Sucrose laurate is an important food additives which can be used as surfactants, emulsifiers, etc. Because of its high safety and anti-starch aging effect, it has a wide range of applications in food, sugar and other industries. Using Novozym 435 as a catalyst and sucrose and vinyl laurate as substrates, sucrose laurate monoester was synthesized in a tert-amyl alcohol system. Afterwards, amorphous sucrose was used as a substrate to improve the dissolution characteristics of sucrose, the yield of sucrose esters was further increased. The reaction conditions of the enzyme catalytic system were optimized: 0.09 mol/L amorphous sucrose, 0.15 mol/L vinyl laurate, 16.7 g/L Novozym 435, 2 g/L sodium laurate and 20 g/L molecular sieve were added in 15 mL of tert-amyl alcohol. After reacting at 75 ℃ for 60 h, the concentration of sucrose laurate monoester reached 23.2 g/L, the conversion rate reached 49.2%, and the formation of diesters was not detected. The research can lay the foundation for the industrialization of sucrose laurate monoester by enzymatic synthesis in the future, and it can also provide new ideas for the development of similar products.
HE Mengdi
,
ZHANG Kerui
,
CHEN Xiaolong
,
FAN Yongxian
,
CHEN Hanchi
,
ZHU Linjiang
,
LU Yuele
. The synthesis of sucrose laurate monoester catalyzed by deprotonation-activated Novozym 435 from amorphous sucrose[J]. Food and Fermentation Industries, 2021
, 47(18)
: 65
-69
.
DOI: 10.13995/j.cnki.11-1802/ts.027712
[1] NETA N S, TEIXEIRA J A, RODRIGUES L R.Sugar ester surfactants:Enzymatic synthesis and applications in food industry[J].Critical Reviews in Food Science and Nutrition, 2015, 55(5):595-610.
[2] 张雄, 贾康乐, 文武, 等.蔗糖酯表面活性剂化学合成工艺研究进展[J].精细化工, 2020, 37(11):2 193-2 199.
ZHANG X, JIA K L, WEN W, et al.Research progress of chemical synthesis technology of sucrose esters surfactants[J].Fine Chemicals, 2020, 37(11):2 193-2 199.
[3] SZÜTS A, SZABÓ-RéVéSZ P.Sucrose esters as natural surfactants in drug delivery systems—A mini-review[J].International Journal of Pharmaceutics, 2012, 433(1-2):1-9.
[4] NAGAI Y, KAWANO S, MOTODA K, et al.Solubility testing of sucrose esters of fatty acids in international food additive specifications[J].Biological and Pharmaceutical Bulletin, 2017, 40(3):284-289.
[5] TODOSIJEVIĆ M N, BREZESINSKI G, SAVIĆ S D, et al.Sucrose esters as biocompatible surfactants for penetration enhancement:An insight into the mechanism of penetration enhancement studied using stratum corneum model lipids and Langmuir monolayers[J].European Journal of Pharmaceutical Sciences, 2017, 99:161-172.
[6] LIU Y, BINKS B P.A novel strategy to fabricate stable oil foams with sucrose ester surfactant[J].Journal of Colloid and Interface Science, 2021, 594(15):204-216.
[7] NAKAMURA S, ISHII N, NAKASHIMA N, et al.Evaluation of sucrose fatty acid esters as lubricants in tablet manufacturing[J].Chemical and Pharmaceutical Bulletin, 2017, 65(5):432-441.
[8] 邓伶俐, 刘雨雨, 康雪帆, 等.蔗糖酯对大豆分离蛋白乳化性的影响及作用机理[J].中国食品学报, 2016, 16(12):43-49.
DENG L L, LIU Y Y, KANG X F, et al.Effect of sucrose ester on the emulsifying properties of soy protein isolate[J].Journal of Chinese Institute of Food Science and Technology, 2016, 16(12):43-49.
