Effects of Reaction Parameters on the Incorporation of Caprylic Acid Into Soybean Oil for Production of Structured Lipids

Turan, Semra; Karabulut, İhsan; Vural, Halil

doi:10.1111/j.1745-4522.2006.00054.x

Cited by 22 publications

(19 citation statements)

References 17 publications

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“…It was observed that the amount of SFAs incorporated was gradually increased with the enzyme dosages increased. These results are consistent with the data obtained by Paez et al (22) and Turan et al (2). Similar observations have also been reported by Akoh and Huang (30) who studied the transesterification of triolein and caprylic acid and by Fomuso and Akoh (23) who studied the incorporation of caproic and butyric acids into triolein.…”

Section: Resultssupporting

confidence: 95%

Fatty Acid Selectivity of Lipases during Acidolysis Reaction between Triolein and Saturated Fatty Acids Varying from Caproic to Behenic Acids

Karabulut

Durmaz

Hayaloğlu

2009

J. Agric. Food Chem.

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The chain length selectivity of three immobilized lipases, namely, Lipozyme TL IM from Thermomyces lanoginosus, Lipozyme RM IM from Rhizomucor miehei, and Novozym 435 from Candida antarctica, was determined in acidolysis performed in hexane using the homologous series of even carbon number, saturated fatty acids (SFAs) of 6-22 carbons. Triolein with individual SFAs or a mixture of equimolar quantities of SFAs was used as the substrate. The effects of operating variables including the mole ratio of fatty acid to triolein, temperature, enzyme dosage, and time on incorporation were also investigated. Incorporation abilities of the enzymes tested were found to be significantly different for most of FAs at the experimental conditions evaluated. Lipases acted weakly on SFAs of which the carbon chain length was shorter than eight carbon atoms and higher than 18 carbon atoms. Lipases showed a bell-shaped distribution in incorporation vs chain length plot with a maximum around C12-C16. Among the experimental parameters tested, the effect of the substrate mole ratio was greater than those of the others, and the highest incorporation was observed for C12 (36.98%), C14 (37.63%), and C16 (38.66%) at a 4:1 substrate mole ratio with Lipozyme TL IM. Lipases caused significantly different levels of acyl migration from sn-1,3 to sn-2 positions.

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Section: Resultssupporting

confidence: 95%

Fatty Acid Selectivity of Lipases during Acidolysis Reaction between Triolein and Saturated Fatty Acids Varying from Caproic to Behenic Acids

Karabulut

Durmaz

Hayaloğlu

2009

J. Agric. Food Chem.

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“…Therefore, the changes can be made at sn-1 and sn-3 glycerol positions but not at sn-2 position, where the ester group remains unchanged [4]. The sn-1,3-specific lipases have been used to promote the incorporation of medium-chain fatty acids, such as caprylic (C8:0) and capric (C10:0) acids, into TAG molecule of several vegetable and fish oils to obtain SL with important clinical and nutritional properties [5][6][7][8][9][10][11].…”

Section: Introductionmentioning

confidence: 99%

Production of MLM‐Type Structured Lipids Catalyzed by Immobilized Heterologous Rhizopus oryzae Lipase

Nunes

Pires-Cabral

Guillén

et al. 2010

J Americ Oil Chem Soc

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This work aims to produce triacylglycerols (TAG) containing a medium-chain fatty acid (M) at positions sn-1,3 and a long-chain fatty acid (L) at sn-2 position, i.e. TAG of MLM type, by acidolysis of virgin olive oil with caprylic (C8:0) or capric (C10:0) acids, catalyzed by 1,3-selective Rhizopus oryzae heterologous lipase (rROL) immobilized in Eupergit Ò C and modified sepiolite. This lipase was produced by the methylotrophic yeast Pichia pastoris. Reactions were performed at 25 and 40°C, for 24 h, either in solvent-free or in n-hexane media, at a molar ratio 1:2 (olive oil:free fatty acid). Higher incorporations of C8:0 (21.6 mol%) and C10:0 (34.8 mol%) into the TAG were attained in solvent-free media, at 40°C, when rROL immobilized in Eupergit Ò C was used. In organic media, at 40°C, only 15.9 and 14.1 mol%, incorporation of C8:0 or C10:0 were, respectively observed. Lower incorporations were attained for both acids (3.4-7.0 mol%) when native ROL (nROL) in both supports and rROL in modified sepiolite were used. rROL in Eupergit Ò C maintained its activity during the first four or three 23-h batches, respectively when C8:0 (half-life time, t 1/2 = 159 h) or C10:0 (t 1/2 = 136 h) were used, decreasing thereafter following a time delay model. Keywords Acidolysis Á Capric acid Á Caprylic acid Á Olive oil Á Rhizopus oryzae lipase Á Structured lipids Abbreviations FFA Free fatty acid(s) L Long-chain fatty acid(s) M Medium-chain fatty acid(s) MAG Monoacylglycerol(s) MLM Triacylglycerol(s) containing medium-chain fatty acid at sn-1 and sn-3 positions (M) and a long-chain fatty acid (L) at position sn-2 nROL Native ROL rROL Heterologous ROL ROL Rhizopus oryzae lipase SL Structured lipid(s) TAG Triacylglycerol(s) t

