149428-74-0

Basic information

• Product Name: 3-METHOXY-4-(2-PHENYLETHOXY)BENZALDEHYDE
• Synonyms: 3-METHOXY-4-(2-PHENYLETHOXY)BENZALDEHYDE;AKOS B029048;OTAVA-BB BB7018801973
• CAS NO: 149428-74-0
• Molecular Formula: C₁₆H₁₆O₃
• Molecular Weight: 256.3
• Mol File: 149428-74-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-METHOXY-4-(2-PHENYLETHOXY)BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHOXY-4-(2-PHENYLETHOXY)BENZALDEHYDE(149428-74-0)
• EPA Substance Registry System: 3-METHOXY-4-(2-PHENYLETHOXY)BENZALDEHYDE(149428-74-0)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• HazardClass: IRRITANT
• Hazardous Substances Data: 149428-74-0(Hazardous Substances Data)

Upstream product

• 121-33-5 vanillin 
• 103-63-9 1-phenyl-2-bromoethane 

Downstream Products

• 1021096-44-5 (3-methoxy-4-phenethyloxy-phenyl)-methanol 
• 1026418-09-6 2-(3-methoxy-4-phenethyloxy-phenyl)-N,N-dipropyl-acetamide 
• 149428-92-2 3-Methoxy-4-(2-phenylethoxy)phenylacetic acid 
• 1039815-64-9 4-Chloromethyl-2-methoxy-1-phenethyloxy-benzene 

Relevant articles and documents

Selective cleavage of aryl ether bonds in dimeric lignin model compounds

Lignin is an abundant renewable feedstock with a complicated and ill-defined structure. As β-O-4 aryl ether bonds are dominant among all the linkages in lignin, it is important to explore lignin depolymerization targeting the cleavage of the β-O-4 aryl ether bond for efficiently utilizing this biomass. Selective cleavage of chemical bonds in β-O-4 lignin model compounds was investigated by using Fe2(SO4)3, HZSM-5 and Pd/C as catalysts under microwave irradiation. When Fe2(SO4)3 or HZSM-5 was used as a catalyst, the Cα-Cβ bond of the C3 side chain in the model compound was broken to form aldehyde, secondary alcohol or ketone compounds. When Pd/C and formate were used as the catalyst, the β-O-4 aryl bond of the non-phenolic model compound was selectively cleaved and hydrogenation of C=C on the side chain occurred at the same time. However, the hydrogenation reaction of C=C on the side chain was faster than that of cleavage of the ether bond. Increasing Pd content favored the selective cleavage of the β-O-4 bond, and microwave irradiation accelerated the cleavage of the β-O-4 bond dramatically. At a high dosage of formate or high temperature, the condensation reaction among phenolic products was promoted due to the presence of an active phenolic hydroxyl group. The β-O-4 bond of the phenolic model compound was also selectively cleaved with Pd/C as the catalyst, and the reaction temperatures of cleaving about one half β-O-4 bonds of the non-phenolic and phenolic model compounds were 120 and 100°C, respectively.

Synthesis, biological activity and structure-activity relationships of new benzoic acid-based protein tyrosine phosphatase inhibitors endowed with insulinomimetic effects in mouse C2C12 skeletal muscle cells

Insulin resistance is a complex altered metabolic condition characterized by impaired insulin signaling and implicated in the pathogenesis of serious human diseases, such as diabetes, obesity, neurodegenerative pathologies. In pursuing our aim to identify new agents able to improve cellular insulin sensitivity, we have synthesized new 4-[(5-arylidene-4-oxo-2-phenylimino/ oxothiazolidin-3-yl)methyl]benzoic acids (5, 8) and evaluated their inhibitory activity towards human protein tyrosine phosphatases PTP1B, LMW-PTP and TCPTP, enzymes which are involved in the development of insulin resistance. Compounds 5 and 8 showed from moderate to significant selectivity toward PTP1B over both the highly homologous TCPTP and the two isoforms of human LMW-PTP. In addition, most of the tested compounds selectively inhibited LMW-PTP IF1 over the isoform IF2. Docking studies into the active sites of PTP1B and LMW-PTP aided the rationalization of the observed PTP inhibitory profile. Moreover, most tested compounds were capable to induce the insulin metabolic pathway in mouse C2C12 skeletal muscle cells by remarkably stimulating both IRβ phosphorylation and 2-deoxyglucose cellular uptake.

Design, synthesis, structure-activity relationships, and biological characterization of novel arylalkoxyphenylalkylamine σ ligands as potential antipsychotic drugs

Receptor antagonists may be effective antipsychotic drugs that do not induce motor side effects caused by ingestion of classical drugs such as haloperidol. We obtained evidence that 1-(2-dipropylaminoethyl)-4-methoxy- 6H-dibenzo[b,d]pyran hydrochloride 2a had selective affinity for σ receptor over dopamine D2 receptor. This compound was designed to eliminate two bonds of apomorphine 1 to produce structural flexibility for the nitrogen atom and to bridge two benzene rings with a -CH2O- bond to maintain the planar structure. In light of the evidence, N,Y-dipropyl-2-(4-methoxy-3- benzyloxylphenyl)ethylamine hydrochloride 10b was designed. Since compound 10b had eliminated a biphenyl bond of 6H-dibenzo[b,d]pyran derivative 2a, it might be more released from the rigid structure of apomorphine 1 than compound 2a. The chemical modification of compound 10b led to the discovery that N,N-dipropyl-2-[4-methoxy-3-(2-phenylethoxyl)phenyl]ethylamine hydrochloride 10g (NE- 100), the best compound among arylalkoxyphenylalkylamine derivatives 3, had a high and selective affinity for σ receptor and had a potent activity in an animal model when the drug was given orally. We report here the design, synthesis, structure-activity relationships, and biological characterization of novel arylalkoxyphenylalkylamine derivatives 3.

Alkoxyphenylalkylamine derivatives

An alkoxyphenylalkylamine derivative represented by the following formula: STR1 (wherein X1 and X2 may be either the same or different from each other and each represents a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy g