N-(4-羟基-3-甲氧基苄基)-癸酰胺的合成及其生理活性

Synthesis and Physiological Activity of N-(4-Hydroxy-3-methoxybenzyl)-decanoylamide

以香草醛、正癸酸、SOCl2为原料,3步反应合成了辣椒碱类物质——N-(4-羟基-3-甲氧基苄基)-癸酰胺,其结构经IR、1HNMR、13CNMR和元素分析确认。对比研究目标产物与天然辣椒碱生理活性:两物质辣度相近,目标产物辣度仅比天然辣椒碱低0.4%;目标产物镇痛活性优于天然辣椒碱30%;两物质抗菌活性基本相同,强于苯甲酸钠;驱避老鼠活性相似;两物质毒性级别均为3级(低毒)。因此,合成辣椒碱——N-(4-羟基-3-甲氧基苄基)-癸酰胺在上述生理活性上有替代天然辣椒碱的使用价值。

With vanillin,decanoic acid and sulfinyl chloride as initial material,capsaicinoid of N-（4-hydroxy-3-methoxybenzyl）-decanoylamide was synthesized successfully in three mere steps.Its molecular structure was ascertained by means of IR,1HNMR,13CNMR and elemental analysis.A comparative study on the physiological activity of natural capsaicinoid and the target compound shows that N-（4-hydroxy-3-methoxybenzyl）-decanoylamide was similar to natural capsaicinoid in potency of pungency and the former was 0.4% lower than the latter in pungency;the antinociceptive effect of the target compound was 30% greater than natural capsaicinoid;they were almost the same in their antibacterial activity,which is superior to sodium benzoate;they were also similar as a repellent for mice.The target compound and natural capsaicinoid were both in the toxicity grade of 3（low toxicity）.In conclusion,the synthetic capsaicinoid of N-（4-hydroxy-3-methoxybenzyl）-decanoylamide has the value of replacing natural capsaicin in the above biological activity application.