Feruloylated Products from Coconut Oil and Shea Butter

The synthesis of feruloylated coconut oil and feruloylated shea butter were demonstrated in 0.5-L scale, shaken, batch reactions. Ethyl ferulate and the vegetable oil/fat were combined in a 1.0:1.3 mol ratio in the presence of Candida antartica lipase B immobilized on an acrylic resin (Novozym 435) at 60 °C. The transesterification of ethyl ferulate with coconut oil and shea butter reached equilibrium conversions, after 22 days, of 63 and 70%, respectively, with the shea butter transesterifications producing a white precipitate not observed in the coconut oil transesterifications. The faster transesterification rates, equilibrium conversions and white precipitate were shown to result from di- and monoacylglycerols (DAG and MAG) present in the shea butter. The transesterification of ethyl ferulate and coconut oil was also tested in a continuous, enzymatic, packed-bed bioreactor using Novozym 435 at 60 °C to produce feruloylated coconut oil at rates of 0.5–0.9 kg/day over 4.5 months. The feruloylated coconut oil acylglycerol species were identified by LC–MS analysis of transesterification reactions of ethyl ferulate with medium chain triacylglycerol (TAG) standards, C8–C14. The feruloylated vegetable oils possessed an ultra violet (UV) absorbing λ _max 328 nm, making them good UVAII absorbers, as defined by the U.S. Food and Drug Administration. The feruloylated coconut oil possessed a 17.5% higher absorption capacity than feruloylated shea butter on a per weight basis. All the feruloylated vegetable oils possessed rapid antioxidant capacity (50% reduction of initial radical concentration <5 min) at the concentrations tested, 0.5–2.5 mM. Feruloylated coconut oil possessed chemical and physical characteristics that suggested it would be fungible for feruloylated soybean oil in current retail formulations.     

Mass spectrometric identification of triacylglycerols of enzymatically modified butterfat separated on a polarizable phenylmethylsilicone column

Original butter oil, butter oil interesterified withPseudomonas fluorescens lipase as catalyst, and the saturated, monoene, diene and triene fractions of interesterified butter oil from silver ion chromatography on ap-propylbenzene sulfonic acid column were analyzed on a polarizable phenyl(65%)methylsilicone column. Major and also some minor molecular species of triacylglycerols (TG) were identified from the electron-impact (EI) gas chromatography/mass spectrometry analytical data for the original and lipase-modified butter oil and the four fractions. Acyl + 74 and acyl + 128 fragments of EI mass spectral data proved useful, in addition to acyl and M - RCOO fragments, in the identification of molecular species of TG. The TG compositions of the modified butter oils were compared with the composition calculated according to random distribution and with the TG composition of original butter oil.     

Influence of physical pretreatments of sheanuts (Vitellaria paradoxa Gaertn.) on butter quality

Shea butter, usually extracted from kernels of Vitellaria paradoxa Gaertn. by rural women in Sub‐Saharran Africa, has multiple traditional and industrial uses. Traditional processing methods are not standardized and often lead to the production of poor quality butter, which attract low market prices. The aim of this work was to study the different pretreatments locally applied to sheanuts during processing in order to identify those that can affect butter quality. The effect of cooking, soaking as well as drying on the amount of butter extracted and its minor constituents were investigated. All these pretreatments significantly affected oil quality. The effect of soaking of the kernels on improving oil extraction yields (55%) was comparable to that of kernels digested with α‐amylase, acid protease, cellulase/hemicellulase, pectinase, and glucanase enzymes before oil extraction reported in the literature. Drying had a significant negative effect on tocopherol contents of the oil. However, residual amounts of tocopherols in the oil after drying were high enough to suggest that it may still confer anti‐oxidant activities. Soaking, cooking, and drying are important pretreatments involved in the production of shea butter locally that need to be standardized in order to produce better quality butter. Practical applications: In this work, we carried out scientific analysis of methods already used by rural women to process shea fruits into shea butter. This work should be useful for establishing processing conditions for obtaining good quality shea butter.     

