Isomeric distribution and rapid determination of trans-octadecenoic acids in German brands of partially hydrogenated edible fats

The determination of trans fatty acids (TFA), in particular trans-octadecenoic acids, in edible fats is of current interest, since just in the last years a variety of negative physiological effects has been related to TFA. A main source of C18:1 trans fatty acids are partially hydrogenated fats. Besides the total content of trans-octadecenoic acids, their isomeric distribution seems to be even more important, as fats of different origin, e.g. partially hydrogenated fats and ruminant fats, possibly show different physiological properties. In this study, 46 margarines and 16 shortenings and cooking fats, purchased in August of 1994, were analyzed for trans-octadecenoic acid isomers by a two-step method (Ag-TLC/HRGC). The mean relative isomeric distributions (g/100 g TFA) of both groups determined with a 100 m-column were comparable, with Δ9 and Δ10 being the main isomers. By repeated analysis of 15 brands between August of 1994 and January of 1996, the mean total C18:1 TFA content was found to have decreased in these margarines (n = 8) from 9.58% to 4.62% but not in shortenings/cooking fats (n = 7; 11.62% to 11.92%). The relative isomeric distribution was not affected in both groups. To avoid the problem of overlaps between cis-and trans-C18:1 isomers with GC analysis, formulae for the rapid determination of total C18:1 TFA contents in margarines and shortenings/cooking fats from direct GC data were statistically derived. Thus, applying these formulae and considering the mean relative distributions, absolute contents of all individual isomers of trans-octadecenoic acids can rapidly be determined from direct GC.     

Bouillon cubes: assessment of the state of degradation of the lipid fraction

An experimental investigation was carried out to assess the oxidative and hydrolytic quality of the lipid fraction of bouillon cubes. Besides the routine analyses prescribed by EC regulations, determinations of fatty acid composition and unsaturated fatty acid trans isomers were also performed. From the lipid fraction extracted from each cube, polar compounds were separated by silica gel column chromatography and then submitted to HPSEC (high‐performance size exclusion chromatography) analysis to determine the classes of substances deriving from oxidation, polymerisation and hydrolysis of triglycerides. The data obtained showed that the determination of trans isomers and the subsequent HPSEC analysis of polar compounds enable one to ascertain the actual degradation of the lipid fraction of such food preparations. The degree of degradation of the lipid fraction of bouillon cubes was similar to that normally found in olive‐pomace oil, which is the poorest olive oil commercial class. Finally, the contents of trans isomers and triglyceride oligopolymers are shown to be significantly higher in hydrogenated than in non‐hydrogenated vegetable fats. Copyright © 2003 Society of Chemical Industry     

Production of trans‐free margarine stock by enzymatic interesterification of rice bran oil,palm stearin and coconut oil

BACKGROUND: Trans‐free interesterified fat was produced for possible usage as a spreadable margarine stock. Rice bran oil, palm stearin and coconut oil were used as substrates for lipase‐catalyzed reaction. RESULTS: After interesterification, 137–150 g kg^?1 medium‐chain fatty acid was incorporated into the triacylglycerol (TAG) of the interesterified fats. Solid fat contents at 25 °C were 15.5–34.2%, and slip melting point ranged from 27.5 to 34.3 °C. POP and PPP (β‐tending TAG) in palm stearin decreased after interesterification. X‐ray diffraction analysis demonstrated that the interesterified fats contained mostly β′ polymorphic forms, which is a desirable property for margarines. CONCLUSIONS: The interesterified fats showed desirable physical properties and suitable crystal form (β′ polymorph) for possible use as a spreadable margarine stock. Therefore, our result suggested that the interesterified fat without trans fatty acid could be used as an alternative to partially hydrogenated fat. Copyright © 2010 Society of Chemical Industry     

EFFECT OF CHEMICAL INTERESTERIFICATION ON PHYSICOCHEMICAL PROPERTIES AND INDUSTRIAL APPLICATIONS OF CANOLA OIL AND FULLY HYDROGENATED COTTONSEED OIL BLENDS

