Progress in Synthesis of Monoglycerides for Use in Food and Pharmaceuticals

https://doi.org/10.14499/jfps

Nilesh Ramesh Rarokar(1*), Sunil Menghani(2), Deweshri Kerzare(3), Pramod Bhujangrao Khedekar(4)

(1) Department of Pharmaceutical Sciences Rashtrasant Tukadoji Maharaj Nagpur University Nagpur (M.S.), India 440033
(2) Department of Pharmaceutical Sciences Rashtrasant Tukadoji Maharaj Nagpur University Nagpur (M.S.), India 440033
(3) Department of Pharmaceutical Sciences Rashtrasant Tukadoji Maharaj Nagpur University Nagpur (M.S.), India 440033
(4) Department of Pharmaceutical Sciences Rashtrasant Tukadoji Maharaj Nagpur University Nagpur (M.S.), India 440033
(*) Corresponding Author

Abstract


Glycerides are lipid esters of the glycerol molecule and fatty acids. Their primary function is the storage of energy. Due to its structure and properties, glycerol participates in the formulation or synthesis of many compounds such as food products, cosmetics, pharmaceuticals, liquid detergents. Monoglycerides (MGs) can be formed by both industrial chemical glycerolysis and biological or enzymatic processes. Chemical glycerolysis bring issues of low MGs yield, high operating temperature, formation of undesirable by-products and high energy consumption. On the other hand enzymatic processes have advantages of mild reaction conditions and high purity of MGs. But, several purification steps are required to obtain food or pharmaceutical grade MG, such as neutralization of the reaction media and discoloration followed by expensive molecular distillation. The purpose of this article is to review the main challenges in the synthesis of MGs from triglycerides (TGs) contained in the various fixed oils and application thereof in the food and pharmaceuticals.

 

Keywords:  Catalyzation, glycerolysis, molecular distillation, monoglycerides, solid catalysts.


Full Text:

PDF


References

Corma A, Huber GW, Sauvanaud L, O’Connor P. Processing biomass-derived oxygenates in the oil refinery: catalytic cracking (FCC) reaction pathways and role of catalyst. J Catal 2007; 247: 307–327.

Shabaker JW, Huber GW, Dumesic JA. Aqueous-phase reforming of oxygenated hydrocarbons over Sn-modified Ni catalysts. J Catal 2004; 222 :180–191.

Karinen RS, Krause AOI. New biocomponents from glycerol. Appl Catal A: Gen 2006; 306:128–133.

Corma A, Iborra S, Velty A. Chemical routes for the transformation of biomass into chemicals. Chem Rev 2007; 107: 2411–2502.

Zheng Y, Chen X, Shen Y. Commodity chemicals derived from glycerol, an important biorefinery feedstock. Chem Rev 2008; 108: 5253–5277.

Krog NJ. Food emulsifiers and their chemical and physical properties. In Food Emulsion; Friberg, S E, Larsson, K, editors. Marcel Dekker: NY, 1997, p. 141-188.

Corma A, Hamid SBA, Iborra S, Velty A. Lewis and Bronsted basic active siteson solid catalysts and their role in the synthesis of monoglycerides. J Catal 2005; 234: 340–347.

Damstrup ML, Jensen T, Sparso FV, Kiil SZ, Jensen AD, Xu X. Production of heat-sensitive monoacylglycerols by enzymatic glycerolysis in tert-pentanol: process optimization by response surface methodology. J Am Oil Chem Soc 2006; 83:27–33.

Devinat G, Coustille JL. Reesterification on a pilot scale of the fatty acids of Colza and soybean. Rev Fran Corps Gras 1983;30: 463-468.

Swern D. Industrial Oil and Fats Products. Wiley, New York 1979; 1: 497- 601.

Sonntag NOV. Glycerolysis of fats and methylesters-Status, review and critique. J Am. Oil Chem Soc 1982; 59: 795A-802A.

Gross AT, Feuge RO. J Am Oil Chem Soc 1949;26: 704.

