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4-Ethylphenol

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4-Ethylphenol
Names
Preferred IUPAC name 4-Ethylphenol
Other names p-Ethylphenol
1-Ethyl-4-hydroxybenzene
1-Hydroxy-4-ethylbenzene
4-Hydroxyphenylethane
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.181 Edit this at Wikidata
EC Number
  • 204-598-6
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H10O/c1-2-7-3-5-8(9)6-4-7/h3-6,9H,2H2,1H3Key: HXDOZKJGKXYMEW-UHFFFAOYSA-N
  • InChI=1/C8H10O/c1-2-7-3-5-8(9)6-4-7/h3-6,9H,2H2,1H3Key: HXDOZKJGKXYMEW-UHFFFAOYAF
SMILES
  • Oc1ccc(cc1)CC
Properties
Chemical formula C8H10O
Molar mass 122.167 g·mol
Appearance White solid
Odor leather-like
Melting point 45.1 °C (113.2 °F; 318.2 K)
Boiling point 218 °C (424 °F; 491 K)
Hazards
GHS labelling:
Pictograms GHS05: Corrosive
Signal word Danger
Hazard statements H314
Precautionary statements P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501
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
Flash point 104 °C (219 °F; 377 K)
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

Ethylphenol (4-EP) is an organic compound with the formula C2H5C6H4OH. It is one of three isomeric ethylphenols. A white solid, it occurs as an impurity in xylenols and as such is used in the production of some commercial phenolic resins. It is also a precursor to 4-vinylphenol.

Natural occurrences

In wine and beer, 4-EP is produced by the yeast Brettanomyces. At concentrations greater than 140 μg/L (typical sensory threshold) it gives the wine aromas described as barnyard, medicinal, band-aids, and mousy. In certain Belgian beer styles, a high 4-EP level may be desirable; however, very high levels of the compound in wine can render it undrinkable. The level of 4-EP is roughly proportional to Brettanomyces concentration and activity, and can therefore be used as an indicator of the yeast's presence. There are significant differences between strains of Brettanomyces in their ability to produce 4-EP.

4-EP is also a component of castoreum, the exudate from the castor sacs of the mature North American beaver (Castor canadensis) and the Eurasian beaver (Castor fiber), used in perfumery.

Biochemistry

4-EP is biosynthesized in two steps from p-coumaric acid. Decarboxylation gives 4-vinylphenol as catalyzed by the enzyme cinnamate decarboxylase. 4-Vinylphenol is further reduced to 4-ethylphenol by the enzyme vinyl phenol reductase. Coumaric acid is sometimes added to microbiological media, enabling the positive identification of Brettanomyces by smell.

The conversion of p-coumaric acid to 4-EP by Brettanomyces

See also

References

  1. "4-Ethylphenol MSDS". Archived from the original on 2002-11-08. Retrieved 2002-11-08.
  2. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 690. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. Only one name is retained, phenol, for C6H5-OH, both as a preferred name and for general nomenclature. The structure is substitutable at any position. Locants 2, 3, and 4 are recommended, not o, m, and p.
  3. Fiege, Helmut; Voges, Heinz-Werner; Hamamoto, Toshikazu; Umemura, Sumio; Iwata, Tadao; Miki, Hisaya; Fujita, Yasuhiro; Buysch, Hans-Josef; Garbe, Dorothea; Paulus, Wilfried (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN 3527306730.
  4. Brettanomyces Monitoring by Analysis of 4-ethylphenol and 4-ethylguaiacol Archived 2008-02-19 at the Wayback Machine at etslabs.com

External links

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