Octenyl Succinate Research Articles

Effect of degree of substitution of octenyl succinate on starch micelles for synthesis and stability of selenium nanoparticles: Towards selenium supplements

To develop a promising selenium supplement that overcomes the instability and poor water dispersibility of selenium nanoparticles (SeNPs), we synthesized a series of amphiphilic octenyl succinic anhydride starch (OSAS) through esterification. As the degree of substitution (DS) increased, the particle size of OSAS micelles and the critical micelle concentration (CMC) decreased. FTIR and XRD analysis confirmed the successful introduction of octenyl succinic anhydride groups onto starch. Subsequently, OSAS micelles were used as carriers to synthesize SeNPs via in situ chemical reduction, forming SeNPs-loaded self-assembled starch nano-micelles (OSAS-SeNPs). The OSAS-SeNPs exhibited spherical dispersion in water with an average diameter of 116.1 ± 2.3 nm, contributed to enhanced hydrophobic interactions. TEM images showed a core-shell structure with SeNPs as the core and OSAS as the shell. FTIR results indicated hydrogen bonding interactions between OSAS and SeNPs. Due to the negatively charged OSAS shell and hydrogen bonding (OH⋯Se), OSAS-SeNPs remained non-aggregated for one month at room temperature, demonstrating remarkable stability. This study suggests that using OSAS can address the synthesis and stability issues of SeNPs, making it a potential selenium supplement candidate for further evaluation as an anticancer agent.

Preparation and Biological Activity Studies of Octenyl Succinic Anhydride Starch-Based Emulsions Containing Natural Essential Oils and Their Components

In this study, clove essential oil (CL), eugenol (EU), and cinnamaldehyde (CI) were immobilized in starch sodium octenyl succinate (SSO) using an emulsification method. The main characteristics, stability, and biological properties of the prepared emulsions were established. Particle size analyses using dynamic light scattering showed that the smaller droplets were characteristic of emulsions containing CI (205–218 nm) and EU (181–236 nm), while the largest droplets were determined for CL emulsions (293–348 nm). Moreover, the highest antioxidant activity was determined for CL (79–83%) and EU (80–88%) emulsions, while CI emulsions showed the greatest antibacterial activity. The obtained emulsions were applied to the paper sheets and the bioactive properties of coated paper were studied. Evaluation of antioxidant properties revealed that high antioxidant activity reaching 76–92% and 87–91% was characteristic of coatings containing CL and EU, respectively. Meanwhile, coatings containing CI showed quite low antioxidant activity (4–9%) but demonstrated the greatest antimicrobial effect on Gram-negative and Gram-positive bacteria as well as yeasts. Hence, CL and EU emulsions could be used as effective natural antioxidants, whereas CI emulsions could be applied as an antimicrobial agent on cellulose-based substrates for a wide range of human health protection applications.

Enhancing the Solubility, Stability, and Bioavailability of Retinol Acetate through Mechanochemistry.

This study utilizes mechanochemistry to prepare retinol acetate (RA) solid dispersion (RA-sodium starch octenyl succinate (SSOS)), resulting in improved solubility, stability, and bioavailability compared with raw RA and commercial RA microcapsules. RA, poloxamer 188, SSOS, and milling beads (8 mm) were mixed in a ratio of 2:1:8:220 (w/w) and ball-milled at 100 rpm for 3 h. RA-SSOS exhibited a solubility of 1020.35 μL/mL and a 98.09% retention rate after aging at 30 °C. Rats fed with RA-SSOS showed an ∼30% increase in organ RA content. Characterization analysis attributed the solubility and stabilization of RA-SSOS to hydrogen bonding between RA and SSOS, along with an amorphous state. RA-SSOS offers significant advantages for the pharmaceutical and food industries, leveraging mechanochemistry to enhance solid dispersions for hydrophobic compounds and optimize drug delivery.

Impact of Esterification with Octenyl Succinic Anhydride on the Structural Characteristics and Glucose Response in Mice of Wheat Starch.

