Monomethyl Fumarate (HCID 5369209)

Overview

Monomethyl fumarate is a dicarboxylic acid monoester resulting from the formal condensation of one of the carboxy groups of fumaric acid with methanol. Is is a metabolite of dimethyl fumarate and used for the the treatment of patients with relapsing multiple sclerosis (MS). It also induces the NFE2L2 (Nrf2) transcription factor by binding to KEAP1. It has a role as an antioxidant, a drug metabolite and an immunomodulator. It is a methyl ester, a dicarboxylic acid monoester and an enoate ester. It is functionally related to a fumaric acid.

Names & identifiers

Preferred name: Monomethyl Fumarate
IUPAC: (E)-4-methoxy-4-oxobut-2-enoic acid
English name: Monomethyl fumarate
Molecular formula: C5H6O4
Molecular weight: 130.1

Names & synonyms

Monomethyl fumarate2756-87-8Fumaric acid monomethyl esterBafiertam45IUB1PX8RmethylhydrogenfumarateCHEBI:167450NSC-523835DTXSID801016498RefChem:55666DTXCID30209463220-412-6

Show more names

TAK438 Impurity 110MethylhydrogenfumaratMonomethylFumarate>Vonoprazan Impurity 110Mono-Methyl fuMarate 97%

Methyl FumaratemonomethylfumarateMethyl hydrogen fumarate4-methoxy-4-oxobut-2-enoic acidmono-Methyl fumarate(E)-4-methoxy-4-oxobut-2-enoic acid(2E)-4-Methoxy-4-oxobut-2-enoic acid2-Butenedioic acid (2E)-, 1-methyl ester

Database identifiers

CAS: 2756-87-8
PubChem CID: 5369209
DTXSID: DTXSID801016498
ChEMBL: CHEMBL589586
ChEBI: CHEBI:167450
UNII: 45IUB1PX8R
EC Number: 220-412-6
Nikkaji: J121.400D、J520.491G

Properties

Computed structural properties

XLogP: 0.4
Topological polar surface area: 63.6 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 4
Rotatable bonds: 3
Heavy atoms: 9
Formal charge: 0
Complexity: 147

Experimental & physicochemical properties

DrugsPharmaceuticals -> Metabolite of Dimethyl fumarate

SpringerMaterials PropertiesCrystal structure

Human Drugs · 2 items

FDA approved drugs -> Active ingredient

Food Contact SubstancesFCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR

Physicochemical properties

Melting point: 144 · 144-145 °C (lit.)
Boiling point: 250 · 250.0±23.0 °C(Predicted)
Density: 1.37 g/cm3 · 1.37 g/cm3
storage temp.: 2 · 2-8°C
solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
pka: 3.4 · 3.40±0.10(Predicted)
form: Solid
color: Off-White
λmax: 209 nm · 209nm(MeOH)(lit.)
InChI: InChI=1S/C5H6O4/c1-9-5(8)3-2-4(6)7/h2-3H,1H3,(H,6,7)/b3-2+
InChIKey: NKHAVTQWNUWKEO-NSCUHMNNSA-N
SMILES: C(OC)(=O)/C=C/C(O)=O
FDA 21 CFR: 175.105 · 175.105
Indirect Additives used in Food Contact Substances: MONOMETHYL FUMARATE
CAS DataBase Reference: 2756 · 2756-87-8(CAS DataBase Reference)
FDA UNII: 45 IUB1PX8R · 45IUB1PX8R
UNSPSC Code: 41116107 · 41116107
NACRES: 24 · NA.24
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 319 · H319
Precautionary statements: 264 · P264-P280-P305+P351+P338-P337+P313
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xi
Risk Statements: 41 · 41
Safety Statements: 26 · 26-39
WGK Germany: 3 · 3
HS Code: 29171900 · 29171900
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 · Eye Irrit. 2
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 26.2% (37 of 141) of reports.

Danger

H318 (72.3%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

P264+P265, P280, P305+P354+P338, and P317 (click each P-code to see the statement)

Aggregated GHS information provided per 141 reports by companies from 7 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory InformationStatus: Active Update: 23-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/29959

Hazard Classes and CategoriesEye Dam. 1 (72.3%)

Toxicology

Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Monomethyl fumarate

Ambiguous-DILI-concern

4

Warnings & precautions

DOI:10.1016/j.drudis.2016.02.015

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
hs_code: 29171900
risk_code: 41
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-39
Storage Class: 11 - Combustible Solids
Hazard statements: H319
REACH Registrations: Active
Hazard Classifications: Eye Irrit. 2
Precautionary statements: P264-P280-P305+P351+P338-P337+P313

Chemistry & industry

Pharmacology

ATC CodeL - Antineoplastic and immunomodulating agents

Applications · 2 items

DescriptionMonomethyl fumarate (MMF), a bioactive metabolite of fumaric acid ester, is an immunotherapy for psoriasis that causes decreased production of Th1 cytokines and lymphocytopenia. Monomethyl fumarate was shown to decrease DC response to LPS and decreased IL-12p70 and IL-10 production.

UsesMonomethyl fumarate is used to treat the relapsing forms of multiple sclerosis (MS), including clinically isolated syndrome, relapsing-remitting disease, and active secondary progressive disease. This medicine will not cure MS, but it may slow some of the disabling effects and decrease the number of relapses of the disease.Fumaric Acid Monomethyl Ester is one of the most bioactive anti-psoriatic fumaric acid ester metabolite. Fumaric Acid Monomethyl Ester is potent nicotinic acid receptor agonist. Fumaric Acid Monomethy l Ester has also been shown to selectively stimulate of T helper 2 cytokine response.

Preparation methods

PreparationMonomethyl fumarate was synthesized by maleic anhydride and methanol. monomethyl fumarate could inhibit the growth of mold, and the storage time of feed could be prolonged.

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

衢州润东化工有限公司0570-8789886 18892685668 · [email protected]

合肥翰刚医药科技有限公司+8618062405514 · [email protected]

Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]

Hebei Yanxi Chemical Co., Ltd.+86-17531190177 · [email protected]

Additional notes · 1 item

DefinitionChEBI: Monomethyl fumarate is a dicarboxylic acid monoester resulting from the formal condensation of one of the carboxy groups of fumaric acid with methanol. Is is a metabolite of dimethyl fumarate and used for the the treatment of patients with relapsing multiple sclerosis (MS). It also induces the NFE2L2 (Nrf2) transcription factor by binding to KEAP1. It has a role as an immunomodulator, an antioxidant and a drug metabolite. It is an enoate ester, a methyl ester and a dicarboxylic acid monoester. It derives from a fumaric acid.