alpha-Ketobutyric acid

α-Ketobutyric acid

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Names
IUPAC name 2-oxobutanoic acid
Identifiers
CAS Number	600-18-0 Y
ChEBI	CHEBI:30831 Y
ChEMBL	ChEMBL171246 Y
ChemSpider	57 Y
DrugBank	DB04553 Y
Jmol 3D model	Interactive image
KEGG	C00109 Y
MeSH	Alpha-ketobutyric+acid
PubChem	58
InChI InChI=1S/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7) Y Key: TYEYBOSBBBHJIV-UHFFFAOYSA-N Y InChI=1/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7) Key: TYEYBOSBBBHJIV-UHFFFAOYAT
SMILES O=C(C(=O)O)CC
Properties
Chemical formula	C4H6O3
Molar mass	102.089 g/mol
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

α-Ketobutyric acid is a product of the lysis of cystathionine. It is also one of the degradation products of threonine, produced by the catabolism of the amino acid by threonine dehydratase. It is also produced by the degradation of homocysteine and the metabolism of methionine.

α-Ketobutyric acid is transported into the mitochondrial matrix, where it is converted to propionyl-CoA by Branched-chain alpha-keto acid dehydrogenase complex. Further mitochondrial reactions produce succinyl CoA. This is first through the enzyme mitochondria Propionyl-CoA carboxylase with biotin as a cofactor to produce S-methylmalonyl-CoA. This is subsequently converted to R-methylmalonyl-CoA by mitochondrial methylmalonyl-CoA epimerase. Finally, mitochondrial methylmalonyl-CoA mutase with cofactor adenosylcobalamin produces succinyl-CoA which enters the citric acid cycle.

Conversion in sotolon in French vin jaune

Vin jaune is marked by the formation of sotolon from alpha-ketobutyric acid.

See also

• Butyric acid