Advertisement

Journal of the American Oil Chemists' Society

, Volume 94, Issue 2, pp 271–284 | Cite as

Comparative Fingerprint Changes of Toxic Volatiles in Low PUFA Vegetable Oils Under Deep-Frying

  • L. Molina-Garcia
  • C. S. P. Santos
  • S. C. Cunha
  • S. CasalEmail author
  • J. O. Fernandes
Original Paper

Abstract

The volatile fraction of three vegetable oils recommended for deep-frying due to their high MUFA:PUFA ratios, namely extra-virgin olive oil, peanut oil and canola oil, was compared before and after frying potatoes, with a particular focus on toxic volatiles. For the purpose, a headspace solid-phase-micro extraction technique coupled with gas chromatography and mass spectrometry was optimized, with semi-quantification achieved using two internal standards. Significant qualitative and quantitative differences were observed, both before and after frying. From a total of 51 compounds, aldehydes were the main group formed after deep-frying, their nature and abundance being highly associated with the initial fatty acid composition, particularly linoleic acid (r 2 = −0.999, p ≤ 0.001). Globally, extra-virgin olive oil revealed fewer formations of unsaturated aldehydes, including toxic ones, and correlated with lower amounts of degradation indicators, as polar compounds (r 2 = 0.998, p ≤ 0.001) and p-anisidine value (r 2 = 0.991, p ≤ 0.001). Despite the similarities in total unsaturation degree between canola and peanut oils, the former presented lower amount of volatiles, including E,E-2,4-decadienal and acrolein, the more toxic ones. These results highlight for the pertinence of volatile analyses to evaluate and compare oil degradation under thermal and oxidative stress, while complementing other degradation indicators. Additionally, the optimized methodology allows a direct comparison of different oil matrices, supporting further developments into more general methods for volatiles quantification, enabling more efficient comparison of results between research teams.

Keywords

Deep-frying Volatile fraction Oxidative stability E,E-2,4-decadienal Acrolein Aldehydes HS–SPME–GC–MS 

Notes

Acknowledgements

The authors acknowledge the financial support from PRODER (Contract No. 53989), co-financed by FAEDER, and from project UID/QUI/50006/2013-POCI/01/0145/FEDER/007265 with financial support from FCT/MEC through national funds, co-financed by FEDER, under the Partnership Agreement PT2020 and the PhD Grant—SFRH/BD/82285/2011 attributed to CSPS. LMG also acknowledges the financial support from Campus de Excelencia Internacional Agroalimentario (ceiA3) and University of Jaén, from Spain.

