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Abstract

Objective:This study aimed to increase the added value of Yanbian yellow cattle fat.Methods:Using immobilized lipase Lipozyme RM IM as a catalyst, and tallow fatty acid ethyl ester (self-made by ethanol hydrolysis) and glycerol as raw materials to prepare 1,3-diglyceride, using nuclear magnetic resonance to investigate the effect of lipase addition, substrate molar ratio, reaction time and reaction temperature on the content of 1,3-diglyceride in the crude reaction mixture. The changes in fatty acid composition of the tallow and diglyceride products was clarified before and after the alcoholysis and transesterification.Results:The best conditions for the synthesis of 1,3-diglycerides were the addition of 1% (mass fraction) of lipase Lipozyme RM IM, with the molar ratio of substrate of 2∶1, and reaction for 6 h, at 50 ℃. Under the control of those conditions, the production rate of 1,3-diglycerides was 72.5%, and the yield of glycerides was 77%; the purity increased to 90.79% after purification. After testing, compared with crude oil (flavored tallow), the content of linoleic acid and oleic acid in the diglyceride product increased by 13.65% and 6.47%, respectively, and the degree of saturation decreased by 7.17%.Conclusion:the preparation of 1,3-diglycerides from Yanbian Yellow Cattle fat changes not only the glyceride structure, but also the fatty acid composition of cattle fat and reduces the saturation. This experiment enables the high-quality utilization of Yanbian Yellow Cattle fat.

