15001-27-1

Basic information

• Product Name: 3,4-DIMETHOXYBENZYLIDENEACETONE
• Synonyms: LABOTEST-BB LT00454316;(E)-4-(3,4-DIMETHOXYPHENYL)BUT-3-EN-2-ONE;3,4-DIMETHOXYBENZYLIDENEACETONE;4-(3,4-Dimethoxy)phenyl-3-buten-2-one;3,4-DIMETHOXYBENZYLIDENEACETONE, 98+%;1-(3,4-Dimethoxyphenyl)-1-butene-3-one;3-(3,4-Dimethoxyphenyl)-3-buten-2-one
• CAS NO: 15001-27-1
• Molecular Formula: C₁₂H₁₄O₃
• Molecular Weight: 206.24
• EINECS: 239-095-0
• Mol File: 15001-27-1.mol
• Article Data: 58

Chemical Properties

• Melting Point: 85-87°C
• Boiling Point: 347.5°Cat760mmHg
• Flash Point: 155.2°C
• Appearance: /
• Density: 1.073g/cm³
• Vapor Pressure: 5.37E-05mmHg at 25°C
• Refractive Index: 1.539
• BRN: 1967327
• CAS DataBase Reference: 3,4-DIMETHOXYBENZYLIDENEACETONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIMETHOXYBENZYLIDENEACETONE(15001-27-1)
• EPA Substance Registry System: 3,4-DIMETHOXYBENZYLIDENEACETONE(15001-27-1)

Safety Data

• Safety Statements: 22-24/25
• Hazardous Substances Data: 15001-27-1(Hazardous Substances Data)

Usage

General Description

3,4-DIMETHOXYBENZYLIDENEACETONE, also known as DMBA, is a chemical compound with the molecular formula C11H14O3. It is a yellow crystalline solid that is commonly used as a starting material in the synthesis of various pharmaceuticals and agrochemicals. DMBA has been studied for its potential anti-inflammatory and antioxidant properties, and it has been found to exhibit cytotoxic effects against certain cancer cell lines. Additionally, it has been used as a reagent in the preparation of chiral catalysts in asymmetric synthesis. However, DMBA is considered a hazardous substance and should be handled with caution due to its potential for skin and eye irritation, as well as its potential harmful effects if ingested or inhaled.

InChI:InChI=1/C12H14O3/c1-9(13)4-5-10-6-7-11(14-2)12(8-10)15-3/h4-8H,1-3H3/b5-4+

Upstream product

• 64-17-5 ethanol 
• 64-19-7 acetic acid 
• 110-89-4 piperidine 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 6302-60-9 4-(3,4-dimethoxy-phenyl)-butan-2-one 
• 97387-80-9 1-(3,4-dimethoxy-phenyl)-but-3-en-1-ol 
• 155586-41-7 1-(3,4-Dimethoxy-phenyl)-buta-2,3-dien-1-one 
• 1454271-71-6 (E)-1-(3,4-dimethoxyphenyl)-3-fluorobut-2-en-1-one 
• 121-33-5 vanillin 
• 1080-12-2 (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-one 
• 74-88-4 methyl iodide 
• 1139874-39-7 (R)-4-(3,4-dimethoxyphenyl)-4-((4-methoxyphenyl)amino)butan-2-one 
• 74-83-9 methyl bromide 
• 93-03-8 (3,4-dimethoxyphenyl)methanol 

Downstream Products

• 76539-81-6 6-(3,4-Dimethoxy-phenyl)-4-pyrrolidin-1-yl-5,6-dihydro-thiopyran-2-thione 
• 76539-80-5 6-(3,4-Dimethoxy-phenyl)-4-piperidin-1-yl-5,6-dihydro-thiopyran-2-thione 
• 130001-17-1 5-(3,4-Dimethoxy-phenyl)-1,3-bis-(3-methoxy-phenyl)-7-methyl-2-thioxo-1,2,3,5-tetrahydro-pyrano[2,3-d]pyrimidin-4-one 
• 89690-20-0 (4R*,9aR*)-4-(3,4-dimethoxyphenyl)octahydro-2H-quinolizin-2-one 
• 79622-76-7 3,4-Dimethoxy-(3'-hydroxybutyl)-benzol 
• 143015-71-8 (E)-3-hydroxy-1-(3,4-dimethoxyphenyl)but-1-ene 
• 79622-77-8 3,4-Dimethoxy-(2',3'-dideuterio-3'-hydroxybutyl)-benzol 
• 61696-80-8 3-(3,4-dimethoxyphenyl)-1-tetralone 
• 14367-32-9 2-<3,4-Dimethoxy-phenyl>-4,6-dioxo-cyclohexancarbonsaeure-ethylester 
• 2316-26-9 3,4-dimethoxycinnamic acid 
• 276681-05-1 (E)-3-tert-butyldimethylsiloxy-1-(3,4-dimethoxyphenyl)-1,3-butadiene 
• 160096-59-3 4',4''-O,O-dimethylcurcumin 
• 889653-79-6 C₁₂H₁₆O₃ 
• 1433962-86-7 (2R,3S)-ethyl 3-(3,4-dimethoxyphenyl)-2-nitro-5-oxohexanoate 

