Release Of Vanillin Research Articles

Preparation and characterization of Chitosan based edible coating containing vanillin/HPβCD inclusion complex and its application in chicken preservation

In order to develop the plant-derived active substance vanillin, 2-hydroxypropyl-β-cyclodextrin was used to encapsulate vanillin, and a chitosan-based edible coating: vanillin-HPβCD/CH was developed for chicken preservation. First, vanillin was inserted into the internal cavity of HPβCD through an ultrasonic-assisted method to form vanillin/HPβCD-IC. The inclusion complex of vanillin/HPβCD-IC was demonstrated to be successfully synthesized by ultraviolet–visible spectroscopy, Fourier transform infrared spectroscopy (FTIR), X-ray diffraction (XRD) and scanning electron microscopy (SEM). Through antibacterial testing, thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC), it was verified that inclusion improved the thermal stability of vanillin while retaining the antibacterial effect of vanillin. The release of vanillin from encapsulated particle exhibited pH-dependent slow controlled release, and can described by First order model. Subsequently, vanillin/HPβCD-IC was compounded with chitosan through a composite film-forming method to prepare an edible coating: vanillin-HPβCD/CH. By characterizing the performance of vanillin-HPβCD/CH, it was found that the addition of vanillin/HPβCD-IC can improve the stability, isolation hydrophobicity and antibacterial performance of the plastic wrap. Finally, vanillin-HPβCD/CH was applied to chicken preservation, and it was found that vanillin-HPβCD/CH could effectively extend the shelf life of chicken and maintain sensory quality by slowing down the rise in pH, preventing the proliferation of microorganisms, and inhibiting lipid oxidation. In summary, vanillin-HPβCD/CH is an edible coating with superior performance and a promising packaging material for chicken freshness preservation.

Formulation, optimization, and in-vitro evaluation of polymeric microsponges for topical delivery of vanillin

The development of ethylcellulose-based polymeric microsponges for the topical delivery of therapeutic agents has attracted the interest of pharmaceutical scientists around the globe in recent years. This work represents preparation, optimization (using Box–Behnken design [BBD]), and characterization (in-vitro and ex-vivo) of ethylcellulose microsponges loaded with vanillin for effective topical delivery to treat wounds. Vanillin-ethylcellulose microsponges were prepared by using quasi-emulsion solvent diffusion and optimized formulation (F9) (containing 100 mg ethylcellulose, 10 mL dichloromethane, 100 mg vanillin, and 90 mg polyvinyl alcohol) developed showed particle size (90.3 ± 2.9 µm), high entrapment of vanillin (79.0 ± 2.8%), and optimum colloidal properties (zeta potential = −37.91 ± 2.44 mV; polydispersity index (PDI) = 0.224 ± 0.23). Optimized formulation extended the release of vanillin (96.68 ± 3.11%) in-vitro for 24 h. Vanillin-ethylcellulose microsponges (F9) dispersed in Carbopol 940 gel showed limited ex-vivo skin permeation (steady-state flux, JSS = 243.7 ± 6.2 µg/cm2/h) and higher skin retention (82.46 ± 6.74%) for 24 h in pig ear skin compared to plain vanillin Carbopol 940 gel (steady-state flux, JSS = 1350 ± 10.8 µg/cm2/h, skin retention = 33.66 ± 4.53%). Results of confocal laser scanning microscopy (CLSM) of Vanillin-ethylcellulose microsponges (F9) Carbopol 940 gel revealed accumulation of microsponges in the stratum corneum layer of skin as a depot. Microsponges-based Carbopol 940 gel also displayed excellent in-vitro antibacterial activity (zone of inhibition = 24.2 ± 1.3 mm) against Staphylococcus aureus for 24 h compared to plain vanillin Carbopol 940 gel (zone of inhibition = 10.30 ± 1.2 mm) that was considered good for its wound healing activity. Therefore, developed vanillin-loaded ethylcellulose microsponges could be effectively used in the treatment of wounds by reducing side effects associated with vanillin and promoting its localized delivery in Carbopol 940 gel form.

Lactic acid bacteria as a tool for biovanillin production: A review.

