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

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

Used in Pharmaceutical Industry:
3-Isomangostin is used as a new class of MTH1 inhibitor for its potential role in cancer treatment. It has been discovered through X-ray crystallography screening and can help in the development of novel anticancer drugs.
Used in Neurodegenerative Disease Management:
3-Isomangostin is used as an inhibitor of amyloidogenesis, which can reduce amyloid fibril formation by human V30M transthyretin variant. This property makes it a potential candidate for the treatment of neurodegenerative diseases associated with amyloid fibril formation.
Used in Drug Development:
3-Isomangostin is used in the preparation of novel xanthone derivatives for their potential use against cancer. These derivatives can be further optimized and developed into more effective anticancer agents.

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.

Activation of phenolic oxygen atom using polyphosphoric acid: Synthesis of carbonyl-containing dihydrobenzofurans/dihydrobenzopyrans

Carbonyl-containing dihydrobenzofurans/dihydrobenzopyrans were prepared from carbonyl-containing ortho-allyl/prenylphenols by activation of phenolic oxygen atom using polyphosphoric acid (PPA). Various substrates were investigated, and the corresponding d

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.

Novel Xanthone Derivatives and Composition for Treating Cancer Comprising the Same as Active Ingredient

The present invention relates to a novel xanthone derivative compound, and an anticancer composition comprising the compound as an active ingredient. The xanthone derivative compound of the present invention exhibits excellent anticancer activities against various human cancer cells and remarkably enhanced water solubility compared to an alpha-mangostin compound which is a parent compound. Therefore, the xanthone derivative compound of the present invention can be developed into anticancer drugs having excellent activities.COPYRIGHT KIPO 2016

Bicyclomangostin: A new acid-catalysed cyclization product from mangostin

Cyclization of mangostin with p-toluenesulfonic acid gave 1-isomangostin, 3-isomangostin, and a new cyclization product, bicyclomangostin (4). The structure of bicyclomangostin was determined by spectroscopic and X-ray crystallographic studies. The methyl ether derivatives (8) and (9) or (10) were produced on methylation of bicyclomangostin, depending on the method used.

Acid-catalysed Cyclisations of Xanthones: Structure of a New Xanthone from Garcinia mangostana Linn.

Acid-catalysed cyclisations of hydroxyprenylxanthone metabolites, mangostin (I) and normangostin (VI) from Garcinia mangostana Linn. have been studied.A new xanthone garcinone-E has also been isolated from G.mangostana and the structure (IX) is established on the basis of its cyclised dihydropyranoxanthone derivative (X).