Structure via PubChem · Public domain (PubChem)
4-ethylguaiacol
Sign in to save4-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
- Subclass of
- chemical compound
- 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
via Wikidata · CC0
~1 min read
Encyclopedic overview
4 sectionsContents
- 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.