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K1750

Sigma-Aldrich

α-Ketoglutaric acid

≥98.5% (NaOH, titration)

Synonym(s):

2-Oxoglutaric acid, 2-Oxopentanedioic acid

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About This Item

Linear Formula:
HOOCCH2CH2COCOOH
CAS Number:
328-50-7
Molecular Weight:
146.10
Beilstein:
1705689
EC Number:
206-330-3
MDL number:
MFCD00004165
UNSPSC Code:
12352204
PubChem Substance ID:
57654314
NACRES:
NA.32

Quality Level

200

Assay

≥98.5% (NaOH, titration)

form

powder

solubility

water: 100 mg/mL, clear to slightly hazy, colorless to faintly yellow

storage temp.

2-8°C

SMILES string

OC(=O)CCC(=O)C(O)=O

InChI

1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)

InChI key

KPGXRSRHYNQIFN-UHFFFAOYSA-N

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General description

α-Ketoglutaric acid (α-KG) is produced in the tricarboxylic acid cycle.

Application

α-Ketoglutaric acid (α-KG) has been used:
  • to study its effects on swine fecal microflora in an in vitro fermentation system
  • to study its effects on the activation of CD8+ T-cells
  • as a substrate in glutamate oxaloacetate transaminase (GOT2) mitochondrial lysate assay

Biochem/physiol Actions

α-Ketoglutaric acid (α-KG) has a wide range of applications in the animal feed, food, pharmaceutical and fine chemistry industries.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338

Hazard Classifications

Eye Dam. 1

Storage Class Code

11 - Combustible Solids

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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J Kitaura et al.
European journal of pediatrics, 158(5), 410-413 (1999-05-20)
Two cases of hyperinsulinaemic hypoglycaemia associated with persistent hyperammonaemia in unrelated infants of 7 days and 4 months of age are reported. Blood ammonia levels were 100-300 micromol/l (normal values <40 micromol/l). The hyperammonaemia was asymptomatic and not associated with
F Rocchiccioli et al.
Biomedical mass spectrometry, 11(1), 24-28 (1984-01-01)
Quantification of 2-ketoglutaric acid in plasma and cerebrospinal fluid as its O-trimethylsilyl++-quinoxalinol derivative by gas chromatography chemical ionization mass spectrometry is described with benzoylformic acid as internal standard. This technique, with ammonia as reactant gas, only detects the protonated molecular
Agata M Pudlik et al.
Applied and environmental microbiology, 79(4), 1095-1101 (2012-12-04)
Transamination is the first step in the conversion of amino acids into aroma compounds by lactic acid bacteria (LAB) used in food fermentations. The process is limited by the availability of α-ketoglutarate, which is the best α-keto donor for transaminases
Victoria I Bunik et al.
International journal of molecular sciences, 21(11) (2020-05-30)
Genetic up-regulation of mitochondrial 2-oxoglutarate dehydrogenase is known to increase reactive oxygen species, being detrimental for cancer cells. Thiamine diphosphate (ThDP, cocarboxylase) is an essential activator of the enzyme and inhibits p53-DNA binding in cancer cells. We hypothesize that the
Ivanhoe K H Leung et al.
Journal of medicinal chemistry, 56(2), 547-555 (2012-12-14)
The human 2-oxoglutarate (2OG) dependent oxygenases belong to a family of structurally related enzymes that play important roles in many biological processes. We report that competition-based NMR methods, using 2OG as a reporter ligand, can be used for quantitative and
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