α-Ketoisocaproic acid

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Alpha-Ketoisocaproic acid
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α-Ketoisocaproic acid
Skeletal formula of alpha-ketoisocaproic acid
Names
IUPAC name
4-Methyl-2-oxopentanoic acid
Systematic IUPAC name
4-Methyl-2-oxopentanoic acid[1]
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
)
3DMet
1701823
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard
 100.011.304 Edit this at Wikidata
EC Number
  • 212-435-5
IUPHAR/BPS
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) checkY
    Key: BKAJNAXTPSGJCU-UHFFFAOYSA-N checkY
  • 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:
GHS05: Corrosive
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).
checkY verify (what is checkY☒N ?)

α-Ketoisocaproic acid (α-KIC), also known as 4-methyl-2-oxovaleric acid, and its

resistance exercises in people who do not usually perform those exercises.[9]

Biological activity

Supplements

α-KIC has been studied as a

beta-hydroxy beta-methylbutyrate (HMB), participants reported delayed onset of muscle soreness, as well as other positive effects such as increased muscle girth.[9] It is important to note that studies have also suggested that ɑ-KIC taken alone did not have any significant positive impacts on physical performance, so it should be taken in conjunction with other ergogenic substances.[10] ɑ-KIC is not available as a supplement on its own, but its decarboxylated form HMB is available in calcium salt capsules or powder.[4]

Applications

The biochemical implications of α-KIC are largely connected to other

Protein Synthesis, skeletal muscle regeneration, and skeletal muscle proteolysis have all been noted to change when ɑ-KIC is taken. There is not much research into the specific mechanisms taking part in these processes, but there is a noticeable correlation between ɑ-KIC ingestion and increased skeletal muscle protein synthesis, regeneration, and proteolysis.[4]

Toxicity

Multiple studies have demonstrated that there have been no adverse effects on humans nor animals that ingested α-KIC or HMB.[11][12]

In patients with maple syrup urine disease, who are unable to metabolize the branched chain alpha keto acids, α-KIC is believed to be one of the key mediators of neurotoxicity.[13]

Medical use

Branched-chain alpha-keto acids such as α-KIC are found in high concentrations in the urine of people who suffer from Maple Syrup Urine Disease. This is disease is caused by a partial

excreted in the urine as α-KIC, HMB, and many other similar keto acids. Flare-ups in people who have this condition are caused due to poor diet.[7] Symptoms of Maple Syrup Urine Disease include sweet smelling urine, irritability, lethargy, and in serious cases edema of the brain, apnea, coma, or respiratory failure.[14][7] Treatment includes lowering leucine intake and a specialized diet to make up for the lack of leucine ingestion.[7]

Leucine metabolism

Diagram of leucine, HMB, and isovaleryl-CoA metabolism in humans
α-Ketoglutarate
Glutamate
Glutamate
Pyruvate
Muscle: α-Ketoisocaproate (α-KIC)
Liver: α-Ketoisocaproate (α-KIC)
mitochondria
)
Excreted
in urine
(10–40%)


(
HMG-CoA
lyase
HMG-CoA 
synthase
Unknown
enzyme
β-Hydroxybutyrate
Acetoacetate
Mevalonate
The image above contains clickable links
Human metabolic pathway for HMB and isovaleryl-CoA relative to L-leucine.[2][15][16] Of the two major pathways, L-leucine is mostly metabolized into isovaleryl-CoA, while only about 5% is metabolized into HMB.[2][15][16]

References

  1. ^ CID 70 from PubChem
  2. ^
    PMID 23374455
    .
  3. ^ "Leucine".
  4. ^
    PMID 23374455
    .
  5. ^
    S2CID 11120110
    .
  6. ^
    ISBN 978-0-12-387784-0
    .
  7. ^ a b c d Strauss, Kevin A; Puffenberger, Erik G; Carson, Vincent J (1993). "Maple Syrup Urine Disease". GeneReviews. University of Washington, Seattle.
  8. ^
    ISBN 978-0-12-396454-0
    .
  9. ^
    PMID 16286672
    .
  10. PMID 17908285
    .
  11. PMID 10917905
    .
  12. PMID 16006030
    .
  13. S2CID 1253267
    .
  14. ^
    PMID 20061171
    .
  15. ^
    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
    Figure 8.57: Metabolism of L-leucine
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