2,3-Dihydroxybenzoic acid

A chemical compound used in various biological processes

2,3-Dihydroxybenzoic acid is an organic compound with the formula C₇H₆O₄. It is one of the several isomers of dihydroxybenzoic acid. This compound is a type of phenolic acid and is characterized by the presence of two hydroxyl groups attached to the benzene ring.

Structure and properties

2,3-Dihydroxybenzoic acid consists of a benzene ring with two hydroxyl groups (-OH) and a carboxylic acid group (-COOH) attached. The hydroxyl groups are located at the 2 and 3 positions on the benzene ring, which distinguishes it from other isomers such as 2,5-dihydroxybenzoic acid and 3,4-dihydroxybenzoic acid.

The presence of hydroxyl groups makes this compound a phenol, and the carboxylic acid group contributes to its acidic properties. It is a crystalline solid that is soluble in water and organic solvents.

Biological significance

2,3-Dihydroxybenzoic acid is involved in various biological processes. It is a known siderophore, which means it can bind and transport iron in biological systems. This property is crucial for microorganisms that require iron for growth and metabolism.

In humans, 2,3-dihydroxybenzoic acid is a metabolite of salicylic acid, which is a major component of aspirin. It is also involved in the shikimate pathway, a biosynthetic route used by bacteria, fungi, and plants to synthesize aromatic compounds.

Applications

Due to its ability to chelate iron, 2,3-dihydroxybenzoic acid is used in research to study iron metabolism and transport. It is also used in the synthesis of various pharmaceuticals and biochemical compounds.

Synthesis

2,3-Dihydroxybenzoic acid can be synthesized through the hydroxylation of salicylic acid or by the Kolbe-Schmitt reaction, which involves the carboxylation of phenol derivatives.

Related pages

• Dihydroxybenzoic acid
• Phenolic acid
• Siderophore
• Shikimate pathway

Gallery

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  Structural formula of 2,3-Dihydroxybenzoic acid

2,3-Dihydroxybenzoic acid

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  2,3-Dihydroxybenzoic acid structure