491-78-1

Basic information

• Product Name: 5-HYDROXYFLAVONE
• Synonyms: PRIMULETIN;TIMTEC-BB SBB000768;5-HYDROXYFLAVONE;5-Hydroxy-2-phenylchromone;5-hydroxy-2-phenyl-4-benzopyrone;5-Hydroxyflavone,97%;5-Hydroxy-2-phenyl-4H-1-benzopyran-4-one;5-hydroxy-2-phenyl-chromen-4-one
• CAS NO: 491-78-1
• Molecular Formula: C₁₅H₁₀O₃
• Molecular Weight: 238.24
• EINECS: 207-743-1
• Product Categories: Mono-substituted Flavones;Biochemistry;Flavonoids;Benzopyrans;Bioactive Small Molecules;Building Blocks;Cell Biology;Chemical Synthesis;H;Heterocyclic Building Blocks
• Mol File: 491-78-1.mol

Chemical Properties

• Melting Point: 158-160°C
• Boiling Point: 425 °C at 760 mmHg
• Flash Point: 165.4 °C
• Appearance: /
• Density: 1.34 g/cm³
• Vapor Pressure: 7.97E-08mmHg at 25°C
• Refractive Index: 1.666
• PKA: 6.76±0.40(Predicted)
• BRN: 194429
• CAS DataBase Reference: 5-HYDROXYFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-HYDROXYFLAVONE(491-78-1)
• EPA Substance Registry System: 5-HYDROXYFLAVONE(491-78-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-36/37/39-27-37
• WGK Germany: 3
• Hazardous Substances Data: 491-78-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
5-HYDROXYFLAVONE is used as a reactant for the synthesis of copper(II) complexes, which serve as bioactive molecules to combat antioxidants. These complexes have potential applications in the development of novel drugs and therapies.
5-HYDROXYFLAVONE is also used in thermal behavior studies of vanadyl complexes with flavone derivatives, which are considered as insulin-mimetic agents. This application is significant for the development of treatments for diabetes and related metabolic disorders.
Used in Chemical Research:
In the field of chemical research, 5-HYDROXYFLAVONE is used as a reactant in O-methylation reactions with di-Me carbonate. This process allows for the modification of the molecule's properties, which can be useful in the synthesis of new compounds with specific applications.
Furthermore, 5-HYDROXYFLAVONE is utilized in Density Functional Theory (DFT) studies on excited-state intramolecular proton transfer. These studies contribute to the understanding of the molecule's behavior and can lead to the development of new materials with unique properties.

InChI:InChI=1/C15H10O3/c16-11-7-4-8-13-15(11)12(17)9-14(18-13)10-5-2-1-3-6-10/h1-9,16H

Upstream product

• 42079-78-7 5-methoxyflavone 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 103-73-1 Phenetole 
• 108-46-3 recorcinol 
• 101-84-8 diphenylether 
• 699-83-2 2,6-dihydroxylacetophenone 
• 98-88-4 benzoyl chloride 
• 2555-29-5 8-acetyl-7-hydroxy-4-methyl-2H-chromen-2-one 
• 93339-98-1 1-(2-fluoro-6-hydroxyphenyl)ethan-1-one 
• 17375-96-1 2-hydroxy-1-(2-hydroxyphenyl)ethanone 
• 536-74-3 phenylacetylene 
• 703-23-1 2'-hydroxy-6'-methoxyacetophenone 
• 100-52-7 benzaldehyde 
• 525-82-6 FLAVONE 

Downstream Products

• 71802-04-5 5-β-D-glucopyranosyloxy-2-phenyl-chromen-4-one 
• 162787-72-6 5-ethoxy-2-phenyl-4H-chromen-4-one 
• 920286-84-6 trifluoro-methanesulfonic acid 4-oxo-2-phenyl-4H-chromen-5-yl ester 
• 139653-00-2 5-[3-(4-hydroxypiperidinyl)propoxy]-2-phenyl-4H-1-benzopyran-4-one hydrochloride 
• 140439-10-7 5-[4-(4-Hydroxypiperidinyl)butoxy]-2-phenyl-4H-1-benzopyran-4-one hydrochloride 
• 6665-92-5 5-Deuteroxy-flavon 
• 1247006-92-3 5,6''-biflavone 
• 1247006-93-4 5,7''-biflavone 
• 1247006-94-5 5,8''-biflavone 
• 42079-78-7 5-methoxyflavone 
• 480-40-0 5,7-dihydroxy-2-phenyl-chromen-4-one 
• 491-67-8 5,6,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one 
• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 93327-97-0 5-acetoxyflavone 

Relevant articles and documents

Flavonoid compound as well as preparation method and application thereof

The invention discloses a flavonoid compound as well as a preparation method and application thereof, wherein the flavonoid compound comprises flavonoid compound FLM_M_1-24. Flavone derivatives FLM_M_25-40 and isoflavone derivatives FLM_M_M_41-48. The flavonoid compound can be used for preparing a modulator with an adjusting effect on Huh7-Nogo expression of B cells of human liver cancer cell lines, and specifically, the flavonoids compound has good inhibitory activity on Huh7-Nogo expression of human liver cancer cell line B cells.

