W315605

Sigma-Aldrich

4-Ethylphenol

≥98%, FG

Linear Formula:
C2H5C6H4OH
CAS Number:
Molecular Weight:
122.16
FEMA Number:
3156
Beilstein/REAXYS Number:
1363317
EC Number:
Council of Europe no.:
550
MDL number:
eCl@ss:
39023356
PubChem Substance ID:
Flavis number:
4.022
NACRES:
NA.21

Quality Level

biological source

synthetic

grade

FG
Halal
Kosher

Agency/Method

follows IFRA guidelines

reg. compliance

EU Regulation 1223/2009
EU Regulation 1334/2008 & 872/2012

vapor density

4.2 (vs air)

vapor pressure

0.13 mmHg ( 20 °C)

assay

≥98%

bp

218-219 °C (lit.)

mp

40-42 °C (lit.)

Documentation

see Safety & Documentation for available documents

Featured Industry

Flavors and Fragrances

Organoleptic

smoky; phenolic

food allergen

no known allergens

fragrance allergen

no known allergens

SMILES string

CCc1ccc(O)cc1

InChI

1S/C8H10O/c1-2-7-3-5-8(9)6-4-7/h3-6,9H,2H2,1H3

InChI key

HXDOZKJGKXYMEW-UHFFFAOYSA-N

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General description

4-Ethylphenol is a volatile phenol. It has been synthesized from p-coumaric acid by employing a synthetic medium containing Dekkera bruxellensis ISA 1791. It has been identified as an aroma compound in red wine.
4-Ethylphenol (4-EP) is a para-substituted phenolic compound. It is one of the important aroma compounds in red wine. The aroma associated with 4-EP in red wine has been described as ′′horsy′′, ′′leather′′, ′′medicinal′′, ′′smoky′′, ′′barnyard′′, ′′animal′′ and ′′sweaty saddle′′-like. Production of 4-EP from p-coumaric acid in synthetic media utilizing several yeast species associated with wine production has been reported. Its electroactive center and oxidation pathways have been studied by voltammetric techniques at a glassy carbon electrode (GCE). Hydrogenolysis of lignin has been reported to form 3.1% of 4-EP. This method may be a potential alternative to the conventional petrochemical route of its synthesis. A sensor based on the molecularly imprinted nanoparticles to selectively detect 4-EP has been developed. The ability of polyaniline (PANI) materials and suberin extracted from cork in removing 4-EP from wine has been investigated.

Application

4-Ethylphenol is suitable for use in the determination of 4-ethylguaiacol and 4-ethylphenol in the aroma of red wines using headspace-solid-phase microextraction method.
4-Ethylphenol may be used in the preparation of optically active 1-(4′-hydroxyphenyl)- ethanol, via hydroxylation by Pseudomonas putida and p-cresol methylhydroxylase.

Packaging

10 kg in fiber drum
1 kg in glass bottle

Other Notes

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Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 2430 8 / PGIII

WGK Germany

WGK 1

Flash Point(F)

212.0 °F - closed cup

Flash Point(C)

100 °C - closed cup

Removal of 4-Ethylphenol and 4-Ethylguaiacol with Polyaniline-Based Compounds in Wine-Like Model Solutions and Red Wine.
Carrasco-Sanchez V, et al.
Molecules (Basel), 20(8), 14312-14325 (2015)
Phenol and para-substituted phenols electrochemical oxidation pathways.
Enache TA and Oliveira-Brett AM.
Journal of Electroanalytical Chemistry, 655(1), 9-16 (2011)
Identification of yeasts isolated from wine-related environments and capable of producing 4-ethylphenol.
Dias L, et al.
Food Microbiology, 20(5), 567-574 (2003)
Sorption of 4-ethylphenol and 4-ethylguaiacol by suberin from cork.
Gallardo-Chacon JJ and Karbowiak T.
Food Chemistry, 181, 222-226 (2015)
W McIntire et al.
The Biochemical journal, 224(2), 617-621 (1984-12-01)
Enzymic hydroxylation of 4-ethylphenol by (a) Pseudomonas putida and (b) highly purified p-cresol methylhydroxylase gave optically active 1-(4'-hydroxyphenyl)-ethanol. The products were transformed into the phenolic methyl ethers and shown to contain 69.5% and 65.6%, respectively, of the (S)-(-)-isomer. The stereochemistry...

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