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Chemistry and Industry of Forest Products ›› 2015, Vol. 35 ›› Issue (6): 33-38.doi: 10.3969/j.issn.0253-2417.2015.06.006

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Synthesis and Antibacterial Activities of Carboxylic Myrtanyl Esters

LIAO Sheng-liang, SHANG Shi-bin, SI Hong-yan, SHEN Ming-gui, RAO Xiao-ping, SONG Zhan-qian   

  1. Institute of Chemical Industry of Forest Products, CAF; National Engineering Lab.for Biomass Chemical Utilization; Key and Open Lab.of Forest Chemical Engineering, SFA;Key Lab.of Biomass Energy and Material, Jiangsu Province, Nanjing 210042, China
  • Received:2014-10-28 Online:2015-12-25 Published:2015-12-28

Abstract: Myrtanol was prepared via hydroboration-oxidation reaction from β-pinene, then eight novel carboxylic myrtanyl esters (myrtanyl acetate(4a), myrtanyl propionate(4b), myrtanyl butyrate(4c), myrtanyl valerate(4d), myrtanyl cyclohexanecarboxylate(4e), myrtanyl benzoate(4f), myrtanyl p-methylbenzoate(4g) and myrtanyl p-methoxybenzoate(4h) were obtained through the reaction of myrtanol and carboxylic acids using N, N'-dicyclohexylcarbodiimide/dimethylaminopyridine (DCC/DMAP) as catalyst.Structure characterizations were achieved by FT-IR, 1H NMR and ESI-MS.Antibacterial activity assays were carried out by agar dilution method.The results showed that compounds 4b, 4c, 4f, 4g and 4h exhibited inhibitory activities (MIC was 256 mg/L) against the Gram positive bacterial Staphylococcus aureus, and compounds 4a, 4b, 4c and 4e exhibited inhibitory activities (MICs were ranged from 128 to 256 mg/L) against the Gram negative bacterial Escherichia coli.more importantly.Compound 4a showed comparable activity (MIC was 128 mg/L) to that of bromogeramine against E.coli.Comparing with the starting compound β-pinene and the intermediate myrtanol, this series of esters showed better antibacterial activities.

Key words: turpentine, β-pinene, myrtanol, ester, antibacterial

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