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D95654

Sigma-Aldrich

Diethyl fumarate

98%

Synonyme(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

Formule linéaire :
C2H5OCOCH=CHCOOC2H5
Numéro CAS:
623-91-6
Poids moléculaire :
172.18
Numéro Beilstein :
775347
Numéro CE :
210-819-7
Numéro MDL:
MFCD00064455
Code UNSPSC :
12352100
ID de substance PubChem :
24894309
Nomenclature NACRES :
NA.22

Niveau de qualité

200

Pureté

98%

Forme

liquid

Indice de réfraction

n20/D 1.44 (lit.)

Point d'ébullition

218-219 °C (lit.)

Pf

1-2 °C (lit.)

Densité

1.052 g/mL at 25 °C (lit.)

Chaîne SMILES 

[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+

Clé InChI

IEPRKVQEAMIZSS-AATRIKPKSA-N

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Description générale

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).

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

197.6 °F - closed cup

Point d'éclair (°C)

92 °C - closed cup

Équipement de protection individuelle

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

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A kinetic study of the Diels-Alder reaction: An experiment illustrating simple second-order reaction kinetics
Michael S G et al.
Journal of Chemical Education, 66, 690-690 (1989)
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)
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
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
A Lahti et al.
Contact dermatitis, 12(3), 139-140 (1985-03-01)
The contact urticariagenic properties of diethyl fumarate were studied using the guinea pig ear swelling assay and by open application on the human upper back skin. Diethyl fumarate caused non-immunologic contact urticaria in both human and guinea pig skin, and
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