Spinochrome B

Spinochrome B
Names
	Preferred IUPAC name 2,3,5,7-Tetrahydroxynaphthalene-1,4-dione
Identifiers
CAS Number	604-46-6 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	14617131 ;
PubChem CID	135449020;
UNII	8F4EG354EB ;
CompTox Dashboard (EPA)	DTXSID30314748 ;
	InChI InChI=1S/C10H6O6/c11-3-1-4-6(5(12)2-3)8(14)10(16)9(15)7(4)13/h1-2,11-12,15-16H Key: RWRKDUHFUYRCIT-UHFFFAOYSA-N ; InChI=1/C10H6O6/c11-3-1-4-6(5(12)2-3)8(14)10(16)9(15)7(4)13/h1-2,11-12,15-16H Key: RWRKDUHFUYRCIT-UHFFFAOYAA;
	SMILES O=C(C1=C2C(O)=CC(O)=C1)C(O)=C(O)C2=O; Oc1cc(O)c2c(c1)C(=O)C(\O)=C(\O)C2=O;
Properties
Chemical formula	C10H6O6
Molar mass	222.15 g/mol
	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 B (2,3,5,7-tetrahydroxynaphthoquinone) is an organic compound with formula C
₁₀H
₆O
₄, formally derived from 1,4-naphthoquinone through the replacement of four hydrogen atoms by hydroxyl (OH) groups.

Spinochrome B occurs naturally as pigment in the shell and spines of sea urchins such as the Japanese dull red species aka-uni (Pseudocentrotus depressus), the greenish-black murasaki-uni (Heliocidaris crassispina), and the brown bafun-uni (Strongylocentrotus pulcherrimus).^[1]^[2] It is soluble in methanol and crystallizes as bright red needles that sublime above 200 °C.^[2]

The compound gives a greenish yellow solution when treated with sodium hydroxide, a green solution with ferric chloride, and a green precipitate with lead acetate. It forms a fourfold acetate ester, C
₁₀H
₂O
₂(CH
₃COO)₄, that crystallizes from methanol as yellow needles that melt at 157 °C.^[2]

References

^ Chika KURODA and Masae OKAJIMA (1958), Studies on the Derivatives of Naphthoquinones, XIV. The pigments of sea urchins, IX. Proc. Japan Acad., volume 34, pages 616--618. Online version accessed on 2010-02-01. Pigment M₂ is drawn as 2,3,6,8-thNQ but that is the same as 2,3,5,7-thNQ. The genus Heliocedaris should be Heliocidaris and the species purcherrmus should be pulcherrimus.
^ ^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.

[kurodaXIV-1] Chika KURODA and Masae OKAJIMA (1958), Studies on the Derivatives of Naphthoquinones, XIV. The pigments of sea urchins, IX. Proc. Japan Acad., volume 34, pages 616--618. Online version accessed on 2010-02-01. Pigment M₂ is drawn as 2,3,6,8-thNQ but that is the same as 2,3,5,7-thNQ. The genus Heliocedaris should be Heliocidaris and the species purcherrmus should be pulcherrimus.

[kurodaXVIII-2] 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]

[2]

Spinochrome B

See also

References