Sucrose Oleate Research Articles

Effect of type of fatty acid attached to sucrose ester on the stability of water-in-oil Pickering emulsion

Water-in-oil (W/O) Pickering emulsions have a broad range of potential for use in the food industries. However, because of the scarcity of edible W/O-type particles, the production and stabilization of W/O Pickering emulsion is challenged. Sucrose esters (SEs) have great promise as W/O-type particles, whose properties vary with fatty acid moiety attached. This study investigated the effect of fatty acid residue type on the interface activity of SE and corresponding emulsion properties, in order to select the most suitable SE. Sucrose stearate (SE-S), sucrose palmitate (SE-P), sucrose laurate (SE-L), sucrose erucic acid ester (SE-E) and sucrose oleate (SE-O) were applied. Results showed that the saturation of fatty acid residues caused the difference of crystallinity of SE: SE-S＞SE-P＞SE-L＞SE-E＞SE-O. The lower crystallinity resulted in the increased hydrophilicity of SE-O with a closer θ (101.4°) to 90°, which facilitated interfacial adsorption and rearrangement, and larger decrease of interfacial tension (3.93 mN/m). Consequently, SE-O was capable of stabilizing more water volume fraction (75%). Moreover, the emulsion stabilized by SE-O was observed smaller droplet sizes, higher gel strength, and physical stability. The results revealed that SE-O was more appropriate for the preparation of W/O Pickering emulsion.

Formulation engineering of water-in-oil-in-water emulsions for salt reduction with sucrose oleate as a PGPR-alternative lipophilic emulsifier

Formulation engineering of water-in-oil-in-water emulsions for salt reduction with sucrose oleate as a PGPR-alternative lipophilic emulsifier

Formulation Engineering of Water-in-Oil-in-Water Emulsions for Salt Reduction with Sucrose Oleate as a Pgpr-Alternative Lipophilic Emulsifier

Formulation Engineering of Water-in-Oil-in-Water Emulsions for Salt Reduction with Sucrose Oleate as a Pgpr-Alternative Lipophilic Emulsifier

Prominent efficiency in skin delivery of resveratrol by novel sucrose oleate microemulsion.

To achieve an efficient skin delivery of resveratrol using sucrose fatty acid ester microemulsions and to clarify the mechanism of enhanced penetration. Skin delivery of resveratrol using different sucrose fatty acid ester microemulsions was examined in vitro. Vehicle-skin interaction was assessed by applying blank microemulsions to skin. Skin incorporation of microemulsion components was also assessed. The microemulsion consisting of sucrose oleate (SO), ethanol, isopropyl myristate (IPM) and water (MESO-E) showed a prominent increase in the amount of skin incorporation of resveratrol, which was more than 5-fold higher than those of all microemulsions we previously examined. Using MESO-E, resveratrol was rapidly incorporated into skin and mainly located in the dermis. When applied in the concentration range of 5-55 mm, the amount of skin incorporation of resveratrol increased with the applied concentration up to 30 mm, whereas skin incorporation efficiency was inversely proportional to the concentration. The microemulsion-skin interaction seemed to be involved in the enhanced skin delivery process of resveratrol by MESO-E. Stratum corneum modification due to the penetration of IPM, ethanol and SO is also involved in this interaction. MESO-E would be a promising vehicle for the efficient skin delivery of resveratrol, especially when applied at a low concentration.

Effects of Particle Size of Sucrose Suspensions and Pre‐incubation of Enzymes on Lipase‐Catalyzed Synthesis of Sucrose Oleic Acid Esters

AbstractThe effects of high‐speed homogenization, high‐intensity ultrasound, and their combination were evaluated for the reduction of the particle size of sucrose crystals to enhance solvent‐free lipase‐catalyzed synthesis of sucrose oleate at 65 °C. The combination of homogenization and ultrasound greatly decreased the particle size of suspended sucrose crystals in mixtures of oleic acid/sucrose oleate (86 wt% monoester and 14 wt% diester at a ratio of 90/10 w/w) from 88 to 18 μm. The suspension‐based medium was charged to a stirred tank bioreactor that also contained immobilized lipase from Rhizomucor miehei or Candida antarctica (Lipozyme®IM and Novozym® 435, respectively; Novozymes, Franklinton, NC, USA), that was pre‐incubated in oleic acid for several different temperatures (23–60 °C), durations (4–24 h), and stir rates (50–400 rpm, radius of 3 cm), prior to use. The optimal performance was achieved using C. antarctica lipase (83.3 wt% ester, consisting of 46 wt% monoester) in the presence of molecular sieves (18 wt%). The low water concentration (~0.12 wt%) did not affect the activity of C. antarctica lipase.

Preparation of astaxanthin nanodispersions using gelatin-based stabilizer systems.

