Preparation of meadowfoam dimer acids and dimer esters,and their use as lubricants

Meadowfoam dimer acids have been prepared in a thermal clay-catalyzed reaction. Reaction conditions have been optimized, and yields of 44% were obtained with 2% water and 6–8% of an acid-washed montmorillonite clay, based on the meadowfoam fatty acids. Purity of the distilled dimer acids was 79–89% with most of the remaining 11–22% being residual mono- and tribasic acids. Dimethyl, di-(2-ethylhexyl), and di-n-butyl meadowfoam dimer ester derivatives were also prepared. Color, viscosity, and wear-preventive characteristics of the meadowfoam dimer acids and dimer ester derivatives were compared to those of commercial dimer acids and dimer esters. The viscosity of the meadowfoam dimer acids is similar to that of Empol® 1010, which is also derived from a highly monounsaturated fatty acid source. Viscosities of the meadowfoam dimer esters were also comparable to those of commercial dimer esters. Wear prevention characteristics, as determined by the four-ball test method, of the meadowfoam dimer acids and dimer esters were similar to those of the commercial products. In one case, the di-n-butyl esters, the meadowfoam derivative showed a significantly smaller wear scar than that shown by the di-n-butyl derivative of Unidyme® 14.     

Estolides from meadowfoam oil fatty acids and other monounsaturated fatty acids

The formation of estolides was detected during the studies on dimerization of meadowfoam oil fatty acids. By adjusting the reaction conditions, it was possible to produce monoestolides with little dimer or trimer formations. Estolides have potential use in lubricant, cosmetic and ink formulations and in plasticizers. This paper reports the conditions for production of estolides from mixed meadow-foam fatty acids, commercial oleic acid, high-oleic sun-flower oil fatty acids,cis-5,cis-13-docosadienoic acid, petroselinic acid and linoleic acid.     

Biodegradation of estolides from monounsaturated fatty acids

Mono- and polyestolides, made from oleic acid, meadowfoam oil fatty acids and erucic acid, were subjected to biodegradation with mixed cultures of Penicillium verucosum, Mucor racemosus, and Enterobacter aerogenes. Fermentations were continued for 3, 5, 10, 15, 20, or 30 d. Meadowfoam oil and its fatty acids, oleic acid and soybean oil were also biodegraded under the same conditions. After 10 d, oleic acid and soybean oil were degraded 99.8 and 99.2%, respectively; meadowfoam oil and its fatty acids were degraded 89.0 and 97.7%, respectively. After 30 d, oleic acid-derived poly- and monoestolides were degraded 98.6 and 90.0%, respectively, meadowfoam estolides were degraded 75.7%, and erucic acid estolides were degraded 84.0%.     

Selectivity of lipases: isolation of fatty acids from castor,coriander, and meadowfoam oils

The lipase‐catalyzed hydrolysis of castor, coriander, and meadowfoam oils was studied in a two‐phase water/oil system. The lipases from Candida rugosa and Pseudomonas cepacia released all fatty acids from the triglycerides randomly, with the exception of castor oil. In the latter case, the P. cepacia lipase discriminated against ricinoleic acid. The lipase from Geotrichum candidum discriminated against unsaturated acids having the double bond located at the Δ‐6 (petroselinic acid in coriander oil) and Δ‐5 (meadowfoam oil) position or with a hydroxy substituent (ricinoleic acid). The expression of the selectivities of the G. candidum lipase was most pronounced in lipase‐catalyzed esterification reactions, which was exploited as part of a two‐step process to prepare highly concentrated fractions of the acids. In the first step the oils were hydrolyzed to their respective free fatty acids, in the second step a selective lipase was used to catalyze esterification of the acids with 1‐butanol. This resulted in an enrichment of the targeted acids to approximately 95—98% in the unesterified acid fractions compared to the 70—90% content in the starting acid fractions.     

