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Phenylacetaldehyde

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Phenylacetaldehyde
Names
IUPAC name 2-Phenylacetaldehyde
Other names Hyacinthin
Phenylethanal
Identifiers
CAS Number
3D model (JSmol)
ECHA InfoCard 100.004.159 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
SMILES
  • O=Ccc1ccccc1
Properties
Chemical formula C8H8O
Molar mass 120.15 g/mol
Melting point −10 °C (14 °F; 263 K)
Boiling point 193 °C (379 °F; 466 K)
Hazards
Flash point 87 °C
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkverify (what is  ?) Infobox references
Chemical compound

Phenylacetaldehyde is an aromatic compound found in buckwheat, chocolate and many other foods and flowers. It is also responsible for the antibiotic activity of maggot therapy and it is also a compound that is added to cigarettes to improve their aroma.

Many insects (Lepidoptera, Hymenoptera, Coleoptera and Neuroptera) use this substance for communication.

The aroma of pure substance can be described as: honey-like, sweet, rose, green, grassy.

Phenylacetaldehyde is often contaminated with polystyrene oxide polymer because of the especial lability of the benzylic alpha proton and the reactivity of the aldehyde. Aldol condensation of the initial dimer gives rise to a range of Michael acceptors and donors.

References

  1. Janes D, Kantar D, Kreft S, Prosen H (2009). "Identification of buckwheat (Fagopyrum esculentum Moench) aroma compounds with GC-MS". Food Chemistry. 112 (1): 120–124. doi:10.1016/j.foodchem.2008.05.048.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. Schnermann, P., and Schieberle, P. 1997. Evaluation of key odorants in milk chocolate and cocoa cass by aroma extract dilution analyses. J. Agric. Food Chem. 45:867-872.
  3. Pavillard, E. R., Wright, E. A. An antibiotic from maggots. Nature 1957; 180: 916-917.74
  4. Semiochemical - 2-phenylacetaldehyde at Pherobase.com
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