A systematic characterization of the reversion flavor of soybean oil View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

1967-08

AUTHORS

Thomas H. Smouse, Stephen S. Chang

ABSTRACT

The volatile flavor compounds in a reverted soybean oil with a peroxide number of 4.3 meq/kg were isolated by a semicontinuous counter-current vacuum steam-distillation process, fractionated by repeated gas chromatography, and identified by infrared and mass spectrometry. A total of 71 compounds were identified, which included 19 acids, 39 nonacidic compounds, and 13 tentatively identified compounds. The acids consisted of eight normal saturated acids, nine α,β-unsaturated acids, a branch-chain acid, one hydroxy acid, two keto acids, three lactones, and one aromatic acid. The nonacidic compounds consisted of two esters, eight normal saturated aldehydes, two branched-chain aldehydes, five 2-enals, three dienals, eight ketones, eight alcohols, six hydrocarbons, and four aromatic compounds.The mechanism of formation of the identified compounds indicated that they were mostly primary or secondary autoxidation products of the hydroperoxides of the unsaturated fatty esters. Since many of the identified compounds were produced from oleic and linoleic acids, it is doubtful that linolenic acid was solely responsible for the reversion flavor.Of the compounds identified two are of unusual interest. They are 1-decyne and 2-pentyl furan. The former is the first acetylenic compound reported as the autoxidation products of unsaturated fatty esters which contained only double bonds. The latter imparts to an oil at concentrations of 5–10 ppm a beany and grassy flavor reminiscent of that of a reverted soybean oil. Since this compound is postulated as being produced by the autoxidation of linolenic acid, it is suggested that the presence of linolenic acid catalyzes the autoxidation of linoleic acid and possibly alters the decomposition pattern of its hydroperoxides. More... »

PAGES

509-514

References to SciGraph publications

  • 1948-04. Flavor reversion in soybean oil. IV. Isolation of reversion compounds in soybean oil in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1953-06. The volatile decomposition products and the organoleptic characteristics of the oxidative polymers of ethyl linoleate in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1946-12. Flavor reversion in soybean oil in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1949-08. The flavor problem of soybean oil. V. Some considerations in the use of metal scavengers in commercial operations in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1967-02. Chemical reactions involved in the deep fat frying of foods. II. Identification of acidic volatile decomposition products of corn oil in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1966-04. Chemical reactions involved in the catalytic hydrogenation of oils. III. Further identification of volatile by-products in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1961-01. Isolation of two pairs of isomeric 2,4-alkadienals from soybean oil-reversion flavor concentrate in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1961-01. 3-cis-hexenal, the “Green” reversion flavor of soybean oil in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1962-10. 1-Octen-3-ol and its relation to other oxidative cleavage products from esters of linoleic acid in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1960-09. Effect of autoxidation prior to deodorization on oxidative and flavor stability of soybean oil in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1952-08. Variations in the chemical, physical, and organoleptic properties of soybean oil hydrogenated under widely varying conditions in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1949-08. Flavor reversion in hydrogenated soybean oil. I. The effect of boudle-degumming. II. The effect of unsaponifiable matter in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1961-12. A new technique for the isolation of flavor components from fats and oils in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1941-05. The stability of vegetable oils IV. Flavor reversion in soybean oil in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1954-08. The relationship between the oxidative polymers of soybean oil and flavor reversion in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1952-09. Volatile cleavage products of autoxidized soybean oil in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1953-08. Volatile decomposition products of the oxidative polymers of ethyl linolenate in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1962-07. Soybean unsaponifiables: Chromatographic separations and characterization in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1957-12. Determination of the extent of oxidation of fats in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1961-12. Characterization of the reversion flavor of soybean oil in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1950-10. Flavor reversion in soybean oil. VI. Isolation and identification of reversion compounds in unhardened soybean oil in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • Identifiers

    URI

    http://scigraph.springernature.com/pub.10.1007/bf02908549

    DOI

    http://dx.doi.org/10.1007/bf02908549

    DIMENSIONS

    https://app.dimensions.ai/details/publication/pub.1013097365

    PUBMED

    https://www.ncbi.nlm.nih.gov/pubmed/6069348


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