Synthesis of Chloroalkoxy eicosanoic and docosanoic acids from meadowfoam fatty acids by oxidation with aqueous sodium hypochlorite

Chloroalkoxy substituted C₂₀ and C₂₂ fatty acids can be synthesized from the unsaturated fatty acids in meadow-foam oil by reaction of the fatty acids with primary or secondary alcohols and an aqueous sodium hypochlorite solution (commercial bleach). The reactions are conducted at room temperature for 3 h. Chlorohydroxy fatty acid derivatives are formed as by-products owing to the presence of water in the reaction mixture. Chlorinated δ-lactones are also produced by direct reaction of sodium hypochlorite with the Δ5 unsaturated fatty acids present in meadowfoam or by ring closure of the 6-chloro-5-hydroxy fatty acids. The product yield of chloroalkoxy fatty acids is dependent on the nature and volume of the alcohol used in the reaction, as well as the concentration and pH of the sodium hypochlorite solution. Primary alcohols such as methanol and butanol produce maximal yields (50–60%) of chloroalkoxy fatty acids whereas the secondary alcohol 2-propanol gives a 30% yield. Chloroalkoxy fatty acid yields can be increased to 75–80% by elimination of water from the reaction mixture through a procedure that partitions sodium hypochlorite from water into hexane/ethyl acetate mixtures. All of the reaction products were fully characterized using nuclear magnetic resonance and gas chromatography-mass spectrometry.     

Purification of docosahexaenoic acid by selective esterification of fatty acids from tuna oil with Rhizopus delemar lipase

To purify docosahexaenoic acid (DHA), we attempted the selective esterification of fatty acids originating from tuna oil with lipases. Tuna oil was hydrolyzed in NaOH-ethanol solution, and the resulting fatty acid mixture [DHA, 23.2%; named tuna-free fatty acid (FFA)] was used as a starting material. Rhizopus delemar which acted lightly on DHA, was a suitable catalyst for the selective esterification of tuna-FFA, and lauryl alcohol was the best substrate. The reaction proceeded most effectively when a mixture of 2.4 g lauryl alcohol/tuna-FFA (2:1, mol/mol), 0.6 g water, and 600 U Rhizopus lipase was incubated at 30°C for 20 h with stirring at 500 rpm. Under these conditions 72% of tuna-FFA was esterified, and 84% of DHA was recovered in the unesterified fatty acid fraction. The DHA content in the fatty acid fraction rose from 23 to 73% with this reaction. To further elevate the DHA content, the unesterified fatty acids were extracted, and then esterified again under the same conditions. By this repeated esterification, DHA was purified to 89% with a recovery of 71% of its initial content.     

The rate of ring opening of γ-and δ-lactones derived from meadowfoam fatty acids

δ-Lactones derived from meadowfoam (Limnanthes) fatty acids were reacted with amine and alcohol nucleophiles in a second-order reaction to provide the acyclic 5-hydroxy eicosanoic acid esters and amides. The rate of reaction for the ring opening of δ-lactones was compared to the rate of ring opening of γ-lactones and the rate of derivatization of meadowfoam fatty acids. δ-Lactones showed a much larger rate for the formation of derivatives than the corresponding γ-lactones or fatty acids. γ-Lactone had a rate constant >7700 times larger for the formation of butyl ester than meadowfoam fatty acids. The formation of amides from δ-lactones is even faster than the esterification reaction and requires no catalyst or solvent when conducted at the melting point of the lactone.     

Deodorization of vegetable oils: Prediction of trans polyunsaturated fatty acid content

