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Synthesis of Sucrose Octaacetate and Characterization of Its N. Petkova et al., “Green” Synthesis of Sucrose Octaacetate and Characterization…, Chem. Biochem. Eng. Q., 31 (4) 395–402 (2017) 395 “Green” Synthesis of Sucrose Octaacetate This work is licensed under a and Characterization of Its Physicochemical Properties Creative Commons Attribution 4.0 and Antimicrobial Activity* International License N. Petkova,a D. Vassilev,b,** R. Grudeva,a Y. Tumbarski,c I. Vasileva,a M. Koleva,b and P. Deneva aUniversity of Food Technologies, Organic Chemistry Department, Maritza 26 Blvd, Plovdiv, 4002, Bulgaria bTechnical University of Gabrovo, Department “Physics, chemistry doi: 10.15255/CABEQ.2017.1117 & ecology”, Gabrovo, 5300, Bulgaria, 4 H. Dimitar str. Original scientific paper cUniversity of Food Technologies, Department of Microbiology, Received: March 13, 2017 Maritza 26 Blvd, Plovdiv, 4002, Bulgaria Accepted: November 6, 2017 Sucrose octaacetate (octa-O-acetylsucrose) has been synthesized by esterification of sucrose with acetic anhydride using ultrasound-assisted irradiation. This sucrose ester is a white, water-insoluble substance with a bitter taste. The FT-IR and NMR spectra con- firmed acetylation and revealed the hydrophobic incorporation in sucrose molecule. Fur- thermore, the foamability, foam stability, emulsification and antimicrobial properties of octa-O-acetylsucrose were evaluated. Foams and 50 % (oil/water) model emulsions were prepared with 2 % (w/w) octa-O-acetylsucrose. The obtained results demonstrate the formation of emulsions and foams with high stability (50–70 %). The antimicrobial ac- tivity of octa-O-acetylsucrose was evaluated against seventeen microorganisms (Gram-positive and Gram-negative bacteria, yeasts, and fungi). Octa-O-acetylsucrose inhibited the growth of fungi Penicillium sp., Rhizopus sp. and Fusarium moniliforme at 5 mg cm–3, and yeasts Candida albicans at 1 mg cm–3. Inhibition against Gram-positive and Gram-negative bacteria was not observed. The obtained results demonstrate the po- tential applications of octa-O-acetylsucrose as a foaming agent, oil-in-water emulsion stabilizer, and antifungal substance in pharmaceutical and cosmetic preparations. Keywords: octa-O-acetylsucrose, ultrasound-assisted synthesis, foam, antimicrobial properties Introduction Food and Drug Administration as both a direct and indirect food additive, and as a nail-biting and Sucrose fatty acid esters have been the cause of thumb-sucking deterrent in over-the-counter drug increased interest as odorless, nontoxic, and biode- products. Sucrose octaacetate may be directly added gradable nonionic surfactants with a large scale ap- to food as synthetic flavoring substance, adhesive, plication in the food industry as emulsifiers, an- packaging material, and adjuvant. Its commercial ti-fungal and anti-bacterial agents1–5, edible coating uses include its addition to lacquers and plastics7. reagents6, solubilizator and detergents in cosmetics This wide application of sucrose acetates requires and pharmaceuticals7, insecticides in agriculture7–9 effective and environmentally friendly methods for and as bio-plasticizers in engineering5–7. In addition, their production. The novel approach to the acetyla- sugar esters are produced from cheap and available tion of sucrose includes lipase-catalyzed esterifica- renewable raw materials8,9. Furthermore, acetylated tion of partially acetylated sucrose for the produc- esters of sucrose are naturally found and derived tion of biodegradable and biocompatible from several plant species of Nicotiana and Petu- emulsifiers12. Some reports have demonstrated the nia10,11. acetylation of various mono- and disaccharides with Sucrose octaacetate is used in many pesticide Ac2O–NaOAc under microwave and conventional products and insecticides because of its inert and conditions13–15. Some encouraging results have been safety status. It has also been approved by the US published in relation to the acetylation of lactose by ultrasound-assisted irradiation14 and in the modifi- *Presented at the “4th International Symposium on Environmental Management – Towards Circular Economy (SEM2016), December cation of some long chain fatty acids sucrose es- 4,5,16 7 – 9, Zagreb, Croatia” ters . So far, no detailed results have been pub- **Corresponding author: [email protected] lished regarding the acetylation of sucrose using the N. Petkova et al., “Green” Synthesis of Sucrose Octaacetate and Characterization… 395–402 396 N. Petkova et al., “Green” Synthesis of Sucrose Octaacetate and Characterization…, Chem. Biochem. Eng. Q., 31 (4) 395–402 (2017) environmentally friendly approach of cavitation F254 plates (Merck, Germany) with toluene/ethyl ac- caused by ultrasonic waves. Moreover, relevant in- etate/methanol/water 10:5:4.5:0.2 (v/v/v/v) as an formation on the physicochemical properties of su- eluent. Spots were detected by spraying the plates crose octatacetate is not available in comparison with 10 % (v/v) H2SO4 in methanol, and visualized with sucrose esters with long fatty acid chains. by heating in an oven at 120 °C for 5 min9. Therefore, the aim of the present research is to ac- FT-IR spectroscopy The infrared spectra of the celerate the eco-friendly synthesis of sucrose octa- samples were recorded on a Nicolet FT-IR Avatar acetate by using a “green” method – ultrasound-as- Nicolet (Thermo Science, USA) spectrometer using sisted esterification, and to evaluate its foaming and KBr pellets, and the absorption was reported in emulsifying properties for its potential application wavenumbers (cm–1) in the frequency range of in agriculture, pharmacy, and cosmetics. 4000–400 cm–1. Each spectrum was recorded after 120 scans. 1 13 Materials and methods NMR analysis Similarly, the H and C NMR spectra of the sucrose octaacetate were recorded on Reagents and materials a Bruker Advance III 500 MHz spectrometer using 13 CDCl3 as a solvent. C NMR spectrum was record- D-(+)-Sucrose octaacetate (98 % purity) was ed operating at 151 MHz. All chemical shifts were purchased from Sigma-Aldrich and used as re- reported in ppm with reference to TMS. ceived. All other reagents and solvents were of ana- Hydrophilic-lipophilic balance (HLB) calcu- lytical grade. lation Sucrose octaacetate HLB values were calcu- lated by Griffin`s methods17. Synthesis of octa-O-acetyl-sucrose Foamability and foaming stability Foamability Sucrose octaacetate was synthesized by the re- and foaming stability of the sucrose octaacetate action of 10.0 g (0.029 mol) sucrose with 30 cm3 were evaluated by the previously described method2 (0.27 mol) acetic anhydride in a two-neck round-bot- with slight modifications18. In brief, the aqueous tom flask with 3.0 g (0.036 mol) sodium acetate as dispersion of sucrose octaacetate 0.2 g dm–3 was a catalyst under the following conditions: placed in 50 cm3 in stoppered graduated cylinders – direct heating (over a hot plate, 800 W) upon and the height of each solution (H0, cm) was mea- boiling for 60 min (conventional synthesis); sured. The solution was then shaken for 1 min, and the foam height (H , cm) and the total height (H , – ultrasonic irradiation in a VWR ultrasonic 2 1 bath (VWR, power 30 W, 45 kHz) for 30 min (US cm) were determined immediately. Following a stay synthesis). for 1, 5, 10, 15, 20, 25, 30 min and 60 min, the foam height (H3, cm) was recorded at 25 °C. All the A tube containing anhydrous calcium chloride experiments were performed in triplicate. Foama- was fixed on the top of the reflux and a digital ther- bility and foaming stability were calculated using mometer was placed in the flask for temperature the following equations: monitoring. The reaction mixture was then poured 3 into a 200 cm water-ice mixture, stirred vigorously, Foamability (%) = [(H1–H0)/H0] ·100 (1) and left at 18 °C overnight. Octa-O-acetyl-sucrose Foaming stability (%) = (H /H ) · 100 (2) was precipitated in an excess of cold water as a 3 2 white solid, filtered, and then washed again with Characterization of 50/50 O/W model emul- cold water. The acetyl ester was recrystallized from sions with sucrose octaacetate Twenty-milliliter 95 % ethanol and re-precipitated with water, and solution (2.0 wt %) was homogenized with 20 cm3 then dried in a vacuum-oven to constant weight. sunflower oil for 5 min at 1000 rpm on a homoge- The sucrose octaacetate was characterized by phys- nizer (Ultra Turrax IKA T18 Basic, Germany). icochemical methods. Emulsion stability of the prepared 50/50 oil-in-wa- ter (O/W) emulsions was evaluated by centrifuga- Methods for characterization tion and determination of separated phases. Ten cm3 Melting point and water activity Sample melt- of each emulsion were placed in graduated centri- –1 ing point was determined on an electro-thermal fuge tubes, and centrifuged at 314 rad s for 15 melting point apparatus BŰCHI 510 (Germany) in a min19. Emulsion stability (S) was defined by the for- mula (3): capillary glass tube. Here, water activity (aw) was measured with a water activity meter (AquaLab S (%) = [(V – V)/V ] · 100 (3) Pre, Labcell Ltd., UK). o o 3 Thin layer chromatography (TLC) The TLC where: Vo –volume of the emulsion cm ; V –volume analysis was performed on silica gel Kieselgel 60 of the separated oil phase, cm3 18. N. Petkova et al., “Green” Synthesis of Sucrose Octaacetate and Characterization…, Chem. Biochem. Eng. Q., 31 (4) 395–402 (2017) 397 It was also evaluated by a temperature test. US (synthesized by ultrasound-assisted irradiation). Five cm3 of each emulsion was placed in test tubes, For determination of antimicrobial activity, the disc which
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