Ultrasound-assisted lipase catalyzed hydrolysis of aspirin methyl ester

Pranali P Chiplunkar; Xiaoman Zhao; Prerana D Tomke; Jennifer Noro; Bo Xu; Qiang Wang; Carla Silva; Amit P Pratap; Artur Cavaco-Paulo

doi:10.1016/j.ultsonch.2017.08.004

Ultrasound-assisted lipase catalyzed hydrolysis of aspirin methyl ester

Ultrason Sonochem. 2018 Jan;40(Pt A):587-593. doi: 10.1016/j.ultsonch.2017.08.004. Epub 2017 Aug 5.

Authors

Pranali P Chiplunkar¹, Xiaoman Zhao², Prerana D Tomke³, Jennifer Noro⁴, Bo Xu⁵, Qiang Wang⁵, Carla Silva⁴, Amit P Pratap⁶, Artur Cavaco-Paulo⁷

Affiliations

¹ International Joint Research Laboratory for Textile and Fiber Bioprocesses, Jiangnan University, Wuxi 214122, China; Department of Oils, Oleochemicals and Surfactants Technology, Institute of Chemical Technology, Matunga (E), Mumbai 400019, India.
² International Joint Research Laboratory for Textile and Fiber Bioprocesses, Jiangnan University, Wuxi 214122, China; Jiangsu Engineering Technology Research Center for Functional Textiles, Institute of Chemical Technology, Matunga (E), Mumbai 400019, India; Key Laboratory of Science and Technology of Eco-Textiles, Ministry of Education, Jiangnan University, Wuxi 214122, Jiangsu, China.
³ International Joint Research Laboratory for Textile and Fiber Bioprocesses, Jiangnan University, Wuxi 214122, China; Department of Chemical Engineering, Institute of Chemical Technology, Matunga (E), Mumbai 400019, India.
⁴ Centre of Biological Engineering, University of Minho, Campus de Gualtar, 4710-057, Braga, Portugal.
⁵ International Joint Research Laboratory for Textile and Fiber Bioprocesses, Jiangnan University, Wuxi 214122, China.
⁶ Department of Oils, Oleochemicals and Surfactants Technology, Institute of Chemical Technology, Matunga (E), Mumbai 400019, India.
⁷ International Joint Research Laboratory for Textile and Fiber Bioprocesses, Jiangnan University, Wuxi 214122, China; Centre of Biological Engineering, University of Minho, Campus de Gualtar, 4710-057, Braga, Portugal. Electronic address: artur@deb.uminho.pt.

PMID: 28946463
DOI: 10.1016/j.ultsonch.2017.08.004

Abstract

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 (¹H 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.

Keywords: Aspirin methyl ester; Hydrolysis; Lipase; Ultrasound; Water.

MeSH terms

Aspirin / chemistry*
Biocatalysis*
Enzymes, Immobilized* / chemistry
Enzymes, Immobilized* / metabolism
Fungal Proteins / chemistry
Fungal Proteins / metabolism*
Hydrolysis
Lipase / chemistry
Lipase / metabolism*
Solvents / chemistry
Ultrasonic Waves*

Substances

Enzymes, Immobilized
Fungal Proteins
Solvents
Lipase
lipase B, Candida antarctica
Aspirin