Publication Date

7-7-2022

First Page

210

Last Page

215

DOI

10.13652/j.issn.1003-5788.2022.02.035

References

[1] 胡忠昌.延黄牛ALDH1A1基因对脂代谢的影响及其遗传变异分析[D].延吉:延边大学,2019:1.HU Zhong-chang.The effect of yanhuang cattle ALDH1A1 gene on lipid metabolism and its genetic variation analysis[D].Yanji:Yanbian University,2019:1.
[2] 冯伟玲.牛油特征性风味化合物筛选及品质质量控制研究[D].成都:西华大学,2018:1-2.FENG Wei-ling.Research on the screening and quality control of characteristic flavor compounds of butter[D].Chengdu:Xihua University,2018:1-2.
[3] 刘佳敏,何新益,刘晓东,等.精炼对牛油主要理化指标及挥发性成分的影响[J].食品与机械,2020,36(4):62-67.LIU Jia-min,HE Xin-yi,LIU Xiao-dong,et al.The effect of refining on the main physical and chemical indicators and volatile components of butter[J].Food & Machinery,2020,36(4):62-67.
[4] 曾朝懿,史颖,张丽珠,等.棕榈油复合火锅底料不同贮藏温度品质变化及货架期预测[J].中国调味品,2016,41(4):32-37.ZENG Chao-yi,SHI Ying,ZHANG Li-zhu,et al.The quality change and shelf life prediction of palm oil compound hot pot base at different storage temperatures[J].China Condiments,2016,41(4):32-37.
[5] TAGUCHI H,NAGAO T,WATANABE H,et al.Energy value and digestibility of dietary oil containing mainly 1,3-diacylglycerol are similar to those of triacylglycerol[J].Lipids,2001,36(4):379-382.
[6] 胡士恒.玉米油酶法合成甘油二酯研究[D].吉林:吉林大学,2013:3-7.HU Shi-heng.Enzymatic synthesis of diglycerides from corn oil[D].Jilin:Jilin University,2013:3-7.
[7] 高正松,王保成,徐松泉,等.甘油二酯的合成及纯化研究进展[J].广州化工,2020,48(17):4-8.GAO Zheng-song,WANG Bao-cheng,XU Song-quan,et al.Research progress on synthesis and purification of diglycerides[J].Guangzhou Chemical Industry,2020,48(17):4-8.
[8] 马靖轩,马传国,司天雷,等.分子蒸馏精制棕榈油甘油二酯工艺研究[J].中国油脂,2018,43(3):6-9.MA Jing-xuan,MA Chuan-guo,SI Tian-lei,et al.Research on refining palm oil diglyceride by molecular distillation[J].China Oils and Fats,2018,43(3):6-9.
[9] VERSAN KOK M,VARFOLOMEEV M A,NURGALIEV D K.Determination of SARA fractions of crude oils by NMR technique[J].Journal of Petroleum Science and Engineering,2019,179:1-6.
[10] 孟祥河,杨奇波,肖丹,等.香榧籽油金松酸的分离及其1,3-甘油二酯的制备研究[J].中国粮油学报,2020,35(7):72-78.MENG Xiang-he,YANG Qi-bo,XIAO Dan,et al.Separation of torrenia seed oil and preparation of 1,3-diglyceride[J].Journal of the Chinese Cereals and Oils Association,2020,35(7):72-78.
[11] VÁZQUEZ L,GONZÁLEZ N,REGLERO G,et al.Solvent-free lipase-catalyzed synthesis of diacylgycerols as low-calorie food ingredients[J].Frontiers in Bioengineering and Biotechnology,2016,4:6.
[12] 郭婷婷,曾俊鹏,彭斌,等.分子蒸馏纯化花生油甘油二酯及其成分变化研究[J].中国食品学报,2020,20(12):176-183.GUO Ting-ting,ZENG Jun-peng,PENG Bin,et al.Research on molecular distillation purification of peanut oil diglyceride and its composition changes[J].Chinese Journal of Food Science,2020,20(12):176-183.
[13] 仇宏图,王家镔,张华.降低延边黄牛脂饱和脂肪酸含量的分提研究[J].延边大学农学学报,2018,40(4):65-69.QIU Hong-tu,WANG Jia-bin,ZHANG Hua.Study on the fractional extraction of reducing the saturated fatty acid content of Yanbian yellow tallow[J].Journal of Agricultural Science Yanbian University,2018,40(4):65-69.
[14] 何娜.鲢鱼鱼油多不饱和脂肪酸纳米脂质体的制备及其性质研究[D].南昌:南昌大学,2016:23-29.HE Na.Preparation and properties of polyunsaturated fatty acid nano-liposomes from silver carp and fish oil[D].Nanchang:Nanchang University,2016:23-29.
[15] 傅红,裘爱泳.鱼油脂肪酸乙酯化工艺研究[J].粮食与油脂,2004(5):27-30.FU Hong,QIU Ai-yong.Study on the ethyl esterification of fish oil fatty acids[J].Food and Oils,2004(5):27-30.
[16] 仇宏图,李光春,吴明根,等.菜籽油脂质成分分析及甲酯化研究[J].安徽农业大学学报,2019,46(4):583-588.QIU Hong-tu,LI Guang-chun,WU Ming-gen,et al.Analysis of rapeseed oil lipid composition and study on methyl esterification[J].Journal of Anhui Agricultural University,2019,46(4):583-588.
[17] MARIA D G,AINHOA R.Rapid simultaneous determination by proton NMR of unsaturation and composition of acyl groups in vegetable oils[J].European Journal of Lipid Science & Technology,2010,105(11):688-696.
[18] GHAMGUI H,MILED N,REBA A,et al.Production of mono-olein by immobilized Staphylococcus simulans lipase in a solvent-free system:Optimization by response surface methodology[J].Enzyme & Microbial Technology,2006,39(4):717-723.
[19] 李兰香,何腊平,张义明,等.水活度对全细胞脂肪酶GZUF36催化合成1,3-甘油二酯中的影响[J].中国食品添加剂,2015(2):77-82.LI Lan-xiang,HE La-ping,ZHANG Yi-ming,et al.The effect of water activity on the synthesis of 1,3-diglyceride by whole-cell lipase GZUF36[J].China Food Additives,2015(2):77-82.
[20] 〖JP2〗鲁珊,黄健花,王兴国.无溶剂体系酶催化酯化反应合成1,3-甘油二酯的研究[J].食品与生物技术学报,2013,32(4):358-361.LU Shan,HUANG Jian-hua,WANG Xing-guo.Study on synthesis of 1,3-diglyceride by enzyme-catalyzed esterification in solvent-free system[J].Journal of Food and Biotechnology,2013,32(4):358-361.
[21] 黄楚楚,熊辉煌,龚斌,等.脂肪酶催化单油酸甘油酯制备功能性1,3-甘油二酯[J].食品科学,2015,36(22):1-5.HUANG Chu-chu,XIONG Hui-huang,GONG Bin,et al.Lipase-catalyzed preparation of functional 1,3-diglycerides from glycerol monooleate[J].Food Science,2015,36(22):1-5.
[22] QI Jin-feng,WANG Xiang-yu,ZHANG Hua,et al.Optimization of omega-3 enriched-diacylglycerol production by enzymatic esterification using a response surface methodology[J].Food Science and Biotechnology,2014,23(4):1 129-1 136.
[23] LASZLO J A,COMPTON D L,VERMILLION K E.Acyl migration kinetics of vegetable oil 1,2-diacylglycerols[J].Journal of the American Oil Chemists Society,2008,85(4):307-312.
[24] DAVID L,COMPTON D L.Purification of 1,2-diacylglycerols from vegetable oils:Comparison of molecular distillation and liquid CO2 extraction[J].Industrial Crops and Products,2008,28(2):113-121.
[25] GUILLEN M D,URIARTE P S.Study by 1H-NMR spectroscopy of the evolution of extra virgin olive oil composition submitted to frying temperature in an industrial fryer for a prolonged period of time[J].Food Chemistry,2012,134(1):162-172.

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