Glycerol Monooleate Research Articles

Characterization and optimization of GMO-based gels with long term release for intraarticular administration

Osteoarthritis is characterized by slow degenerative processes in the articular cartilage within synovial joints. It could be interesting to develop a sustained-release formulation that could be effective on both pain/inflammation and restoration of mechanical integrity of the joint. Recently, an injectable system based on glycerol monooleate (GMO), containing clonidine as a model hydrophilic analgesic/anti-inflammatory drug and hyaluronic acid as a viscoelastic scaffold, showed promising potential as a biodegradable and biocompatible preparation to sustain the drug activity. However, drug release from the system is relatively fast (complete within 1 week) and the underlying drug release mechanisms not fully understood. The aims of this study were: (i) to significantly improve this type of local controlled drug delivery system by further sustaining clonidine release, and (ii) to elucidate the underlying mass transport mechanisms. The addition of FDA-approved inactive ingredients such as sodium oleate or purified soybean oil was found to be highly effective. The release rate could be substantially reduced (e.g., 50% release after 10 days), due to the increased hydrophobicity of the systems, resulting in slower and reduced water uptake and reduced drug mobility. Interestingly, Fick's second law of diffusion could be used to quantitatively describe drug release.

Isothermal crystallization kinetics and mechanical properties of polycaprolactone composites with zinc oxide, oleic acid, and glycerol monooleate

The isothermal crystallization and mechanical behavior of polycaprolactone (PCL) with zinc oxide (ZnO) with oleic acid and glycerol monooleate (GMO) were studied. Theoretical melting points calculated by the Flory–Huggins and Thompson–Gibbs models were thoroughly compared with differential scanning calorimetry experimental observations. The isothermal crystallization kinetic parameters by Avrami analysis showed that crystallization was controlled by nucleation, crystal growth was spherical, and the nucleation type changed between thermal and athermal nucleation. X‐ray diffraction showed that when the additives were used together both the crystal thickness and the degree of crystallinity increased. A multiple‐response regression analysis was made with the ZnO, oleic acid, and GMO concentrations as variables and the crystallinity as output. Interaction parameters by the Pukanzky model were calculated from the tensile strength at the yield point and indicated that the addition of oleic acid or GMO improved the interface between the ZnO particles and PCL. © 2013 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 130: 1259‐1275, 2013

Ultra-low friction of tetrahedral amorphous diamond-like carbon (ta-C DLC) under boundary lubrication in poly alpha-olefin (PAO) with additives

Diamond-like carbon (DLC) coatings have increased demand as protective hard coating for mechanical components due to their exceptional mechanical and tribological performance. They provide ultra-low friction, excellent anti-wear properties and adhesive protection. In recent years, researches focus on the use of DLC coatings under boundary lubricated contacts to increase fuel efficiency of automotive by controlling the friction and to reduce the emission of harmful elements. Commercially available fully formulated oils are designed for ferrous surfaces and contain various additives to enhance the base oils, but interaction between DLC surfaces and those formulated oils is not yet fully understood. In this study we investigated frictional properties of ta-C DLC coating when lubricated with a base oil poly alpha-olefin (PAO) and PAO containing friction modifier glycerol mono-oleate (GMO), anti-wear additives ZnDTP and mixture of GMO+ZnDTP to understand the mechanism of ultra-low friction. The results exhibit that ta-C give ultra-low friction in pure PAO for DLC/steel and DLC/DLC tribopair. GMO additivated PAO provide smooth run-in period for transition to ultra-low friction regime and also enhance the durability of coating. ZnDTP behave differently depending on the presence of ferrous surfaces on the contact. It forms pad-like wear protective tribofilm both on ta-C and steel surfaces for DLC/steel contact, while it form thin white layer on ta-C surfaces for DLC/DLC contact. Using GMO and ZnDTP together does not show any synergistic correlation for steel/steel, DLC/steel and DLC/DLC combinations.

