Showing papers in "Journal of the American Oil Chemists' Society in 1996"

Antioxidative activity and phenolic composition of pilot-plant and commercial extracts of sage and rosemary

Abstract: Eight sage (Salvia officinalis) and twenty-four rosemary (Rosmarinus officinalis) extracts, originating from pilot-plant or commercial sources, had different antioxidative activities as measured by accelerated autoxidation of methyl linoleate. Twenty-seven compounds were characterized in the Labiatae family extracts by high-performance liquid chromatography (HPLC) coupled with mass spectrometry, equipped with an atmospheric pressure chemical ionization interface, and by HPLC coupled with a photodiode array spectrophotometer. Twenty-two compounds were identified, including phenolic acids, carnosol derivatives, and flavonoids. The extracts showed great variation in their HPLC profiles, and no correlation was apparent between their antioxidative efficiency and their composition, in twenty specific phenols. Data indicated that the most effective compounds were carnosol, rosmarinic acid, and carnosic acid, followed by caffeic acid, rosmanol, rosmadial, genkwanin, and cirsimaritin.

Antioxidant activity of tocopherols and phenolic compounds of virgin olive oil

Abstract: The antioxidant effects of hydrophilic phenols and tocopherols on the oxidative stability in virgin olive oils and in purified olive oil have been evaluated. Total hydrophilic phenols and the oleosidic forms of 3,4-dihydroxyphenolethanol (3,4-DHPEA) were correlated (r=0.97) with the oxidative stability of virgin olive oil. On the contrary, tocopherols showed low correlation (r=0.05). Purified olive oil with the dialdehydic form of elenolic acid linked to 3,4-DHPEA, an isomer of oleuropeine aglycon, and 3,4-DHPEA had good oxidative stability. A synergistic effect was observed in the mixture of 3,4-DHPEA and its oleosidic forms with α-tocopherol in purified olive oil by the Rancimat method at 120°C.

Lipase-catalyzed production of biodiesel

Abstract: Lipases were screened for their ability to transesterify triglycerides with short-chain alcohols to alkyl esters. The lipase fromMucor miehei was most efficient for converting triglycerides to their alkyl esters with primary alcohols, whereas the lipase fromCandida antarctica was most efficient for transesterifying triglycerides with secondary alcohols to give branched alkyl esters. Conditions were established for converting tallow to short-chain alkyl esters at more than 90% conversion. These same conditions also proved effective for transesterfying vegetable oils and high fatty acid-containing feedstocks to their respective alkyl ester derivatives.

Changes in the characteristics and composition of oils during deep-fat frying

Abstract: Refined, bleached, and deodorized soybean oil and vanaspati (partially hydrogenated vegetable oil blend consisting of peanut, cottonseed, nigerseed, palm, rapeseed, mustard, rice bran, soybean, sunflower, corn, safflower, sesame oil, etc., in varying proportions) were used for deep-fat frying potato chips at 170, 180, and 190°C. Refractive index, specific gravity, color, viscosity, saponification value, and free fatty acids of soybean oil increased with frying temperature, whereas the iodine value decreased. The same trend was observed in vanaspati, but less markedly than in soybean oil, indicating a lesser degree of deterioration. Iodine values of soybean oil and vanaspati decreased from their initial values of 129.8 and 74.7 to 96.2 and 59.6, respectively, after 70 h of frying. Polyunsaturated fatty acids decreased in direct proportion to frying time and temperature. Losses were highest in soybean oil with a 79% decrease in trienoic acids and a 60% decrease in dienoic acids. Levels of nonurea adduct-forming esters were proportional to the losses of unsaturated fatty acids. Butylated hydroxyanisole and tertiary butylhydroquinone did not affect deterioration of soybean oil at frying temperatures.

