66051-14-7

Usage

Uses

Used in Pharmaceutical Industry:
(Z)-α-methyl-cinnamaldehyde is used as an impurity in the production of Epalrestat (E565300), an aldose reductase inhibitor. The application reason is that it is a byproduct in the synthesis process of Epalrestat, which is utilized for the treatment of diabetic neuropathy. The presence of this impurity is crucial for the development and manufacturing of the drug, as it can impact the efficacy and safety of the final product.
In the pharmaceutical industry, the management and control of impurities like (Z)-α-methyl-cinnamaldehyde are essential to ensure the quality, safety, and efficacy of the final drug product. This involves rigorous testing, quality control measures, and adherence to regulatory guidelines to minimize the presence of impurities and maintain the desired therapeutic effects of the drug.

Upstream product

• 99405-12-6 α-(triethylsilyl)propionaldehydr tert-butylimine 
• 100-52-7 benzaldehyde 
• 147227-25-6 α,α-bis(trimethylsilyl)-tert-butylpropionaldimine 
• 78-85-3 2-methylpropenal 
• 71-43-2 benzene 
• 1504-55-8 2-methyl-3-phenylprop-2-en-1-ol 
• 7042-33-3 ethyl 2-methylcinnamate 

Downstream Products

• 22436-06-2 2-methyl-3-phenylpropanol 
• 73756-58-8 rac-1-Chlor-2-methyl-3-phenylpropan 

Relevant academic research and scientific papers

Assembly of indenamine derivatives through in situ formed N-sulfonyliminium ion initiated cyclization

An expedient route to structurally diverse indenamine derivatives through condensation of the readily accessible substituted cinnamylaldehydes and sulfonylamines under the catalysis of FeCl3 has been developed, featuring high efficiency in the generation of two bonds and one ring in a single-step and water as the only by-product. This journal is the Partner Organisations 2014.

A general route to α-alkyl (E)-α,β-unsaturated aldehydes

Bis(trimethylsilyl)-tert-butylaldimines 3 react with aldehydes in the presence of zinc bromide at room temperature to give, after hydrolysis, the desired α-alkyl α,β-ethylenic aldehydes in good yield and with very high E stereoselectivity. The reaction was believed to proceed via the α-silyl β-siloxyimines 4.

Oxidative coupling of benzenes with α,β-unsaturated aldehydes by the Pd(OAc)2/molybdovanadophosphoric acid/O2 system

The oxidative coupling reaction of benzene with an α,β- unsaturated aldehyde was examined by the combined catalytic system of Pd(OAc)2 with molybdovanadophosphoric acid (HPMoV) under atmospheric dioxygen. Thus, the reaction of benzene with acrolein under dioxygen (1 atm) by the use of catalytic amounts of Pd(OAc)2 and H4PMo 11VO40·26H2O in the presence of dibenzoylmethane as a ligand in propionic acid at 90 °C for 1.5 h afforded cinnamaldehyde in 59% yield and β-phenylcinnamaldehyde in 5% yield. This catalytic system was extended to the direct oxidative coupling through the C-H bond activation of various arenes with acrolein and methacrolein.

Syntheses of amino nitrones. Potential intramolecular traps for radical intermediates in monoamine oxidase-catalyzed reactions

Monoamine oxidase (MAO) is a flavin-dependent enzyme that catalyzes the oxidative deamination of a variety of amine neurotransmitters and toxic amines. Although there have been several studies that support the intermediacy of an amine radical cation and a

A Simple and Highly Stereoselective Route to E-α,β-Unsaturated Aldehydes

Zinc bromide mediated reaction of α,α-bis(trimethylsilyl)-tert-butylacetaldimine (3) with a wide range of aldehydes takes place under mild conditions and affords the corresponding α,β-unsaturated aldehydes in good yields and with high E stereoselectivity (>98percent).This procedure is successfully applied to the preparation of intermediates for retinoid and natural product synthesis.

A HIGHLY SELECTIVE METHOD FOR THE SYNTHESIS OF (E)-α-METHYL-α,β-UNSATURATED ALDEHYDES

Anhydrous acidic treatment of E,Z mixtures of α-methyl-α,β-unsaturated imines followed by hydrolysis gives the corresponding aldehydes with >= 100:1 E:Z ratios.