Czech J. Food Sci., 2009, 27(6):463-469 | DOI: 10.17221/181/2009-CJFS

Antimicrobial properties of 11-cyclohexylundecanoic acid

Jan ©midrkal, Tereza Karlová, Vladimír Filip, Markéta Zárubová, Iveta Hrádková
Department of Dairy and Fat Technology, Faculty of Food and Biochemical Technology, Institute of Chemical Technology in Prague, Prague, Czech Republic

The fact that milk fat contains many minor fatty acids is mostly neglected. It is known that 11-cyclohexylundecanoic acid is contained in cow's milk fat in the amount of 0.1-0.2%. It is also contained in human milk. 11-Cyclohexylundecanoic acid was synthesised, purified to 99.5% (GC) and its antimicrobial properties were investigated. It was found that 11-cyclohexylundecanoic acid has inhibitory effects on Bacillus cereus, Escherichia coli, and Fusarium culmorum from the concentration of 0.05 mmol/l, however, no antimicrobial effect on Saccharomyces cerevisiae has been determined. 11-Cyclohexylundecanoic acid was found also in goat and cow milk fat on the level of 0.1-0.2%. It is convenient to hydrogenate the sample of fat before the determination of 11-cyclohexylundecanoic acid by GC method. Keywords:

Keywords: milk fat; fatty acids; antimicrobial properties; 11-cyclohexylundecanoic acid; GC

Published: December 31, 2009  Show citation

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©midrkal J, Karlová T, Filip V, Zárubová M, Hrádková I. Antimicrobial properties of 11-cyclohexylundecanoic acid. Czech J. Food Sci. 2009;27(6):463-469. doi: 10.17221/181/2009-CJFS.
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    References

    1. Biermann U., Metzger J.O. (2004): Alkylaton of alkenes: ethylaluminum sesquichloride-mediated hydro-alkyl additions with alkyl chloroformates and di-tert-butylpyrocarbonate. Journal of the American Chemical Society, 126: 10319-10330. Go to original source... Go to PubMed...
    2. Boer J.B., Jansen C.P., Kentie A., Knol H.W. (1947): The growth - promoting action of vaccenic acid. Journal of Nutrition, 33: 359-360. Go to original source... Go to PubMed...
    3. Christopherson S.W., Glass R.L. (1969): Preparation of milk fat methyl esters by alcoholysis in an essentially nonalcoholic solution. Journal of Dairy Science, 52, 1289-1290. Go to original source...
    4. DeRosa M., Gambacorta A., Minale L.J., Bullock D. (1971): Cyclohexane fatty acids from a thermophilic bacterium. Journal of the Chemical Society D: Chemical Communications: 1334. Go to original source...
    5. DGF Einheitsmethoden (2001): C-VI-10 a - Gaschromatographie, Analyse von Fettsäuren und Fettsäurenvertelilung. 2. Auflage. Wissenschaftliche Verlagsgesellschaft mbH, Stuttgart.
    6. Egge H., Murawsky U., Gyorgy P., Zilliken F. (1969): Minor constituents of human milk. I. Identification of cyclohexaneundecanoic acid and phytanic acid in human milk fat by a combination gas chromatographmass spectrometer. FEBS Letters, 2: 255-258. Go to original source... Go to PubMed...
    7. Hiers G.S., Adams R. (1926): ω-Cyclohexyl derivatives of various normal aliphatic acids IV. Journal of the American Chemical Society, 48: 2385-2393. Go to original source...
    8. IDF (1996) : Determination of milk fat content - RöseGottlieb - Gravimetric method. Joint IDF/ISO/AOAC International Standard. Method 1D.
    9. Jaroą J., Pavlík J., Turzík D. (1998): Mathematical Expectation and Statistics. Institute of Chemical Technology, Prague.
    10. Karlová T., Poláková L., ©midrkal J., Fillip V. (2010): Antimicrobial effects of fatty acid fructose esters. Czech Journal of Food Sciences, 28 (in press) Go to original source...
    11. Levy L. (1975): The activity of chaulmoogra acids against Mycobacterium leprae. American Review of Respiratory Disease, 111: 703-705. Go to PubMed...
    12. Lock A.L., Bauman D.E. (2004): Modifying milk fat composition of dairy cows to enhance fatty acids beneficial to human health. Lipids, 39: 1197-1206. Go to original source... Go to PubMed...
    13. Schogt J.C.M., Begemann P.H. (1965): Isolation of 11-cyclohexylundecanoic acid from butter. Journal of Lipid Research, 6: 466-470. Go to original source... Go to PubMed...
    14. Suzuki K., Saito K., Kawaguchi A., Okuda S.; Komagata K. (1981): Occurrence of ω-cyclohexyl fatty acids in Curtobacterium pusillum strains. Journal of General and Applied Microbiology, 27: 261-266. Go to original source...
    15. Vanhatalo A., Kuoppala K., Toivonen V., Shingfield K.J. (2007): Effects of forage species and stage of maturity on bovine milk fatty acid composition. European Journal of Lipid Science and Technology, 109: 856-867. Go to original source...
    16. Williams C.M. (2000): Dietary fatty acids and human health. Annales de Zootechnie, 49: 165-180. Go to original source...
    17. Wahle K.W., Heys S.D., Rotondo D. (2004): Conjugated linoleic acids: Are they beneficial to human health? Progress in Lipid Research, 43: 553-587. Go to original source... Go to PubMed...

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