Preparation and structural characterization of epoxidized soybean oils-based pressure sensitive adhesive grafted with tea polyphenol palmitate.

Vegetable oils-based pressure sensitive adhesives (PSAs) are green and sustainable but face unsatisfactory adhesion strengths and are prone to aging during storage and application due to the existence of residual double bonds and massive ester bonds. Nine common antioxidants (tea polyphenol palmitate (TPP), caffeic acid, ferulic acid, gallic acid, butylated hydroxytoluene, tertiary butylhydroquinone, butylated hydroxyanisole, propyl gallate, and tea polyphenols) were grafted into epoxidized soybean oils-PSA (ESO-PSA) system to enhance antiaging properties and adhesion strengths. Results showed ESO-PSAs grafted with caffeic acid, tertiary butylhydroquinone, butylated hydroxyanisole, propyl gallate, tea polyphenols, or TPP didn't occur failure with TPP having best performance. The optimal conditions were ESO reacted with 0.9 % TPP, 70 % rosin ester, and 7.0 % phosphoric acid at 50 °C for 5 min, under which peel strength and loop tack increased to 2.460 N/cm and 1.66 N, respectively, but peel strength residue reduced to 138.09 %, compared with control (0.407 N/cm, 0.43 N, and 1669.99 %). Differential scanning calorimetry and thermogravimetric results showed TPP grafting increased the glass transition temperature of ESO-PSA slightly but improved its thermal stability significantly. Fourier transform infrared spectroscopy and 1H nuclear magnetic resonance results showed TPP, phosphoric acid, and rosin ester all partially participated in the covalently crosslinking polymerization of ESO-PSAs and the rest existed in the network structures in the free form.

Applications of Prolamin-Based Edible Coatings in Food Preservation: A Review.

Foods are susceptible to deterioration and sour due to external environmental influences during production and storage. Coating can form a layer of physical barrier on the surface of foods to achieve the purpose of food preservation. Because of its good barrier properties and biocompatibility, prolamin-based film has been valued as a new green and environment-friendly material in the application of food preservation. Single prolamin-based film has weaknesses of poor toughness and stability, and it is necessary to select appropriate modification methods to improve the performance of film according to the application requirements. The practical application effect of film is not only affected by the raw materials and the properties of the film itself, but also affected by the selection of preparation methods and processing techniques of film-forming liquid. In this review, the properties and selection of prolamins, the forming mechanisms and processes of prolamin-based coatings, the coating techniques, and the modifications of prolamin-based coatings were systematically introduced from the perspective of food coating applications. Moreover, the defects and deficiencies in the research and development of prolamin-based coatings were also reviewed in order to provide a reference for the follow-up research on the application of prolamin-based coatings in food preservation.

Effects of tea polyphenols and tertiary butylhydroquinone on quality of palm oils and losses of endogenous vitamin E during batch frying and oxidative stability of fried instant noodles.

The effects of tea polyphenols (TP) on the quality of palm oils (PO) and losses of endogenous vitamin E during batch frying of instant noodles as well as oxidative stability of fried instant noodles were investigated. PO without antioxidant addition was negative control and with tertiary butylhydroquinone (TBHQ) addition positive control. TP and TBHQ addition inhibited the increase of peroxide, p-anisidine, and total oxidation values of PO and reduced tocopherol and tocotrienol losses with 200 mg/kg of TP having the best performance, but didn't affect acid value and triglyceride composition. 200 mg/kg of TP and 100 mg/kg of TBHQ inhibited unsaturated fatty acid losses. During frying, TBHQ was mainly volatilized but TP transformed. TP more effectively reduced tocopherol and tocotrienol losses than TBHQ, reducing PO deterioration. The extended lifecycles of PO and shelf life of fried instant noodles are attributed to nonvolatility of TP and antioxidative properties of its transformation products.

Synthesis, Characterization and Evaluation of a Novel Tetraphenolic Compound as a Potential Antioxidant.