Antioxidant activity of lipid-soluble phenolic diterpenes from rosemary

Abstract: A high-performance liquid chromatography method for analyzing the phenolic diterpenes present in rosemary (Rosmarinus officinalis L.) and commercial rosemary extracts is reported. Carnosic acid was the major phenolic diterpene present in rosemary leaves, with lesser amounts of 12-methoxycarnosic acid and carnosol. Several commercial rosemary extracts also were analyzed by this method, and in addition to these three compounds other phenolic diterpenes, such as 7-methoxyrosmanol, 7-methoxy-epirosmanol, and rosmanol, were found in some samples. These latter three compounds seem to be artifacts, produced from carnosic acid by oxidation and cyclization. The major phenolic diterpenes were isolated, and their relative antioxidatn activities in soybean oil were measured by the Rancimat. The potency of carnosic acid was more than twice that of any other compound. The antioxidant activity of pure carnosic acid was compared to butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), and tertiary butylhydroquinone (TBHQ) and was several times greater than BHT and BHA but less than TBHQ. Nuclear magnetic resonance data for several of the compounds that were incompletely characterized in previous literature are reported.

Production of docosahexaenoic and docosapentaenoic acids bySchizochytrium sp. isolated from Yap Islands

Abstract: A marine microbe (strain SR21) from the coral reef area of the Yap Islands was isolated by a screening test for polyunsaturated fatty acids and was found to accumulate lipid that contained 22:5n-6 docosapentaenoic acid (DPA) as well as 22:6n-3 docosahexaenoic acid (DHA). Strain SR21 was identified as genusSchizochytrium in Labyrinthulomycota, owing to its ultrastructural character and life cycle, which is composed of vegetative cell, zoosporangium, and zoospore stages. After cultural optimization, both in flask and fermenter, the highest DHA and DPA productivities of 2.0 and 0.44 g/L per day, respectively, were obtained in a medium of 60 g/L glucose and corn steep liquor/ammonium sulfate in a half salt concentration of seawater in fermenter culture at 28°C and pH 4. This productivity was almost twice that obtained with flask culture, indicating its high resistance to mechanical stirring. The lipid extracted from the cell was about 50% of the dry cell weight and was composed of 93% triacylglycerol (TG). DHA content of the lipid was 34% of total fatty acids. The TG profile was simple, and the content of the most dominant TG, 1,3-dipalmitoyl-2-DHA-TG, was 27%. TG that contained DHA and n-6-DPA amounted to 57 and 17%, respectively, of total TG molecules. Strain SR21 was revealed to be an excellent source of microbial DHA and n-6 DPA.

Fuel Properties and Emissions of Soybean Oil Esters as Diesel Fuel

Abstract: The effects of using blends of methyl and isopropyl esters of soybean oil with No. 2 diesel fuel were studied at several steady-state operating conditions in a four-cylinder turbocharged diesel engine. Fuel blends that contained 20, 50, and 70% methyl soyate and 20 and 50% isopropyl soyate were tested. Fuel properties, such as cetane number, also were investigated. Both methyl and isopropyl esters provided significant reductions in particulate emissions compared with No. 2 diesel fuel. A blend of 50% methyl ester and 50% No. 2 diesel fuel provided a reduction of 37% in the carbon portion of the particulates and 25% in the total particulates. The 50% blend of isopropyl ester and 50% No. 2 diesel fuel gave a 55% reduction in carbon and a 28% reduction in total particulate emissions. Emissions of carbon monoxide and unburned hydrocarbons also were reduced significantly. Oxides of nitrogen increased by 12%.

Improving the Low-Temperature Properties of Alternative Diesel Fuels: Vegetable Oil-Derived Methyl Esters

Abstract: This work explores near-term approaches for improving the low-temperature properties of triglyceride oil-derived fuels for direct-injection compression-ignition (diesel) engines. Methyl esters from transesterified soybean oil were evaluated as a neat fuel and in blends with petroleum middle distillates. Winterization showed that the cloud point (CP) of methyl soyate may be reduced to −16°C. Twelve cold-flow additives marketed for distillates were tested by standard petroleum methodologies, including CP, pour point (PP), kinematic viscosity, cold filter plugging point (CFPP), and low-temperature flow test (LTFT). Results showed that additive treatment significantly improves the PP of distillate/methyl ester blends; however, additives do not greatly affect CP or viscosity. Both CFPP and LTFT were nearly linear functions of CP, a result that compares well with earlier studies with untreated distillate/methyl ester blends. In particular, additives proved capable of reducing LTFT of neart methyl esters by 5–6°C. This work supports earlier research on the low-temperature properties; that is, approaches for improving the cold flow of methyl ester-based diesel fuels should continue to focus on reducing CP.

