Allyl Caproate Research Articles

Influence of carriers on the functional properties of spray-dried flavors during storage

Encapsulation is a process of protecting functional ingredients like flavors against physical and chemical changes that may occur, especially during storage. In this study, the effect of selected carriers, namely maltodextrin (MD), gum Arabic (GA), and sodium caseinate (SC), was investigated on the functional properties of aroma compounds during storage. Spray-dried aroma compounds (linalool, citral, Orange oil, allyl caproate, and isoamyl acetate) were formulated using GA, MD, and SC as carriers with different concentrations then stored in desiccators at room temperature for one year. In addition to moisture content, morphology and extent of non-enzymatic browning (NEB) of stored spray-dried aroma were examined using a scanning electron microscope (SEM) and chromameter. While flavor retention was evaluated using gas chromatography-mass spectrometry (GC-MS). After storage microcapsules for 12 months, the water content of the microcapsules of spray-dried flavorings is ranged between 2.96 to 5.97%. SEM analysis showed little cracks, porosity, or breaks which negatively affected the retention of the flavoring. The spray-dried citral browning recorded the highest intensity, followed by Orange oil, isoamyl acetate, linalool, and allyl caproate, respectively. Linalool and isoamyl acetate were the most retained aroma identified by GC-MS compared to the other investigated stored spray-dried flavors. Better retention overtime was achieved when GA was used in higher content than MD at constant SC. Chemical and physical analysis of the spray-dried microcapsules after storage revealed the possibility of using spray-dried flavors in the food matrix for a long time without affecting the product quality.

Exploring the Characteristics of an Aroma-Blending Mixture by Investigating the Network of Shared Odors and the Molecular Features of Their Related Odorants.

The perception of aroma mixtures is based on interactions beginning at the peripheral olfactory system, but the process remains poorly understood. The perception of a mixture of ethyl isobutyrate (Et-iB, strawberry-like odor) and ethyl maltol (Et-M, caramel-like odor) was investigated previously in both human and animal studies. In those studies, the binary mixture of Et-iB and Et-M was found to be configurally processed. In humans, the mixture was judged as more typical of a pineapple odor, similar to allyl hexanoate (Al-H, pineapple-like odor), than the odors of the individual components. To explore the key features of this aroma blend, we developed an in silico approach based on molecules having at least one of the odors—strawberry, caramel or pineapple. A dataset of 293 molecules and their related odors was built. We applied the notion of a “social network” to describe the network of the odors. Additionally, we explored the structural properties of the molecules in this dataset. The network of the odors revealed peculiar links between odors, while the structural study emphasized key characteristics of the molecules. The association between “strawberry” and “caramel” notes, as well as the structural diversity of the “strawberry” molecules, were notable. Such elements would be key to identifying potential odors/odorants to form aroma blends.

Effects of Carriers on Spray-dried Flavors and Their Functional Characteristics.

Encapsulation is an effective method to keep the quality of and avoid changes in flavors or essential oils due to oxidation, heating, volatilization, or chemical interactions. This study aims to microencapsulate key flavorings by traditional wall materials, namely, gum arabic (GA), maltodextrin (MD) and sodium caseinate (SC) and evaluate the effects of different wall materials on the properties of the flavor microcapsules. The emulsions of flavor compounds (linalool, citral, orange oil, allyl caproate and isoamyl acetate) were prepared using GA, SC and MD as carriers with different concentrations and then encapsulated in powder form by a spray dryer. Physical properties, including encapsulation efficiency, viscosity, emulsion stability and moisture, were studied before and after the spray drying process. Moreover, the morphology and extent of the nonenzymatic browning (NEB) of powder particles were performed using a scanning electron microscope (SEM) and a chroma meter. The effect of encapsulation on flavor retention and chemical composition was evaluated using gas chromatography-mass spectrometry (GC-MS). Orange oil shows the maximum retention efficiency (84.5-97.9%), whereas isoamyl acetate is less retained during drying (44.4-72.5%) compared with other volatile compounds. Increasing the concentration of GA provides the highest retention for all aroma compounds and improves the viscosity and the emulsion stability of spray-dried powder. The presence of MD as the main encapsulating agent enables the formation of several homogeneous capsules with a good spherical shape and a smooth surface, according to SEM. The NEB is observed intensively in encapsulated samples containing citral and orange oils, whereas the least browning occurs in isoamyl acetate microcapsules. Wall material formulation affects the retention, morphology and physical properties of the encapsulated flavors, which can be used in food or nutraceutical powder premixes.

