Anthranilic acid
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Anthranilic acid is an aromatic acid with the formula C6H4(NH2)(CO2H) and has a sweetish taste.[5][6][7] The molecule consists of a benzene ring, ortho-substituted with a carboxylic acid and an amine. As a result of containing both acidic and basic functional groups, the compound is amphoteric. Anthranilic acid is a white solid when pure, although commercial samples may appear yellow. The anion [C6H4(NH2)(CO2)]−, obtained by the deprotonation of anthranilic acid, is called anthranilate. Anthranilic acid was once thought to be a vitamin and was referred to as vitamin L1 in that context, but it is now known to be non-essential in human nutrition.[8]
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Names | |||
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Preferred IUPAC name
2-Aminobenzoic acid[1] | |||
Systematic IUPAC name
2-Aminobenzenecarboxylic acid | |||
Other names
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Identifiers | |||
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3D model (JSmol) |
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3DMet | |||
471803 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider |
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DrugBank |
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ECHA InfoCard | 100.003.898 | ||
EC Number |
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3397 | |||
KEGG |
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PubChem CID |
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RTECS number |
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UNII | |||
CompTox Dashboard (EPA) |
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Properties | |||
C7H7NO2 | |||
Molar mass | 137.138 g·mol−1 | ||
Appearance | white or yellow solid | ||
Odor | odorless | ||
Density | 1.412 g/cm3 | ||
Melting point | 146 to 148 °C (295 to 298 °F; 419 to 421 K)[2] | ||
Boiling point | 200 °C (392 °F; 473 K) (sublimes) | ||
0.572 g/100 mL (25 °C) | |||
Solubility | very soluble in chloroform, pyridine soluble in ethanol, ether, ethyl ether slightly soluble in trifluoroacetic acid, benzene | ||
log P | 1.21 | ||
Vapor pressure | 0.1 Pa (52.6 °C) | ||
Acidity (pKa) |
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-77.18·10−6 cm3/mol | |||
Refractive index (nD) |
1.578 (144 °C) | ||
Thermochemistry | |||
Std enthalpy of formation (ΔfH⦵298) |
-380.4 KJ/mol | ||
Hazards | |||
GHS labelling: | |||
Danger | |||
H318, H319 | |||
P264, P280, P305+P351+P338, P310, P337+P313 | |||
NFPA 704 (fire diamond) | |||
Flash point | > 150 °C (302 °F; 423 K) | ||
> 530 °C (986 °F; 803 K) | |||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) |
1400 mg/kg (oral, rat) | ||
Safety data sheet (SDS) | External MSDS | ||
Legal status | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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