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131-55-5 Usage

Application

2,2',4,4'-Tetrahydroxybenzophenone (BZP-2) is water-soluble and light-yellow powder (figure 1). BZP-2 is widely used in perfumes to prevent their degradation due to light. BZP-2 is a UV-absorber that helps protect against product degradation because of UV-light exposure and it is widely used in sunscreens and in cosmetics (figure 2), such as: anti-aging” creams and hair sprays and shampoos, paints and plastics. It can also mask odor associated with a formulation’s composition. In addition, the hypolipemiant drug fenofibrate is also a substituted benzophenone.

Potential Exposure & Risk

Although 2,2',4,4'-Tetrahydroxybenzophenone is used as a UV-blocker in cosmetics, plastics and automotive car products, its safety issue still should be noted. Such as workers that use BZP-2 may breathe in dust or have direct skin contact and the general population may be exposed by dermal contact with products containing this compound. Skin allergic reaction has been reported in some people using sunscreens or cosmetics containing this compound. 2,2',4,4'-Tetrahydroxybenzophenone(BZP-2) is a member of a group of chemicals known as endocrine disruptors, which may alter the function and/or development of the reproductive system. Limited evidence indicates that exposure to benzophenone UV-absorbing chemicals, including BZP-2, is associated with an altered ratio of males to females at birth (increased females).

Chemical Properties

yellow to brown crystalline powder

Uses

Different sources of media describe the Uses of 131-55-5 differently. You can refer to the following data:
1. 2,2′,4,4′-Tetrahydroxybenzophenone are benzophenone-type UV filters with known or suspected endocrine disrupting properties detected in surface waters, sunscreens, personal care products, clothing and food packaging. It is used to protect the skin and materials from the adverse effects of UV-radiation.
2. 2,2',4,4'-Tetrahydroxybenzophenone is a uV-absorber that helps protect against product degradation because of uV-light exposure. It can also mask odor associated with a formulation’s composition.
3. 2,2',4,4'-Tetrahydroxybenzophenone is used as the raw material of ultraviolet absorbers in cosmetics, plastics, resins and rubber. It is used as pharmaceutical intermediates and light-sensitive materials. It is also used as pharmaceutical adjuvant.

Preparation

Obtained (small amount) by melting a fluorescin chloride/sodium hydroxide mixture in the presence of a very few water at 230–240° for 2–3 h.

Contact allergens

BZP-2 is widely used in perfumes to prevent their degradation due to light. It can cause allergic contact dermatitis.

Safety Profile

Moderately toxic by ingestion. Aneye irritant. Mutation data reported. When heated todecomposition it emits toxic fumes of NOx.

Check Digit Verification of cas no

The CAS Registry Mumber 131-55-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 1 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 131-55:
(5*1)+(4*3)+(3*1)+(2*5)+(1*5)=35
35 % 10 = 5
So 131-55-5 is a valid CAS Registry Number.

131-55-5 Well-known Company Product Price

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  • Alfa Aesar

  • (A10237)  2,2',4,4'-Tetrahydroxybenzophenone, 98+%   

  • 131-55-5

  • 25g

  • 348.0CNY

  • Detail
  • Alfa Aesar

  • (A10237)  2,2',4,4'-Tetrahydroxybenzophenone, 98+%   

  • 131-55-5

  • 100g

  • 1068.0CNY

  • Detail

131-55-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,2',4,4'-Tetrahydroxybenzophenone

1.2 Other means of identification

Product number -
Other names Seesorb 106

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:131-55-5 SDS

131-55-5Synthetic route

carbonylbis(benzene-4,1,3-triyl) tetraacetate

carbonylbis(benzene-4,1,3-triyl) tetraacetate

2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

Conditions
ConditionsYield
With hydrogenchloride In water at 20 - 100℃; for 6h; Temperature; Autoclave; Large scale;82.1%
4-hydroxysalicylic acid
89-86-1

