Studies on characterization and variation in triglyceride fatty acids from punt/us sarana body lipids

Body lipids of P. sarana of four different sizes were fractionated into phospholipids, neutral lipids, nonsaponifiables, total fatty acids, polyunsaturated, monounsaturated and saturated fatty acid fractions. Percentage composition of each fraction was determined. The triglyceride fatty acids were identified by thin layer and gas liquid chromatography. C₈ to C₂₃ fatty acids including both odd numbered and branched chain acids were detected. The major constituents were C₁₄, C₁₅, C₁₆, C_16:1, C₁₈ C_18:1, C_18:2, C_18:3; forty-three other acids were detected in lower proportions. Composition of each fatty acids and their variation with size have been discussed.tP. sarana body lipids in general showed a behavior typical of fresh water fish by having a higher percentage of saturated C₁₆ and unsaturated C₁₈ acids and a lower percentage of unsaturated C₂₀ acid.     

High pressure reverse phase liquid chromatography of fatty acidp-bromophenacyl esters

High pressure reverse phase liquid chromatography has been employed to rapidly separate saturated and unsaturated fatty acids as the correspondingp-bromophenacyl esters. Through the use of a highly efficient C₁₈ reverse phase column packing, it has also been possible to distinguish among geometrical and positional isomers of the unsaturated acids. The use of ultroviolet-sensitive esters has permitted the detection of low (nanogram range) concentrations of fatty acids. The time required for analysis has been further reduced by employing a novel and rapid method for the preparation of the esters.     

Synthesis and Surface Active Properties of Sulfonated Acrylate Esters Based on Al‐Cedre Oil

Sulfonated acrylate esters have been synthesized by using renewable raw materials such as fatty alcohols of Al‐Ceder oil. Mixed fatty acids were isolated from Al‐Ceder oil by hydrolysis; both saturated and unsaturated fatty acids were isolated from the mixed fatty acids. The methyl esters of mixed fatty acid, saturated and unsaturated acids of Al‐Cedre oil were subjected to reduction with (LiAlH4) to give the corresponding fatty alcohols. The products of the reduction process were saponified and the hydroxyl values were estimated to further confirm the reduction occurrence. The acrylate esters were synthesized by esterification of acrylic acid with fatty alcohols of C_16:0, C_18:0, C_18:1, and C_18:2 mixed saturated, mixed unsaturated and mixed fatty acids of Al‐Cedre oil, respectively. This esterification was followed by addition of NaHSO₃ to form bisulfite adducts. The structures of the prepared surfactants were characterized by IR and ¹HNMR spectroscopy. A series of useful surface parameters, stability towards acids and base hydrolysis and calcium stability have been determined.     

Chemical Composition and Nutritional Characteristics of the Seed Oil of Wild <Emphasis Type="Italic">Lathyrus</Emphasis>, <Emphasis Type="Italic">Lens</Emphasis> and <Emphasis Type="Italic">Pisum</Emphasis> Species from Southern Spain

The fatty acid composition of the seed oil of 19 wild legume species from southern Spain was analyzed by gas chromatography. The main seed oil fatty acids ranged from C_14:0 to C_20:0. Among unsaturated fatty acids, the most abundant were linoleic, oleic and linolenic acids, except for Lathyrus angulatus, L. aphaca, L. clymenum, L. sphaericus and L. nigricans where C_18:3 contents were higher than C_18:1 contents. Palmitic acid was the most abundant saturated acid in studied species, ranging from 11.6% in Lathyrus sativus to 19.3% in Lens nigricans. All studied species showed higher amounts of total unsaturated fatty acids than saturated ones. Among studied species, the ω6/ω3 ratio was variable, ranging from 2.0% in L. nigricans to 13.8% in L. sativus, there being eight species in which the ω6/ω3 ratio was below 5. The fatty acids observed in these plants supports the use of these plants as a source of important dietary lipids.     

