105026-89-9Relevant articles and documents
Combined infrared spectroscopic and computational study on simpler capsaicin derivatives and their anion intermediates in the scavenging of free radicals
Anichina, K.,Nikolova, S.,Stamboliyska, B.,Stoyanov, S.,Velcheva, E.,Yancheva, D.
, (2020)
Two capsaicin analogues – N-(4-hydroxy-3-methoxybenzyl)acetamide and N-(4-hydroxy-3-methoxybenzyl)benzamide, were studied by DFT methods in order to estimate their ability to act as antioxidants. A comparative study on the stability of benzylic, phenoxyl and amide radicals has outlined the most reactive site for hydrogen atom abstraction and proton transfer. The enthalpies related to the formation of those species were modeled in gas phase, benzene, DMSO and water in order to determine the most probable mechanism of antioxidant action in polar and nonpolar medium. The formation of phenoxyl anion, energetically favoured in polar medium, was investigated by infrared spectroscopy methods based on the conversion of the benzamide derivative.
Highly efficient synthesis of capsaicin analogues by condensation of vanillylamine and acyl chlorides in a biphase H2O/CHCl3 system
Wang, Bo,Yang, Fan,Shan, Yi-Fan,Qiu, Wen-Wei,Tang, Jie
supporting information; experimental part, p. 5409 - 5412 (2009/10/17)
Highly efficient synthesis of capsaicin analogues was developed using condensation of vanillylamine with acyl chlorides in a biphase H2O/CHCl3 system under mild conditions. For C4-C18 aliphatic or aromatic acyl chlorides, the yields were up to 93-96% with high purity after a simple work-up procedure, and only 1-1.16 equiv of acyl chloride was needed in the reaction.