Methyl anthranilate, also known as MA, methyl 2-aminobenzoate or carbomethoxyaniline, is an ester

Ester

Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol. Esters are usually derived from an inorganic acid or organic acid in which at least one -OH group is replaced by an -O-alkyl group, and most commonly from carboxylic acids and...

 of anthranilic acid

Anthranilic acid

Anthranilic acid is the organic compound with the formula C6H4COOH. This amino acid is a white solid when pure, although commercial samples may appear yellow. The molecule consists of a benzene ring with two adjacent functional groups, a carboxylic acid and an amine...

. Its chemical formula is C₈H₉NO₂.

Chemical properties

It is a clear to pale yellow liquid with melting point 24 °C and boiling point 256 °C. It shows a light blue fluorescence

Fluorescence

Fluorescence is the emission of light by a substance that has absorbed light or other electromagnetic radiation of a different wavelength. It is a form of luminescence. In most cases, emitted light has a longer wavelength, and therefore lower energy, than the absorbed radiation...

. It is very slightly soluble in water, and soluble in ethanol

Ethanol

Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...

 and propylene glycol

Propylene glycol

Propylene glycol, also called 1,2-propanediol or propane-1,2-diol, is an organic compound with formula C3H8O2 or HO-CH2-CHOH-CH3...

. It is insoluble in paraffin oil and glycerol

Glycerol

Glycerol is a simple polyol compound. It is a colorless, odorless, viscous liquid that is widely used in pharmaceutical formulations. Glycerol has three hydroxyl groups that are responsible for its solubility in water and its hygroscopic nature. The glycerol backbone is central to all lipids...

. It is combustible, with flash point

Flash point

The flash point of a volatile material is the lowest temperature at which it can vaporize to form an ignitable mixture in air. Measuring a flash point requires an ignition source...

 at 104 °C. At full concentration, it has fruity grape smell; at 25 ppm it has sweet fruity concord grape like smell with a musty and berry nuance.

Uses

Methyl anthranilate acts as a bird repellent

Animal repellent

Animal repellents are products designed to keep certain animals away from objects, areas, people, plants, or other animals.-Overview:Repellents generally work by taking advantage of an animal's natural aversion to something, and often the thing chosen is something that the animal has learned to...

. It is food-grade and can be used to protect corn, sunflowers, rice, fruit, and golf courses. Dimethyl anthranilate (DMA) has a similar effect. It is also used for the flavor of grape KoolAid.

Occurrence

Methyl anthranilate naturally occurs in the Concord grape

Concord grape

Concord grapes are a cultivar derived from the grape species Vitis labrusca which are used as table grapes, wine grapes and juice grapes....

s and other Vitis labrusca

Vitis labrusca

Vitis labrusca is a species of grapevines belonging to the Vitis genus in the flowering plant family Vitaceae. The vines are native to the eastern United States and are the source of many grape cultivars, including Catawba and Concord grapes, and many hybrid grape varieties such as Agawam,...

 grapes or hybrids thereof, and in bergamot

Bergamot

Bergamot may refer to:*The Bergamot orange*Monarda, genus of herbs of similar odor to the Bergamot orange; in particular**Monarda didyma, called Bergamot, Scarlet Beebalm, Scarlet Monarda, Oswego Tea, or Crimson Beebalm...

, black locust

Black locust

Robinia pseudoacacia, commonly known as the Black Locust, is a tree in the subfamily Faboideae of the pea family Fabaceae. It is native to the southeastern United States, but has been widely planted and naturalized elsewhere in temperate North America, Europe, Southern Africa and Asia and is...

, champaca, gardenia

Gardenia

Gardenia is a genus of 142 species of flowering plants in the coffee family, Rubiaceae, native to the tropical and subtropical regions of Africa, southern Asia, Australasia and Oceania....

, jasmine

Jasmine

Jasminum , commonly known as jasmines, is a genus of shrubs and vines in the olive family . It contains around 200 species native to tropical and warm temperate regions of the Old World...

, lemon

Lemon

The lemon is both a small evergreen tree native to Asia, and the tree's ellipsoidal yellow fruit. The fruit is used for culinary and non-culinary purposes throughout the world – primarily for its juice, though the pulp and rind are also used, mainly in cooking and baking...

, mandarin

Mandarin orange

The orange, also known as the ' or mandarine , is a small citrus tree with fruit resembling other oranges. Mandarin oranges are usually eaten plain or in fruit salads...

, neroli

Neroli

Neroli oil is a plant oil produced from the blossom of the bitter orange tree . Its scent is sweet, honeyed and somewhat metallic, whereas bergamot, being rich in linalool , has more of an aromatic, soft, floralcy.- Production :The blossoms are gathered, usually by hand, in late April to...

, orange

Orange (fruit)

An orange—specifically, the sweet orange—is the citrus Citrus × sinensis and its fruit. It is the most commonly grown tree fruit in the world....

s, rue oil, strawberry

Strawberry

Fragaria is a genus of flowering plants in the rose family, Rosaceae, commonly known as strawberries for their edible fruits. Although it is commonly thought that strawberries get their name from straw being used as a mulch in cultivating the plants, the etymology of the word is uncertain. There...

, tuberose

Tuberose

The tuberose is a perennial plant related to the agaves, extracts of which are used as a middle note in perfumery. The common name derives from the Latin tuberosa, meaning swollen or tuberous in reference to its root system. It consists of about 12 species...

, wisteria

Wisteria

Wisteria is a genus of flowering plants in the pea family, Fabaceae, that includes ten species of woody climbing vines native to the eastern United States and to China, Korea, and Japan. Aquarists refer to the species Hygrophila difformis, in the family Acanthaceae, as Water Wisteria...

, galangal

Galangal

Galangal is a rhizome of plants of the genus Alpinia or Kaempferia in the ginger family Zingiberaceae, with culinary and medicinal uses originated from Indonesia...

 and ylang ylang. It is also a primary component of the essential apple flavor, along with ethyl acetate and ethyl butyrate . It is used for flavoring of candy, soft drinks (e.g. grape soda), gums, and drugs. It is also secreted by the musk glands of foxes and dogs, and lends a "sickly sweetness" to the smell of rotting flesh.