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This work presents liquid–liquid equilibrium data for systems formed of organic solvents (acetone and dimethyl sulfoxide) and a vegetable oil blend composed of palm and coconut oils (MOPC). The MOPC represents the crude oil of the microalgae Chlorella pyrenoidosa as a basis for studying the liquid–liquid extraction in the oil refining stage. The equilibrium data for the MOPC + dimethyl sulfoxide + acetone systems were determined at four temperatures (293.15, 298.15, 308.15, and 318.15 K). Experimental binodal curves were performed by the cloud point determination, showing a decrease of the biphasic region with temperature increment. The UNIQUAC model was used to correlate the experimental data, using tripalmitin triacylglycerol properties to represent the vegetable oil blend. The standard deviation between the experimental and calculated data was 1.33%. The quality of experimental data and regressed parameters were checked by analyzing the Gibbs energy of the mixing function’s topology.

The effect of matrix-assisted laser desorption ionization-mass spectrometry (MALDI-MS) in analysis of small-molecule compounds, including amino acid, oligosaccharide and triglyceride, was investigated using a nano-triiron tetraoxide (Fe3O4) matrix. After comparing with other nanoparticle matrices and organic-inorganic binary matrices, Fe3O4 nanoparticles were selected as the matrix in MALDI-MS analysis of D,L-pyroglutamic acid, D,L-aspartic acid, L-proline, L-phenylalanine, sucrose, raffinose, tripalmitin and triolein. The effects of MALDI-MS experimental conditions on MS peak noise and signal intensity were investigated. The results showed that Fe3O4 increased the MS peak strength and reduced the background noise. Nano-matrix was used to cover the sample, and the MS acquisition parameters were set to positive polarity and 70% laser power. The results showed that nano-Fe3O4 was an ideal matrix for the detection of amino acids, oligosaccharides and triglycerides, and had better reproducibility and sensitivity than other matrices. The MALDI-MS analyses of D,L-pyroglutamic acid, sucrose, and triolein were performed using the nano-Fe3O4 matrix. The relative standard deviations (RSDs) in in-spot and spot-to-spot repeatability were less than 3.2% and 6.0%, respectively. The linear correlation coefficients (R2) between MS peak intensity and concentrations were no less than 0.997 in the concentration range of 0.05–1.0 mg/mL. The results showed the potential quantitative power of the MALDI-MS analysis.

In 2015, the US Food and Drug Administration passed a ban on the “generally recognized as safe” status of partially hydrogenated oils (PHOs), and in June 2018, PHOs were prohibited from being used. Our objective was to develop a predictive model to quantify trans-fat concentrations in bakery and snacks products using a portable mid-infrared (MIR) spectrometer. The approach was tested using 24 calibration standards (consisting of trielaidin in triolein and tripalmitin) and 87 bakery and snack products ranging from ND to 65% trans-fat. The fat was extracted by grinding products into powders and extracting the fat using petroleum ether. Gas Chromatography (AOCS Cd 14c-94) was used to determine the fatty acid profile and trans-fat content. Spectra were acquired by directly placing the fat (200 μL) onto the heated (65 ± 1°C) 5–reflection ZnSe crystal of a portable MIR spectrometer. Partial least squares regression (PLSR) models were developed using the calibration standards and extracted fats spectra targeting the signal of the C–H out-of-plane deformation band at 966 cm−1. Best model performances were obtained using the spectra of the extracted fat from bakery and snack products with the standard error of prediction of 0.5 g of trans-fats per 100 g of fat. We found that 25% of products labeled as zero trans-fat/serving did not comply with the maximum tolerance levels based on GC-FAME analysis. Portable FTIR devices operating in attenuated total reflection (ATR) mode can provide the food industry and government food inspectors with rapid, accurate, and high throughput measurements for routine screening to facilitate regulatory compliance.

This study evaluates the influence of the polymorphs of triacylglycerol (TAGs) seed crystals on the crystallization of coconut oil (CO) using seeding techniques. Tripalmitin (PPP) and tristearin (S...

Crystalline glycerides play an important role in the formation of multiphase systems such as emulsions and foams. The stabilization of oil/water interfaces by glyceride crystals has been extensively studied compared to only few studies which have been dedicated to oil/air interfaces. This study investigates the crystallization and network formation of tripalmitin (TP) and monopalmitin (MP) at the middle-chain triglyceride (MCT) oil/air interface. TP crystals were found to crystallize in the bulk before aggregating as large rectangular crystal conglomerates at the MCT oil/air interface. This leads to the slow formation of a plastic deformable, macroscopic crystal layer with high interfacial rheological moduli. MP crystals form directly at the MCT oil/air interface resulting in a comparatively fast formation of an elastic deformable network. Crystals with tentacle-like morphology were found to be responsible for the network elasticity. In this work, we show how interfacial crystallization dynamics and mechanical strength can be linked to the molecular structure and crystallization behavior of glyceride crystals. © 2020 American Chemical Society. ISSN:0743-7463 ISSN:1520-5827

Hydrochlorothiazide (HCT) multiparticulate systems (MPS) were hot melt coated with the binary mixture of tripalmitin (PPP) and polysorbate 65 (PS 65) to gain an immediate release profile. Once, HCT MPS were produced with a constant ratio of PPP/PS 65 (90:10) at three different coating amounts (15, 25, and 60%w/w) and once the PPP/PS 65 ratio was varied on 98:2 and 80:20, by keeping the coating amount at 60%w/w. PS 65 induced the polymorphic transformation of PPP from the α-form to its most stable β-form right after the hot melt coating (HMC). A release alteration of HCT, either accelerated or decelerated, occurred after the storage under accelerated conditions. The effect of the API core on the lipid lamellar configuration, the thermal behavior of lipid coating, and the effect of PS 65 concentration on the crystal growth of PPP were investigated via X-ray diffraction and DSC. While a low amount of PS 65 was sufficient to promote crystal growth of PPP and resulted in a decelerated release of HCT from the coating, a higher PS 65 concentration favored phase separation of PPP and PS 65 and led to an accelerated release. The increase in PS 65 reinforced the molecular interaction with the lipophilic HCT, reflected in less crystal growth and decelerated release. The knowledge presented in this study supports understanding the instability of binary emulsifier-lipid coating systems, paving the way for developing robust HMC formulations.