[9] TENG Y L, STEWART S G, HAI Y W, et al.Sucrose fatty acid esters:Synthesis, emulsifying capacities, biological activities and structure-property profiles[J].Critical Reviews in Food Science and Nutrition, 2020:1-21.
[10] FERRER M, SOLIVERI J,PLOU F J, et al.Synthesis of sugar esters in solvent mixtures by lipases from Thermomyces lanuginosus and Candida antarctica B, and their antimicrobial properties[J].Enzyme and Microbial Technology, 2005, 36(4):391-398.
[11] REYES-DUARTE D, LÓPEZ-CORTéS N, FERRER M, et al.Parameters affecting productivity in the lipase-catalysed synthesis of sucrose palmitate[J].Biocatalysis and Biotransformation, 2005, 23(1):19-27.
[12] FERRER M, CRUCES M A, BERNABé M, et al.Lipase-catalyzed regioselective acylation of sucrose in two-solvent mixtures.[J].Biotechnology and Bioengineering, 1999, 65(1):10-16.
[13] KLIBANOV A M.Improving enzymes by using them in organic solvents[J].Nature, 2001, 409(6 817):241-246.
[14] PARTRIDGE J, HALLING P J, MOORE B D.Solid-state proton/sodium buffers:“chemical pH stats” for biocatalysts in organic solvents[J].Journal of the Chemical Society, Perkin Transactions 2, 2000, (3):465-471.
[15] HALLING P J.Biocatalysis in low-water media:Understanding effects of reaction conditions[J].Current Opinion in Chemical Biology, 2000, 4(1):74-80.
[16] WOUDENBERG-VAN OOSTEROM M, VAN RANTWIJK F, SHELDON R A.Regioselective acylation of disaccharides in tert-butyl alcohol catalyzed by Candida antarctica lipase[J].Biotechnology and Bioengineering, 1996, 49(3):328-333.
[17] MORROW E A, TERBAN M W, THOMAS L C, et al.Effect of amorphization method on the physicochemical properties of amorphous sucrose[J].Journal of Food Engineering, 2019, 243:125-141.
[18] FLORES M V,NARAGHI K,ENGASSER J M, et al.Influence of glucose solubility and dissolution rate on the kinetics of lipase catalyzed synthesis of glucose laurate in 2-methyl 2-butanol[J].Biotechnology and Bioengineering, 2002, 78(7):815-821.
[19] ADHIKARI B, HOWES T, BHANDARI B R, et al.Effect of addition of proteins on the production of amorphous sucrose powder through spray drying[J].Journal of Food Engineering, 2009, 94(2):144-153.
[20] 李延科, 张淑芬,杨锦宗.蔗糖酯的薄层色谱分析[J].色谱, 2002, 20(5):476-478.
LI Y K, ZHANG S F, YANG J Z.Analysis of sucrose esters by thin-layer chromatography[J].Chinese Journal of Chromatography, 2002, 20(5):476-478.
[21] DANG H T,OBIRI O,HAYES D G.H.Feed batch addition of saccharide during saccharide-fatty acid esterification catalyzed by immobilized lipase:time course, water activity, and kinetic model[J].Journal of the American Oil Chemists′ Society, 2005, 82(7):487-493.
[22] SHI Y G, WU Y, LU X Y, et al.Lipase-catalyzed esterification of ferulic acid with lauryl alcohol in ionic liquids and antibacterial properties in vitro against three food-related bacteria[J].Food Chemistry, 2017, 220:249-256.
[23] YE R, HAYES D G, BURTON R.Effects of particle size of sucrose suspensions and pre-incubation of enzymes on lipase-catalyzed synthesis of sucrose oleic acid esters[J].Journal of the American Oil Chemists′ Society, 2014, 91(11):1 891-1 901.
[24] YE R, HAYES D G, BURTON R, et al.Solvent-free lipase-catalyzed synthesis of technical-grade sugar esters and evaluation of their physicochemical and bioactive properties[J].Catalysts, 2016, 6(6):78.
