Methyl anthranilate

Methyl anthranilate
Names


Preferred IUPAC name Methyl 2-aminobenzoate
Identifiers
CAS Number	134-20-3^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:73244^N
ChemSpider	13858096^N
ECHA InfoCard	100.004.667
EC Number	205-132-4
KEGG	C20634^N
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
SMILES Nc1c(C(OC)=O)cccc1
Properties
Chemical formula	C₈H₉NO₂
Molar mass	151.165
Density	1.168 g/cm^3
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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is ^YN ?)
Infobox references

Methyl anthranilate, also known as MA, methyl 2-aminobenzoate, or carbomethoxyaniline, is an ester of anthranilic acid. Its chemical formula is C₈H₉NO₂.

It is a clear 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 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.

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 Kool-Aid. It is used for flavoring of candy, soft drinks , e.g. grape soda, chewing gum, drugs, 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 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, produced by combining methyl anthranilate and hydroxycitronellal.

Methyl anthranilate naturally occurs in the Concord grapes and other Vitis labrusca grapes and hybrids thereof, and in bergamot, black locust, champak, 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.

...
Wikipedia