Monomethyl fumarate

Modify Date: 2025-08-25 16:56:26

Monomethyl fumarate Structure
Monomethyl fumarate structure
 Common Name Monomethyl fumarate
CAS Number 2756-87-8 Molecular Weight 130.099
Density 1.3±0.1 g/cm3 Boiling Point 250.0±23.0 °C at 760 mmHg
Molecular Formula C5H6O4 Melting Point 144-145ºC
MSDS Chinese USA Flash Point 108.9±16.1 °C
Symbol GHS05
GHS05		 Signal Word Danger

 Use of Monomethyl fumarate


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].

 Names

Name Fumaric Acid Monomethyl Ester
Synonym More Synonyms

 Monomethyl fumarate 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
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
InChIKey NKHAVTQWNUWKEO-NSCUHMNNSA-N
SMILES COC(=O)C=CC(=O)O

 Safety Information

Symbol GHS05
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

 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%

 Articles6

More 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...

 Synonyms

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
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