Purpurogallin

Chemical compound From Wikipedia, the free encyclopedia

Purpurogallin is an aglycone natural product. It is an orange-red solid that is soluble in polar organic solvents but not in water. Its glycoside (ether-linked to sugar), called dryophantin, is found in nutgalls and oak barks. Purpurogallin can be prepared by oxidation of pyrogallol with sodium periodate.[1]

Quick facts Names, Identifiers ...
Purpurogallin
Chemical structure of purpurogallin
Chemical structure of purpurogallin
Names
Preferred IUPAC name
1,7,8,9-Tetrahydroxy-2H-benzo[7]annulen-2-one
Other names
Purpurogalline
2,3,4,6-Tetrahydroxybenzocyclohepten-5-one
PPG
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.478 Edit this at Wikidata
KEGG
MeSH C026133
UNII
  • InChI=1S/C11H8O5/c12-6-3-1-2-5-4-7(13)10(15)11(16)8(5)9(6)14/h1-4,13,15-16H,(H,12,14) X markN
    Key: WDGFFVCWBZVLCE-UHFFFAOYSA-N X markN
  • C1=CC(=O)C(=C2C(=C1)C=C(C(=C2O)O)O)O
Properties
C11H8O5
Molar mass 220.180 g·mol−1
Appearance Red crystalline solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Medicinal aspects

Purpurogallin is bioactive[2] It can inhibit 2-hydroxy and 4-hydroxyestradiol methylation by catechol-O-methyltransferase.[3] It potently and specifically inhibits TLR1/TLR2 activation pathway.[4]

Historical work

Purpurogallin, obtained by oxidation of pyrogallol, attracted attention for dyeing. Arthur George Perkin (son of William Henry Perkin, discoverer of the dye mauvine) reported early characterization including the formation of trimethyl ether and the triacetate.[5]

References

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