Nonglyceride complex of the seed oil ofOnopordum acanthium

Extraction of the comminuted seeds has yielded an oil from which have been isolated: C₃₃-C₂₅, C₁₈ and C₁₇ paraffinic hydrocarbons, C_18:1, C_18:2, C_18:3, C_17:1, C_17:2 and C_17:3 olefinic hydrocarbons, ethyl esters of C_32:0, C_31:0, C_30:0, C_29:0, and C_28:0 fatty acids, sterols with molecular weights of 414, 412, and 400, and the alcohols α-amyrin and lupeol with their natural acetates. Extraction of the uncomminuted seeds has shown that the paraffinic hydrocarbons, ethyl esters, and alcohol acetates pass into the oil from the husks of the seeds. This is the first time that the C_31:0 and C_29:0 fatty acids have been detected as natural compounds, and it is the first time that the ethyl esters of C₃₄, C₃₃, C₃₂, C₃₁, and C₃₀ fatty acids have been isolated from seed oils of higher plants.     

Nonglyceride lipids of the seed coats ofArtemisia absinthium andOnopordum acanthium

The seed coats ofArtemisia absinthium andOnoporum acanthium have been shown to contain paraffinic hydrocarbons (C₃₁-C₂₅ and C₃₁-C₂₇, respectively), wax esters (C₃₂-C₂₃ and C₅₁-C₃₃), acetyltriterpenols (six types, five types), and acyltriterpenols with a predominance of palmitoyltriterpenols (esters of higher saturated unbranched C_32:0-C_12:0 fatty acids and triterpenols with a molecular weight of 426 belonging to the ursene group).Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 154–157, March–April, 1981.     

Analysis of thermal,oxidative and cold flow properties of methyl and ethyl esters prepared from soybean and mustard oils

Oilseed crop with high oil content and promising ecological adaptability are potential sources for competitive biodiesel production. This study investigates the scope of utilizing biodiesel development through the methyl and ethyl ester from soybean and mustard oil as an alternative fuel. Methyl and ethyl esters of oils having different fatty acids compositions such as soybean (SOME and SOEE) and mustard oil (MUME and MUEE) were prepared by transesterification with methanol and ethanol in the presence of an alkali-KOH catalyst. The gas chromatographic (GC) analysis of oil samples revealed that primary fatty acid composition in soybean oil was linoleic acid (C_18:2, 51.93%), followed by oleic acid (C_18:1, 22.82%), palmitic acid (C_16:0, 11.56%), linolenic acid (C_18:3, 5.95%) and stearic acid (C_18:0, 4.32%). Whereas, the main components in mustard oil were erucic acid (C_22:1, 32.81%), oleic acid (C_18:1, 24.98%), eicosenoic acid (C_20:1, 10.44%), linolenic acid (C_18:3, 8.61%) and palmitic acid (C_16:0, 2.80%). The physicochemical properties (acid value, iodine value, calorific value, flash point, pour point etc.) of methyl and ethyl ester samples were estimated and found to be within the acceptable range of ASTM D6751 standards specifications. The prepared esters and oil samples were examined for cold flow properties by differential scanning calorimetry (DSC). Results revealed better cold flow properties for MUME (−2.55 °C) and MUEE (−3.10 °C) than SOME (3.21 °C) and SOEE (1.83 °C) due to more unsaturated fatty acid content in MU. Thermal and oxidative stability of samples was determined by thermogravimetric analysis (TG) and differential thermal analysis (DTA). The thermal and oxidative stability ranking of the samples was in the order of oil > methyl esters > ethyl esters.

     

Evaluation of vinasses from sugarcane molasses distillation as a new source of sugarcane wax

Molasses, a by-product of sugar manufacturing, are the most common raw material for rum manufacturing. During the fermentation and distillation process, vinasses are produced in large quantities and disposed in landfills. In this study, they were evaluated as a new source of sugarcane wax. The chemical composition of the wax was studied by GC-Mass spectroscopy. A series of n-alkanes (C₂₃–C₃₃) and ethyl and methyl esters of fatty acids (palmitate and oleate are the predominant), of phytosterols (stigmasterol, β-sitosterol, campesterol), free fatty acids (C_12:0–C_36:0), and triglycerides constitute the main components. In addition, 2-ketones (C₂₇–C₃₃), aldehydes (C₂₈, C₃₂, C₃₄), ketosteroids (derivatives of stigmasterol, β-sitosterol, and campesterol), and fatty alcohol acetates (alcohol moiety: C₂₈, C₃₀, C₃₂) were found as minor products. Published in Khimiya Prirodnykh Soedinenii, No. 5, pp. 448–450, September-October, 2008. Original article submitted March 19, 2007.     

