De-oiled canola meals are sources of protein-containing flavor-active phenolic compounds. Conventional canola oil processing utilizes an excess amount of solvents and is associated with the release of high-intensity bitter flavor-active phenolic compounds, limiting the use of the canola meal. Recent advances in the extraction and isolation of the bitter favor-active phenolic compounds from canola by-products produce protein isolates, however, would benefit the industry by producing a side-stream ingredient rich in phenolics. High temperature and pressure-aided processing, namely the accelerated solvent extraction (ASE) was investigated to extract the flavor-active bitter molecules from the canola meal. The extractability of flavor-active phenolic compounds including the major sinapates, kaempferol derivatives, and other thermo-generative compounds including thomasidioc acid (TA) was evaluated. The effects of temperature, solvent extractant and concentration, and the particle size of the meal, were examined on the extraction efficiency of these phenolic compounds. Extraction temperature (180oC) was the primary determinant (p<0.05) for the attenuation of major sinapates including sinapine and sinapic acid. Both ethanol and methanol extractants at a concentration of 70% (v/v) significantly (p<0.05) extracted the flavor-active phenolic compounds. The pressurized high temperature through optimized ASE conditions attenuated the bitter undesirable flavor-active phenolic molecules from canola meal thereby facilitating a potential value-added phenolic-rich by-product.

Current research on wax-based oleogels indicates wax esters to be the key component in many natural waxes. This necessitates understanding the properties of pure wax esters to unravel the gelling mechanism in wax-based oleogels. Therefore, wax esters with different carbon numbers and symmetries were studied and characterized regarding their thermal (DSC) and viscoelastic (oscillatory rheology) behavior. Pure wax esters and binary mixtures of wax esters were studied as such and in oleogels formed in combination with medium chained triglyceride oil at WE-inclusion levels of 10 % (w/w). Interpretation of the observations was based on detailed analysis of pre-existing data on crystallographic (SAXS) and thermal properties. It is found that all observations concerning single pure WE’s obey a systematic framework linking molecular make up, crystal structure and behavior. The study on the gelling of four different binary mixtures of wax esters revealed that substantial chain length differences do have the expected consequence of separate crystallization. Mixtures of wax esters with only limited chain length difference reconfirmed earlier speculations on mixing and crystal structure. Applying mixtures of wax esters only differing in their position of the ester bond indicated ideal mixing behavior in the solid phase of the gels. Actually, the data revealed that despite these expected observations in both systems, additional thermal events occur at specific mixing ratios. Their supposed relation to compound formation certainly needs further confirmation. Rheological analysis confirmed that sequential crystallization results in highest firmness values for the systems studied.

The food industry is seeking natural antioxidants for edible oils that have comparable activity to synthetic counterparts. In this study, Osage orange extract (OOE) rich in osajin (42.9%) and pomiferin (30.0%) was obtained after hexane extraction of the fruit, and its antioxidant activity was examined in stripped soybean oil (SBO) and fish oil (FO), in which antioxidants and polar compounds were removed. The antioxidant activity of OOE was compared with commercial natural antioxidants (i.e., rosemary extract and mixed tocopherols) and a synthetic antioxidant, butylated hydroxytoluene (BHT), during storage at 25 and 40 ℃. The 0.1% OOE had stronger antioxidant activity than 0.1% rosemary extract and 0.1% mixed tocopherols in both oils at 25 and 40 ℃. Its activity was similar to 0.02% BHT in SBO and was similar or slightly stronger than 0.02% BHT in FO. When OOE was studied at 0.05, 0.1, and 0.2%, there was a weak dose-response in SBO but a stronger dose-response in FO. Headspace volatile analysis using solid phase micro-extraction (SPME) combined with GC-MS indicated that 0.1% OOE was very effective in preventing the formation of volatile oxidation products in both oils. Although it should be further tested for safety before the actual use, this study shows that OOE can be developed as an antioxidant for edible oils.

