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:

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
• Description: Daphnetin, mainly extracted from Yu Ruixiang Changbai Daphne (Daphne Korean Nakai), Daphne giraldii Nitsche bark, and root bark, is the main efficacy component of the plants D.tangutica Maxim and D.retttsa Hemsl. Changbai daphnes has the pharmacological effects of warming the spleen and stomach, relaxing the muscles and joints, and promoting circulation. In TCM, it’s commonly used as medicines for treatment of injuries. Because Changbai daphne is a pungent and warm natured herbal medicine, it was used to warm the spleen and stomach by dispelling cold.
• Physical properties: Appearance: white or off-white powder, odorless, and tasteless; Solubility: slightly soluble in methanol (equilibrium solubility of 485.4? μg/mL), slightly soluble in ethanol (equilibrium solubility of 230.06?μg/mL), and insoluble in water (equilibrium solubility of 176.7?μg/mL) ; Melting point: 262–264?°C.
• Uses: Daphnetin is a natural coumarin derivative providing anti-inflammatory and protective properties to those suffering from lung injury.
• Indications: This product is contained in national standards for chemical drugs, mainly used in Buerger’s disease, occlusive vascular disease, and coronary heart disease.
• Clinical Use: It has been verified by a large number of clinical cases that oral daphnetin capsule can significantly improve thromboangiitis obliterans; oral daphnetin has a better curative effect than intramuscular injection of Changbai daphne in patients with angina pectoris due to coronary heart disease. Daphnetin shows an obvious analgesic sedative effect on surgical and nonsurgical pain-relieved patients after intravenous drip or injection of daphnetin; oral daphnetin capsule shows significant therapeutic effects on rheumatoid arthritis.There are no reports about serious adverse reactions. Two cases of whole-body red itch were reported. It sometimes has mild gastrointestinal reaction when continuously used.

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:

hydrangetin

7,8-dimethoxy-chromen-2-one

2-oxo-2H-chromene-7,8-diyl diacetate

8-hydroxy-7-methoxy-2H-chromen-2-one

Refernces

• 1、 Ahmad,Shakeel-U-Rehman,Chisti,Shaw,Taneja. "Chemical constituents of rhododendron lepidotum". . p. 195 - 197. Retrieved 2010.
• 2、 Malik, Abdul,Riaz, Muhammad,Akbar, Erum,Rafique, Muhammad,Afza, Nighat. "C-alkylated coumarin and coumarin glycoside from Daphne oleoides". . p. 947 - 951. Retrieved 2003.
• 3、 álvarez, José María,Jorge, Zacarías D.,Massanet, Guillermo M.. "Study of the Oxidative Cleavage Proposed in the Biogenesis of Transtaganolides/Basiliolides: Pyran-2-one Aromaticity-Mediated Regioselective Control and Biogenetic Implications". supporting information. . Retrieved 2020/03/05.
• 4、 Bola?os, Gustavo,Contreras, Adolfo,Pardo-Casta?o, Camilo,Vásquez, Daniel. "Strong antimicrobial activity of collinin and isocollinin against periodontal and superinfectant pathogens in vitro". . . Retrieved 2020/02/03.