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10680

Sigma-Aldrich

Anthranilic acid

puriss. p.a., ≥99.5% (T)

Synonym(s):

2-AA, 2-Aminobenzoic acid

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About This Item

Linear Formula:
2-(H2N)C6H4CO2H
CAS Number:
118-92-3
Molecular Weight:
137.14
Beilstein/REAXYS Number:
471803
EC Number:
204-287-5
MDL number:
MFCD00007712
UNSPSC Code:
12352100
PubChem Substance ID:
57646812
NACRES:
NA.21

vapor density

4.7 (vs air)

Quality Level

200

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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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

related product

Product No.
Description
Pricing

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H318

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCC1236
BCBV0749
BCBM7853V
BCBG6182V
BCBB5180V

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"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)
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
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)
"Microbial transformation of carbazole to anthranilic acid by Pseudomonas stutzeri"
Hisatsuka K and Sato M
Bioscience, Biotechnology, and Biochemistry, 58(01), 213-214 (1994)
Water-Soluble Poly (aniline-co-o-anthranilic acid) Copolymers.
Nguyen MT and Diaz AF.
Macromolecules, 28(9), 3411-3415 (1995)
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