3-Isomangostin

Base Information

• Chemical Name: 3-Isomangostin
• CAS No.: 19275-46-8
• Molecular Formula: C24H26O6
• Molecular Weight: 410.46
• European Community (EC) Number: 683-185-6
• UNII: 2RCN2CT95D
• ChEMBL ID: CHEMBL464119
• DSSTox Substance ID: DTXSID701317245
• Metabolomics Workbench ID: 49405
• Nikkaji Number: J866.785C
• Pharos Ligand ID: 1ZUD9MGJXSW7
• Wikidata: Q27463227
• Mol file: 19275-46-8.mol

Synonyms:3-isomangostin;mangostanol

Chemical Property of 3-Isomangostin

Chemical Property:

• Melting Point: 155-160oC
• Boiling Point: 615.9 °C at 760 mmHg
• PKA: 7.04±0.40(Predicted)
• Flash Point: 212.3 °C
• PSA: 89.13000
• Density: 1.257 g/cm³
• LogP: 4.97830
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 410.17293854
• Heavy Atom Count: 30
• Complexity: 683

Purity/Quality:

99% ^*data from raw suppliers

3-Isomangostin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1=C(C(=CC2=C1C(=O)C3=C(C4=C(C=C3O2)OC(CC4)(C)C)O)O)OC)C
• 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.

Technology Process of 3-Isomangostin

There total 7 articles about 3-Isomangostin 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%

α-mangostin (6147-11-1) → 3-isomangostin (19275-46-8)

Guidance literature:

With polyphosphoric acid; air; In N,N-dimethyl-formamide; at 130 ℃; for 2h;

DOI:10.1080/00397911.2021.1902537

Reference yield: 65.0%

α-mangostin (6147-11-1) → 3-isomangostin (19275-46-8) + 1-isomangostin (19275-44-6)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 0.5h; Reflux; Dean-Stark;

DOI:10.1016/j.bmcl.2020.127494

Reference yield: 63.0%

α-mangostin (6147-11-1) → 1-isomangostin hydrate (26063-95-6) + 3-isomangostin (19275-46-8)

Guidance literature:

With sulfuric acid; In toluene; at 40 ℃; for 4h; Inert atmosphere; Molecular sieve;

DOI:10.1080/14786419.2014.986729

upstream raw materials:

α-mangostin

Downstream raw materials:

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

Refernces

• 1、 Yang, Qian,Wang, Yu,Yang, Juan,Wu, Yi,Li, Liang-qun,Chen, Fa-ju,Wang, En-hua,Li, Li-lang,Yang, Yan,Yan, Yan-fang,Wang, Li,Ge, Li-juan,Yang, Li-shou,Yang, Xiao-sheng. "Activation of phenolic oxygen atom using polyphosphoric acid: Synthesis of carbonyl-containing dihydrobenzofurans/dihydrobenzopyrans". supporting information. p. 1723 - 1730. Retrieved 2021/04/09.
• 2、 -. "Novel Xanthone Derivatives and Composition for Treating Cancer Comprising the Same as Active Ingredient". Paragraph 0093; 0094. . Retrieved 2016/10/08.