2-Methylacetoacetic acid

• CAS: 2382-59-4
• Catalog Number: ACM2382594
• Category: Main Products
• Molecular Weight: 116.12
• Molecular Formula: C₅H₈O₃
• Synonyms: 2-METHYLACETOACETIC ACID;2-Methyl-3-oxo-butanoic acid;2-Methyl-3-ketobutyric acid;Butanoic acid, 2-methyl-3-oxo- (9CI);2-Acetylpropanoic Acid
• IUPAC Name: 2-methyl-3-oxobutanoicacid
• SMILES: CC(C(=O)C)C(=O)O
• InChI Key: GCXJINGJZAOJHR-UHFFFAOYSA-N
• Boiling Point: 227.9ºC at 760mmHg
• Flash Point: 105.9ºC
• Density: 1.125g/cm³
• Exact Mass: 116.04700

Case Study

2-Methylacetoacetic Acid as a Metabolic Inhibitor of Aerobic Energy Production in the Developing Rat Cerebral Cortex

Rosa, R. B., et al. Journal of inherited metabolic disease 28.4 (2005): 501-515.

2-Methylacetoacetic acid acts as a neurotoxic metabolite accumulating in beta-ketothiolase deficiency that inhibits aerobic energy metabolism in cerebral cortex, contributing to the pathogenesis of neurological dysfunction in this inherited disorder of isoleucine catabolism.
Experimental Protocol: Cortical homogenates from 30-day-old rats are pre-incubated for 15 min at 35 degrees Celsius, then incubated for 60 min with radiolabeled glucose, acetate or citrate in the presence of the acid at concentrations from 0.01 to 1.0 mmol/L under an oxygen carbon dioxide atmosphere. Respiratory chain enzyme activities are measured at 1.0 mmol/L, and creatine kinase is assayed after pre-incubation at 37 degrees Celsius.
Performance Evaluation: The metabolite inhibits carbon dioxide production from all three substrates by up to 35%, with effects already detectable at 0.01 mmol/L from citrate. At 1.0 mmol/L it reduces respiratory chain complex II activity by 12% and succinate dehydrogenase by 18%. Creatine kinase and the other respiratory complexes remain unaffected, demonstrating a specific blockade of the Krebs cycle and a mild impairment of the electron transport chain. Structurally similar acetoacetate and beta-hydroxybutyrate do not alter any of these activities, confirming the specificity of the inhibition.

Custom Q&A

What is the molecular formula of 2-Methylacetoacetic acid?

The molecular formula is C5H8O3.

What are the synonyms of 2-Methylacetoacetic acid?

The synonyms are 2-methyl-3-oxobutanoic acid, 2-methyl-3-oxo-butyric acid, and 2-methyl-3-ketovaleric acid.

What is the molecular weight of 2-Methylacetoacetic acid?

The molecular weight is 116.11 g/mol.

When was 2-Methylacetoacetic acid created?

It was created on July 19, 2005.

When was 2-Methylacetoacetic acid last modified?

It was last modified on October 21, 2023.

What is the IUPAC name of 2-Methylacetoacetic acid?

The IUPAC name is 2-methyl-3-oxobutanoic acid.

What is the InChI key of 2-Methylacetoacetic acid?

The InChI key is GCXJINGJZAOJHR-UHFFFAOYSA-N.

What is the Canonical SMILES of 2-Methylacetoacetic acid?

The Canonical SMILES is CC(C(=O)C)C(=O)O.

What is the CAS number of 2-Methylacetoacetic acid?

The CAS number is 2382-59-4.

What is the hydrogen bond donor count of 2-Methylacetoacetic acid?

The hydrogen bond donor count is 1.