16049-42-6

Basic information

• Product Name: Flavocommelin
• Synonyms: Flavocommelin;2-[4-(β-D-Glucopyranosyloxy)phenyl]-5-hydroxy-6-(β-D-glucopyranosyl)-7-methoxy-4H-1-benzopyran-4-one;6-β-D-Glucopyranosyl-2-[4-[(β-D-glucopyranosyl)oxy]phenyl]-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one;6-β-D-Glucopyranosyl-4'-(β-D-glucopyranosyloxy)-5-hydroxy-7-methoxyflavone;Flavocommelinin;Swertisin 4'-O-β-D-glucopyranoside
• CAS NO: 16049-42-6
• Molecular Formula: C₂₈H₃₂O₁₅
• Molecular Weight: 608.54468
• Mol File: 16049-42-6.mol

Chemical Properties

• Melting Point: 216-217 °C
• Boiling Point: 892.3±65.0 °C(Predicted)
• Appearance: /
• Density: 1.642±0.06 g/cm3(Predicted)
• PKA: 5.75±0.40(Predicted)
• CAS DataBase Reference: Flavocommelin(CAS DataBase Reference)
• NIST Chemistry Reference: Flavocommelin(16049-42-6)
• EPA Substance Registry System: Flavocommelin(16049-42-6)

Safety Data

• Hazardous Substances Data: 16049-42-6(Hazardous Substances Data)

Upstream product

• 749256-81-3 5-acetoxy-6-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranozyl)-7-methoxyflavone 
• 162489-61-4 2,3,4,6-tetra-O-acetyl-α,β-D-glucopyranosyl fluoride 
• 749256-76-6 5,4'-diacetoxy-6-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-7-methoxyflavan 
• 749256-79-9 5-acetoxy-6-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-7-methoxyflavanone 
• 749256-77-7 5,4'-diacetoxy-6-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-7-methoxyflavan 
• 749256-78-8 5,4'-diacetoxy-6-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-7-methoxyflavanone 
• 749256-80-2 5'-acetoxy-6-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranozyl)-7-methoxyflavanone 
• 1437307-71-5 5-benzoyl-4'-benzyloxy-6-C-(2'',3'',4'',6''-tetra-O-benzyl-β-D-glucopyranosyl)-7-methoxyflavone 
• 1437307-76-0 5-benzoyl-6-C-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-4'-O-(2''',3''',4''',6'''-tetra-O-acetyl-β-D-glucopyranosyl)-7-methoxyflavone 
• 1437307-74-8 4'-acetoxy-5-benzoyl-6-C-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-7-methoxyflavone 
• 1437307-75-9 5-benzoyl-4'-hydroxy-6-C-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-7-methoxyflavone 
• 10299-59-9 1‐(2‐(benzyloxy)‐6‐hydroxy‐4‐methoxyphenyl)ethan‐1‐one 
• 169566-44-3 6-benzyloxy-3-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2-hydroxy-4-methoxyacetophenone 
• 89025-46-7 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl fluoride 

Downstream Products

• 6991-10-2 swertisin 

Relevant articles and documents

Concise synthesis of flavocommelin, 7-O-methylapigenin 6-C-, 4′-O-bis-β-d-glucoside, a component of the blue supramolecular pigment from Commelina communis

Flavocommelin, 7-O-methylapigenin 6-C-, 4′-O-bis-β-d-glucoside, was synthesized in 9 steps from the C-glycosylation of 6-O-benzy-4-O- methylphloroacetophenone via the introduction of a cinnamoyl residue by aldol condensation and the formation of a C-ring by regioselective and oxidative ring-closure to regio- and stereoselective O-glycosylation for an overall yield of 31%.

Total synthesis of flavocommelin, a component of the blue supramolecular pigment from Commelina communis, on the basis of direct 6-C-glycosylation of flavan

We succeeded in a first total synthesis of flavocommelin (1), a component of the blue supramolecular pigment, commelinin (2), from Commelina communis, by direct 6-C-glycosylation of the flavan 4 using perbenzylglucosyl fluoride 8 in the presence of MS 5 A in CH2Cl2 and a catalytic amount of BF3·Et2O. After 6-C-glycosylation of 4, oxidation with CAN to flavanone 18 and subsequent 4′-O-glycosylation, promoted with a combination of BF3·Et2O and DTBMP, afforded diglucosylflavanone 20. DDQ oxidation of 20 and deprotection successively gave 1.