86849-77-6

Basic information

• Product Name: IRISTECTORIGENINA
• Synonyms: IRISTECTORIGENINA;3-[3-Hydroxy-4-methoxyphenyl]-5,7-dihydroxy-6-methoxy-4H-1-benzopyran-4-one;4',6-Dimethoxy-3',5,7-trihydroxyisoflavone;6,4'-Dimethoxy-5,7,3'-trihydroxyisoflavone;Iristetrigenin B;Iristectrigenin B
• CAS NO: 86849-77-6
• Molecular Formula: C₁₇H₁₄O₇
• Molecular Weight: 330.2889
• Mol File: 86849-77-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 621.2°Cat760mmHg
• Flash Point: 232.8°C
• Appearance: /
• Density: 1.483g/cm³
• Vapor Pressure: 5.01E-16mmHg at 25°C
• Refractive Index: 1.67
• PKA: 6.43±0.20(Predicted)
• CAS DataBase Reference: IRISTECTORIGENINA(CAS DataBase Reference)
• NIST Chemistry Reference: IRISTECTORIGENINA(86849-77-6)
• EPA Substance Registry System: IRISTECTORIGENINA(86849-77-6)

Safety Data

• Hazardous Substances Data: 86849-77-6(Hazardous Substances Data)

Usage

General Description

IRISTECTORIGENINA is a chemical compound that is found naturally in the plant Iris tectorum, also known as the roof iris. It belongs to the class of compounds known as isoflavonoids and has been studied for its potential pharmaceutical and health benefits. IRISTECTORIGENINA has been found to have antioxidant, anti-inflammatory, and antiproliferative properties, and may have potential as a therapeutic agent for various illnesses. Additionally, it has been researched for its potential in cancer prevention and treatment. Further studies are needed to fully understand the biological activity and potential uses of IRISTECTORIGENINA.

InChI:InChI=1/C17H14O7/c1-22-12-4-3-8(5-10(12)18)9-7-24-13-6-11(19)17(23-2)16(21)14(13)15(9)20/h3-7,18-19,21H,1-2H3

Upstream product

• 38836-54-3 3-benzyloxy-4-methoxyphenylpyruvic acid oxime 
• 6274-74-4 2,6-dibenzyloxy-1,4-dimethoxybenzene 
• 204591-47-9 2-(3-Benzyloxy-4-methoxy-phenyl)-1-(4,6-bis-benzyloxy-2-isopropoxy-3-methoxy-phenyl)-3,3-dimethoxy-propan-1-one 
• 204591-45-7 (Z)-3-(3-Benzyloxy-4-methoxy-phenyl)-1-(4,6-bis-benzyloxy-2-isopropoxy-3-methoxy-phenyl)-propenone 
• 204590-57-8 1-(4,6-Bis-benzyloxy-2-isopropoxy-3-methoxy-phenyl)-ethanone 
• 188927-31-3 4-benzyloxy-6-hydroxy-3-methoxy-2-isopropoxyacetophenone 
• 204591-49-1 7-Hydroxy-3-(3-hydroxy-4-methoxy-phenyl)-5-isopropoxy-6-methoxy-chromen-4-one 
• 37744-61-9 iristectorin A 
• 1699-39-4 2-(3-(benzyloxy)-4-methoxyphenyl)acetonitrile 
• 64640-60-4 2,4-dihydroxy-3,6-dimethoxyphenyl-3-hydroxy-4-methoxybenzyl ketone 
• 64640-61-5 7-hydroxy-3-(3-hydroxy-4-methoxy-phenyl)-5,8-dimethoxy-chromen-4-one 

Downstream Products

• 50901-39-8 3',5,7-Triacetyl-4',6-dimethoxy-isoflavon 

Relevant articles and documents

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.

ISOFLAVONES OF IRIS SPURIA

A new isoflavone, 5,7-dihydroxy-6,2-dimethoxyisoflavone, together with iristectorigenin A and iristectorin A were isolated and characterized from the methanol extract of Iris spuria.Key Word Index - Iris spuria; Iridaceae; isoflavones; iristectorigenin A; iristectorin A.