124555-63-1

Basic information

• Product Name: 4-Methoxy-2-(MethoxyMethoxy)benzaldehyde
• Synonyms: 4-Methoxy-2-(MethoxyMethoxy)benzaldehyde
• CAS NO: 124555-63-1
• Molecular Formula: C₁₀H₁₂O₄
• Molecular Weight: 196.19988
• Mol File: 124555-63-1.mol

Chemical Properties

• Melting Point: 62-62.5 °C
• Boiling Point: 126-127 °C(Press: 0.05 Torr)
• Appearance: /
• Density: 1.140±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 4-Methoxy-2-(MethoxyMethoxy)benzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methoxy-2-(MethoxyMethoxy)benzaldehyde(124555-63-1)
• EPA Substance Registry System: 4-Methoxy-2-(MethoxyMethoxy)benzaldehyde(124555-63-1)

Safety Data

• Hazardous Substances Data: 124555-63-1(Hazardous Substances Data)

Upstream product

• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 107-30-2 chloromethyl methyl ether 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 7087-68-5 N-ethyl-N,N-diisopropylamine 

Downstream Products

• 124555-64-2 2'-Hydroxy-4-methoxy-2,4',6'-tri(methoxymethoxy)chalcone 
• 201049-11-8 (E)-3-(4-Methoxy-2-methoxymethoxy-phenyl)-1-(4-methoxy-phenyl)-propenone 
• 209404-20-6 2-[2-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-3-hydroxy-3-(2-methoxymethoxy-phenyl)-propionic acid methyl ester 
• 209404-22-8 methyl 2-(2'-tert-butyldimethylsilyloxy-4'-methoxyphenyl)-3-hydroxy-3-(2''-O-methoxymethyl-4''-methoxyphenyl)propanoate 
• 343256-36-0 methyl 2-{(1,1-dimethylethyl)dimethylsilyloxy}-3-{4-methoxy-2-(O-methoxymethylenoxy)phenyl}prop-2-enoate 

Relevant articles and documents

Design, synthesis, and evaluation of orally available clioquinol-moracin M hybrids as multitarget-directed ligands for cognitive improvement in a rat model of neurodegeneration in Alzheimer's disease

A novel series of clioquinol-moracin hybrids were designed and synthesized by fusing the pharmacophores of clioquinol and moracin M, and their activities as multitarget-directed ligands against Alzheimer's disease were evaluated. Biological activity results demonstrated that these hybrids possessed significant inhibitory activities against phosphodiesterase 4D (PDE4D) and Aβ aggregation as well as remarkable antioxidant effects and excellent blood-brain barrier permeability. The optimal compound, 18d (WBQ5187), exhibited excellent PDE4D inhibitory potency (IC50 = 0.32 μM), significant antioxidant effects, appropriate biometal chelating functions, and interesting properties that modulated self- and metal-induced Aβ aggregation. Two-dimensional NMR studies revealed that 18d had significant interactions with Aβ1-42 at the R5, H6, H14, Q15, and F20 residues. Furthermore, this typical hybrid possessed preeminent neuroprotective effects against inflammation in microglial cells. Most importantly, oral administration of 18d·HCl demonstrated marked improvements in cognitive and spatial memory in a rat model of Alzheimer's disease and protected hippocampal neurons from necrosis.

A chiral pool approach for asymmetric syntheses of both antipodes of equol and sativan

For the first time, both antipodes of the isoflavans, equol and sativan were synthesized in >98% ee with good overall yields starting from readily available starting materials. The chiral isoflavan, (?)-equol is produced from soy isoflavones, formonentin and daidzein by the action of intestinal bacteria in certain groups of population and other chiral isoflavans are reported from various phytochemical sources. To produce these chiral isoflavans in gram quantities, Evans’ enantioselective aldol condensation was used as a chiral-inducing step to introduce the required chirality at the C-3 position. Addition of chiral boron-enolate to substituted benzaldehyde resulted in functionalized syn-aldol products with >90% yield and excellent diastereoselectivity. Functional group transformations followed by intramolecular Mitsunobu reaction and deprotection steps resulted the target compounds, S-(?)-equol and S-(+)-sativan, with high degree of enantiopurity. By simply switching the chiral auxiliary to (S)-4-benzyloxazolidin-2-one and following the same synthetic sequence the antipodes, R-(+)-equol and R-(?)-sativan were achieved. Both enantiomers are of interest from a clinical and pharmacological perspective and are currently being developed as nutraceutical and pharmacological agents. This flexible synthetic process lends itself quite readily to the enantioselective syntheses of other biologically active C-3 chiral isoflavans.

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BRIDGED AND FUSED ANTIDIABETIC COMPOUNDS

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PHENOXYALKANOIC ACID COMPOUND

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