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Details

Stereochemistry MIXED
Molecular Formula C21H24O4
Molecular Weight 340.4129
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BISPHENOL A DIGLYCIDYL ETHER

SMILES

CC(C)(C1=CC=C(OCC2CO2)C=C1)C3=CC=C(OCC4CO4)C=C3

InChI

InChIKey=LCFVJGUPQDGYKZ-UHFFFAOYSA-N
InChI=1S/C21H24O4/c1-21(2,15-3-7-17(8-4-15)22-11-19-13-24-19)16-5-9-18(10-6-16)23-12-20-14-25-20/h3-10,19-20H,11-14H2,1-2H3

HIDE SMILES / InChI
Molecular Formula C21H24O4
Molecular Weight 340.4129
Charge 0
Count
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Bisphenol A diglycidyl ether (BADGE) is a ligand for peroxisome proliferator-activated receptor gamma (PPARgamma); in addition, this compound can antagonize the ability of agonist ligands such as rosiglitazone to activate the transcriptional and adipogenic action of this receptor. The elevation of BADGE concentration in epoxy resins-coated aluminium tubes poses a risk of developing contact dermatitis to patients sensitized to epoxy resins.

Approval Year

1994
149
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
 100.0 µM [IC50]
PubMed

PubMed

TitleDatePubMed
A synthetic antagonist for the peroxisome proliferator-activated receptor gamma inhibits adipocyte differentiation.
2000 Jan 21
Peroxisome proliferator-activated receptor gamma ligands suppress the transcriptional activation of cyclooxygenase-2. Evidence for involvement of activator protein-1 and CREB-binding protein/p300.
2001 Apr 13
Contact allergy to epoxy resin based on diglycidyl ether of bisphenol F.
2001 Feb
Preliminary assessment of the skin sensitizing activity of selected rodent carcinogens using the local lymph node assay.
2001 May 28
Inhibition of RXR and PPARgamma ameliorates diet-induced obesity and type 2 diabetes.
2001 Oct
Bisphenol a diglycidyl ether (BADGE) suppresses tumor necrosis factor-alpha production as a PPARgamma agonist in the murine macrophage-like cell line, RAW 264.7.
2002
Determination of bisphenol-type contaminants from food packaging materials in aqueous foods by solid-phase microextraction-high-performance liquid chromatography.
2002 Jul 19
Bisphenol A diglycidyl ether induces apoptosis in tumour cells independently of peroxisome proliferator-activated receptor-gamma, in caspase-dependent and -independent manners.
2002 Mar 15
Regulation of uncoupling protein-2 mRNA in L6 myotubules: I: Thiazolidinediones stimulate uncoupling protein-2 gene expression by a mechanism requiring ongoing protein synthesis and an active mitogen-activated protein kinase.
2002 Nov
The role of mitogen-activated protein kinases and their relationship with NF-kappaB and PPARgamma in indomethacin-Induced apoptosis of colon cancer cells.
2002 Nov
Regulation of retinoic acid receptor beta expression by peroxisome proliferator-activated receptor gamma ligands in cancer cells.
2003 Jul 1
Zinc modulates PPARgamma signaling and activation of porcine endothelial cells.
2003 Oct
The induction of gene mutations and micronuclei by oxiranes and siloranes in mammalian cells in vitro.
2004 Jan
Study on anti-androgenic effects of bisphenol a diglycidyl ether (BADGE), bisphenol F diglycidyl ether (BFDGE) and their derivatives using cells stably transfected with human androgen receptor, AR-EcoScreen.
2004 Jun
Effect of rosiglitazone and 15-deoxy-Delta12,14-prostaglandin J2 on bleomycin-induced lung injury.
2005 Feb
Simultaneous determination of bisphenol-A-diglycidyl ether, bisphenol-F-diglycidyl ether, and their derivatives in oil-in-water and aqueous-based canned foods by high-performance liquid chromatography with fluorescence detection.