Canola Proteins Used as Co‐Emulsifiers with Phospholipids Influence Oil Oxidability,Enzymatic Lipolysis,and Fatty Acid Absorption in Rats

The objective of this study is to formulate and characterize oil‐in‐water emulsions with plant‐derived ingredients only, that is, proteins extracted from canola oil bodies, used as co‐emulsifiers with a canola lecithin, and to assess their suitability for food applications. Using the protein extract increases the chemical stability of rapeseed oil emulsions toward oxidation, based on the delay in conjugated diene formation under accelerated storage conditions, and favors pancreatic lipase activity. Bioaccessibility of rapeseed fatty acids is compared in lymph‐duct‐cannulated rats fed oil or emulsion. Fatty acid absorption by the intestine is increased by 78% when the oil is emulsified with canola proteins as co‐emulsifier: 28.7 mg mL^?1 versus 16.1 mg mL^?1 for oil (p < 0.05). In vitro lipolysis results are in overall agreement with fatty acid absorption in vivo. Practical Applications: Results obtained for rapeseed oil emulsified with canola proteins and phospholipids suggest that increased bioaccessibility of n‐3 polyunsaturated fatty acids could be offered in vegan food products.     

Quantification of Phorbol Esters in Jatropha curcas by HPLC‐UV and HPLC‐ToF‐MS with Standard Addition Method

Established analytic methods for the quantification of phorbol esters (PE), which are some toxic components in Jatropha curcas L., include HPLC with UV‐detection with the commercially available phorbol myristate acetate (PMA) as internal standard or HPLC coupled with MS detection with an external calibration, mostly also with PMA. The differences in the fatty acid side chains and connection to the base structure of PMA compared to PE leads to different UV absorption and MS ionization effects and cause problems for exact quantitative measurements. In this paper, a method is presented which combines both detection types and shows differences between both results. For this purpose, an extraction routine is performed on a PE‐containing seed oil to get a PE standard in high purity, which was used for a standard addition method on two real J. curcas oil samples, derived from Ghana and Mexico. Furthermore, a detection window of ±10 ppm for the high accurate ToF‐MS detection is set to eliminate isobaric interferences from co‐eluting material. Method evaluation of inter‐ and intra‐day variance as well as the recovery rate are performed and determined. With this method a limit of detection of 62 ng mL^?1 (UV) and 11 ng mL^?1 (MS) can be achieved. Practical Applications: Due to the good biological and technical properties of Jatropha curcas L., its seed oil seems perfect for the application as biodiesel feedstock. The toxicity on the other hand could cause problems when converting side products from the oil production to products of higher value. With the here described method an accurate and precise analysis procedure for the quantification of the toxic compounds namely, phorbol esters, could be applied for toxicity studies or routine checks in industry which is converting plant material from J. curcas, so that no toxic material is used for example as animal feed. In this paper, an exact and robust analysis method is described for the quantification of phorbol esters (PE) in Jatropha curcas L. seed oil. This method procedure includes the extraction of PE in methanol, chromatographic separation on a reverse phase C18 HPLC column and the quantification by standard addition method. For the standard addition method a highly pure PE standard is used, which is extracted and purified by semi preparative HPLC right before the measurements. The used detector for identification and quantification is UV set at 280 nm and ESI‐ToF‐MS with a ±10 ppm mass difference of the deprotonated and formate adduct pseudo molecular ion of PE.

