Skip to main content
Log in

Characterisation of the key aroma compounds in commercial native cold-pressed rapeseed oil by means of the Sensomics approach

  • Original Paper
  • Published:
European Food Research and Technology Aims and scope Submit manuscript

Abstract

A systematic approach for the characterisation of the most important aroma-active compounds in a commercial native cold-pressed rapeseed oil on the basis of the Molecular Sensory Science Concept, consisting of aroma extract dilution analysis (AEDA), identification experiments by gas chromatography–olfactometry and gas chromatography–mass spectrometry, stable isotope dilution analysis (SIDA), calculation of odour activity values (OAVs), and recombination experiments, was performed. Forty-nine aroma-active compounds, isolated by thin layer distillation, were identified with a flavour dilution factor ≥8 during AEDA and headspace AEDA, 23 thereof reported in native cold-pressed rapeseed oil for the first time. Twenty-three odorants were quantitated via SIDA revealing for 11 compounds concentrations above their respective odour thresholds. Thereby, 2-isopropyl-3-methoxypyrazine, dimethyl trisulphide, dimethyl sulphide, butanoic acid, and octanal showed the highest OAVs (ratio of concentration divided by respective odour threshold). For data validation, a reconstitution model was prepared by mixing the odorants in their natural occurring concentrations in an odourless oily matrix showing an aroma profile very similar to the profile of the original rapeseed oil, confirming that all key aroma compounds were identified and quantitated successfully.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. Abdellatif AMM, Vles RO (1970) Pathological effects of dietary rapeseed oil in rats. Nutr Metab Cardiovasc 12:285–295

    Article  CAS  Google Scholar 

  2. Snyder JM (1995) Volatile analysis of oxidized oils by a direct supercritical fluid extraction method. J Food Lipids 2:25–33

    Article  CAS  Google Scholar 

  3. Park D, Maga JA, Johnson DL, Morini G (1995) Major volatiles in toasted canola oil. J Food Lipids 2:249–258

    Article  CAS  Google Scholar 

  4. Dunkel A, Steinhaus M, Kotthoff M, Nowak B, Krautwurst D, Schieberle P, Hofmann T (2014) Nature’s chemical signatures in human olfaction: a foodborne perspective for future biotechnology. Angew Chem Int Ed 53:7124–7143

    Article  CAS  Google Scholar 

  5. Jeleń HH, Obuchowska M, Zawirska-Wojtasiak R, Wąsowicz E (2000) Headspace solid-phase microextraction use for the characterization of volatile compounds in vegetable oils of different sensory quality. J Agric Food Chem 48:2360–2367

    Article  Google Scholar 

  6. Jeleń HH, Mildner-Szkudlarz S, Jasińska I, Wąsowicz E (2007) A headspace-SPME-MS method for monitoring rapeseed oil autoxidation. J Am Oil Chem Soc 84:509–517

    Article  Google Scholar 

  7. 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 52:5207–5214

    Article  CAS  Google Scholar 

  8. Tynek M, Pawlowicz R, Gromadzka J, Tylingo R, Wardencki W, Karlovits G (2012) Virgin rapeseed oils obtained from different rape varieties by cold pressed method-their characteristics, properties, and differences. Eur J Lipid Sci Technol 114:357–366

    Article  CAS  Google Scholar 

  9. Schieberle P, Hofmann T (2012) Mapping the combinatorial code of food flavors by means of molecular sensory science approach. In: Jelen H (ed) Food flavors. Chemical, sensory and technological properties. Chemical and functional properties of food components series. CRC Press, Boca Raton, FL, pp 413–438

    Google Scholar 

  10. Pollner G, Schieberle P (2016) Characterization of the key odorants in commercial cold-pressed oils from unpeeled and peeled rapeseeds by the Sensomics approach. J Agric Food Chem 64:627–636

    Article  CAS  Google Scholar 

  11. Ullrich F, Grosch W (1988) Identification of the most intense odor compounds formed during autoxidation of methyl linolenate at room temperature. J Am Oil Chem Soc 65:1313–1317

    Article  CAS  Google Scholar 

  12. Schieberle P, Grosch W (1991) Potent odorants of the wheat bread crumb. Differences from the crust and effect of a longer dough fermentation. Z Lebensm Unters Forsch 192:130–135

    Article  CAS  Google Scholar 

  13. Dollmann B, Wichmann D, Schmitt A, Koehler H, Schreier P (1996) Quantitative analysis of 2-aminoacetophenone in off-flavored wines by stable isotope dilution assay. J AOAC Int 79:583–586

