bluuebunny/crossref_metadata_2025 huggingface dataset:
Multivariate model for the prediction of soluble condensed tannins in crude extracts of polyphenols from canola and rapeseed hulls
Authors: Naczk M. , Pink J. , Amarowicz R. , Pink D. , Shahidi F.
Published: November 2006

The feasibility of using ultraviolet spectrophotometry to develop multivariate models for prediction of soluble condensed tannins (SCT) content in crude polyphenols extracts from canola and rapeseed hulls was investigated. The polyphenols were extracted from hulls using 70% (vol/vol) aqueous acetone. Partial least squares regression was used to correlate the spectral data of the crude polyphenols in methanol between 265–295 nm with the SCT content in hulls. Both the proanthocyanidin (P) and the vanillin (V) assays were used to provide reference data for creating the models. The predictive ability of the models is good, as indicated by the RPD values [the ratio of the standard deviation of data to the standard error of calibration (SEC) of above 5. Additionally, the SEC values suggest that P is superior to V in predicting the SCT content of hulls using this method.
Selective hydrogenation of sunflower seed oil in a three‐phase catalytic membrane reactor
Authors: Veldsink Jan W.
Published: November 2006

Continuous hydrogenation of sunflower seed oil has been carried out in a novel three‐phase catalytic membrane hydrogenation reactor. The membrane reactor consisted of a membrane impregnated with Pd as the active catalyst, which provided a catalytic interface between the gas phase (H2) and the oil. Hydrogenations were carried out at different pressures, temperatures, and selectivities, and the formation of trans isomers was monitored during the hydrogenation runs. For the three‐phase catalytic membrane reactor, interfacial transport resistances and intraparticle diffusion limitations did not influence the hydrogenation reaction. Hydrogenation runs under kinetically controlled conditions showed that oleic and elaidic acid were not hydrogenated in the presence of linoleic acid. Initial formation of stearic acid was caused by direct conversion of linoleic acid into stearic acid by a shunt reaction. Furthermore, high selectivities led to high trans levels, which is in accordance with the many published data on hydrogenation of vegetable oils in slurry reactors. Finally, the catalytic membrane showed severe catalyst deactivation. Only partial recovery of the catalyst activity was possible.
Natural refining of extruded‐expelled soybean oils having various fatty acid compositions
Authors: Wang Tong , Johnson Lawrence A.
Published: November 2006

Simple, low‐capital‐investment oil refining techniques, which may also meet the needs of natural or organic food industries, were explored to process extruded‐expelled (E‐E) soybean oils with various fatty acid compositions. Most settled E‐E oils are naturally low in phosphatides (<100 ppm phosphorus) and were easily water degummed to low phosphorus levels (<55 ppm). Free fatty acids were reduced to 0.04% by adsorption with 3% Magnesol®. Magnesol reduced residual phosphorus contents to negligible levels. This material also adsorbed primary and secondary oil oxidation products. Our adsorption refining procedure was much milder than conventional refining, as indicated by little formation of primary and secondary lipid oxidation products and less loss of tocopherol. The remaining challenge to effective natural refining is the removal of off‐flavor components. Our adsorption treatment reduced the natural flavor of soybean oil but flavor was still present, probably too strong for many consumers. Polyunsaturated oils oxidized more easily than did the other types of oils; therefore, precautions should be taken when refining such oils. High‐oleic soybean oil, on the other hand, had excellent oxidative stability and better flavor characteristics after degumming and adsorption with Magnesol compared with other oils.
Characterization of oil exhibiting high γ‐linolenic acid from a genetically transformed canola strain
Authors: Liu Jim‐Wen , DeMichele Stephen , Bergana Marti , Bobik Emil , Hastilow Christine , Chuang Lu‐Te , Mukerji Pradip , Huang Yung‐Sheng
Published: November 2006

The seed oil from a genetically transformed canola (Brassica napus) containing 43% (w/w) of γ‐linolenic acid (G, 18∶3n−6), 22% linoleic acid (L, 18∶2n−6), and 16% oleic acid (O, 18∶1n−9) was evaluated. In this high γ‐linolenic acid canola oil (HGCO), the predominant 18∶3n−6‐containing triacylglycerol (TG) molecular species were GGL (23%), GLO (20%), and GGG (11%). In the total TG, approximately 75% of the 18∶3n−6 was located at the sn‐1,3 positions, while only 34% of linoleic acid was at the sn‐1,3 positions. The GGL molecular species of HGCO contained approximately equal amounts of GLG and GGL positional isomers, while the GLO molecular species had 95% GOL and 5% GLO isomers. The general characteristics and the tocopherol and phytosterol contents were mostly similar between HGCO and nontransformed canola oil. No detectable amounts of amino acids and nucleotides were observed in the HGCO.
Improved synthesis of sucrose fatty acid monoesters
Authors: Cruces M. Angeles , Plou Francisco J. , Ferrer Manuel , Bernabé Manuel , Ballesteros Antonio
Published: November 2006

The base‐catalyzed synthesis of four sucrose fatty acid esters (caprylate, laurate, myristate, and palmitate) was performed in dimethylsulfoxide by transesterification of sucrose with the corresponding vinyl esters using disodium hydrogen phosphate as catalyst. In using a molar ratio sucrose/vinyl ester 4∶1 and mild reaction conditions (40°C and atmospheric pressure), yields were higher than 85%. The isolated sucroesters had a higher percentage of monoesters (≥90%) and a lower content of diesters in comparison with commercial derivatives. In all cases, 2‐O‐acylsucrose was the major product (≥60%) in the monoester fraction.
Foaming properties of soybean protein‐based plywood adhesives
Authors: Hojilla‐Evangelista Milagros P. , Dunn Larson B.
Published: November 2006