Vanilla is the most commonly used natural flavoring agent in industries like food, flavoring, medicine, and fragrance. Vanillin can be obtained naturally, chemically, or through a biotechnological process. However, the yield from vanilla pods is low and does not meet market demand, and the use of vanillin produced by chemical synthesis is restricted in the food and pharmaceutical industries. As a result, the biotechnological process is the most efficient and cost-effective method for producing vanillin with consumer-demanding properties while also supporting industrial applications. Toxin-free biovanillin production, based on renewable sources such as industrial wastes or by-products, is a promising approach. In addition, only natural-labeled vanillin is approved for use in the food industry. Accordingly, this review focuses on biovanillin production from lactic acid bacteria (LAB), which is generally recognized as safe (GRAS), and the cost-cutting efforts that are utilized to improve the efficiency of biotransformation of inexpensive and readily available sources. LABs can utilize agro-wastes rich in ferulic acid to produce ferulic acid, which is then employed in vanillin production via fermentation, and various efforts have been applied to enhance the vanillin titer. However, different designs, such as response surface methods, using immobilized cells or pure enzymes for the spontaneous release of vanillin, are strongly advised.

Facile synthesis of self-dispersed β-cyclodextrin-coupled cellulose microgel for sustained release of vanillin

A self-dispersed β-cyclodextrin-coupled cellulose (β-CD-Cel) microgel was firstly synthesized via chemically coupling cellulose and β-CD in NaOH/urea aqueous solution. Following, after encapsulating the hydrophobic vanillin molecules into the cavities of β-CD-Cel microgel through host-guest interaction, cellulose-based long-lasting fragrance-released complex was obtained. β-CD was mainly bonded onto the hydroxyl groups at C6 in the AGU units of cellulose, and about 0.5 β-CD molecule were introduced into the AGU unit when cellulose skeleton contained the β-CD content of 19.33%. FTIR, 1H NMR, XRD, and UV–Vis provided evidences for the encapsulation of vanillin in the cavity of β-CD-Cel, and the encapsulating efficiency of vanillin for the β-CD-Cel inclusion complex was upped to 86.9%, which exceeded that of single β-CD small molecule encapsulating fragrance. Benefiting from the reversible host-guest interaction between β-CD and vanillin molecule, the continuous fragrance release time could exceed 196 h, and the sustained release behavior of β-CD-Cel complex could be adjusted by temperature. Also, the fragrance-released β-CD-Cel composite film showed high transparency, strong water resistance, and good flexibility. The vanillin retention of the composite film can keep 40% after soaking in ethanol solution for 96 h. This study will provide a new approach for the development of biomass functional coating.

In situ formation and post-formation treatment of bacterial cellulose/κ-carrageenan composite pellicles

Bacterial cellulose (BC)/κ-carrageenan composite pellicles were prepared by in situ formation and subjected to post-formation alkali and neutralization treatments. κ-Carrageenan was incorporated into BC pellicles by in situ formation to form a gel by post-formation treatment with a solution containing K+. Structural analyses indicated that BC/κ-carrageenan pellicles had a double-stage structure, consisting dominantly of cellulose in the upper part and κ-carrageenan in the under part. BC/κ-carrageenan pellicles became weaker upon application of a tensile force and were harder compared with the BC pellicles. Vanillin was used to study the release of active agents from the pellicles. The fractional release of vanillin from BC/κ-carrageenan pellicles relative to the initial release (30–60 min) was greater than that from BC pellicles. These findings should aid basic research on BC/κ-carrageenan pellicles and help in determining their suitability for application in the biomedical and cosmetic industries.

Multifunctional food supplements based on layered zinc hydroxide salts intercalated with vitamin anions and adsolubilized with vanillin.

A layered hydroxide salt (LHS) was used as an inorganic matrix to obtain multifunctional food compounds. The aim is to obtain higher thermal stability for vitamin anions and a slow release of aroma. Thus, vitamin B3 (nicotinate), vitamin B5 (phantothenate) and vitamin L (2-aminobenzoate) anions were intercalated by co-precipitation method. The results show an increase in thermal stability of intercalated vitamin anion since decomposition of pure vitamin B3 starts at 120°C and after intercalation, the HSL-B3 decomposition starts at 313°C. The intercalation products were than reacted with vanillin (3-methoxy-4-hydroxybenzaldehyde). A kinetic study showed that the release of vanillin from its nanohybrid was found to occur in a controlled manner, evidencing that the synthesized compounds can be used in formulations for the sustained release of aromas. Results showed that the intercalated anions and adsolubilized vanillin were not only less volatile since it causes the aroma to remain in the LHS for a longer period of time resulting in slow release but also have higher thermal stability when they are confined between layers. In summary, the multifunctional food supplements obtained seems to have nutraceutical, olfactory and better thermal resistance properties being suitable for potential applications in the food industry.

