816-66-0
Chemical Structure
4-Methyl-2-oxopentanoic acid
Synonym(s): α-Ketoisocaproic acid
- CAS No.: 816-66-0
- Formula:C6H10O3
- Molecular Weight:130.14
IUPAC Name: 4-methyl-2-oxopentanoic acid
InChIKey: BKAJNAXTPSGJCU-UHFFFAOYSA-N
SMILES: CC(C)CC(C(O)=O)=O
Biological Activity: 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].
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4-Methyl-2-oxopentanoic acid | 98.49% | 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. | ||||||||||||||||||||
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4-Methyl-2-oxopentanoic acid (Standard) | 95.67% | 4-Methyl-2-oxopentanoic acid (Standard) is the analytical standard of 4-Methyl-2-oxopentanoic acid. This product is intended for research and analytical applications. 4-Methyl-2-oxopentanoic acid (α-Ketoisocaproic acid), an abnormal metabolite, is both a neurotoxin and a metabotoxin. | ||||||||||||||||||||
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Sodium α-ketoisocaproic acid-13C2 | 99.95% | Sodium α-ketoisocaproic acid-13C2 is the 13C labeled Sodium α-ketoisocaproic acid. | ||||||||||||||||||||
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- [1]. Yudkoff M, et al. Brain amino acid requirements and toxicity: the example of leucine. J Nutr. 2005 Jun;135(6 Suppl):1531S-8S. [Content Brief]
- [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. [Content Brief]
- [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. [Content Brief]
- [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. [Content Brief]
- [5]. Amaral, et al. α-Ketoisocaproic acid and leucine provoke mitochondrial bioenergetic dysfunction in rat brain. Brain research 1324 (2010): 75-84. [Content Brief]
