Isovaleric acid
(Redirected from 3-Methylbutanoic acid)
Isovaleric acid is a branched-chain fatty acid with the chemical formula (CH₃)₂CHCH₂COOH. It is a colorless liquid that is sparingly soluble in water but highly soluble in most organic solvents. Isovaleric acid is known for its pungent odor, which is often described as similar to that of sweaty feet or cheese.
Chemical Properties
Isovaleric acid is a carboxylic acid and is classified as a short-chain fatty acid. It is a structural isomer of valeric acid, differing in the branching of its carbon chain. The presence of a methyl group on the second carbon atom gives isovaleric acid its characteristic structure and properties.
Biological Role
In biological systems, isovaleric acid is a product of the metabolism of the amino acid leucine. It is involved in various metabolic pathways and can be found in the human body as well as in other organisms. Isovaleric acid is also a component of sweat and contributes to the characteristic odor of body odor.
Industrial Uses
Isovaleric acid is used in the production of various esters, which are employed as flavoring agents and fragrances. It is also used in the synthesis of pharmaceuticals and agrochemicals.
Isovaleric Acidemia
Isovaleric acidemia is a rare metabolic disorder caused by a deficiency of the enzyme isovaleryl-CoA dehydrogenase, which is involved in the breakdown of leucine. This condition leads to the accumulation of isovaleric acid in the body, resulting in symptoms such as vomiting, lethargy, and a distinctive "sweaty feet" odor. Management of isovaleric acidemia involves dietary restrictions and supplementation with glycine and carnitine.
Synthesis
Isovaleric acid can be synthesized through various chemical processes. One common method involves the oxidation of isovaleraldehyde. It can also be produced by the fermentation of certain bacteria that metabolize leucine.
Related Compounds
Isovaleric acid is related to several other compounds, including:
Related Pages
Branched-chain fatty acid
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