5084-31-1

Usage

Uses

Used in Pharmaceutical Industry:
1,3,5,6-Tetrahydroxyxanthone is used as a potential therapeutic agent for the development of new cancer treatments. It has been found to exhibit cytotoxicity against cancer cells, making it a promising candidate for further research and development in oncology.
Used in Antioxidant and Anti-inflammatory Applications:
1,3,5,6-Tetrahydroxyxanthone is used as a natural antioxidant and anti-inflammatory agent for the development of pharmaceuticals to treat conditions related to oxidative stress and inflammation. Its antioxidant properties can help protect cells from damage caused by reactive oxygen species, while its anti-inflammatory effects can help reduce inflammation and alleviate symptoms associated with various inflammatory conditions.

Upstream product

• 108-73-6 3,5-dihydroxyphenol 
• 610-02-6 2,3,4-trihydroxybenzoic acid 
• 3660-86-4 1,3,5,6-tetramethyoxyxanthone 
• 3811-29-8 jacareubin 
• 2144-08-3 2,3,4-trihydroxybenzylaldehyde 
• 7169-07-5 3,4,5-(trimethoxy)benzoyl chloride 
• 573-11-5 2,3,4-Trimethoxy-benzoic acid 
• 83-30-7 acide 2,4,6-trihydroxybenzoique 
• 87-66-1 2-hydroxyresorcinol 
• 4090-81-7 1,3,5,6-tetrahydroxyxanthone tetraacetate 

Downstream Products

• 4090-62-4 1-Hydroxy-3,5,6-trimethoxy-xanthon 
• 3660-86-4 1,3,5,6-tetramethyoxyxanthone 
• 951243-14-4 7,9-dihydroxy-2,2-diphenyl-6H-[1,3]dioxolo[4,5-c]xanthen-6-one 
• 1313722-38-1 9-(methoxymethoxy)-6-oxo-2,2-diphenyl-6H-[1,3]dioxolo[4,5-c]xanthen-7-yl acetate 
• 1313722-40-5 1-acetoxy-3,5,6-tribenzyloxy-9H-xanthen-9-one 
• 42833-97-6 C₃₄H₂₆O₆ 
• 1429303-78-5 C₃₇H₄₂N₂O₆ 
• 1429303-75-2 C₃₅H₃₆O₈ 
• 1429303-74-1 C₃₄H₃₄O₈ 
• 1429302-91-9 C₃₅H₃₈O₇ 
• 1429302-43-1 C₃₄H₃₆O₇ 
• 1383484-46-5 8,10-dihydroxy-1,11-bis(3-methylbut-2-en-yl)-4-phenylacetyloxymethyl-3,3a,4,5-tetrahydro-1,5-methano-1H,7H-furo[3,4-d]xanthene-7,13-dione 
• 1383484-42-1 4-benzoyloxymethyl-8,10-dihydroxy-1,11-bis(3-methylbut-2-en-yl)-3,3a,4,5-tetrahydro-1,5-methano-1H,7H-furo[3,4-d]xanthene-7,13-dione 

Relevant academic research and scientific papers

A novel and efficient route to the construction of the 4-oxa-tricyclo[4.3.1.0]decan-2-one scaffold

A short and efficient route to the synthesis of 4-oxa-tricyclo[4.3.1.0]decan-2-one scaffold 12 in good yield is reported. Essential to the synthesis was the implementation of selective protection of the catechol system in xanthone 2 with Ph2CCl

Biomimetic total synthesis of forbesione and desoxymorellin utilizing a tandem Claisen/Diels-Alder/Claisen rearrangement

A concise synthesis of forbesione (1) and desoxymorellin (3) is presented. Central to the strategy is a biomimetic Claisen/Diels-Alder/Claisen reaction cascade that proceeds in a regioselective manner and produces the desired scaffold exclusively. The observed regioselectivity and product distribution of the Claisen/Diels-Alder/Claisen reaction are attributed to the electronic effects of the xanthone oxygen (O10), the C9 carbonyl group and the nature of the C1 functionality.

Synthesis, structure-activity relationship and in vitro pharmacodynamics of A-ring modified caged xanthones in a preclinical model of inflammatory breast cancer

Inflammatory breast cancer (IBC) is a highly metastatic, lethal form of breast cancer that lacks targeted therapeutic strategies. Inspired by the promising cytotoxicity of gambogic acid and related caged xanthones in spheroidsMARY-X, an in vitr

Synthesis and antitumor, antityrosinase, and antioxidant activities of xanthone

Ten substituted 1,3-dihydroxyxanthones were synthesized in one step. The yields ranged from 40 to 76%. Compounds 8–10 were first reported. Next, the compounds’ in vitro anti-proliferative activities against nine human cancer cell lines, antityrosinase, and antioxidant activities were evaluated. Compounds 1, 4, 6–7, and 9–10 exhibited enhanced cytotoxicity against certain cancer cells. Compounds 2, 8, 9, and 10 inhibited tyrosinase activity to a certain extent. In addition, compound 4 exhibited the best antioxidant activity, which was consistent with theoretical calculations. These results demonstrated that compounds 1–2, 4, and 6–10 were promising leads for further investigation.

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.

Synthesis and anti-tumor evaluation of B-ring modified caged xanthone analogues of gambogic acid

Gambogic acid (GA, 1), the most prominent member of Garcinia natural products, has been reported to be a promising anti-tumor agent. Previous studies have suggested that the planar B ring and the unique 4-oxa-tricyclo[4.3.1. 03,7]dec-2-one cage

Identification of Xanthones as Selective Killers of Cancer Cells Overexpressing the ABC Transporter MRP1

Multidrug-resistance protein1 (MRP1) belongs to the ATP-binding cassette (ABC) transporter family. MRP1 mediates MDR (multidrug resistance) by causing drug efflux either by conjugation to glutathione (GSH) or by co-transport with free GSH (without covalen

Total synthesis of aldehyde-containing Garcinia natural products isomorellin and gaudichaudione A

The natural products, isomorellin and gaudichaudione A, with a 4-oxa-tricyclo[4.3.1.03,7] dec-8-en-2-one scaffold were synthesized for the first time using an efficient method. The key improvement of this method was the simultaneous bisalkylation of 5,6-dihydroxyxanthone with the bulky 2-methylbutyne group. This method obviously shortened the synthetic route and enhanced the total yield. Four analogues named forbesione, desoxymorellin, desoxygaudichaudione A, and gambogin containing the same caged structure were prepared using this method.

Relationship between protective effect of xanthone on endothelial cells and endogenous nitric oxide synthase inhibitors

1,3,5,6-tetrahydroxyxanthone was synthesized. The relationship between protective effect of xanthone on endothelial cells and endogenous nitric oxide synthase inhibitors was investigated. Endothelial cells were treated with ox-LDL (100 μg/mL) for 48 h. Ad

γ-Pyrone compounds. II: Synthesis and antiplatelet effects of tetraoxygenated xanthones

Norathyriol and its analogues, 1,3,5,6-, 3,4,5,6-, 3,4,6,7- and 2,3,6,7- tetrahydroxyxanthone, were synthesized from benzophenone precursors by Friedel-Crafts acylation and subsequent base-catalyzed cyclization to eliminate methanol. Both 3,4,6,7- and 2,3,6,7-tetrahydroxyxanthone tetraacetate showed potent anti-platelet aggregation effects on arachidonic acid-induced platelet aggregation. 3,4,6,7-Tetrahydroxyxanthone tetraacetate and 1,3,5,6-tetrahydroxyxanthone showed potent and significant anti-platelet aggregation effects on collagen-induced platelet aggregation.