Blends of canola oil (CO) and fully hydrogenated cottonseed oil (FHCSO), with 20, 25, 30, 35 and 40% FHCSO (w/w) were interesterified under the following conditions: 0.4% sodium methoxide, 500 rpm stirring, 100C, 20 min. The original and interesterified blends were examined for triacylglycerol composition, melting point, solid fat content (SFC) and consistency. Interesterification caused considerable rearrangement of triacylglycerol species, reduction of trisaturated triacylglycerol content and increase in disaturated-monounsaturated and monosaturated-diunsaturated triacylglycerols in all blends, resulting in lowering of respective melting points. The interesterified blends showed reduced SFC at all temperatures and more linear melting profiles if compared with the original blends. Consistency, expressed as yield value, significantly decreased after the reaction. Iso-solid curves indicated eutectic interactions for the original blends, which were eliminated after randomization. The 80:20, 75:25, 70:30 and 65:35 (w/w) CO: FHCSO interesterified blends showed characteristics which are appropriate for their application as soft margarines, spreads, fat for bakery/all-purpose shortenings, and icing shortenings, respectively.

PRACTICAL APPLICATIONS

Recently, a number of studies have suggested a direct relationship between trans isomers and increased risk of vascular disease. In response, many health organizations have recommended reducing consumption of foods containing trans fatty acids. In this connection, chemical interesterification has proven the main alternative for obtaining plastic fats that have low trans isomer content or are even trans isomer free. This work proposes to evaluate the chemical interesterification of binary blends of canola oil and fully hydrogenated cottonseed oil and the specific potential application of these interesterified blends in food products.     

Recent trends in the fatty acid composition of German sunflower margarines, shortenings and cooking fats with emphasis on individual C16:1, C18:1, C18:2, C18:3 and C20:1 trans isomers

In some countries the content of trans fatty acids (TFA) in margarines has strongly decreased as a result of the continuous discussion on their disadvantages regarding aspects of nutritional physiology. However, still in 1994 almost 1/3 of total fatty acids in part of German sunflower margarines, shortenings and cooking fats comprised these unfavourable TFA. In the present study the main interest was laid on trans-C16:1, trans-C18:1, trans-C20:1, trans-C18:2 and trans-C18:3 fatty acids and particularly their individual isomers, as negative metabolic activity of TFA possibly might only be attributable to certain isomers. By combining argentation thin-layer chromatography with gas chromatography using a 100-m capillary column (CP-Sil 88) trans fatty acid contents were determined in nearly all German brands of sunflower margarines (SFM; n = 9) and of cooking fats and shortenings (CFS; n = 10). Concerning the above-mentioned groups of isomers mean TFA contents of 0.01, 4.88, 0.00, 0.45 and 0.03% for SFM as well as of 0.01, 5.02, 0.03, 0.70 and 0.17% for CFS were established, respectively. The re-evaluation of samples from 1994 and 1996 exhibited that the total TFA content (sum of all mentioned isomers) in SFM decreased from 21.77% (range: 13.78-26.29; n = 11) to 5.37% (1.98-6.15%; n = 9) between 1994 and 1999. Also the total TFA content in CFS on average strongly decreased from 11.77% (0.08-33.63; n = 16) in 1994 and 12.52% (1.61-26.79%; n = 7) in 1996 to 5.91% (0.43-19.72%; n = 10) in 1999. However, even the newest CFS samples partly exhibited relative high TFA contents. In addition to the total TFA contents all positional isomers of trans-C18:1, trans-C18:2 and trans-C18:3 in SFM and CFS were quantified and compared between different years. The conjugated linoleic acid (cis delta 9, trans delta 11) occurred only in small amounts of 0.03% and 0.02% in current SFM and CFS.     

An investigation on the physicochemical characterization of interesterified blends of fully hydrogenated palm olein and soybean oil

In this study, the effect of interesterification (using sodium methoxide) on physicochemical characteristics of fully hydrogenated palm olein (FHPO)/soybean oil blends (10 ratios) was investigated. Interesterification changed free fatty acid content, decreased oil stability index, solid fat content (SFC) and slip melting point (SMP), and does not affected the peroxide value. With the increase of FHPO ratio, oil stability index, SFC and SMP increased in both the interesterified and non-interesterified blends. Fats with higher FHPO ratio had narrower plastic range, as well. Compared to the initial blends, interesterified fats had wider plastic ranges at lower temperatures. Both the non-interesterified and interesterified blends showed monotectic behavior. The Gompertz function could describe SFC curve (as a function of temperature, saturated fatty acid (SFA) content or both) and SMP (as a function of SFA) of the interesterified fats with high R² and low mean absolute error.     