The incorporation of lipophilic nutrients, such as astaxanthin (a fat soluble carotenoid) in nanodispersion systems can either increase the water solubility, stability and bioavailability or widen their applications in aqueous food and pharmaceutical formulations. In this research, gelatin and its combinations with sucrose oleate as a small molecular emulsifier, sodium caseinate (SC) as a protein and gum Arabic as a polysaccharide were used as stabilizer systems in the formation of astaxanthin nanodispersions via an emulsification-evaporation process. The results indicated that the addition of SC to gelatin in the stabilizer system could increase the chemical stability of astaxanthin nanodispersions significantly, while using a mixture of gelatin and sucrose oleate as a stabilizer led to production of nanodispersions with the smallest particle size (121.4 ± 8.6 nm). It was also shown that a combination of gelatin and gum Arabic could produce optimal astaxanthin nanodispersions in terms of physical stability (minimum polydispersity index (PDI) and maximum zeta-potential). This study demonstrated that the mixture of surface active compounds showed higher emulsifying and stabilizing functionality compared to using them individually in the preparation of astaxanthin nanodispersions.

Facile and direct synthesis of long-chain chitin from chitobiose via proton-assisted nonaqueous biocatalysis

Facile and direct enzymatic synthesis of long-chain chitin from chitobiose without activation of an anomeric carbon via traditional organic chemistry was first achieved in a one-step and one-pot reaction by the combined use of a surfactant-enveloped enzyme (SEE) and an organic protic acid co-catalyst in the aprotic nonaqueous solvent, N,N-dimethylacetamide. The SEE biocatalyst was successfully prepared by enveloping lysozyme, having chitinase activity, with sucrose oleate surfactant. When o-nitrobenzenesulfonic acid was used as a co-catalyst, a degree of polymerization of synthesized chitin reached ca. 210 in ca. 79% yield by proton-assisted SEE-mediated biocatalysis. The conversion ratios and average chain lengths depended on the types of organic protic acids, and high catalytic efficiencies were maintained in each case, resulting in high yields of ca. 40–80%. The SEE biocatalyst, which has enzymatic activity even in aprotic organic media containing strong organic acids, allowed the facile and high-yielding efficient synthesis of long-chain chitin from chitobiose in its original form. Therefore, proton-assisted SEE-mediated biocatalysis should prove useful for the glycosynthesis of many glycomaterials.

Mortality of Bemisia tabaci biotype B (sternorrhyncha: aleyrodidae) adults by aliphatic and aromatic synthetic sucrose esters

The B-strain of Bemisia tabaci Gennadius is a key pest of several crops and chemical control is the main control method used by growers, although reduction in efficacy due to insecticide resistance has already been reported. The aim of this work was to investigate the insecticidal effect of an array of synthetic sucrose esters with the aliphatic and aromatic groups on whitefly adults. Sucrose butyrate, caprate, octanoate, palmitate, oleate, octaacetate, phthalate, benzoate, and sucrose diacetate hexaisobutyrate were tested. The solutions were prepared and applied on the adults caught on yellow sticky traps using the Potter spray tower. Long-chains sucrose aliphatic esters were more effective against the silverleaf whiteflies and the highest mortality was obtained with sucrose oleate and sucrose octanoate. Since these compounds were tensoactive, sodium dodecylsulphate was also tested for the comparison but no effect was observed. Sucrose butyrate and other aliphatic and aromatic sucrose polyesters showed negligible effect on the silverleaf whiteflies.

Surfactant Chain Length Effect on the Structural Parameters of Nonionic Microemulsions

In this study we estimated the structural parameters of (water+propylene glycol)/sucrose esters/(benzaldhyde+ethanol) systems. The weight ratios of water/propylene glycol and that of benzaldhyde/ethanol equal 2 and 1, respectively. The sucrose esters were sucrose laurates (L595, L1695, and SM1200), sucrose myristate (M1695), sucrose palmitate (P1670), sucrose oleate (O1570), and sucrose stearate (S1570). The pseudoternary phase behavior at 37°C was explored to determine the extension of the microemulsion phase regions. A one‐phase microemulsion region extending from the oil rich region to the water rich corner was observed in these systems. It was found that minor changes in the surfactant chain length, structure, and composition suffice to provoke a considerable change in the aggregation number, core radius and interfacial area per surfactant and cosurfactant molecules head groups in the formed microemulsions. The interfacial area per surfactant head group decreases with the increase in the surfactant chain length. For a sucrose ester with a given chain length the interfacial area per surfactant head group decreases with the increase in the surfactant monoester content. The interfacial area per surfactant head group increases with the increase in the surfactant concentration and the water core volume in the formulated microemulsions.

