Phenethyl alcohol

From Wikipedia, the free encyclopedia
Phenethyl alcohol[1]
IUPAC name

2-Phenylethanol

Other names

Phenethyl alcohol
Benzyl carbinol
β-Hydroxyethylbenzene
Benzenethanol

Identifiers
CAS number 60-12-8 YesY
PubChem 6054
ChemSpider 5830 YesY
UNII ML9LGA7468 YesY
DrugBank DB02192
ChEBI CHEBI:49000 YesY
ChEMBL CHEMBL448500 YesY
Jmol-3D images Image 1
Properties
Molecular formula C8H10O
Molar mass 122.16 g/mol
Odor Soft, like roses
Density 1.017 g/cm3
Melting point −27 °C; −17 °F; 246 K
Boiling point 219–221 °C
Hazards
MSDS JT Baker MSDS
NFPA 704
1
1
0
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Phenethyl alcohol, or 2-phenylethanol, is an aromatic alcohol. It 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 also an autoantibiotic produced by the fungus Candida albicans[2]

This colourless liquid 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, particularly when the smell of rose is desired.[3] 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 is prepared commercially via two routes. Most common is the Friedel-Crafts reaction between benzene and ethylene oxide in the presence of aluminium trichloride.

C6H6 + CH2CH2O + AlCl3 → C6H5CH2CH2OAlCl2 + HCl

The reaction affords the aluminium alkoxide that is subsequenly 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.[3]

Other methods

Phenethyl alcohol can also be prepared by the reaction between phenylmagnesium bromide and ethylene oxide:

C6H5MgBr + CH2CH2O → C6H5CH2CH2OMgBr
C6H5CH2CH2OMgBr + H+ → C6H5CH2CH2OH

Phenethyl alcohol can also be produced by biotransformation from L-phenylalanine using immobilized yeast Saccharomyces cerevisiae.[4]

See also

References

  1. ↑ Merck Index (11th ed.). p. 7185. 
  2. ↑ Lingappa, BT; Prasad, M; Lingappa, Y; Hunt, DF; Biemann, K (1969). "Phenethyl alcohol and tryptophol: Autoantibiotics produced by the fungus Candida albicans". Science 163 (3863): 192–4. PMID 5762768. 
  3. ↑ 3.0 3.1 Fahlbusch, Karl-Georg; Hammerschmidt, Franz-Josef; Panten, Johannes; Pickenhagen, Wilhelm; Schatkowski, Dietmar; Bauer, Kurt; Garbe, Dorothea; Surburg, Horst (2003). "Flavors and Fragrances". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a11_141. ISBN 978-3-527-30673-2. 
  4. ↑ 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. 
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