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| Names | |
|---|---|
| IUPAC name 2-Phenylethanol | |
| Other names 2-Phenylethanol Phenethyl alcohol Benzyl carbinol β-Hydroxyethylbenzene Benzeneethanol | |
| Identifiers | |
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3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
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| DrugBank |
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| ECHA InfoCard | 100.000.415 |
| KEGG | |
| UNII | |
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| Properties | |
| C8H10O | |
| Molar mass | 122.167 g·mol−1 |
| Odor | Soft, like roses |
| Density | 1.017 g/cm3 |
| Melting point | −27 °C (−17 °F; 246 K) |
| Boiling point | 219 to 221 °C (426 to 430 °F; 492 to 494 K) |
| logP | 1.36[2] |
| Hazards | |
| NFPA 704 (fire diamond) | |
| Safety data sheet (SDS) | JT Baker MSDS |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Phenethyl alcohol, or2-phenylethanol, is anorganic compound with thechemical formulaC6H5CH2CH2OH. It is a colourless liquid with a pleasant floral odor. It occurs widely in nature, being found in a variety ofessential oils. It is slightly soluble in water (2ml per 100 ml ofH2O), but miscible with mostorganic solvents. The molecule of phenethyl alcohol consists of a phenethyl group (C6H5CH2CH2−) attached to ahydroxyl group (−OH).
Phenethyl alcohol is prepared commercially via two routes. Most common is theFriedel-Crafts reaction betweenbenzene andethylene oxide in the presence ofaluminium trichloride.
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 ofstyrene oxide also affords phenethyl alcohol.[3]
Phenethyl alcohol can also be prepared by the reaction betweenphenylmagnesium bromide andethylene oxide:
Phenethyl alcohol can also be produced bybiotransformation fromL-phenylalanine using immobilizedyeastSaccharomyces cerevisiae.[4] It is also possible to produce phenethyl alcohol by thereduction ofphenylacetic acid usingsodium borohydride andiodine inTHF.[5]
Phenethyl alcohol is found in extract ofrose,carnation,hyacinth,Aleppo pine,orange blossom,ylang-ylang,geranium,neroli, andchampaca. It is also anautoantibiotic produced by the fungusCandida albicans.[6]
Fusel alcohols like phenethyl alcohol are grain fermentation byproducts, and therefore trace amounts of phenethyl alcohol are present inmany alcoholic beverages.
It is therefore a common ingredient in flavors and perfumery, particularly when the odor of rose is desired.[3] It is used as anadditive in cigarettes. It is also used as apreservative insoaps due to its stability inbasic conditions. It is of interest due to itsantimicrobial properties.