A study was conducted to evaluate the potential of soy protein‐based plywood glues for foam extrusion. Foaming properties were the first criterion used to screen several soy protein sources. Foaming capacities and stabilities of glue mixes containing animal blood (control) or soy products (meals, flours, concentrates, and isolates) were compared and correlated with molecular weights and surface hydrophobicity indices (So) in an attempt to identify structure/function relationships. The blood‐based glue mix produced more foam than any of the soy‐based glues. Soy flours and concentrates generally produced greater foam volumes and more stable foams than soy meal and isolates. Differences in foaming properties could not be explained by solubility profiles or So. However, results of gel electrophoresis indicated that soy products with poor foaming properties had extensive structure modifications or contained considerably lesser amounts of protein available for foaming reactions. Glue mixes containing the soy flours ISU‐CCUR, Honeysoy 90, Nutrisoy 7B, and defatted Soyafluff and the soy concentrates Arcon F, ISU‐CCUR, and Procon 2000 demonstrated the desired mixing and foaming properties for foam extrusion.
Production of alkyl esters from tallow and grease using lipase immobilized in a phyllosilicate sol‐gel
Authors: Hsu An‐Fei , Jones Kerby , Marmer William N. , Foglia Thomas A.
Published: November 2006

The lipase‐catalyzed synthesis of alkyl esters from tallow and grease using Pseudomonas cepacia lipase (PS‐30) immobilized within a phyllosilicate sol‐gel matrix was investigated. The effects of the presence of alcohol and of the amount of enzyme used were studied. The matrix‐immobilized PS‐30 lipase effectively converted grease and tallow to ethyl esters in greater than 95% yield when using ethanol. The final conversion of grease or tallow to alkyl esters was aided by the addition of molecular sieves (0.4 wt% of substrates) to the reaction mixture. The matrix‐immobilized PS‐30 enzyme was easily recovered and could be reused at least five times without losing its activity. Accordingly, the phyllosilicate sol‐gel immobilized PS‐30 lipase is potentially useful for the economic production of biodiesel fuel.
Identification of (e)‐11‐hydroxy‐9‐octadecenoic acid and (E)‐9‐hydroxy‐10‐octadecenoic acid by biotransformation of oleic acid by Pseudomonas sp. 32T3
Authors: Rodríguez E. , Espuny M. J. , Manresa A. , Guerrero A.
Published: November 2006

Pseudomonas sp. 32T3, a newly identified strain originally isolated from a vegetable oil‐contaminated soil, produces three monohydroxy acids—(E)‐11‐hydroxy‐9‐octadecenoic acid, (E)‐10‐hydroxy‐8‐octadecenoic acid, and (E)‐9‐hydroxy‐10‐octadecenoic acid—as bioconversion products of oleic acid. The bacterial cells were grown in a mineral medium containing oleic acid as the main carbon substrate. The compounds were identified as the corresponding methyl esters on the basis of their chromatographic and spectroscopic (1H and 13C nuclear magnetic resonance and gas chromatography‐mass spectrometry) features.
Detection of pressed hazelnut oil in admixtures with virgin olive oil by analysis of polar components
Authors: Gordon Michael H. , Covell Christopher , Kirsch Nicole
Published: November 2006

Analysis of the polar fraction from virgin olive oil and pressed hazelnut oil by high‐performance liquid chromatography showed marked differences in the chromatograms of the polar components in the two oils. Six commercial samples of pressed hazelnut oil and 12 samples of virgin olive oil (or blended olive oil including virgin olive oil) were analyzed. The phenolic content of the pressed hazelnut oil samples was 161±6 mg·kg−1. Inspection of the chromatograms showed that the pressed hazelnut oil extracts contained a component that eluted in a region of the chromatogram that was clear in the olive oil samples, and consequently this component could be used to detect adulteration of virgin olive oil by pressed hazelnut oil. The component had a relative retention time of 0.9 relative to 4‐hydroxybenzoic acid added to the oil as an internal standard. The ultraviolet spectrum of the component showed a maximum at 293.8 nm, but the component could not be identified. Analysis of blends of oils showed that adulteration of virgin olive oil by commercial pressed hazelnut oil could be detected at a level of about 2.5%.
Trans‐free bakery shortenings from mango kernel and mahua fats by fractionation and blending
Authors: Reddy S. Yella , Jeyarani T.
Published: November 2006

Bakery shortenings prepared by hydrogenation contain high levels of trans fatty acids, which are considered to be risk factors for cardiovascular disease. The shortenings prepared from maogo kernel and mahua fats have no trans fatty acids. Mahua fat was fractionated by dry fractionation to obtain a high‐melting fraction (10% yield, Mh1). Mango fat was fractionated by two‐stage solvent fractionation, separating about 15% high‐melting fraction (Mk1) in the first stage, followed by 40% stearin (Mk2) in the second stage. The formulation containing 80% Mh1 and 20% of mango middle stearin fraction (Mk2) showed melting characteristics and onset and enthalpy of crystallization similar to those of commercial hydrogenated shortenings designed for cakes and biscuits. The formulation suitable for puff pastry shortening was prepared by blending 50% mango 1st stearin (Mk1) and 50% mahua fat with addition of 5–7% of fully hydrogenated vegetable oil. The formulations having melting characteristics similar to those of commercial cake and biscuit shortenings were also prepared by blending 40% mango fat and 60% mahua fat with 5–7% incorporation of fully hydrogenated peanut oil. However, these formulations showed delayed transition to the stable forms compared to those of commercial samples. Fatty acid composition revealed that commercial hydrogenated shortenings consisted of 18–29% trans oleic acid, whereas the formulations we prepared did not contain any trans acids. The iodine values of commercial samples were 57–58, whereas the value for the formulations prepared were 47–53. The consistency of the prepared samples as measured by cone penetrometer was slightly harder than commercial samples. These studies showed that it is possible to prepare bakery shortenings with no trans fatty acids by using mango and mahua fats and their fractions.
β‐Apo‐8′‐Carotenoic acid and its esters in sunflower oil oxidation
Authors: Yanishlieva N. V. , Marinova E. M. , Raneva V. G. , Partali V. , Sliwka H. ‐R.
Published: November 2006