Kinetics of the formation of trans linoleic acid and trans linolenic acid were compared. Pilot plant-scale tests on canola oils were carried out to validate the laboratory-scale kinetic model of geometrical isomerization of polyunsaturated fatty acids described in our earlier publication. The reliability of the model was confirmed by statistical calculations. Formation of the individual trans linoleic and linolenic acids was studied, as well as the effect of the degree of isomerization on the distribution of the trans fatty acid isomers. Oil samples were deodorized at temperatures from 204 to 230°C from 2 to 86 h. Results showed an increase in the relative percentage of isomerized linolenic and linoleic acid with an increase in either the deodorization time or the temperature. The percentage of trans linoleic acid (compared to the total) after deodorization ranged from <1 to nearly 6%, whereas the percentage of trans linolenic acid ranged from <1 to >65%. Applying this model, the researchers determined the conditions required to produce a specially isomerized oil for a nutritional study. The practical applications of these trials are as follows: (i) the trans fatty acid level of refined oils can be predicted for given deodorization conditions, (ii) the conditions to meet increasingly strict consumer demands concerning the trans isomer content can be calculated, and (iii) the deodorizer design can be characterized by the deviation from the theoretical trans fatty acid content of the deodorized oil.     

The isolation and recovery of fatty acids with Δ5 unsaturation from meadowfoam oil by lipase-catalyzed hydrolysis and esterification

This report examines the use of lipases for isolating fatty acids with Δ5 unsaturation from the seed oil ofLimnanthes alba, or meadowfoam. Seven lipase types and three enzyme configurations (immobilized, “free” and reversemicellar encapsulated) were examined. All lipases discriminated against Δ5 acids to varying degrees, but the degree of discrimination was independent of enzyme configuration. Lipase-catalyzed esterification of meadowfoam oil’s free fatty acids was much more successful for isolating Δ5 acyl groups than was lipolysis. For example, esterification directed byChromobacterium viscosum lipase yielded a free fatty acid product containing >95% of the Δ5 acyl groups at >99% purity.     

Esterification of glycerol with conjugated linoleic acid and long-chain fatty acids from fish oil

Free fatty acids from fish oil were prepared by saponification of menhaden oil. The resulting mixture of fatty acids contained ca. 15% eicosapentaenoic acid (EPA) and 10% docosahexaenoic acid (DHA), together with other saturated and monounsaturated fatty acids. Four commercial lipases (PS from Pseudomonas cepacia, G from Penicillium camemberti, L2 from Candida antarctica fraction B, and L9 from Mucor miehei) were tested for their ability to catalyze the esterification of glycerol with a mixture of free fatty acids derived from saponified menhaden oil, to which 20% (w/w) conjugated linoleic acid had been added. The mixtures were incubated at 40°C for 48h. The ultimate extent of the esterification reaction (60%) was similar for three of the four lipases studied. Lipase PS produced triacylglycerols at the fastest rate. Lipase G differed from the other three lipases in terms of effecting a much slower reaction rate. In addition, the rate of incorporation of omega-3 fatty acids when mediated by lipase G was slower than the rates of incorporation of other fatty acids present in the reaction mixture. With respect to fatty acid specificities, lipases PS and L9 showed appreciable discrimination against esterification of EPA and DHA, respectively, while lipase L2 exhibited similar activity for all fatty acids present in the reaction mixture. The positional distribution of the various fatty acids between the sn-1,3 and sn-2 positions on the glycerol backbone was also determined.     

Conjugated linoleic acid production from linoleic acid by lactic acid bacteria

After screening 14 genera of lactic acid bacteria, Lactobacillus plantarum AKU 1009a was selected as a potential strain for CLA production from linoleic acid. Washed cells of L. plantarum with high levels of CLA production were obtained by cultivation in a nutrient medium with 0.06% (wt/vol) linoleic acid (cis-9,cis-12-octadecadienoic acid). Under the optimal reaction conditions with the free form of linoleic acid as the substrate, washed cells of L. plantarum produced 40 mg CLA/mL reaction mixture (33% molar yield) from 12% (wt/vol) linoleic acid in 108 h. The resulting CLA was a mixture of two CLA isomers, cis-9,trans-11 (or trans-9,cis-11)-octadecadienoic acid (CLA1, 38% of total CLA) and trans-9,trans-11-octadecadienoic acid (CLA2, 62% of total CLA), and accounted for 50% of the total FA obtained. A higher yield (80% molar yield to linoleic acid) was attained with 2.6% (wt/vol) linoleic acid as the substrate in 96 h, resulting in CLA production of 20 mg/mL reaction mixture [consisting of CLA1 (2%) and CLA2 (98%)] and accounting for 80% of total FA obtained. Most of the CLA produced was associated with the cells (ca. 380 mg CLA/g dry cells), mainly as FFA.     

