European Journal of Lipid Science and Technology

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Origin of fatty acids in the body: endogenous synthesis versus dietary intakes
European Journal of Lipid Science and Technology - Tập 108 Số 6 - Trang 521-525 - 2006
Cláudio Galli, Patrizia Risè
Comparative evaluation of structured oil systems: Shellac oleogel, HPMC oleogel, and HIPE gel
European Journal of Lipid Science and Technology - Tập 117 Số 11 - Trang 1772-1781 - 2015
Ashok R. Patel, Koen Dewettinck

In lipid‐based food products, fat crystals are used as building blocks for creating a crystalline network that can trap liquid oil into a 3D gel‐like structure which in turn is responsible for the desirable mouth feel and texture properties of the food products. However, the recent ban on the use of trans‐fat in the US, coupled with the increasing concerns about the negative health effects of saturated fat consumption, has resulted in an increased interest in the area of identifying alternative ways of structuring edible oils using non‐fat‐based building blocks. In this paper, we give a brief account of three alternative approaches where oil structuring was carried out using wax crystals (shellac), polymer strands (hydrophilic cellulose derivative), and emulsion droplets as structurants. These building blocks resulted in three different types of oleogels that showed distinct rheological properties and temperature functionalities. The three approaches are compared in terms of the preparation process (ease of processing), properties of the formed systems (microstructure, rheological gel strength, temperature response, effect of water incorporation, and thixotropic recovery), functionality, and associated limitations of the structured systems. The comparative evaluation is made such that the new researchers starting their work in the area of oil structuring can use this discussion as a general guideline.

Practical applications: Various aspects of oil binding for three different building blocks were studied in this work. The practical significance of this study includes (i) information on the preparation process and the concentrations of structuring agents required for efficient gelation and (ii) information on the behavior of oleogels to temperature, applied shear, and presence of water. This information can be very useful for selecting the type of structuring agents keeping the final applications in mind. For detailed information on the actual edible applications (bakery, chocolate, and spreads) which are based on the oleogel systems described in this manuscript, the readers are advised to refer our recent papers published elsewhere. (Food & Function 2014, 5, 645–652 and Food & Function 2014, 5, 2833–2841).

Photographs and comparative rheological evaluation of shellac oleogel, HPMC oleogel, and HIPE gel.

Contribution to the aroma characteristics of mutton process flavor from oxidized suet evaluated by descriptive sensory analysis, gas chromatography, and electronic nose through partial least squares regression
European Journal of Lipid Science and Technology - Tập 116 Số 11 - Trang 1522-1533 - 2014
Honglei Tian, Ping Zhan, Weiguo Li, Xiaoming Zhang, Xiaoyan He, Ma Yong-guang, Zhili Guo, Deqing Zhang

Changes in the aroma characteristics of mutton process flavors (MFSs) prepared from non‐oxidized suet and oxidized suet (OS) of different oxidation degrees were assessed by GC–MS, descriptive sensory analysis (DSA), and electronic nose (E‐nose). Six sensory attributes (muttony, meaty, suety, simulate, burnt, and off‐flavor) were selected to assess MFSs. DSA results showed a distinct difference among the sample MFS1 with non‐oxidized suet and other MFS samples with added OS of different oxidation degrees in terms of almost all sensory attributes. Also, MFS4 and MFS5 with moderate OS4 and OS5 showed very strong muttony, meaty, suety, and simulate attributes, but the weakest burnt and off‐flavor attributes. GC–MS analysis of volatiles indicated that MFS5, which had moderate OS5, generated a more appropriate content proportion of the characteristic flavor compounds than the others. Moreover, E‐nose analysis confirmed the results of GC–MS and DSA. Results of correlation analysis among 19 selected odor‐active compounds, DSA, and E‐nose data further confirmed that the moderate OS with a peroxide value (PV) of 103.29–287.61 meqO2 kg−1, the p‐anisidine value (p‐AV) of 61.03–262.52, and the acid value (AV) of 1.98–5.11 mg KOH/g suet may be a desirable precursor for the sensory characteristics of MFS.

Species‐species mutton flavor can be enhanced by heating suet in air through the coordination of Maillard reaction and lipid oxidation. Through the partial least squares regression analysis of the descriptive sensory analysis data, odor‐active compounds and E‐nose data, moderate oxidized suet was recommended for preparing mutton process flavors.

