bluuebunny/crossref_metadata_2025_split huggingface dataset:
Oxidation of synthetic triacylglycerols containing eicosapentaenoic and docosahexaenoic acids: Effect of oxidation system and triacylglycerol structure
Authors: Endo Yasushi , Hoshizaki Sanae , Fujimoto Kenshiro 
Published: May 2007

AbstractThirteen synthetic triacylglycerols (TAG) containing eicosapentaenoic acid (EPA) or docosahexaenoic acid (DHA) were oxidized in the presence of 2,2′‐azobis(2,4‐dimethyl‐valeronitrile) (AMVN) and 2,2′‐azobis(2‐amidinopropane)dihydrochloride (AAPH) as aqueous and nonaqueous radical initiators to investigate the influence of TAG structure and oxidation system on the oxidative stability of TAG that contain highly unsaturated fatty acids (HUFA). A 2:1 (mol/mol) mixture of trieicosapentaenoylglycerol and tripalmitoylglycerol was most susceptible to the AMVN‐initiated oxidation among three types of TAG that contained EPA and palmitic acid (2:1, mol/mol). Compared with 1,2 (or 2,3)‐dieicosapentaenoyl‐3(or 1)‐palmitoylglycerol (EEP) and 1,3‐dieicosapentaenoyl‐2‐palmitoylglycerol (EPE), the oxidative rate of EEP was somewhat higher. A similar result was obtained for DHA‐containing TAG. The oxidative rate of TAG that contained EPA and palmitic acid (1:2, mol/mol) showed a positive correlation with the amount of EPA in a single TAG molecule. Moreover, in the nonaqueous system, the oxidative rate of EPA‐containing TAG was affected by unsaturation and carbon chainlength of constituent fatty acids. In the AAPH‐initiated oxidation in the aqueous system, the oxidative rate of TAG with EPA and palmitic acid was higher with the increased quantity of EPA in a single TAG molecule. Also, constituent fatty acids modified the oxidative rate of EPA‐containing TAG in an aqueous system. The glycerol position of EPA and DHA also affected the oxidative rate of the TAG. EPA and DHA located at the 1,2 (or 2,3)‐position of glycerol were more oxidizable than those at the 1,3‐position during AAPH‐initiated oxidation. Thus, 1,2(or2,3)‐dipalmitoyl‐3(or 1)‐eicosapentaenoylglycerol was oxidized faster than 1,3‐dipalmitoyl‐2‐eicosapentaenoylglycerol. These observations suggest that the oxidative stability of TAG that contain HUFA could be modulated by the oxidation system and TAG structure.
Antioxidant activity of mung bean hulls
Authors: Duh Pin‐Der , Yen Wen Jye , Du Pin‐Chan , Yen Gow‐Chin 
Published: May 2007

AbstractThe antioxidant activity of methanolic extracts of mung bean hulls was investigated. Extracts at a concentration of 100 ppm exhibited stronger antioxidant activity than 100 ppm dl‐α‐tocopherol (Toc) or 100 ppm butylated hydroxyanisole on the peroxidation of linoleic acid. Moreover, a synergistic effect was observed when 100 ppm of the extract was mixed with 100 ppm Toc. Also, the extracts showed good inhibitory activity in soybean oil oxidation, which was examined by peroxide value, thiobarbituric acid, and gas chromatography of oxidized fatty acid methyl esters. The extracts can reduce the formation of both primary and secondary oxidation products of soybean oil. The extracts had reducing power and scavenged 1,1‐diphenyl‐2‐picrylhydrazyl radical, which may in part be responsible for their antioxidant activity. Based on the results obtained, mung bean hulls are a potential source of natural antioxidants owing to their marked antioxidant activity.
Quality and consumption of oxidized lipids from deep‐frying fats and oils in New Zealand
Authors: Lake R. J. , Scholes P. 
Published: May 2007

