7560-49-8

Usage

Uses

Used in Chemical Industry:
3,4,5-Trimethoxybenzeneacrylic acid methyl ester is used as an intermediate in the synthesis of other complex compounds. Its presence in the chemical industry is crucial for the production of various chemical products due to its unique chemical properties.
Used in Pharmaceutical Industry:
3,4,5-Trimethoxybenzeneacrylic acid methyl ester is used as a building block for the development of new pharmaceutical compounds. Its versatility in chemical reactions and the potential for creating novel drug molecules make it a valuable asset in the pharmaceutical sector.
Used in Research and Development:
3,4,5-Trimethoxybenzeneacrylic acid methyl ester is used as a research compound for studying its chemical properties and potential applications. Its unique structure and reactivity provide opportunities for exploring new chemical reactions and discovering innovative uses in various fields.

InChI:InChI=1/C13H16O5/c1-15-10-7-9(5-6-12(14)17-3)8-11(16-2)13(10)18-4/h5-8H,1-4H3/b6-5+

Upstream product

• 88738-78-7 bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 853751-44-7 N-(3,4,5-trimethoxybenzylidene)methanesulfonamide 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 6093-59-0 trans-3-(3,4,5-trihydroxyphenyl)-2-propenoic acid 
• 77-78-1 dimethyl sulfate 
• 14546-70-4 3-(3,4,5-trimethoxy-phenyl)-oxiranecarboxylic acid methyl ester 
• 67-56-1 methanol 
• 90-50-6 3,4,5-trimethoxycinnamic acid 
• 530-59-6 sinapinic acid 
• 74-88-4 methyl iodide 
• 10263-19-1 3',4',5'-trimethoxycinnamoyl chloride 
• 4698-21-9 3-(3,4,5-trimethoxyphenyl)propiolic acid 
• 186581-53-3 diazomethane 

Downstream Products

• 20329-99-1 (Z)3,4,5-trimethoxycinnamic acid 
• 71616-31-4 (E)-3,4-methylenedioxycinnamyl (Z)-3-(3,4,5-trimethoxyphenyl)acrylate 
• 90-50-6 3,4,5-trimethoxycinnamic acid 
• 53560-25-1 methyl 3-(3,4,5-trimethoxyphenyl)propionate 
• 79117-99-0 methyl 2-(3,4,5-trimethoxyphenyl)cyclopropanecarboxylate 
• 141396-27-2 dimethyl t-3,t-4-di-(3,4,5-trimethoxyphenyl)cyclobutane-r-1,c-2-dicarboxylate 
• 141341-76-6 dimethyl t-3,c-4-di-(3,4,5-trimethoxyphenyl)cyclobutane-r-1,t-2-dicarboxylate 
• 73307-44-5 7-amino-10-hydroxy-1,2,3-trimethoxy-6,7-dihydro-5H-benzo[a]heptalen-9-one 
• 79117-98-9 methyl 4-(3,4,5-trimethoxyphenyl)butanoate 
• 79117-97-8 methyl α-(2-hydroxy-4-methoxy-5-oxobicyclo<4.1.0>hept-3-en-1-yl)-α-(β-(3,4,5-trimethoxyphenyl)ethyl)acetate 
• 73276-13-8 2-(2-Hydroxy-4,5,5-trimethoxy-bicyclo[4.1.0]hept-3-en-2-yl)-4-(3,4,5-trimethoxy-phenyl)-butyric acid methyl ester 
• 243666-37-7 (±)-7-methoxy-4-(3,4,5-trimethoxyphenyl)-3,4-dihydrocoumarin 
• 1013933-93-1 3,4-dihydro-5,7-dimethoxy-4-(3,4,5-trimethoxyphenyl)coumarin 
• 1240483-57-1 8-(3,4,5-trimethoxyphenyl)-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]-chromen-6-one 

Relevant academic research and scientific papers

Synthesis of novel 1-phenyl-benzopyrrolizidin-3-one derivatives and evaluation of their cytoneuroprotective effects against NMDA-induced injury in PC12 cells

A range of novel 1-phenyl-benzopyrrolizidin-3-one derivatives were synthesized and evaluated for neuroprotective effects against N-methyl-?-aspartate (NMDA)-induced injury in PC12 cells. Interestingly, derivatives that 1-phenyl moiety bearing electron-donating group, especially benzyloxy, and the trans-forms exhibited better protective activity against NMDA-induced neurotoxicity. Compound 11 m demonstrated the best neuroprotective potency and shown a dose-dependent prevention. The increased intracellular calcium (Ca2+) influx caused by NMDA in PC12 cells was reversed in the case of compound 11 m pretreatment at 15 μM. These results suggested that the synthesized 1-phenyl-benzopyrrolizidin-3-one derivatives exerted neuroprotective effect on NMDA-induced excitotoxicity in PC12 cells associated with inhibition of Ca2+ overload and can be further optimized for the development of neuroprotective agents.

