Rapanone

Base Information

• Chemical Name: Rapanone
• CAS No.: 573-40-0
• Molecular Formula: C19H30 O4
• Molecular Weight: 322.445
• Hs Code.: 2914690090
• European Community (EC) Number: 675-435-8
• NSC Number: 340285
• UNII: SH52PPU72X
• DSSTox Substance ID: DTXSID80205915
• Nikkaji Number: J11.538J
• Wikidata: Q27108148
• Pharos Ligand ID: FLUAZ4UGGRS5
• Metabolomics Workbench ID: 68058
• ChEMBL ID: CHEMBL462801
• Mol file: 573-40-0.mol

Synonyms:rapanone

Chemical Property of Rapanone

Chemical Property:

• Vapor Pressure: 2.85E-10mmHg at 25°C
• Melting Point: 142-145°C
• Boiling Point: 457°Cat760mmHg
• Flash Point: 244.3°C
• PSA: 74.60000
• Density: 1.099g/cm³
• LogP: 5.09330
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 12
• Exact Mass: 322.21440943
• Heavy Atom Count: 23
• Complexity: 460

Purity/Quality:

98%min ^*data from raw suppliers

2,5-Dihydroxy-3-tridecylcyclohexa-2,5-diene-1,4-dione 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCC1=C(C(=O)C=C(C1=O)O)O

Technology Process of Rapanone

There total 13 articles about Rapanone 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: 89.0%

2-hydroxy-5-methoxy-3-tridecylcyclohexa-2,5-diene-1,4-dione (19833-82-0) → rapanone (573-40-0)

Guidance literature:

With sodium hydroxide; In ethanol; water; at 70 ℃; for 2h;

DOI:10.1021/jo702101w

Reference yield: 78.0%

2,5-dimethoxy-3-tridecylcyclohexa-2,5-diene-1,4-dione (3565-77-3) → rapanone (573-40-0)

Guidance literature:

With sodium hydroxide; In ethanol; water; at 70 ℃; for 2h;

DOI:10.1016/j.ejmech.2015.02.042

Reference yield:

tetradecanoic peroxyanhydride (3530-28-7) → rapanone (573-40-0)

Guidance literature:

With acetic acid;

upstream raw materials:

2,5-bis-methylamino-3-tridecyl-[1,4]benzoquinone

2-hydroxy-5-methoxy-3-tridecylcyclohexa-2,5-diene-1,4-dione

Di-O-acetyl-rapanon (11β-Hydroxy-coroglaucigenin)

tetradecanoic peroxyanhydride

Downstream raw materials:

Bis-<2.5-dihydroxy-3.6-dioxo-4-tridecyl-3.6-dihydro-phenyl>-methan

2,8-dihydroxy-10-(4-hydroxy-3-methyl-phenyl)-3,7-ditridecyl-10H-phenoxazine-1,4,6,9-tetraone

10-(4-diethylamino-phenyl)-2,8-dihydroxy-3,7-ditridecyl-10H-phenoxazine-1,4,6,9-tetraone

10-(4-dimethylamino-phenyl)-2,8-dihydroxy-3,7-ditridecyl-10H-phenoxazine-1,4,6,9-tetraone

Refernces

• 1、 McErlean, Christopher S. P.,Moody, Christopher J.. "First synthesis of N-(3-carboxylpropyl)-5-amino-2-hydroxy-3-tridecyl-1,4- benzoquinone, an unusual quinone isolated from Embelia ribes". . p. 10298 - 10301. Retrieved 2008/03/28.