α-Ketoglutaric acid-d6, α-Ketopentanoic acid-d6 Chemical Properties

Melting point:

114-117 °C

form 

Solid

color 

White to off-white

InChI

1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)/i1D2,2D2/hD2

InChIKey

KPGXRSRHYNQIFN-DTDGFSOZSA-N

SMILES

[2H]OC(=O)C(=O)C([2H])([2H])C([2H])([2H])C(=O)O[2H]

CAS Number Unlabeled

328-50-7

Safety Information

Hazard Codes 

Xi

Risk Statements 

37/38-41

Safety Statements 

26-39

WGK Germany 

WGK 3

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Dam. 1
Skin Irrit. 2
STOT SE 3

α-Ketoglutaric acid-d6, α-Ketopentanoic acid-d6 Usage And Synthesis

Uses

2-Ketoglutaric acid-d6 is the deuterium labeled 2-Ketoglutaric acid[1]. 2-Ketoglutaric acid (Alpha-Ketoglutaric acid) is an intermediate in the production of ATP or GTP in the Krebs cycle. 2-Ketoglutaric acid also acts as the major carbon skeleton for nitrogen-assimilatory reactions. 2-Ketoglutaric acid is a reversible inhibitor of tyrosinase (IC50=15 mM)[2].

References

[1] Russak EM, et al. Impact of Deuterium Substitution on the Pharmacokinetics of Pharmaceuticals. Ann Pharmacother. 2019 Feb;53(2):211-216. DOI:10.1177/1060028018797110
[2] Huergo LF, et al. The Emergence of 2-Oxoglutarate as a Master Regulator Metabolite. Microbiol Mol Biol Rev. 2015 Dec;79(4):419-35. DOI:10.1128/MMBR.00038-15
[3] Gou L, et al. The effect of alpha-ketoglutaric acid on tyrosinase activity and conformation: Kinetics and molecular dynamics simulation study. Int J Biol Macromol. 2017 Dec105(Pt 3):1654-1662. DOI:10.1016/j.ijbiomac.2016.12.015