The oxidation kinetics of sunflower oil (SO) and pure triacylglycerols of sunflower oil (TGSO) in the presence of different concentrations (0.0008–0.02%, 1.9–32.7×10−5 M) of β‐apo‐8′‐carotenoic acid (CA), ethyl β‐apo‐8′‐carotenoate (EC), and β‐apo‐8′‐carotenoylglycerol (CG) were studied. The process was performed at high (kinetic regime) and low (diffusion regime) oxygen concentrations at room temperature and at 100°C and in the dark and in daylight. CA, EC, and CG were not antioxidants in TGSO systems. However, the carotenoid derivatives, especially CA, increased the stability of tocopherol‐containing SO at room temperature and in daylight. The stabilization effect was more evident in a kinetic regime of oxidation. The synergism between the carotenoids and tocopherols was characterized by the increase of the stabilization factor F and activity A. F and A were highest for CA (F=1.2–5.5, A=2.4–78.6), followed by EC (F=1.2–3.5, A=1.7–14.6) and CG (F=1.1–2.1, A=1.6–5.5) in the kinetic regime for SO exposed to daylight at room temperature.
Preparation of micron‐scale monodisperse oil‐in‐water microspheres by microchannel emulsification
Authors: Kobayashi Isao , Nakajima Mitsutoshi , Nabetani Hiroshi , Kikuchi Yuji , Shohno Atsushi , Satoh Kazumi
Published: November 2006

Micron‐scale monodisperse oil‐in‐water (O/W) micropheres (MS) were prepared using a novel microchannel (MC) emulsification technique. The characteristics of the MS preparation and the O/W‐MS prepared were studied. Soybean oil and medium‐chain triacyglycerol (MCT) were used as the disprrsed phase, and physiological saline was used as the continuous phase. Silicon MC with 1 to 3μm‐equivalent channel diameters were employed. A novel MC module was devised to easily recover the O/W‐MS prepared. The effects of the channel shape on the behavior of MS formation, on the MS size, and on the distribution were investigated. An MC with a terrace at the MC outlet stably yielded micron‐scale monodisperse O/W‐MS; the MS had diameters of about 5 μm, and their coefficients of variation were below 9%. Monodisperse food‐grade O/W‐MS with diameters of about 4 μm could be obtained by using polyglycerol fatty acid ester as the surfactant. The size and size distribution of the recovered O/W‐MS remained almost constant over 60 d, demonstrating their long‐term stability.
Damage detection in horse mackerel (Trachurus trachurus) during chilled storage
Authors: Aubourg Santiago P.
Published: November 2006

Sensory and chemical analyses were performed during the chilled storage of whole and filleted horse mackerel (Trachurus trachurus), an underutilized medium‐fat fish species. For both kinds of fish products, satisfactory correlations with the storage time were obtained for amine formation (total volatile basenitrogen and trimethylamine‐nitrogen), lipid damage (free fatty acid formation), and formation of interaction compounds (fluorescence detection in the aqueous phase). Sensory analyses showed a gradual lower grading with time, with a shelf life of 14 d for whole‐fish samples and 12 d for fillet samples. Correlation and multivariate analyses between the sensory attributes and the chemical indices showed that trimethylamine‐nitrogen detection was the most accurate chemical method for damage assessment during the chilled storage of whole and filleted horse mackerel.
Thermal and mechanical properties of plastics molded from urea‐modified soy protein isolates
Authors: Mo Xiaoqun , Sun Xiuzhi
Published: November 2006

Soy protein has been considered as a potential alternative of some petroleum polymers in the manufacture of plastics. The purpose of this investigation was to characterize the thermal and mechanical properties of plastics made from urea‐modified soy protein. Soy protein isolate was separated from the defatted soy flour, modified with various urea concentrations, and compression‐molded into plastics. Differential scanning calorimetry showed that the temperatures of denaturation and the enthalpies of denaturation of the modified soy protein decreased as urea concentrations increased above 1 M. At the same urea concentration, molded plastics made from the modified soy proteins showed a similar temperature of denaturation as the modified soy protein, but a lower enthalpy of denaturation. Tensile strength and Young's modulus of the molded plastics from the modified soy proteins increased as urea concentration increased and reached their maximum values at 8 M urea modification. Both storage modulus and glass transition temperature of the plastics from the modified soy proteins increased as urea concentration increased. The plastics made from the 2 M urea‐modified soy proteins showed improvements in elongation, tough fracture behavior, and water resistance. The urea may function as a denaturant, a plasticizer, and a filler.
Analysis of the wax ester fraction of olive oil and sunflower oil by gas chromatography and gas chromatography‐mass spectrometry
Authors: Reiter Birgit , Lorbeer Eberhard
Published: November 2006

The wax ester fractions of solvent‐extracted sunflower oil and “extra virgin” olive oil were obtained by solid‐phase extraction and subsequently subjected to gas‐chromatographic and gas chromatographic‐mass spectrometric analysis. The comprehensive qualitative analysis of these fractions, which was carried out by the interpretation of mass spectral data, revealed several types of wax esters. In olive oil, shortchain, even‐numbered wax esters, saturated and unsaturated long‐chain, even‐numbered wax esters, benzyl esters, and the diterpenic esters phytyl and geranylgeranyl ester (the latter as a minor component) are present. With the exception of benzyl esters, all these esters occur in sunflower oil as well, but in considerably different amounts compared to those in olive oil. Whereas unsaturated wax esters are present in a negligible amount, diterpenic esters, mainly geranylgeranyl esters, represent the major part of the wax ester fraction.
Comparison of near‐infrared, fourier transform‐infrared, and fourier transform‐raman methods for determining olive pomace oil adulteration in extra virgin olive oil
Authors: Yang Hong , Irudayaraj Joseph
Published: November 2006

