1,3-Dihydroxyanthraquinone

Chemical compound From Wikipedia, the free encyclopedia

1,3-Dihydroxyanthraquinone, also called purpuroxanthin or xanthopurpurin, is an organic compound with formula C
14H
8O
4 that occurs in the plant Rubia cordifolia (Indian madder).[1] It is one of ten dihydroxyanthraquinone isomers. Its molecular structure can be viewed as being derived from anthraquinone by replacement of two hydrogen atoms (H) by hydroxyl groups (-OH).

Quick facts Names, Identifiers ...
1,3-Dihydroxyanthraquinone
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name
1,3-Dihydroxyanthracene-9,10-dione
Other names
Purpuroxanthin; Xanthopurpurin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C14H8O4/c15-7-5-10-12(11(16)6-7)14(18)9-4-2-1-3-8(9)13(10)17/h1-6,15-16H checkY
    Key: WPWWKBNOXTZDQJ-UHFFFAOYSA-N checkY
  • InChI=1/C14H8O4/c15-7-5-10-12(11(16)6-7)14(18)9-4-2-1-3-8(9)13(10)17/h1-6,15-16H
    Key: WPWWKBNOXTZDQJ-UHFFFAOYAR
  • O=C2c1ccccc1C(=O)c3c2cc(O)cc3O
Properties
C14H8O4
Molar mass 240.21 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 Â°C [77 Â°F], 100 kPa).
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Xanthopurpurin occurs in small amounts (as a glycoside) in the root of the common madder plant, Rubia tinctorum, together with alizarin, purpurin and other anthraquinone derivatives.[2]

Properties

Xanthopurpurin is insoluble in hexane but soluble in chloroform. It can be obtained from solutions in the latter as reddish crystals that melt at 270–273 Â°C.[1]

Like many dihydroxy- and trihydroxyanthraquinones, it has a purgative action, although only 1/6 as effective as 1,2,7-trihidroxyanthraquinone (anthrapurpurin).[3]

See also

References

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