Barbigerone

Base Information

• Chemical Name: Barbigerone
• CAS No.: 75425-27-3
• Molecular Formula: C23H22O6
• Molecular Weight: 394.424
• UNII: 9BE3F2B4GD
• DSSTox Substance ID: DTXSID30226352
• Nikkaji Number: J939.589J
• Wikipedia: Barbigerone
• Wikidata: Q4859690
• Metabolomics Workbench ID: 22214
• ChEMBL ID: CHEMBL3311038
• Mol file: 75425-27-3.mol

Synonyms:barbigerone

Chemical Property of Barbigerone

Chemical Property:

• Vapor Pressure: 3.36E-13mmHg at 25°C
• Boiling Point: 574.4°C at 760 mmHg
• Flash Point: 250.5°C
• Density: 1.229g/cm³
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 394.14163842
• Heavy Atom Count: 29
• Complexity: 683

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(C=CC2=C(O1)C=CC3=C2OC=C(C3=O)C4=CC(=C(C=C4OC)OC)OC)C

Technology Process of Barbigerone

There total 9 articles about Barbigerone 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:

C25H30O8 → 2',4',5'-trimethoxy-6'',6''-dimethylpyrano(2'',3'':7,8)isoflavone (75425-27-3)

Guidance literature:

With hydrogenchloride; In methanol; water; for 6h; Reflux;

DOI:10.1016/j.fitote.2014.06.002

Reference yield:

asaraldehyde (4460-86-0,14374-62-0) → 2',4',5'-trimethoxy-6'',6''-dimethylpyrano(2'',3'':7,8)isoflavone (75425-27-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 80percent aq. KOH / ethanol / 24 h

3: 30percent H₂O₂, 5percent aq. NaOH / methanol; acetone / Ambient temperature

4: BF₃ etherate / benzene / 3 h / Ambient temperature

5: conc. HCl / acetic acid / 2 h / boiling water bath

6: K₂CO₃, KI / dioxane / 20 h / Heating

With hydrogenchloride; potassium hydroxide; sodium hydroxide; boron trifluoride diethyl etherate; dihydrogen peroxide; potassium carbonate; potassium iodide; In 1,4-dioxane; methanol; ethanol; acetic acid; acetone; benzene;

Reference yield:

4'-Benzyloxy-2'-hydroxy-2,4,5-trimethoxychalcone (91735-51-2) → 2',4',5'-trimethoxy-6'',6''-dimethylpyrano(2'',3'':7,8)isoflavone (75425-27-3)

Guidance literature:

Multi-step reaction with 5 steps

2: 30percent H₂O₂, 5percent aq. NaOH / methanol; acetone / Ambient temperature

3: BF₃ etherate / benzene / 3 h / Ambient temperature

4: conc. HCl / acetic acid / 2 h / boiling water bath

5: K₂CO₃, KI / dioxane / 20 h / Heating

With hydrogenchloride; sodium hydroxide; boron trifluoride diethyl etherate; dihydrogen peroxide; potassium carbonate; potassium iodide; In 1,4-dioxane; methanol; acetic acid; acetone; benzene;

upstream raw materials:

3-chloro-3-methylbut-1-yne

7-hydroxy-3-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one

asaraldehyde

4'-Benzyloxy-2'-hydroxy-2,4,5-trimethoxychalcone

Refernces

• 1、 Pathak, V. P.,Saini, T. R.,Khanna, R. N.. "Synthesis of Barbigerone, a Naturally Occurring Pyranoisoflavone". . p. 89 - 90. Retrieved 2007/10/02.