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

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

anthranilic acid Anthranilic acid is an aromatic acid with the formula C6H4(NH2)(CO2H) and has a sweetish taste. The molecule consists of a benzene ring, ''ortho''-substituted with a carboxylic acid and an amine. As a result of containing both acidic and basic f ...

. Its chemical formula is C₈H₉NO₂. It has a strong and fruity grape smell, and one of its key uses is as a flavoring agent.

Chemical properties

It is a colorless to pale yellow liquid with melting point 24 °C and boiling point 256 °C. It has a density of 1.168 g/cm³ at 20 °C. It has a refractive index of 1.583 at 589 nm of wavelength and 20 °C. It shows a light blue-violet

fluorescence Fluorescence is one of two kinds of photoluminescence, the emission of light by a substance that has absorbed light or other electromagnetic radiation. When exposed to ultraviolet radiation, many substances will glow (fluoresce) with colore ...

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

ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...

and

propylene glycol Propylene glycol ( IUPAC name: propane-1,2-diol) is a viscous, colorless liquid. It is almost odorless and has a faintly sweet taste. Its chemical formula is CH3CH(OH)CH2OH. As it contains two alcohol groups, it is classified as a diol. An al ...

. It is insoluble in paraffin oil. It is combustible, with

flash point The flash point of a material is the "lowest liquid temperature at which, under certain standardized conditions, a liquid gives off vapours in a quantity such as to be capable of forming an ignitable vapour/air mixture". The flash point is somet ...

at 104 °C. Pure, it has a fruity grape smell; at 25 ppm it has a sweet, fruity,

Concord grape The Concord grape is a cultivar derived from the grape species ''Vitis labrusca'' (also known as fox grape) that are used as table grapes, wine grapes and juice grapes. They are often used to make grape jelly, grape juice, grape pies, grape- ...

-like smell with a musty and berry nuance.The Good Scents Company: Methyl anthranilate
/ref>The Japan Food Chemical Research Foundation
/ref>

Uses

Methyl anthranilate acts as a bird repellent by irritating sensory receptors. Dimethyl anthranilate (DMA) has a similar effect. It is also used for part of the flavor of grape

Kool-Aid Kool-Aid is an American brand of flavored drink mix owned by Kraft Heinz based in Chicago, Illinois. The powder form was created by Edwin Perkins in 1927 based upon a liquid concentrate named Fruit Smack. History Kool-Aid was invented by E ...

. It is used for

flavoring A flavoring (or flavouring), also known as flavor (or flavour) or flavorant, is a food additive that is used to improve the taste or smell of food. It changes the perceptual impression of food as determined primarily by the chemoreceptors of ...

of candy, soft drinks (e.g.

grape soda Grape drinks (also known as grape soda, grape pop, or purple drink in certain regions of the U.S.) are sweetened drinks with a grape flavor and a deep purple color. They may be carbonated (e.g., Fanta) or not (e.g., Kool-Aid). ''Grapeade'' first ...

), fruit (e.g. Grāpples), chewing gum, and nicotine products. Methyl anthranilate both as a component of various natural essential oils and as a synthesised aroma-chemical is used extensively in modern perfumery. It is also used to produce

Schiff base In organic chemistry, a Schiff base (named after Hugo Schiff) is a compound with the general structure ( = alkyl or aryl, but not hydrogen). They can be considered a sub-class of imines, being either secondary ketimines or secondary aldim ...

s with

aldehyde In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...

s, many of which are also used in perfumery. In a perfumery context the most common Schiff's Base is known as aurantiol, produced by combining methyl anthranilate and hydroxycitronellal. In organic synthesis, methyl anthranilate can be used as a source of the highly reactive

aryne In organic chemistry, arynes and benzynes are a class of highly Reactivity (chemistry), reactive chemical Chemical species, species derived from an aromatic ring by removal of two substituents. Arynes are examples of didehydroarenes (1,2-didehydro ...

, benzyne. It is obtained by

diazotization Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group where R can be any organic group, such as an alkyl or an aryl, and X is an inorganic or organic anion, such as a halide. The parent, compou ...

of the amine group using sodium nitrite which eliminates nitrogen and CO₂ giving benzyne as an intermediate for Diels-Alder addition or other substitution at the ring.

Occurrence

Methyl anthranilate naturally occurs in the

s and other ''

Vitis labrusca ''Vitis labrusca'', the fox grape, is a species of grapevines belonging to the ''Vitis'' genus in the flowering plant family Vitaceae. The vines are native to eastern North America and are the source of many grape cultivars, including Catawba, ...

