Tissue fatty acid changes and tumor incidence in C3H mice ingesting cottonseed oil

The incidence of spontaneous mammary tumors in C3H mice at 35 wk was higher in mice fed rations containing cottonseed oil than in mice fed fats of comparable fatty acid composition. The time to 50% (T₅₀) incidence was also shorter in the first group. The fatty acid composition of tissue lipids from mice fed the cottonseed oil showed changes indicating the presence of cyclopropene fatty acids-higher levels of saturates and lower oleate/stearate and palmitoleate/palmitate ratios. A possible association between the development of a spontaneous mammary tumor in the C3H mouse and the presence of cyclopropene fatty acids in the cottonseed oil is indicated.     

Isopropanol as a solvent for extraction of cottonseed oil

Phase equilibrium data for the system; cottonseed oil-isopropanol-water were determined at 30°C. and compared with data for the system; cottonseed oilethanol-water. The relative phase distribution of fatty acids and cottonseed oil in mixtures with isopropanol and water was studied under varying conditions of water and fatty acid concentrations. These tests showed the fatty acids to be highly concentrated in the alcohol-water phase. Flaked cottonseed meats were extracted in continuous extraction apparatus with 91% isopropanol, 99% isopropanol, and mixtures of commercial hexane and isopropanol. Analytical data on the extractions show that 91% isopropanol is an efficient solvent for extracting active gossypol along with the oil. Rat and swine feeding tests of the isopropanol extracted meal showed it to be highly superior to hydraulic meal as a source of protein. A method was developed for treatment of the cottonseed-isopropanol miscella by liquid-liquid extraction to separate purified oil and fatty acid fractions from other materials in the extract.     

Fatty acid composition of corn endosperm and germ oils as influenced by different extraction procedures

Gas liquid chromatography was used to determine fatty acid composition of oil obtained from corn (Zea mays L.) inbred lines by different extraction procedures. Kernels were separated into endosperm and germ fractions for nine inbreds which had a considerable range in fatty acid composition of oil. Oil obtained from the endosperm by different extraction procedures was significantly different in composition for all fatty acids. Oil obtained from the germ by different extraction procedures was similar in fatty acid composition. The differences in response of endosperm and germ oils to extraction procedures were attributed to the type of lipid found in each fraction. It was concluded that choice of extraction procedures was of little importance in studies of oil from the corn germ, but that specific extraction procedures must be recognized as a factor when studying oil composition of the endosperm. Approved as Journal Series Paper No. 696, University of Georgia, College of Agriculture Experiment Stations.     

Adulterated butterfat: Fatty acid composition of triglycerides and 2-monoglycerides

Beef tallow and cottonseed oil were mixed with a pure butterfat in the ratios of 2%, 4% and 6% to obtain admixtures of beef tallow with butterfat and cottonseed oil with butterfat. The hydrolysis of individual triglycerides was carried out using the lipase to obtain 2-monoglycerides. The results indicated that butterfat had a higher percentage of C14:0 and C16:0 acids than found in the triglycerides and 2-monoglycerides of beef tallow and cottonseed oil. Beef tallow contained a higher proportion of C18:0 and C18:1 acids than butterfat and cottonseed oil triglycerides or 2-monoglycerides. Cottonseed oil had a higher percentage of C18:2 acid located in triglyceride or 2-monoglyceride than found in butterfat or beef tallow triglycerides and 2-monoglycerides. The analysis of the samples of butterfat containing 2%, 4% and 6% beef tallow revealed that the addition of beef tallow to butterfat affected the fatty acid composition of butterfat triglycerides and 2-monoglycerides with C18:0 and C18:1 acids; the effect was increased with increasing percentages of beef tallow. The addition of cottonseed oil to butterfat in the ratios of 2%, 4% and 6% affected the fatty acid composition of butterfat triglycerides and 2-monoglycerides. It was found that both C18:1 and C18:2 increased as the added cottonseed oil percentages increased.     

