
2002 Apr
Detecting endocrine-disrupting compounds by fast impedance measurements.
2002 Apr 1
The activity of bisphenol A depends on both the estrogen receptor subtype and the cell type.
2002 Aug
DNA microarray analysis of differentially expressed genes responsive to bisphenol A, an alkylphenol derivative, in an in vitro mouse Sertoli cell model.
2002 Aug
[Extraction of bisphenol-A from a cardiopulmonary bypass circuit].
2002 Aug
Effects on extrahepatic UDP-glucuronosyltransferases in hypophysectomized rat.
2002 Aug
Male-specific suppression of hepatic microsomal UDP-glucuronosyl transferase activities toward sex hormones in the adult male rat administered bisphenol A.
2002 Dec 15
Choriogenin mRNA induction in male medaka, Oryzias latipes as a biomarker of endocrine disruption.
2002 Dec 3
Acute toxicity, mutagenicity, and estrogenicity of bisphenol-A and other bisphenols.
2002 Feb
Developmental increases in rat hepatic microsomal UDP-glucuronosyltransferase activities toward xenoestrogens and decreases during pregnancy.
2002 Feb
Interaction of estrogen mimics, singly and in combination, with plasma sex steroid-binding proteins in rainbow trout (Oncorhynchus mykiss).
2002 Feb
Investigation of the stability of a mixture of single-based propellants and resins or polymers.
2002 Feb 14
Metabolism of 2-hydroxy-4-methoxybenzophenone in isolated rat hepatocytes and xenoestrogenic effects of its metabolites on MCF-7 human breast cancer cells.
2002 Feb 20
Degradation of bisphenol-A (BPA) in the presence of reactive oxygen species and its acceleration by lipids and sodium chloride.
2002 Jan
Comparison of reporter gene assay and immature rat uterotrophic assay of twenty-three chemicals.
2002 Jan 15
Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids.
2002 Jul
Gene expression profile induced by 17alpha-ethynyl estradiol, bisphenol A, and genistein in the developing female reproductive system of the rat.
2002 Jul
Determination of bisphenol-type contaminants from food packaging materials in aqueous foods by solid-phase microextraction-high-performance liquid chromatography.
2002 Jul 19
Phenylphenols, biphenols, bisphenol-A and 4-tert-octylphenol exhibit alpha and beta estrogen activities and antiandrogen activity in reporter cell lines.
2002 Jul 31
Early cerebral activities of the environmental estrogen bisphenol A appear to act via the somatostatin receptor subtype sst(2).
2002 Jun
Endocrine disrupter bisphenol a induces orphan nuclear receptor Nur77 gene expression and steroidogenesis in mouse testicular Leydig cells.
2002 Jun
Stimulation of calbindin-D(9k) mRNA expression in the rat uterus by octyl-phenol, nonylphenol and bisphenol.
2002 Jun 14
Effect of endocrine disrupters on immune responses in vitro.
2002 Mar 1
Bisphenol A induces apoptosis and G2-to-M arrest of ovarian granulosa cells.
2002 Mar 29
Low dose effect of in utero exposure to bisphenol A and diethylstilbestrol on female mouse reproduction.
2002 Mar-Apr
Developmental effects of perinatal exposure to bisphenol-A and diethylstilbestrol on reproductive organs in female mice.
2002 Mar-Apr
Endocrine disruptors and dental materials: health implications associated with their use in Brazil.
2002 Mar-Apr
In utero exposure to low doses of bisphenol A lead to long-term deleterious effects in the vagina.
2002 Mar-Apr
Effect of an endocrine disruptor on mammalian fertility. Application of monoclonal antibodies against sperm proteins as markers for testing sperm damage.
2002 May
Estrogen receptor binding assay of chemicals with a surface plasmon resonance biosensor.
2002 May
Validation of HPLC and GC-MS systems for bisphenol-A leached from hemodialyzers on the basis of FUMI theory.
2002 May 15
The nuclear pregnane X receptor: a key regulator of xenobiotic metabolism.
2002 Oct
Acute toxicity, mutagenicity, and estrogenicity of biodegradation products of bisphenol-A.
2002 Oct
Low doses of the endocrine disruptor bisphenol-A and the native hormone 17beta-estradiol rapidly activate transcription factor CREB.
2002 Oct
Sulfation of bisphenol A abolished its estrogenicity based on proliferation and gene expression in human breast cancer MCF-7 cells.
2002 Oct
Oxidative degradation of bisphenol a by crude enzyme prepared from potato.
2002 Oct 23
Development of a fish reporter gene system for the assessment of estrogenic compounds and sewage treatment plant effluents.
2002 Sep
No androgenic/anti-androgenic effects of bisphenol-A in Hershberger assay using immature castrated rats.
2002 Sep 5
Patents

Patents

JP1014267A
2
JP1024713A
2
JP1026690A
2
JP1033120A
2
JP1033122A
2
JP1036622A
2
JP1040523A
2
JP1043557A
2
JP1043558A
2
JP1051429A
5
JP1054024A
2
JP1065117A
2
JP1065138A
2
JP1069611A
2
JP1071732A
3
JP1074283A
2
JP1079253A
2
JP2000017051A
2
JP2000034406A
2
JP2000038524A
2
JP2000044654A
2
JP2000053744A
2
JP2000095923A
2
JP2000103964A
2
JP2000104012A
3
JP2000109672A
2
JP2000128817A
2
JP2000128977A
2
JP2000144071A
2
JP2000169571A
2
JP2000186171A
2
JP2000204342A
2
JP2000219733A
2
JP2000239622A
2
JP2000248047A
2
JP2000256440A
2
JP2000264950A
2
JP2000265042A
3
JP2000273206A
2
JP2000273276A
2
JP2000281747A
2
JP2000290617A
3
JP2000297137A
4
JP2000303362A
2
JP2000319619A
3
JP2000327614A
2
JP2000336250A
2
JP2000336333A
2
JP2001011159A
2
JP2001011197A
3
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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