β-Ketoisocaproic acid

β-Ketoisocaproic acid
Names
	Preferred IUPAC name 4-Methyl-3-oxopentanoic acid
	Other names 4-Methyl-3-oxopentanoic acid; 4-Methyl-3-oxovaleric acid; Isobutanoylacetic acid; Isobutyrylacetic acid
Identifiers
CAS Number	5650-76-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:29024 ;
ChemSpider	389038 ;
KEGG	C03467 ;
MeSH	Beta-ketoisocaproic+acid
PubChem CID	440024;
UNII	FWW4Q5U8HP ;
CompTox Dashboard (EPA)	DTXSID60331463 ;
	InChI Key: ZXLSKTZECNUVIS-UHFFFAOYSA-N ;
	SMILES CC(C)C(CC(O)=O)=O;
Properties
Chemical formula	C6H10O3
Molar mass	130.143 g·mol−1
Density	1.1 g cm−3 (at 20 °C)
Boiling point	236 °C (457 °F; 509 K) ±23 at 760 mmHg
log P	0.36
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H314
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

β-Ketoisocaproic acid, also known as 4-methyl-3-oxopentanoic acid, is an intermediate in the metabolism of leucine.^[1]^[2] Its metabolic precursor and metabolic product in the leucine metabolic pathway are β-leucine and β-ketoisocaproyl-CoA, respectively.^[1]

References

^ ^a ^b Kohlmeier M (May 2015). "Leucine". Nutrient Metabolism: Structures, Functions, and Genes (2nd ed.). Academic Press. pp. 385–388, Figure 8.57. ISBN 978-0-12-387784-0. Retrieved 6 June 2016. Energy fuel: Eventually, most Leu is broken down, providing about 6.0kcal/g. About 60% of ingested Leu is oxidized within a few hours ... Ketogenesis: A significant proportion (40% of an ingested dose) is converted into acetyl-CoA and thereby contributes to the synthesis of ketones, steroids, fatty acids, and other compounds ...
^ "Leucine metabolism". BRENDA. Technische Universität Braunschweig. Archived from the original on 17 August 2016. Retrieved 12 August 2016.

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