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{{chembox
{{chembox
| Verifiedfields = changed
| verifiedrevid = 477205270
| ImageFile = Xanthopurpurin.svg
| ImageFile = Xanthopurpurin.svg
| ImageSize = 250px
| ImageSize = 200px
| ImageName = Skeletal formula
⚫
| IUPACName = 1,3-dihydroxyanthracene-9,10-dione
| ImageFile1 = Xanthopurpurin-3D-balls.png
| OtherNames =
| ImageSize1 = 220px
⚫
| Section1 = {{Chembox Identifiers
| ImageName1 = Ball-and-stick model
⚫
| PIN = 1,3-Dihydroxyanthracene-9,10-dione
| OtherNames = Purpuroxanthin; Xanthopurpurin
⚫
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 37502
| ChemSpiderID = 170598
| ChemSpiderID = 170598
| 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
| 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
| InChIKey = WPWWKBNOXTZDQJ-UHFFFAOYAR
| InChIKey = WPWWKBNOXTZDQJ-UHFFFAOYAR
| ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫
| CASNo = 518-83-2
| ChEMBL = 372711
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WPWWKBNOXTZDQJ-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
⚫
| CASNo = 518-83-2
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 9RBB2G1GQB
| PubChem = 196978
| PubChem = 196978
| SMILES = O=C2c1ccccc1C(=O)c3c2cc(O)cc3O
| SMILES = O=C2c1ccccc1C(=O)c3c2cc(O)cc3O
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| Formula = C<sub>14</sub>H<sub>8</sub>O<sub>4</sub>
| Formula = C<sub>14</sub>H<sub>8</sub>O<sub>4</sub>
| MolarMass = 240.21 g/mol
| MolarMass = 240.21 g/mol
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| BoilingPt =
| BoilingPt =
| Solubility = }}
| Solubility = }}
| Section3 = {{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards =
| MainHazards =
| FlashPt =
| FlashPt =
| Autoignition = }}
| AutoignitionPt = }}
}}
}}


'''1,3-Dihydroxyanthraquinone''', also called '''purpuroxanthin''' or '''xanthopurpurin''' is an [[organic compound]] with formula {{chem|C|14|H|8|O|4}} that occurs in the plant ''[[Rubia cordifolia]]'' (Indian [[madder]]).<ref name=vankar>
'''1,3-Dihydroxyanthraquinone''', also called '''purpuroxanthin''' or '''xanthopurpurin''', is an [[organic compound]] with formula {{chem|C|14|H|8|O|4}} that occurs in the plant ''[[Rubia cordifolia]]'' (Indian madder).<ref name=vankar>
Padma S. Vankar, Rakhi Shanker, Debajit Mahanta and S.C. Tiwari (2008), ''Ecofriendly sonicator dyeing of cotton with ''Rubia cordifolia'' Linn. using biomordant''. Dyes and Pigments, Volume 76, Issue 1, Pages 207-212. {{doi|10.1016/j.dyepig.2006.08.023}}
Padma S. Vankar, Rakhi Shanker, Debajit Mahanta and S.C. Tiwari (2008), ''Ecofriendly sonicator dyeing of cotton with ''Rubia cordifolia'' Linn. using biomordant''. Dyes and Pigments, Volume 76, Issue 1, Pages 207-212. {{doi|10.1016/j.dyepig.2006.08.023}}
</ref> It is one of ten [[dihydroxyanthraquinone]] isomers. Its molecule can be viewed as deriving from [[anthraquinone]] by replacement of two [[hydrogen]] atoms (H) by [[hydroxyl]] groups (-OH).
</ref> 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).


Xanthopurpurin occurs in small amounts (as a [[glicoside]]) in the root of the [[madder]] plant, ''[[Rubia tinctorum]]'', together with [[alizarin]], [[purpurin]] and other anthraquinone derivatives.<ref name=derk>
Xanthopurpurin occurs in small amounts (as a [[glycoside]]) in the root of the common madder plant, ''[[Rubia tinctorum]]'', together with [[alizarin]], [[Purpurin (dye)|purpurin]] and other anthraquinone derivatives.<ref name=derk>
Goverdina C. H. Derksen, Harm A. G. Niederländer and Teris A. van Beek (2002), ''Analysis of anthraquinones in ''Rubia tinctorum'' L. by liquid chromatography coupled with diode-array UV and mass spectrometric detection''. Journal of Chromatography A, Volume 978, Issues 1-2, Pages 119-127, {{doi|10.1016/S0021-9673(02)01412-7}}
Goverdina C. H. Derksen, Harm A. G. Niederländer and Teris A. van Beek (2002), ''Analysis of anthraquinones in ''Rubia tinctorum'' L. by liquid chromatography coupled with diode-array UV and mass spectrometric detection''. Journal of Chromatography A, Volume 978, Issues 1-2, Pages 119-127, {{doi|10.1016/S0021-9673(02)01412-7}}
</ref>
</ref>


