Lipase‐catalysed production and chemical composition of diacylglycerols from soybean oil deodoriser distillate

Lo, Seong Koon; Baharin, Badlishah Sham; Tan, Chin Ping; Lai, Oi‐Ming

doi:10.1002/ejlt.200300888

Cited by 38 publications

(19 citation statements)

References 20 publications

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“…However, for Lipozyme TL IM, dramatically lower conversion of lauric acid was obtained. To further test the activity of TL IM in esterification reaction, oleic acid was employed (in the case of unsaturated fatty acids, other than air bubbling, N 2 bubbling was adopted), while conversion of oleic acid turned out low (35.2 ± 0.8%), indicating that Lipozyme TL IM was unlikely suitable for esterification reaction, which was agreed with some previous reports demonstrating Lipozyme TL IM to be less active in esterification reaction [12,16-18]. As consequence, Lipozyme RM IM was selected for subsequent experiments.…”

Section: Resultssupporting

confidence: 85%

Solvent-free enzymatic synthesis of 1, 3-Diacylglycerols by direct esterification of glycerol with saturated fatty acids

Zhong

Gui

et al. 2013

Lipids Health Dis

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BackgroundPure 1, 3-diacylglycerols (1, 3-DAG) have been considered to be significant surfactants in food, cosmetics and pharmaceutical industries, as well as the effect on obesity prevention.MethodsIn this study, a vacuum-driven air bubbling operation mode was developed and evaluated for the enzymatic synthesis of 1, 3-DAG of saturated fatty acids, by direct esterification of glycerol with fatty acids in a solvent-free system. The employed vacuum-driven air bubbling operation mode was comparable to vacuum-driven N2 bubbling protocol, in terms of lauric acid conversion and 1, 3-dilaurin content.ResultsSome operation parameters were optimized, and 95.3% of lauric acid conversion and 80.3% of 1, 3-dilaurin content was obtained after 3-h reaction at 50°C, with 5 wt% of Lipozyme RM IM (based on reactants) amount. Of the lipases studied, both Lipozyme RM IM and Novozym 435 exhibited good performance in terms of lauric acid conversion. Lipozyme TL IM, however, showed low activity. Lipozyme RM IM showed good operational stability in this operation protocol, 80.2% of the original catalytic activity remained after 10 consecutive batch applications. Some other 1, 3-DAG were prepared and high content was obtained after purification: 98.5% for 1, 3-dicaprylin, 99.2% for 1, 3-dicaprin, 99.1% for 1, 3-dilaurin, 99.5 for 1, 3-dipalmitin and 99.4% for 1, 3-disterin.ConclusionThe established vacuum-driven air bubbling operation protocol had been demonstrated to be a simple-operating, cost-effective, application practical and efficient methodology for 1, 3-DAG preparation.

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Section: Resultssupporting

confidence: 85%

Solvent-free enzymatic synthesis of 1, 3-Diacylglycerols by direct esterification of glycerol with saturated fatty acids

Zhong

Gui

et al. 2013

Lipids Health Dis

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“…DAG oil was manufactured enzymatically by lipasecatalysed esterification of glycerol with fatty acids from natural edible plant oils such as soybean, canola, and corn oil, and is composed largely of randomized diacylglycerols (DAG) [3,4]. Effects of reaction parameters such as reaction time, temperature, enzyme type, enzyme load, substrate molar ratio and water content were studied extensively in the past [4].…”

Section: Introductionmentioning

confidence: 99%

“…Effects of reaction parameters such as reaction time, temperature, enzyme type, enzyme load, substrate molar ratio and water content were studied extensively in the past [4]. DAG oil contains approximately 80% diacylglycerols (DAG), 20% triacylglycerols (TAG), 3% monoacylglycerols (MAG), \0.2% emulsifiers (polyglycerol esters of fatty acids), and antioxidants, mainly mixed tocopherols (0.075%).…”

Section: Introductionmentioning

confidence: 99%

High‐Resolution NMR Spectroscopy: An Alternative Fast Tool for Qualitative and Quantitative Analysis of Diacylglycerol (DAG) Oil

Hatzakis

Agiomyrgianaki

Kostidis

et al. 2011

J Americ Oil Chem Soc

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Multinuclear ( 1 H, 13 C, 31 P) and multidimensional NMR spectroscopy was employed for the analysis of diacylglycerol (DAG) oil and the quantification of its acylglycerols and acyl chains composition. A number of gradient selected two dimensional NMR techniques (TOCSY, HSQC-DEPT, HSQC-TOCSY, and HMBC) facilitated the assignment of the complex one dimensional 1 H-and 13 C-NMR spectra. In several cases, the aforementioned 2D-NMR techniques offered solid proof of earlier assignments based on chemical shift changes induced by the presence and relative positions of double bonds within the acyl chains. Integration of the appropriate signals in the NMR spectra of the three nuclei allowed the determination of DAG oil composition, which was found to be within the limits accepted for this oil, namely 1-monoacylglycerols 0.40-0.60%; 2-monoacylglycerols 0.40-0.50%; 1,3-diacylglycerols 57-62%; 1,2-diacylglycerols 28-32%; triacylglycerols 9-11%; saturated fatty acids 3-5%; oleic acid 37-45%; linoleic acid 49-53%; and linolenic acid 5-6.5%; tocopherols 0.24-0.27%. The compositional results obtained from the NMR spectra of the three nuclei were compared and discussed in terms of repeatability and ease of performance.

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“…However, few reports are available on the synthesis of DAG as the primary target. Esterification reactions with and without the use of an organic solvent have been tested for the synthesis of DAG (13)(14)(15). Glycerolysis reactions also have been used for the synthesis of DAG (16)(17)(18).…”

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confidence: 99%

Diacylglycerol synthesis by enzymatic glycerolysis: Screening of commercially available lipases

Kristensen

2005

J Americ Oil Chem Soc

108

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Seven lipases were screened for their ability to synthesize DAG in the glycerolysis of rapeseed oil. In batch reactions with free glycerol, the lipase carrier was of great importance for catalysis. Catalysis did not take place in reactions with lipases having hydrophilic carriers. The best DAG yield (approx. 60 wt%) was achieved with Novozym 435 and Lipase PS-D after 7 h, and an equilibrium was obtained. Stepwise addition of glycerol allowed catalysis with Novozym CALB L (immobilized) to take place in spite of the hydrophilic carrier; however, the DAG yield was only 19 wt%. This result suggests that glycerol forms a layer around the hydrophilic lipase particles, limiting contact between the lipases and the hydrophobic oil phase. With glycerol absorbed on silica gel, all lipases catalyzed the glycerolysis reaction. Faster conversion of TAG was obtained with Lipase PS-D, Lipase AK, and Lipase F-AP15 than in reactions with free glycerol, but the DAG yield remained approximately 60-65 wt%. Nonspecific lipases yielded more 1,3-DAG early in the reaction.Paper no. J10954 in JAOCS 82, 329-334 (May 2005).

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Lipase‐catalysed production and chemical composition of diacylglycerols from soybean oil deodoriser distillate

Cited by 38 publications

References 20 publications

Solvent-free enzymatic synthesis of 1, 3-Diacylglycerols by direct esterification of glycerol with saturated fatty acids

Solvent-free enzymatic synthesis of 1, 3-Diacylglycerols by direct esterification of glycerol with saturated fatty acids

High‐Resolution NMR Spectroscopy: An Alternative Fast Tool for Qualitative and Quantitative Analysis of Diacylglycerol (DAG) Oil

Diacylglycerol synthesis by enzymatic glycerolysis: Screening of commercially available lipases

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