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W253200

Sigma-Aldrich

Guaiacol

natural, ≥99%, FG

Synonym(s):
Catechol monomethyl ether, 2-Methoxyphenol, Pyrocatechol monomethyl ether
Linear Formula:
(CH3O)C6H4OH
CAS Number:
Molecular Weight:
124.14
FEMA Number:
2532
Beilstein:
508112
EC Number:
Council of Europe no.:
173
MDL number:
PubChem Substance ID:
Flavis number:
4.005
NACRES:
NA.21

Quality Level

grade

FG
Halal
Kosher
natural

agency

follows IFRA guidelines
meets purity specifications of JECFA

reg. compliance

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

vapor density

4.27 (vs air)

vapor pressure

0.11 mmHg ( 25 °C)

assay

≥99%

form

liquid
solid

refractive index

n20/D 1.543 (lit.)

bp

205 °C (lit.)

mp

26-29 °C (lit.)

density

1.129 g/mL at 25 °C (lit.)

Documentation

see Safety & Documentation for available documents

Organoleptic

medicinal; woody; smoky; spicy; vanilla

application(s)

flavors and fragrances

food allergen

no known allergens

fragrance allergen

no known allergens

SMILES string

COc1ccccc1O

InChI

1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3

InChI key

LHGVFZTZFXWLCP-UHFFFAOYSA-N

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General description

Guaiacol is a flavor compound occurs naturally in tomatoes and wine that is matured in oak barrels.

Application

Guaiacol can be used to prepare vanillin, a well-known food flavoring agent.

Packaging

5, 10 kg in poly drum
1 kg in glass bottle

Biochem/physiol Actions

Guaiacol, along with 2,4,6-trichloroanisole, is responsible for cork taint in wine. A method has been developed for extraction and quantitation of the two compounds.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

194.0 °F - closed cup

Flash Point(C)

90 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

A Solanum lycopersicum catechol?O?methyltransferase involved in synthesis of the flavor molecule guaiacol.
Mageroy MH, et al.
The Plant Journal, 69(6), 1043-1051 (2012)
Engineers of scent
Waltz E
Nature Biotechnology, 33(4), 329?332-329?332 (2015)
Phenol Derivatives
Ullmann's Encyclopedia of Industrial Chemistry, 33(4), 329?332-329?332 (2000)
Feng Li et al.
Food chemistry, 135(2), 332-337 (2012-08-08)
Hexahydrocurcumin, 1-dehydro-[6]-gingerdione, 6-dehydroshogaol and 6-shogaol were evaluated for their antioxidant and anti-inflammatory activities in the present study. The relative antioxidant potencies of ginger compounds decreased in similar order of 1-dehydro-[6]-gingerdione, hexahydrocurcumin>6-shogaol>6-dehydroshogaol in both 1,1-diphenyl-2-picyrlhydrazyl (DPPH) radical-scavenging and trolox equivalent antioxidant
Joel D Mainland et al.
Nature neuroscience, 17(1), 114-120 (2013-12-10)
Humans have ~400 intact odorant receptors, but each individual has a unique set of genetic variations that lead to variation in olfactory perception. We used a heterologous assay to determine how often genetic polymorphisms in odorant receptors alter receptor function.

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