chemistry

Methyl anthranilate

Methyl anthranilate 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 Methyl anthranilate rather than just read about it. In short: Methyl anthranilate, also known as MA, methyl 2-aminobenzoate, or carbomethoxyaniline, is an ester of anthranilic acid. Its chemical formula is C8H9NO2.

Key takeaways

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

Reference excerpt

Methyl anthranilate, also known as MA, methyl 2-aminobenzoate, or carbomethoxyaniline, is an ester of anthranilic acid. Its chemical formula is C8H9NO2. It has a strong and fruity grape smell, and one of its key uses is as a flavoring agent.

Physical properties Methyl anthranilate has a light blue-violet fluorescence. The pure substance has a fruity grape smell; at 25 ppm it has a sweet, fruity, Concord grape-like smell with a musty and berry nuance.

Uses Methyl anthranilate acts as a bird repellent by irritating sensory receptors. Dimethyl anthranilate has a similar effect. It is also used for part of the flavor of grape Kool-Aid. It is used for flavoring of candy, soft drinks (e.g. grape soda), fruit (e.g. Grāpples), chewing gum, and nicotine products. Its characteristic blue fluorecence can lead to mis-analysis of products containing it as containing other banned fluorescent dyes.

Schiff bases in perfumery Methyl anthranilate is one of the two amines most commonly used to form Schiff bases in the fragrance industry, the other being ethyl anthranilate. When methyl anthranilate reacts with an aldehyde, water is released and a single, heavier compound is formed. These compounds are typically yellow-to-orange, viscous liquids that are more stable than their parent aldehydes and have greater tenacity, or staying power, on skin, though they darken over time. Several methyl anthranilate-based Schiff bases are sold under trade names and are widely used across the fragrance industry, such as:

Aurantiol, formed with hydroxycitronellal, has an orange blossom and neroli character and is described as the most widely used Schiff base in perfumery. Verdantiol (also sold as Lilyantine), formed with Lilial, has a linden blossom character with orange blossom undertones. Lyrame (also sold as Lyrantion), formed with the aldehyde Lyral, has a fresh lily-of-the-valley character with notes of orange blossom. Helioforte, formed with Helional, has a marine, almondy character and was developed by the Florasynth company. A Schiff base of methyl anthranilate and Triplal, sold under several trade names including Vertosine, Ligantraal, and Agrumea, was noted by Calkin and Jellinek in the early 1990s as a comparatively recent addition to the category. Perfumers can also add methyl anthranilate as a plain, separate ingredient alongside an aldehyde such as hydroxycitronellal, Lyral, or Helional, allowing the Schiff base to form gradually inside the finished compound over a period of weeks or months, in a process known as maceration. This gradual reaction continues even after a perfume has been bottled; perfumery analysts note that older samples may show Schiff bases that were not present when the fragrance was originally formulated, which complicates efforts to determine an exact original formula from chemical analysis alone. Unintended post-bottling formation can also change a finished fragrance's scent: perfumer Paul Kiler has pointed to Roja Parfums Enigma Pour Homme (2013, sold as Creation-E in the United States) as a case in which a Schiff base formed between methyl anthranilate and vanillin roughly a year after bottling, darkening the fragrance and giving it an unintended root beer-like note. Although once widely used, Schiff bases have become less common in modern perfumery, in part because of the strong color many of them produce.

Occurrence Methyl anthranilate naturally occurs in the Concord grapes and other Vitis labrusca grapes and hybrids thereof, and in bergamot, black locust, champak, gardenia, jasmine, lemon, mandarin orange, neroli, oranges, rue oil, strawberry, tuberose, wisteria, galangal, and ylang ylang. It is also a primary component of the essential apple flavor, along with ethyl acetate and ethyl butyrate.

References

Illustrations

Worked examples

Example 1 — a first encounter with Methyl anthranilate

Start with the simplest possible case. Write down what Methyl anthranilate 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 Methyl anthranilate 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 Methyl anthranilate 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 Methyl anthranilate

In research: Methyl anthranilate 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 Methyl anthranilate 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: Methyl anthranilate is common in secondary-school and first-year university syllabi. It links to neighbouring topics 2-Aminophenyl compounds, Anthranilates, Flavors, so understanding it makes those chapters shorter.
In everyday life: Look for Methyl anthranilate 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 Methyl anthranilate in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Methyl anthranilate 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 Methyl anthranilate out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Methyl anthranilate in simple terms?

Methyl anthranilate, also known as MA, methyl 2-aminobenzoate, or carbomethoxyaniline, is an ester of anthranilic acid. Its chemical formula is C8H9NO2.

Why does Methyl anthranilate 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 Methyl anthranilate?

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 Methyl anthranilate.