Berger M, Schneider MP. Enzymatic esterification of glycerol II. Lipase-catalyzed synthesis of regioisomerically pure 1(3) - rac-monoacylglycerols. J Am Oil Chem Soc 1992; 69: 961–965.

Freitas L, Bueno T, Perez VH, Castro HF. Monoglycerides: production by enzymatic route and applications. Quim Nova 2008; 31: 1514–1521.

Bornscheuer UT. Lipase-catalyzed syntheses of monoacylglycerols. Enzyme Microb Technol 1995; 17: 578–586.

Sagalowicz L, Leser ME, Watzke HJ, Michel M. Trends in Food Science & Technology. Trends Food Sci Technol 2006;17: 204–214.

Ferreira-Dias S, Correia AC, Fonseca MMR. Response surface modelling of glycerolysis catalysed by Candida rugosa lipase immobilized in different polyurethane foams for the production of partial glycerides. J Mol Catal B: Enzym 2003; 21: 71–80.

Kaewthong W, Sirisansaneeyakul S, Prasertsan P, H-Kittikun A. Continuous production of monoacylglycerols by glycerolysis of palm oil with immobilized lipase. Process Biochem 2005; 40:1525–1530.

Kaewthong W, H-Kittikun A. Glycerolysis of palm olein by immobilized lipase PS in organic solvents. Enzyme Microb Technol 2004; 35: 218–222.

Yesiloglu Y. Immobilized lipase-catalyzed ethanolysis of sunflower oil. J Am Oil Chem Soc 2004; 81:157–160.

Ferreira-Dias S, Correia AC, Baptista FO, da Fonseca MMR. Contribution of response surface design to the development of glycerolysis systems catalyzed by commercial immobilized lipases, J Molecular Catalysis B: Enzymatic 2001; 11: 699-711.

Holmberg K and Osterberg E. Enzymatic preparation of monoglycerides in microemulsion. J Am- Oil Chem- Soc 1988; 65:1544-1548.

Akoh CC, Cooper C, Nwosu CV. Lipase G-catalyzed synthesis of monoglycerides in organic solvent and analysis by HPLC. J Am Oil Chem Soc 1992; 69:257–260.

Cheirsilp B, Jeamjounkhaw P, H-Kittikun A. Optimizing an alginate immobilized lipase for monoacylglycerol production by the glycerolysis reaction. J Mol Catal B: Enzyme 2009; 59:206–211.

Ferretti CA, Soldano A , Apesteguia CR, Di Cosimo JI. Monoglyceride synthesis by glycerolysis of methyl oleate on solid acid–base catalysts. Chemical Engineering Journal 2010; 161: 346–354.

Van Der Padt A, Keurentjes JTF, Sewalt JJW, Van Dam EM, Van Dorp LJ, Vant Riet K. Enzymatic Synthesis of Monoglycerides in a Membrane Bioreactor with an In-line Absorption Column. J Am Oil Chem Soc 1992; 69:748–754.

Castillo E, Dossat V, Marty A, Condoret JS, Combes D. The role of silica gel in lipase-catalyzed esterification reactions of high-polar substrates. J Am Oil Chem Soc 1997; 74:77–85.

Langone MAP, De Abreu ME, Rezende MJC, Sant’Anna Jr GL. Enzymatic synthesis of medium chain monoglycerides in a solvent -free system. Appl Biochem Boitechnol 2002; 98: 987-996.

Freitas L, Perez VH, Santos JC, de Castro HF. Enzymatic synthesis of glyceride esters in solvent-free system: Influence of the molar ratio. Brazil Chem Soc 2007; 18:1360–1366.

Duan Zhang-Qun, Du Wei, Liu De-Hua. Improved synthesis of 1.3-diolein by Novozym 435-mediated esterification of monoolein with oleic acid. Journal of molecular catalysis B:Enzymatic 2013; 89: 1-5.

Wang W, Li T, Ning Z, Wang Y, Yang B, Yang X. Production of extremely pure diacylglycerol from soybean oil by lipase-catalyzed Glycerolysis. Enzyme and Microbial Technology 2011; 49:192–196.