The Effect of Aerosols on the Air Microflora of the Indoor Air

This research work assessed the microflora of rooms sprayed with different insecticides and air freshners with the aim of investigating the effect of the aerosols on the types of microflora in the room environment. Eight (8) different samples of chemical aerosols were used they are: Mobile insecticide(Imidacloprid), Raid multipurpose insect killer(1R-trans Phenothrin), Morten Insecticide(pyrethroids), Rambo Insecticide(pyrethroid compound). as categorized as Insecticides, while Febreze(hydroxypropyl beta-cyclodextrin), Air wick(Dipropylene glycol monomethyl ether (aka dipropylene glycol methyl ether), Glade(allyl 3-cyclohexylpropionate, allyl caproate, benzyl alcohol, butylated hydroxytoluene (BHT) and Top breeze(Cyclodextrin) were purchased as air fresheners/fragrance and eight (8) different rooms were used. Microorganisms isolated from the rooms before and after spraying with aerosols were: Staphylococus aureus, Lactobacillus jensenii, Bacillus coagulans, Aspergillus flavus, Aspergillus niger, Micrococcus spp., Aerococcus viridans, Pediococcus cerevisiae, Streptococcus spp., Aspergillus fumigatus and Aspergillus niger. The result of eight different rooms sprayed with different aerosol as Insecticide and air fresheners showed that, some aerosols were able to inhibit some organisms that were initially present in some rooms while there were introduction of another organisms from some aerosols into some rooms. The occurrence of Staphylococus aureus (100%) was the highest in all the rooms followed by Aspergillus niger (87.5) and A. flavus (75%). Lactobacillus jensenii, Bacillus coagulans and Micrococcus spp. had the lowest frequency of occurrence (12.5%).

Metathetic Degradation of Styrene-Butadiene Rubber via Ru-Alkylidene Complex Catalyzed Reaction

Metathetic degradation and functionalization of styrene-butadiene rubber (SBR) were performed with allyl hexanoate, allyl chloroacetate, 5-hexenyl acetate and trifluoroethyl methacrylate as chain transfer agents (CTAs) using Grubbs 2 nd generation catalyst. It has been demonstrated that the catalyst concentration, CTA concentration and reaction time were major factors influencing the molecular weights and polydispersity indices of targeted telechelic SBR oligomers. Well-defined oligomers with molecular weights ranging from 700 to 36600 g mol -1 and polydispersity indices ranging from 1.17 to 4.79 were realized. The structures of the SBR oligomers were determined by FTIR and 1 H NMR analyses, which indicated that the functional groups of the CTAs were successfully attached onto the end of the polymer chains. To further investigate the performance of SBR oligomers, differential scanning calorimetry (DSC) analysis was performed, which indicated that the glass transition temperature (T g ) of the metathesis products decreased with longer reaction time.

Study of volatile compounds of Pyrus mamorensis Trab. a characteristic plant of Mamora forest (north-western Morocco)

Pyrus mamorensis Trab. commonly called “wild pear” was considered for long time as an endemic of the Mamora forest of Morocco (north-west). Although lack of protection and it is threatened with extinction in its range, this tree is of great interest due to its ecological and medicinal properties . This study focused on evaluation of volatiles in Pyrus mamorensis for its valorisation as a natural resource. So, the volatile compounds from different parts (leaves, stems, fruits, and flowers) were investigated after extraction by cold maceration in ethyl ether and analyzed by gas chromatography coupled to the mass spectrometry (GC - MS). Thirty one (31) compounds were identified and quantified including fifteen (15) terpenes, seven (7) alcans, two (2) aldehydes, four (4) esters and three (3) allyl alkoxybenzen derivatives. Estragol was the dominant component of the plant and that was only detected in leaves (83,09 %), while hexadecane (36,92 %) and allyl hexanoate (29,39 %) were mainly detected in the stems. The fruits showed relatively high levels (20,59 %) of benzyl butanoate, whereas in the flowers, limonene is the most abundant constituent (30,12 %). The analysis of the relative rates of different classes of volatile compounds, revealed the diversity of these compounds in P. mamorensis compared to two cultivars of edible species : P. communis L. et P. pyrifolia . The significant difference in composition in this case could be due to the wild character of P. mamorensis .

Synthesis of allyl caproate copolymers with styrene and study of these compounds as viscous additives to petroleum oils

Viscous additives resistant to destructive actions and corresponding to increased requirements to machines have been obtained. The copolymerization of allyl caproate with styrene by the radical mechanism in presence of a radical initiator was carried out, and the influence of various factors on the process and the quality of the viscous additives to petroleum oils was studied.