Large-scale purification of γ-linolenic acid by selective esterification using Rhizopus delemar lipase

γ-Linolenic acid (GLA) is a physiologically valuable fatty acid, and is desired as a medicine, but a useful method available for industrial purification has not been established. Thus, large-scale purification was attempted by a combination of enzymatic reactions and distillation. An oil containing 45% GLA (GLA45 oil) produced by selective hydrolysis of borage oil was used as a starting material. GLA45 oil was hydrolyzed at 35°C in a mixture containing 33% water and 250 U/g-reaction mixture of Pseudomonas sp. lipase; 91.5% hydrolysis was attained after 24 h. Film distillation of the dehydrated reaction mixture separated free fatty acids (FFA; acid value 199) with a recovery of 94.5%. The FFA were selectively esterified at 30°C for 16 h with two molar equivalents of lauryl alcohol and 50 U/g of Rhizopus delemar lipase in a mixture containing 20% water. The esterification extent was 52%, and the GLA content in the FFA fraction was raised to 89.5%. FFA and lauryl esters were not separated by film distillation, but the FFA-rich fraction contaminated with 18% lauryl esters was recovered by simple distillation. To further increase the GLA content, the FFA-rich fraction was selectively esterified again under similar conditions. As a result, the GLA content in the FFA fraction was raised to 97.3% at 15.2% esterification. After simple distillation of the reaction mixture, lauryl esters contaminating the FFA-rich fraction were completely eliminated by urea adduct fractionation. When 10 kg of GLA45 oil was used as a starting material, 2.07 kg of FFA with 98.6% GLA was obtained with a recovery of 49.4% of the initial content.     

Trans fatty acids in Canadian margarines: Recent trends

The fatty acid composition and the trans fatty acid content of the top-selling 109 Canadian margarines were determined by a combined capillary gas-liquid chromatography/infrared spectroscopy method. The 109 brands accounted for 68% of the margarine brands sold in Canada and represented 74% of the market share. The mean level of total trans content in tub margarines (n=79) was 18.8% (g/100 g fatty acids) and ranged from 0.9 to 46.4%. The most frequent occurrence of trans in tub margarines was in the 15–20% range; 48 of the 79 tub brands were in this range but seven brands contained more than 40% trans. The trans content of hard margarines (n=30) ranged from 16.3 to 43.7% and the mean value was 34.3%. In 20 of the 109 brands, the levels of trans,trans isomers of linoleic acid exceeded the maximum level of 1% recommended for Canadian margarines. The levels of cis,trans/trans,cis isomers of linoleic acid were also high; 78 brands contained more than 1% and in 16 brands, the levels were in the 6–7% range. Linoleic acid content in the 109 brands ranged from 1.0 to 45.2% and averaged 18.3%. In 33 samples, linoleic acid was below the level of 5% recommended by an ad hoc committee of Health Canada. Moreover, in these, the total trans content exceeded 30%, and trans polyunsaturated fatty acid level was greater than 5%. There were eight margarines prepared from nonhydrogenated fat and their total trans content was below 2.5%. From the trans content and market share of each of the margarine brands, the average intake of trans fatty acids from margarine was estimated as 0.96 g/person/d. The intake of trans fatty acids in Canada from various sources was previously estimated by us as 8.4 g/person/d. Thus it is suggested that only 11% of the dietary trans fatty acids are supplied by margarines and the majority of trans fatty acids in the Canadian diet is derived from hidden fats in fast foods and bakery products.     

