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128422

Sigma-Aldrich

mono-Ethyl fumarate

95%

Synonym(s):

Fumaric acid monoethyl ester, Monoethyl fumarate

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About This Item

Linear Formula:
C2H5OCOCH=CHCOOH
CAS Number:
2459-05-4
Molecular Weight:
144.13
Beilstein:
1723588
EC Number:
219-544-7
MDL number:
MFCD00002699
UNSPSC Code:
12352100
PubChem Substance ID:
24847858
NACRES:
NA.22

Assay

95%

form

solid

bp

147 °C/16 mmHg (lit.)

mp

66-68 °C (lit.)

SMILES string

CCOC(=O)\C=C\C(O)=O

InChI

1S/C6H8O4/c1-2-10-6(9)4-3-5(7)8/h3-4H,2H2,1H3,(H,7,8)/b4-3+

InChI key

XLYMOEINVGRTEX-ONEGZZNKSA-N

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Application

mono-Ethyl fumarate (fumaric acid monoethyl ester, monoethyl fumarate) was used in the preparation of photo-crosslinkable macromers. It was also used to synthesize Ugi/intramolecular Diels-Alder (IMDA) cycloaddition products.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H317,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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K Paulvannan
The Journal of organic chemistry, 69(4), 1207-1214 (2004-02-14)
An efficient approach to rigid tricyclic nitrogen heterocycles via sequential and tandem Ugi/intramolecular Diels-Alder (IMDA) cycloaddition of pyrrole is described. The one-pot Ugi four-component condensation (4CC) reaction was used as the key transformation to prepare trienes with a carboxamide substituent
Janine Jansen et al.
Acta biomaterialia, 8(10), 3652-3659 (2012-06-19)
Photo-crosslinked networks were prepared from fumaric acid monoethyl ester-functionalized poly(D,L-lactic acid) oligomers and N-vinyl-2-pyrrolidone. Two model proteins, lysozyme and albumin, were incorporated into the network films as solid particles and their release behavior was studied. By varying the NVP content
Janine Jansen et al.
Biomacromolecules, 10(2), 214-220 (2008-12-19)
Polymer networks were prepared by photocross-linking fumaric acid monoethyl ester (FAME) functionalized, three-armed poly(D,L-lactide) oligomers using N-vinyl-2-pyrrolidone (NVP) as diluent and comonomer. The use of NVP together with FAME-functionalized oligomers resulted in copolymerization at high rates, and networks with gel
Treatment of recurrent aphthous stomatitis with fumaric acid esters.
Emmanuella Guenova et al.
Archives of dermatology, 147(3), 282-284 (2011-03-23)
D Werdenberg et al.
Biopharmaceutics & drug disposition, 24(6), 259-273 (2003-09-16)
Psoriasis is a chronic inflammatory skin disease. Its treatment is based on the inhibition of proliferation of epidermal cells and interference in the inflammatory process. A new systemic antipsoriasis drug, which consists of dimethylfumarate and ethylhydrogenfumarate in the form of
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