References

  1. 1.
    Choe E, Min DB (2007) Chemistry of deep-fat frying oils. J Food Sci 72:R77–R86CrossRefGoogle Scholar
  2. 2.
    Petersen KD, Jahreis G, Busch-Stockfisch M, Fritsche J (2013) Chemical and sensory assessment of deep-frying oil alternatives for the processing of French fries. Eur J Lipid Sci Technol 115:935–945CrossRefGoogle Scholar
  3. 3.
    Omar MNB, Nor NNM, Idris NA (2007) Changes of headspace volatile constituents of palm olein and selected oils after frying French fries. Pak J Biol Sci 10:1044–1049CrossRefGoogle Scholar
  4. 4.
    Zhang Q, Saleh ASM, Chen J, Shen Q (2012) Chemical alterations taken place during deep-fat frying based on certain reaction products: a review. Chem Phys Lipids 165:662–681CrossRefGoogle Scholar
  5. 5.
    Gertz C, Matthäus B (2012) Optimum deep-frying. Recommendations by the German society for fat science. DGF Deutsche Gesellschaft für Fettwissenschaft e.V.,  Frankfurt/Main, GermanyGoogle Scholar
  6. 6.
    Gupta MK (2004) Selection of frying oil. In: Gupta MK, Warner K, White PJ (eds) Frying technology and practices. AOCS Press, Champaign, IL, pp 29–36Google Scholar
  7. 7.
    Casal S, Malheiro R, Sendas A, Oliveira BPP, Pereira JA (2010) Olive oil stability under deep-frying conditions. Food Chem Toxicol 48:2972–2979CrossRefGoogle Scholar
  8. 8.
    Boskou D (2011) Olive oil. In: Gunstone FD (ed) Vegetable oils in food technology: composition, properties and uses. Blackwell Publishing Ltd, Oxford, pp 243–271CrossRefGoogle Scholar
  9. 9.
    DGE (2013) Directorate-general for education. General recommendation 3/DSEEAS/DGE/2013 on guidelines for scholar canteens, PortugalGoogle Scholar
  10. 10.
    Dean LL, Davis JP, Sanders TH (2011) Groundnut (Peanut) Oil. In: Gunstone FD (ed) Vegetable oils in food technology: composition, properties and uses. Blackwell Publishing Ltd, Oxford, pp 225–242CrossRefGoogle Scholar
  11. 11.
    Prybylski R (2011) Canola/Rapeseed Oil. In: Gunstone FD (ed) Vegetable oils in food technology: composition, properties and uses. Blackwell Publishing Ltd, Oxford, pp 107–136CrossRefGoogle Scholar
  12. 12.
    Martinez-Yusta A, Guillen MD (2014) Deep-frying food in extra virgin olive oil: a study by H-1 nuclear magnetic resonance of the influence of food nature on the evolving composition of the frying medium. Food Chem 150:429–437CrossRefGoogle Scholar
  13. 13.
    Romano R, Giordano A, Le Grottaglie L, Manzo N, Paduano A, Sacchi R, Santini A (2013) Volatile compounds in intermittent frying by gas chromatography and nuclear magnetic resonance. Eur J Lipid Sci Technol 115:764–773CrossRefGoogle Scholar
  14. 14.
    Sghaier L, Vial J, Sassiat P, Thiebaut D, Watiez M, Breton S, Rutledge DN, Cordella CBY (2016) An overview of recent developments in volatile compounds analysis from edible oils: technique-oriented perspectives. Eur J Lipid Sci Technol. doi: 10.1002/ejlt.201500508 Google Scholar
  15. 15.
    Kataoka H, Lord HL, Pawliszyn J (2000) Applications of solid-phase microextraction in food analysis. J Chrom A 880:35–62CrossRefGoogle Scholar
  16. 16.
    Balasubramanian S, Panigrahi S (2011) Solid-phase microextraction (SPME) techniques for quality characterization of food products: a review. Food Bioprocess Technol 4:1–26CrossRefGoogle Scholar
  17. 17.
    Osawa CC, Goncalves LAG, Da Silva MAAP (2013) Odor significance of the volatiles formed during deep-frying with palm olein. J Am Oil Chem Soc 90:183–189CrossRefGoogle Scholar
  18. 18.
    Liu X, Jin Q, Liu Y, Huang J, Wang X, Mao W, Wang S (2011) Changes in volatile compounds of peanut oil during the roasting process for production of aromatic roasted peanut oil. J Food Sci 76:C404–C412CrossRefGoogle Scholar
  19. 19.
    Vichi S, Castellote AI, Pizzale L, Conte LS, Buxaderas S, Lopez-Tamames E (2003) Analysis of virgin olive oil volatile compounds by headspace solid-phase micro extraction coupled to gas chromatography with mass spectrometric and flame ionization detection. J Chrom A 983:19–33CrossRefGoogle Scholar
  20. 20.
    Commission Regulation (EU) N.º2568/91 (1991) On the characteristics of olive oil and olive-residue oil and on the relevant methods of analysis. Off J Eur Union L 248:1Google Scholar
  21. 21.
    Márquez-Ruiz G, Jorge N, Martín-Polvillo M, Dobarganes MC (1996) Rapid, quantitative determination of polar compounds in fats and oils by solid-phase extraction and size-exclusion chromatography using monostearin as internal standard. J Chrom A 749:55–60CrossRefGoogle Scholar
  22. 22.
    Dobarganes MC, Velasco J, Dieffenbacher A (2000) Determination of polar compounds, polymerized and oxidized triacylglycerols, and diacylglycerols in oils and fats. Results of collaborative studies and the standardized method (technical report). Pure Appl Chem 78:1563–1575Google Scholar
  23. 23.
    ISO 6885:2006. (2006). Animal and vegetable fats and oils—determination of Anisidine Value. International Organization for Standardization, SwitzerlandGoogle Scholar
  24. 24.
