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α-Ketoisovaleric acid

α-Ketoisovaleric acid

Names
Preferred IUPAC name 3-Methyl-2-oxobutanoic acid
Other names 2-Ketoisovaleric acid; α-Ketovaline
Identifiers
CAS Number	759-05-7 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16530 Y
ChEMBL	ChEMBL146554 Y
ChemSpider	48 Y
DrugBank	DB04074 Y
ECHA InfoCard	100.010.969
KEGG	C00141 Y
PubChem CID	49
UNII	34P71D50E0 Y
CompTox Dashboard (EPA)	DTXSID6061078
InChI InChI=1S/C5H8O3/c1-3(2)4(6)5(7)8/h3H,1-2H3,(H,7,8) Y Key: QHKABHOOEWYVLI-UHFFFAOYSA-N Y InChI=1/C5H8O3/c1-3(2)4(6)5(7)8/h3H,1-2H3,(H,7,8) Key: QHKABHOOEWYVLI-UHFFFAOYAY
SMILES O=C(C(=O)O)C(C)C
Properties
Chemical formula	C5H8O3
Molar mass	116.116 g·mol−1
Appearance	colorless or white solid or oil
Melting point	31.5 °C (88.7 °F; 304.6 K)
Boiling point	170.5 °C (338.9 °F; 443.6 K)
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

Chemical compound

α-Ketoisovaleric acid is an organic compound with the formula (CH₃)₂CHC(O)CO₂H. It is a ketoacid. With a melting point just above room temperature, it is usually an oil or semi-solid. The compound is colorless. It is a metabolite of valine and a precursor to pantothenic acid, a prosthetic group found in several cofactors. In the biological context, is usually encountered as its conjugate base ketoisovalerate, (CH₃)₂CHC(O)CO₂⁻.^[1]

Synthesis and reactions[edit]

α-Ketoisovalerate undergoes hydroxymethylation to give ketopantoate:^[1]

(CH₃)₂CHC(O)CO₂⁻ + CH₂O → HOCH₂(CH₃)₂CC(O)CO₂⁻

This conversion is catalyzed by ketopantoate hydroxymethyltransferase.

Like many α-ketoacids, α-ketoisovaleric acid is prone to decarboxylation to give isobutyraldehyde:

(CH₃)₂CHC(O)CO₂H → (CH₃)₂CHCHO + CO₂

Genetic engineering has been used to produce the biofuel isobutanol by reduction of isobutyraldehyde obtained from ketoisovalerate.^[2]

See also[edit]

• α-Ketovaleric acid

References[edit]

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