Irisolidone

Base Information

• Chemical Name: Irisolidone
• CAS No.: 2345-17-7
• Molecular Formula: C17H14 O6
• Molecular Weight: 314.295
• Hs Code.: 2914509090
• UNII: 081ORX70ZR
• ChEMBL ID: CHEMBL265945
• DSSTox Substance ID: DTXSID30946104
• Metabolomics Workbench ID: 22521
• Nikkaji Number: J13.258F
• Wikidata: Q27106953
• Mol file: 2345-17-7.mol

Synonyms:5,7-dihydroxy-6-methoxy-3-(4-methoxyphenyl)-4H-chromen-4-one;irisolidone

Chemical Property of Irisolidone

Chemical Property:

• Vapor Pressure: 2.15E-13mmHg at 25°C
• Melting Point: 190-191 °C
• Boiling Point: 565.5°Cat760mmHg
• PKA: 6.48±0.20(Predicted)
• Flash Point: 212.3°C
• PSA: 89.13000
• Density: 1.402g/cm³
• LogP: 2.88840
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 314.07903816
• Heavy Atom Count: 23
• Complexity: 468

Purity/Quality:

≥98% ^*data from raw suppliers

Irisolidone 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C2=COC3=C(C2=O)C(=C(C(=C3)O)OC)O

Technology Process of Irisolidone

There total 11 articles about Irisolidone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(Z)-1-(4,6-Bis-benzyloxy-2,3-dimethoxy-phenyl)-3-(4-methoxy-phenyl)-propenone → 4'-methoxytectorigenin (2345-17-7)

Guidance literature:

Multi-step reaction with 6 steps

1: thallium (III) nitrate * 3H₂O / methanol; CHCl₃ / 20 h / 30 °C

2: H₂ / 10percent Pd/C / methanol

3: 10percent aq. HCl / methanol / 2 h / Heating

4: 100 percent / pyridine

5: AlBr₃ / acetonitrile / 0.67 h / 20 °C

6: 16percent aq. HCl / methanol / 2 h / Heating

With pyridine; hydrogenchloride; aluminum tri-bromide; hydrogen; thallium(III) nitrate; palladium on activated charcoal; In methanol; chloroform; acetonitrile;

DOI:10.1248/cpb.46.222

Reference yield:

1-(4,6-Bis-benzyloxy-2,3-dimethoxy-phenyl)-3,3-dimethoxy-2-(4-methoxy-phenyl)-propan-1-one (204590-55-6) → 4'-methoxytectorigenin (2345-17-7)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / 10percent Pd/C / methanol

2: 10percent aq. HCl / methanol / 2 h / Heating

3: 100 percent / pyridine

4: AlBr₃ / acetonitrile / 0.67 h / 20 °C

5: 16percent aq. HCl / methanol / 2 h / Heating

With pyridine; hydrogenchloride; aluminum tri-bromide; hydrogen; palladium on activated charcoal; In methanol; acetonitrile;

DOI:10.1248/cpb.46.222

Reference yield:

5-hydroxy-6,4'-dimethoxyisoflavone-7-glucoside (6009-88-7) → 4'-methoxytectorigenin (2345-17-7)

Guidance literature:

With hydrogenchloride;

DOI:10.1002/ardp.19372750504

upstream raw materials:

5-hydroxy-6,4'-dimethoxyisoflavone-7-glucoside

7-hydroxy-4',5,6-trimethoxyisoflavone

Acetic acid 5,6-dimethoxy-3-(4-methoxy-phenyl)-4-oxo-4H-chromen-7-yl ester

1-(4,6-Bis-benzyloxy-2,3-dimethoxy-phenyl)-3,3-dimethoxy-2-(4-methoxy-phenyl)-propan-1-one

Downstream raw materials:

5,7-diacetoxy-6-methoxy-3-(4-methoxy-phenyl)-chromen-4-one

4H-benzopyran-4-one-5-hydroxy-6,7-dimethoxy-3-(4-methoxyphenyl)

4',5,6,7-tetramethoxyisoflavone

5-hydroxy-6,7-dimethoxy-3-(4'-methoxyphenyl)-8-methyl-4H-1-benzopyran-4-one

Refernces

• 1、 All, A. A.,El-Emary, N. A.,El-Moghazi, M. A.,Darwish, F. M.,Frahm, A. W.. "THREE ISOFLAVONOIDS FROM IRIS GERMANICA". . p. 2061 - 2064. Retrieved 1983.
• 2、 Mua, Yan-Ling,Xie, Yan-Ying,Zhou, Ling,Zhong, Ying,Liu, Lu,Bai, Hong,Wang, Yuan-Shu,Zhang, Xiu-Mei. "Cardioprotective effect of 'methylamine irisolidone', a new compound, in hypoxia/reoxygenation injury in cultured rat cardiac myocytes". experimental part. p. 1170 - 1177. Retrieved 2010/04/23.