In this study, we investigated the structural properties and digestibility of wheat starch treated with octenyl succinic anhydride (OSA). For the experiment, the samples were reacted with 2, 4, 6, 8, and 10% OSA (pH 8.5-9.0) for 2 h. A light micrograph showed that there was no difference in the morphology and Maltese cross between native and OSA-treated starch. The X-ray diffraction (XRD) patterns of the native and OSA-treated starches showed typical A-type diffraction. In addition, the Fourier transform infrared (FT-IR) spectrum showed a distinct carbonyl peak at approximately 1730 cm-1, indicating the stretching vibration of the C=O bond of the ester group. The degree of substitution (DS) and content of resistant starch (RS) increased with increasing concentrations of treated OSA because of the increase in ester bonds. In particular, RS was thermostable compared to the RS content in uncooked and cooked starch. Blood glucose levels and response in vivo decreased as the OSA concentration increased. Treatment of wheat starch with 8% OSA concentration produced 35.6% heat-stable resistant starch. These results suggest that starch modified with OSA can be used to produce functional foods for diabetes.

Oral soluble shell prepared from OSA starch incorporated with tea polyphenols for the microencapsulation of Sichuan pepper oleoresin: Characterization, flavor stability, release mechanisms and its application in mooncake

The market share of Sichuan pepper oleoresin (SPO) in the flavor industry is increasing steadily; however, its high volatility, low water solubility, and poor stability continue to pose significant challenges to application. The microencapsulation prepared by emulsion embedding and spray drying is considered as an effective technique to solve the above problems. Sodium octenyl succinate starch (OSA starch) and tea polyphenols (TPs) were used to develop OSA-TPs complex as encapsulants for SPO to prepare orally soluble microcapsules. And the optimum doping of TPs was determined. SPO microcapsules have good properties with high encapsulation efficiency up to 88.13 ± 1.48% and high payload up to 41.58 ± 1.86% with low water content and high heat resistance. The binding mechanism of OSA starch with TPs and its regulation mechanism and effect on SPOs were further analyzed and clarified. The binding mechanism between OSA starch and TPs was clarified in further analyses. The OSA-TPs complexes enhanced the rehydration, release in food matrix and storage stability of SPO, and exhibited good sensory immediacy. Flavor-improved mooncakes were successfully developed, achieving the combination of mooncake flavor and SPO flavor. This study provided a valuable way to prepare flavoring microcapsules suitable for the catering industry, opened up the combined application of SPO and bakery ingredients, and was of great practical value and significance for improving the processing quality of flavor foods, driving the development of the SPO industry, and enhancing the national dietary experience.

Comparative Study on the Emulsification of Octenyl Succinic Anhydride Modified Sweet Potato Starch: As Macromolecular and Particulate Stabilizers

AbstractSweet potato is one of the essential starch materials for food and feed world widely. However, its application is limited by the low viscosity and poor stability of native starches. Herein, sweet potato starch is modified by octenyl succinic anhydride (OSA) in the aqueous system. The optimization for esterification is studied using response surface methodology. The characteristics of OSA‐modified sweet potato starch are investigated, and its emulsifying properties as macromolecular and particulate stabilizers in the oil‐in‐water systems are compared. The optimal process conditions for OSA modification are: reaction time 4.0 h, temperature 38.8 °C, pH of the reaction system 8.2, starch concentration 32.2%, OSA amount 3.0%. The degree of substitution is 0.0185, and reaction efficiency is 79.7% under the optimum conditions. The new peaks at 1725 and 1573 cm−1 are observed by Fourier transform infrared spectroscopy. Compared with native starch, OSA‐modified sweet potato starch exhibits higher viscosities, improved paste clarity, and decreased retrogradation. The confocal laser scanning microscope results show that the gelatinized starch macromolecule and ungelatinized starch particles can arrange at the water–oil interface. The OSA‐modified sweet potato starch is both an effective macromolecular emulsifier and a particulate stabilizer, effectively stabilizing oil‐in‐water emulsions.

