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W267112

Sigma-Aldrich

2-Methoxy-4-methylphenol

natural, 97%, FG

Synonym(s):

2-Hydroxy-5-methylanisole, 2-Methoxy-p-cresol, 4-Hydroxy-3-methoxytoluene, 4-Methylguaiacol, Creosol

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About This Item

Linear Formula:
CH3OC6H3(CH3)OH
CAS Number:
93-51-6
Molecular Weight:
138.16
FEMA Number:
2671
Beilstein:
1862340
EC Number:
202-252-9
Council of Europe no.:
175c
MDL number:
MFCD00002378
UNSPSC Code:
12164502
PubChem Substance ID:
24901237
Flavis number:
4.007
NACRES:
NA.21

grade

FG
Halal
Kosher
natural

Quality Level

400

reg. compliance

EU Regulation 1334/2008 & 178/2002
FDA 21 CFR 117

Assay

97%

refractive index

n20/D 1.537 (lit.)

bp

221-222 °C (lit.)

mp

5 °C (lit.)

density

1.092 g/mL at 25 °C (lit.)

application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

food allergen

no known allergens

Organoleptic

clove; leathery; smoky; spicy; smoky; sweet; vanilla

SMILES string

COc1cc(C)ccc1O

InChI

1S/C8H10O2/c1-6-3-4-7(9)8(5-6)10-2/h3-5,9H,1-2H3

InChI key

PETRWTHZSKVLRE-UHFFFAOYSA-N

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General description

2-Methoxy-4-methylphenol is a phenolic flavor compound reported in commercial liquid smoke flavoring and wood smoke.

Biochem/physiol Actions

Taste at 1.0-1.25 ppm

Other Notes

Natural occurrence: Coffee, gruyere cheese, pork, beer, rum, bourbon whiskey, malt, sherry, cocoa, tea, mushroom, bourbon vanilla, green mate, jasmine flowers.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

210.2 °F - closed cup

Flash Point(C)

99 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBQ0131
SHBP5935
SHBL5503
MKCJ3300
MKBS9051V

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Study of a commercial liquid smoke flavoring by means of gas chromatography/mass spectrometry and Fourier transform infrared spectroscopy.
Guillen MD, et al.
Journal of Agricultural and Food Chemistry, 43(2), 463-468 (1995)
The flavor chemistry of wood smoke.
Maga JA
Food Reviews International, 3(1-2), 139-183 (1987)
Day-Shin Hsu et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 16(10), 3121-3131 (2010-02-02)
An efficient and short entry to polyfunctionalized linear triquinanes from 2-methoxyphenols is described by utilizing the following chemistry. The Diels-Alder reactions of masked o-benzoquinones, derived from 2-methoxyphenols, with cyclopentadiene afford tricyclo[5.2.2.0(2,6)]undeca-4,10-dien-8-ones. Photochemical oxa-di-pi-methane (ODPM) rearrangements and 1,3-acyl shifts of the
Anthea L Fudge et al.
Journal of agricultural and food chemistry, 60(1), 52-59 (2011-12-02)
In this study, the suitability of mid-infrared (MIR) spectroscopy, combined with principal component analysis (PCA) and linear discriminant analysis (LDA), was evaluated as a rapid analytical technique to identify smoke tainted wines. Control (i.e., unsmoked) and smoke-affected wines (260 in
N Ogata et al.
Pharmacology, 51(3), 195-204 (1995-09-01)
Wood creosote, principally a mixture of non-, alkyl- and/or alkoxy-substituted phenolic compounds, was orally administered to adult male volunteers to determine its metabolites and pharmacokinetic parameters. After a 133-mg single dose, its major constituents (i.e. phenol 15 mg, guaiacol 32
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