77333-99-4

Upstream product

• 1080-12-2 (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-one 
• 123-72-8 butyraldehyde 
• 121-33-5 vanillin 
• 130878-31-8 (E)-3-methoxy-4-trimethylsilyloxybenzylideneacetone 

Downstream Products

• 77398-90-4 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)octan-3-one 

Relevant academic research and scientific papers

Discovery and Characterization of Pure RhlR Antagonists against Pseudomonas aeruginosa Infections

Pseudomonas aeruginosa (P. aeruginosa) is an opportunistic human pathogen that forms biofilms and produces virulence factors via quorum sensing (QS). Blocking the QS system in P. aeruginosa is an excellent strategy to reduce biofilm formation and the production of virulence factors. RhlR plays an essential role in the QS system of P. aeruginosa. We synthesized 55 analogues based on the chemical structure of 4-gingerol and evaluated their RhlR inhibitory activities using the cell-based reporter strain assay. Comprehensive structure-activity relationship studies identified the alkynyl ketone 30 as the most potent RhlR antagonist. This compound displayed selective RhlR antagonism over LasR and PqsR, strong inhibition of biofilm formation, and reduced production of virulence factors in P. aeruginosa. Furthermore, the survival rate of Tenebrio molitor larvae treated with 30 in vivo greatly improved. Therefore, compound 30, a pure RhlR antagonist, can be utilized for developing QS-modulating molecules in the control of P. aeruginosa infections.

Syntheses of the (+/-)--Gingerols (Pungent Principles of Ginger) and Related Compounds through Regioselective Aldol Condensations: Relative Pungency Assays

The deprotonation of trimethylsilylzingerone (13) by lithium di-isopropylamide at -78 deg C has been found to be regioselective (92 : 8 in favour of less-substituted enolate): the anion was condensed with alkanals and acyl imidazoles to give convenient syntheses of (+/-)--- and --gingerols (1) and -, -, and -gingerdiones (9).Similary, 3-methoxy-4-trimethylsilyloxybenzylideneacetone (17) gave the (+/-)---dehydrogingerols (8) and -, -, and -dehydrogingerdiones (10).The aldol reaction to -gingerol and methyl -gingerol was also conducted through a vinyloxyborane or through the enol silyl ether (TiCl4 catalysis).Results of organoleptic assays on these compounds are discussed, and the relation between pungency in the gingerols and in capsaicin is commented on.The aldol method was also used to synthesise the natural β-ketols(+/-)-daphneolone (25) and (+/-)-hexahydrocurcumin (4).