A novel antioxidant containing four hydroxyl groups, namely 2,2'-(2-methylpropane-1,3-diyl)bis(hydroquinone) (MPBHQ), was synthesized using hydroquinone and methylallyl alcohol as the raw materials, phosphoric acid as the catalyst, and toluene as the solvent system. The structure of MPBHQ was characterized by mass spectrometry, nuclear magnetic resonance, ultraviolet spectroscopy, and infrared spectroscopy. The results showed that MPBHQ has a good radical scavenging effect, as measured by the ORAC assay, DPPH radical scavenging assay, ABST radical scavenging assay, and Rancimat test. In fatty acid methyl ester and lard without exogenous antioxidants, MPBHQ showed better antioxidant performance than butylated hydroxytoluene (BHT), hydroquinone (HQ), tert-butyl hydroquinone (TBHQ), and propyl gallate (PG), meeting the need for a new antioxidant with better properties to ensure the oxidative stability of lipids and biodiesel.

Effects of monoacylglycerols with different saturation degrees on physical and whipping properties of milk fat-based whipping creams.

Milk fat-based whipping cream is primarily comprised of cream and whole milk. It has melt-in-the-mouth texture and unique milk flavor. However, milk fat-based whipping cream suffers from poor emulsion stability and foam firmness. The effects of monoacylglycerols (MAGs) with different saturation degrees (M1: 98% saturation, M2: 70% saturation and M3: 30% saturation) on emulsion properties (average particle size, viscosity, and emulsion stability) and whipping properties (overrun, firmness, shape retention ability, and foam stability) of milk fat-based whipping creams were investigated in this study. MAGs significantly decreased particle sizes (from 2.84 to 1.16 µm) and enhanced viscosity (from 350 to 490 cP) of the milk fat-based emulsions (emulsion without MAGs: M0, 5.01 µm, 298 cP) (P < 0.05). MAGs increased the stability of the milk fat-based emulsions with lesser phase separation during centrifugation tests and lower changes in particle sizes and viscosities during temperature cycling tests. Emulsion M1 with highest degree of saturation is less likely to destabilize and phase inverse. The decrease sharply in conductivity can be attributed to the entrapment of large amounts of air. Following that, the conductivity of M1 with low variation indicating high whipping resistance and less likely to coalescence and phase separation. Adding MAGs can significantly enhance overrun (M1: 205.3%, M2: 198.5%, M3: 141.4%) as compared to the control sample (M0: 97.9%) (P < 0.05). In emulsions containing MAGs with high degree of saturation (M1 and M2), firmness (M1: 95 g, M2: 109 g) and shape retention ability of the whipped creams were reduced as compared to control emulsion without MAG (M0: 173 g), but the foam stability (M1: 89%, M2: 91%) was enhanced (M0: 81%); M3 (firmness: 507 g; foam stability: 66%) has the contrasted effects. Whipping cream M2 demonstrated the best whipping properties with high overrun (198.46%), good firmness (109 g), shape retention ability and foam stability (91%). Good quality whipping creams can be obtained by selecting suitable MAGs.

Fabrication and Characterization of Novel Food-Grade Bigels Based on Interfacial and Bulk Stabilization.

Novel food-grade bigels were fabricated using zein nanoparticles for interfacial stabilization and non-surfactant gelators (beeswax and tapioca) for bulk stabilization. The present study demonstrated the importance of interfacial stability for biphasic gels and sheds light on the roles of the gelation mechanism and the oil/water ratio of a bigel on its microstructure, physical properties, and digestion behaviors. The results indicated that it is not an easy task to realize homogenization and subsequent gelation in beeswax-tapioca biphasic systems, as no amphiphilic components existed. However, applying the binding of zein nanoparticles at the oil-water interface allowed us to produce a homogeneous and stable bigel (oil fraction reach 40%), which exhibited enhanced structural and functional properties. Oleogel structures play a crucial role in determining the deformation response of bigel systems. As the oil content increased, the mechanical strength and elastic properties of bigels were enhanced. In the meantime, clear bigel-type transitions were observed. In addition, the fabricated bigels were shown to be beneficial for delayed digestion, and the lowest degree of lipolysis could be found in bigel with 50% oleogel.