The adulteration of extra virgin olive oil with cheaper oils is a major problem in the olive oil market. In this study, near‐infrared, mid‐infrared, and Raman spectroscopic techniques were used to quantify the amount of olive pomace oil adulteration in extra virgin olive oil. The concentration of olive pomace oil in extra virgin olive oil was in the range between 0 and 100% in 5% increments by weight. Of the methods studied, Fourier transform‐Raman spectroscopy gave the highest correlation with a correlation coefficient of 0.997 and a standard error of prediction of 1.72%. The spectroscopic techniques have the potential to become a tool for rapid determination of adulteration in extra virgin olive oil, because they are casy to use and cost‐effective.
Transgenic cotton plants with increased seed oleic acid content
Authors: Chapman Kent D. , Austin‐Brown Shea , Sparace Salvatore A. , Kinney Anthony J. , Ripp Kevin G. , Pirtle Irma L. , Pirtle Robert M.
Published: November 2006

Cottonseed typically contains about 15% oleic acid. Here we report the development of transgenic cotton plants with higher seed oleic acid levels. Plants were generated by Agrobacterium‐mediated transformation. A binary vector was designed to suppress expression of the endogenous cottonseed †‐12 desaturase (fad2) by subcloning a mutant allele of a rapeseed fad2 gene downstream from a heterologous, seedspecific promoter (phaseolin). Fatty acid profiles of total seed lipids from 43 independent transgenic lines were analyzed by gas chromatography. Increased seed oleic acid content ranged from 21 to 30% (by weight) of total fatty acid content in 22 of the primary transformants. The increase in oleic acid content was at the expense of linoleic acid, consistent with reduced activity of cottonseed FAD2. Progeny of some lines yielded oleic acid content as high as 47% (three times that of standard cottonseed oil). Molecular analyses of nuclear DNA from transgenics confirmed the integration of the canola transgene into the cotton genome. Collectively, our results extend the metabolic engineering of vegetable oils to cottonseed and should provide the basis for the development of a family of novel cottonseed oils.
Enzyme‐assisted aqueous extraction of rice bran oil
Authors: Sharma Aparna , Khare S. K. , Gupta M. N.
Published: November 2006

In the present study, rice brain oil was extracted by enzyme‐assisted aqueous extraction under optimized aqueous extraction conditions using mixtures of ProtizymeTM (protease; Jaysons Agritech Pvt. Ltd., Mysore, India), PalkodexTM (α‐amylase; Maps India Ltd., Ahmedabad, India), and cellulase (crude cellulase; Central Drug House, Delhi, India). The optimal conditions used were: mixtures of amylase (80 U), protease (368 U), and cellulase (380 U), with 10 g of rice brain in 40 mL distilled water, pH 7.0, temperature 65°C, extraction time 18 h with constant shaking at 80 rpm. Centrifugation of the mixture at 10,000×g for 20 min yielded a 77% recovery of the oil.
Measuring stereoselectivity in lipase‐catalyzed acidolysis reactions by ultra‐high resolution 13C nuclear magnetic resonance
Authors: Chandler Ian C. , Howarth Oliver W. , Crout David H. G.
Published: November 2006

Elucidating the stereoselectivity of lipases in synthetic reactions of triacylglycerols has hitherto been carried out using traditional analytical techniques to determine the composition of the reaction products. These methods are laborious and are not always appropriate for analysis of certain triacylglycerol types. A direct method, utilizing a stereospecific deuterium‐labeled triacylglycerol substrate, has been developed where the stereoisomeric composition of the reaction product is determined by ultra‐high resolution 13C nuclear magnetic resonance (NMR) spectroscopy. Through lipase‐catalyzed transesterification of deuterium‐labeled trilauroylglycerol with oleic acid, chemical shifts were induced in the 13C NMR spectrum by the deuterium atom and olefinic double bonds, enabling unambiguous stereospecific assignment of triacylglycerol species. By this method of analysis, we found an effect of the degree of reaction conversion on the extent of stereoisomerism in the triacylglycerol product. Stereoselectivity was greatest (for sn‐1) with lipase from Rhizomucor miehei. Lipases from Rhizopus niveus, Candida rugosa, Carica papaya, and the cutinase from Fusarium sp. were also found to exhibit stereoselectivity, with preference for either sn‐1 or sn‐3 acyl exchange.
Extractability of protein in physically processed rice bran
Authors: Anderson Alfred K. , Guraya Harmeet S.
Published: November 2006

Commercially obtained defatted (DF), full‐fat stabilized (FFS), and full‐fat unstabilized (FFU) rice bran were processed by colloid milling and homogenization to affect bran breakdown and extraction of rice protein. Relative to unprocessed samples, there were moderate to slight increases in the amount of protein extracted from the various fractions of processed bran. Colloid milling and homogenizing slightly influenced the distribution of proteins in the various fractions obtained, with the FFU showing the greatest effect compared to DF and FFS protein fractions. The protein content of the supernatant fraction of FFU bran increased from 21.8 to 33.0% after colloid milling with a further increase to 38.2% after homogenizing, representing an overall increase of 75.2% in protein content. The supernatant fractions of DF bran increased from 13.9 to 14.7% after colloid milling, and to 16.5% after colloid milling and homogenizing, for an overall increase of 18.7%. Sodium dodecyl sulfate polyacrylamide gel electrophoresis showed a molecular weight distribution ranging from 6.0 to 97.4 kDa. Few detectable differences between protein bands of unprocessed and processed DF and FFU bran were observed. However, FFS bran showed breakdown in size distribution of protein after colloid milling and homogenizing, because certain high molecular weight proteins shifted to lower molecular weight units.
Neutral and polar lipid phase transition of soybeans with various saturated fatty acid contents
Authors: Wang Tong , Hammond Earl G. , Fehr Walter R.
Published: November 2006

