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10680

Sigma-Aldrich

Anthranilic acid

puriss. p.a., ≥99.5% (T)

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Synonym(s):
2-AA, 2-Aminobenzoic acid
Linear Formula:
2-(H2N)C6H4CO2H
CAS Number:
Molecular Weight:
137.14
Beilstein/REAXYS Number:
471803
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

vapor density

4.7 (vs air)

Quality Level

grade

puriss. p.a.

assay

≥99.5% (T)

form

solid

ign. residue

≤0.05% (as SO4)

mp

144-148 °C (lit.)
145-147 °C

anion traces

chloride (Cl-): ≤500 mg/kg
sulfate (SO42-): ≤100 mg/kg

cation traces

Ca: ≤100 mg/kg
Cd: ≤5 mg/kg
Co: ≤5 mg/kg
Cr: ≤5 mg/kg
Cu: ≤5 mg/kg
Fe: ≤5 mg/kg
K: ≤50 mg/kg
Mg: ≤5 mg/kg
Mn: ≤5 mg/kg
Na: ≤50 mg/kg
Ni: ≤5 mg/kg
Pb: ≤5 mg/kg
Zn: ≤5 mg/kg

SMILES string

Nc1ccccc1C(O)=O

InChI

1S/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10)

InChI key

RWZYAGGXGHYGMB-UHFFFAOYSA-N

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1 of 4

This Item
A898558.20112709530
Anthranilic acid puriss. p.a., ≥99.5% (T)

10680

Anthranilic acid

Anthranilic acid reagent grade, ≥98%

A89855

Anthranilic acid

Anthranilic acid for synthesis

8.20112

Anthranilic acid

Anthranilic acid-(phenyl-13C6) 99 atom % 13C, 98% (CP)

709530

Anthranilic acid-(phenyl-13C6)

assay

≥99.5% (T)

assay

≥98%

assay

≥99.0% (acidimetric)

assay

98% (CP)

Quality Level

200

Quality Level

100

Quality Level

200

Quality Level

-

form

solid

form

powder

form

solid

form

powder

mp

144-148 °C (lit.), 145-147 °C

mp

144-148 °C (lit.)

mp

146-148 °C

mp

144-148 °C

cation traces

Ca: ≤100 mg/kg, Co: ≤5 mg/kg, Cu: ≤5 mg/kg, K: ≤50 mg/kg, Mn: ≤5 mg/kg, Ni: ≤5 mg/kg, Zn: ≤5 mg/kg, Cd: ≤5 mg/kg, Fe: ≤5 mg/kg, Na: ≤50 mg/kg, Cr: ≤5 mg/kg, Pb: ≤5 mg/kg, Mg: ≤5 mg/kg

cation traces

-

cation traces

-

cation traces

-

General description

Anthranilic acid is an ortho-substituted aniline derivative. Anthranilic acid can be obtained from carbozole via microbial transformation using Pseudomonas stutzeri. It is a substrate of enzyme anthranilate hydroxylase found in Aspergillus niger.

Application

Anthranilic acid (AA) may be employed for the following studies:
  • Fluorescent labeling of glycans.
  • Synthesis of triptycene and derivatives, via diazotization reaction.
  • As fluorescent label for the facile labeling of oligosaccharides (acidic and neutral).
  • As fluorescent label for carbohydrate analysis.
  • Derivatization of oligosaccharides.
  • Preparation of poly(aniline-co-o-anthranilic acid) copolymers.
Anthranilic acid has been used in the microwave-assisted preparation of 2-heptyl-3-hydroxy-4(1H)-quinolone, also called as Pseudomonas quinolone signal, which finds applications in quorum sensing mechanism.
Used for non-selective, efficient fluorescent labeling of glycans.

Other Notes

Sales restrictions may apply

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Description
Pricing

pictograms

Corrosion

signalword

Danger

hcodes

Hazard Classifications

Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

302.0 °F - closed cup

flash_point_c

150 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


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K R Anumula et al.
Glycobiology, 8(7), 685-694 (1998-06-11)
Facile labeling of oligosaccharides (acidic and neutral) in a nonselective manner was achieved with highly fluorescent anthranilic acid (AA, 2-aminobenzoic acid) (more than twice the intensity of 2-aminobenzamide, AB) for specific detection at very high sensitivity. Quantitative labeling in acetate-borate
"Microwave-assisted preparation of the quorum-sensing molecule
2-heptyl-3-hydroxy-4 (1H)-quinolone and structurally related analogs"
Hodgkinson TJ, et al
Nature Protocols, 7(06), 1184-1192 (2012)
Benzynes via aprotic diazotization of anthranilic acids: a convenient synthesis of triptycene and derivatives.
Friedman L and Logullo FM.
Journal of the American Chemical Society, 85(10), Benzynes via aprotic-Benzynes via aprotic (1963)
Water-Soluble Poly (aniline-co-o-anthranilic acid) Copolymers.
Nguyen MT and Diaz AF.
Macromolecules, 28(9), 3411-3415 (1995)
"Microbial transformation of carbazole to anthranilic acid by Pseudomonas stutzeri"
Hisatsuka K and Sato M
Bioscience, Biotechnology, and Biochemistry, 58(01), 213-214 (1994)

Protocols

The development of modern mass spectrometry (MS) equipment with high resolution and mass accuracy has led to its use in analyzing glycans for both profiling and structural studies.

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