alpha-Ketoisocaproic acid

α-Ketoisocaproic acid
IUPAC name
4-Methyl-2-oxopentanoic acid
Systematic IUPAC name
4-Methyl-2-oxopentanoic acid[1]
Other names
4-Methyl-2-oxovaleric acid
816-66-0 YesY
3D model (Jmol) Interactive image
Interactive image
3DMet B00066
ChEBI CHEBI:48430 YesY
ChEMBL ChEMBL445647 YesY
ChemSpider 69 YesY
DrugBank DB03229 YesY
ECHA InfoCard 100.011.304
EC Number 212-435-5
KEGG C00233 YesY
MeSH Alpha-ketoisocaproic+acid
PubChem 70
UN number 3265
Molar mass 130.14 g·mol−1
Density 1.055 g cm−3 (at 20 °C)
Melting point 8 to 10 °C (46 to 50 °F; 281 to 283 K)
Boiling point 85 °C (185 °F; 358 K) at 13 mmHg
log P 0.133
Acidity (pKa) 2.651
Basicity (pKb) 11.346
R-phrases R34
S-phrases S26, S36/37/39, S45
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

α-Ketoisocaproic acid is an intermediate in the metabolism of leucine.[2]

Leucine metabolism

Human metabolic pathway for HMB and isovaleryl-CoA, relative to leucine.[2] Of the two major pathways, leucine is mostly metabolized into isovaleryl-CoA, while only 5% or so is metabolized into HMB.[2]


  2. 1 2 3 Wilson JM, Fitschen PJ, Campbell B, Wilson GJ, Zanchi N, Taylor L, Wilborn C, Kalman DS, Stout JR, Hoffman JR, Ziegenfuss TN, Lopez HL, Kreider RB, Smith-Ryan AE, Antonio J (February 2013). "International Society of Sports Nutrition Position Stand: beta-hydroxy-beta-methylbutyrate (HMB)". J. Int. Soc. Sports. Nutr. 10 (1): 6. doi:10.1186/1550-2783-10-6. PMC 3568064Freely accessible. PMID 23374455.

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