Characterization of oils from low-gland and glandless cottonseed

New varieties of cotton which contain few or no gossypol pigment glands are being developed. Commercial production of such varieties should contribute to improving meal quality and reducing the color problems encountered with cottonseed oil. Samples of gland-containing, low-gland, and glandless seed grown in California were obtained, and the oils were extracted and characterized. With regard to the over-all characteristics the oils from the low-gland and glandless seed were indistinguishable from regular cottonseed oil. Iodine values, contents of unsaponifiables, cloud- and pour-points, response to the Halphen test, and similar characteristics resembled those of commercial cottonseed oil. No differences were found in behavior during winterization. Determination of the component fatty acids by gas chromatography showed the fatty acid composition of the oils to be typical. Determination of the positions of the double bonds in the unsaturated acyl groups showed no differences between the oils from gland-containing, low-gland, and glandless seed. Ultraviolet, visible, and infrared spectra of the oils revealed no differences other than the presence of gossypol in the crude oil from the gland-containing seed. The infrared spectra of the unsaponifiable fractions obtained from the oils showed some differences, which were not believed to be important. Presented at the fall meeting, American Oil Chemists’ Society, New York, N.Y., October 17–19, 1960. Trainee, Institute of International Education, UNESCO (present address: Union of Burma Applied Research Institute, Rangoon, Burma). One of the laboratories of the Southern Utilization Research and Development Division, Agricultural Research Service, U.S. Department of Agriculture.     

Composition of Glycolipids and Phospholipids of Desilked Silkworm Pupae Oil (Bombyx mori L.)

The desilked silkworm pupae (Bombyx mori L.) collected from Kollegala, Malavalli and Ramanagaram belt of Karnataka State (South India) were extracted with chloroform : methanol = 2:1 (v/v). The oil was fractionated on activated silica gel column into neutral, glyco- and phospholipids. The fractions of glyco- and phospholipid;; were saponified seperately. The saponifiable fractions were analysed for fatty acids and un-saponifiable fractions for sterols. The glycolipid fraction contains mainly oleic, palmitic, stearic, palmitoleic, linolenic, linoleic, arachidic, myristic and lauric acids. Phospholipids had similar fatty acids, however their proportions were varying. Traces of cholesterol were observed in the unsaponifiables of glycolipids, which was absent in phospholipids.     

Studies on Herbaceous Seed Oils XI

Seeds from eight species were analysed by standard procedures for oil and protein contents. The fatty acid composition of the oils was determined by GLC. Five species were found to contain oils above 20% and none of them is rich in protein. Some of the oils have a composition fairly similar to the oils at present in common use. Five seed oils are interesting in having more than 50% of saturated acids of the total fatty acids. T. involucrata seed seems to be a promising species because of its high oil and linoleic acid (61.7%) contents.     

Amino acids of citrus seed meal

Defatted seed meal from oranges and grapefruit contained more sulfur amino acids but less lysine than some common oilseed proteins. Grapefruit seed meal had less tryptophan and more sulfur amino acids than orange seed meal. Probable annual yields of Florida citrus seed oil, meal and hulls are 17, 23 and 13 million lb, respectively. Florida Agricultural Experiment Station Journal Series No. 4313.     

Minor component fatty acids of common vegetable oils

A combination of gas-liquid chromatography (GLC) and oxidative cleavage on fractions isolated by mercury derivative chromatography has shown the presence of previously unreported minor component fatty acids in olive, soybean, cottonseed, corn, peanut, rapeseed and safflower oil. All of the oils examined contain small amt of saturated acids above arachidic, some as high as hexacosanoic acid.Cis-11-octadecenoic acid was found in amt ranging from 0.5~2.0%.Cis-11-eicosenoic acid is present in the 0.04~1.4% range (rapeseed oil excluded). The tetracosenoic acid present in rapeseed (0.4%) and safflower oil (0.1%) has been identified as thecis-15-tetracosenoic acid. No unusual polyenoic species were detected with the exception of those in rapeseed oil, which contains 0.6% of both 11,14-eicosadienoic and 13,16-docosadienoic acid.     