Chemical interesterification of olive oil-tristearin blends for margarines

Refined olive oil–glycerol tristearate blends were interesterified using sodium methoxide as catalyst. The glyceride structure of the randomized fats was studied and the relationship between the structure and physical properties was examined. The rearranged fats were investigated for Solid Fat Index, melting behaviour, consistency and spreadability and the values obtained were compared to those of zero-trans margarines or commercially available products prepared from hydrogenated olive oil and other vegetable oils. The 80:20 and 75:25 olive oil–tristearin blends after randomization have properties very close to those of soft tub and packet margarines.     

Essential fatty acids and trans contents of some oils,margarine and other food fats

Levels of polyunsaturated fatty acids (PUFA), cis, cis-methylene interrupted polyunsaturated fatty acids (i.e. essential fatty acids—EFA) and isolated trans double bonds in six crude vegetable oils, seven commercial oils, eighteen margarines, two butter fats and fats from two types each of crisps and butter biscuits have been determined. The ratios between the PUFA or EFA and the saturated fatty acids of various samples have been tabulated. Normal (i.e. high linoleic) safflower seed oil gave the highest ratio. Margarines which were estimated to contain partially hydrogenated fish oils (45–90%, on fat basis) gave high values of trans double bonds. Butter fat having a similar EFA level to that present in a ‘hydrogenated fish oil’ margarine contained a much lower level of trans isomers. Almost all the PUFA in the oils of crips, and about half the PUFA content of butter biscuits, existed as ‘true’ essential fatty acids.     

Recent trends in the fatty acid composition of German sunflower margarines,shortenings and cooking fats with emphasis on individual C16 : 1, C18 : 1, C18 : 2, C18 : 3 and C20 : 1trans isomers

In some countries the content oftransfatty acids (TFA) in margarines has strongly decreased as a result of the continuous discussion on their disadvantages regarding aspects of nutritional physiology. However, still in 1994 almost 1/3 of total fatty acids in part of German sunflower margarines, shortenings and cooking fats comprised these unfavourable TFA. In the present study the main interest was laid ontrans‐C16 : 1,trans‐C18 : 1,trans‐C20 : 1,trans‐C18 : 2 and trans‐C18 : 3 fatty acids and particularly their individual isomers, as negative metabolic activity of TFA possibly might only be attributable to certain isomers. By combining argentation thin‐layer chromatography with gas chromatography using a 100‐m capillary column (CP‐Sil 88) trans fatty acid contents were determined in nearly all German brands of sunflower margarines (SFM; n = 9) and of cooking fats and shortenings (CFS; n = 10). Concerning the above‐mentioned groups of isomers mean TFA contents of 0.01, 4.88, 0.00, 0.45 and 0.03% for SFM as well as of 0.01, 5.02, 0.03, 0.70 and 0.17% for CFS were established, respectively. The re‐evaluation of samples from 1994 and 1996 exhibited that the total TFA content (sum of all mentioned isomers) in SFM decreased from 21.77% (range: 13.78–26.29; n = 11) to 5.37% (1.98–6.15%; n = 9) between 1994 and 1999. Also the total TFA content in CFS on average strongly decreased from 11.77% (0.08–33.63; n = 16) in 1994 and 12.52% (1.61–26.79%; n = 7) in 1996 to 5.91% (0.43–19.72%; n = 10) in 1999. However, even the newest CFS samples partly exhibited relative high TFA contents. In addition to the total TFA contents all positional isomers of trans‐C18 : 1,trans‐C18 : 2 and trans‐C18 : 3 in SFM and CFS were quantified and compared between different years. The conjugated linoleic acid (cis Δ9,trans Δ11) occurred only in small amounts of 0.03% and 0.02% in current SFM and CFS.     

An Improved Silver Ion HPLC Combined with Capillary Gas Chromatography of cis/trans Fatty Acids in Alimentary Fats and Human Milk Fat

A technique of analysis is described using a silver ion-loaded HPLC (Ag⁺/HPLC) column, gradient elution, and a laser light scattering detector followed by capillary gas chromatography (GC) for the determination of the fatty acid methyl ester (FAME) composition of rapeseed oil, the respective hydrogenated fat, some dietary fats, and human milk fat. With the use of Ag⁺/HPLC, FAMEs were separated into the following classes: saturated, trans-monounsaturated, cis-monounsaturated, trans–trans-di-unsaturated, trans–cis-di-unsaturated, cis–cis-di-unsaturated, and higher unsaturated FAMEs. Within each class, partial separation of positional isomers was also possible. Fractions of the eluate containing trans and cis C18:1 were separately collected and re-analyzed by GC in order to quantitate the positional isomers eight trans and nine cis in rapeseed oil and in human milk fat. The profiles of eight trans positional isomers in human milk fat and in hydrogenated rapeseed oil were alike but entirely different from that of six C18:1 trans isomers in bovine milk fat. Out of nine C18:1 cis isomers found in hydrogenated fat, only C18:1-9c and C18:1-11c were found in both human and bovine milk fat which may indicate some discrimination which occurs for certain isomers in fatty acid metabolism.     

