20511-03-9

Basic information

• Product Name: 4-(3-Hydroxyphenyl)-3-buten-2-one
• Synonyms: 4-(3-Hydroxyphenyl)-3-buten-2-one
• CAS NO: 20511-03-9
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.1852
• Mol File: 20511-03-9.mol
• Article Data: 17

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-(3-Hydroxyphenyl)-3-buten-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3-Hydroxyphenyl)-3-buten-2-one(20511-03-9)
• EPA Substance Registry System: 4-(3-Hydroxyphenyl)-3-buten-2-one(20511-03-9)

Safety Data

• Hazardous Substances Data: 20511-03-9(Hazardous Substances Data)

Upstream product

• 100-83-4 meta-hydroxybenzaldehyde 
• 67-64-1 acetone 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 106-96-7 propargyl bromide 
• 52945-15-0 4-(3-amino-phenyl)-but-3-en-2-one 

Downstream Products

• 868666-20-0 3',5'-trimethoxy-biphenyl-3-ol 
• 20766-31-8 (E)-4-(3-methoxyphenyl)but-3-en-2-one 
• 1612860-88-4 1-(3-hydroxyphenyl)-7-(3-methoxyphenyl)-1,4,6-heptatrien-3-one 
• 1612860-84-0 1,7-bis(3-hydroxyphenyl)-1,4,6-heptatrien-3-one 
• 1612860-87-3 1-(3-methoxyphenyl)-7-(3-hydroxyphenyl)-1,4,6-heptatrien-3-one 
• 1416332-50-7 tert-butyl (2-(3-(6-methyl-2-oxo-1,2-dihydropyridin-4-yl)phenoxy)ethyl)carbamate 
• 1416332-51-8 N-(2-(3-(6-methyl-2-oxo-1,2-dihydropyridin-4-yl)phenoxy)ethyl)-2-nitrobenzenesulfonamide 
• 1416332-49-4 2-(3-(6-methyl-2-oxo-1,2-dihydropyridin-4-yl)phenoxy)ethyl benzoate 
• 1416332-44-9 (E)-2-nitro-N-(2-(3-(3-oxobut-1-en-1-yl)phenoxy)ethyl)benzenesulfonamide 
• 1416332-42-7 (E)-2-(3-(3-oxobut-1-en-1-yl)phenoxy)ethyl benzoate 
• 1438389-30-0 (E)-3-hydroxystyryl acetate 

Relevant articles and documents

Design, green synthesis, antioxidant activity screening, and evaluation of protective effect on cerebral ischemia reperfusion injury of novel monoenone monocarbonyl curcumin analogs

Antioxidants with high efficacy and low toxicity have the potential to treat cerebral ischemia reperfusion injury (CIRI). Dienone monocarbonyl curcumin analogs (DMCA) capable of overcoming the instability and pharmacokinetic defects of curcumin possess notable antioxidant activity but are found to be significantly toxic. In this study, a novel skeleton of the monoenone monocarbonyl curcumin analogue sAc possessing reduced toxicity and improved stability was designed on the basis of the DMCA skeleton. Moreover, 32 sAc analogs were obtained by applying a green, simple, and economical synthetic method. Multiple sAc analogs with an antioxidant protective effect in PC12 cells were screened using an H2O2-induced oxidative stress damage model, and quantitative evaluation of structure–activity relationship (QSAR) model with regression coefficient of R2 = 0.918921 was built through random forest algorithm (RF). Among these compounds, the optimally active compound sAc15 elicited a potent protective effect on cell growth of PC12 cells by effectively eliminating ROS generation in response to oxidative stress injury by activating the Nrf2/HO-1 antioxidant signaling pathway. In addition, sAc15 exhibited good protection against CIRI in the mice middle cerebral artery occlusion (MCAO) model. In this paper, we provide a novel class of antioxidants and a potential compound for stroke treatment.

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.

Poly(N-isopropylacrylamide-co-l-proline)-catalyzed Claisen-Schmidt and Knoevenagel condensations: Unexpected enhanced catalytic activity of the polymer catalyst

The polymer catalyst is more effective than the corresponding monomer catalyst? Yes! The proline-modified polymer, poly(N-isopropylacrylamide-co-l-proline), was unexpectedly found to be more effective than the corresponding monomer l-proline catalyst in Claisen-Schmidt and Knoevenagel condensation reactions. 1H NMR, GC analysis and control reactions revealed that this abnormal phenomenon might be attributed to an enhanced concentration of the reactant on the surface of the polymer catalyst, which might be due to adsorption of the reactants to the polymer through hydrogen-bonding of the proline moiety with the reactants. This new polymer catalyst was so robust that it could be reused at least 10 times without deactivation. The polymer-catalyzed method was rather tolerant of substrates bearing sensitive groups that are usually incompatible with conventional acid- or base-catalyzed methods, reducing the protection-deprotection steps of the substrates.