Release Kinetic Models of Vanillin and Physicomechanical Properties of Thermoplastic Starch and Chitosan Nanocomposite Films: Effects of Mixing Order

The effects of mixing sequence of starch–chitosan nanocomposite films on antimicrobial properties of vanillin, the release kinetics of vanillin, and physicomechanical changes of films have been reported. Four types of films were prepared based on the order of mixing. SC1: starch–glycerol–MMT–vanillin; SC2: starch–glycerol–chitosan–MMT–vanillin; SC3: starch–MMT–glycerol–vanillin–chitosan and SC4: starch–chitosan–glycerol–vanillin–MMT. All formulation exhibited high antimicrobial activity against E. coli, S. enterica, and Z. bailii, except P. aeruginosa, which showed lower sensitivity. Migration dynamics of vanillin from films into simulants showed high vanillin migrated into water and 10% ethanol at 25 and 40 °C as analyzed by high-performance liquid chromatography (HPLC). The diffusion coefficients of vanillin in water ranged between 0.38 × 10−13m2 s−1 and 4.30 × 10−13m2 s−1 and in 10% ethanol between 1.38 × 10−13m2 s−1 and 5.16 × 10−13m2 s−1 following the Fickian diffusion mechanism and first-order kinetics. The diffusion was temperature-dependent following the Arrhenius equation with high activation energies of 15.00–52.80 kJmol−1 in water and 35.80–56.50 kJ mol−1 in 10% ethanol. The plot of the mass fraction of $${{m_{t} } \mathord{\left/ {\vphantom {{m_{t} } {m_{\infty } }}} \right. \kern-\nulldelimiterspace} {m_{\infty } }}$$ against time for each sample shows the burst release of vanillin in between 30 min and 1 h and then attained the steady-state migration over 48 h. The plasticization effect of vanillin reduced the tensile strength and elastic modulus of films, while it increased the elongation at the break by 154% that was reversed after the addition of chitosan. These nanostructured starch films showed promising applications in the antimicrobial packaging industry.

Antibacterial porous xanthan‐based films containing flavoring agents evaluated by near infrared chemical imaging technique

AbstractXanthan gum (XG) is a widely applied natural polysaccharide in food industry as thickening agent. Nowadays, one of the major problems is that some food products are found to be contaminated by pathogenic bacteria such as Escherichia coli and Staphylococcus aureus reducing so, their shelf life. This research aims to demonstrate the antibacterial activity of some biodegradable formulation XG‐lignin hydrogel films and their potential application as carriers for controlled release of flavoring compounds. The XG‐lignin films containing an aspen wood lignin type showed a high antibacterial activity against Salmonella Typhymurium ATCC 14028, E. coli ATCC 25922 and Listeria monocytogenes ATCC 25922 bacteria compared with those containing softwood lignin, or lignin from annual plants. Surface morphology indicated a homogeneous distribution of both components within the hydrogel network and the generation of a porous structure after swelling and lyophilization. Additionally, near infrared chemical imaging technique was used as nondestructive method to observe the spatial distribution of the polymeric components and vanillin into the hydrogel films as well as its release profile. The vanillin release rate dependence on the lignin type was also evidenced, a retarded release of vanillin being observed. These results give an important insight into the use of XG, lignin, and vanillin for the development of new edible films for active packaging materials.

