Sterol composition of 19 vegetable oils

The unsaponifiables from 19 vegetable oils were divided into a sterol and three other fractions by thin-layer chromatography. All except olive and palm kernel oils gave the sterol fraction in a large quantity. Compositions of the sterol fractions were determined by gas liquid chromatography. Identification of each sterol was carried out by gas liquid chromatography and combined gas chromatograph-mass spectrometry. Campesterol, stigmasterol and β-sitosterol were present in all oils, and a minor amount of cholesterol in majority of the oils. Brassicasterol occurrence was widespread but its content was extremely small in oils other than rapeseed oil. Other sterols, presumably δ⁷-stigmastenol and δ⁵- and δ⁷-avenasterol were detected in most of the oils.     

Lipid composition of selected margarines

Results of analytical studies on the composition of 10 selected margarines representative of consumeravailable hard and soft types are presented. Paired hard and soft products from the same manufacturer were chosen where possible. All of the margarines were compared on the basis of total fatty acid composition, polyunsaturated to saturated fatty acid ratios, totaltrans and thetrans content of the monoene and diene fractions, location of the double bond in the monoene isomers, per cent conjugation, distribution of the fatty acids at the 2 position of the triglycerides, tocopherol content, and the ratios of α-tocopherol to polyunsaturated fatty acids. As expected the soft margarines contained more polyunsaturated fatty acids than their companion hard types, but all soft margarines did not contain more polyunsaturated fatty acids than all of the hard margarines. The one margarine containing safflower oil had the highest polyunsaturated to saturated ratio. Eight of the ten margarines contained more than 15%trans monoene and nine contained less than 5%trans diene. Positional isomers in the monoene fraction were Δ6 toΔ12 with thecis Δ9 isomer predominating. All of the margarines contained less than 1.9% conjugation. The percentage oftrans monoene at the 2 position was greater for some margarines than that in the total fatty acid. This was attributed to the preferential placement of polyunsaturated fatty acids at the 2 position in the original vegetable oils. The forms of tocopherol found were characteristic of the original vegetable oils. Ratios of α-tocopherol to PUFA varied from 0.1 to 0.5 mg/g. Determination of the relationship of the amount of tocopherol content to either source or hardness is not possible on the basis of our data.     

Effect of physical refining on selected minor components in vegetable oils

The final quality of vegetable oils is largely determined by the deodorization process. From an organoleptic point of view, oils should be light in color with a bland taste and a good cold and/or oxidative stability. Today, however, more and more attention is paid to the real nutritional quality. Oils should contain low trans fatty acid levels, low polymeric triglycerides, and secondary oxidation products and at the same time being rich in natural antioxidants. In order to comply to these new quality requirements, the deodorization technology has been modified substantially. Mathematical models were established describing the influence of different process parameters (time, temperature, steam, and pressure) on trans fatty acid formation, tocopherol stripping, and production of oxidized and polymeric triacylglycerides during physical refining of soybean oil. Trans fatty acid (TFA) formation was influenced only by time and temperature. No significant influence of pressure or sparging steam could be observed. Models expressing the relative degree of cis/trans-isomerization of linoleic (DI_18:2) and α-linolenic acid (DI_18:3) could be extrapolated to other oils and deodorizer designs. Tocopherol removal was mainly influenced by process temperature and sparging steam. Additionally, tocopherol retention seemed to be dependent on the deodorizer design (steam injection geometry and sparging steam distribution). During physical refining, oxidized and polymerized triacylglycerols were not significantly influenced by any of the investigated process parameters. Industrially, process conditions are adapted to minimize trans fatty acid formation and maximize tocopherol retention. These goals can be achieved in a so-called DUAL TEMP^copy; deodorizer.     

Predicting temperature-dependence viscosity of vegetable oils from fatty acid composition

The viscosities of 12 vegetable oils were experimentally determined as a function of temperature (5 to 95°C) by means of a temperature-controlled rheometer. Viscosities of the oil samples decreased exponentially with temperature. Of the three models [modified Williams-Landel-Ferry (WLF), power law and Arrhenius] that were used to describe the effects of temperature on viscosity, the modified WLF model gave the best fit. The amounts of monounsaturated FA or polyunsaturated fatty acids (PUFA) highly correlated (R ²>0.82) with the viscosities of the oil samples whereas and the amounts of saturated or unsaturated FA. An exponential equation was therefore used to relate the viscosity of these vegetable oil samples to the amounts of monounsaturated FA or PUFA. The models developed are valuable for designing or evaluating systems and equipment that are involved in the storage, handling, and processing of vegetable oils.     