AbstractSamples of beef dripping and plant oil‐based deep‐frying fat were obtained from fast‐food premises in Christchurch, New Zealand, as well as samples of deep‐fried battered fish and potato chips. The fat in these samples was analyzed for level of oxidation by measuring acid value, peroxide value, polar compounds, thiobarbituric acid‐reactive substances (TBARS), and conjugated dienes. The acid and peroxide value results were contradictory when compared with limits set in the New Zealand Food Regulations 1984, but the levels of polar compounds were generally below 25%, indicating that the fats were well maintained. The TBARS and conjugated diene levels were compared with those for oxidized corn oil used in a feeding trial and indicated a similar oxidation level, although the amount of fat consumed in the feeding trial would be 30–50% higher. These results show that well‐maintained deep‐frying fat has oxidation levels sufficient to cause elevation of plasma lipid oxidation levels as observed in a human feeding trial.
Characterization of olive oil produced with a new enzyme processing aid
Authors: Ranalli Alfonso , De Mattia Gabriella 
Published: May 2007

AbstractBy carrying out olive oil extraction experiments with three olive varieties (Dritta, Coratina, and Leccino), a new processing cytolase enzyme aid was tested. The oils, obtained with the enzyme adjuvant upon extraction, were characterized (with respect to reference oils) by: (i) relatively higher content of natural antioxidants (free and linked phenols, ortho‐diphenols, tocopherols), trans‐2‐hexenal, total aromatic substances, chlorophyllic pigments, and steroid hydrocarbons; (ii) slightly lower content of aliphatic alcohols, triterpene alcohols, triterpene dialcohols, β‐sitosterol, and total sterols; (iii) slightly higher values of integral color index, resistance to autoxidation, and global quality indices; (iv) lower values of carotenoid color index, alcoholic index and some qualitative ratios, such as trans‐2‐hexenal/hexanal, trans‐2‐hexenal/total aroma, campesterol/stigmasterol; and (v) a higher sensory score. Hence, they exhibited better overall qualitative characteristics. The enzyme adjuvant, in addition, led to higher oil extraction outputs.
Polymorphic behavior of gondoic acid and phase behavior of its binary mixtures with asclepic acid and oleic acid
Authors: Sato K. , Yano J. , Kawada I. , Kawano M. , Kaneko F. , Suzuki M. 
Published: May 2007

AbstractMolecular properties of polymorphic forms of gondoic acid [cis‐C20:1Δ11ω9 (GOA)] have been studied by X‐ray diffraction (XRD), differential scanning calorimetry (DSC), optical microscopy, and Raman scattering, in comparison to those of six principal unsaturated fatty acids: oleic acid [cis‐C18:1Δ9ω9 (OA)], erucic acid [cis‐C22:1Δ13ω9 (ERA)], petroselinic acid [cis‐C18:1Δ6ω12 (PSA)], asclepic acid [cis‐C18:1Δ11ω7 (APA)], palmitoleic acid [cis‐C16:1Δ9ω7 (POA)], and elaidic acid [trans‐C18:1Δ9ω9 (ELA)]. In addition, phase behavior of binary mixtures of GOA and APA and OA was examined by XRD and DSC. The polymorphic structures of GOA are quite similar to those of APA, ERA, POA, and partly to OA. In particular, DSC and Raman scattering studies have shown that gondoic acid exhibits conformational disordering on heating at the ω‐chain, a chain segment between the double bond and CH3 group, as a transition from all‐trans (γ form) to gauche‐rich (α form) conformations. A miscible mixing phase was observed in the mixture of GOA and APA, yet eutectic phases were observed in the GOA and OA mixtures. This is a remarkable contrast because the binary mixture systems of varying combinations of cis‐unsaturated fatty acids examined so far exhibited either eutectic nature or molecular compound formation. It is expected that specific molecular interactions between GOA and APA that originate from the equivalence of the length of the Δ‐chain, the chain segment between the cis‐double bond and COOH group, and also from the presence of the γ‐α order‐disorder transformation would be operating to form the miscible mixing phase.
Gradients of n‐heptane and acetonitrile in silver‐ion high‐performance liquid chromatography analyses of cis and trans bonds in lipids
Authors: Elfman‐Börjesson Inger , van den Hark Sander , Härröd Magnus 
Published: May 2007

