Phenylacetaldehyde

Source: Wikipedia, the free encyclopedia.
Phenylacetaldehyde
Names
Preferred IUPAC name
Phenylacetaldehyde
Identifiers
3D model (
JSmol
)
385791
ChEBI
ChemSpider
ECHA InfoCard
 100.004.159 Edit this at Wikidata
EC Number
  • 204-574-5
KEGG
UNII
  • InChI=1S/C8H8O/c9-7-6-8-4-2-1-3-5-8/h1-5,7H,6H2 ☒N
    Key: DTUQWGWMVIHBKE-UHFFFAOYSA-N ☒N
  • O=CCc1ccccc1
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
Occupational safety and health (OHS/OSH):
Main hazards
 Harmful, Flammable
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H302, H314, H317
P260, P261, P264, P270, P272, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P333+P313, P363, P405, P501
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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Phenylacetaldehyde is an

polymers.[1] Phenylacetaldehyde is an aldehyde that consists of acetaldehyde bearing a phenyl substituent; the parent member of the phenylacetaldehyde class of compounds. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is an alpha-CH2-containing aldehyde and a member of phenylacetaldehydes.[2]

Phenylacetaldehyde is one important oxidation-related aldehyde. Exposure to styrene gives phenylacetaldehyde as a secondary metabolite. Styrene has been implicated as reproductive toxicant, neurotoxicant, or carcinogen in vivo or in vitro. Phenylacetaldehyde could be formed by diverse thermal reactions during the cooking process together with C8 compounds is identified as a major aroma–active compound in cooked pine mushroom. Phenylacetaldehyde is readily oxidized to phenylacetic acid. Therefore will eventually be hydrolyzed and oxidized to yield phenylacetic acid that will be excreted primarily in the urine in conjugated form.[2]

Natural occurrence

Phenylacetaldehyde occurs extensively in nature because it can be

flowers, and communication pheromones from various insect orders.[5] 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.[6]

Uses

Fragrances and flavors

The aroma of pure substance can be described as honey-like, sweet, rose, green, grassy and is added to

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.[7]

MAOI

Theoretically, hydrazone formation and subsequent reduction of the phenylethylidenehydrazine gives phenelzine.[citation needed]

Preparation

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

Reactivity

Phenylacetaldehyde is often contaminated with polystyrene oxide

Michael acceptors
and donors.

References

  1. ^
    ISBN 9783527334773
    .
  2. ^ a b "Phenylacetaldehyde". pubchem.ncbi.nlm.nih.gov. National Library of Medicine. Retrieved 16 July 2020. Public Domain This article incorporates text from this source, which is in the public domain.
  3. doi:10.1021/jf960670h
    .
  4. doi:10.1016/j.foodchem.2008.05.048
    .
  5. ^ 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.
  6. ISSN 0046-225X
    .
  7. S2CID 4155906
    .
  8. doi:10.1002/jlac.19134010102
    .
  9. ISBN 9780471005285
    . Retrieved 15 June 2014.
  10. doi:10.1002/jlac.19485600102
    .
  11. hdl:2433/75368
    .
  12. doi:10.1021/cr60156a002
    .
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