Dihydroxynaphthoquinone


A dihydroxynaphthoquinone is any of several organic compounds that can be viewed as derivatives of naphthoquinone through replacement of two hydrogen atoms by hydroxyl groups.
The unqualified term "dihydroxynaphthoquinone" usually means a derivative of 1,4-naphthoquinone. Other dihydroxy- compounds can be derived from the two other known isomers, 1,2-naphthoquinone and 2,6-naphthoquinone.

Isomers

From 1,4-naphthoquinone

Due to the symmetry of the parent quinone, there are only nine distinct isomers of dihydroxy-1,4-naphthoquinone:
  • 2,3-Dihydroxy-1,4-naphthoquinone.
  • 2,5-Dihydroxy-1,4-naphthoquinone.
  • 2,6-Dihydroxy-1,4-naphthoquinone.
  • 2,7-Dihydroxy-1,4-naphthoquinone.
  • 2,8-Dihydroxy-1,4-naphthoquinone.
  • 5,6-Dihydroxy-1,4-naphthoquinone.
  • 5,7-Dihydroxy-1,4-naphthoquinone.
  • 5,8-Dihydroxy-1,4-naphthoquinone.
  • 6,7-Dihydroxy-1,4-naphthoquinone.

From 1,2-naphthoquinone

From 1,2-naphthoquinone there are 12 possible dihydroxy- isomers:
  • 3,4-Dihydroxy-1,2-naphthoquinone
  • 3,5-Dihydroxy-1,2-naphthoquinone
  • 3,6-Dihydroxy-1,2-naphthoquinone
  • 3,7-Dihydroxy-1,2-naphthoquinone
  • 3,8-Dihydroxy-1,2-naphthoquinone
  • 4,5-Dihydroxy-1,2-naphthoquinone
  • 4,6-Dihydroxy-1,2-naphthoquinone
  • 4,7-Dihydroxy-1,2-naphthoquinone
  • 4,8-Dihydroxy-1,2-naphthoquinone
  • 5,6-Dihydroxy-1,2-naphthoquinone
  • 5,7-Dihydroxy-1,2-naphthoquinone
  • 5,8-Dihydroxy-1,2-naphthoquinone
  • 6,7-Dihydroxy-1,2-naphthoquinone
  • 6,8-Dihydroxy-1,2-naphthoquinone
  • 7,8-Dihydroxy-1,2-naphthoquinone

From 2,6-naphthoquinone

From the symmetrical 2,6-naphthoquinone there are only nine dihydroxy- isomers:
  • 1,3-Dihydroxy-2,6-naphthoquinone
  • 1,4-Dihydroxy-2,6-naphthoquinone
  • 1,5-Dihydroxy-2,6-naphthoquinone
  • 1,7-Dihydroxy-2,6-naphthoquinone
  • 1,8-Dihydroxy-2,6-naphthoquinone
  • 3,4-Dihydroxy-2,6-naphthoquinone
  • 3,7-Dihydroxy-2,6-naphthoquinone
  • 3,8-Dihydroxy-2,6-naphthoquinone
  • 4,8-Dihydroxy-2,6-naphthoquinone