Homolytic decomposition of linoleic acid hydroperoxide: Identification of fatty acid products

An isomeric mixture of linoleic acid hydroperoxides, 13-hydroperoxy-cis-9,trans-11-octadecadienoic acid (79%) and 9-hydroperoxy-cis-12,trans-10-octadecadienoic acid (21%), was decomposed homolytically by Fe(II) in an ethanol-water solution. In one series of experiments, the hydroperoxides were decomposed by catalytic concentrations of Fe(II). The 10⁻⁵ M Fe(III) used to initiate the decomposition was kept reduced as Fe(II) by a high concentration of cysteine added to the reaction in molar excess of the hydroperoxides. Nine different monomeric (no detectable dimeric) fatty acids were identified from the reaction. Analyses of these fatty acids revealed that they were mixtures of positional isomers identified as follows: (I) 13-oxo-trans,trans-(andcis,trans-) 9,11-octadecadienoic and 9-oxo-trans,trans- (andcis,trans-) 10,12-octadecadienoic acids; (II) 13-oxo-trans-9,10-epoxy-trans-11-octadecenoic and 9-oxo-trans-12, 13-epoxy-trans-10-octadecenoic acids; (III) 13-oxo-cis-9,10-epoxy-trans-11-octadecenoic and 9-oxo-cis-12, 13-epoxy-trans-10-octadecenoic acids; (IV) 13-hydroxy-9,11-octadecadienoic and 9-hydroxy-10,12-octadecadienoic acids; (V) 11-hydroxy-trans-12, 13-epoxy-cis-9-octadecenoic and 11-hydroxy-trans-9, 10-epoxy-cis-12-octadecenoic acids; (VI) 11-hydroxy-trans-12, 13-epoxy-trans-9-octadecenoic and 11-hydroxy-trans-9,10-epoxy-trans-12-octadecenoic acids; (VII) 13-oxo-9-hydroxy-trans-10-octadecenoic acids; (VIII) isomeric mixtures of 9, 12, 13-dihydroxyethoxy-trans-10-octadecenoic and 9, 10, 13-dihydroxyethoxy-trans-11-octadecenoic acids; and (IX) 9, 12, 13-trihydroxy-trans-10-octadecenoic and 9, 10, 13-trihydroxy-trans-11-octadecenoic acids. In another experiment, equimolar amounts of Fe(II) and hydroperoxide were reacted in the absence of cysteine. A large proportion of dimeric fatty acids and a smaller amount of monomeric fatty acids resulted. The monomeric fatty acids were examined by gas liquid chromatography-mass spectroscopy. Spectra indicated that the monomers were largely similar to those produced by the Fe(III)-cysteine reaction. Presented in part at the American Chemical Society Meeting, Los Angeles, March 1974. ARS, USDA.     

Metabolism of meadowfoam oil fatty acids in mice

Meadowfoam oil is unusual because over 95% of the fatty acids are 20- and 22-carbon aliphatic acids withcis double bonds located principally at the 5- and/or 13-position. Since little information is available on the metabolism of the 5c−20∶1 and 5c,13c−22∶2 fatty acids, an exploratory study in mice was conducted to investigate the metabolism of purified samples of the free fatty acids isolated from meadowfoam oil, and to determine the effect of meadowfoam oil on weight gain and tissue lipid composition. Mice fed diets containing 5% by wt of the purified 5c−20∶1 or 5c,13c−22∶2 for 6 days exhibited no apparent physiological problems. Total liver lipids from mice fed the purified fatty acid diets contained mean values of 2.0% 5c−20∶1 and 2.1% 5c,13c−22∶2; total heart lipids contained 1.7% 5c−20∶1 and 10.7% 5c,13c−22∶2. Liver total phospholipids from mice fed a 5% meadowfoam oil diet for 19 wk contained 1.4% 5c−20∶1 and 1.9% 5c,13c−22∶2. There was no evidence of desaturation, elongation or retroconversion. Weight gain for mice fed the meadowfoam oil diet for 19 wk was similar to mice fed corn oil, and was higher than for mice fed hydrogenated cottonseed oil. Considering the high 5c−20∶1 and 5c,13c−22∶2 content of the diets, the percentages of these fatty acids in mouse tissue lipids from both the short- and long-term studies were low. Weight gain was surprisingly good since the meadowfoam oil diet was essential fatty acid-deficient. Results of this initial investigation suggest that the 5c−20∶1 and 5c,13c−22∶2 fatty acids were utilized primarily for energy. In the short-term study, these fatty acids did not produce toxic effects or cause metabolic problems. The mention of firm names or trade products does not imply that they are endorsed or recommended by the U.S. Department of Agriculture over other firms or similar products not mentioned.     