4-hydroxysalicylic acid

recorcinol
108-46-3

recorcinol

2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

Conditions
ConditionsYield
With zinc(II) chloride; trichlorophosphate at 65℃; for 3h; Inert atmosphere;73%
With zinc(II) chloride; trichlorophosphate
With zinc(II) chloride at 125 - 140℃;
1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

Conditions
ConditionsYield
With aluminium trichloride; 1,2-dichloro-ethane
2.4-dioxy-2'.4'-diacetoxy-benzophenone-imide

2.4-dioxy-2'.4'-diacetoxy-benzophenone-imide

2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

Conditions
ConditionsYield
With sulfuric acid
With sodium hydroxide
fluorescein chloride

fluorescein chloride

A

2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

B

benzoic acid , 2',4'-dioxy-benzophenone-carboxylic acid-(2), resorcinol

benzoic acid , 2',4'-dioxy-benzophenone-carboxylic acid-(2), resorcinol

Conditions
ConditionsYield
With sodium hydroxide
bis(2-hydroxy-4-methoxyphenyl)-methanone
131-54-4

bis(2-hydroxy-4-methoxyphenyl)-methanone

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

Conditions
ConditionsYield
AlCl3
bis(2-hydroxy-4-methoxyphenyl)-methanone
131-54-4

bis(2-hydroxy-4-methoxyphenyl)-methanone

2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

Conditions
ConditionsYield
With urea; AlCl3
2,2',4,4'-tetramethoxybenzophenone
3555-85-9

2,2',4,4'-tetramethoxybenzophenone

1,2-dichloro-benzene
95-50-1

1,2-dichloro-benzene

2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

Conditions
ConditionsYield
AlCl3 In water
recorcinol
108-46-3

recorcinol

2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: chloroform / 4 h / 20 - 65 °C / Large scale
1.2: Large scale
2.1: aluminum (III) chloride / N,N-dimethyl-formamide; cis-1,2-Dichloroethylene / 30 - 85 °C / Large scale
3.1: hydrogenchloride / water / 6 h / 20 - 100 °C / Autoclave; Large scale
View Scheme
2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

3,6-dihydroxy-xanthen-9-one
1214-24-0

3,6-dihydroxy-xanthen-9-one

Conditions
ConditionsYield
In water at 220℃; under 1900 Torr;100%
In water at 190℃; for 48h;100%
In water at 200℃; for 6h; Sealed tube;100%
2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

2,2',4,4'-tetra-tert-butyldimethylsilyloxybenzophenone
265975-39-1

2,2',4,4'-tetra-tert-butyldimethylsilyloxybenzophenone

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; silylation;96%
2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

tetramethyl 2,2′,2″,2‴‐[(carbonylbis(benzene‐4,1,3‐triyl))tetrakis(oxy)]tetraacetate

tetramethyl 2,2′,2″,2‴‐[(carbonylbis(benzene‐4,1,3‐triyl))tetrakis(oxy)]tetraacetate

Conditions
ConditionsYield
With potassium carbonate In acetone for 24h; Williamson Ether Synthesis; Reflux;93%
With potassium carbonate In acetone at 65℃;
3-(1H-imidazol-1-yl)propan-1-amine
5036-48-6

3-(1H-imidazol-1-yl)propan-1-amine

2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

C19H19N3O4
1325729-75-6

C19H19N3O4

Conditions
ConditionsYield
In toluene; butan-1-ol for 5h; Inert atmosphere; Reflux;92%
2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

