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4-Methyl-2-oxopentanoic acid

4-Methyl-2-oxopentanoic acid (α-Ketoisocaproic acid) is a metabolite of L-leucine and is involved in energy metabolism. 4-Methyl-2-oxopentanoic acid increases endoplasmic reticulum stress, promotes lipid accumulation in preadipocytes and insulin resistance by impairing mTOR and autophagy signaling pathways. 4-Methyl-2-oxopentanoic acid also causes oxidative damage, leading to cognitive deficits, inhibits α-ketoglutarate dehydrogenase activity, acts as an oxidative phosphorylation uncoupler and metabolic inhibitor. 4-Methyl-2-oxopentanoic acid acts as a nutrient signal and stimulates skeletal muscle protein synthesis. 4-Methyl-2-oxopentanoic acid can be used in the study of maple syrup urine disease[1][2][3][4][5].

Product Specifications

CAS Number

[816-66-0]

Product Name Alternative

α-Ketoisocaproic acid

UNSPSC

12352211

Hazard Statement

H314

Target

Autophagy; Endogenous Metabolite; mTOR; SOD

Type

Natural Products

Related Pathways

Autophagy; Immunology/Inflammation; Metabolic Enzyme/Protease; PI3K/Akt/mTOR

Applications

Metabolism-sugar/lipid metabolism

Field of Research

Metabolic Disease; Neurological Disease

Assay Protocol

https://www.medchemexpress.com/4-Methyl-2-oxopentanoic_acid.html

Purity

99.51

Solubility

DMSO : 100 mg/mL (ultrasonic) |H2O : 100 mg/mL (ultrasonic)

Smiles

CC(C)CC(C(O)=O)=O

Molecular Formula

C6H10O3

Molecular Weight

130.14

Precautions

H314

References & Citations

[1]Yudkoff M, et al. Brain amino acid requirements and toxicity: the example of leucine. J Nutr. 2005 Jun;135 (6 Suppl) :1531S-8S.|[2]Park, et al. α-ketoisocaproic acid promotes ER stress through impairment of autophagy, thereby provoking lipid accumulation and insulin resistance in murine preadipocytes. Biochemical and Biophysical Research Communications 603 (2022) : 109-115.|[3]Taschetto, et al. Acute and long-term effects of intracerebroventricular administration of α-ketoisocaproic acid on oxidative stress parameters and cognitive and noncognitive behaviors. Metabolic brain disease 32 (2017) : 1507-1518.|[4]Escobar, et al. Leucine and α-ketoisocaproic acid, but not norleucine, stimulate skeletal muscle protein synthesis in neonatal pigs. The Journal of nutrition 140.8 (2010) : 1418-1424.|[5]Amaral, et al. α-Ketoisocaproic acid and leucine provoke mitochondrial bioenergetic dysfunction in rat brain. Brain research 1324 (2010) : 75-84.

Shipping Conditions

Room Temperature

Storage Conditions

4°C (Powder, protect from light)

Scientific Category

Natural Products

Clinical Information

No Development Reported

Isoform

Human Endogenous Metabolite

Available Sizes

Curated Selection

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