1,3-dihydroxyxanthone

Base Information

• Chemical Name: 1,3-dihydroxyxanthone
• CAS No.: 3875-68-1
• Molecular Formula: C13H8 O4
• Molecular Weight: 228.204
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID00192030
• Nikkaji Number: J540.487H
• Wikidata: Q83064626
• Metabolomics Workbench ID: 133342
• ChEMBL ID: CHEMBL388525
• Mol file: 3875-68-1.mol

Synonyms:Xanthen-9-one,1,3-dihydroxy- (6CI,7CI,8CI); 1,3-Dihydroxyxanthen-9-one; 1,3-Dihydroxyxanthone

Chemical Property of 1,3-dihydroxyxanthone

Chemical Property:

• Vapor Pressure: 2.76E-10mmHg at 25°C
• Melting Point: 259°C(lit.)
• Refractive Index: 1.4977 (estimate)
• Boiling Point: 491.5°Cat760mmHg
• Flash Point: 199.1°C
• PSA: 70.67000
• Density: 1.516g/cm³
• LogP: 2.35740
• Solubility.: soluble in Dimethylformamide
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 228.04225873
• Heavy Atom Count: 17
• Complexity: 317

Purity/Quality:

98%min ^*data from raw suppliers

1,3-Dihydroxy-9H-xanthen-9-one >98.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)C3=C(C=C(C=C3O2)O)O

Technology Process of 1,3-dihydroxyxanthone

There total 18 articles about 1,3-dihydroxyxanthone 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: 95.0%

3,5-dihydroxyphenol (108-73-6) + salicylic acid (69-72-7,25496-36-0,8052-31-1) → 1,3-dihydroxyxanthone (3875-68-1)

Guidance literature:

With methanesulfonic acid; phosphorus pentoxide; at 80 ℃; for 0.333333h;

DOI:10.3184/174751915X14373971129805

Reference yield: 95.0%

1,3-dimethoxyl-9H-xanthen-9-one (3722-53-0) → 1,3-dihydroxyxanthone (3875-68-1)

Guidance literature:

With hydrogen iodide; phenol; at 160 ℃; for 8h;

DOI:10.1002/jps.2600820103

Reference yield: 76.3%

salicylic acid (69-72-7,25496-36-0,8052-31-1) + recorcinol (108-46-3) → 1,3-dihydroxyxanthone (3875-68-1)

Guidance literature:

With zinc(II) chloride; trichlorophosphate; at 75 ℃; for 0.5h; Microwave irradiation;

DOI:10.1016/j.ejmech.2017.03.068

upstream raw materials:

4,6-dimethoxy-2-hydroxy-2'-methoxybenzophenone

2'-ethoxy-2-hydroxy-4,6-dimethoxy-benzophenone

3,5-dihydroxyphenol

salicylic acid

Downstream raw materials:

1-hydroxy-3-methoxy-xanthen-9-one

Refernces

• 1、 Yang, Aihong,Yu, Qiao,Ju, Hui,Song, Lulu,Kou, Xiaodi,Shen, Rui. "Design, Synthesis and Biological Evaluation of Xanthone Derivatives for Possible Treatment of Alzheimer's Disease Based on Multi-Target Strategy". . . Retrieved 2020.
• 2、 Woo, Sangwook,Jung, Ji,Lee, Chongsoon,Kwon, Youngjoo,Na, Younghwa. "Synthesis of new xanthone analogues and their biological activity test-Cytotoxicity, topoisomerase II inhibition, and DNA cross-linking study". . p. 1163 - 1166. Retrieved 2007.
• 3、 Fedunov, Roman G.,Rogozina, Marina V.,Khokhlova, Svetlana S.,Ivanov, Anatoly I.,Tikhomirov, Sergei A.,Bondarev, Stanislav L.,Raichenok, Tamara F.,Buganov, Oleg V.,Olkhovik, Vyacheslav K.,Vasilevskii, Dmitrii A.. "Electronic structures and population dynamics of excited states of xanthione and its derivatives". . p. 1 - 10. Retrieved 2017.
• 4、 Dai, Jinwei,Ding, Hongmei,Huang, Lei,Li, Tiejun,Mao, Junqin,Wang, Jing,Wu, Junqi,Yu, Shichong,Zhang, Yuefan,Zhang, Yuyang. "Synthesis of novel xanthone analogues and their growth inhibitory activity against human lung cancer a549 cells". . p. 4239 - 4246. Retrieved 2019.
• 5、 Song, Gao-Peng,Li, Su-Mei,Si, Hong-Zong,Li, Yi-Bin,Li, Ya-Sheng,Fan, Ji-Hong,Liang, Qian-Qian,He, Hui-Bing,Ye, Han-Ming,Cui, Zi-Ning. "Synthesis and bioactivity of novel xanthone and thioxanthone l-rhamnopyranosides". . p. 36092 - 36103. Retrieved 2015.
• 6、 Anand,Jain. "-". . p. 1026. Retrieved 1972.
• 7、 Khammee, Thongchai,Jongsu, Warakorn,Kuno, Mayuso,Suksamrarn, Sunit. "Allylxanthone derivatives as xanthine oxidase inhibitors: Synthesis, biological evaluation and molecular docking study". . p. 38 - 44. Retrieved 2018.
• 8、 Chattopadhyay, Pronobesh,Das, Aparoop,Gogoi, Urvashee,Johari, Surabhi,Pathak, Manash Pratim. "Design, Synthesis, Computational and Biological Evaluation of Two New Series of 1, 3- and 1,6-dihydroxy Xanthone Derivatives as Selective COX-2 Inhibitors". . p. 884 - 914. Retrieved 2022/01/31.