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利用米根霉脂肪酶高效合成及放大制备对甲氧基肉桂酸2-乙基己酯的环保方法及其生物学评价

Eco-friendly methodology for efficient synthesis and scale-up of 2-ethylhexyl-p-methoxycinnamate using Rhizopus oryzae lipase and its biological evaluation.

作者信息

Kumar Vinod, Jahan Firdaus, Kameswaran Karthikeya, Mahajan Richi V, Saxena Rajendra Kumar

机构信息

Department of Microbiology, University of Delhi South Campus, New Delhi, 110021, India.

出版信息

J Ind Microbiol Biotechnol. 2014 Jun;41(6):907-12. doi: 10.1007/s10295-014-1429-0. Epub 2014 Mar 26.

DOI:10.1007/s10295-014-1429-0
PMID:24668019
Abstract

Lipase-mediated synthesis of phenolic acid esters is a green and economical alternative to current chemical methods. Octyl methoxycinnamate, an important UVB-absorbing compound, was synthesized by the esterification of p-methoxycinnamic acid with 2-ethyl hexanol using Rhizopus oryzae lipase. A molar ratio of 1:2 of p-methoxycinnamic acid and 2-ethyl hexanol was found to give an optimum yield using cyclo-octane (50 ml) as reaction solvent, at a temperature of 45 °C, and 750 U of lipase, resulting in a yield of 91.3 % in 96 h. This reaction was successfully scaled up to 400-ml reaction size where 88.6 %bioconversion was achieved. The synthesized compound was found to have superior antioxidant activity as compared to ascorbic acid. The synthesized compound also exhibited good antimicrobial activity against Escherichia coli, Klebsiella pneumonia, Salmonella typhi, Staphylococcus aures, Candida albicans (yeast), Aspergillus niger, Alternaria solani, and Fussarium oxysporum by well diffusion method in terms of zone of inhibitions (in mm).

摘要

脂肪酶介导的酚酸酯合成是一种比当前化学方法更绿色、更经济的替代方法。通过米根霉脂肪酶催化对甲氧基肉桂酸与2-乙基己醇的酯化反应,合成了一种重要的紫外线吸收化合物甲氧基肉桂酸辛酯。在以环辛烷(50毫升)为反应溶剂、温度为45℃、脂肪酶用量为750单位的条件下,发现对甲氧基肉桂酸与2-乙基己醇的摩尔比为1:2时产率最佳,96小时内产率达到91.3%。该反应成功放大至400毫升反应规模,生物转化率达到88.6%。与抗坏血酸相比,合成的化合物具有更强的抗氧化活性。通过平板扩散法,合成的化合物对大肠杆菌、肺炎克雷伯菌、伤寒沙门氏菌、金黄色葡萄球菌、白色念珠菌(酵母)、黑曲霉、链格孢菌和尖孢镰刀菌也表现出良好的抗菌活性(抑菌圈大小,单位为毫米)。

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