Misplaced Pages

4-Ethylphenol: Difference between revisions

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively
Page 1
Page 2
← Previous editContent deleted Content addedVisualWikitext
Revision as of 14:36, 6 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report errors or [[user← Previous edit Latest revision as of 10:22, 21 October 2024 edit undoJWBE (talk | contribs)Extended confirmed users10,127 edits added Category:4-Hydroxyphenyl compounds using HotCat 
(44 intermediate revisions by 26 users not shown)
Line 1: Line 1:
{{chembox {{Chembox
| Watchedfields = changed
| verifiedrevid = 443351568 | 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
| ImageFile = P-Ethylphenol.svg | Name = 4-Ethylphenol
| 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
Line 20: Line 23:
| 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
Line 26: Line 30:
| 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
| MeltingPt = 42-45 °C | MeltingPtC = 45.1
| MeltingPt_notes =
| BoilingPt = 218 °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>
⚫ '''4-Ethylphenol''', often abbreviated to '''4-EP''', is a ] compound with the molecular formula C<sub>8</sub>H<sub>10</sub>O. In ] and ] it is produced by the spoilage ] '']''. When it reaches concentrations greater than the ] (140&nbsp;µg/L) it can give the wine ]s described as ''barnyard'', ''medicinal'', '']s'', 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-ethylphenol 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-ethylphenol.

== 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== ==Biochemistry==
4-Ethylphenol is produced from the precursor ]. ''Brettanomyces'' converts this to ] via the enzyme ].<ref> 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. 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-ethyphenol by Brettanomyces]]<br style="clear:left;"/> :] to 4-EP by ''Brettanomyces'']]{{clear|left}}


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


==References== == References ==
<references/> <references/>


==External links== == External links ==
* *


{{DEFAULTSORT:Ethylphenol, 4-}} {{DEFAULTSORT:Ethylphenol, 4-}}
] ]
] ]

]