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
| 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 |
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 |
|---|---|---|
| Involvement of PPAR-gamma in curcumin-mediated beneficial effects in experimental dementia. | 2010-06 |
|
| PPARgamma agonists inhibit angiogenesis by suppressing PKCalpha- and CREB-mediated COX-2 expression in the human endothelium. | 2010-05-01 |
|
| 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. | 2010-05 |
|
| Analysis of reaction products of food contaminants and ingredients: bisphenol A diglycidyl ether (BADGE) in canned foods. | 2010-04-28 |
|
| Computer-aided discovery, validation, and mechanistic characterization of novel neolignan activators of peroxisome proliferator-activated receptor gamma. | 2010-04 |
|
| Acute testis toxicity of bisphenol A diglycidyl ether in Sprague-Dawley rats. | 2010-03 |
|
| PPARgamma regulates LIF-induced growth and self-renewal of mouse ES cells through Tyk2-Stat3 pathway. | 2010-03 |
|
| Activation of peroxisome proliferator-activated receptor gamma in brain inhibits inflammatory pain, dorsal horn expression of Fos, and local edema. | 2010-02 |
|
| Suppression effects of AICAR on insulin secretion involved in peroxisome proliferator-activated receptor gamma changes in INS-1 cells. | 2010-01-27 |
|
| Comparison and prediction of the retention in micellar electrokinetic chromatography and microemulsion electrokinetic chromatography for disubstituted benzenes. | 2010-01 |
|
| Clinical evaluation of resin-based composites in posterior restorations: 12-month results. | 2010-01 |
|
| Reduced sensitizing capacity of epoxy resin systems: a structure-activity relationship study. | 2009-11 |
|
| Bone-marrow adipocytes as negative regulators of the haematopoietic microenvironment. | 2009-07-09 |
|
| Repressive effect of the phytoestrogen genistein on estradiol-induced uterine leiomyoma cell proliferation. | 2009-06 |
|
| Activation of peroxisome proliferator-activated receptor-gamma potentiates pro-inflammatory cytokine production, and adrenal and somatotropic changes of weaned pigs after Escherichia coli lipopolysaccharide challenge. | 2009-06 |
|
| Chemical and structural characterisation of DGEBA-based epoxies by time of flight secondary ion mass spectrometry (ToF-SIMS) as a preliminary to polymer interphase characterisation. | 2009-04 |
|
| Regulation of adipose triglyceride lipase by rosiglitazone. | 2009-02 |
|
| IgE-mediated occupational asthma from epoxy resin. | 2009 |
|
| Contamination of semi-solid dosage forms by leachables from aluminium tubes. | 2008-11 |
|
| Bisphenol A bis(2,3-dihydroxypropyl) ether (BADGE.2H2O) induces orphan nuclear receptor Nur77 gene expression and increases steroidogenesis in mouse testicular Leydig cells. | 2008-07-31 |
|
| Intrathecal rosiglitazone acts at peroxisome proliferator-activated receptor-gamma to rapidly inhibit neuropathic pain in rats. | 2008-07 |
|
| JNK- and IkappaB-dependent pathways regulate MCP-1 but not adiponectin release from artificially hypertrophied 3T3-L1 adipocytes preloaded with palmitate in vitro. | 2008-05 |
|
| Agonists at PPAR-gamma suppress angiotensin II-induced production of plasminogen activator inhibitor-1 and extracellular matrix in rat cardiac fibroblasts. | 2008-04 |
|
| Concentrations of bisphenol a, bisphenol a diglycidyl ether, and their derivatives in canned foods in Japanese markets. | 2008-03-26 |
|
| Pioglitazone and dexamethasone induce adipogenesis in D1 bone marrow stromal cell line, but not through the peroxisome proliferator-activated receptor-gamma pathway. | 2008-03-12 |
|
| 4-tert-octylphenol regulates the differentiation of C3H10T1/2 cells into osteoblast and adipocyte lineages. | 2008-03 |
|
| Oxidative stress in the thyroid gland: from harmlessness to hazard depending on the iodine content. | 2008-01 |
|
| PPARgamma Inhibitors as Novel Tubulin-Targeting Agents. | 2008 |
|
| Comparison of resolution in microemulsion EKC and MEKC employing suppressed electroosmosis: application to bisphenol-A-diglycidyl ether and its derivatives. | 2007-10 |
|
| Apoptotic action of peroxisome proliferator-activated receptor-gamma activation in human non small-cell lung cancer is mediated via proline oxidase-induced reactive oxygen species formation. | 2007-09 |
|
| Risk assessment of topically applied products. | 2007-07-01 |
|
| Developmental toxicity by exposure to bisphenol A diglycidyl ether during gestation and lactation period in Sprague-Dawley male rats. | 2007-03 |
|
| 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. | 2007-02-01 |
|
| Trans-10, cis-12-conjugated linoleic acid increases phagocytosis of porcine peripheral blood polymorphonuclear cells in vitro. | 2007-01 |
|