Characterization of the carbonyl compounds in reverted soybean oil1,2,3

Twenty-one mono-carbonyl compounds were identified in a reverted but not rancid soybean oil with a peroxide number of 2.7 meq/kg and a flavor score of 6.0. Six of the carbonyl compounds were saturated methyl ketones, ten were saturated aldehydes and five were 2-enals. The amount of 2,4-dienals in the reverted soybean oil was too small to be fractionated and identified. One fraction of the 2,4-dinitrophenylhydrazones of mono-carbonyl compounds obtained was different in chemical properties from those of the four known classes of compounds; viz. saturated aldehydes, saturated ketones, 2-enals, and 2,4-dienals. The chemical identity of this fraction has not been completely established. The technique used for the identification of the mono-carbonyl compounds consisted of essentially five steps: (a) passing a hexane solution of the soybean oil through a celite column, which was homogeneously impregnated with 2,4-dinitrophenylhydrazine and phosphoric acid, in order to convert quantitatively all the carbonyl compounds in the oil into their 2,4-dinitrophenylhydrazones; (b) removing the soybean oil from the solution with a Seasorb-Celite Column; (c) removing decomposition products and 2,4-dinitrophenylhydrazones of ketoglycerides with an Alumnia Column; (d) separating, by adsorption chromatography, the 2,4-dinitrophenylhydrazones of mono-carbonyl compounds into four classes; viz. saturated ketones, saturated aldehydes, 2-enals, and 2,4-dienals; and (e) identifying the individual components in each class of compounds by the Rf values of liquid-liquid partition chromatography. Supported by a research grant from the National Soybean Processors Association and Soybean Council of Am. Presented at the AOCS meeting in Chicago, Ill., 1961. Paper of the Journal Series, New Jersey Agricultural Experiment Station. Rutgers Univeriity, the State University of N. J., Department of Food Science, New Brunswick.     

GC-FID/MS Analysis of Fatty Acids in Indian Cultivars of Moringa oleifera: Potential Sources of PUFA

In the present investigation, the fatty acid profile was analysed in vegetative and reproductive parts of eight commercially cultivated Indian cultivars of Moringa oleifera and verified by gas chromatography mass spectra. In leaves, α-linolenic acid (C_18:3, cis-9,12,15) was found in the highest quantity (49–59 %) followed by palmitic acid (C_16:0) (16–18 %), and linoleic acid (C_18:2, cis-9,12) (6–13 %). The total content of saturated fatty acids and unsaturated fatty acids showed a ratio of 0.33 (cv. DHANRAJ) to 0.39 (cv. PKM-2) in leaves, 0.53 in flowers and 0.56 in tender pods. Similarly, polyunsaturated fatty acids and total monounsaturated fatty acids were found in a ratio of 5.68 (cv. DHANRAJ) to 9.71 (cv. CO-1) in leaves, 1.11 in flowers and 2.79 in tender pods. The total lipid content was recorded in the range of 1.92 % (flowers) to 4.82 % (leaves, cv. CO-1). When considering health benefits, M. oleifera leaves contain low amounts of saturated fatty acids, a high mono- and polyunsaturated fatty acid content, which can enhance the health benefits of Moringa-based products.     

The Effects of Insect Extracts and Some Insect-Derived Compounds on the Settling Behavior of Liposcelis bostrychophila

Extracts of whole booklice (Liposcelis bostrychophila)—sequentially extracted in hexane and aqueous 80% methanol (80%MeOH)—repel conspecifics. A methanol-soluble fraction (MFr) of the 80% methanol extract was more repellent than either its corresponding water fraction (WFr) or the hexane extract. The repellent effect of the MFr was repeatable across extracts prepared on different occasions over a 1 month period. Gas chromatography, mass-spectrometry (GC-MS) analyses showed that saturated (C₁₆; C₁₈) monoenoic (C_16:1; C_18:1) and a dienoic fatty acid (C_18:2) and the corresponding methyl esters of all but C_16:1 and C₁₈ constituted approximately 95% and 30%, of the detected compounds in the methanol fractions and the hexane extract, respectively. Qualitative thin layer chromatography showed that cholesterol was present in methanol fractions and the hexane extract, and also enabled tentative identification of triacylglycerols and phospholipids in the methanol fractions. Extracts of wheatgerm, dried skimmed milk powder, active yeast, and wholemeal flour—L. bostrychophila dietary components—were analyzed by GC-MS, and C₁₆, C_18:1 and C_18:2 were detected, indicating that C₁₈ and the methyl esters were not directly extractable and/or that they were products of booklice metabolism. A fatty acid amide (stearamide) previously identified in cuticular extracts of L. bostrychophila was not detected, and therefore was not responsible for the observed biological activity. Pure fatty acids and fatty acid methyl esters repelled settling of L. bostrychophila at 10 mM, with the exception of palmitic and stearic acids, indicating, among other things, a difference between the efficacy of saturated and unsaturated fatty acids. The effect of concentrations <10 mM was less significant, although palmiteoleic acid appeared to be attractive to L. bostrychophila at 0.1 mM. Fatty acids and fatty acid methyl esters were at a much lower concentration than 10 mM in the repellent methanol fractions, indicating that an interaction between known and as yet unidentified compounds is likely. The significance of fatty acids in relation to the biology and behavior of L. bostrychophila and their potential for use in traps and monitoring are discussed.     

