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Johnson AR, Murray KE, Fogerty AC, et al. The reaction of methyl sterculate and malvalate with silver nitrate-silica gel and its use as a basis for the estimation of cyclopropene fatty acids. Lipids. 1967;2(4):316-22doi: 10.1007/BF02532118.
Johnson, A. R., Murray, K. E., Fogerty, A. C., Kennett, B. H., Pearson, J. A., & Shenstone, F. S. (1967). The reaction of methyl sterculate and malvalate with silver nitrate-silica gel and its use as a basis for the estimation of cyclopropene fatty acids. Lipids, 2(4), 316-22. https://doi.org/10.1007/BF02532118
Johnson, A R, et al. "The reaction of methyl sterculate and malvalate with silver nitrate-silica gel and its use as a basis for the estimation of cyclopropene fatty acids." Lipids vol. 2,4 (1967): 316-22. doi: https://doi.org/10.1007/BF02532118
Johnson AR, Murray KE, Fogerty AC, Kennett BH, Pearson JA, Shenstone FS. The reaction of methyl sterculate and malvalate with silver nitrate-silica gel and its use as a basis for the estimation of cyclopropene fatty acids. Lipids. 1967 Jul;2(4):316-22. doi: 10.1007/BF02532118. PMID: 17805758.
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Lipids. 1967 Jul;2(4):316-22. doi: 10.1007/BF02532118.

The reaction of methyl sterculate and malvalate with silver nitrate-silica gel and its use as a basis for the estimation of cyclopropene fatty acids.

Lipids

A R Johnson, K E Murray, A C Fogerty, B H Kennett, J A Pearson, F S Shenstone

Affiliations

  1. Division of Food Preservation, Commonwealth Scientific and Industrial Research Organization, Ryde, N.S.W., Australia.

PMID: 17805758 DOI: 10.1007/BF02532118

Abstract

When in contact with silver nitratesilica gel, methyl esters of cyclopropene fatty acids undergo ring opening to yield pairs of isomers with methylene, hydroxymethyl, or nitratomethyl side-chains at the original ring positions. Thus the main products from methyl sterculate were the methyl 9 (or 10)-methylene octadec-10 (or 8)-enoates, and, in lesser quantities, the methyl 9 (or 10)-(nitratomethyl)-octadec-9-enoates and the methyl 9 (or 10)-(hydroxymethyl)-octadec-9-enoates. Hydrogenation quantitatively converted this mixture of isomeric pairs to a mixture of methyl 9- and methyl 10-methyloctadecanoates.Chromatography on silver nitrate-silica gel, followed by gas chromatography of the hydrogenated products, has been used as the basis of a new method for estimating individual cyclopropene and cyclopropane acids in lipids.

References

  1. J Lipid Res. 1961 Apr;2:135-41 - PubMed
  2. Lipids. 1966 Jan;1(1):10-5 - PubMed
  3. Lipids. 1967 Jul;2(4):308-15 - PubMed

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