Azaleatin

Base Information

• Chemical Name: Azaleatin
• CAS No.: 529-51-1
• Molecular Formula: C16H12O7
• Molecular Weight: 316.267
• Hs Code.: 2914509090
• UNII: SO52512D8G
• ChEMBL ID: CHEMBL470848
• DSSTox Substance ID: DTXSID80200945
• Metabolomics Workbench ID: 25629
• Nikkaji Number: J833H
• Pharos Ligand ID: H9BSKM7AKLZC
• Wikidata: Q2875086
• Wikipedia: Azaleatin
• Mol file: 529-51-1.mol

Synonyms:Azaleatin;529-51-1;5-O-Methylquercetin;Quercetin 5-methyl ether;5-O-Methyl Quercetin;3,3',4',7-Tetrahydroxy-5-methoxyflavone;2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxychromen-4-one;2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-4H-chromen-4-one;CHEBI:2945;CHEMBL470848;SO52512D8G;2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-4H-1-benzopyran-4-one;5-METHOXY-3,3',4',7-TETRAHYDROXYFLAVONE;4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-;SCHEMBL890990;UNII-SO52512D8G;O-METHYLQUERCETIN, 5-;DTXSID80200945;HY-N7653;BDBM50326483;LMPK12112546;MFCD00017427;AKOS040760285;MS-24650;5-O-MethylquercetinQuercetin 5-methyl ether;CS-0134981;FT-0632310;Q-100928;Q2875086;FLAVONE, 3,3',4',7-TETRAHYDROXY-5-METHOXY-;2-(3,4-DIHYDROXYPHENYL)-3,7-DIHYDROXY-5-METHOXY-4H-1-BENZOPYRAN-4-ONE 5-O-METHYLQUERCETIN

Chemical Property of Azaleatin

Chemical Property:

• Vapor Pressure: 3.59E-18mmHg at 25°C
• Melting Point: 322℃
• Refractive Index: 1.74
• Boiling Point: 657.3 °C at 760 mmHg
• PKA: 6.46±0.40(Predicted)
• Flash Point: 250.2 °C
• PSA: 120.36000
• Density: 1.634 g/cm³
• LogP: 2.29100
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 316.05830272
• Heavy Atom Count: 23
• Complexity: 503

Purity/Quality:

99%, ^*data from raw suppliers

5-O-Methyl Quercetin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC2=C1C(=O)C(=C(O2)C3=CC(=C(C=C3)O)O)O)O
• Uses: As O-Methylated analogue of the flavanoid Quercertin (Q509500), 5-O-Methyl Quercetin;2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-5-Methoxy-4H-1-benzopyran-4-one is a small molecule inhibitor of NADPH Oxidase 4 enzyme. It is used in studies of flavonoid structure requirement for the increment of ocular blood flow in the rabbit and retinal function recovery in rat eyes. O-Methylated analogue of the flavanoid Quercertin (Q509500). It is a small molecule inhibitor of NADPH Oxidase 4 enzyme. It is used in studies of flavonoid structure requirement for the increment of ocular blood flow in the rabbit and retinal function recovery in rat eyes.

Technology Process of Azaleatin

There total 17 articles about Azaleatin 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: 97.0%

5-O-Methyl-3,3',4',7-Tetrapivaloyl-Quercetin (157650-21-0) → 5-O-methylquercetin (529-51-1)

Guidance literature:

With hydrogenchloride; In methanol; at 85 ℃; for 2h;

DOI:10.1002/ardp.19943270813

Reference yield: 95.0%

2-(3,4-bis(benzyloxy)phenyl)-3,7-(dibenzyloxy)-5-methoxy-4H-chromen-4-one (1592-68-3) → 5-O-methylquercetin (529-51-1)

Guidance literature:

With 10% palladium on activated carbon; hydrogen; In ethanol; at 20 ℃; for 6h;

DOI:10.1055/s-0030-1258310

Reference yield: 92.0%

3,7-bis(benzyloxy)-2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5-methoxy-4H-chromen-4-one (1393953-70-2) → 5-O-methylquercetin (529-51-1)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; ethanol; for 12h; under 760.051 Torr;

DOI:10.1016/j.ejmech.2012.04.044

upstream raw materials:

2-benzoyloxy-1-(2,4-dihydroxy-6-methoxy-phenyl)-ethanone

3,4-bis-benzoyloxy-benzoic acid-anhydride

quercetol

5-O-Methyl-3,3',4',7-Tetrapivaloyl-Quercetin

Downstream raw materials:

5-methoxyresorcinol

Refernces

• 1、 Villaume, Sydney A.,Fu, Jian,N'Go, Inès,Liang, Hui,Lou, Huayong,Kremer, Laurent,Pan, Weidong,Vincent, Stéphane P.. "Natural and Synthetic Flavonoids as Potent Mycobacterium tuberculosis UGM Inhibitors". supporting information. p. 10423 - 10429. Retrieved 2017/08/07.
• 2、 Shi, Zhi-Hao,Li, Nian-Guang,Tang, Yu-Ping,Shi, Qian-Ping,Tang, Hao,Li, Wei,Zhang, Xu,Fu, Hai-An,Duan, Jin-Ao. "Biological evaluation and SAR analysis of O-methylated analogs of quercetin as inhibitors of cancer cell proliferation". . p. 455 - 462. Retrieved 2015/04/14.