AbstractCis and trans isomers of fatty acid methyl esters, fatty alcohols, and triacylglycerols were analyzed with a silverion high‐performance liquid chromatography system. Gradients of n‐heptane and acetonitrile were used to elute molecules with up to nine cis double bonds. The analyses were as fast and reliable and had a resolution similar to that of the best published analyses. However, published analyses were performed with chlorinated solvents, and these solvents are carcinogenic and mutagenic. The solvents we used, heptane and acetonitrile, are less dangerous to the analyst.
Offset printing inks based on rapeseed and sunflower oil. Part I: Synthesis and characterization of rapeseed oil‐and sunflower oil‐modified alkyd resins
Authors: Sabin Pascale , Benjelloun‐Mlayah Bouchra , Delmas Michel 
Published: May 2007

AbstractTwo sets of alkyd resins of variable oil lengths with the required properties for offset printing ink formulations, modified by sunflower and rapeseed oil, were synthetized according to the “monoglyceride” process. The influence of the acyl composition of the modifying vegetable oil and of the oil content on alkyds’ properties was determined by detailed chemical and rheological characterization. Molecular structure, size, and molecule size distribution appeared to be linked to these two factors. A comparative study with two usual linseed oil‐modified alkyds led to determination of the more appropriate alkyds for applications in offset varnishes.
Effect of lecithin on organogel formation of 12‐hydroxystearic acid
Authors: Tamura T. , Ichikawa M. 
Published: May 2007

AbstractOptically active 12‐d‐hydroxystearic acid (12‐HSA) gives a thermally reversible organogel in several organic solvents. When a small amount of lecithin coexists with 12‐HSA in organic solvents, the mechanical strength of the organogel is remarkably reduced. Interaction of lecithin with 12‐HSA was studied by using infrared (IR) spectrometry, nuclear magnetic resonance (NMR) spectrometry, and scanning electron microscopy (SEM). Incorporating lecithin into 12‐HSA reduced the absorbance in IR spectra, derived from hydrogen bonding between the hydroxyl groups and the carboxyl groups of 12‐HSA molecules. Based on NMR measurements, the polar head groups of lecithin associate with the carboxyl groups of 12‐HSA in a 1:1 molar ratio. SEM showed that the shape of the fibrous aggregates varied from a helically extended form to a spherical form. These results suggest that intermolecular 1:1 complexes were formed between lecithin and 12‐HSA, which caused a structural change in the fibrous network in the 12‐HSA organogel and consequently induced gel deformation.
Capillary supercritical fluid chromatographic analysis of shark liver oils
Authors: Borch‐Jensen C. , Magnussen M. P. , Mollerup J. 
Published: May 2007

AbstractThe liver oils of six different shark species have been analyzed by supercritical fluid chromatography (SFC). The liver oils were from the species Pseudotriakis microdon (False catshark), Centroscymnus coelepsis (Portuguese dogfish), Centrophorus squanosus (Leafscalp gulper shark), Deanea calceus (Birdbeak dogfish), Etmopterus princips (Greater lantern shark), and Centroscymnus crepidater (Longnose velvet dogfish). The method was capable of direct quantitation of squalene and cholesterol, while quantitation of triacylglycerols, cholesterol esters, and diacylglycerol ethers required thin‐layer chromatographic fractionation prior to SFC analysis. The iodine values of the liver oil samples gave a linear correlation when plotted against the squalene content found by SFC. The variation of squalene content within one shark species is large, and there are large differences in squalene content from species to species. The squalene contents varied between 0.22 and 82.54 wt%. The identity of the glycerol ethers was investigated by SFC of the unsaponifiable matter. The major glycerol ethers contained chimyl, batyl, and selachyl alcohol.
Development of steryl ester analysis for the detection of admixtures of vegetable oils
Authors: Gordon Michael H. , Miller Luke A. D. 
Published: May 2007

