Merck
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K1128

Sigma-Aldrich

α-Ketoglutaric acid

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

Synonym(s):
2-Oxoglutaric acid, 2-Oxopentanedioic acid
Linear Formula:
HOOCCH2CH2COCOOH
CAS Number:
Molecular Weight:
146.10
Beilstein:
1705689
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.32

product line

BioReagent

Quality Level

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

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General description

Alpha-ketoglutarate (αKG), a vital intermediate in the tricarboxylic acid (TCA)/Krebs cycle, is located between succinyl-CoA and isocitrate.[82]

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
[82]
  • for chemical treatments to compare the treatment effects of several compounds on lifespan between manual and automated lifespan machine (ALM) platforms
  • [43]
  • as a printed chemotaxis ligand to screen chemotaxis receptors with high-throughput technologies and verify the interactions with surface plasmon resonance (SPR)
  • [77]

    Biochem/physiol Actions

    Alpha-ketoglutarate (αKG), a nitrogen scavenger, is an important source of glutamate and glutamine.[61] It controls the synthesis of ATP and decreases the generation of equivalent (NAD+/NADH) in the tricarboxylic acid (TCA) cycle.[82] It promotes the synthesis of protein and prevents protein degradation in muscles. This immune nutrient factor participates in the general immune and collagen metabolism.[61] In aged rodents, αKG accelerates the healing of bone defects. It may possess potential anti-aging effects.[82] 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

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    Certificate of Origin

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