| Revision as of 12:08, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Saving copy of the {{chembox}} taken from revid 441693977 of page Phenoxyethanol for the Chem/Drugbox validation project (updated: 'ChEMBL'). |
Latest revision as of 22:47, 18 January 2025 edit Smokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers75,053 edits →Safety: biodeg |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Reference = <ref name="a">{{Ullmann| author1=Helmut Fiege | author2=Heinz-Werner Voges | author3=Toshikazu Hamamoto | author4=Sumio Umemura | author5=Tadao Iwata | author6=Hisaya Miki | author7=Yasuhiro Fujita | author8=Hans-Josef Buysch | author9=Dorothea Garbe | author10=Wilfried Paulus | contribution=Phenol Derivatives | year=2007 | doi=10.1002/14356007.a19_313}}</ref><ref>{{citation | entry=Phenoxyethanol | title=British Pharmacopoeia | volume=2 | year=2009 | isbn=978-0-11-322799-0| title-link=British Pharmacopoeia | last1=Commission | first1=British Pharmacopoeia | publisher=Stationery Office }}</ref><ref>{{citation | editor=David R. Lide | title=CRC Handbook of Chemistry and Physics | edition=90th | year=2010 | publisher=CRC Press| title-link=CRC Handbook of Chemistry and Physics }}</ref> |
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| Verifiedfields = changed |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 399164662 |
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| verifiedrevid = 464200667 |
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| Name = Phenoxyethanol |
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| Name = Phenoxyethanol |
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| ImageFileL1 = 2-phenoxyethanol-Line-Structure.svg |
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| ImageFile = 2-phenoxyethanol-Line-Structure.svg |
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| ImageSizeL1 = 120px |
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| ImageFile1 = Phenoxyethanol 3d structure.png |
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| ImageFileR1= Phenoxyethanol_3d_structure.png |
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| ImageName = |
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| ImageSizeR2 = 120px |
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| PIN = 2-Phenoxyethan-1-ol |
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| ImageName = |
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| OtherNames = Phenoxyethanol<br />Ethylene glycol monophenyl ether<br />Phenoxytolarosol<br />Dowanol EP / EPH<br /> Protectol PE<br /> Emery 6705<br />Rose ether<br />1-Hydroxy-2-phenoxyethane<br />β-hydroxyethyl phenyl ether<br />Phenyl cellosolve<br />Phenoxetol® |
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| IUPACName = 2-Phenoxy-1-ethanol |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = Phenoxyethanol<br />Ethylene glycol monophenyl ether<br />Phenoxytolarosol<br />Dowanol EP / EPH<br />Emery 6705<br />Rose ether<br />1-Hydroxy-2-phenoxyethane<br />β-hydroxyethyl phenyl ether<br />Phenyl cellosolve |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 13848467 |
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| ChemSpiderID = 13848467 |
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| PubChem = 31236 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = <!-- blanked - oldvalue: 1229846 --> |
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| ChEBI = 64275 |
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| ChEMBL_Ref = {{ebicite|changedll|EBI}} |
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| ChEMBL = 1229846 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = HIE492ZZ3T |
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| UNII = HIE492ZZ3T |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 122-99-6 |
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| CASNo = 122-99-6 |
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| SMILES = c1ccc(cc1)OCCO |
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| SMILES = c1ccc(cc1)OCCO |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| C=8|H=10|O=2 |
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| Formula = C<sub>8</sub>H<sub>10</sub>O<sub>2</sub> |
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| Appearance = Colorless oily liquid |
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| MolarMass = 138.16 g/mol |
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| Odor = faint rose-like |
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| Appearance = colourless oily liquid |
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| Density = 1.102 g/cm<sup>3</sup> |
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| Density = 1.102 g/cm<sup>3</sup> |
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| MeltingPt = 11 - 13 °C |
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| MeltingPtC = -2 |
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| BoilingPt = 247 °C |
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| BoilingPtC = 247 |
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| VaporPressure = {{convert|0.001|kPa|abbr=on}} |
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| ThermalConductivity = 0.169 W/(m⋅K) |
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| RefractIndex = 1.534 (20 °C) |
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| Solubility = 26 g/kg |
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| Solubility1 = slightly |
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| Solvent1 = peanut oil |
