2,6-Dimethoxyphenol Chemical Properties

Melting point:

50-57 °C(lit.)

Boiling point:

261 °C(lit.)

Density 

1.1690 (rough estimate)

refractive index 

1.4745 (estimate)

FEMA 

3137 | 2,6-DIMETHOXYPHENOL

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Crystalline Powder, Crystals, or Crystalline Solid

pka

9.97±0.10(Predicted)

color 

Off-white or gray to brown

Odor

at 1.00 % in dipropylene glycol. smoky phenolic balsamic bacon powdery woody

Odor Type

smoky

Water Solubility 

2 g/100 mL (13 ºC)

JECFA Number

721

BRN 

1526871

InChIKey

KLIDCXVFHGNTTM-UHFFFAOYSA-N

LogP

0.77

CAS DataBase Reference

91-10-1(CAS DataBase Reference)

NIST Chemistry Reference

Phenol, 2,6-dimethoxy-(91-10-1)

EPA Substance Registry System

Phenol, 2,6-dimethoxy- (91-10-1)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-36-37/39

RIDADR 

UN 2811 6.1/PG 1

WGK Germany 

3

RTECS 

SL0900000

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29095090

MSDS

• Language:English Provider:2,6-Dimethoxyphenol

2,6-Dimethoxyphenol Usage And Synthesis

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.)

Uses

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.]

2,6-Dimethoxyphenol(91-10-1)Related Product Information

• 4-Methoxyphenol
• Dimethyl carbonate
• Guaiacol
• 4-Ethoxyphenol
• 3,4-Dimethoxyphenol
• p-(2-Methoxyethyl) phenol
• Diphenyldimethoxysilane
• 2,6-Dimethoxybenzaldehyde
• Metformin
• 3,5-Dimethoxyphenol
• Dimethyldimethoxysilane
• 1,1-Dimethoxyethane
• 3-Methoxyphenol
• 2,6-Dimethoxybenzoic acid
• Dimethoxymethane
• 2,3,4-Trimethoxybenzoic acid
• Syringic acid
• 3,4,5-Trimethoxyphenylacetonitrile