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L-Dopaquinone

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
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • 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).

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

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]

  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.

L-Dopaquinone

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