95310-88-6

Basic information

• Product Name: (S)-3-HYDROXYGLUTARATE ETHYL
• Synonyms: ETHYL (S)-3-HYDROXYGLUTARATE
• CAS NO: 95310-88-6
• Molecular Formula: C₇H₁₂O₅
• Molecular Weight: 176.17
• Product Categories: Alcohols, Hydroxy Esters and Derivatives;Chiral Compounds
• Mol File: 95310-88-6.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-3-HYDROXYGLUTARATE ETHYL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-HYDROXYGLUTARATE ETHYL(95310-88-6)
• EPA Substance Registry System: (S)-3-HYDROXYGLUTARATE ETHYL(95310-88-6)

Safety Data

• Hazardous Substances Data: 95310-88-6(Hazardous Substances Data)

Usage

Description

(S)-3-Hydroxyglutarate ethyl, with the molecular formula C6H10O5, is a chemical compound derived from 3-hydroxyglutaric acid. (S)-3-HYDROXYGLUTARATE ETHYL plays a role in various metabolic pathways within the human body and has garnered interest for its potential therapeutic applications, particularly in cancer and metabolic diseases. Its unique structure and properties position it as a promising candidate for further research and development in pharmaceuticals and medical treatments. However, additional studies are necessary to comprehensively understand its mechanisms of action and potential benefits across different disease states.

Uses

Used in Pharmaceutical Industry:
(S)-3-Hydroxyglutarate ethyl is used as a therapeutic agent for its potential applications in treating cancer and metabolic diseases. Its involvement in key metabolic pathways makes it a candidate for targeted interventions and novel treatment strategies.
Used in Medical Research:
In the field of medical research, (S)-3-Hydroxyglutarate ethyl serves as a subject of investigation to better understand its mechanisms of action and how it can be leveraged for the development of new pharmaceuticals and medical treatments.
Used in Drug Development:
(S)-3-Hydroxyglutarate ethyl is utilized as a compound in drug development, with the aim of creating new medications that can effectively target and treat cancer and metabolic diseases by modulating the metabolic pathways in which this compound is involved.

Upstream product

• 113036-11-6 (3R)-3-(acetyloxy)-5-ethoxy-5-oxopentanoic acid 
• 91967-12-3 ethyl 3-acetoxypentanedioate 
• 141942-85-0 (R)-ethyl 4-cyano-3-hydroxybutyrate 
• 32328-03-3 diethyl 3-hydroxyglutarate 

Downstream Products

• 113036-11-6 (3R)-3-(acetyloxy)-5-ethoxy-5-oxopentanoic acid 
• 917752-46-6 ethyl (3R)-(tert-butyldimethylsilyloxy)-5-oxo-6-(triphenylphosphoranylidene)-hexanoate 

Relevant articles and documents

Enzymatic synthesis of a key intermediate for rosuvastatin by nitrilase-catalyzed hydrolysis of ethyl (R)-4-cyano-3-hydroxybutyate at high substrate concentration

An enzymatic method for the synthesis of ethyl (R)-3-hydroxyglutarate from ethyl (R )-4-cyano-3-hydroxybutyate was developed by using free and immobilized recombinant Escherichia coli BL21(DE3)pLysS harboring a nitrilase gene from Arabidopsis thaliana (AtNIT2). The hydrolysis of ethyl (R)-4-cyano-3-hydroxybutyate proceeded with the freely suspended cells of the biocatalyst under the optimized conditions of 1.5 molL-1 (235.5 gL-1) substrate concentration and 6.0 wt% loading of wet cells at pH 8.0 and 25 °C, with 100% conversion obtained in 4.5 h. Furthermore, immobilization of the whole cells enhanced their substrate tolerance, stability, and reusability. Under the optimized conditions (100 mmolL-1 tris(hydroxymethyl) aminomethane hydrochloride buffer, pH 8.0, 25 °C), the immobilized biocatalyst could be reused for up to 16 batches, with a biocatalyst productivity of 55.6 ggwet cells-1 and a spacetime productivity of 625.5 gL-1 d-1. These results demonstrated that the immobilized whole cells might be used as a biocatalyst in the industrial production of ethyl (R)-3-hydroxyglutarate, a key intermediate for the synthesis of rosuvastatin.

Efficient biosynthesis of ethyl (R)-3-hydroxyglutarate through a one-pot bienzymatic cascade of halohydrin dehalogenase and nitrilase

An effective one-pot bienzymatic synthesis of ethyl (R)-3-hydroxyglutarate (EHG) from ethyl (S)-4-chloro-3-hydroxybutyrate (ECHB) was achieved by using recombinant Escherichia coli cells expressing separately or co-expressing a mutant halohydrin dehalogenase gene from Agrobacterium radiobacter AD1 and a nitrilase gene from Arabidopsis thaliana. The activity of nitrilase was inhibited by high concentration of ECHB and NaCN. Consequently, the one-pot one-step process was implemented by fed-batch of ECHB and NaCN with high accumulative product concentration (up to 0.9 mol L-1). The biotransformation of ECHB to EHG was successfully achieved at 1.2 mol L-1 substrate concentration by a one-pot two-step process. As such, this one-pot bienzymatic transformation should be useful in synthesizing these important optical pure β-hydroxycarboxylic acids.

Bifunctional chiral synthons via biochemical methods. 5. Preparation of (S)-ethyl hydrogen-3-hydroxyglutarate, key intermediate to (R)-4-amino-3-hydroxybutyric acid and L-carnitine

Microbial enantioselective hydrolysis of diethyl-3-hydroxyglutarate afforded (S)-ethyl hydrogen-3-hydroxyglutarate, which was transformed into (R)-4-amino-3-hydroxybutyric acid and L-carnitine, via a Curtius and Hunsdiecker rearrangement, respectively.