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| Solubility2 = slightly |
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| Solvent2 = olive oil |
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| Solubility3 = miscible |
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| Solvent3 = acetone |
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| Solubility4 = miscible |
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| Solvent4 = ethanol |
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| Solubility5 = miscible |
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| Solvent5 = glycerol |
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| SolubleOther = ], ], ]: soluble<!-- formerly #6, #7, #8 params that do not exist. Mar 2016 --> |
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| Section3 = |
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| Section7 = {{Chembox Hazards |
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| FlashPt = 113 °C (closed cup) |
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| Section7 = {{Chembox Hazards |
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| FlashPtC = 126 |
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| AutoignitionPtC = 430 |
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| LD50 = 1850 mg/kg (rat, oral) |
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| NFPA-H = 3 |
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| NFPA-F = 1 |
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| NFPA-R = 0 |
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| GHSPictograms = {{GHS07}} |
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| GHSSignalWord = Warning |
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| MainHazards = Harmful if swallowed<br />Causes serious eye irritation |
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| Section9 = {{Chembox Related |
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| OtherCompounds = ] |
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'''Phenoxyethanol''' is the ] with the formula C<sub>6</sub>H<sub>5</sub>OC<sub>2</sub>H<sub>4</sub>OH. It is a colorless oily liquid. It can be classified as a ] and a ]. It is a common preservative in vaccine formulations.<ref>{{cite journal |doi=10.1002/jps.20976|title=Antimicrobial preservative use in parenteral products: Past and present|year=2007|last1=Meyer|first1=Brian K.|last2=Ni|first2=Alex|last3=Hu|first3=Binghua|last4=Shi|first4=Li|journal=Journal of Pharmaceutical Sciences|volume=96|issue=12|pages=3155–3167|pmid=17722087}}</ref> It has a faint rose-like aroma.<ref name=":0" /> |
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== Use == |
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Phenoxyethanol has ] and ] properties.<ref>{{Cite journal |last1=Nolan |first1=Richard A. |last2=Nolan |first2=William G. |date=1972 |title=Phenoxyethanol as a Fungal Enzyme Extractant and Preservative |url=https://www.jstor.org/stable/3757974 |journal=Mycologia |volume=64 |issue=6 |pages=1344–1349 |doi=10.2307/3757974 |jstor=3757974 |issn=0027-5514}}</ref> It is often used together with ]s. |
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Phenoxyethanol is used as a ]; an ]; an ];<ref>{{Cite journal |last=Rosenberg |first=Herb |date=1992 |title=Improve Laboratory Conditions with Neutralizing Agent |url=https://www.jstor.org/stable/4449498 |journal=The American Biology Teacher |volume=54 |issue=6 |pages=327 |doi=10.2307/4449498 |jstor=4449498 |issn=0002-7685}}</ref> a ] for ], dyes, inks, and resins; a preservative for pharmaceuticals, cosmetics and lubricants;<ref>{{Cite journal |last1=Nakanishi |first1=Mikiye |last2=Wilson |first2=Allan C. |last3=Nolan |first3=Richard A. |last4=Gorman |first4=George C. |last5=Bailey |first5=George S. |date=1969 |title=Phenoxyethanol: Protein Preservative for Taxonomists |url=https://www.jstor.org/stable/1726343 |journal=Science |volume=163 |issue=3868 |pages=681–683 |doi=10.1126/science.163.3868.681 |jstor=1726343 |pmid=5762931 |bibcode=1969Sci...163..681N |issn=0036-8075}}</ref> an ] in fish aquaculture;<ref>{{Cite journal |last1=Rooney |first1=Seán M. |last2=Wightman |first2=Glen |last3=Ó'Conchúir |first3=Ruairi |last4=King |first4=James J. |date=2015 |title=Behaviour of sea lamprey (Petromyzon marinus L.) at man-made obstacles during upriver spawning migration: use of telemetry to assess efficacy of weir modifications for improved passage |url=https://www.jstor.org/stable/10.3318/bioe.2015.14 |journal=Biology and Environment: Proceedings of the Royal Irish Academy |volume=115B |issue=2 |pages=125–136 |doi=10.3318/bioe.2015.14 |jstor=10.3318/bioe.2015.14 |issn=0791-7945}}</ref><ref>{{Cite journal |last1=Danabas |first1=Durali |last2=Yildirim |first2=Nuran Cikcikoglu |last3=Yildirim |first3=Numan |last4=Onal |first4=Ayten Oztufekci |last5=Uslu |first5=Gulsad |last6=Unlu |first6=Erhan |last7=Danabas |first7=Seval |last8=Ergin |first8=Cemil |last9=Tayhan |first9=Nilgun |date=2016 |title=Cytokine Responses in Gills of Capoeta umbla as Biomarkers of Environmental Pollution |url=https://www.jstor.org/stable/44134400 |journal=Water Environment Research |volume=88 |issue=3 |pages=217–222 |doi=10.2175/106143016X14504669767616 |jstor=44134400 |pmid=26931532 |bibcode=2016WaEnR..88..217D |issn=1061-4303}}</ref> and in ]. |
