A Single Bout of Exercise Increases the Expression of Glucose but not Fatty Acid Transporters in Skeletal Muscle of IL-6 KO Mice

IL-6 is a biologically active cytokine released during exercise by contracting skeletal muscles. It appears to be highly involved in the regulation of muscles energy substrate utilization. Whether an ablation of IL-6 (IL-6 KO) in mice subjected to a single bout of exercise affects lipid and/or glucose metabolism is currently unknown. In the present study we examined fatty acid (FAT/CD36, FABPpm, FATP-1, FATP-4) as well as glucose (GLUT-1, GLUT-4) transporters expression in IL-6 KO mice. In addition, intramuscular glycogen and lipid content was also evaluated. The expression of all fatty acid transporters (FAT/CD36: +25 %; FATP-1: +31 %; FABPpm: +12.7 %; FATP-4: +7.2 %) was increased in muscles from IL-6 KO mice compared to wild type (WT) mice. Accordingly intramuscular lipid content was also increased in these muscles (FFA: +38 %; DAG: +36 % and TAG: +160 %). Interestingly, IL-6 deficiency had only minor effect on glucose transporters expression (GLUT-1: ?4 %, and GLUT-4: ?5.1 %), with no apparent difference in muscular glycogen content. A single bout of exercise increased the glucose transporters (GLUT-1: +8 %; GLUT-4: +15 %) as well as FA transporters (FAT/CD36: +13 %; FABPpm: +4.5 %; FATP: +2.5 %, FATP-4: +10 %) expression but only in WT skeletal muscles. In muscles from IL-6 KO mice exercise induced changes only in glucose (GLUT-1: +20 %; GLUT-4: +35 %) but not in the content of FA transporters. Concomitantly, IL-6 KO mice displayed shorter time toward exhaustion with more pronounced reductions in intramuscular lipid and glycogen content. We may speculate, that IL-6 deficiency provokes more pronounced glucose utilization over lipid oxidation during a single bout of exhausting exercise.     

Site-specific differences in the fatty acid composition of human adipose tissue

The fatty acid composition of triacylglycerols from fifteen distinct adipose depots taken from each of seven adult male human subjects was compared. Oleic, palmitic, linoleic, stearic, myristic, palmitoleic and vaccenic acids accounted for more than 90% of the triacylglycerol fatty acids in all sites from all subjects; a number of other fatty acids were also identified and quantified. There were large differences in theaverage fatty acid composition between individual subjects. There were no site-specific differences in the proportions of myristic (3.8–4.7% of triacylglycerol fatty acids), palmitic (23–29%), linoleic (6.7–9.8%) or vaccenic (4.1–4.7%) acids or in the proportions of any of the less abundant fatty acids. There were some significant site-specific differences in the proportions of palmitoleic, oleic and stearic acids. The calf depot contained more palmitoleic acid (6.41±1.09%) than the trapezius (3.12±0.55%), perirenal (3.59±0.50%) and mesenteric (3.70±0.43%) depots, more oleic acid (42.13±1.27%) than the trapezius (36.03±2.18%), perirenal (36.50±1.56%) and breast (37.13±1.55%) depots and less stearic acid (5.18±0.89%) than the trapezius (8.57±0.97%), perirenal (8.49±0.75%), mesenteric (7.87±0.42%), breast (8.02±0.75%) and clavicular (8.34±0.78%) depots. The buttock depot contained less stearic acid (6.06±0.65%) than the perirenal, mesenteric and clavicular depots, while the anterior thigh depot contained less stearic acid (6.07±0.70%) than the perirenal depot. These findings indicate that, while most human adipose depots differ little in fatty acid composition, some sites, in particular the calf, perirenal, trapezius and mesenteric depots, have site-specific properties.     