Antimicrobial properties of 1‐monoacylglycerols prepared from undecanoic (C11:0) and undecenoic (C11:1) acid
European Journal of Lipid Science and Technology - Tập 112 Số 10 - Trang 1106-1114 - 2010
Magda Janalí­ková, Rahula Janiš, Hana Svobodová, Věra Kašpárková, Petr Humpolíček, Jiří Krejčí
Abstract

Antimicrobial activity of monoacylglycerols (MAG) with odd number of carbons prepared from undecanoic (MAG C11:0) and undecenoic (MAG C11:1) was investigated. Data showed that both studied substances successfully inhibited Gram‐positive cocci (Staphylococcus aureus) and spore‐forming rods (Bacillus cereus). Gram‐negative bacteria were highly resistant against MAG C11:0 and showed considerable tolerance against MAG C11:1. Minimum inhibitory concentration (MIC) of MAG C11:1 was possible to determine for Escherichia coli only. Complete inhibition of three fungi genera (Alternaria, Cladosporium, Trichothecium) was achieved using MAG C11:1 with a concentration higher than 750 µg/mL. The growth of Aspergillus niger, Mucor racemosus, Phoma, Scopulariopsis, Trichoderma was significantly reduced. Generally, MAG C11:1 was more efficient than MAG C11:0 against all tested microorganisms. Due to a rich production of degradation enzymes, some fungi species surprisingly adapted their metabolism during growth and were even able to utilise tested MAG as a source of carbon.

Practical applications: MAG composed of fatty acids with odd number of carbons in molecule are a promising group of substances applicable in food industry and cosmetics. They represent materials with broad spectrum of antimicrobial activity, especially against Gram‐positive bacteria. More efficient MAG C11:1 with a double bond in molecule can be recommended for reduction of S. aureus that cause food enterotoxicosis.

Sea Buckthorn Oil Tocopherol Extraction's By‐Product Utilization in Green Synthesis of Polyurethane Coating
European Journal of Lipid Science and Technology - Tập 122 Số 4 - 2020
Mayur S. Prabhudesai, Pavan M. Paraskar, Rahul P. Kedar, Ravindra D. Kulkarni
Abstract

The focus of the present study is to utilize a by‐product obtained during extraction of tocopherols, a valuable vitamin E compound, from sea buckthorn (SBT) oil and in doing so find a reliable alternative to petrochemical based polyols. Bio‐based polyurethane (PU) is prepared by using SBT oil based fatty acid methyl ester polyesteramide polyols (SBTPEP) with toluene diisocyanate (TDI). The fatty acid methyl ester is converted to the corresponding fatty amide by reaction with diethanolamine. The formed fatty amide is then esterified with phthalic anhydride to synthesize polyesteramide polyol. Characterization techniques used to evaluate polyesteramide polyol are Fourier‐transform infrared spectroscopy (FTIR) and NMR. The cured PU coating is also put through various mechanical tests to analyze the physical properties. The cured PU coating shows good surface and mechanical properties. It shows a gloss value of 87.4 and passes impact, adhesion, and chemical resistance tests. It is hydrophobic which is evident from its contact angle of 100.2°. It has good thermal stability which is evident by its glass transition temperature of 53.9 °C. Use of phthalic anhydride contributes to the bio‐based characteristics of synthesized PU.

Practical Application: The present study presents a synthesis route which has minimal dependence on hazardous feedstock by utilization of green feedstock. The results obtained from physical and mechanical evaluations favor the use of this PU formulation in the coating sector. The adhesion and impact strength test results show potential application in the industrial sector coatings where the applied coat must be able to withstand high levels of physical stress and strain. The presence of aromatic rings and oil‐based moiety, that is the fatty acid hydrocarbon chain, contributes to the hydrophobic nature of the PU coating. Hydrophobic coatings have tremendous application in various fields such as marine coatings, automotive, electronics, and decorative coatings. These are potential fields of application for the synthesized green PU coating obtained from tocopherol extraction by‐products.

