Mesaconic acid

Names

[ CAS No. ]:
498-24-8

[ Name ]:
Mesaconic acid

[Synonym ]:
Methylfumaric Acid
EINECS 207-859-2
Mesaconic Acid
MFCD00002653
2-Butenedioic acid,2-methyl-, (2E)-

Chemical & Physical Properties

[ Density]:
1.387 g/cm3

[ Boiling Point ]:
336.6ºC at 760 mmHg

[ Melting Point ]:
200-202ºC

[ Molecular Formula ]:
C₅H₆O₄

[ Molecular Weight ]:
130.09900

[ Flash Point ]:
171.5ºC

[ Exact Mass ]:
130.02700

[ PSA ]:
74.60000

[ LogP ]:
0.10190

[ Vapour Pressure ]:
0mmHg at 25°C

[ Index of Refraction ]:
1.514

[ Storage condition ]:
2-8°C

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OX5075000

CHEMICAL NAME :: Mesaconic acid

CAS REGISTRY NUMBER :: 498-24-8

BEILSTEIN REFERENCE NO. :: 1722680

LAST UPDATED :: 199701

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C5-H6-O4

MOLECULAR WEIGHT :: 130.11

WISWESSER LINE NOTATION :: QVY1&U1VQ -T

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CBCCT* "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. (National Academy of Science Library, 2101 Constitution Ave., NW, Washington, DC 20418) Volume(issue)/page/year: 6,147,1954

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
OX5075000

[ HS Code ]:
2917190090

Precursor & DownStream

Precursor

Itaconic acid
Citraconic acid
Itaconic acid diethyl ester
(2S,3S)-2-AMINO-3-METHYLSUCCINIC ACID
Citraconic anhydride
Ethyl 2-methylacetoacetate
2-Methylcyclohexa-2,5-diene-1,4-dione
(2S,3S)-[3-2H]-3-methylaspartic acid
2-Toluenesulfonic acid
D,L-threo-β-methylaspartic acid

DownStream

(R)-(+)-Methylsuccinic Acid
(2S)-2-methylbutanedioic acid
Methacrylic acid
Citraconic acid
Itaconic acid
tetrahydro-5-oxo-3-furancarboxylic acid
2-Hydroxyisobutyric acid
propene
L-Valine hydrochloride
2-methylbut-2-enedioyl dichloride

Customs

[ HS Code ]: 2917190090

[ Summary ]:
2917190090 acyclic polycarboxylic acids, their anhydrides, halides, peroxides, peroxyacids and their derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

Articles

The antipsoriatic agent monomethylfumarate has antiproliferative, prodifferentiative, and anti-inflammatory effects on keratinocytes.

J. Pharmacol. Exp. Ther. 352(1) , 90-7, (2015)

Monomethylfumarate (MMF) is thought to be the bioactive ingredient of the drug Fumaderm (Biogen Idec, Cambridge, MA), licensed in Germany since 1994 for the treatment of moderate-to-severe psoriasis. ...

In vitro pharmacokinetics of anti-psoriatic fumaric acid esters.

BMC Pharmacol. 4 , 22, (2004)

Psoriasis is a chronic inflammatory skin disease that can be successfully treated with a mixture of fumaric acid esters (FAE) formulated as enteric-coated tablets for oral use. These tablets consist o...

The psoriasis drug monomethylfumarate is a potent nicotinic acid receptor agonist.

Biochem. Biophys. Res. Commun. 375(4) , 562-5, (2008)

Nicotinic acid has been used for several decades to treat dyslipidemia. In mice, the lipid-lowing effect of nicotinic acid is mediated by the Gi coupled receptor PUMA-G. In humans, high (GPR109A) and ...