349631
Dimethyl 2-oxoglutarate
96%
Synonym(s):
Dimethyl α-ketoglutarate
Sign Into View Organizational & Contract Pricing
All Photos(1)
About This Item
Linear Formula:
CH3O2CCH2CH2COCO2CH3
CAS Number:
Molecular Weight:
174.15
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
![1,4-Diazabicyclo[2.2.2]octane ReagentPlus®, ≥99%](/deepweb/assets/sigmaaldrich/product/structures/366/129/a6ff4175-974d-4fac-9038-b35e508ef252/640/a6ff4175-974d-4fac-9038-b35e508ef252.png)
Quality Level
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.)
functional group
ester
ketone
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
Choose from one of the most recent versions:
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
Customers Also Viewed
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
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
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)
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
Articles
Sigma article discusses tumor cell metabolic pathways, focusing on aerobic glycolysis and mitochondrial activity.
Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.
Contact Technical Service