The occurrence of ricinoleic acid inLinum seed oils

Thirty-oneLinum species, representing each of the 5 taxonomic sections of the genus, were analyzed for fatty acid composition of the seed oils. Linolenic acid was the major component of the seed oil of species from the sectionsLinum andDasylinum, whereas linoleic acid predominated in those from the sectionsSyllinum, Linastrum andCatbartolinum. All 5 species tested from the sectionSyllinum contained ricinoleic acid as a minor component, ranging between 3% and 8% of total fatty acids. Ricinoleic acid was not present in any other species analyzed. An unidentified fatty acid was present as a minor component in species from the sectionsLinum andDasylinum but absent in species from other sections of the genus.     

Fatty acid composition in seed oils of some onagraceae

The seeds ofOenothera picensis, O. indecora, Ludwigia longifolia andL. peruviana (Onagraceae) contained 18.3, 16.4, 13.9 and 10.1% oil, respectively. Chromatographic analyses showed high levels of linoleic acid (>71.5%) in the seed oils.     

Fatty acid composition of some pine seed oils

The fatty acid composition of seeds from seven species of the genusPinus (P. pinaster, P. griffithii, P. pinea, P. koraiensis, P. sylvestris, P. mughus, andP. nigra) was established. Pine seeds are rich in oil (31–68% by weight) and contain several unusual polymethylene-interrupted unsaturated fatty acids with acis-5 ethylenic bond. These are thecis-5,cis-9 18:2,cis-5,cis-9,cis-12 18:3,cis-5,cis-11 20:2, andcis-5,cis-11,cis-14 20:3 acids, with a trace ofcis-5,cis-9,cis-12,cis-15 18:4 acid. Their percentage relative to total fatty acids varies from a low of 3.1% (P. pinea) to a high of 30.3% (P. sylvestris), depending on the species. The majorcis-5 double bond-containing acid is generally thecis-5,cis-9,cis-12 18:3 acid (pinolenic acid). In all species, linoleic acid represents approximately one-half the total fatty acids, whereas the content of oleic acid varies in the range 14–36% inversely to the sum of fatty acids containing acis-5 ethylenic bond. The easily available seeds fromP. koraiensis appear to be a good source of pinolenic acid: their oil content isca. 65%, and pinolenic represents about 15% of total fatty acids. These values appear to be rather constant.Pinus pinaster, which is grown on several thousand acres in the southwest of France, is an interesting source ofcis-5,cis-11,cis-14 20:3 acid (7% in the oil, which isca. 35% of the dehulled seed weight), an acid sharing in common three double bonds with arachidonic acid. Apparently,P. sylvestris seed oil contains the highest level ofcis-5 double bond-containing acids among pine seed oils that have ever been analyzed.     

The unusual occurrence of 14-methylhexadecanoic acid in pinaceae seed oils among plants

14-Methylhexadecanoic (14-MHD) acid has been identified in a sample of pine seed oil (Pinus contorta) by gas-liquid chromatography-mass spectrometry of its picolinyl ester derivative: Its identification (through its equivalent chain length) and its distribution in four conifer families have been checked. It occurred only in Pinaceae, where it was found in 72 species belonging to the genera Pinus, Abies, Cedrus, Tsuga, Pseudotsuga, Larix, and Picea, in the range 0.02–1.15%. 14-MHD acid could not be detected in the lipids of Taxaceae (Taxus baccata), Cupressaceae (Juniperus communis), or Taxodiaceae (Sciadopytis verticillata), even after a 10-fold concentration of the saturated acid fraction isolated by argentation thinlayer chromatography. It is concluded that Pinaceae, along with Ginkgo biloba seed lipids, are major exceptions in the plant kingdom with regard to 14-MHD acid, which otherwise occurs almost exclusively in lipids of animals and microorganisms. The biosynthesis and metabolic role of 14-MHD acid, which other-wise also occur in wood and leaf lipids, remain unknown.     

Epoxy oleic acid inQuamoclit seed oils

Quamoclit phoenicea Choisy andQuamoclit coccinea Moench. (Syn.Ipomoea coccinea Linn), belonging to the Convolvulaceae plant family, was found to contain palmitic (22.2%, 33.3%), stearic (11.3%, 1.7%) oleic (13.5%, 14.6%), linoleic (40.1%, 30.8%), vernolic (6.4%, 10.2%), arachidic (3.5%, 6.8%) and behenic (3.8%, 2.6%) acids, respectively.     

Fatty acid composition ofcuphea seed oils

Nineteen species of 10 taxonomic sections ofCuphea were analyzed for fatty acid composition of the seed oils. Two sections of the genus,Trispermum andPseudocircaea, previously unreported, are included. Lauric acid is the major component of the seed oil in seven of the species surveyed; capric andmyristic each predominate in five. Linolenic acid, previously thought to be only a trace component ofCuphea seed oils, is the major constituent of two species. Two others are rich in linoleic acid, another minor component of mostCupbea oils.     

