69693-12-5

Upstream product

• 1196-92-5 Vanillylamin 
• 112-64-1 tetradecanoyl chloride 
• 124-10-7 methyl myristoate 
• 7149-10-2 vanillylamine hydrochloride 
• 544-63-8 n-tetradecanoic acid 

Downstream Products

• 69693-13-6 Palvanil 

Relevant academic research and scientific papers

Application of hansch's model to capsaicinoids and capsinoids: A study using the quantitative structure-activity relationship. A novel method for the synthesis of capsinoids

We describe a synthetic approach for two families of compounds, the capsaicinoids and capsinoids, as part of a study of the quantitative relationship between structure and activity. A total of 14 capsaicinoids of increasing lateral chain lengths, from 2 to 16 carbon atoms, were synthesized. In addition, 14 capsinoids with identical lateral chains, as well as capsiate and dihydrocapsiate, have been synthesized, and a new method for the synthesis of these compounds has been developed. The yields range from 48.35 to 98.98%. It has been found that the synthetic capsaicinoids and capsinoids present a lipophilia similar to those of the natural compounds and present similar biological activity. The bioactivity of the synthetic capsaicinoids and capsinoids decreases proportionally to the degree of difference in lipophilia (higher or lower) compared to the natural compounds. Biological activity was determined using the etiolated wheat (Triticum aestlvum L.) coleoptiles bioassay and by comparing results of the synthesis with those presented by their counterpart natural compounds. The bioactivities found correlated directly to the lipophilic properties of the synthesized compounds.

Highly efficient synthesis of capsaicin analogues by condensation of vanillylamine and acyl chlorides in a biphase H2O/CHCl3 system

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.

Lipophilicity of capsaicinoids and capsinoids influences the multiple activation process of rat TRPV1

Analogs of capsaicin, such as capsaicinoids and capsinoids, activate a cation channel, transient receptor potential cation channel vanilloid subfamily 1 (TRPV1), and then increase the intracellular calcium concentration ([Ca2+]i). Th

A novel acylase from Streptomyces mobaraensis that efficiently catalyzes hydrolysis/synthesis of capsaicins as well as N-acyl-L-amino acids and N-acyl-peptides

A novel enzyme that catalyzes efficient hydrolysis of capsaicin (8-methyl-N-vanillyl-6-nonenamide) was isolated from the culture broth of Streptomyces mobaraensis. The enzyme consisted of two dissimilar subunits with molecular masses of 61 and 19 KDa. The enzyme was activated and stabilized in the presence of Co2+. It showed a pH optimum of about 8 and was stable at temperatures of up to 55°C for 1 h at pH 7.8. The specific activity of the enzyme for the hydrolysis of capsaicin was 10 2-104 times higher than those for the enzymes reported to date. In an aqueous/n-hexane biphasic system, capsaicin analogues such as octanoyl, decanoyl, and lauroyl vanillylamides were synthesized from the corresponding fatty acids and vanillylamine at yields of 50% or greater. In addition, the enzyme catalyzed the deacylation of N-lauroyl-L-amino acids and N-lauroyl-L-dipeptides and the efficient synthesis of Nα-lauroyl-L-lysine, Nε-lauroyl-L-lysine, and various N-lauroyl-peptides in aqueous solution in both the absence and the presence of glycerol.

Anti-tumor pharmaceutical composition comprising N-vanillyl fatty acid amide

The present invention provides an anti-tumor pharmaceutical composition having a high anti-tumor effect with low side-effects. The anti-tumor pharmaceutical composition comprises a N-vanillyl fatty acid amide of formula (1): wherein —CO—R group represents

Enzymatic synthesis of capsaicin analogs with liver acetone powder

The enzymatic synthesis of capsaicin analogs with saturated or unsaturated acyl moieties has been achieved by using liver acetone powder as a catalyst.