632-85-9

Basic information

• Product Name: Wogonin
• Synonyms: 5,7-dihydroxy-8-methoxy-2-phenyl-4h-1-benzopyran-4-on;vogonin;5,7-dihydroxy-8-methoxy-2-phenyl-4h-1-benzopyran-4-one;5,7-DIHYDROXY-8-METHOXYFLAVON;5,7-DIHYDROXY-8-METHOXYFLAVONE;WOGONIN;WOGONIN 98.0% BY HPLC;WOOGONIN
• CAS NO: 632-85-9
• Molecular Formula: C₁₆H₁₂O₅
• Molecular Weight: 284.26
• EINECS: 1592732-453-0
• Product Categories: Tri-substituted Flavones;Caspases/Apoptosis;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors
• Mol File: 632-85-9.mol
• Article Data: 11

Chemical Properties

• Melting Point: 203-206°C
• Boiling Point: 518.8 °C at 760 mmHg
• Flash Point: 198.3 °C
• Appearance: /
• Density: 1.42 g/cm³
• Vapor Pressure: 2.21E-11mmHg at 25°C
• Refractive Index: 1.668
• Storage Temp.: 2-8°C
• Solubility: DMSO: ≥20mg/mL
• PKA: 6.83±0.40(Predicted)
• CAS DataBase Reference: Wogonin(CAS DataBase Reference)
• NIST Chemistry Reference: Wogonin(632-85-9)
• EPA Substance Registry System: Wogonin(632-85-9)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: LK8331000
• Hazardous Substances Data: 632-85-9(Hazardous Substances Data)

Usage

Uses

Wogonin acts as an anti-inflammatory agent, attenuating ovalbumin antigen-influenced neutrophillic airway inflammation. In addition, it reverses multi-drug resistance of human myelogenous leukemia.

Definition

ChEBI: A dihydroxy- and monomethoxy-flavone in which the hydroxy groups are positioned at C-5 and C-7 and the methoxy group is at C-8.

General Description

Wogonin is a flavonoid component of Scutellaria baicalensis Georgi roots.

Biochem/physiol Actions

Wogonin is an anti-inflammatory agent and COX-2 inhibitor, which inhibits the induction of both iNOS and COX-2. Wogonin inhibits COX-2 (IC50 = 46 μM) without affecting COX-1. Wogonin inhibits iNOS induction and thus inhibts activation-induced C6 glial cell death. Specifically, Wogonin inhibits NF-kappaB-mediated iNOS induction.

InChI:InChI=1/C16H12O5/c1-20-15-12(19)7-10(17)14-11(18)8-13(21-16(14)15)9-5-3-2-4-6-9/h2-8,17,19H,1H3

Upstream product

• 93-97-0 benzoic acid anhydride 
• 4431-41-8 5,7-dihydroxy-8-methoxyflavanone 
• 102-92-1 Cinnamoyl chloride 
• 70185-52-3 6′-hydroxy-2′,3′,4′-trimethoxychalcone 
• 4443-09-8 norwogonin 
• 54299-50-2 2',4'-dihydroxy-3',6'-dimethoxychalcone 
• 20032-42-2 2,5-dimethoxyresorcinol 
• 42528-81-4 2,6-bis-benzyloxy-benzene-1,4-diol 
• 55020-64-9 1,2,3-tris-benzyloxybenzene 
• 87-66-1 2-hydroxyresorcinol 
• 82475-01-2 wogonoside methyl ester 
• 146329-57-9 tetramethylammonium 5,7-dihydroxy-4-oxo-2-phenyl-4H-chromen-8-yl sulfate 
• 857564-84-2 1-(2,4-bis-benzoyloxy-3,6-dimethoxy-phenyl)-ethanone 
• 3542-63-0 7-benzyloxy-5,8-dihydroxy-2-phenyl-4H-chromen-4-one 

Downstream Products

• 84757-43-7 5,7-dihydroxy-6-formyl-8-methoxyflavone 
• 1356855-04-3 C₁₆H₁₂O₅*C₄₂H₇₀O₃₅ 
• 1178583-19-1 5‐hydroxy‐8‐methoxy‐2-phenyl-7‐(4‐(pyrrolidin‐1‐yl)butoxy)‐4H‐chromen‐4‐one 
• 1175077-25-4 5-hydroxy-8-methoxy-7-(4-(4-methylpiperazin-1-yl)butoxy)-2-phenyl-4H-chromen-4-one 

Relevant articles and documents

A Practical and Efficient Approach to the Preparation of Bioactive Natural Product Wogonin

A scalable and practical route to wogonin, a bioactive natural product with multiple pharmacological activities which is currently under phase I/II clinical studies, is described. Wogonin was obtained via a four-step process starting from commercially ava

Synthesis, evaluation and quantitative structure–activity relationship (QSAR) analysis of Wogonin derivatives as cytotoxic agents

A novel series of 49 wogonin derivatives were synthesized by introducing group at 7-, 8- or B ring of wogonin. The cytotoxic activities against HepG2, A549 and BCG-823 cancer cell lines were also investigated in vitro. Several of them showed obvious cytotoxic activities and compound 3h possessed the highest potency against HepG2, A549, and BCG-823 with IC50 values of 1.07 μM, 1.74 μM and 0.98 μM, respectively. A quantitative structure-activity relationship (QSAR) study of these synthetic derivatives as well as wogonin indicated that high solubility and low octanol/water partition coefficient are favorable, and excessive electrostatic properties and refractivity are unfavorable for the cytotoxic activities of these wogonin derivatives. These findings and results provide a base for further investigations.

Preparation method of flavonoids

The invention discloses a preparation method of flavonoids. The method comprises the following step: in a solvent, in the presence of iodine and a silver salt or in the presence of iodine and a copper salt, performing an iodination reaction on a compound 1 to obtain a compound 2. Raw materials used in the method are easy to acquire, and the method has high yields and simple post processes, and does not need column chromatography.