beta-Mangostin

Base Information

• Chemical Name: beta-Mangostin
• CAS No.: 20931-37-7
• Molecular Formula: C25H28O6
• Molecular Weight: 424.494
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID40420546
• Nikkaji Number: J15.918B
• Wikidata: Q72488190
• Metabolomics Workbench ID: 47408
• ChEMBL ID: CHEMBL261706
• Mol file: 20931-37-7.mol

Synonyms:beta-mangostin

Chemical Property of beta-Mangostin

Chemical Property:

• Appearance/Colour: faintly yellow powder
• Vapor Pressure: 8.64E-16mmHg at 25°C
• Melting Point: 175-176 °C
• Refractive Index: 1.597
• Boiling Point: 616.5 °C at 760 mmHg
• PKA: 7.05±0.20(Predicted)
• Flash Point: 208.3 °C
• PSA: 89.13000
• Density: 1.213 g/cm³
• LogP: 5.39200
• Storage Temp.: 2-8°C
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 424.18858861
• Heavy Atom Count: 31
• Complexity: 692

Purity/Quality:

98%Min ^*data from raw suppliers

β-Mangostin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1=C(C=C2C(=C1O)C(=O)C3=C(O2)C=C(C(=C3CC=C(C)C)OC)O)OC)C
• Description: β-Mangostin is a xanthone originally isolated from G. mangostana with diverse biological activites. It inhibits growth of methicillin-resistant S. aureus (MRSA) and methicillin-susceptible S. aureus (MSSA; MICs = 6.25-12.5 and 6.25-25 μg/ml, respectively), P. falciparum (IC50 = 3 μg/ml), and M. tuberculosis (MIC = 6.25 μg/ml). β-Mangostin inhibits fatty acid synthase (FASN) with an IC50 value of 24.83 μM. It induces cell cycle arrest at the G2/M phase and intrinsic and mitochondrial apoptosis in MCF-7 breast cancer cells. β-Mangostin also inhibits LPS-induced nitric oxide and prostaglandin E2 (PGE2; ) production in RAW264.7 cells and reduces neutrophil infiltration and TNF-α and IL-1β production in a mouse model of carrageenan-induced peritonitis.

Technology Process of beta-Mangostin

There total 14 articles about beta-Mangostin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

3-(allyloxy)-8-hydroxy-2,6-dimethoxy-1,7-bis(3-methylbut-2-en-1-yl)-9H-xanthene-9-one (1607022-18-3) → β-mangostin (20931-37-7)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In methanol; at 20 - 80 ℃; for 5h;

DOI:10.1016/j.bmcl.2014.03.047

Reference yield: 70.3%

dimethylmangostin (15404-76-9) → β-mangostin (20931-37-7)

Guidance literature:

With sodium methylate; In dimethyl sulfoxide; for 4h; Reflux; Inert atmosphere;

Reference yield:

3',3''-dichlorotetrahydrodimethylmangostin (15404-68-9) → β-mangostin (20931-37-7) + dimethylmangostin (15404-76-9)

Guidance literature:

With potassium tert-butylate; In dimethyl sulfoxide; at 100 - 105 ℃; for 6h;

DOI:10.1039/P19810003205

upstream raw materials:

3',3''-dichlorotetrahydrodimethylmangostin

dimethyl sulfate

3,4-dihydro-7-hydroxy-5-methoxy-2,2-dimethyl-2H-1-benzopyran-8-yl 3,4-dihydro-6,8-dimethoxy-2,2-dimethyl-2H-1-benzopyran-5-yl ketone

1,7-bis(3-chloro-3-methylbutyl)-2,8-dihydroxy-3,6-dimethoxyxanthen-9-one

Downstream raw materials:

dimethylmangostin

Refernces

• 1、 -. "A preparing method and uses of mangostin and mangostin analogues". Paragraph 0034; 0035. . Retrieved 2017/04/22.
• 2、 -. "Novel Xanthone Derivatives and Composition for Treating Cancer Comprising the Same as Active Ingredient". Paragraph 0093; 0094; 0128; 0129. . Retrieved 2016/10/08.