2-monoglyceride (2-MAG) was essential to produce high purity of 1, 3-Oleoyl-2-palmitoylglycerol (OPO), an important infant formula additive. Traditional synthesis of 2-MAG requires chemical solvent to solve the high melting point substrate, yielding the risk of solvent residue in OPO. This paper developed a solvent-free synthesis route of 2-MAG by alcoholysis of high melting point tripalmitin (PPP). Ethyl palmitate (EP), one of the reaction byproducts, was added in the beginning of alcoholysis process to promote the solubleness of high melting point PPP, avoiding the addition of toxic chemical solvent. The product of alcoholysis was separated by two-step molecular distillations. Separated DAG was used to produce 2-MAG and the final conversion of 2-MAG reached about 85.90%, with the purity of 92.36%. 2-MAG was trans-esterified to OPO with ethyl oleate, and the yield of OPO was up to 85.06% with 80.17% palmitic acid located on sn-2 position. The solvent-free synthesis route avoids the usage of hazardous chemical solvents, providing safer infant formula additive.

Considering the large consumption of Afrostyrax Lepidophyllus seeds, chemical analyses is necessary to ascertain its use as food spice and also its medicinal potential. Inductively coupled plasma mass spectrometry and gas chromatography mass spectrometry were used to evaluate the mineral and volatile contents respectively while column chromatography enabled the isolation of some compounds. Seventeen compounds were identified by gas chromatography mass spectrometry. Amongst detected sulphur containing compounds, methylsulfinyl(methylthio) methane was in highest amount with percentage composition of 12.25%. Fatty acids and their methyl esters were most abundant constituents notably n-hexadecanoic acid (28.86%) and methyl (E)-9-octadecenoate (21.85%). Some important unsaturated fatty acids notably linoleic acid and oleic acid were identified. Major elements detected in the sample were sodium (42,137.57 ppb), magnesium (456.90 ppb), phosphorus (1703.31 ppb), potassium (4948.88 ppb) and calcium (88.37 ppb. Trace elements detected in the sample are Cr (0.81 ppb), Mn (5.66 ppb), Fe (107.08 ppb), Co (0.14 ppb), Ni (6.77 ppb), Cu (50.05 ppb), Zn (32.06 ppb) and B (6.65 ppb). Other detected elements involved Al (42.25 ppb) and Pb (2.63 ppb) while Cd and Hg were below detectable limits. Five compounds were isolated and identified from their NMR spectral data as tripalmitin (AL23), n-hexadecanoic acid (AL40-45), ursolic acid (AL65), stigmasterol glycoside (AL192) and saccharose (AS329). Ursolic acid showed moderate ROS inhibition with IC50 = 18.5 ± 3.1 µg/mL compared to 11.2 ± 1.9 µg/mL for ibuprofen. NO inhibition and cytotoxicity on NIH-3T3 cell lines were low for tested compounds. This study fills knowledge gap on chemical analyses of A. lepidophyllus.

Fat crystal networks result from a crystallization process, forming interlinked crystal aggregates of viscoelastic character. Palm oil-based fat crystal networks, such as chocolate and nougat spreads, often show liquid oil separation during storage because the fat crystal network is too weak to retain the liquid oils trapped within its structure. To explore the relationship between crystallization kinetics and subsequent mechanical properties, i) palm oil from three different geographical origins and with diverging crystallization properties, ii) mixtures of Ghanaian palm oil with gradually increasing additions of hazelnut oil, and iii) blends of Ecuadorian palm oil with palm stearin as a tripalmitin (PPP)-rich fraction were investigated. Kinetic parameters were acquired from an extended Avrami model by isothermal differential scanning calorimetry measurements, and the results combined with the elastic properties measured by oscillation rheology since studying crystallization kinetics alone insufficiently informs about the mechanical/structural properties needed to overcome liquid oil separation. Rate constants of all investigated fats followed bell-shaped curves, with curve progression strongly dependent on the lipid composition. Ameliorating crystallization properties entailed enhanced elastic properties. The higher the maximum rate constants, the higher the elastic modulus and the gel rigidity of the respective fats. However, two different linear regions of elastic modulus versus PPP or solid fat content resulted, depending on whether palm oil was diluted with hazelnut oil or blended with a PPP-rich fraction. Hazelnut oil strongly diluted crystallizable portions of the structuring fat, thereby decreasing the mechanical properties in a power-law fashion, because the fat crystal network became less connected between fat crystal aggregates.

© 2019 This neutron diffraction study of deuterated tripalmitin has provided further insight into a forensic observation of the crystallisation of lipids under high-shear conditions. To achieve this, an experimental set up was designed to enable simultaneous rheological data from a Couette cell to be recorded with neutron powder diffraction, enabling the influence of shear on the polymorph transformation on cooling to be monitored in real time. Tripalmitin was observed to directly transform from a liquid phase to a β polymorph under the influence of shear. Although the liquid to β transition was not observed to be influenced by shear rate, the degree of crystallinity, qualitatively denoted by an increase in the sharpness of the diffraction peaks, was observed at higher shear rates. Evidence is also presented that the rate of cooling influences the ordering in the β-polymorph produced in zero shear conditions.

Hot melt coating (HMC) of an active pharmaceutical ingredient (API) powder with lipid-based excipients is an innovative method for manufacturing patient-convenient dosage forms. However, drug release instability is still its main industrial challenge. The correlation between the unstable pharmaceutical product performance with the solid-state alteration of lipids is currently well-investigated. The remaining problem is the inconsistent release alteration of different APIs coated with the same lipid after storage, such as faster release in some cases and slower release in others. The interaction between API surface and lipid-based coating and its alteration during storage were investigated in this work. The surface properties of five different APIs and the coating composition of tripalmitin and polysorbate 65 were screened via Washburn and pendant drop methods, respectively. Metformin hydrochloride and hydrochlorothiazide particles were each coated with the coating composition. The water sorption alteration of coated particles and the crystal growth of tripalmitin in the coating after storage were measured via tensiometry and X-ray diffraction. The cleavage work necessary to overcome the adhesion of coating composition on the core surface was calculated for each API. The accelerated release of the polar core (metformin) after storage was correlated with a low cleavage work and a distinctive phase separation. In contrast, a decelerated release of the hydrophobic core (hydrochlorothiazide) was favored by the crystal growth of the lipid-based coating. The gained knowledge can be used to design the product stability during the formulation development.