     

Selectivity of lipases: isolation of fatty acids from castor,coriander, and meadowfoam oils

The lipase‐catalyzed hydrolysis of castor, coriander, and meadowfoam oils was studied in a two‐phase water/oil system. The lipases from Candida rugosa and Pseudomonas cepacia released all fatty acids from the triglycerides randomly, with the exception of castor oil. In the latter case, the P. cepacia lipase discriminated against ricinoleic acid. The lipase from Geotrichum candidum discriminated against unsaturated acids having the double bond located at the Δ‐6 (petroselinic acid in coriander oil) and Δ‐5 (meadowfoam oil) position or with a hydroxy substituent (ricinoleic acid). The expression of the selectivities of the G. candidum lipase was most pronounced in lipase‐catalyzed esterification reactions, which was exploited as part of a two‐step process to prepare highly concentrated fractions of the acids. In the first step the oils were hydrolyzed to their respective free fatty acids, in the second step a selective lipase was used to catalyze esterification of the acids with 1‐butanol. This resulted in an enrichment of the targeted acids to approximately 95—98% in the unesterified acid fractions compared to the 70—90% content in the starting acid fractions.     

Production of Lipase from Geotrichum candidum Using Corn Steep Liquor in Different Bioreactors

The production of an extracellular lipase using corn steep liquor (CSL) as the nitrogen source in the cultivation of Geotrichum candidum NRRLY‐552 was evaluated. The optimized conditions in shake flasks were CSL, 8.0 % w/v, soybean oil, 0.6 % w/v, pH 7.0, 30 °C, 250 rpm, and 48 h, resulting in a maximum lipase productivity of 0.438 U mL^?1 h^?1(U = the amount of enzyme required to liberate 1 μmol of fatty acid per minute). Scale‐up was evaluated with airlift and stirred tank reactors; the best conditions, respectively, were 1 vvm(volume of gas per volume of medium per minute) of aeration which resulted in 0.535 U mL^?1 h^?1 (32 h) and 1 vvm and 300 rpm resulting in 0.563 U mL^?1 h^?1 (16 h). To facilitate downstream processes, lipase production was also evaluated using CSL previously clarified with activated charcoal resulting in 0.275 U mL^?1 h^?1 (24 h) using 12 % (w/v) of clarified CSL in shake flasks. The obtained results showed that CSL leads to similar productivity compared to peptone using the same microorganism under similar conditions. In addition the cost of fermentation medium using CSL is much lower because it is a very inexpensive by‐product from corn processing.     

Enzymatic acidolysis of an arachidonic acid single-cell oil with capric acid

Incorporation of capric acid (CA) into arachidonic acid (AA) single-cell oil, using five commercial lipases, indicated that lipase PS-30 from Pseudomonas sp. was most effective. The optimal conditions included an oil-to-CA mole ratio of 1∶3, a temperature of 45°C, incubation time of 24 h, 4% lipase from Pseudomonas sp., and a 2% (w/w) water content. Examination of positional distribution of FA on the glycerol backbone of modified AA single-cell oil with CA showed that 89.7% of CA was concentrated in the sn-1,3 positions of the TAG molecules. AA was mainly located at the sn-2 position of the modified AA single-cell oil. Enzymatically modified AA single-cell oil had a higher conjugated dienes (CD) value than its unmodified counterpart. TBARS values of both modified and unmodified AA single-cell oils increased progressively during the entire storage period, but no significant difference existed between TBARS values of both oils. Thus, enzymatically modified oil was more susceptible to oxidation than its unmodified counterpart, when considering both CD and TBARS values. Removal of natural antioxidants during oil modification might play a significant role in rapid oxidative deterioration of enzymatically modified oils. This possibility was confirmed when starting materials were subjected to the same reaction process in the absence of any enzyme, as the resultant oil was indeed significantly less stable than the control oil.     

