4',6-Dihydroxyflavone

Base Information

• Chemical Name: 4',6-Dihydroxyflavone
• CAS No.: 63046-09-3
• Molecular Formula: C15H10O4
• Molecular Weight: 254.242
• Hs Code.: 2914501900
• UNII: 05J1QNC3FW
• DSSTox Substance ID: DTXSID7022467
• Nikkaji Number: J354.019G
• Wikidata: Q27116015
• Metabolomics Workbench ID: 74504
• ChEMBL ID: CHEMBL484663
• Mol file: 63046-09-3.mol

Synonyms:6,4'-Dihydroxyflavone;4',6-dihydroxyflavone;63046-09-3;6-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one;6-hydroxy-2-(4-hydroxyphenyl)chromen-4-one;UNII-05J1QNC3FW;05J1QNC3FW;MLS001049030;CHEBI:34359;SMR000024483;4H-1-Benzopyran-4-one, 6-hydroxy-2-(4-hydroxyphenyl)-;SR-01000471690;EMD-20262;Oprea1_744925;BIDD:ER0182;SCHEMBL311405;SPECTRUM1500717;CHEMBL484663;cid_182362;DTXSID7022467;BDBM76563;HMS1612C09;HMS2769P06;FLAVONE, 4',6-DIHYDROXY-;CCG-18946;MFCD00017693;STL284535;AKOS001656516;6-hydroxy-2-(4-hydroxyphenyl)chromone;NCGC00096034-01;J354.019G;EU-0042537;FT-0640866;2-(4-hydroxyphenyl)-6-oxidanyl-chromen-4-one;AB00583691-06;6-hydroxy-2-(4-hydroxyphenyl)-1-benzopyran-4-one;SR-01000471690-1;SR-01000471690-3;BRD-K46836114-001-04-3;Q27116015

Chemical Property of 4',6-Dihydroxyflavone

Chemical Property:

• Vapor Pressure: 3.87E-11mmHg at 25°C
• Melting Point: 340oC (dec.)
• Boiling Point: 512.8°C at 760 mmHg
• PKA: 9.00±0.40(Predicted)
• Flash Point: 201.2°C
• PSA: 70.67000
• Density: 1.443g/cm³
• LogP: 2.87120
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 254.05790880
• Heavy Atom Count: 19
• Complexity: 382

Purity/Quality:

98% ^*data from raw suppliers

6-Hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C=CC(=C3)O)O
• Uses: 6-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one (cas# 63046-09-3) is a flavenoid which, as a class of compounds, have broad pharmacological activity, including binding to biomolecules such as enzymes, hormone carriers, and DNA, chelating transition metal ions, catalyzing electron transport, and scavenging free radicals. It is an inhibitor of HIV-1 integrase as well as a ligand to the estrogen receptor.

Technology Process of 4',6-Dihydroxyflavone

There total 8 articles about 4',6-Dihydroxyflavone 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: 92.0%

1-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-3-(2,5-dihydroxy-phenyl)-propane-1,3-dione → 6,4'-dihydroxyflavone (63046-09-3)

Guidance literature:

With sulfuric acid; In acetic acid; at 95 - 100 ℃; for 1h;

DOI:10.1021/jo00016a015

Reference yield: 22.8%

6,4'-di(methoxymethoxy)flavone → 6,4'-dihydroxyflavone (63046-09-3)

Guidance literature:

With hydrogenchloride; In methanol; for 3h;

DOI:10.1211/0022357011775983

Reference yield:

4-(tert-butyldimethylsilanyloxy)benzoic acid methyl ester (133642-20-3) → 6,4'-dihydroxyflavone (63046-09-3)

Guidance literature:

Multi-step reaction with 2 steps

1: LiHMDS / THF 1) 1 h, -78 deg C 2) 2 h, -10 deg C 3) 1 h, -78 deg C 4) 16 h, r.t.

2: 92 percent / 0.5percent H₂SO₄ / acetic acid / 1 h / 95 - 100 °C

With sulfuric acid; lithium hexamethyldisilazane; In acetic acid;

DOI:10.1021/jo00016a015

upstream raw materials:

4,2',5'-trihydroxychalcone

4-(tert-butyldimethylsilanyloxy)benzoic acid methyl ester

methyl 4-hydroxylbenzoate

Refernces

• 1、 Lim, Soon Sung,Jung, Sang Hoon,Ji, Jun,Shin, Kuk Hyun,Keum, Sam Rok. "Synthesis of flavonoids and their effects on aldose reductase and sorbitol accumulation in streptozotocin-induced diabetic rat tissues". . p. 653 - 668. Retrieved 2007/10/03.