Effects of stearic acid on plasma lipid and lipoproteins in humans

More than 40 years ago, saturated FA with 12, 14, and 16 carbon atoms (lauric acid, myristic acid, and palmitic acid) were demonstrated to be “hypercholesterolemic saturated FA.” It was further concluded that the serum total cholesterol level would hardly be changed by isocaloric replacement of stearic acid (18∶0) by oleic acid (cis-18∶1n−9) or carbohydrates. These earlier studies did not address the effects of the various FA on the serum lipoprotein profile. Later studies found that the hypercholesterolemic saturated FA increase serum total cholesterol levels by raising concentrations of both the atherogenic LDL and the antiatherogenic HDL. Consequently, the ratio of total to HDL cholesterol will hardly change when carbohydrates replace these saturated FA. Compared with other saturated FA, stearic acid lowers LDL cholesterol. Studies on the effects on HDL cholesterol are less conclusive. In some, the effects on HDL cholesterol were comparable to those of palmitic acid, oleic acid, and linoleic acid, whereas in others a decrease was observed. This may suggest that in this respect the source of stearic acid is of importance, which needs however further study. From all these studies, however, it can be concluded that stearic acid may decrease the ratio of total to HDL cholesterol slightly when compared with palmitic or myristic acid. Without doubt, the effects of stearic acid are more favorable than those of trans monounsaturated FA.     

Two-step preparation of fly ash-based composites for microwave absorption

To develop a novel utilization avenue for fly ash (FA), the Co-loaded FA (CoFA) was constructed utilizing FA as raw material to acquire the enhanced microwave absorption (MA) performance. In this study, the CoFA composites were fabricated by a two-step method, including the construction of FA-based ceramic matrix and a subsequent loading of magnetic components. The results of XRD, SEM, and elemental mapping images revealed that Co particles generated from the carbothermal reduction were well dispersed over the interior and surface of matrix. Compared with pure FA, the as-prepared CoFA composites demonstrated the impressive MA performances, which were attributed to the good impedance matching, conduction loss, and interfacial polarization effect between the matrix and Co. When the annealing temperature kept at 700°C, the minimum reflection loss (RL_min) of as-prepared CoFA700 reached up to −40.5 dB and the broad absorption band was measured to be 4.7 GHz with a thickness of 2.0 mm, which was superior to pure FA. Our strategy might provide a new direction to the fabrication of high-efficient MA materials derived from FA.     

Lipid Composition of Garlic

Neutral, glyco- and phospholipids of garlic were resolved into their component fractions by thin layer chromatography. Neutral lipids contained considerable quantities of monoglycerides (18.5%), diglycerides (14.2%), sterols (16.3%) and triglycerides (41.5%) respectively. The phospholipid fraction was rich in phosphatidyl choline (23.5%), phosphatidyl ethanolamine (17.9%), lysophosphatidyl choline (11.8%) and lysophosphatidyl ethanolamine (8.2%). Digalactosyl diglyceride (10.1%), sterol glycoside (15.6%), cerebrosides (8.1%), acylsterol glycoside (38.6%) and monogalactosyl diglyceride (22.5%) were the major components of the glycolipids of garlic. Lauric, myristic, palmitic and linoleic acids constituted the major fatty acids of monoglycerides, diglycerides and free fatty acid fractions whereas palmitic, linoleic and linolenic acids were the major fatty acids of triglycerides. Palmitic and linoleic acids were the major fatty acids of garlic phospholipids. Except the acylsterol glycoside fraction glycolipids were rich in lauric, palmitic, linoleic and linolenic acids; palmitic acid was the only major fatty acid of acylsterol glycosides.     

A high-saturated fat diet enriched with phytosterol and pectin affects the fatty acid profile in guinea pigs

This paper presents the results of a study whose aim was to test the effects of several doses of pectin and phytosterols on the body weight gain and the FA content in emale guinea pigs. The treatments resulted from supplementing with pectin and plant sterol a guinea pig diet (rich in saturated FA), following a 3×3 factorial design, with three levels of pectin (0,3.67 and 6.93%) and three levels of phytosterols (0, 1.37, and 2.45%). Seventy-two female Dunkin Hartley guinea pigs were randomly assigned to the treatment groups (8 animals/group), the duration of the treatment being 4 wk. Pectin dietary intake led to a significant increase in body weight (P<0.001), food consumption (P=0.025), and feed efficiency (P<0.001), but no influence of phytosterols on weight gain or food consumption was detected. We found a significant negative effect of the addition of phytosterols on lauric, myristic, and palmitic acid concents in feces, and a positive effect on their concentration in plasma and liver, but no significant effect on stearic acid content. Apparent FA absorption was assessed by calculating the ratio of FA in feces and diets that the absorption of the different FA could be compared, and the negative effect of phytosterol supplementation on these ratios, especially for lauric and myristic acids, was established.     