Soybeans with modified saturated fatty acid compositions sometimes have lower seed germination rate or other undesirable agronomic traits. To determine if seed germination could be related to the melting transitions of their lipids, triacylglycerols (TAG) and phospholipids (PL) from soybeans with a wide range of saturated fatty acid compositions were examined by differential scanning calorimetry. The melting transition temperatures of both TAG and PL increased with increasing palmitate and stearate percentages. The mean melting points of the various lipids calculated on the basis of the melting points of their fatty acids correlated with the observed transition temperatures. Increased lipid saturation and elevated phase transition temperatures may have contributed to the reduced germination and seedling growth rates of these modified seeds.
Detection of alkanes and alkenes for identifying irradiated cereals
Authors: Hwang Keum Taek , Hong Jin Sun , Yang Jae Seung , Sohn Hee Sook , Weller Curtis L.
Published: November 2006

Alkanes and alkenes can be produced from lipids in maize, brown rice, and wheat by irradiation. The purpose of this study was to determine whether the detection pattern of the hydrocarbons can be used for identifying postirradiation of cereals. Maize, brown rice, and wheat were irradiated at 0.5, 1, and 3 kGy. Oils were extracted from the samples using hexane and anhydrous Na2SO4. Hydrocarbon‐containing fractions, isolated using Florisil column chromatography, were analyzed using gas chromatography (GC). The first six Florisil column chromatography fractions of 10 mL each were collected. Prominent radiation‐induced alkenes 17∶1, 16∶2, 17∶2, and 16∶3 appeared mainly in the third, fourth, and fifth fractions. Those three fractions were combined and evaporated to a total volume of 4 mL for GC analyses. Alkenes 17∶1, 16∶2, 17∶2, and 16∶3 were detected in all irradiated samples but not in the non‐irradiated ones. The levels of the hydrocarbons changed little by roasting the nonirradiated and irradiated cereals.
Lipase‐catalyzed esterification of stearic acid with ethanol, and hydrolysis of ethyl stearate, near the critical point in supercritical carbon dioxide
Authors: Nakaya Hideki , Nakamura Kozo , Miyawaki Osato
Published: November 2006

The effect of pressure on the lipase‐catalyzed reaction in supercritical carbon dioxide (SCCO2) was investigated for the esterification of steric acid (SA) with ethanol and the hydrolysis of ethyl stearate (ES) near the critical point, ranging from 6 to 20 MPa in pressure and 35 to 60°C in temperature. The esterification rate of SA began to increase near the critical point and kept increasing steadily with an increase in pressure, reflecting the increase in SA solubility in SCCO2. The hydrolysis rate of ES showed a maximum at a pressure near the critical point. When the reaction was carried out with an initial overall ES concentration below its solubility limit in SCCO2, the maximum pressure shifted along the extended line of the gas‐liquid equilibrium in the supercritical region in the pressure‐temperature phase plane. This seems to be related to the singular behavior of some properties in SCCO2 along this line reported in the literature. These results show the importance of pressure, as well as temperature, as a parameter to control enzyme reactions in SCCO2.
High‐purity γ‐linolenic acid from borage oil fatty acids
Authors: Ju Yi‐Hsu , Chen Tor‐Chern
Published: November 2006

High‐purity γ‐linolenic acid (GLA) was obtained by employing a modified low‐temperature solvent crystallization process, followed by a lipase‐catalyzed esterification, to borage oil fatty acid. By applying a two‐stage solvent crystallization process to the borage oil fatty acid, GLA content was increased from 23.4 to 92.1% with a yield of 89.3%. After the esterification of GLA‐rich fatty acid with butanol catalyzed by Lipozyme IM‐60, GLA content in the fatty acid was further raised from 92.1 to 99.1%. The overall yield of the combined process was 72.8%. The effects of operation parameters on the Lipozyme IM‐60 catalyzed esterification between fatty acid and alcohol were systematically investigated.
Immobilization of Pseudomonas cepacia lipase by sol‐gel entrapment and its application in the hydrolysis of soybean oil
Authors: Noureddini H. , Gao X. , Joshi S. , Wagner P. R.
Published: November 2006

The immobilization of Lipase PS from Pseudomonas cepacia by entrapment within a chemically inert hydrophobic solgel support was studied. The gel‐entrapped lipase was prepared by the hydrolysis of tetramethoxysilane (TMOS) with methyltrimethoxysilane (MTMS), isobutyltrimethoxysilane (iso‐BTMS), and n‐butyltrimethoxysilane. The immobilized lipase was subsequently used in the hydrolysis of soybean oil to determine its activity, recyclability, and thermostability. The biocatalyst so prepared was equal to or better than the free enzyme in its hydrolytic activity. The catalytic activity of the entrapped lipase strongly depended on the type of precursor that was used in its preparation. The lipase entrapped within TMOS/iso‐BTMS showed the highest activity. The catalytic activity of the immobilized lipase was more pronounced during the earlier stages of the reaction. Thermostability of the lipase was significantly improved in the immobilized form. The immobilized lipase was stable up to 70°C, whereas for the free enzyme, moderate to severe loss of activity was observed beyond 40°C. The immobilized lipase was consistently more active and stable than the free enzyme. The immobilized lipase also proved to be very stable, as it retained more than 95% of its initial activity after twelve 1‐h reactions.
The conjugation and epoxidation of fish oil
Authors: Marks David W. , Larock Richard C.
Published: November 2006

