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52479-85-3

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52479-85-3 Usage

Description

3,4,5,2',3',4'-Hexahydroxybenzophenone is a naturally occurring compound with a unique chemical structure characterized by six hydroxyl groups attached to a benzophenone core. It is known for its potent antioxidant, anti-inflammatory, and free radical scavenging properties, making it a valuable compound for various applications in different industries.

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.

Check Digit Verification of cas no

The CAS Registry Mumber 52479-85-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,2,4,7 and 9 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 52479-85:
(7*5)+(6*2)+(5*4)+(4*7)+(3*9)+(2*8)+(1*5)=143
143 % 10 = 3
So 52479-85-3 is a valid CAS Registry Number.

52479-85-3Synthetic route

2,3,4-trihydroxybenzoic acid
610-02-6

2,3,4-trihydroxybenzoic acid

2-hydroxyresorcinol
87-66-1

2-hydroxyresorcinol

2,3,4,3',4',5'-hexahydroxybenzophenone
52479-85-3

2,3,4,3',4',5'-hexahydroxybenzophenone

Conditions
ConditionsYield
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

3,4,5-trihydroxybenzoic acid

2-hydroxyresorcinol
87-66-1

2-hydroxyresorcinol

2,3,4,3',4',5'-hexahydroxybenzophenone
52479-85-3

2,3,4,3',4',5'-hexahydroxybenzophenone

Conditions
ConditionsYield
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

2,3,4,3',4',5'-hexahydroxybenzophenone

α-bromoacetophenone
70-11-1

α-bromoacetophenone

A

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

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

B

2-{4-[3,5-Dihydroxy-4-(2-oxo-2-phenyl-ethoxy)-benzoyl]-2,3-dihydroxy-phenoxy}-1-phenyl-ethanone

2-{4-[3,5-Dihydroxy-4-(2-oxo-2-phenyl-ethoxy)-benzoyl]-2,3-dihydroxy-phenoxy}-1-phenyl-ethanone

Conditions
ConditionsYield
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

2,3,4,3',4',5'-hexahydroxybenzophenone

methyl iodide
74-88-4

methyl iodide

A

(2,3,4-trihydroxyphenyl)(3',5'-dihydroxy-4'-methoxyphenyl)methanone

(2,3,4-trihydroxyphenyl)(3',5'-dihydroxy-4'-methoxyphenyl)methanone

B

(2,3-dihydroxy-4-methoxyphenyl)(3',5'-dihydroxy-4'-methoxyphenyl)methanone

(2,3-dihydroxy-4-methoxyphenyl)(3',5'-dihydroxy-4'-methoxyphenyl)methanone

Conditions
ConditionsYield
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

2,3,4,3',4',5'-hexahydroxybenzophenone

CH3X

CH3X

(2,3,4-trihydroxyphenyl)(3',5'-dihydroxy-4'-methoxyphenyl)methanone

(2,3,4-trihydroxyphenyl)(3',5'-dihydroxy-4'-methoxyphenyl)methanone

Conditions
ConditionsYield
With lithium carbonate In N,N-dimethyl-formamide15%
2,3,4,3',4',5'-hexahydroxybenzophenone
52479-85-3

2,3,4,3',4',5'-hexahydroxybenzophenone

pivaloyl chloride
3282-30-2

pivaloyl chloride

3,4,5,4',5',6',-hexapivaloyloxybenzophenone

3,4,5,4',5',6',-hexapivaloyloxybenzophenone

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

52479-85-3Relevant articles and documents

Evaluation of polyhydroxybenzophenones as α-glucosidase inhibitors

Hu, Xuesen,Xiao, Yang,Wu, Jianlong,Ma, Lin

experimental part, p. 71 - 77 (2011/09/21)

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

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