Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Phenylacetic acid: Difference between pages

{{Chembox

|Watchedfields = changed

|verifiedrevid = 464200948

|ImageFile = Kwas fenylooctowy.svg

|ImageSize = 200

|ImageName = Structural formula

|ImageFile1 = Phenylacetic acid molecule ball.png

|ImageSize1 = 180

|ImageName1 = Ball-and-stick model of phenylacetic acid

|PIN = Phenylacetic acid

|SystematicName = 2-Phenylethanoic acid

|OtherNames = α-Toluic acid<br>Benzeneacetic acid<br>2-Phenylacetic acid<br>β-Phenylacetic acid

|Section1={{Chembox Identifiers

|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

|ChemSpiderID = 10181341

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

|UNII = ER5I1W795A

|InChI = 1/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)

|InChIKey = WLJVXDMOQOGPHL-UHFFFAOYAR

|ChEMBL_Ref = {{ebicite|correct|EBI}}

|ChEMBL = 1044

|PubChem = 999

|EINECS = 203-148-6

|RTECS = AJ2430000

|DrugBank = DB09269

|KEGG = C07086

|Beilstein =1099647

|Gmelin = 68976

|3DMet = B02157

|StdInChI_Ref = {{stdinchicite|correct|chemspider}}

|StdInChI = 1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)

|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

|StdInChIKey = WLJVXDMOQOGPHL-UHFFFAOYSA-N

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

|CASNo = 103-82-2

|ChEBI_Ref = {{ebicite|correct|EBI}}

|ChEBI = 30745

|SMILES = O=C(O)Cc1ccccc1

|Section2={{Chembox Properties

|Formula = C₈H₈O₂

|Appearance = white solid

|Odor = honey-like

|MolarMass = 136.15 g/mol

|Density = 1.0809 g/cm³

|pKa = 4.31 (H₂O)<ref name="CRC97">{{cite book | editor= Haynes, William M. | year = 2016 | title = CRC Handbook of Chemistry and Physics | edition = 97th | publisher = [[CRC Press]] | isbn = 978-1498754286 | pages=5–89 | title-link = CRC Handbook of Chemistry and Physics }}</ref>

|MeltingPtC = 76 to 77

|BoilingPtC = 265.5

|Solubility = 15 g/L

|MagSus = -82.72·10⁻⁶ cm³/mol

|Section7={{Chembox Hazards

|ExternalSDS = [http://ptcl.chem.ox.ac.uk/MSDS/PH/phenylacetic_acid.html External MSDS]

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

|GHSSignalWord = Danger

|HPhrases = {{H-phrases|318|319}}

|PPhrases = {{P-phrases|264|280|305+351+338|310|337+313}}

|NFPA-H=2

|NFPA-F=1

|NFPA-R=0

}}

|Section8={{Chembox Legal status

| legal_AU =

| legal_BR = D1

| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-15 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-04-04}}</ref>

| legal_US =

| legal_UK =

| legal_UN =

}}

|Section9={{Chembox Related

|OtherCompounds = [[Benzoic acid]], [[Phenylpropanoic acid]], [[Cinnamic acid]]

}}

}}

'''Phenylacetic acid''' ([[conjugate acid|conjugate base]] '''phenylacetate'''), also known by [[#Names|various synonyms]], is an [[organic compound]] containing a [[phenyl]] [[functional group]] and a [[carboxylic acid]] functional group. It is a white solid with a strong honey-like [[odor]]. [[Endogeny (biology)|Endogenously]], it is a [[catabolism|catabolite]] of [[phenylalanine]]. As a [[chemical industry|commercial chemical]], because it can be used in the illicit production of [[phenylacetone]] (used in the manufacture of [[substituted amphetamine]]s), it is subject to [[Chemical Diversion and Trafficking Act|controls]] in countries including the [[United States]] and [[China]].<ref>{{cite web|url=http://www.chemsafetypro.com/Topics/China/Drug_Precursor_Chemicals_List.html|title=List of Regulated Drug Precursor Chemicals in China|access-date=27 April 2015|url-status=dead|archive-url=https://web.archive.org/web/20150817022812/http://www.chemsafetypro.com/Topics/China/Drug_Precursor_Chemicals_List.html|archive-date=17 August 2015}}</ref>

==Occurrence==

Phenylacetic acid has been found to be an active [[auxin]] (a type of [[plant hormone]]),<ref>{{cite journal |author1=Wightman, F. |author2=Lighty, D. L. | title = Identification of phenylacetic acid as a natural auxin in the shoots of higher plants | journal = Physiologia Plantarum | year = 1982 | volume = 55 | issue = 1 | pages = 17–24 | doi = 10.1111/j.1399-3054.1982.tb00278.x }}</ref> found predominantly in [[fruit]]s. However, its effect is much weaker than the effect of the basic auxin molecule [[indole-3-acetic acid]]. In addition the molecule is naturally produced by the metapleural gland of most ant species and used as an antimicrobial. It is also the oxidation product of [[phenethylamine]] in humans following metabolism by [[monoamine oxidase]] and subsequent metabolism of the intermediate product, [[phenylacetaldehyde]], by the [[aldehyde dehydrogenase]] enzyme; these enzymes are also found in many other organisms.

