Phenethyl alcohol
{{Chembox
| Watchedfields = changed
| verifiedrevid = 464200140
| Name = Phenethyl alcohol
| Reference = {{Cite book|title=Merck Index|edition=11th|page=7185}}
| ImageFile = Phenethyl alcohol.png
| ImageName = Skeletal formula
| ImageFile1 = Phenethyl-alcohol-3D-balls.png
| ImageName1 = Ball-and-stick model
| IUPACName = 2-Phenylethanol
| SystematicName =
| OtherNames = 2-Phenylethanol
Phenethyl alcohol
Benzyl carbinol
β-Hydroxyethylbenzene
Benzeneethanol
| Section1 = {{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = ML9LGA7468
| InChI = 1S/C8H10O/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2
| InChIKey1 = WRMNZCZEMHIOCP-UHFFFAOYSA-N
| InChI1 = 1S/C8H10O/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2
| CASNo = 60-12-8
| CASNo_Ref = {{cascite|correct|CAS}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB02192
| KEGG = D00192
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 49000
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WRMNZCZEMHIOCP-UHFFFAOYSA-N
| SMILES = c1ccc(cc1)CCO
| PubChem = 6054
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5830
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 448500
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C8H10O/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2
}}
| Section2 = {{Chembox Properties
| Formula = {{chem2|C8H10O}}
| Odor = Soft, like roses
| C=8|H=10|O=1
| Density = 1.017 g/cm3
| MeltingPtC = -27
| BoilingPtC = 219 to 221
| LogP =1.36 {{Cite web|url=https://www.chemsrc.com/en/cas/60-12-8_509692.html|title=Phenylethyl alcohol_msds}}
}}
| Section3 =
| Section4 =
| Section5 =
| Section6 =
| Section7 = {{Chembox Hazards
| NFPA-H = 1
| NFPA-F = 1
| NFPA-R = 0
| ExternalSDS = [http://hazard.com/msds/mf/baker/baker/files/p1861.htm JT Baker MSDS]
}}
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Phenethyl alcohol, or 2-phenylethanol, is an organic compound with the chemical formula {{chem2|C6H5CH2CH2OH}}. It is a colourless liquid with a pleasant floral odor. It occurs widely in nature, being found in a variety of essential oils. It is slightly soluble in water (2 ml per 100 ml of Water), but miscible with most organic solvents. The molecule of phenethyl alcohol consists of a phenethyl group ({{chem2|C6H5CH2CH2\s}}) attached to a hydroxyl group ({{chem2|\sOH}}).
Synthesis
Phenethyl alcohol is prepared commercially via two routes. Most common is the Friedel-Crafts reaction between benzene and ethylene oxide in the presence of aluminium trichloride.
:{{chem2|C6H6 + CH2CH2O + AlCl3 → C6H5CH2CH2OAlCl2 + HCl}}
The reaction affords the aluminium alkoxide that is subsequently hydrolyzed to the desired product. The main side product is diphenylethane, which can be avoided by use of excess benzene. Hydrogenation of styrene oxide also affords phenethyl alcohol.
=Laboratory methods=
Phenethyl alcohol can also be prepared by the reaction between phenylmagnesium bromide and ethylene oxide:
:{{chem2|C6H5MgBr + (CH2CH2)O → C6H5CH2CH2OMgBr}}
:{{chem2|C6H5CH2CH2OMgBr + H+ → C6H5CH2CH2OH + MgBr+}}
Phenethyl alcohol can also be produced by biotransformation from L-phenylalanine using immobilized yeast Saccharomyces cerevisiae.{{cite journal|vauthors=Eshkol N, Sendovski M, Bahalul M, Katz-Ezov T, Kashi Y, Fishman A|title=Production of 2-phenylethanol from L-phenylalanine by a stress tolerant Saccharomyces cerevisiae strain|journal=Journal of Applied Microbiology|year=2009|volume=106|pages=534–542|doi=10.1111/j.1365-2672.2008.04023.x|pmid=19200319|issue=2|doi-access=free}} It is also possible to produce phenethyl alcohol by the reduction of phenylacetic acid using sodium borohydride and iodine in THF. {{cite journal|vauthors=Kanth JV, Periasamy M|title=Selective Reduction of Carboxylic Acids into Alcohols Using NaBH and I2|journal=Journal of Organic Chemistry|year=1991|volume=56|pages=5964–5965|doi=10.1021/jo00020a052}}
Occurrence and uses
Phenethyl alcohol is found in extract of rose, carnation, hyacinth, Aleppo pine, orange blossom, ylang-ylang, geranium, neroli, and champaca. It is also an autoantibiotic produced by the fungus Candida albicans.{{Cite journal|pmid=5762768|year=1969|last1=Lingappa|first1=BT|last2=Prasad|first2=M|last3=Lingappa|first3=Y|last4=Hunt|first4=DF|last5=Biemann|first5=K|title=Phenethyl alcohol and tryptophol: Autoantibiotics produced by the fungus Candida albicans|volume=163|issue=3863|pages=192–4|journal=Science |doi=10.1126/science.163.3863.192|bibcode=1969Sci...163..192L|s2cid=12430791}}
Fusel alcohols like phenethyl alcohol are grain fermentation byproducts, and therefore trace amounts of phenethyl alcohol are present in many alcoholic beverages.
It is therefore a common ingredient in flavors and perfumery, particularly when the odor of rose is desired.{{cite book |doi=10.1002/14356007.a11_141 |chapter=Flavors and Fragrances |title=Ullmann's Encyclopedia of Industrial Chemistry |year=2003 |last1=Fahlbusch |first1=Karl-Georg |last2=Hammerschmidt |first2=Franz-Josef |last3=Panten |first3=Johannes |last4=Pickenhagen |first4=Wilhelm |last5=Schatkowski |first5=Dietmar |last6=Bauer |first6=Kurt |last7=Garbe |first7=Dorothea |last8=Surburg |first8=Horst |isbn=978-3-527-30673-2}} It is used as an additive in cigarettes. It is also used as a preservative in soaps due to its stability in basic conditions. It is of interest due to its antimicrobial properties.