Dimethyl malonate

Names

[ CAS No. ]:
108-59-8

[ Name ]:
Dimethyl malonate

[Synonym ]:
dimethyl propanedioate
Propanedioic acid, dimethyl ester
Dimethyl malonate
MFCD00008460
Malonic acid dimethyl ester
methyl malonate
EINECS 203-597-8
Malonic acid, dimethyl ester

Biological Activity

[Description]:

Dimethyl malonate is a competitive inhibitor of succinate dehydrogenase (SDH). Dimethyl malonate is able to cross the blood-brain barrier and hydrolyse to malonate. Dimethyl malonate reduces neuronal apoptosis[1].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Neurological Disease

[In Vivo]

Dimethyl malonate (6 mg/kg/min; intravenous infusion; 51 min) promotes return of spontaneous circulation (ROSC) and neurological performance in rats after cardiac arrest[1]. Animal Model: Sprague-Dawley male rats, cardiac arrest model[1] Dosage: 6 mg/kg/min Administration: Intravenous infusion, 51 min Result: Improved ROSC after CA. Prevented the decline in neurological function and inhibited the apoptosis of hippocampal neurons at day 3 after CPR. Inhibited caspase-3 cleavage and increased HIF-1α expression at day 3 after CPR. Decreased the level of oxidative stress at day 3 after CPR. Inhibited excessive hyperpolarization of MMP and restrained the leakage of cytochrome C after 45 min reperfusion.

[References]

[1]. Xu J, et al. Inhibiting Succinate Dehydrogenase by Dimethyl Malonate Alleviates Brain Damage in a Rat Model of Cardiac Arrest. Neuroscience. 2018 Nov 21;393:24-32.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
177.1±8.0 °C at 760 mmHg

[ Melting Point ]:
−62 °C(lit.)

[ Molecular Formula ]:
C₅H₈O₄

[ Molecular Weight ]:
132.115

[ Flash Point ]:
90.0±0.0 °C

[ Exact Mass ]:
132.042252

[ PSA ]:
52.60000

[ LogP ]:
-0.36

[ Vapour density ]:
>1 (vs air)

[ Vapour Pressure ]:
1.1±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.402

[ Stability ]:
Stable. Incompatible with strong oxidizing agents. Flammable.

[ Water Solubility ]:
negligible

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OO0950000

CHEMICAL NAME :: Malonic acid, dimethyl ester

CAS REGISTRY NUMBER :: 108-59-8

LAST UPDATED :: 199709

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C5-H8-O4

MOLECULAR WEIGHT :: 132.13

WISWESSER LINE NOTATION :: 1OV1VO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 17,363,1979 ** ACUTE TOXICITY DATA **

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 5331 mg/kg

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

REFERENCE :: FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 17,363,1979

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >5 gm/kg

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

REFERENCE :: FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 17,363,1979

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

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

[ Personal Protective Equipment ]:
Eyeshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Hazard Codes ]:
Xi:Irritant

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ WGK Germany ]:
1

[ RTECS ]:
OO0950000

[ HS Code ]:
29171910

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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

Characterization of the cardiac succinylome and its role in ischemia-reperfusion injury.

J. Mol. Cell. Cardiol. 88 , 73-81, (2015)

Succinylation refers to modification of lysine residues with succinyl groups donated by succinyl-CoA. Sirtuin5 (Sirt5) is a mitochondrial NAD(+)-dependent deacylase that catalyzes the removal of succi...

Enantioselective modular synthesis of 2,4-disubstituted cyclopentenones by iridium-catalyzed allylic alkylation.

Angew. Chem. Int. Ed. Engl. 45(15) , 2466-9, (2006)

A rapid method for the synthesis of methylmalonyl-coenzyme A and other CoA-esters.

Anal. Biochem. 214(1) , 318-20, (1993)

A rapid and high-yield synthesis of methylmalonyl coenzyme A is reported. The two-step procedure involves preparation of the thiophenyl ester of methylmalonic acid using dicyclohexylcarbodiimide as a ...