Development of cyclosporine A-loaded dry-emulsion formulation using highly purified glycerol monooleate for safe inhalation therapy

The main objective of this study was to improve the safety and oxidative stability of glycerol monooleate (GMO)-based dry-emulsion (DE) formulation containing cyclosporine A (CsA) for inhalation therapy. GMO or highly purified GMO (hpGMO) was used as surfactant for the DE formulations (GMO/DE or hpGMO/DE), the toxicological and physicochemical properties of which were characterized with a focus on oxidative stability, in vitro/in vivo toxicity, and dissolution property. Incubation of GMO at oxidation accelerating conditions for 10 days at 60°C resulted in the formation of lipid peroxides as evidenced by increased malondialdehyde (111 μmol/mg); however, hpGMO samples exhibited increase of only 20.7 μmol/mg in malondialdehyde level. No significant acute cytotoxicity was observed in rat alveolar L2 cells exposed to hpGMO (0.28mM), and intratracheal administration of hpGMO powder in rats did not cause an increase of the plasma LDH level. The hpGMO/DE exhibited marked improvement in dissolution behavior of CsA, and stable fine micelles with a mean diameter of 320 nm were formed when suspended in water. A respirable powder formulation of hpGMO/DE (hpGMO/DE-RP) was newly prepared, and its in vitro inhalation property and in vivo efficacy were also evaluated. The hpGMO/DE-RP exhibited high dispersibility in laser diffraction analysis and significantly improved potency to attenuate recruitment of inflammatory cells into airway and thickening of airway wall in an animal model. Thus, the strategic use of hpGMO would improve oxidative stability and local toxicity compared with a GMO-based DE formulation, and its application to RP formulation could be a promising approach for effective inhalation therapy.

Invert and double emulsions as a base for microheterogeneous matrices for transdermal delivery of lipophilic drugs

Stable invert emulsions water/oil and double emulsions oil1/water/oil2 containing polyisobuthylene as pressure-sensitive polymeric adhesive are prepared. The dispersed phase of the invert emulsions contained micelles of the surfactant Tween 80 (Tw) with solubilized drug (Felodipine) and a skin permeation enhancer (glycerol monooleate, GMO). The active components (Felodipine and GMO) of the double emulsions were incorporated into the internal dispersed phase, while the intermediate water layer contained Tw and hydroxypropylcellulose. Ultradispersed polymer films with good adhesion to skin were prepared from both types of emulsions. The films based on double emulsions demonstrate the ability to release Felodipine at therapeutically effective levels and maintain these levels during the first 24 h to attain a therapeutically required dose. The invert and double emulsions were for the first time utilized as bases for microheterogeneous matrices for delivery of a lipophilic drug in bioavailable form.

Nanomechanical and boundary lubrication properties of titanium carbide and diamond-like carbon nanoperiod multilayer and nanocomposite films

To develop a new low friction and wear resistant coating, nanometer period TiC and DLC multilayer films composed of titanium carbide and hydrogen-free diamond-like carbon (DLC) layers were deposited by bias rf sputtering. Nanoperiod multilayer films were deposited by controlling the opposing time of the substrate to each of the titanium carbide and graphite targets. Below the 6-nm target layer period, nanocomposite films with nm-scale particles were deposited. Above the 12-nm target layer period, multilayer films were deposited. The nanoindentation hardness and nanowear resistance of the nanoperiod multilayer (TiC/DLC)n films change with the layer period. The 12-nm-target-period (TiC/DLC)n film shows higher hardness and nanowear resistance. The dependence of boundary lubrication properties on target period under poly (alpha-olefin) (PAO), PAO with glycerol monooleate (GMO) and water was investigated by an oscillating tribotest. The boundary lubrication properties of the (TiC/DLC)n films are significantly improved compared with those of the DLC monolayer film. Moreover, the hard and nanowear-resistant 12-nm-target-period multilayer film shows the lowest friction coefficient and a small damage depth under boundary lubrication using PAO, PAO with GMO and water. It is deduced that the 12-nm-target-period multilayer (TiC/DLC)n film has the shortest period and the largest number of interfaces that prevent damage elongation, and it is hard and shows superior nanowear resistance.

Modulation of physical properties of reverse hexagonal mesophases: A dielectric spectroscopy study

The structural, dynamic, and kinetic aspects of the HII systems based on glycerol monooleate (GMO), phosphatidylcholine (PC), triacylglycerol (TAG), and water were investigated by dielectric spectroscopy in a frequency range of 10-2–106 Hz, and a temperature range of 290–320 K. Three distinct processes as well as a temperature-activated dc conductivity were detected and examined. These were assigned to the reorientation of the GMO polar heads, the tangential movement of counterions at the interface, the transport of TAGs through the lipids tails, and the ion mobility within the water cylinders.Upon addition of PC, the critical temperature (T0) of the dehydration of the GMO headgroups increased. The optimal concentration found for structural stabilization of the HII mesophase was 10 wt% PC, since it imparted the strongest bonding at the interfacial layer and increased the association between the lipid tails. Within the HII cluster, TAG percolated and shifted between the hexagonal rods themselves.The present study demonstrated the benefit of controlling the critical temperature of the HII mesophase partial dehydration and softening, as well as the percolation of TAGs. These factors influence the diffusion mode of embedded drugs in the physiological temperature range.

