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Chemistry of Formation and Prevention of Undesirable Reversion Grassy Flavor in Soybean Oil

History and Statistics of Soybean Oil. Soybean oil produced undesirable reversion grassy flavor, which made it less acceptable or unacceptable to consumers and food manufacturers until 1990s. Soybean oil could not effectively compete with corn oil, cottonseed oil or sunflower oil due to reversion

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Chemistry of Formation and Prevention of Undesirable Reversion Grassy Flavor in Soybean Oil

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    1. Chemistry of Formation and Prevention of Undesirable Reversion Grassy Flavor in Soybean Oil David B. Min  Department of Food Science and Technology The Ohio State University Columbus, Ohio, USA

    2. History and Statistics of Soybean Oil

    3. Compositions of Vegetable Oils

    4. Soybean Oil Reversion Grassy Flavor The return of good deodorized soybean oil flavor to the undesirable crude oil grassy flavor within a very short period of time is termed “Reversion Grassy Flavor”. The development of a characteristic grassy flavor in deodorized soybean oil is commonly called reversion flavor.

    5. Reversion grassy flavor has been an important classical problem of soybean oil industry and the most extensively studied research subject in oils and foods since 1930. Reversion grassy flavor makes soybean oil less acceptable or unacceptable to consumers and food manufacturers. Soybean Oil Reversion Grassy Flavor

    6. American Soybean Oil Processors Association

    7. K. S. Markley’s Review on Soybean Oil Reversion Grassy Flavor in 1951 Reversion flavor is a characteristic property in soybean oil. Reversion flavor occurs even at peroxide value of 2. Linolenic acid may be responsible for reversion flavor. Antioxidants were not effective in reversion flavor. None of the physical and chemical methods was effective to prevent soybean oil reversion flavor.

    8. E. N. Frankel’s Review on Soybean Oil Reversion Flavor in 1980 Linolenic acid, phospholipids, unsaponifiable compounds, and light may be responsible for reversion flavor. Antioxidants did not slow down or retard the reversion flavor of soybean oil. K. S. Markley’s review on reversion flavor of soybean oil in 1951.

    9. T. H. Smouse’s Review on Soybean Oil Reversion Grassy Flavor in 1985 Reversion flavor is observed in soybean oil in a few hours of storage under light. 2-Pentenyl furan could be formed from linolenic acid. 2-Pentenyl furan was synthesized from tetrahydrofuran and n-butyl lithium. He reported “Although much has been learned since 1930s, we do not know how to make soybean oil that will not produce reversion grassy flavor”.

    10. Proposed Theories on Reversion Grassy Flavor Formation

    11. What is the Next Approach to Solve Soybean Oil Reversion Grassy Flavor?

    12. Soybean Oil Reversion Grassy Flavor Literatures from 1932 to 1985 Reversion flavor is observed in soybean oil in a few hours of storage. Activation energy for reversion flavor reaction is very low. Antioxidants were not effective in reversion flavor. Reversion flavor is not free radical reaction. Soybean oil with reversion flavor has peroxide value. Reversion flavor formation requires oxygen. Ordinary triplet oxygen requires high activation energy to react with soybean oil. Triplet oxygen reacts with soybean oil by free radical reaction.

    13. 1772 Scheele & Priestley: Discovered Triplet Oxygen   1811 Avogadro: Triplet Oxygen is a Diatomic Molecule   1848 Faraday: Triplet Oxygen is a Paramagnetic Molecule   1934 Herzberg: Observation of Singlet Oxygen   1969 Foote & Wexler: Rediscovered Singlet Oxygen  

    14. Food Oxidation Triplet oxygen oxidation Singlet oxygen oxidation

    21. Soybean Oil Reversion Grassy Flavor Formation and Singlet Oxygen

    22. Singlet Oxygen Formation in Foods

    28. Soybean Oil Purification by Chromatography

    29. Identified Compounds in Soybean Oil

    30. Effect of Chlorophyll on 2-Pentenylfuran and Reversion Grassy Flavor in Soybean Oil

    31. Mass Spectrum of 2-Pentenylfuran

    32. 2-Pentenylfuran from Linolenic Acid by 1O2

    34. 2-Pentenylfuran Formation from Linolenic Acid of Soybean Oil by 1O2

    36. Carotenoids

    38. Effects of ?-apo-8’-Carotenal, ?-Carotene or Canthaxanthin on 2-Pentenylfuran of Soybean Oil with 3 ppm Chlorophyll

    40. Production of Reversion Grassy Flavor Free Soybean Oil

    41. Conclusion Food industry has been producing reversion grassy flavor free soybean oil for foods very successfully and economically by removing chlorophyll using effective bleaching materials without extra costs. Soybean oil has now become the most important edible oil as food and food ingredient in the world due to the successful and noble research for the prevention of the reversion grassy flavor .

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