Survey of seed oils for use as diesel fuels

Abstract: Fifty-one out of 364 plant seeds being surveyed had fatty acid contents greater than 15% (dry weight), and their methyl esters had cetane indices higher than 50. Rambutan seed was an exception, with a lipid content of only 14.7%, but a high cetane index (67.1); thus, it was included in this report. Twenty seed oil methyl esters had cetane indices greater than 60. Three seed oils from the Sapindaceae family not only had high cetane indices but also contained long-chain fatty acids of 20 carbon atoms. Gross heats of combustion of the fatty acid methyl esters were slightly higher than those of neat oil, ranging from 38.2 to 40.8 j/g, whereas the heating values of the oils ranged from 37.4 to 40.5 j/g. Thus, these plant seed oils have great potential for development as diesel fuel or diesel fuel extender.

Relationship between volatile compounds and sensory attributes of olive oils by the sensory wheel

Abstract: Sixty-five volatile compounds and 103 sensory attributes were evaluated in 32 virgin olive oil samples from three different Mediterranean countries. Volatile compounds were analyzed with a dynamic headspace gas-chromatographic technique by using a thermal desorption cold-trap injector. The sensory analysis was conducted by six panels composed of assessors from the United Kingdom, Spain, the Netherlands, Greece and Italy. Principal-components analysis of sensory attributes was used to construct a statistical sensory wheel that represents the whole virgin olive oil flavor matrix. This wheel is composed of seven sectors that show the basic perceptions produced by the oil: green, bitter-pungent, undesirable, ripe olives, ripe fruit, fruity and sweet. The boundaries of each sector were calculated from the circular standard deviation of its sensory attributes. The relationship between sensory and instrumental analysis was determined by projecting volatiles onto the sensory wheel. Correlations of each volatile with the first two components of the principal-components analysis were taken as its coordinates (x, y) in the sensory wheel. Volatiles took up the most appropriate place within the sector that corresponded with their perception, and often close to the sensory attributes that explained their sensory properties. A gas-chromatographic/sniffing method was applied to virgin olive oil samples to assess the aroma notes that corresponded to olive oil volatile compounds and to verify the relationships found by the sensory wheel procedure. Most (89%) of the volatiles were well classified. Use of the statistical sensory wheel as an appropriate method to relate volatile and sensory data was clearly demonstrated.

Minor constituents of vegetable oils during industrial processing

Abstract: We report the effects of individual steps of industrial refining, carried out in Brazil, on the alteration of selected minor constituents of oils, such as corn, soybean, and rapeseed oils. Total sterols, determined by capillary gas chromatography (GC), decreased by 18–36% in the fully refined oils, compared with the crude oils. The total steradienes, dehydration products of sterols, were determinedvia a simple clean-up on a short silica gel column, followed by high-performance liquid chromatography (HPLC) with ultraviolet detection. The level of steradienes, normally not present in crude oils, increased after each refining step, especially after deodorization. Thus, the content of steradienes increased after deodorization by about 15- to 20-fold in corn and soybean oils, and by about 2-fold in rapeseed oil. The total steryl esters were also determinedvia clean-up on a short silica gel column, followed by HPLC with evaporative light scattering mass detection. A minor decrease in the level of steryl esters was observed after complete refining. The individual tocopherols and tocotrienols were determined by HPLC with a fluorescence detector. The level of total tocopherols and tocotrienols decreased by about 2-fold after complete refining of corn oil and by about 1.5-fold in soybean and rapeseed oils. In all three cases, maximum reduction of tocopherols was observed after the deodorization step. The level of polymeric glycerides, determinedvia clean-up on a short silica gel column followed by size-exclusion HPLC, increased to some extent (0.4–1%) during refining. The level oftrans fatty acids, determined by capillary GC, also increased to a substantial extent (1–4%) after refining.

Comparison of isopropanol and hexane for extraction of vitamin E and oryzanols from stabilized rice bran

Abstract: The effects of solvent-to-bran ratio (2∶1 and 3∶1, w/w), extraction temperature (40 and 60°C), and time (5, 10, 15, 20, and 30 min) were studied for hexane and isopropanol extraction. Increasing the solvent-to-bran ratios and extraction temperature increased the amounts of crude oil, vitamin E and oryzanol recovered for both solvents. An extraction time of 15 min was sufficient for optimum crude oil, vitamin E, and oryzanol extraction. Preheated isopropanol (3∶1 solvent/bran ratio and 60°C) extracted less crude oil (P .05) relative to preheated hexane. The data suggest that isopropanol is a promising alternative solvent to hexane for extraction of oil from stabilized rice bran.