Excellent Properties of Dimer Fatty Acid Esters as Biolubricant Produced by Catalyst‐ and Solvent‐Free Esterification
European Journal of Lipid Science and Technology - Tập 121 Số 11 - 2019
Abu Hassan Noor Armylisas, Siti Hazirah Mohamad Fauzi, Noor Khairin Mohd, Shoot Kian Yeong, Idris Zainab, Nor Azwadi Che Sidik
Abstract

Currently most technologies available to produce esters require acid or base catalysts for esterification or transesterification reactions. Production of dimerate esters (DE) exhibiting potential as a biolubricant for low temperature applications using catalyst‐ and solvent‐free approaches is presented in this article. Hydrogenated C36dimer acid and alcohol are reacted under the following conditions: dimer acid/alcohol (1:4.5 molar ratio), 150–200 °C, 24 h, 3Å molecular sieve (15% w/w). The performances of four DE species—dibutyl, dihexyl, di‐(2‐ethylhexyl), and dioctyl dimerate—as lubricant base stocks are evaluated by kinematic viscosity, viscosity index, cloud and pour point (cold flow properties) as well as oxidative stability, and compared with commercial synthetic lubricant base stock and DE, Radialube 7121. High viscosity indexes ranging between 129 and 138 are observed for the synthesized DEs, which are comparable with two commercial base stock, polyalpha olefin (PAO), and polyolester (POE). Significantly low pour point, less than −42 °C, is observed for di‐(2‐ethylhexyl) dimerate attributed to the branching of the side chain. The DEs are categorized as ISO VG 68 based on their viscosity according to ISO 3448 classification and show potential as biolubricant with high viscosity index and excellent cold flow properties.

Practical Applications: DFAE obtained have high potential to be used as lubricant base stock for equipment and machinery operating at extremely low temperature.

Synthesis of Dimer Fatty Acid Methyl Esters by Catalytic Oxidation and Reductive Amination: An Efficient Route to Branched Polyamides
European Journal of Lipid Science and Technology - Tập 120 Số 1 - 2018
Marc von Czapiewski, Michaël A. R. Meier

A novel and versatile route toward dimer fatty acid methyl esters (dimer FAMEs) via catalytic oxidation and reductive amination is described. The oxyfunctionalization of mono‐unsaturated FAMEs bearing different chain lengths (C11, C18, C22) is accomplished by a co‐catalyst‐free Wacker Oxidation process in a high pressure reactor. The applied catalytic system of palladium(II) chloride in a dimethylacetamide/water mixture enabled the formation of keto‐FAMEs in the presence of molecular oxygen as sole re‐oxidant. In a first attempt, partially renewable dimer FAMEs are synthesized by reductive amination of keto‐FAME (C18) in the presence of various aliphatic and aromatic diamines and sodium triacetoxyborohydride as selective reducing agent. In another approach, the keto‐FAMEs directly underwent reductive amination using Raney‐Nickel in order to obtain the corresponding amino‐FAMEs. Subsequently, the keto‐ and amino‐FAMEs are used for the synthesis of fully renewable dimer FAMEs via reductive amination with sodium triacetoxyborohydride as reducing agent. In order to demonstrate a possible application for these new dimer FAMEs, three out of the thirteen synthesized dimer FAMEs are selected and studied in a polycondensation with renewable 1,10‐diaminodecane using TBD as catalyst. The polyamides are obtained in molecular weights (Mn) of up to 33 kDa and are carefully characterized by 1H‐NMR spectroscopy, FTIR, SEC, and DSC analysis.

Practical Applications: The described catalytic route to defined dimer fatty acids has potential applications in lubricants, detergents, polymeric materials, and others. Compared to commercially available dimer fatty acids, a molecularly highly defined mixture of regioisomers is obtained, without contamination of monofunctional or trifunctional fatty acid derivatives, which is advantegous for most of the mentioned applications. Especially for polycondensations, the known stoichiometry of exactly two is a considerable benefit.

The synthesis of keto‐fatty acid methyl esters via a straightforward co‐catalyst‐free Wacker oxidation process allows access to partially and fully renewable dimer fatty acid methyl esters, by using the obtained keto‐fatty acid methyl esters as renewable raw materials in a reductive amination process. Some of the obtained dimer fatty acids are exemplarily studied as monomers for polyamide synthesis.

