Ethyl (R)-3-hydroxybutyrate

Ethyl (R)-3-hydroxybutyrate Basic information
Product Name:Ethyl (R)-3-hydroxybutyrate
Synonyms:(R)-(-)-ETHYL 3-HYDROXYBUTANOATE;(R)-(-)-ETHYL 3-HYDROXYBUTYRATE;(R)-(-)-3-HYDROXYBUTYRIC ACID ETHYL ESTER;(R)-3-HYDROXYBUTYRIC ACID ETHYL ESTER;(R)-(-)-3-HYDROXY-N-BUTYRIC ACID ETHYL ESTER;ENZYME MEMBRANE REACTOR (WITHOUT SUPPLEMENTARY ACCESSORIES) EE 99+%;ETHYL R-(-)-3-HYDROXYBUTANOATE;ETHYL (R)-(-)-3-HYDROXYBUTYRATE
CAS:24915-95-5
MF:C6H12O3
MW:132.16
EINECS:695-003-2
Product Categories:Chiral Alcohols;Alcohols, Hydroxy Esters and Derivatives;Chiral Compounds;Chiral Building Blocks;Simple Alcohols (Chiral);Synthetic Organic Chemistry;Chiral Building Blocks;Esters;Organic Building Blocks
Mol File:24915-95-5.mol
Ethyl (R)-3-hydroxybutyrate Structure
Ethyl (R)-3-hydroxybutyrate Chemical Properties
alpha -45.5 º (589nm, c=1, CHCl3)
Boiling point 75-76 °C/12 mmHg (lit.)
density 1.017 g/mL at 25 °C (lit.)
vapor pressure 17.2Pa at 20℃
refractive index n20/D 1.42(lit.)
Fp 148 °F
storage temp. 2-8°C
form Liquid
pka14.45±0.20(Predicted)
Specific Gravity1.017
color Clear, Colorless
optical activity[α]20/D 46°, c = 1 in chloroform
Water Solubility soluble
LogP0.341 at 20℃
CAS DataBase Reference24915-95-5(CAS DataBase Reference)
Safety Information
Risk Statements 36/37/38-52
Safety Statements 24/25
RIDADR 1993
WGK Germany 3
HS Code 29181990
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
Ethyl (R)-3-hydroxybutyrate Usage And Synthesis
DescriptionEthyl (R)-(-)-3-Hydroxybutyrate is a chiral starting material for the production of numerous biologically active compounds.
Chemical Propertiesclear colorless liquid
UsesEthyl (R)-(-)-3-hydroxybutyrate is a chiral building block for the preparation of bioactive compounds used in the pharmaceutical industry. It is formed during the hydrolysis of poly-3-hydroxybutyrate.
DefinitionChEBI: Ethyl (R)-3-hydroxybutanoate is an ethyl 3-hydroxybutyrate. It is functionally related to a (R)-3-hydroxybutyric acid.
General DescriptionEthyl (R)-3-hydroxybutyrate is an enantiomer of 3-hydroxybutyric acid. It is synthesized from diethyl succinate in a one-pot, stereoselective, high-yield process by using asymmetric synthesis and hydrogenation. The reaction vessel used for this synthesis is a reaction solution that has been optimized to be resistant to high pressure and temperature. This product can be used as a renewable feedstock in the production of polyesters and other polymers.
Synthesis(R)-β-Butryrolactone (20 g, 230 mmol) was dissolved in 500 mLethanol with 1.0 mL H2SO4 and stirred at room temperature. Aliquots(100 μL) were added to 1.0 mL of methanol and analyzed by GC-MS for conversion of the lactone. Upon completion (> 48 h), a small amount of solid sodium bicarbonate was added and the solvent removed by rotary evaporation. The residue was taken up in dichloromethane and washed with water. The water layer was extracted twice with ethyl acetate. The pooled organic layers were dried with magnesium sulfate, which was then filtered and the solvent removed by rotary evaporation to yield Ethyl (R)-3-hydroxybutyrate as a clear oil (20.2 g, 66%).
Ethyl (R)-3-hydroxybutyrate Preparation Products And Raw materials
Raw materialsEthyl (S)-3-hydroxybutyrate-->Ethyl acetoacetate
Preparation Products(R)-(-)-1,3-Butanediol
ETHYL (S)-2-HYDROXY-4-PHENYLBUTYRATE ETHYL 1-OXASPIRO[2.5]OCTANE-2-CARBOXYLATE NONACTIN Ethyl 4-hydroxybutanoate H-THR(BZL)-1/2(COOH)2 (R.S) 4 - ethyl chloro-3 hydroxybutyrate 1H-INDOL-3-OL ETHYL (R)-(+)-4-BROMO-3-HYDROXYBUTYRATE L-Threonine benzyl ester hemioxalate [S]-[+]-Ethyl-cyano-3-hydroxybutyrate Diisopropyl D-tartrate TRI-N-AMYL CITRATE VENTURICIDIN A DIETHYL 3-HYDROXYGLUTARATE ETHYL DL-3-HYDROXYBUTYRATE (S)-4-BROMO-3-HYDROXYBUTYRIC ACID ETHYL ETHER ACETYL TRIALLYL CITRATE Ethyl S-4-chloro-3-hydroxybutyrate

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