Methyl anthranilate

Source: Wikipedia, the free encyclopedia.
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 Edit this at Wikidata
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
Odor grape-like
Density 1.168 g/cm3
Melting point 24 °C (75 °F; 297 K)
Boiling point 256 °C (493 °F; 529 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
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 checkY☒N ?)

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.

Chemical properties

It is a colorless 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.[1] It has a refractive index of 1.583 at 589 nm of wavelength and 20 °C.[2] It shows a light blue-violet 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. Pure, it has a fruity grape smell; at 25 ppm it has a sweet, fruity, Concord grape-like smell with a musty and berry nuance.[3][4]

Uses

Methyl anthranilate acts as a

grape soda), fruit (e.g. Grāpples), chewing gum, and nicotine products.[6]

Methyl anthranilate both as a component of various natural essential oils and as a synthesised aroma-chemical is used extensively in modern perfumery.[3][7] 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,[8] produced by combining methyl anthranilate and hydroxycitronellal.[9]

In organic synthesis, methyl anthranilate can be used as a source of the highly reactive

Diels-Alder addition or other substitution at the ring.[10]

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.[11]

References

  1. doi:10.1002/hlca.19630460506
    .
  2. doi:10.1135/cccc19960751
    .
  3. ^ a b The Good Scents Company: Methyl anthranilate
  4. ^ The Japan Food Chemical Research Foundation
  5. ^ Ahmad, Shahzad, et al. "Effectiveness of methylanthranilate and anthraquinone as repellent against house crows (Corvus splendens) on wheat seeds and seedlings in captivity." Pakistan Journal of Zoology 48.5 (2016).
  6. PMID 24805984
    .
  7. ISBN 978-1-870228-24-4
  8. ISBN 978-085404-824-3
  9. ^ Good Scents Company Page for Aurantiol
  10. PMID 22443517
    . Retrieved 20 November 2022.
  11. ^ Daniele Fraternale, Donata Ricci, Guido Flamini and Giovanna Giomaro. Volatiles Profile of Red Apple from Marche Region (Italy). Rec. Nat. Prod. (2011), 5:3; 202-207. pdf
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