What are the key steps in the complete synthesis of Nonivamide Powder?

- Oct 29, 2020-

Nonivamide Powder (N-vanvillyl nonoylamide) is a natural capsaicin analogue, also called synthetic capsaicin, its spicyness and irritation can be equivalent to 8-methyl-N One vanillyl group ~ 3/5 of 6-nonenyl amide, the synthesis cost is not more than 1/10 of it. It is cost-effective and can replace natural capsaicin in various sspects of the application.

There are two key steps in the total synthesis of Nonivamide Powder. One is the synthesis of vanillin. Generally, the corresponding aldehyde is used as the raw material and a reducing agent is used to reduce a CH group to an NH: group. Generally with the corresponding aldehyde as raw material, use of reducing agent to reduce a CH base to one NH: base. Commonly used methods are: Leuckart method using ammonium formate one-step reduction, but which has harsh reduction conditions and low yield; Or it can first oximize vanillin, and then use zinc/carboxylic acid system, borohydride or catalytic hydrogenation reduction, but there are problems such as expensive raw materials 、complicated operation,it is difficult to repeat verification due to unstable process.

synthesis of Nonivamide Powder Nonivamide Powder.jpg

The second key to the synthesis of Nonivamide Powder is the condensation of vanillin with carboxylic acid chloride. Because vanillyl amine has poor solubility, there are two active groups on the benzene ring in vanillyl amine: molecule-NH: and-OH, they can react with carboxylic acid chloride to form amide and phenol ester respectively under given conditions. Vanillyl amine is directly condensed with carboxylic acid chloride. One is that the yield of the target product is low, and the other is that the by-product phenol ester is not easy to separate, which increases the difficulty of post-processing.

In addition, literature reports on the purification of Synthetic Capsaicin mostly use column chromatography combined with recrystallization, which will not only cause operational inconvenience and consume a lot of organic solvents, but also be difficult to scale production. In order to meet the requirements of increasing yield, reducing costs and reducing environmental pollution, and suitable for industrial production, it is necessary to optimize and improve the traditional process conditions.


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