Methyl anthranilate
Chemical compound
From Wikipedia, the free encyclopedia
Methyl anthranilate, also known as MA, methyl 2-aminobenzoate, or carbomethoxyaniline, is an ester of anthranilic acid. Its chemical formula is C8H9NO2. It has a strong and fruity grape smell, and one of its key uses is as a flavoring agent.
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| Names | |
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| Preferred IUPAC name
Methyl 2-aminobenzoate | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.004.667 |
| EC Number |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C8H9NO2 | |
| Molar mass | 151.165 |
| Appearance | colorless liquid[1] |
| Odor | grape-like |
| Density | 1.168 g/cm3[1] |
| Melting point | 24 °C (75 °F; 297 K)[1] |
| Boiling point | 256 °C (493 °F; 529 K)[1] |
| Very slight | |
| Solubility in ethanol | Soluble |
| Solubility in propylene glycol | Soluble |
| Solubility in mineral oil | Insoluble |
Refractive index (nD) |
1.583 (589 nm at 20 °C)[2] |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H319 | |
| P264, P280, P305+P351+P338, P337+P313 | |
| 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).
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Physical properties
Methyl anthranilate has a light blue-violet fluorescence.[3] The pure substance has a fruity grape smell; at 25 ppm it has a sweet, fruity, Concord grape-like smell with a musty and berry nuance.[4][5]
Uses
Methyl anthranilate acts as a bird repellent by irritating sensory receptors.[6][predatory publication] Dimethyl anthranilate has a similar effect.[7]
It is also used for part of the flavor of grape Kool-Aid. It is used for flavoring of candy, soft drinks (e.g. grape soda), fruit (e.g. Grāpples), chewing gum, and nicotine products.[8] Its characteristic blue fluorecence can lead to mis-analysis of products containing it as containing other banned fluorescent dyes.[3]
Methyl anthranilate both as a component of various natural essential oils and as a synthesised aroma-chemical is used extensively in modern perfumery.[9][10][page needed] 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 aurantiol,[11] produced by combining methyl anthranilate and hydroxycitronellal.[12][page needed]
Occurrence
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.[13]