Solvent-free synthesis of medium chain triacylglycerols by esterification of capric, caprylic acids with 1, 3-specific and non-specific lipases

IF 1.9 4区 农林科学 Q3 CHEMISTRY, APPLIED
V. P. Mayookha, U. Raksha, Nanishankar V. Harohally, G. Suresh Kumar
{"title":"Solvent-free synthesis of medium chain triacylglycerols by esterification of capric, caprylic acids with 1, 3-specific and non-specific lipases","authors":"V. P. Mayookha,&nbsp;U. Raksha,&nbsp;Nanishankar V. Harohally,&nbsp;G. Suresh Kumar","doi":"10.1002/aocs.12904","DOIUrl":null,"url":null,"abstract":"<p>Medium chain triacylglycerols (MCTs) are used as a functional oil in various food and pharmaceutical formulations because of their numerous health benefits and physical properties. Enzymatic esterification of glycerol with caprylic (C8:0) and capric acids (C10:0) in a molar ratio of 1:3.5 [50% (C8:0) and 50% (C10:0)] was carried out for the solvent free synthesis of MCTs using 5% (w/w) 1,3 specific lipase, Lipozyme RM IM and non-specific lipase, Novozym 435 in the presence of molecular sieves (10%) and low pressure conditions (50 and 150 mbar) at 50°C. Novozym 435 was more effective in the esterification reaction under 50 mbar reduced pressure, achieving ~54.74% triacylglycerol formation in 6 h, compared to Lipozyme RMIM, which achieved ~31.25% under the same conditions. Further reactions with Novozym 435 for 24 h showed that the maximum formation of MCTs occurred at 20 h (86.46 ± 3%), after which the reaction reached equilibrium. When 50 mbar was used, the formation of triacylglycerols enhanced 13 times compared with the results obtained at atmospheric pressure condition. Chemical characterization of the final MCTs confirmed the formation of four triacylglycerol species (TAG (8:0/8:0/8:0), TAG (8:0/8:0/10:0), TAG (8:0/10:0/10:0), and TAG (10:0/10:0/10:0) with LC–MS and NMR analysis. The melting and crystallization points of the synthesized oil was found to be −3.47°C and −23.48°C, respectively. Our findings contribute to developing a green process for synthesizing MCTs using two different fatty acids. The final product can be used as a nutraceutical oil or as an ingredient to enhance the food's physical properties.</p>","PeriodicalId":17182,"journal":{"name":"Journal of the American Oil Chemists Society","volume":"102 3","pages":"657-667"},"PeriodicalIF":1.9000,"publicationDate":"2024-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of the American Oil Chemists Society","FirstCategoryId":"97","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/aocs.12904","RegionNum":4,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
引用次数: 0

Abstract

Medium chain triacylglycerols (MCTs) are used as a functional oil in various food and pharmaceutical formulations because of their numerous health benefits and physical properties. Enzymatic esterification of glycerol with caprylic (C8:0) and capric acids (C10:0) in a molar ratio of 1:3.5 [50% (C8:0) and 50% (C10:0)] was carried out for the solvent free synthesis of MCTs using 5% (w/w) 1,3 specific lipase, Lipozyme RM IM and non-specific lipase, Novozym 435 in the presence of molecular sieves (10%) and low pressure conditions (50 and 150 mbar) at 50°C. Novozym 435 was more effective in the esterification reaction under 50 mbar reduced pressure, achieving ~54.74% triacylglycerol formation in 6 h, compared to Lipozyme RMIM, which achieved ~31.25% under the same conditions. Further reactions with Novozym 435 for 24 h showed that the maximum formation of MCTs occurred at 20 h (86.46 ± 3%), after which the reaction reached equilibrium. When 50 mbar was used, the formation of triacylglycerols enhanced 13 times compared with the results obtained at atmospheric pressure condition. Chemical characterization of the final MCTs confirmed the formation of four triacylglycerol species (TAG (8:0/8:0/8:0), TAG (8:0/8:0/10:0), TAG (8:0/10:0/10:0), and TAG (10:0/10:0/10:0) with LC–MS and NMR analysis. The melting and crystallization points of the synthesized oil was found to be −3.47°C and −23.48°C, respectively. Our findings contribute to developing a green process for synthesizing MCTs using two different fatty acids. The final product can be used as a nutraceutical oil or as an ingredient to enhance the food's physical properties.

Abstract Image

中链三酰甘油(MCTs)具有多种健康益处和物理特性,因此被用作各种食品和药物配方中的功能油。为了无溶剂合成 MCTs,在分子筛(10%)存在和 50°C 低压条件(50 和 150 毫巴)下,使用 5% (重量比)1,3 特异性脂肪酶 Lipozyme RM IM 和非特异性脂肪酶 Novozym 435,以 1:3.5 的摩尔比[50%(C8:0)和 50%(C10:0)]对甘油与辛酸(C8:0)和癸酸(C10:0)进行了酶法酯化。与 Lipozyme RMIM 相比,Novozym 435 在 50 毫巴低压条件下的酯化反应更有效,6 小时内形成了 ~54.74% 的三酰甘油,而 Lipozyme RMIM 在相同条件下形成了 ~31.25% 的三酰甘油。与 Novozym 435 进一步反应 24 小时后发现,MCT 的最大形成时间为 20 小时(86.46 ± 3%),之后反应达到平衡。使用 50 毫巴时,三酰甘油的形成比常压条件下的结果提高了 13 倍。通过 LC-MS 和 NMR 分析,最终 MCT 的化学特征证实形成了四种三酰甘油(TAG (8:0/8:0/8:0)、TAG (8:0/8:0/10:0)、TAG (8:0/10:0/10:0) 和 TAG (10:0/10:0/10:0))。合成油的熔点和结晶点分别为 -3.47°C 和 -23.48°C。我们的研究结果有助于开发一种利用两种不同脂肪酸合成 MCT 的绿色工艺。最终产品可用作营养保健油或增强食品物理性质的配料。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 求助全文
来源期刊
CiteScore
4.10
自引率
5.00%
发文量
95
审稿时长
2.4 months
期刊介绍: The Journal of the American Oil Chemists’ Society (JAOCS) is an international peer-reviewed journal that publishes significant original scientific research and technological advances on fats, oils, oilseed proteins, and related materials through original research articles, invited reviews, short communications, and letters to the editor. We seek to publish reports that will significantly advance scientific understanding through hypothesis driven research, innovations, and important new information pertaining to analysis, properties, processing, products, and applications of these food and industrial resources. Breakthroughs in food science and technology, biotechnology (including genomics, biomechanisms, biocatalysis and bioprocessing), and industrial products and applications are particularly appropriate. JAOCS also considers reports on the lipid composition of new, unique, and traditional sources of lipids that definitively address a research hypothesis and advances scientific understanding. However, the genus and species of the source must be verified by appropriate means of classification. In addition, the GPS location of the harvested materials and seed or vegetative samples should be deposited in an accredited germplasm repository. Compositional data suitable for Original Research Articles must embody replicated estimate of tissue constituents, such as oil, protein, carbohydrate, fatty acid, phospholipid, tocopherol, sterol, and carotenoid compositions. Other components unique to the specific plant or animal source may be reported. Furthermore, lipid composition papers should incorporate elements of year­to­year, environmental, and/ or cultivar variations through use of appropriate statistical analyses.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信