Oleogels prepared from hydrocolloids have recently gained a lot of attention as an alternative for trans and saturated fats. Previously we have demonstrated that the freeze-dried foams prepared using a mixture of 5% faba bean or pea protein concentrates with 0.25% xanthan gum at pH 7 and 9 can hold canola oil 30-40 times their weights (Mohanan, Tang, Nickerson and Ghosh, 2020). However, the oleogels suffered from high oil loss, about 30% oil leaked, which negatively affected the rheological properties of the oleogels. The functionality of the cake baked using the oleogels was poorer compared to a shortening baked cake. The present study explored the addition of a small amount of high-melting monoacylglycerol (MAG) and candelilla wax (CW) on reducing oil loss, improving rheological properties and baking qualities of pulse protein-stabilized oleogels. Different concentrations (0.5-3%) of MAG or CW were dissolved in canola oil at 80 ºC. The hot oil was then added into the freeze-dried protein-polysaccharide foams (pH 7) and quickly transferred to a refrigerator. The crystallized additives reinforced the oleogel network, thereby reducing oil loss while increasing the firmness, cohesiveness, and storage modulus. When model cakes were baked with the oleogels, significant improvement in textural properties was observed with the addition of MAG in the foam-templated oleogels. However, in comparison with shortening-based cakes, oleogel-based cakes still showed a negative effect on hardness, chewiness and cohesiveness.

The first part of this study showed that the triglyceride composition of purified oils has little impact on sterol/sterol ester oleogels. Hence, changes in the gels’ properties observed in previous studies must arise from minor polar components, particularly by changing the interactions within the fibrillar network. Selected molecules (oleic acid, tocopheryl acetate, monoglycerides, and water) were added to three purified oils to unravel the individual contributions introduced by different functional groups. While all additives retarded the molecular self-assembly of sitosterol with oryzanol, distinct effects were found for gel hardness, transition temperatures and enthalpies, strain sweep responses, and microstructure. It was discovered that the maximum storage modulus in the linear viscoelastic region does not necessarily relate to the gels’ compression firmness. In samples comprising oleic acid and tocopheryl acetate, discrete interaction mechanisms with the scaffolding elements were suggested since results between the two additives developed differently and were dose-dependent. A network supporting effect was suggested at low concentrations, in line with previous results for oils comprising low levels of thermal deterioration products. The microstructure of oleogels was considerably modified with additives. Unfortunately, effects are difficult to quantify due to the packed surface observed in AFM micrographs.

An international robin round was carried out to validate a method for the quantification of 2-monochloropropane-1,3-diol (2-MCPD), 3-monochloropropane-1,2-diol (3-MCPD) and 2,3-epoxy-1-propanol (Glycidol) being present as fatty acid esters in plant-based food emulsifiers. The evaluated method was a modification of the American Oil Chemist´s Society (AOCS) Official Method Cd29b-13. Briefly, this method consists from parallel analysis of two sample aliquots that are spiked with different sets of internal standards. Mild alkaline interesterification overnight in the freezer releases the core analytes. Reaction stop and glycidol conversion into monobromopropanediol (MBPD) is realised by addition of acidified sodium bromide solution. Subsequently, matrix removal and analyte extraction are achieved by two liquid/liquid (l/l) extraction steps. After derivatisation with phenylboronic acid (PBA) the final extracts are analysed by gas chromatography-mass spectrometry (GC-MS). Quantification is carried out by internal one-point-calibration. 6 laboratories from 4 European countries participated in the trial and reported 8 data sets for 10 test materials (mono- and diacylglycerides as well as polyglycerol polyricinoleates) that were analysed as blind duplicates, giving a total of 20 samples. Result outliers were eliminated according to accepted standards. At 2-MCPD levels above 0.02 mg/kg, 3-MCPD levels above 0.06 mg/kg and glycidol levels above 0.22 mg/kg repeatability (RSDr) ranged from 1.5 % to 24.9 %, reproducibility (RSDR) ranged from 7.8 % to 29.0 % and HORRATR-values ranged from 0.5 to 1.7. The tested method showed to be suitable for the determination of 2-MCPD, 3-MCPD and glycidol in food emulsifiers consisting from mono- and diacylglycerides as well as polyglycerol polyricinoleates.

