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W267104

Sigma-Aldrich

2-Methoxy-4-methylphenol

≥98%, 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.:
175
MDL number:
MFCD00002378
UNSPSC Code:
12164502
PubChem Substance ID:
24901236
Flavis number:
4.007
NACRES:
NA.21

biological source

synthetic

Quality Level

400

grade

FG
Fragrance grade
Halal
Kosher

Agency

follows IFRA guidelines
meets purity specifications of JECFA

reg. compliance

EU Regulation 1223/2009
EU Regulation 1334/2008 & 178/2002
FDA 21 CFR 117
FDA 21 CFR 172.515

Assay

≥98%

color

colorless to light yellow

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

fragrance allergen

no known allergens

Organoleptic

clove; leathery; 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 one of the main volatile aroma compounds identified in wood smoke and oak-aged wines.

Biochem/physiol Actions

Odor at 1.0%
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 and 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Stir bar sorptive extraction for the determination of volatile compounds in oak-aged wines.
Marin J, et al.
Journal of Chromatography A, 1098(1), 1-6 (2005)
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
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
N Ogata et al.
Research communications in chemical pathology and pharmacology, 77(3), 359-366 (1992-09-01)
Wood creosote, a mixture of guaiacol, creosol, and other related phenolic compounds, suppresses the spontaneous longitudinal phasic contractions of an isolated rat ileal segment. Thirty-two phenolic compounds were screened for this activity to identify the active substances in wood creosote.
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