Approach to evaluate the sensory quality deterioration of chicken seasoning using characteristic oxidation indicators.

Sensory quality deterioration of chicken seasoning was investigated using physicochemical properties, gas chromatography-mass spectrometry (GC-MS) and descriptive sensory analysis to approach an evaluation of the chicken seasoning deterioration. It was found that both peroxide value (POV) and total oxidation value (TOTOX) increased with the chicken seasoning deterioration, suggesting a dominant of the lipid oxidation in the sensory quality deterioration of chicken seasoning. Moreover, a continuously decreasing linoleic acid and contradictory increasing in volatile aldehydes (specifically for hexanal) indicated as characteristic oxidation indicators to evaluate the sensory quality deterioration. PLSR results further elucidated that the evolution of aldehydes was highly correlated with sensory quality deterioration. These results suggest the POV, TOTOX and hexanal as valuable indicators and provide a novel approach to quality and rapidly evaluate the sensory quality deterioration of chicken seasoning.

Processing of Flavor-Enhanced Oils: Optimization and Validation of Multiple Headspace Solid-Phase Microextraction-Arrow to Quantify Pyrazines in the Oils.

An efficient and effective multiple headspace-solid phase microextraction-arrow-gas chromatography-mass spectrometry (MHS-SPME-arrow-GCMS) analytical protocol is established and used to quantify the flavor compounds in oils. SPME conditions, such as fiber coating, pre-incubation temperature, extraction temperature, and time were studied. The feasibility was compared between SPME-arrow and the traditional fiber by loading different sample amounts. It was found that the SPME-arrow was more suitable for the MHS-SPME. The limit of detection (LODs) and limit of quantitation (LOQs) of pyrazines were in the range of 2-60 ng and 6-180 ng/g oil, respectively. The relative standard deviation (RSD) of both intra- and inter-day were lower than 16%. The mean recoveries for spiked pyrazines in rapeseed oil were in the range of 91.6-109.2%. Furthermore, this newly established method of MHS-SPME-arrow was compared with stable isotopes dilution analysis (SIDA) by using [2H6]-2-methyl-pyrazine. The results are comparable and indicate this method can be used for edible oil flavor analysis.

Thermal-Oxidation Stability of Soybean Germ Phytosterols in Different Lipid Matrixes.

The stability of soybean germ phytosterols (SGPs) in different lipid matrixes, including soybean germ oil, olive oil, and lard, was studied at 120, 150, and 180 °C. Results on the loss rate demonstrated that SGPs were most stable in olive oil, followed by soybean germ oil, and lard in a decreasing order. It is most likely that unsaturated fatty acids could oxidize first, compete with consumption of oxygen, and then spare phytosterols from oxidation. The oxidation products of SGPS in non-oil and oil systems were also quantified. The results demonstrated that at relatively lower temperatures (120 and 150 °C), SGPs' oxidation products were produced the most in the non-oil system, followed by lard, soybean germ oil, and olive oil. This was consistent with the loss rate pattern of SGPs. At a relatively higher temperature of 180 °C, the formation of SGPs' oxidation products in soybean germ oil was quantitatively the same as that in lard, implying that the temperature became a dominative factor rather than the content of unsaturated fatty acids of lipid matrixes in the oxidation of SGPs.

Dynamics of microbial community and changes of metabolites during production of type Ι sourdough steamed bread made by retarded sponge-dough method.

Dynamics of microbial community and changes of metabolites during production of type Ι sourdough steamed bread made by retarded sponge-dough method (SSB) were studied. Lactobacillus sanfranciscensis and Lactobacillus pontis were the dominant bacterial species. Particularly, relative abundances of Lactobacillus sanfranciscensis were significantly higher than that of other sub-dominant bacterial species. The dominant fungal species were Saccharomyces cerevisiae and Kazachstania humilis, and the latter was the most predominant. A stable bacterial and fungal consortia was established in sponge dough retarded from 12 to 24 h and main dough proofed from 30 to 60 min. Metabolism preference for maltose of Lactobacillus sanfranciscensis favoured a mutualistic association with maltose-negative Kazachstania humilis, and hence contributing to their competitiveness and dominance. Volatile compounds became more abundant with much more esters as sponge retarding time extended. Probably, the accumulation of organic acids and ethanol contributed mostly to formation of ethyl esters in sponge dough during retarding.

