Islandicin

Base Information

• Chemical Name: Islandicin
• CAS No.: 476-56-2
• Molecular Formula: C15H10 O5
• Molecular Weight: 270.241
• European Community (EC) Number: 207-506-2
• NSC Number: 264955
• UNII: VVJ2ULR2M5
• DSSTox Substance ID: DTXSID70197214
• Nikkaji Number: J12.545H
• Wikidata: Q27149783
• Metabolomics Workbench ID: 112954
• ChEMBL ID: CHEMBL477724
• Mol file: 476-56-2.mol

Synonyms:1,4,5-trihydroxy-2-methylanthraquinone;funiculosin (anthraquinone);islandicin

Chemical Property of Islandicin

Chemical Property:

• Vapor Pressure: 7.11E-12mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 530.6 °C at 760 mmHg
• Flash Point: 288.8 °C
• PSA: 94.83000
• Density: 1.583 g/cm³
• LogP: 1.88720
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 270.05282342
• Heavy Atom Count: 20
• Complexity: 434

Purity/Quality:

98%min ^*data from raw suppliers

Islandicin 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(=C2C(=C1O)C(=O)C3=C(C2=O)C(=CC=C3)O)O

Technology Process of Islandicin

There total 48 articles about Islandicin 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: 94.0%

1,4,5-trimethoxy-2-methylanthracene-9,10-dione (50457-06-2) → islandicin (476-56-2)

Guidance literature:

With hydrogen bromide; acetic acid; Heating;

Reference yield: 94.0%

3-Bromojuglone (52431-65-9) + (1E,3Z)-1-Methoxy-3-methyl-1,4-bis-trimethylsilanyloxy-buta-1,3-diene (99097-63-9) → islandicin (476-56-2)

Guidance literature:

3-Bromojuglone; (1E,3Z)-1-Methoxy-3-methyl-1,4-bis-trimethylsilanyloxy-buta-1,3-diene; In benzene; Reflux; Inert atmosphere; Schlenk technique;

With hydrogenchloride; triethylamine; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.joc.1c00920

Reference yield: 89.0%

3-chlorojuglone (18855-92-0) + (1E,3Z)-1-Methoxy-3-methyl-1,4-bis-trimethylsilanyloxy-buta-1,3-diene (99097-63-9) → islandicin (476-56-2)

Guidance literature:

In benzene; for 4h;

DOI:10.1002/ejoc.200700418

upstream raw materials:

1,4-dihydroxy-5-methoxy-2-methylanthracene-1,4-dione

3-hydroxy-2-pyrone

6-chloro-2-methylnaphthazarin

methanol

Downstream raw materials:

1,8-dihydroxy-3-methylanthracen-9(10H)-one

1,8-diacetoxy-3-methyl-anthraquinone

Chrysophanol

Refernces

• 1、 Rao, B. Kesava,Hanumaiah, T.,Rao, C. P.,Rao, G. S. R.,Rao, K. V. J.,Thomson, Ronald H.. "ANTHRAQUINONES IN VENTILAGO SPECIES". . p. 2583 - 2586. Retrieved 1983.
• 2、 Tietze, Lutz F.,Gericke, Kersten M.,Schuberth, Ingrid. "Synthesis of highly functionalized anthraquinones and evaluation of their antitumor activity". . p. 4563 - 4577. Retrieved 2008/02/12.
• 3、 Ahmed, Salman A.,Bardshiri, Esfandiar,McIntyre, C. Rupert,Simpson, Thomas J.. "Biosynthetic Studies on Tajixanthone and Shamixanthone, Polyketide Hemiterpenoid Metabolites of Aspergillus variecolor". . p. 249 - 274. Retrieved 2007/10/02.