Exifone

HCID 40399

Notes Reactions

Substructure search Find similar structures

Basic information

CAS: 52479-85-3
Standard SMILES: O=C(c1cc(O)c(O)c(O)c1)c1ccc(O)c(O)c1O
InChIKey: XEDWWPGWIXPVRQ-UHFFFAOYSA-N
Molecular formula: C13H10O7
Average molar mass: 278.21 g/mol
Monoisotopic mass: 278.04265266

Overview

(2,3,4-trihydroxyphenyl)-(3,4,5-trihydroxyphenyl)methanone is a member of benzophenones.

Names & identifiers

Preferred name: Exifone
IUPAC: (2,3,4-trihydroxyphenyl)-(3,4,5-trihydroxyphenyl)methanone
English name: Exifone
Molecular formula: C13H10O7
Molecular weight: 278.21

Names & synonyms

EXIFONE52479-85-3ExifonaExifonumDTXSID904495038K9TOD4EGNSC-680919DTXCID7024950hexahydro-2,3,4,3',4',5'-benzophenoneRefChem:921423(3,4,5-Trihydroxy-phenyl)-(2,3,4-trihydroxy-phenyl)-methanone257-945-9

Show more names

adloneNsc680919Aids060880Aids-060880Exifone USP/EP/BPExifone, 10 mM in DMSO2,3,3'',4,4''-HEXAHYDROBENZOXYPHENONE3,4,5,2',3',4'-HEXAHYDROXYBENZOPHENONE

2,3,3',4,4',5'-Hexahydroxybenzophenone(2,3,4-Trihydroxyphenyl)(3,4,5-trihydroxyphenyl)methanone4-GalloylpyrogallolExifone [INN](2,3,4-trihydroxyphenyl)-(3,4,5-trihydroxyphenyl)methanoneC13H10O7MFCD00082966Methanone, (2,3,4-trihydroxyphenyl)(3,4,5-trihydroxyphenyl)-

Database identifiers

CAS: 52479-85-3、72841-23-7
PubChem CID: 40399
DTXSID: DTXSID9044950
ChEMBL: CHEMBL329522
ChEBI: CHEBI:125609
UNII: 38K9TOD4EG
EC Number: 257-945-9
Nikkaji: J9.936H

Properties

Computed structural properties

XLogP: 1.7
Topological polar surface area: 138 Å²
Hydrogen bond donors: 6
Hydrogen bond acceptors: 7
Rotatable bonds: 2
Heavy atoms: 20
Formal charge: 0
Complexity: 349

Physicochemical properties

Melting point: 245 °C · 245°C
Boiling point: 674.6 · 674.6±55.0 °C(Predicted)
Density: 1.759 · 1.759±0.06 g/cm3(Predicted)
storage temp.: Sealed in dry,Room Temperature
solubility: DMSO (Slightly), Methanol (Slightly)
form: Solid
pka: 6.99 · 6.99±0.40(Predicted)
color: Yellow
Merck: 3915 · 3915
Stability: Hygroscopic
CAS DataBase Reference: 52479 · 52479-85-3(CAS DataBase Reference)
FDA UNII: 38 K9TOD4EG · 38K9TOD4EG
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319
Precautionary statements: 264 · P264-P270-P280-P301+P312+P330-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P501
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36
RTECS: 4995000 · PC4995000
Toxicity: 50 in · LD50 in rats (g/kg): 0.355 i.p.; 1.425 orally (Gazave)

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Toxicology

Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Exifone

vMost-DILI-concern

Withdrawn

DOI:10.1016/j.drudis.2016.02.015

Safety data

rtecs: PC4995000
Toxicity: LD50 in rats (g/kg): 0.355 i.p.; 1.425 orally (Gazave)
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 26-36
Hazard statements: H302-H315-H319
Precautionary statements: P264-P270-P280-P301+P312+P330-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P501

Chemistry & industry

Applications · 2 items

DescriptionExifone is a nootropic indicated for the treatment of cognitive dysfunctions in geriatric patients. Its reported clinical efficacy is ascribed to pharmacological activities including activation of neuronal oxygen and glucose metabolism, free radical scavenging, and indirect effects on serotonergic and dopaminergic pathways.

UsesExifone is a nootropic drug and cognitive enhancing agent. Exifone is a free radical scavenger shown to have protective effects againts Exifone has been shown to antagonize amnesias induced by benzodiazepines in mice.

Preparation methods · 1 item

PreparationPreparation by condensation of gallic acid with pyrogallol, in the presence of zinc chloride at 120° (good yield) or at 145° for 3 h (Nencki reaction); in the presence of zinc chloride and phosphorous oxychloride at 80° for 2 h, via Fries rearrangement.