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“…Lipasecatalyzed acidolysis, in which medium chain FAs (caprylic, C8:0, or capric acids, C10:0) are used as acyl donors, and vegetable or fish oils are used as the source of glycerol backbone and long chain FAs, is one of the most commonly used methods to produce SL of the MLM-type (Ferreira-Dias et al, 2013). The sn-1,3 specific lipases have currently been used to catalyze the incorporation of medium chain FAs at the sn-1,3 positions of the TAG molecule, while the central position is preferentially occupied by unsaturated long-chain FAs, namely oleic and linoleic acids (Osborn and Akoh, 2002;Turan et al, 2006;Feltes et al, 2009;Nunes et al, 2011a, b). Acidolysis reaction presents some advantages over other lipase-catalyzed reactions, such as esterification and interesterification.…”

Section: Introductionmentioning

confidence: 99%

Incorporation of capric acid in pumpkin seed oil by sn-1,3 regioselective lipase-catalyzed acidolysis

Sousa

Campos

Nunes

et al. 2018

OCL

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-Structured lipids (SLs) are novel triacylglycerols obtained by changing the native fatty acid (FA) profiles or by the incorporation of a new desired FA in the acylglycerol backbone. These modified fats present important medical and functional properties for food applications. This work aimed to synthetize a MLM-type SL, which consists of triacylglycerols containing a medium-chain FA (M) at sn-1,3 positions and a long-chain FA (L) at sn-2 position, by acidolysis of pumpkin seed oil with capric acid, catalyzed by a commercial lipase preparation from Thermomyces lanuginosa (Lipozyme TL IM). Reactions were performed at 45°C, in solvent-free media, at 1:2 molar ratio (pumpkin seed oil:capric acid) and a fixed amount of immobilized lipase of 5%, 10%, 15% or 20%. Incorporations of C10:0 increased with time up to 31 h (29.9 ± 0.7 mol-%) when 5% lipase load was used. Significant differences were only observed between the results obtained with 5 and 20% of biocatalyst load. The subsequent experiment was carried out with 5% lipase load, at 45°C, 1:2 molar ratio and in the presence of n-hexane. The results showed slightly higher incorporation yields in the presence of solvent, namely at 48 h-reaction (34.7 ± 1.0 mol-%). However, since the structured lipids are to be used in food products, together with environmental and economic concerns, solvent-free systems are preferred. In this study, the synthesis of a MLM-type SL from pumpkin seed oil for food uses was well succeeded.Keywords: structured lipid / acidolysis / pumpkin seed oil / capric acid / lipozyme TL IM Résumé -Incorporation d'acide caprique dans de l'huile de pépin de citrouille par acidolyse catalysée par une lipase sn-1,3 régiosélective. Les lipides structurés sont de nouveaux triacylglycérols obtenus en changeant les profils des acides gras (AG) natifs ou par l'incorporation de nouveaux AG souhaités dans le squelette glycérol. Ces graisses modifiées présentent des propriétés médicales et fonctionnelles importantes pour des applications alimentaires. Ce travail vise à synthétiser un lipide structuré de type MLM, qui consiste en des triacylglycérols contenant un AG à chaîne moyenne (M) en positions sn-1,3 et un acide gras à chaîne longue (L) en position sn-2, par acidolyse de l'huile de graine de citrouille avec l'acide caprique, catalysée par une préparation commerciale de lipase de Thermomyces lanuginosa (Lipozyme TL IM). Les réactions ont été effectuées à 45°C, sans solvant, avec un rapport molaire de 1:2 (huile de graines de citrouille: acide caprique) et une quantité fixe de lipase immobilisée de 5 %, 10 %, 15 % ou 20 %. Avec une charge en lipase de 5 %, l'incorporation du C10:0 a augmenté avec le temps jusqu'à 31 h (29,9 ± 0,7 mol %). Des différences significatives ont été observées seulement entre les résultats obtenus avec 5 et 20 % de charge en biocatalyseur. L'expérience suivante a été réalisée avec une charge en lipase de 5 %, à 45°C, un rapport molaire 1:2 et en présence de n-hexane. Les résultats ont montré des rendements d'incorporation lég...

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Effects of Reaction Parameters on the Incorporation of Caprylic Acid Into Soybean Oil for Production of Structured Lipids

Cited by 22 publications

References 17 publications

Fatty Acid Selectivity of Lipases during Acidolysis Reaction between Triolein and Saturated Fatty Acids Varying from Caproic to Behenic Acids

Fatty Acid Selectivity of Lipases during Acidolysis Reaction between Triolein and Saturated Fatty Acids Varying from Caproic to Behenic Acids

Production of MLM‐Type Structured Lipids Catalyzed by Immobilized Heterologous Rhizopus oryzae Lipase

Incorporation of capric acid in pumpkin seed oil by sn-1,3 regioselective lipase-catalyzed acidolysis

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