2345-17-7

Usage

Uses

Used in Perfumery Industry:
Irisolidone is used as a fragrance ingredient for its unique and characteristic scent, imparting a sweet, powdery, and floral aroma to various products.
Used in Skincare and Cosmetic Products:
Irisolidone is used as an active ingredient for its potential antioxidant and anti-inflammatory properties, making it a sought-after ingredient in skincare and cosmetic formulations.

InChI:InChI=1/C17H14O6/c1-21-10-5-3-9(4-6-10)11-8-23-13-7-12(18)17(22-2)16(20)14(13)15(11)19/h3-8,18,20H,1-2H3

Upstream product

• 6009-88-7 5-hydroxy-6,4'-dimethoxyisoflavone-7-glucoside 
• 1218934-52-1 irisolidone-7-O-β-D-glucuronide 
• 611-40-5 tectoridin 
• 204590-55-6 1-(4,6-Bis-benzyloxy-2,3-dimethoxy-phenyl)-3,3-dimethoxy-2-(4-methoxy-phenyl)-propan-1-one 
• 204591-53-7 Acetic acid 5,6-dimethoxy-3-(4-methoxy-phenyl)-4-oxo-4H-chromen-7-yl ester 
• 53505-61-6 7-hydroxy-4',5,6-trimethoxyisoflavone 

Downstream Products

• 4332-74-5 5,7-diacetoxy-6-methoxy-3-(4-methoxy-phenyl)-chromen-4-one 
• 13186-08-8 4H-benzopyran-4-one-5-hydroxy-6,7-dimethoxy-3-(4-methoxyphenyl) 
• 4332-73-4 4',5,6,7-tetramethoxyisoflavone 
• 96300-22-0 5-hydroxy-6,7-dimethoxy-3-(4'-methoxyphenyl)-8-methyl-4H-1-benzopyran-4-one 
• 13539-26-9 6-Hydroxygenistein 
• 548-77-6 tectorigenin 
• 927803-76-7 5,7-dihydroxy-6-methoxy-3-(4-methoxyphenyl)-8-[(methylaminomethyl)]-4H-[1]benzopyran-4-one 
• 1013935-12-0 6,4'-dimethoxy-7-ethoxy-5-hydroxyisoflavone 
• 96300-23-1 5,7-diacetoxy-6-methoxy-3-(4'-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one 
• 14560-51-1 5-acetoxy-6,7-dimethoxy-3-(4-methoxy-phenyl)-chromen-4-one 
• 857564-82-0 1-(2',6'-dihydroxy-3',4'-dimethoxyphenyl)-2-(4''-methoxyphenyl)ethanone 
• 13539-24-7 5-hydroxy-7,8-dimethoxy-3-(4'-methoxyphenyl)-4H-1-benzopyran-4-one 

Relevant academic research and scientific papers

Anti-inflammatory mechanisms of isoflavone metabolites in lipopolysaccharide-stimulated microglial cells

The microglial activation plays an important role in neurodegenerative diseases by producing several proinflammatory cytokines and nitric oxide (NO). We found that three types of isoflavones and their metabolites that are transformed by the human intestin

THREE ISOFLAVONOIDS FROM IRIS GERMANICA

From the rhizome of Iris germanica one new hexaoxygenated isoflavone, two new polyoxygenated isoflavone glucosides, the known isoflavonoids irisolidone, irigenin and iridin and acetovanillone, sitosterol, α-amyrin and β-amyrin were isolated.The structures

Isolation and identification of urinary metabolites of kakkalide in rats

Kakkalide is a major isoflavonoid from the flowers of Pueraria lobata (Willd.) Ohwi, possessing the protective effect against ethanol-induced intoxication and hepatic injury. The metabolism of kakkalide was investigated in rats. Thirteen metabolites were isolated by using solvent extraction and repeated chromatographic methods and identified by using spectroscopic methods including UV, IR, mass spectrometry, NMR, and circular dichroism experiments. Four new compounds were identified as irisolidone-7-Oglucuronide (M-1), tectorigenin-7-O-sulfate (M-2), tectorigenin-4′-O-sulfate (M-3), and biochanin A-6-O-sulfate (M-4) together with nine known compounds identified as irisolidone (M-5), tectorigenin (M-6), tectoridin (M-7), 5,7-dihydroxy-8, 4′-dimethoxyisoflavone (M-8), isotectorigenin (M-9), biochanin A (M-10), genistein (M-11), daidzein (M-12), and equol (M-13). The metabolic pathway of kakkalide was proposed, which is important to understand its metabolic fate and disposition in humans. Copyright

Cardioprotective effect of 'methylamine irisolidone', a new compound, in hypoxia/reoxygenation injury in cultured rat cardiac myocytes

'Methylamine irisolidone' (=5,7-dihydroxy-6-methoxy-3-(4-methoxyphenyl)-8- [(methylamino)-methyl]-4H-[1]benzopyran-4-one), a new compound, is a structurally modified kakkalide with good water solubility. In this study, we investigated its effect on hypoxia/reoxygenation (H/R) injury in cultured rat cardiac myocytes. The results showed that methylamine irisolidone could significantly inhibit lactate dehydrogenase (LDH) release, enhance the mitochondrial membrane potential, decrease intracellular calcium (Ca 2+ ) associated with the attenuation of reactive oxygen species (ROS) generation, reduce contents of malondialdehyde (MDA), and increase the activity of superoxide dismutase (SOD) after H/R in a dose-dependent manner. The present study demonstrated that methylamine irisolidone can directly protect cardiomyocytes against H/R injury, primarily as a result of reduction of the intracellular Ca2+ overload coincident with an attenuation of ROS generation and ROSmediated lipid peroxidation, which may contribute to the preservation of mitochondrion function and antioxidant against H/R injury.

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.