83327-22-4

Basic information

• Product Name: DAPHNETICIN
• Synonyms: DAPHNETICIN;(2R)-2,3-Dihydro-3β-(4-hydroxy-3,5-dimethoxyphenyl)-2α-(hydroxymethyl)-9H-pyrano[2,3-f]-1,4-benzodioxin-9-one
• CAS NO: 83327-22-4
• Molecular Formula: C20H18O8
• Molecular Weight: 386.35212
• Mol File: 83327-22-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 619.5°Cat760mmHg
• Flash Point: 223.4°C
• Appearance: /
• Density: 1.403g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.618
• CAS DataBase Reference: DAPHNETICIN(CAS DataBase Reference)
• NIST Chemistry Reference: DAPHNETICIN(83327-22-4)
• EPA Substance Registry System: DAPHNETICIN(83327-22-4)

Safety Data

• Hazardous Substances Data: 83327-22-4(Hazardous Substances Data)

Usage

General Description

Daphneticin is a natural product isolated from the bark of Daphne genkwa, a plant native to East Asia. It is a type of naphthoquinone compound with potential pharmaceutical applications. Daphneticin has been studied for its anti-inflammatory, anticancer, and antiviral properties. It has also been shown to inhibit the growth of certain cancer cell lines and possess potential as a therapeutic agent for the treatment of cancer. Additionally, daphneticin has shown antiviral activity against the herpes simplex virus, making it a promising candidate for the development of antiviral drugs. Furthermore, daphneticin has been found to exhibit anti-inflammatory effects, making it an attractive compound for the development of anti-inflammatory medications. Its diverse range of potential pharmaceutical applications makes daphneticin an important compound for further research in the fields of medicine and drug development.

InChI:InChI=1/C20H18O8/c1-24-13-7-11(8-14(25-2)17(13)23)18-15(9-21)26-12-5-3-10-4-6-16(22)27-19(10)20(12)28-18/h3-8,15,18,21,23H,9H2,1-2H3/t15-,18-/m1/s1

Upstream product

• 20675-96-1 trans-sinapyl alcohol 
• 486-35-1 daphnetin 
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• 90985-68-5 (E)-4-acetoxy-3,5-dimethoxycinnamic acid 
• 477770-79-9 8-acetoxy-7-hydroxycoumarin 
• 477770-81-3 threo-(1R,2R)-1-(4'-benzyloxy-3',5'-dimethoxyphenyl)-3-O-tosyl-1,2-glycol 
• 93-35-6 7-hydroxy-2H-chromen-2-one 
• 10387-49-2 7-acetyloxycoumarin 
• 6748-68-1 8-acetyl-7-hydroxycoumarin 
• 65535-50-4 7-Benzyloxy-8-hydroxycoumarin 
• 65535-49-1 8-acetyl-7-benzyloxycoumarin 
• 65535-51-5 8-acetoxy-7-benzyloxycoumarin 

Relevant articles and documents

First enantioselective synthesis of daphneticin and its regioisomer

An enantioselective total synthesis of chiral daphneticin and its regioisomer is reported for the first time.

Synthesis and Structural Elucidation of Coumarinolignans

Coumarinolignans are a relatively new class of natural products combining a coumarin skeleton with a phenylpropene moiety.We describe here details of the first biomimetic syntheses of compounds in this series (1-16) utilizing both chemical and enzymatic approaches and the application of the selective INEPT nmr technique for unambiguous structure assignment.Chemical oxidation using silver oxide as an oxidizing agent typically produced two regioisomeric trans-substituted coumarinolignans.Enzymatic oxidation on the other hand normally gave rise to a single regioisomer.Almost all of the known natural coumarinolignans and several new compounds which may subsequently be obtained as natural products were synthesized.Three nmr strategies are described for the structure elucidation of the coumarinolignans, but only one of these techniques, the selective INEPT method, affords an unambiguous structure when only one regioisomer is present.Using this technique the structures and complete proton and carbon-13 chemical shift assignments of sixteen synthetic coumarinolignans were established.The described nmr strategy should prove useful for the unambiguous structure determination of all natural 2-aryl benzodioxanes, including the flavonolignans, the xanthonolignans and certain neolignans.