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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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Long Liu et al.
Journal of biotechnology, 164(1), 97-104 (2013-01-22)
Currently, α-ketoglutaric acid (α-KG) is industrially produced by multi-step chemical synthesis, which can cause heavy environmental pollution. Here we reported a simple one-step approach for the production of α-KG by transforming l-glutamic acid with an engineered l-amino acid deaminase (l-AAD)
G Biagi et al.
Journal of animal science, 85(5), 1184-1191 (2007-02-14)
Adding organic acids to piglet diets is known to be helpful in overcoming postweaning syndrome, and butyric acid is known to be the main energy source for the epithelial cells of the large intestine and the terminal ileum. This study
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
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
R V Durán et al.
Oncogene, 32(38), 4549-4556 (2012-10-23)
Hypoxia-inducible factor (HIF) prolyl hydroxylases (PHDs) are α-ketoglutarate (αKG)-dependent dioxygenases that function as cellular oxygen sensors. However, PHD activity also depends on factors other than oxygen, especially αKG, a key metabolic compound closely linked to amino-acid metabolism. We examined the
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