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Sterculic acid

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Sterculic acid
Names
Preferred IUPAC name 8-(2-Octylcycloprop-1-en-1-yl)octanoic acid
Identifiers
CAS Number
3D model (JSmol)
3DMet
Beilstein Reference 1880442
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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
SMILES
  • CCCCCCCCC1=C(C1)CCCCCCCC(=O)O
Properties
Chemical formula C19H34O2
Molar mass 294.479 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
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.

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. 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

  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. Wiley. pp. 46–55. ISBN 9780470741689.


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