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Revision as of 12:15, 10 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'UNII').← Previous edit		Latest revision as of 21:01, 17 July 2024 edit undo2a02:8071:51e1:3a00:a123:3193:2c61:5c9b (talk)No edit summary
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	{{chembox		{{chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 397065050
			| Watchedfields = changed
⚫	| ImageFile = Phenylacetaldehyde.png
		⚫	| verifiedrevid = 444048413
	| ImageSize = 200px
	| IUPACName = 2-Phenylacetaldehyde		| Name = Phenylacetaldehyde
			| ImageFile = Phenyl ethanal Structure V.1.svg
	| OtherNames = Hyacinthin<br>Phenylethanal
			| SystematicName =
⚫	| Section1 = {{Chembox Identifiers
			| OtherNames =
⚫	| CASNo_Ref = {{cascite}}
		⚫	| PIN = Phenylacetaldehyde
		⚫	| Section1 = {{Chembox Identifiers
		⚫	| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 122-78-1		| CASNo = 122-78-1
	| CASOther =		| Beilstein = 385791
	| PubChem = 998		| ChEBI = 16424
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫	| UNII = U8J5PLW9MR
			| ChemSpiderID = 13876539
⚫	| SMILES = O=Ccc1ccccc1
			| 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		| Section2 = {{Chembox Properties
	| Formula = C<sub>8</sub>H<sub>8</sub>O		| Formula = C<sub>8</sub>H<sub>8</sub>O
	| MolarMass = 120.15 g/mol		| MolarMass = 120.15 g/mol
	| Appearance =		| Appearance = Colorless liquid
	| Density =		| Density = 1.079 g/mL
	| MeltingPtC = -10		| MeltingPtC = -10
	| BoilingPtC = 193		| BoilingPtC = 195
	| Solubility =		| Solubility = 2.210 g/L
			| RefractIndex = 1.526
			| MagSus = -72.01·10<sup>−6</sup> cm<sup>3</sup>/mol
	}}		}}
	| Section3 = {{Chembox Hazards		| Section3 = {{Chembox Hazards
	| ExternalMSDS =		| ExternalSDS =
			| MainHazards = Harmful, Flammable
	| EUClass =
	| NFPA-H = | NFPA-F = | NFPA-R =		| NFPA-H = | NFPA-F = | NFPA-R =
	| FlashPt = 87 °C		| FlashPtC = 87
	| RPhrases = {{R22}} {{R36}} {{R37}} {{R38}}		| GHSPictograms = {{GHS05}}{{GHS07}}
			| GHSSignalWord = Danger
	| SPhrases = {{S26}} {{S36}}
			| HPhrases = {{H-phrases|302|314|317}}
	| Autoignition =
			| 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		| Section4 = {{Chembox Related
	| Function = 2-phenyl aldehydes		| OtherFunction_label = 2-phenyl aldehydes
	| OtherFunctn = ]<br />		| OtherFunction = ]<br />
	]		]
	}}		}}
			| Section5 =
			| Section6 =
	}}		}}
			'''Phenylacetaldehyde''' is an ] used in the ] of ] and ].<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 '']'' metabolite, an '']'' 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 an aromatic compound found in ]<ref>{{cite journal
	| author=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
⚫	| date=2009
⚫	| doi=10.1016/j.foodchem.2008.05.048
	}}</ref>, ]<ref>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.</ref> and many other foods and ].
	It is also responsible for the antibiotic activity of ]<ref>Pavillard, E. R., Wright, E. A. An antibiotic from maggots. ''Nature'' 1957; 180: 916-917.74</ref> and it is also a compound that is ] to improve their aroma.
			Phenylacetaldehyde is one important oxidation-related aldehyde. Exposure to ] 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"/>
	Many ] (], ], ] and ]) use this substance for communication.<ref> at Pherobase.com</ref>
			==Natural occurrence==
	The aroma of pure substance can be described as: honey-like, sweet, rose, green, grassy.
			Phenylacetaldehyde occurs extensively in nature because it can be ] derived from the ] ]. Natural sources of the compound include ],<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> ],<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> ], and communication ]s from various ] ].<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 ]; for example, it is the strongest floral attractor for the ] 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 ] to impart ], ], or ] nuances.<ref name=Ullmann1 /> For similar reasons the compound can sometimes be found in ] and beverages.
			Historically, before ] approaches were developed, phenylacetaldehyde was also used to produce phenylalanine via the ] as a step in the production of ] sweetener.<ref name=Ullmann1 />
			===Polymers===
			Phenylacetaldehyde is used in the synthesis of ]s where it serves as a rate-controlling additive during ].<ref name=Ullmann1 />
			===Natural Medicine===
			Phenylacetaldehyde is responsible for the antibiotic activity of ].<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 ] gives phenelzine.{{citation needed|date=July 2018}}
			==Preparation==
			Phenylacetaldehyde can be obtained via various ] and ]. Notable examples include:
			* ] of ].<ref name=Ullmann1 />
			* ] of ] over ] or ] catalysts.
			* ] between ] and ] ]s.
			* ] of ].
			* ] of ] (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}}</ref>
			* Oxidation of ] with ] ].<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>
			* ] 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==
	Phenylacetaldehyde is often contaminated with polystyrene oxide ] because of the especial lability of the benzylic ] and the reactivity of the aldehyde. ] of the initial dimer gives rise to a range of ] and donors.		Phenylacetaldehyde is often contaminated with polystyrene oxide ] because of the especial lability of the benzylic ] and the reactivity of the aldehyde. ] of the initial dimer gives rise to a range of ] and donors.
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