Hexahydroxy-1,4-naphthalenedione

2,3,5,6,7,8-Hexahydroxy-1,4-naphthalenedione, also called hexahydroxynaphthoquinone or spinochrome E,[1] is an organic compound with formula C
10
H
6
O
8
. It is formally derived from naphthoquinone (1,4-naphtalenedione) through replacement of all six hydrogen atoms by hydroxyl (OH) groups. The numerical prefixes "2,3,5,6,7,8" are superfluous, since there is no other hexahydroxy derivative of 1,4-naphthoquinone.

Hexahydroxy-1,4-naphthalenedione
Names
Preferred IUPAC name
Hexahydroxy-1,4-naphthalenedione
Systematic IUPAC name
Hexahydroxy-1,4-dihydronaphthalene-1,4-dione
Other names
Hexahydroxynaphthalene-1,4-dione; Spinochrome E
Identifiers
3D model (JSmol)
ChemSpider
Properties
C10H6O8
Molar mass 254.15 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

The substance forms red micro-needles which do not melt below 300 °C, and can be sublimed in vacuum at about 265 °C.

The compound occurs in the shell ("test") and spines of the sea urchins Paracentrotus lividus and Psammechinus miliaris.

The compound can be produced by condensation of 3,4,5,6-tetramethoxyphthalaldehyde with glyoxal.[2]

See also

References

  1. T. W. Goodwin, E. Lederer and L. Musajo (1951), The nomenclature of the spinochromes of sea urchins. Cellular and Molecular Life Sciences, Volume 7, Number 10, pages 375-376. doi:10.1007/BF02168905
  2. H. A. Anderson and R. H. Thomson (1966), Naturally Occurring Quinones. Part VIP Synthesis of Spinochrome E. J. Chem. Soc. series C (Organic), pages 426-428. doi:10.1039/J39660000426
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