85593-77-7

Basic information

• Product Name: Benzoic acid, 2,4-bis(phenylmethoxy)-
• CAS NO: 85593-77-7
• Molecular Formula: C21H18O4
• Molecular Weight: 334.372
• Mol File: 85593-77-7.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 2,4-bis(phenylmethoxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 2,4-bis(phenylmethoxy)-(85593-77-7)
• EPA Substance Registry System: Benzoic acid, 2,4-bis(phenylmethoxy)-(85593-77-7)

Safety Data

• Hazardous Substances Data: 85593-77-7(Hazardous Substances Data)

Upstream product

• 89-86-1 4-hydroxysalicylic acid 
• 100-39-0 benzyl bromide 
• 2150-47-2 methyl 2,4-dihydroxybenzoate 
• 85593-76-6 methyl 2,4-bis(benzyloxy)benzoate 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 13246-46-3 2,4-dibenzyloxybenzaldehyde 
• 100-44-7 benzyl chloride 

Downstream Products

• 85593-78-8 2-formyl-4,5-methylenedioxyphenyl 2',4'-dibenzyloxybenzoate 
• 5448-45-3 4-(benzyloxy)-2-hydroxybenzoic acid 
• 125718-81-2 (5-{(S)-2-[2-(2,4-Bis-benzyloxy-phenyl)-acetylamino]-3-carbamoyl-propionylamino}-pentyl)-carbamic acid tert-butyl ester 
• 113978-98-6 dibenzyl-2,4-dihydroxyphenylacetic acid N-hydroxysuccinimide ester 
• 113954-15-7 (S)-N¹-(5-Amino-pentyl)-2-[2-(2,4-bis-benzyloxy-phenyl)-acetylamino]-succinamide 
• 121903-72-8 1-(2,4-Bis-benzyloxy-phenyl)-2-diazo-ethanone 
• 105029-41-2 Argiotoxin 636 
• 174007-70-6 C₇₅H₈₈N₁₀O₁₄ 
• 174007-67-1 (S)-2-[2-(2,4-Bis-benzyloxy-phenyl)-acetylamino]-N¹-(5-hydroxy-pentyl)-succinamide 
• 172992-23-3 (S)-2-[2-(2,4-Bis-benzyloxy-phenyl)-acetylamino]-N¹-(5-oxo-pentyl)-succinamide 
• 1331965-86-6 N-(2,4-bis(benzyloxy)phenyl)-6-iodobenzo[d][1,3]dioxole-5-carboxamide 
• 1331965-90-2 C₃₄H₃₆INO₆Si 
• 1331965-94-6 2,4-bis(benzyloxy)-5-((2-(trimethylsilyl)ethoxy)methyl)-[1,3]dioxolo[4,5-j]phenanthridin-6(5H)-one 
• 724695-86-7 2,4-bis(benzyloxy)aniline 

Relevant articles and documents

Inhibition of Plasmodium falciparum Lysyl-tRNA Synthetase via a Piperidine-Ring Scaffold Inspired Cladosporin Analogues

Plasmodium falciparum lysyl-tRNA synthetase (PfKRS) represents a promising therapeutic anti-malarial target. Cladosporin was identified as a selective and potent PfKRS inhibitor but lacks metabolic stability. Here, we report chemical synthesis, biological evaluation and structural characterization of analogues where the tetrahydropyran (THP) frame of cladosporin is replaced with the piperidine ring bearing functional group variations. Thermal binding, enzymatic, kinetic and parasitic assays complemented with X-ray crystallography reveal compounds that are moderate in potency. Co-crystals of Cla?B and Cla?C with PfKRS reveal key atomic configurations that allow drug binding to and inhibition of the enzyme. Collectively these piperidine ring scaffold inhibitors lay a framework for further structural editing and functional modifications of the cladosporin scaffold to obtain a potent lead.

Lipidated Brartemicin Analogues Are Potent Th1-Stimulating Vaccine Adjuvants

Effective Th1-stimulating vaccine adjuvants typically activate antigen presenting cells (APCs) through pattern recognition receptors (PRRs). Macrophage inducible C-type lectin (Mincle) is a PRR expressed on APCs and has been identified as a target for Th1-stimulating adjuvants. Herein, we report on the synthesis and adjuvanticity of rationally designed brartemicin analogues containing long-chain lipids and demonstrate that they are potent Mincle agonists that activate APCs to produce inflammatory cytokines in a Mincle-dependent fashion. Mincle binding, however, does not directly correlate to a functional immune response. Mutation studies indicated that the aromatic residue of lead compound 9a has an important interaction with Mincle Arg183. In vivo assessment of 9a highlighted the capability of this analogue to augment the Th1 response to a model vaccine antigen. Taken together, our results show that lipophilic brartemicin analogues are potent Mincle agonists and that 9a has superior in vivo adjuvant activity compared to TDB.

Benzoic hydroxamate-based iron complexes as model compounds for humic substances: Synthesis, characterization and algal growth experiments

A series of monomeric and dimeric FeIII complexes bearing benzoic hydroxamates as O,O-chelates has been prepared and characterized by elemental analysis, IR spectroscopy, UV-Vis spectroscopy, electrospray ionization mass spectrometry (ESI-MS), cyclic voltammetry, EPR spectroscopy and for some examples by X-ray diffraction analysis. The stability of the synthesized complexes in pure water and seawater was monitored over 24 h by means of UV-Vis spectrometry. The ability to release iron from the synthesized model complexes has been investigated with algae growth experiments.