Chemical Evaluation of Rapeseed

The seed chemical composition and oil physical and chemical constants of two imported rapeseed German varieties and one locally produced in Egypt were studied. Rapeseeds are characterized by high lipid and protein contents. The fatty acid analysis indicated that palmitic and oleic acids were the most prevalent saturated and unsaturated acids, respectively. Also, the rapeseed oils under study were free from long-chain fatty acids (>C₁₈). The unsaponifiables were fractionated by GLC into 36 different compounds of which 26 hydrocarbons were identified. The hydrocarbons having carbon atoms between C₂₀ and C₂₄ represent the most common compounds. Campesterol, stigmasterol and β-sitosterol were present in appreciable amounts in German varieties while these compounds occurred as trace substances in the seeds produced in Egypt.     

Seed oils fromCitrus sinensis

Comparative analyses of seed oils from the four most important orange varieties at different stages of maturity have shown remarkably similar fatty acid content by GLC. Percentage distribution of fatty acids, refractive index, and iodine number could probably be used to differentiate or help confirmCitrus species since there is enough variation between species to make a valid comparison. Seed content was noted as being related to fruit maturity, as was moisture content of seeds. The oil content of pineappleorange seeds was found to be variable, correlated to moisture content of seeds, and it reached a maximum when seed moisture had decreased to approximately 49%. Journal Series No. 1662. University of Florida Agricultural Experiment Stations.     

Studies of unsaponifiables in several vegetable oils

The unsaponifiable fractions of soybean, cottonseed, coconut, olive, and avocado oils have been studied in detail. The oils differed in the contents of total unsaponifiables, squalene, tocopherols, and sterols and also in the composition of the tocopherol and sterol fractions. The presence of absence of individual unsaponifiable components may help in establishing the identity of each of the investigated oils and in detecting of admixture by another oil.     

Fatty Acid Composition of Bauhinia variegata and Bauhinia malabarica Seed Oils - Comparison of their Physico-Chemical Properties

The physico-chemical properties of two species of Bauhinia seed oils (Bauhinia variegata and Bauhinia malabarica, N.O. Leguminoseae) were investigated. The amounts of oil extracted from both seeds were 16%. Fatty Acid composition as determined by GLC for Bauhinia variegata and Bauhinia malabarica revealed the presence of linolenic (0.55%, 0.81%), Linoleic (36.84%, 47.26%) oleic (26.14%, 15.26%), stearic (16.95%, 19.29%), palmitic (19.52%, 17.18%) and myristic (traces, 0.20%) acids respectively. It has been observed that the seed variety influences to a great extent the distribution of fatty acids in the seeds oil. The residual meal after the extraction of oil contains 41% and 25% protein in Bauhinia variegata and Bauhinia malabarica respectively.     

Nutritional and toxicological evaluation ofHibiscus sabdariffa oil andCleome viscosa oil

Mesta seed oil (Hibiscus sabdariffa), like cottonseed oil, contains cyclopropenoid fatty acids (2.9%) and epoxy fatty acids (2.6%) in addition to normal fatty acids found in vegetable oils.Cleome viscosa (Capparidaceae) seed oil is rich in linoleic acid (70%) and free from any abnormal chemical constituents. Nutritional and toxicological evaluations of these two oils were done by multigeneration breeding studies by feeding the respective oils and groundnut oil as control at 10% level in a 20% protein diet with adequate vitamins and minerals. These studies revealed that rats fed mesta oil had inferior growth and reproductive performance and also had altered liver metabolism. Rats fedC. viscosa oil did not show any abnormal growth or reproductive performance or altered liver lipid levels. Thus, these studies indicate that raw or refined mesta oil may not be suitable for human consumption whereasC. viscosa oil can be used safely by humans.     

呋喃香豆素光化学毒性及其脱敏柑橘精油的研制

调查了柑橘类精油中普遍存在的呋喃香豆素类物质的种类、化学结构与分布,尤其是该类化合物对皮肤的光化学毒性作用。采用UV技术对市售芳香疗法用橙油、柠檬油、葡萄柚精油与佛手柑精油等四种柑橘类精油进行了光敏化合物呋喃香豆素含量测定,并使用液-液萃取分离技术实现了精油脱呋喃香豆素类生产性试验,开发研制了四种脱敏精油。这些脱敏精油在芳香疗法使用剂量下,其呋喃香豆素类化合物的含量控制在20ppm以下,保证使用的安全与可靠。     

Detection of adulteration of cottonseed oil by gas chromatography

To detect adulterant vegetable oils in cottonseed oil, soybean, rapeseed, and ricebran oils were mixed into cottonseed oil extracted experimentally from seeds. These adulterated oils and the component oils were analyzed for sterols, fatty acids, and triglycerides by gas chromatography. In sterol analysis, stigmasterol was determined for adulteration with soybean and ricebran oils. Brassicasterol content seemed to be reliable as the indicator of adulteration for rapeseed oil. In fatty acid analysis, erucic acid for rapeseed oil and linolenic acid for soybean and ricebran oils were proof of adulteration. Triglyceride analysis was not so reliable as sterol analysis for detecting contamination, except that triglycerides with carbon-58, 60, and 62 indicate adulteration with rapeseed oil. Rapeseed oil (5%) and soybean and ricebran oils (10%) were the limits of detection for adulteration in cottonseed oil. Analysis of cottonseed oil from six refineries did not show positive indications of adulteration.     