Plasma Cholesterol-Lowering Activity of Soybean Germ Phytosterols.

Soybean germ phytosterols (SGP) largely exist in soybean germ oil. Our previous study demonstrated that soybean germ oil was effective in reducing plasma cholesterol. However, it remains unknown if its phytosterols are the active ingredients responsible for the plasma cholesterol-lowering activity. The present study aimed to test the effect of SGP on plasma cholesterol and to investigate its associated underlying mechanisms using hamsters as animal model. Male hamsters (n = 40) were randomly divided into five groups (n = 8/group) and fed one of the five diets: a non-cholesterol diet (NCD), a high cholesterol diet (HCD), a HCD diet containing 0.5% cholestyramine (PC), and two HCD diets containing 0.1% (LP) and 0.2% (HP) SGP, respectively, for six weeks. Results showed that SPG reduced plasma cholesterol level in a dose-dependent manner, whereas it dose-dependently increased the excretion of both fecal neutral and acidic sterols. SGP was also effective in displacing cholesterol from micelles. It was concluded that SGP possessed hypocholesterolemic activity, likely by inhibiting cholesterol absorption in the intestine and promoting fecal sterol excretion.

The characterization of soybean germ oil and the antioxidative activity of its phytosterols.

The aim of this study was to characterize the composition of soybean germ and its oil from Northeast (NE-SG) and Shandong Province (SD-SG) of China with a focus on the composition of fatty acids and phytosterols as well as physicochemical properties. The results show that the average contents of water, protein, crude fat, crude fiber and ash of NE-SG and SD-SG were 8.23 ± 0.11%, 40.47 ± 0.10%, 11.65 ± 0.14%, 6.20 ± 0.09% and 4.79 ± 0.14%, respectively. The major fatty acids of the two soybean germ oils were linoleic acid (NE-SGO, 55.45%; SD-SGO, 52.15%), alpha-linolenic acid (NE-SGO, 16.21%; SD-SGO, 18.50%), palmitic acid (NE-SGO, 12.59%; SD-SGO, 11.40%) and oleic acid (NE-SGO, 9.87%; SD-SGO, 10.96%). The soybean germs were rich in phytosterols (NE-SGO, 3168 mg/100 g oil; SD-SGO, 3010 mg/100 g oil) consisting of ß-sitosterol, Δ7-stigmastenol, campesterol, stigmastanol, and citrostadienol. The antioxidant ability of soybean germ phytosterols was evaluated using DPPH˙ and OH˙ radical scavenging assays, ß-carotene protection assay and a heating oil system. The results demonstrated that soybean germ phytosterols had better antioxidant ability in oil systems than in non-oil systems. The antioxidant ability of these phytosterols was temperature- and time-dependent since it was more effective at lower temperatures (60 °C) with longer times as compared to higher temperatures (120 °C and 180 °C) with shorter times. These results prove that soybean germ phytosterols could be used as antioxidants in preventing lipid oxidation in foods stored at a low temperature for a long time.

Influence of acylglycerol emulsifier structure and composition on the function of shortening in layer cake.

The effect of the structure and composition of acylglycerol emulsifiers on the functionality of a palm-based shortening and quality of layer cake was investigated. The emulsifiers evaluated were distilled monoacylglycerol (DMG) and four acylglycerols (40% monoacylglycerol content) of octanoic acid (8:0), palmitic acid (16:0), stearic acid (18:0), and linoleic acid (18:2), designated as GMOct40, GMP40, GMS40, and GML40, respectively. The addition of GMP40 and GMS40 led to shortening with a higher solid fat content, finer crystals, and higher proportion of ß' form. These changes enhanced shortening's function in aiding air incorporation and retention in cake batter, which improved the cake's volume and crumb structure. However, the high monoacylglycerol content in DMG did not improve the properties of shortening and cake as compared to GMP40. In contrast, GML40 and GMOct40 had adverse effects on the functionality of shortening, which generated cakes with inferior crumb structure.

