Source: OHIO STATE UNIVERSITY submitted to NRP
MECHANBISM AND PREVENTION OF REVERSION FLAVOR FORMATION IN SOYBEAN OIL
Sponsoring Institution
National Institute of Food and Agriculture
Project Status
COMPLETE
Funding Source
Reporting Frequency
Annual
Accession No.
0188088
Grant No.
(N/A)
Cumulative Award Amt.
(N/A)
Proposal No.
(N/A)
Multistate No.
(N/A)
Project Start Date
Feb 1, 2001
Project End Date
Sep 30, 2004
Grant Year
(N/A)
Program Code
[(N/A)]- (N/A)
Recipient Organization
OHIO STATE UNIVERSITY
1680 MADISON AVENUE
WOOSTER,OH 44691
Performing Department
FOOD SCIENCE AND TECHNOLOGY
Non Technical Summary
Reversion lowers the economic value of soybean oil To improve the flavor stability of soybean oil by minimizing the singlet oxygen formation.
Animal Health Component
25%
Research Effort Categories
Basic
50%
Applied
25%
Developmental
25%
Classification

Knowledge Area (KA)Subject of Investigation (SOI)Field of Science (FOS)Percent
5011820100040%
5011820200040%
5011844100010%
5011844200010%
Goals / Objectives
The objectives are to study (1) the mechanisms for 2-(1-pentenyl) furan and 2-(2-pentenyl) furan formation from linolenic acid of soybean oil and singlet oxygen, (2) the effects of chlorophyll contents on the formation of 2-(1-pentenyl) furan and 2-(2-pentenyl) furan, (3) the effects of light intensity on the formation of 2-(1-pentenyl) furan and 2-(2-pentenyl) furan (4) the relationship between the concentrations of 2-(1-pentenyl)furan and 2-(2-pentenyl)furan and reversion flavor, and (5) to prevent the formation of 2-(1-pentenyl)furan and 2-(2-pentenyl)furan in soybean oil by removing chlorophyll from soybean oil by proper and optimum refining processing.
Project Methods
Soybean Oils with Chlorophyll The samples of 0, 0.5, 1.0, 1.5, or 2.0ppm chlorophyll in purified soybean oil will be prepared by adding commercially available standard chlorophyll (King and Min, 1998). Fifteen ml of the samples will be placed in 30 ml serum bottles, sealed airtight with Teflon septa and aluminum caps (Supelco, Inc., Bellefontane, PA). Sample Storage Samples will be stored under dark and light storage. A mirrored, wooden box (70 cm x 50 cm x 60 cm) lighted with a 200 watt tungsten bulb at an intensity of 4,000 lux, as will be will be used for light storage of the samples to study the effects of light on the formation of reversion falvor. The samples will be placed on a motor-driven plastic disk (Talboys Engineering Co., Emerson, NJ) rotating at 60 rpm for uniform light exposure (King and Min, 1998). The temperature of the light box and of the dark storage will be 45oC. The headspace of each sample will be analyzed at 1, 2, 4, and 8 hours for oxygen content after equilibrium to 20oC in a water bath for 10 to 15 minutes. Gas chromatographic headspace oxygen analysis will be used to determine the extent of oxidation in each of the samples (King and Min, 1998; Guth and Grosch, 1990). Synthesis of 2-Pentenylfurans The 2-(1-pentenyl) furan will be synthesized according to the method of Ho et al. (1978) and 2-(2-Pentenyl) furan by the method of Smagula et al. (1979). The syntheses require n-butyl lithium; anhydrous ether; anhydrous sodium sulfate; a three-necked, round-bottomed flask with a magnetic stirrer; a reflux condenser; a pressure equalizing dropping funnel; vacuum filtration, and rotary evaporation. Infrared spectroscopy, nuclear magnetic resonance spectroscopy, and mass spectrometry will be used to confirm the structures of the 2-pentenylfurans.

