Skip to main content
SpringerLink
Log in

Combined Short-Path Distillation and Solvent-Assisted Crystallization of Beef Fatty Acid Methyl Esters

  • Original Paper
  • Published:
Journal of the American Oil Chemists' Society

Abstract

Solvent-assisted crystallization has previously been employed to remove long-chain saturated fatty acids (≥ 18 carbons) from animal fat to improve its cold temperature biofuel properties. The same technology can be used for removing long-chain saturated fatty acids (SFA) from animal fats for human consumption, but SFA remaining (i.e., 14:0 and 16:0) are more atherogenic than longer chain SFA. In the present study, an easy and efficient method was developed using short-path distillation prior to solvent-assisted crystallization for the more complete removal of SFA from beef tallow, and for the first time reports the distillation and crystallization behavior of polyunsaturated fatty acid biohydrogenation products (PUFA-BHP). Shorter chain SFA methyl esters (i.e., 14:0 and 16:0) were efficiently removed at 90 °C, 9.3 Pa, with a rotor speed of 70 rpm and either two cycles of distillation at 90 drops/min or three cycles at 110 drops/min. Stearic acid (18:0) was then effectively removed by crystallization at −20 °C using a sample to methanol ratio of 1:10. The remaining fraction enriched with PUFA-BHP (i.e., rumenic acid, c9,t11-18:2, and its precursor vaccenic acid, t11-18:1) have potential use in disease model (i.e., cell culture and animal) studies to help further elucidate their bioactivity and mode of action, and may in the future have functional food or nutraceutical potential.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1

Similar content being viewed by others

Abbreviations

ALA:

α Linolenic acid

BHP:

Biohydrogenation products

CLA:

Conjugated linoleic acids

CLnA:

Conjugated linolenic acids

FAME:

Fatty acid methyl esters

LA:

Linoleic acid

PUFA:

Polyunsaturated fatty acid

References

  1. Mozaffarian D, Micha R, Wallace S (2010) Effects on coronary heart disease of increasing polyunsaturated fat in place of saturated fat: a systematic review and meta-analysis of randomized controlled trials. PLoS Med 7:e1000252

    Article  Google Scholar 

  2. Strohmeier K, Schober S, Mittelbach M (2014) Solvent-assisted crystallization of fatty acid alkyl esters from animal fat. J Amer Oil Chem Soc 91:1217–1224

    Article  CAS  Google Scholar 

  3. Simopoulos AP (1999) New products from the agri-food industry: the return of n-3 fatty acids into the food supply. Lipids 34(Suppl):S297–S301

    Article  CAS  Google Scholar 

  4. Vahmani P, Mapiye C, Prieto N, Rolland DC, McAllister TA, Aalhus JL, Dugan MER (2015) The scope for manipulating the polyunsaturated fatty acid content of beef: a review. J Anim Sci Biotech 6:29

    Article  Google Scholar 

  5. Jenkins TC, Wallace RJ, Moate PJ, Mosley EE (2008) Board invited review: recent advances in biohydrogenation of unsaturated fatty acids within the rumen microbial ecosystem. J Anim Sci 86:397–412

    Article  CAS  Google Scholar 

  6. Doreau M, Ferlay A (1994) Digestion and utilisation of fatty acids by ruminants. Anim Feed Sci Technol 45:379–396

    Article  CAS  Google Scholar 

  7. Vahmani P, Rolland D, McAllister T, Block H, Proctor S, Guan L, Prieto N, López-Campos Ó, Aalhus J, Dugan M (2017) Effects of feeding steers extruded flaxseed on its own before hay or mixed with hay on animal performance, carcass quality, and meat and hamburger fatty acid composition. Meat Sci 131:7–17

  8. Benjamin S, Prakasan P, Sreedharan S, Wright ADG, Spener F (2015) Pros and cons of CLA consumption: an insight from clinical evidences. Nutr Metab 12:4

    Article  CAS  Google Scholar 

  9. Field CJ, Blewett HH, Proctor S, Vine D (2009) Human health benefits of vaccenic acid. Appl Physiol Nutr Metab 34:979–991

    Article  CAS  Google Scholar 

  10. Vahmani P, Rolland DC, Gzyl KE, Dugan MER (2016) Non-conjugated cis/trans 18:2 in beef fat are mainly Δ-9 desaturation products of trans-18:1 isomers. Lipids 51:1427–1433

    Article  CAS  Google Scholar 

  11. Vahmani P, Meadus WJ, Turner TD, Duff P, Rolland DC, Mapiye C, Dugan ME (2015) Individual trans 18:1 isomers are metabolised differently and have distinct effects on lipogenesis in 3T3-L1 adipocytes. Lipids 50:195–204