Fast and simple transesterification of epoxidized soybean oil to prepare epoxy methyl esters at room temperature.

Epoxidized soybean oil methyl esters were prepared via transesterification of epoxidized soybean oil (ESBO) with methanol catalyzed by cheap and stable sodium hydroxide (NaOH). The transesterification could be completed in only 5 min at room temperature (25 °C) without loss of the epoxide function and the transesterification rate was promoted significantly while the utilization of 5% acetone as co-solvent. The afforded products epoxidized methyl esters represent a renewable substrate that is readily converted into surfactants, fuel additives and other valuable industrial products.

Antioxidative Properties and Interconversion of tert-Butylhydroquinone and tert-Butylquinone in Soybean Oils.

During the process of antioxidation of tert-butylhydroquinone (TBHQ) in oil and fat systems, tert-butylquinone (TQ) can be formed, which has higher toxicity than TBHQ. The changes of TBHQ and TQ in edible oils at room temperature (RT) or under thermal treatment were investigated. Under thermal treatment, volatilization was the main pathway of TBHQ loss in edible oils. TQ was the main oxidation product of TBHQ under thermal treatment as well as at RT. The amount of TQ in thermally treated oils was much less than that in oils stored at RT due to the decreased amount of oxygen dissolved in oils and easy volatilization of TQ at high temperature. In addition, TQ can be reduced to TBHQ by reduction components in edible oils, but the conversion amount was very small. Thus, TQ, theoretically having no antioxidative property, presented a very weak antioxidative activity equivalent to that of BHA due to the presence of insignificant amount of TBHQ formed from TQ in edible oils. The narrow potential difference of 0.059 between oxidation and reduction peaks of TBHQ and TQ resulted in easy interconversion of TBHQ and TQ under the action of common oxidation and reduction substances which have a higher oxidation potential or a lower reduction potential than they have.

Simultaneous analysis of tert-butylhydroquinone, tert-butylquinone, butylated hydroxytoluene, 2-tert-butyl-4-hydroxyanisole, 3-tert-butyl-4-hydroxyanisole, α-tocopherol, γ-tocopherol, and δ-tocopherol in edible oils by normal-phase high performance liquid chromatography.

A normal-phase high performance liquid chromatography method for the simultaneous determination of tert-butylhydroquinone, tert-butylquinone, butylated hydroxytoluene, 2-tert-butyl-4-hydroxyanisole, 3-tert-butyl-4-hydroxyanisole, α-tocopherol, γ-tocopherol, and δ-tocopherol in edible oils was investigated. A silica column was used to separate the analytes with the gradient elution. An ultraviolet-visible detector was set at dual wavelengths mode (280 and 310nm). The column temperature was 30°C. The analytes were directly extracted with methanol. Results showed that the normal-phase high performance liquid chromatography method performed well with wide liner ranges (0.10∼500.00µg/mL, R2>0.9998), low limits of detection and quantitation (below 0.40 and 1.21µg/mL, respectively), and good recoveries (81.38∼102.34% in soybean oils and 83.03∼100.79% in lard, respectively). The reduction of tert-butylquinone caused by the reverse-phase high performance liquid chromatography during the injection was avoided with the current normal-phase method. The two isomers of butylated hydroxyanisole can also be separated with good resolution.

Thermal Losses of Tertiary Butylhydroquinone (TBHQ) and Its Effect on the Qualities of Palm Oil.

The rules and patterns of thermal losses of tertiary butylhydroquinone (TBHQ) in palm oil (PO) and its effect on the qualities of PO were investigated by oven heating method. Volatilization and transformation products of TBHQ in PO were also studied in detail under heating treatment. Results showed that at low temperature (< 135°C), TBHQ had better antioxidative properties, while its antioxidative potency to PO was significantly weakened at high temperature (≥ 135°C). In addition, as heating temperatures increased and heating time prolonged, losses of TBHQ significantly increased in PO. Volatilization was the major pathway for losses of TBHQ in PO under heating treatment. Meanwhile, a small portion of TBHQ was transformed and the major transformation product was 2-tertbutyl-1,4- benzoquinone (TQ). Moreover, TQ and several decomposition products of PO were also observed in the volatilization products of TBHQ.