AbstractThe steryl ester content and composition of 28 samples from 10 vegetable oil types have been determined by isolation of the steryl esters by high‐performance liquid chromatography and analysis by gas chromatography. The oils can be classified into oils with a high content (>4000 mg/kg) of steryl esters (corn and rapeseed); oils with a medium content (1400–2400 mg/kg) of steryl esters (sunflower oil and high‐oleic sunflower oil); and oils with a low content (<1200 mg/kg) of steryl esters (safflower, soybean, cottonseed, groundnut, olive, and palm oils). The composition of the steryl ester fraction varies to a greater extent for different oil types than for different varieties of the same oilseed. The developed method is promising for authentication of some oils, and is particularly suitable for detecting admixtures of low levels of corn or rapeseed oils.
Quantitative determination of phospholipids in sunflower oil
Authors: Carelli Amalia A. , Brevedan Marta I. V. , Crapiste Guillermo H. 
Published: May 2007

AbstractPhospholipids from sunflower oil samples were enriched by using solid‐phase extraction (SPE) cartridges and subsequently separated and analyzed by high‐performance liquid chromatography (HPLC) with an ultraviolet detector. The recovery of individual phospholipids at different total concentrations in model oils and the repeatability of the method were investigated. The results demonstrated the utility of SPE‐HPLC for quantitative analysis of phospholipids in sunflower oil and the effectiveness for concentrating, separating, identifying, and quantitating phospholipids in samples with phosphatide contents as low as 0.1%. Samples of sunflower oil at different stages of processing were analyzed, and phospholipid profiles in hexane‐extracted oil, hot‐pressed oil, and water‐degummed oils were compared.
Positional distribution of Δ5‐olefinic acids in triacylglycerols from conifer seed oils: General and specific enrichment in the sn‐3 position
Authors: Wolff Robert L. , Dareville Eric , Martin Jean‐Charles 
Published: May 2007

AbstractTriacylglycerols (TAG) were purified from the storage lipids extracted from the seeds of several conifer species (Taxus baccata, Larix decidua, Sciadopytis verticillata, and Juniperus communis), each species belonging to one of the four families Taxaceae, Pinaceae, Taxodiaceae, and Cupressaceae, respectively. Each species was characterized by a high content of 5,9‐18:2, 5,9,12‐18:3, 5,11,14‐20:3, or 5,11,14,17‐20:4 acids, respectively. TAG were partially deacylated with ethylmagnesium bromide, and the resulting 1,2‐, 2,3‐diacylglycerols (DAG), and 2‐monoacylglycerols (MAG) were purified by thin‐layer chromatography. 1,2‐ and 2,3‐DAG were further fractionated by chiral column high‐performance liquid chromatography of the 3,5‐dinitrophenylurethane derivatives. Alternately, TAG were subjected to porcine pancreatic lipase, and the resulting 2‐MAG were purified for further analysis. Gas‐liquid chromatography of fatty acid methyl esters prepared from the separated DAG and MAG, coupled with appropriate calculations, indicated that the Δ5‐olefinic acids, irrespective of the species, chainlengths and number of ethylenic bonds, were considerably enriched in the sn‐3 position of TAG where they accounted for ca. 35 to 74 mole% of fatty acids esterified to this position (depending on the initial level of total Δ5‐olefinic acids in TAG), which corresponded to 79–94% of Δ5‐olefinic acids esterified to the three positions. On the other hand, Δ5‐olefinic acids were less than 10% in the sn‐2 position and less than 6% in the sn‐1 position of TAG. This specific enrichment of Δ5‐olefinic acids in the sn‐3 position thus appears to be a general characteristic of conifer seed TAG. These results were extended to TAG from the seeds of two pine species (Pinus koraiensis and P. pinaster) that are rich in Δ5‐olefinic acids and available commercially on a ton‐scale.
Syntheses of 12‐aminododecanoic and 11‐aminoundecanoic acids from vernolic acid
Authors: Ayorinde Folahan O. , Nana Erick Y. , Nicely Pete D. , Woods Anthony S. , Price Elvis O. , Nwaonicha Chukwuma P. 
Published: May 2007

