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Revision as of 18:12, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 465358118 of page 4-Ethylphenol for the Chem/Drugbox validation project (updated: '').  Latest revision as of 10:22, 21 October 2024 edit JWBE (talk | contribs)Extended confirmed users10,127 edits added Category:4-Hydroxyphenyl compounds using HotCat 
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{{Chembox
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 443352937 | verifiedrevid = 477221780
| Reference=<ref></ref> | Reference=<ref>{{Cite web |url=http://physchem.ox.ac.uk/MSDS/ET/4-ethylphenol.html |title=4-Ethylphenol MSDS |access-date=2002-11-08 |archive-url=https://web.archive.org/web/20021108024845/http://physchem.ox.ac.uk/MSDS/ET/4-ethylphenol.html |archive-date=2002-11-08 |url-status=dead }}</ref>
| Name = 4-Ethylphenol | Name = 4-Ethylphenol
| ImageFile = P-Ethylphenol.svg | ImageFile = P-Ethylphenol.svg
| ImageSize = 50px | ImageSize = 50px
| PIN = 4-Ethylphenol<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 690 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4 | quote = Only one name is retained, phenol, for C<sub>6</sub>H<sub>5</sub>-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''.}}</ref>
| OtherNames = ''p''-Ethylphenol<br />1-Ethyl-4-hydroxybenzene<br />1-Hydroxy-4-ethylbenzene<br />4-hydroxyphenylethane | OtherNames = ''p''-Ethylphenol<br />1-Ethyl-4-hydroxybenzene<br />1-Hydroxy-4-ethylbenzene<br />4-Hydroxyphenylethane
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 49584 | ChEBI = 49584
| SMILES = Oc1ccc(cc1)CC | SMILES = Oc1ccc(cc1)CC
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 28982 | ChemSpiderID = 28982
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = AGG7E6G0ZC | UNII = AGG7E6G0ZC
| EC_number = 204-598-6
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C13637 | KEGG = C13637
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| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 108475 | ChEMBL = 108475
| PubChem = 31242
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C8H10O/c1-2-7-3-5-8(9)6-4-7/h3-6,9H,2H2,1H3 | StdInChI = 1S/C8H10O/c1-2-7-3-5-8(9)6-4-7/h3-6,9H,2H2,1H3
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| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 123-07-9 | CASNo = 123-07-9
| RTECS = | RTECS =
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=8|H=10|O=1
| Formula = C<sub>8</sub>H<sub>10</sub>O
| MolarMass = 122.16 g/mol | Appearance = White solid
| Odor = leather-like
| Appearance = White solid
| Solvent = solvent | Solvent = solvent
| MeltingPtC = 45.1
| MeltingPt = 42–45&nbsp;°C
| MeltingPt_notes =
| BoilingPt = 218&nbsp;°C
| BoilingPtC = 218
| BoilingPt_notes =
}} }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| NFPA-H = 2
| EUClass = {{Hazchem_Xi}}
| NFPA-H = 2 | NFPA-F = 1
| NFPA-F = 1 | NFPA-R = 0
| NFPA-R = 0 | FlashPtC = 104
| SPhrases = {{S36}} {{S37}} | GHSPictograms = {{GHS05}}
| GHSSignalWord = Danger
| SPhrases = {{S7/9}} {{S26}} {{S36/37/39}} {{S45}}
| HPhrases = {{H-phrases|314}}
| PPhrases = {{P-phrases|260|264|280|301+330+331|303+361+353|304+340|305+351+338|310|321|363|405|501}}
}} }}
}} }}

'''Ethylphenol''' (4-EP) is an ] with the formula C<sub>2</sub>H<sub>5</sub>C<sub>6</sub>H<sub>4</sub>OH. It is one of three isomeric ]s. A white solid, it occurs as an impurity in ]s and as such is used in the production of some commercial ]s. It is also a precursor to 4-vinylphenol.<ref>{{Ullmann |doi=10.1002/14356007.a19_313|title=Phenol Derivatives|year=2000|last1=Fiege|first1=Helmut|last2=Voges|first2=Heinz-Werner|last3=Hamamoto|first3=Toshikazu|last4=Umemura|first4=Sumio|last5=Iwata|first5=Tadao|last6=Miki|first6=Hisaya|last7=Fujita|first7=Yasuhiro|last8=Buysch|first8=Hans-Josef|last9=Garbe|first9=Dorothea|last10=Paulus|first10=Wilfried|isbn=3527306730}}</ref>

== Natural occurrences ==
In ] and ], 4-EP is produced by the ] '']''. At concentrations greater than 140&nbsp;μg/L (typical ]) it gives the wine ]s 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 ], the exudate from the castor sacs of the mature ] (''Castor canadensis'') and the ] (''Castor fiber''), used in perfumery.

==Biochemistry==
4-EP is biosynthesized in two steps from ]. Decarboxylation gives ] as catalyzed by the enzyme ].<ref> {{webarchive|url=https://web.archive.org/web/20080219204946/http://www.etslabs.com/scripts/ets/pagetemplate/blank.asp?pageid=193 |date=2008-02-19 }} at etslabs.com</ref> 4-Vinylphenol is further reduced to 4-ethylphenol by the enzyme ]. Coumaric acid is sometimes added to ], enabling the positive identification of ''Brettanomyces'' by smell.
:] to 4-EP by ''Brettanomyces'']]{{clear|left}}

== See also ==
* ]
* ]
* ]
* ]

== References ==
<references/>

== External links ==
*

{{DEFAULTSORT:Ethylphenol, 4-}}
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