3162-26-3

Basic information

• Product Name: (2R,3R)-3,7-bis(acetyloxy)-2-[3,4-bis(acetyloxy)phenyl]-2,3-dihydro-5-hydroxy-4H-1-benzopyran-4-one
• CAS NO: 3162-26-3
• Molecular Weight: 472.405
• Mol File: 3162-26-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (2R,3R)-3,7-bis(acetyloxy)-2-[3,4-bis(acetyloxy)phenyl]-2,3-dihydro-5-hydroxy-4H-1-benzopyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-3,7-bis(acetyloxy)-2-[3,4-bis(acetyloxy)phenyl]-2,3-dihydro-5-hydroxy-4H-1-benzopyran-4-one(3162-26-3)
• EPA Substance Registry System: (2R,3R)-3,7-bis(acetyloxy)-2-[3,4-bis(acetyloxy)phenyl]-2,3-dihydro-5-hydroxy-4H-1-benzopyran-4-one(3162-26-3)

Safety Data

• Hazardous Substances Data: 3162-26-3(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 6685-67-2 (+/-)-taxifolin pentaacetate 
• 75-36-5 acetyl chloride 
• 480-18-2 taxifolin 

Downstream Products

• 6685-67-2 2-(3,4-diacetoxyphenyl)-4-oxochroman-3,5,7-triyl triacetate 
• 64191-31-7 trans-2-(3,4-dihydroxyphenyl)-2,3-dihydro-3-acetoxy-5,7-dihydroxy-4H-1-benzopyran-4-one 

Relevant articles and documents

Epimerization, transacylation and bromination of dihydroquercetin acetates; Synthesis of 8-bromodihydroquercetin

Dihydroquercetin (dhq) and its 3-acetate react with acetic anhydride in the absence of a base catalyst to yield mixtures of partially acetylated products. Three new esters were characterized by NMR spectroscopy as dhq 3,7,3'-triacetate, 3,7,4'-triacetate and 5,7,3',4'- tetraacetate. At its melting point neat dhq 3,7,3',4'-tetraacetate is partially converted to dhq 3,3',4'-triacetate and dhq pentaacetate by intermolecular acetyl transfer. Dhq 7,3',4'-triacetate yields exclusively dhq 3',4'-di- and 3,7,3',4'-tetraacetate under these conditions. The acetylation/deacetylation reactions are accompanied by partial epimerization: 3 new acetates with 2,3-cis stereochemistry (dhq 3-, 3,7,3',4'-tetra- and penta-) were identified. Dhq and its 3,7,3',4'-tetraacetate undergo regiospecific dibromination at C-6 and C-8 with excess N-bromosuccinimide in polar solvents, and 6,8-dibromo-dhq can be regioselectively debrominated to 8-bromo-dhq with sodium sulfite. Versita Sp. z o.o.

Preparation and partial deacetylation of dihydroquercetin acetates

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