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
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • 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
  • (−)-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
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)
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).
☒N verify (what is checkY☒N ?)

Vernolic acid (leukotoxin B[1] or isoleukotoxin[2]) 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.[3] Vernolic acid was first definitively characterized in 1954[4] and its absolute configuration determined in 1966.[5] 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.

  1. ^ National Center for Biotechnology Information. "PubChem Compound Summary for CID 6449780, Vernolic acid". PubChem. Retrieved 29 May 2023.
  2. ^ Quaranta A, Revol-Cavalier J, Wheelock CE (December 2022). "The octadecanoids: an emerging class of lipid mediators". Biochem Soc Trans. 50 (6): 1569–1582[1575]. doi:10.1042/BST20210644. PMC 9788390. PMID 36454542.
  3. ^ Hildreth K, Kodani SD, Hammock BD, Zhao L (December 2020). "Cytochrome P450-derived Linoleic Acid Metabolites EpOMEs and DiHOMEs: A Review of Recent Studies". The Journal of Nutritional Biochemistry. 86 (article 108484). doi:10.1016/j.jnutbio.2020.108484. PMC 7606796. PMID 32827665.
  4. ^ Gunstone FD (1954). "Fatty acids. Part II. The nature of the oxygenated acid present in Vernonia anthelmintica (Willd.) seed oil". Journal of the Chemical Society. 1954: 1611–1616. doi:10.1039/JR9540001611.
  5. ^ Morris, L.J.; Wharry, D.M. (January 1966). "Naturally occurring epoxy acids. IV. The absolute optical configuration of vernolic acid". Lipids. 1 (1). American Oil Chemists' Society: 41–46. doi:10.1007/BF02668123.