Dimethyl malonate

Modify Date: 2024-01-01 18:39:25

Dimethyl malonate Structure
Dimethyl malonate structure
Common Name Dimethyl malonate
CAS Number 108-59-8 Molecular Weight 132.115
Density 1.1±0.1 g/cm3 Boiling Point 177.1±8.0 °C at 760 mmHg
Molecular Formula C5H8O4 Melting Point −62 °C(lit.)
MSDS Chinese USA Flash Point 90.0±0.0 °C
Symbol GHS07
GHS07
Signal Word Warning

 Use of Dimethyl malonate


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].

 Names

Name Dimethyl malonate
Synonym More Synonyms

 Dimethyl malonate 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
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

 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
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

 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%

 Articles28

More 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 ...

 Synonyms

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