Ethyl (R)-(-)-4-cyano-3-hydroxybutyate Chemical Properties

alpha 

-5 º (neat)

Boiling point:

270 °C(lit.)

Density 

1.114 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.448(lit.)

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)

pka

13.03±0.20(Predicted)

form 

Liquid

Specific Gravity

1.114

color 

Colorless to yellow

optical activity

[α]25/D 5°, neat

BRN 

5328715

InChIKey

LOQFROBMBSKWQY-ZCFIWIBFSA-N

CAS DataBase Reference

141942-85-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

1

HS Code 

29269090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Ethyl (R)-(-)-4-cyano-3-hydroxybutyate Usage And Synthesis

Chemical Properties

yellow liquid

Uses

analgesic, antipyretic, and anti-inflammatory

Uses

(3R)-4-Cyano-3-hydroxybutanoic Acid Ethyl Ester is used in a biocatalytic process for the synthesis of an atorvastatin intermediate and degredation products/impurities.

Application

Hydroxyglutaryl coenzyme A (HMG-CoA) reductase inhibitors are a new class of lipid-lowering drugs, and they have a market share of more than 10 billion US dollars in the current pharmaceutical field. They can selectively inhibit the rate-limiting enzyme HMG-CoA reductase in cholesterol synthesis in the liver, reduce liver lipoprotein production, and increase the expression of low-density lipoprotein (LDL) cholesterol receptors, thereby reducing plasma cholesterol levels. They can also significantly reduce very low-density lipoprotein (VLDL) and triglycerides, and increase anti-atherosclerotic high-density protein (HDL), preventing atherosclerosis and coronary heart disease.
Ethyl (R)-(-)-4-cyano-3-hydroxybutyate is an important intermediate for the synthesis of HMG-CoA reductase inhibitors. If it is used as a raw material, synthetic atorvastatin is mainly used for the treatment of hypercholesterolemia and mixed hyperlipidemia, coronary heart disease and stroke.

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