γ-Linolenic acid inAcer seed oils

The octadecatrienoic acids inAcer negundo L. (maple family) seed oil include both 9,12,15- (1%) and 6.9,12-(7%) isomers. The chief monoenoic acids identified were 9-octadecenoic (21%), 11-eicosenoic (7%), 13-docosenoic (15%), and 15-tetracosenoic (7%). Also present is a considerable amount of 9,12-octadecadienoic acid. Investigation of ten other Aceraceae revealed their seed oils to have a similar fatty acid composition.     

The acetylenic acid inComandra pallida andOsyris alba seed oils

Gas-liquid chromatographic (GLC) analyses are reported for fatty acid methyl esters from seed oils of two previously unreported species of Santalaceae,Comandra pallida A. DC. andOsyris alba L. The major component in each (43 and 57%, respectively) is an enynoic acid, probablytrans-11-octadecen-9-ynoic (ximenynic) acid which has been found in seed oils of other members of this family. Equivalent chain lengths by GLC analysis and infrared and ultraviolet spectra agree with those obtained by our analyses ofXimenia americana L., in which ximenynic acid is known to occur. The spectral data also agree with those in literature reports on ximenynic acid. The positions of unsaturation have, however, not been rigorously established for the two species newly reported. A laboratory of the No. Utiliz. Res. & Dev. Div., ARS, U.S.D.A.     

Studies on the alcoholysis of some seed oils

The effects of time and temperature on the alcoholysis of rubber seed, melon seed, linseed, and soyabean oils have been studied. The following temperatures were investigated: 200, 220, 245, and 260°C. Litharge (PbO) was used as the alcoholysis catalyst. The optimum alcoholysis temperature was found to be 245 ± 2 °C for each of the oils. At lower alcoholysis temperatures (<245°C), there is the preferential alcoholysis of seed oils derived from unsaturated acid; and the general alcoholysis rates were found to be in the following order: linseed oil ≈ rubber seed oil ≥ soyabean oil ≈ melon seed oil. The alcohol‐solubility of the oils is generally observed to begin at 42–45% conversion of oils to monoglycerides. The α‐monoglyceride contents of the alcoholysis mixtures of rubber seed and linseed oils were generally similar at methanol tolerance, and higher than those of melon seed and soyabean oils. © 2000 John Wiley & Sons, Inc. J Appl Polym Sci 78: 1826–1832, 2000     

The fatty acid composition of gymnospermae seed and leaf oils

Of 12 Gymnospermae seed and leaf oils, only 2 contained cyclopropene fatty acids. All-cis 5, 11, 14, 17-eicosatetraenoic acid occurred in concentrations up to 11.9% in 6 seed oils, and up to 61% in 2 leaf oils. The structure of this acid, as its methyl ester, was established by the combination of physical (UV, IR,¹H- and¹³C-NMR and mass spectra) and chemical techniques. Arachidonic acid also occurred in 2 seed oils.     

Fatty acid composition of seed oils of some members of the meliaceae and combretaceae families

Seed oils of some members of the Meliceae (six) and Combretaceae (three) were analyzed for their fatty acid composition. In oils of members of both families palmitic acid was the most abundant saturated acid. Trace amounts of short chain (C12–C14) and long chain (C20–C22) saturated acids were detected in some members of the two families. Oleic acid was the most abundant unsaturated acids in the oils of four members of the Meliaceae. However, in the oils ofCedrella odorata andLovoa trichilloides, dienoic acid (C18:2) was the major unsaturated acid. Strikingly high levels of trienoic (C18:3) and monoenoic (C16:1) acids were detected in the seed oils ofC. odorata andEnthandrophragma angolense, respectively. Oleic acid also was the most abundant unsaturated acid in the Combretaceae. The nutritional value and industrial potentials of these oils are given.     

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.     

cis-5-Monoenoic fatty acids in some chenopodiaceae seed oils

Methyl esters from seed oils of four Chenopodiaceae species are unusual in that they contain methylcis-5-hexadecenoate (4.6–12%) and methyl 5-octadecenoate (1.1–1.2%). There are indications of small amounts of 18∶2^5,9 and 18∶3^{5, 9, 12} along with unsaturated acids commonly found in seed oils-oleic (14–21%), linoleic (53–57%) and linolenic (3.5–7.8%). Fatty acid composition of the oils was determined by gas chromatography, and positions of the double bonds were established by application of gas chromatography-mass spectrometry to the methoxylated methyl esters. N. Market. Nutr. Res. Div., ARS, USDA.     

Fatty acid composition of Iranian citrus seed oils

Fatty acid compositions of seed oils from eight Iranian citrus fruits were determined. The ranges of values for major fatty acids were 21.8–29.4% palmitic, 3.1–7.60% stearic, 0.3–1.3% palmitoleic, 23.5–32.3% oleic, 33.5–39.8% linoleic, and 3.1–7.6% linolenic. Low amounts (up to 0.1%) of myristic and arachidic acids and traces of a few unidentified ones constituted minor fatty acids.     