Normal-phase high-performance liquid chromatography (HPLC) is widely used in combination with evaporative light scattering detection (ELSD) for separating and detecting lipids in various food samples. ELSD responses of different lipids were evaluated to elucidate the possibilities and challenges associated with quantification by means of HPLC-ELSD. Not only the number and type of polar functional groups but also the chain length and degree of unsaturation of (free or esterified) fatty acids (FAs) had a significant effect on ELSD responses. Tripalmitin and trilinolein yielded notably different ELSD responses, even if their constituting free FAs produced identical responses. How FA structure impacts ELSD responses of free FAs is thus not predictive for those of triacylglycerols and presumably other lipids containing esterified FAs. Because ELSD responses of lipids depend on the identity of the (esterified) FA(s) which they contain, fully accurate lipid quantification with HPLC-ELSD is challenging and time-consuming. Nonetheless, HPLC-ELSD is a good and fast technique to semi-quantitatively compare the levels of different lipid classes between samples of comparable FA composition. In this way, lipid profiles of different flours from near-isogenic wheat lines could be compared. ispartof: Foods vol:2021 issue:10 ispartof: location:Switzerland status: published

The binary phase behavior of triacylglycerol (TAG) mixtures constituted by PPP (tripalmitin) and either POP (1,3-dipalmitoyl-2-oleoyl-glycerol), OPO (1,3-dioleoyl-2-palmitoyl-glycerol), or MCPOP/OPO (molecular compound formed by POP/OPO at a 1:1 concentration ratio) was determined by differential scanning calorimetry (DSC), synchrotron (SR-) and laboratory-scale X-ray diffraction (XRD). Steric hindrance due to saturated-unsaturated acyl chain interactions and differences in the thermal stability of TAGs seemed to dictate the independent polymorphic crystallization and transformation observed under kinetic conditions, as well as the very asymmetric eutectic-type phase diagrams obtained from the study of thermodynamically stabilized PPP/POP, PPP/OPO, and PPP/MCPOP/OPO mixtures. Moreover, the solid integration determined for MCPOP/OPO in the βPPP crystalline phase (20-25%), halfway between that of OPO (

We have investigated the polymorphism of triacylglycerol (TAG) crystals as they affect the qualities such as shelf life, mouth feel, and texture of chocolate and other products. Saturated monoacid TAGs, like trilaurin, are considered as models for TAG crystallization, however, there is still debate about the number of their polymorphs that exist. In this study, we characterized a set of novel polymorphs, &beta, forms of saturated monoacid TAGs, which were obtained via different pathways depending on the crystallization history, by polarized light microscopy, X-ray diffraction, and differential scanning calorimetry. Saturated monoacid TAGs were crystallized as the unstable polymorphs, the a or &beta, &rsquo, forms first, and then they were transformed into &beta, forms by solid&ndash, solid transformations. The &beta, form that had transformed from &beta, changed its morphology by a polymorphic transformation, while the &beta, form made from the a form kept its spherulite morphology. The &beta, forms obtained showed different melting points. Additional heat treatment promoted further polymorphic transformation. Four novel &beta, forms were found for each of the saturated monoacid TAGs, trilaurin, trimyristin, tripalmitin, and tristearin. They showed similar polymorphism with the same subcell packing.

A novel lipolytic enzyme-encoding gene, lipO745, from Aspergillus oryzae RIB40 was cloned and expressed in Pichia pastoris. Purified recombinant LipO745 (rLipO745) had a molecular mass of approximately 60 kDa on sodium dodecyl sulfate-polyacrylamide gel electrophoresis. rLipO745 exhibited maximum activity at 40 °C and pH 7.0 and was stable at temperatures ≤ 40 °C. The substrate specificity of purified rLipO745 was analyzed using α-naphthyl esters as artificial substrates and various triacylglycerol and sterol esters as natural substrates. From among a panel of α-naphthyl esters (C2-C16), α-naphthyl butyrate (C4), with an activity of 269 ± 3.3 units/mg protein, was the optimal substrate for hydrolysis by the purified recombinant protein. The Km and kcat values of rLiO745 for the C4 substrate were 0.073 ± 0.0012 mM and 608 ± 108 s-1, respectively. The purified recombinant enzyme had considerable hydrolytic activity toward tributyrin, tripalmitin, and triolein, indicating lipase activity, and toward cholesteryl acetate, butyrate, palmitate, and oleate, indicating sterol esterase activity. Transesterification activities between tributyrin and cholesterol or between tributyrin and campesterol were also determined.

Purpose: Cancer is an example of the most important growing diseases in human society and scientists are trying to treat it without considerable side effects on patient’s health. Solid lipids are colloidal nanoparticles that were used in drug delivery due to their several advantages. Methods: In this work, surface modified targeted solid lipid nanoparticles (SLNs) were fabricated by nano-homogenizer using tripalmitin glyceride and stearic acid as lipid constituents. The size of nanoparticles and morphological evaluations were surveyed using particle size analyzer, scanning electron microscopy; Fourier transforms infrared spectroscopy (FT-IR) and differential scanning calorimetry (DSC). Results: The particle size of 148.5 and appropriate polydispersity index were achieved for lipid nanoparticles with an entrapment efficiency of 86.1%. The FT-IR analysis confirmed the coupling of lysine to the free functional group of SLNs. DSC proved the conjugation of amino acid to the surface of carriers. The in vitro epirubicin (EPI) release test exhibited the further controlled release phenomenon for the lysine conjugated nanoparticles. The cytotoxicity assay showed lower IC50 of lysine conjugated SLNs of EPI on the investigated cell line. Conclusion: These studies showed that the fabricated targeted carrier has a very remarkable anticancer effect on breast cancer cell lines in comparison with pure drug.

The use of amorphous drug delivery systems is an attractive approach to improve the bioavailability of low molecular weight drug candidates that suffer from poor aqueous solubility. However, the pharmaceutical performance of many neat amorphous drugs is compromised by their tendency for recrystallization during storage and lumping upon dissolution, which may be improved by the application of coatings on amorphous surfaces. In this study, hot melt coating (HMC) as a solvent-free coating method was utilized to coat amorphous carvedilol (CRV) particles with tripalmitin containing 10% (w/w) and 20% (w/w) of polysorbate 65 (PS65) in a fluid bed coater. Lipid coated amorphous particles were assessed in terms of their physical stability during storage and their drug release during dynamic in vitro lipolysis. The release of CRV during in vitro lipolysis was shown to be mainly dependent on the PS65 concentration in the coating layer, with a PS65 concentration of 20% (w/w) resulting in an immediate release profile. The physical stability of the amorphous CRV core, however, was negatively affected by the lipid coating, resulting in the recrystallization of CRV at the interface between the crystalline lipid layer and the amorphous drug core. Our study demonstrated the feasibility of lipid spray coating of amorphous CRV as a strategy to modify the drug release from amorphous systems but at the same time highlights the importance of surface-mediated processes for the physical stability of the amorphous form.