==Preparation==

This compound may be prepared by the [[hydrolysis]] of [[benzyl cyanide]]:<ref>{{OrgSynth | author = Adams R. | author2 = Thal, A. F. | title = Phenylacetic acid | year = 1922 | volume = 2 | pages = 59 | collvol = 1 | collvolpages = 436 | prep = cv1p0436 }}</ref><ref>{{OrgSynth | author = Wenner, W. | title = Phenylacetamide | year = 1952 | volume = 32 | pages = 92 | collvol = 4 | collvolpages = 760 | prep = cv4p0760 }}</ref>

:[[File:Synthesis of phenylacetic acid from benzyl cyanide.png|300px]]

[[File:Phenylacetic acid - Phenylessigsäure.JPG|Phenylacetic acid|thumb|200px]]

==Reactions==

Phenylacetic acid undergoes [[ketonic decarboxylation]] to form [[ketone]]s.<ref>{{cite book |doi=10.1002/14356007.a15_077 |chapter=Ketones |title=Ullmann's Encyclopedia of Industrial Chemistry |year=2000 |last1=Siegel |first1=Hardo |last2=Eggersdorfer |first2=Manfred |isbn=9783527306732 }}</ref> It can be condensed with itself to form [[dibenzyl ketone]], or with a large excess of another carboxylic acid (in the form of an [[acid anhydride]]), such as with [[acetic anhydride]] to form [[phenylacetone]].

==Applications==

Phenylacetic acid is used in some [[perfume]]s, as it possesses a [[honey]]-like [[odor]] even in low [[concentration]]s. It is also used in [[benzylpenicillin|penicillin G]] production and [[diclofenac]] production. It is also employed to treat type II hyperammonemia to help reduce the amounts of ammonia in a patient's bloodstream by forming phenylacetyl-CoA, which then reacts with nitrogen-rich glutamine to form [[phenylacetylglutamine]]. This compound is then excreted from the patient's body. It's also used in the illicit production of [[phenylacetone]], which is used in the manufacture of [[methamphetamine]].

The sodium [[salt (chemistry)|salt]] of phenylacetic acid, sodium phenylacetate, is used as a pharmaceutical drug for the treatment of [[urea cycle disorder]]s, including as the [[combination drug]] [[sodium phenylacetate/sodium benzoate]] (Ammonul).<ref name=AHFS2019>{{cite web |title=Sodium Phenylacetate and Sodium Benzoate Monograph for Professionals |url=https://www.drugs.com/monograph/sodium-phenylacetate-and-sodium-benzoate.html |website=Drugs.com |access-date=16 November 2019 |language=en}}</ref>

Phenylacetic acid is used in the preparation of and derived from several pharmaceutical drugs, including [[camylofin]], [[bendazol]], [[triafungin]], [[phenacemide]], [[lorcainide]], [[phenindione]], [[phenelzine]] and [[cyclopentolate]].{{citation needed|date=September 2018}}

==In popular culture==

In the crime drama ''[[Breaking Bad]]'', phenylacetic acid is featured twice as a precursor to [[methamphetamine]], first in the episode titled "[[A No-Rough-Stuff-Type Deal]]", then in "[[Salud (Breaking Bad)|Salud]]".<ref>{{cite web |website=Chemistry Views |publisher=[[Chemistry Europe]] |title=The Chemistry of Breaking Bad |last1=Harnisch |first1=Falk |last2=Salthammer |first2=Tunga |archive-url=https://web.archive.org/web/20240208125657/https://www.chemistryviews.org/details/ezine/5416791/The_Chemistry_of_Breaking_Bad/ |archive-date=8 February 2024 |url=https://www.chemistryviews.org/details/ezine/5416791/The_Chemistry_of_Breaking_Bad/}}</ref>

==See also==

* [[Cathinone]]

* [[Methyl phenylacetate]]

==References==

{{Reflist}}

{{Authority control}}

[[Category:Flavors]]

[[Category:Drug control law in the United States]]

[[Category:Auxins]]

[[Category:Phenylacetic acids| ]]