2005 May 6
Inhibitors of fatty acid amide hydrolase reduce carrageenan-induced hind paw inflammation in pentobarbital-treated mice: comparison with indomethacin and possible involvement of cannabinoid receptors.
2005 Oct
Angiotensin II induces peroxisome proliferator-activated receptor gamma in PC12W cells via angiotensin type 2 receptor activation.
2005 Sep
Differential anti-proliferative actions of peroxisome proliferator-activated receptor-gamma agonists in MCF-7 breast cancer cells.
2006 Aug 28
Inhibition of PPARgamma prevents type I diabetic bone marrow adiposity but not bone loss.
2006 Dec
Neuroprotective effects of stearic acid against toxicity of oxygen/glucose deprivation or glutamate on rat cortical or hippocampal slices.
2006 Feb
Determination of bisphenol diglycidyl ethers in topical dosage forms.
2006 Feb 13
Peroxisome proliferator-activated receptor-gamma and retinoic acid X receptor alpha represses the TGFbeta1 gene via PTEN-mediated p70 ribosomal S6 kinase-1 inhibition: role for Zf9 dephosphorylation.
2006 Jul
Neuroprotective effects of arachidonic acid against oxidative stress on rat hippocampal slices.
2006 Nov 7
Study on mutagenic effects of bisphenol A diglycidyl ether (BADGE) and its derivatives in the Escherichia coli tryptophan reverse mutation assay.
2006 Oct 10
Single laboratory validation of a method for the determination of Bisphenol A, Bisphenol A diglycidyl ether and its derivatives in canned foods by reversed-phase liquid chromatography.
2006 Sep 29
PPARgamma inhibitors reduce tubulin protein levels by a PPARgamma, PPARdelta and proteasome-independent mechanism, resulting in cell cycle arrest, apoptosis and reduced metastasis of colorectal carcinoma cells.
2007 Feb 1
PPARgamma Inhibitors as Novel Tubulin-Targeting Agents.
2008
Agonists at PPAR-gamma suppress angiotensin II-induced production of plasminogen activator inhibitor-1 and extracellular matrix in rat cardiac fibroblasts.
2008 Apr
Intrathecal rosiglitazone acts at peroxisome proliferator-activated receptor-gamma to rapidly inhibit neuropathic pain in rats.
2008 Jul
Pioglitazone and dexamethasone induce adipogenesis in D1 bone marrow stromal cell line, but not through the peroxisome proliferator-activated receptor-gamma pathway.
2008 Mar 12
Concentrations of bisphenol a, bisphenol a diglycidyl ether, and their derivatives in canned foods in Japanese markets.
2008 Mar 26
JNK- and IkappaB-dependent pathways regulate MCP-1 but not adiponectin release from artificially hypertrophied 3T3-L1 adipocytes preloaded with palmitate in vitro.
2008 May
Analysis of reaction products of food contaminants and ingredients: bisphenol A diglycidyl ether (BADGE) in canned foods.
2010 Apr 28
Activation of peroxisome proliferator-activated receptor gamma in brain inhibits inflammatory pain, dorsal horn expression of Fos, and local edema.
2010 Feb
Suppression effects of AICAR on insulin secretion involved in peroxisome proliferator-activated receptor gamma changes in INS-1 cells.
2010 Jul-Aug
Involvement of PPAR-gamma in curcumin-mediated beneficial effects in experimental dementia.
2010 Jun
Acute testis toxicity of bisphenol A diglycidyl ether in Sprague-Dawley rats.
2010 Mar
Field-amplified sample injection-micellar electrokinetic capillary chromatography for the analysis of bisphenol A, bisphenol F, and their diglycidyl ethers and derivatives in canned soft drinks.
2010 May
Patents

