Spinochrome D

Spinochrome D
Names
	Preferred IUPAC name 2,3,5,6,8-Pentahydroxynaphthalene-1,4-dione
Identifiers
CAS Number	1143-11-9 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEMBL	ChEMBL452666 ;
ChemSpider	10287017 ;
PubChem CID	139033598;
UNII	N7SYH8K2SN ;
CompTox Dashboard (EPA)	DTXSID601029285 ;
	InChI 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 Key: HYVDWYISUNRFCU-UHFFFAOYSA-N ; 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;
	SMILES 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
Chemical formula	C10H6O7
Molar mass	238.151 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Spinochrome D (2,3,5,6,8-pentahydroxy-1,4-naphthoquinone) 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]

References

^ ^a ^b ^c 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.

[kuroda-1] 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.

[1]

See also

References