Chemical and structural variations in hazelnut and soybean oils after ozone treatments

H. Uzun; E. G. Kaynak; E. Ibanoglu; S. Ibanoglu

doi:10.3989/gya.1098171

Authors

H. Uzun Gaziantep University, Department of Food Engineering https://orcid.org/0000-0003-1098-3197
E. G. Kaynak Gaziantep University, Department of Food Engineering https://orcid.org/0000-0003-1805-1984
E. Ibanoglu Gaziantep University, Department of Food Engineering https://orcid.org/0000-0003-2665-7919
S. Ibanoglu Gaziantep University, Department of Food Engineering https://orcid.org/0000-0002-0727-4747

DOI:

https://doi.org/10.3989/gya.1098171

Keywords:

FTIR, GC, Hazelnut oil, NMR, Ozone, Soybean oil, Viscosity

Abstract

In the present work, the effect of ozone treatments on the structural properties of soybean oil (SBO) and hazelnut oil (HO) were investigated. The study presents the findings and results about the oxidation of HO and SBO with ozone, which has not been fully studied previously. The HO and SBO were treated with ozone gas for 1, 5, 15, 30, 60, 180 and 360 min. The ozone reactivity with the SBO and HO during the ozone treatment was analyzed by ¹H, ¹³C NMR, FTIR and GC. The iodine value, viscosity and color variables (L*, a* and b*) of untreated and ozone treated oils were determined. Reaction products were identified according to the Criegee mechanism. New signals at 5.15 and 104.35 ppm were assigned to the ring protons of 1,2,4- trioxolane (secondary ozonide) in the ozonated oils in ¹H and ¹³C NMR, respectively. Ozonated oils exhibited peaks at 9.75 and 2.43 ppm in ¹H and NMR, which corresponded to the aldehydic proton and α-methylene group and to the carbonyl carbon, respectively. The peak at 43.9 ppm in ¹³C NMR was related to the α-methylene group and to the carbonyl carbon. The new signals formed in the ozonation process gradually increased with respect to ozone treatment time. After 360 min of ozone treatment, the carbon-carbon double bond signal, which belongs to the unsaturated fatty acids, disappeared completely in the spectrum. An increase in viscosity, a decrease in iodine value and a dramatic reduction in b* of the oil samples on (+) axis were observed with increased ozone treatment time.

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References

Adhvaryu A, Erhan SZ, Liu ZS, Pérez JM. 2000. Oxidation kinetic studies of oils derived from unmodified and genetically modified vegetables using pressurized differential scanning calorimetry and nuclear magnetic resonance spectroscopy. Thermochim. Acta 364, 87–97. https://doi.org/10.1016/S0040-6031(00)00626-2

Alasalvar C, Karamac´ M, Amarowicz R, Shahidi F. 2006. Antioxidant and antiradical activities in extracts of hazelnut kernel (Corylus avellana L.) and hazelnut green leafy cover. J. Agric. Food Chem. 54, 4826–4832. https://doi.org/10.1021/jf0601259 PMid:16787035

Anachkov MP, Rakovski SK, Stefanova RV. 2000. Ozonolysis of 1,4-cis-polyisoprene and 1,4-trans-polyisoprene in solution. Polym. Deg. Stab. 67, 355–363. https://doi.org/10.1016/S0141-3910(99)00137-8

Atungulu GG, Pan Z. 2012. Microbial Decontamination in the Food Industry. Microbial decontamination of nuts and Spices. 125–162.

Benevides CMJ, Veloso MCC, Pereira PAP, Andrade JB. 2011. A chemical study of ?-carotene oxidation by ozone in an organic model system and the identification of the resulting products. Food Chem. 126, 927–934. https://doi.org/10.1016/j.foodchem.2010.11.082

Beuchat LR. 1992. Surface disinfection of raw produce. Dairy, Food and Environ. Sanit. 12(1), 6–9.

