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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

Quality Level

100

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

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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)
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
An efficient synthesis of 4-aryl kainic acid analogs.
Maeda H, et al.
Tetrahedron, 55(4), 943-954 (1999)
Yuan Cao et al.
Theranostics, 7(12), 3021-3033 (2017-08-26)
Increased glutamine metabolism is a hallmark of cancer. Mitochondrial glutamic pyruvate transaminase (GPT2) catalyzes the reversible transamination between alanine and α-ketoglutarate (α-KG), also known as 2-oxoglutarate, to generate pyruvate and glutamate during cellular glutamine catabolism. However, the precise role of
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
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Glutamine Metabolism in Cancer Cells

Sigma article discusses tumor cell metabolic pathways, focusing on aerobic glycolysis and mitochondrial activity.

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