词条 | 2,3,5,7-Tetrahydroxy-1,4-naphthalenedione |
释义 |
| 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
References1. ^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. {{DEFAULTSORT:Tetrahydroxy-1,4-naphthalenedione, 2,3,5,7-}}2. ^1 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. 5 : 1,4-Naphthoquinones|Catechols|Resorcinols|Tetrols|Hydroxynaphthoquinones |
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