Abstract
Methyld 8- and [1-13C] 5,8,11,14-eicosatetraenoate (arachidonate) were prepared from a common synthetic precursor, 4,7,10,13-nonadecatetrayn-1-ol. The purified products were characterized by gas chromatography-mass spectrometry. Mass spectra oft-butyldimethylsilyl esters ofd 8-and [1-13C]-arachidonic acid showed a most intense [M-57]+ peak at high mass. The isotopic purity of methyl [1-13C] arachidonate was 99% and that of methyld 8-arachidonate was 56%. Whend 8-arachidonic acid was prepared by direct deuteration of 5,8,11,14-eicosatetraynoic acid, the isotopic purity of the sample was 86%.
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References
Hamberg, M., W.G. Niehaus, and B. Samuelsson, Anal. Biochem. 22:143 (1968).
Emken, E.A., W.K. Rohwedder, H.J. Dutton, R. Dougherty, J.M. Iacono, and J. Mackin, Lipids 11:135 (1976).
Stockton, G.W., C.F. Polnaszek, A.P. Tulloch, F. Hasan, and I.C.P. Smith, Biochemistry 15:954 (1976).
Seelig, A., and J. Seelig, Biochemistry 13:4839 (1974).
Corey, E.J., and A. Venkateswarlu, J. Am. Chem. Soc. 94:6190 (1972).
Biemann, K., “Mass Spectrometry, Organic Chemical Applications,” McGraw Hill, New York, 1962, p. 223.
Spercher, H., Lipids 6:889 (1971).
Lindlar, H., Helv. Chim. Acta 35:446 (1952).
Baumann, W.J., and H.K. Mangold, J. Org. Chem. 29:3055 (1964).
Baumann, W.J., and H.K. Mangold, J. Lipid Res. 9:287 (1968).
Wood, R., and F. Snyder, J. Am. Oil Chem. Soc. 43:53 (1966).
Phillipou, G., D.A. Bigham, and R.F. Seamark, Lipids 10:714 (1975).
Green, K., M. Hamberg, B. Samuelsson, and J.C. Frölich, in “Progress in Prostaglandin and Thromboxane Resaerch”, Vol. 5, Edited by J.C. Frölich, Raven Press, New York, 1978, p. 44.
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Do, U.H., Sundaram, M.G., Ramachandran, S. et al. Synthesis and characterization of [1-13C]-and d8-arachidonic acid. Lipids 14, 819–821 (1979). https://doi.org/10.1007/BF02533522
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DOI: https://doi.org/10.1007/BF02533522