A high-field1H nuclear magnetic resonance study of the minor components in virgin olive oils

Abstract: High-field (600 MHz) nuclear magnetic resonance (NMR) spectroscopy was applied to the direct analysis of virgin olive oil. Minor components were studied to assess oil quality and genuineness. Unsaturated and saturated aldehyde resonances, as well as those related to other volatile compounds, were identified in the low-field region of the spectrum by two-dimensional techniques. Unsaturated aldehydes can be related to the sensory quality of oils. Other unidentified peaks are due to volatile components, because they disappear after nitrogen fluxing. The statistical analysis performed on the intensity of these peaks in several oil samples, obtained from different olive varieties, allows clustering and identification of oils arising from the same olive variety. Diacylglycerols, linolenic acid, other volatile components, water, acetic acid, phenols, and sterols can be detected simulteneously, suggesting a useful application of high-field NMR in the authentication and quality assessment of virgin olive oil.

Assessment of potential prooxidant and antioxidant actions.

Abstract: Suggestions that oxidative stress plays a role in human diseases have led to the proposal that health might be improved by increased dietary intake of antioxidants. Plant-derived antioxidants, such as flavonoids or rosemary extracts, are increasingly proposed as important dietary antioxidant factors, and foods rich in antioxidants are also receiving attention. Before widescale usage of natural and synthetic antioxidants can be suggested, it is necessary to establish the properties of such molecules. Assays for characterizing the potential prooxidant/antioxidant actions of food additives, antioxidant supplements, antioxidant drug molecules, and nutrient components have been developed for this purpose.

Integral centrifuges for olive oil extraction. The qualitative characteristics of products

Abstract: Oil extraction experiments with three olive varieties (Coratina, Nebbio, and Grossa di Cassano) were carried out to compare the two-phase centrifugal decanter with conventional three-phase equipment The results showed that the two-phase centrifugal extractor renders better qualitative characteristics in the oils, which were comparable to pressed or filtered oils The two-phase decanter product exhibited higher contents of polyphenols,ortho-diphenols, hydroxytyrosol, tocopherols,trans-2-hexenal and total aromatic volatile substances Furthermore, the oils received a higher sensorial score and were characterized by higher values of oxidative stability and campersterol/stigmasterol ratio; lower values of turbidity, alcohol index and chromatic indices; lower content of pigments, steroid hydrocarbons, stigmastatriene, waxes and aliphatic and triterpenic alcohols

Reducing the crystallization temperature of biodiesel by winterizing methyl soyate

Abstract: Methyl soyate, made from typical soybean varieties, has a crystallization onset temperature (T co) of 3.7°C and, as a biodiesel fuel, is prone to crystallization of its high-melting saturated methyl esters at cold operating temperatures. Removal of saturated esters by winterization was assessed as a means of reducing theT co of methyl soyate. Winterizing neat methyl esters of typical soybean oil produced aT co of −7.1°C, but this was not an efficient way of removing saturated methyl esters because of the low yield (26%) of the separated liquid fraction. However, aT co of −6.5°C with 86% yield was obtained by winterizing the neat methyl esters of a low-palmitate soybean oil; aT co of −5.8°C with 77% yield was obtained by winterizing methyl esters of normal soybean oil diluted with hexane.

Deacidification of soybean oil by membrane technology

Abstract: After extracting free fatty acids (FFA) from a model crude vegetable oil with methanol, FFA were separated from methanol by nanofiltration. Of the several commercially available membranes that were evaluated, the best resulted in FFA rejection of >90% and flux of >25 Lm−2h−1. A combination of high-rejection and low-rejection membranes resulted in a retentate stream of 35% FFA and a permeate stream with less than 0.04% FFA, which can be recycled to the extractor. No alkali is required, no soapstock is formed, and almost all streams within the membrane process are recycled with little discharged as effluent.

