Fatty acids in lipids of maturing wheat

Two varieties of hard red winter wheat were sampled at various stages of maturity. The lipids in those samples were fractionated into free polar, free nonpolar and bound lipids. Fatty acids of those fractions were determined. Major acids present were palmitic, oleic, linoleic and linolenic. Both wheat samples showed similar qualitative, but not quantitative patterns in distribution of fatty acids during maturation. In the free polar lipid fraction, the palmitic acid content decreased with maturation while the linoleic acid content increased. The free nonpolar fractions showed a slight increase in linoleic acid; the concentration of other acids decreased slightly as the wheat matured. The bound lipid fraction showed a marked increase in linoleic acid, accompanied by decreases in the other major fatty acids, especially linolenic. Cooperative investigations of Kansas Agricultural Experiment Station and Crops Research Div., ARS, USDA.     

Search for new industrial oils. XIV. Seed oils of labiatae

Seed of 194 species in 56 genera of Labiatae, representing six of the eight subfamilies, were analyzed for oil and protein and for fatty acid composition of the oil. The oils are diverse and include some that contain up to 70% oleic acid, 79% linoleic acid, or 72% linolenic acid. An allenic function occurs in a third of the samples from the subfamily Stachyoideae and in the one sample analyzed from the Prasioideae. A method for determining the allene was devised. Oils fromTeucrium species containtrans unsaturation in unidentified components. Oils from twoLamium species have both allenic andtrans unsaturation. Two species ofThymus appear to produce hydroxy acids. Presented in part at the AOCS Meeting, Houston, April 1965. No. Utiliz. Res. Dev. Div., ARS, USDA. Crops Research Div., ARS, USDA.     

Compositional variation in seed oils of theCrepis genus

Seed oils from eight species of the genusCrepis (family Compositae) fall into three groups differing in chemical composition. Besides conventional fatty acids the oils contain either vernolic acid (47–68%), crepenynic (36–65%), or both (18–35% vernolic and 7–11% crepenynic). Within any one section of the genus, the oils are chemically similar, among the limited groups of samples examined. No. Utiliz. Res. Dev. Div., ARS, USDA. Crops Research Division, ARS, USDA.     

Industrial chemical uses of polyunsaturated fatty acids

Production of vegetable, animal and marine oils containing more than about 40% unsaturated fatty acids totaled 15,000 million pounds in 1968, almost on the scale of petrochemical production. The greater share (64%) of this nonfossil oil production was directed toward food uses, the remainder toward industrial and animal feed uses. The variety of chemical reactions carried out on these unsaturated fatty acid products include hydrogenation, interesterification, dimerization, sulfation, formation of nitrogen compounds, epoxidation, alkaline cleavage and oxidative ozonolysis. Some of these reactions have been developed at Utilization Research and Development Divisions of the Agricultural Research Service, U.S. Department of Agriculture. Research is continuing in developing new reactions for potential industrial application. An example is reductive ozonolysis of unsaturated fatty esters to produce monofunctional aldehydes and bifunctional aldehyde esters. Presented at the ISF-AOCS World Congress, Chicago, September 1970. No. Market. Nutr. Res. Div., ARS, USDA.     

Synthesis of conjugated trienoic fatty acids by a cell-free preparation of tung endosperm

An acetone-insoluble fraction that catalyzes the synthesis of conjugated trienoic fatty acid was prepared from maturing tung nuts. Greatest synthesis with the enzymic fraction occurred in the presence of CoASH, NADH and either ATP or ADP. S. Market. Nutr. Res. Div., ARS, USDA.     

Lipoxygenase inChlorella pyrenoidosa

The presence of lipoxygenase enzyme is observed when cells ofChlorella pyrenoidosa are homogenized under anaerobic conditions. This is the first report of this enzyme in a lower form of plant life. The major product ofChlorella lipoxygenase with linoleic acid as substrate is 13-hydroperoxyoctadecadienoic acid. Research Chemist, ARS, USDA, in cooperation with the North Dakota Agricultural Experiment Station.     

Search for new industrial oils. XII. Fifty-eight euphorbiaceae oils,including one rich in vernolic acid

Seed oil ofEuphorbia lagascae Spreng. contains 57% ofcis-12,13-epoxy-cis-9-octadecenoic (vernolic) acid. The amt of trivernolin in the glycerides of this species indicates random or restricted random distribution of the vernolic acid. Seed from 57 additional species in the Euphorbiaceae were analyzed for oil and protein contents and also for fatty acid composition of the oils. Iodine values (I.V.) of the oils ranged from 87–221. Among these oils, samples were encountered with as much as 76% linolenic, 77% linoleic or 84% oleic acid. Presented at the AOCS in New Orleans, 1964. A laboratory of the No. Utiliz. Res. & Dev. Div., ARS, USDA. ARS, USDA.     

