Vernolic acid

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Vernolic acid
Vernolic Acid.png
IUPAC name
(+)-(12S,13R)-Epoxy-cis-9-octadecenoic acid
Other names
Linoleic acid 12:13-oxide
CAS number 503-07-1 YesY
ChemSpider 4444572 (−)-isomer N
4952464 (+)-isomer N
Jmol-3D images Image


PubChem 5281128 (−)-isomer
6449780 (+)-isomer
Molar mass 296.44 g·mol−1
Appearance Colorless oil
Melting point 23 to 25 °C (73 to 77 °F; 296 to 298 K)
Solubility in other solvents organic solvents
Main hazards flammable
Related compounds
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

Vernolic acid is an organic compound and a fatty acid. This monounsaturated long chain carboxylic acid contains an epoxide. This isomer of coronaric acid was first definitively characterized in 1954.[1] 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.

Vernonia oil[edit]

Vernonia oil is extracted from the seeds of the Vernonia galamensis (or 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. Products that can be made from vernonia oil include epoxies for manufacturing 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.[2]

This use of vernonia oil offers potential environmental benefits, since its use could reduce emissions associated with man-made chemicals.

In its application as an epoxy oil,[3] 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 more comparable to partially epoxidized linseed or soybean oil.[4]

Other plant sources[edit]

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.[5]


  1. ^ Gunstone F. D. (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. 
  2. ^ T.M. Teynor et al.. "Vernonia". Alternative Field Crops Manual. Retrieved 2006-09-10. 
  3. ^ A.I Mohamed, T. Mebrahtu, and T. Andebrhan (1999). J. Janick, 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. 
  4. ^ Muturi, Patrick; Wang, Danqing; Dirlikov, Stoil (1994). "Epoxidized vegetable oils as reactive diluents I. Comparison of vernonia, epoxidized soybean and epoxidized linseed oils". Progress in Organic Coatings 25: 85. doi:10.1016/0300-9440(94)00504-4. 
  5. ^ Edgar B. Cahoon, Kevin G. Ripp, Sarah E. Hall, and Brian McGonigle (February 2002). "Transgenic Production of Epoxy Fatty Acids by Expression of a Cytochrome P450 Enzyme from Euphorbia lagascae Seed". Plant Physiol. 128 (2): 615–624. doi:10.1104/pp.010768. PMC 148923. PMID 11842164.