Restructing butterfat through blending and chemical interesterification. 1. Melting behavior and triacylglycerol modifications

Abstract: Chemical interesterification of butterfat-canola oil blends, ranging from 100% butterfat to 100% canola oil in 10% increments, decreased solid fat content (SFC) of all blends in a nonlinear fashion in the temperature range of 5 to 40°C except for butterfat and the 90∶10 butterfat/canola oil blend, whose SFC increased between 20 and 40°C. The sharp melting associated with butterfat at 15–20°C disappeared upon interesterification. Heats of fusion for butterfat to the 60∶40 butterfat/canola oil blend decreased from 75 to 60 J/g. Blends with >50% canola oil displayed a much sharper drop in enthalpy. Heats of fusion were 30–50% lower on average for interesterified blends than for their noninteresterified counterparts. Both noninteresterified and interesterified blends deviated substantially from ideal solubility, with greater deviation as the proportion of canola oil increased. The change in the entropy of melting was consistently higher for noninteresterified blends than for interesterified blends. Chemical interesterification generated statistically significant differences for all triacylglycerol carbon species (C) from C30 to C56′ except for C42′ and in SFC at most temperatures for all blends.

Validation of the rancimat test for the assessment of the relative stability of fish oils

Abstract: The induction periods for the peroxidation of various fish oils at 55–90°C were studied by the Rancimat test. The natural logarithms of the induction periods varied linearly with respect to temperature, with a mean coefficient of −7.5×10−2°C−1, which was significantly different from that reported for vegetable oils. The activation energy for the formation of volatile acids had a mean value of 38.9 kJ/mol and was independent of the fish oil source. Peroxide formation under Rancimat test conditions followed first-order kinetics. The same kinetics were followed under Schaal Oven test conditions (forced-air oven, 60°C). On the basis of the results obtained, the Rancimat test appears to be useful in determining the relative stabilities of fish oils without the change in peroxide decomposition kinetics that may occur at elevated temperatures.

In-situ alcoholysis of soybean oil

Abstract: In-situ alcoholysis of soybean oil with methanol, ethanol,n-propanol, andn-butanol was investigated, as well as the extraction of the oil with these solvents, to explain the progress ofin-situ alcoholysis and to determine the parameters that affect this reaction Because methanol is a poor solvent for soybean oil, the amount of oil dissolved in methanol and converted to methyl esters was low afterin-situ alcoholysis Ethyl, propyl, and butyl esters of soybean fatty acids could be obtained in high yields fromin-situ alcoholysis of soybean oil with these alcoholsIn-situ alcoholysis proceeded through dissolution and alcoholysis of triglycerides successively, and the overall reaction rate was determined by the extraction and alcoholysis rates The parameters, affecting yield and purity of the product esters, were mainly those that favor extraction rate

Surface-active properties of novel cationic surfactants with two alkyl chains and two ammonio groups

Abstract: A series ofbis-quaternary ammonium salts was easily prepared by the reaction of a long-chaintert-alkylamine with epichlorohydrin, and their surface-active properties were measured. The prepared amphipathic compounds had good water solubility and showed characteristic surface-active properties, particularly, extremely excellent foaming ability and foam stability for some specific compounds, such as the compound with a dodecyl and a tetradecyl group as the lipophilic chains. Their critical micelle concentration, which decreased with increased alkyl chainlength, is two orders of magnitude lower compared with the conventionalmono-quaternary ammonium salts. In comparison with surface-active properties ofbis-quaternary ammonium salts, prepared from various organic dichlorides, there are little differences based on the kind of connecting group in the surface-active properties except for foaming.

Recovered oil from palm-pressed fiber: A good source of natural carotenoids, vitamin E, and sterols

Abstract: Recovered fiber from pressed palm fruits, which is normally burned as fuel to provide energy for the palm oil mills, has now been found to be a rich source of carotenoids, vitamin E (tocopherol and tocotrienols), and sterols. Residual oil (5–6% on dry basis) extracted from palm press fibers contains a significant quantity of carotenoids (4000–6000 ppm), vitamin E (2400–3500 ppm), and sterols (4500–8500 ppm). The major identified carotenoids are α-carotene (19.5%), β-carotene (31.0%), lycopene (14.1%), and phytoene (11.9%). In terms of vitamin E, α-tocopherol constitutes about 61% of the total vitamin E present, the rest being tocotrienols (α-, γ-, and δ-). The major sterols present are β-sitosterol (47%), campesterol (24%), and stigmasterol (15%). The oil extracted from palm-pressed fiber is contaminated with about 30% of palm kernel oil. The quality of this fiber oil is slightly lower than that of crude palm oil in terms of the content of free fatty acids, peroxide value, and anisidine value.

