18651-15-5

Basic information

• Product Name: 7-HYDROXY-3-METHYLFLAVONE
• Synonyms: 7-HYDROXY-3-METHYLFLAVONE;7-Hydroxy-3-methyl-2-phenyl-4H-1-benzopyran-4-one;7-hydroxy-3-methyl-2-phenyl-4H-chromen-4-one
• CAS NO: 18651-15-5
• Molecular Formula: C₁₆H₁₂O₃
• Molecular Weight: 252.26
• Product Categories: Di-substituted Flavones
• Mol File: 18651-15-5.mol

Chemical Properties

• Melting Point: 278°C
• Boiling Point: 452.2 °C at 760 mmHg
• Flash Point: 173.3 °C
• Appearance: /
• Density: 1.289 g/cm³
• Vapor Pressure: 8.57E-09mmHg at 25°C
• Refractive Index: 1.643
• CAS DataBase Reference: 7-HYDROXY-3-METHYLFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-HYDROXY-3-METHYLFLAVONE(18651-15-5)
• EPA Substance Registry System: 7-HYDROXY-3-METHYLFLAVONE(18651-15-5)

Safety Data

• Hazardous Substances Data: 18651-15-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
7-HYDROXY-3-METHYLFLAVONE is used as a therapeutic agent for its antioxidant, anti-inflammatory, and anti-cancer properties. It is employed to scavenge free radicals, reduce inflammation, and inhibit the growth of cancer cells, making it a potential candidate for the development of new drugs or treatments for various health conditions.
Used in Neuroprotection:
7-HYDROXY-3-METHYLFLAVONE is used as a neuroprotective agent due to its ability to protect the nervous system from damage and degeneration. Its antioxidant and anti-inflammatory properties contribute to the prevention of neurodegenerative diseases and promotion of overall brain health.
Used in Cardioprotection:
7-HYDROXY-3-METHYLFLAVONE is used as a cardioprotective agent to safeguard the heart from oxidative stress and inflammation. Its antioxidant properties help maintain cardiovascular health and prevent the development of heart-related diseases.

InChI:InChI=1/C16H12O3/c1-10-15(18)13-8-7-12(17)9-14(13)19-16(10)11-5-3-2-4-6-11/h2-9,17H,1H3

Upstream product

• 18651-16-6 3-methyl-7-methoxy-2-phenyl-4H-benzopyran-4-one 
• 5792-36-9 2',4'-dihydroxypropiophenone 
• 93-97-0 benzoic acid anhydride 
• 124039-97-0 7-Propargyloxy-3-methylflavone 
• 77609-88-2 7-(3'-Methylbut-2'-enyloxy)-3-methylflavone 
• 98-88-4 benzoyl chloride 
• 412017-82-4 1-(2-hydroxy-4-methoxy-phenyl)-2-methyl-3-phenyl-propane-1,3-dione 
• 412017-83-5 1-(2-benzoyloxy-4-methoxy-phenyl)-propan-1-one 
• 6270-44-6 2-hydroxy-4-methoxypropiophenone 
• 108-46-3 recorcinol 
• 401607-01-0 1-(2,4-bis-benzoyloxy-phenyl)-propan-1-one 
• 858258-32-9 7-benzoyloxy-3-methyl-2-phenyl-chromen-4-one 

Downstream Products

• 39818-46-7 7-hydroxy-3-methyl-4-oxo-2-phenyl-4H-chromene-8-carbaldehyde 
• 18651-22-4 7-methoxy-3-methyl-2-phenyl-8-(prop-2-en-1-yl)-4H-1-benzopyran-4-one 

Relevant articles and documents

Synthesis of novel substituted pyrano annulated flavones

A simple and efficient one pot method has been developed for the synthesis of some new functionalized pyrano fused flavone derivatives, alkyl 4,8-dioxo-2-phenyl-4,8-dihydropyrano[2,3-f]chromene-10-carboxylates and dialkyl 4-oxo-2-phenyl-4,8-dihydropyrano[2,3-f]chromene-8,9-dicarboxylates, from 7-hydroxy flavones and 7-hydroxy 8-formyl flavones using dialkylacetalynedicarboxylates in the presence of triphenyl phosphine. The structures of all synthesized compounds were elucidated by FT-IR, 1H and 13C NMR and Mass spectral analysis.

