57695-98-4

Basic information

• Product Name: 3-METHOXY-4-PROPOXY-BENZALDEHYDE
• Synonyms: AKOS B000245;AKOS BBS-00006610;3-METHOXY-4-PROPOXY-BENZALDEHYDE;ASISCHEM U93005;AURORA 2592;ART-CHEM-BB B000245;3-METHOXY-4-N-PROPOXYBENZALDEHYDE
• CAS NO: 57695-98-4
• Molecular Formula: C₁₁H₁₄O₃
• Molecular Weight: 194.23
• Mol File: 57695-98-4.mol

Chemical Properties

• Melting Point: 59-60 °C
• Boiling Point: 304.7 °C at 760 mmHg
• Flash Point: 129 °C
• Appearance: /
• Density: 1.066 g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-METHOXY-4-PROPOXY-BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHOXY-4-PROPOXY-BENZALDEHYDE(57695-98-4)
• EPA Substance Registry System: 3-METHOXY-4-PROPOXY-BENZALDEHYDE(57695-98-4)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 57695-98-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-METHOXY-4-PROPOXY-BENZALDEHYDE is used as a key intermediate in the synthesis of chalcone derivatives of benzo[b]furan. These derivatives have been identified as potential antibacterial agents, making them valuable in the development of new drugs to combat bacterial infections.
Application Reason:
3-METHOXY-4-PROPOXY-BENZALDEHYDE's unique structure allows for the formation of chalcone derivatives with potential antibacterial properties. These derivatives can be further studied and optimized to develop effective treatments for various bacterial diseases, contributing to the ongoing efforts to address the global challenge of antibiotic resistance.

Upstream product

• 121-33-5 vanillin 
• 540-54-5 1-Chloropropane 
• 29515-39-7 1-methoxy-2-n-propoxybenzene 
• 93-61-8 N-methyl-N-phenylformamide 
• 90-05-1 2-methoxy-phenol 
• 106-94-5 propyl bromide 
• 107-08-4 1-iodo-propane 

Downstream Products

• 103859-81-0 (3-methoxy-4-propoxyphenyl)methanol 
• 1335128-35-2 4-((4-chlorophenyl)(hydroxyl)methyl)-1-(3-methoxy-4-propoxybenzyl)-1H-1,2,3-triazole 
• 1335128-04-5 C₁₂H₁₈O₃ 
• 1335128-11-4 2-(3-methoxy-4-propoxyphenyl)ethyl tosylate 
• 1335128-17-0 C₁₂H₁₇N₃O₂ 
• 1335128-31-8 4-(azidomethyl)-2-methoxy-1-propoxybenzene 
• 261359-02-8 4-(propyloxy)-3-methoxybenzyl bromide 
• 1340261-69-9 C₁₂H₁₆O₂ 
• 121-33-5 vanillin 

Relevant articles and documents

Potent human dihydroorotate dehydrogenase inhibitory activity of new quinoline-4-carboxylic acids derived from phenolic aldehydes: Synthesis, cytotoxicity, lipophilicity and molecular docking studies

A series of novel 2-substituted quinoline-4-carboxylic acids was synthesized by Doebner reaction starting from freely available protocatechuic aldehyde and vanillin precursors. Human dihydroorotate dehydrogenase (hDHODH) was recognised as a clear molecular target for these heterocycles. All compounds were also tested for their antiproliferative potential against three cancer cells (MCF-7, A549, A375) and one normal cell line (HaCaT) to evaluate the selective cytotoxicity. Quinoline derivatives 3f and 3g were identified as potent hDHODH inhibitors while 3k and 3l demonstrated high cytotoxic activity against MCF-7 and A375 cells and good selectivity. In addition, the logD7.4 values obtained by the experimental method were found to be in the range from ?1.15 to 1.69. The chemical structures of all compounds were confirmed by IR, NMR and elemental analysis. The compounds pharmacology on the molecular level was revealed by means of molecular docking, highlighting the structural differences that distinguish highly active from medium and low active hDHODH inhibitors.

Novel vanillin derivatives containing a 1,3,4-thiadiazole moiety as potential antibacterial agents

In this study, thirty-four novel vanillin derivatives containing a 1,3,4-thiadiazole structure were obtained and their antibacterial activities were evaluated. The results indicate that most of the title compounds displayed inhibitory effects on Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas oryzae pv. oryzicola (Xoc). Among them, compound 29 exhibited excellent antibacterial activities against Xoo and Xoc in vitro, with the EC50 values of 3.14 and 8.83 μg/mL, respectively, much superior to thiodiazole copper (87.03 and 108.99 μg/mL) and bismerthiazol (67.64 and 79.26 μg/mL). Under greenhouse condition, the protective efficiency of compound 29 against rice bacterial leaf blight was 49.34%, and curative efficiency was 40.96%. In addition, compound 29 can reduce the exopolysaccharides production of Xoo, increase the permeability of cell membrane and damage cell membrane.

First Discovery of Novel Pyrido[1,2- a]pyrimidinone Mesoionic Compounds as Antibacterial Agents

Plant bacterial diseases cause tremendous decreases in crop yield and quality, and there is a lack of highly effective and low-risk antibacterial agents. A series of novel pyrido[1,2-a]pyrimidinone mesoionic compounds containing vanillin moieties were synthesized, and the application of these mesoionic compounds as plant antibacterial agents was reported here for the first time. The bioassay results revealed that the mesoionic compounds had good antibacterial activity. Of these compounds, compound 11 showed excellent in vitro activity against Xanthomonas oryzae pv. oryzae, with an EC50 value of 1.1 μg/mL, which was substantially better than that of bismerthiazol (92.7 μg/mL) and thiodiazole copper (105.4 μg/mL). Moreover, greenhouse condition trials indicated that the protective and curative activities of compound 11 against rice bacterial leaf blight were 75.12 and 72.04%, respectively, which were better than those of bismerthiazol (62.24 and 50.83%, respectively) and thiodiazole copper (53.35 and 65.04%, respectively). These results provide a basis for the application of mesoionic vanillin moieties as new antibacterial agents.

