Chemistry:Sterculic acid
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| Preferred IUPAC name
8-(2-Octylcycloprop-1-en-1-yl)octanoic acid | |
| Identifiers | |
3D model (JSmol)
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| 3DMet | |
| 1880442 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| KEGG | |
PubChem CID
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| UNII | |
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| Properties | |
| 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). | |
 verify (what is   ?)
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| 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.
References
- ↑ Nunn, J. R. (1952). "The structure of sterculic acid". J. Chem. Soc.: 313–318. doi:10.1039/JR9520000313.
- ↑ Dewick, Paul (2009). Medicinal Natural products. Wiley. pp. 46–55. ISBN 9780470741689. https://archive.org/details/medicinalnatural00dewi_880.
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