Abstract
Methyl esters of 8 16-carbon acids which occur in cutin of plants have been synthesized from methyl 16,17-dihydroxy-7-oxo- and 16,17-dihydroxy-9-oxoheptadecanoates. 16-Hydroxy-7-oxo- and 16-hydroxy-9-oxohexadecanoates were prepared by lead tetraacetate cleavage followed by sodium triacetoxyborohydride reduction; 16-hydroxy-8-oxo- and 16-hydroxy-10-oxohexadecanoates were prepared by successive ketalization, ester reduction, diol cleavage, acylation, oxidation and methanolysis. Dihydroxy esters were prepared by reduction of oxo esters with sodium borohydride. Mass spectra of TMS ethers of the esters, of pyrrolides and of TMS esters of pyrrolidides have been compared. Mass spectra of mixtures of hydroxyoxo derivatives and of dihydroxy derivatives show that correction factors are required for quantitative analysis, particularly when 7-substituted isomers are present.
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Tulloch, A.P. Cutin acids: Synthesis and mass spectrometry of methyl 16-hydroxy-7-oxo-, 16-hydroxy-8-oxo-, 16-hydroxy-9-oxo-, 16-hydroxy-10-oxo- and 7,16-, 8,16-, 9,16- and 10,16-dihydroxyhexadecanoates. Lipids 15, 881–888 (1980). https://doi.org/10.1007/BF02534409
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DOI: https://doi.org/10.1007/BF02534409