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词条 2,3,5,7-Tetrahydroxy-1,4-naphthalenedione
释义

  1. See also

  2. References

{{chembox
| verifiedrevid = 477210185
| ImageFile = Spinochrome B.svg
| ImageSize = 170px
| ImageName = Skeletal formula
| ImageFile1 = Spinochrome-B-3D-balls.png
| ImageSize1 = 170px
| ImageName1 = Ball-and-stick model
| IUPACName = 1,4,5,7-tetrahydroxynaphthalene-2,3-dione
| OtherNames =
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 14617131
| 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
| InChIKey = RWRKDUHFUYRCIT-UHFFFAOYAA
| SMILES1 = Oc1cc(O)c2c(c1)C(=O)C(\\O)=C(\\O)C2=O
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = RWRKDUHFUYRCIT-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo =
| PubChem = 324101
| SMILES = O=C(C1=C2C(O)=CC(O)=C1)C(O)=C(O)C2=O }}
|Section2={{Chembox Properties
| Formula = C10H6O6
| MolarMass = 222.15 g/mol
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}

2,3,5,7-Tetraahydroxy-1,4-naphthalenedione, also called 2,3,5,7-tetrahydroxynaphthoquinone or spinochrome B, is an organic compound with formula {{chem|C|10|H|6|O|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, {{chem|C|10|H|2|O|2}}({{chem|CH|3|COO}})4, that crystallizes from methanol as yellow needles that melt at 157 °C.[2]

See also

  • Hexahydroxynaphthoquinone (spinochrome E)
  • 2,3,5,6,8-Pentahydroxy-1,4-naphthalenedione (spinochrome D)

References

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{{Dead link|date=March 2019 |bot=InternetArchiveBot |fix-attempted=yes }} 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.
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{{Dead link|date=March 2019 |bot=InternetArchiveBot |fix-attempted=yes }} accessed on 2010-02-01.
{{DEFAULTSORT:Tetrahydroxy-1,4-naphthalenedione, 2,3,5,7-}}

5 : 1,4-Naphthoquinones|Catechols|Resorcinols|Tetrols|Hydroxynaphthoquinones

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