Composition of oils extracted from potato chips by supercritical fluid extraction

To determine effects of two extraction procedures on oil compositions, tocopherols, monoacylglycerol, diacylglycerol, triacylglycerol, free fatty acids, polymers and polar components were determined in oils after extraction from potato chips by either supercritical carbon dioxide or hexane. Potato chips were fried in cottonseed oil or low linolenic acid soybean oil and sampled after 1, 10 and 20 h of oil use. Both extraction methods recovered comparable amounts of oil from the potato chips. Compositions of triacylglycerol and non‐triacylglycerol components including tocopherols, monomer, polymer, monoacylglycerol, diacylglycerol were similar for samples of chips fried in either oil except for the δ‐tocopherol data for potato chips fried in the low linolenic acid soybean oil used for 10 h of frying. There were some differences between the composition of low linolenic acid soybean oil extracted from the potato chips compared to the fryer oil at the 20 h sampling time. These results showed that the supercritical carbon dioxide extraction gave similar results to hexane extraction in yield and composition of oils from potato chips.     

Cottonseed oil

Research on the effects of genetics and growing location on cottonseed has shown that oil and fatty acid composition could be improved if geneticists and agronomists would strive for improved seed quality as vigorously as they do for improved fiber quality. Breeding of glandless or gossypol-free cottonseed was a genetic breakthrough. Glandless varieties are now available that produce yields having the quality of fiber and seed equivalent to those of glanded cultivars. Oil, food-grade lecithin and meal byproducts are readily processed from glandless cottonseeds because of the absence of gossypol. Major research programs on cottonseed processing include: (a) testing alternative screw-press and extrusion operations for efficient direct solvent oil extraction; (b) developing alternative solvent extraction systems with ethanol, isopropanol and supercritical fluids; (c) using gas chromatographic/mass spectrophotometric techniques to characterize enzymatic and nonenzymatic mechanisms that produce secondary oxidation off-flavor products; and (d) controlling hexane losses in solvent extraction systems.     

双液相萃取棉籽油制备脂肪酸甲酯

以双液相萃取技术处理棉籽,在得到脱毒棉粕的同时得到含有高质量毛油的非极性相。以非极性相作为与甲醇进行酯交换反应的原料,得到脂肪酸甲酯和甘油。考察了非极性相溶剂石油醚与棉籽油的比例对酯交换转化率和洗涤粗产品用水量的影响,确定了石油醚与棉籽油的最佳质量比为3,在此条件下,洗涤用水量可降低一半。考察了醇油比、催化剂用量、反应温度、反应时间等参数对转化率的影响。应用正交实验的方法找出酯交换反应的适宜条件为：醇油比6：1,催化剂用量1.1％,反应温度60℃,反应时间120min。在此反应条件下,产物中脂肪酸甲酯的含量可达97.4％。     

A simplified process for the elimination of the halphen-test response in cottonseed oils

Since certain biological effects have been ascribed to the cyclopropenoids that give a positive response to the Halphen test, processes were explored to eliminate this response from cottonseed oils. Heating alkali-refined, Halphen-positive cottonseed oils in a modified laboratory deodorizer in the presence of cottonseed oil fatty acids, capric acid, citric acid, or phosphoric acid was found to be an effective method of eliminating this response. These treated, Halphen-negative cottonseed oils, the untreated Halphen-positive cottonseed oil, and a corn oil control were incorporated into rations fed to different groups of laying hens. Hens that ingested either the Halphen-negative cottonseed oil or the corn control produced normal eggs, whereas hens fed the Halphen-positive cottonseed oil produced eggs with pink whites, decreased pH of whites, and increased pH of yolks on storage, and lower ratios of oleic acid to stearic acid in the yolk lipids. The simple processes presented—particularly the use of cottonseed oil fatty acids—appear to offer a practical means of inactivating the cyclo-propenoids in cottonseed oil and thus eliminating the biological effects attributed to them. Presented at AOCS Meeting in Houston, 1965. Honorable Mention, Bond Award Competition. So. Utiliz. Res. Dev. Div., ARS, USDA.     