The interesterification-induced changes in olive and palm oil blends

Refined olive oil and partially hydrogenated palm oil (PHPO) blends of varying proportions were subjected to both chemical and enzymatic interesterifications. The rearranged fats were investigated for their melting points, solid fat contents at selected temperatures, fatty acid compositions and trans isomer contents, as well as evaluations, by an expert sensory panel, of their spreadibility and appearance characteristics. The analytical results were compared with those of commercial Turkish margarines. The 30:70 olive oil-PHPO blend after enzymatic interesterification was found to have properties very similar to those of Turkish package margarines, with the additional advantage of possessing higher amounts of monounsaturated fatty acids.     

Analytical Methods for Quantification of Modified Fatty Acids and Sterols Formed as a Result of Processing

Fats and oils are often submitted to technological treatments before being consumed. Some treatments like refining, hydrogenation, and frying often lead to the formation of modified fatty acids such as cyclic fatty acid monomers (CFAM), geometrical fatty acid isomers, and/or oxidized fatty acids and sterols (cholesterol and phytosterols). Both cholesterol oxidation products (COP) and phytosterol oxidation products (POP), may be present in foods. As some of the newly formed components may present some adverse effects upon consumption, methods have been developed to analyze these compounds in food products and biological samples. Gas liquid chromatography (GC) on long polar columns (100m) is a good choice to quantify trans mono- and poly-unsaturated fatty acids. In some cases a pre-fractionation step using silver nitrate thin layer chromatography (AgNO₃-TLC) may be necessary to avoid GC overlapping of cis and trans isomers. Analysis of CFAM usually involves transformation of the sample in fatty acid methyl esters (FAME) which after addition of an internal standard (IS) are further hydrogenated. An enrichment step using reverse phase high performance liquid chromatography (RP-HPLC) permits to obtain a fraction which consists of a mixture of CFAM and the IS. This fraction is further analyzed by GC on a polar column. The analysis of oxidized triacylglycerol monomers (oxTG) as a group was feasible by a combination of adsorption and size-exclusion chromatography. Quantification in used frying fats and oils around the limit of rejection for human consumption (25% polar compounds) has shown that the amount of oxTG range 5.9–9.4% expressed on fat or oil weight. In foods and biological tissues, the level of oxidized sterols (SOP) is often a very small fraction of their unoxidized forms. Analysis of SOP involved extraction of lipids, saponification or transesterification, enrichment, and subsequent qualitative and quantitative determination by GC and GC-MS, or HPLC and HPLC-MS. In addition, enrichment of SOP requires complete separation from the unoxidized sterols in order to separate these compounds even by high resolution GC capillary columns.     

Trans Fatty Acid Contents in Selected Dietary Fats in the Estonian Market

In response to public concern, this study assessed the fatty acid (FA) composition of blended spreads, margarines and shortenings in the Estonian retail market in 2011. Special attention was paid to the trans fatty acids (TFA) composition. The changes in these characteristics of selected dietary fats in the market over recent years are also presented. Twenty-six edible fat brands, available in the Estonian retail market in 2011, were purchased and FA compositions were analyzed by chromatography. Saturated fatty acids (SFA) were the dominant group of FAs for all blended spreads (49.6 to 65.8%), and for the majority of shortenings (from 21.1 to 54.6%). Cis monounsaturated fatty acids (MUFA) were the dominant group of FAs for the majority of margarines, ranging from 25.3% to 50.5%. The total TFA for blended spreads varied from 1.18% to 9.08%, for margarines from 0.04% to 34.96% and for shortenings from 0.14% to 39.50%. Octadecenoic (C18:1) isomers were the main TFA found. Compared to 2008/2009, the industrially produced TFA (IP-TFA) content in several of the dietary fat brands was much reduced in 2011. This voluntary reformulation was probably a response to consumer demand associated with a public health campaign directed against IP-TFA in Estonian foods, and were mainly achieved by replacing TFA with SFA C12:0-C16:0. Practical Application: Present paper is directed toward public health related institutions and food industries producing foods with potentially high contents of trans fatty acids (TFA). According to the public concern TFA content in domestic blended spreads has declined significantly over the past 3 y in Estonia. The reduction in the TFA content was achieved by replacing TFA with saturated fatty acids (SFA) (C12:0-C16:0). To shift food composition toward healthier product formulations, mandatory labeling of the sum of IP-TFA and SFA (C12:0-C16:0) was recommended.     

