:Phenoxyethanol
{{chembox
| Reference = {{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}}{{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 }}{{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 }}
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 464200667
| Name = Phenoxyethanol
| ImageFile = 2-phenoxyethanol-Line-Structure.svg
| ImageFile1 = Phenoxyethanol 3d structure.png
| ImageName =
| PIN = 2-Phenoxyethan-1-ol
| OtherNames = Phenoxyethanol
Ethylene glycol monophenyl ether
Phenoxytolarosol
Dowanol EP / EPH
Protectol PE
Emery 6705
Rose ether
1-Hydroxy-2-phenoxyethane
β-hydroxyethyl phenyl ether
Phenyl cellosolve
Phenoxetol®
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 13848467
| PubChem = 31236
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 64275
| ChEMBL_Ref = {{ebicite|changedll|EBI}}
| ChEMBL = 1229846
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = HIE492ZZ3T
| InChI = 1/C8H10O2/c9-6-7-10-8-4-2-1-3-5-8/h1-5,9H,6-7H2
| InChIKey = QCDWFXQBSFUVSP-UHFFFAOYAU
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C8H10O2/c9-6-7-10-8-4-2-1-3-5-8/h1-5,9H,6-7H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = QCDWFXQBSFUVSP-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 122-99-6
| SMILES = c1ccc(cc1)OCCO
}}
| Section2 = {{Chembox Properties
| C=8|H=10|O=2
| Appearance = Colorless oily liquid
| Odor = faint rose-like
| Density = 1.102 g/cm3
| MeltingPtC = -2
| BoilingPtC = 247
| VaporPressure = {{convert|0.001|kPa|abbr=on}}
| ThermalConductivity = 0.169 W/(m⋅K)
| RefractIndex = 1.534 (20 °C)
| Solubility = 26 g/kg
| Solubility1 = slightly
| Solvent1 = peanut oil
| Solubility2 = slightly
| Solvent2 = olive oil
| Solubility3 = miscible
| Solvent3 = acetone
| Solubility4 = miscible
| Solvent4 = ethanol
| Solubility5 = miscible
| Solvent5 = glycerol
| SolubleOther = Chloroform, Alkali, diethyl ether: soluble
}}
| Section3 =
| Section4 =
| Section5 =
| Section6 =
| Section7 = {{Chembox Hazards
| FlashPtC = 126
| AutoignitionPtC = 430
| LD50 = 1850 mg/kg (rat, oral)
| NFPA-H = 3
| NFPA-F = 1
| NFPA-R = 0
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| MainHazards = Harmful if swallowed
Causes serious eye irritation
| HPhrases =
| PPhrases =
}}
| Section9 = {{Chembox Related
| OtherCompounds = phenetole
}}
}}
Phenoxyethanol is the organic compound with the formula C6H5OC2H4OH. It is a colorless oily liquid. It can be classified as a glycol ether and a phenol ether. It is a common preservative in vaccine formulations.{{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}} It has a faint rose-like aroma.
Use
Phenoxyethanol has germicidal and germistatic properties.{{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|url-access=subscription }} It is often used together with quaternary ammonium compounds.
Phenoxyethanol is used as a perfume fixative; an insect repellent; an antiseptic;{{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|url-access=subscription }} a solvent for cellulose acetate, dyes, inks, and resins; a preservative for pharmaceuticals, cosmetics and lubricants;{{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|url-access=subscription }} an anesthetic in fish aquaculture;{{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|url-access=subscription }}{{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|url-access=subscription }} and in organic synthesis.
It is an alternative to formaldehyde-releasing preservatives.{{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}} In Japan and the European Union, its concentration in cosmetics is restricted to 1%.{{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}}
History and synthesis
Phenoxyethanol was first prepared by W. H. Perkin Jr. and his graduate student Edward Haworth in 1896.{{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}} They reacted sodium, phenol and 2-chloroethanol in anhydrous ethanol.{{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}} Starting from the 1920s, it has been commercially available as a cellulose acetate solvent under the trademark of "Phenyl cellosolve".{{Cite book |last=Corporation |first=Union Carbide |url=https://books.google.com/books?id=aBchAQAAMAAJ&q=Phenyl+cellosolve |title=Report |date=1929 |language=en}}
The compound is produced in the industry by the hydroxyethylation of phenol (Williamson synthesis), for example, in the presence of alkali-metal hydroxides or alkali-metal borohydrides.
Efficacy
Phenoxyethanol is effective against gram-negative and gram-positive bacteria, and the yeast Candida albicans.{{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 }}
| class="wikitable sortable"
|+ Effective concentration and contact time to kill germs with aromatic alcohols{{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 }} ! rowspan=2 | Aromatic alcohol ! rowspan=2 | Concentration (%) ! colspan=4 | Contact time (minutes) |
| Escherichia coli |
|---|
| Benzyl alcohol
| 1 | >30 | >30 | >30 | >30 |
| rowspan=2 | Phenethyl alcohol
| 1.25 | 2.5 | 2.5 | 2.5 | >30 |
| 2.5
| 2.5 | 2.5 | 2.5 | 5 |
| rowspan=2 | Phenoxyethanol
| 1.25 | 15 | 2.5 | 2.5 | >30 |
| 2.5
| 2.5 | 2.5 | 2.5 | >30 |
Safety
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.{{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}} It reversibly inhibits NMDAR-mediated ion currents.{{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 }}
Environmental considerations
In view of phenoxyethanol's widespread use, its biodegradation has been examined. One pathway entails initial conversion to phenol and acetaldehyde.{{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 |doi-access=free }}