mono-Methyl fumarate - CAS 2756-87-8
Catalog: |
BB019613 |
Product Name: |
mono-Methyl fumarate |
CAS: |
2756-87-8 |
Synonyms: |
(E)-4-methoxy-4-oxobut-2-enoic acid |
Application: |
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 monomethyl ester has also been shown to selectively stimulate of T helper 2 cytokine response. It is also the active metabolite of Dimethyl Fumarate (D464965), a compound that is used as a treatment for the relapsing forms of multiple sclerosis and psoriasis. |
IUPAC Name: | (E)-4-methoxy-4-oxobut-2-enoic acid |
Description: | Monomethyl Fumarate is one of the most bioactive anti-psoriatic fumaric acid ester metabolite. It is potent nicotinic acid receptor agonist. It has also been shown to selectively stimulate of T helper 2 cytokine response. |
Molecular Weight: | 130.10 |
Molecular Formula: | C5H6O4 |
Canonical SMILES: | COC(=O)C=CC(=O)O |
InChI: | InChI=1S/C5H6O4/c1-9-5(8)3-2-4(6)7/h2-3H,1H3,(H,6,7)/b3-2+ |
InChI Key: | NKHAVTQWNUWKEO-NSCUHMNNSA-N |
Boiling Point: | 250 °C at 760 mmHg |
Melting Point: | 143-146 °C |
Purity: | > 95 % |
Density: | 1.265 g/cm3 |
Appearance: | Off-white solid |
MDL: | MFCD00063174 |
LogP: | -0.19980 |
GHS Hazard Statement: | H318 (99.02%): Causes serious eye damage [Danger Serious eye damage/eye irritation] |
Precautionary Statement: | P280, P305+P351+P338, and P310 |
Signal Word: | Danger |
Publication Number | Title | Priority Date |
US-10105335-B2 | Fumarate ester dosage forms | 20150831 |
US-9566259-B1 | Fumarate ester dosage forms | 20150831 |
US-9636318-B2 | Fumarate ester dosage forms | 20150831 |
US-9636319-B1 | Fumarate ester dosage forms | 20150831 |
US-9814692-B2 | Fumarate ester dosage forms | 20150831 |
PMID | Publication Date | Title | Journal |
32020584 | 20200501 | The IUPHAR Guide to Immunopharmacology: connecting immunology and pharmacology | Immunology |
32059809 | 20200401 | Advances in oral immunomodulating therapies in relapsing multiple sclerosis | The Lancet. Neurology |
28958667 | 20180101 | Dimethyl fumarate influences innate and adaptive immunity in multiple sclerosis | Journal of autoimmunity |
27625306 | 20160913 | Chemical proteomic map of dimethyl fumarate-sensitive cysteines in primary human T cells | Science signaling |
24139424 | 20131001 | Tolerability and pharmacokinetics of delayed-release dimethyl fumarate administered with and without aspirin in healthy volunteers | Clinical therapeutics |
Complexity: | 147 |
Compound Is Canonicalized: | Yes |
Covalently-Bonded Unit Count: | 1 |
Defined Atom Stereocenter Count: | 0 |
Defined Bond Stereocenter Count: | 1 |
Exact Mass: | 130.02660867 |
Formal Charge: | 0 |
Heavy Atom Count: | 9 |
Hydrogen Bond Acceptor Count: | 4 |
Hydrogen Bond Donor Count: | 1 |
Isotope Atom Count: | 0 |
Monoisotopic Mass: | 130.02660867 |
Rotatable Bond Count: | 3 |
Topological Polar Surface Area: | 63.6 Å2 |
Undefined Atom Stereocenter Count: | 0 |
Undefined Bond Stereocenter Count: | 0 |
XLogP3: | 0.4 |
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