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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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16530 ;
ChEMBL	ChEMBL146554 ;
ChemSpider	48 ;
DrugBank	DB04074 ;
ECHA InfoCard	100.010.969
KEGG	C00141 ;
PubChem CID	49;
UNII	34P71D50E0 ;
CompTox Dashboard (EPA)	DTXSID6061078 ;
	InChI InChI=1S/C5H8O3/c1-3(2)4(6)5(7)8/h3H,1-2H3,(H,7,8) Key: QHKABHOOEWYVLI-UHFFFAOYSA-N ; 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). verify (what is ?) Infobox references

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

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]

References

^ ^a ^b Leonardi, Roberta; Jackowski, Suzanne (April 2007). "Biosynthesis of Pantothenic Acid and Coenzyme A". EcoSal Plus. 2 (2). doi:10.1128/ecosalplus.3.6.3.4. ISSN 2324-6200. PMC 4950986. PMID 26443589.
^ Atsumi, Shota; Hanai, Taizo; Liao, James C. (2008). "Non-Fermentative Pathways for Synthesis of Branched-Chain Higher Alcohols as Biofuels". Nature. 451 (7174): 86–89. Bibcode:2008Natur.451...86A. doi:10.1038/nature06450. PMID 18172501. S2CID 4413113.

[biosyn-1] Leonardi, Roberta; Jackowski, Suzanne (April 2007). "Biosynthesis of Pantothenic Acid and Coenzyme A". EcoSal Plus. 2 (2). doi:10.1128/ecosalplus.3.6.3.4. ISSN 2324-6200. PMC 4950986. PMID 26443589.

[2] Atsumi, Shota; Hanai, Taizo; Liao, James C. (2008). "Non-Fermentative Pathways for Synthesis of Branched-Chain Higher Alcohols as Biofuels". Nature. 451 (7174): 86–89. Bibcode:2008Natur.451...86A. doi:10.1038/nature06450. PMID 18172501. S2CID 4413113.

[1]

[2]

LIMSwiki

Synthesis and reactions

See also

References