{"title":"丁香酚曼尼希和甲基化合成四烷基铵化合物及其抑菌活性","authors":"Sabarmin Perangin-angin, Sri Wahyuni Barus","doi":"10.5220/0008879202230228","DOIUrl":null,"url":null,"abstract":"6-[(N-iodo-N-methyl-N-methyl-N-methylamino)methyl]-4-alyl-2-methoxyphenol was synthesized through Mannich and methylation reaction. Mannich reaction was carried out by reacting eugenol, formaldehyde 37%, and dimethylamine 40% with ethanol at temperature of 78°C for 90 minutes and 4-allyl-6(dimethylamino)methyl-2-methoxyphenol was obtained with yield of 83,03%. Quartenary ammonium salt, 6-[(N-iodo-N-methyl-N-methyl-N-methylamino)methyl]-4-allyl-2-methoxyphenol, was obtained through methylation reaction of 4-allyl-6-(dimethylamino)methyl-2-methoxyphenol with methyl iodide in ethanol. In the FTIR spectrum, the specific peak of ammonium salt was exhibited at 948.98 and 455.20 cm-1. The antibacterial activity of 6-[(N-iodo-N-metil-N-methyl-N-methylamino)methyl]-4-allyl-2-methoxyphenol was performed against E. coli and S. aureus, this quaternary ammonium salt exhibited a strong activity.","PeriodicalId":20533,"journal":{"name":"Proceedings of the 1st International Conference on Chemical Science and Technology Innovation","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"1","resultStr":"{\"title\":\"Synthesis of Quatenary Ammonium Compounds from Eugenol through Mannich and Methylation Reactions and Its Antibacterial Activity\",\"authors\":\"Sabarmin Perangin-angin, Sri Wahyuni Barus\",\"doi\":\"10.5220/0008879202230228\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"6-[(N-iodo-N-methyl-N-methyl-N-methylamino)methyl]-4-alyl-2-methoxyphenol was synthesized through Mannich and methylation reaction. Mannich reaction was carried out by reacting eugenol, formaldehyde 37%, and dimethylamine 40% with ethanol at temperature of 78°C for 90 minutes and 4-allyl-6(dimethylamino)methyl-2-methoxyphenol was obtained with yield of 83,03%. Quartenary ammonium salt, 6-[(N-iodo-N-methyl-N-methyl-N-methylamino)methyl]-4-allyl-2-methoxyphenol, was obtained through methylation reaction of 4-allyl-6-(dimethylamino)methyl-2-methoxyphenol with methyl iodide in ethanol. In the FTIR spectrum, the specific peak of ammonium salt was exhibited at 948.98 and 455.20 cm-1. The antibacterial activity of 6-[(N-iodo-N-metil-N-methyl-N-methylamino)methyl]-4-allyl-2-methoxyphenol was performed against E. coli and S. aureus, this quaternary ammonium salt exhibited a strong activity.\",\"PeriodicalId\":20533,\"journal\":{\"name\":\"Proceedings of the 1st International Conference on Chemical Science and Technology Innovation\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2019-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"1\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Proceedings of the 1st International Conference on Chemical Science and Technology Innovation\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.5220/0008879202230228\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Proceedings of the 1st International Conference on Chemical Science and Technology Innovation","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.5220/0008879202230228","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 1
摘要
通过曼尼希和甲基化反应合成了6-[(n -碘- n -甲基- n -甲基- n -甲氨基)甲基]-4-烯丙基-2-甲氧基苯酚。以丁香酚、甲醛37%、二甲胺40%与乙醇在78℃下反应90 min,得到4-烯丙基-6(二甲胺)甲基-2-甲氧基苯酚,产率为83,03%。以4-烯丙基-6-(二甲氨基)甲基-2-甲氧基苯酚为原料,与碘化甲酯在乙醇中甲基化,制得6-[(n -碘- n -甲基- n -甲基- n -甲氨基)甲基]-4-烯丙基-2-甲氧基苯酚季铵盐。在FTIR光谱中,铵盐的比峰出现在948.98和455.20 cm-1处。研究了6-[(n -碘- n -甲二醇- n -甲基- n -甲氨基)甲基]-4-烯丙基-2-甲氧基苯酚对大肠杆菌和金黄色葡萄球菌的抑菌活性,表明该季铵盐具有较强的抑菌活性。
Synthesis of Quatenary Ammonium Compounds from Eugenol through Mannich and Methylation Reactions and Its Antibacterial Activity
6-[(N-iodo-N-methyl-N-methyl-N-methylamino)methyl]-4-alyl-2-methoxyphenol was synthesized through Mannich and methylation reaction. Mannich reaction was carried out by reacting eugenol, formaldehyde 37%, and dimethylamine 40% with ethanol at temperature of 78°C for 90 minutes and 4-allyl-6(dimethylamino)methyl-2-methoxyphenol was obtained with yield of 83,03%. Quartenary ammonium salt, 6-[(N-iodo-N-methyl-N-methyl-N-methylamino)methyl]-4-allyl-2-methoxyphenol, was obtained through methylation reaction of 4-allyl-6-(dimethylamino)methyl-2-methoxyphenol with methyl iodide in ethanol. In the FTIR spectrum, the specific peak of ammonium salt was exhibited at 948.98 and 455.20 cm-1. The antibacterial activity of 6-[(N-iodo-N-metil-N-methyl-N-methylamino)methyl]-4-allyl-2-methoxyphenol was performed against E. coli and S. aureus, this quaternary ammonium salt exhibited a strong activity.