13111-57-4

Basic information

• Product Name: PSI-TECTORIGENIN
• Synonyms: 4’,5,7-trihydroxy-8-methoxy-isoflavon;5,7-dihydroxy-3-(4-hydroxyphenyl)-8-methoxy-4h-1-benzopyran-4-on;isotectorigenin;pseudotectorigenin;5,7-DIHYDROXY-3-[4-HYDROXYPHENYL]-8-METHOXY-4H-1-BENZOPYRAN-4-ONE;PSI-TECTORIGENIN;ψ:-Tectorigenin;5,7-Dihydroxy-3-(4-hydroxyphenyl)-8-methoxy-4H-chromen-4-one
• CAS NO: 13111-57-4
• Molecular Formula: C₁₆H₁₂O₆
• Molecular Weight: 300.26
• Mol File: 13111-57-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 578.1 °C at 760 mmHg
• Flash Point: 220.9 °C
• Appearance: /
• Density: 1.512 g/cm³
• Vapor Pressure: 5.78E-14mmHg at 25°C
• Refractive Index: 1.697
• Storage Temp.: 2-8°C
• CAS DataBase Reference: PSI-TECTORIGENIN(CAS DataBase Reference)
• NIST Chemistry Reference: PSI-TECTORIGENIN(13111-57-4)
• EPA Substance Registry System: PSI-TECTORIGENIN(13111-57-4)

Safety Data

• WGK Germany: 3
• RTECS: DJ3000000
• Hazardous Substances Data: 13111-57-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H12O6/c1-21-15-12(19)6-11(18)13-14(20)10(7-22-16(13)15)8-2-4-9(17)5-3-8/h2-7,17-19H,1H3

Upstream product

• 27181-83-5 2-(4-hydroxyphenyl)-1-(2,4,6-trihydroxy-3-methoxyphenyl)ethanone 
• 4755-77-5 Ethyl oxalyl chloride 
• 20032-42-2 2,5-dimethoxyresorcinol 
• 101169-69-1 2,4,4'-trihydroxy-3,6-dimethoxy-deoxybenzoin 
• 548-77-6 tectorigenin 
• 204591-02-6 2-(4-Benzyloxy-phenyl)-1-(2,4-bis-benzyloxy-3,6-dimethoxy-phenyl)-3,3-dimethoxy-propan-1-one 
• 54121-34-5 (Z)-3-(4-Benzyloxy-phenyl)-1-(2,4-bis-benzyloxy-3,6-dimethoxy-phenyl)-propenone 
• 204591-12-8 1-(2,4-Dihydroxy-3,6-dimethoxy-phenyl)-2-(4-hydroxy-phenyl)-3,3-dimethoxy-propan-1-one 
• 3162-51-4 1-(2,4-Bis-benzyloxy-3,6-dimethoxy-phenyl)-ethanone 
• 114003-37-1 7-acetoxy-3-(4-acetoxy-phenyl)-5,8-dimethoxy-chromen-4-one 
• 487-71-8 Iretol 
• 14191-95-8 4-cyanomethylphenol 
• 68-12-2 N,N-dimethyl-formamide 
• 204591-30-0 Acetic acid 3-(4-acetoxy-phenyl)-5-hydroxy-8-methoxy-4-oxo-4H-chromen-7-yl ester 

Downstream Products

• 27181-88-0 5,7-diacetoxy-3-(4-acetoxy-phenyl)-8-methoxy-chromen-4-one 

Relevant articles and documents

ISOFLAVONES FROM THE GALL AND WOOD OF WISTERIA BRACHYBOTRYS

Two new isoflavones, 6-methoxy-7,8,4'-trihydroxyisoflavone and isotectorigenin 7-O-β-D-glucopyranoside, were isolated from the gall and wood of Wisteria brachybotrys, together with 15 known isoflavonoids.Key Word Index - Wisteria brachybotrys; Leguminosae; isoflavonoid; isoflavone glucoside; 6-methoxy-7,8,4'-trihydroxyisoflavone; isotectorigenin 7-O-β-D-glucopyranoside.

Efficient method for the synthesis of tectorigenin

Tectorigenin, isolated from the rhizomes of Belamcanda chinensis, shows a wide variety of biological activities. The interest in its biological activities has been matched by a corresponding interest in its synthesis. We herein reported a convenient synth

Studies of the selective O-Alkylation and dealkylation of flavonoids. XXIV. A convenient method for synthesizing 6- and 8-methoxylated 5,7- dihydroxyisoflavones

2',4'-Bis(benzyloxy)-3',6'-dimethoxychalcones (5), which were obtained from the dibenzyl ether of 2,4-dihydroxy-3,6-dimethoxyacetophenone (3), were oxidatively rearranged with thallium (III) nitrate in methanol and the resultant products were converted into 7-hydroxy-5,8-dimethoxyisoflavones (8) by hydrogenolysis, followed by cyclization. The isoflavones were quantitatively demethylated to 5,7-dihydroxy-8-methoxyisoflavones (2) via their acetates. The isomeric 5,7-dihydroxy-6-methoxyisoflavones (1) were also synthesized from the chalcones, obtained from 2,3-dimethoxy- (16) or 2- isopropoxy-3-methoxy-4,6-bis(benzyloxy)acetophenones (21), by a similar method. On the other hand, the isoflavones with two hydroxy groups at the 2'- and 4'-positions were easily synthesized by the following method. Treatment of the rearranged product from 2,2',4,4'-tetrakis(benzyloxy)-3'6'- dimethoxychalcone (5f) with hydrochloric acid (HCl) in acetic acid afforded 2',4',7-tris(benzyloxy)-5,8-dimethoxyisoflavone (10f). The 5-methoxy group in the isoflavone was quantitatively cleaved to give the corresponding 5- hydroxyisoflavone (11f), which was isomerized to 2',4',7-tris(benzyloxy)-5- hydroxy-6-methoxyisoflavone (25f) in the presence of anhydrous potassium carbonate. Hydrogenolysis of the two 5-hydroxyisoflavones proceeded smoothly to give 2',4',5,7-tetrahydroxy-8-(2f) and 6-methoxyisoflavones (1f), respectively. The 13C-NMR spectra of these isoflavones supported the proposed structures of polyhydroxyisoflavones. The proposed structures of two natural isoflavones were revised.