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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:
623-91-6
Molecular Weight:
172.18
Beilstein/REAXYS Number:
775347
EC Number:
210-819-7
MDL number:
MFCD00064455
UNSPSC Code:
12352100
PubChem Substance ID:
24894309
NACRES:
NA.22

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
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

197.6 °F - closed cup

flash_point_c

92 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL4767
BCCK4888
BCCH3226
BCCC0138
BCBW6573

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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.
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
Pattama Saisaha et al.
Organic & biomolecular chemistry, 8(19), 4444-4450 (2010-08-18)
A practical method for the multigram scale selective cis-dihydroxylation of electron deficient alkenes such as diethyl fumarate and N-alkyl and N-aryl-maleimides using H(2)O(2) is described. High turnovers (>1000) can be achieved with this efficient manganese based catalyst system, prepared in
W Raab
Zeitschrift fur Hautkrankheiten, 59(10), 671-679 (1984-05-15)
Fumaric acid may not be regarded as an antipsoriatic drug. Beneficial effects on psoriatic lesions may be explained by secondary changes such as the acidification of gastric juice in cases of anacidity or hypacidity . Monoethylfumarate exerts true antipsoriatic activities
Joachim C U Lehmann et al.
The Journal of investigative dermatology, 127(4), 835-845 (2007-01-20)
A mixture of different fumaric acid esters (FAE) is established for systemic therapy of psoriasis, a frequent inflammatory skin disease. The main active compound of FAE, however, has not been identified so far, and the mechanisms of activity are only
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