We performed a multiscale study to understand the impact of pure exogenous compounds at low concentration on the crystallization of triacylglycerols (TAGs) in anhydrous milk fat (AMF). We selected butyric acid, an inhibitor of crystallization, and palmitic acid, a promotor, to investigate the influence of the chain length. Tripalmitin was also used as a promotor to assess the impact of fatty acid esterification. Melted blends containing the additives (1 wt%) were quenched at 25 °C. X-ray scattering data showed that AMF TAGs crystallized directly in the β’-2L form. The presence of additives did not modify the nanostructure of TAG crystals. However, they significantly altered the microstructure of AMF, as revealed by polarized light microscopy and rheology. This study emphasizes the interest of a multiscale approach to gain knowledge about the behavior of complex fat blends and of the use of modulators at low concentration to monitor their textural properties.

tert-Butylhydroquinone (TBHQ) losses and the residual levels of 2-tert-butyl-1,4-benzoquinone (TBBQ) in tripalmitin at different heating temperatures with or without reflux over various time intervals were investigated. Heating at 120 °C resulted in the slowest TBHQ loss and the highest TBBQ levels (52.61–62.93 μg/mL). The highest TBBQ concentrations (111.73–164.67 μg/mL) at 5 and 8 h and residual concentrations of 10.23–46.95 μg/mL during heating at 170 °C over 24 h were observed. Furthermore, the potential cytotoxicity of TBBQ to RAW 264.7 cells was evaluated with the MTT assay, Hoechst 33258 staining test, and flow cytometry analysis. Results indicate that TBBQ dose- and time-dependently decreased the growth of cells and inhibited DNA synthesis by regulating the S/G2 transition. The TBBQ concentration giving 50% inhibition in RAW 264.7 cells was 10.71 μg/mL. This threshold value is lower than the residual level of TBBQ in oil, indicating the necessity for concerns over the safety of fried food in terms of TBBQ residues.

We developed carriers of a 19F magnetic resonance imaging (19F MRI) agent, capable of responding to the temperature difference for cancer diagnosis. The carriers were based on high melting point (mp) neutral lipids, namely, tripalmitin (TPT) and tristearin (TSR) and triarachidin (TAC). Lipid nano-emulsions (LNEs) containing a fluorine compound, i.e., a modified α-tocopherol (19F-TP), were respectively prepared as TPT-LNE, TSR-LNE, TAC-LNE1, and TAC-LNE2 and studied by 19F NMR spectroscopy. In LNE prepared with soybean oil as a control, the full width at half maximum (FWHM) values of the 19F NMR signal of 19F-TP remained constant at 25, 37, and 42°C, while those of the LNEs prepared from a neutral lipid with a high mp showed a sharp decrease between 25 and 37°C. The magnitude of the decrease followed the order: TPT-LNE

Made available in DSpace on 2022-04-28T19:11:02Z (GMT). No. of bitstreams: 0 Previous issue date: 2018-01-01 Fundação de Amparo à Pesquisa do Estado de Minas Gerais (FAPEMIG) In this work, it was developed a novel bioreactor consisting of Aspergillus niger lipase (ANL) entrapped in a supermacroporous polyacrylamide cryogel. Bioreactor performance in catalyzing the flavor ester butyl butyrate was optimized as a function of temperature (°C), substrate molar ratio (butyric acid: n-butanol) and added water (% (v/v)). The bioreactor was also applied to interesterification reactions. The maximum esterification yield (46%) for butyl butyrate synthesis was found at 40 °C, with a butyric acid:n-butanol molar ratio of 1:1.43 and added water of 65% (v/v). The bioreactor showed to be reusable with four consecutive reuses in the esterification reaction, with a volumetric activity of 31.6 mmol/mL·h. An interesterification yield of 17.35% was achieved when the substrate concentrations of tripalmitin and triolein were both 15 mmol/L, 35% added water (v/v) and temperature of 40 °C. These results showed that the bioreactor is a promising biocatalyst for biotechnological applications. Federal University of Lavras Department of Food Science São Paulo State University Department of Food Engineering and Technology Federal University of Viçosa Department of Food Technology Federal University of Viçosa Department of Chemistry São Paulo State University Department of Food Engineering and Technology

Low-quality waste oils and fats such as the oily content of trap grease offer an alternative to fossil fuel oil, but they are not fully utilized since they contain saturated fatty acids (SFAs) and saturated triglycerides (STGs), which have relatively high melting points. For practical use of the oily content, it is necessary to remove the components that are solid at room temperature. In this study, we measured the liquidus curves of systems comprising an SFA (stearic acid, palmitic acid, or myristic acid) or an STG (tristearin, tripalmitin, or trimyristin) plus fuel oil A by differential scanning calorimetry. At the same mass fraction of the solid component, the STG plus fuel oil A systems had higher liquidus temperatures than the SFA plus fuel oil A systems with the same fatty acid chains. In both of the SFA plus fuel oil A systems and the STG plus fuel oil A systems, the system in which the solid component had a longer carbon chain had a higher liquidus temperature. On the assumption that fuel oil A is a pseudo-pure component, we proposed two simple methods for predicting liquidus temperature, from the ideal solution approximation and the Dortmund-UNIFAC model, and evaluated their prediction performance by comparing the experimental liquidus curves and the calculated results.

A novel diacylglycerol-based galloyl structured lipid, 1,2-dipalmitoylgalloylglycerol (DPGG), was synthesized using the enzymatic transesterification of propyl gallate (PG) and tripalmitin under solvent-free condition. An immobilized and commercially available food-grade Candida antarctica lipase B, Lipozyme® 435, was used as the biocatalyst. The reaction variables that affect the yield of DPGG were optimized using a 33 full factorial design. At 70 °C, DPGG was obtained at a yield of 33.0 ± 2.0% with PG conversion at 44.8 ± 1.8% when the following condition was used: 25 substrate molar ratio of tripalmitin to PG, 120 h reaction time, and 25% enzyme load relative to the total substrate weight. The structure of reaction product was elucidated using Fourier-transform infrared spectroscopy (FT-IR), electrospray ionization high-resolution accurate-mass tandem mass spectrometry (ESI-HRAM-MS/MS), and 1D and 2D nuclear magnetic resonance spectroscopy (NMR). The effects of different lipases and galloyl donors/acceptors on the transesterification were also investigated.

This study is devoted to preparation of novel solid lipid nanoparticles (SLNs) for the encapsulation of curcumin which is produced by micro-emulsion and ultrasonication using stearic acid and tripalmitin as solid lipids, tween80 and span80 as surfactants. The relation between particle size and entrapment efficiency of the produced SLNs was operated by central composite design (CCD) under response likes surface method (RSM). The variables including the ratio of lipids (X1), the ratio of surfactants (X2), drug/lipid ratio (X3), time of sonication (X4) and time of homogenization (X5). Particle size and entrapment efficiency of the loaded curcumin was justified according to the minimum particle size and maximum entrapment efficiency. The curcumin loaded SLNs presented fairly spherical shape with the mean diameter and entrapment efficiency of 112.0±2.6nm and 98.7±0.3%, respectively. The optimized SLNs were characterized by X-ray diffraction analysis (XRD), differential scanning calorimetry (DSC), photon correlation spectroscopy (PCS) and field emission scanning electron microscopy (FESEM). The drug release profile of the optimal formulated material was examined in aqueous media and almost 30% of the curcumin loaded in SLNs was gradually released during 48h, which reveals efficient prolonged release of the drug.