Fractionation of ethylcellulose oleogels during setting

The use of ethylcellulose (EC) polymers as a means to structure edible oils for fat replacement is beginning to show great promise and the use of these 'oleogels' has recently been shown to be feasible in food products. These gels are very versatile, as the mechanical properties can be tailored by altering either the fatty acid profile of the oil component, or the viscosity or concentration of the polymer component. Here we report the observation that certain formulation of EC oleogels tend to separate into two distinct phases; a soft interior core surrounded by a firm exterior sheath. It was found that the extent of this effect depends on EC viscosity, and can also be induced through the addition of certain surfactants, such as sorbitan monostearate and sorbitan monooleate, though not by glycerol monooleate. Although the two visually distinct regions were shown to be chemically indistinct, the cooling rate during gel setting was found to play a large role; rapid setting of the gels reduces the fractionation effect, while slow cooling produced a completely homogeneous structure. In addition, by reheating only the soft region of the gel, a firm and soft fractionated gel could again be produced. Finally, it was observed that oleogels prepared with castor oil or mineral oil have the ability to remove or induce the gel separation, respectively. Taken together, these results indicate chemical interactions may incite the separation into two distinct phases, but the process also seems to be driven by the cooling conditions during gel setting. These findings lend insight into the EC-oleogel gelation process and should provide a stepping stone for future research into the manufacturing of these products.

Deposition and tribological properties of multilayer and mixed films composed of gold and polytetrafluoroethylene

To develop electroconductive solid lubricant films with low surface-free energy, multilayer and mixed films composed of gold, which has high electrical conductivity, and polytetrafluoroethylene (PTFE), which has low surface energy, were deposited by biased radio-frequency sputtering. Their surface-free energies, nanoindentation, and tribological properties were then evaluated. These gold and PTFE multilayer and mixed films were found to have low surface-free energies and high electrical conductivities. The electrical resistivities of the mixed films with lower fluorine and carbon contents were approximately 0.02Ω·cm. The contact angles of the multilayer and mixed films with water were large, and their surface-free energy could be reduced to 29mN/m by increasing their fluorine and carbon contents. The friction coefficients of the multilayer films deposited at a lower power were as low as μ=0.05 in air, as revealed by a low-load friction test. The friction properties and wear durability of the multilayer and mixed films deposited under a higher power were superior under boundary lubrication with distilled water, tap water, and polyalphaolefin without and with glycerol monooleate as an additive, as clarified by a high-load oscillating friction test.

Effect of High-Pressure Homogenization and Stabilizers on The Physicochemical Properties of Curcumin-Loaded Glycerol Monooleate/Chitosan Nanostructures

The objective of this study was to investigate the influence of the high-pressure homogenization (HPH) process and stabilizers on the physicochemical properties of glycerol monooleate (GMO)/chitosan nanostructures using curcumin as a model hydrophobic drug. The oil-in-water nanoemulsion of the GMO/chitosan system was prepared by sonication and HPH techniques using two different stabilizers (polyvinyl alcohol [PVA] and poloxamer 407). The particle size (PS), ζ-potential (ZP) and physical stability of the nanoemulsion were investigated. These nanoemulsions were lyophilized and characterized for PS, ZP, surface morphology, moisture content and physical form of the drug in the nanostructures. The in vitro release and the uptake of curcumin in Caco-2 cells were evaluated using an ultra-performance liquid chromatography method. Three cycles of HPH produced a 50-65% reduction in the PS of the nanoemulsion. A change in stabilizer, from PVA to poloxamer, did not affect the PS, physical stability, moisture content or the physical form of the drug in the formulation. However, there was a significant change in the ZP, surface morphology, in vitro release rate and cellular uptake from the two formulations. The process of HPH effectively reduces the PS of the GMO/chitosan nanoemulsions loaded with the hydrophobic drug. The type of stabilizer used affects several physicochemical properties of the GMO/chitosan nanostructures. Compared with PVA, poloxamer 407 is a more effective stabilizer for stabilizing the GMO/chitosan system containing a hydrophobic drug nanoemulsion at low concentrations.

