69134-53-8

Basic information

• Product Name: Diethyl2-hydroxyglutarate,2-Hydroxyglutaricaciddiethylester
• Synonyms: Diethyl2-hydroxyglutarate,2-Hydroxyglutaricaciddiethylester;Diethyl2-hydroxyglutarate;2-Hydroxyglutaric acid diethyl ester;Pentanedioic acid, 2-hydroxy-, diethyl ester;Pentanedioic acid, 2-hydroxy-, 1,5-diethyl ester;Diethyl 2-hydroxypentanedioate
• CAS NO: 69134-53-8
• Molecular Formula: C₉H₁₆O₅
• Molecular Weight: 204.22034
• Mol File: 69134-53-8.mol

Chemical Properties

• Boiling Point: 291.8°C at 760 mmHg
• Flash Point: 107.8°C
• Appearance: /
• Density: 1.122g/cm³
• Vapor Pressure: 0.000205mmHg at 25°C
• Refractive Index: 1.448
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• PKA: 12.84±0.20(Predicted)
• CAS DataBase Reference: Diethyl2-hydroxyglutarate,2-Hydroxyglutaricaciddiethylester(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl2-hydroxyglutarate,2-Hydroxyglutaricaciddiethylester(69134-53-8)
• EPA Substance Registry System: Diethyl2-hydroxyglutarate,2-Hydroxyglutaricaciddiethylester(69134-53-8)

Safety Data

• Hazardous Substances Data: 69134-53-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Diethyl 2-hydroxyglutarate, 2-hydroxyglutaric acid diethyl ester is used as a reagent in organic synthesis for the preparation of various chemical compounds and intermediates. Its unique structure and functional groups make it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Antioxidant and Anti-inflammatory Applications:
Diethyl 2-hydroxyglutarate, 2-hydroxyglutaric acid diethyl ester is used as an antioxidant and anti-inflammatory agent due to its ability to scavenge free radicals and modulate inflammatory pathways. This makes it a potential candidate for the development of therapeutic agents to treat oxidative stress-related diseases and inflammatory conditions.
Used in Neurological Disorder Treatment:
Diethyl 2-hydroxyglutarate, 2-hydroxyglutaric acid diethyl ester has been investigated for its potential as a treatment for certain neurological disorders. Its neuroprotective properties and ability to modulate neurotransmitter levels make it a promising candidate for the development of drugs targeting neurological conditions such as Alzheimer's disease, Parkinson's disease, and other neurodegenerative disorders.
Used in Cancer Therapy:
Diethyl 2-hydroxyglutarate, 2-hydroxyglutaric acid diethyl ester is used as a potential candidate for cancer therapy due to its ability to inhibit the activity of certain enzymes involved in cancer metabolism. This makes it a promising agent for the development of targeted cancer therapies, particularly for cancers that rely on specific metabolic pathways for growth and survival.
Used in Drug Delivery Systems:
To enhance the bioavailability, delivery, and therapeutic outcomes of diethyl 2-hydroxyglutarate, 2-hydroxyglutaric acid diethyl ester, various drug delivery systems have been developed. These systems, including organic and metallic nanoparticles, aim to improve the compound's solubility, stability, and targeted delivery to cancer cells, thereby enhancing its anticancer efficacy and reducing side effects.

InChI:InChI=1/C9H16O5/c1-3-13-8(11)6-5-7(10)9(12)14-4-2/h7,10H,3-6H2,1-2H3

Upstream product

• 2889-31-8 2-hydroxyglutaric acid 
• 368-39-8 triethyloxonium fluoroborate 
• 7209-00-9 diethyl 2-bromoglutarate 
• 110-94-1 1,5-pentanedioic acid 
• 328-50-7 α-ketoglutaric acid 
• 305-72-6 α-ketoglutaric acid disodium salt 
• 64-17-5 ethanol 
• 73178-43-5 (E)-diethyl glutaconate 
• 5965-53-7 diethyl 2-ketoglutarate 

Downstream Products

• 1126-51-8 (+/-)-tetrahydro-5-oxo-2-furancarboxylic acid ethyl ester 
• 1126-51-8 (S)-(+)-tetrahydro-5-oxo-2-furancarboxylic acid ethyl ester 
• 33019-03-3 (R)-(-)-tetrahydro-5-oxo-2-furancarboxylic acid ethyl ester 

Relevant articles and documents

Biotechnological properties of sponges from northeast Brazil: Cliona varians as a Biocatalyst for Enantioselective Reduction of Carbonyl Compounds

To research the potential ability of whole marine sponges to act as biocatalysts, this paper describes for the first time the employment of whole Cliona varians sponge in the stereoselective reduction of prochiral α-keto esters and isatin to the corresponding chiral alcohols. The addition of D-fructose, D-glucose or sucrose remarkably increased the conversion ratios and stereoselectivities by this marine sponge. Furthermore, in the presence of D-glucose and D-maltose, the reduction of isatin by C. varians afforded the corresponding 3-hydroxyindolin-2-one with high conversions (85-90percent) and good enantioselectivities (60-74percent). These results showed that the marine sponge presents great potential to be used as biocatalyst for stereoselective reduction of carbonyl compounds.

