Phenylacetaldehyde: Difference between revisions

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 444048413

| Name = Phenylacetaldehyde

| ImageFile = Phenyl ethanal Structure V.1.svg

| SystematicName =

| OtherNames =

| PIN = Phenylacetaldehyde

| Section1 = {{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| Beilstein = 385791

| ChEBI = 16424

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 13876539

| EC_number = 204-574-5

| KEGG = C00601

| PubChem = 998

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = U8J5PLW9MR

| SMILES = O=CCc1ccccc1

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C8H8O/c9-7-6-8-4-2-1-3-5-8/h1-5,7H,6H2

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = DTUQWGWMVIHBKE-UHFFFAOYSA-N

| Section2 = {{Chembox Properties

| Formula = C₈H₈O

| MolarMass = 120.15 g/mol

| Appearance = Colorless liquid

| Density = 1.079 g/mL

| MeltingPtC = -10

| BoilingPtC = 195

| Solubility = 2.210 g/L

| RefractIndex = 1.526

| MagSus = -72.01·10⁻⁶ cm³/mol

| Section3 = {{Chembox Hazards

| ExternalSDS =

| MainHazards = Harmful, Flammable

| NFPA-H = | NFPA-F = | NFPA-R =

| FlashPtC = 87

| GHSPictograms = {{GHS05}}{{GHS07}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|302|314|317}}

| PPhrases = {{P-phrases|260|261|264|270|272|280|301+312|301+330+331|302+352|303+361+353|304+340|305+351+338|310|321|330|333+313|363|405|501}}

| Section4 = {{Chembox Related

| OtherFunction_label = 2-phenyl aldehydes

| OtherFunction = [[3,4-Dihydroxyphenylacetaldehyde]]<br />

| Section5 =

| Section6 =

'''Phenylacetaldehyde''' is an [[organic compound]] used in the [[organic synthesis|synthesis]] of [[Aroma compound|fragrances]] and [[polymers]].<ref name=Ullmann1>{{cite journal|last1=Kohlpaintner|first1=Christian|last2=Schulte|first2=Markus|last3=Jürgen|first3=Falbe|last4=Lappe|first4=Peter|last5=Jürgen|first5=Weber|last6=Frey|first6=Guido|title=Aldehydes, Araliphatic|journal=Ullmann's Encyclopedia of Industrial Chemistry|date=2014|volume=1|isbn=9783527334773|doi=10.1002/14356007.m01_m03.pub2|url=https://books.google.com/books?id=NJJ7AgAAQBAJ&q=10.1002%2F14356007.mo1_mo3.pub2&pg=PA59}}</ref> 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.<ref name="PubChem">{{cite web |title=Phenylacetaldehyde |url=https://pubchem.ncbi.nlm.nih.gov/compound/Phenylacetaldehyde |website=pubchem.ncbi.nlm.nih.gov |publisher=National Library of Medicine |accessdate=16 July 2020 |language=en}} {{PD-notice}}</ref>

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.<ref name="PubChem"/>

==Natural occurrence==

Phenylacetaldehyde occurs extensively in nature because it can be [[biosynthesis|biosynthetically]] derived from the [[amino acid]] [[phenylalanine]]. Natural sources of the compound include [[chocolate]],<ref>{{cite journal|last1=Schnermann|first1=Petra|last2=Schieberle|first2=Peter|title=Evaluation of Key Odorants in Milk Chocolate and Cocoa Mass by Aroma Extract Dilution Analyses|journal=Journal of Agricultural and Food Chemistry|date=1997|volume=45|issue=3|pages=867–872|doi=10.1021/jf960670h}}</ref> [[buckwheat]],<ref>{{cite journal

|vauthors=Janes D, Kantar D, Kreft S, Prosen H | title=Identification of buckwheat (Fagopyrum esculentum Moench) aroma compounds with GC-MS

| journal=Food Chemistry

| volume=112

| issue=1

| pages=120–124

| year=2009

| doi=10.1016/j.foodchem.2008.05.048

}}</ref> [[flowers]], and communication [[pheromone]]s from various [[insect]] [[Order (biology)|orders]].<ref>{{cite web|last1=El-Sayed|first1=Ashraf|title=Semiochemical-2-phenylacetaldehyde|url=http://www.pherobase.com/database/compound/compounds-detail-2-phenylacetaldehyde.php|website=The Pherobase: Database of Insect Pheromones and Semiochemicals|publisher=Extensive Database of Insect Pheromones and Semiochemicals|accessdate=26 November 2014|archive-url=https://web.archive.org/web/20170630213539/http://www.pherobase.com/database/compound/compounds-detail-2-phenylacetaldehyde.php|archive-date=30 June 2017|url-status=dead}}</ref> 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.<ref>{{Cite journal|last1=Heath|first1=Robert R.|last2=Landolt|first2=Peter J.|last3=Dueben|first3=Barbara|last4=Lenczewski|first4=Barbara|date=1992-08-01|title=Identification of Floral Compounds of Night-Blooming Jessamine Attractive to Cabbage Looper Moths|journal=Environmental Entomology|volume=21|issue=4|pages=854–859|doi=10.1093/ee/21.4.854|issn=0046-225X|doi-access=free}}</ref>

