5303. α-Ketoglutaric Acid

Nomenclature

CAS number: 328-50-7
2-Oxopentanedioic acid; 2-oxoglutaric acid; 2-oxo-1,5-pentanedioic acid.
C5H6O5; mol wt 146.10.
C 41.10%, H 4.14%, O 54.75%.
HOOCCH2CH2COCOOH.

Description and references

Plays an important role in amino acid metabolism (transamination) see Severo Ochoa, “Enzymic Mechanisms in the Citric Acid Cycle” in Adv. Enzymol. 15, 183-270 (1954). Prepn: Friedman, Kosower, Org. Synth. coll. vol. III, 510 (1955); Bottorff, Moore, ibid. coll. vol. V, 687 (1973). Microbial synthesis using a strain of Pseudomonas: Lockwood et al., US 2443919 (1948); Berger, Witt, US 2841616 (1958).

Properties

Crystals from acetone-benzene, mp 113.5°. Freely sol in water, alcohol. Very sparingly sol in ether.

Derivative

Diethyl ester.
C9H14O5; mol wt 202.20.
C 53.46%, H 6.98%, O 39.56%.

Properties

Liq, bp23 160°, bp13 144°.

Derivative

Compound with l(+)-ornithine.

Nomenclature

l(+)-Ornithine α-ketoglutarate; Ornicetil (Logeais; Nordmark).
C10H18N2O7; mol wt 278.26.
C 43.16%, H 6.52%, N 10.07%, O 40.25%.

Use

Can be converted to l-glutamic acid by Aeromonas spp. see Good, US 2933434 (1960 to International Minerals & Chem. Corp.).