Related Experiment Video
Updated: Oct 3, 2026

Identification of Fatty Acids in Bacillus cereus
Published on: December 5, 2016
Total synthesis of the novel bacterial fatty acid 16-methyl-8(Z)-heptadecenoic acid
1Department of Chemistry, University of Puerto Rico, P.O. Box 23346, San Juan 00931-3346, Puerto Rico. ncarball@upracd.upr.clu.edu
Abstract:
The recently discovered bacterial fatty acid 16-methyl-8(Z)-heptadecenoic acid was synthesized for the first time in four steps (22% overall yield) starting from commercially available 8-methylnonanoic acid. The synthetic approach provided enough material to corroborate the structure and stereochemistry of the acid, which was recently identified in a Micrococcus bacterium from Lake Pomorie in Bulgaria. Reference equivalent-chain length values in nonpolar capillary gas chromatography for methyl 16-methyl-8(Z)-heptadecenoate and methyl 16-methyl-8(E)-heptadecenoate are also reported. This information will be helpful in subsequent characterizations of these fatty acids, as well as in the total identification of the fatty acid profile of bacteria producing these compounds.
More Related Videos
Related Concept Videos
Overview of Fatty Acid Metabolism
Fatty acids are catabolized in a process called beta-oxidation, which takes place in the matrix of the mitochondria and converts their fatty acid chains into two-carbon units of acetyl groups. The acetyl...
Biosynthesis of Lipids
Formation of Lipopolysaccharides
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Peptidoglycan Synthesis
Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives

