The decomposition of secondary esters of castor oil with fatty acids

In this study, thermal splitting of secondary fatty acid esters of castor oil was investigated to determine the reaction kinetics under various conditions. Zinc oxide,p toluenesulfonic acid and sulfuric acid were used as catalysts. Reactions were carried out at 260, 270, and 280°C. Experimental data fitted the first-order rate equation for the catalyzed and noncatalyzed reactions. In addition to the kinetic investigation, the splitting (pyrolysis) mixture was evaluated in the preparation of a synthetic drying oil. For this purpose, the mixed fatty acids of linseed, sunflower andEcballium elaterium seed oils were used in the esterification stage of the process. Pyrolysis mixtures were converted to drying oils by combining the liberated acids with equivalent amounts of glycerol. The oils thus obtained show good drying oil properties.     

Chemical and physical analyses of oils from four species of cucurbitaceae

The seed oils ofCucumeropsis mannii, two varieties ofLagenaria sicceraria andTelfairia occidentalis were evaluated. The oil contents by mechanical expression were 33.2%, 33.4%, 34.2% and 32.8% from the roasted kernels ofC. mannii, L. sicceraria var. 1,L. sicceraria var. 2 andT. occidentalis, respectively. Lower oil contents (26.4-28.6%) were obtained from unroasted kernels of the species. The difference in oil yield between the unroasted and roasted kernels was significant (p ≤ 0.05). Roasting of the kernels did not affect the quality factors of the oils, except for the color. The color of oil from roasted kernels was golden, whereas that from unroasted kernels was pale yellow. The predominant fatty acids were palmitic, stearic, oleic and linoleic. The oils from the varieties ofL. sicceraria were more unsaturated (80.2-80.3%) than the oils fromC. mannii (71.4%) andT. occidentalis (69.3%). The smoke (149.5-180.1°C) and flash (204.8-291.5°C) points varied considerably among the oils.Cucumeropsis mannii andT. occidentalis kernel oils failed a cold test, while the oils fromL. sicceraria passed.     

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.     

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.     

Occurrence of 24(E)-ethylidene sterols in two solanaceae seed oils and rice bran oil

The occurrence of two 24 (E)-ethylidene sterols, fucosterol and 28-isocitrostadienol, in the unsaponifiable matters of two Solanaceae seed oils fromDatura stramonium andCapsicum annuum, and rice bran oil from the seeds ofOryza sativa (Gramineae) was demonstrated by their isolation or by gas liquid chromatography. AlthoughZ-isomers of the above two 24-ethylidene sterols, 28-isofucosterol and citrostadienol, are a frequent occurrence in higher plant materials including some Solanaceae seed oils and rice bran oil, the report might be the second instance of the unambiguous demonstration of the occurrence of the 24(E)-ethylidene sterols in higher plants.     

Cis-5-monoenoic fatty acids ofCarlina (Compositae) seed oils

Seed oils ofCarlina corymbosa L. andC. acaulis L. containcis-5-octadecenoic acid as a major fatty acid (21–24%). This acid has not been previously reported as a constituent of Compositate seed oils. The predominant fatty acid in theCarlina oils is linoleic (50–52%); lesser amounts (≦10% each) of palmitic, stearic and oleic acids are also present. The oil ofC. acaulis has almost 2% ofcis-5-hexadecenoic acid;C. corymbosa oil includes minor amounts of some oxygenated fatty acids. Presented at the AOCS Meeting, New York, October 1968. No. Utiliz. Res. Dev. Div., ARS, USDA.     

γ-Linolenic and stearidonic acids in Mongolian Boraginaceae

Seeds of nine Central Asian species of Boraginaceae were investigated for the first time for their oil content and for the fatty acid composition of their seed oils by capillary gas chromatography. Levels of γ-linolenic acid ranged from 6.6 to 13.0% and levels of stearidonic acid ranged from 2.4 to 21.4% of total seed fatty acids. The seed oil ofHackelia deflexa exhibited the highest stearidonic acid content (21.4%) that has been found so far in nature. Other high contents of this fatty acid were in threeLappula species (17.2 to 18.1%). Seed oils ofCynoglossum divaricatum andAmblynotus rupestris contain considerable amounts ofcis-11-eicosenoic (5.3 to 5.8%) andcis-13-docosenoic acid (7.0 to 9.7%) besides γ-linolenic (10.2 to 13.0%) and stearidonic acid (2.4 to 6.5%), which distinguish these oils from those of other Boraginaceae genera. This paper was presented as a poster at 10th Minisymposium and Workshop on Plant Lipids, Sept. 3–6, 1995, in Berne, Switzerland.     

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.     

Kamlolenic acid and other conjugated fatty acids in certain seed oils

The major fatty acid of the seed oil ofTrewia nudiflora is shown to be α-kamlolenic acid, not α-eleostearic acid as believed earlier. Other conjugated acids were found and identified in seed oils not previously studied, viz., α-eleostearic acid inParinari insularum andRicinodendron rautanenii; trans,8-trans,10-cis,12-octadecatrienoic acid inCalendula stellata. The identity of the conjugated acids in four other seed oils was established, viz., α-eleostearic acid inPrunus yedoensis andValeriana officinalis; punicic acid inCucurbita digitata andC. palmata. Issued as N.R.C. No. 9063.     

13C nuclear magnetic resonance spectroscopic analysis of seed oils containing conjugated unsaturated acids

¹³C Nuclear magnetic resonance spectroscopy has been used in a nondestructive investigation of conjugated unsaturated acids in seed oil triacylglycerols. Spectra of seven seed oils, fromPunica granatum, Cucurbita palmata, Jacaranda mimosifolia, Centranthus ruber, Catalpa bignonioides, Chilopsis linearis andCalendula officinalis, containing among them six isomeric trienoic acids,cis,trans,cis- andtrans,trans,cis-8,10,12-,cis,trans,cis-, cis,trans,trans-, trans,trans,cis- andtrans,trans,trans-9,11,13-octadecatrienoic acids, and of the oil ofImpatiens balsamina containingcis,trans,trans,cis-9,11,13,15-octadecatetraenoic acid, have been examined. Structures of component acids were derived from shifts of double bond carbons and of carbons close to the double bond systems. Compositions of the oils were obtained from signal intensities. Results were similar to those obtained by older methods. Only oil ofCentranthus ruber contained more than one major conjugated acid; bothcis,trans,trans- andtrans,trans,trans-9,11,13-octadecatrienoic acids were found. The latter acid is now thought to occur naturally. Presented in part at the International Society for Fat Research/American Oil Chemists' Society World Congress, New York, 1980. NRCC no. 20405.     

Agricultural and genetic potentials of cruciferous oilseed crops

Oilseed crops of the Cruciferae are widely adapted and are of particular importance to countries in the northern latitudes. Cruciferous seed oils from the crops, rapeseed, mustard, Camelina, oilseed radish and Crambe, enter edible or industrial markets, or both. The oil-seed meal can be used either as a high protein feed supplement or as an organic fertilizer. The spring and winter forms of the two species of rapeseed,Brassica napus andB. campestris, are commercially the most important. Advances in crop management and plant breeding have resulted in a 40% to 50% increase in seed yield over the past 25 years. In the next 10 to 15 years, application of newer plant-breeding techniques will result in varieties even higher in yield and seed with improved oil and meal quality. Some of the quality improvements will be new patterns in fatty acid composition, higher oil and protein content, lower fiber content, and removal of the undesirable glucosinolate compounds from the meal. The mustard cropsBrassica juncea andB. hirta are important condiment crops which have considerable potential as edible oil sources. Oilseed radish,Raphanus sativus, yields significantly less seed and oil than other cruciferous oil crops but its oil, which contains a low level of erucic acid (3.7%) and a relatively high content of 16-carbon fatty acids (9.3%), may be useful in blending with normal or zero erucic acid rapeseed oils.Camelina sativa or false flax has many desirable agronomic characteristics but the oil of camelina seed contains too high a level of linolenic acid (36%) to penetrate the edible oil market and too low to compete industrially with linseed oil.Crambe abyssinica andC. hispanica are potentially important producers of high erucic acid industrial oils. Factors limiting Crambe development are the high cost of seed transportation due to the high volume to weight ratio of the threshed seed and the need for extra seed processing steps to render the meal suitable as a high protein feed supplement for livestock and poultry. One of 9 papers presented at the Symposium, “Cruciferous Oilseeds,” ISF-AOCS World Congress, Chicago, September 1970. Contribution No. 425, Research Station, Canada Department of Agriculture, Saskatoon, Saskatchewan, Canada.     

