Enzymatic synthesis of palm-based ascorbyl esters

Burham, Hamidah; Rasheed, Raizatul Ainaa Gafoor Abdul; Noor, Noorullhamezon Md.; Badruddin, Suzaini; Sidek, Hamidah

doi:10.1016/j.molcatb.2008.12.012

Cited by 47 publications

(30 citation statements)

References 13 publications

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“…This is in accordance with some previous reports, and it was probably due to diffusion limitation induced by linoleic acid high viscosity and/or reduced solubility of vitamin C in reaction medium with higher log P value (Burham et al, 2009). Side product of esterification reaction between linoleic acid and vitamin C is water.…”

Section: Optimization Of Reaction Conditionssupporting

confidence: 93%

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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Section: Optimization Of Reaction Conditionssupporting

confidence: 93%

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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“…Generally, lipases capable of ascorbyl ester synthesis are very rare, hence enzyme preparation used in our study Novozyme ® 435 was used in majority of reported studies 2,10,12,13,24 so comparison with results is simple. Applied enzyme concentrations were usually high, up to 2 w/v .…”

Section: Enzyme Loading Effectmentioning

confidence: 99%

“…Applied enzyme concentrations were usually high, up to 2 w/v . In a several studies the effect of enzyme amount was optimized, with simple one-factor at the time variation 2,16 or using RSM 12, 23 25 and obtained values were in range 0.18-1 w/v 2, 12, 16, 23 25 .…”

Section: Enzyme Loading Effectmentioning

confidence: 99%

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

et al. 2013

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“…Therefore, the modification of L-ascorbic acid via esterification or transesterification with acyl donors can be used as a tool to alter solubility in oil-based formulae and emulsion. The esterification process can be either chemical or enzymatic; however, the latter is preferred because of its advantages-high catalytic efficiency, high regioselectivity, mild reaction condition and inherent selectivity of the natural catalyst [3,4].…”

Section: Introductionmentioning

confidence: 99%

Kinetic biosynthesis of l-ascorbyl acetate by immobilized Thermomyces lanuginosus lipase (Lipozyme TLIM)

Zhang

Zhi

et al. 2011

Bioprocess Biosyst Eng

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Thermomyces lanuginosus lipase (Lipozyme TLIM)-catalyzed esterification of L-ascorbic acid was studied. It was suggested that Lipozyme TLIM was a suitable biocatalyst for enzymatic esterification of L-ascorbic acid. Three solvents were investigated for the reaction, and acetone was found to be a suitable reaction medium. Furthermore, it was found that water activity could notably affect the conversion. Moreover, pH memory of Lipozyme TLIM lipase for catalyzing L-ascorbic acid esterification in acetone was observed and the effect of pH on the reaction was estimated. In addition, the influences of other parameters such as substrate mole ratio, enzyme loading, and reaction temperature and reusability of lipase on esterification of L-ascorbic acid were also analyzed systematically and quantitatively. Kinetic characterization of Lipozyme TLIM showed that K(m,a) and V(max) were 80.085 mM and 0.747 mM min(-1), respectively. As a result, Lipozyme TLIM-catalyzed esterification of L: -ascorbic acid gave a maximum conversion of 99%.

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Enzymatic synthesis of palm-based ascorbyl esters

Cited by 47 publications

References 13 publications

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

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

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

Kinetic biosynthesis of l-ascorbyl acetate by immobilized Thermomyces lanuginosus lipase (Lipozyme TLIM)

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