Sterculic acid
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Preferred IUPAC name 8-(2-Octylcycloprop-1-en-1-yl)octanoic acid | |
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Beilstein Reference | 1880442 |
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Properties | |
Chemical formula | C19H34O2 |
Molar mass | 294.479 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references |
Sterculic acid is a cyclopropene fatty acid. It is found in various plants of the genus Sterculia, including being the main component of Sterculia foetida seed oil.[1]
Biosynthesis
The biosynthesis of sterculic acid begins with the cyclopropanation of the alkene of phospholipid-bound oleic acid, an 18-carbon cis-monounsaturated fatty acid. This transformation involves two mechanistic steps: electrophilic methylation with S-adenosyl methionine to give a carbocationic reactive intermediate, followed by cyclization via loss of H+ mediated by a cyclopropane-fatty-acyl-phospholipid synthase enzyme. The product, dihydrosterculic acid, is converted to sterculic acid by dehydrogenation of the cis-disubstituted cyclopropane to cyclopropene.[2] An additional step of α oxidation removes one carbon from the carboxy chain to form the 17-carbon-chain structure of malvalic acid.
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