25173-72-2

Basic information

• Product Name: 3-(3,4,5-TRIMETHOXYPHENYL)PROPIONIC ACID
• Synonyms: TIMTEC-BB SBB000794;3,4,5-TRIMETHOXYHYDROCINNAMIC ACID;3-(3,4,5-TRIMETHOXYPHENYL)PROPANOIC ACID;3-(3,4,5-TRIMETHOXYPHENYL)PROPIONIC ACID;AKOS BBS-00006959;LABOTEST-BB LT00233171;BETA-(3,4,5-TRIMETHOXYPHENYL)PROPIONIC ACID;B-(3,4,5-TRIMETHOXYPHENYL)PROPIONIC ACID
• CAS NO: 25173-72-2
• Molecular Formula: C₁₂H₁₆O₅
• Molecular Weight: 240.25
• EINECS: 246-706-4
• Product Categories: Aromatic Propionic Acids;API intermediates
• Mol File: 25173-72-2.mol
• Article Data: 23

Chemical Properties

• Melting Point: 100-104 °C(lit.)
• Boiling Point: 373℃
• Flash Point: 140℃
• Appearance: White to almost white/Crystalline Powder
• Density: 1.169
• Vapor Pressure: 3.1E-06mmHg at 25°C
• Refractive Index: 1.5140 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: methanol: 0.1 g/mL, clear
• PKA: 4.70±0.10(Predicted)
• BRN: 1471912
• CAS DataBase Reference: 3-(3,4,5-TRIMETHOXYPHENYL)PROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3,4,5-TRIMETHOXYPHENYL)PROPIONIC ACID(25173-72-2)
• EPA Substance Registry System: 3-(3,4,5-TRIMETHOXYPHENYL)PROPIONIC ACID(25173-72-2)

Safety Data

• Statements: 36/37/38
• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 25173-72-2(Hazardous Substances Data)

Usage

Description

3-(3,4,5-TRIMETHOXYPHENYL)PROPIONIC ACID, also known as trimethoprim, is a monocarboxylic acid derived from propionic acid with a 3,4,5-trimethoxyphenyl substituent at the 3-position. It is a white to almost white crystalline powder and is known for its various applications in different industries.

Uses

Used in Pharmaceutical Industry:
3-(3,4,5-TRIMETHOXYPHENYL)PROPIONIC ACID is used as an active pharmaceutical ingredient for the treatment of bacterial infections. It works by inhibiting the bacterial enzyme dihydrofolate reductase, which is essential for the synthesis of nucleic acids and proteins in bacteria, thus preventing their growth and multiplication.
Used in Veterinary Medicine:
In the veterinary field, 3-(3,4,5-TRIMETHOXYPHENYL)PROPIONIC ACID is used as an antimicrobial agent for the treatment of bacterial infections in animals. It is often combined with other antibiotics, such as sulfonamides, to enhance its effectiveness against a broader range of bacterial pathogens.
Used in Research and Development:
3-(3,4,5-TRIMETHOXYPHENYL)PROPIONIC ACID is also used in research and development for the synthesis of various chemical compounds and as a starting material for the development of new drugs with potential applications in different therapeutic areas.
Used in Chemical Synthesis:
In the chemical industry, 3-(3,4,5-TRIMETHOXYPHENYL)PROPIONIC ACID serves as an intermediate in the synthesis of various organic compounds, including dyes, pigments, and other specialty chemicals. Its unique structure and reactivity make it a valuable building block for the creation of novel molecules with specific properties and applications.

InChI:InChI=1/C12H16O5/c1-15-9-6-8(4-5-11(13)14)7-10(16-2)12(9)17-3/h6-7H,4-5H2,1-3H3,(H,13,14)/p-1

Upstream product

• 20329-98-0 (E)-3,4,5-trimethoxy-cinnamic acid 
• 1878-29-1 ethyl (E)-3-(3,4,5-trimethoxyphenyl)acrylate 
• 71277-13-9 3,4,5-trimethoxycinnamaldehyde 
• 87212-60-0 5-[(3,4,5-trimethoxyphenyl)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 4521-61-3 3,4,5-Trimethoxybenzoyl chloride 
• 3840-30-0 5-(chloromethyl)-1,2,3-trimethoxybenzene 
• 112044-75-4 2-(4-dimethylamino-phenylimino)-3-oxo-5-(3,4,5-trimethoxy-phenyl)-valeronitrile 
• 36974-47-7 3,4,5-trimethoxy-N-phenyl-benzimidoyl chloride 
• 3840-31-1 (3,4,5-trimethoxyphenyl)methanol 
• 530-56-3 syringic alcohol 
• 20069-09-4 piperlongumine 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 2033-24-1 cycl-isopropylidene malonate 
• 90-50-6 3,4,5-trimethoxycinnamic acid 

Downstream Products

• 1370002-66-6 C₂₀H₂₀N₄O₃S 
• 1370002-67-7 C₂₀H₁₉FN₄O₃S 
• 121667-80-9 {3-[1-Azido-3-(3,4,5-trimethoxy-phenyl)-propyl]-phenoxy}-tert-butyl-dimethyl-silane 
• 121667-79-6 N-[1-[3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-3-(3,4,5-trimethoxy-phenyl)-propyl]-acetamide 
• 121667-81-0 N-[1-(3-Hydroxy-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propyl]-acetamide 
• 122483-58-3 1-[3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-3-(3,4,5-trimethoxy-phenyl)-propan-1-ol 
• 121667-82-1 tert-Butyl-dimethyl-{3-[3-(3,4,5-trimethoxy-phenyl)-propyl]-phenoxy}-silane 
• 17301-91-6 (+/-)-cis-dihydroanhydropodorhizol 
• 80465-01-6 Acetic acid 3-acetoxy-1-{4-[6-(3-acetoxy-propyl)-benzo[1,3]dioxol-5-yl]-3,5-dimethoxy-phenyl}-propyl ester 
• 139448-51-4 (E)-3-(benzo[d][1,3]dioxol-5-yl)allyl 2-bromo-3-(3,4,5-trimethoxyphenyl)propanoate 
• 127951-15-9 2-Bromo-3-(3,4,5-trimethoxy-phenyl)-propionyl chloride 
• 88298-62-8 Acetic acid 6-methoxy-2-methyl-5-oxo-1-[2-(3,4,5-trimethoxy-phenyl)-ethyl]-1,2,3,4,5,6-hexahydro-isoquinolin-6-yl ester 
• 108937-34-4 5-Benzyloxy-6-methoxy-2-methyl-1-[2-(3,4,5-trimethoxy-phenyl)-ethyl]-1,2,3,4-tetrahydro-isoquinoline 
• 108937-31-1 5-Benzyloxy-6-methoxy-1-[2-(3,4,5-trimethoxy-phenyl)-ethyl]-3,4-dihydro-isoquinoline 

Relevant articles and documents

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Synthesis, mitochondrial localization of fluorescent derivatives of cinnamamide as anticancer agents

Mitochondria are considered as a therapeutic target for new drug design toward all kinds of cancer. Hence in order to enhance the dosage in mitochondrial fraction of cinnamamides, the mitochondria-targeted derivatives were designed by the incorporation of cinnamamides into a fluorophore carrier of coumarin-3-carboxamide with a 1:1 stoichiometry. Using the amide linkers, twenty-one compounds were synthesized and the cytotoxicity against a panel of cancer cells (MCF-7, Hela, HepG2, HL-60) was tested. In particular, compound 18c displayed the potent cytotoxicity toward HL-60 leukaemia cells, which could quickly and efficiently entry into HL-60 cells and specifically localize within mitochondria. And 18c preferred enrichment in HL-60 cells than in PBMC normal cells, accounting for the higher toxicity to cancer cells than to normal cells. Moreover, the dissipations of mitochondrial membrane potential and enhancement of cellular ROS level were also preceded upon 18c treatment, leading to cell cycle arrest and apoptosis/necrosis in HL-60 cells. Besides, acted as a Michael acceptor, 18c initiated a thia-Michael addition reaction toward cysteamine (1:2 stoichiometry), detecting by the UV-Vis spectrum and HRMS analysis. This could result in the blue emission of 18c in mitochondria after the procedure of cell fixation, owing to the formation of covalent bond with mitochondrial thiols. Our study reported 18c might be useful for the further development into a mitochondria-targeted anti-leukemia agent and the Michael acceptor might be a versatile functional group.

Synthesis, in vitro and in silico evaluation of diaryl heptanones as potential 5LOX enzyme inhibitors

A new series of diaryl heptanones (12a-q) were synthesized and their structures were confirmed by its 1H, 13C NMR and Mass spectral data. These analogs were evaluated for their anti-oxidant activity and potential to inhibit 5-lipoxygenase. Compounds 12k and 12o showed potent in vitro 5-lipoxygenase enzyme inhibitory activity with IC50 values of 22.2, 21.5 μM, which are comparable to curcumin (24.4 μM). Further they also have shown significant antioxidant activity. Molecular docking studies clearly showed correlation between binding energy and potency of these compounds.