| Bisphenol A (BPA) and its source in foods in Japanese markets. | 2007-01 |
|
| Inhibition of PPARgamma prevents type I diabetic bone marrow adiposity but not bone loss. | 2006-12 |
|
| Neuroprotective effects of arachidonic acid against oxidative stress on rat hippocampal slices. | 2006-11-07 |
|
| Study on mutagenic effects of bisphenol A diglycidyl ether (BADGE) and its derivatives in the Escherichia coli tryptophan reverse mutation assay. | 2006-10-10 |
|
| Identification and estrogenic characterization of impurities in commercial bisphenol A diglycidyl ether (BADGE). | 2006-10 |
|
| 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. | 2006-09-29 |
|
| PPARgamma antagonists reverse the inhibition of neural antigen-specific Th1 response and experimental allergic encephalomyelitis by Ciglitazone and 15-deoxy-Delta12,14-prostaglandin J2. | 2006-09 |
|
| Differential anti-proliferative actions of peroxisome proliferator-activated receptor-gamma agonists in MCF-7 breast cancer cells. | 2006-08-28 |
|
| 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. | 2006-07 |
|
| Stability of silorane dental monomers in aqueous systems. | 2006-07 |
|
| Transcriptional regulation of nephrin gene by peroxisome proliferator-activated receptor-gamma agonist: molecular mechanism of the antiproteinuric effect of pioglitazone. | 2006-06 |
|
| Fish oil regulates adiponectin secretion by a peroxisome proliferator-activated receptor-gamma-dependent mechanism in mice. | 2006-04 |
|
| Determination of bisphenol diglycidyl ether residues in canned foods by pressurized liquid extraction and liquid chromatography-tandem mass spectrometry. | 2006-02-24 |
|
| Neuroprotective effects of stearic acid against toxicity of oxygen/glucose deprivation or glutamate on rat cortical or hippocampal slices. | 2006-02 |
|
| Effect of peroxisome proliferator-activated receptor-gamma ligands on the expression of retinoic acid-inducible gene-I in endothelial cells stimulated with lipopolysaccharide. | 2005-12 |
|
| Dietary exposure to chemical migrants from food contact materials: a probabilistic approach. | 2005-10 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 20:34:54 GMT 2025
by
admin
on
Mon Mar 31 20:34:54 GMT 2025
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| Record UNII |
F3XRM1NX4H
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| Record Status |
Validated (UNII)
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| Record Version |
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NDF-RT |
N0000185508
Created by
admin on Mon Mar 31 20:34:54 GMT 2025 , Edited by admin on Mon Mar 31 20:34:54 GMT 2025
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| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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N0000175629
Created by
admin on Mon Mar 31 20:34:54 GMT 2025 , Edited by admin on Mon Mar 31 20:34:54 GMT 2025
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PRIMARY | Increased Histamine Release [PE] | ||
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m2568
Created by
admin on Mon Mar 31 20:34:54 GMT 2025 , Edited by admin on Mon Mar 31 20:34:54 GMT 2025
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PRIMARY | Merck Index | ||
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216-823-5
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1675-54-3
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N0000171131
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admin on Mon Mar 31 20:34:54 GMT 2025 , Edited by admin on Mon Mar 31 20:34:54 GMT 2025
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PRIMARY | Allergens [Chemical/Ingredient] | ||
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2286
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DTXSID6024624
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DB14083
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N0000184306
Created by
admin on Mon Mar 31 20:34:54 GMT 2025 , Edited by admin on Mon Mar 31 20:34:54 GMT 2025
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PRIMARY | Cell-mediated Immunity [PE] | ||
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SUB61066
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F3XRM1NX4H
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BISPHENOL A DIGLYCIDYL ETHER
Created by
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100000134284
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5022
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F3XRM1NX4H
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1368138
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331
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C019273
Created by
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