Plasma Levels of 14:0, 16:0, 16:1n-7, and 20:3n-6 are Positively Associated,but 18:0 and 18:2n-6 are Inversely Associated with Markers of Inflammation in Young Healthy Adults

Inflammation is a recognized risk factor for the development of chronic diseases, such as type 2 diabetes and atherosclerosis. Evidence suggests that individual fatty acids (FA) may have distinct influences on inflammatory processes. The goal of this study was to conduct a cross-sectional analysis to examine the associations between circulating FA and markers of inflammation in a population of young healthy Canadian adults. FA, high-sensitivity C-reactive protein (hsCRP), and cytokines were measured in fasted plasma samples from 965 young adults (22.6 ± 0.1 years). Gas chromatography was used to measure FA. The following cytokines were analyzed with a multiplex assay: regulated upon activation normal T cell expressed and secreted (RANTES/CCL5), interleukin 1-receptor antagonist (IL-1Ra), interferon-γ (IFN-γ), interferon-γ inducible protein 10 (IP-10), and platelet-derived growth factor β (PDGF-ββ). Numerous statistically significant associations (p < 0.05, corrected for multiple testing) were identified between individual FA and markers of inflammation using linear regression. Myristic (14:0), palmitic (16:0), palmitoleic (16:1n-7), and dihomo-γ-linolenic (20:3n-6) acids were positively associated with all markers of inflammation. In contrast, stearic acid (18:0) was inversely associated with hsCRP and RANTES, and linoleic acid (18:2n-6) was inversely associated with hsCRP, RANTES and PDGF-ββ. In conclusion, our results indicate that specific FA are distinctly correlated with various markers of inflammation. Moreover, the findings of this study suggest that FA profiles in young adults may serve as an early indicator for the development of future complications comprising an inflammatory component.     

The hydrolysis of soap solutions. II. The solubilities of higher fatty acids

Summary The solubilities of capric, lauric, myristic, palmitic, and stearic acids in water at 25° and 50°C. were determined by use of conductivity measurements. Correction was made for carbon dioxide; and total solubilities, together with the concentration of dissociated and of undissociated acid were calculated. Their solubilities range from 359×10⁻⁶ M for capric acid to 2.1×10⁻⁶ M for stearic acid at 25°C. The solulility of laric and myristic is approximately doubled by an increase of temperature from 25° to 50°C., that of capric, palmitic, and stearic acids increases by 25 to 40%.     

Chemical Composition and Characteristics of <Emphasis Type="Italic">Commiphora wightii</Emphasis> (Arnott) Bhandari Seed Oil

The seeds of Commiphora wightii (Arnott) Bhandari contain 9.8 ± 0.7% oil. The fatty acid composition and chemical properties of the extracted oil were determined. Gas liquid chromatography of the methyl esters of the fatty acids shows the presence of 46.62% saturated fatty acids and 51.40% unsaturated fatty acids. The fatty acid composition is as follows: capric acid 3.50%, myristic acid 14.51%, palmitic acid 6.68%, stearic acid 4.70%, arachidic acid 3.18%, behenic acid 14.05%, myristoleic acid 1.34%, palmitoleic acid 12.07%, oleic acid 14.15%, eicosenoic acid 0.11%, linoleic acid 22.34% and alpha linoleic acid 1.37%.     

Modification of butterfat by selective hydrolysis and interesterification by lipase: Process and product characterization

Butterfat was chemically modified via combined hydrolysis and interesterification, catalyzed by a commercial lipase immobilized onto a bundle of hydrophobic hollow fibers. The main goal of this research effort was to engineer butterfat with improved nutritional properties by taking advantage of the sn-1,3 specificity and fatty acid specificity of a lipase in hydrolysis and ester interchange reactions, and concomitantly decrease its level of long-chain saturated fatty acid residues (viz., lauric, myristic, and palmitic acids) and change its melting properties. All reactions were carried out at 40°C in a solvent-free system under controlled water activity, and their extent was monitored via chromatographic assays for free fatty acids, esterified fatty acid moieties, and triacylglycerols; the thermal behavior of the modified butterfat was also assessed via calorimetry. Lipase-modified butterfat possesses a wider melting temperature range than regular butterfat. The total saturated triacylglycerols decreased by 2.2%, whereas triacylglycerols with 28–46 acyl carbons (which contained two or three lauric, myristic, or palmitic acid moieties) decreased by 13%. The total monoene triacylglycerols increased by 5.4%, whereas polyene triacylglycerols decreased by 2.9%. The triacylglycerols of interesterified butterfat had ca. 10.9% less lauric, 10.7% less myristic, and 13.6% less palmitic acid residues than those of the original butterfat.     

