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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:
Molecular Weight:
130.10
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

form

solid

mp

144-145 °C (lit.)

functional group

carboxylic acid
ester

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

Signal Word

Warning

Hazard Statements

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

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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)
A selective inhibitor and probe of the cellular functions of Jumonji C domain-containing histone demethylases.
Luo X, et al.
Journal of the American Chemical Society, 133(24), 9451-9456 (2011)
A concise synthesis of (?)-methoxyfumimycin ethyl ester.
Zhou Z, et al.
J. Chem. Res. (M), 38(6) (2014)
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
Laura Northrup et al.
Molecular pharmaceutics, 14(1), 66-80 (2017-01-04)
Current therapies to treat autoimmune diseases often result in side effects such as nonspecific immunosuppression. Therapies that can induce antigen-specific immune tolerance provide an opportunity to reverse autoimmunity and mitigate the risks associated with global immunosuppression. In an effort to

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