Reduction of glyceride oils to fatty alcohols with sodium borohydride-t-butanol-methanol

Various glyceride oils were reduced to fatty alcohols by refluxing them with sodium borohydride in a mixture oft-butanol and methanol. Chemical characteristics and infrared spectral analyses showed the products to consist mainly of alcohols and the unreduced oils. Olefinic unsaturation was not affected. Castor, coconut and mustard oils yielded 89, 84 and 60% alcohols, respectively, and cottonseed, safflower, linseed, soybean andHydnocarpus wightiana seed oils yielded 72–78% alcohols.     

Occurrence of punicic acid inTrichosanthes bracteata andTrichosanthes nervifolia seed oils

The seeds ofTrichosanthes bracteata andTrichosanthes nervifolia (Cucurbitaceae) contained 31.6 and 27.9% oil and 18.8 and 16.7% protein, respectively. Spectral, chromatographic and chemical analyses showed the punicic acid to occur to an extent of 41.8% inT. bracteata and 51.7% inT. nervifolia seed oils.     

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     

Fruit oil composition and characteristics of two spurge species of Turkish origin

Content and characteristics of the triglyceride fruit oils of two spurge (Euphorbia L.) subspecies, namelyE. glaerosa Pallas ex Bieb. (var.lasiocarpa Boiss.) andE. niciciana Borbas ex Novak, were investigated. For both taxa, oil content of the capsules enclosing the seeds ranged between 15.7 and 16.4% on dry basis, while the decapsulated seeds contained 33.0–34.0% oil, also on dry basis. The average saponification, iodine and acid values were 192, 190 and 6.0, respectively; linolenic acid was detected as the major constituent fatty acid. Consequently, these seed oils are characterized as typical drying oils.     

Seed Oil Characteristics of Onopordum tauricum Willd. and Prunus laurocerasus L

The characteristics of fatty oils recovered from seeds of Onopordum tauricum Willd. and Prunus laurocerasus L. have been investigated. Gas chromatographic analysis showed that linoleic and oleic acids are predominant component fatty acids of Onopordum tauricum and Prunus laurocerasus seed oils, respectively. In view of technological evaluation, Onopordum tauricum seed oil can be regarded as a semidrying oil while the other shows characteristics of a nondrying oil.     

Characterization of triterpene alcohols of seed oils from some species of theaceae,phytolaccaceae and sapotaceae

Triterpene alcohol constituents of the unsaponifiable lipids separated from tea seed oil fromThea sinensis L. (Theaceae), camellia seed oil fromCamellia japonica L. (Theaceae), pokeweed seed oil fromPhytolacca americana L. (Phytolaccaceae) and shea butter from the seed kernels ofButyrospermum parkii (Sapotaceae) were studied. Among a number of triterpene alcohols present in these oils, 19 components were identified as cycloartenol, 24-methylenecycloartanol, parkeol, 24-methylene-24-dihydroparkeol, lanosterol, euphol, butyrospermol, tirucallol, tirucalla-7,24-dienol, dammaradienol, 24-methylenedammarenol, α-amyrin, β-amyrin, lupeol, germanicol, taraxasterol, ψ-taraxasterol, taraxerol and myricadiol. Tirucalla-7,24-dienol and butyrospermol are the predominant components of the 2 Theaceae and pokeweed seed oils. Shea butter, on the other hand, contains α-amyrin followed by butyrospermol and lupeol as the major triterpene constituents. Presented at the AOCS Annual Meeting, San Francisco, April/May 1979.     

