European Food Research and Technology

, Volume 244, Issue 12, pp 2231–2241 | Cite as

Delta-7-stigmastenol: quantification and isomeric formation during chemical refining of olive pomace oil and optimization of the neutralization step

  • Malika Drira
  • Hazem Jabeur
  • Fatma Marrakchi
  • Mohamed BouazizEmail author
Original Paper



The aim of this study is to evaluate the formation of the increase of Δ-7-stigmastenol during the chemical refining of pomace olive oil (POO) and the optimal neutralization by NaOH concentration of 20 °Be at a temperature of 70 °C. A comparison has been made between virgin olive oil (VOO) and consecutive steps of refining process in the amounts of Δ-7-stigmastenol of the POO oil samples. Among the oils, refined olive oil particularly the neutralized olive oil (NOO) by soda (NaOH) contained a high-level of Δ-7-stigmastenol. A mean result found in NOO by different concentration of NaOH from 15 to 25 °Be showed increased values significantly (p < 0.05) from 0.70 ± 0.01% to 0.78 ± 0.01% of Δ-7-stigmastenol and increased significantly (p < 0.05) the levels of erythrodiol and uvaol from 26.34 ± 0.39% to 28.11 ± 0.42%. Then, the concentration of the ∆-7-stigmastenol was evaluated using a GC–MS instrument. Besides, further analyses were performed to ensure the uniqueness of the peak of Δ-7-stigmastenol and absence of any overlap. In all cases, the level of Δ-7-stigmastenol was higher than the limit set by the International Olive Council.

Graphical abstract


Δ-7-Stigmastenol Chemical refining processes Neutralization Optimization GC/MS 



Virgin olive oil


Pomace–olive oil


Refined pomace olive oil


Free fatty acids


Trans-fatty acids


Gas chromatography/mass spectrometry


International olive council


Neutralization olive oil



The authors would like to thank the “Ministère de l’Enseingement Supérieur et de la Recherche Scientifique, Tunisia LR14ES08” and “Ministère de l’Agriculture et des Ressources Hydrauliques, Tunisia” for the support of this research work. The authors acknowledge also National Funds through Ministry of Higher Education-Tunisia for financing MedOOmics Project—“Mediterranean Extra Virgin Olive Oil Omics: profiling and fingerprinting”—“Arimnet2/0001/2015”, Strategic Projects UID/AGR/00115/2013. The authors would like also to thank Madam. Mariem DRIRA for English correcting of this manuscript.

Compliance with ethical standards

Conflict of interest

The authors declare no conflict of interest.

Compliance with Ethics requirements

This article does not contain any studies with human or animal subjects.