Lipase‐catalyzed alcoholysis of vegetable oils

Fatty acid alkyl esters were produced from various vegetable oils by transesterification with different alcohols using immobilized lipases. Using n‐hexane as organic solvent, all immobilized lipases tested were found to be active during methanolysis. Highest conversion (97%) was observed with Thermomyces lanuginosa lipase after 24 h. In contrast, this lipase was almost inactive in a solvent‐free reaction medium using methanol or 2‐propanol as alcohol substrates. This could be overcome by a three‐step addition of methanol, which works efficiently for a range of vegetable oils (e.g. cottonseed, peanut, sunflower, palm olein, coconut and palm kernel) using immobilized lipases from Pseudomonas fluorescens (AK lipase) and Rhizomucor miehei (RM lipase). Repeated batch reactions showed that Rhizomucor miehei lipase was very stable over 120 h. AK and RM lipases also showed acceptable conversion levels for cottonseed oil with ethanol, 1‐propanol, 1‐butanol and isobutanol (50‐65% conversion after 24 h) in solvent‐free conditions. Methyl and isopropyl fatty acid esters obtained by enzymatic alcoholysis of natural vegetable oils can find application in biodiesel fuels and cosmetics industry, respectively.     

Effect of Thymus haussknechtii and Origanum acutidens essential oils on the stability of cow milk butter

The aim of this study was to investigate the effects of different essential oils (from Thymus haussknechtii Velen and Origanum acutidens Hand.‐Mazz. Letswaart; endemic species in Turkey) on butter stability. These essential oils were added to butter at two concentrations (0.1 and 0.2 wt‐%). The antioxidant activities of the essential oils were compared with control samples (without antioxidant) and containing butylated hydroxytoluene (BHT). All samples were stored at 4 ± 1 °C for 90 days and their peroxide values (PV), thiobarbituric acid (TBA) values, % titratable acidity and some microbiological properties were analyzed. As a result, the lowest PV and TBA values were determined in the samples containing BHT and 0.2% essential oils; however, TBA and PV were at the highest levels in the control samples during storage. The amount of 0.2% of essential oils exhibited strong antioxidant activity, which was almost equal to that of BHT. T. haussknechtii essential oil showed a stronger antioxidant effect as compared to O. acutidens. None of the essential oils showed remarkable antifungal activity. However, the antimicrobial activity of O. acutidens on coliform bacteria was found to be higher than that of T. haussknechtii. Sensory analysis of the butter showed that the samples containing 0.2% essential oils had lower flavor scores than those with 0.1% essential oils. The present results indicate that these essential oils can be considered as an alternative source of natural antioxidants in the manufacture of butter.     

Production of structured TAG rich in 1,3-capryloyl-2-arachidonoyl glycerol from <Emphasis Type="Italic">Mortierella</Emphasis> single-cell oil

Two oils containing a large amount of 2-arachidonoyl-TAG were selected to produce structured TAG rich in 1,3-capryloyl-2-arachidonoyl glycerol (CAC). An oil (TGA58F oil) was prepared by fermentation of Mortierella alpina, in which the 2-arachidonyoyl-TAG content was 67 mol%. Another oil (TGA55E oil) was prepared by selective hydrolysis of a commercially available oil (TGA40 oil) with Candida rugosa lipase. The 2-arachidonoyl-TAG content in the latter was 68 mol%. Acidolysis of the two oils with caprylic acid (CA) using immobilized Rhizopus oryzae lipase showed that TGA55E oil was more suitable than TGA58F oil for the production of structured TAG containing a higher concentration of CAC. Hence, a continuous-flow acidolysis of TGA55E oil was performed using a column (18×125 mm) packed with 10 g immobilized R. oryzae lipase. When a mixture of TGA55E oil/CA (1∶2, w/w) was fed at 35°C into the fixed-bed reactor at a flow rate of 4.0 mL (3.6 g)/h, the degree of acidolysis initially reached 53%, and still achieved 48% even after continuous operation for 90 d. The reaction mixture that flowed from the reactor contained small amounts of partial acylglycerols and tricaprylin in addition to FFA. Molecular distillation was used for purification of the structured TAG, and removed not only FFA but also part of the partial acylglycerols and tricaprylin, resulting in an increase in the CAC content in acylglycerols from 44.0 to 45.8 mol%. These results showed that a process composed of selective hydrolysis, acidolysis, and molecular distillation is effective for the production of CAC-rich structured TAG.     