Progress 02/01/01 to 09/30/04

Outputs
Soybean oil containing 0, 1, 5 or 10 ppm chlorophyll was stored under light at 4, 20 and 40 C for 7 days to compared the effects of light exposure, chlorophyll concentration and storage temperature on the production of volatile compounds in soybean oil. Volatile compounds were analyzed by solid phase microextraction and gas chromatography. The amounts of pentane, pentanal, 1-pentenol, 2-pentenal, hexane, 2-hexene, 2-hexanal, heptanal, 2-heptenal, 2-pentyl furan, 2,4-heptadienal, 2,4-nonadienal, 1-octen-3-ol and 2-octenal were significantly affected by chlorophyll concentration within 1 to 2 days of light exposure. Relative to the triplet oxygen product hexanal, the singlet oxygen product 2-heptenal increased in quantity rapidly in 5 ppm or 10 ppm chlorophyll soybean oil when exposed to light even at 4 C. The presence of 5 to 10 ppm chlorophyll was the most significant factor to the amount of volatile compounds during the first 2 days of light exposure; however, storage temperature was the most significant factor after 2 days of light exposure. 2-Pentylfuran and isomers of 2-pentenylfuran are known to be mainly responsible for the undesirable reversion flavor of soybean oil. Solid phase microextraction-gas chromatography-mass spectrometry was used to isolate, separate, and identify 2-pentylfuran and isomers of 2-pentenylfuran from soybean oil containing 5 ppm chlorophyll in a gas-tight sample bottle during oxidation under light. Both 2-pentylfuran and isomers of 2-pentenylfuran increase as light exposure time and added chlorophyll increased. The compounds were neither formed in the oil containing 5 ppm chlorophyll under dark nor in the chlorophyll-free soybean oil under light. The singlet oxygen oxidation mechanism for the formation of 2-pentylfuran from linoleic acid and isomers of 2-pentenylfuran from linolenic acid are proposed. Removal of chlorophyll will reduce reversion flavor formation.

Impacts
This simple, easy to use. and rapid and sensitive analytical flavor analysis method will greatly improve the analysis of flavor qualities of foods

Publications

  • David B. Min. 2002. Chemistry of Singlet and Triplet Oxygen Oxidation in Foods. Food Science and Industry, Vol. 35 No. 2, 57-63.
  • King. J. M. and D. B. Min, 2002. Riboflavin Photosensitized Singlet Oxygen Oxidation Products of Vitamin D. J. Am. Oil Chem. Soc. 983-987
  • Min, David B., Amanda L. Callison, and Hyung Ok Lee. 2003. Singlet Oxygen Oxidation for 2-Pentylfuran and 2-Pentenylfuran Formation in Soybean Oil. J. Fd. Sci.1175-1178
  • Min, David B., and Eun Ok Choe. 2003. Effects of Singlet Oxygen Oxidation on the Flavor of Foods and Stability of Vitamins. J. Fd. Sci & Biotech.582-586
  • Ozcelik, B., J. H. Lee and D. B. Min. 2003. Scavenging Mechanism of 2, 2-Diphenyl-1-Picrylhydrazyl in Acetone and Soybean Oil. J. Am. Oil Chem. Soc.487-490
  • Lee, J. H., B. Ozcelik and D. B. Min. 2003. Electron Donation Mechanism of b-Carotene as a Free Radical Scavenger. J. Fd. Sci. 861-865
  • Bradley, D. and D. B. Min, 2003. Singlet Oxygen Detection in Skim Milk by Electron Spin Resonance Spectroscopy. J. Fd. Sci. 491-494
  • Min, S., Behroze S. Mistry, Hyung O. Lee, and David B. Min, 2003 Improvement of Oxidative and Emulsion Stability of Model Salad Dressing by Glucose Oxidase-Catalase, J. Fd Sci. 1272-1275
  • Boff, J. M. and David B. Min. 2003. Effects of Chlorophyll Content and Temperature on the Production of Volatile Compounds in Soybean Oil exposed to Light, Edward F. Hayes Graduate Research Forum. The Ohio State University, 15-27


Progress 01/01/03 to 12/31/03

Outputs
Analysis of volatile compounds and headspace oxygen and carbon dioxide in full fat soy flour Soy flour can be a good protein source and used to improve the color, texture and water binding capacity in baked products. The flavor quality of soy flour very often determines the quality of final products. A sensitive and reproducible method is thus necessary to monitor the off-odor in soy flour. Seven g of full fat soy flour was put in a 50-mL serum bottle and sealed air-tightly with a Teflon-coated rubber septum and an aluminum cap. Samples were kept at -20 C dark, 60 C dark and 60 C light for 10 days. Volatile compounds were isolated by 100 micron meter PDMS for 30 min at 60 C and analyzed in a gas chromatograph (GC) and GC-mass selective detector. The headspace oxygen and carbon dioxide were determined every other day for 10 days by GC with a thermal conductivity detector. The coefficient of variation of SPME analysis on the soy flour was within 5 % in total peak area. As storage time increased from 0 to 10 days, total peak area of 60 C dark and light samples increased by 220 and 250%, respectively, comparing to that of -20 C dark samples. Headspace oxygen of 60 C dark and light samples decreased by 4 and 5%, respectively, during storage due to lipid oxidation. On the other hand, headspace carbon dioxide increased by 2.6 and 2.3%, respectively, due to the non-enzymatic browning reaction. Forty eight volatile compounds were identified and 9 furan and pyrazine compounds were detected only in 60 C dark and light samples. SPME was a reproducible and sensitive method to detect volatile compounds in solid matrix food.