Phase behavior and SANS investigations of edible sugar–limonene microemulsions

We have studied the phase behavior and microstructure of edible microemulsions of d-limonene with concentrated aqueous sugar solutions (>65 wt%) using sucrose laurate and sucrose oleate as surfactants. The phase behavior of these mixtures was systematically studied as a function of temperature and surfactant composition, identifying the specific effects of sugar concentration, surfactant chain length, and oil loading on the formation of microemulsion and lamellar phases. Small-angle neutron scattering experiments confirm the presence of well-structured microemulsions with domain sizes ranging from ∼35 to 60 nm. With few exceptions, the patterns of microemulsion phase behavior with concentrated sugar solutions are very similar to that of aqueous systems.

Influence of Sucrose Esters on the In Vivo Percutaneous Penetration of Octyl Methoxycinnamate Formulated in Nanocapsules, Nanoemulsion, and Emulsion

ABSTRACTThe influence of sucrose laureate and sucrose oleate on the in vivo percutaneous penetration of octyl methoxycinnamate (OMC) formulated in i) colloidal suspensions (nano-emulsions and nanocapsules), and ii) conventional o/w emulsions was evaluated. The results showed that nano-emulsions formulated with sucrose laureate exhibited the highest penetration in the stratum corneum compared to the other formulations. A two-fold increase in OMC skin deposition was observed with the nano-emulsion containing sucrose laureate when compared to the control. The data obtained suggest that the total amount of OMC detected in the stratum corneum and the penetration depth are strongly dependent upon the formulation's nature, the particle size, and the type of enhancer.

Skin permeation enhancement by sucrose esters: A pH-dependent phenomenon

The purpose of the present study was to evaluate the effect of sucrose esters (particularly, sucrose laureate and sucrose oleate in Transcutol ®) on the percutaneous penetration of a charged molecule as a function of ionization. We have investigated the influence of these sucrose esters on the in vitro diffusion profiles of lidocaine hydrochloride, a weak ionizable base (p K a = 7.9), at different pH values, using porcine ear skin as the barrier membrane. As expected, lidocaine flux in the absence of an enhancer, increased from pH 5 to 9 with a corrresponding increase in the level of the unionized base. However, when skin was pretreated with 2% laureate in Transcutol (2% L-TC), drug permeation was higher at pH 5.0 and 7.0 than at 9.0. A different trend was observed in experiments with 2% oleate in Transcutol (2% O-TC), where skin flux was maximal at a more basic pH, when the degree of ionization is low. The results suggest that sucrose laureate enhances the penetration of the ionized form of the drug (12-fold greater flux relative to control), whereas sucrose oleate is more effective in promoting permeation of the unionized species. The structural properties of the sucrose esters as well as the degree of ionization of the drug are important characteristics affecting the transdermal flux of lidocaine.

Mathematical modelling of ester synthesis by lipase in biphasic system

The invented mathematical model of ester synthesis in a biphasic system using the immobilised Mucor circinelloides lipase, situated in organic phase, was experimentally verified by butyl oleate, oleyl oleate, sucrose oleate and sucrose caprylate synthesis. The model took into consideration the fact revealed in experiments that water being a by-product of a reaction, created a separate phase thus influencing a value of equilibrium constant in the organic phase (KO). The applied mathematical model makes it possible to determine with high accuracy the yield of ester synthesis that can be obtained in the reaction poststational state.

DSC Study of Effects of Addition of Sucrose Fatty Acid Esters on Oil Phase Crystallization of Oil in Water Emulsion

Differential scanning calorymetry (DSC) was conducted to clarify the crystallization behavior of n-hexadecane dispersed in oil-in-water emulsions (n-hexadecane : water=20 : 80). Tween 20 was used for emulsification and four sucrose fatty acid esters; sucrose laurate (L-195), sucrose palmitate (P-170), sucrose stearate (S-170) and sucrose oleate (O-170) were added to n-hexadecane. Crystallization temperature (Tc) of n-hexadecane in the emulsion system was 3.4°C and the melting temperature (Tm) was 17.4°C. Tc and Tm were 16.9°C and 18.5°C for bulk n-hexadecane, respectively. P-170 and S-170 addition resulted in considerable increase in Tc of n-hexadecane/water emulsions but L-195 had only slight effect. O-170, possessing oleic acid moieties as its hydrophobic portion had no effect on Tc of n-hexadecane/water emulsions. In bulk liquid, none of the sucrose esters showed any effect on Tc or Tm of n-hexadecane.With the addition of P-170 and S-170, small endothermic peaks appeared at 3.6°C and 4.1°C (on heating) and exothermic peaks at -3.2 and -3.0°C (on cooling) appeared in addition to the crystallization and melting peaks of n-hexadecane. These peaks corresponded to phase transitions of molecular aggregates formed emulsion interfaces. The mechanisms for acceleration of crystallization of n-hexadecane and molecular aggregate formation are discussed with consideration to interface adsorption and mesophase formation due to sucrose fatty acid ester addition in n-hexadecane.

