CAS 2756-87-8|Monomethyl fumarate
| 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 | ChineseUSA | Flash Point | 108.9±16.1 °C |
| Symbol | GHS05 | Signal Word | Danger |
Names
| Name | Fumaric Acid Monomethyl Ester |
|---|---|
| Synonym | More Synonyms |
Monomethyl fumarate BiologicalActivity
| 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 >>GPR109AResearch Areas >>Inflammation/ImmunologyResearch 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 |
| InChIKey | NKHAVTQWNUWKEO-NSCUHMNNSA-N |
| SMILES | COC(=O)C=CC(=O)O |
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 |
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 |