Insecticidal and repellent action of allyl esters against Acyrthosiphon pisum (Hemiptera: Aphididae) and Tribolium castaneum (Coleoptera: Tenebrionidae)

In this project, three allyl esters from middle-chain fatty acids (allyl octanoate, allyl heptanoate and allyl hexanoate) and two from aromatic acids (allyl cinnamate and allyl 2-furoate) were investigated against two differential pests. Lethal and sublethal repellent effects by topical and ingestion exposure were tested against the pea aphid Acyrthosiphon pisum (Harris) and the red flour beetle Tribolium castaneum (Herbst) as these represent two insect pest orders of Hemiptera and Coleoptera each with a specific feeding behavior using piercing–sucking and biting–chewing mouthparts, respectively.Significant mortalities against aphid nymphs were produced when fed via diet containing allyl cinnamate, allyl 2-furoate and allyl heptanoate at 0.1mgmL−1, and in dose–response tests allyl cinnamate was the most active with an LC50 of 0.03 (0.02–0.05) mgmL−1. Although topical application on aphids was only effective at doses of 0.1mg aphid−1 for allyl cinnamte, beetles of T. castaneum adults were sensitive to all allyl esters assessed with LC50's ranging between 0.1 and 0.2mg insect−1.In binary choice bioassays, none of the allyl esters produced repellent effects on A. pisum aphids, neither by ingestion (0.1mgmL−1 in the diet) nor by contact (100μgcm−2 on filter paper). In contrast, all allyl esters, except allyl hexanoate, showed high to moderate repellence effects on T. castaneum beetles at 10μgcm−2. Interestingly, the repellent activity of allyl cinnamate was equal to the commercial insect repellent N,N-diethyl-m-toluamide (DEET). The data obtained suggest a possible role of allyl esters in insect pest control.

TOXICITY OF ALLYL ESTERS IN INSECT CELL LINES AND IN SPODOPTERA LITTORALIS LARVAE

We investigated the effects of five allyl esters, two aromatic (allyl cinnamate and allyl 2-furoate) and three aliphatic (allyl hexanoate, allyl heptanoate, and allyl octanoate) in established insect cell lines derived from different species and tissues. We studied embryonic cells of the fruit fly Drosophila melanogaster (S2) (Diptera) and the beet armyworm Spodoptera exigua (Se4) (Lepidoptera), fat body cells of the Colorado potato beetle Leptinotarsa decemlineata (CPB) (Coleoptera), ovarian cells of the silkmoth Bombyx mori (Bm5), and midgut cells of the spruce budworm Choristoneura fumiferana (CF203) (Lepidoptera). Cytotoxicity was determined with use of MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide] and trypan blue. In addition, we tested the entomotoxic action of allyl cinnamate against the cotton leafworm Spodoptera littoralis .The median (50%) cytotoxic concentrations (EC₅₀s) of the five allyl esters in the MTT bioassays ranged between 0.25 and 27 mM with significant differences among allyl esters (P = 0.0012), cell lines (P < 0.0001), and the allyl ester-cell line interaction (P < 0.0001). Allyl cinnamate was the most active product, and CF203 the most sensitive cell line. In the trypan blue bioassays, cytotoxicity was produced rapidly and followed the same trend observed in the MTT bioassay. In first instars of S. littoralis, allyl cinnamate killed all larvae at 0.25% in the diet after 1 day, while this happened in third instars after 5 days. The LC₅₀ in first instars was 0.08%. In addition, larval weight gain was reduced (P < 0.05) after 1 day of feeding on diet with 0.05%. In conclusion, the data provide evidence of the significant but differential cytotoxicity among allyl esters in insect cells of different species and tissues. Midgut cells show high sensitivity, indicating the insect midgut as a primary target tissue. Allyl cinnamate caused rapid toxic effects in S. littoralis larvae at low concentrations, suggesting further potential for use in pest control.

Quantification of allyl hexanoate in pineapple beverages and yogurts as a case study to characterise a source of uncertainty in dietary exposure assessment to flavouring substances

One source of uncertainty in the estimation of dietary exposure to flavouring substances is the uncertainty in the occurrence and concentration levels of these substances naturally present or added to foodstuffs. The aim of this study was to assess the variability of concentration levels of allyl hexanoate, considered as a case study, in two main food categories to which it is often added: pineapple juice-based beverages and yogurts containing pineapple. Thirty-four beverages and 29 yogurts, with pineapple fruit or juice and added flavourings declared as ingredients on the package, were purchased from the local market (in Rome) and analysed. Analytical methods based on the stir bar sorptive extraction (SBSE) technique for the isolation of the target analyte, and on GC-MS analysis for final determination, were developed for the two food categories. In beverages, allyl hexanoate concentrations ranged from less than 0.01 to 16.71 mg l−1, whereas in yogurts they ranged from 0.02 to 89.41 mg kg−1. Average concentrations in beverages and yogurts with pineapple as the main fruit ingredient (1.91 mg l−1 for beverages, 9.61 mg kg−1 for yogurts) were in fair agreement with average use level data reported from industry surveys for the relevant food categories (4.5 and 6.0 mg kg−1, respectively). Within the group of yogurts a single product was found to contain a level of allyl hexanoate more than 10-fold higher than the average reported use level. The screening techniques developed by the European Food Safety Authority (EFSA) using use level data provided by industry gave estimates of exposure that were of the same order of magnitude as the estimates obtained for regular consumers who would be loyal to the pineapple yogurt and beverage products containing the highest observed concentration of the substance of interest. In this specific case the uncertainty in the results obtained with the use of standard screening techniques for exposure assessment based on industry reported use levels is low.

