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D3415

Sigma-Aldrich

Bisphenol A diglycidyl ether

viscous liquid, PPARγ inhibitor

Synonym(s):

BADGE, DGEBA, NSC 5022, 2,2-Bis[4-(glycidyloxy)phenyl]propane, 4,4′-Isopropylidenediphenol diglycidyl ether, D.E.R.™ 332

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About This Item

Empirical Formula (Hill Notation):
C21H24O4
CAS Number:
1675-54-3
Molecular Weight:
340.41
Beilstein/REAXYS Number:
299026
EC Number:
216-823-5
MDL number:
MFCD00080480
UNSPSC Code:
12352200
PubChem Substance ID:
57654090
NACRES:
NA.77

product name

Bisphenol A diglycidyl ether,

form

viscous liquid

composition

Epoxide equivalent weight, 172-176

density

1.16 g/mL at 25 °C (lit.)

SMILES string

CC(C)(c1ccc(OCC2CO2)cc1)c3ccc(OCC4CO4)cc3

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

InChI key

LCFVJGUPQDGYKZ-UHFFFAOYSA-N

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General description

Bisphenol A diglycidyl ether is an epoxy resin.

Application

Bisphenol A diglycidyl ether has been used:
  • to study its effects on propiomelanocortin (POMC):enhanced green fluorescent protein (EGFP) expression in our transgenic fish
  • to study the curing behavior, kinetics of epoxy, polyamidoamine systems and the influence of the incorporation of Fe3O4 magnetic nanoparticles (MNPs)
  • as a thermosetting resin
  • to determine the optimum composition of the epoxy-polysiloxane blend
  • for the preparation of transparent epoxy-based nanocomposite coatings
  • for the preparation, coating and curing of epoxy-graphene (E/G)

Biochem/physiol Actions

PPARγ inhibitor that blocks rosiglitazone- and insulin-induced adipogenesis.

Features and Benefits

This compound is featured on the Nuclear Receptors (PPARs) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Linkage

Epoxy resin often used in conjunction with DER 732 to form blocks of varying strength and hardness.

Legal Information

D.E.R. is a trademark of The Dow Chemical Company or an affiliated company of Dow

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

Hazard Classifications

Aquatic Chronic 2 - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1

Storage Class

10 - Combustible liquids

wgk_germany

WGK 2

flash_point_f

507.2 - 514.4 °F - closed cup

flash_point_c

264 - 268 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Enhanced protective properties and UV stability of epoxy/graphene nanocomposite coating on stainless steel.
Alhumade H, et al.
Express Polymer Letters, 10(12) (2016)
Transparent nanocomposite coatings based on epoxy and layered double hydroxide: nonisothermal cure kinetics and viscoelastic behavior assessments
Rastin H, et al.
Progress in Organic Coatings, 113, 126-135 (2017)
H M Wright et al.
The Journal of biological chemistry, 275(3), 1873-1877 (2000-01-15)
While searching for natural ligands for the peroxisome proliferator-activated receptor (PPAR) gamma, we identified a synthetic compound that binds to this receptor. Bisphenol A diglycidyl ether (BADGE) is a ligand for PPARgamma with a K(d(app)) of 100 microM. This compound
Hoa H Le et al.
Endocrinology, 151(12), 5689-5699 (2010-10-12)
Estrogenic endocrine disrupting chemicals (EDCs) constitute a diverse group of man-made chemicals and natural compounds derived from plants and microbial metabolism. Estrogen-like actions are mediated via the nuclear hormone receptor activity of estrogen receptor (ER)α and ERβ and rapid regulation
Design and Manufacture of Textile Composites (2005)
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