52479-85-3

Basic information

• Product Name: 3,4,5,2',3',4'-Hexahydroxybenzophenone
• Synonyms: 3,4,5,2',3',4'-HEXAHYDROXYBENZOPHENONE;(2,3,4-trihydroxyphenyl)(3,4,5-trihydroxyphenyl)methanone;2,3,3',4,4',5'-HEXAHYDROXYBENZOPHENONE;2,3,4,3',4',5'-HEXAHYDROXY BENZOPHENONE;EXIFONE;(2,3,4-trihydroxyphenyl)(3,4,5-trihydroxyphenyl)-methanon;4-galloylpyrogallol;adlone
• CAS NO: 52479-85-3
• Molecular Formula: C₁₃H₁₀O₇
• Molecular Weight: 278.21
• EINECS: 257-945-9
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Neurochemicals;Pharmaceuticals
• Mol File: 52479-85-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: 245°C
• Boiling Point: 674.6 °C at 760 mmHg
• Flash Point: 375.8 °C
• Appearance: /
• Density: 1.759 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 6.99±0.40(Predicted)
• Merck: 3915
• CAS DataBase Reference: 3,4,5,2',3',4'-Hexahydroxybenzophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5,2',3',4'-Hexahydroxybenzophenone(52479-85-3)
• EPA Substance Registry System: 3,4,5,2',3',4'-Hexahydroxybenzophenone(52479-85-3)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• RTECS: PC4995000
• Hazardous Substances Data: 52479-85-3(Hazardous Substances Data)

Usage

Description

Exifone 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.

Chemical Properties

yellow amorphous powder

Originator

Pharmascience (France)

Uses

Exifone 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

Preparation 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.

Brand name

Adlone

Synthetic route

2,3,4-trihydroxybenzoic acid (610-02-6) + 2-hydroxyresorcinol (87-66-1) → 2,3,4,3',4',5'-hexahydroxybenzophenone (52479-85-3)

Conditions	Yield
With zinc(II) chloride; trichlorophosphate at 70℃; for 2.5h; Friedel-Crafts reaction;	90%
Stage #1: 2,3,4-trihydroxybenzoic acid; 2-hydroxyresorcinol With zinc(II) chloride; trichlorophosphate at 70℃; for 2.5h; Stage #2: With water at 4℃; for 24h; Cooling with ice;	90%

3,4,5-trihydroxybenzoic acid (149-91-7) + 2-hydroxyresorcinol (87-66-1) → 2,3,4,3',4',5'-hexahydroxybenzophenone (52479-85-3)

Conditions	Yield
With zinc(II) chloride at 125 - 140℃;
With zinc(II) chloride at 120℃;
in Gegenwart eines Kondensationsmittels;

2,3,4,3',4',5'-hexahydroxybenzophenone (52479-85-3) + α-bromoacetophenone (70-11-1) → <2,3,4-trihydroxyphenyl><3',5'-dihydroxy-4'-(2-oxo-2-phenylethoxy)phenyl>methanone (167566-22-5) + 2-{4-[3,5-Dihydroxy-4-(2-oxo-2-phenyl-ethoxy)-benzoyl]-2,3-dihydroxy-phenoxy}-1-phenyl-ethanone

Conditions	Yield
With lithium carbonate In N,N-dimethyl-formamide for 15h; Ambient temperature;	A 40% B 20%

2,3,4,3',4',5'-hexahydroxybenzophenone (52479-85-3) + methyl iodide (74-88-4) → (2,3,4-trihydroxyphenyl)(3',5'-dihydroxy-4'-methoxyphenyl)methanone + (2,3-dihydroxy-4-methoxyphenyl)(3',5'-dihydroxy-4'-methoxyphenyl)methanone

Conditions	Yield
With lithium carbonate In N,N-dimethyl-formamide at 30℃; for 15h;	A 15% B 30%

2,3,4,3',4',5'-hexahydroxybenzophenone (52479-85-3) + CH3X → (2,3,4-trihydroxyphenyl)(3',5'-dihydroxy-4'-methoxyphenyl)methanone

Conditions	Yield
With lithium carbonate In N,N-dimethyl-formamide	15%

2,3,4,3',4',5'-hexahydroxybenzophenone (52479-85-3) + pivaloyl chloride (3282-30-2) → 3,4,5,4',5',6',-hexapivaloyloxybenzophenone

Conditions	Yield
With pyridine at 50℃; for 2h;

Upstream product

• 610-02-6 2,3,4-trihydroxybenzoic acid 
• 87-66-1 2-hydroxyresorcinol 
• 149-91-7 3,4,5-trihydroxybenzoic acid 

Downstream Products

• 167566-22-5 <2,3,4-trihydroxyphenyl><3',5'-dihydroxy-4'-(2-oxo-2-phenylethoxy)phenyl>methanone 

Relevant articles and documents

Evaluation of polyhydroxybenzophenones as α-glucosidase inhibitors

This experiment was designed to synthesize 18 kinds of polyhydroxybenzophenones by using Friedel-Crafts reaction, and to measure the inhibitory activity on α-glucosidase with p-nitrophenyl-β-D- galactopyranoside (PNPG) as a substrate. Here, acarbose (IC50a= a1674.75aaμmolaL-1) was used as the reference inhibitor. The results demonstrated that most of the target compounds had remarkable inhibitory activities on α-glucosidase. Among all these compounds, 2,4,4′,6-butahydroxydiphenylketone (11) was found to be the most potent α-glucosidase inhibitor with an IC50 value of 10.62aaμmolaL-1. In addition, we found these compounds were competitive inhibitors through the kinetic analysis. The results suggested that such compounds might be utilized for the development of new candidates for diabetes treatment. A series of polyhydroxybenzophenones was synthesized and evaluated as α-glucosidase inhibitors. Compound 11 was found to be the most potent inhibitor. Copyright