Glycerol Monooleate-Based Nanocarriers for siRNA Delivery in Vitro

We present studies of the delivery of short interfering ribonucleic acid (siRNA) into a green fluorescent protein (GFP) expressing cell line, using lipid nanocarriers in cubic lyotropic liquid crystal form. These carriers are based on glycerol monooleate (GMO) and employ the use of varying concentrations of cationic siRNA binding lipids. The essential physicochemical parameters of the cationic lipid/GMO/siRNA complexes such as particle size, ζ otential, siRNA uptake stability, lyotropic mesophase behavior, cytotoxicity,and gene silencing efficiency were systematically assessed. We find that the lipid nanocarriers were effectively taken up by mammalian cells and that their siRNA payload was able to induce gene silencing in vitro. More importantly, it was found that the nonlamellar structure of some of the lipid nanocarrier formulations were more effective at gene silencing than their lamellar structured counterparts. The development of cationic lipid functionalized nonlamellar GMO-based nanostructured nanoparticles may lead to improved siRNA delivery vehicles.

Direct esterification of olive-pomace oil using mesoporous silica supported sulfonic acids

Mesoporous silica MCM-41 and SBA-15 containing propyl sulfonic acid groups were synthesized according to the literature and were characterized by X-ray diffraction, N2 adsorption and the H+ exchange capacities of the sulfonic acid groups were titrated. The esterification reaction of glycerol with olive-pomace oil has been carried out by using prepared functionalized mesoporous silica (MCM-41 and SBA-15) as catalysts. It has been monitored by GC two fatty acids (palmitic and oleic acids) as reactants in olive-pomace oil and their related monoacylglycerols (Glycerol monopalmitate GMP and monooleate GMO) as reaction product. The catalytic activities of the functionalized mesoporous silica were compared with commercial catalysts, these included homogeneous catalysts (p-toluenesulfonic acid) and heterogeneous catalysts (Amberlyst-15). The total yield of monoacylglycerols (GMO+GMP) was nearly 40%. Remarkably, we found that MCM-41-SO3H was recycled at least 3 times without any loss of activity.

A new asymmetric diamide from the seed cake of Jatropha curcas L.

A new asymmetric diamide (E)-N-(3-acetamidopropyl)-cinnamamide named curcamide (1) has been isolated from the ethanol extract of the seed cake of Jatropha curcas L. along with 7 known compounds identified as isoamericanin (2), isoprincepin (3), caffeoylaldehyde (4), isoferulaldehyde (5), glycerol monooleate (6), syringaldehyde (7), and β-ethyl-d-glucopyranoside (8). The synthesis and antibacterial activity of the new compound have been also studied.

Structural Behavior and Interactions of Dendrimer within Lyotropic Liquid Crystals, Monitored by EPR Spectroscopy and Rheology

Micro- and macrostructural behaviors of three different lyotropic liquid crystals (LLCs) loaded with a dendrimer, namely second generation poly(propylene imine) (PPI-G2), were studied by means of rheology and electron paramagnetic resonance (EPR). The three mesophases were L(α), Q(224), and H(II) composed of glycerol monooleate (GMO) and water-PPI-G2 solution (and d-α-tocopherol (vitamin E) in the case of H(II)). We characterized the impact of PPI-G2 interactions with the components of the host mesophases on their structural characteristics on different length scales. The incorporation of PPI-G2 within the L(α) and H(II) systems induced the formation of more elastic hexagonal systems with a "solidlike" behavior, while in the Q(224) system a different trend with a "liquidlike" behavior was observed. As a result, the dendrimer induced a remarkable change in both the structural and viscoelastic properties of the systems. Hence, the microenvironment in the interface region within the systems was monitored by computer-aided EPR using 5-doxylstearic acid (5-DSA) as a pH-dependent probe. The microviscosity (τ) and order (S) of systems were found to be sensitive to the PPI-G2 presence: when PPI-G2 concentration increased, τ and S increased in both the L(α) and Q(224) systems. In the H(II) systems two trends were observed, reflecting a decrease in τ and S up to 10 wt % PPI-G2 and subsequently their increase at higher dendrimer concentrations. It was assessed that PPI-G2 interacted strongly with the GMO hydroxyl groups in the L(α) phase, with the water molecules in the Q(224) systems. In the H(II) mesophase strong interactions with both the water and GMO hydroxyl molecules were detected.

