Guaiacol

Guaiacol is a naturally occurring organic compound with the formula C6H4(OH)(OCH3). Although it is biosynthesized by a variety of organisms, this yellowish aromatic oil is usually derived from guaiacum or wood creosote. Samples darken upon exposure to air and light. Guaiacol is present in wood smoke, resulting from the pyrolysis of lignin. The compound contributes to the flavor of many substances such as whisky and roasted coffee.

Chemical Properties

Guaiacol is a derivative of phenol with a methoxy group in the ortho position. It is a slightly yellow crystalline solid with a strong, penetrating odor. It is soluble in water and common organic solvents. Guaiacol is readily oxidized by the heme iron of peroxidases including the peroxidase of cyclooxygenase (COX) enzymes to form a variety of products.

Uses

Guaiacol is used in the synthesis of other organic compounds such as vanillin. It is also used as an expectorant, an antiseptic, and a local anesthetic. Guaiacol is also used in the preparation of synthetic flavors and in perfumery.

Health Effects

Exposure to guaiacol can cause irritation to the skin, eyes, and respiratory tract. Ingestion can lead to symptoms such as nausea, vomiting, and abdominal pain. Long-term exposure can lead to more serious health effects such as liver and kidney damage.

See Also

• Phenol
• Vanillin
• Wood creosote

Guaiacol Resources
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