4-Ethylguaiacol
From Wikipedia, the free encyclopedia
| 4-Ethylguaiacol | ||
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| General | ||
| Systematic name | 4-Ethyl-2-methoxy-phenol | |
| Other names | p-Ethylguaiacol homocresol Guaiacyl ethane 2-Methoxy-4-ethylphenol |
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| Molecular formula | C9H12O2 | |
| SMILES | CCC1=CC(=C(C=C1)O)OC | |
| Molar mass | 152.19 g/mol | |
| Appearance | colourless liquid | |
| CAS number | 2785-89-9 | |
| Properties | ||
| Melting point | 15°C | |
| Boiling point | 234-236°C | |
| Hazards | ||
| MSDS | External MSDS | |
| EU classification |  Xi |
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| NFPA 704 |
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| R-phrases | R36/37/38 | |
| S-phrases | S26, S37/39 | |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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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 aggressing, the presence of the compound often signifies a wine fault. Interestingly the stoichiometric ratio in which 4-EP and 4-EG are present can greatly affected the organoleptic properties of the wine.