Regulation of fine structure of different types of natural waxes by octenyl succinate starch in starch bioplastics

This work conducted a comparative study on the ability of octenyl succinate starch to regulate the fine structure and physicochemical properties of starch-based plastics containing different types (beeswax, candelilla wax, carnauba wax) and contents of waxes. All the waxes increased the apparent viscosity and storage modulus of the film-forming solution, and obstructed the establishment of hydrogen bond within the film matrix. The limited emulsifying capacity of octenyl succinate starch resulted in different distributions of the three waxes in the matrices, thereby forming different films' microstructures. Carnauba wax negatively affected the hydrophobicity, barrier and mechanical properties of the films due to its poor compatibility with the starches. In contrast, the addition of beeswax and candelilla wax effectively improved the hydrophobicity and moisture barrier, especially for some appropriate wax heterostructures presented in the matrices. Results suggested that octenyl succinate starch could be well emulsified and compatible with beeswax (5%–15% w/w content) to regulate the fine structure to achieve lower water sensibility of starch bioplastics.

Effects of gelatin type and concentration on the preparation and properties of freeze-dried fish oil powders

The effects of gelatin type (porcine skin gelatin, PSG; bovine skin gelatin, BSG; fish gelatin, FG; or cold-water fish skin gelatin, CFG) and concentration on the preparation and properties of fish oil powders were investigated in this work. The oil powders were prepared using the combination method of gelatin-sodium hexametaphosphate complex coacervation with starch sodium octenyl succinate (SSOS)-aided freeze-drying. Compared with the other gelatins, CFG—with an unobvious isoelectric point, a lower molecular weight, more hydrogen bonds, and longer gel formation time—could not form complex coacervates, which are necessary to prepare oil powders. For oil powders obtained from the other gelatins, gelatin type and concentration did not have obvious effects on microscale morphologies; they did, however, have significant effects on physicochemical properties. The highest peroxide values of the oil powders were mainly dependent on the gelatins, expressed in the following manner: PSG (153 ± 5 – 168 ± 3 meq/Kg oil) < BSG (176 ± 5 – 188 ± 1 meq/Kg oil) < FG (196 ± 11 – 201 ± 22 meq/Kg oil). Acidic and neutral pH could not dissolve the complex coacervates. However, the oil powders could be quickly dissolved to form emulsion droplets in the gastric phase, and that SSOS increased coacervate stability and promoted oil digestion during the in vitro gastrointestinal process. In sum, this study contributes fundamental information to understanding the development of fish oil solid encapsulation preparations.

A Novel Strategy to Enhance the pH Stability of Zein Particles through Octenyl Succinic Anhydride-Modified Starch: The Role of Preparation pH.

Ensuring the stability of zein nanoparticles at different pH levels is crucial for their application as nanocarriers. In this study, octenyl succinic anhydride-modified starch (OSA-modified starch) was employed to enhance the stability of zein nanoparticles against different pH levels by forming complex nanoparticles with OSA-modified starch. The effect of preparation pH on the stability of the zein/OSA-modified starch nanoparticles was investigated. Sedimentation occurred in zein nanoparticles as the pH reached the isoelectric point. However, the stability of zein nanoparticles at various pH levels significantly improved after adding OSA-modified starch to form zein/OSA-modified starch nanoparticles regardless of whether they were prepared under acidic or alkaline pH conditions. Notably, the stability of zein/OSA-modified starch nanoparticles prepared at an acidic pH was higher than that of those prepared at an alkaline pH, thereby highlighting the critical role of the preparation pH for zein/OSA-modified starch in maintaining the stability of zein. The stable zein/OSA-modified starch nanoparticles developed in this study exhibit significant potential for use in delivery systems across various pH environments.

