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75890

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/REAXYS Number:
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

signalword

Danger

hcodes

H318

Hazard Classifications

Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL6411
BCCM4790
BCCM1228
BCCL0231
BCCK1590

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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)
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)
N. Anderson et al.
Journal of Food Science, 43, 1595-1595 (1978)
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
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
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