Synthesis of Diverse Oxa-Carbocycle-Annulated Flavones Using the Combined Claisen Rearrangement and Ring-Closing Metathesis

A simple and efficient route for the synthesis of oxepine-, oxocine-, oxepinone-, and dioxocine-angularly annulated flavone skeletons has been developed. The combined Claisen rearrangement and the ring-closing metathesis are used as key steps for the construction of C7/C8–C6–C6tricyclic core structures.

Synthesis, in vitro evaluation, and docking studies of novel chromone derivatives as HIV-1 protease inhibitor

Novel chromone derivatives with a benzopyran-4-one scaffold have been prepared by the one-pot cyclization reaction. The in vitro inhibitory activity of these new compounds towards HIV-1 protease have been evaluated using stop time HPLC method as the preliminary screening. The most potent compound, 7,8-dihydroxy-2-(3′-trifluoromethyl phenyl)-3-(3″- trifluoromethylbenzoyl)chromone (32), showed IC50 = 0.34 μM. The molecular docking study supported results from experimental activity testing and also provided structure-activity relationship of this series.

Facile synthesis of 9-acetyl/formyl/cyano-substituted pyrano[2,3-f]flavones and chromones using the baylis-hillman reaction

Condensation of 8-formyl-7-hydroxyflavones (2a-f) and 8-formyl-7-hydroxy-2- (2'-furyl)-3-methylchromone (2g) with methyl vinyl ketone (3), acrolein (4), and acrylonitrile (5) in the presence of diazabicyclo[2.2.2]octane (DABCO) under an N2 atmosphere at room temperature using Baylis-Hillman reaction conditions afforded 9-acetyl/formyl/cyano-substituted pyrano2,3-f]flavones (6a-f, 7a-f, 8a-f) and chromones (6g, 7g, 8g).

A New Synthesis of 9-Methylfuroflavones

9-Methylfuroflavones (III) have been synthesised by thermal Claisen rearrangement of 7-propargyloxy flavones (II).

Claisen Rearrangement of 7-(3'-Methylbut-2'-enyloxy)flavones and Isoflavones

The Claisen rearrangement of 7-(3'-methylbut-2'-enyloxy)-3-methylflavone (IIb) in N,N-dimethylaniline yields an abnormal open-chain product 7-hydroxy-8-(1',2'-dimethylallyl)-3-methylflavone (IIIb), the normal cyclisation product 2",3"-dihydro-2",3",3",3-tetramethylfuroflavone (Vb) and 2",3"-dihydro-2",2",3",3-tetramethylfuroflavone (VIb).Rearrangement of IIb in vacuo yields 7-hydroxy-3-methylflavone (Ib) and VIb.The Claisen rearrangement of IIb in Ac2O-NaOAc gives 7-acetoxy-8-(1',1'-dimethylallyl)-3-methylflavone (VIIIb) which on alkaline hydrolysis yields 7-hydroxy-8-(1',1'-dimethylallyl)-3-methylflavone (VIIb) (normal open-chain product).Claisen rearrangement of VIIb gives a mixture of IIIb, Vb and VIb.Rearrangement of 7-(3'-methylbut-2'-enyloxy)flavone (IIa) in N,N-dimethylaniline furnishes 7-hydroxy-8-(1',2'-dimethylallyl)flavone (IIIa) and 2",3"-dihydro-2",3",3"-trimethylfuroflavone (Va).Under similar conditions 7-(3'-methylbut-2'-enyloxy)-3-phenylflavone (IIc) and 7-(3'-methylbut-2'-enyloxy)-2-methylisoflavone (IId) yield only 2",3"-dihydro-2",3",3"-trimethylfuro derivatives (Vc) and (Vd) respectively.Acid-catalysed cyclisation of IIIa, IIIb and VIIIb gives VIa, VIb and Vb respectively.In all the Claisen rearrangements, only the angular rearrangement products (i.e. rearrangement to 8-position of flavonoid nucleus) are isolated.It is believed that unstable 7-hydroxy-8-(1',1'-dimethylallyl) compound (VII) acts as an intermediate for the formation of III, V and VI.