bisphenol A diglycidyl ether

Synonyms: "2,2-bis(4-glycidyloxyphenyl)propane", "epoxide A", "epophen EL 5", "BADGE", "DGEBA", "dian diglycidyl ether", "diglycidyl bisphenol A"

Source: bisphenol A diglycidyl ether is a chemical compound used as constituent of epoxy resins.

Identifiers:

IUPAC Name: 2-[[4-[2-[4-(oxiran-2-ylmethoxy)phenyl]propan-2-yl]phenoxy]methyl]oxirane
CAS Number: 1675-54-3
PubChem ID: 2286
InChiKey: LCFVJGUPQDGYKZ-UHFFFAOYSA-N
Canonical SMILES: CC(C)(C1=CC=C(C=C1)OCC2CO2)C3=CC=C(C=C3)OCC4CO4

Structural Properties:

Molecular Formula: C₂₁H₂₄O₄
Molecular Weight: 340.413

Pharmacophore Features:

Number of bond donors: 0
Number of bond acceptors: 4
Number of atoms different from hydrogen: 25

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Evidence Supporting This Chemical as an Endocrine Disruptor
TEDX List of Potential Endocrine Disruptors

Bishop-Bailey D, Hla T, Warner TD. 2000. Bisphenol A diglycidyl ether (BADGE) is a PPAR gamma agonist in an ECV304 cell line. Br J Pharmacol 131(4):651-654.

Letcher RJ, Sanderson JT, Bokkers A, Giesy JP, Van Den Berg M. 2005. Effects of bisphenol A-related diphenylalkanes on vitellogenin production in male carp (Cyprinus carpio) hepatocytes and aromatase (CYP19) activity in human H295R adrenocortical carcinoma cells. Toxicol Appl Pharmacol 209(2):95-104.

Li H, Ruan XZ, Powis SH, Fernando R, Mon WY, Wheeler DC, Moorhead JF, Varghese Z. 2005. EPA and DHA reduce LPS-induced inflammation responses in HK-2 cells: evidence for a PPAR-gamma-dependent mechanism. Kidney Int 67(3):867-874.

Satoh K, Ohyama K, Aoki N, Iida M, Nagai F. 2004. 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. Food & Chemical Toxicology 42(6):983-993.

Wright HM, Clish CB, Mikami T, Hauser S, Yanagi K, Hiramatsu R, Serhan CN, Spiegelman BM. 2000. A synthetic antagonist for the peroxisome proliferator-activated receptor gamma inhibits adipocyte differentiation. J Biol Chem 275(3):1873-1877.