A study of lipids in commercial feeds

Summary and Conclusions The total extract, phospholipid, unsaponifiable matter, and total fatty acids were determined on 6 samples each of soybean oil meal, cottonseed oil meal, meat and bone scraps, alfalfa leaf meal, wheat gray shorts with screenings, and whole oats and on 5 samples of barley, using both the 16-hour anhydrous ether method and a 3+1 alcohol-ether method of extraction. With the exception of whole oats and barley the total ether soluble extract was considerably greater by alcohol-ether extraction than by ether extraction, especially so in the case of soybean meal and cottonseed meal. The non-phospholipid fatty acids, however, showed no significant difference between the two methods of extraction, the differences in total fatty acids being accounted for by the different amounts of phospholipid fatty acids. The total extract is a poor criterion of the lipid feed value of some feeds, especially alfalfa leaf meal and soybean meal. However, the ethyl ether method more nearly approximates the total fatty acid content than does the alcohol ether method of extraction. Much of the total extract cannot be accounted for in the sum of the phopholipid, unsaponifiable matter and fatty acid contents as determined. A method is presented for the determination of phospholipid in plant tissue. The significance of the lipid analysis of the feeds investigated and the relative values of the anhydrous ether and a 3+1 alcohol ether methods of analyses are discussed.     

Spectrophotometric estimation of soybean oil in admixture with cottonseed and peanut oils

Conclusion A spectrophotometric method has been described for the determination of soybean oil in admixture with cottonseed oil. The method provides a simple and rapid means of detecting gross adulteration of one oil with another and permits an accurate determination of linolenic acid for use as a criterion of the economic value of an oil mixture and as a guide in oil processing. The factor limiting the precision of the method is variation in composition of the cottonseed and soybean oils in the mixtures to be analyzed. Variations in composition affect the proportion of measured triene conjugation, due to the linolenic acid content of the soybean oil and the apparent linolenic acid content of the cottonseed oil. Thus, for unknown mixtures only average value corrections can be made for apparent linolenic acid content and the accuracy of a particular analysis will depend upon how well the composition of the oils in the particular mixture follows those of the average mixture. The method described can be extended to mixtures other than those of soybean and cottonseed oils. Thus, soybean oil may be determined in admixture with a peanut oil. In general, any oil which has an unsaturated fatty acid capable of producing triene conjugation upon alkali isomerization can be determined in the presence of any other oil containing no appreciable quantity of unsaturated fatty acids which can produce triene conjugation by such treatment. Presented before The American Oil Chemists’ Society, New Orleans, Louisiana, May 10–12, 1944. One of the laboratories of the Bureau of Agricultural and Industrial Chemistry, Agricultural Research Administration, U. S. Department of Agriculture.     

Effect of plant population densities and application of growth retardants on cottonseed yield and quality

In field trials at Giza in 1986–1987, cotton cv. Giza 75 was sown at 166,000, 222,000 and 333,000 plants/ha and given foliar applications of 0, 250, 500 and 750 ppm Cycocel (chlormequat) or Alar (daminozide). As plant density increased, there was a decrease in cottonseed yield/ha, seed index, seed protein content, oil and protein yields/ha, oil refractive index, iodine value, unsaponifiable matter and unsaturated fatty acids (myristoleic, oleic and linoleic). In contrast, as plant density increased, there was an increase in oil acid value, saponification value and saturated fatty acids (caprylic, capric, lauric, tridecylic, myristic, palmitic and stearic). Application of Cycocel or Alar increased cottonseed yield/ha, seed index, seed protein content and oil and protein yield/ha, oil refractive index, iodine value, unsaponifiable matter and unsaturated fatty acids. However, there was a decrease in oil acid value and saponification value. There were no differences among application rates of either chemical on cottonseed yield/ha. The highest oil and protein yield/ha was observed with Cycocel applied at 750 ppm, followed by Alar at 250 ppm. Applying Cycocel at 250 ppm gave the highest oil refractive index and unsaponifiable matter, and the lowest acid value. Application of Alar at 250 ppm gave the highest oil iodine value and the lowest saponification value, and also at 250 or 500 ppm gave the highest oil unsaturated fatty acid composition. Interaction was positive between plant density, Cycocel and Alar and affected cottonseed yield/ha. The 166,000 plants/ha and application of Cycocel at 750 and Alar at 250 ppm are recommended for the improvement of cottonseed yield and quality.     