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It is an alternative to ].<ref>{{cite journal |journal=Acta Anat (Basel) |year=1989 |volume=136 |issue=2 |pages=155–8 |title=Phenoxyethanol as a nontoxic preservative in the dissection laboratory |vauthors=Wineski LE, English AW |pmid=2816264 |doi=10.1159/000146816}}</ref> In Japan and the European Union, its concentration in cosmetics is restricted to 1%.<ref>{{cite journal |vauthors=Tokunaga H, Takeuchi O, Ko R, Uchino T, Ando M |title=市販化粧水中のフェノキシエタノールおよびパラベン類の分析法に関する研究 |trans-title=Studies for analyzing phenoxyethanol and parabens in commercial lotions |language=ja |journal=Kokuritsu Iyakuhin Shokuhin Eisei Kenkyūjo Hōkoku |issue=121 |pages=25–9 |year=2003 |pmid=14740401 |url=http://www.nihs.go.jp/library/eikenhoukoku/2003/2003_notes_25.pdf}}</ref> |
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== History and synthesis == |
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Phenoxyethanol was first prepared by ] and his graduate student Edward Haworth in 1896.<ref>{{Cite book |url=https://books.google.com/books?id=uCZEAQAAMAAJ&pg=RA1-PA40 |title=Abstracts of the Proceedings of the Chemical Society |date=1895 |publisher=Chemical Society |language=en}}</ref> They reacted ], ] and ] in anhydrous ethanol.<ref>{{Cite journal |last1=Bentley |first1=William Henry |last2=Haworth |first2=Edward |last3=Perkin |first3=William Henry |date=1896 |title=On γ-phenoxy-derivatives of malonic acid and acetic acid, and various compounds used in the synthesis of these acids |url=https://books.google.com/books?id=qQnjBugq3X0C&pg=PA165 |journal=Journal of the Chemical Society, Transactions |language=en |volume=69 |pages=161–175 |doi=10.1039/CT8966900161 |issn=0368-1645}}</ref> Starting from the 1920s, it has been commercially available as a ] solvent under the trademark of "Phenyl cellosolve".<ref>{{Cite book |last=Corporation |first=Union Carbide |url=https://books.google.com/books?id=aBchAQAAMAAJ&q=Phenyl+cellosolve |title=Report |date=1929 |language=en}}</ref> |
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The compound is produced in the industry by the hydroxyethylation of phenol (]), for example, in the presence of ] or alkali-metal borohydrides.<ref name="a" /> |
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== Efficacy == |
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Phenoxyethanol is effective against ] and ], and the ] ].<ref>{{cite journal |journal=Lett Appl Microbiol |year=1994 |volume=18 |issue=2 |pages=115–6 |title= The antimicrobial activity of phenoxyethanol in vaccines |vauthors=Lowe I, Southern J |pmid=7764595 |doi=10.1111/j.1472-765X.1994.tb00820.x|s2cid=12124463 }}</ref> |
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{| class="wikitable sortable" |
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|+ Effective concentration and contact time to kill germs with aromatic alcohols<ref name=":0">{{citation | author=Hans-P. Harke | contribution=Disinfectants | title=Ullmann's Encyclopedia of Industrial Chemistry | edition=7th | publisher=Wiley | year=2007 | pages=1–17 | doi=10.1002/14356007.a08_551| title-link=Ullmann's Encyclopedia of Industrial Chemistry | isbn=978-3-527-30673-2 }}</ref> |
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! rowspan=2 | Aromatic alcohol |
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! rowspan=2 | Concentration (%) |
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! colspan=4 | Contact time (minutes) |
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! '']'' |
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| 1 |
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| >30 |
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| >30 |
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| 1.25 |
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| rowspan=2 | Phenoxyethanol |
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| 1.25 |
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== Safety == |
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Phenoxyethanol is a vaccine preservative and potential allergen, which may result in a nodular reaction at the site of injection. Possible symptoms include rashes, eczema, and possible death.<ref>{{citation | author1=M. H. Beck | author2=S. M. Wilkinson | chapter=Contact Dermatitis: Allergic | editor1=Tony Burns | editor2=Stephen Breathnach | editor3=Neil Cox | editor4=Christopher Griffiths | title=Rook's Textbook of Dermatology | edition=8th | volume=2 | year=2010 | publisher=Wiley-Blackwell | page=26.46 | isbn=978-1-4051-6169-5}}</ref> It reversibly inhibits ]-mediated ion currents.<ref>{{cite journal |vauthors=Schmuck G, Steffens W, Bomhard E |title=2-Phenoxyethanol: a neurotoxicant? |journal=Archives of Toxicology |volume=74 |issue=4–5 |pages=281–7 | date=July 2000 |pmid=10959804 |doi=10.1007/s002040000110|bibcode=2000ArTox..74..281S |s2cid=6999187 }}</ref> |
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==Environmental considerations== |
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In view of phenoxyethanol's widespread use, its biodegradation has been examined. One pathway entails initial conversion to phenol and acetaldehyde.<ref>{{cite journal |doi=10.1016/j.watres.2017.02.001 |title=Anaerobic biodegradation of (Emerging) organic contaminants in the aquatic environment |date=2017 |last1=Ghattas |first1=Ann-Kathrin |last2=Fischer |first2=Ferdinand |last3=Wick |first3=Arne |last4=Ternes |first4=Thomas A. |journal=Water Research |volume=116 |pages=268–295 |pmid=28347952 |bibcode=2017WatRe.116..268G }}</ref> |
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== References == |
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{{reflist|2}} |
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