Studies on the properties of polyesters and polyester blends of selected vegetable oils

Melon‐seed and rubber‐seed oils have been used in the synthesis of polyester resins. Results reveal that rubber‐seed oil can completely be substituted for linseed and soyabean oils in the synthesis of both long and medium‐oil–length polyester resins. Melon‐seed oil was found to be a substitute for 50% of linseed oil and 50% of soyabean oil in the synthesis of long‐oil–length polyester resins. It also substituted for 15% of linseed oil and 50% of soyabean oil in the synthesis of medium‐oil–length polyester resins. © 2000 John Wiley & Sons, Inc. J Appl Polym Sci 75: 1441–1446, 2000     

Modification of vegetable oils

Journal of the American Oil Chemists' Society - From the analysis of several series of hydrogenated cottonseed, soybean, and linseed oils, made by the spectral and other methods, estimates have...     

Modification of vegetable oils

Summary 1. An investigation has been made of low-temperature crystallization from organic solvents as a means of effecting practical separations of the solid and liquid acids of unhydrogenated and hydrogenated cottonseed oils. 2. At any fixed temperature the most efficient separations were obtained in the highly polar solvents, acetone and methyl acetate. However, it was possible in any case to make nonpolar petroleum naphtha (Skellysolve B) fully equivalent to the polar solvents simply by conducting the crystallization at a temperature approximately 10° F. lower than that employed with the polar solvents. Ethyl acetate and methyl ethyl ketone were intermediate between petroleum naphtha and acetone or methyl acetate in their effectiveness. 3. By employing a solvent-fatty acid ratio of 4 to 1 by weight and conducting crystallizations at 5° F. or lower from acetone and −5° F. or lower from petroleum naphtha, the liquid fatty acids from unhydrogenated cottonseed oil could be reduced to below −2° C. in titer and to below about 3 per cent in saturated acid content. Under these conditions there was no appreciable crystallization of oleic acid. 4. At a solvent-fatty acid ratio of 6 to 1 and the same temperatures (5° F. for acetone and − 5° F. for petroleum naphtha) equally good separations could be made of the saturated fatty acids present in the mixed acids from hydrogenated cottonseed oil (I.V.=70). Separation of “iso-oleic” acids from the fatty acids of the hydrogenated oil took place over a wide range of temperatures, beginning at 35° F. in acetone and at 25° F. in petroleum naptha, and being incomplete (according to Twitchell analyses of the liquid acids) in either solvent at −15° F. However, the bulk of the higher melting iso-oleic acids was precipitated as the temperature approached −5° F. in acetone and −15° F. in petroleum naphtha. One of the laboratories of the Bureau of Agricultural and Industrial Chemistry, Agricultural Research Administration, U. S. Department of Agriculture.     

Modification of vegetable oils

Summary 1. Selective hydrogenation, followed by fractional crystallization from a solvent, has been used to prepare from cottonseed oil a hard butter, very similar to cocoa butter. 2. The new product differs somewhat in composition from cocoa butter, due to an unavoidable content of iso-oleic acid. 3. Examination of the new product by a micropenetration technique, by a standard solidification test, and by means of the dilatometer, reveals minor physical differences between it and cocoa butter. 4. The new fat has a slightly longer plastic range than cocoa butter. It supercools less strongly and contracts slightly less upon solidification. It exhibits the phenomenon of polymorphism to a less pronounced degree than cocoa butter. 5. A relatively low yield of the new fat is inherent in the process used for preparing it. In the case of the product most closely resembling cocoa butter, a yield of approximately 28 percent was obtained in the laboratory. The residual 72 percent is suitable for use as a hardening agent in shortening and similar products. Presented before the 34th Annual Meeting of the American Oil Chemists’ Society, New Orleans, Louisiana, May 12–14, 1943.     

Raman spectroscopic analysis of thecis/trans isomer composition of edible vegetable oils

A new method is presented for determining thecis/trans isomer content of edible vegetable oils. The intensities of Raman lines near 1656 and 1670 cm⁻¹ are associated with thecis andtrans configuration, respectively. A precision of ca. 1% can be obtained in thecis/trans isomer analysis of binary mixtures of methyl esters and triglycerides of monoenes and dienes and of hydrogenated vegetable oils. The spectroscopic data also provide the iodine value of vegetable oils or isolated fractions with precision for a single determination of ca. 1%. Presented at the AOCS meeting, Houston, May 1971. W. Market. Nutr. Res. Div., ARS, USDA.     