4-(6-hydrazino-1H-indazol-3-yl)-1,3-benzenediol
117767-15-4

4-(6-hydrazino-1H-indazol-3-yl)-1,3-benzenediol

Conditions
ConditionsYield
With ammonium chloride; hydrazine hydrate at 200 - 210℃; for 4h; sealed tube;86%
With hydrazine hydrate at 200℃;
methyl 2-(bromomethyl)propenoate
4224-69-5

methyl 2-(bromomethyl)propenoate

2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

C18H16O7

C18H16O7

Conditions
ConditionsYield
With methyltriethylammonium monomethyl carbonate In acetonitrile at 15℃; for 48h; Solvent; Temperature; Reagent/catalyst; Inert atmosphere;85.8%
methyl 2-(bromomethyl)propenoate
4224-69-5

methyl 2-(bromomethyl)propenoate

2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

C23H22O9

C23H22O9

Conditions
ConditionsYield
With caesium carbonate In acetonitrile at 55℃; for 24h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere;85.5%
2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

C13H6(2)H4O5

C13H6(2)H4O5

Conditions
ConditionsYield
With perchloric acid; d(4)-methanol at 75℃; for 72h; Inert atmosphere;85%
2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

phenylhydrazine
100-63-0

phenylhydrazine

bis(2,4-dihydroxylphenyl)methanone phenylhydrazone
117767-19-8

bis(2,4-dihydroxylphenyl)methanone phenylhydrazone

Conditions
ConditionsYield
With ammonium chloride at 200 - 210℃; for 4h; sealed tube;80%
2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

methyl iodide
74-88-4

methyl iodide

2,2',4,4'-tetramethoxybenzophenone
3555-85-9

2,2',4,4'-tetramethoxybenzophenone

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;79%
2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

4-(6-hydroxy-1H-indazol-3-yl)-1,3-benzenediol
117767-16-5

4-(6-hydroxy-1H-indazol-3-yl)-1,3-benzenediol

Conditions
ConditionsYield
With ammonium chloride; hydrazine hydrate In water Heating;75%
2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

(2,4-dinitro-phenyl)-hydrazine
119-26-6

(2,4-dinitro-phenyl)-hydrazine

2,2',4,4'-tetrahydroxybenzophenon-2,4-dinitrophenylhydrazone

2,2',4,4'-tetrahydroxybenzophenon-2,4-dinitrophenylhydrazone

Conditions
ConditionsYield
With sulfuric acid In methanol at 50℃; for 0.5h;75%
2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

3-chloromethylpyridinium chloride
6959-48-4

3-chloromethylpyridinium chloride

2,2′-dihydroxy-4,4′-bis(pyridin-3-ylmethoxy)benzophenone

2,2′-dihydroxy-4,4′-bis(pyridin-3-ylmethoxy)benzophenone

Conditions
ConditionsYield
Stage #1: 2,2',4,4'-tetrahydroxybenzophenone With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h;
Stage #2: 3-chloromethylpyridinium chloride In N,N-dimethyl-formamide; mineral oil at 20℃; for 13h;
69%
2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

methylhydrazine
60-34-4

methylhydrazine

4-(6-hydroxyl-1-methyl-H-indazol-3-yl)-1,3-benzenediol
117767-17-6

4-(6-hydroxyl-1-methyl-H-indazol-3-yl)-1,3-benzenediol

Conditions
ConditionsYield
With ammonium chloride at 200 - 210℃; for 4h; sealed tube;63%
triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

2,2',4,4'-tetra(1'',4'',7'',10''-tetraoxaundecyl)benzophenone

2,2',4,4'-tetra(1'',4'',7'',10''-tetraoxaundecyl)benzophenone

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 20℃; for 24h;52%
2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

dimethyl sulfate
77-78-1

dimethyl sulfate

2,2',4,4'-tetramethoxybenzophenone
3555-85-9

2,2',4,4'-tetramethoxybenzophenone

Conditions
ConditionsYield
With 18-crown-6 ether; potassium carbonate In acetonitrile for 20h; Heating;40%
With potassium carbonate In acetone for 8h; Reflux;1.4 g
1-Bromo-11-hydroxyundecane
1611-56-9