Comprehensive studies on the trans fatty acid content of Austrian foods: Convenience products,fast food and fats

Due to reported detrimental health effects of diets high in trans fatty acids (TFA) in particular on blood lipids, convenience products, trade margarines, fats for cooking and frying and fast food products available on the Austrian market were comprehensively investigated on TFA, using gas chromatography.     

Thermal and crystal characteristics of enzymatically interesterified fats of fatty acid-balanced oil and fully hydrogenated soybean oil in supercritical CO2 system

Blends of fatty acid-balanced oil that was prepared by the aqueous enzymatic extraction, and with fully hydrogenated soybean oil in different weight ratios from 30:70 to 80:20 (wt%) were interesterified using Lipozyme RM IM in a supercritical CO₂ system. The optimal immobilized enzyme dosage, pressure, substrate ratio, temperature, and time were 6% (w/w) of initial substrates, 8 MPa, blend ratio with 60:40 (wt%) of fatty acid-balanced oil and fully hydrogenated soybean oil, a temperature of 70°C, and reaction time of 2 h, respectively. It was observed that at the optimal conditions, under supercritical CO₂ conditions, the reaction time of the interesterification was shorter than that of conventional enzymatic interesterification. The slip melting point, solid fat content, fatty acid composition, differential scanning calorimetry, polymorphic form and crystal morphology of the enzymatically interesterified fats were evaluated. The results indicated that the interesterified fats showed desirable physical properties with lower slip melting point and solid fat content, suitable crystal form (β′ polymorph), and without trans-fatty acid for possible use as a shortening and margarine stock.     

Qualitative and quantitative characterisation of the lipid fraction of bouillon cubes

An experimental investigation was performed to characterise the fat fraction of bouillon cubes. Besides the routine analyses, the analytical methods used were: silica-gel column chromatography to separate polar compounds, high performance size-exclusion chromatography (HPSEC) for the qualitative and quantitative determination of the single classes of substances constituting the polar compounds, and gas chromatography to determine the acid composition and the trans isomers of unsaturated fatty acids. The fats blended into the bouillon preparations were highly variable and were mainly made up of refined vegetable oils that had undergone hardening, by hydrogenation in most cases. Determination of the free fatty acids and of the peroxide values yielded figures that in some cases exceeded the limits set for the commercialisation of refined vegetable oils. Compared to the routine analyses, the HPSEC analysis of the polar compounds provided a better evaluation of the level of degradation of the fat extracted from the bouillon formulations. The levels of oxidative and hydrolytic degradation were rather high, and similar to those reported for poor quality oils. Analyses of the trans isomers of oleic acid yielded particularly high values (even over 20%) and differentiated the cubes on the basis of the type of fat added.     

Effects of chemical interesterification on solid fat content and slip melting point of fat/oil blends

Fat/oil blends, formulated by mixing fully hydrogenated palm oil stearin or palm oil stearin with vegetable oils (canola oil and cottonseed oil) in different ratios from 30:70 to 70:30 (w/w %), were subjected to chemical interesterification reactions on a laboratory scale. Fatty acid (FA) composition, iodine value, slip melting point (SMP) and solid fat content (SFC) of the starting blends were analysed and compared with those of the interesterified blends. SMPs of interesterified blends were decreased compared to starting blends because of extensive rearrangement of FAs among triacylglycerols. These changes in SMP were reflected in the SFCs of the blends after the interesterification. SFCs of the interesterified blends also decreased with respect to the starting blends, and the interesterified products were softer than starting blends. These interesterified blends can be used as an alternative to partial hydrogenation to produce a plastic fat phase that is suitable for the manufacture of margarines, shortenings and confectionary fats.     

