Monomethyl fumarate

Names

[ Name ]:
Monomethyl fumarate

[Synonym ]:
MFCD00063174
(2E)-4-Methoxy-4-oxobut-2-enoic acid
2-Butenedioic acid, monomethyl ester, (2E)-
EINECS 220-412-6
(2E)-4-Methoxy-4-oxo-2-butenoic acid
Methyl Hydrogen Fumarate
2-Butenedioic acid, monomethyl ester
Monomethyl Fumarate
4-Methoxy-4-oxobut-2-enoic acid
Fumaric acid, monomethyl ester

Biological Activity

[Description]:

Monomethyl fumarate, an active metabolite of Dimethyl fumarate (DMF), is a potent GPR109A agonist. Monomethyl fumarate has the potential for multiple neuroprotective pathways and other models of retinal disease[1][2][3].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> GPR109A

Research Areas >> Inflammation/Immunology

Research Areas >> Neurological Disease

[In Vitro]

Monomethyl fumarate completely inhibits forskolin induced cAMP synthesis with an IC50 of 70 nM. Monomethyl fumarate induces a dose-dependent Ca2+ signal in GPR109A transfected cells with an EC50 of 9.4 μM[1]. Monomethyl fumarate (25 μM; 24 hours) attenuates 7β-OHC-induced cytotoxicity: cell growth inhibition; decreased cell viability; mitochondrial dysfunction; and cell death induction[3].

[In Vivo]

A single dose of Monomethyl fumarate (50-100 mg/kg; IP) before light exposure prevents these morphologic changes (bright light exposure induced photoreceptor death) in a dose-dependent manner[2]. Monomethyl fumarate (100 mg/kg) reduces retinal inflammation and oxidative stress. Monomethyl fumarate significantly suppresses light-induced retinopathy (LIR) upregulated genes in the NFkB pathway including: Nlrp3, Casp1, Il-1β, and Tnf-α[2]. Animal Model: Albino BALB/c mice (male, 6 weeks old)[2] Dosage: 50, 65, 75, 100 mg/kg Administration: IP Result: Prevented these morphologic changes (bright light exposure induced photoreceptor death) in a dose-dependent manner.

[References]

[1]. Tang H, et al. The psoriasis drug monomethylfumarate is a potent nicotinic acid receptor agonist. Biochem Biophys Res Commun. 2008 Oct 31;375(4):562-5.

[2]. Jiang D, et al. Monomethyl Fumarate Protects the Retina From Light-Induced Retinopathy. Invest Ophthalmol Vis Sci. 2019 Mar 1;60(4):1275-1285.

[3]. Sghaier R, et al. Dimethyl fumarate and monomethyl fumarate attenuate oxidative stress and mitochondrialalterations leading to oxiapoptophagy in 158N murine oligodendrocytes treated with 7β-hydroxycholesterol. J Steroid Biochem Mol Biol. 2019 Nov;194:105432.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
250.0±23.0 °C at 760 mmHg

[ Melting Point ]:
144-145ºC

[ Molecular Formula ]:
C₅H₆O₄

[ Molecular Weight ]:
130.099

[ Flash Point ]:
108.9±16.1 °C

[ Exact Mass ]:
130.026611

[ PSA ]:
63.60000

[ LogP ]:
-0.24

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.469

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS05

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H318

[ Precautionary Statements ]:
P280-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R41

[ Safety Phrases ]:
S26-S39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2918990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2918990090

[ Summary ]:
2918990090. other carboxylic acids with additional oxygen function and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

Altered Oligodendrocyte Maturation and Myelin Maintenance: The Role of Antiretrovirals in HIV-Associated Neurocognitive Disorders.

J. Neuropathol. Exp. Neurol. 74 , 1093-118, (2015)

Despite effective viral suppression through combined antiretroviral therapy (cART), approximately half of HIV-positive individuals have HIV-associated neurocognitive disorders (HAND). Studies of antir...

Structure-activity relationships of trans-substituted-propenoic acid derivatives on the nicotinic acid receptor HCA2 (GPR109A).

Bioorg. Med. Chem. Lett. 21 , 2736-9, (2011)

Nicotinic acid (niacin) has been used for decades as an antidyslipidemic drug in man. Its main target is the hydroxy-carboxylic acid receptor HCA2 (GPR109A), a G protein-coupled receptor. Other acids ...

Dimethyl fumarate induces necroptosis in colon cancer cells through GSH depletion/ROS increase/MAPKs activation pathway.

Br. J. Pharmacol. 172 , 3929-43, (2015)

Dimethyl fumarate (DMF) is a newly approved drug for the treatment of relapsing forms of multiple sclerosis and relapsing-remitting multiple sclerosis. Here, we investigated the effects of DMF and its...