Continuous monitoring of phospholipid vesicle hydrolysis by phospholipase D (PLD) reveals differences in hydrolysis by PLDs from 2 Streptomyces species

Phospholipase D (PLD)-mediated hydrolysis of phosphatidylcholine (PC) in large unilamellar vesicles (LUVs) consisting of PC and either glycerol monooleate (GMO) or methyl oleate (MeO) were monitored in situ and in real time by using a choline oxidase-immobilized oxygen electrode. This technique revealed reaction differences between 2 bacterial PLDs. PLD from Streptomyces chromofuscus, which is closely homologous to bacterial alkaline phosphatase, hydrolyzed only 6% of surface PC owing to product inhibition. The catalytic activity of this enzyme was not sensitive to the addition of GMO. On the other hand, typical bacterial PLD from Streptomyces sp. was found to hydrolyze all the PC molecules at the outer surface of LUVs suggesting that this enzyme is free from product inhibition. Introduction of GMO or MeO into the bilayer increased exposure of the PC headgroup and facilitated PC hydrolysis mediated by PLD from Streptomyces sp. GMO and MeO have the same lipophilic tail but the latter lacks hydroxyl groups on its polar head. From kinetic analysis by using the Michaelis–Menten model extended to the reaction at the interface, these compounds were found to activate PLD from Streptomyces sp. in different ways, i.e., MeO increased the protein binding to membranes and GMO stimulated the enzyme-substrate complex formation at membrane surface.

Characterization of Bupivacaine-Loaded Formulations Based on Liquid Crystalline phases and Microemulsions: The Effect of Lipid Composition

This report details the structural characterization and the in vitro drug-release properties of different local anesthetic bupivacaine (BUP)-loaded inverted-type liquid crystalline phases and microemulsions. The effects of variations in the lipid composition and/or BUP concentration on the self-assembled nanostructures were investigated in the presence of the commercial distilled glycerol monooleate Myverol 18-99K (GMO) and medium-chain triglycerides (MCT). Synchrotron small-angle X-ray scattering (SAXS) and rotating dialysis cell model were used to characterize the BUP formulations and to investigate the in vitro BUP release profiles, respectively. The evaluation of SAXS data for the BUP-loaded GMO/MCT formulations indicates the structural transition of inverted-type bicontinuous cubic phase of the symmetry Pn3m → inverted-type hexagonal (H(2)) phase → inverted-type microemulsion (L(2)) with increasing MCT content (0-40 wt %). In the absence of MCT, the solubilization of BUP induces the transition of Pn3m → H(2) at pH 7.4; whereas a transition of Pn3m → (Pn3m + H(2)) is detected as the hydration is achieved at pH 6.0. To mimic the drug release and transport from in situ formed self-assembled systems after subcutaneous administration, the release experiments were performed by injecting low viscous stimulus-responsive precursors to a buffer in the dialysis cell leaving the surface area between the self-assembled system and the release medium variable. Our results suggest that the pH-dependent variations in the lipidic partition coefficient, K(l/w), between the liquid crystalline nanostructures and the surrounding buffer solution are significantly affecting BUP release rates. Thus, a first step toward understanding of the drug-release mechanism of this drug-delivery class has been undertaken tackling the influence of drug ionization as well as the type of the self-assembled nanostructure and its release kinetics under pharmaceutically relevant conditions.

Penetratin-induced transdermal delivery from HII mesophases of sodium diclofenac

Penetratin, a cell penetrating peptide is embedded within a reversed hexagonal (HII) mesophase for improved transdermal delivery of sodium diclofenac (Na-DFC). The HII mesophase serves as the solubilization reservoir and gel matrix whereas penetratin is the transdermal penetration enhancer for the drug. The systems were characterized and the interactions between the components were determined by SAXS, ATR-FTIR and SD-NMR. High affinity of Na-DFC to glycerol monooleate (GMO) was revealed, associated with increasing the order within the water channels. This affinity is enhanced upon heating and seems to be associated with GMO dehydration. Penetratin (PEN) is entrapped at the hydrophilic region of the HII mesophase, between the GMO headgroups, reducing the order of the system and decreasing the size of the hexagonal domains.The transdermal delivery rate of Na-DFC through porcine skin, from the HII mesophases, was enhanced by PEN and so also the cumulative transport crossing the skin. PEN induced accelerated drug diffusion through the stratum corneum, towards the different skin layers.The transdermal delivery enhancement is explained from the results of the ATR-FTIR analysis. It seems that PEN accelerates the structural transition of skin lipids from hexagonal to liquid. The disordering results in enhanced diffusion of Na-DFC through the stratum corneum, followed by enhanced overall penetration of the drug.