Wilkinson's catalyst [RhCl(PPh3)3] has been used to conjugate fish oils in high yields under very mild reaction conditions. A catalyst load of 0.35 mol% of RhCl(PPh3)3, 0.43 mol% of (o‐CH3C6H4)3P, and 0.87 mol% of SnCl2·2H2O in ethanol solvent at 60°C for 2 d produces 82% conjugated Norway fish oil affords 90% conjugated fish oil in 93% yield. The Sharpless epoxidation procedure has also been employed to epoxidize fish oils. Using 0.34 mol% of CH3ReO3, 8.15 mol% of pyridine, and 1.03 equivalents of aq. 30% hydrogen peroxide in methylene chloride solvent at 25°C for 6 h, the Norway fish oil ethyl ester can be 100% epoxidized in an 86% yield. The Capelin fish oil gives 100% epoxidized fish oil in a 72% yield. Decreasing the amounts of CH3ReO3 and pyridine used in the reaction results in partially epoxidized fish oils.
The effect of the N‐linked glycans on structural features and physicochemical functions of soybean β‐conglycinin homotrimers
Authors: Maruyama Nobuyuki , Salleh Mohamad Ramlan Mohamed , Takahashi Koji , Yagasaki Kazuhiro , Goto Hideyuki , Hontani Naho , Nakagawa Shuko , Utsumi Shigeru
Published: November 2006

β‐Conglycinin is a trimeric protein consisting of three subunits, α,α′,and β, which are N‐glycosylated. The α and α′ subunits contain extension regions in addition to core regions common to all subunits. We purified homogeneous trimers consisting of only α, α′, or β from mutant soybean cultivars containing β‐conglycinin lacking one or two subunits: α homotrimers from an α′‐lacking mutant, α′ homotrimers from an α‐lacking mutant, and β homotrimers from an α‐and α′‐lacking mutant. Structural features and physicochemical functions of the three homotrimers were examined and compared with those of recombinant homotrimers having no N‐linked glycans. The native homotrimers have secondary structures very similar to those of the recombinant ones. In analogy with the recombinant homotrimers, the native ones exhibit different thermal stabilities from one another (β>α′>α), and the native α and α′ homotrimers exhibit better solubility, emulsifying ability, and heat‐induced association than the native β homotrimer. Further, the N‐linked glycans contribute to solubilities of the three subunits at low ionic strength (μ=0.08) and to the emulsifying ability of the native β homotrimer. N‐Linked glycans also prevent heat‐induced associations of the native α and α′ homotrimers but do not contribute to the secondary structure and the thermal stability of β‐conglycinin.
Oil‐binding capacity of plastic fats: Effects of intermediate melting point TAG
Authors: Jahaniaval Firouz , Kakuda Yukio , Abraham Varghese
Published: November 2006

The oil‐binding capacity (OBC) of fat crystals was investigated as a function of intermediate melting point TAG (IMP‐TAG) and stearin composition. Samples were prepared by melting 14% hard fraction (palm‐canola stearin and IMP‐TAG blends) in 86% liquid oil (olive, canola, safflower, and triolein) and crystallizing the mixture under fast and slow cooling conditions. Under fast cooling conditions, the OBC increased as the IMP‐TAG/stearin ratio increased. The OBC is the grams of bound oil (determined by centrifugation) divided by the grams of solid fat (determined by pulse NMR). The maximum OBC was observed at 14% IMP‐TAG and 0% stearin. In constrast, under slow cooling conditions, the 14% IMP‐TAG and 0% stearin sample did not form crystals, and only free oil was present. The OBC for each liquid oil was lower under slow cooling conditions than under fast cooling conditions when compared at the same IMP‐TAG/ stearin ratio. Solid fat content and RP‐HPLC analyses indicated that IMP‐TAG were retained in the crystal structure when processed under fast cooling conditions. RP‐HPLC analyses also revealed that TAG with two saturated FA were retained in the crystal structure and that the monosaturated TAG were not. It was concluded that the TAG composition and cooling conditions played an important role in determining the OBC.
Polar content vs. TAG oligomer content in the frying‐life assessment of monounsaturated and polyunsaturated oils used in deep‐frying
Authors: Bastida S. , Sánchez‐Muniz F. J.
Published: November 2006

The frying‐lives of olive oil (OO), sunflower oil (SO), and a blend of these oils (BO) were assessed and compared by measuring the polar content (PC) and the TAG oligomer content (TOC) in the oils. Oil was replenished with fresh oil every 10 uses in all three oils. Changes in the PC and TOC in relation to the number of frying uses were fitted to different curvilinear models. The power model yields the highest R2 value in the three oils. The 25% PC was surpassed after 32.2 fryings [95% confidence interval (95% Cl) 29.1–36.8] in the OO, 22.5 (95% Cl, 21.0–24.6) fryings in the SO, and 27.5 (95% Cl, 25.5–30.1) fryings for BO. However, according to the 10% TOC cutoff point, OO should be discarded after 25.0 (95% Cl, 22.8–28.7) fryings, SO after 15.0 (95% Cl, 14.8–15.4) fryings, and BO after 17.7 (95% Cl, 17.0–19.1) fryings. Nevertheless, changes in PC and TOC were different only between OO and SO (P<0.05 and P<0.02, respectively), indicating that OO performs better than SO, and that BO can be used as an alternative when both frying‐life and price are under consideration. Present findings suggest the need to unify criteria in different countries for oil disposal because the 25% PC corresponds to a TOC higher than 10%.
Enhanced biosurfactant production by Corynebacterium alkanolyticum ATCC 21511 using self‐cycling fermentation
Authors: Crosman John T. , Pinchuk Robert J. , Cooper David G.
Published: November 2006