    Cecchi T, Alfei B (2013) Volatile profiles of Italian monovarietal extra virgin olive oils via HS-SPME-GC-MS: newly identified compounds, flavors molecular. Food Chem 141:2025–2035CrossRefGoogle Scholar
  25. 25.
    Cajka T, Riddellova K, Klimankova E, Cerna M, Pudil F, Hajslova J (2010) Traceability of olive oil based on volatiles pattern and multivariate analysis. Food Chem 121:282–289CrossRefGoogle Scholar
  26. 26.
    Rani AKS, Reddy SY, Chetana R (2010) Quality changes in trans and trans free fats/oils and products during frying. Eur Food Res Technol 230:803–811CrossRefGoogle Scholar
  27. 27.
    Fereidoon S, Ying Z (2005) Lipid oxidation: measurement methods. In: Fereidoon S (ed) Bailey’s industrial oil and fat products. Wiley, New York, pp 357–385Google Scholar
  28. 28.
    Uriarte PS, Guillen MD (2010) Formation of toxic alkylbenzenes in edible oils submitted to frying temperature influence of oil composition in main components and heating time. Food Res Int 43(8):2161–2170CrossRefGoogle Scholar
  29. 29.
    Kalua CM, Allen MS, Bedgood DR Jr, Bishop AG, Prenzler PD, Robards K (2007) Olive oil volatile compounds, flavour development and quality: a critical review. Food Chem 100:273–286CrossRefGoogle Scholar
  30. 30.
    Przybylski R, Mickael Eskin NA (1995) Methods to measure volatile compounds and the flavor significance of volatile compounds. In: Warner K, Mickael Eskin NA (eds) Methods to assess quality and stability of oils and fat-containing foods. AOCS Press, Champaign, IL, pp 107–133  Google Scholar
  31. 31.
    Vranova J, Ciesarova Z (2009) Furan in food—a review. Czech J Food Sci 27:1–10Google Scholar
  32. 32.
    Vichi S, Pizzale L, Conte LS, Buxaderas S, Lopez-Tamames E (2003) Solid-phase microextraction in the analysis of virgin olive oil volatile fraction: modifications induced by oxidation and suitable markers of oxidative status. J Agric Food Chem 51:6564–6571CrossRefGoogle Scholar
  33. 33.
    Fullana A, Carbonell-Barrachina AA, Sidhu S (2004) Comparison of volatile aldehydes present in the cooking fumes of extra virgin olive, olive, and canola oils. J Agric Food Chem 52:5207–5214CrossRefGoogle Scholar
  34. 34.
    Guillen MD, Uriarte PS (2012) Aldehydes contained in edible oils of a very different nature after prolonged heating at frying temperature: presence of toxic oxygenated alpha, beta unsaturated aldehydes. Food Chem 131:915–926CrossRefGoogle Scholar
  35. 35.
    Issaoui M, Flamini G, Hajaij ME, Cioni PL, Hammami M (2011) Oxidative evolution of virgin and flavored olive oils under thermo-oxidation processes. J Am Oil Chem Soc 88:1339–1350CrossRefGoogle Scholar
  36. 36.
    Katragadda HR, Fullana A, Sidhu S, Carbonell-Barrachina AA (2010) Emissions of volatile aldehydes from heated cooking oils. Food Chem 120:59–65CrossRefGoogle Scholar
  37. 37.
    Ontanon I, Cullere L, Zapata J, Villanueva B, Ferreira V, Escudero A (2013) Application of a new sampling device for determination of volatile compounds released during heating olive and sunflower oil: sensory evaluation of those identified compounds. Eur Food Res Technol 236:1031–1040CrossRefGoogle Scholar
  38. 38.
    Procida G, Cichelli A, Compagnone D, Maggio RM, Cerretani L, Del Carlo M (2009) Influence of chemical composition of olive oil on the development of volatile compounds during frying. Eur Food Res Technol 230:217–229CrossRefGoogle Scholar
  39. 39.
    Sghaier L, Vial J, Sassiat P, Thiebaut D, Watiez M, Breton S, Rutledge DN, Cordella CBY (2016) Analysis of target volatile compounds related to fishy off-flavor in heated rapeseed oil: a comparative study of different headspace techniques. Eur J Lipid Sci Technol 118:906–918CrossRefGoogle Scholar
  40. 40.
    Feron VJ, Til HP, Devrijer F, Woutersen RA, Cassee FR, Vanbladeren PJ (1991) Aldehydes: occurrence, carcinogenic potential, mechanism of action and risk assessment. Mutat Res 259:363–385CrossRefGoogle Scholar
  41. 41.
    Perkins EG (2007) Volatile odor and flavor components formed in deep frying. In: Erickson MD (ed) Deep frying (chemistry, nutrition and practical applications). AOCS Press, Urbana, IL, pp 51–56Google Scholar
  42. 42.
    Frankel EN, Neff WE, Selke E (1981) Analysis of autoxidized fats by gas chromatography mass spectrometry: VII. volatile thermal decomposition products of pure hydroperoxides from autoxidized and photosensitized oxidized methyl oleate, linoleate and linolenate. Lipids 16:279–285CrossRefGoogle Scholar
  43. 43.
    Boskou G, Salta FN, Chiou A, Troullidou E, Andrikopoulos NK (2006) Content of trans, trans-2,4-decadienal in deep-fried and pan-fried potatoes. Eur J Lipid Sci Technol 108:109–115CrossRefGoogle Scholar

Copyright information

© AOCS 2017

Authors and Affiliations

  • L. Molina-Garcia
    • 1
    • 2
  • C. S. P. Santos
    • 1
  • S. C. Cunha
    • 1
  • S. Casal
    • 1
    • 3
    Email author
  • J. O. Fernandes
    • 1
  1. 1.LAQV-REQUIMTEPortoPortugal
  2. 2.Department of Physical and Analytical Chemistry, Faculty of Experimental SciencesUniversity of JaénJaénSpain
  3. 3.EPIUnit-ISPUPUniversity of PortoPortoPortugal

Personalised recommendations