80547-69-9

Usage

Uses

Used in Pharmaceutical Industry:
3-Hydroxy-4-methoxy-5-nitrobenzaldehyde is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic effects.
Used in Dye Industry:
3-Hydroxy-4-methoxy-5-nitrobenzaldehyde is used as a key component in the production of dyes, where its chemical structure allows for the creation of a wide range of colorants for various applications.
Used in Organic Compounds Synthesis:
3-Hydroxy-4-methoxy-5-nitrobenzaldehyde is used as an intermediate in the synthesis of organic compounds, leveraging its chemical reactivity to form new molecules with diverse applications.
Used in Agriculture:
3-Hydroxy-4-methoxy-5-nitrobenzaldehyde is used as an antibacterial and antifungal agent in agricultural applications, helping to protect crops from diseases and improve yield.
Used in Industrial Chemistry:
3-Hydroxy-4-methoxy-5-nitrobenzaldehyde is utilized in various industrial chemical processes due to its versatile chemical properties, contributing to the development of new materials and chemical products.

InChI:InChI=1/C8H7NO5/c1-14-8-6(9(12)13)2-5(4-10)3-7(8)11/h2-4,11H,1H3

Upstream product

• 621-59-0 isovanillin 
• 80547-72-4 acetic acid 5-formyl-2-methoxy-3-nitrophenyl ester 
• 881-57-2 isovanillin acetate 

Downstream Products

• 100966-07-2 4-methoxy-5,3'-dinitro-3,4'-oxy-di-benzaldehyde 
• 130929-57-6 entacapone 
• 1047659-01-7 entacapone; piperidine salt 
• 116314-52-4 ethyl 2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)prop-2-enoate 
• 1081273-75-7 phenethyl (E)-3-(3,4-dihydroxy-5-nitrophenyl)acrylate 
• 116313-85-0 3,4-dihydroxy-5-nitrobenzaldehyde 
• 1314797-69-7 C₁₇H₂₁NO₁₀ 
• 886442-73-5 (Z)-2-(3'-tert-butyldimethylsilyloxy-4'-methoxy-5'-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)ethene 
• 519060-27-6 2-Methoxy-3-nitro-5-[(Z)-2-(3,4,5-trimethoxy-phenyl)-vinyl]-phenol 
• 886442-65-5 3-tert-butyldimethylsilyloxy-4-methoxy-5-nitrobenzaldehyde 
• 343867-62-9 3-Amino-5-hydroxy-4-methoxy-benzaldehyde 

Relevant academic research and scientific papers

Synthesis and Biochemical Evaluation of 3-Phenoxy-1,4-diarylazetidin-2-ones as Tubulin-Targeting Antitumor Agents

Structure-activity relationships for a series of 3-phenoxy-1,4-diarylazetidin-2-ones were investigated, leading to the discovery of a number of potent antiproliferative compounds, including trans-4-(3-hydroxy-4-methoxyphenyl)-3-phenoxy-1-(3,4,5-trimethoxyphenyl)azetidin-2-one (78b) and trans-4-(3-amino-4-methoxyphenyl)-3-phenoxy-1-(3,4,5-trimethoxyphenyl)azetidin-2-one (90b). X-ray crystallography studies indicate the potential importance of the torsional angle between the 1-phenyl A ring and 4-phenyl B ring for potent antiproliferative activity and that a trans configuration between the 3-phenoxy and 4-phenyl rings is generally optimal. These compounds displayed IC50 values of 38 and 19 nM, respectively, in MCF-7 breast cancer cells, inhibited the polymerization of isolated tubulin in vitro, disrupted the microtubular structure in MCF-7 cells as visualized by confocal microscopy, and caused G2/M arrest and apoptosis. Compound 90b possessed a mean GI50 value of 22 nM in the NCI60 cell line screen, displayed minimal cytotoxicity, and was shown to interact at the colchicine-binding site on β-tubulin. Phosphate and amino acid prodrugs of both 78b and 90b were synthesized, of which the alanine amide 102b retained potency and is a promising candidate for further clinical development.

Synthesis and antitumor activity of feruloyl and caffeoyl derivatives This paper is dedicated to Prof. Wei-xiao Hu for his lifelong commitment to mentoring graduate students

We developed two efficient protocols for the synthesis of feruloyl and caffeoyl derivatives from commercial vanillin and veratraldehyde. Pharmacological activities were assessed against a panel of human cancer cell lines in vitro. Most synthesized compounds demonstrated attractive cytotoxicity. Several new compounds demonstrated significant antiproliferative and cytotoxic activities against HeLa and Bewo tumor cell lines. In particular, 5-nitro caffeic adamantyl ester showed broad spectrum of tumor inhibition in 10 cell lines, and reduced tumor weight by 36.7% in vivo when administered at a dose of 40 mg kg-1.

Regioselectivity of the nitration of phenol by acetyl nitrate adsorbed on silica gel

The reaction of phenol with acetyl nitrate in chloroform gives nitrophenol with an ortho/para ratio of 1.8. This ratio increase to 13.3 when the reaction was carried out with acetyl nitrate pre-adsorbed on dry silica gel. Silica may be acting as a template to bring phenol close to acetyl nitrate by hydrogen bonds forming a ternary complex, which undergoes a six- center rearrangement to o-nitrophenol. The formation of this ternary complex is evaluated by ab initio molecular orbital calculation.