Enhanced biosurfactant production by Corynebacterium alkanolyticum ATCC 21511 was accomplished in a self‐cycling fermenter (SCF) on a hexadecane substrate. The phospholipid biosurfactant produced during each cycle could be monitored rapidly using fluorescence spectroscopy. By optimizing the cycling pattern of the SCF, significantly better yields of biosurfactant were obtained than previously reported for this microorganism. It was also possible to virtually eliminate the hydrocarbon residue in the product. Harvest concentrations of 1.9 g L−1 were obtained by using a two‐stage fermentation. The first step was the growth of C. alkanolyticum in an SCF to yield a harvest of synchronous cells. These cells were transferred to a second vessel for the production stage. The concentration of biosurfactant could be further increased to 2.7 g L−1 by the addition of more hexadecane at the beginning of the second stage.
Model studies and the ADMET polymerization of soybean oil
Authors: Tian Qingping , Larock Richard C.
Published: November 2006

Grubbs' ruthenium catalyst 2 has been employed in model studies of the acyclic diene metathesis (ADMET) polymerization of soybean oil. In the presence of 0.1 mol% of catalyst 2, the ADMET polymerization of ethylene glycol dioleate afforded the isomerized (E)‐dioleate (27%), dimer (18%), trimer (13%), tetramer (7%), pentamer (5%), hexamer (4%), heptamer (4%), and 9‐octadecene (21%). Only a trace of any intramolecular cyclized product was formed. Under the same conditions, glycerol trioleate underwent ADMET polymerization to produce dimer, trimer, tetramer, pentamer, and monocyclic oligomers, with monocyclic oligomers predominating. The high number of repeat units in the monocyclic oligomers (n≅6, 10, and 21) in dicates that cross‐linking occurs readily in this process. Based on our model system studies, we have examined the ADMET polymerization of soybean oil and succeeded in producing polymeric materials ranging from sticky oils to rubbers.
Preparation of monodispersed emulsion with large droplets using microchannel emulsification
Authors: Sugiura Shinji , Nakajima Mitsutoshi , Seki Minoru
Published: November 2006

Microchannel (MC) emulsification is a novel technique for producing monodispersed emulsions with coefficients of variation of less than 5%. To produce emulsions with large droplets, we designed three MC with large dimensions. The MC structure consists of two parts: a channel and a terrace. Terrace length was defined as the length from the exit of the MC to the end of the terrace. The MC plates used in this study have deeper channels and longer terraces. The size limit of droplets prepared by MC emulsification was studied. Monodispersed emulsions with droplets as large as 100 μm were prepared using an MC with a depth of 16 μm and a terrace length of 240 μm. The average diameter (coefficient of variation) of the emulsion droplets was 98.1 μm (2.5%). Emulsions with larger‐diameter droplets were prepared using an MC with a longer terrace. The effect of the applied pressure on emulsification behavior was studied and discussed from the viewpoint of the droplet formation mechanism. At low applied pressures, droplet diameters were independent of the applied pressure, and monodispersed emulsions were produced. The pressure ranges of constant droplet diameter for large‐droplet emulsions were narrower than those for the 5 to 30 μm droplet size emulsions because interfacial tension is more significant on a smaller scale compared with the other forces.
Excess molar volumes and refractive indices of mixtures formed by acetates with sunflower oil at different temperatures
Authors: González Cristina , Resa José M. , Lanz Juan , Fanega M. Angeles
Published: November 2006

The aim of this work is to measure the densities and refractive indices of mixtures formed of acetates (ethyl, vinyl, propyl, isopropyl, and butyl acetate) with sunflower oil. From these measurements, excess molar volumes and variations of the refractive index of the mixtures have been calculated. The properties were measured at temperatures varying from 288.15 to 298.15 K. The excess molar volumes and variations of refractive index data were correlated vs. composition with Redlich‐Kister polynomials. Densities of the mixtures were predicted by the Rackett and modified Rackett equations. Refractive indices of the mixtures were predicted by several mixing rules and compared with experimental values. In all cases, SD between predicted and experimental data were less than 5%.
Speed of sound and isentropic compressibility of organic solvents + sunflower oil mixtures at 298.15 K
Authors: González Cristina , Resa José M. , Lanz Juan , Fanega M. Angeles
Published: November 2006

The speed of sound in binary liquid mixtures of organic solvents with sunflower oil was measured over the entire range of concentrations at 298.15 K. The solvents considered were: n‐hexane, n‐heptane, n‐octane, n‐nonane, ethanol, 1‐propanol, 2‐propanol, 1‐butanol, ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, and vinyl acetate. The speed of sound data were used to calculate isentropic compressibilities and excess isentropic compressibilities. The excess isentropic compressibilities vs. concentrations were correlated using Redlich‐Kister polynomials. Speed of sound determinations in the mixtures were predicted using two mixing rules proposed in the literature, and values were compared with experimental data. In all cases, SD between predicted and experimental data were less than 3.5%.
Genetic regulation of elevated stearic acid concentration in soybean oil
Authors: Pantalone V. R. , Wilson R. F. , Novitzky W. P. , Burton J. W.
Published: November 2006

