529-49-7

Basic information

• Product Name: GENTISEIN
• Synonyms: 1,3,7-Trihydroxy-9H-xanthen-9-one;Gentisein(NSC 329491)
• CAS NO: 529-49-7
• Molecular Formula: C₁₃H₈O₅
• Molecular Weight: 244.2
• Product Categories: Xanthones
• Mol File: 529-49-7.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 558.1°Cat760mmHg
• Flash Point: 224.7°C
• Appearance: /
• Density: 1.64g/cm³
• Vapor Pressure: 4.62E-13mmHg at 25°C
• Refractive Index: 1.758
• CAS DataBase Reference: GENTISEIN(CAS DataBase Reference)
• NIST Chemistry Reference: GENTISEIN(529-49-7)
• EPA Substance Registry System: GENTISEIN(529-49-7)

Safety Data

• Hazardous Substances Data: 529-49-7(Hazardous Substances Data)

Usage

Definition

ChEBI: A member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at positions 1, 3 and 7.

InChI:InChI=1/C13H8O5/c14-6-1-2-10-8(3-6)13(17)12-9(16)4-7(15)5-11(12)18-10/h1-5,14-16H

Upstream product

• 490-79-9 2,5-dihydroxybenzoic acid. 
• 108-46-3 recorcinol 
• 108-73-6 3,5-dihydroxyphenol 
• 106296-25-7 methyl 2,5-bis(phenylmethoxy)benzoate 
• 2150-46-1 Methyl 2,5-dihydroxybenzoate 
• 900501-59-9 (2,5-dibenzyloxyphenyl)(2,4,6-trimethoxyphenyl)methanone 
• 900501-63-5 (2,5-dihydroxyphenyl)(2,4,6-trimethoxyphenyl)methanone 
• 39838-86-3 7-hydroxy-1,3-dimethoxy-9H-xanthen-9-one 
• 81991-99-3 4-C-glucosyl-1,3,7-trihydroxyxanthone 
• 3722-54-1 1,3,7-Trimethoxyxanthon 
• 42833-59-0 2'-Hydroxy-2,4',5,6'-tetramethoxybenzophenon 
• 491-64-5 isogentisine 
• 500-99-2 3,5-dimethoxyphenol 
• 2612-02-4 5-methoxysalicylic acid 

Downstream Products

• 20245-39-0 1,3,7-trihydroxy-2-(3-methylbut-2-enyl)xanthone 
• 841276-85-5 3,7-dimethoxy-1-(toluene-4-sulfonyloxy)-xanthen-9-one 
• 529-61-3 euxanthone 
• 1043-08-9 osajaxanthone 
• 437-50-3 gentisin 
• 3722-54-1 1,3,7-Trimethoxyxanthon 
• 13379-35-6 1-hydroxy-3,7-dimethoxyxanthone 

Relevant articles and documents

TWO NEW XANTHONE GLYCOSIDES FROM TRIPTEROSPERMUM LANCEOLATUM

Oleanolic acid, mangiferin, and two new xanthone glucosides, named lanceoside (1,8-dihydroxy-3,7-dimethoxyxanthone-4-O-β-D-glucoside) and lancerin (C-4-β-D-glucosyl-1,3,7-trihydroxyxanthone), respectively, were isolated from the aerial parts of Tripterospermum lanceolatum.Key Word Index - Tripterospermum lanceolatum; Gentianaceae; xanthone glucoside; lanceoside; 1,8-dihydroxy-3,7-dimethoxyxanthone-4-O-β-D-glucoside; lancerin; C-4-β-D-glucosyl-1,3,7-trihydroxyxanthone.

Incorporation of nitric oxide donor into 1,3-dioxyxanthones leads to synergistic anticancer activity

Fifty 1,3-dioxyxanthone nitrates (4a ～ i-n, n = 1–6) were designed and synthesized based on molecular similarity strategy. Incorporation of nitrate into 1,3-dioxyxanthones with electron-donating groups at 6–8 position brought about synergistic anticancer effect. Among them, compound 4g-4 was confirmed the most active agent against HepG-2 cells growth with an IC50 of 0.33 ± 0.06 μM. It dose-dependently increased intramolecular NO levels. This activity was attenuated by either NO scavenger PTIO or mitochondrial aldehyde dehydrogenase (mtADH) inhibitor PCDA. Apoptosis analysis indicated different contributions of early/late apoptosis and necrosis to cell death for different dose of 4g-4. 4g-4 arrested more cells on S phase. Results from Western Blot implied that 4g-4 regulated p53/MDM2 to promote cancer cell apoptosis. All the evidences support that 4g-4 is a promising anti-cancer agent.

Synthesis of xanthone derivatives and studies on the inhibition against cancer cells growth and synergistic combinations of them

34 Xanthones were synthesized by microwave assisted technique. Their in?vitro inhibition activities against five cell lines growth were evaluated. The SAR has been thoroughly discussed. 7-Bromo-1,3-dihydroxy-9H-xanthen-9-one (3-1) was confirmed as the most active agent against MDA-MB-231?cell line growth with an IC50 of 0.46?±?0.03?μM. Combination of 3-1 and 5,6-dimethylxanthone-4-acetic acid (DMXAA) showed the best synergistic effect. Apoptosis analysis indicated different contributions of early/late apoptosis and necrosis to cell death for both monomers and the combination. Western Blot implied that the combination regulated p53/MDM2 to a better healthy state. Furthermore, 3-1 and DMXAA arrested more cells on G2/M phase; while the combination arrested more cells on S phase. All the evidences support that the 3-1/DMXAA combination is a better anti-cancer therapy.