Hostname: page-component-8448b6f56d-tj2md Total loading time: 0 Render date: 2024-04-19T03:53:15.363Z Has data issue: false hasContentIssue false

A compound responsible for metallic flavour in dairy products: II. Theoretical consideration of the mechanism of formation of oct-1-en-3-one

Published online by Cambridge University Press:  01 June 2009

R. A. Wilkinson
Affiliation:
Division of Dairy Research, C.S.I.R.O., Melbourne, Australia
W. Stark
Affiliation:
Division of Dairy Research, C.S.I.R.O., Melbourne, Australia

Summary

Possible mechanisms are considered for the formation of a metallic flavour component, oct-1-en-3-one, in a vacuum-packed butterfat-antioxidant-synergist mixture, and in washed cream and butter with free access to atmospheric oxygen. The oct-1-en-3-one is likely to be derived from linoleic or arachidonic acids, or both. A complex of reactions linking oxygen, catalysts, substrate, radicals, and antioxidants is discussed. Pathways for the production of intermediates giving rise to oct-1-en-3-one are suggested for systems with free and with limited access to oxygen. These mechanisms would involve secondary oxidations with formation of polyfunctional monomers and would be competing for oxygen with those giving rise to polymers. The reasons why they compete to a significant extent are discussed in relation to the detailed environmental conditions including lipid reactivity, effective oxygen pressure in situ, steric effects at phase boundaries and the role of acidity and of ionic intermediates.

Type
Original Articles
Copyright
Copyright © Proprietors of Journal of Dairy Research 1967

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

REFERENCES

Bateman, L. (1954). Q. Rev. chem. Soc. 8, 147.CrossRefGoogle Scholar
Bateman, L. & Hughes, H. (1952). J. chem. Soc. p. 4594.CrossRefGoogle Scholar
Bateman, L., Hughes, H. & Morris, A. L. (1953). Discuss. Faraday Soc. no. 14, 190.Google Scholar
Bawn, C. E. H. (1953). Discuss. Faraday Soc. no. 14, 181.CrossRefGoogle Scholar
Bawn, C. E. H., Pennington, A. A. & Tipper, C. F. H. (1951). Discuss. Faraday Soc. no. 10, 282.CrossRefGoogle Scholar
Bergström, S., Blomstrand, R. & Laurell, S. (1950). Acta chem. scand. 4, 245.Google Scholar
Bosworth, A. W. & Sisson, E. W. (1934). J. biol. Chem. 107, 489.CrossRefGoogle Scholar
Brown, W. H., Tracy, P. H. & Prucha, M. J. (1936). J. Dairy Sci. 19, 488.Google Scholar
Desai, I. D. & Tappel, A. L. (1963). J. Lipid Res. 4, 204.CrossRefGoogle Scholar
El-Negoumy, A. M., de Puchal, M. S. & Hammond, E. G. (1962). J. Dairy Sci. 45, 311.Google Scholar
El-Negoumy, A. M. & Hammond, E. G. (1960). J. Dairy Sci. 43, 840.Google Scholar
El-Negotjmy, A.M., Miles, D. M. & Hammond, E. G. (1961). J. Dairy Sci. 44, 1047.CrossRefGoogle Scholar
Flitman, R. & Frieden, E. (1957). J. Am. chem. Soc. 79, 5198.Google Scholar
Forss, D. A., Dunstone, E. A. & Stark, W. (1960a). J. Dairy Res. 27, 211.CrossRefGoogle Scholar
Forss, D. A., Dunstone, E. A. & Stark, W. (1960b). J. Dairy Res. 27, 373.Google Scholar
Frieden, E. (1958). Biochim. biophys. Acta 27, 414.Google Scholar
Hammond, E. G., El-Negoumy, A. M. & De Puchal, M. S. (1961). J. Dairy Sci. 44, 1170.Google Scholar
Hoffmann, G. (1962). J. Am. Oil Chem. Soc. 39, 439.Google Scholar
Ingold, C. K. (1953, repr. 1957). Structure and Mechanism in Organic Chemistry London: G. Bell and Sons.Google Scholar
Kochi, J. K. & Rust, F. F. (1962). J. Am. chem. Soc. 84, 3946.CrossRefGoogle Scholar
Kummerow, F. A. (1961). Proceedings Flavor Chemistry Symposium, Camden, New Jersey p. 109. Organized by the Campbell Soup Co.Google Scholar
Lea, C. H. (1943). J. Soc. chem. Ind. Lond. 62, 200.Google Scholar
Lea, C. H. (1960). A. Rep. low temp. Res. Stn p. 23.Google Scholar
O'Neill, L. A. (1954). Chemy Ind. p. 384.Google Scholar
Pokorny, J. (1963). Fette Seifen AnstrMittl. 65, 278.Google Scholar
Pont, E. G., Forss, D. A., Dunstone, E. A. & Gunnis, L. F. (1960). J. Dairy Res. 27, 205.Google Scholar
Privett, O. S. (1959). J. Am. Oil Chem. Soc. 36, 507.CrossRefGoogle Scholar
Privett, O. S. (1961). Proceedings Flavor Chemistry Symposiump. 147. Camden, New Jersey, Organized by the Campbell Soup Co.Google Scholar
Privett, O. S. & Quackenbush, F. W. (1954). J. Am. Oil Chem. Soc. 31, 271.Google Scholar
Sohaffer, P. S. & Holm, G. E. (1950). J. Dairy Sci. 33, 865.CrossRefGoogle Scholar
Scott, W. E., Herb, S. F., Magidman, P. & Riemenschneider, R. W. (1959). J. agric. Fd Chem. 7, 125.Google Scholar
Shemyakin, M. M. & Shchukina, L. A. (1957). Usp. Khim. 26, (5), 528.Google Scholar
Shorland, F. B. & Johannesson, D. L. (1951). Nature, Lond. 168, 75.Google Scholar
Smith, L. M. & Lowry, R. R. (1962). J. Dairy Sci. 45, 581.CrossRefGoogle Scholar
Stark, W. & Forss, D. A. (1962). J. Dairy Res. 29, 173.Google Scholar
Stark, W. & Forss, D. A. (1964). J. Dairy Res, 31, 253.CrossRefGoogle Scholar
Stull, J. W., Herreid, E. O. & Tracy, P. H. (1951). J. Dairy Sci. 34, 187.CrossRefGoogle Scholar
Wilkinson, R. A. (1964). Int. Rep. no. 4 Div. Dairy Res. C.S.I.R.O. Aust.Google Scholar