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) |
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| 1701823 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.011.304 |
| EC Number |
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| KEGG | |
| MeSH | Alpha-ketoisocaproic+acid |
PubChem CID |
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| UNII | |
| UN number | 3265 |
CompTox Dashboard (EPA) |
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| 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).
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.