Improved synthesis and characterization of saturated branched‐chain fatty acid isomers
European Journal of Lipid Science and Technology - Tập 114 Số 2 - Trang 213-221 - 2012
Helen L. Ngo, Eunha Hoh, Thomas A. Foglia
Abstract

The development of viable technologies for producing green products from renewable fats and oils is highly desirable since such materials can serve as replacements for non‐renewable and poorly biodegradable petroleum‐based products. Mixtures of saturated branched‐chain fatty acid isomers (sbc‐FAs), commonly referred to as isostearic acid, are important intermediates for the production of biodegradable lubricants, cosmetics, emollients, and hydraulic fluids. Present methods for producing sbc‐FAs, however, often give low yields of sbc‐FAs or sbc‐FA preparations with a high content of dimer acid fatty acid co‐products. This study reports an improved route to synthesizing sbc‐FAs from monounsaturated fatty acids using a modified H‐Ferrierite zeolite catalyst in conjunction with small amounts of triphenylphosphine additive. The yields of sbc‐FAs (up to 80 wt%) and co‐products (up to15 wt%) were determined using a modification of a previously reported GC method. A more detailed analysis of the distribution of sbc‐FA isomers in the products was made by the combined use of GC × GC‐TOF‐MS. Additionally, it was found that the H‐Ferrierite zeolite catalyst was recyclable and reusable up to 10 times without significant loss of activity and selectivity for sbc‐FAs.

Sesame Oil Oxidation Control by Active and Smart Packaging System Using Wheat Gluten/Chlorophyll Film to Increase Shelf Life and Detecting Expiration Date
European Journal of Lipid Science and Technology - Tập 122 Số 3 - 2020
Sona Chavoshizadeh, Sajad Pirsa, Forough Mohtarami
Abstract

In this study, a smart biodegradable film based on wheat gluten modified with chlorophyll (WG/Ch) is presented. The effect of chlorophyll on the antioxidant activity and mechanical properties of WG/Ch film is studied. Scanning electron microscopy and Fourier‐transform infrared spectroscopy (FT‐IR) analyses are used to study the structure and chemical composition of gluten‐based films. The WG/Ch film is used in the packaging of sesame oil. The effect of WG/Ch film on increasing the shelf life and detecting expiration time of oil is studied. FT‐IR results show that weak interactions are created between gluten and chlorophyll. The antioxidant activity of the WG film is 60% and it increases to 85% by the addition of chlorophyll. The results show that with the increasing storage time of oil samples, oxidative indices are increased, but the WG/Ch film decreases the sesame oil oxidation significantly (almost in the all oxidative indices 50% decrease is observed).

Practical Applications: The WG/Ch film is used in the packaging of sesame oil. The effect of WG/Ch film on the increasing of shelf life and detecting expiration time of oil is studied. By increasing storage time and oxidant, acidity, acid number, PA, and oil color change are increased, but the WG/Ch active film decreases the sesame oil oxidation significantly. Also, by examining the color properties of the active film, it is observed that with increasing storage time and oxidant percent, the color of the film is changed (from green to yellow), which can be used to estimate the oil expiration time. It should be mentioned that the film's color changes are visible to the naked eye.

Evaluation of polycyclic aromatic hydrocarbons content in different types of olive and olive pomace oils produced in Turkey and Spain
European Journal of Lipid Science and Technology - Tập 115 Số 9 - Trang 1078-1084 - 2013
Pelin Günç Ergönül, Sebastián Sánchez

Characterization of 15 polycyclic aromatic hydrocarbons (PAHs) in extra virgin, virgin, second centrifugation, lampante, refined, crude olive pomace, and refined olive pomace oils was carried out in 24 different types of olive oils and seven different types of pomace oils produced in Turkey and Spain. The extraction method was followed by liquid–liquid extraction, a solid phase clean up using C18 and Florisil cartridges, and evaporation. Then the evaporated residue dissolved in tetrahydrofuran/methanol 50:50 v/v, was analyzed by reversed phase high‐performance liquid chromatography with fluorescence detector using two excitations (280, 256 nm) and emission (410, 446 nm) wavelenghts channels. PAHs content of crude and refined olive pomace oils were found higher than in the other oils. In the samples analyzed, the highest concentrations of PAHs corresponded to benzo[ghi]perylene, naphthalene, pyrene, acenaphthene, benzo[k]fluoranthene, and phenanthrene.

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