In this study, Candida lipolytica lipase (CLL) was immobilized on magnetic multi-walled carbon nanotubes (mMWCNTs) via hydrophobic and cation-exchange interaction. The resultant immobilized CLL showed much better thermal stability, biocatalyst activity and easier recycling than the free form. A method for efficient enzymatic acidolysis of tripalmitin (PPP) with oleic acid (OA), to produce OPO-rich TAGs, was developed, using the immobilized CLL as the biocatalyst. Under optimized conditions (2% water, 20mg/ml enzyme, 1:6 PPP/OA, 50°C, 2h), the content of OPO in the final product reached 46.5%. CLL@mMWCNTs had a better activity and manipulative stability than commercial lipases. More importantly, the feasibility of CLL@mMWCNTs was also validated in the practical production of OPO-rich TAGs, using lard and restructured palm oil as the raw material. These results suggest that CLL@mMWCNTs is a promising biocatalyst for the OPO-rich TAGs production and will be helpful for the infant formula industry.

The irreversibly diminishing reserves and the fluctuating price of crude oil, together with the serious concerns on the global environment and energy security, all suggests an unpleasant future of fossil fuel. Within this context, it is imperative to find alternative eco-friendly fuel with properties that highly mimic fossil fuel. Aliphatic alka(e)nes generated from renewable resources via biosynthetic pathways perfectly suits the criteria and represents the ideal ″drop-in″ biofuels. α-Alkenes are special microbial natural products. These biohydrocarbons have attracted much attention due to their potential application as biofuels and biomaterials. By coupling the activity of lipase and P450 decarboxylase, lipids (i.e. triglycerides) can be transformed into α-alkenes via free fatty acid intermediates. To improve the conversion efficiency of lipids to α-alkenes, in this study, four different versions of fusion proteins of the lipase TlL from Thermomyces lanuginosus and the P450 decarboxylase OleTJE from Jeotgalicoccus sp. ATCC 8456, including FusA (His6-TlL-linker-OleTJE), FusB (TlL-Linker-OleTJE-His6), FusC (His6-OleTJE-linker-TlL) and FusD (OleTJE- linker-TlL-His6), were constructed and comparatively evaluated. The optimal fusion enzyme FusC was able to convert a number of triacylglycerols including trilaurin (C12), trimyristin (C14) and tripalmitin (C16) into corresponding α-alkenes via the coupled hydrolysis and decarboxylation. The 31.7% yield of 1-tridecene from trimyristin demonstrates good substrate channeling effect. Due to the higher catalytic efficiency compared to the mixed TlL and OleTJE, as well as the simplified enzyme purification and hence the lower cost, this fusion strategy may hold significant potential of application.

The objective of this study was to investigate the effects of adding monoacylglycerols (MAGs) to triacylglycerols (TAGs) on the crystallisation properties in a fat system. Differential scanning cal...

In this study, decomposition products of glycidyl palmitate (GP) of fatty acids heated at high temperature such as deep frying were investigated. When GP and tripalmitin (TP) were heated at 180 and 200 °C, they were decreased with heating time. The weight of GP was less than that of TP, although both GP and TP were converted to polar compounds after heating. The decomposition rate of GP was higher than TP. Both GP and TP produced considerable amounts of hydrocarbons and aldehydes during heating. Aldehydes produced from GP and TP included saturated aldehydes with carbon chain length of 3–10, while hydrocarbons consisted of carbon chain length of 8–15. It was observed that major hydrocarbons produced from GP during heating were pentadecane. Moreover, the level of carbon dioxide (CO2) released from GP was higher than that of TP. It was suggested that fatty acids in GE might be susceptible to decarboxylation. From these results, GP might be quickly decomposed to hydrocarbons, aldehydes and CO2 besides polar compounds by heating, in comparison with TP.

The objective of this study was to induce crystallization in enzymatically interesterified fats (IE) with 20 and 30% palmitic acid at the sn-2 position using high intensity ultrasound (HIU). The physical blends (PB) used to prepare these two IE were consisted of tripalmitin and high oleic sunflower oil and contained 13.2 and 27.1% tripalmitin, respectively. Crystallization behavior of IE was compared with PB at supercoolings of 9, 6 and 3 °C. Results show that the melting point, SFC, and crystallization rate of PB were higher than IE and were driven mainly by tripalmitin content. HIU induced crystallization and generated small crystals in the IE samples. At 9 °C supercooling, sonication did not increase the viscosity of IE C16:0 20%, while that of the IE C16:0 30% increased significantly from 192.4 ± 118.9 to 3297.7 ± 1368.6 Pa·s. The elastic modulus (G’) for IE C16:0 30% increased from 12521 ± 2739.8 to 75076.7 ± 18259 Pa upon sonication at 9 °C supercooling, while the G’ of the IE C16:0 20% did not increase. Similar behavior was observed for the other supercoolings tested. This research suggests that HIU can improve the functional properties of IE with low content of C16:0 creating more viscous and elastic materials. These fats with low C16:0 content and improved functional properties could be used as trans-free fat alternatives.

Solid–liquid equilibria (SLE) for the binary systems of C12–C18 saturated fatty acids or their triglycerides + hexadecane (systems of dodecanoic acid (lauric acid), tetradecanoic acid (myristic acid), hexadecanoic acid (palmitic acic), octadecanoic acid (stearic acid), 1,2,3-propanetriyl tridodecanoate (trilaurin), 1,2,3-propanetriyl tritetradecanoate (trimyristin), 1,2,3-propanetriyl trihexadecanoate (tripalmitin), or 1,2,3-propanetriyltrioctadecanoate (tristearin), + hexadecane) were measured in the hexadecane fractions of 0 to 1 and temperatures from (273.2 to 353.2) K, using differential scanning calorimetry. These systems were selected as model systems for blending oily content extracted from restaurant trap grease with fossil fuel oils. The obtained liquidus curves were discussed in terms of the effects of carbon chain length, chemical form, and variation in the liquid component. In addition, the experimental liquidus curves were compared with predictions based on ideal solution approximation and on...

This paper proposed a two-step method to synthesize 1,3-Oleyl-2-Palmitoylglycerol (OPO) which is an important ingredient in the infant formula using an economical lipase from Candida sp. 99–125. In the first step, tripalmitin (PPP) is enzymatically alcoholyzed to monopalmitin (2-MP) by Candida sp. 99–125 lipase. MP is then recovered through solvent extraction at 78.03% yield and 98.01% purity, which are better than crystallization purification (75.85% yield and 86.37% purity). In the second step, the recovered 2-MP is solvent-free esterified with oleic acid, using the same lipase. OPO was obtained at a yield of 65%, including 75% palmitic acid in the Sn-2 position. This study has shown that the two-step method could give a higher yield of OPO than the previously reported one-step method using economical lipase.

