Abstract
Methyl 4-decenoate (10∶1ω6), methyl dodeca-3,6-dienoate (12∶2ω6), methyl tetradeca-5,8-dienoate (14∶2ω6) and methyl hexadeca-7,10-dienoate (16∶2ω6) were prepared by total synthesis. Rats raised on a fat-deficient diet for 2 1/2 months received 100 mg per day of one of the experimental acids or methyl linoleate for a period of 16 days. The liver lipids were extracted, converted to methyl esters and analyzed by gas-liquid chromatography. Neither 10∶1ω6 nor 12∶2ω6 served as biosynthetic precursors for linoleate. Small amounts of 14∶2ω6 were convered to linoleate while 16∶2ω6 served as an efficient precursor for linoleate and longer chain ω6 acids. None of the short chain ω6 acids were incorporated directly into liver lipids.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Mead, J. F., Federation Proc.20, 952–955 (1961).
Stoffel, W., Z. Physiol. Chem. Hoppe-Seylers333, 71–88 (1963).
Davis, J. T., and J. G. Coniglio, J. Biol. Chem.241, 610–612 (1966).
Klenk, E., Experientia17, 199–204 (1961).
Klenk, E., in “Advances in Lipid Research,” Vol. 3, Paoletti, R., and D. Kritchevsky, (ed.), Academic Press, N. Y., 1965, p. 6.
Brenner, R. R., O. Mercuri and M. E. DeTomas, J. Nutr.77, 203–209 (1962).
Reiser, R., N. L. Murty and H. Rakoff, J. Lipid Res.3, 56–59 (1962).
Gensler, W. J., and G. R. Thomas, J. Am. Chem. Soc.73, 4601–4604 (1951).
Sprecher, H., Biochim. Biophys. Acta44, 296–304 (1967).
Campbell, K. N., and B. K. Campbell, in “Organic Syntheses,” Vol. 4, RabJohn, N. (3d), John Wiley and Sons, N. Y., 1963, p. 117.
Stoffel, W., and E. Bierwith, Angew. Chem.74, 905 (1962).
Gunstone, F. D., and P. J. Sykes, J. Chem. Soc.— 3055–3058 (1962).
Eglinton, G., and M. C. Whiting, J. Chem. Soc.— 3052–3059 (1953).
Osbond, J. M., P. G. Philpott and J. C. Wickens, J. Chem. Soc.—2779–2787 (1961).
Lindlar, H., Helv. Chim. Acta35, 446–450 (1952).
Stoffel, W., H. Caesar and R. Ditzer, Z. Physiol. Chem. Hoppe-Seylers339, 182–193 (1964).
Kennedy, J., A. Lewis, N. J. McCorkindale and R. A. Raphael, J. Chem. Soc.—4945–4948 (1961).
Folch, J., M. Lees and G. H. Sloane-Stanley, J. Biol. Chem.226, 497–509 (1957).
Stoffel, W., F. Chu and E. H. Ahrens, Anal. Chem.31, 307–308 (1957).
Hofstetter, H. H., N. Sen and R. T. Holman, JAOCS42, 537–540 (1965).
Mohrhauer, H., and R. T. Holman, J. Lipid Res.4, 151–159 (1963).
Rahm, J. J., and R. T. Holman, J. Lipid Res.5, 169–176 (1964).
Verdino, B., M. L. Blank, O. S. Privett and W. O. Lundberg, J. Nutr.83, 234–238 (1964).
Brenner, R. R., and R. O. Peluffo, J. Biol. Chem.241, 5213–5219 (1966).
Fulco, A. J., and J. F. Mead, J. Biol. Chem.235, 3379–3384 (1960).
Anderson, R. E., and R. Reiser, Lipids1, 233–234 (1966).
Hsu, R. Y., G. Wasson and J. W. Porter, J. Biol. Chem.240, 3736–3746 (1965).
Nugteren, D. H., Biochim. Biophys. Acta106, 280–290 (1965).
Holman, R. T., and H. H. Hofstetter JAOCS42, 540–544 (1965).
Stoffel, W., and A. Scheid, Z. Physiol. Chem. Hoppe-Seylers348, 205–226 (1967).
Stoffel, W., H. G. Schiefer and G. D. Wolf, Z. Physiol. Chem. Hoppe Seylers347, 102–117 (1966).
Author information
Authors and Affiliations
About this article
Cite this article
Sprecher, H. The total synthesis and metabolism of 4-decenoate, dodeca-3,6-dienoate, tetradeca-5,8-dienoate and hexadeca-7,10-dienoate in the fat-deficient rat. Lipids 3, 14–20 (1968). https://doi.org/10.1007/BF02530962
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02530962