22292-71-3

Basic information

• Product Name: (E)-4-(3-ethoxy-4-hydroxyphenyl)but-3-en-2-one
• Synonyms: (E)-4-(3-ethoxy-4-hydroxyphenyl)but-3-en-2-one
• CAS NO: 22292-71-3
• Molecular Weight: 206.241
• Mol File: 22292-71-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (E)-4-(3-ethoxy-4-hydroxyphenyl)but-3-en-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-4-(3-ethoxy-4-hydroxyphenyl)but-3-en-2-one(22292-71-3)
• EPA Substance Registry System: (E)-4-(3-ethoxy-4-hydroxyphenyl)but-3-en-2-one(22292-71-3)

Safety Data

• Hazardous Substances Data: 22292-71-3(Hazardous Substances Data)

Upstream product

• 121-32-4 4-hydroxy-3-ethoxybenzaldehyde 
• 67-64-1 acetone 

Downstream Products

• 569646-79-3 4-(3-ethoxy-4-hydroxyphenyl)-2-butanone 

Relevant articles and documents

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.

Anti-tumor agents 255: Novel glycyrrhetinic acid-dehydrozingerone conjugates as cytotoxic agents

Esterification of glycyrrhetinic acid (GA) with dehydrozingerone (DZ) resulted in a novel cytotoxic GA-DZ conjugate. Based on this exciting finding, we conjugated eleven different DZ analogs with GA or other triterpenoids, including oleanoic acid (OA) or ursolic acid (UA). In an in vitro anti-cancer assay using nine different human tumor cell lines, most of the GA-DZ conjugates showed significant potency. Particularly, compounds 5, 29, and 30 showed significant cytotoxic effects against LN-Cap, 1A9, and KB cells with ED50 values of 0.6, 0.8, and 0.9 μM, respectively. Similar conjugates between DZ and OA or UA were inactive suggesting that the GA component is critical for activity. Notably, although GA-DZ conjugates showed potent cytotoxic activity, the individual components (GA and DZ analogs) were inactive. Thus, GA-DZ conjugates are new chemical entities and represent interesting hits for anti-cancer drug discovery and development.