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Methyl anthranilate

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Identification
Molecular formula
C8H9NO2
CAS number
134-20-3
IUPAC name
methyl 2-aminobenzoate
State
State

At room temperature, methyl anthranilate is typically in a liquid state. It is not volatile and has a strong, sweet smell reminiscent of grapes, contributing to its use in various applications.

Melting point (Celsius)
24.00
Melting point (Kelvin)
297.15
Boiling point (Celsius)
256.00
Boiling point (Kelvin)
529.15
General information
Molecular weight
151.16g/mol
Molar mass
151.1640g/mol
Density
1.1680g/cm3
Appearence

Methyl anthranilate is a clear to pale yellow liquid with a distinctive grape-like smell. It is used in flavoring and perfuming applications due to its pleasant aromatic scent.

Comment on solubility

Solubility of Methyl 2-Aminobenzoate

Methyl 2-aminobenzoate, known for its aromatic character due to the presence of an amino group, exhibits noteworthy solubility characteristics. Its solubility can greatly influence various applications, particularly in organic synthesis and pharmaceutical formulations.

When examining the solubility of this compound, consider the following key points:

  • Polar Nature: The amino group contributes to an increase in polarity, enhancing its solubility in polar solvents.
  • Solvent Compatibility: Methyl 2-aminobenzoate is typically soluble in:
    • Water (to a limited extent)
    • Alcohols such as methanol and ethanol
    • Some organic solvents like acetone or ethyl acetate
  • Temperature Dependence: Solubility tends to increase with temperature, making warmer solvents generally more effective.
  • pH Influence: The solubility may also vary with pH, as the amino group can exist in both protonated and deprotonated forms, affecting its interactions with solvents.

In conclusion, the solubility of methyl 2-aminobenzoate is a dynamic property, influenced by its functional groups and the surrounding environment. Understanding these factors is essential for harnessing its full potential in different applications.

Interesting facts

Interesting Facts About Methyl 2-Aminobenzoate

Methyl 2-aminobenzoate, commonly referred to as methyl anthranilate, is a fascinating compound that has garnered attention in various fields of study. Here are some interesting points about this intriguing molecule:

  • Natural Occurrence: Methyl 2-aminobenzoate is found in nature, particularly in the essential oils of citrus fruits. Its pleasant aroma contributes to its use in food flavoring.
  • Aroma and Flavor: Known for its sweet, grape-like scent, methyl 2-aminobenzoate is widely used in the food and fragrance industries. It's often used to enhance the flavor of candies and beverages.
  • Biological Significance: The compound has been studied for its potential biological activities, including anti-inflammatory and antibacterial effects. Researchers are exploring its properties for medicinal applications.
  • Synthesis: Methyl 2-aminobenzoate can be synthesized through various methods, typically involving the reaction of 2-aminobenzoic acid with methanol under acidic conditions.
  • Insect Deterrent: Studies have shown that methyl 2-aminobenzoate could act as an insect repellent, making it of interest in agricultural practices for pest control.

The compound's unique properties make it a subject of interest not only in chemistry but also in biology and environmental science. As scientists continue to explore the versatility of methyl 2-aminobenzoate, we may uncover even more applications and benefits derived from this compound.

Synonyms
METHYL ANTHRANILATE
Methyl 2-aminobenzoate
134-20-3
2-Aminobenzoic acid methyl ester
Methyl o-aminobenzoate
o-Carbomethoxyaniline
2-Carbomethoxyaniline
Anthranilic acid methyl ester
Methylanthranilate
2-(Methoxycarbonyl)aniline
Benzoic acid, 2-amino-, methyl ester
Anthranilic acid, methyl ester
O-methyl anthranilate
FEMA No. 2682
o-Aminobenzoic acid methyl ester
Amino methyl benzoate, o-
NSC 3109
Methyl anthranilate (natural)
CCRIS 1349
o-Amino methyl benzoate
Methylester kyseliny anthranilove
CHEBI:73244
HSDB 1008
methyl antranilate
Carbomethoxyaniline
EINECS 205-132-4
MFCD00007710
Epa Pesticide Chemical Code 128725
UNII-981I0C1E5W
BRN 0606965
Methylester kyseliny anthranilove [Czech]
DTXSID6025567
AI3-01022
FEMA 2682
o-Aminobenzoic acid, methyl ester
2-Aminobenzoic acid, methyl ester
981I0C1E5W
Methyl ester of o-Aminobenzoic acid
NSC-3109
DTXCID105567
METHYL ANTHRANILATE [MI]
2-Aminobenzoic acid-methyl ester
METHYL ANTHRANILATE [FCC]
2-amino-benzoic acid methyl ester
METHYL ANTHRANILATE [FHFI]
METHYL ANTHRANILATE [HSDB]
METHYL ANTHRANILATE [VANDF]
METHYL ANTHRANILATE [MART.]
METHYL ANTHRANILATE [WHO-DD]
BENZOIC ACID METHYL ESTER,2-AMINO
Methyl 2-Aminobenzoate (Methyl Anthranilate)
aniline, 2-methoxycarbonyl-
METHYL ANTHRANILATE (MART.)
Benzoic acid, amino-, methyl ester
CAS-134-20-3
METHYL-2-AMINOBENZOATE
Methylanthranilate; Methyl 2-aminobenzoate; 2-Aminobenzoic acid methyl ester
oCarbomethoxyaniline
methyl aminobenzoate
2Carbomethoxyaniline
Methyl oaminobenzoate
methyl 2aminobenzoate
Neroli oil artificial
BIRD SHIELD
methyl anthranilic acid
o-methoxycarbonylaniline
REJEX-IT
methyl 2-amino-benzoate
Anthranilate methyl ester
2(Methoxycarbonyl)aniline
Amino methyl benzoate, o
O-Methyl anthranilic acid
Methyl O-aminobenzoic acid
WLN: ZR BVO1
REJEX-IT AP 50
REJEX-IT TP 40
O-Aminobenzoate methyl ester
2-Aminobenzoate methyl ester
SCHEMBL57713
Methyl 2-aminobenzoate, 99%
oAminobenzoic acid methyl ester
2Aminobenzoic acid methyl ester
METHY ORTHO-AMINOBENZOATE
CHEMBL1493986
2-Aminobenzoic-acid methyl ester
NSC3109
2-amino benzoic acid methyl ester
METHYL ANTHRANILATE [INCI]
Benzoic acid, 2amino, methyl ester
STR00871
Tox21_201657
Tox21_300347
BDBM50581836
methyl ester of o-amino benzoic acid
STK045541
AKOS000119222
CS-W019645
FM01597
USEPA/OPP Pesticide Code: 128725
Methyl anthranilate, >=98%, FCC, FG
NCGC00091409-01
NCGC00091409-02
NCGC00091409-03
NCGC00254347-01
NCGC00259206-01
AC-11600
HY-77342
Methyl-2-aminobenzoate;Methyl anthranilate
DB-042220
Methyl anthranilate, natural, >=99%, FG
A0500
NS00002018
C20634
D77860
Methyl 2-aminobenzoate, ReagentPlus(R), >=99%
Methyl anthranilate, natural (US), >=99%, FG
Q420894
F2141-0131
Methyl 2-aminobenzoate, Vetec(TM) reagent grade, 98%
205-132-4