Khellin

Base Information

• Chemical Name: Khellin
• CAS No.: 82-02-0
• Molecular Formula: C14H12 O5
• Molecular Weight: 260.246
• Hs Code.: 2932999099
• European Community (EC) Number: 201-392-8
• NSC Number: 755826,37744,25509,8519
• UNII: 5G117T0TJZ
• DSSTox Substance ID: DTXSID9045267
• Nikkaji Number: J24.827D
• Wikipedia: Khellin
• Wikidata: Q2079998
• NCI Thesaurus Code: C75957
• Pharos Ligand ID: 22HUDC9BL3GY
• Metabolomics Workbench ID: 27986
• ChEMBL ID: CHEMBL44746
• Mol file: 82-02-0.mol

Synonyms:Khellin;Visammin

Chemical Property of Khellin

Chemical Property:

• Appearance/Colour: light yellow crystalline
• Vapor Pressure: 1.88E-09mmHg at 25°C
• Melting Point: 150-154°C
• Refractive Index: 1.595
• Boiling Point: 482.1 °C at 760 mmHg
• Flash Point: 218.8 °C
• PSA: 61.81000
• Density: 1.301 g/cm³
• LogP: 2.86480
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 247.2g/L(25 oC)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 260.06847348
• Heavy Atom Count: 19
• Complexity: 405

Purity/Quality:

97% ^*data from raw suppliers

Khellin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-38-36/37/38-23/24/25
• Safety Statements: 36/37/39-45-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)C2=C(C3=C(C(=C2O1)OC)OC=C3)OC
• General Description: KHELLIN, also known by numerous synonyms such as Visnagin, Khelline I, and Amicardine, is a naturally occurring furanochromone compound with historical medicinal uses, particularly as a vasodilator and spasmolytic agent. Recent research has explored its derivatives as potential blockers of the voltage-gated potassium channel Kv1.3, a target for autoimmune disease therapy, by modifying its 4- or 7-position to enhance selectivity and potency. Additionally, synthetic studies on khellin analogs aim to elucidate its chemical properties and expand its pharmacological applications. These efforts highlight khellin's versatility as a scaffold for drug development, though further research is needed to optimize its therapeutic potential.

Technology Process of Khellin

There total 38 articles about Khellin 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%

7-hydroxydihydrokhellin → Khellin (82-02-0)

Guidance literature:

With hydrogenchloride; In methanol; at 80 ℃; for 0.166667h;

DOI:10.3987/COM-88-4510

Reference yield:

3-acetyl-5,9-dimethoxy-2-methyl-4H-furo[3,2-g]chromen-4-one (85518-13-4) → 5-acetyl-6-hydroxy-4,7-dimethoxybenzofuran (484-51-5) + Khellin (82-02-0)

Guidance literature:

Reference yield:

3-acetyl-5,9-dimethoxy-2-methyl-4H-furo[3,2-g]chromen-4-one (85518-13-4) → 5-acetyl-6-hydroxy-4,7-dimethoxybenzofuran (484-51-5) + Khellin (82-02-0)

Guidance literature:

upstream raw materials:

4,9-Dihydroxy-7-methyl-5H-furo<3,2-g><1>benzopyran-5-one

khellinol

4,9-dimethoxy-7-methyl-2,3-dihydro-furo[3,2-g]chromen-5-one

6-hydroxy-4,7-dimethoxy-5-acetoacetylbenzofuran

Downstream raw materials:

4,9-dimethoxy-7-(4t-phenyl-buta-1,3-dien-t-yl)-furo[3,2-g]chromen-5-one

4,9-dimethoxy-7-(4-methyl-trans-styryl)-furo[3,2-g]chromen-5-one

4,9-dimethoxy-7-(4-nitro-trans-styryl)-furo[3,2-g]chromen-5-one

NSC₃₃₀₇₉₆

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.

Preparation of Some Simple Structural Analogs of Khellin

10.1021/jo01091a006

The research encompasses two distinct studies. The first study aims to synthesize simple structural analogs of khellin, a compound with known physiological activity, to further explore its chemistry and potential applications. Key chemicals used in this study include 2,3,4,6-tetramethoxy-3-ethylacetophenone (VI), 2-hydroxy-3,4,6-trimethoxy-5-ethylacetophenone (V), and various reagents such as copper-chromium oxide catalyst, dimethyl sulfate, acetyl chloride, aluminum chloride, and piperonal. The second study investigates the reaction of o-alkenylphenols with peracetic acid to understand the products and mechanisms involved. Key chemicals used in this study include o-allylphenol, o-propenylphenol, peracetic acid, acetic anhydride, and sulfuric acid. The study concludes that the product from o-allylphenol is 2-hydroxymethylcoumaran, not the previously reported epoxide, and that the product from o-propenylphenol is 1-(o-hydroxyphenyl)-2-propanone, formed through a different mechanism than previously thought. This research provides a clearer understanding of the reactions involving o-alkenylphenols and peracetic acid, correcting and expanding upon earlier findings.