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Fatty acids
Vernolic acid
Другие языки:

Vernolic acid

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Vernolic acid
Vernolic Acid.png
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)
ChemSpider
PubChem CID
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).
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Vernolic acid (leukotoxin) is a long chain fatty acid that is monounsaturated and contains an epoxide. It is the R,R-cis epoxide derived from the C12–C13 alkene of linoleic acid. Vernolic acid was first definitively characterized in 1954. 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.

Occurrence

Vernonia oil is extracted from the seeds of the Vernonia galamensis (ironweed), a plant native to eastern Africa. The seeds contain about 40 to 42% oil of which 73 to 80% is vernolic acid. The best varieties of V. anthelmintica contain about 30% less vernolic acid.

Vernolic acid is not commonly found in plants in significant quantities, but some plants which do contain it are Vernonia, Stokesia, Crepis (from the daisy family), and Euphorbia lagascae and Bernardia pulchella from the Euphorbiaceae.

Potential applications

Vernonia oil has been proposed as a precursor to adhesives, varnishes and paints, and industrial coatings. Its low viscosity recommends its use as a nonvolatile solvent in oil-based paints since it will become incorporated in the dry paint rather than evaporating into the air.

In its application as an epoxy oil, vernonia oil competes with soybean or linseed oil, which supply most of the market for these applications. Its low viscosity makes it more desirable than fully epoxidized linseed or soybean oils. It is comparable to partially epoxidized linseed or soybean oil.

Toxicity

In a variety of mammalian species, vernolic acid is made by the metabolism of linoleic acid by cytochrome P450 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).

Related compounds


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