Methyl Anthranilate

Figure 1: Methyl Anthranilate structure.¹

Methyl anthranilate, also known as MA, methyl 2-aminobenzoate, or carbomethoxyaniline, is an ester of anthranilic acid. The chemical formula for this compound is C₈H₉NO₂. Methyl anthranilate is a clear to pale yellow liquid with a melting point of 24°C and a boiling point of 256°. It shows a light blue fluorescence. It is very slightly soluble in water, and soluble in ethanol and propylene glycol.¹ Methyl anthranilate acts as a bird repellant. It is food-grade and can be used to protect corn, sunflowers, rice, fruit, and even golf courses. It is also used for the flavoring of grape Kool-Aid. Methyl anthranilate naturally occurs in Concord grapes, lemon, strawberry, wisteria, and oranges. It is used for flavoring of soft drinks, candy, gum, and drugs.²

An ester is the product of a reaction between an alcohol and an acid, usually an organic acid.³ Methyl anthranilate is derived from the reaction of methanol and anthranilic acid. Sulfuric acid is used as a catalyst during this reaction. Amides are carboxylic acids derivatives, and can be formed by the conversion of the carboxylic acid into an ammonium salt, which then produces an amide upon heating. Anthranilic acid is a carboxylic acid, which forms the amide anthranilamide, when placed into the previous conditions.⁴

References:

1.      Methyl Anthranilate; CAS No. 134-20-3; ScienceLab.com; Houston TX; 2008;  http://www.sciencelab.com/msds.php?msdsId=9924665; Accessed April 10, 2011

2.      Umeda, K; Sullivan, L; Evaluation of Methyl Anthranilate for Use as a Bird Repellant in Selected Crops; 2000; http://ag.arizona.edu/pubs/crops/az1252/az1252-1a.pdf; Accessed April 10, 2011

3.      Fromm, J; Introduction to Esters; 1998; http://www.3rd1000.com/chem301/chem301v.htm; Accessed April 10, 2011

4.      Making Amides; Jim Clark; 2004; http://www.chemguide.co.uk/organicprops/amides/preparation.html; Accessed April 10, 2011