Phenylacetaldehyde

Phenylacetaldehyde is an organic compound used in the synthesis of fragrances and polymers.[1]

Phenylacetaldehyde
Names
Preferred IUPAC name
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Other names
2-Phenylacetaldehyde
Hyacinthin
jatin bri
Identifiers
3D model (JSmol)
385791
ChemSpider
ECHA InfoCard 100.004.159
UNII
Properties
C8H8O
Molar mass 120.15 g/mol
Appearance Colorless liquid
Density 1.079 g/mL
Melting point −10 °C (14 °F; 263 K)
Boiling point 195 °C (383 °F; 468 K)
2.210 g/L
-72.01·10−6 cm3/mol
1.526
Hazards
Main hazards Harmful, Flammable
R-phrases (outdated) R22 R36 R37 R38
S-phrases (outdated) S26 S36
Flash point 87 °C (189 °F; 360 K)
Related compounds
Related 2-phenyl aldehydes
 3,4-Dihydroxyphenylacetaldehyde

Phenylglyoxal

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Natural Occurrence

Phenylacetaldehyde occurs extensively in nature because it can be biosynthetically derived from the amino acid phenylalanine. Natural sources of the compound include chocolate,[2] buckwheat,[3] flowers, and communication pheromones from various insect orders.[4] It is notable for being a floral attractant for numerous species of Lepidoptera; for example, it is the strongest floral attractor for the cabbage looper moth.[5]

Uses

Fragrances and flavors

The aroma of pure substance can be described as honey-like, sweet, rose, green, grassy and is added to fragrances to impart hyacinth, narcissi, or rose nuances.[1] For similar reasons the compound can sometimes be found in flavored cigarettes and beverages.

Historically, before biotechnology approaches were developed, phenylacetaldehyde was also used to produce phenylalanine via the Strecker reaction as a step in the production of aspartame sweetener.[1]

Polymers

Phenylacetaldehyde is used in the synthesis of polyesters where it serves as a rate-controlling additive during polymerization.[1]

Natural Medicine

Phenylacetaldehyde is responsible for the antibiotic activity of maggot therapy.[6]

MAOI

Theoretically, hydrazone formation and subsequent reduction of the phenylethylidenehydrazine gives phenelzine.

Preparation

Phenylacetaldehyde can be obtained via various synthetic routes and precursors. Notable examples include:

Reactivity

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. Kohlpaintner, Christian; Schulte, Markus; Jürgen, Falbe; Lappe, Peter; Jürgen, Weber; Frey, Guido (2014). "Aldehydes, Araliphatic". Ullmann's Encyclopedia of Industrial Chemistry. 1. doi:10.1002/14356007.m01_m03.pub2. ISBN 9783527334773.
  2. Schnermann, Petra; Schieberle, Peter (1997). "Evaluation of Key Odorants in Milk Chocolate and Cocoa Mass by Aroma Extract Dilution Analyses". Journal of Agricultural and Food Chemistry. 45 (3): 867–872. doi:10.1021/jf960670h.
  3. 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.
  4. El-Sayed, Ashraf. "Semiochemical-2-phenylacetaldehyde". The Pherobase: Database of Insect Pheromones and Semiochemicals. Extensive Database of Insect Pheromones and Semiochemicals. Archived from the original on 30 June 2017. Retrieved 26 November 2014.
  5. Heath, Robert R.; Landolt, Peter J.; Dueben, Barbara; Lenczewski, Barbara (1992-08-01). "Identification of Floral Compounds of Night-Blooming Jessamine Attractive to Cabbage Looper Moths". Environmental Entomology. 21 (4): 854–859. doi:10.1093/ee/21.4.854. ISSN 0046-225X.
  6. Pavillard, E.R.; Wright, E. A. (1957). "An Antibiotic from Maggots". Nature. 180 (4592): 916–917. doi:10.1038/180916b0. PMID 13483556.
  7. Weerman, R.A. (1913). "Einwirkung von Natriumhypochlorit auf Amide ungesättigter Säuren". Justus Liebigs Annalen der Chemie. 401 (1): 1–20. doi:10.1002/jlac.19134010102.
  8. Adams, Rodger (1946). Organic Reactions Volume III (PDF). Newyork: John Wiley and Sons Inc. pp. 275, 276, & 285. ISBN 9780471005285. Retrieved 15 June 2014.
  9. Reppe, Walter; Schlichting, Otto; Klager, Karl; Toepel, Tim (1948). "Cyclisierende Polymerisation von Acetylen I Über Cyclooctatetraen". Justus Liebigs Annalen der Chemie. 560 (1): 1–92. doi:10.1002/jlac.19485600102.
  10. Kunichika, Sango (1953). "Cyclopolyolefins Derived from Acetylene". Bulletin of the Institute for Chemical Research, Kyoto University. 31 (5): 323–335. hdl:2433/75368.
  11. Schonberg, Alexander; Radwan, Moubacher (1952). "The Strecker Degradation of α-Amino Acids". Chemical Reviews. 52 (2): 261–277. doi:10.1021/cr60156a002.
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