Acid heating treatment of octenyl succinate anhydride starch and its application in Pickering emulsion stability

Acid heating treatment of octenyl succinate anhydride starch and its application in Pickering emulsion stability

Composite formation of whey protein isolate and OSA starch for fabricating high internal phase emulsion: A comparative study at different pH and their application in biscuits

The composites formed by whey protein isolate (WPI) and octenyl succinate anhydride (OSA)-modified starch were characterized with a focus on the effect of pH, and their potential in fabricating high internal phase emulsions (HIPEs) as fat substitutes was evaluated. The particles obtained at pH 3.0, 6.0, 7.0, and 8.0 presented a nanosized distribution (122.04 ± 0.84 nm–163.24 ± 4.12 nm) while those prepared at pH 4.0 and 5.0 were remarkably larger. Results from the shielding agent reaction and Fourier transform infrared spectroscopy (FT-IR) showed that the interaction between WPI and OSA starch was mainly hydrophobic at pH 3.0–5.0, while there was a strong electrostatic repulsion at pH 6.0–8.0. A quartz crystal microbalance with dissipation (QCM-D) study showed that remarkably higher ΔD and lower Δf/n were observed at pH 3.0–5.0 after successive deposition of WPI and OSA starch, whereas slight changes were noted for those made at higher pH values. The WPI-OSA starch (W–O) composite-based HIPEs made at pH 3.0 and 6.0–8.0 were physically stable after long-term storage, thermal treatment, or centrifugation. Incorporation of HIPE into the biscuit formula yielded products with a desirable sensory quality.

Preparation, Characterization and In-vitro Evaluation of Nano Encapsulated 1-Octacosanol for Solubility Enhancing by using Various Polymers through Spray Drying Approach

This research aimed to develop a nano-encapsulated free-flow powder of 1-octacosanol for functional food application. We had prepared stable green nano-emulsion oil in water by Dyno Mill and spray dryer for free flow powder by using different polymers (Hydroxypropyl methylcellulose, polyvinylpyrrolidone, octenyl succinate starches) as hydrophilic polymers in different ratios for enhancing the solubility. Zeta potential, X-ray diffraction (XRD), fourier transform infrared spectroscopy (FTIR), encapsulation efficiency, particle size distribution, surface morphology, differential scanning calorimetry spectroscopy and in-vitro dissolution research were used to analyze 1-octacosanol. The optimized nano-emulsion preparation F15 consists of an average particle size 720.9 nm, zeta potential -24.5 mV shows stable nano-emulsion oil in water type, and encapsulation efficiency was found to be 96.76%, FTIR studies did not show any evidence of interaction between the herbal extract and the polymers. XRD shows the conversion of crystalline to amorphous nature of powder. In differential scanning calorimetry (DSC), spectroscopy studies found three major peaks in standard herbal extract peaks is 60.21, 67.16, 81.27°C and nano-encapsulated spray dried powder peaks are 58.18, 66.44, 79.25°C with minor moisture absorbed by the polymer in formulation. This evaluation shows significant improvement between normal herbal extract of 1-octacosanol and encapsulated spray-dried powder of 1-octacosanol for functional food application successfully improving the water solubility without changing a structural and chemical properties of the 1-octacosanol crystal.

Revisiting the Formation of Starch-Monoglyceride-Protein Complexes: Effects of Octenyl Succinic Anhydride Modification.

Starch-lipid-protein complexes are attracting increasing attention due to their unique structure and low enzymatic digestibility. However, the mechanisms underlying the formation of these ternary complexes, especially those with monoglycerides as the lipid component, remain unclear. In the present study, potato starch or octenyl succinic anhydride (OSA)-modified potato starch (OSAPS), various monoglycerides (MGs), and beta-lactoglobulin (βLG) were used in model systems to characterize the formation, structure, and in vitro digestibility of the respective ternary complexes. Colorimetry and live/dead staining assays demonstrated that the OSAPS had good biocompatibility. Experimental data and molecular dynamics simulations showed that both unmodified potato starch and OSAPS formed starch-lipid-protein complexes with MGs and βLG. Of the two types of starch, OSA formed a greater amount of the more stable type II V-crystallites in complexes, which had greater resistance to in vitro enzymic digestion. This study demonstrated for the first time that starch can interact with MGs and βLG to form ternary complexes and that OSA esterification of starch promoted the formation of more complexes than unmodified starch.

Development of Emulsion Gels Stabilized by Chitosan and Octenyl Succinic Anhydride-Modified β-Cyclodextrin Complexes for β-Carotene Digestion and 3D Printing.

