o-Aminobenzoic acid; 2-Aminobenzoic acid; Vitamin L1; Anthranilate
|Jmol 3D model||Interactive image
|Molar mass||137.14 g·mol−1|
|Appearance||white or yellow solid|
|Melting point||146 to 148 °C (295 to 298 °F; 419 to 421 K)|
|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
|Vapor pressure||0.1 Pa (52.6 °C)|
Refractive index (nD)
|1.578 (144 °C)|
Std enthalpy of
|Safety data sheet||External MSDS|
|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)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Anthranilic acid (or o-amino-benzoic acid) is an aromatic acid with the formula C6H4(NH2)(CO2H). The molecule consists of a substituted benzene ring, hence is classed as aromatic, with two adjacent, or "ortho-" functional groups, a carboxylic acid and an amine. The compound is consequently amphoteric. In appearance, anthranilic acid is a white solid when pure, although commercial samples may appear yellow. It is sometimes referred to as vitamin L1 and has a sweetish taste. The anion [C6H4(NH2)(CO2)]−, obtained by the deprotonation of anthranilic acid, is called anthranilate.
Many routes to anthranilic acid have been described. Industrially it is produced from phthalic anhydride, beginning with amination:
- C6H4(CO)2O + NH3 + NaOH → C6H4(C(O)NH2)CO2Na + H2O
- C6H4(C(O)NH2)CO2Na + HOCl → C6H4NH2CO2H + NaCl + CO2
A related method involves treating phthalimide with sodium hypobromite in aqueous sodium hydroxide, followed by neutralization. In the era when indigo dye was obtained from plants, it was degraded to give anthranilic acid.
Anthranilic acid was first obtained by base-induced degradation of indigo.
Industrially, anthranilic acid is an intermediate in the production of azo dyes and saccharin. It and its esters are used in preparing perfumes to imitate jasmine and orange, pharmaceuticals (loop diuretics e.g. furosemide) and UV-absorber as well as corrosion inhibitors for metals and mold inhibitors in soy sauce.
Fenamic acid is a derivative of anthranilic acid,:235 which in turn is a nitrogen isostere of salicylic acid, which is the active metabolite of aspirin.:235 Several non-steroidal anti-inflammatory drugs, including mefenamic acid, tolfenamic acid, flufenamic acid, and meclofenamic acid are derived from fenamic acid or anthranilic acid and are called "anthranilic acid derivatives" or "fenamates".:17
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- Sriram D, Yogeeswari P. Medicinal Chemistry, 2nd Edition. Pearson Education India, 2010. ISBN 9788131731444
- Auburn University course material. Jack DeRuiter, Principles of Drug Action 2, Fall 2002 1: Non-Steroidal Antiinflammatory Drugs (NSAIDS)
- He, Lin; Li, Haoquan; Chen, Jianbin; Wu, Xiao-Feng (2014). "Recent advances in 4(3H)-quinazolinone syntheses". RSC Advances 4 (24): 12065. doi:10.1039/c4ra00351a. ISSN 2046-2069.
- Anthranilate Fluorescence Marks a Calcium-Propagated Necrotic Wave That Promotes Organismal Death in C. elegans mention of Anthranilic acid in news about organismic death process