Methyl anthranilate
[CAS# 134-20-3]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Halogen-containing, sulfur-containing, nitrogen-containing compounds >> Nitrogen-containing compound fragrance
• Name: Methyl anthranilate
• Synonyms: Methyl 2-aminobenzoate
• Molecular Formula: C₈H₉NO₂
• Molecular Weight: 151.16
• CAS Registry Number: 134-20-3
• EC Number: 205-132-4
• FEMA: 2682
• SMILES: COC(=O)C1=CC=CC=C1N

Properties

• Density: 1.2±0.1 g/cm³ Calc.^*, 1.168 g/mL (Expl.)
• Melting point: 24 °C (Expl.)
• Boiling point: 256.0 °C 760 mmHg (Calc.)^*, 256 °C (Expl.)
• Flash point: 104.4 °C (Calc.)^*, 123 °C (Expl.)
• Index of refraction: 1.566 (Calc.)^*, 1.582 (Expl.)
• Water solubility: slightly soluble

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H319
• Safety Statements: P264+P265-P280-P305+P351+P338-P337+P317

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Flammable solids	Flam. Sol.	1	H228

Discovery and Applications

Methyl anthranilate is an aromatic ester formed from anthranilic acid and methanol, characterized by a benzene ring bearing adjacent amino and ester functional groups. It is widely recognized for its strong, sweet, grape-like odor and has been studied extensively in the context of natural product chemistry, flavor science, and industrial applications. The history of methyl anthranilate is closely tied to the broader investigation of aromatic esters and amino-substituted benzoic acid derivatives.

The discovery of methyl anthranilate can be traced to nineteenth-century research on anthranilic acid, which itself was identified as an important intermediate in the chemistry of indigo dyes and other aromatic compounds. As esterification reactions became better understood, chemists prepared methyl anthranilate as part of systematic studies on anthranilic acid derivatives. Early characterization focused on its physical properties, distinctive odor, and chemical reactivity, which set it apart from many other simple aromatic esters.

Chemically, methyl anthranilate exhibits properties that reflect the influence of both its ester group and its ortho-amino substituent. The proximity of the amino group to the ester functionality affects intramolecular interactions and contributes to its relatively high stability among aromatic esters. These features made methyl anthranilate a useful model compound in studies of structure–property relationships within substituted benzoates. Its synthesis, typically achieved through acid-catalyzed esterification of anthranilic acid or through related transesterification routes, became well established in laboratory and industrial settings.

One of the most significant applications of methyl anthranilate has been in the flavor and fragrance industries. It occurs naturally in a variety of fruits and flowers, including grapes, strawberries, and jasmine, and it is a key contributor to characteristic aroma profiles. Because of this natural association, methyl anthranilate has been widely used as a flavoring agent to impart grape-like notes in foods and beverages, as well as a fragrance component in perfumes, soaps, and personal care products. Its sensory properties and relative chemical stability have supported its long-standing commercial use.

Beyond flavor and fragrance applications, methyl anthranilate has played an important role in agricultural and environmental contexts. It has been investigated and employed as a bird repellent, exploiting its odor to deter birds from crops, airfields, and other sensitive areas. This application emerged from behavioral studies demonstrating aversive responses in certain bird species. The compound’s effectiveness, combined with its relatively low persistence in the environment, contributed to its adoption in non-lethal wildlife management strategies.

Methyl anthranilate has also been relevant in organic synthesis and chemical research. The compound serves as a precursor or intermediate in the preparation of more complex molecules, including heterocyclic compounds derived from anthranilic acid frameworks. Its reactivity has been explored in transformations involving the amino group, such as acylation and cyclization reactions, making it useful in teaching laboratories and synthetic methodology development.

In biological and toxicological studies, methyl anthranilate has been examined to assess safety and exposure, particularly because of its widespread use in consumer products. These investigations have helped define acceptable usage levels and informed regulatory evaluations in different jurisdictions. Such studies reinforced its suitability for use in food and fragrance applications when handled according to established guidelines.

Overall, methyl anthranilate exemplifies how a relatively simple organic molecule can achieve broad scientific and practical significance. From its origins in fundamental aromatic chemistry to its diverse applications in flavoring, fragrance, agriculture, and synthesis, the compound illustrates the intersection of chemical discovery and applied science. Its continued relevance reflects both its distinctive sensory properties and its versatility as a chemically well-understood aromatic ester.

References

2025. Assessing the efficacy of nanofabricated plant-based antifungal formulation against the growth and zearalenone toxin production by Fusarium graminearum. Brazilian Journal of Microbiology.
DOI: 10.1007/s42770-025-01744-4

2025. Engineering of Corynebacterium glutamicum for the synthesis of aromatic compounds. Applied Microbiology and Biotechnology.
DOI: 10.1007/s00253-025-13520-3