Abstract12‐Aminododecanoic acid and 11‐aminoundecanoic acid, monomer precursors for nylon‐12 and nylon‐11, respectively, have been synthesized from vernolic (cis‐12,13‐epoxy‐cis‐9‐octadecenoic) acid via a reaction sequence that includes the formation of 12‐oxododecanoic acid oxime. Saponification of vernonia oil, followed by a low‐temperature recrystallization at −20°C, gave 51% vernolic acid (97% purity, m.p. 23–25°C). Hydrogenation afforded cis‐12,13‐epoxystearic acid (m.p. 52–54°C, lit. m.p. 52–54°C), which upon oxidation with periodic acid in tertiary butyl alcohol gave 12‐oxododecanoic acid with an isolated yield of 71.0%. Reaction of the oxoacid with hydroxylamine hydrochloride gave 12‐oxododecanoic acid oxime, which was catalytically reduced to give 12‐aminododecanoic acid with a yield greater than 85% and a melting point of 184–186°C (lit. m.p. 185–187°C). 11‐Aminoundecanoic acid was prepared from the 12‐oxododecanoic acid oxime via a three‐step reaction sequence that involved a Beckmann rearrangement, Hofmann degradation, and hydrolysis. Thus, the aldoxime acid was hydrolyzed in the presence of nickel acetate tetrahydrate to give 11‐carbamoylundecanoic acid (48% yield, m.p. 129–131°C, lit. m.p. 129–130°C). The amide was then treated with a solution of sodium methoxide and bromine at 70–80°C to give 11‐(methoxycarbonylamino)undecanoic acid at 75% yield (m.p. 84–86°C; elemental analysis, calculated for C13H25NO4: C, 60.19; H, 9.73; N, 5.40; O, 24.68%; found C, 60.02; H, 9.81; N, 5.26; O, 24.91%), which upon alkaline hydrolysis and subsequent neutralization gave 11‐aminoundecanoic acid at 34% yield (m.p. 189–192°C, lit. m.p. 190°C). Mass spectrometric and 13C nuclear magnetic resonance data of the previously unreported 11‐(methoxycarbonylamino)undecanoic acid is provided.
Autoxidation of synthetic isomers of triacylglycerol containing eicosapentaenoic acid
Authors: Endo Yasushi , Hoshizaki Sanae , Fujimoto Kenshiro 
Published: May 2007

AbstractSeveral triacylglycerols (TAG) that contained eicosapentaenoic acid (EPA) were chemically synthesized and stored at 25°C to assess the influence of TAG structure on oxidative stability and formation of oxidation products. Oxidative stability was evaluated by oxygen consumption during storage of the TAG. Autoxidation products of TAG were analyzed by high‐performance liquid chromatography (HPLC) and liquid chromatography‐mass spectrometry (LC‐MS). Results showed that a 2:1 (mole/mole) mixture of trieicosapentaenoylglycerol (EEE) and tripalmitoylglycerol (PPP) was most susceptible to autoxidation. The oxidative stability of TAG that contained EPA and palmitic acid was negatively correlated with the moles of EPA in a single TAG molecule. When TAG with one EPA and two other fatty acids were oxidized, chainlength of constituent fatty acids hardly affected the oxidative stability of EPA‐containing TAG molecules, except for stearic acid. HPLC and LC‐MS analyses showed that monohydroperoxides were major oxidation products regardless of type of TAG. Bis‐ and tris‐hydroperoxides were formed during autoxidation of EEE and dieicos‐apentaenoylpalmitoylglycerol. Monohydroperoxy epidioxides were found in all autoxidized TAG. These observations suggested that TAG structure affected the oxidation of TAG with highly unsaturated fatty acids.
Antioxidant activity of Magnolol, honokiol, and related phenolic compounds
Authors: Ogata Masahiro , Hoshi Midori , Shimotohno Kumiko , Urano Shiro , Endo Toyoshige 
Published: May 2007

