13087-18-8

Usage

Preparation

Preparation by diazotization of 4,4′ -diamino- 2,2′ -di-hydroxybenzophenone, followed by treatment of the diazonium salt formed with 50% hypophosphorous acid (26%).

Upstream product

• 69-72-7 salicylic acid 
• 108-46-3 recorcinol 
• 89-86-1 4-hydroxysalicylic acid 
• 108-95-2 phenol 
• 131-53-3 (2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone 
• 151-10-0 1,3-Dimethoxybenzene 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 118-61-6 2-hydroxy-benzoic acid ethyl ester 
• 33077-87-1 2,2',4-trimethoxybenzophenone 

Downstream Products

• 131-53-3 (2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone 
• 1373220-66-6 C₂₆H₂₂ClNO₃ 
• 1373220-65-5 C₂₆H₂₂FNO₃ 
• 1373220-64-4 C₂₆H₂₃NO₃ 
• 1373220-61-1 4-(allyl(4-chlorobenzyl)amino)-3-(allyloxy)-9H-xanthen-9-one 
• 1373220-60-0 4-(allyl(4-fluorobenzyl)amino)-3-(allyloxy)-9H-xanthen-9-one 
• 1373220-59-7 4-(allyl(benzyl)amino)-3-(allyloxy)-9H-xanthen-9-one 
• 109556-89-0 2,4,2'-triacetoxy-benzophenone 
• 3722-51-8 3-hydroxyxanthen-9-one 

Relevant academic research and scientific papers

Dioxybenzone triggers enhanced estrogenic effect via metabolic activation: in silico, in vitro and in vivo investigation

Dioxybenzone is widely used in cosmetics and personal care products and frequently detected in multiple environmental media and human samples. However, the current understanding of the metabolic susceptibility of dioxybenzone and the potential endocrine disruption through its metabolites in mimicking human estrogens remains largely unclear. Here we investigated the in vitro metabolism of dioxybenzone, detected the residue of metabolites in rats, and determined the estrogenic disrupting effects of these metabolites toward estrogen receptor α (ERα). In vitro metabolism revealed two major metabolites from dioxybenzone, i.e., M1 through the demethylation of methoxy moiety and M2 through hydroxylation of aromatic carbon. M1 and M2 were both rapidly detected in rat plasma upon exposure to dioxybenzone, which were then distributed into organs of rats in the order of livers > kidneys > uteri > ovaries. The 100 ns molecular dynamics simulation revealed that M1 and M2 formed hydrogen bond to residue Leu387 and Glu353, respectively, on ERα ligand binding domain, leading to a reduced binding free energy. M1 and M2 also significantly induced estrogenic effect in comparison to dioxybenzone as validated by the recombinant ERα yeast two-hybrid assay and uterotrophic assay. Overall, our study revealed the potential of metabolic activation of dioxybenzone to induce estrogenic disrupting effects, suggesting the need for incorporating metabolic evaluation into the health risk assessment of benzophenones and their structurally similar analogs. Dioxybenzone was metabolized into two major metabolites via hydroxylation and demethylation, which exhibited higher binding affinity and agonistic activity toward ERα than dioxybenzone.

2. 2' - dihydroxy - 4 - methoxy benzophenone preparation method

A preparation method of 2,2'-dihydroxy-4-methoxybenzophenone comprises the following steps: synthesizing 2,2'4-trihydroxybenzophenone from salicylic acid and resorcinol, and carrying out a methylation reaction on 2,2'4-trihydroxybenzophenone and dimethyl sulfate to prepare 2,2'-dihydroxy-4-methoxybenzophenone. The method has the advantages of high purification efficiency, good separation effect of byproducts, high product purity reaching 99.5%, and realization of industrial production requirements of the above product.

ULTRAVIOLET LIGHT ABSORBERS

The present invention relates to compounds that have ultraviolet light absorbing properties, and which can also have mesogenic properties. The present invention also relates to compositions that include one or more such compounds, and to articles of manufacture that include one or more such compounds, such as optical elements that include an optical substrate and a layer that includes at least one compound of the present invention.

Synthesis and evaluation of novel aza-caged Garcinia xanthones

Inspired by the therapeutic potential of the simplified caged xanthones, we have developed a chemical strategy for synthesizing novel aza-caged Garcinia analogues through a regioselective Claisen/Diels-Alder cascade reaction. The origin of regioselectivity has been explained using the DFT method. We have further evaluated the cell proliferation and IKKβ inhibitory activities of these compounds and studied their binding mode with IKKβ by molecular docking. The results suggested that the aza-caged scaffold provides a suitable modification site and the introduction of a hydrophobic moiety leads to improvement in the cytotoxicity and IKKβ inhibitory activity. The aza-caged compound 6c exhibited an IC50 value of 2.68, 2.10, 8.02 μM against the HepG2, A549 cells and IKKβ, respectively. Mechanism studies with 6c showed that the aza-caged compounds induce apoptosis and cell cycle S phase arrest in A549 cells.

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

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.

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.

Bromoalkoxyxanthones as promising antitumor agents: Synthesis, crystal structure and effect on human tumor cell lines

In a study involving the synthesis of bis-intercalators, a bisxanthone and a minor product, 1-(6-bromohexyloxy)-xanthone were obtained. Although no capacity to inhibit the growth of human tumor cell lines was observed for the bisxanthone, the bromoalkoxyx

Method of purifying arylphenones

Hydroxy and alkyloxy benzophenones, also known as arylphenones, are efficiently and economically purified by contacting them with inorganic phosphorous compounds in the presence of a non-polar solvent. Best results are obtained when the arylphenone is then treated with an activated carbon and/or activated clay.

Studies in Synthesis of Xanthone Derivatives: Part III+ - A New One-step Synthesis of Xanthones

Ethyl salicylate condenses with different phenols in refluxing diphenyl ether to give various xanthones in good yields.In the case of resorcinol, hydroquinone, catechol and 3,4-xylenol corresponding phenyl salicylate derivatives are also obtained.Condensation with hydroxycoumarins affords pyranoxanthones, which can not be prepared by the Pechmann condensation of hydroxyxanthones.The structures of the intermediates and final products are established by spectral data (IR, PMR and 13C NMR).