Catechol

Catechol (also known as 1,2-dihydroxybenzene or pyrocatechol) is an organic compound with the molecular formula C6H4(OH)2. It is a type of benzene derivative and is one of the three isomeric benzenediols, the others being resorcinol (1,3-dihydroxybenzene) and hydroquinone (1,4-dihydroxybenzene).

Structure and Properties

Catechol consists of a benzene ring with two adjacent hydroxyl groups. It is a colorless compound that is soluble in water and exhibits a characteristic phenolic odor. The presence of the hydroxyl groups makes catechol a relatively reactive compound, capable of undergoing various chemical reactions such as oxidation and electrophilic substitution.

Synthesis

Catechol can be synthesized through several methods, including the hydroxylation of phenol using hydrogen peroxide in the presence of a catalyst. Another common method involves the hydrolysis of o-dichlorobenzene.

Applications

Catechol is used in a variety of industrial and research applications. It serves as a precursor to various chemicals, including pesticides, pharmaceuticals, and flavoring agents. In the field of biochemistry, catechol is used as a substrate in enzyme assays to study the activity of catechol oxidase and other related enzymes.

Biological Role

In nature, catechol is found in various plants and is involved in the biosynthesis of lignin, a complex polymer that provides structural support to plant cell walls. It also plays a role in the defense mechanisms of plants against herbivores and pathogens.

Safety and Handling

Catechol is classified as a hazardous substance and should be handled with care. It can cause skin and eye irritation and may be harmful if ingested or inhaled. Proper safety measures, including the use of personal protective equipment, should be followed when handling catechol.

Related Compounds

• Resorcinol
• Hydroquinone
• Phenol
• Benzenediol

See Also

• Phenol
• Benzenediol
• Catecholamine
• Lignin

References

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Catechol gallery

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  Brenzcatechin

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  Catechol from crystal orientation 2 3D