Lipase-Catalyzed Synthesis of Ascorbyl Oleate in Acetone: Optimization of Reaction Conditions and Lipase Reusability

Stojanović, Mirjana D.; Veličković, Dušan; Dimitrijević, Aleksandra; Milosavić, Nenad; Knežević‐Jugović, Zorica; Bezbradica, Dejan

doi:10.5650/jos.62.591

Cited by 20 publications

(9 citation statements)

References 40 publications

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“…Less pronounced discrepancies were observed with optimum values of the substrate molar ratio ( x 4 ), since the optimum was 1:18 for conversion (Figure S1a of the Supporting Information) and 1:13 for the specific product yield (Figure S1b of the Supporting Information). Obviously optimization based solely on substrate conversion as output, which is used in the majority of studies of lipase-catalyzed reactions, could be somewhat misleading because high conversion of the substrate is favored by very high consumption of enzyme at low substrate concentrations. , It was already noticed that the optimization based on the specific product yield gives much better insight into the productivity of the enzymatic process and the development of a cost-efficient process . Also, values of specific yields obtained in our experiments were significantly higher in comparison with those from other published studies of phloridzin esters of long chain fatty acids and lauric acid: 0.73 mmol g –1 and 1.25 mmol g –1 , respectively. , …”

Section: Resultsmentioning

confidence: 55%

“…The specific product yield was used as an output parameter (besides the prevalently used conversion of limiting substrate) since the high cost of enzyme is a significant limitation for the development of economically efficient lipase-catalyzed processes of ester synthesis, and it has been proven in our previous study that optimum values of several factors significantly differ for different outputs. 28 The highest conversion was 76.2% and it was achieved in experiment 17, with the maximum value of reaction time (2) Second order regression models describing the effects of factors on outputs were obtained after the Fisher test for model adequacy and the Student test for the significance of model parameters. After the elimination of insignificant terms, second order regression models that describe the effects of experimental factors on conversion (Y 1 ) (eq 2) and specific yield (Y 2 ) (eq 3) were obtained.…”

Section: Resultsmentioning

confidence: 99%

“…All experiments have been performed with molar excess of oleic acid; hence conversion was calculated with respect to phloridzin since it was the limiting substrate. The specific product yield was used as an output parameter (besides the prevalently used conversion of limiting substrate) since the high cost of enzyme is a significant limitation for the development of economically efficient lipase-catalyzed processes of ester synthesis, and it has been proven in our previous study that optimum values of several factors significantly differ for different outputs . The highest conversion was 76.2% and it was achieved in experiment 17, with the maximum value of reaction time (2) and central values (0) of all other factors.…”

Section: Resultsmentioning

confidence: 99%

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Lipase-Catalyzed Esterification of Phloridzin: Acyl Donor Effect on Enzymatic Affinity and Antioxidant Properties of Esters

Milisavljević

Stojanović

Carević

et al. 2014

Ind. Eng. Chem. Res.

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Lipase-catalyzed acylation of phloridzin with a wide range of fatty acids and antioxidant activities of synthesized esters were investigated in this study. Polar solvents were suitable reaction media for esterification, and the highest yield was achieved in acetonitrile. By using statistically designed optimization of key experimental factors for the synthesis of phloridzil oleate as the model reaction, great improvements in achieved conversion and yield per enzyme mass were enabled. The most significant progress has been made in the cost-effectiveness of the reaction, since the specific yield of 5.45 mmol g −1 was obtained at 58°C, with 0.09 M phloridzin, 1.17 M oleic acid, and only 0.5% (w/v) biocatalyst. All examined fatty acids were suitable acyl donors, since the chain length and unsaturation degree had slight effects on esterification and all products yielded over 70%. Phloridzil caprate, myristate, and oleate exhibited the highest antioxidant activities among the obtained esters.

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Section: Resultsmentioning

confidence: 55%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Lipase-Catalyzed Esterification of Phloridzin: Acyl Donor Effect on Enzymatic Affinity and Antioxidant Properties of Esters

Milisavljević

Stojanović

Carević

et al. 2014

Ind. Eng. Chem. Res.