Formation and distribution of oxidized fatty acids during deep‐ and pan‐frying of potatoes

The formation of cis‐9,10‐epoxystearate, trans‐9,10‐epoxystearate, cis‐9,10‐epoxyoleate, cis‐12,13‐epoxyoleate, trans‐9,10‐epoxyoleate, trans‐12,13‐epoxyoleate and the co‐eluting 9‐ and 10‐ketostearates during eight successive pan‐ and deep‐frying sessions of pre‐fried potatoes in five different types of vegetable oils – namely cottonseed oil, sunflower oil, vegetable shortening, palm oil and virgin olive oil – was followed and quantified both in fried oils and in fried potatoes by GC/MS after derivatization to methyl esters. These oxidized fatty acids were present at relatively low concentrations in the fresh oils and pre‐fried potatoes while they increased linearly with frying time, reaching up to 1140.8 µg/g in virgin olive oil (VOO) and 186.9 µg/g in potatoes pan‐fried in VOO after eight pan‐frying sessions, with trans‐9,10‐epoxystearate predominating in all cases. The formation of polymerized triacylglycerols (PTG) was also quantified in frying oils by size exclusion HPLC. Pan‐frying caused higher oxidized fatty acid and PTG formation compared to deep‐frying. Epoxyoleates and PTG concentrations were increased after frying in polyunsaturated oils, while epoxystearate and 9‐ and 10‐ketostearate concentrations were increased after frying in monounsaturated oils. No specific absorption of the oxidized fatty acids by the fried potatoes seems to occur. The dietary intake of oxidized fatty acids and PTG by the consumption of fried potatoes was discussed.     

Identification of triacylglycerols in the enzymatic transesterification of rapeseed and butter oil

A blend of rapeseed and butter oil was transesterified using immobilized Thermomyces lanuginosus lipase (Lipozyme® TL IM) as catalyst. The reaction was followed by reversed-phase HPLC and the triacylglycerol peaks were tentatively identified from their elution times by calculating equivalent carbon numbers. Further identification was made using HPLC-electrospray tandem mass spectrometry. A few of the triacylglycerols detected were typical combinations of fatty acids originating from rapeseed oil, such as α-linolenic acid, and short-chain fatty acids from butter oil. Due to the regioselectivity of the lipase, the transesterification reaction involved mainly fatty acids in the sn-1 and sn-3 positions. However, significant changes in the fatty acid composition in the sn-2 position were detected after 6 h.     

Characterization of triterpene alcohols of seed oils from some species of theaceae,phytolaccaceae and sapotaceae

Triterpene alcohol constituents of the unsaponifiable lipids separated from tea seed oil fromThea sinensis L. (Theaceae), camellia seed oil fromCamellia japonica L. (Theaceae), pokeweed seed oil fromPhytolacca americana L. (Phytolaccaceae) and shea butter from the seed kernels ofButyrospermum parkii (Sapotaceae) were studied. Among a number of triterpene alcohols present in these oils, 19 components were identified as cycloartenol, 24-methylenecycloartanol, parkeol, 24-methylene-24-dihydroparkeol, lanosterol, euphol, butyrospermol, tirucallol, tirucalla-7,24-dienol, dammaradienol, 24-methylenedammarenol, α-amyrin, β-amyrin, lupeol, germanicol, taraxasterol, ψ-taraxasterol, taraxerol and myricadiol. Tirucalla-7,24-dienol and butyrospermol are the predominant components of the 2 Theaceae and pokeweed seed oils. Shea butter, on the other hand, contains α-amyrin followed by butyrospermol and lupeol as the major triterpene constituents. Presented at the AOCS Annual Meeting, San Francisco, April/May 1979.     

