2-Alkylcyclobutanones as markers for irradiated foodstuffs-I. Synthesis of saturated and unsaturated standards

Radiation Physics and Chemistry

Volumn 55, Issue 3, 1999, Pages 337-344

  Miesch, M ^a   Ndiaye, B ^b   Hasselmann, C ^b   Marchioni, E ^b  

^a UNIVERSITÉ LOUIS PASTEUR   (France)

^b UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; ASSAYS; FOOD PRODUCTS; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; RADIATION EFFECTS; SYNTHESIS (CHEMICAL);

ALKYLCYCLOBUTANONE; KETOALDEHYDE; PHOSPHORANES; WITTIG REACTION;

KETONES;

ALDEHYDE; BIOCHEMICAL MARKER; CYCLOBUTANONE DERIVATIVE; PHOSPHORANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; FOOD IRRADIATION; GAMMA IRRADIATION; STANDARD; SYNTHESIS;

EID: 0033166196     PISSN: 0969806X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0969-806X(98)00338-7     Document Type: Article

References (13)

1. Anon, 1996. European Committee for Standardization. Foodstuffs. Detection of irradiated food containing fat. Gas chromatographic/Mass spectrometric analysis of 2-alkylcyclobutanones. EN 1785.
2. Boyd D.R., Hamilton J.T.G., Hand M.V., Stevenson M.H., Stevenson P.J. Synthesis, characterisation and potential use of 2-dodecylcyclobutanone as a marker for irradiated chicken. J. Agric. Food Chem. 39:1991;789.
3. Clark, D.E., Holton, P.G., Meredith, R.F.K., Ritchie, A.C., Walker, T., Whiting, D.E., 1962. Emetine and related compounds. Part II. The stereospecific synthesis of (±)-2,3 dehydroemetine and (±)-2,3 dehydroisoemetine. J. Chem. Soc. 2479.
4. Crone A.V.J., Hamilton J.T.G., Stevenson M.H. Effect of storage and cooking on the dose response of 2-dodecylcyclobutanone, a potential marker for irradiated chicken. J. Sci. Food Agr. 58:1992;249.
5. Crone A.V.J., Hand M.V., Hamilton J.T.G., Sharma N.D., Boyd D.R., Stevenson M.H. Synthesis, characterisation and use of 2-tetradecylcyclobutanone together with other cyclobutanones as markers of irradiated liquid whole egg. J. Sci. Food Agr. 62:1993;361.
6. Gruseck U., Heuschmann M. Preparation of donor-acceptor substituted vinylcyclobutanes. Chem. Ber. 123:1990;1905.
7. Hamilton, L., Stevenson, M.H., Boyd, D.R., Brannigan, I.N., Treacy, A.B., Hamilton, J.T.G., McRobert, W.C., Elliot, C.T., 1995. Detection of 2-substituted cyclobutanones as irradiation products of lipid-containing foods: synthesis and applications of cis- and trans-2-(tetradec-5′-enyl) cyclobutanones and 11-(2′oxocyclobutyl)-undecanoic acid. J. Chem. Soc. Perkin Trans. 139.
8. Kirmse W., Schneider S. Eliminierungsreaktionen an 2-tosyloxymethyl-cycloalkanon acetalen. Chem. Ber. 102:1969;2440.
9. Kumar V., Dev S. Chemistry of ayurvedic crude drugs. Tetrahedron. 43:1987;5933.
10. Miller S.A., Gadwood R.C. Synthesis of cyclobutanones via 1-bromo-1-ethoxycyclopropane: (E)-2-(1-propenyl) cyclobutanones. Org. Synth. 67:1988;210.
11. Stevenson M.H., Crone A.V.J., Hamilton J.T.G. Irradiation detection. Nature. 344:1990;202.
12. Stevenson M.H., Crone A.V.J., Hamilton J.T.G., McMurray C.H. The use of 2-dodecylcyclobutanone for the identification of irradiated chicken meat and eggs. Radiat. Phys. Chem. 42:1993;363.
13. Stevenson M.H. Identification of irradiated foods. Food Technol. 48:1994;141.