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L-Dopaquinone

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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
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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-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/s1Key: AHMIDUVKSGCHAU-LURJTMIEBS
SMILES
  • N(CC1=CC(=O)C(=O)C=C1)C(O)=O
Properties
Chemical formula C9H9NO4
Molar mass 195.174 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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

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.

References

  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


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