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

Description

GENTISEIN, also known as 1,3,7-trihydroxyxanthone, is a member of the xanthone class of compounds. It is characterized by the presence of hydroxy groups at positions 1, 3, and 7 on the 9H-xanthen-9-one structure. GENTISEIN exhibits various biological activities and has potential applications in different industries due to its unique chemical properties.

Uses

Used in Pharmaceutical Industry:
GENTISEIN is used as a pharmaceutical agent for its potential therapeutic effects. It has been found to possess antioxidant, anti-inflammatory, and antimicrobial properties, making it a promising candidate for the development of new drugs targeting various diseases.
Used in Cosmetic Industry:
In the cosmetic industry, GENTISEIN is used as an active ingredient for its skin-whitening and anti-aging properties. Its antioxidant and anti-inflammatory activities contribute to the protection and rejuvenation of the skin, making it a valuable component in skincare products.
Used in Food Industry:
GENTISEIN is used as a natural additive in the food industry, where it can enhance the flavor and color of certain products. Its antioxidant properties also help in preserving the freshness and quality of the food items.
Used in Agricultural Industry:
In agriculture, GENTISEIN can be employed as a natural pesticide or fungicide due to its antimicrobial properties. It can help protect crops from various diseases and pests, promoting sustainable and eco-friendly farming practices.
Used in Research and Development:
GENTISEIN is also used in research and development for its potential applications in various fields. Scientists are exploring its properties and interactions with other compounds to develop new drugs, materials, and technologies that can benefit society.

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

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

Downstream Products

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

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.