19F NMR method for the determination of quality of virgin olive oil

Authors

  • L. L. Zhou School of Environmental and Chemical Engineering
  • C. Li School of Environmental and Chemical Engineering
  • X. C. Weng School of Environmental and Chemical Engineering
  • X. M. Fang Shanghai Entry-Exit Inspection Quarantine Bureau
  • Z. H. Gu Shanghai Food Security Officce

DOI:

https://doi.org/10.3989/gya.0242151

Keywords:

Alcohols, Diglycerides, 4-Fluorobenzoyl chloride, 19F NMR, Quality of olive oil

Abstract


This paper reported a potential analytical technique based on NMR spectroscopy for the determination of quality of olive oil. The model compounds with active hydrogen, including free sterols, free aliphatic alcohols, phenolics, and free fatty acids were determined by 19F NMR upon derivation with 4-fluorobenzoyl chloride. Integration of the appropriate signals of the derivatives of the compounds in the corresponding 19F NMR spectrum allows for the quantification of these compounds. 37 Samples of commercial olive oil and 5 samples of other plant oils were determined by 19F NMR. The amount of diglycerides and the ratio of 1,2-diglycerides to the total amount of diglycerides were analyzed to monitor whether extra virgin olive oil was adulterated with low price olive oil and other plant oils or not. The results showed that the total diglyceride content should not be higher than 2.5% and the ratio (D) of 1,2-diglycerides to total diglycerides should be higher than 0.35 for extra virgin olive oil. This method is an easier, simpler, safer, faster and more reliable technique for the determination of the quality of olive oil and can also be extended to monitoring the quality of ordinary edible oils.

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References

Benito M, Lasa JM, Gracia P, Oria R, Abenoza M, Varona L, Sánchez-Gimeno AC. 2013. Olive oil quality and ripening in super-high-density Arbequina orchard. J. Sci. Food Agric. 93, 2207–2220. http://dx.doi.org/10.1002/jsfa.6028 PMid:23413119

Berger M, Laumen K, Schneider MP. 1992. Enzymatic Esterification of Glycerol I. Lipase-Catalyzed Synthesis of Regioisomerically Pure 1,3-sn-Diacylglycerols. J. Am. Oil. Chem. Soc. 69, 955–960. http://dx.doi.org/10.1007/BF02541057

Covas M, Ruiz-Gutiérrez V, de la Torre R, Kafatos A, Lamuela-Raventós RM, Osada J, Owen RW, Visioli F. 2006. Minor components of olive oil: evidence to date of health benefits in humans. Nutr. Rev. 64, s20–s30. http://dx.doi.org/10.1111/j.1753-4887.2006.tb00260.x

European Community, Commission Regulation. 2001. No. 1513/2001 July 23 amending Regulations No. 136/66/EEC and No. 1638/98 as regards the extension of the period of validity of the aid scheme and the quality strategy for olive oil. Official Journal of European Communities, L201, 4–7.

Fragaki G, Spyros A, Siragakis G, Salivaras E, Dais P. 2005. Detection of Extra Virgin Olive Oil Adulteration with Lampante Olive Oil and Refined Olive Oil Using Nuclear Magnetic Resonance Spectroscopy and Multivariate Statistical Analysis. J. Agric. Food. Chem. 53, 2810–2816. http://dx.doi.org/10.1021/jf040279t PMid:15826023

Fronimaki P, Spyros A, Christophoridou S, Dais P. 2002. Determination of the Diglyceride Content in Greek Virgin Olive Oils and Some Commercial Olive Oils by Employing 31P NMR Spectroscopy. J. Agric. Food. Chem. 50, 2207–2213. http://dx.doi.org/10.1021/jf011380q PMid:11929272

Gakh YG, Gakh AA, Gronenborn AM. 2000. Fluorine as an NMR probe for structural studies of chemical and biological systems. Magn. Reson. Chem. 38, 551–558. http://dx.doi.org/10.1002/1097-458X(200007)38:7<551::AID-MRC686>3.0.CO;2-Q

Hatzakis E, Dagounakis G, Agiomyrgianaki A, Dais P. 2010. A facile NMR method for the quantification of total, free and esterified sterols in virgin olive oil. Food Chem. 122, 346–352. http://dx.doi.org/10.1016/j.foodchem.2010.02.043

Paquot C, Havtfenne A. 1987. Standard methods for analysis of oils, fats and derivatives. International Union of Pure and Applied Chemistry IUPAC.

