Khellinone

Base Information

• Chemical Name: Khellinone
• CAS No.: 484-51-5
• Molecular Formula: C12H12 O5
• Molecular Weight: 236.224
• Hs Code.: 2932999099
• European Community (EC) Number: 207-607-1
• UNII: VJ1360YWR9
• DSSTox Substance ID: DTXSID70197512
• Nikkaji Number: J12.489C
• Wikidata: Q83070354
• ChEMBL ID: CHEMBL78293
• Mol file: 484-51-5.mol

Synonyms:5-acetyl-4,7-dimethoxy-6-hydroxybenzofuran;khellinone

Chemical Property of Khellinone

Chemical Property:

• Vapor Pressure: 7.02E-06mmHg at 25°C
• Melting Point: 90-101 °C
• Boiling Point: 366.3°Cat760mmHg
• PKA: 7.67±0.50(Predicted)
• Flash Point: 175.3°C
• PSA: 68.90000
• Density: 1.281g/cm³
• LogP: 2.35820
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 236.06847348
• Heavy Atom Count: 17
• Complexity: 293

Purity/Quality:

99% ^*data from raw suppliers

1-(6-Hydroxy-4,7-dimethoxybenzofuran-5-yl)ethanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: R36/37/38:Irritating to eyes, respiratory system and skin.
• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S36:Wear suitable prot

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=C(C2=C(C(=C1O)OC)OC=C2)OC

Technology Process of Khellinone

There total 34 articles about Khellinone 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: 97.0%

5-acetyl-4,7-dimethoxy-6-ethoxybenzofuran (98362-17-5) → 5-acetyl-6-hydroxy-4,7-dimethoxybenzofuran (484-51-5)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 25 ℃; for 15h;

DOI:10.1021/jo00276a024

Reference yield: 95.0%

Khellin (82-02-0) → 5-acetyl-6-hydroxy-4,7-dimethoxybenzofuran (484-51-5)

Guidance literature:

With potassium hydroxide; In water; at 25 - 105 ℃;

DOI:10.1002/ejoc.201700471

Reference yield: 61.0%

methanol (67-56-1) + 1-(6-hydroxy-7-methoxy-5-benzofuranyl)-ethanone (88897-95-4) → 5-acetyl-6-hydroxy-4,7-dimethoxybenzofuran (484-51-5)

Guidance literature:

With thallium(III) nitrate; 1.) - 25 deg C, 30 min. 2.)2-3 min reflux;

DOI:10.1016/S0040-4039(00)99051-8

upstream raw materials:

2,3-dihydrokhellinone

Khellin

Ammiol

1-(6-acetoxy-4,7-dimethoxy-benzofuran-5-yl)-ethanone

Downstream raw materials:

1-(6-hydroxy-4,7-dimethoxy-benzofuran-5-yl)-3-(4-hydroxy-phenyl)-propenone

1-{4-[1-(6-Hydroxy-4,7-dimethoxy-benzofuran-5-yl)-eth-(E)-ylideneamino]-phenyl}-ethanone

4,9-dimethoxy-7-(4-methoxy-phenyl)-furo[3,2-g]chromen-5-one

4,9-dimethoxy-7-(4-methoxy-phenyl)-6,7-dihydro-furo[3,2-g]chromen-5-one

Refernces

• 1、 Gammill, Ronald B.,Hyde, Bruce R.. "Total Synthesis of the Lipid-Altering and Antiatherosclerotic Furochromone Khellin. The Furoic Acid Route to Highly Functionalized Benzofurans". . p. 3863 - 3865. Retrieved 1983.
• 2、 Abu-Hashem, Ameen Ali,Hussein, Hoda A. R.,Aly, Ahmed S.. "Synthesis and antimicrobial activity of novel 1, 2, 4-triazolopyrimido-furo-quinazolinones from natural furochromones (Visnagenone and khellinone)". . p. 707 - 723. Retrieved 2021/04/02.
• 3、 Abd El-Rahman Selim, Ahmed Abbass Mohamed,Abdel Jaleel, Gehad A.,El-Fattah Ragab, Fatma Abd,Mohammed, Enas Ibrahim,Nissan, Yassin Mohammed. "Synthesis of Hydroxybenzofuranyl-Pyrazolyl and Hydroxyphenyl-pyrazolyl Chalcones and Their Corresponding Pyrazoline Derivatives as COX Inhibitors, Anti-inflammatory and Gastroprotective Agents". . p. 742 - 752. Retrieved 2020/09/18.