METHOD FOR THE SYNTHESIS AND PURIFICATION OF ARYL ACID ESTERS

The general inventive concepts are directed to the discovery that certain aryl acids can be esterified under particular conditions to provide the resulting ester as a solid that precipitates in good yield from the reaction mixture. The esters may then be isolated and purified with relative ease. Accordingly, a method for the esterification, isolation, and purification of aryl acids is provided.

Synthesis and discovery of 18β-glycyrrhetinic acid derivatives inhibiting cancer stem cell properties in ovarian cancer cells

Despite advances in ovarian cancer treatment, the five-year overall survival rate is less than 30% with the presence of cancer stem cells (CSCs). To develop CSC-targeting therapy, a series of 18β-glycyrrhetinic acid (GA) derivatives containing cinnamamide moiety have been designed, synthesized, and screened for their antiproliferative activity in SKOV3 and OVCAR3 cells. Most of the compounds exhibited stronger antiproliferative activity than GA, and compound 7c was the most active one. Further biological studies showed that compound 7c could induce apoptosis and suppress migration. In addition, compound 7c could not only observably decrease the colony formation and sphere formation ability, but also significantly reduce the CD44+, CD133+, and ALDH+ subpopulation in SKOV3 and OVCAR3 cells. In conclusion, these results indicate that compound 7c is a promising anti-CSC agent for further anti-ovarian cancer studies.

Biological activity of sinapic acid derivatives isolated from raphanus sativus

Radish sprout (Raphanus sativus) is a vegetable sprout that contains various sinapic acid derivatives. In this study, three sinapic acid derivatives 1-3 isolated from R. sativus, sinapic acid (4), and compounds 5-7, derived from the methylation of compoun

Stereoselective olefination of N-sulfonyl imines with stabilized phosphonium ylides for the synthesis of electron-deficient alkenes

An unprecedented protocol has been developed for thestereoselective synthesis of structurally diverse electron-deficient alkenes in moderate to excellent yields from readily accessible N-sulfonyl imines and stabilized phosphonium ylides. Significantly, the olefination reaction of N-sulfonylimines with nitrile-stabilized phosphonium ylides affords an array of α,β-unsaturated nitriles with high Z selectivity, and the reactions with ester-, amide-, and ketone-stabilized phosphonium ylides afford α,β-unsaturated esters, amides, and ketones with high E selectivity, respectively. Spectroscopic analysis of the reaction mixtures and trapping of the intermediates allow plausible mechanisms to be proposed. Initialimine/ylide addition leads to the formation of betaines that cyclize to form 1,2-azaphosphetanes that subsequently eliminate iminophosphoranes to yield alkenes. For the synthesis of electron-deficient 1,2-disubstituted alkenes, the presence of an electron-withdrawing group in the betaine allows rapid interconversion between its two diastereomers through proton transfer. The Z/E selectivity for alkene synthesis is determined by the different rates at which the two betaine diastereomers form the corresponding 1,2-azaphosphetane diastereomers. In contrast, the Z/E selectivity for the synthesis of electron-deficient trisubstituted alkenes originates from the diastereoselective addition of stabilized phosphonium ylides to N-sulfonyl imines.

Synthesis, crystal structure, and fungicidal activity of novel 1,5-Diaryl-1H-pyrazol-3-oxyacetate derivatives

A series of ethyl 2-(1,5-diaryl-1H-pyrazol-3-yloxy)acetate derivatives (5a-5i) have been efficiently synthesized by the reaction of 1,5-diaryl-1H-pyrazol-3-ols (4a-4i) with ethyl 2-bromoacetate. The structures of the newly synthesized compounds were characterized by 1H NMR spectra and elemental analysis, and the crystal structure of the compound ethyl 2-(5-(4-chlorophenyl)-1-phenyl-1H-pyrazol-3-yloxy)acetate (5c) was determined by single crystal X-ray diffraction analysis. The compound 5c belongs to triclinic system with space group P(-1), a = 5.8170(12) A, b = 11.804(2) A, c = 12.783(2) A, α = 83.89(2)°, β = 89.24(3)°, γ = 89.73(3)°, Formula weight: 356.80, Triclinic V = 872.7(3) A3, Dc = 1.358 mg/m3, Z = 2, F (000) = 372. Bioassay results indicated that the compound ethyl 2-(5-(4-fluorophenyl)-1- phenyl-1H-pyrazol-3-yloxy)acetate (5d) exhibited moderate inhibitory activity against Gibberella zeae at the dosage of 10 μg/mL.

A new synthesis of podophyllum lignans by Weitz' aminium salt-induced free radical cycloaddition reaction of a doubly unsaturated ester

(±)-Isopodophyllotoxin (1e) and related lactones 12, 13, 14 were synthesized by a biomimetic procedure from the doubly unsaturated esters 11a and 11b by means of an oxidative free radical cycloaddition reaction utilizing a stable cation radical salt, Weitz' aminium salt, in one step. (±)-Isopicropodophyllin (1g), the trans-fused lactones, 12, 13, and 16, and the cis-fused lactone 17 were also synthesized from the esters 11c and 11d by the reaction with the same reagent.