Phenethyl alcohol
| Phenethyl alcohol[1] | |
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2-Phenylethanol |
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Other names
Phenethyl alcohol |
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| Identifiers | |
| CAS number | 60-12-8  |
| PubChem | 6054 |
| ChemSpider | 5830 |
| UNII | ML9LGA7468 |
| DrugBank | DB02192 |
| ChEBI | CHEBI:49000 |
| ChEMBL | CHEMBL448500 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C8H10O |
| Molar mass | 122.16 g/mol |
| Density | 1.017 g/cm3 |
| Melting point |
-27 °C, 246 K, -17 °F |
| Boiling point |
219–221 °C |
| Hazards | |
| MSDS | JT Baker MSDS |
| NFPA 704 |
 1
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 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Phenethyl alcohol, or 2-phenylethanol, is the organic compound with the formula C6H5CH2CH2OH. This colourless liquid occurs widely in nature, being found in a variety of essential oils, including rose, carnation, hyacinth, Aleppo pine, orange blossom, ylang-ylang, geranium, neroli, and champaca. It is slightly soluble in water (2 mL/100 mL H2O), but miscible with ethanol and ether.
Phenethyl alcohol is an alcohol with a pleasant floral odor. It is therefore a common ingredient in flavors and perfumery,[2] particularly when the smell of rose is desired. It is used as an additive in cigarettes. It is also used as a preservative in soaps due to its stability in basic conditions. In biology it is of interest due to its antimicrobial properties.
Synthesis
Phenethyl alcohol can be prepared by a variety of procedures, such as by a Grignard reaction between phenylmagnesium bromide and ethylene oxide:
- C6H5MgBr + CH2CH2O → C6H5CH2CH2OMgBr
- C6H5CH2CH2OMgBr + H+ → C6H5CH2CH2OH
However, the Friedel-Crafts reaction between benzene and ethylene oxide may also be employed:
- C6H6 + CH2CH2O (+ AlCl3) → C6H5CH2CH2OH (+AlCl3)
Phenethyl alcohol can also be prepared by biotransformation from L-phenylalanine using immobilized yeast Saccharomyces cerevisiae.[3]
References
- ^ Merck Index, 11th Edition, 7185.
- ^ http://www.thegoodscentscompany.com/data/rw1010051.html
- ^ Eshkol, N.; M. Sendovski M. Bahalul T. Katz-Ezov Y. Kashi & A. Fishman (2009). "Production of 2-phenylethanol from L-phenylalanine by a stress tolerant Saccharomyces cerevisiae strain". Journal of Applied Microbiology 2 (106): 534–542. doi:10.1111/j.1365-2672.2008.04023.x. PMID 19200319. Retrieved 29 April 2013.