Magnetic Mesoporous Palladium Catalyzed Selective Hydrogenation of Sunflower Oil.

In this paper, a novel magnetic mesoporous Pd catalyst is used to catalyse selective hydrogenation of sunflower oil at a mild temperature of 50°C. Effects of reaction temperature, stirring speed, time, catalyst loading and hydrogen pressure on the reaction activity, trans fatty acid (TFA) and stearic acid formation were studied. Under the condition of 3.2 mg Pd/100 g oil, 50°C, 1300 rpm stirring speed and 19.0 atm of H2, the lowest amount of TFA generated during the reaction (IV = 80) was 14.9 ± 0.4% while 11.4 ± 0.4% of stearic acid was produced. And this magnetic Pd-catalyst can be reused easily for at least six times without significant catalyst deactivation, the amount of TFA almost remained unchanged. Moreover, this Pd-catalyst shows a good magnetic separation, which provides a potential method for the facile oil modification.

Simultaneous Analysis of Tertiary Butylhydroquinone and 2-tert-Butyl-1,4-benzoquinone in Edible Oils by Normal-Phase High-Performance Liquid Chromatography.

During the process of antioxidation of tertiary butylhydroquinone (TBHQ) in oil and fat systems, 2-tert-butyl-1,4-benzoquinone (TQ) can be formed. The toxicity of TQ was much more than that of TBHQ. In the work, a normal-phase high-performance liquid chromatography (NP-HPLC) method for the accurate and simultaneous detection of TBHQ and TQ in edible oils was investigated. A C18 column was used to separate TBHQ and TQ, and the gradient elution solutions consisted of n-hexane containing 5% ethyl acetate and n-hexane containing 5% isopropanol. The ultraviolet (UV) detector was set at dual wavelength mode (280 nm for TBHQ and 310 nm for TQ). The column temperature was 30 °C. Before the NP-HPLC analysis, TBHQ and TQ were first extracted by methanol, subjected to vortex treatment, and then filtered through a 0.45 µm membrane filter. Results showed that linear ranges of TBHQ and TQ were both within 0.10-500.00 µg/mL (R(2) > 0.9999). The limit of detection (LOD) and limit of quantification (LOQ) of TBHQ and TQ were below 0.30 and 0.91 µg/mL and below 0.10 and 0.30 µg/mL, respectively. The recoveries of TBHQ and TQ were 98.92-102.34 and 96.28-100.58% for soybean oil and 96.11-99.42 and 98.83-99.24% for lard, respectively. These results showed that NP-HPLC can be successfully used to analyze simultaneously TBHQ and TQ in the oils and fats.

Comparative Study of Soybean Oil and the Mixed Fatty Acids as Acyl Donors for Enzymatic Preparation of Feruloylated Acylglycerols in Ionic Liquids.

Feruloylated acylglycerols (FAGs) are the lipophilic derivatives of ferulic acid. In this work, soybean oil (SBO) and the mixed fatty acids (MFA) were selected as fatty acyl donors, and reacted with glyceryl monoferulate (GMF) to prepare FAGs in ionic liquids (ILs). Effect of various reaction parameters (time, temperature, enzyme concentration, and substrate ratio) and ILs on the GMF conversion and the reaction selectivity for FAGs formation were investigated. Response surface methodology (RSM) based on a 3-level-4-factor Box-Behnken experimental design was employed to evaluate the inactive effect of reaction parameters. For the esterification of GMF with MFA, the maximum GMF conversion (98.9 ± 0.9%) and FAG yield (88.9 ± 0.6%) were achieved in [C10mim]PF6. However, for the transesterification of GMF with SBO, the maximum GMF conversion (94.3 ± 0.7%) and FAG yield (83.8 ± 1.0%) were obtained in [C12mim]PF6. High FAG selectivities (∼0.90) were also obtained using SBO or MFA as acyl donors.