β-cyclodextrin (β-CD)-based emulsion gels encapsulated with nutrition for three-dimensional (3D) printing are promising, while obstacles such as low bioaccessibility of bioactive compounds and the molding process in food manufacturing hinder their application. This study intended to develop stable composite emulsion gels using the complexes of chitosan (CS) and octenyl succinic anhydride (OSA)-modified β-CD (OCD) to conquer these challenges. The esterification of OSA generated more negatively charged OCD and ester groups, which aided in the combination of OCD and CS through enhanced electrostatic and hydrogen bonding interactions. The addition of CS improved the emulsification properties of the complexes and acted as a bridge link in the aqueous phase, thereby increasing the gel strength of the composite emulsion gels. Moreover, the encapsulation of β-carotene destabilized the strength of the emulsion gels by lowering the interfacial tension. The emulsion gel stabilized by OCD3/CS-0.75% at an initial pH not only successfully encapsulated β-carotene and presented the highest bioaccessibility of 41.88 ± 0.87% in the in vitro digestion but also showed excellent 3D printability. These results provided a promising strategy to enhance the viscoelasticity of β-CD-based emulsion gels and accelerate their application in bioactive compound delivery systems and 3D food printing.

Effect of sodium starch octenyl succinate-based Pickering emulsion on the physicochemical properties of hairtail myofibrillar protein gel subjected to multiple freeze-thaw cycles

A Pickering emulsion based on sodium starch octenyl succinate (SSOS) was prepared and its effects on the physicochemical properties of hairtail myofibrillar protein gels (MPGs) subjected to multiple freeze-thaw (F-T) cycles were investigated. The whiteness, water-holding capacity, storage modulus (G′) and texture properties of the MPGs were significantly improved by adding 1 %–2 % Pickering emulsion (P < 0.05). Meanwhile, Raman spectral analysis demonstrated that Pickering emulsion promoted the transformation of secondary structure, enhanced hydrogen bonds and hydrophobic interactions, and promoted the transition of disulfide bond conformation from g-g-g to g-g-t and t-g-t. At an emulsion concentration of 2 %, the α-helix content decreased by 10.37 %, while the β-sheet content increased by 7.94 %, compared to the control. After F-T cycles, the structure of the MPGs was destroyed, with an increase in hardness and a decrease in whiteness and water-holding capacity, however, the quality degradation of MPGs was reduced with 1 %–2 % Pickering emulsion. These findings demonstrated that SSOS-Pickering emulsions, as potential fat substitutes, can enhance the gel properties and the F-T stability of MPGs.

A New Strategy for Consumption of Functional Lipids from Ericerus pela (Chavannes): Study on Microcapsules and Effervescent Tablets Containing Insect Wax-Derived Policosanol.

In this study, we addressed various challenges associated with the consumption of functional lipids from the Ericerus pela (Chavannes), including unfavorable taste, insolubility in water, difficulty in oral intake, low bioavailability, and low psychological acceptance. Our study focused on the microencapsulation of policosanol, the key active component of insect wax, which is a mixture of functional lipids secreted by the Ericerus pela (Chavannes). We developed two innovative policosanol products, microcapsules, and effervescent tablets, and optimized their preparation conditions. We successfully prepared microcapsules containing insect wax-derived policosanol using the spray-drying method. We achieved 92.09% microencapsulation efficiency and 61.67% powder yield under the following conditions: maltodextrin, starch sodium octenyl succinate, and (2-hydroxy)propyl-β-cyclodextrin (HPβCD) at a ratio of 1:1:1, core-to-wall materials at a ratio of 1:10, 15% solid content, spray dryer feed temperature at 60 °C, inlet air temperature at 140 °C, and hot-air flow rate at 0.5 m3/min. The microcapsules exhibited a regular spherical shape with a minimal water content (1.82%) and rapid dispersion in water (within 143.5 s). These microcapsules released policosanol rapidly in simulated stomach fluid. Moreover, effervescent tablets were prepared using the policosanol-containing microcapsules. The tablets showed low friability (0.32%), quick disintegration in water (within 99.5 s), and high bubble volume. The microcapsules and effervescent tablets developed in this study presented effective solutions to the insolubility of policosanol in water. These products were portable and offered customizable tastes to address the psychological discomfort related to insect-based foods, thus providing a novel strategy for the consumption and secondary processing of insect lipids.

