Isolicoflavonol

Base Information

• Chemical Name: Isolicoflavonol
• CAS No.: 94805-83-1
• Molecular Formula: C20H18 O6
• Molecular Weight: 354.359
• UNII: 355E7H7EHH
• DSSTox Substance ID: DTXSID801317129
• Nikkaji Number: J490.195I
• Wikidata: Q72485402
• Pharos Ligand ID: 7LYT23GKFGWW
• Metabolomics Workbench ID: 25067
• ChEMBL ID: CHEMBL457679
• Mol file: 94805-83-1.mol

Synonyms:Isolicoflavonol;94805-83-1;3,5,7-trihydroxy-2-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]chromen-4-one;MLS000697735;CHEMBL457679;SMR000470986;4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-[4-hydroxy-3-(3-methyl-2-butenyl)phenyl]- (9CI);3,5,7-Trihydroxy-2-[4-hydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-4H-1-benzopyran-4-one;D0E5FV;SCHEMBL5614138;cid_5318585;CHEBI:175544;PGCKDCPTJAQQSQ-UHFFFAOYSA-N;DTXSID801317129;GLXC-18948;HMS2271L11;HY-N3474;BDBM50251003;LMPK12111984;5,7,4'-trihydroxy-3'-prenylflavonol;AKOS040760475;4',5,7-Trihydroxy-3'-prenylflavonol;MS-25516;CS-0024333;SR-01000765807;SR-01000765807-2;3,5,7-Trihydroxy-2-[4-hydroxy-3-(3-methyl-2-butenyl)phenyl]-4H-1-benzopyran-4-one;3,5,7-Trihydroxy-2-[4-hydroxy-3-(3-methyl-2-butenyl)phenyl]-4H-1-benzopyran-4-one, 9CI;4H-1-Benzopyran-4-one,3,5,7-trihydroxy-2-[4-hydroxy-3-(3-methyl-2-butenyl)phenyl]-

Chemical Property of Isolicoflavonol

Chemical Property:

• Boiling Point: 601.2±55.0 °C(Predicted)
• PKA: 6.32±0.40(Predicted)
• PSA: 111.13000
• Density: 1.444±0.06 g/cm3(Predicted)
• LogP: 3.79110
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 354.11033829
• Heavy Atom Count: 26
• Complexity: 605

Purity/Quality:

99%+, ^*data from raw suppliers

Isolicoflavonol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O)C

Technology Process of Isolicoflavonol

There total 11 articles about Isolicoflavonol 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: 37.3%

methanol (67-56-1) + 3,5,7-trimethoxy-3'-isopentenyl-4'-hydroxyflavonol → Isolicoflavonol (94805-83-1)

Guidance literature:

3,5,7-trimethoxy-3'-isopentenyl-4'-hydroxyflavonol; With boron tribromide; In pyridine; at -78 - 20 ℃; for 12h; Inert atmosphere;

methanol; In pyridine; for 1h;

Reference yield:

2’,4’-dimethoxy-6’-hydroxy-4-O-benzylchalcone (19158-99-7) → Isolicoflavonol (94805-83-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: iodine / dimethyl sulfoxide / 12.2 h / 110 °C

2.1: sodium carbonate; sodium hydrogencarbonate / acetone; dichloromethane; water / 0.25 h / Cooling with ice

2.2: 20 °C

3.1: potassium carbonate / acetone / 5 h / Inert atmosphere; Reflux

4.1: 5%-palladium/activated carbon / dichloromethane; methanol / 20 °C / Inert atmosphere

5.1: potassium iodide; potassium carbonate; copper(l) iodide / acetone / 48 h / Inert atmosphere; Reflux

6.1: 5%-palladium/activated carbon; quinoline / dichloromethane; methanol / 0.5 h / 20 °C / Inert atmosphere

7.1: 4 h / 170 °C / Inert atmosphere; Reflux

8.1: boron tribromide / pyridine / 12 h / -78 - 20 °C / Inert atmosphere

8.2: 1 h

With quinoline; copper(l) iodide; 5%-palladium/activated carbon; iodine; boron tribromide; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; potassium iodide; In pyridine; methanol; dichloromethane; water; dimethyl sulfoxide; acetone;

Reference yield:

3,5-dihydroxyphenol (108-73-6) → Isolicoflavonol (94805-83-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: zinc(II) chloride; hydrogenchloride / diethyl ether / 6 h / Cooling with ice

2.1: potassium carbonate / acetone / 1.5 h / Reflux

3.1: potassium hydroxide / methanol / 96 h / 20 °C

4.1: iodine / dimethyl sulfoxide / 12.2 h / 110 °C

5.1: sodium carbonate; sodium hydrogencarbonate / acetone; dichloromethane; water / 0.25 h / Cooling with ice

5.2: 20 °C

6.1: potassium carbonate / acetone / 5 h / Inert atmosphere; Reflux

7.1: 5%-palladium/activated carbon / dichloromethane; methanol / 20 °C / Inert atmosphere

8.1: potassium iodide; potassium carbonate; copper(l) iodide / acetone / 48 h / Inert atmosphere; Reflux

9.1: 5%-palladium/activated carbon; quinoline / dichloromethane; methanol / 0.5 h / 20 °C / Inert atmosphere

10.1: 4 h / 170 °C / Inert atmosphere; Reflux

11.1: boron tribromide / pyridine / 12 h / -78 - 20 °C / Inert atmosphere

11.2: 1 h

With quinoline; hydrogenchloride; copper(l) iodide; 5%-palladium/activated carbon; iodine; boron tribromide; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; potassium iodide; potassium hydroxide; zinc(II) chloride; In pyridine; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; acetone;

upstream raw materials:

2’,4’-dimethoxy-6’-hydroxy-4-O-benzylchalcone

3,5-dihydroxyphenol

2-[4-(benzyloxy)phenyl]-5,7-dimethoxy-4H-chromen-4-one

4'-(benzyloxy)-3,5,7-trimethoxyflavone

Refernces