Palmitic Acid Lipotoxicity in Microglia Cells Is Ameliorated by Unsaturated Fatty Acids

Obesity and metabolic syndrome are associated with cognitive decline and dementia. Palmitic acid (PA) is increased in the cerebrospinal fluid of obese patients with cognitive impairment. This study was therefore designed to examine fatty acid (FA) lipotoxicity in BV2 microglia cells. We found that PA induced time- and dose-dependent decrease in cell viability and increase in cell death without affecting the cell cycle profile and that PA lipotoxicity did not depend on cell surface free fatty acid receptors but rather on FA uptake. Treatment with sulfosuccinimidyl oleate (SSO), an irreversible inhibitor of fatty acid translocase CD36, significantly inhibited FA uptake in BSA- and PA-treated cells and blocked PA-induced decrease in cell viability. Inhibition of ER stress or treatment with N-acetylcysteine was not able to rescue PA lipotoxicity. Our study also showed that unsaturated fatty acids (UFAs), such as linoleic acid (LA), oleic acid (OA), α-linolenic acid (ALA), and docosahexaenoic acid (DHA), were not lipotoxic but instead protected microglia against PA-induced decrease in cell viability. Co-treatment of PA with LA, OA, and DHA significantly inhibited FA uptake in PA-treated cells. All UFAs tested induced the incorporation of FAs into and the amount of neutral lipids, while PA did not significantly affect the amount of neutral lipids compared with BSA control.     

Physicochemical and Antioxidant Characteristics of Kapok (Ceiba pentandra Gaertn.) Seed Oil

In view of the growing demand for vegetable oils and fats, currently exploration of some under-utilized and non-conventional oil seed crops is of great concern. This work presents data on the detailed physicochemical and antioxidant attributes of kapok (Ceiba pentandra Gaertn.) seed oil. The kapok seeds contained an appreciable amount of oil (27.5 %), protein (35.0 %) and fiber (19.0 %). The extracted kapok seed oil (KSO) had an iodine value of 101.8 g of I₂/100 g of oil, a saponification value of 187 mg of KOH/g of oil), and unsaponifiable matter 0.83 %. KSO also showed a good oxidation state as indicated by the measurements of the peroxide value, conjugated dienes, conjugated trienes, para-anisidine and the induction period (Rancimat method). The tested oil showed a considerable amount of total phenolics (2.50 mg/100 g) and an appreciable free radical scavenging capacity. Gas liquid chromatographic analysis of fatty acids (FA) reveals that KSO mainly has linoleic acid (33.6 %) followed by oleic acid (23.4 %) and palmitic acid (22.4 %). Besides, a notable amount of cyclopropenoid fatty acids such as malvalic acid (9.1 %) and sterculic acid (2.8 %) was also detected. The FA composition of the tested oil was further verified by recording FTIR and NMR spectra. Among the oil phytosterols, analyzed by GC/GC–MS, β-sitosterol was found to be the principal component whereas RP-HPLC analysis showed the occurrence of γ-tocopherol (550 mg/kg) as the major tocopherol along with considerable amount of α-tocopherol (91 mg/kg) and δ-tocopherol (5.52 mg/kg). It can be concluded from the results of this comprehensive study that under-utilized kapok seeds are a potential feed stock for the production of a useful oil for edible and/or oleochemical applications.     

Lipase-catalyzed preparation of palmitic and stearic acid-rich phosphatidylcholine

Saturated FA enhance the oxidative stability of phospholipids. In the present study phosphatidylcholine (PC) rich in palmitic and stearic acids was prepared using lipase-catalyzed transesterification from PC isolated from egg and soybean lecithins. Two different lipases, namely, Novozym 435 and Lipozyme TL IM, were used for the transesterification. The reaction conditions were optimized by varying the lipase dosage, molar ratio of PC to FA, and reaction period. Palmitic acid could be incorporated up to 58.6 and 57.1% using Lipozyme TL IM and 56 and 61% using Novozym 435 in egg and soybean PC from an initial content of 37.4 and 16.8%, respectively. Similarly, stearic acid incorporation was up to 44.7 and 46.3% using Lipozyme TL IM and 37.2 and 55.8% using Novozym 435 in egg and soybean PC from an initial content of 8.6 and 2.1%, respectively.     