Britton G. 1995. Structure and Properties of carotenoids in relation to function. Fed. Am. Soc. Exp. Biol. 9, 1551–1558. PMid:8529834

Che Man YB, Setiowaty G. 1999. Application of fourier transform infrared spectroscopy to determine free fatty acid contents in palm olein. Food Chem. 66, 109–114. https://doi.org/10.1016/S0308-8146(98)00254-4

Chen R, Maa F, Li P, Zhang W, Ding X, Zhang Q, Li M, Wanga Y, Xu B. 2014. Effect of ozone on aflatoxins detoxification and nutritional quality of peanuts. Food Chem. 146, 284–288. https://doi.org/10.1016/j.foodchem.2013.09.059 PMid:24176344

Criegee R. 1975. Mechanism of Ozonolysis. Angew. Chem. Int. Edit. 14, 745–752. https://doi.org/10.1002/anie.197507451

Díaz MF, Nú-ez N, Quincose D, Díaz W, Hernández F. 2005. Study of Three Sistems of Ozonized Cocunut Oil. Ozone Sci. Eng. 27, 153–157. https://doi.org/10.1080/01919510590925275

Dogan A, Siyakus G, Severcan F. 2007. FTIR spectroscopic characterization of irradiated hazelnut (Corylus avellana L.). Food Chem. 100, 1106–1114. https://doi.org/10.1016/j.foodchem.2005.11.017

European pharmacopoeia 2004. Iodine value. Council of Europe, 5th edn. Strasbourg Cedex, France, 127–128.

Greene AK, Smith GW, Knight CS. 1999. Ozone in dairy chilling watersystems: Effect on metal materials. Int. J. Dairy Technol. 52, 126–128. https://doi.org/10.1111/j.1471-0307.1999.tb02853.x

Guillén MD, Cabo N. 2000. Some of the most significant changes in the Fourier transform infrared spectra of edible oils under oxidative conditions. J. Sci. Food Agric. 80, 2028–2036. https://doi.org/10.1002/1097-0010(200011)80:14<2028::AID-JSFA713>3.0.CO;2-4

Guillén MD, Cabo N. 1997. Characterization of edible oils and lard by Fourier transform infrared spectroscopy. Relationships between composition and frequency of concrete bands of the fingerprint region. J. Am. Oil Chem. Soc. 74, 1281–1286. https://doi.org/10.1007/s11746-997-0058-4

Gunstone FD. 2002. Vegetable Oils in Food Technology: Composition, Properties and Uses. Blackwell Publishing, CRC Press, USA.

Kim J, Kim DN, Lee, SH, Yoo SH, Lee S. 2010. Correlation of fatty acid composition of vegetable oils with rheological behaviour and oil uptake. Food Chem. 118, 398–402. https://doi.org/10.1016/j.foodchem.2009.05.011

King CJ, Blumberg J, Jenab M, Tucker KL. 2008. Tree Nuts and Peanuts as Components of a Healthy Diet. J. Nutr. 138, 1736–1740. https://doi.org/10.1093/jn/138.9.1736S PMid:18716178

Liu HR, White PJ. 1992. Oxidative stability of soybean oils with altered fatty acid compositions. J. Am. Oil Chem. Soc. 53, 528–532. https://doi.org/10.1007/BF02636103

Murray RW. 1968. Mechanism of ozonolysis. Acc. Chem. Res. 1, 313–320. https://doi.org/10.1021/ar50010a004

Nishikawa N, Yamada K, Matsutani S, Higo M, Kigawa H, Inagaki T. 1995. Structures of ozonolysis products of methyl oleate obtained in a carboxylic-acid medium. J. Am. Oil Chem. Soc. 72, 735–740. https://doi.org/10.1007/BF02635664

Prakash A. 2013. Non-thermal processing technologies to improve the safety of nuts. Improving the Safety and Quality of Nuts 35–55.

Pryor WA. 1994. Mechanisms of radical formation from reactions of ozone with target molecules in the lung. Free Radic. Biol. Med. 17, 451–465. https://doi.org/10.1016/0891-5849(94)90172-4

Rice RG, Robson CM, Miller GW, Hill AG. 1981. Uses of ozone in drinking water treatment. J. Am.Water Works As. 73, 44–57. https://doi.org/10.1002/j.1551-8833.1981.tb04637.x

Rocha AMCN, Morais AMMB. 2003. Shelf life of minimally processed apples (cv. Jonagored) determined by colour changes. Food Control 14, 13–20. https://doi.org/10.1016/S0956-7135(02)00046-4

Rodrigues de Almeida Kogawa N, José de Arruda E, Micheletti AC, De Fatima Cepa Matos M, De Oliveira LCS, Pires de Lima D, Pereira Carvalho NC, Dias de Oliveira P, De Castro Cunha M, Ojeda M, Beatriz A. 2015. Synthesis, Characterization, Thermal Behavior, and Biological Activity of Ozonides from Vegetable Oils. RSC Adv. 5, 65427–36. https://doi.org/10.1039/C5RA02798E

