4-Ethylguaiacol

4-Ethylguaiacol, often abbreviated to 4-EG, is a phenolic compound with the molecular formula C9H12O2. It is produced along with 4-ethylphenol (4-EP) in wine and beer by the spoilage yeast Brettanomyces.[1] 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.

4-Ethylguaiacol
Names
Preferred IUPAC name
4-Ethyl-2-methoxyphenol
Other names
p-Ethylguaiacol
Homocresol
Guaiacyl ethane
2-Methoxy-4-ethylphenol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.018.637
PubChem CID
UNII
CompTox Dashboard (EPA)
Properties
Chemical formula
 C9H12O2
Molar mass 152.193 g·mol−1
Appearance Colorless liquid
Melting point 15 °C (59 °F; 288 K)
Boiling point 234 to 236 °C (453 to 457 °F; 507 to 509 K)
Hazards
Safety data sheet External MSDS
EU classification (DSD) (outdated)
 Xi
S-phrases (outdated) S26 S37/39
NFPA 704 (fire diamond)
1
2
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

See also
  • Yeast in winemaking
  • Wine chemistry

References
  1. Caboni, Pierluigi; Sarais, Giorgia; Cabras, Marco; Angioni, Alberto (2007). "Determination of 4-Ethylphenol and 4-Ethylguaiacol in Wines by LC-MS-MS and HPLC-DAD-Fluorescence". Journal of Agricultural and Food Chemistry. 55 (18): 7288–93. doi:10.1021/jf071156m. PMID 17676867.
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