Plasma Modified Membrane for Daily Recovery of Oil from Repeated Frying Operation with Frequent Oil Replenishment

Sunflower oil was used for deep frying of potatoes at 170 ± 5 °C and for 8 h per day for 5 days in a fryer with an automatic oil filtration system. Three different frying operations were performed: operation (OP)-1, OP-2 and OP-3; that correspond to the oil unfiltered at the end of each frying day, the oil filtered through the fryer's own filter (passive filtration) and the oil firstly subjected to passive filtration and then filtered through a polyethersulfone membrane modified with hexamethyldisiloxane via radio frequency plasma (75 W-5 min, discharge power–time), respectively. The performance of each operation was investigated in terms of free fatty acids (FFA), conjugated dienoic acids (CD), TOTOX value, total polar content (TPC), Hunter color, viscosity, fatty acid composition, and tocopherol content. The results showed that OP-3 could decrease FFA, CD, TOTOX, TPC, L*a*b* value, viscosity and linoleic acid (18:2)/palmitic acid (16:0) ratio in 29.6, 11.7, 25, 30.8, 6.1*11.3*20.8*, 7.8, 12.2 %, respectively, compared to the unfiltered oil (OP-1). Regenerated oil from OP-3 had a frying life approximately 17 h more than oils from both OP-1 and OP-2.     

Lipase-Catalyzed Synthesis of Human Milk Fat Substitutes from Palm Stearin in a Continuous Packed Bed Reactor

Structured lipids (SL) with similar fatty acid (FA) composition and distribution to human milk fat (HMF) were synthesized by lipase-catalyzed acidolysis of chemically interesterified palm stearin (IV = 35.6) with mixed FA of stearic acid and myristic acid and FA from rapeseed oil, sunflower oil, and palm kernel oil in a continuous packed bed reactor. Response surface methodology (RSM) was used to optimize the reaction system with three selected parameters, namely residence time, temperature, and substrate molar ratio. The best-fitting quadratic models were obtained for the contents of palmitic acid (PA) and PA at the sn-2 position (sn-2 PA) by multiple regressions and the determination coefficient (R ²) values for the models were 0.9886 and 0.9799, respectively. The optimal conditions generated from the models were as follows: residence time, 2.7 h; temperature, 58 °C; substrate molar ratio, 9.5 mol/mol. Under these conditions, the contents of PA and sn-2 PA were 28.8 and 53.2%, respectively, and other FA observed in the experiments were all within the range of corresponding FA of HMF. The similarity of the product obtained to HMF was evaluated by the cited model. The scores for total and sn-2 FA of the product were 45.2 and 38.4, respectively, and the total score for the product was 83.6, which indicated a high degree of similarity of the product to HMF.     

Influence of stearic acid on hemostatic risk factors in humans

Stearic acid has been claimed to be prothrombotic. Elevated plasma factor VII coagulant activity (FVIIc) may raise the risk of coronary thrombosis in the event of plaque rupture. Fibrinogen, an acute-phase protein, is necessary for normal blood clotting; however, elevated levels of fibrinogen increase the risk of coronary heart disease (CHD). Here I report the results of three controlled, human dietary intervention studies, which used a randomized crossover design to investigate the hemostatic effects of stearic acid-rich test diets in healthy young men. A diet high in stearic acid (shea butter) resulted in a 13% lower fasting plasma FVIIc than a high palmitic acid diet, and was 18% lower than a diet high in myristic and lauric acids (P=0.001) after 3 wk of intervention. The stearic acid-rich test fat increased plasma fibrinogen concentrations slightly compared with the myristic-lauric acid diet (P<0.01). When investigating the acute effects of fatty meals, those high in stearic acid (synthesized test fat) resulted in a smaller postprandial increase in FVII than those high in trans and oleic FA, indicating a smaller increase in activated FVII after ingesting stearic acid compared with fats high in monounsaturated FA, probably caused by lower postprandial lipemia. Thus, the present investigations did not find dietary stearic acid to be more thrombogenic, in either fasting effects compared with other longchain FA, or in acute effects compared with dietary unsaturated FA, including trans monounsaturated FA. The slightly increased effect on fasting plasma fibrinogen may be biologically insignificant, but it should be investigated further.     

