Dimethyl malate Chemical Properties

Boiling point:

104-108 °C1 mm Hg(lit.)

Density 

1.232 g/mL at 20 °C(lit.)

refractive index 

n20/D 1.441

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

Chloroform (Sparingly), Methanol (Slightly)

pka

11.72±0.20(Predicted)

form 

Liquid

color 

Colorless to pale yellow

optical activity

[α]20/D 6.5°, neat

BRN 

1724363

InChIKey

YSEKNCXYRGKTBJ-BYPYZUCNSA-N

LogP

-0.830 (est)

CAS DataBase Reference

617-55-0(CAS DataBase Reference)

EPA Substance Registry System

Dimethyl L-malate (617-55-0)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-43-41-10

Safety Statements 

26-36-43-37/39-24

RIDADR 

1993

WGK Germany 

3

F 

10-21

HazardClass 

3

PackingGroup 

Ⅲ

HS Code 

29181990

MSDS

• Language:English Provider:SigmaAldrich

Dimethyl malate Usage And Synthesis

Chemical Properties

Colourless Oil

Uses

This chiral synthon has been used to prepare cytochrome P450 metabolites of arachidonic acid, and cyclic sulfolanes with HIV-1 protease inhibition potential.

Synthesis

Thionyl chloride (117 g, 0.98 mol) was slowly added dropwise to a methanol (400 mL) solution of L-malic acid (59.9 g, 0.45 mol) in an ice-water bath. After the dropwise addition, the reaction mixture was stirred at room temperature (25 °C) for overnight reaction. The progress of the reaction was monitored by thin layer chromatography (TLC, unfolding agent ratio ethyl acetate: methanol = 10:1). After completion of the reaction, the solvent was evaporated under reduced pressure. Saturated sodium bicarbonate solution (200 mL) was added to the residue and the aqueous phase was extracted with ethyl acetate (3 x 150 mL). The organic phases were combined, washed sequentially with water (3×80 mL), saturated saline (3×80 mL) and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give dimethyl L-malate as a light yellow oil in 98% yield (71.5 g, 0.44 mol).

References

[1] Bioorganic and medicinal chemistry, 2002, vol. 10, # 6, p. 1829 - 1839
[2] Organic Letters, 2009, vol. 11, # 5, p. 1135 - 1137
[3] RSC Advances, 2016, vol. 6, # 27, p. 22737 - 22748
[4] Tetrahedron, 1992, vol. 48, # 30, p. 6325 - 6334
[5] Tetrahedron Letters, 2003, vol. 44, # 16, p. 3391 - 3395

Dimethyl malate(617-55-0)Related Product Information

• Dimethyl sebacate
• Dimethyl phthalate
• Dimethyl sulfate
• Dimethyl carbonate
• Dimethyl oxalate
• Dimethyl fumarate
• Dimethyl ether
• Dacthal
• ETHANE
• Malic acid
• Dimethyl sulfide
• Dimethyl sulfoxide
• N,N-Dimethylformamide
• Dimethyl malate
• Triethyl citrate
• (-)-Dimethyl D-tartrate
• CITRIC ACID TRIALLYL ESTER
• Acetyl tributyl citrate