Guaiacol

Names

IUPAC name

2-methoxyphenol

Other names

o-methoxyphenol; O-methylcatechol; 2-hydroxyanisole

Identifiers

CAS Number

90-05-1^Y

3D model (Jmol)

CHEBI:28591^Y

ChEMBL13766^Y

447^Y

D00117^Y

6JKA7MAH9C^Y

InChI=1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3^Y

Key: LHGVFZTZFXWLCP-UHFFFAOYSA-N^Y
InChI=1/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3

Key: LHGVFZTZFXWLCP-UHFFFAOYAI

SMILES

COc1ccccc1O

Properties

Chemical formula

C₇H₈O₂

Molar mass

124.14 g/mol

Density

1.112 g/cm³, liquid
1.129 g/cm³, crystals

Melting point

28 °C (82 °F; 301 K)

Boiling point

204 to 206 °C (399 to 403 °F; 477 to 479 K)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(what is ^YN ?)

Infobox references

Guaiacol is a naturally occurring organic compound with the formula C₆H₄(OH)(OCH₃), first isolated by Otto Unverdorben in 1826. 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 compounds, e.g., roasted coffee.

Guaiacol is produced by methylation of catechol, e.g., using potash and dimethyl sulfate:

Guaiacol can be prepared by diverse routes in the laboratory. 2-Aminoanisole, derived in two steps from anisole, can be hydrolyzed via its diazonium derivative. Guaiacol can be synthesized by the dimethylation of catechol followed by selective mono-demethylation.

Guaiacol is a precursor to various flavorants, such as eugenol and vanillin. An estimated 85% of the worlds supply of vanillin comes from guaiacol. The route entails condensation of glyoxylic acid with guaiacol to give mandelic acid, which is oxidized to produce a phenylglyoxylic acid. This acid undergoes a decarboxylation to afford vanillin.

In basic solution, it is readily oxidized, giving yellowish brown and absorbs light maximally at about 470 nm.

Its derivatives are used medicinally as an expectorant, antiseptic, and local anesthetic.

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