The Effects of Vehicles on the Human Dermal Irritation Potentials of Allyl Esters

Allyl esters, frequently used in the fragrance industry, often contain a certain percentage of free allyl alcohol. Allyl alcohol is known to have a potential for delayed skin irritation. Also present in the finished product are different solvent systems, or vehicles, which are used to deliver the fragrances based upon their intended application. This study was conducted to determine whether different vehicles affect the skin irritation potential of five different allyl esters. The allyl esters tested were allyl amyl glycolate, allyl caproate, allyl (cyclohexyloxy)acetate, allyl cyclohexylpropionate, and allyl phenoxyacetate in the vehicles diethyl phthalate, 3:1 diethyl phthalate:ethanol, and 1:3 diethyl phthalate:ethanol at concentrations of 0.1%, 0.5%, 1.0%, and 2.0% (w/w). A modified cumulative irritation test was conducted in 129 human subjects. Test materials (0.3 ml) were applied under occlusion to skin sites on the back for 1 day (24 h) using Hill Top chambers. Irritation was assessed at 1, 2, 4, and 5 days following application of test materials. Cumulative irritation scores varied considerably among test materials. There were no delayed irritation observations. The highest irritation scores were observed at the 2.0% concentration for all test materials. The irritation scores for allyl amyl glycolate, allyl (cyclohexyloxy)acetate, and allyl phenoxyacetate were highest in 1:3 diethyl phthalate:ethanol, thus the resulting calculated no-observed-effect levels, 0.12%, 0.03%, and 0%, respectively, were much lower for this vehicle compared to the diethyl phthalate vehicle, 0.33%, 0.26%, 0.25%, respectively. These data showed a trend for lower concentration thresholds to induce irritation when higher levels of ethanol were used in the vehicle.

Aroma synthesis by immobilized lipase from Mucor sp.

The ability of Mucor sp. lipase immobilized on Amberlite IRC 50 to catalyze the synthesis of flavor esters was investigated in organic media (cyclohexan) at 35 °C. Propionic, butyric, caproic acids, as well as methanol, ethanol, allyl, butanol, isoamyl, geraniol, citronellol and farnesol alcohols were used as substrates in equimolar ratio. Most of the esters were synthesized in good yield (>90%). Different conversion yields were observed according to the affinity of the lipase toward the acids (short or long), or the alcohols (linear or branched and short or long). Rapid and higher conversions of 92 and 98% were observed for methyl caproate and ethyl caproate, respectively after 4 h reaction, and a yield of 95, 100, 93% were obtained for butyl butyrate, butyl caproate and allyl caproate, respectively after 24 h reaction in used conditions.

Preservation of High Moisture Barley Grains with Citral and Allyl Caproate and Preliminary Acceptability Tests with Piglets

(1977). Preservation of High Moisture Barley Grains with Citral and Allyl Caproate and Preliminary Acceptability Tests with Piglets. Acta Agriculturae Scandinavica: Vol. 27, No. 2, pp. 105-109.

Short-term toxicity study of allyl caproate in rats

Groups of 15 male and 15 female rats were given daily oral doses of 0 (control), 35 or 100 mg allyl caproate/kg/day, as a solution in oil, for 14 wk, and ten males and ten females were given 12 mg/kg/day for 13wk. There were no differences between treated and control rats in body weight, water intake, haematological examinations, analysis of urine, renal concentration tests or serum chemistry. There were slight increases in food intake at the highest dose level. The weight of the liver was increased with doses of 35 and 100 mg/kg/day, and all treated groups showed evidence of periportal vacuolation, which was dose-related in both incidence and severity and which, in the rats given 100 mg/kg/day, was accompanied by enlargement of the hepatocytes, focal periportal necrosis and bile-duct proliferation. Weights of the kidneys, spleen, stomach and small intestine were increased at the highest level of treatment. The small-intestine weight was also increased in females given 35 mg/ kg/day. On the basis of these findings it was not possible to establish a no-untoward-effect level for allyl caproate.