2,3,5,6,8-Pentahydroxy-1,4-naphthalenedione
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
2,3,5,6,8-Pentahydroxynaphthalene-1,4-dione
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C10H6O7/c11-2-1-3(12)6(13)5-4(2)7(14)9(16)10(17)8(5)15/h1,11-13,16-17H checkY
    Key: HYVDWYISUNRFCU-UHFFFAOYSA-N checkY
  • InChI=1/C10H6O7/c11-2-1-3(12)6(13)5-4(2)7(14)9(16)10(17)8(5)15/h1,11-13,16-17H
    Key: HYVDWYISUNRFCU-UHFFFAOYAZ
  • O=C(C1=C2C(O)=C(O)C(O)=C1O)C(O)=CC2=O
  • Oc1c(O)cc(O)c2C(=O)C(\O)=C(\O)C(=O)c12
Properties
C10H6O7
Molar mass 238.15 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

2,3,5,6,8-Pentahydroxy-1,4-naphthalenedione, also called 2,3,5,6,8-pentahydroxy-1,4-naphthoquinone or spinochrome D, is an organic compound with formula C
10H
6O
5, formally derived from 1,4-naphthoquinone through the replacement of five hydrogen atoms by hydroxyl (OH) groups.

Spinochrome D occurs naturally as a brownish red pigment in the shell and spines of sea urchins such as the Japanese aka-uni (Pseudocentrotus depressus).[1] It is soluble in diethyl ether and crystallizes as brownish red needles that sublime at 285−295 °C.[1]

The compound gives a yellowish brown solution when treated with sodium hydroxide, a bluish green solution with ferric chloride, and a violet precipitate with lead acetate. It forms a five-fold acetate ester, C
10HO
2(CH
3COO)5, that crystallizes from methanol as yellow needles that melt at 185−186 °C.[1]

See also

References

  1. 1 2 3 Chika KURODA and Masae OKAJIMA (1967), Studies on the Derivatives of Naphthoquinones, XVIII. The pigments of sea urchins, XIII. Proc. Japan Acad., volume 43, pages 41--44. Online version accessed on 2010-02-01.
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