==Properties==
==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 °C.<!-- Vis λ<sub>max</sub> (MeOH) (nm): 425; IR ν<sub>max</sub> (KBr) (cm<sup>−1</sup>): 3310 (–OH), 1660, 1625 (–C=O), 1580 (aromatic –C=C–); MS: ''m''/''z'' 240 (M<sup>+</sup>).--><ref name=vankar/>
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&nbsp;°C.<!-- Vis λ<sub>max</sub> (MeOH) (nm): 425; IR ν<sub>max</sub> (KBr) (cm<sup>−1</sup>): 3310 (–OH), 1660, 1625 (–C=O), 1580 (aromatic –C=C–); MS: ''m''/''z'' 240 (M<sup>+</sup>).--><ref name=vankar/>


Like many dihydroxy- and [[trihydroxyanthraquinone]]s, it has a [[purgative]] action, although only 1/6 as effective as [[1,2,7-Trihidroxyanthraquinone|1,2,7-trihidroxyanthraquinone]] (anthrapurpurin).<ref name= guigan>
Like many [[dihydroxyanthraquinone|dihydroxy]]- and [[trihydroxyanthraquinone]]s, it has a [[purgative]] action, although only 1/6 as effective as [[1,2,7-Trihidroxyanthraquinone|1,2,7-trihidroxyanthraquinone]] (anthrapurpurin).<ref name= guigan>
Hugh Alister McGuigan (1921), ''An introduction to chemical pharmacology; pharmacodynamics in relation to chemistry''. P. Blakiston's son, Philadelphia. [http://www.archive.org/stream/introductiontoch00mcguuoft#page/132 Online version] at archive.org, accessed on 2010-01-30.
Hugh Alister McGuigan (1921), ''An introduction to chemical pharmacology; pharmacodynamics in relation to chemistry''. P. Blakiston's son, Philadelphia. [https://archive.org/stream/introductiontoch00mcguuoft#page/132 Online version] at archive.org, accessed on 2010-01-30.
</ref>
</ref>


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{{reflist}}
{{reflist}}


{{DEFAULTSORT:Dihydroxyanthraquinone, 1,3-}}
{{chem-stub}}

[[Category:Anthraquinone dyes]]
[[Category:Anthraquinone dyes]]
[[Category:Dihydroxyanthraquinones]]
[[Category:Resorcinols]]
[[Category:3-Hydroxypropenals within hydroxyquinones]]

Latest revision as of 07:20, 7 January 2022

1,3-Dihydroxyanthraquinone
Skeletal formula
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 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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).

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[edit]

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 °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[edit]

References[edit]

  1. ^ a b Padma S. Vankar, Rakhi Shanker, Debajit Mahanta and S.C. Tiwari (2008), Ecofriendly sonicator dyeing of cotton with Rubia cordifolia Linn. using biomordant. Dyes and Pigments, Volume 76, Issue 1, Pages 207-212. doi:10.1016/j.dyepig.2006.08.023
  2. ^ Goverdina C. H. Derksen, Harm A. G. Niederländer and Teris A. van Beek (2002), Analysis of anthraquinones in Rubia tinctorum L. by liquid chromatography coupled with diode-array UV and mass spectrometric detection. Journal of Chromatography A, Volume 978, Issues 1-2, Pages 119-127, doi:10.1016/S0021-9673(02)01412-7
  3. ^ Hugh Alister McGuigan (1921), An introduction to chemical pharmacology; pharmacodynamics in relation to chemistry. P. Blakiston's son, Philadelphia. Online version at archive.org, accessed on 2010-01-30.
source: https://en.wikipedia.org/w/index.php?title=1,3-Dihydroxyanthraquinone&diff=1064222712&oldid=341260596

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