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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
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
Glucuronidation of the environmental oestrogen bisphenol A by an isoform of UDP-glucuronosyltransferase, UGT2B1, in the rat liver.
1999 Jun 1
Inhibition of drug-metabolizing enzyme activity in human hepatic cytochrome P450s by bisphenol A.
2000 Apr
[Competitive binding of some alkyl p-hydroxybenzoates to human estrogen receptor alpha and beta].
2000 Dec
Endocrine disrupting chemicals, phthalic acid and nonylphenol, activate Pregnane X receptor-mediated transcription.
2000 Mar
Differential estrogen receptor binding of estrogenic substances: a species comparison.
2000 Nov 15
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
In vitro and in vivo interactions of bisphenol A and its metabolite, bisphenol A glucuronide, with estrogen receptors alpha and beta.
2001 Feb
Mutagenicity of bisphenol A and its suppression by interferon-alpha in human RSa cells.
2001 Feb 20
Oestrogenic potencies of Zeranol, oestradiol, diethylstilboestrol, Bisphenol-A and genistein: implications for exposure assessment of potential endocrine disrupters.
2001 May
Modulation by estrogens and xenoestrogens of recombinant human neuronal nicotinic receptors.
2001 Nov 2
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
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
Low dose effect of in utero exposure to bisphenol A and diethylstilbestrol on female mouse reproduction.
2002 Mar-Apr
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 Fri Dec 15 17:41:10 GMT 2023
Edited
by admin
on Fri Dec 15 17:41:10 GMT 2023
Record UNII
MLT3645I99
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
Structure of DISODIUM BISPHENOL A
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of BISPHENOL A
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