Impacts
This simple, easy to use. and rapid and sensitive analytical flavor analysis method will greatly improve the analysis of flavor qualities of foods

Publications

  • Kim, G., J. H. Lee, and D. B. Min. 2003. Formation Mechanism and Sensory Study of Light-Induced Volatile Compounds in Goat Cheese. J. Ag. Fd. Chem. 1405-1409
  • Lee. J. H. Kim, G., and D. B. Min.2003. Optimization of Solid Phase Microextraction Analysis on the Headspace Volatile Compounds in Parmesan Cheese. J. Ag. Fd. Chem. 1136-1140
  • Troung, T., T. Boff, D. B. Min, and T. Shellhammer. 2003. Effects of Carbon Dioxide in High Pressure Processing on Pectinmethylesterase in Single Strength Orange Juice. J. Fd. Sci. 3058-3062
  • Lee, J. H., J. H. Kang, and D. B. Min. 2003.Optimization of Solid Phase Microextraction For the Analysis of the Headspace Volatile Compounds in Kimchi, a Traditional Korean Fermented Vegetable Product. J. Fd. Sci. 844-848
  • Kang, J. H., J. H. Lee, and S. Min. 2003. Study of Enzymatic and Chemical Changes of Kimchi, a Traditional Korean Fermented Vegetable Product. J. Fd. Sci. 849-854
  • Boff, T., Troung, T., D. B. Min, and T. Shellhammer. 2003. Effect of Carbon Dioxide Assisted High Pressure Processing on Pectinmethylesterase and Chemical Changes in Single Strength Orange Juice During Storage. J. Fd. Sci. 1179-1184
  • Min, David B., Amanda L. Callison, and Hyung Ok Lee. 2003. Singlet Oxygen Oxidation for 2-Pentylfuran and 2-Pentenylfuran Formation in Soybean Oil. J. Fd. Sci.1175-1178
  • Min, D. B., and E. O. Choe. 2003. Effects of Singlet Oxygen Oxidation on the Flavor of Foods and Stability of Vitamins. J. Fd. Sci & Biotech.582-586
  • Ozcelik, B., J. H. Lee and D. B. Min. 2003. Scavenging Mechanism of 2, 2-Diphenyl-1-Picrylhydrazyl in Acetone and Soybean Oil. J. Am. Oil Chem. Soc.487-490
  • Lee, J. H., B. Ozcelik and D. B. Min. 2003. Electron Donation Mechanism of b-Carotene as a Free Radical Scavenger. J. Fd. Sci. 861-865
  • Bradley, D. and D. B. Min, 2003. Singlet Oxygen Detection in Skim Milk by Electron Spin Resonance Spectroscopy. J. Fd. Sci. 491-494
  • Min, S., Behroze S. Mistry, Hyung O. Lee, and David B. Min, 2003 Improvement of Oxidative and Emulsion Stability of Model Salad Dressing by Glucose Oxidase-Catalase, J. Fd Sci. 1272-1275
  • Yoo, S. L., S. Min, Praksah, A. and David B. Min. 2003. Off-odor Study with gamma-irradiated Orange Juice Using Sensory and Volatile Compound Analyses. J. Fd. Sci. 1259-1264
  • Boff, J. M. and David B. Min. 2003Making Sense of Taste. Food Quality. 10: 36-39
  • Vittadini, E., J. H. Lee, N. G. Frega, David B. Min, and Y. Vodovotz. 2003. Differential Scanning Calorimetry Determination of Thermally Oxidized of Olive Oil, J. Am. Oil Chem. Soc. 533-537
  • Lee, J. Y., S. Min, E. O. Lee and D. B. Min. 2003. Volatile Compounds Formation in Soy Flour during Light Storage by Singlet Oxygen Oxidation. J. Fd. Sci. 1933-1937
  • Min, D. B. and Boff, J.M. 2003. Crude Fat Analyses in Food Analysis, S. Nielsen, ed. Kluwer Academic, Plenum Publishers, NY 113-128
  • Boff, J. M. and David B. Min. 2003 Effects of Chlorophyll Content and Temperature on the Production of Volatile Compounds in Soybean Oil exposed to Light, 2003 Edward F. Hayes Graduate Research Forum. The Ohio State University, 15-27


