Daphnetin

Base Information

• Chemical Name: Daphnetin
• CAS No.: 486-35-1
• Molecular Formula: C9H6O4
• Molecular Weight: 178.144
• Hs Code.: 29322090
• European Community (EC) Number: 207-632-8
• UNII: XC84571RD2
• ChEMBL ID: CHEMBL244948
• DSSTox Substance ID: DTXSID00197560
• Metabolomics Workbench ID: 50858
• Nikkaji Number: J6.008I
• NSC Number: 633563
• Wikidata: Q27102315
• Mol file: 486-35-1.mol

Synonyms:7,8-dihydroxy-2H-1-benzopyran-2-one;7,8-dihydroxycoumarin;daphnetin

Chemical Property of Daphnetin

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 5.18E-08mmHg at 25°C
• Melting Point: 265-268 °C (dec.)
• Refractive Index: 1.689
• Boiling Point: 430.4 °C at 760 mmHg
• PKA: 7.61±0.20(Predicted)
• Flash Point: 184.5 °C
• PSA: 70.67000
• Density: 1.563 g/cm³
• LogP: 1.20420
• Storage Temp.: room temp
• Solubility.: soluble in Methanol
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 178.02660867
• Heavy Atom Count: 13
• Complexity: 248

Purity/Quality:

97% ^*data from raw suppliers

Daphnetin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 25-36/37/38-20/21
• Safety Statements: 22-24/25-36-26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C2=C1C=CC(=O)O2)O)O
• General Description: 7,8-Dihydroxycoumarin (daphnetin) is a natural coumarin derivative with a broad spectrum of biological activity, serving as a key scaffold for the synthesis of bioactive analogs. Its structure, featuring hydroxyl groups at positions 7 and 8, allows for chemical modifications such as 4-aminomethylation to enhance bioavailability and pharmacological potential. These derivatives, including those with tertiary N atoms or free N–H groups, are explored for their improved therapeutic properties, making 7,8-dihydroxycoumarin a valuable precursor in medicinal chemistry.

Technology Process of Daphnetin

There total 24 articles about Daphnetin 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: 98.0%

Propiolic acid (471-25-0) + 2-hydroxyresorcinol (87-66-1) → daphnetin (486-35-1)

Guidance literature:

With ytterbium(III) trifluoromethanesulfonate hydrate; at 80 ℃; for 0.0333333h; Reagent/catalyst; Microwave irradiation;

DOI:10.1016/j.tetlet.2016.05.087

Reference yield: 80.0%

7,8-dibenzyloxycoumarin (104819-86-5) → daphnetin (486-35-1)

Guidance literature:

With aluminum tri-bromide; In nitrobenzene; for 0.0833333h;

DOI:10.1248/cpb.34.628

Reference yield: 65.0%

malic acid (617-48-1,78644-42-5) + 2-hydroxyresorcinol (87-66-1) → daphnetin (486-35-1)

Guidance literature:

With sulfuric acid;

upstream raw materials:

8-formyl-7-hydroxycoumarin

7,8-Dihydroxy-2-oxo-2H-1-benzopyran-3-carboxylic acid

malic acid

2-hydroxyresorcinol

Downstream raw materials:

7-Benzyloxy-8-hydroxycoumarin

7,8-dibenzyloxycoumarin

7-methoxy-7',8-oxydicoumarin

8-methoxy-7,7'-oxydicoumarin

Refernces

Synthesis of 4-aminomethyl analogs of daphnetin

10.1007/s10600-007-0183-1

The study primarily focuses on the synthesis of 4-aminomethyl analogs of the natural coumarin daphnetin. The researchers investigated the reaction of 4-chloromethylcoumarins with aliphatic and aromatic amines to develop new bioactive coumarins with improved bioavailability, which are important in medical practice due to their broad spectrum of biological activity. The purpose of using these chemicals was to introduce a basic tertiary N atom and a free N–H group into the coumarin structure, which can enhance the bioavailability of the compounds. The study involved the preparation of starting 4-chloromethylcoumarins through Pechmann condensation and the subsequent alkylation of primary and secondary amines by these substituted 4-chloromethylcoumarins. The synthesized 4-aminomethyl coumarin derivatives were characterized by their physical properties and spectroscopic data, indicating their potential as new pharmacological agents.