20943-11-7

Basic information

• Product Name: Isoembigenin
• Synonyms: Isoembigenin;2-(4-Methoxyphenyl)-7-methoxy-8-(β-D-glucopyranosyl)-5-hydroxy-4H-1-benzopyran-4-one
• CAS NO: 20943-11-7
• Molecular Formula: C₂₃H₂₄O₁₀
• Mol File: 20943-11-7.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Isoembigenin(CAS DataBase Reference)
• NIST Chemistry Reference: Isoembigenin(20943-11-7)
• EPA Substance Registry System: Isoembigenin(20943-11-7)

Safety Data

• Hazardous Substances Data: 20943-11-7(Hazardous Substances Data)

Upstream product

• 3681-93-4 vitexin 
• 20197-48-2 5,7-dimethoxy-2-(4-methoxyphenyl)-8-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4H-1-benzopyran-4-one 
• 163395-88-8 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-8-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4H-1-benzopyran-4-one 
• 73051-76-0 isoswertisin-5-O-β-D-glucoside 
• 2903-76-6 5,7-dihydroxy-2-(4-hydroxy-phenyl)-8-(tetra-O-acetyl-β-D-glucopyranosyl)-chromen-4-one 

Downstream Products

• 94306-05-5 5,7-dimethoxy-2-(4-methoxy-phenyl)-4-oxo-4H-chromene-8-carbaldehyde 
• 100-09-4 4-methoxybenzoic acid 
• 73244-63-0 1-(3-β-D-glucopyranosyl-2-hydroxy-4,6-dimethoxy-phenyl)-ethanone 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Relevant articles and documents

Glycosyl Imidates, 69. - Synthesis of Flavone C-Glycosides Vitexin, Isovitexin, and Isoembigenin

2-Hydroxy-4,6-dimethoxyacetophenone (4) was glycosylated with O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl) trichloroacetimidate (5) and trimethylsilyl triflate as promoter to yield directly the C-glycoside 6.Construction of the flavone system by application of a Baker-Venkataraman-type rearrangement followed by deprotection yielded isoembigenin (2).Glycosylation of 4,6-bis(tert-butyldimethylsilyloxy)-2-hydroxyacetophenone (17) with the trichloroacetimidate 5 afforded the O-glycoside intermediate 18 which was converted via Fries rearrangement into the C-glycoside 21.Applying again the Baker-Venkataraman rearrangement and cyclization gave isovitexin and vitexin derivatives 25 and 26, which were completely deprotected to yield isovitexin (1b) and vitexin (1a), respectively. - Key Words: Glycosides / Flavones / Vitexin / Isovitexin / Isoembigenin / Carbohydrates / Trichloroacetimidates / Fries rearrangement / Baker-Venkataraman rearrangement