Vernolic acid
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
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 B[1]) 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.[2] Vernolic acid was first definitively characterized in 1954.[3] 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.[4]

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.[5]

In its application as an epoxy oil,[6] 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.[7]

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.[8][9] 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).[10][9] 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

References

  1. ^ National Center for Biotechnology Information. "PubChem Compound Summary for CID 6449780, Vernolic acid". PubChem. Retrieved 29 May 2023.
  2. ^ Metzger, J. O.; Bornscheuer, U. (2006). "Lipids as renewable resources: current state of chemical and biotechnological conversion and diversification". Applied Microbiology and Biotechnology. 71 (1): 13–22. doi:10.1007/s00253-006-0335-4. PMID 16604360. S2CID 28601501.
  3. ^ 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.
  4. ^ Cahoon EB, Ripp KG, Hall SE, McGonigle B (February 2002). "Transgenic production of epoxy fatty acids by expression of a cytochrome P450 enzyme from Euphorbia lagascae seed". Plant Physiology. 128 (2): 615–24. doi:10.1104/pp.010768. PMC 148923. PMID 11842164.
  5. ^ Teynor TM, Putnam DJ, Oplinger ES, Oelke EA, Kelling KA, Doll JD (February 1992). "Vernonia". Alternative Field Crops Manual. Retrieved 2006-09-10.
  6. ^ Mohamed AI, Mebrahtu T, Andebrhan T (1999). Janick J (ed.). "Variability in oil and vernolic acid contents in the new Vernonia galamensis collection from East Africa". Perspectives on New Crops and New Uses: 272–274. Retrieved 2006-09-10.
  7. ^ Muturi P, Wang D, Dirlikov S (1994). "Epoxidized vegetable oils as reactive diluents I. Comparison of vernonia, epoxidized soybean and epoxidized linseed oils". Progress in Organic Coatings. 25: 85–94. doi:10.1016/0300-9440(94)00504-4.
  8. ^ Linhartová I, Bumba L, Mašín J, Basler M, Osička R, Kamanová J, Procházková K, Adkins I, Hejnová-Holubová J, Sadílková L, Morová J, Sebo P (November 2010). "RTX proteins: a highly diverse family secreted by a common mechanism". FEMS Microbiology Reviews. 34 (6): 1076–112. doi:10.1111/j.1574-6976.2010.00231.x. PMC 3034196. PMID 20528947.
  9. ^ a b Spector AA, Kim HY (April 2015). "Cytochrome P450 epoxygenase pathway of polyunsaturated fatty acid metabolism". Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids. 1851 (4): 356–65. doi:10.1016/j.bbalip.2014.07.020. PMC 4314516. PMID 25093613.
  10. ^ Greene JF, Newman JW, Williamson KC, Hammock BD (April 2000). "Toxicity of epoxy fatty acids and related compounds to cells expressing human soluble epoxide hydrolase". Chemical Research in Toxicology. 13 (4): 217–26. doi:10.1021/tx990162c. PMID 10775319.
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