Sterculic acid

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Sterculic acid
Sterculic acid.svg
Names
Preferred IUPAC name
8-(2-Octylcycloprop-1-en-1-yl)octanoic acid
Identifiers
3D model (JSmol)
3DMet
1880442
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • 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
  • CCCCCCCCC1=C(C1)CCCCCCCC(=O)O
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).
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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[edit]

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[edit]

  1. ^ Nunn, J. R. (1952). "The structure of sterculic acid". J. Chem. Soc.: 313–318. doi:10.1039/JR9520000313.
  2. ^ Dewick, Paul (2009). Medicinal Natural products. pp. 46–55. ISBN 9780470741689.