6665-86-7

Basic information

• Product Name: 7-HYDROXYFLAVONE
• Synonyms: TIMTEC-BB SBB005921;7-HYDROXYFLAVONE;7-HYDROXY-2-PHENYL-4H-CHROMEN-4-ONE;7-HYDROXY-2-PHENYLCHROMONE;HYDROXYFLAVONE, 7-;7-hydroxy-2-phenyl-4-benzopyrone;7-Hydroxyflavone,98%;HYDROXYFLAVONE, 7-(RG)
• CAS NO: 6665-86-7
• Molecular Formula: C₁₅H₁₀O₃
• Molecular Weight: 238.24
• EINECS: 229-705-3
• Product Categories: Mono-substituted Flavones;Biochemistry;Flavonoids
• Mol File: 6665-86-7.mol
• Article Data: 61

Chemical Properties

• Melting Point: 245-247 °C(lit.)
• Boiling Point: 320.83°C (rough estimate)
• Flash Point: 176.3 °C
• Appearance: off-white crystals
• Density: 1.340±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 1.02E-08mmHg at 25°C
• Refractive Index: 1.5740 (estimate)
• PKA: 7.02±0.40(Predicted)
• Water Solubility: Insoluble in water
• BRN: 194089
• CAS DataBase Reference: 7-HYDROXYFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-HYDROXYFLAVONE(6665-86-7)
• EPA Substance Registry System: 7-HYDROXYFLAVONE(6665-86-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 6665-86-7(Hazardous Substances Data)

Usage

Synthesis

Acetylation of resorcinol acetic acid yields 2,4-dihydroxyacetophenone, which is then subjected to benzoylation and transposition to obtain (2-hydroxy-4-benzoyloxy)benzoylacetophenone. 7-hydroxyflavone was obtained by further cyclization reaction in a mixture of acetic acid and hydrochloric acid at 103° C for 7 h.

Chemical Properties

off-white crystals

Uses

Different sources of media describe the Uses of 6665-86-7 differently. You can refer to the following data:
1. antifungal, analgesic
2. Reactant:Acting as a biologically valuable acceptor in O-glycosidation reactionsInvolved in synthesis of fully phosphorylated flavones for use as pancreatic cholesterol esterase inhibitorsFor O-methylation with di-Me carbonateLinked by a polymethylene chain for synthesis of α1-adrenoceptor antagonistsInvolved in Baylis-Hillman reactionsInvolved in phase-transfer catalyzed glucosylation for synthesis of glucosylated flavonoids

Biological Activity

7-Hydroxyflavone is a flavonoid isolated from M. indica with anti-inflammatory properties. It protects renal cells from nicotine (NIC)-induced cytotoxicity through the ERK/Nrf2/HO-1 pathway.

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

Upstream product

• 5465-06-5 <4-(benzoyloxy)-2-hydroxybenzoyl>benzoylmethane 
• 101279-20-3 3-benzoyl-4,7-dihydroxy-coumarin 
• 95161-88-9 7-(benzyloxy)-2-phenyl-4H-chromen-4-one 
• 117096-61-4 7-hydroxy-2-phenyl-3-benzoylchromone 
• 952018-33-6 1-(2-hydroxy-4-tetrahydropyran-2-yloxy-phenyl)-3-phenyl-propane-1,3-dione 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 98-95-3 nitrobenzene 
• 108-46-3 recorcinol 
• 103-73-1 Phenetole 
• 101-84-8 diphenylether 
• 127-09-3 sodium acetate 
• 64-19-7 acetic acid 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 93-97-0 benzoic acid anhydride 

Downstream Products

• 27654-57-5 7-Butoxycarbonylmethoxy-4-oxo-2-phenyl-4H-chromen 
• 109817-89-2 7-dichloroacetoxy-2-phenyl-chromen-4-one 
• 27654-56-4 (4-oxo-2-phenyl-4H-chromen-7-yloxy)-acetic acid isopropyl ester 
• 27654-55-3 (4-oxo-2-phenyl-4H-chromen-7-yloxy)-acetic acid propyl ester 
• 111270-57-6 (4-oxo-2-phenyl-4H-chromen-7-yloxy)-acetic acid allyl ester 
• 27654-58-6 (4-oxo-2-phenyl-4H-chromen-7-yloxy)-acetic acid isobutyl ester 
• 36556-15-7 (4-oxo-2-phenyl-4H-chromen-7-yloxy)-acetic acid isopentyl ester 
• 36556-14-6 (4-oxo-2-phenyl-4H-chromen-7-yloxy)-acetic acid pentyl ester 
• 36556-16-8 (4-oxo-2-phenyl-4H-chromen-7-yloxy)-acetic acid hexyl ester 
• 42345-27-7 8-acetyl-7-hydroxy-2-phenyl-chromen-4-one 
• 72994-98-0 4-oxo-2-phenyl-4H-chromen-7-yl acetate 
• 27654-54-2 methyl(7-flavonyloxy)acetate 
• 119-41-5 7-ethoxycarbonylmethoxyflavone 
• 65679-28-9 7-allyloxy-2-phenyl-4H-chromen-4-one 

Relevant articles and documents

Divergent synthesis of flavones and flavanones from 2′-hydroxydihydrochalconesviapalladium(ii)-catalyzed oxidative cyclization

Divergent and versatile synthetic routes to flavones and flavanonesviaefficient Pd(ii) catalysis are disclosed. These Pd(ii) catalyses expediently provide a variety of flavones and flavanones from 2′-hydroxydihydrochalcones as common intermediates, depending on oxidants and additives,viadiscriminate oxidative cyclization sequences involving dehydrogenation, respectively, in a highly atom-economic manner.

Identification of inhibitors targeting polyketide synthase 13 of Mycobacterium tuberculosis as antituberculosis drug leads

Polyketide synthase 13 (Pks13) is an essential enzyme in the synthesis of mycolic acids in Mtb. Therefore, Pks13 is a promising drug target for tuberculosis treatment. We used a structure-guided approach to identify novel chemotype inhibitors of Pks13 and assessed them using a Pks13 enzymatic assay and surface plasmon resonance. The structure–activity relationships (SAR) results demonstrated that the substituents at the 2, 5, and 6 positions of the 4H-chromen-4-one scaffold are critical for maintaining the MIC. Compound 6e with 2-hydroxyphenyl at the 2 position of the 4H-chromen-4-one scaffold, exhibited potent activity against Mtb H37Rv (MIC = 0.45 μg/mL) and displayed good Pks13 affinity and inhibition (IC50 = 14.3 μM). This study described here could provide an avenue to explore a novel inhibitor class for Pks13 and aid the further development of antituberculosis drugs.

Flavonoid analogues as urease inhibitors: Synthesis, biological evaluation, molecular docking studies and in-silico ADME evaluation

A series of novel flavonoid analogues were designed and synthesized. The aimed compounds for urease inhibitory activities were clearly superior to the control drug thiourea (more than 10 times). Among these compounds, L2 (IC50 = 1.343 μM) and L12 (IC50 = 1.207 μM) exhibited the most excellent urease inhibitory activity in vitro. The molecular dockings of L2, L12 and L22 into urease were performed to explore the binding modes and their structure-activity relationship. Furthermore, these aimed compounds showed good druggable properties.