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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:
775347
EC Number:
210-819-7
MDL number:
MFCD00064455
UNSPSC Code:
12352100
PubChem Substance ID:
24894309
NACRES:
NA.22

Quality Level

200

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

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 3

Flash Point(F)

197.6 °F

Flash Point(C)

92 °C

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)
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
Phung Xuan Lan et al.
Journal of materials science. Materials in medicine, 20(1), 271-279 (2008-09-03)
Poly(propylene fumarate) (PPF) is an ultraviolet-curable and biodegradable polymer with potential applications for bone regeneration. In this study, we designed and fabricated three-dimensional (3D) porous scaffolds based on a PPF polymer network using micro-stereolithography (MSTL). The 3D scaffold was well
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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