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β-Ketoisocaproic acid

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β-Ketoisocaproic acid
Skeletal formula of beta-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
3D model (JSmol)
ChEBI
ChemSpider
KEGG
MeSH Beta-ketoisocaproic+acid
UNII
  • Key: ZXLSKTZECNUVIS-UHFFFAOYSA-N checkY
  • CC(C)C(CC(O)=O)=O
Properties
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:
GHS05: Corrosive
Danger
H314
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

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  1. ^ 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 ...
  2. ^ "Leucine metabolism". BRENDA. Technische Universität Braunschweig. Archived from the original on 17 August 2016. Retrieved 12 August 2016.