Sterculic acid
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| Names
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Preferred IUPAC name
8-(2-Octylcycloprop-1-en-1-yl)octanoic acid |
| Identifiers
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| 3DMet
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1880442
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| ChEBI
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| ChEMBL
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| ChemSpider
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| KEGG
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| UNII
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InChI=1S/C19H34O2/c1-2-3-4-5-7-10-13-17-16-18(17)14-11-8-6-9-12-15-19(20)21/h2-16H2,1H3,(H,20,21) Key: PQRKPYLNZGDCFH-UHFFFAOYSA-N
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CCCCCCCCC1=C(C1)CCCCCCCC(=O)O
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| Properties
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C19H34O2
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| Molar mass
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294.479 g·mol−1
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Chemical compound
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.
Biosynthesis
References