Quantitative determination of double bond positions in unsaturated fatty acids after oxidative cleavage

The position and amt of unsaturation in fatty acids have been determined, especially in pure fractions of partially hydrogenated fats. In developing a quantitative method for determination of ethylenic bonds in monounsaturated and polyunsaturated fatty acids several procedures were combined. Key features include oxidative cleavage; recovery of cleaved acids as salts; and their conversion to methyl, ethyl or butyl esters for programmed gas-liquid chromatographic analysis. Monobasic analyses closely agree with the corresponding dibasic analyses, except neither malonic nor propionic acid has been quantitatively estimated. Analyses are shown for cleavage of high purity oleic, linoleic and linolenic acids; forcis andtrans monoenates; and for conjugated and nonconjugated dienoates. Demonstrated are the accuracy, precision and applicability of the procedure to a wide range of pure fractions isolated after both heterogeneous and homogeneous partial catalytic hydrogenation of polyunsaturated fatty acids. Presented at AOCS Meeting in New Orleans, 1964. A laboratory of the No. Utiliz. Res. & Dev. Div., ARS, USDA.     

Cyclic fatty acids: Separation from straight-chain fatty acids by urea adducting

A mixture containing 37% cyclic and 63% straight-chain fatty acids, made by high-temperature treatment of linseed oil fatty acids with alkali, was separated by the urea adduct method to give unsaturated cyclic fatty acids (nonadduct) in 95% purity and 90–95% yeild. Previous reports from this Laboratory describe a process for separating cyclic fatty acids from stearic acid by hydrogenation followed by crystallization at −40C. The urea adduct method avoids hydrogenation and low-temperature crystallization, and furthermore, unsaturated cyclic and unsaturated straight-chain products can be recovered as individual fractions. Then, by readducting the unsaturated straight-chain fatty acid fraction, the small amounts of palmitic and stearic acids are removed leaving an unsaturated fraction containing oleic, nonconjugated and conjugated linoleic and some unsaturated cyclic fatty acids. Presented at AOCS Meeting, Los Angeles, April 1966. No. Utiliz. Res. Dev. Div., ARS, USDA.     

Search for new industrial oils,IX.Cuphea,a versatile source of fatty acids

Seed oils from five species ofCuphea show three distinct patterns of fatty acid composition.C. hookeriana andC. painteri oils contain ca. 70% caprylic acid,C. ignea and C.llavea oils have over 80% capric acid, andC. carthagenensis oil contains 57% lauric and 18% capric acids. No. Utiliz. Res. and Dev. Div., ARS, USDA ARS, USDA     

Cyclopropenoid fatty acid content and fatty acid composition of crude oils from twenty-five varieties of cottonseed

The cyclopropenoid acid content of oils extracted from 22 commercial varieties and 3 botanical species of cottonseed have been determined. The malvalic acid content determined by HBr titration varied from a low of 0.56% to a high of 1.17%. Iodine values of the oils ranged from 96.8 to 111.6 No definite correlation could be established between iodine value and malvalic acid content. Equations for regression lines for the major acids have been calculated from plots of fatty acid composition vs. iodine value. The high degree or correlation suggests that for commercial oils the fatty acid composition can be estimated from the iodine value. Oils of the 3 experimental types of different species showed wide variations in fatty acid composition and represented many of the maximum and minimum values reported. So. Utiliz. Res. Dev. Div., ARS, USDA. ARS, USDA.     

Chromatography of polar triglycerides on silicic Acid Columns

Triglycerides containing polar fatty acids are resolved by silicic acid chromatography into molecular species containing increased amounts of the polar acids. Natural fats like isano, oiticica, castor, or kamala seed oils with both nonpolar fatty acids and polar hydroxy or keto acids have been resolved into component glycerides according to the degree of polarity. Silicic acid chromatography offers a means of obtaining specific glycerides from fats for detailed studies on glyceride composition and structure. Presented at the AOCS Meeting, Cincinnati, October 1965. No. Utiliz. Res. Dev. Div., ARS, USDA.     

Cationic fatty acid derivatives aid retention of starch and pigment color in cellulosic pulp

Cellulosic pulp in water suspension treated with 0.06% selected cationic fatty acid derivatives at pH 4.5 retained up to 99% of gelatinized corn starch and a pigment color. No. Utiliz. Res. Dev. Div., ARS, USDA.     

