19275-46-8

Basic information

• Product Name: 3-isomangostin
• Synonyms: 3-isomangostin;3,4-Dihydro-5,9-dihydroxy-8-methoxy-2,2-dimethyl-7-(3-methyl-2-butenyl)-2H,6H-pyrano[3,2-b]xanthen-6-one;3,4-dihydro-5,9-dihydroxy-8-Methoxy-2,2-diMethyl-7-(3-Methylbut-2-enyl)pyrano[3,2-b]xanthen-6(2H)-one;3-Isomangostin, 98%, from Garcinia mangostana L.
• CAS NO: 19275-46-8
• Molecular Formula: C24H26O6
• Molecular Weight: 410.463
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 19275-46-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: 155～160℃
• Boiling Point: 615.9 °C at 760 mmHg
• Flash Point: 212.3 °C
• Appearance: /
• Density: 1.257
• PKA: 7.04±0.40(Predicted)
• CAS DataBase Reference: 3-isomangostin(CAS DataBase Reference)
• NIST Chemistry Reference: 3-isomangostin(19275-46-8)
• EPA Substance Registry System: 3-isomangostin(19275-46-8)

Safety Data

• Hazardous Substances Data: 19275-46-8(Hazardous Substances Data)

Usage

Uses

3-Isomangostin has been discovered as being a new class of MTH1 inhibitor using X-ray crystallography screening, as well as, an inhibitor of amyloidogenesis, which can reduce amyloid fibril formation by human V30M transthyretin variant. It has also been used to prepare novel xanthone derivative to use against cancer.

Upstream product

• 6147-11-1 α-mangostin 

Downstream Products

• 26063-96-7 3,4-dihydro-5,9-dihydroxy-7-(3-hydroxy-3-methylbutyl)-8-methoxy-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one 

Relevant articles and documents

Synthesis of xanthone derivatives based on α-mangostin and their biological evaluation for anti-cancer agents

A xanthone-derived natural product, α-mangostin is isolated from various parts of the mangosteen, Garcinia mangostana L. (Clusiaceae), a well-known tropical fruit. Novel xanthone derivatives based on α-mangostin were synthesized and evaluated as anti-cancer agents by cytotoxicity activity screening using 5 human cancer cell lines. Some of these analogs had potent to moderate inhibitory activities. The structure-activity relationship studies revealed that phenol groups on C3 and C6 are critical to anti-proliferative activity and C4 modification is capable to improve both anti-cancer activity and drug-like properties. Our findings provide new possibilities for further explorations to improve potency.

Modified tetra-oxygenated xanthones analogues as anti-MRSA and P. aeruginosa agent and their synergism with vancomycin

Five isolated xanthones from the C. cochinchinense and G. mangostana were evaluated and tested for antibacterial activities. Isolated 4 and 5 exhibited potent anti-MRSA and P. aeruginosa activity, but showed poor pharmacokinetic properties via ADMET prediction. It led us to improve pharmacokinetic properties of 4 and 5 by partially modifying them in acidic condition yielding fourteen analogues. It was found that analogues 4b, 4d and 5b possessed proper pharmacokinetic properties, while only 4b exhibited the best anti-MRSA and P. aeruginosa activity. The SEM results indicated that 4b may interact with or damage the cell wall of MRSA and P. aeruginosa. Moreover, a combination of 4b and vancomycin exhibits synergistic effect against both MRSA and P. aeruginosa at MIC value of 4.98 (MIC = 18.75 μg/mL for 4b) and 9.52 μg/mL (MIC = 75 μg/mL for 4b), respectively.

Chemistry of α-mangostin. Studies on the semisynthesis of minor xanthones from Garcinia mangostana

α-Mangostin is the major prenylated xanthone from Garcinia mangostana and it has been used also in recent times as starting material for the semisynthetic preparation of various biologically active derivatives. Its structure is characterised by the presence of few functional groups amenable to chemical manipulations, but present in the molecule in multiple instances (three phenolic hydroxyl groups, two prenyl chains and two unsubstituted aromatic carbons). This study represents a first approach to the systematic investigation of the reactivity of α-mangostin and describes the semisynthesis of some minor xanthones isolated from G. mangostana.