Chemical composition ofacacia seeds

The seeds of 12 species ofAcacia, although rich in C-18 unsaturated acids (47.9–93.5%), have low oil content (2.5–10.2%). Highest concentration of octadecatrienoic acid was inA. lenticularis (80.3%),A. suma (76.8%) andA. tortilis (71.7%) oils.A. mollissima was rich in octadecadienoic (69.1%) andA. senegal in octadecenoic (42.5%) acids. All the seed oils showed the presence of epoxy 18:1 acid, 0.6–3.8%. The protein content of the processed seed meals ranged from 13.4–37.2%, the highest being inA. senegal. Fiber content varied from 8.8–11.9%.     

Occurrence of mixtures of geometrical isomers of conjugated octadecatrienoic acids in some seed oils: Analysis by open-tubular gas liquid chromatography and high performance liquid chromatography

Analytical methods to obtain the detailed compositions of the fatty acids in oils containing more than one conjugated octadecatrienoic acid by open-tubular gas liquid chromatography (GLC) and by reversed-phase high performance liquid chromatography (HPLC) were established. Effective GLC separations ofcis,trans,trans-9,11,13-octadecatrienoic acid (ctt-9,11,13–18∶3),ctc-9,11,13–18∶3,ttc-9,11,13–18∶3,ttt-9,11,13–18∶3,ttc-8,10,12–18∶3, andttt-8,10,12–18∶3 were obtained with an opentubular column coated with the nonpolar liquid phase OV-1 using an instrument having all-glass carrier gas pathways. The HPLC method also gave satisfactory separations for the isomeric conjugated octadecatrienoates on the basis of number of thecis andtrans double bonds. Two or three minor conjugated trienoic acids were found along with the principal conjugated trienoic acid in tung oil, and seed oils of cherry,Prunus sp., Momordica charantia, Trichosanthes anguina, Punica granatum, Catalpa ovata, andCalendula officinalis. The mechanism for the formation of the conjugated trienoic acid mixtures in the seed oils is discussed. TheC. ovata seed oil also containedct andtt-9,12-octadecadienoic acids. Thett isomer is presumed to be a precursor ofttc-9,11,13–18∶3, the main conjugated trienoic acid in this oil.     

Determination of conjugated linolenic acid content of selected oil seeds grown in Turkey

Seeds originating from some Turkish sources were analyzed with respect to their characteristics and FA compositions. These seeds represented pomegranate (Punica granatum L.), bitter grourd (Momordica charantia L.), pot marigold (Calendula officinalis L.), catalpa (Catalpa bignonoides), bourdaine (Rhamnus frangula L.), Oregon grape (Mahonia aquifolium), sarsaparilla (Smilax aspera), mahaleb (Prunus mahaleb L.), black-thorn (Prunus spinosa L.), cherry laurel (Prunus laurocerasus L.), and firethorn (Pyracantha coccinea). Bitter gourd and bourdaine seeds contain more than 20% oil. Catalpa, bourdaine, Oregon grape, blackthorn, and cherry laurel seed oil contents ranged from 15 to 20%. In the seeds from plants belonging to the Rosacea family, oil content ranged from 4.5 to 18.5%. Among the seed oils analyzed, pot marigold had one of the lowest oil contents (5.9%). Pomegranate contained the highest amount of total conjugated linolenic acid (CLNA) (86.0%). Seed oils of bitter grourd, pot marigold, mahaleb, and catalpa were rich in CLNA: 60.0, 29.5, 27.6, and 27.5%, respectively. Bourdaine, Oregon grape, and sarsaparilla seeds contained low amounts of CLNA. On the other hand, mahaleb, bourdaine, catalpa, Oregon grape, sarsaparilla, cherry laurel, blackthorn, and firethorn seed oils are basically oleic and linoleic acid-rich oils and therefore have little drying ability (semidrying oil). The results show a potential for the use of endogenous Turkish seeds as a source of CLNA.