Hexahydroxy-1,4-naphthalenedione

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Hexahydroxy-1,4-naphthalenedione
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
2,3,5,6,7,8-Hexahydroxynaphthalene-1,4-dione
Other names
Hexahydroxynaphthalene-1,4-dione; Spinochrome E
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C10H6O8/c11-3-1-2(5(13)9(17)7(3)15)6(14)10(18)8(16)4(1)12/h11,13,15-18H
    Key: RUQPQFLYDCXMGX-UHFFFAOYSA-N
  • OC1=C(O)C(=O)C2=C(C1=O)C(O)=C(O)C(O)=C2O
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

2,3,5,6,7,8-Hexahydroxy-1,4-naphthalenedione, also called hexahydroxynaphthoquinone or spinochrome E,[1] is an organic compound with formula C
10H
6O
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.

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 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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