  1. 1.
    Cecchi L, Innocenti M, Melani F et al (2017) New isobaric lignans from refined olive oils as quality markers for virgin olive oils. Food Chem 219:148–157. CrossRefPubMedGoogle Scholar
  2. 2.
    Gharbi I, Issaoui M, Mehri S et al (2015) Agronomic and technological factors affecting tunisian olive oil quality. Agric Sci 06:513. CrossRefGoogle Scholar
  3. 3.
    Jabeur H, Drira M, Rebai A, Bouaziz M (2017) Putative markers of adulteration of higher-grade olive oil with less expensive pomace olive oil by GC combined with chemometrics. J Agric Food Chem 65:5375–5383. CrossRefPubMedGoogle Scholar
  4. 4.
    Jabeur H, Zribi A, Abdelhedi R, Bouaziz M (2015) Effect of olive storage conditions on Chemlali olive oil quality and the effective role of fatty acids alkyl esters in checking olive oils authenticity. Food Chem 169:289–296. CrossRefPubMedGoogle Scholar
  5. 5.
    Marrakchi F, Kriaa K, Hadrich B, Kechaou N (2015) Experimental investigation of processing parameters and effects of degumming, neutralization and bleaching on lampante virgin olive oil’s quality. Food Bioprod Process 94:124–135. CrossRefGoogle Scholar
  6. 6.
    Antonopoulos K, Valet N, Spiratos D, Siragakis G (2006) Olive oil and pomace olive oil processing. Grasas Aceites 57:56–67Google Scholar
  7. 7.
    Gomes T, Caponio F, Durante V et al (2012) The amounts of oxidized and oligopolymeric triacylglycerols in refined olive oil as a function of crude oil oxidative level. LWT-Food Sci Technol 45:186–190. CrossRefGoogle Scholar
  8. 8.
    García A, Ruiz-Méndez MV, Romero C, Brenes M (2006) Effect of refining on the phenolic composition of crude olive oils. J Am Oil Chem Soc 83:159–164. CrossRefGoogle Scholar
  9. 9.
    Aluyor EO, Aluyor P, Ozigagu CE (2009) Effect of refining on the quality and composition of groundnut oil. Afr J Food Sci ACFS 3:201–205Google Scholar
  10. 10.
    Ortega-García J, Gámez-Meza N, Noriega-Rodriguez JA et al (2006) Refining of high oleic safflower oil: Effect on the sterols and tocopherols content. Eur Food Res Technol 223:775–779. CrossRefGoogle Scholar
  11. 11.
    Krishna AGG, Khatoon S, Shiela PM et al (2001) Effect of refining of crude rice bran oil on the retention of oryzanol in the refined oil. J Am Oil Chem Soc 78:127–131. CrossRefGoogle Scholar
  12. 12.
    Hoed VV, Depaemelaere G, Ayala JV et al (2006) Influence of chemical refining on the major and minor components of rice brain oil. J Am Oil Chem Soc 83:315–321. CrossRefGoogle Scholar
  13. 13.
    Ceci LN, Carelli AA (2007) Characterization of monovarietal argentinian olive oils from new productive zones. J Am Oil Chem Soc 84:1125–1136. CrossRefGoogle Scholar
  14. 14.
    Codex Alimentarius Commission, 3rd ed. (2007) Report of the twentieth session of the codex committee on fats and oils. Rome, Italy.
  15. 15.
    Houshia O, Abueid M, Zaid O et al (2014) The Influence of peacock-eye disease and fruit-fly infection on olive oil ∆7 stigmasterol in Northern West Bank. Int J Ecosyst 4:184–189. CrossRefGoogle Scholar
  16. 16.
    Abu-Alruz K, Afaneh IA, Quasem JM et al (2011) Factors affecting D-7-stigmastenol in palestinian olive oil. J Appl Sci 11:797–805. CrossRefGoogle Scholar
  17. 17.
    Jamie A, Rodney JM, Anthony H et al (2007) La qualit et la stabilite oxydante de l’huile d’olive australienne en fonction de la date de recolte et de l’irrigation Journal of Food Lipids-Wiley Online Library. Accessed 18 Oct 2017
  18. 18.
    Pehlivan B, Yılmaz E (2010) Comparison of oils originating from olive fruit by different production systems. J Am Oil Chem Soc 87:865–875. CrossRefGoogle Scholar
  19. 19.
    Oueslati I, MANAI DJEBALI H, Faouzia H et al (2009) Sterol, triterpenic dialcohol, and triacylglycerol compounds of extra virgin olive oils from some tunisian varieties grown in the region of Tataouine. Food Sci Technol Int 15:5–13. CrossRefGoogle Scholar
  20. 20.
    Mailer R, Ayton J, Graham K (2010) The influence of growing region, cultivar and harvest timing on the diversity of Australian olive oil. JAOCS J Am Oil Chem Soc 87:877–884. CrossRefGoogle Scholar
  21. 21.
    Temime SB, Manai H, Methenni K et al (2008) Sterolic composition of Chétoui virgin olive oil: Influence of geographical origin. Food Chem 110:368–374. CrossRefPubMedGoogle Scholar
  22. 22.
    Guil-Guerrero JL, Urda-Romacho J (2009) Quality of extra virgin olive oil affected by several packaging variables. Grasas Aceites 60:125–133CrossRefGoogle Scholar
