Metil-antranilat

Methyl anthranilate, also known as methyl 2-aminobenzoate or carbomethoxyaniline, has the CAS number 134-20-3. It occurs naturally in Concord grapes and other Vitis labrusca grapes and their hybrids, and in plants such as bergamot, champak, gardenia, jasmine and neroli. It is also found in plants such as sunflowers, corn, cherries, cocoa and black tea. Along with ethyl acetate and ethyl butyrate, it is a primary component of the essential flavor of apple.

In grapes, anthraniloyl-coenzyme A:methanol acyltransferase catalyzes the formation of methyl anthranilate from anthraniloyl-CoA and methanol. Foxy aroma is the term for the unique, earthy and sweet muskiness present in most Vitis labrusca grapes and their hybrids. The foxy aroma of Concord grapes is likely the result of several key volatile compounds, of which methyl anthranilate is the most important. Methyl anthranilate is the dominant foxy compound in Vitis labrusca, even though not all grapes related to V. labrusca accumulate high levels of it. Foxiness makes the Concord grape very popular for the production of non-fermented juice and jellies. For wine grapes, foxy aroma is often perceived as an undesirable attribute.

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Related: Champaca · Champaca Absolute · Frangipani · Frangipani Absolute · Gardenia · Lysylang · Plumeria · Stephanotis

What does methyl anthranilate smell like?

Methyl anthranilate gives the characteristic odor of Concord grapes. Its taste is slightly bitter and pungent.

Properties and other uses

Methyl anthranilate has a light blue-violet fluorescence. This blue fluorescence can lead to products containing it being mistaken for products containing other banned fluorescent dyes. It is soluble in oils and propylene glycol, insoluble in glycerol and slightly soluble in water. The conjugate acid has a pKa of 2.23. It also serves as an oxidation inhibitor, a sunscreen agent and an intermediate in the synthesis of chemicals, dyes and pharmaceuticals.

Use as a bird repellent

Several registered end-use products have methyl anthranilate as the active ingredient, ranging from 14.5% to 40% w/w. It can be applied as a spray or a fog to repel pest birds. The labels do not list mammals as target species. Delivered enterically to European starlings, it achieved the same level of repellency as the secondary repellent methiocarb.