1-Phenylethanol
-Phenylethanol_Structural_Formulae_V.1.svg.png) | |
| Names | |
|---|---|
| IUPAC name
1-phenylethanol | |
| Other names
Styrallyl alcohol | |
| Identifiers | |
| 98-85-1 | |
| 3D model (Jmol) | Interactive image |
| ECHA InfoCard | 100.002.461 |
| EC Number | 202-707-1 |
| UN number | 2937 |
| |
| |
| Properties | |
| C8H10O | |
| Molar mass | 122.167 g mol-1 |
| Appearance | Colourless liquid with a floral[1] or almond-like odor[2] |
| Melting point | 20.7 °C (69.3 °F; 293.8 K) |
| Boiling point | 204 °C (399 °F; 477 K) |
| 1.95 g dm-3 [3] | |
| log P | 1.4 |
| Hazards | |
| Flash point | 93 °C[4] |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
1-Phenylethanol is the chiral positional isomer of phenethyl alcohol. It is a colorless liquid with a mild gardenia-hyacinth scent.[5]
Natural occurrence
1-Phenylethanol is found in nature as a glycoside, together with its hydrolase β-primeverosidase in tea (Camellia sinensis) flowers.[6] It is also reportedly present in cranberries, grapes, chives, Scottish spearmint oil, cheeses, cognac, rum, white wine, cocoa, black tea, filbert, cloudberries, beans, mushrooms, and endives.[7]
Synthesis
1-Phenylethanol can be produced as a racemic mixture by the reduction of acetophenone by reducing agents like sodium borohydride or lithium aluminium hydride. Alternatively, benzaldehyde can be reacted with methylmagnesium chloride or similar organometallic compounds to afford racemic 1-phenylethanol.
References
- ↑ Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 759
- ↑ Gerhartz, W. (exec ed.). Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol A1: Deerfield Beach, FL: VCH Publishers, 1985 to Present., p. VA24 488
- ↑ Southworth GR, Keller JL; Water Air Soil Poll 28: 239-48 (1986)
- ↑ Fire Protection Guide to Hazardous Materials. 12 ed. Quincy, MA: National Fire Protection Association, 1997., p. 325-71
- ↑ Fenaroli's Handbook of Flavor Ingredients. Volume 2. Edited, translated, and revised by T.E. Furia and N. Bellanca. 2nd ed. Cleveland: The Chemical Rubber Co., 1975., p. 348
- ↑ Zhou, Ying; Dong, Fang; Kunimasa, Aiko; Zhang, Yuqian; Cheng, Sihua; Lu, Jiamin; Zhang, Ling; Murata, Ariaki; Mayer, Frank (2014-08-13). "Occurrence of glycosidically conjugated 1-phenylethanol and its hydrolase β-primeverosidase in tea (Camellia sinensis) flowers". Journal of Agricultural and Food Chemistry. 62 (32): 8042–8050. doi:10.1021/jf5022658. ISSN 1520-5118. PMID 25065942.
- ↑ Burdock, George A. (2005). Fenaroli's Handbook of Flavor Ingredients, Fifth Edition. CRC Press.