349631
Dimethyl 2-oxoglutarate
96%
Synonym(s):
Dimethyl α-ketoglutarate
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About This Item
Linear Formula:
CH3O2CCH2CH2COCO2CH3
CAS Number:
Molecular Weight:
174.15
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Assay:
96%
Form:
liquid
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
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
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves
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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
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)