Electron and light microscopical investigation of defect structures in mesophases of pharmaceutical substances

Transmission electron microscopy of freeze fractured and replicated samples (TEM) and polarizing light microscopy (PLM) are used to investigate the defect structures of the thermotropic and lyotropic mesophases of the nonsteroidal antiinflammatory drug fenoprofen sodium and of the thermotropic mesophase of the nonionic surfactant sucrose oleate (O1570). All mesophases have a layered, smectic structure. The thermotropic liquid crystal of fenoprofen sodium is an interdigitated smectic A phase (smectic Ad) having the highest viscosity of the investigated samples. The thermotropic mesophase of the sugar ester is also of the type smectic A, likely to be of subtype smectic A2 (bilayered smectic structure). The lyotropic mesophase is of lamellar liquid crystalline nature and has a much lower viscosity than the thermotropic mesophases. In the PLM the lyotropic fenoprofen mesophase has a strong tendency to form a pseudoisotropic texture, indicating a strong tendency to form undisturbed layered structures. Other textures exhibited in the PLM are fan-shaped texture and maltese-cross texture. Confocal domains, cylinders, pits and peaks as well as screw dislocations are found in great number in the TEM. However, no greater regions of undisturbed lamellar arrangement in the lyotropic mesophase could be detected. The only texture of the thermotropic fenoprofen mesophase visible in the PLM is the fan-shaped texture, indicating confocal domains as predominant structural elements. However, no confocal domains (tori or Dupin cyclides) are found in the TEM. In the PLM the sugar-ester mesophase exhibited a fan-shaped texture, maltese crosses and oily streaks as dominant textures. In the TEM only a few +π and −π disclinations and imperfect confocal domains could be detected. The discrepancies in the appearance of defect structures and textures between the mesophases as well as the discrepancies in the findings in the PLM and in the TEM investigations are caused by the different sample preparation and the different viscosities of the mesophases.

Viability of Listeria monocytogenes, Staphylococcus aureus and psychotrophic spoilage micro-organisms in refrigerated ground beef supplemented with sucrose esters of fatty acids

Populations of Listeria monocytogenes, Staphylococcus aureus and naturally occurring psychotrophic micro-organisms in ground beef supplemented with food-grade sucrose esters of fatty acids were monitored for up to 7 days of storage at 5 or 15°C. Populations of L. monocytogenes in beef containing sucrose laurate (0·30 and 0·49%) or sucrose palmitate (0·32%) were significantly lower (P≤0·05) than populations in the control beef after 1, 2, 4 and 7 days of storage at 5 °C. Ground beef containing 0·32% sucrose palmitate which was stored at 15 °C also contained significantly lower populations of L. monocytogenes throughout the 7-day storage period. No significant (P ≤ 0·05) differences in populations of S. aureus were observed in beef supplemented with sucrose stearate (0·23 and 0·32%) or sucrose oleate (0·09 and 0·15%) when storage was at 5 °C. At 15 °C, inhibition of S. aureus by sucrose laurate, sucrose palmitate and sucrose stearate was significant through day 4. Sucrose oleate (0·15%) was without affect at 15 °C for both pathogens. Populations of psychrotrophs were significantly less (P≤0·05) in beef containing 0·30 or 0·49 sucrose laurate through day 2, regardless of the storage temperature. Supplementation with sucrose esters of palmitic (0·32%), oleic (0·15%) and stearic (0·32%) acids failed to control the growth of naturally occurring psychrotrophic micro-organisms. Studies to determine the effects of higher concentrations of sucrose esters of fatty acids on survival and growth of bacterial pathogens and psychrotrophs in ground beef are warranted.

Influence of surfactant concentration and temperature on the flow behaviour of sucrose oleate aqueous systems

This paper deals with the flow behaviour of aqueous systems of a sucrose oleate with a high hydrophilic—lipophilic balance (HLB, 15). Influences of temperature (10–45°C) and surfactant concentration (10–45 wt.%) have been studied. The flow curves show both a limiting viscosity at low shear rates and a shear-thinning region after a critical shear rate that depends on temperature and sucrose oleate concentration. Experimental flow curves have been shifted on a master curve using the time—temperature superposition method. This master curve includes all the experimental flow curves obtained with the systems having a sucrose oleate concentration between 10 and 30 wt.%. The shift factor shows a complex dependence on temperature, having two different Arrhenius-like regions with two different activation energies. These results can be explained on the basis of the existence of a micellar phase at low concentrations and temperatures and then a lamellar phase, completely developed for concentrations higher than 35 wt.% surfactant.