1-Phenylethanol

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1-Phenylethanol
(RS)-Phenylethanol Structural Formulae V.1.svg
Names
IUPAC name
1-phenylethanol
Other names
Styrallyl alcohol
Identifiers
3D model (JSmol)
ChemSpider
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[5]
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.[6]

Natural occurrence[edit]

1-Phenylethanol is found in nature as a glycoside, together with its hydrolase β-primeverosidase in tea (Camellia sinensis) flowers.[7] 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.[8]

Synthesis[edit]

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[edit]

  1. ^ Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 759
  2. ^ 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
  3. ^ Southworth GR, Keller JL; Water Air Soil Poll 28: 239-48 (1986)
  4. ^ 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
  5. ^ Fire Protection Guide to Hazardous Materials. 12 ed. Quincy, MA: National Fire Protection Association, 1997., p. 325-71
  6. ^ 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.
  7. ^ 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. 
  8. ^ Burdock, George A. (2005). Fenaroli's Handbook of Flavor Ingredients, Fifth Edition. CRC Press.