1675-54-3

Basic information

• Product Name: BISPHENOL A DIGLYCIDYL ETHER RESIN
• Synonyms: BISPHENOL A DIGLYCIDYL ETHER RESIN;DER 332 RESIN;EPON(R) RESIN 828;2,2’-((1-methylethylidene)bis(4,1-phenyleneoxymethylene))bis-oxiran;2,2’-[(1-methylethylidene)bis(4,1-phenyleneoxymethylene)]bis-oxiran;2,2-bis(4-(2,3-epoxpropyloxy)phenyl)propane;2,2-bis(4-(2,3-epoxypropyloxy)phenyl)propane;2,2-bis(p-(2,3-epoxypropoxy)phenyl)-propan
• CAS NO: 1675-54-3
• Molecular Formula: C₂₁H₂₄O₄
• Molecular Weight: 340.41286
• EINECS: 216-823-5
• Product Categories: Aromatics Compounds;Bisphenol A type Compounds (for High-Performance Polymer Research);Functional Materials;Oxiranes;Reagent for High-Performance Polymer Research;Simple 3-Membered Ring Compounds;Aromatics;Inhibitors;Intracellular receptor
• Mol File: 1675-54-3.mol
• Article Data: 17

Chemical Properties

• Melting Point: 40-44 °C
• Boiling Point: 210 °C / 1mmHg
• Flash Point: 148.5 °C
• Appearance: /
• Density: 1,17 g/cm3
• Vapor Pressure: 3.66E-09mmHg at 25°C
• Refractive Index: 1.5735
• Storage Temp.: 2-8°C
• Solubility: Soluble in DMSO (up to 30 mg/ml) or in Ethanol (up to 15 mg/ml)
• Water Solubility: Soluble in 100% ethanol, dimethyl sulfoxide (100 mM), dimethyl formamide, chloroform, methanol, and ethanol (50 mM). Insoluble i
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
• BRN: 299026
• CAS DataBase Reference: BISPHENOL A DIGLYCIDYL ETHER RESIN(CAS DataBase Reference)
• NIST Chemistry Reference: BISPHENOL A DIGLYCIDYL ETHER RESIN(1675-54-3)
• EPA Substance Registry System: BISPHENOL A DIGLYCIDYL ETHER RESIN(1675-54-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38-43
• Safety Statements: 28-37/39
• WGK Germany: 1
• RTECS: TX3800000
• TSCA: Yes
• Hazardous Substances Data: 1675-54-3(Hazardous Substances Data)

Usage

Description

Different sources of media describe the Description of 1675-54-3 differently. You can refer to the following data:
1. Most epoxy resins result from polymerization of bisphenol A diglycidyl ether (BADGE). Delayed hypersensitivity is caused by the low-molecular-weight monomer BADGE (MW 340 g/mol), the dimer having a much lower sensitization power. This allergen caused contact dermatitis in six workers in a plant producing printed circuits boards made of copper sheets and fiberglass fabric impregnated with a brominated epoxy resin. It can also be contained in adhesives.
2. PPARγ is a ligand-activated transcription factor involved in the regulation of lipid homeostasis and may function as a master regulator of adipogenesis. Ligands for PPARγ include antidiabetic drugs of the thiazolidinedione structural class, 15-deoxy-Δ12,14-prostaglandin J2 , and NSAIDS. BADGE is a synthetic compound used in the production of polycarbonate and industrial plastics. This compound was recently identified as an antagonist of PPARγ. BADGE binds to PPARγ with an apparent Kd of 100 μM and interferes with the ability of 3T3-L1 and 3T3-F442A cells to undergo hormone-mediated cell differentiation.

Chemical Properties

Diglycidyl ether of bisphenol A is a colorless to light amber liquid. Slight epoxy odor.

Uses

Different sources of media describe the Uses of 1675-54-3 differently. You can refer to the following data:
1. Bisphenol A derivative. A PPARγ antagonist; exhibits estrogenic activity; An inhibitor of PPARγ and suppressor of TNFα.
2. In the manufacture of epoxy resins and polycarbonates for food packaging.
3. The uniqueness of D.E.R. 332 epoxy resin is reflected in its maximum epoxide equivalent weight of 178. Because of its high purity and lack of polymer factions, samples embedded using D.E.R. 322 have uniform performance, exceptionally low viscosity and color; and improved elevated temperature properties.

Production Methods

The synthesis of the basic epoxy resin molecule involves the reaction of epichlorohydrin with bisphenol A, the latter requiring two basic intermediates for synthesis, acetone and phenol. Theoretically, the production of the bisphenol A diglycidyl ether requires 2 mol of epichlorohydrin for each mole of the phenol. Epoxy resins of higher molecular weight are obtained by reducing the epichlorohydrin/bisphenol A ratio. This reaction involves consumption of the initial epoxy groups in the epichlorohydrin and of some of the groups formed by dehydrohalogenation.

General Description

Odorless yellowish brown liquid. Sinks in water.

Air & Water Reactions

Oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick 1979 p.151-154, 164]. Insoluble in water.