Comparative studies on composition of cardiac phospholipids in rats fed different vegetable oils

Male Sprague-Dawley rats were fed diets for 1 or 16 weeks, containing 20% by weight vegetable oils differing widely in their oleic, linoleic and linolenic acid content. No significant changes were observed in the level of the cardiac lipid classes. The fatty acid composition of the 2 major phospholipids, phosphatidylcholine and phosphatidylethanolamine, showed a remarkable similarity between diets in the concentration of total saturated, C22 polyunsaturated and arachidonic acids. Monounsaturated acids were incorporated depending on their dietary concentration, but the increases were moderate. Dietary linolenic acid rapidly substituted C22 polyunsaturated fatty acids of the linoleic acid family (n−6) with those from the linolenic acid family (n−3). The results suggest that dietary linolenic acid of less than 15% does not inhibit the conversion of linoleic to arachidonic acid but the subsequent conversion of arachidonic acid to the C22 polyunsaturates was greatly reduced. Significant amounts of dietary monounsaturated fatty acids were incorporated into cardiac cardiolipin accompanied by increases in polyunsaturated fatty acids, apparently to maintain an average of 2 double bonds/molecule. The cardiac sphingomyelins also accumulated monounsaturated fatty acids depending on the dietary concentration. It is quite evident from the results of this study that the incorporation of oleic acid and the substitution of linolenic for linoleic acid-derived C22 polyunsaturated fatty acids into cardiac phospholipids was related to the dietary concentration of these fatty acids and was not peculiar to any specific oil. Even though it is impossible to estimate the effect of such changes in cardiac phospholipids on membrane structure and function, results are discussed which suggest that the resultant membrane in the Sprague-Dawley male rat is more fragile, leading to greater cellular breakdown and focal necrosis. Contribution No. 914 from the Animal Research Institute.     

Antioxidants for vegetable oils

Several chemical compounds having antioxidant efficacy in food fats and oils and cleared for food use by governmental regulatory agencies are available for such use by vegetable oil processors in many nations of the world. These antioxidants are reviewed with particular attention to major benefits and possible shortcomings they may afford when added to vegetable oils. Some guidelines in selecting antioxidants to achieve optimum results are offered. Also, precautions to be observed in adding antioxidants to fats and oils are discussed.     

The stability of vegetable oils

Summary Eighty-four samples of soybean oils, representing various types of processing and different refining procedures, have been examined spectrophotometrically and the spectral-transmissive curves for 35 of them are reproduced in this communication. The spectral-transmissive properties of these oils have been discussed with particular reference to the effect which variations in processing have on these properties. In the light of the results obtained in these studies it is apparent that: (1) The spectral-transmissive properties of soybean oils are influenced by the method used in removing the oil from the bean as well as by subsequent processing procedures; (2) the Lovibond color readings give at best only approximate information concerning the spectral color of an oil; and (3) the carotenoids are removed during refining operations, the greatest loss usually occurring during the deodorizing treatment. Chlorophyll, which is present in various concentrations in the crude oil, is completely absent from the finished oil so far as spectrophotometric evidence is concerned. A cooperative organization participated in by the Bureaus of Agricultural Chemistry and Engineering and Plant Industry of the U. S. Department of Agriculture and the Agricultural Experiment Stations of the North Central States of Illinois, Indiana. Iowa, Kansas, Michigan, Minnesota, Missouri, Nebraska, North Dakota, Ohio, South Dakota, and Wisconsin.     

Friction properties of vegetable oils

Vegetable oils are a renewable and an environmentally friendly alternative to petroleum-based oils in lubrication and other important application areas. Vegetable oils fall into two broad chemical categories: triesters (or TG) and monoesters. Most vegetable oils are triesters of glycerol with FA, whose characteristics are dependent on the chemistry and composition of the FA residues. A small percentage of vegetable oils are monoesters of long-chain FA and fatty alcohols of varying chemistries. In this work, the free energy of adsorption (ΔG _ads) of safflower (SA), high-oleic safflower (HOSA), and jojoba (JO), methyl oleate (MO), and methyl palmitate (MP) on steel were investigated. SA and HOSA are TG of vegetable oils with FA residues of radically different degrees of unsaturation. JO is a monoester vegetable oil. ΔG _ads is one of the major factors affecting the boundary friction properties of lubricant ingredients. ΔG _ads was found to increase in the order: HOSA≤SA<JO<MO≤MP. The results are consistent with the degree of functionality and other chemical properties of the oils studied.     

Thermal modification of vegetable oils

This article reviews old and recent literature concerning the hypothesis that the Diels‐Alder reaction is the dominant reaction in the thermal polymerization of vegetable oil. Both triacylglycerol oils and methyl esters are used to show that this mechanism is unlikely to be a significant contributor en route to the reaction products. The products formed under a range of different reaction conditions are reviewed, including dimer acid, where Diels‐Alder chemistry is not claimed, to the polymerization of mono‐unsaturated methyl oleate in the presence of oxygen. In these, and even in the system where Diels‐Alder chemistry is claimed, the polymerization of conjugated methyl linoleate, six‐membered ring structures are not found in levels detectable by ¹³C NMR. Since such structures are formed by a Diels‐Alder reaction, it is unlikely that any more than 5% of the reaction could be formed by that method. Other factors against the Diels‐Alder contribution to this process, such as conformation and electron withdrawing ability of the substrates are also discussed.