Preparation and Release of Vanillin from Sporopollenin Microcapsules

Sporopollenin is a potential carrier for active ingredient due to its uniform size, central cavity, as well as chemical and thermal stability. Sporopollenin microcapsules were obtained by a series of processes on the pollens of Typhae angustfolia. Vanillin was embedded in sporopollenin using passive loading and evaporating techniques. Raw cattail pollen, sporopollenin, vanillin, and vanillin-loaded microcapsules were characterized by Fourier transform infrared spectroscopy, thermogravimetric analysis, and scanning electron microscopy. The results show that sporopollenin exhibits structural integrity, porosity, and good thermal stability. The encapsulation efficiencies of the microcapsules prepared by passive loading technique and evaporating loading technique were found to be 7.2 ± 0.8% and 40.5 ± 1.6%, respectively. The release profile and kinetics of the vanillin-loaded sporopollenin microcages were conducted to evaluate the suitability of sporopollenin microcapsules for loading. Release behavior of vanillin from microcapsules was more aligned with Fickian diffusion, with an initial rapid cumulative release followed by a lower speed of release. These findings demonstrated that sporopollenin from the cattail pollen of T. angustfolia could be a suitable medium for sustained release of nutritional components.

Synthesis and behavior of click cross-linked alginate hydrogels: Effect of cross-linker length and functionality

Various bismaleimides and trismaleimides of varying molar masses, chemical architectures and functionalities were explored as cross-linkers for furan-modified alginate chains via Diels-Alder click reactions. An environmentally friendly approach is described for the preparation of hydrogels based on naturally occurring biomacromolecules, without catalysts. The behavior of the resulting polysaccharides-based hydrogels was analyzed in terms of swelling, rheological properties and drug-release efficiency, in connection with potential biomedical applications. The use of the different cross-linkers allows tuning the mechanical properties as well as the pulsatile swelling behavior of the hydrogels. When using trifunctional cross-linkers stiffer hydrogels were formed with high storage modulus whereas the chain length and the composition of the cross-linker clearly influence the swelling of the hydrogel network. In connection with drug delivery applications, release of vanillin as a traceable aromatic biobased model drug was also monitored as a function of hydrogel composition. To the best of our knowledge, for the first-time furan-modified alginates were reacted and studied with polyethylene glycol-based bis or trismaleimides with different molar masses and architectures, resulting in advanced hydrogels with different behavior.

Development of vanillin/β-cyclodexterin inclusion microcapsules using flax seed gum-rice bran protein complex coacervates.

Encapsulation of vanillin through β-cyclodexterin inclusion complex coacervates (β-CD-IC) was developed to achieve higher thermal stability and controlled release of vanillin. The effect of protein to polysaccharide (Pr:Ps) ratio and core (Vanillin/β-CD-IC) to wall (coacervate) ratio on the vanillin encapsulation as well as thermal, microstructural and physical characteristics of microcapsules were investigated. Microcapsules had particle size ranging from 0.75 to 4.5 μm with negative surface charge and narrow size distribution. Although particle size and encapsulation efficiency were increased by increasing the Pr:Ps ratio and core to wall ratio, the zeta-potential decreased. Vanillin/β-cyclodexterin loaded microcapsules had the maximum encapsulation efficiency about 85% at core to wall ratio of 1:3 and Pr:Ps ratio of 9:1. Structural studies by Fourier-transform infrared spectroscopy (FTIR) indicated the entrapment of encapsulant and X-Ray diffraction data and scanning electron microscopy (SEM) images showed that microcapsules have amorphous structure with soft surface. Furthermore, FTIR results indicated the formation of vanillin/β-cyclodextrin inclusion is the result of chemical interactions, but physical interaction between core and shell leads to encapsulate vanillin/β-cyclodextrin inclusion in rice bran protein-flaxseed gum (RBP-FG) coacervates. Microencapsulation increased the vanillin thermostability and its shelf life. Therefore, it is possible to increase thermal stability of vanillin against environmental conditions.

Polyelectrolyte complex from cationized casein and sodium alginate for fragrance controlled release.

CA/NaAlg polyelectrolyte complex (PEC) novelly obtained from cationized casein (CA) and sodium alginate (NaAlg) via electrostatic interactions was designed for fragrance (vanillin) controlled release. Structural variation between pristine CA/NaAlg PEC and vanillin-loaded CA/NaAlg PEC were investigated by ultraviolet (UV), fourier transform infrared (FI-TR) and X-ray diffraction (XRD). Pristine CA/NaAlg PEC and vanillin-loaded CA/NaAlg PEC were demonstrated spherical in shape by transmission electron microscopy (TEM). Thermogravimetric analysis (TGA) showed that PEC's encapsulating could enhance the stability of vanillin whilst the vanillin encapsulation efficiency was 41.39% and the vanillin loading efficiency was 19.83%. The data also proved sustained release of vanillin in vitro. This work offers a feasible pathway of fabricating microcapsules for controlled releasing system, which have a great potential use in several fields, such as food packaging, cosmetics and textile.