The present work provides a systematic study to delineate the reaction mechanism and develop a mechanistic kinetic model for the hydrodeoxygenation (HDO) of triglycerides (TG) over alumina supported nickel catalyst. The HDO of 1:2 molar mixtures of tripalmitin and tristearin was studied in a batch reactor over a wide range of process conditions. The results showed that TG instantaneously converted to respective fatty acids. The fatty acids further converted to the fatty aldehydes. The fatty aldehydes, then, rapidly converted to alkanes by two parallel reaction pathways. The decarbonylation of fatty aldehyde (RP-I) was the dominating route compared to the reduction of the fatty aldehyde to fatty alcohol followed by its dehydration and hydrogenation (RP-II). A mechanistic kinetic model was developed based on the observed reaction pathway to correlate the experimental results. The rate constants for the conversion of palmitic acid and stearic acid to alkanes were matched closely with each other thereby demonstrating that HDO is independent of fatty acid chain length. The developed kinetic model was further validated using experimental data at various hydrogen-to-nitrogen mole ratios in the gas phase. Furthermore, the rate constants obtained for various catalyst loadings were correlated by a linear equation with zero intercept.

We present a high-resolution neutron powder diffraction study of the triclinic β form of tripalmitin as well as in situ crystallisation experiments, monitored with neutron diffraction, conducted over three different cooling rates. We use the results from the high-resolution study to anticipate if neutron diffraction could be beneficial in differentiating the polymorphism in triacylglycerol systems. We extend on this to present analysis of a diffraction pattern of cocoa butter, to establish the potential for neutron diffraction to study the (hydrogenous) forms of triacylglycerols used in food production.

Solid lipid nanoparticles (SLNs) have a crystalline lipid core which is stabilised by interfacial surfactants. SLNs are considered favorable candidates for drug delivery vehicles since their ability to store and release organic molecules can be tailored through the identity of the lipids and surfactants used. When stored, polymorphic transitions in the core of drug-loaded SLNs lead to the premature release of drug molecules. Significant experimental studies have been conducted with the aim of investigating the physico-chemical properties of SLNs, however, no molecular scale investigations have been reported on the behaviors that drive SLN formation and their polymorphic transitions. We have therefore used a combination of small angle neutron scattering (SANS) and all-atom molecular dynamics simulations (MS) to yield a detailed atomistic description of the internal structure of an SLN comprising of triglyceride, tripalmitin, and the nonionic surfactant, Brij O10 (C18:1E10). We uncover the molecular scale mechanisms by which the surfactants stabilise the crystalline structure of the SLN lipid core. By comparing these results to simulated liquid and solid aggregates of tripalmitin lipids, we demonstrate how the morphology of the lipids vary between these systems providing further insight into the mechanisms that control drug encapsulation and release from SLNs.

A novel and simple optical biosensor to detect triglycerides (TGs) has been successfully constructed by using pectin hydrogel membrane as the indicator pH and chromoionophore ETH 5294 (CI), with lipase as the catalyst. The enzymatic working system against TGs releasing H+ ions will affect the color absorbance of CI. The characterization results show that a TG biosensor has the optimum condition and sensitivity at the phosphate buffer concentration of 50 mM, pH 7, and enzyme loading of 60 &mu, g. The biosensor works at the tripalmitin (TP) concentration range of 100&ndash, 400 mg/dL. With the sensitivity of 0.001 (∆A/(mg/dL)), the biosensor response reaches stability after five minutes, and the limit of detection (LOD) of the TG optical biosensor is 15 mg/dL. Relative standard deviation (RSD) in a reproducibility test was 2.5%, with a 15-day lifespan.

In human milk fat, the saturated fatty acids,namely palmitic acid, are located at the sn-2 position of triacylglycerols (TAG) while unsaturated fatty acids (e.g. oleic acid) are esterified at position sn-1,3. Thus, sn- 1,3-dioleoyl-2-palmitoylglycerol (OPO) is the target TAG to be used as human milk fat substitutes (HMFS) in infant formulas. In this study, the noncommercial recombinant lipase/acyltransferase from Candida parapsilosis (CpLIP2) was immobilized in Accurel MP1000, and used as a biocatalyst for the interesterification of tripalmitin with ethyl oleate in a solvent-free medium, to obtain structured lipids used as HMFS. Different molar ratios (MR) of ethyl oleate to tripalmitin (2:1–8:1) were used. After 4 h reaction at 60ºC, about 30 mol% of oleic acid incorporation was already observed for all tested MR. An apparent equilibrium was reached after 8–24 h, with 32–51 mol% final incorporation, increasing with the MR. The incorporation of oleic acid into TAG was compared with the maximum predicted values when a random or a sn-1,3-regioselective biocatalyst was used. The obtained values are consistent with the maximum incorporation expected for a sn-1,-3-regioselective enzyme. In fact, the amount of oleic acid at position sn-2 was approximately 15% for all the MR tested, which is explained by the acyl migration phenomenon. CpLIP2 exhibited higher activity than most commercial immobilized lipases (e.g. faster reaction in solvent-free media, low enzyme load, and low MR needed), and showed a recognized sn-1,3 regioselective behavior. info:eu-repo/semantics/publishedVersion

Interest has recently been rising in the development of food-compatible Pickering emulsions, i.e., particle-stabilized emulsions, and various biobased particles have been demonstrated as useful for such a purpose. Most of the related work has focused on the physical stability of the emulsions, but whether such particles can be advantageous in terms of chemical stability, and in particular, with regard to lipid oxidation, is largely unexplored. Recently, we found that colloidal lipid particles (CLPs) are efficient Pickering stabilizers, and the objective of the present study was to investigate the oxidative stability of emulsions stabilized with those particles. Three types of sunflower oil-in-water (O/W) emulsions were considered: Pickering emulsions stabilized with colloidal lipid particles (CLPs) made of high melting point (HMP) fat (tripalmitin or palm stearin), adsorbed onto the liquid oil droplets; and, as references, two conventional sodium caseinate-stabilized emulsions, of which one contained only liquid oil, and the other liquid oil mixed with HMP fat as the core of the emulsion droplets. In the presence of iron, the latter oxidized faster than conventional liquid oil and Pickering emulsions, resulting in 2- to 3-fold higher amounts of primary and secondary lipid oxidation products. This may be due to intra-droplet HMP fat pushing oxidizable lipids towards the oil-water interface, which would promote lipid oxidation. This shows that the localization of solid fat in O/W emulsions affects lipid oxidation. We also found that CLP-stabilized Pickering emulsions had similar oxidation rates as conventional sodium caseinate-stabilized emulsions containing only liquid oil. This suggests that the potential of such Pickering particles to prevent lipid oxidation is limited. This could be because diffusion of small pro-oxidant molecules is not hindered by Pickering particles, as they cannot form an interfacial barrier that is structurally homogeneous at such a small scale.

