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Sigma-Aldrich

α-Ketoglutaric acid

99.0-101.0% (T)

Synonym(s):

alpha-Ketoglutarate, alpha-Ketoglutaric acid, 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:
12352115
PubChem Substance ID:
329766750
NACRES:
NA.22

Quality Level

300

Assay

99.0-101.0% (T)

form

crystals

mp

114-118 °C

solubility

H2O: 1 g/10 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

α-Ketoglutaric acid is a 2-oxocarboxylic acid (2-OCA) that is formed as a metabolite in the Kreb′s cycle.

Application

α-ketoglutaric acid along with L-arginine can undergo reduction with sodium cyanoborohydride to form the diastereomers, nopaline and isonopaline.

Other Notes

Reagent for the analysis of tryptophan; Substrate for glutamate dehydrogenase

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG9572
BCCG9573
BCCG8856
BCCG6762
BCCG2986

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A useful synthesis of nopaline, a crown gall tumor metabolite
Jensen RE, et al.
Biochemical and Biophysical Research Communications, 75(4), 1066-1070 (1977)
Ewa Tomaszewska et al.
Animals : an open access journal from MDPI, 10(12) (2020-12-23)
The aim of the experiment was to assess the effect of dietary alpha-ketoglutarate (AKG) supplementation on performance, serum hormonal indices, duodenum and jejunum histomorphometry, meat quality characteristics, bone quality traits and cartilage degradation in laying hens with a mature skeletal
White biotechnology for green chemistry: fermentative 2-oxocarboxylic acids as novel building blocks for subsequent chemical syntheses
Stottmeister U, et al.
Journal of Industrial Microbiology & Biotechnology, 32(11-12), 651-664 (2005)
Ewa Tomaszewska et al.
Foods (Basel, Switzerland), 10(3) (2021-04-04)
The current study aimed to assess the effects of dietary alpha-ketoglutarate (AKG) supplementation to laying hens on the fatty acid (FA) profile and cholesterol levels of the egg yolk at the end of production cycle. The experiment was performed on
N. Anderson et al.
Journal of Food Science, 43, 1595-1595 (1978)
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