Ultrasound-assisted lipase catalyzed hydrolysis of aspirin methyl ester

被引:17
作者
Chiplunkar, Pranali P. [1 ,2 ]
Zhao, Xiaoman [1 ,3 ,4 ]
Tomke, Prerana D. [1 ,5 ]
Noro, Jennifer [6 ]
Xu, Bo [1 ]
Wang, Qiang [1 ]
Silva, Carla [6 ]
Pratap, Amit P. [2 ]
Cavaco-Paulo, Artur [1 ,6 ]
机构
[1] Jiangnan Univ, Int Joint Res Lab Text & Fiber Bioproc, Wuxi 214122, Peoples R China
[2] Inst Chem Technol, Dept Oils Oleochem & Surfactants Technol, Bombay 400019, Maharashtra, India
[3] Inst Chem Technol, Jiangsu Engn Technol Res Ctr Funct Text, Bombay 400019, Maharashtra, India
[4] Jiangnan Univ, Minist Educ, Key Lab Sci & Technol Ecotext, Wuxi 214122, Jiangsu, Peoples R China
[5] Inst Chem Technol, Dept Chem Engn, Bombay 400019, Maharashtra, India
[6] Univ Minho, Ctr Biol Engn, Campus Gualtar, P-4710057 Braga, Portugal
关键词
Hydrolysis; Aspirin methyl ester; Lipase; Ultrasound; Water; WASTE COOKING OIL; CANDIDA-ANTARCTICA; ORGANIC-SOLVENTS; MICROBIAL LIPASES; ENZYMATIC-SYNTHESIS; FATTY-ACIDS; CAVITATION; ACETATE; TRANSESTERIFICATION; BIOCATALYST;
D O I
10.1016/j.ultsonch.2017.08.004
中图分类号
O42 [声学];
学科分类号
070206 ; 082403 ;
摘要
The ultrasound-assisted hydrolysis of aspirin methyl ester (AME) was investigated using immobilized Candida antarctica lipase B (CALB) (1%) in the presence of solvents like triolein, chloroform (CHCl3) and dichloromethane (DCM). The effect of ultrasound and the role of water on the conversion rates have also been investigated. Proton nuclear magnetic resonance spectroscopic (H-1 NMR) was chosen to calculate hydrolysis convertion rates. We observed that lipase-ultrasound assisted hydrolysis of AME in the presence of triolein and water showed the highest hydrolysis conversion rate (65.3%). Herein low water amount played an important role as a nucleophile being crucial for the hydrolysis yields obtained. Lipase activity was affected by the conjugated action of ultrasound and solvents (35.75% of decrease), however not disturbing its hydrolytic efficiency. It was demonstrated that lipase is able to hydrolyse AME to methyl 2-hydroxy benzoate (methyl salicylate), which applications include fragrance agents in food, beverages and cosmetics, or analgesic agent in liniments.
引用
收藏
页码:587 / 593
页数:7
相关论文
共 59 条
[1]   Use of Lecitase-Ultra immobilized on styrene-divinylbenzene beads as catalyst of esterification reactions: Effects of ultrasounds [J].
Alves, Joana S. ;
Garcia-Galan, Cristina ;
Danelli, Daiane ;
Paludo, Natalia ;
Barbosa, Oveimar ;
Rodrigues, Rafael C. ;
Fernandez-Lafuente, Roberto .
CATALYSIS TODAY, 2015, 255 :27-32
[2]   Combined Effects of Ultrasound and Immobilization Protocol on Butyl Acetate Synthesis Catalyzed by CALB [J].
Alves, Joana S. ;
Garcia-Galan, Cristina ;
Schein, Mirela F. ;
Silva, Alexandre M. ;
Barbosa, Oveimar ;
Ayub, Marco A. Z. ;
Fernandez-Lafuente, Roberto ;
Rodrigues, Rafael C. .
MOLECULES, 2014, 19 (07) :9562-9576
[3]   One biocatalyst - Many applications: The use of Candida antarctica B-lipase in organic synthesis [J].
Anderson, EM ;
Karin, M ;
Kirk, O .
BIOCATALYSIS AND BIOTRANSFORMATION, 1998, 16 (03) :181-204
[4]   Lipase-catalyzed diacylglycerol production under sonochemical irradiation [J].
Babicz, Ivelize ;
Leite, Selma G. F. ;
de Souza, Rodrigo O. M. A. ;
Antunes, O. A. C. .
ULTRASONICS SONOCHEMISTRY, 2010, 17 (01) :4-6
[5]   Ultrasound assisted lipase catalysed synthesis of isoamyl butyrate [J].
Bansode, Sneha R. ;
Rathod, Virendra K. .
PROCESS BIOCHEMISTRY, 2014, 49 (08) :1297-1303
[6]   Assessment of two immobilized lipases activity and stability to low temperatures in organic solvents under ultrasound-assisted irradiation [J].
Batistella, Luciane ;
Ustra, Mara K. ;
Richetti, Aline ;
Pergher, Sibele B. C. ;
Treichel, Helen ;
Oliveira, J. V. ;
Lerin, Lindomar ;
de Oliveira, Debora .
BIOPROCESS AND BIOSYSTEMS ENGINEERING, 2012, 35 (03) :351-358
[7]   ASPIRIN PRODRUGS - SYNTHESIS AND HYDROLYSIS OF 2-ACETOXYBENZOATE ESTERS OF VARIOUS N-(HYDROXYALKYL)AMIDES [J].
BUNDGAARD, H ;
NIELSEN, NM ;
BUUR, A .
INTERNATIONAL JOURNAL OF PHARMACEUTICS, 1988, 44 (1-3) :151-158
[8]   Enzyme catalyzed hydrolysis of esters using reversibly soluble polymer conjugated lipases [J].
Charusheela, A ;
Arvind, L .
ENZYME AND MICROBIAL TECHNOLOGY, 2002, 30 (01) :19-25
[9]   Effect of ultrasound on enzymatic acylation of konjac glucomannan [J].
Chen, Zhi-Gang ;
Zong, Min-Hua ;
Gu, Zhen-Xin ;
Han, Yong-Bin .
BIOPROCESS AND BIOSYSTEMS ENGINEERING, 2008, 31 (04) :351-356
[10]   Ultrasound-Assisted SWNTs Dispersion: Effects of Sonication Parameters and Solvent Properties [J].
Cheng, Qiaohuan ;
Debnath, Sourabhi ;
Gregan, Elizabeth ;
Byrne, Hugh J. .
JOURNAL OF PHYSICAL CHEMISTRY C, 2010, 114 (19) :8821-8827