Vernolic acid is an organic compound

Organic compound

An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 and a fatty acid

Fatty acid

In chemistry, especially biochemistry, a fatty acid is a carboxylic acid with a long unbranched aliphatic tail , which is either saturated or unsaturated. Most naturally occurring fatty acids have a chain of an even number of carbon atoms, from 4 to 28. Fatty acids are usually derived from...

. This monounsaturated long chain carboxylic acid

Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of at least one carboxyl group. The general formula of a carboxylic acid is R-COOH, where R is some monovalent functional group...

 contains an epoxide

Epoxide

An epoxide is a cyclic ether with three ring atoms. This ring approximately defines an equilateral triangle, which makes it highly strained. The strained ring makes epoxides more reactive than other ethers. Simple epoxides are named from the parent compound ethylene oxide or oxirane, such as in...

. This isomer of coronaric acid was first definitively characterized in 1954. It is the key component in vernonia oil, which is produced in abundance by the genuses Vernonia and Euphorbia and is a potentially useful biofeedstock.

Vernonia oil

Vernonia oil is extracted from the seeds of the Vernonia galamensis

Vernonia galamensis

Vernonia galamensis is a plant in the sunflower family, known for its use as an oilseed. This species, often called ironweed, is the largest source of vernonia oil, which is rich in a useful epoxy fatty acid called vernolic acid and is used to make plastics, rubbery coatings, and drying agents...

 (or ironweed), a plant native to eastern Africa

Africa

Africa is the world's second largest and second most populous continent, after Asia. At about 30.2 million km² including adjacent islands, it covers 6% of the Earth's total surface area and 20.4% of the total land area...

. 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 adhesive

Adhesive

An adhesive, or glue, is a mixture in a liquid or semi-liquid state that adheres or bonds items together. Adhesives may come from either natural or synthetic sources. The types of materials that can be bonded are vast but they are especially useful for bonding thin materials...

s, varnish

Varnish

Varnish is a transparent, hard, protective finish or film primarily used in wood finishing but also for other materials. Varnish is traditionally a combination of a drying oil, a resin, and a thinner or solvent. Varnish finishes are usually glossy but may be designed to produce satin or semi-gloss...

es and paint

Paint

Paint is any liquid, liquefiable, or mastic composition which after application to a substrate in a thin layer is converted to an opaque solid film. One may also consider the digital mimicry thereof...

s, and industrial coatings. Its low viscosity

Viscosity

Viscosity is a measure of the resistance of a fluid which is being deformed by either shear or tensile stress. In everyday terms , viscosity is "thickness" or "internal friction". Thus, water is "thin", having a lower viscosity, while honey is "thick", having a higher viscosity...

 recommends its use as a nonvolatile solvent

Solvent

A solvent is a liquid, solid, or gas that dissolves another solid, liquid, or gaseous solute, resulting in a solution that is soluble in a certain volume of solvent at a specified temperature...

 in oil-based paints since it will become incorporated in the dry paint rather than evaporating into the air.

This use of vernonia oil offers potential environmental

Natural environment

The natural environment encompasses all living and non-living things occurring naturally on Earth or some region thereof. It is an environment that encompasses the interaction of all living species....

 benefits, since its use could reduce emissions associated with man-made chemicals.

In its application as an epoxy

Epoxy

Epoxy, also known as polyepoxide, is a thermosetting polymer formed from reaction of an epoxide "resin" with polyamine "hardener". Epoxy has a wide range of applications, including fiber-reinforced plastic materials and general purpose adhesives....

 oil, vernonia oil competes with soybean

Soybean oil

Soybean oil is a vegetable oil extracted from the seeds of the soybean . It is one of the most widely consumed cooking oils. As a drying oil, processed soybean oil is also used as a base for printing inks and oil paints...

 or linseed oil

Linseed oil

Linseed oil, also known as flaxseed oil, is a clear to yellowish oil obtained from the dried ripe seeds of the flax plant . The oil is obtained by cold pressing, sometimes followed by solvent extraction...

, which supply most of the market for these applications. Its low viscosity

Viscosity

Viscosity is a measure of the resistance of a fluid which is being deformed by either shear or tensile stress. In everyday terms , viscosity is "thickness" or "internal friction". Thus, water is "thin", having a lower viscosity, while honey is "thick", having a higher viscosity...

 makes it more desirable than fully epoxidized linseed or soybean oils. It is more comparable to partially epoxidized linseed or soybean oil.

Other plant sources

Vernolic acid is not commonly found in plants in significant quantities, but some plants which do contain it are Vernonia

Vernonia

Vernonia is a genus of about 1000 species of forbs and shrubs in the family Asteraceae. Some species are known as Ironweed. Some species are edible and of economic value. They are known for having intense purple flowers. The genus is named for English botanist William Vernon. There are numerous...

, Stokesia

Stokesia (plant)

Stokesia laevis is a species of flowering plant native to southeastern North America, the only species in the genus Stokesia. It is in the daisy family. The flowers appear in the summer and are purple . The plant is cultivated and several cultivars are available...

, Crepis

Crepis

Crepis, commonly known in some parts of the world as hawksbeard or hawk's-beard , is a genus of about 200 annual and perennial flowering plants of the family Asteraceae superficially resembling the dandelion, the most conspicuous difference being that Crepis usually has branching...

 (from the daisy family

Asteraceae

The Asteraceae or Compositae , is an exceedingly large and widespread family of vascular plants. The group has more than 22,750 currently accepted species, spread across 1620 genera and 12 subfamilies...

), and Euphorbia lagascae and Bernardia

Bernardia

Bernardia is a plant genus of the family Euphorbiaceae....

 pulchella from the Euphorbiaceae

Euphorbiaceae

Euphorbiaceae, the Spurge family are a large family of flowering plants with 300 genera and around 7,500 species. Most are herbs, but some, especially in the tropics, are also shrubs or trees. Some are succulent and resemble cacti....

.