# 4-Ethylphenol > Mediated Wiki article. Canonical URL: https://mediated.wiki/source/4-Ethylphenol > Markdown URL: https://mediated.wiki/source/4-Ethylphenol.md > Source: https://en.wikipedia.org/wiki/4-Ethylphenol > Source revision: 1326779059 > License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/) 4-Ethylphenol[1] Names Preferred IUPAC name 4-Ethylphenol[2] Other names p-Ethylphenol 1-Ethyl-4-hydroxybenzene 1-Hydroxy-4-ethylbenzene 4-Hydroxyphenylethane Identifiers CAS Number 123-07-9 Y 3D model (JSmol) Interactive image ChEBI CHEBI:49584 Y ChEMBL ChEMBL108475 Y ChemSpider 28982 Y ECHA InfoCard 100.004.181 EC Number 204-598-6 KEGG C13637 Y PubChem CID 31242 UNII AGG7E6G0ZC Y CompTox Dashboard (EPA) DTXSID4021977 InChI InChI=1S/C8H10O/c1-2-7-3-5-8(9)6-4-7/h3-6,9H,2H2,1H3 Y Key: HXDOZKJGKXYMEW-UHFFFAOYSA-N Y InChI=1/C8H10O/c1-2-7-3-5-8(9)6-4-7/h3-6,9H,2H2,1H3 Key: HXDOZKJGKXYMEW-UHFFFAOYAF SMILES Oc1ccc(cc1)CC Properties Chemical formula C8H10O Molar mass 122.167 g·mol−1 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 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) 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 [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references Chemical compound **Ethylphenol** (4-EP) is an [organic compound](/source/Organic_compound) with the formula C2H5C6H4OH. It is one of three isomeric [ethylphenols](/source/Ethylphenol). A white solid, it occurs as an impurity in [xylenols](/source/Xylenol) and as such is used in the production of some commercial [phenolic resins](/source/Phenolic_resin). It is also a precursor to 4-vinylphenol.[3] ## Production 4-Ethylphenol is produced by careful [sulfonation](/source/Sulfonation) of [ethylbenzene](/source/Ethylbenzene) to 4-ethylphenylsulfonic acid.[3] The sulfonic acid is subsequently subjected to [alkaline fusion](/source/Alkaline_fusion), the dissolution of the sulfonic acid in molten alkali metal base. The main steps in the synthesis are shown: - EtC6H5 + SO3 → EtC6H4SO3H (Et = ethyl) - EtC6H4SO3H + NaOH → EtC6H4ONa + NaHSO3 - EtC6H4ONa + H+ → ArOH + Na+ ## Natural occurrences In [wine](/source/Wine) and [beer](/source/Beer), 4-EP is produced by the [yeast](/source/Yeast) *[Brettanomyces](/source/Brettanomyces)*. At concentrations greater than 140 μg/L (typical [sensory threshold](/source/Sensory_threshold)) it gives the wine [aromas](/source/Aroma) 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](/source/Castoreum), the exudate from the castor sacs of the mature [North American beaver](/source/North_American_beaver) (*Castor canadensis*) and the [Eurasian beaver](/source/Eurasian_beaver) (*Castor fiber*), used in perfumery. ## Biochemistry 4-EP is biosynthesized in two steps from [*p*-coumaric acid](/source/P-coumaric_acid). Decarboxylation gives [4-vinylphenol](/source/4-vinylphenol) as catalyzed by the enzyme [cinnamate decarboxylase](/source/Cinnamate_decarboxylase).[4] 4-Vinylphenol is further reduced to 4-ethylphenol by the enzyme [vinyl phenol reductase](/source/Vinyl_phenol_reductase). Coumaric acid is sometimes added to [microbiological media](/source/Growth_medium), enabling the positive identification of *Brettanomyces* by smell. - The conversion of [*p*-coumaric acid](/source/P-Coumaric_acid) to 4-EP by *Brettanomyces* ## See also - [4-Ethylguaiacol](/source/4-Ethylguaiacol) - [Yeast in winemaking](/source/Yeast_in_winemaking) - [Wine fault](/source/Wine_fault) - [Wine chemistry](/source/Wine_chemistry) ## References 1. **[^](#cite_ref-1)** ["4-Ethylphenol MSDS"](https://web.archive.org/web/20021108024845/http://physchem.ox.ac.uk/MSDS/ET/4-ethylphenol.html). Archived from [the original](http://physchem.ox.ac.uk/MSDS/ET/4-ethylphenol.html) on 2002-11-08. Retrieved 2002-11-08. 1. **[^](#cite_ref-iupac2013_2-0)** *Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)*. Cambridge: [The Royal Society of Chemistry](/source/Royal_Society_of_Chemistry). 2014. p. 690. [doi](/source/Doi_(identifier)):[10.1039/9781849733069-FP001](https://doi.org/10.1039%2F9781849733069-FP001). [ISBN](/source/ISBN_(identifier)) [978-0-85404-182-4](https://en.wikipedia.org/wiki/Special:BookSources/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*. 1. ^ [***a***](#cite_ref-Ull_3-0) [***b***](#cite_ref-Ull_3-1) 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](/source/Ullmann's_Encyclopedia_of_Industrial_Chemistry)*. Weinheim: Wiley-VCH. [doi](/source/Doi_(identifier)):[10.1002/14356007.a19_313](https://doi.org/10.1002%2F14356007.a19_313). [ISBN](/source/ISBN_(identifier)) [3527306730](https://en.wikipedia.org/wiki/Special:BookSources/3527306730). 1. **[^](#cite_ref-4)** [Brettanomyces Monitoring by Analysis of 4-ethylphenol and 4-ethylguaiacol](http://www.etslabs.com/scripts/ets/pagetemplate/blank.asp?pageid=193) [Archived](https://web.archive.org/web/20080219204946/http://www.etslabs.com/scripts/ets/pagetemplate/blank.asp?pageid=193) 2008-02-19 at the [Wayback Machine](/source/Wayback_Machine) at etslabs.com ## External links - [4-Ethylphenol oral toxicity data](https://web.archive.org/web/20040105113802/http://wwwdb.mhlw.go.jp/ginc/cgi-bin/db1_search.pl?CAS=123-07-9&MID=177) --- Adapted from the Wikipedia article [4-Ethylphenol](https://en.wikipedia.org/wiki/4-Ethylphenol) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/4-Ethylphenol?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.