74628-44-7

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-2,3-dihydro-3,5-dihydroxy-7-methoxy-, (2R,3R)-
• CAS NO: 74628-44-7
• Molecular Formula: C18H18O7
• Molecular Weight: 346.337
• Mol File: 74628-44-7.mol

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-2,3-dihydro-3,5-dihydroxy-7-methoxy-, (2R,3R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-2,3-dihydro-3,5-dihydroxy-7-methoxy-, (2R,3R)-(74628-44-7)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-2,3-dihydro-3,5-dihydroxy-7-methoxy-, (2R,3R)-(74628-44-7)

Safety Data

• Hazardous Substances Data: 74628-44-7(Hazardous Substances Data)

Upstream product

• 77-78-1 dimethyl sulfate 
• 186581-53-3 diazomethane 
• 480-18-2 taxifolin 

Downstream Products

• 29080-58-8 5-hydroxy-3',4',7-trimethoxyflavone 
• 70987-96-1 5-hydroxy-3′4′7-trimethoxy flavanone 

Relevant articles and documents

Structure-activity relationship for (+)-taxifolin isolated from silymarin as an inhibitor of amyloid β aggregation

Silymarin, the seed extract of Silybium marianum, has preventive effects against Alzheimer's disease-like pathogenesis in vivo. We isolated (+)-taxifolin (4) from silymarin as an inhibitor of aggregation of the 42- residue amyloid -protein. Structure-activity relationship studies revealed the 30,40-dihydroxyl groups to be critical to the anti-aggregative ability, whereas the 7-hydroxyl group and the stereochemistry at positions 2 and 3 were not important.

LEUCOCYANIDIN: SYNTHESIS AND PROPERTIES OF (2R,3S,4R)-(+)-3,4,5,7,3',4'-HEXAHYDROXYFLAVAN

An isomer of leucocyanidin, (2R,3S,4R)-(+)-3,4,5,7,3',4'-hexahydroxyflavan has been synthesized from (+)-taxifolin, isolated in its phenolic form, and characterized by 1H and 13C NMR, and formation of the 5,7,3',4'-tetramethyl ether.Leucocyanidin readily polymerizes in acid solution to form a procyanidin polymer of high MW. - Key Word Index: Leucocyanidin; flavan-3,4-diols; synthesis; polymerization; phytochemical significance.

Photochemical Deoxygenation of an α-Ketol: The Dihydroflavonol-Flavanone Conversion

Irradiation of optically pure 2,3-trans-3-hydroxyflavanones in anhydrous ethyl acetate leads directly to free phenolic flavanone analogues with complete retention of configuration at C(2).Similarly their methyl ethers give the corresponding flavanones and flavones.The reaction represents the photochemical equivalent of a reduction under Clemmensen conditions.