3034-04-6

Basic information

• Product Name: 6-METHOXYFLAVANONE
• Synonyms: METHOXYFLAVANONE, 6-;6-METHOXYFLAVANONE;6-METHOXYFLAVANONE 98%;METHOXYFLAVANONE, 6-(P);2-Phenyl-6-methoxy-2,3-dihydro-4H-1-benzopyran-4-one;2-Phenyl-6-methoxy-2H-1-benzopyran-4(3H)-one;2-Phenyl-6-methoxychroman-4-one;6-Methoxyflavanone,98%
• CAS NO: 3034-04-6
• Molecular Formula: C₁₆H₁₄O₃
• Molecular Weight: 254.28
• EINECS: -0
• Product Categories: Flavanones;Biochemistry;Flavonoids
• Mol File: 3034-04-6.mol
• Article Data: 24

Chemical Properties

• Melting Point: 141-143 °C(lit.)
• Boiling Point: 425.5°Cat760mmHg
• Flash Point: 202.9°C
• Appearance: /
• Density: 1.199g/cm³
• Vapor Pressure: 1.91E-07mmHg at 25°C
• Refractive Index: 1.587
• BRN: 248912
• CAS DataBase Reference: 6-METHOXYFLAVANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-METHOXYFLAVANONE(3034-04-6)
• EPA Substance Registry System: 6-METHOXYFLAVANONE(3034-04-6)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 36/37/39-26
• WGK Germany: 3
• Hazardous Substances Data: 3034-04-6(Hazardous Substances Data)

Usage

Chemical Properties

slightly yellowish-green crystalline powder

InChI:InChI=1/C16H14O3/c1-18-12-7-8-15-13(9-12)14(17)10-16(19-15)11-5-3-2-4-6-11/h2-9,16H,10H2,1H3/t16-/m1/s1

Upstream product

• 705-15-7 1-(2-hydroxy-5-methoxyphenyl)ethan-1-one 
• 100-52-7 benzaldehyde 
• 26964-24-9 6-methoxyflavone 
• 102-92-1 Cinnamoyl chloride 
• 490-78-8 2,5-Dihydroxyacetophenone 
• 3262-89-3 triphenylboroxine 
• 59887-88-6 6-methoxy-chromen-4-one 
• 99430-05-4 1-(2-hydroxy-5-methoxyphenyl)-3-phenyl-1-propanone 
• 100-46-9 benzylamine 
• 150-76-5 4-methoxy-phenol 
• 5802-17-5 6-methoxychroman-4-one 
• 98-80-6 phenylboronic acid 
• 63815-39-4 2-(4-Methoxyphenoxy)cyanoethane 
• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 

Downstream Products

• 1431952-43-0 3-ferrocenylmethylidenyl-6-methoxy-2-phenylchroman-4-one 
• 76279-00-0 4-oxo-2-phenylchroman-6-yl acetate 
• 1289081-28-2 6-propionoxyflavanone 
• 6665-83-4 6-hydroxyflavone 
• 1228118-69-1 (-)-(S)-6,4'-dihydroxyflavanone 
• 4250-77-5 6-hydroxyflavanone 
• 1266399-40-9 8-methoxy-4-phenyl-4H-benzopyran[4,3-d][1,2,3]selenadiazole 
• 1266399-51-2 C₁₇H₁₇N₃O₃ 
• 1175542-34-3 8-methoxy-4-phenyl-1,4-dihydrochromeno[4,3-d][1,2,3]triazole 
• 84963-03-1 6-methoxy-2-phenylchroman-4-one 
• 190831-06-2 6-methoxy-2-phenylchroman-4-one 

Relevant articles and documents

Synthesis of Flavanone and Quinazolinone Derivatives from the Ruthenium-Catalyzed Deaminative Coupling Reaction of 2′-Hydroxyaryl Ketones and 2-Aminobenzamides with Simple Amines

The cationic Ru–H complex [(C6H6)(PCy3)(CO)RuH]+BF4– (1) with 3,4,5,6-tetrachloro-1,2-benzoquinone (L1) was found to be a highly effective catalyst for the deaminative coupling reaction of 2′-hydroxyaryl ketones with simple amines to form 3-substituted flavanone products. The analogous deaminative coupling reaction of 2-aminobenzamides with branched amines directly formed 3,3-disubstituted quinazolinone products. The catalytic method efficiently installs synthetically useful flavanone and quinazolinone core structures without employing any reactive reagents.

Organocatalytic Approach for Assembling Flavanones via a Cascade 1,4-Conjugate Addition/oxa-Michael Addition between Propargylamines with Water

A DBU-catalyzed one-pot cascade reaction of propargylamines and water for the synthesis of flavanones has been developed. This process proceeds via a sequence of 1,4-conjugate addition of water to alkynyl o-quinone methide (o-AQM), followed by the alkyne-allene isomerization and subsequent intramolecular oxa-Michael addition. This strategy provides a convenient method for accessing a broad range of flavanones in good to excellent yields with good functional-group tolerance, in particular, the reactive halo functional groups.

Discovery of a Prenylated Flavonol Derivative as a Pin1 Inhibitor to Suppress Hepatocellular Carcinoma by Modulating MicroRNA Biogenesis

Peptidyl-prolyl cis-trans isomerase Pin1 plays a crucial role in the development of human cancers. Recently, we have disclosed that Pin1 regulates the biogenesis of miRNA, which is aberrantly expressed in HCC and promotes HCC progression, indicating the therapeutic role of Pin1 in HCC therapy. Here, 7-(benzyloxy)-3,5-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one (AF-39) was identified as a novel Pin1 inhibitor. Biochemical tests indicate that AF-39 potently inhibits Pin1 activity with an IC50 values of 1.008 μm, and also displays high selectivity for Pin1 among peptidyl prolyl isomerases. Furthermore, AF-39 significantly suppresses cell proliferation of HCC cells in a dose- and time-dependent manner. Mechanistically, AF-39 regulates the subcellular distribution of XPO5 and increases miRNAs biogenesis in HCC cells. This work provides a promising lead compound for HCC treatment, highlighting the therapeutic potential of miRNA-based therapy against human cancer.