AbstractThe antioxidant activity of 10 Japanese and Chinese crude drugs (Kampo drugs) was determined in vitro. Extract of Magnolia cortex, which had the highest antioxidant activity, contained phenolic compounds magnolol and honokiol. However, inhibitory effects of these compounds on lipid oxidation were weaker than that of α‐tocopherol as measured by thiobarbituric acid assay. The structure‐activity relationship of phenolic compounds showed that antioxidant activities were in the order 4‐allyl‐2,6‐dimethoxyphenol ≥ p,p′‐biphenol > eugenol > 2‐allyl‐6‐methylphenol > honokiol > magnolol > caffeic acid > p‐ethylphenol > guaiacol. As expected, these results showed that an electron donor and/or bulky groups at the ortho‐ or para‐position of the phenol were required for inhibition of lipid oxidation. Electron spin resonance spin trapping experiments showed that phenol compounds with an allyl substituent on their aromatic rings directly scavenged superoxide (O2−), and that only eugenol trapped hydroxyl radicals. These findings suggest that phenolic compounds that contain allyl groups may be effective antioxidants because of the scavenging ability of O2− or hydroxyl radical, whereas other phenols, without an allyl moiety such as α‐tocopherol, may play a role in the termination of free radical chain reactions.
Biodegradation of estolides from monounsaturated fatty acids
Authors: Erhan Selim M. , Kleiman Robert 
Published: May 2007

AbstractMono‐ and polyestolides, made from oleic acid, meadowfoam oil fatty acids and erucic acid, were subjected to biodegradation with mixed cultures of Penicillium verucosum, Mucor racemosus, and Enterobacter aerogenes. Fermentations were continued for 3, 5, 10, 15, 20, or 30 d. Meadowfoam oil and its fatty acids, oleic acid and soybean oil were also biodegraded under the same conditions. After 10 d, oleic acid and soybean oil were degraded 99.8 and 99.2%, respectively; meadowfoam oil and its fatty acids were degraded 89.0 and 97.7%, respectively. After 30 d, oleic acid‐derived poly‐ and monoestolides were degraded 98.6 and 90.0%, respectively, meadowfoam estolides were degraded 75.7%, and erucic acid estolides were degraded 84.0%.
Applications of lipase
Authors: Gandhi Neena N. 
Published: May 2007

AbstractLipases are endowed with a substrate specificity that surpasses that of any other known enzyme. This confers on these enzymes an application potential that is literally boundless. Lipases can be employed in the production of pharmaceuticals, cosmetics, leather, detergents, foods, perfumery, medical diagnostics, and other organic synthetic materials. This review attempts to present a comprehensive discussion on the present status of this unique group of enzymes in industry, as well as the actual potential. It represents an endeavor to provide a sincere answer to the question, “What can be done with this enzyme?” as well as, “Can lipase be utilized for this purpose?” It is intended that the manuscript will cover or at least mention all known applications, based on the exploitation of a particular type of reaction catalyzed by lipases. An attempt will be made to cover as large a number of references as possible, so as to further underline the importance and significance of lipase action for industry.
Drying properties of metathesized soybean oil
Authors: Erhan Sevim Z. , Bagby Marvin O. , Nelsen T. C. 
Published: May 2007

AbstractSoybean oil was metathesized with the standard homogenous metathesis catalyst, which consisted of tungsten hexachloride (WCl6) and tetramethyl tin (Me4Sn) in chlorobenzene as solvent. The reactions were terminated at different time intervals. Soybean oil was mixed with metathesized soybean oil in the presence of cobalt‐drier to evaluate drying properties. Five weight percentage (% w) of metathesized oil was found to be all that was needed to decrease the drying time of soybean oil from 312 to 182 min. Drying times for heat‐polymerized soybean oil with Gardner‐Holdt viscosity of Z1–Z2 and Z3–Z4 were 71 and 75 min, respectively. In both cases, 5% weight metathesized soybean oil in the blend gave the best results for reducing drying time to 67 and 69 min, respectively.