Sodium dichloroacetate Chemical Properties

Melting point:

198 °C (dec.) (lit.)

storage temp. 

Inert atmosphere,2-8°C

solubility 

Methanol (Slightly), Water (Slightly)

form 

Powder

color 

White

PH

6.0 to 8.5(50g/L, 25 ℃)

Water Solubility 

soluble in cold water

Sensitive 

Moisture Sensitive

Stability:

Hygroscopic

InChI

InChI=1S/C2H2Cl2O2.Na.H/c3-1(4)2(5)6;;/h1H,(H,5,6);;

InChIKey

LUPNKHXLFSSUGS-UHFFFAOYSA-M

SMILES

C(Cl)(Cl)C(=O)O.[NaH]

CAS DataBase Reference

2156-56-1(CAS DataBase Reference)

EPA Substance Registry System

Sodium dichloroacetate (2156-56-1)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-40

Safety Statements 

26-37/39-36-36/37

RIDADR 

2811

WGK Germany 

2

RTECS 

AG9275000

HS Code 

29154000

MSDS

• Language:English Provider:Dichloroacetic acid sodium salt
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Sodium dichloroacetate Usage And Synthesis

Uses

Sodium dichloroacetate (DCA) is a mitochondrial pyruvate dehydrogenase kinase inhibitor, and is an orally absorbable small molecular compound for MELAS syndrome, and children with congenital lactic acidosis and other diseases that are treated in the clinic. Recent studies had found that DCA acts as a potential vasoprotective agent by inhibiting PDK2 and reducing coronary endarterium proliferation. Further, DCA promotes brain regeneration after cerebral ischemia, which indicates that DCA might play an important role in VD.

Chemical Properties

white powder

Uses

Treatment of neurologic injury (pyruvate dehydrogenase activator).

Uses

Sodium dichloroacetate is an inhibitor of mitochondrial pyruvate dehydrogenase kinase.

brand name

Ceresine (Cypros).

General Description

Sodium dichloroacetate is a mitochondrial pyruvate dehydrogenase kinase (PDK) inhibitor that exhibits potent anti-leukemic activity.

Biological Activity

Inhibitor of mitochondrial pyruvate dehydrogenase kinase (PDK). Shifts pyruvate metabolism from glycolysis and lactate production to glucose oxidation in the mitochondria. Induces mitochondrial-dependent apoptosis and reverses the inhibition/downregulation of K V 1.5 channels in cancer but not normal cells. Decreases tumor growth in vitro and in vivo .

Synthesis

General procedure for the synthesis of sodium dichloroacetate from dichloroacetic acid: Cl2CHCO2H (135 μL, 1.64 mmol) was dissolved in H2O (2 mL), treated with 1.00 M NaOH (1.60 mL, 1.60 mmol), and the reaction was stirred for 2 hours at room temperature. Upon completion of the reaction, the volatiles were removed under vacuum to give a pale yellow residue. The residue was suspended in acetone, the suspension was filtered, the resulting colorless solid was washed with acetone and finally dried under vacuum. Yield: 227 mg, 96% yield.

storage

Desiccate at RT

References

[1] Journal of Organometallic Chemistry, 2018, vol. 869, p. 201 - 211

Sodium dichloroacetate(2156-56-1)Related Product Information

• Dichloroacetic acid methyl ester
• Trisodium phosphate
• Sodium diethyldithiocarbamate trihydrate
• Dichloroacetic acid
• Sodium chloride
• Diclofenac sodium
• Sodium citrate
• Sodium benzoate
• Sodium acetate
• Sodium hydroxide
• Sodium chloroacetate
• Sodium bicarbonate
• Sodium chlorite
• Sodium dichloroisocyanurate
• Sodium dimethyl 5-sulphonatoisophthalate
• 8-CHLOROADENOSINE-3',5'-CYCLIC MONOPHOSPHOROTHIOATE, RP-ISOMER SODIUM SALT
• Chloroacetic acid
• SODIUM TRICHLOROACETATE