'' grapes and hybrids thereof, and in bergamot,

black locust ''Robinia pseudoacacia'', commonly known as black locust, is a medium-sized hardwood deciduous tree, belonging to the tribe Robinieae of the legume family Fabaceae. It is native to a few small areas of the United States, but it has been widely pl ...

champak Champak is a popular fortnightly magazine for children published by the Delhi Press Group since 1969 in India. ''Champak'' competes with Amar Chitra Katha Amar Chitra Katha (ACK Comics) is an Indian comic book publisher, based in Mumbai, ...

gardenia ''Gardenia'' is a genus of flowering plants in the coffee family, Rubiaceae, native to the tropical and subtropical regions of Africa, Asia, Madagascar, Pacific Islands, and Australia. The genus was named by Carl Linnaeus and John Ellis after ...

jasmine Jasmine (botanical name: ''Jasminum'', pronounced ) is a genus of shrubs and vines in the olive family of Oleaceae. It contains around 200 species native to tropical and warm temperate regions of Eurasia, Africa, and Oceania. Jasmines are wid ...

lemon The lemon (''Citrus'' × ''limon'') is a species of small evergreen tree in the ''Citrus'' genus of the flowering plant family Rutaceae. A true lemon is a hybrid of the citron and the bitter orange. Its origins are uncertain, but some ...

mandarin orange A mandarin orange (''Citrus reticulata''), often simply called mandarin, is a small, rounded citrus tree fruit. Treated as a distinct species of orange, it is usually eaten plain or in fruit salads. The mandarin is small and oblate, unlike the ...

neroli Neroli oil is an essential oil produced from the blossom of the bitter orange tree (''Citrus aurantium subsp. amara'' or ''Bigaradia''). Its scent is sweet, honeyed and somewhat metallic with green and spicy facets. Orange blossom is also extract ...

oranges The orange, also called sweet orange to distinguish it from the bitter orange (''Citrus × aurantium''), is the fruit of a tree in the family Rutaceae. Botanically, this is the hybrid ''Citrus'' × ''sinensis'', between the pomelo (''Citrus m ...

rue ''Ruta graveolens'', commonly known as rue, common rue or herb-of-grace, is a species of the genus '' Ruta'' grown as an ornamental plant and herb. It is native to the Mediterranean. It is grown throughout the world in gardens, especially for i ...

oil,

strawberry The garden strawberry (or simply strawberry; ''Fragaria × ananassa'') is a widely grown Hybrid (biology), hybrid plant cultivated worldwide for its fruit. The genus ''Fragaria'', the strawberries, is in the rose family, Rosaceae. The fruit ...

tuberose ''Agave amica'', formerly ''Polianthes tuberosa'', the tuberose, is a perennial plant in the family Asparagaceae, subfamily Agavoideae, extracts of which are used as a Note (perfumery), note in perfumery. Now widely grown as an ornamental plant, ...

wisteria ''Wisteria'' is a genus of flowering plants in the legume family, Fabaceae (Leguminosae). The genus includes four species of woody twining vines that are native to China, Japan, Korea, Vietnam, southern Canada, the Eastern United States, and nor ...

galangal Galangal () is a rhizome of plants in the ginger family Zingiberaceae, with culinary and medicinal uses originating in Indonesia. It is one of four species in the genus ''Alpinia'', and is known for its pungent, aromatic flavor. Greater gal ...

, and ylang ylang. It is also a primary component of the essential apple flavor, along with

ethyl acetate Ethyl acetate commonly abbreviated EtOAc, ETAC or EA) is the organic compound with the formula , simplified to . This flammable, colorless liquid has a characteristic sweet smell (similar to pear drops) and is used in glues, nail polish removers, ...

and

ethyl butyrate Ethyl butyrate, also known as ethyl butanoate, or butyric ether, is an ester with the chemical formula CH3CH2CH2COOCH2CH3. It is soluble in propylene glycol, paraffin oil, and kerosene. It has a fruity odor, similar to pineapple, and is a key ing ...

.Daniele Fraternale, Donata Ricci, Guido Flamini and Giovanna Giomaro. Volatiles Profile of Red Apple from Marche Region (Italy). ''Rec. Nat. Prod.'' (2011), 5:3; 202-207
pdf
/ref>

References

{{Reflist Anthranilates Methyl esters Flavors