Dairy Lecithin from Cheese Whey Fat Globule Membrane: Its Extraction, Composition, Oxidative Stability, and Emulsifying Properties

An ethanol extraction method was studied for the production of dairy lecithin from cheese whey-derived milk fat globule membrane (MFGM). A two-step ethanol extraction of MFGM involving first extraction at pH 6.5, followed by second extraction at pH 4.5 yielded 17.2 % lipids. The extracted material contained about 90 % lipids, 4.5 % ash, and 1.2 % moisture. The phospholipid content of the ethanol extract was 31 % and the remainder was mostly neutral lipids. The phospholipid fraction contained 34 % sphingomyelin, 31 % phosphatidylcholine, 27 % phosphatidylethanolamine, 4.6 % phosphatidylserine, and 3.1 % phosphatidylinositol. Since the ethanol extract contained 31 % phospholipids, it can be technically termed as dairy lecithin. The major fatty acid components were linoleic acid (5.1 %), myristic acid (8.3 %), palmitic acid (29 %), stearic acid (14 %), oleic acid (25 %), and the remainder was minor fatty acids with chain length ranging from C4:0 to C22:5. The dairy lecithin was semi-solid at room temperature and exhibited a major phase transition at about 35 °C. Owing to its low polyunsaturated fatty acid content, the dairy lecithin was reasonably stable to oxidation as measured by the rate and extent of hexanal production during 35 days of storage at 45 °C. Oil-in-water emulsions made with less than 2 % dairy lecithin (relative to the total emulsion weight) were unstable; however, emulsions made with greater than 4 % dairy lecithin were very stable for more than 60 days at room temperature. The results of this study indicated that a highly functional dairy lecithin can be commercially produced using cheese whey-derived MFGM as the starting material.     

Positional distribution of fatty acids in the triglycerides of bovine milk fat with elevated levels of linoleic acid

A stereospecific distribution of fatty acids in bovine milk fat containing 15.5% linoleic acid has been compared with the distribution in bovine milk fat containing a normal level (1.8%) of linoleic acid. The positional distribution was obtained by the separate analysis of milk fat triglycerides of high, medium, and low molecular weight. The order of preference for linoleic acid in the high molecular weight triglycerides was position 3>position 2 >position 1. There was an accompanying altered distribution of myristic acid and palmitic acid in favor of position 1 at the expense of position 3. However, the proportions of myristic acid and palmitic acid in position 2, relative to positions 1 and 3 were identifical in the high molecular weight fractions of the two milk fats. The distribution of linoleic acid in the medium molecular weight triglycrides of linoleic-rich milk fat was position 1=position 2>position 3. This resulted in a change in the distribution of 18 carbon monounsaturated fatty acids in favor of position 2 at the expense of position 1, but the distribution of myristic acid and palmitic acid was virtually unaltered. The distribution of linoleic acid in the low molecular weight triglycerides was position 2>position 1>position 3. The amounts of myristic acid and palmitic acid in position 2 and of palmitic acid in position 1 decreased in the low molecular weight triglycerides of the milk fat containing elevated levels of linoleic acid. Changes in the distribution of fatty acids which were observed in the separate analysis of the high, medium, and low molecular weight triglycerides were not apparent when comparing the distribution in the total milk fats. For example, the distribution of myristic acid and palmitic acid appeared to be unchanged, while the distribution of 18 carbon monounsaturated fatty acids was slightly altered in favor of positions 2 and 3. Moreover, linoleic acid showed an almost equal preference for the three positions of the glycerol moiety in milk fat containing elevated levels of this fatty acid with some concentration at position 2.     

Separation of Oleic Acid from Fatty Acid Impurities

Abstract

A method of oleic acid purification is described. The method consists of the following five steps: 1) cooling of the sample to 4°C for a partial separation of palmitic acid by crystallization, 2) distillation at reduced pressure (0.8 mmHg) for removal of lauric and myristic acids, 3) crystallization of stearic and palmitic acids from acetone at -25°C, 4) separation of oleic acid from palmitoleic and linoleic acids by oleic acid crystallization from aqueous methanol solutions at ?10°C, 5) reduced pressure (0.5 mmHg) distillation of the resulting oleic acid sample for removal of water and methanol. By utilizing the procedure described above, a sample containing only 82% oleic acid was refined to a product containing 98.7–98.9% oleic acid.