Reactivity Profile

Epoxides, such as BISPHENOL A DIGLYCIDYL ETHER RESIN, are highly reactive. They polymerize in the presence of catalysts or when heated. These polymerization reactions can be violent. Compounds in this group react with acids, bases, and oxidizing and reducing agents. They react, possibly violently with water in the presence of acid and other catalysts.

Health Hazard

Contact with liquid irritates eyes. Prolonged or repeated contact with skin causes irritation and dermatitis.

Fire Hazard

BISPHENOL A DIGLYCIDYL ETHER RESIN is probably combustible.

Biological Activity

PPAR γ pure antagonist with micromolar affinity in 3T3-L1 and 3T3-F442A preadipocyte cells; selective over PPAR δ and PPAR α . Antagonizes the ability of rosiglitazone to stimulate transcriptional activity of PPAR γ . Acts as a PPAR γ agonist in an ECV304 cell line. Also produces PPARg-independent apoptosis of tumor cells via several mechanisms. Active in vivo .

Contact allergens

Most epoxy resins result from polymerization of bisphenol A diglycidyl ether (BADGE). Delayed hypersensitivity is caused by the low-molecular-weight monomer BADGE (Molecular Weight 340 g/mol), the dimer having much a lower sensitization power. This allergen caused contact dermatitis in six workers in a plant producing printed circuits boards made of copper sheets and fiber glass fabric impregnated with a brominated epoxy resin. It can be contained in adhesives.

Biochem/physiol Actions

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

Potential Exposure

Diglycidyl ether of bisphenol A is used as a basic active ingredient of epoxy resins.

Carcinogenicity

In summary, a number of carcinogenicity studies involving the topical application of pure BADGE as well as EPON Resin 828 and other commercial BADGE-based resins have been carried out in experimental animals.Viewing the studies as a whole, the weight of evidence does not show that BADGE or BADGE-based epoxy resins are carcinogenic.

Incompatibilities

Easily oxidized in air; presumed to form unstable and explosive peroxides in storage. Incompatible with strong acids; strong oxidizers.

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.

References

1) Cuzzocrea?et al. (2004),?Rosiglitazone , a ligand of the peroxisome proliferator-activated receptor-gamma, reduces acute inflammation; Eur. J. Pharmacol.,?483?79 2) Fehlberg?et al. (2003),?Bisphenol A diglycidyl ether-induced apoptosis involves Bax/Bid-dependent mitochondrial release of apoptosis-inducing factor (AIF), cytochrome c and Smac/DIABLO; Br. J. Pharmacol.,?139?495 3) Chamorro-Garcia?et al.?(2012),?Bisphenol A diglycidyl ether induces adipogenic differentiation of multipotent stromal stem cells through a peroxisome proliferator-activated receptor gamma-independent mechanism; Environ. Health Perspect.,?120?984 4) Duque?et al. (2013),?Pharmacological inhibition of PPARgamma increases osteoblastogenesis and bone mass in male C57BL/6 mice; J. Bone Miner. Res.,?28?639

InChI:InChI=1/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/t19-,20-/m1/s1

Upstream product

• 80-05-7 BPA 
• 106-89-8 epichlorohydrin 
• 3739-67-1 bisphenol A diallyl ether 
• 4809-35-2 1-chloro-3-[4-[2-[4-(3-chloro-2-hydroxypropoxy)phenyl] propan-2-yl]phenoxy]propan-2-ol 

Downstream Products

• 81214-95-1 1-[Benzyl-(1,4,6-trioxa-spiro[4.4]non-2-ylmethyl)-amino]-3-{4-[1-(4-{3-[benzyl-(1,4,6-trioxa-spiro[4.4]non-2-ylmethyl)-amino]-2-hydroxy-propoxy}-phenyl)-1-methyl-ethyl]-phenoxy}-propan-2-ol 
• 76002-91-0 2-[4-(2,3-epoxypropanyloxy)phenyl]-2-[4-(2,3-dihydroxypropanyloxy)phenyl]propane 
• 69303-52-2 2,2-bis[4-{3-[N-butyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino]-2-hydroxypropoxy}phenyl]propane 
• 69268-71-9 2,2-bis[4-{2-hydroxy-3-[N-(2-hydroxyethyl)-N-(2,2,6,6-tetramethyl-4-piperidyl)amino]propoxy}phenyl]propane 
• 69268-80-0 2,2-bis[4-{2-hydroxy-3-[(1,2,2,6,6-pentamethyl-4-piperidyl)amino]propoxy}phenyl]propane 
• 85023-51-4 4,4'-(((propane-2,2-diylbis(4,1-phenylene))bis(oxy))bis(methylene))bis(1,3-dioxolan-2-one) 
• 20844-45-5 3,3'-dibutyl-5,5'-[4,4'-(1-methyl-ethane-1,1-diyl)-bis-phenoxymethyl]-bis-oxazolidin-2-one 
• 21242-15-9 5,5′-(((propane-2,2-diylbis(4,1-phenylene))bis(oxy))bis-(methylene))bis(3-(p-tolyl)oxazolidin-2-one) 
• 122118-96-1 2,2-bis-[4-(2,3-diacetoxy-propoxy)-phenyl]-propane 

Relevant articles and documents

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