Methyl anthranilate

Methyl anthranilate, also known as MA, is an organic compound with the formula C_7H_7NO_2. It is a derivative of anthranilic acid, where the amino group of the acid is methylated. This colorless liquid is often found in the essential oils of various plants and is widely used in the flavor and fragrance industry. Methyl anthranilate has a fruity grape-like odor and taste, making it a popular additive in food, beverages, and the production of perfumes.

Properties

Methyl anthranilate is slightly soluble in water but highly soluble in most organic solvents. It has a boiling point of 256 °C and a melting point of 24 °C, which classifies it as a liquid at room temperature. Its molecular weight is 151.13 g/mol. The compound is also known for its ability to absorb ultraviolet (UV) light, which makes it useful as a UV filter in various cosmetic products.

Sources

Naturally, methyl anthranilate is found in the essential oils of several plants, including oranges, grapes, jasmine, and neroli. It is also present in the concord grape aroma, which is why it is commonly used to flavor grape-flavored products.

Synthesis

Methyl anthranilate can be synthesized through the esterification of anthranilic acid with methanol, usually in the presence of an acid catalyst. This reaction is straightforward and yields methyl anthranilate as the main product.

Applications

Flavoring Agent Due to its pleasant, grape-like aroma and taste, methyl anthranilate is extensively used as a flavoring agent in food and beverages. It is particularly popular in grape-flavored products but can also be found in the flavoring of candies, soft drinks, and chewing gum.

Fragrance In the fragrance industry, methyl anthranilate is used to impart floral and fruity odors to perfumes and cosmetic products. Its stability and solubility in various solvents make it a versatile ingredient in the formulation of fragrances.

Agriculture Methyl anthranilate has been used as a bird repellent on crops. Birds dislike its taste, and its application can help protect fruits and other crops from bird damage without harming the birds.

Pharmaceuticals In the pharmaceutical industry, methyl anthranilate serves as an intermediate in the synthesis of various compounds. It is also investigated for its potential therapeutic effects, including anti-inflammatory and analgesic properties.

Safety

Methyl anthranilate is generally regarded as safe when used in accordance with established guidelines. However, like many chemicals, it should be handled with care, and appropriate safety measures should be taken to avoid ingestion, inhalation, or skin contact in concentrated forms.

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  Methyl anthranilate structure

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  Methyl anthranilate 3D model