Jimeno SA. 1982. The Spanish toxic symptoms. Trends Anal. Chem. 1, 4–6.

López-Miranda J, Pérez-Jiménez F, Ros E, De Caterina R, Badimón L, Covas MI, et al. 2010. Olive oil and health: summary of the II international conference on olive oil and health consensus report, Jaén and Córdoba (Spain) 2008. Nutr Metab Cardiovasc Dis. 20, 284–294. http://dx.doi.org/10.1016/j.numecd.2009.12.007 PMid:20303720

Maggio RM, Cerretani L, Chiavaro E, Kaufman TS, Bendini A. 2010. A novel chemometric strategy for the estimation of extra virgin olive oil adulteration with edible oils. Food Control. 21, 890–895. http://dx.doi.org/10.1016/j.foodcont.2009.12.006

Medeiros MD. 2001. Olive oil and health benefits, In R.E.C. Wildman (Ed.) Handbook of Nutraceuticals and Functional Foods. USA: CRC press, Boca Raton, 261–267.

Pérez-Camino MC, Moreda W, Cert A. 2001. Effects of Olive Fruit Quality and Oil Storage Practices on the Diacylglycerol Content of Virgin Olive Oils. J. Agric. Food. Chem. 49, 699–704. http://dx.doi.org/10.1021/jf001064w PMid:11262015

Sacchi R, Addeo F, Paolillo L. 1997. 1H and 13C NMR of Virgin Olive Oil. An Overview. Magn. Reson. Chem. 35, S133–S145. http://dx.doi.org/10.1002/(SICI)1097-458X(199712)35:13<S133::AID-OMR213>3.0.CO;2-K

Sacchi R, Paolillo L, Giudicianni I, Addeo F. 1991. Rapid 1H-NMR determination of 1,2 and 1,3 diglycerides in virgin olive oils. Ital J Food Sci. 3, 253–262.

Sacchi R, Patumi M, Fontanazza G, Barone P, Fiordiponti P, Mannina L, Rossi E, Segre AL. 1996. A High-Field 1H Nuclear Magnetic Resonance Study of the Minor Components in Virgin Olive Oils. J. Am. Oil. Chem. Soc. 73,747–758. http://dx.doi.org/10.1007/BF02517951

Spratt MP, Don HC. 1984. p-Fluorobenzoyl Chloride for Characterization of Active Hydrogen Functional Groups by Fluorine- 19 Nuclear Magnetic Resonance Spectrometry. Anal Chem. 56, 2038–2043. http://dx.doi.org/10.1021/ac00276a014

Spyros A, Dais P. 2000. Application of 31P NMR Spectroscopy in Food Analysis. 1. Quantitative Determination of the Monoand Diglyceride Composition of Olive Oils. J. Agric. Food. Chem. 48, 802–805. http://dx.doi.org/10.1021/jf9910990 PMid:10725153

Tay A, Singh RK, Krishnan SS, Gore JP. 2002. Authentication of Olive Oil Adulterated with Vegetable Oils Using Fourier Transform Infrared Spectroscopy. LWT- Food Sci Technol. 35, 99–103.

Vigli G, Philippidis A, Spyros A, Dais P. 2003. Classification of Edible Oils by Employing 31P and 1H NMR Spectroscopy in Combination with Multivariate Statistical Analysis. A Proposal for the Detection of Seed Oil Adulteration in Virgin Olive Oils. J. Agric. Food. Chem. 51, 5715–5722. http://dx.doi.org/10.1021/jf030100z PMid:12952424

Visioli F, Caruso D, Grande S, Bosisio R, Villa M, Galli G, Sirtori C, Galli C. 2005. Virgin Olive Oil Study (VOLOS): vasoprotective potential of extra virgin olive oil in mildly dyslipidemic patients. Eur J Nutr. 44, 121–127. http://dx.doi.org/10.1007/s00394-004-0504-0 PMid:15309433

Published

2015-12-30

How to Cite

1.
Zhou LL, Li C, Weng XC, Fang XM, Gu ZH. 19F NMR method for the determination of quality of virgin olive oil. Grasas aceites [Internet]. 2015Dec.30 [cited 2024Apr.18];66(4):e106. Available from: https://grasasyaceites.revistas.csic.es/index.php/grasasyaceites/article/view/1572

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Section

Research