Methyl anthranilate

Not to be confused with Menthyl anthranilate.
Methyl anthranilate
Names
Preferred IUPAC name
Methyl 2-aminobenzoate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.667
EC Number
  • 205-132-4
KEGG
UNII
  • 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
  • COC(=O)c1c(N)cccc1
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
1.583 (589 nm at 20 °C)[2]
Hazards
GHS labelling:
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).
N verify (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 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 substnace 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] 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.[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,[10] produced by combining methyl anthranilate and hydroxycitronellal.[11]

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. ^ a b c d 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.
  2. ^ 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. ^ a b 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. ^ a b "Methyl anthranilate, 134-20-3". The Good Scents Company.
  5. ^ "The Japan Food Chemical Research Foundation" (PDF).
  6. ^ Saleem, Zobia; Ahmad, Shahzad; Jabeen, Farhat; Khan, Hammad Ahmad; Yaqub, Sajid; Samiullah, Khizar; Shaheen, Robina; Irfan, Muhammad; Masih, Asif (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. Retrieved 6 January 2026.
  7. ^ 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. 7 533. doi:10.3389/fvets.2020.00533. PMC 7466561. PMID 32974401.
  8. ^ 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.
  9. ^ Curtis, Tony; Williams, David G. (2009). An Introduction to Perfumery (2nd ed.). ISBN 978-0-9608752-8-3.
  10. ^ Sell, Charles (ed.). The Chemistry of Fragrances: From Perfumer to Consumer. ISBN 978-085404-824-3.
  11. ^ "Hydroxycitronellal / methyl anthranilate schiff's base, 89-43-0". The Good Scents Company.
  12. ^ Fraternale, Daniele; Ricci, Donata; Flamini, Guido; Giomaro, Giovanna (2011). "Volatiles Profile of Red Apple from Marche Region (Italy)" (PDF). Rec. Nat. Prod. 5 (3): 202–207.
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