Poor cold flow property is a major issue that hinders the application of biodiesel-diesel blends. In this work, a series of methacrylate-benzyl methacrylate-N-vinyl-2-pyrrolidone terpolymers (RMC-MB-NVP, R= C12, C14, C16, C18) was synthesized and used as the pour point depressants (PPDs) for waste cooking oil biodiesel blends. To further improve their depressive effects, dispersants, including Tween (40, 60, and 80), Span (40, 60, and 80), phthalic acid esters (PAEs), and fatty alcohol polyoxyethylene ether (FAPE; FAPE 5, FAPE 7, and FAPE 9), were optimized and combined with the C14MC-MB-NVP terpolymers. The effects of C14MC-MB-NVP terpolymers and combined PPDs (PPDC) on the cloud point (CP), cold filter-plugging point (CFPP), and pour point (PP) of biodiesel blends were studied. Here, results showed that the presence of dispersants can efficiently enhance the solubility and dispersibility of polymeric PPDs in biodiesel blends; thus, the PPDC presents better depressive effects. Among of them, C16MC-MB-NVP (5:1:1) combined with FAPE 7 dispersant at 4:1 mass ratio (PPDC-FAPE 7) showed the best synergistic effect, and the CP, CFPP, and PP of B20 treated with 2000 ppm PPDC-FAPE 7 decreased by 4, 10 and 19 °C, respectively. Moreover, differential scanning calorimetry, polarizing optical microscope and rheological analyses were performed to rationalize the action mechanism of these PPDs and dispersants in biodiesel blends.

Vegetable fats are complex multi-component mixtures of triglycerides. Here, the solidification behavior of a few vegetable fats is calculated using the Hildebrand equation. This calculation assumes, in the liquid phase, ideal mixing of the different components, in combination with literature data about the temperatures and enthalpies of fusion of the individual triglycerides. It further assumes a decomposition of the triglyceride blend into binary blends dissolved in an inert solvent. The solid fat content is calculated as function of the temperature, assuming that all triglycerides solidify in a single crystal habit (all α or all β or all β’). The minor triglyceride components are explicitly taken into account. The calculated solid fat contents for cocoa butter, palm oil, inter-esterified palm oil and palm kernel olein oil are compared to pNMR data, reported in the literature. Temperature ranges are found, in which specific crystal modifications match to the pNMR data for the solid fat content. These temperature ranges are found to be consistent with literature data obtained using X-ray diffraction. As a by-product, the calculation presented here, enables the construction of scenarios that describe which triglyceride solidifies in which temperature interval.

The role of solvent composition, in particular, minor oil components on sterol/sterol ester oleogels, has been studied recently [1]. Reportedly, deterioration products hamper network formation and modify the gel’s macroscopic properties, probably due to alterations of the scaffolding elements’ interactions. However, the role of the FA composition of TAGs has not yet been addressed. In this study, minor oil components of three vegetable oils with varying degrees of unsaturation (iodine values) were removed, and the oils were chemically and physically characterized before and after the treatment. Consequently, β sitostero/γ-oryzanol oleogels were produced, and the gel-sol (DSC) and sol-gel (rheology) transitions were monitored. Moreover, large and small deformation tests were performed, and the results were linked to oil parameters. In contrast to minor oil components, the FA composition has little impact on oleogel properties. The decline in gel hardness with IV is possibly linked to a lower solvent viscosity. However, a considerable drop in gel-sol transition temperature was observed with increasing IV indicating fewer elements of scaffolding. That was linked to the rapid formation of primary oxidation products in purified flaxseed oil during oleogel preparation, impairing tube formation. Similar to previous results on deterioration products, these minor components seem to aid network strength at low concentrations resulting in similar transition enthalpies and G’. That might be due to shifted network interactions in the presence of molecular species with functional groups. In the second part of this study, these modified interactions in the presence of selected minor components will be discussed.

