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

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

Uses

Used in Pharmaceutical Industry:
3,4,5,2',3',4'-Hexahydroxybenzophenone is used as a therapeutic agent for its antioxidant, anti-inflammatory, and free radical scavenging properties. It can be employed in the development of drugs targeting various diseases, including neurodegenerative disorders, cardiovascular diseases, and cancer, due to its ability to protect cells from oxidative stress and inflammation.
Used in Cosmetic Industry:
3,4,5,2',3',4'-Hexahydroxybenzophenone is used as an active ingredient in cosmetic products for its antioxidant and anti-aging properties. It can help protect the skin from environmental stressors, such as UV radiation and pollution, and promote skin health by reducing the visible signs of aging, such as fine lines and wrinkles.
Used in Food Industry:
3,4,5,2',3',4'-Hexahydroxybenzophenone is used as a natural preservative and antioxidant in the food industry. It can help extend the shelf life of perishable products by neutralizing free radicals and preventing lipid oxidation, which can lead to rancidity and spoilage.
Used in Agricultural Industry:
3,4,5,2',3',4'-Hexahydroxybenzophenone can be used as a natural pesticide or fungicide in the agricultural industry. Its antioxidant and anti-inflammatory properties can help protect crops from various diseases and pests, promoting healthy plant growth and increased crop yields.
Used in Environmental Applications:
3,4,5,2',3',4'-Hexahydroxybenzophenone can be utilized in environmental applications, such as water and air purification, due to its ability to neutralize harmful pollutants and toxins. It can be employed in the development of eco-friendly technologies for the remediation of contaminated sites and the reduction of environmental pollution.

Originator

Pharmascience (France)

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.

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

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

Synthesis and biological evaluation of polyhydroxy benzophenone as mushroom tyrosinase inhibitors

A series of polyhydroxy benzophenone were synthesized and evaluated as mushroom tyrosinase inhibitors. The results demonstrated that most of the target compounds had remarkable inhibitory activities on mushroom tyrosinase. Among all these compounds, 2,3,4,3′,4′,5′-hexahydroxy-diphenylketone 10 was found to be the most potent tyrosinase inhibitor with IC50 value of 1.4 μM. In addition, the inhibition kinetics analyzed by Lineweaver-Burk plots revealed that such compounds were competitive inhibitors. These results suggested that such compounds might be utilized for the development of new candidate for treatment of dermatological disorders.