4-Ethylguaiacol

4-Ethylguaiacol
IUPAC name 4-Ethyl-2-methoxy-phenol
Other names p-Ethylguaiacol Homocresol Guaiacyl ethane 2-Methoxy-4-ethylphenol
Identifiers
CAS number	2785-89-9 Y
PubChem	62465
ChemSpider	56245 Y
UNII	C9NFD83BJ5 Y
Jmol-3D images	Image 1
SMILES Oc1ccc(cc1OC)CC
InChI InChI=1S/C9H12O2/c1-3-7-4-5-8(10)9(6-7)11-2/h4-6,10H,3H2,1-2H3 Y Key: CHWNEIVBYREQRF-UHFFFAOYSA-N Y InChI=1/C9H12O2/c1-3-7-4-5-8(10)9(6-7)11-2/h4-6,10H,3H2,1-2H3 Key: CHWNEIVBYREQRF-UHFFFAOYAE
Properties
Molecular formula	C9H12O2
Molar mass	152.19 g mol−1
Appearance	Colorless liquid
Melting point	15 °C; 59 °F; 288 K
Boiling point	234–236 °C
Hazards
MSDS	External MSDS
EU classification	Xi
S-phrases	S26 S37/39
NFPA 704	1 2 0
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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 affected the organoleptic properties of the wine.

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.