The goal of the present study is to demonstrate 1H LF-NMR time relaxation measurements for efficient and rapid evaluation of Omega-3 polyunsaturated fatty acids (PUFA)-rich linseed oil (LSO) oxidative aging mechanisms, by monitoring primary chemical and structural changes occurring during thermal oxidative stress. The LF NMR monitors the different proton spin-spin coupling energy relaxation times, T2 within LSO molecular segments, from the initiation of free radical generation and hydroperoxide formation to the propagation of alkoxy radicals, and alpha, beta-unsaturated aldehydes formation, and a termination phase of crosslinked polymerization end products. The 1H LF NMR T2 values monitors both the covalent and secondary bonding interactions (e.g., electrostatic and hydrogen bonding) during the different oxidation phases. The present paper shows that LSO tail segments mobility in terms of T2 multi-exponential relaxation decays, generated by data reconstructing of 1H transversal relaxation components are providing a clear, sharp and informative understanding of LSO sample’s autoxidation aging processes. This is supported by high field band selective 1H NMR pulse excitation for hydroperoxide and aldehydes quantification of the same LSO samples at 25, 40, 60, 80, 100, and 120oC with pumped air for 168 h. Peroxide value, viscosity and self-diffusion, as well as fatty acids profile and by- products determined by GC-MS were also carried out, and correlated with the LSO tail T2 relaxation results. In conclusion the selective determination of LSO alkyl tail T2 energy relaxation time domain values was demonstrated as a rapid evaluation marker for following omega-3 PUFA-rich oils oxidative aging.

In this study, the effects of solid-state fermentation (SSF), including strain (Aspergillus niger NRRL 334 and A. oryzae NRRL 5590) and fermentation time (24, 48, and 72 h) on the nutritional value of cold-pressed (CP) and hexane-extracted (HE) canola meals were examined. SSF increased the protein content of both types of meals (from ~36 to ~40%) while reducing the oil content of CP meals (from ~12 to 9%). There was a significant reduction (~80%) in the phytic acid content of both types of meals after fermentation using either fungi. Overall, fermented samples showed a decrease in the total phenolic content from 2.7-3.1 to ~1.0 mg gallic acid equivalents (GAE)/g DM (a ~65% reduction), of which specifically the HE meal fermented with A. niger sample had the greatest decrease from 3.1 to 0.6 mg GAE/g DM (~81% reduction). Seventy-two hours of fermentation decreased the in vitro protein digestibility (IVPD) of the meals. In contrast, a shorter fermentation time (24 h) increased the IVPD as compared to the controls (from ~73% to 77-81%), with the exception of the CP meal fermented with A. niger which had decreased IVPD at all fermentation times. Overall, the changes indicate that SSF using A. niger or A. oryzae can be useful to positively modify the composition of different canola meals and improve their nutritional value by significantly increasing the protein content, decreasing the levels of antinutrients, while only slightly reducing IVPD.