Distribution of individual fatty acids in the crystallization fractions of lard

Distribution of the individual fatty acids in the triglycerides of lard was determined by fractional crystallization, partial enzymatic hydrolysis with steapsin, and fatty acid analyses by GLC. It was found that none of the individual fatty acids corresponded to a random distribution in the crystallization fractions, but that the distribution of the total saturated and total unsaturated acids was very nearly random. The short chain fatty acids, C₁₄ and C₁₆, both saturated and unsaturated, were found to be more predominant in the 2-position than in the 1- and 3-positions of the lard triglycerides. All of the C₁₈ fatty acids were found to be more predominant in the 1- and 3-positions.     

Fatty acids of bovine milk glycolipids and phospholipids and their specific distribution in the diacylglycerophospholipids

Milk lipids were fractionated by silicic acid column chromatography and preparative thinlayer chromatography (TLC). Ceramide monohexoside (CMH), ceramide dihexoside (CDH), phosphatidyl ethanolamine (PE), phosphatidyl choline (PC), phosphatidyl serine (PS), and sphingomyelin (Sph) were isolated, and the purity of each was checked by infrared spectroscopy and TLC. The diacylphospholipids were hydrolyzed with phospholipase A and the products separated by TLC. Fatty acid methyl esters were prepared from the various fractions and analyzed by gas chromatography. The glycolipids, CMH and CDH, and Sph contained large amounts of long-chain saturated fatty acids, especially C_22:0, C_23:0, and C_24:0, PE, PS, and PC contained C₁₀-C₂₂ normal and branched-chain saturated fatty acids, and C₁₅-C₂₀ unsaturated fatty acids (mainly monoenes). The distributions of saturated acids between the α′- and β-positions were respectively: PE, 46 and 11%; PS, 65 and 19%; and PC, 72 and 53%. PC was exceptional in that there was 10.8% myristic acid in the β-position and only 5.6% in the α′-position. PE and PS were similar in composition except that in PE oleic acid was evenly distributed, and in PS was largely in the β-position. In general, PC was much more saturated than PE or PS, and there was no overall pattern governing the specific distribution of the fatty acids in the three diacylphospholipids. Comparison with PC from other bovine tissues and from egg lecithin showed that fatty acids are located much less specifically in milk phospholipids than in PC from other sources. Presented at the AOCS Meeting, Houston, Texas, April, 1965.     

Supercritical Carbon Dioxide Fractionation of Anhydrous Milk Fat

Supercritical carbon dioxide was used to fractionate anhydrous milk fat. Six fractions were produced at 40, 50 and 60 °C using pressure values of 10, 20, 25, 30, 33 and 36 MPa. The fractions were analyzed for fatty acids, thermal behavior, iodine and color values. Composition and yield of fatty acid methyl esters were evaluated at different fractionation conditions in relation to the original milk fat values. Short chain fatty acids (C₄–C₈), medium chain fatty acids (C₁₀–C₁₄) and total saturated fatty acids were decreased from fraction obtained in the order of 10–36 MPa, while long chain fatty acids (C₁₆–C_18:2) and total unsaturated fatty acids were increased. Fractions obtained in the raffinate stage of the fractionation exhibited higher melting behavior that obtained at the low CO₂ pressures. The higher iodine value of raffinate fraction indicated that fraction was richer in oleic acid. Fractions produced at low pressures had lower melting behavior than those obtained at high pressures. Yellowness Index and b* values increased in raffinate fraction due to concentration of carotenoids.     

Component fatty acids of marine fish liver oils

Summary 1. Two liver oils (Elasmobranch) fromCarcharias melanopterus andPristis cuspidatus, caught off the Madras coast are studied, and their component fatty acids are reported. 2. The mixed acids were separated into three groups (varying unsaturation) of acids, and their methylesters were fractionated. 3. The liver oils are found to belong to the fourth group of Tsujimoto’s classification of Elasmobranch fish liver oils.Carcharias melanopterus liver oil contains 31.1% unsaturated acids (myristic 3.1, palmitic 18.4, stearic 9.5, and 0.1% arachidic) and 68.9% unsaturated acids (C₁₆ 10.8, C₁₈ 19.7, C₂₀ 15.2, C₂₂ 17.1, C₂₄ 5.3%, and traces of C₁₄ monoethenoid).Pristis cuspidatus liver oil contains 36.9% saturated acids (myristic 1.2, palmitic 22.9, stearic 12.7, and arachidic 0.1%) and 67.1% unsaturated acids (C₁₆ 8.2, C₁₈ 28.5, C₂₀ 16.4, C₂₂ 5.2, C₂₄ 4.6%, and traces of C₁₄ monoethenoid). The unsaturations of the different groups of acids are almost of the same order. 4. The abnormal content of saturated acids can be explained by the process of bio-hydrogenation. The relatively less amount of saturated acids inCarcharias melanopterus liver oil along with its higher content of polyethylenic acids (C₂₀ and above) points strongly to the possible presence of intermediate types of fats among the four groups of Elasmobranch oils.     

