α-Ketoglutaric acid

α-Ketoglutaric acid
Names
	Preferred IUPAC name 2-Oxopentanedioic acid
	Other names 2-Ketoglutaric acid; alpha-Ketoglutaric acid; 2-Oxoglutaric acid; Oxoglutaric acid
Identifiers
CAS Number	328-50-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:30915 ;
ChemSpider	50 ;
DrugBank	DB02926 ;
ECHA InfoCard	100.005.756
IUPHAR/BPS	3636;
KEGG	C00026 ;
MeSH	alpha-ketoglutaric+acid
PubChem CID	51;
UNII	8ID597Z82X ;
CompTox Dashboard (EPA)	DTXSID5033179 ;
	InChI InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10) Key: KPGXRSRHYNQIFN-UHFFFAOYSA-N ; InChI=1/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10) Key: KPGXRSRHYNQIFN-UHFFFAOYAN;
	SMILES O=C(O)C(=O)CCC(=O)O;
Properties
Chemical formula	C5H6O5
Molar mass	146.098 g·mol−1
Melting point	115 °C (239 °F; 388 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

α-Ketoglutaric acid (AKG) is an organic compound with the formula HO₂CCO(CH₂)₂CO₂H. A white, nontoxic solid, it is a common dicarboxylic acid. Relevant to its biological roles, it exists in water as its conjugate base α-ketoglutarate. It is also classified as a 2-ketocarboxylic acid. β-Ketoglutaric acid is an isomer. "Ketoglutaric acid" and "ketoglutarate", when not qualified as α or β, almost always refers respectively to α-ketoglutaric acid or α-ketoglutarate.

α-Ketoglutarate is an intermediate in the citric acid cycle, a set of cyclic reactions that supplies energy to cells. It is also an intermediate in or product of several other metabolic pathways. These include its being a component of metabolic pathways that: make amino acids and in the process regulate the cellular levels of carbon, nitrogen, and ammonia; reduce the cellular levels of potentially toxic reactive oxygen species; and synthesize the neurotransmitter γ-aminobutyric acid (GABA).

A large body of preclinical (i.e., conducted in animal models of disease or on animal or human tissues) research has been conducted on the role of endogenous (generated within the body) α-ketoglutarate. A small amount of preclinical research has been done to determine the effects of providing additional exogenous α-ketoglutarate to biological systems. There is currently no randomized controlled trials showing α-ketoglutarate to have any pharmacological (drug-like) effects on humans. The Food and Drug Administration classifies α-ketoglutaric acid as "503A Category 3: Bulk Drug Substances Nominated Without Adequate Support".