Relevant articles and documents

One-pot sequential oxidation and aldol-condensation reactions of veratryl alcohol catalyzed by the Ru@ZIF-8 + CuO/basic ionic liquid system

The development of green and efficient methods to transform lignin into fuels and high value-added chemicals is of great importance. In this work, we studied one-pot sequential oxidation and aldol-condensation reactions of veratryl alcohol in a basic ionic liquid (BIL) 1-butyl-3-methylimidazolium 5-nitrobenzimidazolide, which acted as the solvent and provided the basic conditions required for the reactions. The effects of different factors such as the type of catalyst, reaction time, reaction temperature, and the amount of BIL on the oxidation reaction were investigated. It was demonstrated that the catalytic performance of individual Ru@ZIF-8 (zeolitic imidazolate framework-8) or CuO was very poor for the oxidation of veratryl alcohol to veratryl aldehyde. Interestingly, Ru@ZIF-8 + CuO was very efficient for the oxidation reaction and a high yield of veratryl aldehyde could be obtained, indicating the excellent synergistic effect of the two catalysts in the BIL. The veratryl aldehyde generated by the oxidation of veratryl alcohol could react directly with acetone to form 3,4-dimethoxybenzylideneacetone by aldol-condensation reaction catalyzed by the BIL in high yield.

Novel substituted 5-methyl-4-acylaminoisoxazoles as antimitotic agents: Evaluation of selectivity to LNCaP cancer cells

A series of novel antimitotic agents was designed using the replacement of heterocyclic cores in two tubulin-targeting lead molecules with the acylated 4-aminoisoxazole moiety. Target compounds were synthesized via heterocyclization of β-aryl-substituted vinylketones by tert-butyl nitrite in the presence of water as a key step. 4-Methyl-N-[5-methyl-3-(3,4,5-trimethoxyphenyl)isoxazol-4-yl]benzamide (1aa) was found to stimulate partial depolymerization of microtubules of human lung carcinoma A549 cells at a high concentration of 100 μM and to totally inhibit cell growth (IC50 = 0.99 μM) and cell viability (IC50 = 0.271 μM) in the nanomolar to submicromolar concentration range. These data provide evidence of the multitarget profile of the cytotoxic action of compound 1aa. The SAR study demonstrated that the 3,4,5-trimethoxyphenyl residue is the key structural parameter determining the efficiency both towards tubulin and other molecular targets. The cytotoxicity of 3-methyl-N-[5-methyl-3-(3,4,5-trimethoxyphenyl)isoxazol-4-yl]benzamide (1ab) to the androgen-sensitive human prostate adenocarcinoma cancer cell line LNCaP (IC50 = 0.301 μM) was approximately one order of magnitude higher than that to the conditionally normal cells lines WI-26 VA4 (IC50 = 2.26 μM) and human umbilical vein endothelial cells (IC50 = 5.58 μM) and significantly higher than that to primary fibroblasts (IC50 > 75 μM).

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.

The construction of novel and efficient hafnium catalysts using naturally existing tannic acid for Meerwein-Ponndorf-Verley reduction

The conversion of carbonyl compounds into alcohols or their derivatives via the catalytic transfer hydrogenation (CTH) process known as Meerwein-Ponndorf-Verley reduction is an important reaction in the reaction chain involved in biomass transformation. The rational design of efficient catalysts using natural and renewable materials is critical for decreasing the catalyst cost and for the sustainable supply of raw materials during catalyst preparation. In this study, a novel hafnium-based catalyst was constructed using naturally existing tannic acid as the ligand. The prepared hafnium-tannic acid (Hf-TA) catalyst was characterized by scanning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FTIR), and thermogravimetry (TG). Hf-TA was applied in the conversion of furfuraldehyde (FD) to furfuryl alcohol (FA) using isopropanol (2-PrOH) as both the reaction solvent and the hydrogen source. Both preparation conditions and the effects of the reaction parameters on the performance of the catalyst were studied. Under the relatively mild reaction conditions of 70 °C and 3 h, FD (1 mmol) could be converted into FA with a high yield of 99.0%. In addition, the Hf-TA catalyst could be reused at least ten times without a notable decrease in activity and selectivity, indicating its excellent stability. It was proved that Hf-TA could also catalyze the conversion of various carbonyl compounds with different structures. The high efficiency, natural occurrence of tannic acid, and facile preparation process make Hf-TA a potential catalyst for applications in the biomass conversion field.