| Description | 4-Ethylphenol, often abbreviated to 4-EP, is a phenolic compound with the formula C8H10O. It is colorless or white needles with a powerful woody-phenolic and yet somewhat sweet odor and tends to be yellow on exposure to light. It is slightly solouble in water, solouble in alcohol, ether and benzene and carbon disulfide. It is found in arabica coffee and can be produced in wine and beer by the spoilage yeast Brettanomyces. It is the starting material for the production of 4-vinylphenol and of various antioxidants and can also be used as an intermediate for pharmaceuticals and dyes. |
| References | 1. https://en.wikipedia.org/wiki/4-Ethylphenol
2. http://www.hmdb.ca/metabolites/HMDB29306
3. https://toxnet.nlm.nih.gov/cgi-bin/sis/search2/f?./temp/~x8ypqu:1:cpp
4. https://toxnet.nlm.nih.gov/cgi-bin/sis/search2/f?./temp/~x8ypqu:1:manf |
| Chemical Properties | off-white solid |
| Chemical Properties | p-Ethylphenol has a powerful woody-phenolic, medicinal, yet somewhat sweet odor. |
| Occurrence | Reported found in yellow passion fruit, smoked fish, lean fish, beer, cognac, rum, whiskey, cider, sherry, grape wines and coffee |
| Uses | Intermediates of Liquid Crystals |
| Uses | 4-Ethylphenol is suitable for use in the determination of 4-ethylguaiacol and 4-ethylphenol in the aroma of red wines using headspace-solid-phase microextraction method. It is a chemical reagent used in the synthesis of 5-HT1A receptor agonists endowed with antinociceptive activity in vivo. It is also used in the preparation of isopropylamides as potent and noncovalent proteosome inhibitors. |
| Uses | 4-Ethylphenol is suitable for use in the determination of 4-ethylguaiacol and 4-ethylphenol in the aroma of red wines using headspace-solid-phase microextraction method. |
| Definition | ChEBI: 4-ethylphenol is a member of the class of phenols carrying an ethyl substituent at position 4. It has a role as a fungal xenobiotic metabolite. |
| Preparation | By catalytic reaction between phenol and ethylene or ethanol; by heating 8-chloro-3-ethylbenzene with NaOH in the presence of copper powder. |
| Aroma threshold values | Detection: 42 to 130 ppb |
| Synthesis Reference(s) | The Journal of Organic Chemistry, 14, p. 1089, 1949 DOI: 10.1021/jo01158a018 |
| General Description | 4-Ethylphenol is a volatile phenol. It has been synthesized from p-coumaric acid by employing a synthetic medium containing Dekkera bruxellensis ISA 1791. It has been identified as an aroma compound in red wine. |
| Hazard | Toxic material. |
| Safety Profile | Poison by intravenous route. When heated to decomposition it emits acrid smoke and irritating vapors. |
| Purification Methods | Non-acidic impurities are removed by passing steam through a boiling solution containing 1 mole of the phenol and 1.75 moles of NaOH (as an aqueous 10% solution). The residue is cooled and acidified with 30% (v/v) H2SO4, and the free phenol is extracted into diethyl ether. The extract is washed with water, dried with CaSO4 and the ether is evaporated. The phenol is distilled at 100mm pressure through a Stedman gauze-packed column (p 11). It is further purified by fractional crystallisation by partial freezing, and by zone refining, under N2 [Biddiscombe et al. J Chem Soc 5764 1963]. Alternatively purify it via the benzoate, as for phenol. The 4-nitrophenylbenzoate has m 80o (from EtOH). [Beilstein 6 H 470, 6 III 1663, 5 IV 3020.] |
