N-(4-羟基-3-甲氧基苄基)-癸酰胺的合成及其生理活性

Synthesis and biological Activity of N-( 4-hydroxy-3-methoxybenzyl )-decanoylamide

摘要:

以香草醛、正癸酸、SOCl2为原料，三步合成出辣椒碱类物质——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；两物质毒性级别为均为3(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。

Abstract:

With vanillin, decanoic acid and sulfinyl chloride as initial material, capsaicinoid of N-( 4-hydroxy-3-methoxybenzyl )-decanoylamide was synthesized successfully by three synthesis procedures only. According to IR, 1HNMR, 13CNMR and elemental analysis data, its molecular structure was confirmed. Comparative research on physiological activity for natural capsaicinoid and target compound was made.And the experiment results on physiological activity were as follows: N-( 4-hydroxy-3-methoxybenzyl )-decanoylamide was similar to natural capsaicinoid in potency of pungency and the former was 0.4% smaller than the latter in pungency; the antinociceptive effect of target compound was stronger 30% than natural capsaicin; they were almost same and stronger than sodium benzoate in antibacterial activity; 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) As a conclusion, the synthetic capsaicinoid of N-( 4-hydroxy-3-methoxybenzyl )-decanoylamide had the value of replacing natural capsaicin in the above biological activity.