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D95654

Sigma-Aldrich

Diethyl fumarate

98%

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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
Linear Formula:
C2H5OCOCH=CHCOOC2H5
CAS Number:
623-91-6
Molecular Weight:
172.18
Beilstein:
775347
EC Number:
210-819-7
MDL number:
MFCD00064455
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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

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

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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 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)
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
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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