14004-48-9

Upstream product

• 55969-56-7 5,7-dihydroxy-8-methyl-2-phenylchromen-4-one 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 14004-47-8 5,7-dimethoxy-8-methyl-2-phenylchromen-4-one 
• 23121-32-6 1-(2-hydroxy-4,6-dimethoxy-3-methyl-phenyl)-ethanone 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 1775-97-9 flavokawain B 
• 137203-34-0 bis(trimethylaluminum)–1,4-diazabicyclo[2.2.2]octane adduct 
• 26505-96-4 5,7-di-O-methyl-8-iodochrysin 
• 21392-57-4 Dimethyl-chrysin 
• 2811-30-5 5-hydroxy-7-methoxy-8-methylflavanone 
• 519-59-5 5,7-dihydroxy-8-methylflavanone 
• 93-97-0 benzoic acid anhydride 

Downstream Products

• 14004-47-8 5,7-dimethoxy-8-methyl-2-phenylchromen-4-one 
• 529-52-2 6-Methylchrysine 
• 55969-56-7 5,7-dihydroxy-8-methyl-2-phenylchromen-4-one 
• 109251-29-8 Strobochrysin dimethylether 
• 55969-57-8 5-hydroxy-7-methoxy-6-methyl-2-phenyl-chromen-4-one 

Relevant academic research and scientific papers

Unveiling the 6,8-Rearrangement in 8-Phenyl-5,7-dihydroxyflavylium and 8-Methyl-5,7-dihydroxyflavylium through Host–Guest Complexation

8-Phenyl-5,7-dihydroxyflavylium and 8-methyl-5,7-dihydroxyflavylium were synthesized to observe the 6,8-rearrangement. 8-Phenyl and 8-methyl residues were introduced by Suzuki–Miyaura reaction of 8-iodochrysin, then reduced by LiAlH4 to give the corresponding 3-deoxyanthocyanidins. At pH 1.0 the stable form is the 8-substituted flavylium cation in both compounds. At higher pH values the quinoidal bases are the stable species and some evidence for the 6,8-rearrangement was obtained, but the respective spectral variations are very small. This was overcome by using a modified cyclodextrin (captisol), which favors the formation of the trans-chalcone at the expense of the quinoidal bases. The trans-chalcone was isolated and dissolved in CD3OD/DCl (pD + m/z 253). The 6-isomer slowly reverts to the most stable 8-isomer. The 6,8-rearrangement was also observed after irradiation of the trans-chalcone (in the presence of captisol) at pH 5. Acidification of this photostationary state gave a mixture of both flavylium cations. The UV/Vis absorption of the flavylium cation (6-isomer) was blueshifted in comparison to the 8-isomer.

Anti-AIDS agents 68. The first total synthesis of a unique potent anti-HIV chalcone from genus Desmos

The first total synthesis of a unique highly functionalized and potent anti-HIV chalcone 1, isolated from genus Desmos, was achieved from commercially available 2,4,6-trihydroxytoluene (3) or 2,4,6-trihydroxybenzaldehyde (2) in five (from 3) or six steps (from 2).