Synthesis of 9Z, 11E-octadecadienoic and 10E, 12Z-octadecadienoic acids, the major components of conjugated linoleic acid

Lipids

Volumn 34, Issue 8, 1999, Pages 879-884

  Chen, Chien An ^a   Lu, Wei ^a   Sih, Charles J ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BUTANOL; LINOLEIC ACID; POTASSIUM HYDROXIDE; TRIACYLGLYCEROL LIPASE;

ARTICLE; ASPERGILLUS NIGER; ENZYME ANALYSIS; ESTERIFICATION; LIPID COMPOSITION; LIPID METABOLISM; NONHUMAN; STEREOCHEMISTRY;

ANIMALS; CATTLE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FATTY ACIDS, UNSATURATED; LINOLEIC ACIDS; LIPASE; MEAT; METHODS; STEREOISOMERISM;

EID: 0032846440     PISSN: 00244201     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11745-999-0436-y     Document Type: Article

References (25)

1. Ha, Y.L., Grimm, N.K., and Pariza, M.W. (1987) Anticarcinogens from Fried Ground Beef: Heat-Altered Derivatives of Linoleic Acid, Carcinogenesis 8, 1881-1887.
2. Lee, K.N., Kritchevsky, D., and Pariza, M.W. (1994) Conjugated Linoleic Acid and Atherosclerosis in Rabbits, Atherosclerosis 108, 19-25.
3. Ha, Y.L., Storkson, J., and Pariza, M.W. (1990) Inhibition of Benzo(a)pyrene-Induced Mouse Forestomach Neoplasia by Conjugated Dienoic Derivitives of Linoleic Acid, Cancer Res. 50, 1097-1101.
4. Pariza, M.W. (1991) CLA, A New Cancer Inhibitor in Dairy Products, Bull. Int. Dairy Fed. 257, 29-30.
5. Ip, C., Chin, S.F., Scimeca, J.A., and Pariza, M.W. (1991) Mammary Cancer Prevention by Conjugated Dienoic Derivatives of Linoleic Acid, Cancer Res. 51, 6118-6124.
6. Park, Y., Albright, K.J., Liu, W., Storkson, J.M., Cook, M.E., and Pariza, M.W. (1997) Effect of Conjugated Linoleic Acid on Body Composition in Mice, Lipids 32, 853-858.
7. Nichols, P.L., Herb, S.F., and Riemenschneider, R.W. (1951) Isomers of Conjugated Fatty Acids. I. Alkali-Isomerized Linoleic Acid, J. Am. Chem. Soc. 73, 247-252.
8. Sehat, N., Yurawecs, M.P., Roach, J.A.G., Mossoba, M.M., Kramer, J.K.G., and Ku, Y. (1998) Silver Ion-High-Performance Liquid Chromatographic Separation and Identification of Conjugated Linoleic Acid Isomers, Lipids 33, 217-221.
9. Chen, C.A., and Sih, C.J. (1998) Chemoenzymatic Synthesis of Conjugated Linoleic Acid, J. Org. Chem. 63, 9620-9621.
10. Lee, K.M. (1996) Conjugated Linoleic Acid and Lipid Metabolism, Ph.D. Thesis, University of Wisconsin-Madison, pp. 1-170.
11. Salamonczyk, G.M., Han, K., Zuo, Z.W., and Sih, C.J. (1996) Synthesis of Cryptophycins via a Chemoenzymatic Approach, J. Org. Chem. 61, 6893-6900.
12. Schlosser, M., and Schneider, P. (1980) Regioselektive metallierung des phenylcyclopropans sowie leichte analagerung des 1-phenylcyclopropyl-kaliums an athylen, Helv. Chim. Acta 63, 2404-2410.
13. Schlosser, M. (1998) Superbases for Organic Syntheses, Pure Appl. Chem. 60, 1627-1634.
14. Schlosser, M., and Rauchschwalbe, G. (1978) 2-Methylpentadienyl- and 2,4-Dimethylpentadienylpotassium: First Examples of U-Shaped, Though Open-Chain, Organometallics, J. Am. Chem. Soc. 100, 3258-3260.
15. Privett, O.S., and Nickell, E.C. (1966) Determination of the Specific Positions of cis and trans Double Bonds in Polyenes, Lipids 1, 98-103.
16. 3-MeOH: A Single Reagent for Ozonolysis of Monoethylenic Unsaturation, Lipids 12, 293-296.
17. Ryhage, R., and Stenhagen, E., Mass Spectrometry of Long-Chain Esters, in Mass Spectrometry of Organic Ions (McLafferty, F.W., ed.) Academic Press, New York, 1963, p. 399-452.
18. Jensen, R.G. (1974) Symposium: Microbial Lipolytic Enzymes, Lipids 9, 149-157.
19. Baillargeon, M.W., Bistline, R.G., Jr., and Sonnet, P.E. (1989) Evaluation of Strains of Geotrichum candidum for Lipase Production and Fatty Acid Specificity, Appl. Microbiol. Biotechnol. 30, 92-96.
20. Chen, C.S., Fujimoto, Y., Girdaukas, G., and Sih, C.J. (1982) Quantitative Analyses of Biochemical Kinetic Resolutions of Enantiomers, J. Am. Chem. Soc. 104, 7294-7299.
21. Chen, C.S., and Sih, C.J. (1989) General Aspects and Optimization of Enantioselective Biocatalysis in Organic Solvents: The Use of Lipases, Angew. Chem. Int. Ed. Engl. 28, 695-707.
22. Berdeaux, O., Christie, W.W., Gunstone, F.D., and Sébédio, J.L. (1997) Large-Scale Synthesis of Methyl cis-9,trans-11-Octadecadienoate from Methyl Ricinoleate, J. Am. Oil Chem. Soc. 74, 1011-1015.
23. Lie Ken Jie, M.S.F., Pasha, M.K., and Alam, M.S. (1997) Synthesis and Nuclear Magnetic Resonance Properties of All Geometrical Isomers of Conjugated Linoleic Acids, Lipids 32, 1041-1044.
24. Body, D.R., and Shorland, F.B. (1965) The Geometric Isomers of Conjugated Octadecadienoates from Dehydration of Methyl Ricinoleate, J. Am. Oil Chem. Soc. 42, 5-8.
25. Gunstone, F.D., and Said, A.I. (1971) Methyl 12-Mesyloxyoleate as a Source of Cyclopropane Esters and of Conjugated Octadecadienoates, Chem. Phys. Lipids 7, 121-134.