Methyl anthranilate

Methyl anthranilate

Identifiers
CAS Registry Number	134-20-3 N
ChEBI	CHEBI:CHEBI:73244 N
ChemSpider	13858096 N
EC number	205-132-4
InChI InChI=1S/C8H9NO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,9H2,1H3 N Key: VAMXMNNIEUEQDV-UHFFFAOYSA-N N InChI=1/C8H9NO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,9H2,1H3 Key: VAMXMNNIEUEQDV-UHFFFAOYAV
Jmol-3D images	Image
KEGG	C20634 N
SMILES Nc1c(C(OC)=O)cccc1
Properties
Chemical formula	C8H9NO2
Molar mass	151.165
Melting point	24 °C (75 °F; 297 K)
Boiling point	256 °C (493 °F; 529 K)
Hazards
Flash point	104 °C (219 °F; 377 K)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Methyl anthranilate, also known as MA, methyl 2-aminobenzoate, or carbomethoxyaniline, is an ester of anthranilic acid. 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. It is very slightly soluble in water, and soluble in ethanol and propylene glycol. It is insoluble in paraffin oil. It is combustible, with flash point at 104 °C. At full concentration, it has a fruity grape smell; at 25 ppm it has a sweet, fruity, Concord grape-like smell with a musty and berry nuance.^[1]

Uses

Methyl anthranilate acts as a bird repellent. 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. It is used for flavoring of candy, soft drinks (e.g. grape soda), gums, and drugs.

Methyl anthranilate both as a component of various natural essential oils and as a synthesised aroma-chemical is used extensively in modern perfumery.^[1][2] It is also used to produce Schiff's Bases with aldehydes, many of which are also used in perfumery. In a perfumery context the most common Schiff's Base is known as aurantiol^[3] - produced by combining methyl anthranilate and hydroxycitronellal.^[4]

Methyl anthranilate is used to make Benzydamine.

Occurrence

Methyl anthranilate naturally occurs in the Concord grapes and other Vitis labrusca grapes and hybrids thereof, and in bergamot, black locust, champaca, gardenia, jasmine, lemon, mandarin orange, neroli, oranges, rue oil, strawberry, tuberose, wisteria, galangal, and ylang ylang. It is also a primary component of the essential apple flavor, along with ethyl acetate and ethyl butyrate.^[5] It is also secreted by the musk glands of foxes and dogs, and lends a "sickly sweetness" to the smell of rotting flesh.

References