1-Bromo-11-hydroxyundecane

2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

2,2',4,4'-tetra(11''-hydroxy-1''-undecanoxy)benzophenon

2,2',4,4'-tetra(11''-hydroxy-1''-undecanoxy)benzophenon

Conditions
ConditionsYield
With 18-crown-6 ether; potassium carbonate In acetonitrile for 24h; Heating;35%
2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

acetic anhydride
108-24-7

acetic anhydride

carbonylbis(benzene-4,1,3-triyl) tetraacetate

carbonylbis(benzene-4,1,3-triyl) tetraacetate

Conditions
ConditionsYield
at 140℃; for 48h; Reflux;30%
With pyridine
2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

prenyl bromide
870-63-3

prenyl bromide

(5-hydroxy-2,2-dimethylchroman-6-yl)(2'-hydroxy-4'-(tertpentyloxy)phenyl)methanone
1316308-41-4

(5-hydroxy-2,2-dimethylchroman-6-yl)(2'-hydroxy-4'-(tertpentyloxy)phenyl)methanone

Conditions
ConditionsYield
With Montmorillonite K10 clay at 90℃; Microwave irradiation;6%
2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

2,2',4,4'-tetramethoxybenzophenone
3555-85-9

2,2',4,4'-tetramethoxybenzophenone

Conditions
ConditionsYield
With potassium carbonate; acetone; dimethyl sulfate
With potassium carbonate; dimethyl sulfate In [(2)H6]acetone; ethanol; water; ethyl acetate
2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

3,6-dihydroxy-xanthen-9-one oxime

3,6-dihydroxy-xanthen-9-one oxime

Conditions
ConditionsYield
With ethanol; hydroxylamine hydrochloride; sodium acetate
2-chloro-5,5-dimethyl[1,3,2]dioxaphosphinane 2-oxide
4090-55-5

2-chloro-5,5-dimethyl[1,3,2]dioxaphosphinane 2-oxide

2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

(2,4-Dihydroxy-phenyl)-[4-(5,5-dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yloxy)-2-hydroxy-phenyl]-methanone

(2,4-Dihydroxy-phenyl)-[4-(5,5-dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yloxy)-2-hydroxy-phenyl]-methanone

Conditions
ConditionsYield
With potassium carbonate In acetonitrile
2-chloro-5,5-dimethyl[1,3,2]dioxaphosphinane 2-oxide
4090-55-5

2-chloro-5,5-dimethyl[1,3,2]dioxaphosphinane 2-oxide

2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

Bis-[4-(5,5-dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yloxy)-2-hydroxy-phenyl]-methanone

Bis-[4-(5,5-dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yloxy)-2-hydroxy-phenyl]-methanone

Conditions
ConditionsYield
With potassium carbonate In acetonitrile
2-chloro-5,5-dimethyl[1,3,2]dioxaphosphinane 2-oxide
4090-55-5

2-chloro-5,5-dimethyl[1,3,2]dioxaphosphinane 2-oxide

2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

[2,4-Bis-(5,5-dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yloxy)-phenyl]-[4-(5,5-dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yloxy)-2-hydroxy-phenyl]-methanone

[2,4-Bis-(5,5-dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yloxy)-phenyl]-[4-(5,5-dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yloxy)-2-hydroxy-phenyl]-methanone

Conditions
ConditionsYield
With potassium carbonate In acetonitrile
2-chloro-5,5-dimethyl[1,3,2]dioxaphosphinane 2-oxide
4090-55-5

2-chloro-5,5-dimethyl[1,3,2]dioxaphosphinane 2-oxide

2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

Bis-[2,4-bis-(5,5-dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yloxy)-phenyl]-methanone

Bis-[2,4-bis-(5,5-dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yloxy)-phenyl]-methanone

Conditions
ConditionsYield
With potassium carbonate In acetonitrile
3-methylpentanoyl chloride
51116-72-4

