Skip to Content
Merck
All Photos(1)

Documents

K1128

Sigma-Aldrich

α-Ketoglutaric acid

BioReagent, suitable for cell culture, suitable for insect cell culture

Synonym(s):

2-Oxoglutaric acid, 2-Oxopentanedioic acid

Sign Into View Organizational & Contract Pricing


About This Item

Linear Formula:
HOOCCH2CH2COCOOH
CAS Number:
Molecular Weight:
146.10
Beilstein:
1705689
EC Number:
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.32

product line

BioReagent

Assay

≥98.5% NaOH basis (titration)

form

powder or crystals

technique(s)

cell culture | insect: suitable
cell culture | mammalian: suitable

solubility

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

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

Looking for similar products? Visit Product Comparison Guide

General description

Alpha-ketoglutarate (αKG), a vital intermediate in the tricarboxylic acid (TCA)/Krebs cycle, is located between succinyl-CoA and isocitrate.

Application

α-Ketoglutaric acid has been used:
  • as a supplement in minimum essential medium α (α-MEM) to culture primary mesenchymal stromal/stem cells (MSCs) to study its effects on age-related osteoporosis
  • for chemical treatments to compare the treatment effects of several compounds on lifespan between manual and automated lifespan machine (ALM) platforms
  • as a printed chemotaxis ligand to screen chemotaxis receptors with high-throughput technologies and verify the interactions with surface plasmon resonance (SPR)

Biochem/physiol Actions

Alpha-ketoglutarate (αKG), a nitrogen scavenger, is an important source of glutamate and glutamine. It controls the synthesis of ATP and decreases the generation of equivalent (NAD+/NADH) in the tricarboxylic acid (TCA) cycle. It promotes the synthesis of protein and prevents protein degradation in muscles. This immune nutrient factor participates in the general immune and collagen metabolism. In aged rodents, αKG accelerates the healing of bone defects. It may possess potential anti-aging effects. This Krebs cycle molecule can be used as a supplement in insect and mammalian cell cultures.

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Precautionary Statements

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Nan Wu et al.
Biomolecules & therapeutics, 24(1), 1-8 (2016-01-14)
Alpha-ketoglutarate (AKG) is a key molecule in the Krebs cycle determining the overall rate of the citric acid cycle of the organism. It is a nitrogen scavenger and a source of glutamate and glutamine that stimulates protein synthesis and inhibits
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
Yuan Wang et al.
Nature communications, 11(1), 5596-5596 (2020-11-07)
Age-related osteoporosis is characterized by the deterioration in bone volume and strength, partly due to the dysfunction of bone marrow mesenchymal stromal/stem cells (MSCs) during aging. Alpha-ketoglutarate (αKG) is an essential intermediate in the tricarboxylic acid (TCA) cycle. Studies have
Christopher J Day et al.
Methods in molecular biology (Clifton, N.J.), 1729, 303-317 (2018-02-13)
Ligand-receptor interactions triggering signal transduction components of many sensory pathways, remain elusive due to paucity of high-throughput screening methods. Here we describe our use of small molecule microarrays comprising of small glycans, amino and organic acids, salts, and other known
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

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