Progress 01/01/02 to 12/31/02

Outputs
Photosensitizers like chlorophyll exposed to light can generate singlet oxygen from ordinary triplet oxygen. 2-Pentylfuran, 2-heptenal, and 1-octene-3-ol can come from C10, C12, and C10 hydroperoxide of linoleic acid, respectively. The singlet oxygen oxidation mechanisms for 2-pentylfuran 2-heptenal, 1-octene-3-ol, and 2-octene-1-ol from linoleic acid were proposed.

Impacts
Oils with good flavor quality and stability cqan be produced by minimizing photosensitized oxidation

Publications

  • King. J. M. and D. B. Min, 2002. Riboflavin Photosensitized Singlet Oxygen Oxidation Products of Vitamin D. J.Am. Oil Chem. Soc. 983-987
  • Steenson, D. L., J. W. Lee, and D. B. Min, 2002. Solid Phase Liquid Extraction Analyses of Vegetable Oils. J. Food Sci. 71-76
  • Yang, W. T., J. H. Lee and D. B. Min, 2002. Quenching Mechanism and Kinetics of Tocopherol and Carotene on the Photosensitizing Effects of Synthetic Food Colorant FD&C Red No.3. J. Food Sci. 507-510
  • Min D. B. and J. M. Boff, 2002, Singlet Oxygen Oxidation of Foods, Comprehensive Reviews on Food Science and Safety 58-72
  • Chung, M. S, J. H. Lee and D. B. Min, 2002. Effects of Pseudomonas putrifaciens and Acinetobacter spp. on the Flavor Quality of Raw Ground Beef, J. Food Sci. 77-83.
  • Foley, D. M., K. Pickett, J. Varon, J. H. Lee, D. B. Min, F. Caporaso, and A. Prakash 2002, Pasteurization of Fresh Orange Juice using Gamma Irradiation: Microbilogical, Flavor, and Sensory Analyses. J. Food Sci.1495-1501.
  • David B. Min. 2002. Chemistry of Singlet and Triplet Oxygen Oxidation in Foods. Food Science and Industry, Vol. 35 No. 2, 57-63.
  • King. J. M. and D. B. Min, 2002. Riboflavin Photosensitized Singlet Oxygen Oxidation Products of Vitamin D. J. Am. Oil Chem. Soc. 983-987


Progress 01/01/01 to 12/31/01

Outputs
The volatile compounds for reversion flavor compounds have been isolated and separated by a combination of solid phase micro extraction and gas chromatography. The compounds have been identified as isomers of 2-pentenyl furan by a combination of gas chromatography and mass spectrometry

Impacts
Undesirable beany flavor compounds in soybean oil are formed by singlet oxygen oxidation of linoleic and linolenic acids in the presence of chlorophyll and light. The results provide an understanding of a problem that puzzled researchers for decades and stifled competitiveness of soybean oil. As a result, major food companies improved the oxidative stability of edible oils, frying oils and other foods, improving flavor, shelf life and economics of many products. Major oil processing companies in the U. S. monitor and remove the chlorophyll in soybean oil. Research to the improvement on the oxidative stability of soybean oil, one of the most important export commodities, has helped make soybean oil very competitive in foreign markets.

Publications

  • Steenson, D. L. and D. B. Min, 2001. Effects of carotene and Lycopene Thermal Degradation Products on the Oxidative Stability of Soybean Oil. J. Am. Oil Chem. 1153-1160
  • Ayhan, Z., H. W. Yeom, Q. H. Zhang, and D. B. Min, 2001. Flavor, Color and Vitamin C Retention of PEF Processed Orange Juice in Different Packaging Materials. J. Ag. Fd. Chem. 4707-4713
  • Yeom, H. W., C. B. Streaker, H. Q. Zhang and D. B. Min, 2001. Effects of Pulsed Fields on the Quality of Orange Juice and Comparison with Heat Pasteurization. J. Ag. Fd. Chem. (48) 4597-4603