Vernolic acid

Vernolic acid
	(−)-(12R,13S)-EpOME
Names
	Preferred IUPAC name (9Z)-(12S,13R)-12,13-epoxyoctadecenoic acid
	Other names Racemic: Linoleic acid 12,13-oxide; cis-12-Epoxyoctadeca-cis-9-enoic acid; Single-enantiomer (corresponding to IUPAC-name isomer): (+)-(12S,13R)-epoxy-cis-9-octadecenoic acid; 12S,13R-EpOME;
Identifiers
CAS Number	503-07-1 (+)-isomer ; 32381-42-3 (−)-isomer ; 17966-13-1 (racemate) ;
3D model (JSmol)	(−)-isomer: Interactive image; (+)-isomer: Interactive image;
ChEBI	CHEBI:38300 (−)-isomer ; CHEBI:27706 (+)-isomer ;
ChemSpider	4444572 (−)-isomer ; 4952464 (+)-isomer ;
PubChem CID	5281128 (−)-isomer; 6449780 (+)-isomer;
UNII	FR42854EPW (+)-isomer ; FF156V3318 (−)-isomer ; 4S5JF40ZOQ (racemate) ;
CompTox Dashboard (EPA)	DTXSID001205124 ;
	InChI InChI=1S/C18H32O3/c1-2-3-10-13-16-17(21-16)14-11-8-6-4-5-7-9-12-15-18(19)20/h8,11,16-17H,2-7,9-10,12-15H2,1H3,(H,19,20)/b11-8-/t16-,17+/m0/s1 Key: CCPPLLJZDQAOHD-BEBBCNLGSA-N ; (−)-isomer: InChI=1/C18H32O3/c1-2-3-10-13-16-17(21-16)14-11-8-6-4-5-7-9-12-15-18(19)20/h8,11,16-17H,2-7,9-10,12-15H2,1H3,(H,19,20)/b11-8-/t16-,17+/m0/s1 Key: CCPPLLJZDQAOHD-BEBBCNLGBK; (+)-isomer: InChI=1/C18H32O3/c1-2-3-10-13-16-17(21-16)14-11-8-6-4-5-7-9-12-15-18(19)20/h8,11,16-17H,2-7,9-10,12-15H2,1H3,(H,19,20)/b11-8-/t16-,17+/m1/s1 Key: CCPPLLJZDQAOHD-GJGKEFFFBZ; (+)-isomer: InChI=1S/C18H32O3/c1-2-3-10-13-16-17(21-16)14-11-8-6-4-5-7-9-12-15-18(19)20/h8,11,16-17H,2-7,9-10,12-15H2,1H3,(H,19,20)/b11-8-/t16-,17+/m1/s1 Key: CCPPLLJZDQAOHD-GJGKEFFFSA-N;
	SMILES (−)-isomer: O=C(O)CCCCCCC/C=C\C[C@H]1O[C@H]1CCCCC; (+)-isomer: O=C(O)CCCCCCC/C=C\C[C@@H]1O[C@@H]1CCCCC;
Properties
Chemical formula	C18H32O3
Molar mass	296.451 g·mol−1
Appearance	Colorless oil
Melting point	23 to 25 °C (73 to 77 °F; 296 to 298 K)
Solubility in water	Insoluble
Solubility in other solvents	organic solvents
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	flammable
Related compounds
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Vernolic acid (leukotoxin B or isoleukotoxin) is a long chain fatty acid that is monounsaturated and contains an epoxide. It is a cis epoxide derived from the C12–C13 alkene of linoleic acid. Vernolic acid was first definitively characterized in 1954 and its absolute configuration determined in 1966. It is a major component in vernonia oil, which is produced in abundance by the genera Vernonia and Euphorbia and is a potentially useful biofeedstock.