An Efficient One-Pot Synthesis and Anticancer Activity of 4'-Substituted Flavonoids

A number of 4'-substituted (R = H, Me, Cl, F) flavone derivatives is synthesized from 2-hydroxyacetophenones using the modified Baker–Venkataraman reaction. Compound [3-(4-fluorobenzoyl)-5- hydroxy-4'-fluoroflavone] was synthesized for the first time with the yield of 12%. Antiproliferative assays indicate that the synthesized flavones with F substituent at the 4' position demonstrate higher activity than the other flavone derivatives, particularly against HeLa and MCF-7 with the IC50 9.5 and 2.7 μM, respectively.

Unified Approach to (Thio)chromenones via One-Pot Friedel-Crafts Acylation/Cyclization: Distinctive Mechanistic Pathways of β-Chlorovinyl Ketones

A facile synthetic method to chromenones and thiochromenones has been developed using a one-pot Friedel-Crafts acylation of alkynes with suitably substituted benzoyl chlorides. This unified approach to (thio)chromenones is readily applicable to aryl- and alkylalkynes where the stereochemically well-defined β-chlorovinyl ketone intermediates undergo distinctively different cyclization pathways. The ready availability of both starting materials, alkynes and benzoyl chlorides, coupled with the experimental simplicity makes the current synthetic method to (thio)chromenones fast, efficient, and practical.

2-substituted benzopyran-4-one compounds and application thereof

The invention relates to the technical field of medicine and discloses 2-substituted benzopyran-4-one compounds with a structure shown in general formula I and an application of the compounds in preparation of antifungal drugs and synergistic antifungal drugs. The compounds can be jointly used with azole antifungal drugs, can improve sensibility of drug-resistance bacteria to the azole drugs, reverses drug resistance and produces a synergistic antifungal function.

Ru(II)-Catalyzed Site-Selective Hydroxylation of Flavone and Chromone Derivatives: The Importance of the 5-Hydroxyl Motif for the Inhibition of Aurora Kinases

An efficient protocol for Ru(II)-catalyzed direct C-H oxygenation of a broad range of flavone and chromone substrates was developed. This convenient and powerful synthetic tool allows for the rapid installation of the hydroxyl group into the flavone, chromone, and other related scaffolds and opens the way for analog synthesis of highly potent Aurora kinase inhibitors. The molecular docking simulations indicate that the formation of bidentate H-bonding patterns in the hinge regions between the 5-hydroxyflavonoids and Ala213 was the significant binding force, which is consistent with experimental and computational findings.

COMPOUNDS THAT EXPAND HEMATOPOIETIC STEM CELLS

The present invention relates to compounds and compositions for expanding the number of CD34+ cells for transplantation. The invention further relates to a cell population comprising expanded hematopoietic stem cells (HSCs) and its use in autologous or allogeneic transplantation for the treatment of patients with inherited immunodeficient and autoimmune diseases and diverse hematopoietic disorders to reconstitute the hematopoietic cell lineages and immune system defense.

Synthesis of γ-benzopyranone by TfOH-promoted regioselective cyclization of o-alkynoylphenols

Regioselective cyclization of o-alkynoylphenols forming γ-benzopyranones has been demonstrated. Trifluoromethanesulfonic acid (TfOH) induced 6-endo cyclization of o-alkynoylphenols without forming 5-exo cyclized benzofuranone derivatives to provide the corresponding γ-benzopyranones in high yields.

An efficient one-pot synthesis of flavones

Flavones were prepared using a one-pot procedure starting from the corresponding 2′-hydroxyacetophenones. The latter were treated with 3 equiv of aroyl chloride in wet K2CO3/acetone (1% w/w water) to afford a good yield of flavone and a smaller amount of 3-aroylflavone. Evidence was obtained that the reaction proceeds via a triketone intermediate. When the reactants were heated in 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and pyridine, the 3-aroylflavone was obtained exclusively. Use of a stoichiometric amount of aroyl chloride afforded only the corresponding flavone.

An effective synthesis of 5,4′-disubstituted flavones via a cesium enolate assisted intramolecular ipso-substitution reaction

A variety of 5,4′-disubstituted flavones, which are anticipated to be androgen receptor antagonists to treat diseases mediated by the androgen receptor, were synthesized. It was found that an intramolecular ipso-substitution reaction via cesium enolate using 2-fluoro-6- hydroxyacetophenone and various benzoyl chlorides was effective in the preparation of 5-hydroxy-4′-alkylflavones.

Microwave enhanced palladium catalysed coupling reactions: A diversity-oriented synthesis approach to functionalised flavones

Microwave enhanced diversity-oriented synthesis (MEDOS) using palladium catalysed protocols is introduced as a powerful new strategy for the synthesis of systematically modified small molecules and is highlighted by application to functionalised flavones. The Royal Society of Chemistry 2006.