Sterculic acid

Sterculic acid

Names
Preferred IUPAC name 8-(2-Octylcycloprop-1-en-1-yl)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). N verify (what is YN ?) 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.

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.