Vernolic acid

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Name = Vernolic acid
ImageFile = Vernolic Acid.png ImageSize = 200px
IUPACName = (+)-(12S,13R)-Epoxy-cis-9-octadecenoic acid
OtherNames = Linoleic acid 12:13-oxide
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Section2 = Chembox Properties
Formula = C₁₈H₃₂O₃
MolarMass = 310.47 g/mol
Appearance = colorless oil
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Solubility = insoluble in water
Solvent = other solvents
SolubleOther = organic solvents
MeltingPt = 23-25 °C
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Section7 = Chembox Hazards
MainHazards = flammable
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Function = compounds
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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. [Gunstone F. D. “Fatty acids. Part II. The nature of the oxygenated acid present in "Vernonia anthelmintica" (Willd.) seed oil” Journal of the Chemical Society, 1954, pages 1611 – 1616. {DOI|10.1039/JR9540001611.] It is the key component in vernonia oil, which is produced in abundance by the genuses Vernonia and Euphorbia and is a potentially useful biofeed stock.

Vernonia oil

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." [cite book
url=http://www.hort.purdue.edu/newcrop/afcm/vernonia.html
title=Alternative Field Crops Manual
chapter=Vernonia
author=T.M. Teynor "et al"
accessdate=2006-09-10]

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, [cite journal
url=http://www.hort.purdue.edu/newcrop/proceedings1999/v4-272.html
author=A.I Mohamed, T. Mebrahtu, and T. Andebrhan
year=1999
title=Variability in oil and vernolic acid contents in the new Vernonia galamensis collection from East Africa
pages=272–274
editor=J. Janick
journal=Perspectives on new crops and new uses
accessdate=2006-09-10] vernonia oil competes with soybean or linseed oil, which supply most of the market for these applications. Vernonia oil is claimed to have superior qualities in this application, compared to these oils. [cite web
title=Vernonia
author=David A. Dierig
url=http://www.uswcl.ars.ag.gov/EPD/NewCrops/Vernonia.htm
accessdate=2006-09-10]

References