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Biomass Chemical Engineering ›› 2020, Vol. 54 ›› Issue (3): 31-36.doi: 10.3969/j.issn.1673-5854.2020.03.005

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

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

  1. 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

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

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