Methyl anthranilate

Methyl anthranilate
Identifiers
CAS number	134-20-3 Y
Jmol-3D images	Image 1
SMILES Nc1c(C(OC)=O)cccc1
Properties
Molecular formula	C8H9NO2
Molar mass	151.165
Melting point	24 °C
Boiling point	256 °C
Hazards
Flash point	104 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 and glycerol. It is combustible, with flash point 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.^[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.

Occurrence

Methyl anthranilate naturally occurs in the Concord grapes and other Vitis labrusca grapes or hybrids thereof, and in bergamot, black locust, champaca, gardenia, jasmine, lemon, mandarin, 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^[2] . 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.

References

1. ^ The Good Scents Company: Methyl anthranilate
2. ^ Daniele Fraternale; |Donata Ricci, Guido Flamini and Giovanna Giomaro. "Volatiles Profile of Red Apple from Marche Region (Italy)". ACG Publications. http://www.acgpubs.org/RNP/2011/Volume%205/.../26-RNP-1010-380.pdf. Retrieved 2011-04-20.