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651419

Sigma-Aldrich

mono-Methyl fumarate

97%

Synonym(s):

Fumaric acid monomethyl ester, Methyl hydrogen fumarate

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About This Item

Linear Formula:
HO2CCH=CHCO2CH3
CAS Number:
2756-87-8
Molecular Weight:
130.10
EC Number:
220-412-6
MDL number:
MFCD00063174
UNSPSC Code:
12352100
PubChem Substance ID:
24883828
NACRES:
NA.22

Assay

97%

form

solid

mp

144-145 °C (lit.)

SMILES string

COC(=O)\C=C\C(O)=O

InChI

1S/C5H6O4/c1-9-5(8)3-2-4(6)7/h2-3H,1H3,(H,6,7)/b3-2+

InChI key

NKHAVTQWNUWKEO-NSCUHMNNSA-N

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Application

mono-Methyl fumarate can be used as a reactant to synthesize:
  • Jumonji C domain-containing histone demethylases (JCHDMs) inhibitor.
  • (−)-Xylariamide A, a fungal metabolite.
  • (±)-Methoxyfumimycin ethyl ester, a potential bacterial peptide deformylase inhibitor.

It is also a wide spectrum antibacterial agent with a powerful antioxidant activity.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Modification of chitosan with monomethyl fumaric acid in an ionic liquid solution.
Wang Z, et al.
Carbohydrate Polymers, 117, 973-979 (2015)
Jennifer N Hahn et al.
Journal of immunology (Baltimore, Md. : 1950), 197(10), 3850-3860 (2016-10-14)
Extracellular matrix metalloproteinase inducer (EMMPRIN, CD147) is a transmembrane glycoprotein that is upregulated on leukocytes in active lesions in multiple sclerosis (MS) and its animal model, experimental autoimmune encephalomyelitis (EAE). Administration of anti-EMMPRIN Abs reduces the severity of EAE. Minocycline
A concise synthesis of (?)-methoxyfumimycin ethyl ester.
Zhou Z, et al.
J. Chem. Res. (M), 38(6) (2014)
Isolation and structure elucidation of the new fungal metabolite (−)-xylariamide A.
Davis R A, et al.
Journal of Natural Products, 68(5), 769-772 (2005)
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