Isovaleric acid

Chemical Compound
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Isovaleric acid, also known as 3-methylbutanoic acid, is an organic compound with the formula (CH₃)₂CHCH₂COOH. It is classified as a branched-chain fatty acid and is commonly found in various natural oils and plant extracts. Isovaleric acid is notable for its strong, pungent odor, which is often described as resembling sweaty feet or aged cheese.

Properties

Isovaleric acid is a colorless liquid that is sparingly soluble in water, but well soluble in most common organic solvents such as ethanol and diethyl ether. The compound has a boiling point of approximately 176°C and a melting point of -31°C.

Production

Isovaleric acid can be produced through several methods, including the oxidation of isovaleryl aldehyde or the fermentation of amino acids such as leucine. It is also a natural byproduct of the metabolic processes in various organisms.

Applications

Isovaleric acid has several applications in different industries. In the food industry, it is used as a flavoring agent to impart a distinctive flavor to certain food products. In perfumery, it is used to create musky or sweaty odors. Additionally, it serves as an intermediate in the manufacture of plasticizers, lubricants, and pharmaceuticals.

Biological Significance

In humans, elevated levels of isovaleric acid can be indicative of a rare genetic disorder known as Isovaleric acidemia. This condition is characterized by the body's inability to properly process the amino acid leucine, leading to a buildup of isovaleric acid in the blood, which can be toxic and cause severe metabolic disturbances.

Safety

Isovaleric acid can be irritating to the skin, eyes, and respiratory system. Adequate ventilation and protective equipment are recommended when handling this chemical in industrial settings.

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  Structure of Isovaleric Acid
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  Synthesis of HMB