Green synthesis routes toward triglycerides of conjugated linoleic acid

Busch, Stefan; Horlacher, Peter; Both, Sabine; Westfechtel, Alfred; Schörken, Ulrich

doi:10.1002/ejlt.201000111

Cited by 8 publications

(12 citation statements)

References 14 publications

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“…Both forms of CLA, free fatty acid and TAG, are rather equal for biological activity and for the absorption into chylomicrons 6. The TAG form of CLA can be ingested more easily than free fatty acid form because the major drawbacks of free CLA, such as a bitter taste and changes of acidity, can be reduced 6, 7.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of CLA‐enriched TAG by Candida antarctica lipase under vacuum

Hong

Kim

Yoon

et al. 2012

Euro J Lipid Sci & Tech

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Conjugated linoleic acid (CLA)-enriched triacylglycerol (TAG) of 90 wt% was successfully synthesized in 10 h by direct esterification of glycerol and CLA using an immobilized lipase from Candida antarctica under vacuum. The best operating conditions for the synthesis of TAG were investigated according to the three parameters of temperature, enzyme loading, and vacuum. The synthesis of TAG increased with increasing temperature but it did not significantly change above 608C ( p>0.05). The increase of enzyme loading lead to an enhanced conversion of TAG, but enzyme loading of more than 10% (based on the total weight of the substrates) was not effective. Moreover, when vacuum increased, the conversion of TAG increased, but the conversion rate decreased when the vacuum level was too high. The best combination of temperature, enzyme loading, and vacuum level were 608C, 10% of the total weight of the substrates, and 0.4 kPa, respectively. During the initial 6 h of reaction, Candida antarctica lipase had more selectivity for 10t,12c-CLA than 9c,11t-CLA onto the glycerol backbone, and a preference for the incorporation at the sn-1,3 positions of glycerol rather than at the sn-2 position.

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Section: Introductionmentioning

confidence: 99%

“…Transesterification and direct esterification have been used for the synthesis of TAG from fatty acid using lipase 4, 7, 16–22. Direct esterification produced purer reaction products and required shorter reaction times than transesterification 23, 24.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of CLA‐enriched TAG by Candida antarctica lipase under vacuum

Hong

Kim

Yoon

et al. 2012

Euro J Lipid Sci & Tech

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“…Liquid and powder formulations as well as immobilized enzyme preparations of CalB are available commercially. In most studies, ester synthesis is conducted with immobilized enzyme under continuous water removal, which leads to an equilibrium shift towards full conversion . However, water removal is not an easy task in large scale operation at low temperature.…”

Section: Resultsmentioning

confidence: 99%

“…Additionally, according to an overall LCA assessment, the enzymatic process is more eco‐friendly than the chemical one . Besides production of green emollients for the cosmetic industry, vacuum‐based synthesis with immobilized lipase CalB is applied for the production of omega‐3 fatty acid and conjugated linoleic acid based triglycerides [27,.…”

Section: Introductionmentioning

confidence: 99%

Native lipase dissolved in hydrophilic green solvents: A versatile 2‐phase reaction system for high yield ester synthesis

Kleiner¹,

Schörken²

2015

Euro J Lipid Sci & Tech

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Native lipase B from Candida antarctica was evaluated for ester production in the presence of hydrophilic green solvents including DES. Ester yields of up to 98% were achieved without removing water from the system in single step transformations. Analysis of the lipid phase exhibited a low water content of 0.29 mg/mL in the presence of DES in contrast to 2.5 mg/mL without solvent. Thus, water adsorbing properties of the hydrophilic solvents are responsible for the equilibrium shift towards ester synthesis, which was even observed in the presence of more than 20% water in total. Non-immobilized CalB was surprisingly active in hydrophilic solvents with logP-values below À1, when 5-10% water was added to the solvent phase and initial reaction velocities were significantly higher than with other organic solvents. Optimum reaction conditions were in the range of 40-50°C with a minimum content of 50 mg/kg pure CalB needed for full conversion. The solvent phase was easily separated by decantation and final product purification with established refinement procedures yielded esters of high quality. Stability testing of soluble lipase B revealed that enzyme stability in glycerol and ChCl:Gly is exceptionally high and stabilization of lipase in denaturing ChCl:U was possible in the presence of a lipid interface. The hydrophilic solvents were superior to less polar organic solvents in regards to ester yield and initial reaction velocity. A drawback of some hydrophilic solvents in lipase-catalyzed reactions is byproduct formation due to their chemical structure containing hydroxyl groups.Practical applications: The proposed biocatalytic process is suited for the preparation of green esters for cosmetic and technical applications in "low-cost" production equipment. As no water removal is needed to obtain high yields and no complex downstream processing is applied, the process may be conducted in simple stirred tank reactors. The recycling of the non-volatile hydrophilic solvent by example decantation can easily be done in most production units. The utilization of soluble lipases in small quantities even allows for single-use enzyme application, though the active enzyme may be recovered with the solvent and used again to minimize catalyst costs.Abbreviations: CalB, lipase B from Candida antarctica; ChCl:Gly, glycerol based DES; ChCl:U, urea based DES; DES, deep eutectic solvents Eur.

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“…CLA-enriched TAG can be synthesized chemically or enzymatically through esterification or transesterification processes [11,12,13]. Compared with chemical methods, lipase-catalysed esterification provides an alternative process due to its mild performance conditions, which prevents CLA from being destroyed.…”

Section: Introductionmentioning

confidence: 99%

Enzymatic Synthesis of Extremely Pure Triacylglycerols Enriched in Conjugated Linoleic Acids

Cao

Wang

et al. 2013

Molecules

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This work was objectively targeted to synthesize extremely pure triacylglycerols (TAG) enriched in conjugated linoleic acids (CLAs) for medical and dietetic purposes. Extremely pure CLA-enriched TAG was successfully synthesized by using the multi-step process: TAG was primarily synthesized by lipase-catalyzed esterification of CLA and glycerol and then the lower glycerides [monoacylglycerol (MAG) and diacylglycerol (DAG)] in the esterification mixtures was hydrolyzed to free fatty acids (FFAs) by a monoand di-acylglycerol lipase (lipase SMG1), finally, the FFAs were further separated from TAG by low temperature (150 °C) molecular distillation. The operation parameters for the lipase SMG1-catalyzed hydrolysis were optimized using response surface methodology based on the central composite rotatable design (CCRD). The operation parameters included water content, pH and reaction temperature and all of these three parameters showed significant effects on the hydrolysis of lower glycerides. The optimal conditions were obtained with a water content of 66.4% (w/w, with respect to oil mass), pH at 5.7 and 1 h of reaction time at 19.6 °C. Under these conditions, the content of lower glycerides in the reaction mixture decreased from 45.2% to 0.3% and the purity of CLA-enriched TAG reached 99.7%. Further purification of TAG was accomplished by molecular distillation and the final CLA-enriched TAG product yielded 99.8% of TAG. These extremely pure CLA-enriched TAG would be used for in vivo studies in animals and humans in order to get specific information concerning CLA metabolism.

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Green synthesis routes toward triglycerides of conjugated linoleic acid

Cited by 8 publications

References 14 publications

Synthesis of CLA‐enriched TAG by Candida antarctica lipase under vacuum

Synthesis of CLA‐enriched TAG by Candida antarctica lipase under vacuum

Native lipase dissolved in hydrophilic green solvents: A versatile 2‐phase reaction system for high yield ester synthesis

Enzymatic Synthesis of Extremely Pure Triacylglycerols Enriched in Conjugated Linoleic Acids

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