Soybean [Glycine max (L.) Merr.] oil from commercial cultivars typically contains ca. 3% stearic acid (18∶0). However, germplasm carrying different mutations at the locus governing stearic acid (Fas) may contain 3% to about 35% 18∶0. Among these germplasm, a newly developed line, FAM94‐41 (9% 18∶0), carries a serendipitous natural mutation that is temporarily designated as the recessive fasnc allele, and the germplasm A6 (26% 18∶0) carries the recessive fasa allele. Mendelian genetic analysis of progeny from FAM94‐41×A6 revealed that fasnc and fasa are allelic to each other and represent different mutations in the same structural gene. However, the gene products (enzymes) produced by these alleles are unknown. The observation that 18∶0 concentrations among progeny from FAM94‐41×A6 increased primarily at the expense of unsaturated C18 FA suggests that fas alleles may reduce either 18∶0‐acyl carrier protein (AcP) desaturase or 18∶1‐ACP thioesterase activity. However, it also is conceivable that elevated 18∶0 concentrations may result from increased 3‐keto‐acyl‐ACP synthetase (KAS) II activity. To test the latter possibility, a population was created that segregated for the fasnc and the fap2 alleles (the latter of which is associated with reduced KAS‐II activity). Mendelian genetic analysis showed that these alleles represent independent genes at different gene loci and interact in an additive genetic manner to increase the total saturate concentration in this population. Based on this finding, we speculate that fas alleles probably encode 18∶0‐ACP desaturase or 18∶1‐ACP thioesterase in soybeans.
Production of structured lipids in a packed‐bed reactor with thermomyces lanuginosa lipase
Authors: Xu Xuebing , Porsgaard Trine , Zhang Hong , Adler‐Nissen Jens , Høy Carl‐Erik
Published: November 2006

Lipase‐catalyzed interesterification between fish oil and medium‐chain TAG has been investigated in a packedbed reactor with a commercially immobilized enzyme. The enzyme, a Thermomyces lanuginosa lipase immobilized on silica by granulation (lipozyme TL IM; Novozymes A/S, Bagsvaerd, Denmark), has recently been developed for fat modification. This study focuses on the new characteristics of the lipase in a packed‐bed reactor when applied to interesterification of TAG. The degree of reaction was strongly related to the flow rate (residence time) and temperature, whereas formation of hydrolysis by‐products (DAG and FFA) were only slightly affected by reaction conditions. The degree of reaction reached equilibrium at 30–40 min residence time, and the most suitable temperature was 60°C or higher with respect to the maximal degree of reaction. The lipase was stable in a 2‐wk continuous operation without adjustment of water content or activity of the column and the substrate mixture.
A potential biodegradable rubber—Viscoelastic properties of a soybean oil‐based composite
Authors: Xu Jingyuan , Liu Zengshe , Erhan Sevim Z. , Carriere Craig J.
Published: November 2006

Scientists are more and more interested in biodegradable materials owing to their environmental advantage. We investigated viscoelastic properties of a newly developed biomaterial made from epoxidized soybean oil (ESO). ESO cross‐linked by triethylene glycol diamine exhibited viscoelastic solid properties. The storage modulus (G′) was 2×104 Pa over four frequency decades. The phase angles were 14–18°. Stress relaxation measurements showed that there was no relaxation up to 500 s. From the plateau modulus we estimated that the M.W. of this cross‐linked soybean oil was on the order of 105. The composites of cross‐linked ESO with three different fibers had 50 times higher elasticity (G′) than those without fiber. Phase shifts were the same as those of cross‐linked oil without fibers, but the linear range of rheological properties was much narrower than that of the material without fibers. All these results indicated that this new biopolymer made from soybean oil exhibited strong viscoelastic solid properties similar to synthetic rubbers. These rheological properties implied that this biomaterial has high potential to replace some of the synthetic rubber and/or plastics.
Preparation and characterization of soy protein isolate films modified with sorghum wax
Authors: Kim Ki Myong , Hwang Keum Taek , Weller Curtis L. , Hanna Milford A.
Published: November 2006

The effect of increasing the concentration of sorghum wax paste on the characteristics of soy protein isolate (SPI) films was investigated. Water vapor permeability (WVP), tensile strength (TS), elongation at break (E), and total soluble matter (TSM) of cast SPI films were determined. Sorghum wax paste extracted with ethanol was added to film‐forming solutions of SPI at 5, 10, 15, or 20% w/w of protein. As the concentration of wax paste increased, mean WVP, E, and TSM values of SPI‐sorghum‐wax‐paste composite films decreased and were lower than those of control SPI films. Mean TS values were lower than the control upon addition of 5 and 10% wax paste; however, TS values increased at 15 and 20% was concentrations. Although no differences in components of sorghum wax were observed between paste extracted with ethanol and wax extracted with hexane, paste extracted with ethanol was miscible with the filmforming solution. SPI‐sorghum wax paste films had better water barrier and physical properties compared to control films.
Binary phase behavior of 1,3‐distearoyl‐2‐oleoyl‐sn‐glycerol (SOS) and 1,3‐distearoyl‐2‐linoleoyl‐sn‐glycerol (SLS)
Authors: Takeuchi M. , Ueno S. , Flöter E. , Sato K.
Published: November 2006

The binary phase behavior of SOS (1,3‐distearoyl‐2‐oleoyl‐sn‐glycerol) and SLS (1,3‐distearoyl‐2‐linoleoyl‐sn‐glycerol) was examined by using DSC and conventional and synchrotron radiation X‐ray diffraction. The solid‐solution phases were observed in the metastable α and γ forms in all concentration ranges. Results indicated that the miscible γ form did not transform to the β′ form when the mixtures were subjected to simple cooling from a high‐temperature liquid to a low‐temperature solid phase. However, and α‐melt‐mediated transformation into β′ and β2 resulted in the formation of immiscible phases in concentration ranges of SLS below 30%. By contrast, at SLS concentration ranges above 30%, the α‐melt‐mediated transformation caused crystallization of only the γ form, and β′ and β2 crystals did not appear. These results show that the specific interactions between SOS and SLS are operative in the phase behavior of the mixture states of SOS and SLS.