Asymmetric synthesis of alkyl 5-oxotetrahydrofuran-2-carboxylates by enantioselective hydrogenation of dialkyl 2-oxoglutarates over cinchona modified Pt/Al2O3 catalysts

The first direct asymmetric synthesis of chiral alkyl 5- oxotetrahydrofuran-2-carboxylates (up to 96% ee), which are important building blocks in the synthesis of natural products by heterogeneous cinchona-modified Pt-catalyzed hydrogenation of α-ketoglutaric acid esters and subsequent cyclization of hydroxy esters is described.

Stereochemistry of the methyl group in (R)-3-methylitaconate derived by rearrangement of 2-methylideneglutarate catalysed by a coenzyme B12-dependent mutase

2-Methylideneglutarate mutase is an adenosylcobalamin (coenzyme B12)-dependent enzyme that catalyses the equilibration of 2-methylideneglutarate with (R)-3-methylitaconate. This reaction is believed to occur via protein-bound free radicals derived from substrate and product. The stereochemistry of the formation of the methyl group of 3-methylitaconate has been probed using a 'chiral methyl group'. The methyl group in 3-([2H1,3H]methyl)itaconate derived from either (R)- or (S)-2-methylidene[3-2H1,3-3H1]glutarate was a 50 : 50 mixture of (R)- and (S)-forms. It is concluded that the barrier to rotation about the C-C bond between the methylene radical centre and adjacent C-atom in the product-related radical [CH2CH(-O2CC=CH2)CO2-] is relatively low, and that the interaction of the radical with cob(1I)alamin is minimal. Hence, cob(I1)alamin is a spectator of the molecular rearrangement of the substrate radical to product radical.

Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters from dialkyl 2-oxoglutarates

Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters can be prepared either by enzymatic resolution of the racemic γ-lactones themselves or by bioreduction with baker's yeast of dialkyl 2-oxoglutarates and subsequent cyclization of the resulting dialkyl 2-hydroxyglutarates. The best results were obtained by the former route, by which the desired compounds were isolated in high enantiomeric excess. Bioreductions were less satisfactory. In fact the hydroxyester intermediates were initially formed as racemic mixtures and their final enantiomeric enrichment was reached by asymmetric destruction, occurring in the bioreaction medium, however at the same time large amounts of alkyl 4-hydroxybutanoates were formed as side products.

Stereochemical control in microbial reduction. Part 31: Reduction of alkyl 2-oxo-4-arylbutyrates by baker's yeast under selected reaction conditions

Treatment of baker's yeast with phenacyl chloride in an aqueous-organic solvent has been proven to be an effective method of inhibiting the enzymes that afford (S)-enantiomers of α-hydroxy esters in the reduction of α-keto esters. The procedure is effective for the whole-cell system to produce the (R)-product with high chemical yield and high enantiomeric excess.

The chemistry of phosphapeptides: Investigations on the synthesis of phosphonamidate, phosphonate, and phosphinate analogues of glutamyl-γ-glutamate

The synthesis of the phosphonamidate, 1d, and phosphonate, 1e, analogues of a γ-glutamyl peptide are reported. Michaelis-Albuzov reaction with the alkyl halide, 7b, derived from L-glutamic acid, yielded dimethyl phosphonate, 8b. Selective aminolysis of th

A New and Facile Method for the Direct Preparation of α-Hydroxycarboxylic Acid Esters from α,β-Unsaturated Carboxylic Acid Esters with Molecular Oxygen and Phenylsilane Catalyzed by Bis(dipivaloylmethanato)manganese(II) Complex

In the presence of a catalytic amount of bis(dipivaloylmethanato)manganese(II) complex, the oxygenation of benzyl crotonate with molecular oxygen and phenylsilane proceeds smoothly under a mild condition to give benzyl 2-hydroxybutyrate in high yield.The reaction provides a new and convenient method for the direct preparation of various α-hydroxycarboxylic acid esters starting from α,β-unsaturated carboxylic acid esters.The influence of substituents of olefins on regioselectivity is also studied.

Meerwein Reduction of Levulinic Acid Derivatives: A New Route for the Synthesis of Glutamic Acid

Glutamic acid has been prepared from levulinic acid by a new route.In this method α-ketoglutaric (III) acid is obtained by oxidation of δ-benzallevulinic acid (II) and converted into diethyl ester (IV) which on Meerwein-Pondorff-Verley reduction furnishes the hydroxy derivative (V).The latter (V) is converted into chloro derivative (VI) which on amination gives glutamic acid (VII) in a good yield.Meerwein-Pondorff-Verley reduction of ethyl levulinate, ethyl β-bromolevulinate and 2,7-octanedione has also been studied.However, such a reduction of ethyl β-aminolevulinate remains unsuccessfull.