Facile Synthesis of Chitosan-Coated Silica Nanocapsules via Interfacial Condensation Approach for Sustained Release of Vanillin

Chitosan-coated silica nanocapsules with a double-shelled structure were crafted using Pluronic F127 as the template via the interfacial condensation approach. The shell of these nanocapsules was c...

Active wrapping paper against mango anthracnose fungi and its releasing profiles

Active wrapping papers varied in bio‐based coating materials (chitosan and carboxymethyl cellulose) and vanillin concentrations (0.5%, 1.0%, 2.0%, and 4.0% (w/v)) were prepared to study their antifungal effects and release properties. Chitosan‐coated paper with 1% (w/v) vanillin gave the best inhibition against mycelial growth of mango anthracnose fungi and could inhibit its conidiospores germination. The release of vanillin from a chitosan‐coated paper under different conditions of temperatures (13°C, 25°C, and 37°C), relative humidity (RH) (75%, 86%, and 96% RH), and pH values (pH 3.8, 5.2, and 6.2) was studied. Moreover, the vanillin release from the paper to mango fruit under an actual commercial storage condition (13°C, 90% RH) was also investigated. The predominant mechanism of vanillin release under low temperatures (13‐25°C) and all RH studied was a Fickian diffusion, whereas the high temperature (37°C) and in all buffers varying pH showed a non‐Fickian behaviour. Increasing temperature and RH enhanced in diffusion coefficient (D value) from 78.24 × 10−10 to 162.10 × 10−10 cm2/s and 42.87 × 10−10 to 59.98 × 10−10 cm2/s, respectively. Meanwhile, the increasing pH value reduced the D value from 233.87 × 10−10 to 122.74 × 10−10 cm2/s. The kinetic of vanillin release under an actual wrapping application exhibited a non‐Fickian behaviour, and the D value was considerably low (approximately 65.36 × 10−12 cm2/s). The developed active wrapping paper can be great interest for food industry and is practically reasonable for postharvest mango fruits.

A study on the release kinetics and mechanisms of vanillin incorporated in almond gum/polyvinyl alcohol composite nanofibers in different aqueous food simulants and simulated saliva

AbstractVanillin incorporated almond gum/polyvinyl alcohol (PVA) composite nanofibers were prepared using electrospinning. The release mechanisms and kinetics of incorporated vanillin were evaluated in different aqueous food simulants (distilled water, 10% ethanol, 50% ethanol and 3% acetic acid) and simulated saliva. Vanillin content in different media was determined by high‐performance liquid chromatography (HPLC). Vanillin release data were fitted to first order, Kopcha, Korsmeyer‐Peppas and Peppas‐Sahlin models to evaluate release mechanisms and kinetics. Release kinetics of vanillin in all mentioned media followed a pseudo‐Fickian diffusion mechanism. The vanillin release data in distilled water, 10% ethanol, 50% ethanol and simulated saliva fitted well to Peppas‐Sahlin model with regression coefficients 0.9937, 0.9936 and 0.9912, 0.9903, respectively. The release kinetics of vanillin in 3% acetic acid fitted to the Korsmeyer‐Peppas model with regression coefficient 0.9661. The release study in different aqueous food simulants showed burst release of vanillin within the first 5 min, followed by sustained release for 180 min. Nanofibers showed relatively good stability under dry ambient condition and maintained around 58 percentage of the incorporated vanillin for 90 days. Copyright © 2016 John Wiley & Sons, Ltd.

Delivery of vanillin by poly(lactic-acid) nanoparticles: Development, characterization and in vitro evaluation of antioxidant activity

Poly(lactic acid) (PLA) nanoparticles containing vanillin were prepared using an emulsion-solvent evaporation technique and were characterized and assessed for their in vitro antioxidant potential. Physicochemical properties of the nanoparticles were characterized by size, polydispersity index, zeta potential, encapsulation efficiency and stability. Solid state and thermal properties were assessed using X-ray diffraction and differential scanning calorimetry, while in vitro drug release profile was also evaluated. Results showed PLA nanoparticles having a characteristic amorphous structure, sizes in the range of 240nm with high homogeneity in size distribution, zeta potential of −22mV and vanillin encapsulation efficiency of 41%. In vitro release study showed a slow and sustained release of vanillin governed by diffusion. Nanoparticles were stable over a period of three months. Antioxidant ability of the vanillin-loaded PLA nanoparticles in scavenging the radical 2,2-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) was inferior to free vanillin and due to its prolonged release showed a profile that was both time and concentration dependent, while free vanillin showed concentration-dependent activity. The study concluded that PLA nanoparticles are potential carriers for vanillin delivery.