Fatty acid composition ofThalictrum L. seed oils

The fatty acid composition of five representatives of theThalictrum L. genus of the plant familyRanunculaceae has been investigated. The fatty acids include mainly acids with double bonds in thetrans-5 position (about 60%). Although the main component of the fatty acids is a triene acid (trans-5,cis-9,cis-12-octadecatrienoic acid), the oils investigated are semidrying.     

Analysis and fatty acid composition of tobacco seed oils

Summary THE fatty acid compositions of twelve samples of oil representing a number of different types and varieties of tobacco were determined by the thiocyanometric method. The samples were remarkably uniform in composition, containing on the average 75% linoleic, 15% oleic, and 10% saturated acids. Spectrophotometric determination of the linoleic acid content of two samples of oil gave values 3.0 and 5.4% higher than those by the thiocyanometric method. A more complete investigation of the fatty acid constituents of one sample of flue-cured tobacco seed oil was carried out by analysis of fractions obtained by distillation of the methyl esters and by low-temperature crystallization of the distilled ester fractions. The composition calculated from these analyses agreed well with that determined from analysis directly on the oil. The saturated acids consisted of palmitic and stearic acids, the proportions being about 7 and 3%, respectively, of the total fatty acids. Analysis of this sample of oil showed that it contained 0.043% of tocopherol. From its composition, tobacco seed oil would seem to be particularly suitable for the manufacture of nonyellowing alkyds or for the preparation of technical linoleic acid. One of the laboratories of the Bureau of Agricultural and Industrial Chemistry, Agricultural Research Administration, United States Department of Agriculture.     

Quality and compositional studies of some edible leguminosae seed oils in Botswana

Seed oils were extracted with n-hexane from three edible Leguminosae seeds: Tylosema esculentum, Xanthocercis zambesiaca, and Bauhinia petersiana, giving yields of 48.2, 17.6, and 20.8% (w/w), respectively. Some physical and chemical parameters were determined to ascertain the general characteristics of the oils. The saponification and iodine values indicated that all three oil samples could be classified among the olive group of oils. This inference was supported by the results of the detailed fatty acid composition of the oils as determined by capillary gas chromatography. The ratio of total unsaturated to total saturated fatty acids in all three oil samples was approximately 70:30, with either oleic or linoleic acid being the dominant fatty acid. These results were in agreement with a proton nuclear magnetic resonance analysis of the fatty acid classes in the seed oils. Thus, the analysis served to justify the use of the three Leguminosae seed oils in food preparations. The work has further indicated that, with their attractive properties, the seed oils from T. esculentum, X. zambesiaca, and B. petersiana are good candidates for further studies to evaluate their future commercial prospects in the Southern African region.     

Characterization of the seed oils of some commercial cultivars of melon

Proximate analysis of the seeds from three commercial melon cultivars (Honey Dew, Hy‐mark and Orange Flesh) showed high percentage of lipids (25.7—27.6%) and proteins (15.2—19.2%). The physico‐chemical properties of the hexane‐extracted oil from the seeds of these cultivars were determined. Gas chromatographic analysis of the oils showed the presence of almost all fatty acids starting from C₆— C₂₄ except that of C₁₁ , C₂₁ C₂₃ , C_18:2 being the principal fatty acid followed by C_18:1 , C_16:0 , and C_18:0 fatty acids. The number of fatty acids, which were present in concentrations higher than 0.01% of total fatty acids, was 17, 14, and 13, respectively, in these cultivars     

Eicosenoic acid and other fatty acids ofSapindaceae seed oils

The seed oils of 11 species ofSapindaceae were examined, and their fatty acid composition was determined.cis-11-Eicosenoic acid was identified as the major fatty acid ofKoelreuteria paniculata. It was present in nine of the 11 species in amounts from 8–60% of the total fatty acids and is evidently a common component of oils of this plant family. Arachidic acid was present in amounts up to 11%. Only three of the oils had acids of chain length greater than C-20. Seed oils of certain species ofKoelreuteria andCardiospermum are good potential sources of 11-eicosenoic acid. N.R. C. No. 9537.     

Epoxy acid in seed oils ofMalvaceae and preparation of (+)threo-12,13-Dihydroxyoleic acid

Seed oils of six species ofMalvaceae, representing four genera, were found to containcis-12,13-epoxyoleic acid in amounts estimated at 1,5–7% of the total fatty acids. Acetolysis of the oils gave the corresponding dihydroxyoleic acid, which was shown to be predominantly adextro-rotatory form ofthreo-12,13-dihydroxyoleic acid. It was obtained optically pure, and its structure was confirmed by orthodox methods. The hydrogenation product, (+)-threo-12,13-dihydroxystearic acid, was also obtained optically pure and characterized. The best yield of dihydroxyoleic acid was obtained from the seed oil ofMalope trifida. Samples of oil from four other species ofMalvaeae had a very low or negligible content of epoxy acid. Presented in part at the annual meeting, American Oil Chemists’ Society, New Orleans, La., April 20 – 22, 1959. Issued as N.R.C. 6042.