75291-75-7

Upstream product

• 186581-53-3 diazomethane 
• 72247-82-6 5,7-dihydroxy-8-C-prenylflavanone 
• 77-78-1 dimethyl sulfate 
• 72247-79-1 2',6'-dihydroxy-4-methoxy-3-C-prenylchalcone 
• 7507-89-3 2,6-dihydroxy-4-methoxy-acetophenone 
• 129750-75-0 2,6-di(methoxymethoxy)-4-methoxyacetophenone 
• 100-52-7 benzaldehyde 
• 246143-29-3 2,6-di(methoxymethoxy)-4-methoxy-3-C-prenylacetophenone 
• 480-39-7 pinocembrin 
• 870-63-3 prenyl bromide 
• 1220680-24-9 7-methoxy-5-(3-methylbut-2-enyloxy)flavanone 

Downstream Products

• 75672-55-8 candidone 
• 33523-62-5 1-(2’-hydroxy-4’,6’-dimethoxy-3’-(3’’-methyl-2’’-buten-1’’-yl)phenyl)ethanone 

Relevant academic research and scientific papers

Efficient microwave-assisted prenylation of pinostrobin and biological evaluation of its derivatives as antitumor agents

Pinostrobin (5-hydroxy-7-methoxyflavanone) obtained in relatively large amounts from fingerroot (Boesenbergia pandurata) was converted to its C-6 and C-8 prenylated derivatives. The Mitsunobu reaction, europium(III)-catalyzed Claisen-Cope rearrangement, and Claisen reaction coupled with cross-metathesis were used as the key steps. Using a sealed-vessel microwave reactor, the Mitsunobu and Claisen/Cope reactions occurred smoothly with short reaction times and in satisfactory yields. The target compounds and five new intermediary substances showed cytotoxic activity toward SK-BR-3, MCF-7, PC-3, and Colo-320DM human tumor cell lines, and all of them had significantly lower IC50 (μM) values than pinostrobin. Crown Copyright

Synthesis of 5-hydroxy-7-methoxy-8-C-prenylflavanone

5-Hydroxy-7-methoxy-8-C-prenylflavanone (7, 7-methylglabranin) isolated from the roots and stems of Glycyrriza lepidota has been synthesized by following an unambiguous route. All the new products have been characterized on the basis of spectral data.

Variations in the chemical shift of the 5-hydroxyl proton of 7-o-prenylated flavanones

In 1H nmr examination of 6- or 8-prenylated flavanone 7-methyl and 7-prenyl ethers, the signals of hydrogen-bonded hydroxyl proton appeared in relatively narrow region. Relatively large solvent effect was observed on the signal of 6-prenylflavanone 7-methyl and 7-prenyl ethers.

ANTIMICROBIAL AGENTS FROM HIGHER PLANTS: PRENYLATED FLAVONOIDS AND OTHER PHENOLS FROM GLYCYRRHIZA LEPIDOTA

Bioassay directed fractionation of extracts of American licorice, Glycyrrhiza lepidota (Leguminosae), resulted in identification of the known bibenzyl, 3,5-dihydroxy-4-(3-methyl-2-butenyl)-bibenzyl, and the known flavones, glabranin and pinocembrin, as well as the isolation and structure determination of the new flavonol, glepidotin A and the new dihydroflavonol, glepidotin B as antimicrobial agents.Key Word - Glycyrrhiza lepidota; Leguminosae; prenylated flavones; biphenyls; antimicrobial activity.