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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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Treatment of recurrent aphthous stomatitis with fumaric acid esters.
Emmanuella Guenova et al.
Archives of dermatology, 147(3), 282-284 (2011-03-23)
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
H B Thio et al.
The British journal of dermatology, 131(6), 856-861 (1994-12-01)
Systemic administration of fumaric acid (FA) derivatives was originally an empirical antipsoriatic treatment, which showed promising clinical results. In the present study, FURA-2-loaded suspensions of cultured normal keratinocytes and SV40-transformed keratinocytes (SVK-14 cells) were used to study the effects of
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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