Concentration of linoleic acid from cottonseed oil by starch complexation

The extraction of linoleic acid from fatty acids(FA) of the cottonseed oil using starch–FA complexes was developed for the first time. We showed that starch can form inclusion complexes of different strengths with FA and that the different strengths stem from the differences in chain length, degree of unsaturation, and position of double bonds of FA. The optimal separation conditions were determined as follows: The inclusion temperature is 69 °C, the inclusion time is 30 min, the starch/FA mass ratio is 10:1, and the ratio of the volume of methanol–water solution and the mass of FA is 18:1. Compared to urea inclusion complexation, starch complexation has milder reaction temperature and shorter reaction time. Under these conditions, linoleic acid can be concentrated from 38.9% to 70.04% by one-off extraction. Moreover, the experimental results demonstrate the almost perfect reusability of starch. These results show that starch complexation is a promising method that can be used to obtain highly concentrated linoleic acid from cottonseed oil.     

Germination and free fatty acids in seed stock lots of cottonseed

Summary The relationship of the free fatty acid content in the oil to the percentage germination for 254 samples of cottonseed of different varieties indicates that the free fatty acid content may be used as a practical screening index for use in selecting lots of cottonseed to be reserved for seeding purposes and subsequent testing for germination. The percentage germination decreases in general with increasing free fatty acid content. The mathematical probability that a given lot of seed will exceed a specified minimum germination value decreases markedly as the free fatty acid content of the oil increases. Insofar as practical, it is suggested that cottonseed reserved for seeding have a low free fatty acid content, less than 0.75% in the oil if at all possible. One of the laboratories of the Bureau of Agricultural and Industrial Chemistry, Agricultural Research Administration, U. S. Department of Agriculture. In cooperation with the Production and Marketing Administration, U. S. Department of Agriculture, under Marketing Act of 1946.     

Chemical evaluation of egyptian citrus seeds as potential sources of vegetable oils

Seeds of the citrus fruits orange, mandarin, lime and grapefruit were analyzed. Petroleum ether-extracted oils of such seeds amounted to more than 40% of each. Physical and chemical properties of the extracted oils are presented. Samples of the extracted oils were saponified and the unsaponifiables and fatty acid fractions isolated. The isolated unsaponifiables and fatty acids were analyzed by GLC. GLC analysis of the unsaponifiables revealed compositional patterns differ-ent in number, type and relative concentration of fractions according to type of citrus seed oil, depending on the solvent system used for oil extraction and unsaponifiable matter isolation. The compositional patterns of the unsaponifiables were similar to that of cottonseed oil. Mandarin and grapefruit oils are free of cholesterol. The data demonstrate that the fatty acid compositional patterns of the oils differ; Mandarin seed oil contains the largest number of fatty acids, and grapefruit seed oil contains the lowest. The total amounts of volatile fatty acids in these oils are generally higher than those of other edible oils. Lime seed oil is similar, in the degree of unsaturation, to soybean oil. The orange oil pattern is similar to cottonseed oil. The amount of total essential fatty acids in lime seed oil is the highest of the oils studied.     

