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% ^*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
• General Description: 3-Hydroxyflavone is a flavonoid derivative that exhibits potential as a mushroom tyrosinase inhibitor, which could be relevant for treating pigmentation-related disorders, and also demonstrates antimicrobial properties. Its scaffold serves as a key structure for synthesizing bioactive derivatives, with studies highlighting its role in structure-activity relationships and molecular interactions with enzymes.

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

Exploring 3-hydroxyflavone scaffolds as mushroom tyrosinase inhibitors: synthesis, X-ray crystallography, antimicrobial, fluorescence behaviour, structure-activity relationship and molecular modelling studies

10.1080/07391102.2020.1805364

The study focuses on the synthesis and evaluation of 3-hydroxyflavone derivatives as inhibitors of mushroom tyrosinase, an enzyme involved in melanin production. A series of 3-hydroxyflavone scaffolds were synthesized using the Algar-Flynn-Oyamada reaction, and these compounds were screened for their in vitro inhibitory activity against tyrosinase. The chemicals used in the study included o-hydroxyacetophenone, various substituted benzaldehydes, sodium hydroxide, methanol, and hydrogen peroxide. These chemicals served the purpose of reacting together to form the desired 3-hydroxyflavone derivatives, which were then tested for their antimicrobial potential and their ability to inhibit tyrosinase, providing insights into their potential use as therapeutic agents for pigmentation-related disorders and as antimicrobial agents. The study also involved the use of spectroscopic techniques and mass spectrometry for compound characterization, as well as molecular modeling to explore binding interactions with the tyrosinase enzyme.