Xanthone

Base Information

• Chemical Name: Xanthone
• CAS No.: 90-47-1
• Molecular Formula: C13H8O2
• Molecular Weight: 196.205
• Hs Code.: 29329990
• European Community (EC) Number: 201-997-7
• NSC Number: 14978
• UNII: 9749WEV0CA
• DSSTox Substance ID: DTXSID6021795
• Nikkaji Number: J4.319B
• Wikipedia: Xanthone
• Wikidata: Q421789
• Pharos Ligand ID: 5DSQ8HDF23G4
• Metabolomics Workbench ID: 55650
• ChEMBL ID: CHEMBL186784
• Mol file: 90-47-1.mol

Synonyms:9-Oxoxanthene;xanthen-9-one;xanthone

Chemical Property of Xanthone

Chemical Property:

• Appearance/Colour: off-white powder
• Vapor Pressure: 4.53E-05mmHg at 25°C
• Melting Point: 174-176 °C
• Refractive Index: 1.642
• Boiling Point: 350 °C at 760 mmHg
• Flash Point: 169.8 °C
• PSA: 30.21000
• Density: 1.277 g/cm³
• LogP: 2.94620
• Storage Temp.: Store below +30°C.
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• Water Solubility.: It is Soluble in water (partly), chloroform, hot Toluene, ether (slightly), and hot alcohol.
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 196.052429494
• Heavy Atom Count: 15
• Complexity: 237

Purity/Quality:

99% ^*data from raw suppliers

Xanthone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xn,Xi
• Statements: 22
• Safety Statements: 24/25-62-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Aromatic Compounds
• Canonical SMILES: C1=CC=C2C(=C1)C(=O)C3=CC=CC=C3O2
• Description: Xanthone is a compound that has been shown to have a significant cytotoxicity against HL-60 cells and to inhibit the cyclase enzyme. It also inhibits the protein production of mcl-1, which is necessary for the development of cancer cells.
• Uses: Acts as an inhibitor of human cancer cell lines. Xanthone is used predominantly as oxygenated polycyclic aromatic compounds, and as a vasorelaxant. It can be used as a fluorescent agent, as well as an intermediate in organic synthesis and chemical research.

Technology Process of Xanthone

There total 384 articles about Xanthone 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: 100.0%

para-chlorotoluene (106-43-4) + 9-phenyl-9H-xanthen-9-ol (596-38-3) → xanth-9-one (90-47-1) + 4-Methylbiphenyl (644-08-6)

Guidance literature:

With palladium diacetate; caesium carbonate; tricyclohexylphosphine; In o-xylene; for 4h; Heating;

DOI:10.1021/jo0344034

Reference yield: 59.0%

malonodiamide (108-13-4) + 9-Benzylidene-9H-xanthene (27980-52-5) → xanth-9-one (90-47-1) + benzylidene 1,1-diacetate (581-55-5) + 2-Carbamoyl-3,4,4-tris(4-methoxyphenyl)-2-buten-4-olide (96784-43-9) + 9-(α-Acetoxybenzyl)-9-xanthenol (96784-24-6)

Guidance literature:

With manganese triacetate; acetic acid; for 0.0166667h; Heating;

DOI:10.1246/bcsj.58.217

Reference yield: 47.0%

phenyl Salicylate (118-55-8) + recorcinol (108-46-3) → xanth-9-one (90-47-1) + 3-hydroxyxanthen-9-one (3722-51-8) + 1-hydroxy-9H-xanthen-9-one (719-41-5)

Guidance literature:

at 325 ℃;

upstream raw materials:

acetic anhydride

salicylic acid

phenol

pyridine

Downstream raw materials:

2-phenoxybenzoic acid

9-(2-tolyl)xanthen-9-ol

xanthene

9-cyclohexylxanthen-9-ol

Refernces

• 1、 Turner, Penelope A.,Samiullah,Geden, Joanna V.,White, Alexander,Clarkson, Guy J.,Shipman, Michael. "New strategies for the synthesis and functionalization of tetrahydroxanthones". . p. 9433 - 9438. Retrieved 2015.
• 2、 Xu, Fan,Cao, Xueqin,Cao, Zhengbai,Zou, Lei. "A new method for the preparation of 2,3-cycloalkeno-5,6-cycloalkeno-4H-pyran-4-ones". . p. 10257 - 10261. Retrieved 2000.
• 3、 Fedorov, Alexey,Fu, Changchun,Linden, Anthony,Heimgartner, Heinz. "Reaction of thioketones with (R)-2-vinyloxirane: Regio- and stereoselective formation of (sS)-4-vinyl-1,3-oxathiolanes". . p. 1613 - 1619. Retrieved 2005.
• 4、 Goez, Martin,Hussein, Belal Hussein Mohammed. "Photoionization of xanthone via its triplet state or via its radical anion". . p. 5490 - 5497. Retrieved 2004.
• 5、 Hirota et al.. "-". . p. 2537. Retrieved 1964.
• 6、 Liu, Ling-Yan,Zhang, Yan,Huang, Kai-Meng,Chang, Wei-Xing,Li, Jing. "1,3-Dichloro-tetra-n-butyl-distannoxane: A new application for catalyzing the direct substitution of 9H-xanthen-9-ol at room temperature". . p. 9 - 15. Retrieved 2012.
• 7、 Chen, Dan,Chen, Long,Chen, Weiben,Chen, Weihua,Li, Shen,Xing, Guolong,Zhang, Guang. "N-Rich 2D Heptazine Covalent Organic Frameworks as Efficient Metal-Free Photocatalysts". . p. 616 - 623. Retrieved 2022/01/12.
• 8、 Ju, Zhao-Yang,Song, Li-Na,Chong, Ming-Ben,Cheng, Dang-Guo,Hou, Yang,Zhang, Xi-Ming,Zhang, Qing-Hua,Ren, Lan-Hui. "Selective Aerobic Oxidation of Csp3-H Bonds Catalyzed by Yeast-Derived Nitrogen, Phosphorus, and Oxygen Codoped Carbon Materials". supporting information. p. 3978 - 3988. Retrieved 2022/03/16.