Lipolysis and structure controlled drug release from reversed hexagonal mesophase

The present work investigates a system composed of a ternary reversed hexagonal mesophase (HII) loaded with a lipase for modulating drug delivery capabilities of the system. Thermomyces lanuginosa lipase was solubilized into HII mesophase for the benefits of continuing lipolysis of the lipids, consequently disordering and decomposing the hexagonal mesophase and thereby enhancing the diffusion of the encapsulated drug.A single transition from the HII structure to a random micellar phase was detected during the lipolysis. In the first lipolysis stage the hexagonal system (glycerol monooleate, tricaprylin, and water) preserved its symmetry within ca. 200min. During this step about 40–60% molar of the lipids were hydrolyzed, and a gradual shrinking of the HII cylinders (decrease of 8Å in lattice parameter) was detected. In the second lipolysis stage, the HII mesophase gradually disintegrated (faster rate) and the release of a model drug (sodium diclofenac) was significantly enhanced, which was assumed to be lipolysis rate-controlled. After about 15h the HII mesophase was disintegrated into two dispersed immiscible phases.The release obeyed two-step Higuchi kinetics with two consecutive linear correlations of the drug release.

Development and evaluation of a self-emulsifying drug delivery system of amphotericin B

Amphotericin B is a polyene antifungal antibiotic belonging to Class IV of Biopharmaceutics Classification System which is not absorbed from the gastrointestinal tract after oral administration. The aim of this research work was to develop a self-emulsifying drug delivery system (SEDDS) of amphotericin B and to evaluate the dissolution and permeability of amphotericin B from the formulation. The solubility of amphotericin B in various oils, surfactants and cosurfactants was determined.Various SEDDS formulations were prepared with varying amounts of oil, surfactant and co-surfactant. Evaluation parameters for formulation optimization were drug content, self-emulsification, droplet size analysis, and precipitation studies. In vitro dissolution was studied in comparison to the pure drug. Permeability was studied using non-everted intestinal sac method. The optimized formulation consisted of glycerol mono-oleate (10%, w/w), tween 80 (36%, w/w), polyethylene glycol 400 (27%, w/w), and propylene glycol (27%, w/w) with a drug content of about 8 mg per ml. The self-emulsifying formulation showed 100% dissolution within 30 minutes whereas the pure drug exhibited a very poor rate of dissolution.In vitro intestinal permeability was studied by noneverted intestinal sac method using rat intestine. The self-emulsifying formulation showed 100% drug permeation within 30 minutes compared to negligible permeation from the drug suspension. The study demonstrates that SEDDS approach may be useful for enhancement of dissolution and intestinal permeation of amphotericin B belonging to class IV of Biopharmaceutic Classification System.

Elimination of Glycidyl Palmitate in Diolein by Treatment with Activated Bleaching Earth

In this study, activated bleaching earth (ABE) was used to eliminate glycidyl esters from both triacyl- and diacylglycerol oils. To investigate the mechanism, glycerol dioleate containing glycidyl palmitate (GP) was treated with ABE and the fate of the GP was monitored by analyzing the feed, treated, and ABE-absorbed oils using a gas-liquid chromatograph equipped with a flame-ionized detector. GP was completely removed from both the treated and absorbed oils. This indicates that this treatment is useful for GE removal from diacylglycerol oil, although it was not achieved by absorption of GE on ABE but rather by modification of GP. The results of composition analysis demonstrate that GP is transformed to glycerol monopalmitate, glycerol palmitate oleate, and glycerol dipalmitate at a recovery rate of 99.1 ± 1.3 %. An increase in glycerol monooleate and trace amounts of free glycerol and fatty acids were also observed after treatment. The transformation is proposed to involve a ring-opening reaction of GP with water contained in the ABE and in the bulk oil followed by an interesterification reaction among the resultant monopalmitate and the glycerol dioleate of the bulk oil. All the generated compounds were simple acylglycerols and glycerol. Therefore, ABE treatment could be useful for GE removal during the manufacture of edible oils.