Gas-liquid chromatographic analysis of cyclopropene fatty acids

A gas-liquid chromatographic method is described for the quantitative estimation of cyclopropene fatty acids as their methyl mercaptan derivatives. This method estimates individual cyclopropene acids as well as normal and cyclopropane acids. Nine seed oils were analyzed for their cyclopropene fatty acid content. Evidence was obtained for the presence of a cyclopropene fatty acid of shorter chain length than malvalic inAlthaea rosea cav and one with a higher chain length than sterculic inBombacopsis glabra seed oil. This method is less accurate for cottonseed oil than for the other oils tested because of the appearance of some unsymmetrical peaks of unknown origin. The mercaptan derivatives of the cyclopropene acids may be isolated by silver ion thin-layer chromatography. Small amounts of cyclopropane fatty acids were found in a number of the oils analyzed for cyclopropene fatty acids. Presented at the AOCS meeting, Chicago, October 1964.     

A rapid and quantitative procedure for the preparation of methyl esters of butteroil and other fats

A simple and convenient method for the quantitative preparation of methyl esters of fatty acids from glyceride fats and oils is described. The procedure, using potassium methylate as catalyst and a heating interval of 2 min at 65C in a closed vial, is applicable to fats containing both low and high molecular weight fatty acids such as butteroil. The methyl esters of samples ranging from a few mg to 30 mg are isolated by CS₂ extraction and a TLC technique. A similar procedure using sulfuric acid in methanol as catalyst is described for the conversion of free fatty acids to methyl esters. For the routine analysis by GLC of fats and oils such as lard, tallow, soybean, cottonseed oil or butteroil, no isolation of the methyl ester is required. A CS₂ extraction carried out in the reaction vial allows the GLC analysis immediately after the reaction period (2 min). Presented at the AOCS Meeting, Philadelphia, October 1966. E. Utiliz. Ees. Dev. Div., ABS, USDA.     

Studies in interesterification. II. Acidolysis of some vegetable oils with lauric acid

Acidolysis reactions of cottonseed oil, peanut oil, mahua oil (Madhuca latifolia), and palm oil with lauric acid were investigated with special reference to the influence of catalysts and the relative proportions of oil and lauric acid on the extent and type of fatty acids displaced from an oil. Catalysts such as sulfuric acid, zinc oxide, calcium oxide, magnesium oxide, aluminum oxide, and mercuric sulfate were used. The reaction generally was carried out by heating oil and lauric acid at 150C±2 for 3 hr. The reaction products were separated and then analyzed by UV spectrophotometry and GLC. Sulfuric acid was found to be the best catalyst with 1 part of oil and 1.2 parts of the displacing acid (lauric acid) for displacement of high-molecular-weight fatty acids from an oil by low-molecular-weight fatty acids. The nature of the displacement of fatty acids varied from oil to oil, depending on their compositions. It was further indicated that linoleic acid was displaced preferentially over oleic acid in an amount dependent on its initial content in an oil with a corresponding increase in saturated acids content. A broad similarity in displacement patterns, in general, was noted; the fatty acids above C₁₈ were not displaced as in the case of peanut oil. The results demonstrate the feasibility of introducing lauric acid in the vegetable oils for the production of interesting oils with vastly different physical and chemical properties.     

Dihydrosterculic acid,a major fatty acid component ofEuphoria longana seed oil

The seed oil ofEuphoria longana, Sapindaceae, contains 17.4% of 9,10-methyleneoctadecanoic (dihydrosterculic) acid. This identification is based on information from thin layer chromatography, infrared analysis, gas liquid chromatography, nuclear magnetic resonance and mass spectroscopy. Since GLC of the oil showed components that emerged between the usual triglycerides, the cyclopropanoid acid is apparently a triglyceride constituent. The presence of smaller amounts, less than 1%, of cyclopropanoid fatty acids of different chain lengths is indicated by GLC and TLC analyses of the methyl esters. The other major fatty acids in this oil are: 16∶0 (19%), 18∶0 (7%), 18∶1 (36%), 18∶2 (6%), 18∶3 (5%) and 20∶0 (4%).Euphoria oil contains considerably larger amounts of cyclopropanoid fatty acids than previously reported in other seed oils. Presented at the AOCS-AACC Joint Meeting, Washington, D.C., April 1968. No. Utiliz. Res. Dev. Div.; ARS, USDA.     

