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Details

Stereochemistry ACHIRAL
Molecular Formula C15H14O2.2Na
Molecular Weight 272.25
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DISODIUM BISPHENOL A

SMILES

[Na+].[Na+].CC(C)(C1=CC=C([O-])C=C1)C2=CC=C([O-])C=C2

InChI

InChIKey=WGMBWDBRVAKMOO-UHFFFAOYSA-L
InChI=1S/C15H16O2.2Na/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;;/q;2*+1/p-2

HIDE SMILES / InChI
Molecular Formula C15H14O2
Molecular Weight 226.2705
Charge -2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula Na
Molecular Weight 22.98976928
Charge 1
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
Growth stimulation of a rat pituitary cell line MtT/E-2 by environmental estrogens in vitro and in vivo.
1999 Aug
Exposure to bisphenol A advances puberty.
1999 Oct 21
High concentrations of bisphenol A induce cell growth and prolactin secretion in an estrogen-responsive pituitary tumor cell line.
2000 Feb 1
Molecular analysis of the inhibition of monocyte chemoattractant protein-1 gene expression by estrogens and xenoestrogens in MCF-7 cells.
2000 Jan
Sulfation of environmental estrogen-like chemicals by human cytosolic sulfotransferases.
2000 Jan 7
Endocrine disrupting chemicals, phthalic acid and nonylphenol, activate Pregnane X receptor-mediated transcription.
2000 Mar
Strain differences in vaginal responses to the xenoestrogen bisphenol A.
2000 Mar
Potential estrogenic effects of bisphenol-A estimated by in vitro and in vivo combination assays.
2001 Aug
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
Differential activation of wild-type and variant forms of estrogen receptor alpha by synthetic and natural estrogenic compounds using a promoter containing three estrogen-responsive elements.
2001 Jul
Thermostable (SULT1A1) and thermolabile (SULT1A3) phenol sulfotransferases in human osteosarcoma and osteoblast cells.
2001 Jun
Metabolism of bisphenol A in isolated rat hepatocytes and oestrogenic activity of a hydroxylated metabolite in MCF-7 human breast cancer cells.
2001 Mar
Bisphenol-A differently affects estrogen receptors-alpha in estrous-cycling and lactating female rats.
2001 Sep 7
Mutagenicity of bisphenol A (4,4'-isopropylidenediphenol) in vitro: effects of nitrosylation.
2002
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
Choriogenin mRNA induction in male medaka, Oryzias latipes as a biomarker of endocrine disruption.
2002 Dec 3
Developmental increases in rat hepatic microsomal UDP-glucuronosyltransferase activities toward xenoestrogens and decreases during pregnancy.
2002 Feb
Effect of endocrine disrupters on immune responses in vitro.
2002 Mar 1
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
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
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 20:49:19 GMT 2025
Edited
by admin
on Mon Mar 31 20:49:19 GMT 2025
Record UNII
RW57K3X12M
Record Status Validated (UNII)
Record Version
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Name Type Language
BISPHENOL A DISODIUM SALT
HSDB  
Preferred Name English
DISODIUM BISPHENOL A
Systematic Name English
PHENOL, 4,4'-(1-METHYLETHYLIDENE)BIS-, SODIUM SALT (1:2)
Systematic Name English
BISPHENOL A DISODIUM SALT [HSDB]
Common Name English
DIPHENYLOLPROPANE DISODIUM SALT
Common Name English
BISPHENOL A SODIUM SALT
Common Name English
BISPHENOL A DISODIUM
Systematic Name English
4,4'-(1-METHYLETHYLIDENE) BISPHENOL DISODIUM SALT
Common Name English
Code System Code Type Description
HSDB
5660
Created by admin on Mon Mar 31 20:49:19 GMT 2025 , Edited by admin on Mon Mar 31 20:49:19 GMT 2025
PRIMARY
CAS
2444-90-8
Created by admin on Mon Mar 31 20:49:19 GMT 2025 , Edited by admin on Mon Mar 31 20:49:19 GMT 2025
PRIMARY
ECHA (EC/EINECS)
219-488-3
Created by admin on Mon Mar 31 20:49:19 GMT 2025 , Edited by admin on Mon Mar 31 20:49:19 GMT 2025
PRIMARY
EPA CompTox
DTXSID0027480
Created by admin on Mon Mar 31 20:49:19 GMT 2025 , Edited by admin on Mon Mar 31 20:49:19 GMT 2025
PRIMARY
PUBCHEM
17127
Created by admin on Mon Mar 31 20:49:19 GMT 2025 , Edited by admin on Mon Mar 31 20:49:19 GMT 2025
PRIMARY
FDA UNII
RW57K3X12M
Created by admin on Mon Mar 31 20:49:19 GMT 2025 , Edited by admin on Mon Mar 31 20:49:19 GMT 2025
PRIMARY
Related Record Type Details
Structure of BISPHENOL A
PARENT -> SALT/SOLVATE
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