Structure via PubChem · Public domain (PubChem)
purpurogallin
Sign in to saveAlso known as 2,3,4,6-tetrahydroxybenzocyclohepten-5-one, 2,3,4,6-tetrahydroxy-5H-benzocycloheptene-5-one, purpurogalline
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.
In the Vinony graph
Within Vinony's link graph, purpurogallin is referenced by 5 other articles, and connects out to digital object identifier, chemical formula and molar mass.
It is catalogued under topics including Azulenes, Chembox image size set and ECHA InfoCard ID from Wikidata.
Its subject is documented across 7 Wikipedia language editions.
Chemical data
- Formula
- C11H8O5
- Molecular weight
- 220.18 g/mol
- IUPAC name
- 2,3,4,5-tetrahydroxybenzo[7]annulen-6-one
- SMILES
- C1=CC(=O)C(=C2C(=C1)C=C(C(=C2O)O)O)O
- InChIKey
- WDGFFVCWBZVLCE-UHFFFAOYSA-N
- XLogP
- 0.5
- Polar surface area
- 98 Ų
- H-bond donors
- 4
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
111 papers- Purpurogallin is a novel mitogen-activated protein kinase kinase 1/2 inhibitor that suppresses esophageal squamous cell carcinoma growth in vitro and in vivo.Molecular carcinogenesis · 2019
- Purpurogallin.Journal of the Chemical Society · 1948
- Purpurogallin Reverses Neuronal Apoptosis and Enhances "M2" Polarization of Microglia Under Ischemia via Mediating the miR-124-3p/TRAF6/NF-κB Axis.Neurochemical research · 2023
- Purpurogallin carboxylic acid exhibits synergistic effects with 5‑fluorouracil on liver cancer cells in vitro by targeting ABCG2.Experimental and therapeutic medicine · 2024
- Purpurogallin improves neurological functions of cerebral ischemia and reperfusion mice by inhibiting endoplasmic reticulum stress and neuroinflammation.International immunopharmacology · 2022
via PubMed
Wikidata facts
- Subclass of
- polyphenol
- Mass
- 220.037
Show 3 more facts
- canonical SMILES
- C1=CC(=O)C(=C2C(=C1)C=C(C(=C2O)O)O)O
- chemical formula
- C₁₁H₈O₅
- found in taxon
- Quercus
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Medicinal aspects
- Historical work
- References
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.
==Medicinal aspects== Purpurogallin is bioactive It can inhibit 2-hydroxy and 4-hydroxyestradiol methylation by catechol-O-methyltransferase. It potently and specifically inhibits TLR1/TLR2 activation pathway.
Excerpted from Wikipedia’s “purpurogallin” article, available under the CC BY-SA 4.0 licence.