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

• 146329-57-9 tetramethylammonium 5,7-dihydroxy-4-oxo-2-phenyl-4H-chromen-8-yl sulfate 
• 4431-41-8 5,7-dihydroxy-8-methoxyflavanone 
• 102-92-1 Cinnamoyl chloride 
• 70185-52-3 6′-hydroxy-2′,3′,4′-trimethoxychalcone 
• 55020-64-9 1,2,3-tris-benzyloxybenzene 
• 87-66-1 2-hydroxyresorcinol 
• 82475-01-2 wogonoside methyl ester 
• 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 
• 110506-85-9 7-(benzyloxy)-5-hydroxy-2-phenyl-4H-chromen-4-one 
• 480-40-0 5,7-dihydroxy-2-phenyl-chromen-4-one 
• 93-97-0 benzoic acid anhydride 
• 7499-99-2 1-(2,4-dihydroxy-3,6-dimethoxy)phenylethanone 
• 70185-52-3 (2E)-1-(6-hydroxy-2,3,4-trimethoxyphenyl)-3-phenylprop-2-en-1-one 

Downstream Products

• 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

Short-step syntheses of naturally occurring polyoxygenated aromatics based on site-selective transformation

Wogonin and astringin were synthesized from inexpensive chrysin and piceid in short steps. The key feature of these syntheses is site-selective transformation. The target molecules were obtained in 27 and 62% yields from the starting materials, respectively.

Preparation method and intermediates of flavonoids

The invention discloses a preparation method and intermediates of flavonoids. The preparation method comprises the following steps: in a solvent, in the presence of an acid, performing a ring-opening reaction and an elimination reaction on a compound 8 to obtain a compound 9. 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.

An efficient, scalable approach to hydrolyze flavonoid glucuronides via activation of glycoside bond

Hydrolyzing flavonoid glucuronides into corresponding aglycones posed some significant challenges. To improve acid-catalyzed hydrolysis process of flavonoid glucuronide, structures of glucuronide, hydrolysis parameters and post-processing were optimized. The optimized condition was performed by hydrolysis flavonoid glycoside methyl ester in a mixed solvent consisting of 2?mol/L H2SO4/EtOH/H2O (1/8/1, v/v/v) at 95?°C for 7?h and resulted in up to 90% aglycone yields, minimal byproduct formations and milder hydrolysis conditions. Furthermore, the optimized method avoids tedious purification steps and is easily conducted on a relatively large-scale using economical and commercially available reagents.