Lipids of the petals ofCarthamus tinctorius

The following compounds have been identified in the lipids of the petals ofCarthamus tinctorius: C₃₂ and C₂₉ isoparaffins; free fatty acids, the main component of which is palmitic acid; 33 esters of phytol, esterified with three groups of fatty acids — paraffinic, isoparaffinic, and monoenoic of the C₉–C₂₆ series; and β-sitosterol and its β-D-glucopyranoside.     

HPLC of fatty acid esters of mono- and polyhydric alcohols. Part 1: Analytical separation

This paper shows how simply and yet very rapidly fatty acid esters of monohydric alcohols, but particularly partial and full fatty acid esters of fully hydric alcohols can be separated and determined by means of high-pressure liquid chromatography on LiChrosorb RP-8 with methanol/water. We have separated quantitatively the methylesters of the fatty acids C_8:0 to C_22:0 and C_24:0, the i-propyl-, i-butyl-, n-hexyl- and i-octyl-esters of the even-numbered fatty acids C_8:0 to C_18:0, mono- and difatty acid esters of the 1,3-bis-(2-hydroxyethyl)-5,5-dimethyl-hydantoin, mono-, di- and triesters of the trimethylolpropane as well as the tetraesters of the penta-erythrite.     

Separation of Fatty Acids as Their p-Bromophenacyl Esters on a C30-Bonded Silica Column by High Performance Liquid Chromatography

Abstract

A new C₃₀-bonded silica column was developed for high performance liquid chromatography. This column was tested for the fractionation of fatty acids as their p-bromophenacyl esters by the reverse-phase mode. Certain pairs of fatty acid esters that are very difficult to separate on a C₁₈-bonded silica column, i. e., arachidonic (C₂₀:4)-palmitoleic (C₁₆:1); elaidic (trans C₁₈:1)-vaccinic (cis C₁₈:1); behenic (C₂₂:0)-nervonic (C₂₄:1); and arachidonic (C₂₀:0)-erucic (C₂₂:1) esters, were completely resolved on the C₃₀-bonded column using solvent gradients of acetonitrile: water and acetonitrile: p-dioxane. A solvent system of methylene chloride: acetonitrile (2:1, v/v) was developed for this column to achieve good separation of a homologous series of extremely nonpolar C₇₆ to C₈₂ α-mycolic acid esters from Mycobacterium tuberculosis H37Ra.     

Rapid analysis of free medium-chain fatty acids and related ethyl esters in beer using SPE and HRGC

A modification of a procedure by Hage [1] is proposed for the gas chromatographic evaluation of the content of free medium-chain fatty acids and related ethyl esters in beer. The method involves extraction of free fatty acids and ethyl esters by SPE using C₁₈ bonded phase columns, derivatization of free fatty acids and related ethyl esters with diazomethane, and GC analysis using an SP-2340 capillary column. The results obtained have shown the method to be rapid and highly reproducible. The technique has been compared with other methods used for determination of free fatty acids.     

Lipids of the fruit of Feijoa sellowiana

The composition and amounts of liposoluble substances in the flesh and peel of feijoa fruit has been investigated. About 30 groups of lipid substances have been identified. The main groups of lipids in the flesh were triacylglycerols, sterols, cerebrosides, ceramide phosphate inositol oligosides, sulfoquinovosyldiacylglycerols, phosphatidic acids, phosphotidylglycerols and phosphatidylcholines. In the peel, hydrocarbons, sterols, esters of fatty acids and lower alcohols, cerebrosides, digalactosyldiacylglycerols, ceramide oligosides, phosphatidylglycerols, and include predominated. The fatty acids of the flesh were found to include 15 representatives (C_12:0–C_28:0), and those of the flesh 11 representatives tives (C_12:0–C_18:3).M. V. Lomonosov Technological Institute of the Food Industry, Odessa. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 464–467, July–August, 1991.     

