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349631 Sigma-Aldrich

Dimethyl 2-oxoglutarate

96%

Synonym: Dimethyl α-ketoglutarate

  • CAS Number 13192-04-6

  • Linear Formula CH3O2CCH2CH2COCO2CH3

  • Molecular Weight 174.15

  •  MDL number MFCD00048052

  •  PubChem Substance ID 24861693

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, C6 to C7, Cancer Metabolism, Cancer Research, Carbonyl Compounds,
assay   96%
refractive index   n20/D 1.439 (lit.)
bp   90-95 °C/0.4 mmHg (lit.)
density   1.203 g/mL at 25 °C (lit.)
SMILES string   COC(=O)CCC(=O)C(=O)OC
InChI   1S/C7H10O5/c1-11-6(9)4-3-5(8)7(10)12-2/h3-4H2,1-2H3
InChI key   TXIXSLPEABAEHP-UHFFFAOYSA-N

Description

General description

Dimethyl 2-oxoglutarate is a key intermediate formed during the Krebs cycle and an important nitrogen transporter in the biological metabolic pathways. The electrochemical behavior of dimethyl-2-oxoglutarate has been investigated by cyclic voltammetry, square wave voltammetry and differential pulse voltammetry using a glassy carbon electrode.

Application

Dimethyl 2-oxoglutarate can undergo cylocondensation with dinucleophiles, such as 1,2-phenylenediamine, 2-aminophenol and 2-aminobenzenethiol to form novel heterocycles.

Dimethyl 2-oxoglutarate may be used to synthesize the conformationally constrained PNA (peptide nucleic acid) -monomer capable of binding thymine in a triplex motif. It may be used in the synthesis of 4-aryl kainic acid analogs, via highly stereoselective Michael addition reaction with nitrostyrene.

Packaging

5 g in glass bottle

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

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Protocols & Articles

Articles

Glutamine Metabolism is Dysregulated in Many Cancer Cells

Proliferatively active cells require both a source of carbon and of nitrogen for the synthesis of macromolecules. Although a large proportion of tumor cells utilize aerobic glycolysis and shunt metab...
BioFiles v7 n4
Keywords: Aerobic, Cancer, Citric Acid Cycle, Gene expression, Glycolysis, Metabolism, Metabolites, Phosphorylations, Transcription

Peer-Reviewed Papers
15

References

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