Unii-L3Z7U4N28P
Basic information
- CAS
569-77-7- Standard SMILES
O=c1cccc2cc(O)c(O)c(O)c2c1O- InChIKey
WDGFFVCWBZVLCE-UHFFFAOYSA-N- Molecular formula
- C11H8O5
- Average molar mass
- 220.18 g/mol
- Monoisotopic mass
- 220.03717335
Overview
See also: Purpurogallin (preferred).
Names & identifiers
- Preferred name
- Unii-L3Z7U4N28P
- IUPAC
- 2,3,4,5-tetrahydroxybenzo[7]annulen-6-one
- English name
- PURPUROGALLIN
- Molecular formula
- C11H8O5
- Molecular weight
- 220.18
Names & synonyms
UNII-L3Z7U4N28PCCRIS 81393tiyEINECS 209-324-9NSC 35676BRN 1978265PURPUROGALLIN [MI]4-08-00-03456 (Beilstein Handbook Reference)BIDD:ER0545orb1307831MSK181025NSC846469
Show more names
C09964MLS0007NSC 646653AIDS138915CHEBI:8647AIDS-138915AKOS 209-004KBio1_001351KBio2_000828
NSC-846469HY-12136DB-052995CS-0003104F82020T166852,3,4,5-tetrahydroxy-6H-benzo[7]annulen-6-oneQ7261541
Database identifiers
- CAS
569-77-7- PubChem CID
- 5281571
- DTXSID
DTXSID40205436- UNII
- L3Z7U4N28P
- Nikkaji
- J20.746B
Properties
Computed structural properties
- XLogP
- 0.5
- Topological polar surface area
- 98 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 0
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 529
Physicochemical properties
- Melting point
- 275 °C · 275 °C (dec.)(lit.)
- Boiling point
- 321.11 °C · 321.11°C (rough estimate)
- Density
- 1.3824 · 1.3824 (rough estimate)
- refractive index
- 1.514 · 1.5140 (estimate)
- storage temp.
- 20 °C · −20°C
- solubility
- DMSO (Slightly), Methanol (Slightly)
- pka
- 6.75 · 6.75±0.20(Predicted)
- form
- Solid
- color
- Very Dark Brown
- Merck
- 7946 · 7946
- Stability
- Air Sensitive
- Cosmetics Ingredients Functions
- HUMECTANTSKIN CONDITIONING
- LogP
- 2.05 · 2.050 (est)
- FDA UNII
- 3 Z7U4N28P · L3Z7U4N28P
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- rtecs
- DE8380000
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Hazard statements
- H319-H315-H335
- Precautionary statements
- P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P
Chemistry & industry
Applications
DescriptionPurpurogallin is a phenol that has been found in D. divisa and a derivative of pyrogallol that has diverse biological activities, including antimicrobial, antioxidant, and enzyme inhibitory properties. It is active against the Gram-positive bacteria S. aureus, methicillin-resistant S. aureus (MRSA), S. epidermidis, and B. subtilis (MICs = 11-110 μg/ml), the Gram-negative bacteria S. marcescens, P. vulgaris, K. pneumoniae, E. coli, S. typhi, and E. cloacae (MIC = 110 μg/ml for all), as well as P. falciparum strain FCB1 clone NC-1 (IC50 = 55 μM). Purpurogallin (2, 5, and 10 μM) scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; ) radicals in a cell-free assay and reduces hydrogen peroxide- and radiation-induced production of reactive oxygen species (ROS) in HaCaT keratinocytes. It inhibits the activity of EGFR, glutathione-S-transferase (GST), prolyl endopeptidase, and glyoxalase I (IC50s = 27.5, 8, 16, and 50 μM, respectively), as well as catechol O-methyltransferase (COMT; Ki = 0.074 μM), in cell-free assays.
Usesxanthine oxidase inhibitor, antioxidant
Additional notes
DefinitionChEBI: A cyclic ketone that is 5H-benzocycloheptene bearing an oxo group at position 5 and hydroxy groups at positions 2, 3, 4 and 6.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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