491-64-5

Basic information

• Product Name: isogentisin
• Synonyms: 1,3-Dihydroxy-7-methoxy-9H-xanthen-9-one
• CAS NO: 491-64-5
• Molecular Formula: C14H10O5
• Molecular Weight: 258.23
• Product Categories: Xanthones
• Mol File: 491-64-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 241 °C
• Boiling Point: 519.4°Cat760mmHg
• Flash Point: 205°C
• Appearance: /
• Density: 1.48g/cm³
• Vapor Pressure: 2.09E-11mmHg at 25°C
• Refractive Index: 1.68
• PKA: 6.92±0.20(Predicted)
• CAS DataBase Reference: isogentisin(CAS DataBase Reference)
• NIST Chemistry Reference: isogentisin(491-64-5)
• EPA Substance Registry System: isogentisin(491-64-5)

Safety Data

• Hazardous Substances Data: 491-64-5(Hazardous Substances Data)

Usage

Description

Isogentisin, also known as 1,3-dihydroxy-7-methoxyxanthone, is a member of the xanthone class of compounds. It is characterized by the presence of hydroxy groups at positions 1 and 3, and a methoxy group at position 7 on the xanthen-9-one structure. Isogentisin has been recognized for its potential biological activities and applications in various fields.

Uses

Used in Pharmaceutical Industry:
Isogentisin is used as a pharmaceutical compound for its potential therapeutic effects. It has been studied for its antioxidant, anti-inflammatory, and anti-cancer properties, making it a promising candidate for the development of new drugs targeting various diseases.
Used in Cosmetic Industry:
In the cosmetic industry, isogentisin is used as an active ingredient for its potential skin-whitening and anti-aging effects. Its antioxidant and anti-inflammatory properties may contribute to the protection and rejuvenation of the skin.
Used in Traditional Medicine:
Isogentisin has been used in traditional medicine for its various health benefits. It is believed to possess anti-inflammatory, analgesic, and antipyretic properties, which can be useful in the treatment of pain, fever, and inflammation.
Used in Research:
Isogentisin is also used as a research tool in the study of xanthone chemistry and its biological activities. It serves as a valuable compound for understanding the structure-activity relationships and potential applications of xanthones in various fields.

InChI:InChI=1/C14H10O5/c1-18-8-2-3-11-9(6-8)14(17)13-10(16)4-7(15)5-12(13)19-11/h2-6,15-16H,1H3

Upstream product

• 108-73-6 3,5-dihydroxyphenol 
• 2612-02-4 5-methoxysalicylic acid 

Downstream Products

• 529-49-7 gentitein 
• 3722-54-1 1,3,7-Trimethoxyxanthon 
• 13379-35-6 1-hydroxy-3,7-dimethoxyxanthone 

Relevant articles and documents

Design and synthesis of novel xanthone-triazole derivatives as potential antidiabetic agents: α-Glucosidase inhibition and glucose uptake promotion

Inhibiting the decomposition of carbohydrates into glucose or promoting glucose conversion is considered to be an effective treatment for type 2 diabetes. Herein, a series of novel xanthone-triazole derivatives were designed, synthesized, and their α-glucosidase inhibitory activities and glucose uptake in HepG2 cells were investigated. Most of the compounds showed better inhibitory activities than the parental compound a (1,3-dihydroxyxanthone, IC50 = 160.8 μM)and 1-deoxynojirimycin (positive control, IC50 = 59.5 μM)towards α-glucosidase. Compound 5e was the most potent inhibitor, with IC50 value of 2.06 μM. The kinetics of enzyme inhibition showed that compounds 5e, 5g, 5h, 6c, 6d, 6g and 6h were noncompetitive inhibitors, and molecular docking results were consistent with the noncompetitive property that these compounds bind to allosteric sites away from the active site (Asp214, Glu276 and Asp349). On the other hand, the glucose uptake assays exhibited that compounds 5e, 6a, 6c and 7g displayed high activities in promoting the glucose uptake. The cytotoxicity assays showed that most compounds were low-toxic to human normal hepatocyte cell line (LO2). These novel xanthone triazole derivatives exhibited dual therapeutic effects of α-glucosidase inhibition and glucose uptake promotion, thus they could be use as antidiabetic agents for developing novel drugs against type 2 diabetes.

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.

Anti-AIDS agents 85. Design, synthesis, and evaluation of 1R,2R-dicamphanoyl-3,3-dimethyldihydropyrano-[2,3-c]xanthen-7(1H)-one (DCX) derivatives as novel anti-HIV agents

In this study, 1R,2R-dicamphanoyl-3,3-dimethydihydropyrano[2,3-c]xanthen- 7(1H)-one (DCX) derivatives were designed and synthesized as novel anti-HIV agents against both wild-type and non-nucleoside reverse transcriptase (RT) inhibitor-resistant HIV-1 (RTMDR-1) strains. Twenty-four DCX analogs (6-29) were synthesized and evaluated against the non-drug-resistant HIV-1 NL4-3 strain, and selected analogs were also screened for their ability to inhibit the RTMDR-1 strain. Compared with the control 2-ethyl-3′,4′-di-O-(-)- camphanoyl-2′,2′-dimethyldihydropyrano[2,3-f]chromone (2-EDCP, 2), one of the best anti-HIV coumarin derivatives in our prior study, three DCX compounds (7, 12, and 22) showed better activity against both HIV strains with an EC50 range of 0.062-0.081 μM, and five additional compounds (8, 11, 16, 18, and 21) exhibited comparable anti-HIV potency. Six DCX analogs (7, 11-12, 18, and 21-22) also showed enhanced selectivity index (SI) values in comparison to the control. Structure-activity relationship (SAR) information suggested that the extended conjugated system of the pyranoxanthone skeleton facilitates the interaction of the small DCX molecule within the viral binding pocket, consequently leading to enhanced anti-HIV activity and selectivity. Compared to DCP compounds, DCX analogs are a more promising new class of anti-HIV agents.