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
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.

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
CAS Number	476-37-9
3D model (JSmol)	Interactive image
ChemSpider	15712468
PubChem CID	135409398
CompTox Dashboard (EPA)	DTXSID20431231
InChI 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
SMILES OC1=C(O)C(=O)C2=C(C1=O)C(O)=C(O)C(O)=C2O
Properties
Chemical formula	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

• Hexahydroxy-2,3-naphthalenedione, a structural isomer.
• Tetrahydroxybenzoquinone
• Octahydroxyanthraquinone

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