2,6-Dimethoxyphenol

Chemical properties

2,6-Dimethoxyphenol is an off-white or grey to brown crystalline powder that has a woody, medicinal, rather dry odor.

Occurrence

Reported found in beechwood tar creosote, onion, garlic, leek, chive, nira (Allium tuberosum Rotti), nobira (Allium grayi Regal) and caucus (Allium victoralis L.)

The Uses of 2,6-Dimethoxyphenol

2,6-Dimethoxyphenol has been used as a metabolite of lignin depolymerisation.It is also used as flavoring agent or adjuvant.It is reported to be the single most important flavor chemical in smoke flavors. It is used in smoke flavors, whisky, rum, tea, spice, savory, seafood, meat, liquorices, coffee, and nut flavors.

Definition

ChEBI: 2,6-dimethoxyphenol is a member of the class of phenols that is phenol substituted by methoxy groups at positions 2 and 6. It has a role as a plant metabolite. It is a member of phenols and a dimethoxybenzene.

Preparation

2,6-Dimethoxyphenol is prepared by reacting pyrogallol with methyl iodide in alkaline aqueous medium; by demethylation of pyrogallol trimethyl ether in aqueous alkali or in alcohol.

Aroma threshold values

Detection: 400 ppb to 1.85 ppm

Taste threshold values

Taste characteristics at 60 ppm: sweet, medicinal, creamy, meaty, vanilla, spice.

Synthesis Reference(s)

The Journal of Organic Chemistry, 44, p. 4444, 1979 DOI: 10.1021/jo01338a043
Tetrahedron Letters, 34, p. 7667, 1993 DOI: 10.1016/S0040-4039(00)61534-4

General Description

2,6-Dimethoxyphenol has been identified as one of the volatile flavor constituents in shoyu (soy sauce), wine and wood smoke.

Purification Methods

Purify the phenol by zone melting or sublimation in a vacuum. [Beilstein 6 IV 7329.]