Lipids of the fruit of Feijoa sellowiana

The composition and amounts of liposoluble substances in the flesh and peel of feijoa fruit has been investigated. About 30 groups of lipid substances have been identified. The main groups of lipids in the flesh were triacylglycerols, sterols, cerebrosides, ceramide phosphate inositol oligosides, sulfoquinovosyldiacylglycerols, phosphatidic acids, phosphotidylglycerols and phosphatidylcholines. In the peel, hydrocarbons, sterols, esters of fatty acids and lower alcohols, cerebrosides, digalactosyldiacylglycerols, ceramide oligosides, phosphatidylglycerols, and include predominated. The fatty acids of the flesh were found to include 15 representatives (C_12:0–C_28:0), and those of the flesh 11 representatives tives (C_12:0–C_18:3). M. V. Lomonosov Technological Institute of the Food Industry, Odessa. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 464–467, July–August, 1991.     

Homopolymers and vinyl chloride copolymers of vinyl esters of chlorinated fatty acids from umbelliferae and limnanthes douglasii

Homopolymers and copolymers of vinyl esters of chlorinated C₁₈, C₂₀, and C₂₂ fatty acids with vinyl chloride have been prepared and evaluated. The incorporation of the vinyl ester of chlorinated C₁₈, C₂₀, and C₂₂ acids as comonomers with vinyl chloride produced more flexible copolymers than have other comonomers, yet none have imparted the plasticization that can be obtained by an equal amount of external plasticizer.     

An improved derivatization method for sensitive determination of fatty acids by high-performance liquid chromatography using 9-(2-hydroxylethyl)-carbazole as derivatization reagent with fluorescence detection

Summary Tagging techniques with reagents used for fluorescent detection for short and long-chain fatty acids using high-performance liquid chromatography are evaluated in terms of the tagging reactions, handing, flexibility, stability of the reagents. Emphasis is given to the applications of the tagging techniques to relatively high molecular mass fatty acids. The fatty acids or carboxylic compounds were derivatized to their corresponding esters with 9-(2-hydroxy ethyl)-carbazole (HEC) in acetonitrile at 60°C with N, N′-carbonyldiimidazole (CDI) as a coupling agent in the presence of 4-dimethylaminopyridine (DMAP). A mixture of esters of C₁−C₂₀ fatty acids was completely separated with 45 min using gradient elution on a reversed-phase C₁₈ column. The maximum fluorescence emission for the derivatized fatty acids is at 365 nm (λ_ex 293 nm). Studies on derivatization conditions indicated that fatty acids react rapidly and smoothly with HEC in the presence of CDI and DMAP in acetonitrile to give the corresponding sensitively fluorescent derivatives. The application of this method to the analysis of long chain fatty acids in plasma is also investigated. The LC separation shows good selectivity and reproducibility for fatty acids derivatives. The relative standard deviations (n=6) for each fatty acid derivative are <5.0%. The detection limits are at 38–57 fmol levels for C₁₄−C₂₀ fatty acids and lower levels for <C₁₄ fatty acids.     

Determination of fatty acids in atmospheric samples via GC/MS

Summary Atmospheric precipitation and aerosol samples are characterized by a complex mixture of several organic compounds. A simple method for the simultaneous determination of the main compound classes by GC/MS is presented. In detail, seasonal variations of C₈–C₃₂ fatty acids in precipitation in a semirural area have been studied. Total fatty acids concentrations of 7–53 g/l were detected. Summer rain is characterized by high amounts of fatty acids >C₂₀ and lower amounts of C₁₁–C₂₀ species. Two effects may be responsible: larger emission rates of fatty acids during vegetation periods and an increased influence of vapour phase due to higher temperatures during summer. CPI values showed no general trend; lower CPI values for winter rain could not be observed. This would be expected if anthropogenic sources play an important role. Monounsaturated fatty acids (C_16:1, C_18:1) were more abundant during winter than in summer. High concentrations of polyunsaturated fatty acids (C_18:x) could be detected during summer. High relative concentrations of the potential oxidation products of the unsaturated species, nonanedioic acid and w-oxononanoic acid, are associated with relatively low concentrations of their precursors.     

