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4-Ethylguaiacol

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4-Ethylguaiacol
Names
IUPAC name 4-Ethyl-2-methoxy-phenol
Other names p-Ethylguaiacol
Homocresol
Guaiacyl ethane
2-Methoxy-4-ethylphenol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.018.637 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C9H12O2/c1-3-7-4-5-8(10)9(6-7)11-2/h4-6,10H,3H2,1-2H3Key: CHWNEIVBYREQRF-UHFFFAOYSA-N
  • InChI=1/C9H12O2/c1-3-7-4-5-8(10)9(6-7)11-2/h4-6,10H,3H2,1-2H3Key: CHWNEIVBYREQRF-UHFFFAOYAE
SMILES
  • Oc1ccc(cc1OC)CC
Properties
Chemical formula C9H12O2
Molar mass 152.193 g·mol
Appearance Colorless liquid
Melting point 15 °C (59 °F; 288 K)
Boiling point 234–236 °C
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2 1 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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. 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 stoichiometric ratio in which 4-EP and 4-EG are present can greatly affected the organoleptic properties of the wine.

See also

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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