Sterculic acid

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]

Sterculic acid

Names
IUPAC name 8-(2-Octyl-1-cyclopropenyl)octanoic acid
Identifiers
CAS Number	738-87-4
3D model (JSmol)	Interactive image
3DMet	B02241
Beilstein Reference	1880442
ChEBI	CHEBI:9261
ChEMBL	ChEMBL3677268
ChemSpider	12386
KEGG	C08366
PubChem CID	12921
UNII	MXV06G5ROK
CompTox Dashboard (EPA)	DTXSID90970445
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^−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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Infobox references

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

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.