Auriculasin

Base Information

• Chemical Name: Auriculasin
• CAS No.: 60297-37-2
• Molecular Formula: C25H24O6
• Molecular Weight: 420.462
• NSC Number: 285656
• DSSTox Substance ID: DTXSID50418510
• Nikkaji Number: J17.893D
• Wikidata: Q72444083
• Metabolomics Workbench ID: 22384
• ChEMBL ID: CHEMBL459129
• Mol file: 60297-37-2.mol

Synonyms:auriculasin

Chemical Property of Auriculasin

Chemical Property:

• Vapor Pressure: 1.87E-18mmHg at 25°C
• Boiling Point: 668°Cat760mmHg
• PKA: 6.24±0.40(Predicted)
• Flash Point: 231.2°C
• PSA: 100.13000
• Density: 1.314g/cm³
• LogP: 5.26970
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 420.15728848
• Heavy Atom Count: 31
• Complexity: 792

Purity/Quality:

99% ^*data from raw suppliers

Auriculasin 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1=C2C(=C(C3=C1OC=C(C3=O)C4=CC(=C(C=C4)O)O)O)C=CC(O2)(C)C)C

Technology Process of Auriculasin

There total 2 articles about Auriculasin 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: 90.0%

3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6,8-bis(3-methylbut-2-en-1-yl)-4H-chromen-4-one (66777-70-6) → 7-(3,4-dihydroxyphenyl)-5-hydroxy-2,2-dimethyl-10-(3-methylbut-2-enyl)pyrano[3,2-g]chromen-6-one (60297-37-2)

Guidance literature:

With trityl tetrafluoroborate; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1016/S0040-4039(00)94205-9

Reference yield:

→ 7-(3,4-dihydroxyphenyl)-5-hydroxy-2,2-dimethyl-10-(3-methylbut-2-enyl)pyrano[3,2-g]chromen-6-one (60297-37-2)

Guidance literature:

Isoflavon 20, DDQ/Bzl. <Δ>;

DOI:10.1021/jo00412a004

Reference yield: 69.0%

7-(3,4-dihydroxyphenyl)-5-hydroxy-2,2-dimethyl-10-(3-methylbut-2-enyl)pyrano[3,2-g]chromen-6-one (60297-37-2) + p-toluenesulfonyl chloride (98-59-9) → 4-(5-hydroxy-8,8-dimethyl-10-(3-methylbut-2-en-1-yl)-4-oxo-4,8-dihydropyrano[3,2-g]chromen-3-yl)-1,2-phenylene bis(4-methylbenzenesulfonate)

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1016/j.bioorg.2019.03.034

upstream raw materials:

3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6,8-bis(3-methylbut-2-en-1-yl)-4H-chromen-4-one

Downstream raw materials:

3-(3,4-dimethoxy-phenyl)-5-hydroxy-8,8-dimethyl-10-(3-methyl-but-2-enyl)-8H-pyrano[3,2-g]chromen-4-one

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