chemistry

Vernolic acid

Vernolic acid is a chemistry topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand Vernolic acid rather than just read about it. In short: Vernolic acid (leukotoxin B or isoleukotoxin) is a long chain fatty acid that is monounsaturated and contains an epoxide. It is a cis epoxide derived from the C12–C13 alkene of linoleic acid.

Key takeaways

Vernolic acid belongs to chemistry; place it in that map before memorising details.
Learn the definition first, then one example that makes the definition concrete.
Connect Vernolic acid to a quantity you can measure, compute or draw — that is where exam questions come from.
Reproduce the core statement of Vernolic acid from memory before moving on to harder problems.

Reference excerpt

Vernolic acid (leukotoxin B or isoleukotoxin) is a long chain fatty acid that is monounsaturated and contains an epoxide. It is a cis epoxide derived from the C12–C13 alkene of linoleic acid. Vernolic acid was first definitively characterized in 1954 and its absolute configuration determined in 1966. 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. For instance, (12S,13R)-EpOME is converted by soluble epoxide hydrolase (sEH) to (12R,13R)-dihydroxy-9Z-octadecenoic acid due to inversion at C12 carbon atom during hydrolysis. A mixture of this dihydroxy acid with its 12S,13S enantiomer has been termed isoleukotoxin 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 § Linoleic acid).

Related compounds coronaric acid, C9-C10 epoxide of linoleic acid.

References

Illustrations

Worked examples

Example 1 — a first encounter with Vernolic acid

Start with the simplest possible case. Write down what Vernolic acid claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In chemistry, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to Vernolic acid before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about Vernolic acid ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of Vernolic acid

In research: Vernolic acid appears in chemistry research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry: Engineering practice reuses Vernolic acid in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom: Vernolic acid is common in secondary-school and first-year university syllabi. It links to neighbouring topics Alkenoic acids, Epoxides, Fatty acids, so understanding it makes those chapters shorter.
In everyday life: Look for Vernolic acid outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.

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How to study Vernolic acid in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Vernolic acid means in your own words.
Compare your version with the excerpt and mark what you missed.
Work through the three examples above with pen and paper.
Explain Vernolic acid out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Vernolic acid in simple terms?

Vernolic acid (leukotoxin B or isoleukotoxin) is a long chain fatty acid that is monounsaturated and contains an epoxide. It is a cis epoxide derived from the C12–C13 alkene of linoleic acid.

Why does Vernolic acid matter?

Because it connects several chemistry ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study Vernolic acid?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on Vernolic acid.