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Wikipedia

L-Dopaquinone

l-Dopaquinone also known as o-dopaquinone is a metabolite of L-DOPA (L-dihydroxyphenylalanine) and a precursor of melanin.[1][2]

l-Dopaquinone
Names
IUPAC name
3,4-Dioxo-3,4-dihydro-L-phenylalanine
Systematic IUPAC name
(2S)-2-Amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid
Other names
o-Dopaquinone
Identifiers
  • 4430-97-1 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:16852
ChemSpider
  • 388447
  • 439316
UNII
  • 5P7FHT9NL7 Y
  • DTXSID50897220
  • InChI=1S/C9H9NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6H,3,10H2,(H,13,14)/t6-/m0/s1
    Key: AHMIDUVKSGCHAU-LURJTMIESA-N
  • InChI=1/C9H9NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6H,3,10H2,(H,13,14)/t6-/m0/s1
    Key: AHMIDUVKSGCHAU-LURJTMIEBS
  • N[C@@H](CC1=CC(=O)C(=O)C=C1)C(O)=O
Properties
C9H9NO4
Molar mass 195.174 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Biosynthesis of melanin occurs in melanocytes, where tyrosine is converted into DOPA and then dopaquinone, which goes on to be formed into pheomelanin or eumelanin.[3]

References edit

  1. ^ Ito S, Wakamatsu K (2008). "Chemistry of mixed melanogenesis – pivotal roles of dopaquinone". Photochem. Photobiol. 84 (3): 582–92. doi:10.1111/j.1751-1097.2007.00238.x. PMID 18435614.
  2. ^ Hearing VJ (2011). "Determination of melanin synthetic pathways". J. Invest. Dermatol. 131 (E1): E8–E11. doi:10.1038/skinbio.2011.4. PMC 6944209. PMID 22094404.
  3. ^ Schlessinger, Daniel I.; Schlessinger, Joel (January 2020). "Biochemistry, Melanin". StatPearls Publishing. PMID 29083759. Retrieved 22 May 2020.

External links edit


small, small, dopaquinone, dopaquinone, also, known, dopaquinone, metabolite, dopa, dihydroxyphenylalanine, precursor, melanin, dopaquinone, namesiupac, name, dioxo, dihydro, phenylalaninesystematic, iupac, name, amino, dioxocyclohexa, dien, propanoic, acidoth. l Dopaquinone also known as o dopaquinone is a metabolite of L DOPA L dihydroxyphenylalanine and a precursor of melanin 1 2 l Dopaquinone NamesIUPAC name 3 4 Dioxo 3 4 dihydro L phenylalanineSystematic IUPAC name 2S 2 Amino 3 3 4 dioxocyclohexa 1 5 dien 1 yl propanoic acidOther names o DopaquinoneIdentifiersCAS Number 4430 97 1 Y3D model JSmol Interactive imageChEBI CHEBI 16852ChemSpider 388447PubChem CID 439316UNII 5P7FHT9NL7 YCompTox Dashboard EPA DTXSID50897220InChI InChI 1S C9H9NO4 c10 6 9 13 14 3 5 1 2 7 11 8 12 4 5 h1 2 4 6H 3 10H2 H 13 14 t6 m0 s1Key AHMIDUVKSGCHAU LURJTMIESA NInChI 1 C9H9NO4 c10 6 9 13 14 3 5 1 2 7 11 8 12 4 5 h1 2 4 6H 3 10H2 H 13 14 t6 m0 s1Key AHMIDUVKSGCHAU LURJTMIEBSSMILES N C H CC1 CC O C O C C1 C O OPropertiesChemical formula C 9H 9N O 4Molar mass 195 174 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Biosynthesis of melanin occurs in melanocytes where tyrosine is converted into DOPA and then dopaquinone which goes on to be formed into pheomelanin or eumelanin 3 References edit Ito S Wakamatsu K 2008 Chemistry of mixed melanogenesis pivotal roles of dopaquinone Photochem Photobiol 84 3 582 92 doi 10 1111 j 1751 1097 2007 00238 x PMID 18435614 Hearing VJ 2011 Determination of melanin synthetic pathways J Invest Dermatol 131 E1 E8 E11 doi 10 1038 skinbio 2011 4 PMC 6944209 PMID 22094404 Schlessinger Daniel I Schlessinger Joel January 2020 Biochemistry Melanin StatPearls Publishing PMID 29083759 Retrieved 22 May 2020 External links editdopaquinone at the U S National Library of Medicine Medical Subject Headings MeSH nbsp This article about an organic compound is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title L Dopaquinone amp oldid 1171007370, wikipedia, wiki, book, books, library,

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