Patents

JP2007537331A
2
JP2008545024A
4
JPS5871917A
1
Substance Class Chemical
Created
by admin
on Sat Dec 16 00:25:27 GMT 2023
Edited
by admin
on Sat Dec 16 00:25:27 GMT 2023
Record UNII
F3XRM1NX4H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BISPHENOL A DIGLYCIDYL ETHER
HSDB   MI  
Systematic Name English
NSC-5022
Code English
2,2'-(PROPANE-2,2-DIYLBIS(BENZENE-4,1-DIYLOXYMETHANEDIYL))DIOXIRANE
Systematic Name English
2,2'-(2,2-PROPANEDIYLBIS(4,1-PHENYLENEOXYMETHYLENE))DIOXIRANE
Systematic Name English
2,2-BIS(4-GLYCIDYLOXYPHENYL)PROPANE
Common Name English
4,4'-ISOPROPYLIDENEDIPHENOL DIGLYCIDYL ETHER
Systematic Name English
PROPANE, 2,2-BIS((P-2,3-EPOXYPROPOXY)PHENYL)-
Common Name English
BISPHENOL A DIGLYCIDYL ETHER [HSDB]
Common Name English
BADGE
Common Name English
BISPHENOL A DIGLYCIDYL ETHER [MI]
Common Name English
2,2'-(PROPANE-2,2-DIYLBIS(4,1-PHENYLENEOXYMETHYLENE))DIOXIRANE
Systematic Name English
DIGLYCIDYL BISPHENOL A ETHER
Common Name English
DGEBPA
Common Name English
DIGLYCIDYL ETHER OF 4,4'-ISOPROPYLIDENEDIPHENOL
Common Name English
2,2-BIS(4'-GLYCIDYLOXYPHENYL)PROPANE
Common Name English
BISPHENOL A DIGLYCIDYL ETHER [IARC]
Common Name English
2,2'-((1-METHYLETHYLIDENE)BIS(4,1-PHENYLENEOXYMETHYLENE))BISOXIRANE
Systematic Name English
BISPHENOL DIGLYCIDYL ETHER
Systematic Name English
DIGLYCIDYL ETHER OF 2,2-BIS(P-HYDROXYPHENYL)PROPANE
Common Name English
Classification Tree Code System Code
NDF-RT N0000185508
Created by admin on Sat Dec 16 00:25:27 GMT 2023 , Edited by admin on Sat Dec 16 00:25:27 GMT 2023
Code System Code Type Description
NDF-RT
N0000175629
Created by admin on Sat Dec 16 00:25:27 GMT 2023 , Edited by admin on Sat Dec 16 00:25:27 GMT 2023
PRIMARY Increased Histamine Release [PE]
MERCK INDEX
m2568
Created by admin on Sat Dec 16 00:25:27 GMT 2023 , Edited by admin on Sat Dec 16 00:25:27 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
216-823-5
Created by admin on Sat Dec 16 00:25:27 GMT 2023 , Edited by admin on Sat Dec 16 00:25:27 GMT 2023
PRIMARY
CAS
1675-54-3
Created by admin on Sat Dec 16 00:25:27 GMT 2023 , Edited by admin on Sat Dec 16 00:25:27 GMT 2023
PRIMARY
NDF-RT
N0000171131
Created by admin on Sat Dec 16 00:25:27 GMT 2023 , Edited by admin on Sat Dec 16 00:25:27 GMT 2023
PRIMARY Allergens [Chemical/Ingredient]
PUBCHEM
2286
Created by admin on Sat Dec 16 00:25:27 GMT 2023 , Edited by admin on Sat Dec 16 00:25:27 GMT 2023
PRIMARY
EPA CompTox
DTXSID6024624
Created by admin on Sat Dec 16 00:25:27 GMT 2023 , Edited by admin on Sat Dec 16 00:25:27 GMT 2023
PRIMARY
DRUG BANK
DB14083
Created by admin on Sat Dec 16 00:25:27 GMT 2023 , Edited by admin on Sat Dec 16 00:25:27 GMT 2023
PRIMARY
NDF-RT
N0000184306
Created by admin on Sat Dec 16 00:25:27 GMT 2023 , Edited by admin on Sat Dec 16 00:25:27 GMT 2023
PRIMARY Cell-mediated Immunity [PE]
EVMPD
SUB61066
Created by admin on Sat Dec 16 00:25:27 GMT 2023 , Edited by admin on Sat Dec 16 00:25:27 GMT 2023
PRIMARY
FDA UNII
F3XRM1NX4H
Created by admin on Sat Dec 16 00:25:27 GMT 2023 , Edited by admin on Sat Dec 16 00:25:27 GMT 2023
PRIMARY
WIKIPEDIA
BISPHENOL A DIGLYCIDYL ETHER
Created by admin on Sat Dec 16 00:25:27 GMT 2023 , Edited by admin on Sat Dec 16 00:25:27 GMT 2023
PRIMARY
SMS_ID
100000134284
Created by admin on Sat Dec 16 00:25:27 GMT 2023 , Edited by admin on Sat Dec 16 00:25:27 GMT 2023
PRIMARY
NSC
5022
Created by admin on Sat Dec 16 00:25:27 GMT 2023 , Edited by admin on Sat Dec 16 00:25:27 GMT 2023
PRIMARY
DAILYMED
F3XRM1NX4H
Created by admin on Sat Dec 16 00:25:27 GMT 2023 , Edited by admin on Sat Dec 16 00:25:27 GMT 2023
PRIMARY
RXCUI
1368138
Created by admin on Sat Dec 16 00:25:27 GMT 2023 , Edited by admin on Sat Dec 16 00:25:27 GMT 2023
PRIMARY
HSDB
331
Created by admin on Sat Dec 16 00:25:27 GMT 2023 , Edited by admin on Sat Dec 16 00:25:27 GMT 2023
PRIMARY
MESH
C019273
Created by admin on Sat Dec 16 00:25:27 GMT 2023 , Edited by admin on Sat Dec 16 00:25:27 GMT 2023
PRIMARY
Related Record Type Details
Structure of BISPHENOL A DIGLYCIDYL ETHER
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