International audience; Dietary fats are present in the diet under different types of structures, such as spread vs emulsions (notably in processed foods and enteral formula), and interest is growing regarding their digestion and intestinal absorption. In clinical trials, there is often a need to add stable isotope-labeled triacylglycerols (TAGs) as tracers to the ingested fat in order to track its intestinal absorption and further metabolic fate. Because most TAG tracers contain saturated fatty acids, they may modify the physicochemical properties of the ingested labeled fat and thereby its digestion. However, the actual impact of tracer addition on fat crystalline properties and lipolysis by digestive lipases still deserves to be explored. In this context, we monitored the thermal and polymorphic behavior of anhydrous milk fat (AMF) enriched in homogeneous TAGs tracers and further compared it with the native AMF using differential scanning calorimetry and power X-ray diffraction. As tracers, we used a mixture of tripalmitin, triolein and tricaprylin at 2 different concentrations (1.5 and 5.7 wt%, which have been used in clinical trials). The addition of TAG tracers modified the AMF melting profile, especially at the highest tested concentration (5.7 wt%). Both AMF and AMF enriched with 1.5 wt% tracers were completely melted around 37 °C, i.e. close to the body temperature, while the AMF enriched with 5.7 wt% tracers remained partially crystallized at this temperature. Similar trends were observed in both bulk and emulsified systems. Moreover, the kinetics of AMF polymorphic transformation was modified in the presence of tracers. While only β’ form was observed in the native AMF, the β-form was clearly detected in the AMF containing 5.7 wt% tracers. We further tested the impact of tracers on the lipolysis of AMF in bulk using a static in vitro model of duodenal digestion. Lipolysis of AMF enriched with 5.7 wt% tracers was delayed compared with that of AMF and AMF enriched with 1.5 wt% tracers. Therefore, low amounts of TAG tracers including tripalmitin do not have a high impact on fat digestion, but one has to be cautious when using higher amounts of these tracers.

This paper first uses density functional theory combined with the method of quantum chemistry calculations to obtain the electrostatic potential surfaces of the four main triglyceride molecules in palm oil and the water molecule, which reveals the reactivities of triglyceride molecules and the water molecule from a microscopic perspective. In addition, the conductor-like screening model for real solutions (COSMO-RS) method is used to calculate the σ-profile of the main active components of naphthenic mineral oil and the four main triglycerides in palm oil. Then, the COSMO-RS model of the triglyceride-hydrocarbon system is constructed, which theoretically predicts the solubility of the four main triglyceride molecules tripalmitin, tristearin, triolein, and trilinolein in mineral oil. The results show that triglyceride molecules and the mineral oil molecules have similar intermolecular forces, so triglyceride molecules can easily dissolve into the mineral oil. The results of this paper can provide theoretical reference and calculation support for the development of new-type mixed insulating oil for transformers.

Solid acid-catalyzed biodiesel production from inedible oils offers a promising mean to reduce the cost of feedstocks and avoid the competition with edible oil market. Here we demonstrate a series of inner diameter-controlled sulfonic acid functionalized ethyl-bridged-organosilica nanotubes (Ar/PrSO3H–Si(Et)Si) by a toluene swollen mixed Pluronic surfactant micelle-templating co-condensation route for transesterification of tripalmitin or plant oils with methanol to produce fatty acid methyl esters and esterification of glycerol with lauric acid to produce mono- and di-glycerol esters. By combination of superstrong Bronsted acidity, unique hollow tubular nanostructure, excellent porosity properties and hydrophobic surface, the Ar/PrSO3H–Si(Et)Si nanotubes display higher catalytic activity as compared with acidic resin and zeolite. Additionally, the inner diameters and lengths of Ar/PrSO3H–Si(Et)Si nanotubes influence the activity obviously. The Ar/PrSO3H–Si(Et)Si nanotubes also show excellent catalytic reusability, attributing to covalent bonding of Ar/PrSO3H groups within silica/carbon framework and surface hydrophobicity of the catalysts.

An image processing algorithm previously used to analyse the crystallisation of a pure fat (tripalmitin) has been applied to the crystallisation of a multicomponent natural fat (palm oil). In contrast to tripalmitin, which produced circular crystals with a constant growth rate, palm oil produced speckled crystals caused by the inclusion of entrapped liquid, and growth rates gradually decreased with time. This can be explained by the depletion of crystallisable material in the liquid phase, whereas direct impingement of crystals (the basis of the Avrami equation) was less common. A theoretical analysis combining this depletion with assuming that the growth rate is proportional to the supersaturation of a crystallisable pseudo-component predicted a tanh function variation of radius with time. This was generally able to provide good fits to the growth curves. It was found that growth rate was a relatively mild function of temperature but also varied from crystal to crystal and even between different sides of the same crystal, which may be due to variations in composition within the liquid phase. Nucleation rates were confirmed to vary approximately exponentially with decreasing temperature, resulting in much greater numbers of crystals and a smaller final average crystal size at lower temperatures.

Facile synthesis of hybrid solid acids with finely engineered surface properties was successfully realized via sulfonation of polystyrene (PS) dispersed in nanopores of silica hollow nanosphere modified with different organic group. It was found that octyl or perfluorinated octyl could efficiently increase the surface hydrophobicity of the hybrid solid acids. Benefited from the facile adjustability of the surface properties, the catalytic performance of the solid acids could be readily improved in both the esterification of lauric acid with ethanol and the transterification between tripalmitin and methanol. The solid acid modified with perfluorinated octyl shows even higher activity than liquid sulfuric acid in the transesterification reaction. The octyl group incorporated in the silica shell could also prevent the leaching of PS-SO 3 H during the catalytic process.

We report a class of poly(anionic liquid) microgels that undergo stimuli-responsive volume phase transitions. Such a microgel is synthesized by free radical precipitation polymerization of a tetrabutylphosphonium 4-styrenesulfonate monomer and a cross-linker N,N’-methylenebisacrylamide. These microgels can not only undergo reversible volume phase transitions in response to changes in temperature in water, methanol, or water/methanol mixtures, but also undergo re-entrant swelling–shrinking–swelling transitions as the methanol content increases in water/methanol mixtures at a set temperature in our experimental temperature window of 25.0–64.0 °C. Such microgels can be post functionalized, e.g., via ion-exchange treatment with HSO3CF3 to partially transform sulfonate to the catalytic Bronsted acidic –SO3H, whilst the yielded microgels can inherit the responsive properties. With both responsive and catalytic properties simultaneously harnessed on the same object, the functionalized microgels potentially can be used as a highly efficient catalyst for the esterification reaction of palmitic acid and the transesterification reaction of tripalmitin with methanol (as model reactions) at 65.0 °C (temperature of an oil bath), and allow the catalytic activity to be modulated to a certain extent in a non-monotonous way, making it possible to boost the reactions at a relatively lower temperature (e.g., 42.0 °C), while maintaining considerable catalytic activity. These features underlie the feasible use of the microgels in biodiesel production (with waste cooking oil as a model feedstock).

