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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

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
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 5.5 nM [Kd]
Modulator
828
 11.7 µM [IC50]
Antagonist
2778
 80.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Estrogenicity of bisphenol A in a human endometrial carcinoma cell line.
1999 Apr 25
Amphibians as a model to study endocrine disruptors: II. Estrogenic activity of environmental chemicals in vitro and in vivo.
1999 Jan 12
Low-dose bioactivity of xenoestrogens in animals: fetal exposure to low doses of methoxychlor and other xenoestrogens increases adult prostate size in mice.
1999 Jan-Mar
The role of estrogen receptor, androgen receptor and growth factors in diethylstilbestrol-induced programming of prostate differentiation.
2000 Aug
Differential effects of xenoestrogens on coactivator recruitment by estrogen receptor (ER) alpha and ERbeta.
2000 Nov 17
Down-regulation of murine Cyp1a-1 in mouse hepatoma Hepa-1c1c7 cells by bisphenol A.
2000 Nov 2
Relative binding affinity does not predict biological response to xenoestrogens in rat endometrial adenocarcinoma cells.
2000 Oct
Activation of a uterine insulin-like growth factor I signaling pathway by clinical and environmental estrogens: requirement of estrogen receptor-alpha.
2000 Sep
In vitro estrogenicity of polybrominated diphenyl ethers, hydroxylated PDBEs, and polybrominated bisphenol A compounds.
2001 Apr
The endocrine disrupters butyl benzyl phthalate and bisphenol A increase the expression of progesterone receptor messenger ribonucleic acid in the preoptic area of adult ovariectomized rats.
2001 Aug
Water sorption and solubility of dental composites and identification of monomers released in an aqueous environment.
2001 Dec
Cell-transforming activity and estrogenicity of bisphenol-A and 4 of its analogs in mammalian cells.
2001 Jul 1
Modulation by estrogens and xenoestrogens of recombinant human neuronal nicotinic receptors.
2001 Nov 2
Bisphenol-A, an environmental estrogen, activates the human orphan nuclear receptor, steroid and xenobiotic receptor-mediated transcription.
2001 Oct
Bisphenol A enhances cadmium toxicity through estrogen receptor.
2001 Sep
Bisphenol-A differently affects estrogen receptors-alpha in estrous-cycling and lactating female rats.
2001 Sep 7
Bisphenol A affects endocrine physiology and biotransformation enzyme activities of the field vole (Microtus agrestis).
2002 Apr
The activity of bisphenol A depends on both the estrogen receptor subtype and the cell type.
2002 Aug
[Extraction of bisphenol-A from a cardiopulmonary bypass circuit].
2002 Aug
Acute toxicity, mutagenicity, and estrogenicity of bisphenol-A and other bisphenols.
2002 Feb
Investigation of the stability of a mixture of single-based propellants and resins or polymers.
2002 Feb 14
Comparison of reporter gene assay and immature rat uterotrophic assay of twenty-three chemicals.
2002 Jan 15
Determination of bisphenol-type contaminants from food packaging materials in aqueous foods by solid-phase microextraction-high-performance liquid chromatography.
2002 Jul 19
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
Bisphenol A induces apoptosis and G2-to-M arrest of ovarian granulosa cells.
2002 Mar 29
In utero exposure to low doses of bisphenol A lead to long-term deleterious effects in the vagina.
2002 Mar-Apr
Validation of HPLC and GC-MS systems for bisphenol-A leached from hemodialyzers on the basis of FUMI theory.
2002 May 15
Low doses of the endocrine disruptor bisphenol-A and the native hormone 17beta-estradiol rapidly activate transcription factor CREB.
2002 Oct
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.
Name Type Language
BISPHENOL A
HSDB   MI  
Systematic Name English
NSC-1767
Code English
4,4'-ISOPROPYLIDENEDIPHENOL
INCI  
INCI  
Official Name English
BISPHENOL A [HSDB]
Common Name English
4,4'-ISOPROPYLIDENEDIPHENOL [INCI]
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 Fri Dec 15 17:41:10 GMT 2023 , Edited by admin on Fri Dec 15 17:41:10 GMT 2023
PRIMARY RxNorm
MESH
C006780
Created by admin on Fri Dec 15 17:41:10 GMT 2023 , Edited by admin on Fri Dec 15 17:41:10 GMT 2023
PRIMARY
NSC
1767
Created by admin on Fri Dec 15 17:41:10 GMT 2023 , Edited by admin on Fri Dec 15 17:41:10 GMT 2023
PRIMARY
NCI_THESAURUS
C152071
Created by admin on Fri Dec 15 17:41:10 GMT 2023 , Edited by admin on Fri Dec 15 17:41:10 GMT 2023
PRIMARY
FDA UNII
MLT3645I99
Created by admin on Fri Dec 15 17:41:10 GMT 2023 , Edited by admin on Fri Dec 15 17:41:10 GMT 2023
PRIMARY
MERCK INDEX
m2568
Created by admin on Fri Dec 15 17:41:10 GMT 2023 , Edited by admin on Fri Dec 15 17:41:10 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID7020182
Created by admin on Fri Dec 15 17:41:10 GMT 2023 , Edited by admin on Fri Dec 15 17:41:10 GMT 2023
PRIMARY
RS_ITEM_NUM
1075892
Created by admin on Fri Dec 15 17:41:10 GMT 2023 , Edited by admin on Fri Dec 15 17:41:10 GMT 2023
PRIMARY
HSDB
513
Created by admin on Fri Dec 15 17:41:10 GMT 2023 , Edited by admin on Fri Dec 15 17:41:10 GMT 2023
PRIMARY
SMS_ID
100000159488
Created by admin on Fri Dec 15 17:41:10 GMT 2023 , Edited by admin on Fri Dec 15 17:41:10 GMT 2023
PRIMARY
CHEBI
33216
Created by admin on Fri Dec 15 17:41:10 GMT 2023 , Edited by admin on Fri Dec 15 17:41:10 GMT 2023
PRIMARY
EVMPD
SUB169668
Created by admin on Fri Dec 15 17:41:10 GMT 2023 , Edited by admin on Fri Dec 15 17:41:10 GMT 2023
PRIMARY
DAILYMED
MLT3645I99
Created by admin on Fri Dec 15 17:41:10 GMT 2023 , Edited by admin on Fri Dec 15 17:41:10 GMT 2023
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Dec 15 17:41:10 GMT 2023 , Edited by admin on Fri Dec 15 17:41:10 GMT 2023
CONCEPT Industrial Aid
WIKIPEDIA
BISPHENOL A
Created by admin on Fri Dec 15 17:41:10 GMT 2023 , Edited by admin on Fri Dec 15 17:41:10 GMT 2023
PRIMARY
DRUG BANK
DB06973
Created by admin on Fri Dec 15 17:41:10 GMT 2023 , Edited by admin on Fri Dec 15 17:41:10 GMT 2023
PRIMARY
CAS
80-05-7
Created by admin on Fri Dec 15 17:41:10 GMT 2023 , Edited by admin on Fri Dec 15 17:41:10 GMT 2023
PRIMARY
PUBCHEM
6623
Created by admin on Fri Dec 15 17:41:10 GMT 2023 , Edited by admin on Fri Dec 15 17:41:10 GMT 2023
PRIMARY
ECHA (EC/EINECS)
201-245-8
Created by admin on Fri Dec 15 17:41:10 GMT 2023 , Edited by admin on Fri Dec 15 17:41:10 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of BISPHENOL A
SALT/SOLVATE (PARENT)
Structure of DISODIUM BISPHENOL A
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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