Vernolic acid

Vernolic acid

Names
IUPAC name (+)-(12S,13R)-Epoxy-cis-9-octadecenoic acid
Other names Linoleic acid 12:13-oxide
Identifiers
CAS Number	503-07-1 (+)-isomer Y 32381-42-3 (−)-isomer N 58800-58-7 (Racemate) N
3D model (JSmol)	(+)-isomer: Interactive image Interactive image
ChemSpider	4444572 (−)-isomer N 4952464 (+)-isomer N
PubChem CID	5281128 (−)-isomer 6449780 (+)-isomer
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 N Key: CCPPLLJZDQAOHD-BEBBCNLGSA-N 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 O=C(O)CCCCCCC/C=C\C[C@H]1O[C@H]1CCCCC
Properties
Chemical formula	C18H32O3
Molar mass	296.45 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
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).
N  (what is YN ?)
Infobox references

Vernolic acid (leukotoxin) is an organic compound and a fatty acid. This monounsaturated long chain carboxylic acid contains an epoxide and consists of two optical isomers. The (+) optical isomer's IUPAC designation is (+)-(12S,13R)-epoxy-cis-9-octadecenoic acid; it is also termed 12S,13R-EpOME, cis-12-epoxyoctadeca-cis-9-enoic acid, and (9Z)-(12S,13R)-12,13-epoxyoctadecenoic acid. The (-) isomer's IUPAC designation is (-)-(12R,13S)-epoxy-cis-9-octadecenoic acid; it is also termed 12R,13S-EpOME, cis-12-epoxyoctadeca-cis-9-enoic acid, and (9Z)-(12R,13S)-12,13-epoxyoctadecenoic acid. It is an isomer of coronaric acid, which is itself the (+) and (-), i.e. R,S and S,R optical isomers of 9,10-epoxy-12Z-octadecenoic acid (also termed 9(10)-EpOME and (+/-)-9(10)-epoxy-12Z-octadecenoic acid). Vernolic acid was first definitively characterized in 1954. It is the key component in vernonia oil, which is produced in abundance by the genera Vernonia and Euphorbia and is a potentially useful biofeedstock.

In a variety of mammalian species, vernolic acid is made by the metabolism of linoleic acid by certain epoxygenase enzymes; under these circumstances it is termed leukotoxin because of its toxic effects on leukocytes and other cell types and of its ability to produce multiple organ failure and respiratory distress when injected into rodent animal models of the acute respiratory distress syndrome. These effects appear due to the conversion of vernolic acid to its dihydroxy counterparts, 12S,13R- and 12R,13S-dihydroxy-cis-9-octadecenoic acids by soluble epoxide hydrolase (this dihydroxy mixture has been termed leukotoxin diol). Some studies suggest but have not yet proven that vernolic acid is responsible for or contributes to multiple organ failure, respiratory distress, and certain other cataclysmic diseases in humans (see epoxygenase subsection on linoleic acid).