5424-52-2

Usage

Uses

Used in Fragrance and Flavor Industry:
(3E)-4-(2,3-dimethoxyphenyl)but-3-en-2-one is used as a fragrance and flavor ingredient for its pleasant scent.
Used in Pharmaceutical Industry:
(3E)-4-(2,3-dimethoxyphenyl)but-3-en-2-one is used as an intermediate in the synthesis of pharmaceuticals and other organic compounds.
Used in Organic Chemistry:
(3E)-4-(2,3-dimethoxyphenyl)but-3-en-2-one is used as a starting material for the synthesis of more complex molecules in the field of organic chemistry.
It is important to handle (3E)-4-(2,3-dimethoxyphenyl)but-3-en-2-one with care as it may have hazardous effects if not used properly.

Upstream product

• 67-64-1 acetone 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 4202-14-6 dimethyl (2-oxopropyl)phosphonate 

Downstream Products

• 71959-34-7 2-(2,3-Dimethoxy-phenyl)-4,6-dioxo-cyclohexancarbonsaeure-ethylester 
• 1241389-05-8 5-(1-(2,3-dimethoxyphenyl)-3-oxobutyl)furan-2(5H)-one 
• 1263786-47-5 methyl (2R,3S,4aR)-3-(2,3-dimethoxyphenyl)-4a-methyl-1-oxo-1,2,3,4,4a,6-hexahydrobenzo[d]pyrido[2,1-b][1,3]oxazine-2-carboxylate 
• 1293997-23-5 (S)-tert-butyl 2-((S)-1-(2,3-dimethoxyphenyl)-3-oxobutyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate 
• 81885-94-1 4-(2,3-dimethoxyphenyl)butan-2-one 
• 5424-87-3 1t-(2,3-dimethoxy-phenyl)-5-morpholino-pent-1-en-3-one; hydrochloride 
• 1597410-41-7 (E)-S-methyl 4-(2,3-dimethoxyphenyl)-2-oxobut-3-enethioate 
• 7345-82-6 trans-2,3-dimethoxycinnamic acid 

Relevant academic research and scientific papers

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.

Method for synthesizing asymmetrical mono-carbonyl curcumin analogue intermediate

The invention discloses a method for synthesizing an asymmetrical mono-carbonyl curcumin analogue intermediate. The method comprises the following steps: using one of acetone, cyclopentanone, cyclohexanone, pyrone and 4-piperidone and benzaldehyde with a substituent group as reaction raw materials, using anhydrous dimethyl sulfoxide as a solvent, firstly reacting for 48 h under the catalysis of L-proline, then using concentrated hydrochloric acid to provide an acidic condition for dehydration, and carrying out room temperature reaction synthesis to obtain the asymmetrical mono-carbonyl curcumin analogue intermediate. All kinds of raw materials used in the method are generally commercialized, and can be directly purchased and obtained. Compared with the prior art, a great number of solid wastes cannot be generated without using any precious metal catalyst or halogenated solvent. Therefore, the method has the advantages of simple steps, easy operation, little pollution, high yield, easyobtaining for raw materials and the like, and has potential and wide application prospects, so that reference can be provided for the synthesis of the asymmetrical mono-carbonyl curcumin analogue intermediate.

Discovery of new MD2-targeted anti-inflammatory compounds for the treatment of sepsis and acute lung injury

Myeloid differentiation 2 (MD2) is essential to the recognition of lipopolysaccharide (LPS) and the subsequent mediation of toll-like receptor 4 (TLR4)-dependent acute inflammatory disorders including sepsis and acute lung injury. Inhibitors targeting MD2 may provide an alternative means to subdue acute inflammatory diseases. In the present study, 39 bisaryl-1,4-dien-3-one compounds with 5-carbon connection chains were designed and synthesized as MD2 inhibitors based on the analysis of the molecular docking of xanthohumol to MD2. The compound-MD2 interactions were measured by cell-free assays including bis-ANS displacement and SPR, and the active compounds were further tested for MD2 inhibition and anti-inflammatory activities in LPS-challenged macrophages. The most active compound, 1f, was shown to have remarkable protective effects against sepsis shock and pulmonary inflammation. Collectively, we present evidence that bisaryl-1,4-dien-3-one is a new lead structure for the development of anti-inflammatory agents targeting MD2.

Traceless OH-Directed Wacker Oxidation-Elimination, an Alternative to Wittig Olefination/Aldol Condensation: One-Pot Synthesis of α,β-Unsaturated and Nonconjugated Ketones from Homoallyl Alcohols

A new method for one-pot synthesis of β-substituted and β,β-disubstituted α,β-unsaturated methyl ketones from homoallyl alcohols by sequential PdCl2/CrO3-promoted Wacker process followed by an acid-mediated dehydration reaction has been developed. Remarkably, internal homoallyl alcohols delivered regioselectively nonconjugated unsaturated carbonyl compounds under the same protocol. A new starting material-based synthesis of α,β-unsaturated and nonconjugated methyl ketones is demonstrated.

PPh3·HBr-DMSO mediated expedient synthesis of γ-substituted β,γ-unsaturated α-ketomethylthioesters and α-bromo enals: Application to the synthesis of 2-methylsulfanyl-3(2 H)-furanones

An efficient chemoselective general procedure for the synthesis of γ-substituted β,γ-unsaturated α-ketomethylthioesters from α,β-unsaturated ketones has been achieved through an unprecedented PPh3·HBr-DMSO mediated oxidative bromination and Kornblum oxidation sequence. The newly developed reagent system serves admirably for the synthesis of α-bromoenals from enals. Furthermore, AuCl 3-catalyzed efficient access to 3(2H)-furanones from the above intermediates under extremely mild conditions are described. Copyright

INHIBITORS OF CYSTATHIONINE BETA SYNTHASE TO REDUCE THE NEUROTOXIC OVERPRODUCTION OF ENDOGENOUS HYDROGEN SULFIDE

The invention is directed to inhibitors of cystathionine beta synthase which, among other biochemical effects, allow reduction of the neurotoxic overproduction of endogenous hydrogen sulphide. These compounds and pharmaceutical compositions containing them are useful for the prevention and treatment of cognitive disorders such as cognitive disorders in Down syndrome. The invention also relates to methods for preventing or treating cognitive disorders including cognitive disorders in Down Syndrome.

Novel diarylheptanoids as inhibitors of TNF-α production

Synthesis and anti-inflammatory activity of novel diarylheptanoids [5-hydroxy-1-phenyl-7-(pyridin-3-yl)-heptan-3-ones and 1-phenyl-7-(pyridin-3-yl) hept-4-en-3-ones] as inhibitors of tumor necrosis factor-α (TNF-α) production is described in the present article. The key reactions involve the formation of a β-hydroxyketone by the reaction of substituted 4-phenyl butan-2-ones with pyridine-3-carboxaldehyde in presence of LDA and the subsequent dehydration of the same to obtain the α,β-unsaturated ketones. Compounds 4i, 5b, 5d, and 5g significantly inhibit lipopolysaccharide (LPS)-induced TNF-α production from human peripheral blood mononuclear cells in a dose-dependent manner. Of note, the in vitro TNF-α inhibition potential of 5b and 5d is comparable to that of curcumin (a naturally occurring diarylheptanoid). Most importantly, oral administration of 4i, 5b, 5d, and 5g (each at 100 mg/kg) but not curcumin (at 100 mg/kg) significantly inhibits LPS-induced TNF-α production in BALB/c mice. Collectively, our findings indicate that these compounds may have potential therapeutic implications for TNF-α-mediated auto-immune/inflammatory disorders.