Surface activity and premicellar aggregation of some novel diquaternary gemini surfactants

Abstract: A series of novel cationic gemini surfactants, C n H 2n+1 N+(CH3)2CH2CHOHCHOHCH2N+(CH3)2C n H 2n+1 ·2Br−, have been synthesized, and their surface properties were investigated in water, 0.1 N NaCl, and 0.1 N NaBr at 25°C. From surface tension-log molar concentration plots, the pC20, critical micelle concentration (CMC), and γCMC values have been determined, and the area/molecule at the aqueous solution/air interface was calculated. When the number of carbon atoms in the alkyl (hydrophobic) chains is above a certain number, which depends upon the molecular environment, the surface activity of the compounds is less than expected. This appears to be due to formation of small, soluble aggregates below the CMC. Equilibrium constants calculated for this aggregation indicate that a series of oligomers are formed.

The antioxidant capacity of complex mixtures by kinetic analysis of crocin bleaching inhibition

Abstract: The capability of a compound or of a mixture of compounds to quench peroxyl radicals was measured by analyzing the kinetics of the competition of a parallel reaction where peroxyl radicals bleach the carotenoid crocin. This kinetic approach, originally described for the analysis of antioxidants reacting with hydroxyl radicals in water, was modified by both decreasing the polarity of the solvent, thus allowing the analysis of lipophilic compounds, and by substituting a source of peroxyl radicals for the hydroxyl radical generating system. Single compounds as well as complex mixtures were analyzed by kinetic data processing. Overall antioxidant capacity, relative to that of α-tocopherol or of its soluble analog Trolox C, was calculated. As examples of the use of this test, the antioxidant capacities of a crude rosemary extract, Maillard reaction products, and virgin olive oils were measured.

Is plastic fat rheology governed by the fractal nature of the fat crystal network

Abstract: The rheological properties of interesterified and noninteresterified butterfat-canola oil blends do not seem to be strongly related to either solid fat content (SFC) or crystal polymorphic behavior, but rather to the microstructure of the fat crystal network. The microstructure of the fats was quantified by using fractal geometric relationships between the elastic moduli (G′) of the fats and their SFC values using the approach of Shih, W.H., W.Y. Shih, S.I. Kim, J. Liu, and I.A. Aksay [Phys. Rev. A 42:4772–4779 (1990))] for weak-link regimes. Chemical interesterification decreased the fractal dimension of the fat crystal network from 2.46 to 2.15. We propose that fat microstructure, as quantified by a fractal dimensionality, could be modified to attain specific rheological properties.

Eicosapentaenoic acid (20∶5n-3) from the marine microalgaPhaeodactylum tricornutum

Abstract: Eicosapentaenoic acid (EPA, 20∶5n-3) was obtained from the marine microalgaePhaeodactylum tricornutum by a three-step process: fatty acid extraction by direct saponification of biomass, polyunsaturated fatty acid (PUFA) concentration by formation of urea inclusion compounds, and EPA isolation by semipreparative high-performance liquid chromatography (HPLC). Alternatively, EPA was obtained by a similar two-step process without the PUFA concentration step by the urea method. Direct saponification of biomass was carried out with two solvents that contained KOH for lipid saponification. An increase in yield was obtained because the problems associated with emulsion formation were avoided by separating the biomass from the soap solution before adding hexane for extraction of insaponifiables. The most efficient solvent, ethanol (96%) at 60°C for 1 h, extracted 98.3% of EPA. PUFA were concentrated by the urea method with a urea/fatty acid ratio of 4∶1 at a crystallization temperature of 28°C and by using methanol and ethanol as urea solvents. An EPA concentration ratio of 1.73 (55.2∶31.9) and a recover yield of 78.6% were obtained with methanol as the urea solvent. This PUFA concentrate was used to obtain 93.4% pure EPA by semipreparative HPLC with a reverse-phase, C18, 10 mm i.d.×25-cm column and methanol/water (1% acetic acid), 80∶20 w/w, as the mobile phase. Eighty-five percent of EPA loaded was recovered, and 65.7% of EPA present inP. tricornutum biomass was recovered in highly pure form by this three-step downstream process. Alternatively, 93.6% pure EPA was isolated from the fatty acid extract (without the PUFA concentration step) with 100% EPA recovery yield. This two-step process increases the overall EPA yield to 98.3%, but it is only possible to obtain 20% as much EPA as that obtained by three-step downstream processing.