Yang T, Rebsdorf M, Engerlrud U, Xu X. Monoacylglycerol synthesis via enzymatic glycerolysis using a simple and efficient reaction system. J Food Lipids 2005;12:299–312.

Pawongrat R, Xu X, H-Kittikun A. Physico-enzymatic production of monoacylglycerols enriched with very-long-chain polyunsaturated fatty acids. J Sci Food Agric 2008; 88:256–62.

Ferretti CA, Apesteguia CR, Di Cosimo JI. MgO-based catalysts for monoglyceride synthesis from methyl oleate and glycerol: Effect of Li promotion. Applied Catalysis A: General 2011; 399:146–153.

Zuyi L and Ward OP. Lipase-catalyzed alcoholysis to concentrate the ~o-3-polyunsaturated fatty acids of cod liver oil. Enzyme Microb TechnoL 1993;15:601-606.

Rarokar NR, Saoji SD, Raut NA, Taksande JB, Khedekar PB, and Dave VS. Nanostructured Cubosomes in a Thermoresponsive Depot System: An Alternative Approach for the Controlled Delivery of Docetaxel. AAPS PharmSciTech 2015; 17(2):436-445.

Ghamgui H, Miled N, Rebai A, Karra-chaabouni M, Gargouri Y. Production of mono-olein by immobilized Staphylococcus simulans lipase in a solvent-free system: optimization by response surface methodology. Enzyme Microb Technol 2006; 39:717–23.

Perez-Pariente J, Diaz I, Mohino F, Sastre E. Selective synthesis of fatty monoglycerides by using functionalised mesoporous catalysts. Appl Catal A 2003; 254:173–88.

Fregolente LV, Fregolente PBL, Chicuta AM, Batistella CB, Maciel Filho R, Wolf-Maciel MR. Effect of operating conditions on the concentration of monoglycerides using molecular distillation. Chem Eng Res Des 2007; 85:1524–8.

Trivedi R, Singh RP. Modification of oils and fats to produce structured lipids. J Oleo Sci 2005; 54:423–430.

Cyberlipid Center. Monoacylglycerols, http://www.cyberlipid.org; 2009.

Chaibi A, Lahsen HA, Busta FF. Inhibition of bacterial spores and vegetative cells by glycerides. J Food Prot 1996; 59:716–722

Zhang Z, Goff HD. On fat destabilization and composition of the air interface in ice cream containing saturated and unsaturated monoglyceride. Int Dairy J 2005; 15:495–500.

Damstrup ML, Jensen T, Sparso FV, Kiil SZ, Jensen AD, Xu X. Solvent optimization for efficient enzymatic monoacylglycerol production based on a glycerolysis reaction. J Am Oil Chem Soc 2005; 82:559–64.

Moonen H, & Bas H. Mono- and diglycerides. Whitehurst RJ, editor. Emulsifiers in food technology. Oxford: Blackwell Publishing 2004, p. 40-58.

Henry C. Monoglycerides – The Universal Emulsifier. Cereal Foods World 1995; 40(10):734–738.

Pawongrat R, Xu X, H-Kittikun A. Synthesis of monoacylglycerol rich in polyunsaturated fatty acids from tuna oil with immobilized lipase. AK Food Chem 2007; 104:251–8.

Zeng F, Yang B, Wang Y, Wang W, Ning Z, Li L. Enzymatic production of monoacylglycerols with camellia oil by the glycerolysis reaction. J Am Oil Chem Soc 2010; 87:531–7.

Friberg E & Larsson K, editors. Food emulsions. New York: Marcel Dekker; 2004, p. 112-118.

Jerome F, Pouilloux Y, Barrault J. Rational design of solid catalysts for the selective use of glycerol as a natural organic building block. Chem Sus Chem 2008; 1:586–613.



DOI: https://doi.org/10.14499/jfps

Article Metrics

Abstract views : 365 | views : 1379

Refbacks

  • There are currently no refbacks.


Journal of Food and Pharmaceutical Sciences (ISSN: 2339-0948) -  Universitas Gadjah Mada, Indonesia.