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 95+% ^*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:

(4,8-dimethoxy-3-methyl-benzo[1,2-b;5,4-b']difuran-2-yl)-(5-isopropyl-4-methoxy-2-methyl-phenyl)-ketone

1-(4,7-Dimethoxy-6-hydroxy-5-benzofuryl)-3-phenyl-propan-1,3-dion

(4-bromo-phenyl)-(4,8-dimethoxy-3-methyl-benzo[1,2-b;5,4-b']difuran-2-yl)-ketone

1-[6-(2-dimethylamino-ethoxy)-4,7-dimethoxy-benzofuran-5-yl]-ethanone

Refernces

A new class of blockers of the voltage-gated potassium channel Kv1.3 via modification of the 4- or 7-position of khellinone

10.1021/jm050839v

The research focuses on the development of a new class of blockers for the voltage-gated potassium channel Kv1.3, a target for treating autoimmune diseases by selectively suppressing effector memory T cells. The study involves the synthesis and testing of khellinone derivatives, which are selectively alkylated at the 4- or 7-position via the phenolic OH group. The experiments include multiple parallel synthesis to create a library of khellinone derivatives with various substituents at the 4- and 7-positions. The synthesized compounds are then tested for their ability to inhibit Kv1.3 using whole-cell patch-clamp experiments on L929 cells stably expressing Kv1.3. The reactants used in the synthesis include khellinone, khellin, various alkyl or benzyl halides, and other reagents. The analyses involve determining the EC50 values, cytotoxicity, and the effect on human T cell proliferation. The study also explores the structure-activity relationships (SAR) of the synthesized compounds and compares their potency, selectivity, and mechanisms of blockade.

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