3-Hydroxyflavone

Base Information

• Chemical Name: 3-Hydroxyflavone
• CAS No.: 577-85-5
• Molecular Formula: C15H10 O3
• Molecular Weight: 238.243
• Hs Code.: 2932999099
• European Community (EC) Number: 209-416-9
• NSC Number: 57653
• UNII: ZTG9LSS5QH
• DSSTox Substance ID: DTXSID4060365
• Nikkaji Number: J1.628D,J630.345E
• Wikipedia: 3-Hydroxyflavone
• Wikidata: Q5919049
• NCI Thesaurus Code: C68456
• Pharos Ligand ID: 1QZLHPK5TMK5
• Metabolomics Workbench ID: 45126
• ChEMBL ID: CHEMBL294009
• Mol file: 577-85-5.mol

Synonyms:3-hydroxy-2-phenyl-4H-1-benzopyran-4-one;3-hydroxy-2-phenylchromone;3-hydroxyflavone;flavonol

Chemical Property of 3-Hydroxyflavone

Chemical Property:

• Appearance/Colour: yellow fluffy powder
• Vapor Pressure: 6.63E-07mmHg at 25°C
• Melting Point: 171-172 ºC(lit.)
• Refractive Index: 1.5740 (estimate)
• Boiling Point: 393.7 ºC at 760 mmHg
• PKA: 8.80±0.20(Predicted)
• Flash Point: 151.5 ºC
• PSA: 50.44000
• Density: 1.367 g/cm³
• LogP: 3.16560
• Storage Temp.: 0-6°C
• Water Solubility.: Insoluble in water. Soluble in N,N-DMF and ethanol.
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 238.062994177
• Heavy Atom Count: 18
• Complexity: 366

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Hydroxyflavone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Dyes -> Other Dyes
• Canonical SMILES: C1=CC=C(C=C1)C2=C(C(=O)C3=CC=CC=C3O2)O
• Uses: Reactant involved in:? ;Studies of photochemically-induced dioxygenase-type CO-release reactivity1? ;Phase-transfer protection and deprotection of hydroxychromones2? ;O-methylation with di-Me carbonate3Reactant involved in the synthesis of biologically active molecules including:? ;2-Chloropyridine derivatives for studies of antitumor agents and telomerase inhibitors4? ;Dihydrochromenopyrazines and chromenoquinoxalines5Involved in studies of its electrochemical properties using voltammetric methodologies6 3-Hydroxyflavone is a reactant involved in studies of photochemically-induced dioxygenase-type CO-release reactivity; phase-transfer protection and deprotection of hydroxychromones; and O-methylation with di-Me carbonate. As a reactant it is involved in the synthesis of biologically active molecules including 2-chloropyridine derivatives for studies of antitumor agents and telomerase inhibitors; dihydrochromenopyrazines and chromenoquinoxalines. It is also involved in studies of its electrochemical properties using voltammetric methodologies.

Technology Process of 3-Hydroxyflavone

There total 73 articles about 3-Hydroxyflavone 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: 100.0%

3-acetoxyflavonol (7578-68-9) → 3-hydroxyflavone (577-85-5,66585-05-5)

Guidance literature:

With sodium hydrogen telluride; acetic acid; In ethanol; for 0.5h; Heating;

Reference yield: 96.0%

2-[(3-phenyloxirane-2-yl)carbonyl]phenyl methanesulfonate → 3-hydroxyflavone (577-85-5,66585-05-5)

Guidance literature:

With montmorillonite KSF clay; at 120 ℃; for 0.0333333h; Microwave irradiation;

DOI:10.1002/hlca.201200336

Reference yield: 91.0%

FLAVONE (525-82-6,66585-04-4) → 3-hydroxyflavone (577-85-5,66585-05-5)

Guidance literature:

With HOF* CH₃CN; at 0 ℃; for 0.0166667h;

DOI:10.1016/j.tetlet.2004.03.030

upstream raw materials:

tetrachloromethane

N-Bromosuccinimide

rac-trans-3-hydroxy-2-phenyl-3,4-dihydro-2H-chromen-4-one

dibenzoyl peroxide

Downstream raw materials:

3-methoxyflavone

3-hydroxy-2,3-dimethoxyflavan-4-one

2,3-Diethoxy-3-hydroxy-2-phenyl-chroman-4-one

2-phenylchromon-3-yl (trimethylsilyl)acetate

Refernces

• 1、 Rao, T. Sudhakara,Mathur, H. H.,Trivedi, G. K.. "REACTION OF CHROMOUS CHLORIDE WITH 3-NITROFLAVENES. A NOVEL SYNTHESIS OF FLAVONOLS". . p. 5561 - 5562. Retrieved 1984.
• 2、 Golan, Elizabeth,Hagooly, Aviv,Rozen, Shlomo. "An easy way for constructing hard-to-make epoxides employing HOF·CH3CN". . p. 3397 - 3399. Retrieved 2004.
• 3、 Anoop, Anakuthil,Dey, Subhasis,Mandal, Sukanta,Podder, Nirmalya. "Oxygenolysis of a series of copper(ii)-flavonolate adducts varying the electronic factors on supporting ligands as a mimic of quercetin 2,4-dioxygenase-like activity". supporting information. p. 4338 - 4353. Retrieved 2022/04/07.
• 4、 Roy, Tithi,Boateng, Samuel T.,Banang-Mbeumi, Sergette,Singh, Pankaj K.,Basnet, Pratik,Chamcheu, Roxane-Cherille N.,Ladu, Federico,Chauvin, Isabel,Spiegelman, Vladimir S.,Hill, Ronald A.,Kousoulas, Konstantin G.,Nagalo, Bolni Marius,Walker, Anthony L.,Fotie, Jean,Murru, Siva,Sechi, Mario,Chamcheu, Jean Christopher. "Synthesis, inverse docking-assisted identification and in vitro biological characterization of Flavonol-based analogs of fisetin as c-Kit, CDK2 and mTOR inhibitors against melanoma and non-melanoma skin cancers". supporting information. . Retrieved 2021/01/14.