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D95654

Sigma-Aldrich

Diethyl fumarate

98%

Synonym(s):

(2E)-2-Butenedioic acid diethyl ester, (E)-But-2-enedioic acid diethyl ester, Diethyl (E)-but-2-enedioate, Diethyl fumaric acid ester, Ethyl fumarate

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About This Item

Linear Formula:
C2H5OCOCH=CHCOOC2H5
CAS Number:
Molecular Weight:
172.18
Beilstein:
775347
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

98%

form

liquid

refractive index

n20/D 1.44 (lit.)

bp

218-219 °C (lit.)

mp

1-2 °C (lit.)

density

1.052 g/mL at 25 °C (lit.)

SMILES string

[H]\C(=C(\[H])C(=O)OCC)C(=O)OCC

InChI

1S/C8H12O4/c1-3-11-7(9)5-6-8(10)12-4-2/h5-6H,3-4H2,1-2H3/b6-5+

InChI key

IEPRKVQEAMIZSS-AATRIKPKSA-N

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General description

Diethyl fumarate is an electrophilic compound, commonly used in the Diels-Alder reaction.

Application


  • Relaxation and Amorphous Structure of Polymers: This study examines the behavior of polymers with rigid fumarate segments, including diethyl fumarate, and their impact on the relaxation and amorphous structures, enhancing polymer design and processing (Suzuki et al., 2022).

  • Gradient versus End-Capped Degradable Polymer Sequence Variations: The research explores the mechanical properties of photochemically 3D-printed substrates using diethyl fumarate-based polymers, presenting new possibilities in creating tailored biomaterials for medical applications (Shin and Becker, 2022).

  • Novel Curcumin-Diethyl Fumarate Hybrid for Parkinson′s Disease: This study investigates a hybrid molecule combining curcumin and diethyl fumarate, highlighting its dual function as a GSK-3β inhibitor and Nrf2 inducer, which could be significant for Parkinson′s disease treatment strategies (Di Martino et al., 2020).

  • Synthesis and 3D Printing of PEG-Poly(propylene fumarate) Copolymers: This article describes the synthesis and application of diethyl fumarate in the creation of novel diblock and triblock copolymer hydrogels for 3D printing, expanding the utility in biomedicine and tissue engineering (Dilla et al., 2018).

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

197.6 °F - closed cup

Flash Point(C)

92 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Recent advances in understanding NRF2 as a druggable target: development of pro-electrophilic and non-covalent NRF2 activators to overcome systemic side effects of electrophilic drugs like dimethyl fumarate
Takumi S et al.
F1000Research, 6 (2017)
A Lahti et al.
Contact dermatitis, 16(3), 133-135 (1987-03-01)
To investigate the mechanisms of non-immunologic contact urticaria (NICU), the effects of 1g + 1g of acetylsalicylic acid (ASA) on contact reactions to methyl nicotinate, diethyl fumarate, benzoic acid, cinnamic acid, cinnamic aldehyde and dimethyl sulfoxide were studied in 21
B Sebök et al.
Skin pharmacology : the official journal of the Skin Pharmacology Society, 9(2), 99-103 (1996-01-01)
Fumaric acid, fumaric acid dimethylester, and the dithranol derivative C4-lactone were studied in the mouse tail test to evaluate their effects on epidermal cell differentiation compared with other topical antipsoriatic drugs, such as betamethasone, calcipotriol, and dithranol. Mouse tails were
Jin Woo Lee et al.
Biomaterials, 32(3), 744-752 (2010-10-12)
Bony defects have been three-dimensionally (3D) created in many clinical circumstances; however, many defects cannot be reconstructed because most of the current bony substitutes cannot provide the necessary exact 3D structure. Therefore, to overcome this limitation, a 3D scaffold with
A Lahti et al.
Journal of the American Academy of Dermatology, 13(4), 585-589 (1985-10-01)
The decrease in the swelling capacity and the length of the refractory period after nonimmunologic contact urticaria produced by one application of six human nonimmunologic contact urticaria agents was studied with the use of the guinea pig ear test. On

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