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4-ethylguaiacol

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EntityQ229953· pop 14· linked from 12 articles

4-ethylguaiacol

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4-Ethylguaiacol, often abbreviated to 4-EG, is a phenolic compound with the molecular formula C9H12O2 that's a key aromatic component in various products, from food and beverages to cosmetics and pharmaceuticals. It can be produced in wine and beer by Brettanomyces. It is also frequently present in bio-oil produced by pyrolysis of lignocellulosic biomass.

Chemical data

Formula
C9H12O2
Molecular weight
152.19 g/mol
IUPAC name
4-ethyl-2-methoxyphenol
SMILES
CCC1=CC(=C(C=C1)O)OC
InChIKey
CHWNEIVBYREQRF-UHFFFAOYSA-N
XLogP
1.7
Polar surface area
29.5 Ų
H-bond donors
1
H-bond acceptors
2
Formal charge
0

via PubChem

Drug data · ChEMBL

Molecule type
Small molecule

via ChEMBL · EBI

Wikidata facts

Mass
152.084
Show 6 more facts
chemical formula
C₉H₁₂O₂
found in taxon
Coffea
canonical SMILES
CCC1=CC(=C(C=C1)O)OC
melting point
15.0
boiling point
235
Commons category
4-Ethylguaiacol
Sources (3)

via Wikidata · CC0

~1 min read

Encyclopedic overview

4 sections
Contents
  • Winemaking
  • Bio-oil
  • See also
  • References

4-Ethylguaiacol, often abbreviated to 4-EG, is a phenolic compound with the molecular formula C9H12O2 that's a key aromatic component in various products, from food and beverages to cosmetics and pharmaceuticals. It can be produced in wine and beer by Brettanomyces. It is also frequently present in bio-oil produced by pyrolysis of lignocellulosic biomass.

== Winemaking == It is produced along with 4-ethylphenol (4-EP) in wine and beer by the spoilage yeast Brettanomyces. When it is produced by the yeast to concentrations greater than the sensory threshold of >600 μg/L, it can contribute bacon, spice, clove, or smoky aromas to the wine. On their own these characters can be quite attractive in a wine, however as the compound usually occurs with 4-EP whose aromas can be more aggressive, the presence of the compound often signifies a wine fault. The ratio in which 4-EP and 4-EG are present can greatly affect the organoleptic properties of the wine.

Excerpted from Wikipedia’s “4-ethylguaiacol” article, available under the CC BY-SA 4.0 licence.