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Journal of Lipid Research, Vol. 12, 383-395, July 1971
Copyright © 1971 by Lipid Research, Inc.

The biology of methyl ketones

F. W. Forney and A. J. Markovetz

Department of Microbiology, The University of Iowa, Iowa City, Iowa 52240

Examples of the biological occurrence of methyl ketones are reviewed. The lack of significant accumulations of these compounds in the biosphere indicates that a recycling of these organic molecules is occurring. Evidence for biodegradation of acetone by mammals and longer methyl ketones by microorganisms via terminal methyl-group oxidation is discussed. A new mechanism for the subterminal oxidation of methyl ketones by microorganisms is proposed whereby the first intermediate produced is an acetate ester which subsequently is cleaved to acetate and a primary alcohol two carbons shorter than the original ketone substrate.

Methyl ketones can be produced by mammals and fungi by decarboxylation of ßbeta;-keto acids. Some bacteria are able to form methyl ketones via the oxidation of aliphatic hydrocarbons at the methylene carbon to the methyl group. Speculations on the biosynthesis of methyl ketones by insects and plants and a discussion of the possible biological roles of methyl ketones in diverse biological systems are presented.

Supplementary key words ketones • acetone • plant oils • insect secretions • dairy products • abortive ßbeta;-oxidation • Baeyer-Villiger oxidation • rancidity • pheromones • chemical communication

Submitted on November 20, 1970
Accepted on February 26, 1971

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