Methanolysis of seed oils in flowing supercritical carbon dioxide

Abstract: The direct methanolysis of triglycerides in flowing supercritical carbon dioxide by an immobilized lipase is described. The reaction system consists of two syringe pumps for substrate addition and another two syringe pumps for delivering CO2 at 24.1 MPa. Corn oil is pumped into the carbon dioxide stream at a rate of 4 μL/min, and methanol is pumped at 5 μL/min to yield fatty acid methyl esters (FAME) at >98% conversion. Direct methanolysis of soy flakes gives FAME at similar yields. This combined extraction/reaction is performed at 17.2 MPa and 50°C. The fatty acid profiles obtained for these seed oils matches those obtained by classical chemical synthesis.

Chemoenzymatic epoxidation of unsaturated fatty acid esters and plant oils

Abstract: In the presence of an immobilized lipase fromCandida antacrtica (Novozym 435R) fatty acids are converted to peroxy acids by the reaction with hydrogen peroxide. In a similar reaction, fatty acid esters are perhydrolyzed to peroxy acids. Unsaturated fatty acid esters subsequently epoxidize themselves, and in this way epoxidized plant oils can be prepared with good yields (rapeseed oil 91%, sunflower oil 88%, linseed oil 80%). The hydrolysis of the plant oil to mono- and diglycerides can be suppressed by the addition of a small amount of free fatty acids. Rapeseed oil methyl ester can also be epoxidized; the conversion of C=C-bonds is 95%, and the composition of the epoxy fatty acid methyl esters corresponds to the composition of the unsaturated methyl esters in the substrate.

Characterization of enzymatically prepared biosurfactants

Abstract: Various fatty monoesters of sugars and sugar alcohols were prepared enzymatically in organic solvent. Water produced during esterification was removed by refluxing through a dessicant under reduced pressure. Surface properties of these esters such as surface and interfacial tensions and their ability to stabilize emulsions at 30°C were evaluated: oleate esters of glucose, fructose, and sorbitol show similar behavior in reduction of surface and interfacial tensions, and values for the critical micelle concentration are about 8·10−5 M. It was also observed with sorbitol esters that the shorter the alkyl chain, the higher the critical micelle concentration. Generally, emulsions prepared with the emulsifier dissolved in the water or in the oil phase lead to oil-in-water or water-in-oil emulsions, respectively. Sorbitol monolaurate significantly increased the stability of oil-in-water emulsions, with only 5% separation of the phases after 48h at 30°C, compared to 10% for chemically prepared sorbitan monolaurate under the same conditions. Sorbitol monoerucate was very efficient in stabilizing water-in-oil emulsions, with only 1% separation of the phases.

Stabilization of seal blubber and menhaden oils with green tea catechins

Abstract: Catechins, namely (−)epicatechin (EC), (−)epigallocatechin (EGC), (−)epicatechin gallate (ECG) and (−)epigallocatechin gallate (EGCG), were isolated from commercial Chinese green leaves. The antioxidant activity of isolated catechins was compared with those of α-tocopherol, butylated hydroxyanisole (BHA), butylated hydroxytolene (BHT) andtert-butylhydroquinone (TBHQ), all at 200 ppm, in refined, bleached and deodorized seal blubber oil and menhaden oil. The study was carried out under Schaal oven test conditions at 65°C over a 144-h period, except for weight gain measurements, which were continued for up to 200 h. Progression of oxidation was monitored by measuring changes in weight gain and values of peroxide, conjugated diene, and 2-thiobarbituric acid-reactive substances. Oils treated with tea catechins showed excellent oxidative stability as compared with samples that contained commonly used antioxidants, such as α-tocopherol, BHA, BHT, and TBHQ. The potency of catechins in prevention of oxidation of marine oils was in the decreasing order of ECG> EGCG> EGC> EC; ECG was slightly more effective than TBHQ in systems studied.