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“…Previous research has shown that the addition of molecular sieves to an EIE reaction has the main advantage of controlling the water activity of the system 45 . This reduces the extent of hydrolysis reactions and formation of by-products (mainly free fatty acids and DAGs) 46 and increasing the reaction yield by shifting the thermodynamic equilibrium towards ester synthesis 47 . The water activity of Lipozyme RM IM (in powder form) before starting the reaction was 0.423 ± 0.004 at 25 °C.…”

Section: Resultsmentioning

confidence: 99%

Facile lipase-catalyzed synthesis of a chocolate fat mimetic

Ghazani

Marangoni

2018

Sci Rep

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A cocoa butter equivalent (CBE) was synthesized enzymatically from readily available edible fats with fatty acid and triacylglycerol compositions that closely resemble the fat present in chocolate, cocoa butter. A commercially available immobilized fungal lipase, Lipozyme RM IM, was used as the reaction catalyst. Reaction parameters were a temperature of 65 °C, water activity of 0.11, a 4 h reaction time, and a substrate mass ratio of a commercial enzymatically synthesized shea stearin (SS) to palm mid-fraction (PMF) of 6:4 (w/w). Fractionation was also used after reaction completion to further approach the triacylglycerol composition of cocoa butter by removing trisaturated and unsaturated triacylglycerols. The yield of the triglyceride 1-palmitoyl-2-oleoyl, 3-stearoyl-glycerol (POS) produced was 57.7% (w/w). The amounts of 1,3-dipalmitoyl-2-oleoyl-glycerol (POP), (POS) and 1,3-stearoyl-2-oleoyl-glycerol (SOS) in the final CBE were 11.2%, 36.3%, and 34.8%, respectively. In comparison, the amounts of POP, POS and SOS in the cocoa butter used in this study were 15.2%, 38.2%, and 27.8%, respectively. No significant differences (P > 0.05) in melting point and enthalpy of fusion between CB and the CBE were observed. In comparison, a non-interesterified blend of SS and PMF (60:40 w/w) showed significantly (P < 0.05) higher melting point and lower enthalpy of fusion compared to CB. The crystal polymorphic form V of CB (β2-3L) was similar to that of CBE and SS/PMF (60:40 w/w). The solid fat content (SFC) vs. temperature profile of the CBE generally resembled that of CB, except that the CBE had significantly (P < 0.05) higher SFCs at 5, 10, 15, 20 and 25 °C compared to both CB and SS/PMF (60:40 w/w). Addition of 15% (w/w) CBE to CB did not cause any changes in physical properties (melting point, SFC and crystal polymorphic forms) of the CB. This study demonstrates the potential for synthesizing a CB-like CBE using a green, rapid, straightforward one step enzymatic conversion followed by fractionation from widely available edible fats.

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“…Side product of esterification reaction between linoleic acid and vitamin C is water. Therefore, high water content in medium is undesirable for position of reaction equilibrium (Stojanović et al, 2013b). On the other hand, lipases are known to keep their active conformation only if they are surrounded by monomolecular layer of water (Hsieh et al, 2005).…”

Section: Optimization Of Reaction Conditionsmentioning

confidence: 99%

Enzymatic lipophilization of vitamin C with linoleic acid: Determination of antioxidant and diffusion properties of L-ascorbyl linoleate

Ćorović¹,

Milivojevic²,

Carevic³

et al. 2018

Food & Feed Res

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Lipophilic derivatives of vitamin C are additives with antioxidant properties, attractive for application in food, cosmetics and pharmaceutics. They could be synthesized in lipase-catalyzed processes by using various acyl donors. Hereby, we present application of linoleic acid, which is polyunsaturated fatty acid essential in human nutrition, for esterification of vitamin C catalyzed by immobilized enzyme preparation Novozym ® 435 in acetone. Highest specific ester yield, 9.7 mmol/g of immobilized lipase, was accomplished with 0.15 M of vitamin C, 0.6 M of linoleic acid, 3 g/l of enzyme and 0.07% (v/v) of water, at 60 °C. NMR analyses of purified product proved that synthesized molecule was identical to 6-O-ascorbyl linoleate. Capacity of ester for scavenging 2,2-diphenyl-1-picrylhydrazyl radicals was two times higher comparing to parent molecule, vitamin C. Its diffusion coefficient, determined using Franz cell and cellulose acetate membrane, was 40% higher than palmitate and 62% higher than oleate. Obtained results showed that L-ascorbyl linoleate could be successfully synthesized in biocatalyzed processes. Furthermore, it was demonstrated that it possess high potential for application in different lipophilic products due to its liposolubility, high antioxidant efficiency and good diffusion properties.

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Lipase-Catalyzed Synthesis of Ascorbyl Oleate in Acetone: Optimization of Reaction Conditions and Lipase Reusability

Cited by 20 publications

References 40 publications

Lipase-Catalyzed Esterification of Phloridzin: Acyl Donor Effect on Enzymatic Affinity and Antioxidant Properties of Esters

Lipase-Catalyzed Esterification of Phloridzin: Acyl Donor Effect on Enzymatic Affinity and Antioxidant Properties of Esters

Facile lipase-catalyzed synthesis of a chocolate fat mimetic

Enzymatic lipophilization of vitamin C with linoleic acid: Determination of antioxidant and diffusion properties of L-ascorbyl linoleate

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