Assessing the Effects of Sunlight on the Photooxidation of Tropical Oils with Experimental and Computational Approaches

This study aims to investigate the influence of high-intensity sunlight radiation on the photooxidation of tropical oils (TO). Coconut oil (CNO), palm oil (PO), and palm kernel oil (PKO) were chosen for determining the indicators of photooxidation when exposed to and in the absence of sunlight for 7 weeks. The results showed a significant (P < 0.05) increase in free fatty acid (FFA) levels and peroxide value (PV) when the TO were exposed to sunlight. The iodine value and color content decreased significantly (P < 0.05) due to the decomposition of unsaturated FFA owing to the breaking down of the π-bonds and the degradation of color pigments during photooxidation. Fourier transform infrared spectroscopy (FTIR) analysis showed strong vibrational absorptions at 1721 and 3505 cm⁻³, 1720 and 3560 cm⁻³, and 1721 and 3554 cm⁻³ for the CNO, PO, and PKO samples exposed to sunlight, respectively. These bands can be attributed to the presence of secondary oxidation products, which were absent in the TO that were not exposed to sunlight. A simulation was performed to support the FTIR results, which also indicated peaks from the secondary oxidation products at 1744 and 3660 cm⁻³. The study also revealed that the rate of photooxidation was different for each TO. The rate of oxidation followed the order PO > PKO > CNO. In contrast, no notable changes were observed in the TO kept away from sunlight. These results suggest that exposing TO to sunlight influences their oxidation stability and quality.     

Lipase-assisted acidolysis of high-laurate canola oil with eicosapentaenoic acid

The production of structured lipids via acidolysis of high-laurate canola oil (Laurical 15) with EPA in hexane was carried out using lipase from Pseudomonas sp. The optimal reaction conditions used 4% lipase, at a mole ratio of oil to EPA of 1∶3 at 45°C over 36 h. The positional distribution of FA on the glycerol backbone of unmodified oil indicated that lauric acid was mainly located at the sn-1,3 positions. Stereospecific analysis of the oil modified with EPA showed that lauric acid remained mostly esterified to the sn-1,3 positions of the TAG molecules and that EPA was also primarily in the sn-1,3 positions of the TAG molecules. Thus, the resultant structured lipids may have optimal value for use in applications where quick energy release and EPA supplementation are required.     

Identification of oil palm breeding lines producing oils with low acid values

In the oil palm (Elaeis guineensis Jacq.), an active endogenous lipase is responsible for the massive release of free fatty acids (FFA) in the mesocarp of fruits at maturity. This can lead to the production of oils with unacceptable acid values. We have investigated the lipase activities in 39 genotypes of oil palm presently used in breeding programs. While most E. guineensis genotypes exhibited high lipase activity values, four of them with negligible activities were identified. We analyzed in situ lipolysis in the mesocarp upon severe wounding of fruits. The FFA content of high‐lipase fruits ranged from 17 to 55%, while all low‐lipase fruits contained less than 7.5% FFA. The analysis of oil from fallen overripe fruits indicated that all low‐lipase genotypes contained less than 1.2% FFA (oil acidity <5% FFA, FAO‐WHO international norms), while all but one high‐lipase genotypes had FFA contents much higher than the acceptable standards. Because the identified low‐lipase lines are of high agronomical value and at least one of them is an elite genotype, it will soon be possible to provide farmers with new low‐lipase oil palm lines allowing significant savings on labor costs, without any need for further breeding.     

Enhanced lipase production from Aeromonas sp. S1 using Sal deoiled seed cake as novel natural substrate for potential application in dairy wastewater treatment