Rodriguez EB, Rodriguez-Amaya DB. 2007. Formation of apocarotenoids and epoxycarotenoids from b-carotene by reactions and by autoxidation in model systems and processed foods. Food Chem. 101, 563–572. https://doi.org/10.1016/j.foodchem.2006.02.015

Sadowska J, Johansson B, Johannessen E, Friman R, Broniarz-Press L, Rosenholm JB. 2008. Characterization of ozonated vegetable oils by spectroscopic and chromatographic methods. Chem. Phys. Lipids 151, 85–91. https://doi.org/10.1016/j.chemphyslip.2007.10.004 PMid:18023273

Santos JCO, Santos IMG, Conceiça˘o MM, Porto SL, Trindade MFS, Souza AG. 2004. Thermoanalytical, kinetic and rheological parameters of commercial edible vegetable oils. J. Therm. Anal. Calorim. 75, 419–428. https://doi.org/10.1023/B:JTAN.0000027128.62480.db

Sega A, Zanardi I, Chiasserini L, Gabbrielli A, Bocci V, Travagli V. 2010. Properties of sesame oil by detailed 1 H and 13 C NMR assignments before and after ozonation and their correlation with iodine value, peroxide value, and viscosity measurements. Chem. Phys. Lipids 163, 148–156. https://doi.org/10.1016/j.chemphyslip.2009.10.010 PMid:19900426

Silverstein RM, Blaser GC, Morril TC. 1974. Spectrometric Identification of Organic Compounds, 3rd edn., John Wiley and Sons, New York, 73–119.

Skalska K, Ledakowicz S, Perkowski J, Sencio B. 2009. Germicidal Properties of Ozonated Sunflower Oil. Ozone-Sci Eng. 31, 232–237. https://doi.org/10.1080/01919510902838669

Soriano NU, Migo VP, Matsumura M. 2003. Functional group analysis during ozonation of sunflower oil methyl esters by FT-IR and NMR. Chem. Phys. Lipids 126, 133–140. https://doi.org/10.1016/j.chemphyslip.2003.07.001 PMid:14623448

Tan CP, Che Man YB. 1999. Differential Scanning Calorimetric Analysis for monitoring the oxidation of heated oils. Food Chem. 67, 177–184. https://doi.org/10.1016/S0308-8146(99)00115-6

Thomas A. 2000. "Fats and Fatty Oils". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. https://doi.org/10.1002/14356007.a10_173

Tsanev R, Tashkov W, Russeva A. 1998. Content of trans-Fatty Acids in Edible Margarines. J. Am. Oil Chem. Soc. 75, 143–145. https://doi.org/10.1007/s11746-998-0025-8

USDA 1997. Code of Federal Regulations, Title 9, Part 381.66, poultry products; temperatures and chilling and freezing procedures. Office of the Federal Register National Archives and Records Administration, Washington, DC.

Wang T. 2002. Soybean oil. Gunstone FD. (Ed.) Vegetable Oils in Food Technology: Composition, Properties and Uses, Blackwell Publishing, CRC Press, USA.

Wu M, Church DF, Mahier TJ, Barker SA, Pryor W.A. 1992. Separation and spectral data of the six isomeric ozonides from methyl oleate. Lipids 27, 129–135. https://doi.org/10.1007/BF02535812 PMid:1579057

Xu YX, Hanna MA, Josiah SJ. 2007. Hybrid hazelnut oil characteristics and its potential oleochemical application. Ind. Crop. Prod. 26, 69–76. https://doi.org/10.1016/j.indcrop.2007.01.009

Yang PPW, Chen TC. 1979. Effects of ozone treatment on microflora of poultry meat. J. Food Process. Pres. 3, 177–185. https://doi.org/10.1111/j.1745-4549.1979.tb00579.x

Zahardis J, LaFranchi BW, Petrucci GA. 2006. The heterogeneous reaction of particle-phase methyl esters and ozone elucidated by photoelectron resonance capture ionization: Direct products of ozonolysis and secondary reactions leading to the formation of ketones. Int. J. Mass Spectrom. 253, 38–47. https://doi.org/10.1016/j.ijms.2006.02.010

Zanardi I, Travagli V, Gabbrielli A, Chiasserini L, Bocci V. 2008. Physico-chemical characterisation of sesame oil derivatives. Lipids 43, 877–886. https://doi.org/10.1007/s11745-008-3218-x PMid:18679737