Alfalone

Base Information

• Chemical Name: Alfalone
• CAS No.: 970-48-9
• Molecular Formula: C17H14 O5
• Molecular Weight: 298.29
• Hs Code.: 2914509090
• UNII: 9NJ9MMB4ZA
• ChEMBL ID: CHEMBL3982563
• DSSTox Substance ID: DTXSID301297861
• Metabolomics Workbench ID: 22243
• Wikidata: Q104968267
• Mol file: 970-48-9.mol

Synonyms:Alfalone;970-48-9;6-Hydroxy-7,4'-dimethoxyisoflavone;6-hydroxy-7-methoxy-3-(4-methoxyphenyl)-4H-chromen-4-one;6-hydroxy-7-methoxy-3-(4-methoxyphenyl)chromen-4-one;4H-1-Benzopyran-4-one, 6-hydroxy-7-methoxy-3-(4-methoxyphenyl)-;Alfalone (isoflavone);4',7-DIMETHOXY-6-HYDROXYISOFLAVONE;Isoflavone, 6-hydroxy-4',7-dimethoxy-;9NJ9MMB4ZA;CHEMBL3982563;CHEBI:174838;DTXSID301297861;6-Hydroxy-4',7-dimethoxyisoflavone;LMPK12050105;AKOS027380838;7-Methoxy-3-(4-methoxyphenyl)-6-oxidanyl-chromen-4-one;6-Hydroxy-7-methoxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one

Chemical Property of Alfalone

Chemical Property:

• Melting Point: 246-247 °C
• Boiling Point: 516.0±50.0 °C (760 mmHg)
• PSA: 68.90000
• Density: 1.321±0.06 g/cm3(20 °C , 760mmHg)
• LogP: 3.18280
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 298.08412354
• Heavy Atom Count: 22
• Complexity: 438

Purity/Quality:

99% ^*data from raw suppliers

Alfalone ^*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=CC(=C(C=C3C2=O)O)OC

Technology Process of Alfalone

There total 4 articles about Alfalone 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: 93.0%

1-(2,5-dihydroxy-4-methoxyphenyl)-2-(4'-methoxyphenyl)ethanone (79744-55-1) + orthoformic acid triethyl ester (122-51-0) → 6-hydroxy-7-methoxy-3-(4-methoxyphenyl)-4H-chromen-4-one (970-48-9)

Guidance literature:

With dmap; at 100 ℃; for 4h;

DOI:10.3184/030823408X382135

Reference yield: 75.0%

1-(2,5-dihydroxy-4-methoxyphenyl)-2-(4'-methoxyphenyl)ethanone (79744-55-1) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 6-hydroxy-7-methoxy-3-(4-methoxyphenyl)-4H-chromen-4-one (970-48-9)

Guidance literature:

1-(2,5-dihydroxy-4-methoxyphenyl)-2-(4'-methoxyphenyl)ethanone; With boron trifluoride diethyl etherate; In N,N-dimethyl-formamide; at 50 - 60 ℃; Cooling with ice;

N,N-dimethyl-formamide; With methanesulfonyl chloride; at 50 - 70 ℃;

DOI:10.1002/cbdv.201400208

Reference yield:

6,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one (897-46-1) → afromosin (550-79-8) + 6-hydroxy-7-methoxy-3-(4-methoxyphenyl)-4H-chromen-4-one (970-48-9)

Guidance literature:

With O-methyl transferase from cell-free extract of Citrus mitis; <(14)CH3>-S-adenosyl-L-methionine; 2-hydroxyethanethiol; In water; dimethyl sulfoxide; at 35 ℃; for 0.5h; Product distribution; pH 7.5 buffer;

DOI:10.1016/0031-9422(80)85102-8

upstream raw materials:

6,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one

6,7,4'-trihydroxyisoflavone

1-(2,5-dihydroxy-4-methoxyphenyl)-2-(4'-methoxyphenyl)ethanone

orthoformic acid triethyl ester

Downstream raw materials:

6-hydroxy-4',7-dimethoxyisoflavane

Refernces

• 1、 Goto, Hideyuki,Terao, Yoshiyasu,Akai, Shuji. "Synthesis of various kinds of isoflavones, isoflavanes, and biphenyl- ketones and their 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activities". experimental part. p. 346 - 360. Retrieved 2009/12/27.
• 2、 Brunet, Gunter,Ibrahim, Ragai K.. "O-methylation of flavonoids by cell-free extracts of calamondin orange". . p. 741 - 746. Retrieved 2007/10/02.