Flavor evaluation of natural soybean oils of high and low linolenate content

Three varieties of soybeans, Crest, Grant, and Hawkeye, were processed in the laboratory to obtain edible oils containing 10.4, 9.4, and 5.2% linolenate, respectively. Taste panel evaluations were significantly in favor of low-linolenate soybean oils. Both high- and low-linolenate oils gave the typical off-flavors of aged soybean oil. Flavor results indicate that the linolenate content of soybean oil will probably have to be reduced below 5% to achieve a significant quality improvement in commercially processed oils. Soybean oils of excellent quality can be prepared by laboratory processing procedures. A laboratory of the No. Utiliz. Res. and Dev. Div., ARS, USDA. A laboratory of the Crops Res. Div., ARS, USDA.     

Preparation of vinyl esters of some chlorinated new oilseed crops fatty acids

Several mixtures of fatty acids derived from the seed oil of plants being investigated as new crops, have been chlorinated and the chlorinated acids have been converted to the vinyl esters. These products have potential utility as comonomers in vinyl polymerizations. So. Utiliz. Res. Dev. Div., ARS, USDA.     

Search for new industrial oils. XIII. Oils from 102 species of cruciferae

Seed from additional species of Cruciferae have been analyzed for crude protein, oil and fatty acids in the oil. Oils were like those reported earlier from other crucifers, except forCardamine impatiens which is unique among known seed oils because it contains some 25% dihydroxy acids. Erucic acid is present (0.3–55%) in about three-fourths of the 102 samples. Eicosenoic acid is a major constituent (32–53%) in four species and monohydroxy acids (45–72%) in another four. Linolenic acid occurs (2–66%) in oil of all species. Presented at the AOCS meeting in Chicago, Ill., October 11–14, 1964. A laboratory of the No. Utiliz. Res. and Dev. Div., ARS, USDA. ARS, USDA.     

Amide plasticizers from safflower and tall oil derived fatty acids

Fatty acids derived from a high oleic strain of safflower seeds are eminently suited for the preparation of compatible and efficient N,N-disubstituted fatty acid amide polyvinyl chloride plasticizers with low temperature properties in the adipate-azelate range. N,N-disubstituted amides of tall oil-derived acids, Westvaco Type 1480, give comparable plasticizing performance. Polyvinyl chloride compositions plasticized with the hexachlorocyclopentadiene adduct of N,N-dibutyloleamide show no soapy water extraction loss. So. Market. Nutr. Res. Div., ARS, USDA.     

The occurrence of 6,9,12,15-octadecatetraenoic acid inEchium plantagineum seed oil

The seed oil ofEchium plantagineum, a mem-ber of the borage family, has been shown to contain two polyunsaturated fatty acids not com-monly found in vegetable oils: all-cis-6,9,12-octa-deeatrienoic acid and all-cis-6,9,12,15-octadeca-tetraenoic acid. Prior to their discovery in the Boraginaceae, nonconjugated tetraenoid acids were not known to occur in oils of higher plants. A laboratory of the No. Utiliz. Res. and Dev. Div., ARS, USDA.     

Color and the lipid composition of pork muscles

The lipid characteristics of three porcine muscles were investigated. Included in the study were the light and dark portions of the semitendinosus muscle, the semimembranosus (light) and the quadriceps femoris (dark) muscles. The lipids from the semimembranosus and the quadriceps femoris muscles were observed to be statistically different. The light muscles were 20% higher in lipid level and these lipids contained 20% more glycerides and 40% less phospholipids than the dark muscles. The glycerides from both muscle lipids were identical in fatty acid composition but the phospholipid fatty acids differed significantly. The light muscle phospholipid fatty acids were higher in monoenes while the dark muscle phospholipids predominated in polyunsaturates. In the semitendinosus muscle, the light portion was 35% higher in lipid content than the dark portion but the compositions of the lipids from both areas were similar. When these data were compared to the values for the semimembranosus and the quadriceps femoris muscle lipids, the lipid characteristics were found to be intermediate of predominantly light or dark muscle lipids. Presented at the AOCS Meeting, New York, October 1968. E. Utiliz. Res. Dev. Div., ARS, USDA.     

Aflatoxins in hull and meats of cottonseed

We have found that when aflatoxins are a contaminant of cottonseed, they may be distributed both in the hulls and in the meats. The concentrations in hulls and meats do not appear to be correlated. Aflatoxins were found in hulls and not in meats of some seed samples, and the reverse situation also was observed. The amounts of toxins were generally much greater in meats, which contained up to 10,200 ppb, than in hulls, which contained up to 390 ppb aflatoxins. Hulls as well as meats fromAspergillus flavus-damaged seed represent a potential source of aflatoxin contamination, and both should be analyzed in order to accurately assess the total aflatoxins in seeds. Crops Research Division, ARS, USDA. So. Utiliz. Res. Dev. Div., ARS, USDA.