Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Phenoxyethanol: Difference between pages

| 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 }}</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>

| 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<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®

| Section1 = {{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| PubChem = 31236

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 64275

| ChEMBL_Ref = {{ebicite|changedll|EBI}}

| ChEMBL = 1229846

| 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

| = -

| = 247

| VaporPressure = {{convert|0.001|kPa|abbr=on}}

| ThermalConductivity = 0.169 W/(m⋅K)

| RefractIndex = 1.534 (20 °C)

| Solubility = 26&nbsp;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<!-- formerly #6, #7, #8 params that do not exist. Mar 2016 -->

| Section3 =

|

| 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<br />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.<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>

== Use ==

Phenoxyethanol has [[germicidal]] and [[Bacteriostatic agent|germistatic]] 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 [[quaternary ammonium compound]]s.

Phenoxyethanol is used as a [[Fixative (perfumery)|perfume fixative]]; an [[insect repellent]]; an [[antiseptic]];<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 [[solvent]] for [[cellulose acetate]], 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 |jstor=1726343 |issn=0036-8075}}</ref> an [[anesthetic]] 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 |jstor=44134400 |issn=1061-4303}}</ref> and in [[organic synthesis]].

Phenoxyethanol is an alternative to [[Formaldehyde releaser|formaldehyde-releasing preservatives]].<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>

== Production ==

Phenoxyethanol is produced by the hydroxyethylation of phenol ([[Williamson synthesis]]), for example, in the presence of [[Alkali metal hydroxide|alkali-metal hydroxides]] or alkali-metal borohydrides. Phenoxyethanol has a long history of use, with its discovery credited to the German chemist Otto Schott in the early 20th century. Since then, it has been extensively studied and applied in various industries.<ref name="a" />

== Efficacy ==

Phenoxyethanol is effective against [[Gram-negative bacteria|gram-negative]] and [[gram-positive bacteria]], and the [[yeast]] [[Candida albicans]].<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>

{| class="wikitable sortable"

|+ Effective concentration and contact time to kill germs with aromatic alcohols<ref>{{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 }}</ref>

! rowspan=2 | Aromatic alcohol

! rowspan=2 | Concentration (%)

! colspan=4 | Contact time (minutes)

|-

! ''[[Escherichia coli]]''

! ''[[Pseudomonas aeruginosa]]''

! ''[[Proteus mirabilis]]''

! ''[[Staphylococcus aureus]]''

|-

| [[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.<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 [[NMDAR]]-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|s2cid=6999187 }}</ref>

== References ==

{{reflist|2}}

[[Category:Primary alcohols]]

[[Category:Glycol ethers]]

[[Category:Household chemicals]]

[[Category:Antiseptics]]

[[Category:Phenol ethers]]