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.
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.