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W253200

Sigma-Aldrich

Guaiacol

greener alternative

natural, ≥99%, FG

Synonym(s):

2-Methoxyphenol, Catechol monomethyl ether, Pyrocatechol monomethyl ether

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About This Item

Linear Formula:
(CH3O)C6H4OH
CAS Number:
90-05-1
Molecular Weight:
124.14
FEMA Number:
2532
Beilstein:
508112
EC Number:
201-964-7
Council of Europe no.:
173
MDL number:
MFCD00002185
UNSPSC Code:
12164502
PubChem Substance ID:
24901124
Flavis number:
4.005
NACRES:
NA.21

grade

FG
Fragrance grade
Halal
Kosher
natural

Quality Level

400

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

greener alternative product characteristics

Less Hazardous Chemical Syntheses
Use of Renewable Feedstocks
Learn more about the Principles of Green Chemistry.

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.)

application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

food allergen

no known allergens

fragrance allergen

no known allergens

greener alternative category

Aligned

Organoleptic

bacon; smoky; woody; spicy; vanilla

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.
We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives . This product is a Biobased products, showing key improvements in Green Chemistry Principles “Less Hazardous Chemical Syntheses” and “Use of Renewable Feedstock”.

Application

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

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
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319

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

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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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)
Alan P Pollnitz et al.
Journal of agricultural and food chemistry, 52(11), 3244-3252 (2004-05-27)
The deuterium-labeled standards [(2)H(3)]-guaiacol and [(2)H(3)]-4-methylguaiacol were synthesized and utilized in a method employing gas chromatography-mass spectrometry to determine the concentration of guaiacol and 4-methylguaiacol in wine or extracts of oak shavings. The method was combined with previously published methods
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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