Hexahydroxy-1,4-naphthalenedione

2,3,5,6,7,8-Hexahydroxy-1,4-naphthalenedione, also called

Hexahydroxy-1,4-
hexahydroxynaphthoquinone or spinochrome E,[1] is an organic compound with
naphthalenedione
formula C10H6O8. 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 3,4,5,6-

tetramethoxyphthalaldehydewith glyoxal.[2]

See also
Hexahydroxy-2,3-naphthalenedione, a structural isomer. Names
Tetrahydroxybenzoquinone
Preferred IUPAC name
Octahydroxyanthraquinone
Hexahydroxy-1,4-
naphthalenedione
References Systematic IUPAC name
Hexahydroxy-1,4-
1. T. W. Goodwin, E. Lederer and L. Musajo (1951),The nomenclature of dihydronaphthalene-1,4-dione
the spinochromes of sea urchins. Cellular and Molecular Life Sciences,
Other names
Volume 7, Number 10, pages 375-376.doi:10.1007/BF02168905 (http
s://doi.org/10.1007%2FBF02168905) Hexahydroxynaphthalene-1,4-
2. H. A. Anderson and R. H. Thomson (1966),Naturally Occurring
dione
Quinones. Part VIP Synthesis of Spinochrome E
. J. Chem. Soc. series Identifiers
C (Organic), pages 426-428.doi:10.1039/J39660000426(https://doi.org/
CAS Number 476-37-9
10.1039%2FJ39660000426)
3D model Interactive image
(JSmol)
ChemSpider 15712468

InChI
SMILES
Properties
Chemical C10H6O8
formula
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
Retrieved from "https://en.wikipedia.org/w/index.php?title=Hexahydroxy-1,4-naphthalenedione&oldid=797939757
"

This page was last edited on 30 August 2017, at 02:08.

Text is available under theCreative Commons Attribution-ShareAlike License ; additional terms may apply. By using this
site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of theWikimedia
Foundation, Inc., a non-profit organization.