Enzymatic syntheses of fatty acid anilides are important owing to their wide range of industrial applications in detergents, shampoo, cosmetics, and surfactant formulations. The amidation reaction of Mucor miehei lipase Lipozyme IM20 was investigated for direct amidation of triacylglycerol in organic solvents. The process parameters (reaction temperature, substrate molar ratio, enzyme amount) were optimized to achieve the highest yield of anilide. The maximum yield of palmitanilide (88.9%) was achieved after 24 h of reaction at 40 °C at an enzyme concentration of 1.4% (70 mg). Kinetics of lipase-catalyzed amidation of aniline with tripalmitin has been investigated. The reaction rate could be described in terms of the Michaelis-Menten equation with a Ping-Pong Bi-Bi mechanism and competitive inhibition by both the substrates. The kinetic constants were estimated by using non-linear regression method using enzyme kinetic modules. The enzyme operational stability study showed that Lipozyme IM20 retained 38.1% of the initial activity for the synthesis of palmitanilide (even after repeated use for 48 h). Palmitanilide, a fatty acid amide, exhibited potent antimicrobial activity toward Bacillus cereus.

The objective of this study was to produce low saturated, zero-trans, interesterified fats with 20 or 30 % saturated fatty acids (SFA) such as C16:0 or C18:0. Tripalmitin (TP) or tristearin (TS) was blended with high oleic sunflower oil (HOSO) at different ratios (0.1:1, 0.3:1, and 0.5:1 [w/w]). Total C16:0 and C18:0 compositions of the resulting TP/HOSO and TS/HOSO blends, respectively, were plotted against blending ratios. Linear interpolation was used to estimate blending ratios that would yield physical blends (PB) with 20 or 30 % SFA. Interesterified blends (IB) were then synthesized from the customized PB using Lipozyme TL IM as the biocatalyst. Total and sn-2 fatty acid compositions, triacylglycerol (TAG) molecular species, thermal behavior, and oxidative stability of PB and IB were compared. The total fatty acid compositions of PB and IB were similar but fatty acid positional distributions and TAG molecular species composition differed. IB contained 5–10 % more SFA at the sn-2 position than corresponding PB. Furthermore, interesterification generated mono- and disaturated TAG species which resulted in broader melting profiles for IB. However, IB had lower oxidative stability than PB. The reformulation of food products with zero-trans interesterified fats may be advantageous to the reduction of cardiovascular disease burden in the population.

Colloidal lipid particles (CLPs) are promising encapsulation systems for lipophilic bioactives, such as oil-soluble antioxidants that are applied in food and pharmaceutical formulations. Currently, there is no clear consensus regarding the relation between particle structure and the chemical stability of such bioactives. Using α-tocopherol as a model antioxidant, it is shown that emulsifier type (Tween 20 or 40, or sodium caseinate) and lipid composition (tripalmitin, tricaprylin, or combinations thereof) modulated particle morphology and antioxidant stability. The emulsifier affects particle shape, with the polysorbates facilitating tripalmitin crystallization into highly ordered lath-like particles, and sodium caseinate resulting in less ordered spherical particles. The fastest degradation of α-tocopherol is observed in tripalmitin-based CLPs, which may be attributed to its expulsion to the particle surface induced by lipid crystallization. This effect is stronger in CLPs stabilized by Tween 40, which may act as a template for crystallization. This work not only shows how the architecture of CLPs can be controlled through the type of lipid and emulsifier used, but also gives evidence that lipid crystallization does not necessarily protect entrapped lipophilic bioactives, which is an important clue for encapsulation system design. Practical Applications: Interest in enriching food and pharmaceutical products with lipophilic bioactives such as antioxidants through encapsulation in lipid particles is growing rapidly. This research suggests that for efficient encapsulation, the particle architecture plays an important role; to tailor this, the contribution of both the lipid carrier and the emulsifier needs to be considered.

Clarithromycin (CLR) is a macrolide derivative which is included in BCS class 2 with low oral bioavailability. Solid lipid nanoparticles (SLNs) have been studied by many researchers for drug application and are very popular systems that continue to be studied. However, the effects of lipids used in SLN production on the formulation properties are one of the few studied topics. Therefore, the aim of this study was to formulate CLR incorporated SLN formulations by ‘high-speed homogenization technique’’ for oral administration and also elucidate the effect of three types of lipid matrix on particle size (PS), polydispersity index (PDI), drug content, release properties etc. For this reason, three types of major lipid matrix (Glyceryl behenate, Tripalmitin and Stearic acid) were chosen in this study. Seven different formulations were characterized in detail and the results were discussed. The PSs of the CLR incorporated SLNs were between 318 and 526 nm. The average PDI of blank nanoparticles varied between 0.211 and 0.409, whereas the average PDI of CLR incorporated SLNs were between 0.228 and 0.472. The drug content was a range of 63–89%. In vitro release studies of SLNs showed extended-release up to 48 h after the first 6 h of burst effect. Both the burst effect kinetics and the 48-h release kinetics were investigated. The results showed that the burst effect was fitted to the Korsmeyer-Peppas model and 48 h to the Baker-Lonsdale model. The structures of the formulations were clarified by DSC & FT-IR analysis. The results showed that PS, PDI, drug content and release rates of SLNs were directly related to the carbon chain length of lipid. Antibacterial activity of the formulations was tested against Staphylococcus aureus by microdilution and agar well diffusion methods. Formulations A3, A5, A6 and A7 rendered CLR, 2 times more effective against its target according to the microdilution method. As for the agar well method, clear zones around A3, A5, A6, and A7 wells were the same size or larger than clarithromycin zone. The cell viability test was performed with MTT in the NIH 3T3 mouse embryonic fibroblast cell line. At the end of the incubation times, no cell viability differences were observed between CLR and formulations. As a result, in vitro characterization and release data demonstrated the possibility of improved bioavailability of CLR by SLN formulation and the effect of lipid used in this study on formulation characteristics were elucidated in detail. At least in terms of some formulations, improved pharmacodynamic effects were also obtained from antibacterial activity studies. © 2019 Elsevier B.V.