Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 3,4-Dihydroxyphenylacetic acid: Difference between pages

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| PIN = (3,4-Dihydroxyphenyl)acetic acid <!-- the locant ‘2’ for acetic acid is not cited, see P-14.3.4.3 of Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) -->

| OtherNames = 2-(3,4-Dihydroxyphenyl)acetic acid

| InChI = 1/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = KEX5N0R4N5

| MeSHName=3,4-Dihydroxyphenylacetic+Acid

| PubChem=547

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

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

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C01161

| C=8 | H=8 | O=4

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'''3,4-Dihydroxyphenylacetic acid''' ('''DOPAC''') is a [[metabolite]] of the [[neurotransmitter]] [[dopamine]]. Dopamine can be metabolized into one of three substances. One such substance is DOPAC. Another is [[3-methoxytyramine]] (3-MT). Both of these substances are degraded to form [[homovanillic acid]] (HVA). Both degradations involve the enzymes [[monoamine oxidase]] (MAO) and [[catechol-O-methyl transferase]] (COMT), albeit in reverse order: MAO catalyzes dopamine to DOPAC, and COMT catalyzes DOPAC to HVA; whereas COMT catalyzes dopamine to 3-MT and MAO catalyzes 3-MT to HVA. The third metabolic end-product of dopamine is [[norepinephrine]] (noradrenaline).

[[Image:Dopamine degradation.svg|thumb|left|400px|Biodegradation of dopamine]]{{Clear left}}

It can also be found in the bark of ''[[Eucalyptus globulus]]''.<ref>{{cite journal|pmid=21761864|doi=10.1021/jf201801q|title=Characterization of Phenolic Components in Polar Extracts of Eucalyptus globulus Labill. Bark by High-Performance Liquid Chromatography–Mass Spectrometry|year=2011|last1=Santos|first1=Sónia A. O.|last2=Freire|first2=Carmen S. R.|last3=Domingues|first3=M. Rosário M.|last4=Silvestre|first4=Armando J. D.|last5=Neto|first5=Carlos Pascoal|journal=Journal of Agricultural and Food Chemistry|volume=59|issue=17|pages=9386–93}}</ref>

This product has been synthesized (52% yield) from [[4-Hydroxyphenylacetic acid|4-hydroxyphenylacetic acid]] via [[Aerobic organism|aerobic]] [[biotransformation]] using whole cell cultures of ''[[Arthrobacter protophormiae]]''.<ref>{{cite journal|author=Robins, Karen T.|author2=Osorio-Lozada, Antonio|author3=Avi, Manuela|author4=Meyer, Hans-Peter|title=Lonza: Biotechnology – A Key Ingredient for Success in the Future|journal=CHIMIA International Journal for Chemistry|date=2009|volume=63|issue=6|pages=327–330|doi=10.2533/chimia.2009.327}}</ref><ref>{{cite book|author=Sutton, Peter|author2=Whittall, John|title=Practical Methods for Biocatalysis and Biotransformations 2|date=2012|publisher=John Wiley & Sons, Ltd.|location=Chichester, West Sussex|isbn=9781119991397|pages=150–153|url=https://books.google.com/books?id=WlODZ-WX8vIC&q=9781119991397}}</ref>

== References ==

{{Reflist}}

{{Neurotransmitter metabolism intermediates}}

{{DEFAULTSORT:Dihydroxyphenylacetic acid, 3,4-}}

[[Category:Phenolic human metabolites]]

[[Category:Acetic acids]]

[[Category:Catechols]]