Monitoring of Fat Content,Free Fatty Acid and Fatty Acid Profile Including <Emphasis Type="Italic">trans</Emphasis> Fat in Pakistani Biscuits

The fat contents of 12 brands of biscuits were extracted and evaluated for free fatty acids (FFA) and their fatty acid composition (FAC). The oil content and FFA varied from 13.7 to 27.6% and 0.2 to 1.0%, respectively. The FAC was analyzed by gas chromatography–mass spectroscopy with particular emphasis on trans fatty acids (TFA). Total saturated, unsaturated, cis-monounsaturated and polyunsaturated fatty acids were determined in the range of 37.9–46.9, 53.0–62.0, 12.3–43.7 and 0.1–9.2%, respectively. The high amount of TFA was observed in all biscuit samples and varied from 9.3 to 34.9%. The quantity and quality of the lipid fraction of the biscuits indicated that the all analyzed biscuits are a rich source of fat, saturated fatty acids and trans fatty acids, consequently not suitable for the health of consumers. The high content of trans fatty acids and palmitic acid also indicated that blends of RBD palm oil and partially hydrogenated oil had been used in the biscuit manufacturing.     

Lipase-catalyzed fractionation of conjugated linoleic acid isomers

The abilities of lipases produced by the fungus Geotrichum candidum to selectively fractionate mixtures of conjugated linoleic acid (CLA) isomers during esterification of mixed CLA free fatty acids and during hydrolysis of mixed CLA methyl esters were examined. The enzymes were highly selective for cis-9,trans-11–18∶2. A commercial CLA methyl ester preparation, containing at least 12 species representing four positional CLA isomers, was incubated in aqueous solution with either a commercial G. candidum lipase preparation (Amano GC-4) or lipase produced from a cloned high-selectivity G. candidum lipase B gene. In both instances selective hydrolysis of the cis-9,trans-11–18∶2 methyl ester occurred, with negligible hydrolysis of other CLA isomers. The content of cis-9,trans-11–18∶2 in the resulting free fatty acid fraction was between 94 (lipase B reaction) and 77% (GC-4 reaction). The commercial CLA mixture contained only trace amounts of trans-9,cis-11–18∶2, and there was no evidence that this isomer was hydrolyzed by the enzyme. Analogous results were obtained with these enzymes in the esterification in organic solvent of a commercial preparation of CLA free fatty acids containing at least 12 CLA isomers. In this case, G. candidum lipase B generated a methyl ester fraction that contained >98% cis-9,trans-11–18∶2. Geotrichum candidum lipases B and GC-4 also demonstrated high selectivity in the esterification of CLA with ethanol, generating ethyl ester fractions containing 96 and 80%, respectively, of the cis-9,trans-11 isomer. In a second set of experiments, CLA synthesized from pure linoleic acid, composed essentially of two isomers, cis-9,trans-11 and trans-10,cis-12, was utilized. This was subjected to esterification with octanol in an aqueous reaction system using Amano GC-4 lipase as catalyst. The resulting ester fraction contained up to 97% of the cis-9,trans-11 isomer. After adjustment of the reaction conditions, a concentration of 85% trans-10,cis-12–18∶2 could be obtained in the unreacted free fatty acid fraction. These lipase-catalyzed reactions provide a means for the preparative-scale production of high-purity cis-9,trans-11–18∶2, and a corresponding CLA fraction depleted of this isomer.     

