2345-17-7

Basic information

• Product Name: irisolidone
• Synonyms: irisolidone;5,7-Dihydroxy-6-methoxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one;irisoidone;4'-Methoxytectorigenin;4'-O-Methyltectorigenin;5,7-Dihydroxy-6,4'-dimethoxyisoflavon;4H-1-Benzopyran-4-one, 5,7-dihydroxy-6-methoxy-3-(4-methoxyphenyl)-
• CAS NO: 2345-17-7
• Molecular Formula: C₁₇H₁₄O₆
• Molecular Weight: 314.2895
• Mol File: 2345-17-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 190-191 °C
• Boiling Point: 565.5°Cat760mmHg
• Flash Point: 212.3°C
• Appearance: /
• Density: 1.402g/cm³
• Vapor Pressure: 2.15E-13mmHg at 25°C
• Refractive Index: 1.645
• PKA: 6.48±0.20(Predicted)
• CAS DataBase Reference: irisolidone(CAS DataBase Reference)
• NIST Chemistry Reference: irisolidone(2345-17-7)
• EPA Substance Registry System: irisolidone(2345-17-7)

Safety Data

• Hazardous Substances Data: 2345-17-7(Hazardous Substances Data)

Usage

General Description

Irisolidone is a chemical compound commonly found in the essential oils of iris flowers. It is a type of fragrance ingredient that provides a sweet, powdery, and floral aroma. The compound has been widely used in the perfume industry to impart a unique and characteristic scent to various products. Irisolidone is also known for its potential antioxidant and anti-inflammatory properties, making it a sought-after ingredient in skincare and cosmetic products. Overall, irisolidone is a versatile and valuable chemical that is valued for its aromatic and potential medicinal properties.

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

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 
• 13539-24-7 5-hydroxy-7,8-dimethoxy-3-(4'-methoxyphenyl)-4H-1-benzopyran-4-one 
• 857564-82-0 1-(2',6'-dihydroxy-3',4'-dimethoxyphenyl)-2-(4''-methoxyphenyl)ethanone 
• 14560-51-1 5-acetoxy-6,7-dimethoxy-3-(4-methoxy-phenyl)-chromen-4-one 
• 96300-23-1 5,7-diacetoxy-6-methoxy-3-(4'-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one 
• 1013935-12-0 6,4'-dimethoxy-7-ethoxy-5-hydroxyisoflavone 
• 927803-76-7 5,7-dihydroxy-6-methoxy-3-(4-methoxyphenyl)-8-[(methylaminomethyl)]-4H-[1]benzopyran-4-one 

Relevant articles and documents

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

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

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.