Metabolites of the marine sponge <Emphasis Type="Italic">Suberites cf. aurantiacus</Emphasis>

Fractions of free sterols and sterol esters were observed in the ethylacetate extract of the marine sponge Suberites cf. aurantiacus and their compositions were determined. It was found that cholesterol was the predominant component in all sterol forms. The esters had a high content of unsaturated long-chain fatty acids (C₂₄–C₂₆). Sterol acetates have not been previously observed in marine invertebrates.     

Ammonia-treated N-(1-naphthyl) ethylenediamine dihydrochloride as a novel matrix for rapid quantitative and qualitative determination of serum free fatty acids by matrix-assisted laser desorption/ionization-Fourier transform ion cyclotron resonance mass spectrometry

The blood free fatty acids (FFAs), which provide energy to the cell and act as substrates in the synthesis of fats, lipoproteins, liposaccharides, and eicosanoids, involve in a number of important physiological processes. In the present study, matrix-assisted laser desorption/ionization-Fourier transform ion cyclotron resonance mass spectrometry (MALDI-FTICR MS) with ammonia-treated N-(1-naphthyl) ethylenediamine dihydrochloride (ATNEDC) as a novel MALDI matrix in a negative ion mode was employed to directly quantify serum FFAs. Multiple point internal standard calibration curves between the concentration ratios of individual fatty acids to internal standard (IS, C_17:0) versus their corresponding intensity ratios were constructed for C_14:0, C_16:1, C_16:0, C_18:0, C_18:1, C_18:2, C_18:3, C_20:4, and C_22:6, respectively, in their mixture, with correlation coefficients between 0.991 and 0.999 and limits of detection (LODs) between 0.2 and 5.4 μM, along with the linear dynamic range of more than two orders of magnitude. The results indicate that the multiple point internal standard calibration could reduce the impact of ion suppression and improve quantification accuracy in the MALDI mode. The quantitative results of nine FFAs from 339 serum samples, including 161 healthy controls, 118 patients with hyperglycemia and 60 patients without hyperglycemia show that FFAs levels in hyperglycemic patient sera are significantly higher than those in healthy controls and patients without hyperglycemia, and elevated FFA levels are also associated with increased levels of fasting blood glucose (FBG) in hyperglycemic patient sera. Serum FFAs were identified on the basis of the observed accurate molecular masses and reliable isotope distributions obtained by MALDI-FTICR MS.     

An Efficient Method for Determination of the Degree of Substitution of Cellulose Esters of Long Chain Aliphatic Acids

The determination of the degree of substitution (DS) of fatty acid cellulose esters, representing a broad range of substituents (C₆, C₁₂, C₁₈ and C₂₂), was performed by alkaline hydrolysis of the ester groups and the quantification of fatty acids by gas chromatography-mass spectrometry (GC-MS) as their trimethylsilyl derivatives. The method was optimized and compared with established techniques for the DS determination (elemental analysis and alkaline hydrolysis/titrimetry). The results demonstrated that alkaline hydrolysis/GC-MS is a rapid, reliable and powerful method for analysis of fatty acid cellulose esters, particularly when different acyl substituents are present.     

Lipids of the seeds ofSecurinega suffruticosa

The lipid composition of the seeds ofSecurinega suffruticosa (Euphorbiaceae) has been studied, and eight classes of lipids have been identified with a predominance of triacylglycerols; the fatty acid compositions and structures of the triacylglycerols have been determined. Among the hydroxy acids of the hydroxyacylglycerols 13 components belonging to saturated, monoenic, and dienic acids of the C₁₇, C₁₈, and C₂₀ series have been identified; 12-hydroxyheptadecanoic and 12-hydroxyeicosanoic acids are new.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 277–281, May–June, 1986.     