Fatty acid composition of French infant formulas with emphasis on the content and detailed profile oftrans fatty acids

The aim of the present study was to identify and quantitatetrans isomers of C18 fatty acids in some French infant formulas. Twenty powdered infant formulas were purchased in pharmacies and supermarkets in order to assess theirtrans mono- and poly-unsaturated fatty acids content. The fatty acid profiles were examined using methyl and isopropyl ester derivatives. The combination of gas-liquid chromatography, high-performance liquid chromatography, and silver nitrate thin-layer chromatography was needed to describe the detailed fatty acid compositions of the samples, includingtrans isomers of unsaturated C18 fatty acids. All the samples containedtrans isomers of C18∶1 acid (mean level 1.97±0.28% of total fatty acids), with vaccenic acid being generally the major isomer (15 out of 20 samples), thus indicating the origin from bovine milk. All the formulas also contained various isomers of linoleic and α-linolenic acids, but at lower levels.Trans PUFA isomers are the same as those present in deodorized oils. In conclusion, all the infant formulas analyzed in this study contained sometrans fatty acids, including isomers of essential fatty acids. This should be taken into account in the dietary intake of the newborn.     

Low-<Emphasis Type="Italic">trans</Emphasis> Shortening and Spread Fats Produced by Electrochemical Hydrogenation

Partially hydrogenated soybean oils (90–110 IV) were prepared by electrochemical hydrogenation at a palladium/cobalt or palladium/iron cathode, moderate temperature (70–90 °C) and atmospheric pressure. The trans fatty acid (TFA) contents of 90–110 IV products ranged from 6.4 to13.8% and the amounts of stearic acid ranged from 8.8 to 15.4% (the higher stearic acid contents indicated that some reaction selectivity had been lost). The solid fat values and melting point data indicated that electrochemical hydrogenation provides a route to low-trans spreads and baking shortenings. Shortenings produced by conventional hydrogenation contain 12–25% trans fatty acids and up to 37% saturates, whereas shortening fats produced electrochemically had reduced TFA and saturate content. Electrochemical hydrogenation is also a promising route to low-trans spread and liquid margarine oils. Compared to commercial margarine/spread oils containing 8–12% TFA, the use of electrochemical hydrogenation results in about 4% TFA. Names are necessary to report factually an available data: the USDA neither guarantees nor warrants the standard of the product, and the use of the name USDA implies no approval of the product to the exclusion of others that may also be suitable.     

Influence of moderate amounts of trans fatty acids on the formation of polyunsaturated fatty acids

The effect of trans fatty acids from partially hydrogenated soybean oil and butterfat on the formation of polyunsaturated fatty acids was investigated. Five groups of rats were fed diets that contained 20 wt% fat. The content of linoleic acid was adjusted to 10 wt% of the dietary fats in all diets, whereas the amount of trans fatty acids from partially hydrogenated soybean oil (PHSBO) was varied from 4.5 to 15 wt% in three of the five diets. The fourth group received trans fatty acids from butterfat (BF), while the control group was fed palm oil without trans fatty acids. Trans fatty acids in the diet were portionally reflected in rat liver and heart phosphatidylethanolamine (PE), phosphatidylcholine (PC), phosphatidylinositol, and phosphatidylserine. Incorporation in the sn-1 position was compensated by a decrease in saturated fatty acids. Trans fatty acids were not detected in diphosphatidylglycerol. Compared to the presence in the dietary fats, 8t- and 10t-18:1 were discriminated against in the incorporation in PE and PC from liver and heart, whereas 9t- and 12t-18:1 were preferred. The formation of 20:4n-6 was not influenced by 4.5 wt% trans fatty acids (from PHSBO) but apparently was by 10 wt% in liver. In contrast, even a content of 2.5 wt% trans fatty acids from BF reduced the formation of 20:4n-6. The inhibitory effect of trans isomers on linoleic acid conversion was reflected less in heart than in liver and less for PE than for PC. Groups with trans fatty acids showed increased 22:6n-3 and 22:5n-3 deposition in liver and heart PE and PC.