ω-氯甲基莰烯的高效快速合成及抑菌活性

doi:10.3969/j.issn.1673-5854.2020.03.005

生物质化学工程 ›› 2020, Vol. 54 ›› Issue (3): 31-36.doi: 10.3969/j.issn.1673-5854.2020.03.005

ω-氯甲基莰烯的高效快速合成及抑菌活性

霍尚朝,黄道战,蓝虹云*(),林志楠,陆于州

广西民族大学化学化工学院;广西林产化学与工程重点实验室, 广西南宁 530008

收稿日期:2019-07-18 出版日期:2020-05-30 发布日期:2020-06-13
通讯作者: 蓝虹云 E-mail:lanhongyun88@163.com
作者简介:霍尚朝(1993-),男,河北邯郸人,硕士生,研究方向为林产精细化工
基金资助:
广西自然科学基金资助项目(2017GXNSFAA198027);广西创新驱动发展重大专项子课题(桂科AA17204087-21);国家级大学生创新创业训练计划项目(201510608042)

Fast and Highly Efficient Synthesis of ω-Chloromethyl Camphene and Its Antimacrobial Activity

Shangchao HUO,Daozhan HUANG,Hongyun LAN*(),Zhinan LIN,Yuzhou LU

College of Chemistry and Chemical Engineering, Guangxi University for Nationalities;Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Nanning 530008, China

Received:2019-07-18 Online:2020-05-30 Published:2020-06-13
Contact: Hongyun LAN E-mail:lanhongyun88@163.com

摘要/Abstract

摘要：

以ω-乙酰氧甲基莰烯、乙酰氯、无水乙醇为原料，通过卤代反应，合成ω-氯甲基莰烯，通过FT-IR、¹H NMR、¹³C NMR和LC-HRMS等对产物进行了结构表征。研究结果表明：反应时间、反应物料比对卤代反应有较大的影响，在温度为30℃、n（ω-乙酰氧甲基莰烯）：n（乙酰氯）：n（无水乙醇）为1：2：2的条件下反应5 min，ω-乙酰氧甲基莰烯的转化率和ω-氯甲基莰烯产率分别高达97.5%和95.2%。微量肉汤二倍稀释法抑菌活性实验结果表明：ω-氯甲基莰烯能抑制细菌和真菌的生长，对4种细菌（大肠杆菌、肺炎克雷伯菌、金黄色葡萄球菌、枯草芽孢杆菌）的最低抑菌质量浓度（MIC）分别为125、62.5、15.63、250 mg/L，对3种真菌（白色念珠菌、热带念珠菌、黑曲霉）的MIC均为31.25 mg/L，抑菌活性明显高于莰烯、ω-乙酰氧甲基莰烯和ω-羟甲基莰烯，对白色念珠菌的抑菌活性与阳性对照品酮康唑相当。

关键词: ω-氯甲基莰烯, ω-乙酰氧甲基莰烯, 乙酰氯, 卤代反应, 抑菌活性

Abstract:

ω-Chloromethyl camphene was synthesized from ω-acetoxymethyl camphene by facile and fast halogenation procedure, in which acetyl chloride and absolute ethanol was employed as halogenated reagent, and structurally characterized by means of FT-IR, ¹H NMR, ¹³C NMR and LC-HRMS. The results showed that the reaction time and material molar ratio (n(ω-acetoxymethyl camphene):n(acetyl chloride):n(ethanol)) both had strong effects on halogenations reaction. Under the optimum conditions (30 ℃, 5 min, material molar ratio 1:2:2), the conversion of ω-acetoxymethyl camphene was up to 97.5% with the yield of ω-chloromethyl camphene 95.2%. The results of preliminary antimacrobial activity experiment showed that ω-chloromethyl camphene could distinctly inhibit the growth of bacterial and fungus, their minimum inhibitory concentrations (MIC) against four bacteria(Escherichia coli, Klebsiella pneumonia, Staphylococcus aureus and Bacillus subtilis) and three fungus(Candida albicans, Candida tropicalis and Aspergillus niger) were 125, 62.5, 15.63, 250, 31.25, 31.25, 31.25 mg/L, respectively. The antibacterial activity of ω-chloromethyl camphene was clearly higher than that of camphene, ω-acetoxymethyl camphene and ω-hydroxymethyl camphene. In addition, the antibacterial activity of ω-chloromethyl camphene against C. albicans was almost the same as the positive control ketoconazole.

Key words: ω-chloromethyl camphene, ω-acetoxymethyl camphene, acetyl chloride, halogenation, antimacrobial activity

中图分类号:

TQ35

霍尚朝,黄道战,蓝虹云,林志楠,陆于州. ω-氯甲基莰烯的高效快速合成及抑菌活性[J]. 生物质化学工程, 2020, 54(3): 31-36.

Shangchao HUO,Daozhan HUANG,Hongyun LAN,Zhinan LIN,Yuzhou LU. Fast and Highly Efficient Synthesis of ω-Chloromethyl Camphene and Its Antimacrobial Activity[J]. Biomass Chemical Engineering, 2020, 54(3): 31-36.

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参考文献 14

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化合物 compounds	最低抑菌质量浓度minimum inhibitory mass concentration / (mg· L ^{- 1})
化合物 compounds	大肠杆菌 E.coli	肺炎克雷伯菌 K.pneumonia	金黄色葡萄球菌 S.aureus	枯草芽孢杆菌 B.subtilis	白色念珠菌 C.albicans	热带念珠菌 C.tropicalis	黑曲霉 A.niger
莰烯camphene	> 500	> 500	> 500	> 500	> 500	125	> 500
ω-乙酰氧甲基莰烯 ω-acetoxymethyl camphene	> 500	> 500	> 500	> 500	250	> 500	> 500
ω-羟甲基莰烯 ω-hydroxymethyl camphene	> 500	250	250	250	125	125	> 500
ω-氯甲基莰烯ω-chloromethyl camphene	125	62.5	15.63	250	31.25	31.25	31.25
阳性对照品positive control substance	3.91^a	3.91^a	0.242^a	0.976^a	31.25^b	3.91^b	3.91^b

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ω-氯甲基莰烯的高效快速合成及抑菌活性

Fast and Highly Efficient Synthesis of ω-Chloromethyl Camphene and Its Antimacrobial Activity

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