3-methylpentanoyl chloride

2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

2,2',4,4'-tetra(3-methylvaleroyloxy)benzophenone

2,2',4,4'-tetra(3-methylvaleroyloxy)benzophenone

Conditions
ConditionsYield
With pyridine at 50℃; for 2h;
In pyridine
2,2',4,4'-tetrahydroxybenzophenone
131-55-5

2,2',4,4'-tetrahydroxybenzophenone

pivaloyl chloride
3282-30-2

pivaloyl chloride

2,2',4,4'-tetrapivaloyloxybenzophenone

2,2',4,4'-tetrapivaloyloxybenzophenone

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

131-55-5Relevant articles and documents

Method for catalytically synthesizing ultraviolet light absorber BP-2

-

Paragraph 0020; 0030-0033; 0038-0049, (2020/11/23)

The invention discloses a method for catalytically synthesizing an ultraviolet light absorber BP-2. The method comprises the following steps: (1) adding a halogenated hydrocarbon solvent and a composite catalyst into a reactor, uniform stirring and mixing, heating to 90-120 DEG C, adding 2,4-dihydroxybenzoic acid and m-diphenol into the mixture, carrying out stirring dissolving, carrying out a thermal insulation reaction for 2-3 h, after the reaction is finished, filtering while hot to recover the catalyst graphite, adding a proper amount of water into the filtrate, heating to 90-100 DEG C, completely stirring and dissolving, standing for layering, distilling an organic layer to recover a solvent, cooling a water layer to 10-20 DEG C, separating out a large amount of red crystals, carryingout suction filtration, and washing with water to obtain a crude product; and (2) dissolving the crude product with a proper amount of hot water, adding activated carbon to decolorize, boiling for 30-60 minutes, filtering while hot, cooling and crystallizing to obtain a light yellow green crystal ultraviolet light absorber BP-2 product with the melting point of 199-200 DEG C and the purity of more than or equal to 99.8%. The method is high in synthesis yield, simple in production process, high in product purity, low in cost and suitable for industrial production.

Synthesis, SAR and biological evaluation of natural and non-natural hydroxylated and prenylated xanthones as antitumor agents

Zhang, Xiaojin,Li, Xiang,Tao, Lei,Gao, Yuan,Gong, Dandan,Xi, Meiyang,Xu, Xiaoli,Guo, Qinglong,You, Qidong,Ye, Suofu,Zhang, Yu,Meng, Huyan,Zhang, Mingqian,Gao, Wenlei

, p. 1012 - 1025,14 (2012/12/12)

In order to explore the detailed structure-activity relationship (SAR) around xanthone scaffold bearing hydroxyl and prenyl moieties, twenty-nine natural and non-natural hydroxylated and prenylated xanthones have been synthesized and evaluated for their in vitro anti-proliferative activities against five human cancer cell lines, including HepG2 (hepatocelluar carcinoma), HCT-116 (colon carcinoma), A549 (lung carcinoma), BGC823 (gastric carcinoma) and MDAMB- 231 (breast carcinoma). The SAR analysis revealed that the anti-proliferative activity of the xanthones is substantially influenced by the position and number of attached hydroxyl and prenyl groups, and the presence of hydroxyl group ortho to the carbonyl function of xanthone scaffold contributes significantly to their cytotoxicity. The new prenylated xanthone 20 with a relatively simple structure, namely 1,3,8-trihydroxy-2-prenylxanthone, was found to exhibit potent antitumor activities comparable to mangostin against all the five cancer cell lines. Further mechanistic studies suggested that compound 20 induces apoptosis and causes cell cycle arrest at S phase in HepG2 cells. These results have highlighted compound 20 as a new potential lead candidate for future development of novel potent broad-spectrum antitumor agents.

Synthesis and biological evaluation of polyhydroxy benzophenone as mushroom tyrosinase inhibitors

Wu, Jianlong,Hu, Xuesen,Ma, Lin

experimental part, p. 449 - 452 (2012/01/04)

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.

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