Chemical characteristics of oils from naked and husk seeds of Cucurbita pepo L.

Pumpkin seed oils from naked and husk pumpkin seeds, produced by an industrial process and by laboratory extraction, were evaluated for fatty acid composition, tocopherol, sterol and squalene content. The major fatty acids in the oils from both varieties were oleic, linoleic and palmitic acid, followed by stearic acid. The ratios of monounsaturated to polyunsaturated fatty acids for husk and naked seed oils were about 0.60 and 0.75, respectively. Analysis of tocopherols in industrially pressed and laboratory‐extracted oils showed that husk seed oils had higher amounts of total tocopherols than naked seed oils. Oils extracted in the laboratory had higher amounts of tocopherols than industrial oils. Pumpkin seed oil, in general, had a high level of squalene, which was higher in husk seed oils than in naked seed oils and in extracted than in pressed oils. The total amount of sterols was higher in husk than in naked seed oils and in extracted oil samples. The main sterols were Δ7‐sterols and their content was similar in all samples, but the content of Δ5‐sterols was higher in oil samples of husk pumpkin seed and in extracted than in pressed oils.     

Evaluation of Some Egyptian Sweet Melon Seed Oils

The physico-chemical properties of two kinds of Egyptian sweet melon seed oils (King Bahtim and Malty Bahtim) were investigated. The amount of oil extracted from King Bahtim reached 34% while in the other kind this percentage reached 36%. The oil extracted has high acid and iodine values in both kinds in comparison with cotton seed oil. Fatty acid composition by GLC for the two kinds revealed the presence of linolenic, linoleic, oleic, stearic, palmitic and myristic acid in different proportions. The variety of the seeds influences to a great extent the amount of saturated and unsaturated fatty acids. Oil stability investigations in a Warburg apparatus indicated that King Bahtim variety reached the maximum absorption of oxygen after 17 days, while Malty Bahtim variety needs 20 days to reach the same maximum absorption. On the other hand chemical analysis of the residual meal indicated the probability of its usage in animal feed as it contains a high amount of protein and fibers. The residual meal can be considered also as a good source for both phosphorus and potassium.     

Chromatography on silicic acid of the unsaponifiable matter of fats

A method has been described for the separation of unsaponifiables into their major chemical classes by silicie acid adsorption chromatography. Methods are also presented for the isolation of unsaponifiables free of fatty acids. The chromatographic procedure was tested on synthetic mixtures of hydrocarbons, esters, alcohols, and sterols and then applied to the unsaponifiables of extracted and pressed olive oils, soybean, teaseed, and rapeseed oils, lard, and tallow. The major sterol of all the unsaponifiables examined was found to be β-sitosterol. Analytical data such as infrared analysis, carbon-hydrogen analysis, melting points of derivatives, and paper chromatography of the sterol fractions are also presented. Report submitted to the Fourth Congress of the International Society for the Study of Fatty Materials, Graz, September 1–3, 1959.     

Soybean unsaponifiables: Chromatographic separations and characterization

Unsaponifiables extracted from 10 different lots of refined soybean oil were subjected to liquidliquid chromatographic separations. Three major fractions were obtained. The least polar hydrocarbon fraction constituted 15 to 30% of the unsaponifiables; the most highly polar fraction contained the steroids constituting 35 to 45% of the unsaponifiables. The fraction of intermediate polarity varied in composition from lot to lot, but usually it contained more than 50% of the unsaponifiables. These basic fractions were analyzed by thin layer, gas-liquid chromatography, and by chemical tests for functional groups. To determine the effects of soybean unsaponifiables on the oxidative and organoleptic stability of edible fats, various concentrations of the extracted and fractionated materials were examined in cottonseed oil. Effects of extraction methods on yields, fractionation characteristics, and composition of the different lots of soybean unsaponifiables are discussed. Presented at the AOCS meeting in Chicago, 1961. Division, Agricultural Research Service, USDA.