Skip to main content
SpringerLink
Log in

The synthesis of 2-(2-pentenyl) furans and their relationship to the reversion flavor of soybean oil

  • Technical
  • Published:
Journal of the American Oil Chemists’ Society

Abstract

cis- andtrans-2-(2-Pentenyl)furans were synthesized and structures were confirmed by infrared, nuclear magnetic resonance and mass spectroscopy. Preliminary organoleptic evaluation of oil solutions of the compounds indicated that thecis isomer had a flavor threshold of ca. 0.25 ppm. with odor and flavor descriptions of beany, grassy and buttery at 0.50 ppm; and that thetrans isomer had a flavor threshold of ca. 0.50 ppm with odor and flavor descriptions of beany, grassy and buttery at 1 ppm and strong painty and metallic at 4 ppm. These compounds, if found in soybean oil through the autoxidation of linolenate, may contribute to the characteristic reversion flavor.

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

Similar content being viewed by others

References

  1. Ho, C.T., M.S. Smagula, and S.S. Chang, JAOCS 55:233 (1978).

    Article  CAS  Google Scholar 

  2. Chang, S.S., T.H. Smouse, R.G. Krishnamurthy, B.D. Mookherjee, and B.R. Reddy, Chem. Ind. 1926 (1966).

  3. Winterfeldt, E., Synthesis 617 (1975).

  4. Hoyte, R.M., and D.B. Denney, J. Org. Chem. 39:2607 (1974).

    Article  CAS  Google Scholar 

  5. Ramanthan, V., and R. Levine, J. Org. Chem. 27:1216 (1962).

    Article  Google Scholar 

  6. Shono, T., Y. Matsumura, H. Hamaguchi, and K. Nakamura, Tetrahedron Lett. 1249 (1976).

Download references

Author information

Authors and Affiliations

  1. Department of Food Science, Cook College, Rutgers, The State University, 08903, New Brunswick, NJ

    M. S. Smagula, Chi-Tang Ho & S. S. Chang

Authors
  1. M. S. Smagula
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Chi-Tang Ho
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. S. Chang
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Paper of the Journal Series, New Jersey Agricultural Experiment Station, Cook College, Rutgers, The State University of New Jersey.

About this article

Cite this article

Smagula, M.S., Ho, CT. & Chang, S.S. The synthesis of 2-(2-pentenyl) furans and their relationship to the reversion flavor of soybean oil. J Am Oil Chem Soc 56, 516–519 (1979). https://doi.org/10.1007/BF02680192

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02680192

Keywords

Search

Navigation