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Enzymatic Synthesis of Eugenyl Acetate from Essential Oil of Clove Using Lipases in Liquid Formulation as Biocatalyst
Applied Biochemistry and Biotechnology ( IF 3.1 ) Pub Date : 2021-07-22 , DOI: 10.1007/s12010-021-03610-z
Leandro Santolin 1 , Karina G Fiametti 1 , Viviane da Silva Lobo 1 , João H C Wancura 2 , J Vladimir Oliveira 3
Affiliation  

In this research, eugenyl acetate, a compound with flavoring, antioxidant, and antimicrobial properties, was obtained from essential oil of clove (Syzygium aromaticum) via liquid lipase-mediated acetylation. Clove essential oil was extracted by drag water vapor from dry flower buds and its physic-chemical characteristics were analyzed. For the enzymatic synthesis, an extensive evaluation of reaction parameters was accomplished through employment of distinct reaction temperatures, acetic anhydride to eugenol molar ratios, enzyme loads, and three different lipases (a lyophilized enzyme produced by solid-state fermentation of sunflower seed with Penicillium sumatrense microorganism and other two commercial lipases — Lipozyme TL 100L and CALB L). The product eugenyl acetate was confirmed by 1H-NMR, 13C-NMR Distortionless Enhancement by Polarization Transfer (DEPT 135), and Heteronuclear Multiple Bond Correlation (HMBC). Through optimized conditions (55 °C, acetic anhydride to eugenol molar ratio of 1:1, 10 wt% of Lipozyme TL 100L), 91.80% of conversion after 2 h was achieved to the eugenyl acetate production. With the results obtained, it was possible to conclude that the use of lipases in liquid formulation is a promising alternative for the synthesis of essential esters largely applied on food, cosmetic, and pharmaceutical industries.



中文翻译:

以液体制剂中的脂肪酶为生物催化剂从丁香精油酶法合成乙酸丁香酯

在这项研究中,醋酸丁香酚酯是一种具有调味、抗氧化和抗菌特性的化合物,它是从丁香精油 ( Syzygiumaromaticum ) 中通过液体脂肪酶介导的乙酰化作用获得的。从干燥的花蕾中提取水蒸气提取丁香精油并分析其理化特性。对于酶促合成,通过使用不同的反应温度、乙酸酐与丁香酚的摩尔比、酶负荷和三种不同的脂肪酶(向日葵种子与苏门答腊青霉进行固态发酵产生的冻干酶),完成了对反应参数的广泛评估微生物和其他两种商业脂肪酶——Lipozyme TL 100L 和 CALB L)。通过 1H-NMR、13C-NMR 偏振转移无畸变增强 (DEPT 135) 和异核多键相关 (HMBC) 确认产物乙酸丁香酯。通过优化条件(55 ℃,乙酸酐与丁香酚摩尔比为 1:1,Lipozyme TL 100L 为 10 wt%),2 h 后乙酸丁香酯生产的转化率为 91.80%。根据所获得的结果,可以得出结论,在液体制剂中使用脂肪酶是合成主要应用于食品、化妆品和制药行业的必需酯的有希望的替代方案。

更新日期:2021-07-22
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