Α-Ketoisocaproic acid

α-Ketoisocaproic acid
Names
IUPAC name
4-Methyl-2-oxopentanoic acid
Systematic IUPAC name
4-Methyl-2-oxopentanoic acid
Other names
4-Methyl-2-oxovaleric acid
2-Ketoisocaproic acid
2-Oxo-4-methylpentanoic acid
2-Oxo-4-methylvaleric acid
2-Oxoisocaproic acid
2-Oxoleucine
Isobutylglyoxylic acid
Ketoleucine
α-Ketoisocapronic acid
α-Oxoisocaproic acid
Identifiers
3D model (JSmol)
1701823
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.011.304
EC Number
  • 212-435-5
KEGG
MeSH Alpha-ketoisocaproic+acid
UNII
UN number 3265
  • InChI=1S/C6H10O3/c1-4(2)3-5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9) Y
    Key: BKAJNAXTPSGJCU-UHFFFAOYSA-N Y
  • InChI=1/C6H10O3/c1-4(2)3-5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)
    Key: BKAJNAXTPSGJCU-UHFFFAOYAG
  • CC(C)CC(=O)C(O)=O
  • O=C(C(=O)O)CC(C)C
Properties
C6H10O3
Molar mass 130.143 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
Hazards
GHS labelling:
Danger
H314
P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501
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

α-Ketoisocaproic acid (α-KIC), also known as 4-methyl-2-oxovaleric acid, and its conjugate base and carboxylate, α-ketoisocaproate, are metabolic intermediates in the metabolic pathway for L-leucine. Leucine is an essential amino acid, and its degradation is critical for many biological duties. α-KIC is produced in one of the first steps of the pathway by branched-chain amino acid aminotransferase by transferring the amine on L-leucine onto alpha ketoglutarate, and replacing that amine with a ketone. The degradation of L-leucine in the muscle to this compound allows for the production of the amino acids alanine and glutamate as well. In the liver, α-KIC can be converted to a vast number of compounds depending on the enzymes and cofactors present, including cholesterol, acetyl-CoA, isovaleryl-CoA, and other biological molecules. Isovaleryl-CoA is the main compound synthesized from ɑ-KIC. α-KIC is a key metabolite present in the urine of people with Maple syrup urine disease, along with other branched-chain amino acids. Derivatives of α-KIC have been studied in humans for their ability to improve physical performance during anaerobic exercise as a supplemental bridge between short-term and long-term exercise supplements. These studies show that α-KIC does not achieve this goal without other ergogenic supplements present as well. α-KIC has also been observed to reduce skeletal muscle damage after eccentrically biased resistance exercises in people who do not usually perform those exercises.