6515-06-6

Basic information

• Product Name: 3,4-Bis(methoxymethoxy)benzaldehyde
• Synonyms: 3,4-Bis(methoxymethoxy)benzaldehyde
• CAS NO: 6515-06-6
• Molecular Formula: C₁₁H₁₄O₅
• Molecular Weight: 226.23
• Mol File: 6515-06-6.mol
• Article Data: 49

Chemical Properties

• Boiling Point: 354.209 °C at 760 mmHg
• Flash Point: 157.278 °C
• Appearance: /
• Density: 1.161 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.519
• Solubility: Dichloromethane
• CAS DataBase Reference: 3,4-Bis(methoxymethoxy)benzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Bis(methoxymethoxy)benzaldehyde(6515-06-6)
• EPA Substance Registry System: 3,4-Bis(methoxymethoxy)benzaldehyde(6515-06-6)

Safety Data

• Hazardous Substances Data: 6515-06-6(Hazardous Substances Data)

Usage

Uses

3,4-Bis(methoxymethoxy)benzaldehyde is an intermediate used in the synthesis of Okanin (O515750), which extracted from Dalbergia sissoo Roxb. leaves is a good antibacterial agent and possible anti-inflammatory agent. Chalcone. Anti-cancer agent.

InChI:InChI=1/C11H14O5/c1-13-7-15-10-4-3-9(6-12)5-11(10)16-8-14-2/h3-6H,7-8H2,1-2H3

Upstream product

• 13057-17-5 bromethyl methyl ether 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 107-30-2 chloromethyl methyl ether 
• 109-87-5 Dimethoxymethane 

Downstream Products

• 124775-23-1 tetrakis(O-methoxymethyl)butein 
• 849586-50-1 2',4',5',6',3,4-hexa(methoxymethoxy)chalcone 
• 854423-05-5 methyl 2-iodo-3,4-bis(methoxymethoxy)benzoate 
• 99217-68-2 broussochalcone A 
• 1034276-35-1 C₂₉H₃₈O₁₀ 
• 1034276-40-8 C₂₄H₃₀O₁₀ 
• 1446141-01-0 ethyl 3-(3,4-bis(methoxymethoxy)phenyl)-2-((tert-butoxycarbonylamino)methyl)acrylate 
• 1228673-66-2 (2E)-1-(5-hydroxy-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one 
• 552-58-9 eriodictyol 

Relevant articles and documents

Synthetic hispidin, a PKC inhibitor, is more cytotoxic toward cancer cells than normal cells in vitro

The trypanocidal activity of naturally occurring 6-(3,4-dihydroxystyryl)-4-hydroxy-2-pyrone (hispidin) prompted us to examine its cytotoxic activity toward normal and cancerous cells in culture. Hispidin synthesized in our laboratory to a high degree of purity (checked by 1H and 13C NMR spectroscopy) was shown to be cytotoxic (between 10-3 mol/L and 10-7 mol/L) toward normal human MRC-5 fibroblasts, human cancerous keratinocytes (SCL-1 cell line), and human cancerous pancreatic duct cells (Capan-1 cell line). Interestingly, addition of hispidin in three successive doses (between 10-5 mol/L and 10-7 mol/L) led to a 100-fold increase in activity with an enhanced activity on cancer cells compared to normal cells (50%). Synthetic hispidin was found to inhibit isoform β of protein kinase C (IC50 of 2 x 10-6 mol/L), but not E. coli and placental type XV alkaline phosphatases. The enhanced activity of hispidin toward the cancerous cell lines is discussed.

Oxoammonium-Mediated Allylsilane–Ether Coupling Reaction

A new C(sp3)?H functionalization reaction consisting of the oxidative α-allylation of allyl- and benzyl- methyl ethers has been developed. The C?C coupling could be carried out under mild conditions thanks to the use of cheap and green oxoammonium salts. The scope of the reaction was studied over 27 examples, considering the nature of the substituents on the two coupling partners.

Microbial Transformation of Broussochalcones A and B by Aspergillus niger

Broussochalcones A (BCA, 1) and B (BCB, 2) are major bioactive constituents isolated from Broussonetia papyrifera, a polyphenol-rich plant belonging to the family Moraceae. Due to their low yields from natural sources, BCA (1) and BCB (2) were prepared sy

Exploring the 2′-hydroxy-chalcone framework for the development of dual antioxidant and soybean lipoxygenase inhibitory agents

2′-hydroxy-chalcones are naturally occurring compounds with a wide array of bioactiv-ity. In an effort to delineate the structural features that favor antioxidant and lipoxygenase (LOX) inhibitory activity, the design, synthesis, and bioactivity profile of a series of 2′-hydroxy-chalcones bearing diverse substituents on rings A and B, are presented. Among all the synthesized derivatives, chalcone 4b, bearing two hydroxyl substituents on ring B, was found to possess the best combined activity (82.4% DPPH radical scavenging ability, 82.3% inhibition of lipid peroxidation, and satisfac-tory LOX inhibition value (IC50 = 70 μM). Chalcone 3c, possessing a methoxymethylene substituent on ring A, and three methoxy groups on ring B, exhibited the most promising LOX inhibitory activity (IC50 = 45 μM). A combination of in silico techniques were utilized in an effort to explore the crucial binding characteristics of the most active compound 3c and its analogue 3b, to LOX. A common H-bond interaction pattern, orienting the hydroxyl and carbonyl groups of the aromatic ring A towards Asp768 and Asn128, respectively, was observed. Regarding the analogue 3c, the bulky (-OMOM) group does not seem to participate in a direct binding, but it induces an orientation capable to form H-bonds between the methoxy groups of the aromatic ring B with Trp130 and Gly247.