BACKGROUND: Sal (Shorea robusta) deoiled seed cake extract (SDOCE) was assessed for its suitability as a cheap natural substrate for lipase production under submerged fermentation. The bacterial isolate Aeromonas sp. S1 isolated from dairy industry was used for lipase production. Both the isolate and its lipase were shown to be potential tools for treatment of dairy wastewater containing higher organic load. RESULTS: On substituting tributyrin with SDOCE, lipase production was enhanced 24‐fold (195 U mL^?1) compared with the initial 8.13 U mL^?1 lipase activity. Maximum lipase production was obtained at pH 8.0 and incubation temperature 30 °C. The lipase had pH and temperature optima of 10.0 and 55 °C, respectively. The isolate and its crude enzyme preparation were checked separately for applicability in dairy wastewater treatment. The isolate was able to reduce chemical oxygen demand (COD) by 93%, oil and grease (O&G) by 75%, and total suspended solids (TSS) by 47% after 96 h of treatment. Enzymatic preparation gave 86% reduction of COD after 12 h and 75 and 45% reduction of O&G and TSS, respectively, after 96 h of treatment. CONCLUSION: Overall, the study shows the usefulness of Sal seed deoiled cake, a cheap agro‐industrial by‐product for the production of lipase. The isolate and its lipase can also be used effectively for the treatment of dairy wastewater. Copyright © 2011 Society of Chemical Industry     

Synthesis of fatty acid esters from acid oils using lipase B from Candida antarctica

Esterification of corn and sunflower acid oils with straight‐ and branched‐chain alcohols were conducted using lipase B from Candida antarctica (Novozym 435) in n‐hexane. Sunflower acid oil consisted of 55.6% free fatty acids and 24.7% triacylglycerols, while the free fatty acids and triacylglycerols contents of corn acid oil were 75.3% and 8.6%, respectively. After 1.5 h of methanolysis of sunflower acid oil, the highest fatty acid methyl ester content (63.6%) was obtained at 40 °C and the total fatty acid/methanol molar ratio was 1/1, using 15% enzyme based on acid oil weight. The conversion of both acid oils with straight‐ and branched‐chain alcohols was not significantly affected by the chain length of the alcohols. However, the lowest fatty acid methyl ester content (50%) was obtained in the reaction of corn acid oil with methanol. Sunflower acid oil was converted to fatty acid esters using primer alcohols such as n‐propanol, i‐ and n‐butanol, n‐amylalcohols, n‐octanol, and a mixture of amylalcohol isomers, resulting in a fatty acid ester content of about 70% at 40 °C.     

Production of structured triacylglycerols in an immobilised lipase packed‐bed reactor: batch mode operation

Structured triacylglycerols with caprylic acid at the sn‐1 and sn‐3 positions of the glycerol backbone and eicosapentaenoic acid (EPA) at the position sn‐2 were synthesised by acidolysis of a commercially available EPA‐rich oil (EPAX4510, Pronova Biocare) and caprylic acid catalysed by the 1,3‐specific immobilised lipase Lipozyme IM. The reaction was carried out in an immobilised lipase packed‐bed reactor by recirculating the reaction mixture through the bed. The exchange equilibrium constants between caprylic acid and the native fatty acids of EPAX4510 were determined. The n‐3 polyunsaturated fatty acids (PUFAs), EPA and docosohexaenoic acid (DHA), were the most easily displaced by the caprylic acid. The exchange equilibrium constants were 3.68 and 3.06 for EPA and DHA, respectively. The influence of the flow rate of the reaction mixture through the packed‐bed and the substrate concentration in the reaction rate were studied. For flow rates between 74 and 196 cm³ h^?1 (bed of 6.6 mm internal diameter and 0.46 porosity) and triacylglycerol concentrations between 0.036 and 0.108 M , the data fitted well to an empirical kinetic model which allowed representative values of the apparent kinetic constant to be obtained. Hence, the average reaction rates and kinetic constants of exchange of caprylic acid and native fatty acids of EPAX4510 could be calculated. In the conditions indicated, the parameter (lipase mass × time/triacylglycerol mass, m_Lt/V[TG]₀) constituted the intensive variable of the process for use in predicting the composition of structured triacylglycerols at different reaction times. At equilibrium, the structured triacylglycerol produced had the following composition: caprylic acid 59.5%, EPA 9.6%, DHA 2.2% and oleic acid 11.8%. Copyright © 2004 Society of Chemical Industry