Green and efficient synthesis of highly liposoluble and antioxidant L-ascorbyl esters by immobilized lipases. (15th December 2022)

• Record Type: Journal Article
• Authors: Zhang, Tiantian; Zhang, Yi; Deng, Changyue; Zhong, Huaying; Gu, Tingting; Goh, Kheng-Lim; Han, Zhongmu; Zheng, Mingming; Zhou, Yibin
• Is Part Of: Journal of cleaner production. Volume 379:Part 2(2022)
• Publication Date: 2022-12-15
• Subjects: Unsaturated fatty acid ascorbyl esters -- Green synthesis -- Immobilized lipase -- Molecular docking -- Physicochemical properties; Factory and trade waste -- Management -- Periodicals; Manufactures -- Environmental aspects -- Periodicals; Déchets industriels -- Gestion -- Périodiques; Usines -- Aspect de l'environnement -- Périodiques; 628.5
• DOI: 10.1016/j.jclepro.2022.134772
• Languages: English
• ISSNs: 0959-6526

Abstract

Abstract: L-ascorbyl palmitate (LAP) is the permitted antioxidant used in baby food, but its high commercial demand is suppressed by poor liposolubility. In this paper, a cleaner and more efficient method to synthesize the high-liposoluble and antioxidant unsaturated fatty acid ascorbyl esters (UFAAE) is proposed, based on the enzymatic catalysis using CaLB immobilized on the ordered mesoporous silicon (CaLB@OMS-C8 ). The results indicated that the maximum catalytic efficiency (CE) in CaLB@OMS-C8 could reach 20.8 M g −1 h −1, thus facilitating the high conversions of 71.8%, 74.1% and 76.8% for L-ascorbyl oleate (LAO), L-ascorbyl linoleate (LAL) and L-ascorbic acid linolenic ester (LALN), respectively. The higher yield of LALN was explained by molecular docking technology as lipase CaLB presented a high binding affinity to linolenic acid (−18.8 kJ/mol) than those to oleic acid (−9.2 kJ/mol) and linoleic acid (−15.4 kJ/mol). By using unsaturated fatty acids as acyl donors, the synthesized UFAAE exhibited a lower melting point, better liposolubility and comparable antioxidant ability compared to LAP. This method to synthesize the high-soluble and antioxidant L-ascorbyl esters by the enzymatic esterification between L-ascorbic acid and unsaturated fatty acids shows great potential as a clean and efficient approach for future industrial production. Graphical abstract: Image 1 Highlights: Green and clean production of ascorbyl esters by immobilized lipase was proposed. Catalytic efficiency and thermal stability of CaLB@OMS-C8 were largely improved. Enzymatically produced ascorbyl esters had higher solubility and antioxidation. Interactions of lipase and fatty acids were studied by molecular docking technique. This paper highlights the efficiency and sustainability of enzymatic synthesis.