Combining TXRF,FT-IR and GC–MS information for identification of inorganic and organic components in black pigments of rock art from Alero Hornillos 2 (Jujuy,Argentina)

Archaeological samples are complex in composition since they generally comprise a mixture of materials submitted to deterioration factors largely dependent on the environmental conditions. Therefore, the integration of analytical tools such as TXRF, FT-IR and GC–MS can maximize the amount of information provided by the sample. Recently, two black rock art samples of camelid figures at Alero Hornillos 2, an archaeological site located near the town of Susques (Jujuy Province, Argentina), were investigated. TXRF, selected for inorganic information, showed the presence of manganese and iron among other elements, consistent with an iron and manganese oxide as the black pigment. Aiming at the detection of any residual organic compounds, the samples were extracted with a chloroform–methanol mixture and the extracts were analyzed by FT-IR, showing the presence of bands attributable to lipids. Analysis by GC–MS of the carboxylic acid methyl esters prepared from the sample extracts, indicated that the main organic constituents were saturated (C_16:0 and C_18:0) fatty acids in relative abundance characteristic of degraded animal fat. The presence of minor C_15:0 and C_17:0 fatty acids and branched-chain iso-C_16:0 pointed to a ruminant animal source. Figure Rock art painting at Hornillos 2 Cave, Susques, Argentina     

Selective deoxygenation of vegetable oils in the presence of Pt–Sn/Al<Subscript>2</Subscript>O<Subscript>3</Subscript> catalyst

We studied deoxygenation of individual fatty esters and fatty acid triglycerides from vegetable oils and lipid extracts from microalgae in the presence of catalysts prepared by deposition of Pt–Sn-containing compounds onto the γ-aluminum oxide surface. Using individual esters as an example, selective reduction of oxygen into water was demonstrated for the first time to proceed on a catalytic system at the 5 : 1 molar ratio of Sn and Pt active components to afford hydrocarbon components of substrates in virtually quantitative yield. Transformation of vegetable oil in the presence of this catalyst affords the C₃–C₁₈ hydrocarbon fraction in yield up to 99% at the content of C₃ and C₁₈ hydrocarbons up to 90%. The fraction of C₁ and C₂ hydrocarbons and carbon oxides is not higher than 0.5%. The possibility of carbon weight loss minimization during transformation of lipids was shown for the first time.     

Survival of Freeze-dried Leuconostoc mesenteroides and Lactobacillus plantarum Related to Their Cellular Fatty Acids Composition during Storage

Lactic acid bacteria strains Lactobacillus plantarum CWBI-B534 and Leuconostoc ssp. mesenteroïdes (L. mesenteroïdes) Kenya MRog2 were produced in bioreactor, concentrated, with or without cryoprotectants. In general, viable population did not change significantly after freeze-drying (p?>?0.05). In most cases, viable population for cells added with cryoprotectants was significantly lower than those without (p?16:0), palmitoleic (C_16:1), stearic (C_18:0), oleic (C_18:1), linoleic (C_18:2), and linolenic (C_18:3) acids were identified. Four of them, C_16:0, C_16:1, C_18:0, and C_18:1, make up more than 94% or 93% of the fatty acids in L. mesenteroides and L. plantarum, respectively, with another one, namely, C18:3, making a smaller (on average 5–6%, respectively) contribution. The C_18:2 contributed very small percentages (on average?≤?1%) to the total in each strain. C_16:0 had the highest proportion at most points relative to other fatty acids. Moisture content and water activity (a _w) increased significantly during the storage period. It was observed that C_16:1/C_16:0, C_18:0/C_16:0 and C_18:1/C_16:0 ratios for freeze-dried L. mesenteroides or L. plantarum, with or without cryoprotectants, did not change significantly during the storage period. According to the packaging mode and storage temperatures, C_18:2/C_16:0 and C_18:3/C_16:0 ratios for freeze-dried L. mesenteroides and L. plantarum with or without cryoprotectants decreased as the storage time increased. However, a higher C_18:2/C_16:0 or C_18:3/C_16:0 ratio for L. mesenteroides and L. plantarum was noted in the freeze-dried powder held at 4 °C or under vacuum and in dark than at 20 °C or in the presence of oxygen and light.