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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 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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

Certificates of Analysis (COA)

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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
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
An efficient synthesis of 4-aryl kainic acid analogs.
Maeda H, et al.
Tetrahedron, 55(4), 943-954 (1999)
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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Articles

Glutamine Metabolism is Dysregulated in Many Cancer Cells

Sigma-Aldrich presents an article about how 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 metabolites away from mitochondrial oxidative phosphorylation, many tumor cells exhibit increased mitochondrial activity.

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