Senecio scandens derivative and application thereof in drugs

The invention discloses a senecio scandens derivative and application thereof in drugs. The enecio scandens derivative is the derivative of the effective component chlorogenic acid of senecio scandens. The derivative of the chlorogenic acid is a compound as shown in chemical generation formula I, II, III or IV or one or the combination of the stereisomer, geometrical isomer, tautomer, solvate, polymorphic substance, metabolite, ester, pharmaceutically acceptable salt, prodrug, pharmaceutically acceptable prodrug salt, pharmaceutically acceptable carrier, excipient, diluent, adjuvant and intermedium of the compound. The senecio scandens derivative is used for preparing antiviral drugs. The senecio scandens derivative is good in solubility, high in purity, good in antipyretic performance andespecially suitable for being used as the effective component to prepare antipyretic, anti-inflammation and antibacterial drugs.

Synthesis and characterization of new homologous series of unsymmetrical liquid crystalline compounds based on chalcones and 3, 5-disubstituted isoxazoles

Two homologous series of unsymmetrical alkylated chalcones and 3,5-diaryl isoxazoles, consisting of 20 members, with various n-alkyl bromides (n=2?7, 10, 12, 14, 16) have been synthesized and studied for their liquid crystalline property. Simple strategy was employed to achieve the target materials. Flexibility in the synthesized molecules is provided by attaching straight alkoxy chains, where one terminal group is fixed and other terminal group is varied. The synthesized compounds were characterized on the basis of Mass, IR and NMR spectroscopy. The stability and the range of the mesophases increased with the length of the chain on the isoxazoles. The melting point, transition temperatures and enantiotropic liquid crystal morphologies were determined by polarizing optical microscopy (POM) in conjunction with a hot stage and by differential scanning calorimetry (DSC). [Figure not available: see fulltext.]

Ferrocenyl chalcones with O-alkylated vanillins: synthesis, spectral characterization, microbiological evaluation, and single-crystal X-ray analysis

O-alkylated vanillin derivatives 2a–f and acetylferrocene react under Claisen–Schmidt conditions, resulting in good-to-high yields of the corresponding ferrocene chalcones 3a–f. None of the resultant compounds 3b–f has been previously described in the literature. All synthesized compounds were characterized by spectral and physical data, whereas two of them, 1-ferrocenyl-3-(4-ethoxy-3-methoxyphenyl)-prop-2-en-1-one (3b) and 1-ferrocenyl-3-(4-buthoxy-3-methoxy-phenyl)-prop-2-en-1-one (3e), were crystalline substances, suitable for single-crystal X-ray analysis, which confirmed undoubtedly their structures. Chalcones 3a–f were tested for their biological activity and demonstrated relatively good in vitro antimicrobial activity towards different strains of bacteria and fungi. The best antibacterial activity is expressed by compounds 3b and 3c, while compound 3d shows the best antifungal activity.

Concurrent synthesis of vanillin and isovanillin

A method for concurrent synthesis of vanillin and isovanillin has been developed by a nonregioselective Vilsmeier-Haack reaction of O-alkyl guaiacols. O-Alkylation of guaiacol provided the corresponding O-alkyl guaiacol (1), which was then formylated with N-methylformanilide/phosphorus oxychloride to give a mixture of 4-alkoxy-3-methoxy-benzaldehyde (2) and 3-alkoxy-4- methoxybenzaldehyde (3). Finally, the obtained mixture underwent a selective dealkylation by anhydrous aluminium trichloride, while leaving methyl groups intact to simultaneously achieve the significant fine chemicals vanillin and isovanillin.

Synthesis and biological evaluation of isosteric analogs of mandipropamid for the control of oomycete pathogens

A series of isosteric analogs of mandipropamid were designed and synthesized via 'click chemistry'. The amide bond of mandipropamid was substituted by a 1,2,3-triazole functional group. The bioassay results have indicated that some of the title compounds exhibited moderate fungicidal activity against Pseudoperonospora cubensis, and the activity has been systematically studied as a function of molecular structure. The low activity of the mandipropamid analog that contains a lipid chain is likely due to the presence of a weak hydrogen bond donor in the 1,2,3-triazole. Furthermore, we have performed the molecular modeling and found that N-methylamide could be more effective than amide as the surrogates to 1,2,3-triazole, which ultimately leads to a longer distance (1.1A longer) between the two substitutes in the 1,4-disubstituted 1,2,3-triazole compound.

THE PREPARTION AND THE USE OF ETHOXY COMBRETASTATINS AND THEIR PRODRUGS

The invention disclosed a total synthesis process of novel ethoxy combretastatins and their prodrugs. Combretastatins are chemically modified by ethoxy substituted on the 4'-position of their B aryl ring and are converted to be their soluble prodrugs of phosphate or their inner salt of phosphorylcholine by modifying the hydroxyl on the 3'-position of their B aryl ring. Similarly, 3'-amino combretastatin is 4'-ethoxy chemically modified and further side chain of amino acid can be introduced to the amino to form soluble prodrug of amino acidamide. The structure of the said compound is showed as formula (I). Ethoxy combretastatins possess potent tubulin polymerization inhibitory activity and can be used for the treatment of inhibiting tumor or neovascular.

Substituted γ-phenyl-Δ-lactams and uses related thereto

γ-Phenyl-substituted Δ-lactams are disclosed. They may be formulated into pharmaceutical compositions, and/or used in the treatment or prevention of inflammation or other conditions or disease states.