Chemistry:Methyl anthranilate
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| Preferred IUPAC name
Methyl 2-aminobenzoate | |
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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)
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1.583 (589 nm at 20 °C)[2] |
| Hazards | |
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| GHS Signal word | Warning |
| H319 | |
| P264, P280, P305+351+338, P337+313 | |
| 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). | |
 verify (what is   ?)
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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.
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]Template:Predatory publisher Dimethyl anthranilate (fi) 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.[4][9] 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 (zh),[10] produced by combining methyl anthranilate and hydroxycitronellal.[11]{{page needed|date=March 2026}
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.[12]
References
- ↑ 1.0 1.1 1.2 1.3 Kugler, E.; Kováts, E. sz. (1963). "Zur Kenntnis ätherischer Öle. 1. Mitteilung. Zur Kenntnis des Mandarinenschalen-Öls (Citrus reticulata BLANCO, bzw. Citrus nobilis var. deliciosa SWINGLE "Mandarin")". Helvetica Chimica Acta 46 (5): 1480–1513. doi:10.1002/hlca.19630460506.
- ↑ Pytela, Oldřich; Halama, Aleš (1996). "Steric Effects in Acid-Catalyzed Decomposition and Base-Catalyzed Cyclization of 1-(2-Alkoxycarbonylphenyl)-3-phenyltriazenes". Collection of Czechoslovak Chemical Communications 61 (5): 751. doi:10.1135/cccc19960751.
- ↑ 3.0 3.1 Toyoda, Masatake; Ito, Yosido; Iwaida, Masahiro (1979). "Fluorescence in Candies Caused by Methyl Anthranilate, a Flavoring Agent". Journal of Food Protection 42 (8): 658–659. doi:10.4315/0362-028X-42.8.658. PMID 30812312.
- ↑ 4.0 4.1 "Methyl anthranilate, 134-20-3". The Good Scents Company. http://www.thegoodscentscompany.com/data/rw1008211.html.
- ↑ "The Japan Food Chemical Research Foundation". http://www.ffcr.or.jp/zaidan/ffcrhome.nsf/7bd44c20b0dc562649256502001b65e9/916cae3da5a8a11b49256f320018877f/$FILE/D248.pdf.
- ↑ Saleem, Zobia; Ahmad, Shahzad; Jabeen, Farhat; Khan, Hammad Ahmad; Yaqub, Sajid; Samiullah, Khizar; Shaheen, Robina; Irfan, Muhammad et al. (30 April 2015). "Efficacy of methylanthranilate and anthraquinone against house crow (Corvus splendens) from maize seeds and seedlings in aviary conditions in Pakistan". Journal of Biodiversity and Environmental Sciences 6 (4): 435-444. ISSN 2222-3045. https://www.researchgate.net/publication/309528963. Retrieved 6 January 2026.
- ↑ Terčič, D.; Pančur, M.; Jordan, D.; Zupan Šemrov, M. (2020). "Effects of Dimethyl Anthranilate-Based Repellents on Behavior, Plumage Condition, Egg Quality, and Performance in Laying Hens". Frontiers in Veterinary Science 7. doi:10.3389/fvets.2020.00533. PMID 32974401.
- ↑ Brown, Jessica E.; Luo, Wentai; Isabelle, Lorne M.; Pankow, James F. (2014). "Candy Flavorings in Tobacco". New England Journal of Medicine 370 (23): 2250–2252. doi:10.1056/NEJMc1403015. PMID 24805984.
- ↑ Curtis, Tony; Williams, David G. (2009). An Introduction to Perfumery (2nd ed.). ISBN 978-0-9608752-8-3.
- ↑ Sell, Charles, ed. The Chemistry of Fragrances: From Perfumer to Consumer. ISBN 978-085404-824-3.
- ↑ "Hydroxycitronellal / methyl anthranilate schiff's base, 89-43-0". The Good Scents Company. http://www.thegoodscentscompany.com/data/rw1004281.html.
- ↑ Fraternale, Daniele; Ricci, Donata; Flamini, Guido; Giomaro, Giovanna (2011). "Volatiles Profile of Red Apple from Marche Region (Italy)". Rec. Nat. Prod. 5 (3): 202–207. http://www.acgpubs.org/RNP/2011/Volume%205/Issue%201/26-RNP-1010-380.pdf.
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