Chemistry:Methyl anthranilate

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Not to be confused with Menthyl anthranilate.
Methyl anthranilate
Names
Preferred IUPAC name
Methyl 2-aminobenzoate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
EC Number
  • 205-132-4
KEGG
UNII
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 pictograms GHS07: Harmful
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).
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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 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]

Schiff bases in perfumery

Methyl anthranilate is one of the two amines most commonly used to form Schiff bases in the fragrance industry, the other being ethyl anthranilate.[9] When methyl anthranilate reacts with an aldehyde, water is released and a single, heavier compound is formed. These compounds are typically yellow-to-orange, viscous liquids that are more stable than their parent aldehydes and have greater tenacity, or staying power, on skin, though they darken over time.[9][10]

Several methyl anthranilate-based Schiff bases are sold under trade names and are widely used across the fragrance industry, such as:

Anisimea
Formed with anisaldehyde, a powdery mimosa character similar to the sweet smell of common orange flower.
Aurantiol (also sold as Auralva)
Formed with hydroxycitronellal, has an orange blossom and neroli character and is described as the most widely used Schiff base in perfumery.[9][11]. It was discovered in 1908 and its first use in a commercial fragrance was Guerlain L'Heure Bleue (1912).[12]
Verdantiol (also sold as Lilyantine & Lilianth)
Formed with Lilial, has a linden blossom character with orange blossom undertones.[13]
Lyrame (also sold as Lyrantion)
Formed with the aldehyde Lyral, has a fresh lily-of-the-valley character with notes of orange blossom.[14][15]
Helioforte
Formed with Helional, has a marine, almondy character and was developed by the Florasynth company.[16][17]
Vertosine (also sold as Ligantraal, Agrumea)
A Schiff base of methyl anthranilate and Triplal; noted by Calkin and Jellinek in the early 1990s as a comparatively recent addition to the category.[10][18]
A Schiff-base with Trifernal® (3-Phenylbutanal)
This is in the patent literature.

Perfumers can also add methyl anthranilate as a plain, separate ingredient alongside an aldehyde such as hydroxycitronellal, Lyral, or Helional, allowing the Schiff base to form gradually inside the finished compound over a period of weeks or months, in a process known as maceration.[10] This gradual reaction continues even after a perfume has been bottled; perfumery analysts note that older samples may show Schiff bases that were not present when the fragrance was originally formulated, which complicates efforts to determine an exact original formula from chemical analysis alone.[10] Unintended post-bottling formation can also change a finished fragrance's scent: perfumer Paul Kiler has pointed to Roja Parfums Enigma Pour Homme (2013, sold as Creation-E in the United States) as a case in which a Schiff base formed between methyl anthranilate and vanillin roughly a year after bottling, darkening the fragrance and giving it an unintended root beer-like note.[19]

Although once widely used, Schiff bases have become less common in modern perfumery, in part because of the strong color many of them produce.[19]

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.[20]

References

  1. ↑ 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. 
  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. ↑ 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. ↑ "methyl anthranilate". https://scentsandflavors.com/database/9dbb4fd1-382e-47f0-98b0-f7a5193e5e41. 
  5. ↑ "The Japan Food Chemical Research Foundation". http://www.ffcr.or.jp/zaidan/ffcrhome.nsf/7bd44c20b0dc562649256502001b65e9/916cae3da5a8a11b49256f320018877f/$FILE/D248.pdf. 
  6. ↑ 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. 
  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. doi:10.3389/fvets.2020.00533. 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. ↑ 9.0 9.1 9.2 Schmidt, Conrad (January–February 2002). "Schiff Bases — A Primer". Perfumer & Flavorist 27. https://img.perfumerflavorist.com/files/base/allured/all/document/2016/02/pf.PF_27_01_032_01.pdf. 
  10. ↑ 10.0 10.1 10.2 10.3 Calkin, Robert R.; Jellinek, J. Stephan (1994). Perfumery: Practice and Principles. New York: John Wiley & Sons, Inc.. ISBN 0-471-58934-9. https://archive.org/details/PerfumeryPrinciplesAndPractice1994/. 
  11. ↑ "hydroxycitronellal / methyl anthranilate schiff's base". https://www.thegoodscentscompany.com/data/rw1004281.html. 
  12. ↑ Ellena, J.C. (1994). "Creative Perfumery: Composition Techniques". in Muller, P.M.; Lamparsky, D.. Perfumes: Art, Science and Technology. Springer. pp. 333–346. ISBN 978-94-010-5701-1. 
  13. ↑ "lilial / methyl anthranilate schiff's base". https://www.thegoodscentscompany.com/data/rw1006301.html. 
  14. ↑ "Lyrame C". https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4666527.htm. 
  15. ↑ "leerall / methyl anthranilate schiff's base". https://www.thegoodscentscompany.com/data/rw1025921.html. 
  16. ↑ Edwards, Michael (2024). American Legends: The evolution of American fragrances. Nice, France: Exigence Puissance 3. ISBN 978-0-6454839-0-1. 
  17. ↑ "ocean propanal / methyl anthranilate schiff's base". https://www.thegoodscentscompany.com/data/rw1005761.html. 
  18. ↑ "ivy carbaldehyde / methyl anthranilate schiff's base". https://www.thegoodscentscompany.com/data/rw1013971.html. 
  19. ↑ 19.0 19.1 Bulliqi, Eddie (March 2, 2020). "Schiff Base Shuffling: Paul Kiler's New Work with Old Chemistry". Perfumer & Flavorist 45: 18–22. https://archive.org/details/perfumerflavorist202003-dl. 
  20. ↑ 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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