Flavor release by enzymatic hydrolysis of starch samples containing vanillin–amylose inclusion complexes

Hylon VII is a high amylose corn starch which has excellent gelling properties, and its behavior as flavor encapsulant is relevant to the food industry because its ability to regulate a swelling-controlled release in aqueous media. We studied the release of vanillin, encapsulated in Hylon VII under experimental conditions in which the amylose–vanillin inclusion complex is obtained, along with the enzymatic hydrolysis of the starch carried out using salivary amylase of human origin. The flavor release into the aqueous phase was quantified spectrophotometrically and the partition into the headspace was assessed by a gas sensor array. Simultaneously, the progress of the enzymatic reaction was determined by analysis of reducing sugars. The release of flavor into the aqueous phase followed a diffusion/relaxation kinetic, whereas the headspace analysis showed an increase in the aroma intensity according to the increase of reducing sugars concentration in the solution. Furthermore, by using the Unfolded Cluster Analysis methodology it was possible to accurately discriminate the samples corresponding to each of the assayed hydrolysis times. The joint detection of the flavor in the condensed phase and in the headspace compared with the degree of starch hydrolysis provides an overall analytical painting of a daily food intake process.

Preparation and Characterization of Light-Sensitive Microcapsules Based on a Liquid Crystalline Polyester

Photosensitive microcapsules and membranes based on poly(α-methylstilbenesebacoate-co-α-methylstilbeneisophthalate), containing the photosensitive α-methylstilbene moiety, were prepared by a phase-inversion precipitation process. In order to simulate the morphology and behavior of the microcapsule shell under UV irradiation, an exhaustive characterization of a membrane was first performed by ESEM, POM, AFM, and contact angle measurements. The prepared microcapsules contained either chloroform or a concentrated solution of vanillin in chloroform as the core; in all cases, before UV irradiation, their outer surface appeared smooth and dense. The influence of vanillin on microcapsule cross-section morphology was observed by ESEM microscopy. Release of vanillin in water, at room temperature, was markedly influenced by UV irradiation: in the absence of irradiation, it was practically negligible, while when microcapsules were submitted to continuous irradiation with UV light, the surface morphology of the capsules changed drastically and vanillin started to be released after ca. 20 min of irradiation.

Vanillin release from poly(vinyl alcohol)-bacterial cellulose mono and multilayer films

Mono and multilayer materials from PVA and BC incorporating vanillin as natural antimicrobial ingredient were prepared. The composite films were characterized by means of scanning electron microscopy (SEM) and Fourier transform infrared spectroscopy (FTIR). The release mechanism of vanillin from composites films was investigated using a pseudo first order model. The diffusion coefficients, calculated with Fick’s law of diffusion, are ranging from 1.69×10−12 to 3.84×10−12m2s−1. The vanillin release is influenced by films composition; the multilayer films being promising in order to achieve controlled release of vanillin.

Acrylic microspheres as drug‐delivery systems: synthesis through in situ microemulsion photoinduced polymerization and characterization

AbstractAcrylic microspheres bearing a dense shell were successfully prepared by an in situ microemulsion photoinduced polymerization. Experiments following a fractional factorial design were performed for assessing the effect of the main reaction parameters (surfactant concentration in the aqueous phase, stirring rate, organic to water volume ratio, irradiation time) on the morphology of the microspheres and on their encapsulation yield. Environmental scanning electron microscopy and porosity measurements were carried out. Finally, the drug‐delivery features of the obtained products were investigated, evaluating the release of vanillin, chosen as a reference compound. The diffusion coefficients were found to be almost unvaried despite the increase in BET area. Such products show promising potentialities for home and personal care applications. © 2012 Society of Chemical Industry