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

Ethyl (R)-(-)-4-cyano-3-hydroxybutyate
  • CAS No.:141942-85-0
Other grades of this product :
Ethyl (R)-(-)-4-cyano-3-hydroxybutyate Basic information
Product Name:Ethyl (R)-(-)-4-cyano-3-hydroxybutyate
Synonyms:(R)-(-)-4-CYANO-3-HYDROXYBUTYRIC ACID ETHYL ESTER;(R)-4-CYANO-3-HYDROXYBUTYRIC ACID ETHYL ESTER;(R)-(-)-ETHYL 4-CYANO-3-HYDROXYBUTYRATE;(R)-ETHYL 4-CYANO-3-HYDROXYBUTYRATE;(S)-4-CYANO-3-HYDROXYBUTANOATE ETHYL;ETHYL (3R)-4-CYANO-3-HYDROXY-BUTANOATE;ETHYL (S)-4-CYANO-3-HYDROXYBUTANOATE;ETHYL (R)-4-CYANO-3-HYDROXYBUTANOATE
CAS:141942-85-0
MF:C7H11NO3
MW:157.17
EINECS:430-220-6
Product Categories:Atorvastatin intermediates;chiral;Alcohols, Hydroxy Esters and Derivatives;Chiral Compounds;INTERMEDIATESOFATORVASTATIN;API intermediates;Pharmaceutical Intermediates
Mol File:141942-85-0.mol
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.)
Fp >230 °F
storage temp. 2-8°C
solubility Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
pka13.03±0.20(Predicted)
form Liquid
Specific Gravity1.114
color Colorless to yellow
optical activity[α]25/D 5°, neat
BRN 5328715
InChIKeyLOQFROBMBSKWQY-ZCFIWIBFSA-N
CAS DataBase Reference141942-85-0(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 1
HS Code 29269090
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
Ethyl (R)-(-)-4-cyano-3-hydroxybutyate Usage And Synthesis
Chemical Propertiesyellow liquid
UsesAtorvastatin Intermediate
Usesanalgesic, 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.
ApplicationHydroxyglutaryl 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.
Ethyl (R)-(-)-4-cyano-3-hydroxybutyate Preparation Products And Raw materials
Raw materialsButanoic acid, 4-cyano-3-hydroxy-, (3R)--->Ethyl 4-bromo-3-hydroxybutyrate-->Sodium cyanide-->Ethanol-->Ethyl 4-chloroacetoacetate
Preparation Products(3R,5R)-6-Cyano-3,5-dihydroxy-hexanoic Acid tert-Butyl Ester

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