Measurement oftrans and other isomeric unsaturated fatty acids in butterand margarine

A procedure is described for gas liquid chromatographic determination of cis andtrans isomers of unsaturated fatty acids after fractionation of the saturated, monenoic, dienoic, and polyenoic fatty acid methyl esters by argentation thin layer chromatography. To test its reliability, the procedure was used for quantitative measurement of transisomers of unsaturated fatty acids in a known mixture of simple triglycerides containing saturated fatty acids from 4:0 to 24:0 andcis andtrans isomers of 14:1. 16:1, 18:1, and 18:2. Results of the analyses of five margarine and five butter samples are presented, together with results of infrared spectrophotometric analyses fortrans fatty acid concentrations, ultraviolet spectrophotometric analyses for conjugated fatty acid concentrations, and enzymatic analyses forcis-cis-methylene interrupted fatty acid concentrations. The combined argentation thin layer and gas Chromatographic procedure is suitable for determination of the principal fatty acids in complex food lipids such as milk fat.     

Fractional vacuum distillation of herring oil methyl esters

Methyl esters of a Canadian Atlantic herring oil containing 62% monoethylenic fatty acids were subjected to batch fractional distillation under vacuum on a pilot plant scale, to study the feasibility of fractionating fatty acid esters of marine oils of low iodine value into monounsaturated fractions with increased commercial value for industrial chemical uses. A total of 64 methyl ester fractions were collected and analyzed by gas liquid chromatography. Recoveries of the major saturated and monounsaturated acids were close to 100%, and some fractions contained over 90% of the desired 22:1 long chain monounsaturated acids. The short chain polyunsaturated acids were recovered in good yields, but the long chain highly unsaturated acids were recovered in yields of 60% or less due to oxidative and thermal decomposition in the particular apparatus employed. If small amounts of unsaturated acids are acceptable, fractional distillation of low iodine value marine oils could inexpensively supply fractions with high concentrations of methyl esters of longer chain (C₂₀ and C₂₂) monounsaturated and shorter chain (C₁₄) saturated acid or (C₁₆) saturated-monounsaturated acid mixture.     

Nachweis gesättigter cycloaliphatischer und aromatischer Fettsäuremethylester durch Dünnschicht- und Gas-Chromatographie

Detection of the Methyl Esters of Saturated Cycloaliphatic and Aromatic Fatty Acids with Thin-layer and Gas Chromatography Homologous series of methyl esters of saturated cycloaliphatic (CFA) and aromatic fatty acids (AFA), which were prepared by the alkali isomerisation of fish oil followed by hydrogenation and fractionation of the cyclised mixture as well as with the help of cyclising hydrogenation, were analysed by thin-layer and gas chromatography. Even 0.4% CFA and AFA, which do not form urea-adducts, can be detected in the fractions as a substance class in thin-layer chromatography. The equivalent carbon numbers (stearic acid = 18) of the principal isomers of CFA and AFA homologues (C₁₈ to C₂₂), which were obtained as a class in the thin-layer chromatographic separation, were determined by the gas chromatography.     

Preparation and properties of fully esterified erythritol

Pure tetraesters of erythritol with C₁₀, C₁₂, C₁₄, C₁₆, C₁₈ saturated, and C_18:1 unsaturated (oleoyl) fatty acyl chains have been prepared for the first time and characterized using the acylating systems fatty acid/N,N′‐dicyclohexylcarbodiimide/4‐dimethylaminopyridine (DMAP), fatty acid anhydride/DMAP, fatty acyl chloride/pyridine, and fatty acyl chloride/boron trifluoride etherate. For the first three systems the yields were in the range of 80–90% while the fatty acyl chloride/pyridine system has the advantage of lower cost. The fatty acyl chloride/boron trifluoride etherate system gave lower (ca 70%) yields of the tetraesters. The tetraesters of erythritol may have applications analogues to those of triglycerides. In addition, new applications can be envisaged for these compounds, as a result of their differences in physical, chemical, and biochemical properties compared to triglycerides. Practical applications: The tetraesters of erythritol with saturated fatty acyl chains may have applications analogous to those of saturated triglycerides. However, tetraesters with unsaturated fatty acid chains may have greater prospects of having industrial uses after doing chemistry on the carbon–carbon double bonds.     

