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349631

Sigma-Aldrich

Dimethyl 2-oxoglutarate

96%

Synonym(s):

Dimethyl α-ketoglutarate

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About This Item

Linear Formula:
CH3O2CCH2CH2COCO2CH3
CAS Number:
13192-04-6
Molecular Weight:
174.15
MDL number:
MFCD00048052
UNSPSC Code:
12352100
PubChem Substance ID:
24861693
NACRES:
NA.22

Assay

96%

form

liquid

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

Related Categories

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.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Organic syntheses based on 2?oxoglutaric acid. V. Syntheses of novel 2H?1, 4?benzothiazines and a 2, 5?dihydro?1, 5?benzothiazepine.
Blitzke T, et al.
Journal of Heterocyclic Chemistry, 34(2), 453-455 (1997)
Anne Goldbech Olsen et al.
Nucleosides, nucleotides & nucleic acids, 22(5-8), 1331-1333 (2003-10-21)
To expand the triplex recognition repertoire of Nucleic Acids, novel nucleobases that recognize thymine in a T-A base pair are still required. A novel conformationally constrained PNA-monomer (II) capable of binding T in a triplex motif was designed and synthesized
Afzal Shah et al.
Bioelectrochemistry (Amsterdam, Netherlands), 77(2), 145-150 (2009-09-22)
The electrochemical behaviour of dimethyl-2-oxoglutarate (MOG), a key intermediate in the Krebs cycle and an important nitrogen transporter in the metabolic pathways in biological processes, was investigated by cyclic voltammetry, square wave voltammetry and differential pulse voltammetry using a glassy
Nicholas Jones et al.
Nature communications, 10(1), 2042-2042 (2019-05-06)
Metabolic pathways that regulate T-cell function show promise as therapeutic targets in diverse diseases. Here, we show that at rest cultured human effector memory and central memory CD4+ T-cells have elevated levels of glycolysis and oxidative phosphorylation (OXPHOS), in comparison
Daniela Gaglio et al.
Molecular systems biology, 7, 523-523 (2011-08-19)
Oncogenes such as K-ras mediate cellular and metabolic transformation during tumorigenesis. To analyze K-Ras-dependent metabolic alterations, we employed ¹³C metabolic flux analysis (MFA), non-targeted tracer fate detection (NTFD) of ¹⁵N-labeled glutamine, and transcriptomic profiling in mouse fibroblast and human carcinoma
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