The application of nanostructured lipid carrier (NLC) in UV filters encapsulation was found to enhance its safe use. In this work, kenaf seed oil-NLC (KSO-NLC) co-loaded with UV filters encapsulated was used as an active ingredient in α-tocopherol cream to develop a photoprotective prototype. It was then subjected to further analysis to determine the physical properties storage stability and cytotoxicity. The ratio of KSO-NLC to α-tocopherol cream was optimised based on the SPF value using UV transmittance analyser. The physical properties of the samples were analysed and the amount of α-tocopherol was quantified by ultra-high performance liquid chromatography (UHPLC). The optimised sample was then evaluated for in vitro antioxidant activities using DPPH and ABTS assays. Meanwhile, in vitro cytotoxicity was studied on normal human dermal fibroblast (NHDF) cell line using MTT and CCK-8 assays. The sample produced by KSO-NLC to α-tocopherol cream in ratio 1:2 (N3) showed SPF value > 50. Besides, the samples showed microbial stability and sustainable α-tocopherol content upon 12 weeks of storage. The cytotoxicity evaluation of N3 and α-tocopherol cream (N5) showed > 100 % cell proliferation indicated there is no side effect on the cell growth, yet it triggered the cell proliferation with the presence of bioactive compounds. Overall, the results herein gathered are very promising towards the development of new green cosmetic formulations with the utilisation of KSO-NLC and palm-based α-tocopherol cream.

Protein from camelina seed is a valuable co-product that can be derived from the meal remaining after oil extraction. The current study describes the types and physicochemical properties of the major proteins present in camelina meal. Seed coat mucilage, which interferes with protein extraction, was removed from whole seeds by digestion with Viscozyme® and lipids were removed with hexane to obtain demucilaged/defatted meal. Protein comprised 51.3% of meal dry matter and the eight essential amino acids comprised 40.8% of total amino acids. The meal polypeptide profile showed bands originating from cruciferin (~44.1 and 51.7 kDa), napin (~14 kDa) and oil body proteins (OBP; ~15-20 kDa) resembling that of other crucifers. Cruciferins (11 isoforms) were the predominant proteins, while vicilins (6 isoforms) also were identified among the proteins soluble at pH 8.5. Among the proteins soluble at pH 3, napins (5 isoforms) comprised the majority, though late embryogenesis abundant proteins also were found. Camelina cruciferin and napin were confirmed to possess predominantly β-sheet and α-helix secondary structures, respectively. Camelina cruciferin structure was highly sensitive to changes in medium pH and underwent acid-induced denaturation at pH 3, but exhibited high thermal stability (>80°C) at neutral and alkaline pHs. The structure of camelina napins was less sensitive to pH. The major proteins associated with oil bodies were oleosins (6 isoforms). Identification and characterization of the properties of camelina meal proteins will enable strategic paths for co-product valorization.

Oil bodies (OBs) are micron- or submicron-sized sub-organelles widely found in plants seeds and nuts. The structure OBs is composed of a core of triglycerides covered by a phospholipid-protein layer, which ensures the stability of the OBs under extreme environmental conditions and further protects core lipids as energy reserves. As naturally pre-emulsified oil-in-water emulsions, OBs have been gradually applied to replace synthetically engineered oil droplets. In this paper, the recent research on the composition, extraction, stability, delivery system, digestion, food applications and future perspectives of plant OBs are reviewed. Recent studies have focused on the OBs surface protein identification and function, large-scale extraction techniques such as enzyme assisted, high pressure, ultrasound, and extrusion and the reconstituted OBs. Electrostatic deposition of polysaccharides significantly improves the stability of OBs emulsions. OBs emulsions have promising applications to encapsulate bioactive compounds, deliver targeted drugs, and prepare gels and edible functional films. The digestive behavior of OBs emulsions is similar to that of protein-stabilized emulsions, which can increase the satiety, effectively help reduce calorie intake and improve the bioavailability of functional factors. It has also promoted the development of simulated dairy, spices and meat products.