<Emphasis Type="Italic">Trans</Emphasis>-free margarine fat produced using enzymatic interesterification of rice bran oil and hard palm stearin

Trans-free interesterified fats were prepared from blends of hard palm stearin (hPS) and rice bran oil (RBO) at 20:80, 30:70, 40:60, 50:50, 60:40, 70:30, and 80:20 weight % using immobilized Mucor miehei lipase at 60°C for 6 h with a mixing speed of 300 rpm. Physical properties and crystallization and melting behaviors of interesterified blends were investigated and compared with commercial margarine fats. Lipase-catalyzed interesterification modified triacylglycerol compositions and physical and thermal properties of hPS:RBO blends. Slip melting point and solid fat contents (SFC) of all blends decreased after interesterification. Small, mostly β′ form, needle-shaped crystals, desirable for margarines were observed in interesterified fats. Interesterified blend 40:60 exhibited an SFC profile and crystallization and melting characteristics most similar to commercial margarine fats and also had small needle-like β′ crystals. Interesterified blend 40:60 was suitable for use as a transfree margarine fat.     

Enzymatic Production of Trans-Free Hard Fat Stock from Fractionated Rice Bran Oil, Fully Hydrogenated Soybean Oil, and Conjugated Linoleic Acid

ABSTRACT:  Rice bran oil (RBO) was fractionated into 2 phases, solid (S-RBO) and liquid (L-RBO), using acetone at –18 °C and the weight yield of each S-RBO and L-RBO was 45.5% and 54.5%, respectively. Then, trans -free hard fat was synthesized from trans -free substrate of S-RBO and fully hydrogenated soybean oil (FHSBO) at different molar ratios (S-RBO : FHSBO; 1 : 1, 1 : 1.5, 1 : 2, and 1 : 3) with Lipozyme TL IM lipase (10% of total substrate). Conjugated linoleic acid (CLA, 20% of total substrate) was used as functional fatty acids for the production of trans- free hard fat. After fatty acid analysis, CLA (12.2% to 14.2%) was found on the triacylglycerol (TAG) backbone of the interesterified products along with stearic (37.6% to 49%), palmitic (15% to 17.9%), and oleic acids (13.3% to 19.2%). The interesterified product contained higher level of saturated fatty acid (62.6% to 70.1%) at sn -2 position. Total tocopherols (α-, γ-, and δ-; 1.4 to 2.6 mg/100 g) and phytosterols (campesterol, stigmasterol, and β-sitosterol; 220.5 to 362.7 mg/100 g) were found in the interesterified products. From DSC results, solid fat contents of the interesterified products (S-RBO : FHSBO 1 : 1, 1 : 1.5, 1 : 2, and 1 : 3) at 25 °C were 23.1%, 27%, 30.1%, and 44.9%. The interesterified products consisted mostly of β' form crystal with a small portion of β form. The interesterified product (S-RBO : FHSBO 1 : 1.5) was softer than the physical blend but slightly harder than commercial shortenings as measured by texture analyzer. Thus, trans- free hard fat stock, which may have a potential functionality could be produced with various physical properties.     

Characterisation of zero‐trans margarine fats produced from camellia seed oil,palm stearin and coconut oil using enzymatic interesterification strategy

Zero‐trans interesterified fats were produced from camellia seed oil (CSO), palm stearin (PS) and coconut oil (CO) with three weight ratios (CSO/PS/CO, 50:50:10, 40:60:10 and 30:70:10) using Lipozyme TL IM. Results showed that the interesterified products contained palmitic acid (34.28–42.96%), stearic acid (3.96–4.72%), oleic acid (38.73–47.95%), linoleic acid (5.92–6.36%) and total medium‐chain fatty acids (MCFA)s (∑MCFAs, 5.03–5.50%). Compared with physical blends, triacylglycerols of OOO and PPP were decreased and formed new peaks of equivalent carbon number (ECN) 44 in the interesterified products. The product CPC3′ showed a slip melting point of 36.8 °C and a wide plastic range of solid fat content (SFC) (45.8–0.4%) at 20–40 °C. Also, the major β′ form was determined. These data indicated that the zero‐trans interesterified fats would have a potential functionality for margarine fats. Subsequently, the antioxidative stabilities of interesterified products with the addition of α‐tocopherol (α‐TOH) and ascorbyl palmitate (AP) were investigated. The results indicated that AP had a dose‐dependent effect at concentrations of 100, 200 and 400 ppm.