Miscella refining test method for the determination of cottonseed oil color

Most of the cottonseed oil mills in the United States have already converted to expander solvent extraction and miscella refining. This practice permits mills to produce and market a consistently light-colored, prime bleachable summer yellow cottonseed oil at reduced cost and refining loss. A laboratory-scale miscella refining test was developed to asses the oil quality in terms of its color. The test involves the addition of 3 parts oleic acid per 100 parts of crude oil in the miscella followed by refining with 2.5 parts NaOH when crude oil contains less than 4.5% free fatty acid (FFA). When crude oil contains FFA between 4.5 and 7.5%, no oleic acid is added prior to refining with 2.5 parts NaOH. When crude oil contains FFA higher than 7.5%, no oleic acid is added and the caustic addition table in American Oil Chemists' Society Method Ca 9a-52 is followed. The test was conducted at room temperature and gave reproducible colors comparable to commercially refined oils.     

Biodiesel synthesis from vegetable oils with supercritical methanol

Transesterification reactions of sunflower, rapeseed, cottonseed and cameline oils in supercritical methanol were studied in a flow reactor under equal conditions. It was found that the oil type produced insignificant effect on the product composition (fatty acid esters) and oil conversion value.     

The effect of diet on the fatty acid composition of several species of fresh water fish

Summary Four kinds of fresh water fish were captured in the young stage, maintained on a low-fat diet for about two months, and either continued on that diet or transferred to test diets containing 10% cottonseed or menhaden oil for about five weeks. The fish were then sacrificed, and their total body fatty acids were examined for relative amounts of 2, 3, 4, 5 and 6 double bonds. It was found that no significant change from the natural diet occurred in the fatty acids on the low-fat or cottonseed oil diets while on the menhaden oil diet the fatty acid composition changed to resemble the composition of that oil. These changes differed from those of the marine mullet in that the body fat of the latter lost much of its naturally occurring polyunsaturated acids, when placed on the low-fat regimen, and regained it on the menhaden oil diet. Contribution from the Departments of Oceanography and Meteorology and of Biochemistry and Nutirition of The Agricultural and Mechanical College System of Texas, Oceanography and Meteorology Series No. 122, supported in part by Grant No. A-777 from the National Institutes of Health.     

The estimation of the composition of edible oil mixtures

The fatty acid, sterol and tocopherol contents of edible oils were used to determine the composition of oil mixtures by means of a weighted least squares estimator with backwards elimination. The model was tested on 93 samples containing known amounts of sunflowerseed oil, groundnut oil, soybean oil, cottonseed oil, maize oil, olive oil and palm oil. Of these samples 75 were binary mixtures, seven were ternary mixtures, one contained seven oils and 10 were pure oils. Satisfactory results were obtained with 79 of the 93 samples (85%). The differences between the actual and estimated concentrations of the main components were greater than 2.7 times the standard error for six samples; the mean of the absolute differences was 4.7% for all 93 samples. The use of this model is considered superior to the matching of a fatty acid composition, but the model still needs a lot of development.     

Application of principal-component analysis on near-infrared spectroscopic data of vegetable oils for their classification

In the near-infrared (NIR) spectra of oil, information about fatty acid composition is concentrated in the range of 1600–2200 nm. Principal-component analysis (PCA) was applied on the standardized full NIR spectral data of this region for vegetable oils to totally capture the NIR spectral pattern. Nine varieties of vegetable oils (soybean, corn, cottonseed, olive, rice bran, peanut, rapeseed, sesame and coconut oil) could be successfully classified from their PCA scores. Examining the contribution of wavelengths to PCA scores showed that wavelengths with a high loading weight were assigned to characteristic absorption regions that correspond to specific fatty acid moieties. This classification is related to the fatty acid composition of an oil, and it can be carried out rapidly and easily after eigenvectors were obtained.     

棉籽酸化油的理化性质及脂肪酸组成分析

采用气相色谱法分析了棉籽酸化油的脂肪酸组成,并对其理化性质进行了研究。分析结果表明,棉籽酸化油的含油率为91.33%,酸值为144.35mgKOH/g,碘值为116.58gI2/100g,皂化值为199.80mgKOH/g;其主要脂肪酸为棕榈酸(21.29%)、硬脂酸(2.29%)、油酸(23.72%)、亚油酸(50.23%)和亚麻酸(0.39%),其中不饱和脂肪酸的含量高达74%,具有很高的工业利用价值。