We studied the thermomechanical and microstructural properties of oleogels developed with 2.1 to 15.7 Moles of monoglycerides/Mole of lecithin (MG/LC). The oleogels were developed (15°C) in vegetable (VO) and mineral (MO) oils using at each MG/LC 2% or 4% total mass of gelator. During oleogelation a synergistic MG-LC interaction existed deriving in the development of MG-LC cocrystals even below the gelators’ minimum gelling concentration. The cocrystals delayed the Lα→β polymorphic transition and worked as an active filler of the oleogels’ crystal network. In the VO, the oil with the highest relative polarity, the oleogels were structured by a network of β crystals where the cocrystals acted as an active filler. In the MO, the oil with the lowest relative polarity, the cocrystals’ development was favored while the Lα→β transition occurred just in the 15.7 MG/LC oleogels. Then, at all MG/LC the VO oleogels with 2% or 4% total gelator concentration achieved higher G’ than MO oleogels. However, the presence of β crystals will produce deleterious effects in shorter time in the VO oleogels than in the MO oleogels. In both oils the oleogels with the highest G’ and gel-like rheological behavior were achieved at 8.1 MG/LC, particularly at 4% total gelator concentration. Under these conditions the β polymorph was limited developed in the VO oleogels and completely absent in the MO oleogels. Then, we might tailoring the rheology of MG-LC oleogels with storage stability using as design variables the MG/LC, the total gelator concentration, and the polarity of the oil.

The crystallization behavior of mango kernel fat (MKF) at 25 °C with and without the application of high-intensity ultrasound (HIU) (20 kHz, 125 W) was studied as a function of ultrasound amplitude level (30%, 50% and 70% of the maximum amplitude of 180 μm). The irradiation time was fixed at 5 s. It was found that HIU induced MKF crystallization. The crystallization induction time decreased with a decrease in crystal size and an increase in the number of crystals as the HIU amplitude increased. The β′→β transformation was also accelerated with HIU application. This work has shown that there is a great potential for the use of HIU in the food industry to achieve a shorter and more controllable crystallization process. In particular, HIU could be used as an efficient tool for controlling the polymorphic transition of fats.

Quantitative analyses on the coefficient of friction of common coating waxes are necessary and essential for designing systems for coating, conveying, packaging operations, transporting and storing of papers and paperboards, while analyses on wear behavior can be helpful for predicting performance durability of the coating surface. In this study, we investigated the friction and wear behaviors of six waxes including four commercial waxes and two soybean oil-based wax developed in our lab for bulk coating on cardboard. The effect of normal load, sliding velocity, and environmental temperature was evaluated. The friction coefficient of different waxes varies with sliding conditions. Higher normal load, sliding velocity, and environmental temperature resulted in significantly greater wear loss. Crystalline morphology and crystallinity were affected by environmental temperature, and they correlate to the variations in friction coefficient and wear loss of these materials. Overall, the Estercoat developed in our lab had comparable frictional properties and much less wear than paraffin wax under tested conditions and can be a good substitute for paraffin wax.

The conversion of triglycerides in edible oils into diacylglycerols (DAGs) is of great significance for obtaining products with health benefits. Camellia seed oil (C-oil), which is rich in oleic acid and linoleic acid, is an excellent raw material for the production of DAGs. In this study, the hydrolysis rate reached 87.14% under optimal hydrolysis conditions (reaction temperature of 60 °C, reaction time 24 h, 30% water content and 4% enzyme addition) with RMIM as catalyst, and camellia seed oil diacylglycerol (C-DAG) with a content of 62.49% was also given under optimal esterification conditions (vacuum system, 3% enzyme addition, 2% water addition, reaction temperature of 50 oC, and substrate molar ratio of free fatty acid to glycerol of 1:1). The high content of DAG was obtained by a coupled method, which eliminated the purification steps and reduced production costs. C-oil, and C-DAG have been characterized by means of GC, TG, DSC, and GC-IMS. Our results showed that the enzymatic coupling method did not affect the structural composition of the substances themselves, but did affect the crystallization and melting properties of the oils. Moreover, the taste of C-DAG was more delicate flavor than that of C-oil. Finally, the reaction mechanism has been analyzed by means of infrared spectroscopy, which showed that C-oil was mostly hydrolyzed to free fatty acids. C-DAG exhibited ester C-O stretching vibrations in the range 1280–1030 cm-1, indicating successful esterification reaction between camellia seed oil free fatty acids (C-FFAs) and glycerol under catalysis by the enzyme.