    Article  CAS  Google Scholar 

  12. Vahmani P, Meadus WJ, Rolland DC, Duff P, Dugan MER (2016) Trans10, cis15 18:2 isolated from beef fat does not have the same anti-adipogenic properties as Trans10, cis12–18:2 in 3T3-L1 adipocytes. Lipids 51:1231–1239

    Article  CAS  Google Scholar 

  13. Grundy SM (1994) Influence of stearic acid on cholesterol metabolism relative to other long-chain fatty acids. Amer J Clin Nutr 60:986S–990S

    CAS  Google Scholar 

  14. Diane A, Borthwick F, Mapiye C, Vahmani P, David RC, Vine DF, Dugan MER, Proctor SD (2016) Beef fat enriched with polyunsaturated fatty acid biohydrogenation products improves insulin sensitivity without altering dyslipidemia in insulin resistant JCR:lA-cp rats. Lipids 51:821–831

    Article  CAS  Google Scholar 

  15. Kramer JK, Hernandez M, Cruz-Hernandez C, Kraft J, Dugan ME (2008) Combining results of two GC separations partly achieves determination of all cis and trans 16: 1, 18: 1, 18: 2 and 18: 3 except CLA isomers of milk fat as demonstrated using Ag-ion SPE fractionation. Lipids 43:259–273

    Article  CAS  Google Scholar 

  16. Cruz-Hernandez C, Deng Z, Zhou J, Hill AR, Yurawecz MP, Delmonte P, Mossoba MM, Dugan ME, Kramer JK (2004) Methods for analysis of conjugated linoleic acids and trans-18:1 isomers in dairy fats by using a combination of gas chromatography, silver-ion thin-layer chromatography/gas chromatography, and silver-ion liquid chromatography. J AOAC Int 87:545–562

    CAS  Google Scholar 

  17. Gómez-Cortés P, Tyburczy C, Brenna JT, Juárez M, de la Fuente MA (2009) Characterization of cis-9 trans-11 trans-15 C18:3 in milk fat by GC and covalent adduct chemical ionization tandem MS. J Lipid Res 50:2412–2420

    Article  Google Scholar 

  18. Cermak SC, Evangelista RL, Kenar JA (2012) Distillation of natural fatty acids and their chemical derivatives. In: Zereshki S (ed) Distillation-advances from modeling to applications. InTech, Rijeka

  19. Vázquez L, Akoh CC (2010) Fractionation of short and medium chain fatty acid ethyl esters from a blend of oils via ethanolysis and short-path distillation. J Amer Oil Chem Soc 87:917–928

    Article  Google Scholar 

  20. Siurana A, Calsamiglia S (2016) A metaanalysis of feeding strategies to increase the content of conjugated linoleic acid (CLA) in dairy cattle milk and the impact on daily human consumption. Anim Feed Sci Technol 217:13–26

    Article  CAS  Google Scholar 

  21. Turpeinen AM, Mutanen M, Aro A, Salminen I, Basu S, Palmquist DL, Griinari JM (2002) Bioconversion of vaccenic acid to conjugated linoleic acid in humans. Am J Clin Nutr 76:504–510

    CAS  Google Scholar 

  22. Hennessy AA, Ross RP, Devery R, Stanton C (2011) The health promoting properties of the conjugated isomers of α-linolenic acid. Lipids 46:105–119

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors gratefully acknowledge funding support from the Agriculture and Agri-Food Canada Peer Review Program for project J-001396: Larger scale fractionation of novel polyunsaturated fatty acid biohydrogenation products from beef fat and testing their bioactivity and mode of action.

Author information

Authors and Affiliations

  1. Lacombe Research Centre, Agriculture and Agri-Food Canada, Lacombe, AB, T4L 1W1, Canada

    Michael E. R. Dugan, Katherine E. Gzyl, David C. Rolland & Payam Vahmani

Authors
  1. Michael E. R. Dugan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Katherine E. Gzyl
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. David C. Rolland
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Payam Vahmani
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Michael E. R. Dugan.

Ethics declarations

Conflict of interest

The authors declare no conflict of interest.

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Dugan, M.E.R., Gzyl, K.E., Rolland, D.C. et al. Combined Short-Path Distillation and Solvent-Assisted Crystallization of Beef Fatty Acid Methyl Esters. J Am Oil Chem Soc 94, 1503–1508 (2017). https://doi.org/10.1007/s11746-017-3054-3

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11746-017-3054-3

Keywords

Search

Navigation