    CAS  Google Scholar 

  14. Schieberle P, Gassenmeier K, Guth H, Sen A, Grosch W (1993) Character impact odor compounds of different kinds of butter. Food Sci Technol 26:347–356

    CAS  Google Scholar 

  15. Milo C, Grosch W (1996) Changes in the odorants of boiled salmon and cod as affected by the storage of the raw material. J Agric Food Chem 44:2366–2371

    Article  CAS  Google Scholar 

  16. Guth H, Grosch W (1993) Quantitation of potent odorants of virgin olive oil by stable-isotope dilution assays. J Am Oil Chem Soc 70:513–518

    Article  CAS  Google Scholar 

  17. Guth H, Grosch W (1993) Odorants of extrusion products of oat meal-changes during storage. Z Lebensm Unters Forsch 196:22–28 (in German)

    Article  CAS  Google Scholar 

  18. Blank I, Schieberle P, Grosch W (1993) Quantification of the flavor compounds 3-hydroxy-4,5-dimethyl-2(5H)-furanone and 5-ethyl-3-hydroxy-4-methyl-2(5H)-furanone by a stable isotope dilution assay. In: Schreier P, Winterhalter P (eds) Progress in flavour precursor studies. Allured Publishing, Carol Stream, pp 103–109

    Google Scholar 

  19. Sen A, Schieberle P, Grosch W (1991) Quantitative determination of 2,5-dimethyl-4-hydroxy-3(2H)-furanone and its methyl ether using a stable isotope dilution assay. Lebensm Wiss Technol 24:364–369

    CAS  Google Scholar 

  20. Semmelroch P, Grosch W (1996) Studies on character impact odorants of coffee brews. J Agric Food Chem 44:537–543

    Article  CAS  Google Scholar 

  21. Schieberle P, Grosch W (1992) Changes in the concentrations of potent crust odourants during storage of white bread. Flavour Fragr J 7:213–218

    Article  CAS  Google Scholar 

  22. Guth H, Grosch W (1994) Identification of the character impact odorants of stewed beef juice by instrumental analyses and sensory studies. J Agric Food Chem 42:2862–2866

    Article  CAS  Google Scholar 

  23. Poisson L, Schieberle P (2008) Characterization of the key aroma compounds in an American Bourbon whisky by quantitative measurements, aroma recombination, and omission studies. J Agric Food Chem 56:5820–5826

    Article  CAS  Google Scholar 

  24. Guth H, Grosch W (1990) Deterioration of soya-bean oil: quantification of primary flavor compounds using a stable isotope dilution assay. Lebensm Wiss Technol 23:513–522

    CAS  Google Scholar 

  25. Blekas G, Guth H (1995) Evaluation and quantification of potent odorants of Greek virgin olive oils. Dev Food Sci 37:419–427

    Article  Google Scholar 

  26. Kubickova J, Grosch W (1998) Quantification of potent odorants in Camembert cheese and calculation of their odor activity values. Int Dairy J 8:17–23

    Article  CAS  Google Scholar 

  27. Gassenmeier K, Schieberle P (1995) Potent aromatic compounds in the crumb of wheat bread (French-type)—influence of pre-ferments and studies on the formation of key odorants during dough processing. Z Lebensm Unters Forsch 201:241–248

    Article  CAS  Google Scholar 

  28. Billet R (1992) Performance of thin-film distillation and its application. Sep Technol 2:183–191

    Article  CAS  Google Scholar 

  29. Engel W, Bahr W, Schieberle P (1999) Solvent assisted flavour evaporation—a new and versatile technique for the careful and direct isolation of aroma compounds from complex food matrices. Eur Food Res Technol 209:237–241

    Article  CAS  Google Scholar 

  30. Bemelmans JMH (1979) Review of isolation and concentration techniques. In: Land DG, Nursten HE (eds) Progress in flavour research. Applied Science Publishers, London, pp 79–98

    Google Scholar 

  31. Esterbauer H (1968) Autoxidation of methyllinoleate in water III: chromatographic separation of water-soluble reaction products. Fett Wiss Technol 70:1–4 (in German)

    CAS  Google Scholar 

  32. Van den Dool H, Kratz PD (1963) A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography. J Chromatogr 11:463–471

    Article  Google Scholar 

  33. Matheis K, Granvogl M, Schieberle P (2016) Quantitation and enantiomeric ratios of aroma compounds formed by an Ehrlich degradation of l-isoleucine in fermented foods. J Agric Food Chem 64:646–652

