Production of 1, 3-dioleoyl-2-palmitoyl glycerol as a human milk fat substitute using enzymatic interesterification of natural fats and oils

Abstract

Human milk fat substitutes were synthesized using non-preprocessed natural fats and oils with lipase. Enzymatic interesterification of tripalmitin and oleic acid was carried out in isooctane. The reaction reached equilibrium after 12 h and the reaction conditions were partially optimized as a molar ratio of tripalmitin to oleic acid of 1:5, an initial water content of 0.01 g/L, and a water removal time of 1 h. After interesterification of tripalmitin and oleic acid, the reaction products contained 55.2% 1,3-dioleoyl-2-palmitoyl glycerol (OPO). The OPO yield was 25.2% when commercial palm oil and camellia oil were used as substrates, and the OPO concentration was increased to 53.3% after fractional crystallization of the reaction product.

1,3‐Dioleoyl‐2‐palmitoyl glycerol (OPO)—Enzymatic synthesis and use as an important supplement in infant formulas

“…Up until now, a number of immobilized sn‐1,3 regiospecific lipases such as Rhizomucor miehei lipase (RML), Thermomyces lanuginosus lipase (TLL), Candida(Yarrowia) lypolytica lipase (C/YLL), Rhyzopus delemar lipase (RDL) and Rhyzopus oryzae lipase (ROL) have been studied for the production of OPO from various palmitic acid‐rich fats and oleic acid or oleic acid‐rich plant oils (Chen et al., 2004; Gu et al., 2016; Schmid et al., 1999; Tecelão et al., 2012; Zheng et al., 2017; Zou, Jin, et al, 2016). Researchers have successfully used either commercially available immobilized lipases such as Lipozyme RM IM (Wei et al., 2015; Zou et al., 2011; Zou, Jin, et al, 2016), Lipozyme TL IM (Lee et al., 2010; Wei et al., 2015), Lipozyme‐20 (Lee et al., 2015), and Lipozyme‐60 (Chen et al., 2004) or lipases immobilized on different support materials in their laboratories. RML and RDL immobilized on polypropylene EP‐100 (Schmid et al., 1999), ROL immobilized on Accurel ® MP 1000 (Esteban et al., 2011; Robles et al., 2011; Tecelão et al., 2012), Aspergillus oryzae lipase (AOL) immobilized on polystyrene‐based hydrophobic macroporous adsorption resin (Gu et al., 2016) and CLL immobilized on magnetic multiwalled carbon nanotubes (Zheng et al., 2017) have been investigated for OPO synthesis process.…”

“…Several reports have shown that enzymatic interesterification of fats containing higher total PA content and higher percentage of sn2‐PA with commercial OA or oils containing higher total OA content and higher percentage of sn1,3‐OA produce a relatively higher percentage of OPO when compared with substrates of lower PA and OA contents (Lee et al., 2015; Zheng et al., 2017). Lee and his colleagues have reported that 55.2% of OPO is produced when tripalmitin and OA are used as substrates, whereas, only 25.2% OPO is produced when palm oil and camellia oil were used (Lee et al., 2015). Another report by Zheng and his colleagues has also shown that acidolysis of lard with OA produces 45% OPO but only 32.4% OPO is produced when restructured palm oil was used (Zheng et al., 2017).…”

Produção de sucedâneo da gordura do leite humano por interesterificação enzimática: uma revisão

“…Dos nove trabalhos específicos encontrados, seis apresentaram como objetivo a produção de um substituto da gordura do leite humano (HFMS) por processo de interesterificação enzimática a partir de diversas fontes de óleos e gorduras naturais (Yuan et al, 2020;Tecelão et al, 2019;Ghosh et al, 2016;Zou et al, 2016;Djajasoepena et al, 2015;Lee et al, 2015). Yuan et al, (2020), por exemplo sintetizaram Lípidos estruturados enriquecidos com TAGs de cadeia média e longa (MLCTs) por interesterificação de óleo de côco e de Bagre, usando a enzima NS 40086.…”

“…CpLIP2 exibiu maior atividade do que a maioria lipases imobilizadas comerciais (por exemplo, reação mais rápida em meio sem solvente, baixa carga de enzima e baixa razão molar necessária), e mostrou um comportamento regiosseletivo sn-1,3 reconhecido. Lee et al, (2015), produziram os HFMS usando gorduras naturais não pré-processadas e óleos com lipase. Após interesterificação de tripalmitina e ácido oleico em isooctano, os produtos da reação continham 55,2% de 1,3-dioleoil-2-palmitoil (CC BY 4.0) | ISSN 2525-3409 | DOI: http://dx.doi.org/10.33448/rsd-v10i3.13469 glicerol (OPO).…”

Process evaluation of solvent‐free lipase‐catalyzed esterification schemes in the synthesis of structured triglycerides from oleic and palmitic acids

“…The synthesis of OPO is often carried out through top‐down processes such as interesterification or acidolysis 4,5 . These reactions require triglycerides (TG) with PA at the sn ‐2 position, for example, tripalmitin, 6 and regio‐specific lipases, for example, Lipase RM IM 7 or Lipase TL IM, 5 which cleave off fatty acids at sn ‐1 and sn ‐3 positions for replacement with another fatty acid, such as OA. Water formation is absent, which prevents hydrolysis from occurring, but free fatty acids (FFA), which are released through lysis, as well as other TG of an undesired structure are inevitable by‐products of these processes.…”