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Monomethyl fumarate structure, CAS 2756-87-8

Monomethyl fumarate

CAS Number2756-87-8

SynonymsMFCD00063174; (2E)-4-Methoxy-4-oxobut-2-enoic acid; 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

Molecular FormulaHO2CCH=CHCO2CH3

Molecular Weight130.10

Purity97%

Density1.3±0.1 g/cm3

Boiling Point250.0±23.0 °C at 760 mmHg

Melting Point144-145 °C (lit.)

Flash Point

Appearancesolid

EINECS220-412-6

MSDSChineseEnglish

SymbolTransport

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Cat. No.: 2A-9015000 Purity: 97%
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Quality Control of [ 2756-87-8 ] Purity: 97% SDS Specification MoL

COA NMR CNMR HPLC LC-MS
Chemical & Physical Properties
CAS Number2756-87-8
Catalog No.2A-9015000
Chinese Name富马酸单甲酯
SynonymsMFCD00063174; (2E)-4-Methoxy-4-oxobut-2-enoic acid; 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
Molecular FormulaHO2CCH=CHCO2CH3
Molecular Weight130.10
Purity97
Density1.3±0.1 g/cm3
Boiling Point250.0±23.0 °C at 760 mmHg
Melting Point144-145 °C (lit.)
Appearancesolid
Storage ConditionRoom temperature, dry
ApplicationMonomethyl fumarate is the active metabolite of Dimethyl fumarate (DMF), a potent GPR109A agonist. Monomethyl fumarate has potential for use in multiple neuroprotective pathways and other retinal dise
EINECS220-412-6
HTC2918990090
PubChem ID24883828
MDL NumberMFCD00063174
SMILESCOC(=O)\C=C\C(O)=O
InChI1S/C5H6O4/c1-9-5(8)3-2-4(6)7/h2-3H,1H3,(H,6,7)/b3-2+
InChI KeyNKHAVTQWNUWKEO-NSCUHMNNSA-N
NACRES CodeNA.22
UNSPSC12352100
Hazard SymbolsTransport
MSDSmsds/15000_1_2756_87_8.pdf
BioactivityMonomethyl 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 InChIKey NKHAVTQWNUWKEO-NSCUHMNNSA-N SMILES COC(=O)C=CC(=O)O
Use ofMonomethyl 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]. Properties 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 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]. 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 Molecular Formula C5H6O4 Exact Mass 130.026611 PSA 63.60000 LogP -0.24 Index of Refraction 1.469 InChIKey NKHAVTQWNUWKEO-NSCUHMNNSA-N SMILES COC(=O)C=CC(=O)O
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Transport InfoShipping Name: UN
MSDS Transport InfoModule 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available
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