Digestibility and Quality Characteristics of Noodles Added with Octenyl Succinic Anhydride-Modified Wheat Starch

Digestibility and Quality Characteristics of Noodles Added with Octenyl Succinic Anhydride-Modified Wheat Starch

Whether branching-point substitution contributes to improving the emulsifying property of starch modified with octenyl succinic anhydride?

Based on the previous proved fact that substitution position of octenyl succinic (OS) of OSA-starch can be regulated by changing OSA supply mode, the current study aimed at revealing whether and how the substitution position would affect the emulsifying property of OSA-starch. Overall, the results suggested that more OSA substitutions at the branching points of backbone chain under continuous mode (CM) would benefit the emulsifying capacity of OSA-starch by decreasing the initial particle size of emulsion, while more branching-chain substitutions would contribute to improving emulsion stability. By analyzing the interfacial adsorption capacity, it was speculated that the formation of smaller particle size by OSA starch with more backbone-chain branching point substitutions was attributed to its higher effect of reducing surface tension and faster migration rate to oil-water interface. When substitutions at the backbone-chain branching points increased to a certain degree, more branching-chain substitutions would thicken the adsorption layer by affecting the adsorption configuration of OSA-starch molecule, resulting in higher emulsion stability at higher total OSA substitution degree (DS, ≥1.4%). Based on the relationship between substitution position and emulsification performance, combination of traditional mode and CM was proposed to prepared OSA-starch with superior substitution pattern and procession efficiency. Demonstrated by the decreased Δβ-limit value, more branching-point substitutions were achieved for OSA-starch prepared under combination mode, of which its emulsifying activity was conformed to increase by 0.8 m2/g than traditional OSA-starch at 3% OSA limitation.

Lignin and Starch Derivatives with Selenium Nanoparticles for the Efficient Reduction of Dyes and as Polymer Fillers

Selenium nanoparticles (SeNPs) were synthesized and stabilized by biopolymers, namely, sodium lignosulfonate (LS) and starch sodium octenyl succinate (OSA). The obtained selenium nanoparticles were studied for their catalytic activity in the reduction of a dye (C.I. Basic Blue 9, methylene blue) by sodium borohydride. The SeNPs-OSA and SeNPs-LS nanoparticles were also dispersed in a photosensitive matrix and studied as polymer composites. The research confirmed the catalytic abilities of the prepared SeNPs in the reduction of the organic dye. Mechanical tests on the polymers and their composites showed an improvement in the composites’ strength in all tested cases. An increase in hardness and Young’s modulus values of the filled materials compared to the pure matrix was found as well.

Tannic acid enhanced the oxidation stability of vitamin A-vitamin D3 coencapsulated in emulsion based on OSA starch/chitosan: Interfacial absorption, antioxidation and viscoelasticity

In this work, vitamin A (VA) and vitamin D (VD3) were co-encapsulated in the emulsion stabilized by sodium octenyl succinate starch/chitosan/tannic acid (OSA-S/CS/TA) complex. The influence of TA concentration on emulsion stability was estimated, and the underlying mechanism was revealed from the perspective of interface characteristic. The TA incorporation improved the long-term and thermal stability of the emulsion. Compared with the emulsion without TA, the retention rate of VA and VD3 increased by 15.2%–24.5% after storage, and the oxidative product decreased by 23.9%–43.3% after heating. TA was anchored at the oil-water interface to reduce the interfacial tension and form the interfacial film with antioxidation and viscoelasticity. TA and OSA-S/CS were combined by hydrogen bonds at sequential two sites (ΔH1 = −36.42 kJ mol−1, ΔS1 = −0.04 kJ mol−1·K−1, ΔH2 = −2.77 × 103 kJ mol−1, ΔS2 = −9.25 kJ mol−1·K−1). The research expanded the application of TA, VA, and VD3 in food systems.