Neutral lipids of chickpea flour and protein isolates

The neutral lipids composition of defatted chickpea flour and two types of protein isolates has been studied. The main compounds in neutral lipids are triacylglycerols, free fatty acids, and diacylglycerols. Other compounds present are wax esters, free fatty alcohols, and free sterols. The main fatty acids in neutral lipids are C_18:2 and C_18:1 among the unsaturated, and C_16:0 and C_18:0 among the saturated acids. Free and esterified alcohols range from C_16:0 to C_28:0, the majority being those with an even number of carbon atoms. Sterols observed are β-sito-sterol, campesterol, stigmasterol, and δ-5-avenasterol. Triacyl-glycerols are partially hydrolyzed, and the amounts of unsaturated sterols and unsaturated fatty acids are reduced as a result of the chemical treatment during production of the protein isolates.     

Reactions of dimethyl sulfoxide with sulfonate esters of fatty alcohols. I. Synthesis of higher saturated and unsaturated fatty aldehydes

Long-chain saturated fatty aldehydes (C₁₀ to C₁₈), as well as the C₁₈ unsaturated aldehydes (oleyl, linoleyl, and linolenyl), were synthesized in good yields by the selective oxidation of the sulfonate esters of the corresponding alcohols with dimethyl sulfoxide in the presence of sodium bicarbonate. Chromatographic procedures for the isolation of the pure aldehydes from the reaction mixtures are described. The purity of the aldehydes was ascertained by thin-layer chromatography, melting points of their 2,4-dinitrophenyl hydrazones, infrared spectra and other physical methods. Presented at the AOCS Meeting in Houston, April, 1965.     

Die Trennung und Identifizierung der 2,4-Dinitrophenylhydrazone ungesättigter Aldehyde und Methylketone mittels Dünnschicht-Chromatographie

Separation and Identification of 2,4-Dinitrophenylhydrazones of Unsaturated Aldehydes and Methylketones by Thin-Layer Chromatography The unsaturated aldehydes and ketones formed in small amounts by autoxidation of oils and fats were separated as their 2,4-dinitrophenylhydrazones by a combination of partition, adsorption and AgNO₃-thin-layer chromatography.     

Characterization of skin-surface lipids from the monkey (Macaca fascicularis)

Skin-surface lipids from the monkeyMacaca fascicularis are composed of sterol esters (38%), cholesterol (4%) and two types of wax diesters, identified as Type II (IIa and IIb, 17% and 40%, respectively). Type IIa contained diesters of 1,2-alkanediols esterified with two molecules of long-chain (C₁₄−C₃₄) fatty acids having straight and branched chains. In the diesters IIa, fatty acids shorter than C₁₉ predominated in position 1, and fatty acids longer than C₂₀ predominated in position 2. Type IIb contained diesters of 1,2-alkanediols esterified with C₄ and C₅ branched-chain fatty acids (predominantly isovaleric acid) at position 1 and long-chain (C₁₄−C₂₇) acids, having straight and branched chains, at position 2. The shortchain acids were converted to 2-nitrophenylhydrazides and analyzed by high-performance liquid chromatography (HPLC). Ammonia chemical ionization (CI)-gas chromatography (GC)-mass spectrometry (MS) resolved the intact diesters IIb into 12 peaks corresponding to molecular weights ranging from 597 to 748, and showed that the molecular species, such as C₂₁−C₁₆−C₅ (diol, fatty acid in position 2, fatty acid in position 1), C₂₂−C₁₆−C₅ and C₂₃−C₁₆−C₅, were prevalent. The fatty acids from both diesters were mostly (>98%) saturated. The 1,2-alkanediols from both diesters consisted of C₁₆−C₂₆ saturated straight- and branched-chain components. The acyl groups of sterol esters contained 86% C₁₄−C₃₄ branched-chain acids. The unsaturated fatty acids (5.4%) belonged to a straight-chain monoenoic series having extremely long chains (C₁₈−C₃₄). The branched-chain structures in the fatty acids and diols were iso and anteiso. These results show the species-specific profile for the skin-surface lipid synthesis.