A dihydroxynaphthoquinone (formula: ) is any of several
organic compounds that can be viewed as derivatives of
naphthoquinone through replacement of two
hydrogen atoms (H) by
hydroxyl groups (OH).
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
1,2-Naphthoquinone or ''ortho''-naphthoquinone is a polycyclic aromatic organic compound with formula . This yellow solid is prepared by oxidation of 1-amino-2-hydroxynaphthalene with ferric chloride.
Occurrence
This diketone (an ortho- quinone ...
(''ortho''-) and
2,6-naphthoquinone (''amphi''-).
Isomers
From 1,4-naphthoquinone
Due to the symmetry of the parent quinone, there are only nine distinct isomers of dihydroxy-1,4-naphthoquinone:
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2,3-Dihydroxy-1,4-naphthoquinone.
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2,5-Dihydroxy-1,4-naphthoquinone.
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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
Naphthazarin, often called 5,8-dihydroxy-1,4-naphthoquinone or 5,8-dihydroxy-1,4-naphthalenedione (IUPAC), is a naturally occurringThomson R.H. Naturally Occurring Quinones. Academic Press, London (1971). Quoted by Khalafy and Bruce.Thomson R.H. ...
(naphthazarin).
[
J. Khalafy and J.M. Bruce (2002), ''Oxidative dehydrogenation of 1-tetralones: Synthesis of juglone, naphthazarin, and α-hydroxyanthraquinones''. Journal of Sciences, Islamic Republic of Iran, volume 13 issue 2, pages 131-139.
]
*
6,7-Dihydroxy-1,4-naphthoquinone.
From 1,2-naphthoquinone
From 1,2-naphthoquinone there are 12 possible dihydroxy- isomers:
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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:
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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
See also
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Hydroxynaphthoquinone A hydroxynaphthoquinone (formula: ) is any of several organic compounds that can be viewed as derivatives of a naphthoquinone through replacement of one hydrogen atom (H) by a hydroxyl group (-OH).
In general, the term may mean any naphthoquinone d ...
*
Trihydroxynaphthoquinone
*
Dihydroxyanthraquinone A dihydroxyanthraquinone is any of several isomeric organic compounds with formula , formally derived from 9,10-anthraquinone by replacing two hydrogen atoms by hydroxyl groups. Dihyroxyantraquinones have been studied since the early 1900s, and inc ...
References
{{reflist
Hydroxynaphthoquinones