==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 (plant)|hyacinth]], [[narcissi]], or [[rose]] nuances.<ref name=Ullmann1 /> For similar reasons the compound can sometimes be found in [[List of additives in cigarettes|flavored cigarettes]] and beverages.

Historically, before [[biotechnological|biotechnology]] approaches were developed, phenylacetaldehyde was also used to produce phenylalanine via the [[Strecker amino acid synthesis|Strecker reaction]] as a step in the production of [[aspartame]] sweetener.<ref name=Ullmann1 />

===Polymers===

Phenylacetaldehyde is used in the synthesis of [[polyester]]s where it serves as a rate-controlling additive during [[polymerization]].<ref name=Ullmann1 />

===Natural Medicine===

Phenylacetaldehyde is responsible for the antibiotic activity of [[maggot therapy]].<ref>{{cite journal|last1=Pavillard|first1=E.R.|last2=Wright|first2=E. A.|title=An Antibiotic from Maggots|journal=Nature|date=1957|volume=180|issue=4592|pages=916–917|doi=10.1038/180916b0|pmid=13483556|bibcode=1957Natur.180..916P|s2cid=4155906}}</ref>

===MAOI===

Theoretically, hydrazone formation and subsequent reduction of the [[phenylethylidenehydrazine]] gives phenelzine.{{citation needed|date=July 2018}}

==Preparation==

Phenylacetaldehyde can be obtained via various [[organic synthesis|synthetic routes]] and [[precursor (chemistry)|precursors]]. Notable examples include:

* [[Isomerization]] of [[styrene oxide]].<ref name=Ullmann1 />

* [[Dehydrogenation]] of [[2-Phenylethanol]] over [[silver]] or [[gold]] catalysts.

* [[Darzens reaction]] between [[benzaldehyde]] and [[chloroacetate]] [[ester]]s.

* [[Wacker oxidation]] of [[styrene]].

* [[Hofmann rearrangement]] of [[Cinnamamide]] (aka (2E)-3-Phenylacrylamide).<ref>{{cite journal|last1=Weerman|first1=R.A.|title=Einwirkung von Natriumhypochlorit auf Amide ungesättigter Säuren|journal=Justus Liebigs Annalen der Chemie|date=1913|volume=401|issue=1|pages=1–20|doi=10.1002/jlac.19134010102|url=https://zenodo.org/record/1427615}}</ref><ref name=ORIII>{{cite book|last1=Adams|first1=Rodger|title=Organic Reactions Volume III|date=1946|publisher=John Wiley and Sons Inc|location=New York|isbn=9780471005285|pages=275, 276, & 285|url=http://library.sciencemadness.org/library/books/organic_reactions_v3.pdf|accessdate=15 June 2014}}</ref>

* Oxidation of [[Cyclooctatetraene]] with [[aqueous]] [[Mercury(II) sulfate]].<ref>{{cite journal|last1=Reppe|first1=Walter|last2=Schlichting|first2=Otto|last3=Klager|first3=Karl|last4=Toepel|first4=Tim|title=Cyclisierende Polymerisation von Acetylen I Über Cyclooctatetraen|journal=Justus Liebigs Annalen der Chemie|date=1948|volume=560|issue=1|pages=1–92|doi=10.1002/jlac.19485600102}}</ref><ref>{{cite journal|last1=Kunichika|first1=Sango|title=Cyclopolyolefins Derived from Acetylene|journal=Bulletin of the Institute for Chemical Research, Kyoto University|date=1953|volume=31|issue=5|pages=323–335|hdl=2433/75368}}</ref>

* [[Strecker degradation]] of phenylalanine.<ref>{{cite journal|last1=Schonberg|first1=Alexander|last2=Radwan|first2=Moubacher|title=The Strecker Degradation of α-Amino Acids|journal=Chemical Reviews|date=1952|volume=52|issue=2|pages=261–277|doi=10.1021/cr60156a002}}</ref>

==Reactivity==

[[Category:Insect pheromones]]

[[Category:Phenyl compounds]]