  23. 23.
    ISO 660 (2009) Animal and vegetable fats and oils, determination of acid value and acidityGoogle Scholar
  24. 24.
    International Olive Council, COI/T, 20/ Doc. No. 19 Rev.3. (2010) Spectrophotometric investigation in the ultravioletGoogle Scholar
  25. 25.
    International Olive Council, COI/T, 20/Doc. No. 17 (2001) Determination of trans unsaturated fatty acids by capillary column gas chromatographyGoogle Scholar
  26. 26.
    International Olive Council, COI/T, 20/Doc. No. 28 (2009) Determination of the content of waxes fatty acid methyl esters and fatty acid ethyl esters by capillary gas chromatographyGoogle Scholar
  27. 27.
    International Olive Council, COI/T, 20/Doc. No. 30 (2013) Determination of the composition and content of sterols and triterpene dialcohols by capillary column gas chromatographyGoogle Scholar
  28. 28.
    Pal US, Patra RK, Sahoo NR et al (2015) Effect of refining on quality and composition of sunflower oil. J Food Sci Technol 52:4613–4618. CrossRefPubMedGoogle Scholar
  29. 29.
    Vlahakis C, Hazebroek J (2000) Phytosterol accumulation in canola, sunflower, and soybean oils: Effects of genetics, planting location, and temperature. J Am Oil Chem Soc 77:49–53. CrossRefGoogle Scholar
  30. 30.
    Ceriani R, Meirelles AJA (2007) Formation of trans PUFA during deodorization of canola oil: a study through computational simulation. Chem Eng Process 46:375–385CrossRefGoogle Scholar
  31. 31.
    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 49:699–704CrossRefGoogle Scholar
  32. 32.
    Carelli AA, Frizzera LM, Forbito PR, Crapiste GH (2002) Wax composition of sunflower seed oils. J Am Oil Chem Soc 79:763–768. CrossRefGoogle Scholar
  33. 33.
    Samaniego-Sánchez C, Quesada-Granados JJ, de la Serrana HL-G, López-Martínez MC (2010) β-Carotene, squalene and waxes determined by chromatographic method in picual extra virgin olive oil obtained by a new cold extraction system. J Food Compos Anal 23:671–676. CrossRefGoogle Scholar
  34. 34.
    Commission Implementing Regulation (EU) No. 1348, 2013 of 16 December (2013) Amending Regulation (EEC) No. 2568/91 on the characteristics of olive oil and olive-residue oil and on the relevant methods of analysis. Off J L 338:31–67Google Scholar
  35. 35.
    Gómez G, Soledad M (2001) Composición química de distintas calidades de aceites de oliva virgen de la variedad “Empeltre” en el bajo Aragón. Grasas Aceites 52:52–58Google Scholar
  36. 36.
    Jabeur H, Zribi A, Makni J et al (2014) Detection of Chemlali extra-virgin olive oil adulteration mixed with soybean oil, corn oil, and sunflower oil by using GC and HPLC. J Agric Food Chem 62:4893–4904. CrossRefPubMedGoogle Scholar
  37. 37.
    Ranalli A, Angerosa F (1996) Integral centrifuges for olive oil extraction. The qualitative characteristics of products. J Am Oil Chem Soc 73:417–422. CrossRefGoogle Scholar
  38. 38.
    Ceci LN, Carelli AA (2007) Characterization of monovarietal Argentinian olive oils from new productive zones. J Am Oil Chem Soc 84:1125–1136. CrossRefGoogle Scholar
  39. 39.
    Rodriguez-Rodriguez R, Perona JS, Herrera MD, Ruiz-Gutierrez V (2006) Triterpenic compounds from “Orujo” olive oil elicit vasorelaxation in aorta from spontaneously hypertensive rats. J Agric Food Chem 54:2096–2102. CrossRefPubMedGoogle Scholar
  40. 40.
    Essid K, Chtourou M, Trabelsi M, Frikha MH (2009) Influence of the neutralization step on the oxidative and thermal stability of acid olive oil. J Oleo Sci 58:339–346CrossRefGoogle Scholar
  41. 41.
    Chang M, Li D, Wang W et al (2017) Comparison of sodium hydroxide and calcium hydroxide pretreatments on the enzymatic hydrolysis and lignin recovery of sugarcane bagasse. Bioresour Technol 244:1055–1058. CrossRefPubMedGoogle Scholar
  42. 42.
    Kozyuk O, Reimers P (2017) Method for degumming vegetable oil. US 9,845,442Google Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  • Malika Drira
    • 1
  • Hazem Jabeur
    • 1
    • 2
  • Fatma Marrakchi
    • 1
  • Mohamed Bouaziz
    • 1
    • 3
    Email author
  1. 1.Laboratoire d’Electrochimie et EnvironnementEcole National d’Ingénieur de Sfax, Universitéde SfaxSfaxTunisia
  2. 2.Office National de l’HuileSfaxTunisia
  3. 3.Institut Supérieur de Biotechnologie de SfaxUniversité de SfaxSfaxTunisia

Personalised recommendations