    Article  CAS  Google Scholar 

  34. Czerny M, Christlbauer Ma , Christlbauer Mo, Fischer A, Granvogl M, Hammer M, Hartl C, Hernandez NM, Schieberle P (2008) Re-investigation on odour thresholds of key food aroma compounds and development of an aroma language based on odour qualities of defined aqueous odorant solutions. Eur Food Res Technol 228:265–273

    Article  CAS  Google Scholar 

  35. Murray KE, Shipton J, Whitfield FB (1970) 2-Methoxypryazines and the flavor of green peas (Pisum sativum). Chem Ind 4:897–898

    Google Scholar 

  36. Buttery RG, Seifert RM, Guadagni DG, Ling LC (1969) Characterization of some volatile constituents of bell peppers. J Agric Food Chem 17:1322–1327

    Article  CAS  Google Scholar 

  37. Bramwell AF, Burrell JWK, Riezebos G (1969) Characterization of pyrazines in galbanum oil. Tetrahedron Lett 37:3215–3216

    Article  Google Scholar 

  38. Hashizume K, Tozawa K, Hiraga Y, Aramaki I (2001) Purification and characterization of a O-methyltransferase capable of methylating 2-hydroxy-3-alkylpyrazine from Vitis vinifera L. (cv. Cabernet Sauvignon). Biosci Biotechnol Biochem 65:2213–2219

    Article  CAS  Google Scholar 

  39. Nursten HE, Sheen MR (1974) Volatile flavor components of cooked potato. J Sci Food Agric 25:643–663

    Article  CAS  Google Scholar 

  40. Murray KE, Whitfield FB (1975) Occurrence of 3-alkyl-2-methoxypyrazines in raw vegetables. J Sci Food Agric 26:973–986

    Article  CAS  Google Scholar 

  41. Gallois A, Kergomard A, Adda J (1988) Study of the biosynthesis of 3-isopropyl-2-methoxypyrazine produced by Pseudomonas taetrolens. Food Chem 28:299–309

    Article  CAS  Google Scholar 

  42. Belitz H-D, Grosch W, Schieberle P (2001) In: Food chemistry, 6th edn. Springer, Berlin, pp 370–371 (in German)

    Google Scholar 

  43. Scherb J, Kreissl J, Haupt S, Schieberle P (2009) Quantitation of S-methylmethionine in raw vegetables and green malt by a stable isotope dilution assay using LC-MS/MS: comparison with dimethyl sulfide formation after heat treatment. J Agric Food Chem 57:9091–9096

    Article  CAS  Google Scholar 

  44. Ehrlich F (1907) The chemical processes accompanying yeast fermentation. Ber Dtsch Chem Ges 40:1027–1047 (in German)

    Article  CAS  Google Scholar 

  45. Neubauer O, Fromherz K (1911) The decomposition of amino acids in yeast fermentation. Z Physiol Chem 70:326–350 (in German)

    Article  CAS  Google Scholar 

  46. Pham TT, Guichard E, Schlich P, Charpentier C (1995) Optimal conditions for the formation of sotolon from α-ketobutyric acid in the French “Vin Jaune”. J Agric Food Chem 43:2616–2619

    Article  Google Scholar 

  47. Pons A, Lavigne V, Landais Y, Darriet P, Dubourdieu D (2010) Identification of a sotolon pathway in dry white wines. J Agric Food Chem 58:7273–7279

    Article  CAS  Google Scholar 

  48. Blank I, Lin J, Fumeaux R, Welti DH, Fay LB (1996) Formation of 3-hydroxy-4,5-dimethyl-2(5H)-furanone (sotolone) from 4-hydroxy-l-isoleucine and 3-amino-4,5-dimethyl-3,4-dihydro-2(5H)-furanone. J Agric Food Chem 44:1851–1856

    Article  CAS  Google Scholar 

  49. Reiners J, Grosch W (1998) Odorants of virgin olive oils with different flavor profiles. J Agric Food Chem 46:2754–2763

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This IGF Project of the FEI was supported via AiF within the programme for promoting the Industrial Collective Research (IGF) of the German Ministry of Economics and Energy (BMWi), based on a resolution of the German Parliament.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Michael Granvogl.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Compliance with ethics requirements

The authors, Katrin Matheis and Michael Granvogl, hereby confirm that this manuscript follows the COPE guidelines and has not already been published nor is it under consideration for publication elsewhere.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Matheis, K., Granvogl, M. Characterisation of the key aroma compounds in commercial native cold-pressed rapeseed oil by means of the Sensomics approach. Eur Food Res Technol 242, 1565–1575 (2016). https://doi.org/10.1007/s00217-016-2657-5

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00217-016-2657-5

Keywords

Navigation