ChemicalBook Product Catalog Flavors and fragrances Synthetic fragrances Phenols, ethers and epoxides Phenols 2,6-Dimethoxyphenol

2,6-Dimethoxyphenol

Product Name2,6-Dimethoxyphenol
CAS91-10-1
MFC8H10O3
MW154.16
EINECS202-041-1
MOL File91-10-1.mol

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
biological source	synthetic
Water Solubility	2 g/100 mL (13 ºC)
JECFA Number	721
BRN	1526871
Henry's Law Constant	3.7×10¹ mol/(m³Pa) at 25℃, Sagebiel et al. (1992)
InChI	1S/C8H10O3/c1-10-6-4-3-5-7(11-2)8(6)9/h3-5,9H,1-2H3
InChIKey	KLIDCXVFHGNTTM-UHFFFAOYSA-N
SMILES	COc1cccc(OC)c1O
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	TSCA listed
HS Code	29095090
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
2,6-Dimethoxyphenol	English

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.

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.

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.

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.]