| Identification | More | [Name]
4-Ethylphenol | [CAS]
123-07-9 | [Synonyms]
4-ETHYLPHENOL
ETHYLPHENOLS
FEMA 3156
LABOTEST-BB LT00436976
PEP
P-ETHYLPHENOL
(4-Hydroxyphenyl)ethane
(p-Hydroxyphenyl)ethane
1-Ethyl-4-hydroxybenzene
1-Hydroxy-4-ethylbenzene
4-ethyl-pheno
4-hydroxyphenylethane
Paraethylphenol
para-ethylphenol
p-ethyl-pheno
Phenol, p-ethyl-
Phenol,4-ethyl-
Phenol,p-ethyl-
p-Hydroxyethylbenzene
p-Ethyl Phenol 4-Ethyl Phenol | [EINECS(EC#)]
204-598-6 | [Molecular Formula]
C8H10O | [MDL Number]
MFCD00002393 | [Molecular Weight]
122.16 | [MOL File]
123-07-9.mol |
| Chemical Properties | Back Directory | [Appearance]
off-white solid | [Melting point ]
40-42 °C(lit.) | [Boiling point ]
218-219 °C(lit.) | [density ]
1,011 g/cm3 | [vapor density ]
4.2 (vs air)
| [vapor pressure ]
0.13 mm Hg ( 20 °C)
| [FEMA ]
3156 | [refractive index ]
1.5330 | [Fp ]
213 °F
| [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
4.9g/l | [form ]
Crystalline Mass or Crystals | [pka]
pK1:10.0 (25°C) | [color ]
White to brownish | [Specific Gravity]
1.0123 (20℃) | [Odor]
at 1.00 % in dipropylene glycol. phenolic castoreum smoke guaiacol | [Stability:]
Stable. Incompatible with acid chlorides, acid anhydrides, oxidizing agents. | [Odor Type]
smoky | [Water Solubility ]
4.9 g/L (25 ºC) | [Usage]
Intermediates of Liquid Crystals | [JECFA Number]
694 | [BRN ]
1363317 | [InChIKey]
HXDOZKJGKXYMEW-UHFFFAOYSA-N | [LogP]
2.1 at 20℃ and pH7 | [Surface tension]
54mN/m at 998g/L and 22℃ | [CAS DataBase Reference]
123-07-9(CAS DataBase Reference) | [NIST Chemistry Reference]
Phenol, 4-ethyl-(123-07-9) | [EPA Substance Registry System]
123-07-9(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,C | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 2430 8/PG 3
| [WGK Germany ]
3
| [RTECS ]
SL4040000
| [TSCA ]
Yes | [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29071900 | [Safety Profile]
Poison by intravenous route. When heated to decomposition it
emits acrid smoke and irritating vapors. | [Hazardous Substances Data]
123-07-9(Hazardous Substances Data) |
| Hazard Information | Back Directory | [Hazard]
Toxic material. | [Description]
4-Ethylphenol (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. It is an industrially versatile commodity chemical widely applied in the pharmaceutical and food industries. | [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]
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. | [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]
Intermediates of Liquid Crystals | [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.
| [Production Methods]
4-Ethylphenol is produced industrially by sulfonation of ethylbenzene under mild (kinetically controlled) conditions and subsequent alkali fusion of the 4-ethylbenzenesulfonic acid obtained. The purity of the commercial product is 98%.
| [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. | [Toxicology]
4-Ethylphenol is a potentially toxic compound, capable of producing respiratory distress, cardiovascular collapse, shock, ventricular tachycardia, and coma in an adult. Liver, lung, central nervous system and renal injury may also occur. In case of exposure to eyes, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. Monitor for respiratory distress in case of inhalation exposure. Systemic manifestations of toxicity may include nausea, vomiting, diarrhea, dyspnea, tachypnea, pallor, and profuse sweating.
| [storage]
Store at -20°C | [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.] | [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
[5] YING ZHANG Shaojun D Liangkun Long. Heterologous synthesis of 4-ethylphenol in engineered Escherichia coli[J]. Process Biochemistry, 2020, 96: Pages 157-164. DOI:10.1016/j.procbio.2020.06.003.
[6] WOHLFARTH C. Dielectric constant of 4-ethylphenol[C]. 1900: 0. DOI:10.1007/978-3-540-75506-7\_257.
[7] K H JONES D J H P W Trudgill. 4-Ethylphenol metabolism by Aspergillus fumigatus.[J]. Applied and Environmental Microbiology, 1994, 60 6: 1978-1983. DOI:10.1128/aem.60.6.1978-1983.1994. |
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