Cyclic fatty acids/monomers

Romero, A., Cuesta, C., and Sanchez-Muniz, F.-J. 2000. Cyclic fatty acid monomers and thermoxidative alteration compounds formed during frying of frozen foods in extra virgin olive oil, JAOCS, 77(11), 1169-1175. 

Sebedio, J.-L., J.-L. Le Quere, E. Semon, O. Morin, J. Prevost, and A. Grandgirard, Heat Treatment of Vegetable Oils. II. GC-MS and GC-FTIR Spectra of Some Isolated Cyclic Fatty Acid Monomers, J. Am. Oil Chem. Soc. 64 1324-1333 (1987). 

Mossoba, M.M., M.P.Yuracwecz, J.A.G. Roach, H.S. Lin, R.E. McDonald, B.D. Flickinger, and E.G. Perkins, Rapid Determination of Double Bond Configuration and Position along the Hydrocarbon Chain in Cyclic Fatty Acid Monomers, Lipids 29 893-896(1994). 

Le Quere, J.-L., J.-L. Sebedio, R. Henry, F. Couderc, N. Demont, and J.-C. Prome, Gas Chromatography-Mass Spectrometry and Gas Chromatography-Tandem Mass Spectrometry of Cyclic Fatty Acid Monomers Isolated from Heated Fats, J. Chromatogr. 562 659-672 (1991). 

Vat le, J.M., J.-L. Sebedio, and J.-L. Le Qu6re, Cyclic Fatty Acid Monomers Synthesis and Characterization of Methyl co-(2-Alkylcyclopentyl) Alkenoates and Alkanoates, Chem. Phys. Lipids 48 119-128 (1988). 

Martin, J.C., C. Caselli, S. Broquet, P. Juaneda, M. Nour, J.L. Sdb dio, and A. Bernard. 1997. Effect of cyclic fatty acid monomers on fat absorption and transport depends on their positioning within the ingested triacylglycerols. Journal of Lipid Research 38 1666-79. 

Martin, J.C., F. Jofffe, M.H. Siess, M.F. Vernevaut, P. CoUenot, M. Genty, and J.L. Sebedio. 2000. Cyclic fatty acid monomers from heated oil modify the activities of hpid synthesizing and oxidizing enzymes in rat hver. Journal of Nutrition 130 1524—30. 

Figure 5.9 Matrix-isolation Fourier transform infra-red spectra of dimethyloxazoline derivatives of A, 9-(2 -but-c/j-l-enyl-cyclopentenyl)nonanoic acid B, 9-(2 -but-rra j-l-enyl-cyclo-pentenyl)nonanoic acid C, 9-(2 -prop-/ra/w-l-enyl-cyclohex-cw-4-enyl)nonanoate from heated linseed oil. Redrawn from Mossoba, M. M., Yuracwecz, M. P., Roach, J. A. G. et aL, Analysis of cyclic fatty acid monomer 2-alkenyl-4,4-dimethyloxazoline derivatives by gas chromatogra-phy-Fourier transform infra-red spectroscopy, J. Agric. Food Chem., 44, 3193-6, 1996.

Figure 5.10 Scheme for characterization of cyclic fatty acid monomers (CFAMs) from heated vegetable oils. HPLC = high-pressure liquid chromatography GC = gas chromatography FTIR = Fourier transform infra-red (spectroscopy) MS = mass spectrometry DMOX = dismethyloxazoline. 

Le Quere, J.-L., Sebedio, J.-L., Henry, R. et al. (1991) Gas chromatography-mass spectrometry and gas chromatography-tandem mass spectrometry of cyclic fatty acid monomers isolated from heated fats. J. Chromatogr., 562, 659-72. 

Mossoba, M. M., Yuracwecz, M. P., Roach, J. A. G. et al. (1994) Rapid determination of double bond configuration and position along the hydrocarbon chain in cyclic fatty acid monomers. Lipids, 29 (12), 893-6. 

Ribot, E., Grandgirard, A., Sebedio, J.-L. et al (1992) Incorporation of cyclic fatty acid monomers in lipids of rat heart cell cultures. Lipids, 27 (1), 79-81. 

Rojo, J. A. and Perkins, E. G. (1987) Cyclic fatty acid monomer formation in frying fats. 1. Determination and structural study. J. Am. Oil Chem. Soc., 64 (3), 414-21. 

Sebedio, J.-L. (1985) Application of methoxy-bromomercuric-adduct fractionation to the study of cyclic fatty acid monomers from a heated linseed oil. Fette Seifen Anstrichm., 87 (7), 267-73. 

Sebedio, J.-L., Catte, M., Boudier, M. A. et al. (1996a) Formation of fatty acid geometrical isomers and of cyclic fatty acid monomers during the finish frying of frozen prefried potatoes. Food Res. Intemat., 29 (2), 109-16. 

Vatele, J. M., Sebedio, J.-L. and Le Quere, J.-L. (1988) Cyclic fatty acid monomers synthesis and characterization of methyl co-(2-alkylcyclopentyl) alkenoates and alkanoates. Chem. Phys. Lipids, 48, 119-28. 

Cyclopentyl and cyclohexyl fatty acid monomers are present in heated vegetable oils. Sebedio et al. (1989) have used GC/MS to identify the major products from heated linseed oil as a mixture of 1 1 cis and trans cyclopentyl and cyclohexyl isomers the products of heated sunflower oil were found to be mostly cyclopentyl isomers. The major cyclopentyl isomers were the cis and trans isomers of methyl 7-(2 -hexyl cyclopentyl)-heptanoates and methyl 10-(2 -propylcyclopentyl)-decanoates. The major cyclohexyl isomers were trans and cis methyl 9-(2 -propylcyclohexyl)-nonanoates and made up 50% of the cyclic fatty acid isomers of linseed oil. Dobson et al (1995) have used AgNOs and GC/MS for the structural analysis of cyclic diene fatty acids, and Mossoba et al (1996) have presented confirmatory MS data for cyclic fatty acid monomers by using deuteration. 

Sebedio, J. L., LeQuere, J. L., Morin, O. et al. (1989) Heat treatment of vegetable oils. III. GC-MS characterization of cyclic fatty acid monomers in heated sunflower and linseed oils after total hydrogenation. J. Am. Oil Chem. Soc., 66, 704-9. 

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