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Merck
CN

10680

Anthranilic acid

≥99.5% (T), solid, puriss. p.a.

Synonym(s):

2-AA, 2-Aminobenzoic acid

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About This Item

Linear Formula:
2-(H2N)C6H4CO2H
CAS Number:
Molecular Weight:
137.14
NACRES:
NA.21
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
204-287-5
MDL number:
Beilstein/REAXYS Number:
471803
Assay:
≥99.5% (T)
Form:
solid
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Product Name

Anthranilic acid, puriss. p.a., ≥99.5% (T)

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

functional group

carboxylic acid

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

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.

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pictograms

Corrosion

signalword

Danger

hcodes

Hazard Classifications

Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk

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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Protocols

Explore mass spectrometry analysis of glycans for glycomic & glycoproteomic neutral & acidic glycan analysis. See a general mass spec glycan analysis procedure.

该聚糖质谱分析方案,被称之为干液滴法,基于原始的MALDI实验并依然是MS领域中最常用的方法。


"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)
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



Global Trade Item Number

SKUGTIN
282715-5G04061833014011
282715-1G04061826662014
10680-100G04061833371527
10680-25G04061838674401