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
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
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| A synthetic antagonist for the peroxisome proliferator-activated receptor gamma inhibits adipocyte differentiation. | 2000 Jan 21 |
|
| Inhibition of phosphoenolpyruvate carboxykinase (PEPCK) gene expression by troglitazone: a peroxisome proliferator-activated receptor-gamma (PPARgamma)-independent, antioxidant-related mechanism. | 2001 Oct 15 |
|
| Time-temperature study of the kinetics of migration of BADGE (bisphenol-A-diglycidyl-ether) into a fatty medium. | 2002 |
|
| 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 |
|
| Estimates of per capita exposure to substances migrating from canned foods and beverages. | 2002 Sep |
|
| Regulation of retinoic acid receptor beta expression by peroxisome proliferator-activated receptor gamma ligands in cancer cells. | 2003 Jul 1 |
|
| Inhibition of interleukin-4 production in CD4+ T cells by peroxisome proliferator-activated receptor-gamma (PPAR-gamma) ligands: involvement of physical association between PPAR-gamma and the nuclear factor of activated T cells transcription factor. | 2003 Nov |
|
| Zinc modulates PPARgamma signaling and activation of porcine endothelial cells. | 2003 Oct |
|
| Capsaicin, a spicy component of hot pepper, induces apoptosis by activation of the peroxisome proliferator-activated receptor gamma in HT-29 human colon cancer cells. | 2004 Fall |
|
| 15-Deoxy-delta(12,14)-prostaglandin J2 inhibits the IL-1beta-induced expression of granulocyte-macrophage colony-stimulating factor in BEAS-2B bronchial epithelial cells. | 2004 Feb |
|
| Nitric oxide production and regulation of endothelial nitric-oxide synthase phosphorylation by prolonged treatment with troglitazone: evidence for involvement of peroxisome proliferator-activated receptor (PPAR) gamma-dependent and PPARgamma-independent signaling pathways. | 2004 Jan 23 |
|
| Effect of peroxisome proliferator-activated receptor-gamma ligands on the expression of retinoic acid-inducible gene-I in endothelial cells stimulated with lipopolysaccharide. | 2005 Dec |
|
| Effect of rosiglitazone and 15-deoxy-Delta12,14-prostaglandin J2 on bleomycin-induced lung injury. | 2005 Feb |
|
| Dietary exposure to chemical migrants from food contact materials: a probabilistic approach. | 2005 Oct |
|
| Determination of bisphenol diglycidyl ether residues in canned foods by pressurized liquid extraction and liquid chromatography-tandem mass spectrometry. | 2006 Feb 24 |
|
| 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 |
|
| Identification and estrogenic characterization of impurities in commercial bisphenol A diglycidyl ether (BADGE). | 2006 Oct |
|
| PPARgamma antagonists reverse the inhibition of neural antigen-specific Th1 response and experimental allergic encephalomyelitis by Ciglitazone and 15-deoxy-Delta12,14-prostaglandin J2. | 2006 Sep |
|
| 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 |
|
| Intrathecal rosiglitazone acts at peroxisome proliferator-activated receptor-gamma to rapidly inhibit neuropathic pain in rats. | 2008 Jul |
|
| Bisphenol A bis(2,3-dihydroxypropyl) ether (BADGE.2H2O) induces orphan nuclear receptor Nur77 gene expression and increases steroidogenesis in mouse testicular Leydig cells. | 2008 Jul 31 |
|
| 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 |
|
| 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 |
|
| Contamination of semi-solid dosage forms by leachables from aluminium tubes. | 2008 Nov |
|
| IgE-mediated occupational asthma from epoxy resin. | 2009 |
|
| Bone-marrow adipocytes as negative regulators of the haematopoietic microenvironment. | 2009 Jul 9 |
|
| Analysis of reaction products of food contaminants and ingredients: bisphenol A diglycidyl ether (BADGE) in canned foods. | 2010 Apr 28 |
|
| 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 |
|
| PPARgamma agonists inhibit angiogenesis by suppressing PKCalpha- and CREB-mediated COX-2 expression in the human endothelium. | 2010 May 1 |
Patents
| Name | Type | Language | ||
|---|---|---|---|---|
|
Systematic Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
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 | ||
|---|---|---|---|---|---|
|
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] | ||
|
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 | ||
|
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 | |||
|
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 | |||
|
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] | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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] | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
ACTIVE MOIETY
