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Sigma-Aldrich

2,3-Naphthalenedicarboxaldehyde

suitable for fluorescence

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Synonym(s):
NDA
Linear Formula:
C10H6(CHO)2
CAS Number:
7149-49-7
Molecular Weight:
184.19
Beilstein:
2207267
MDL number:
MFCD00016618
PubChem Substance ID:
329762349

form

crystals

Quality Level

100

impurities

≤2% mono- and dicarboxylic acid (1H-NMR)

mp

131-133 °C (lit.)
132-135 °C

fluorescence

λex 420 nm; λem ~480 nm in 0.1 M borate pH 9.3 (after derivatization with glycine [~90 μM glycine, ~20 μM N-])

suitability

suitable for fluorescence

storage temp.

2-8°C

SMILES string

[H]C(=O)c1cc2ccccc2cc1C([H])=O

InChI

1S/C12H8O2/c13-7-11-5-9-3-1-2-4-10(9)6-12(11)8-14/h1-8H

InChI key

ZIPLKLQPLOWLTM-UHFFFAOYSA-N

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General description

2,3-Naphthalenedicarboxaldehyde, also known as NDA, is a novel fluorescent derivatization agent. The fluorescence max. excitation of NDA is in the range of 424 nm and max. emission is achieved at 484nm.

2,3-Naphthalenedicarboxaldehyde is a fluorescent derivatization agent of primary amines, amino acids, and small peptides. The reaction between the amino compounds and NDA results in highly fluorescent and stable derivative compounds.

Application

2,3-Naphthalenedicarboxaldehyde is used as a fluorescent labelling agent for quantification of Histamine in human immunoglobulin preparations. NAD is used as a derivatization agent for glutathione to quantify protein glutathionylation. It is a suitable reagent used for the development of fluorescence-based microtiter plate assay for γ-glutamylcyclotransferase.

Features and Benefits

NDA based fluorescent assays have the following benefits over O-Phthalaldehyde (OPA):

  • High Reaction rate.
  • High Fluorescence quantum yield.
  • No uncommon excitation wavelength.
  • No side reactions.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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O Yassine et al.
Analytica chimica acta, 609(2), 215-222 (2008-02-12)
In this work, we developed a PDMS electrophoresis device able to carry out on-chip derivatization and quantification of amino acids (AAs) using naphthalene-2,3-dicarboxaldehyde (NDA) as a fluorogenic agent. A chemical modification of the PDMS surface was found compulsory to achieve
Automated precolumn derivatization of amino acids, small peptides, brain amines and drugs with primary amino groups for reversed-phase high-performance liquid chromatography using naphthalenedialdehyde as the fluorogenic label.
H Koning et al.
Journal of chromatography, 533, 171-178 (1990-11-30)
Yu-Yen Kao et al.
Journal of chromatography. A, 1217(4), 582-587 (2009-12-17)
We describe simultaneous analysis of naphthalene-2,3-dicarboxaldehyde (NDA)-amino acid and NDA-biogenic amine derivatives by CE in conjunction with light-emitting diode-induced fluorescence detection using poly(ethylene oxide) (PEO) solutions containing sodium dodecyl sulfate (SDS). After sample injection, via EOF 0.1% PEO prepared in
Stéphanie Marchand et al.
Analytica chimica acta, 660(1-2), 158-163 (2010-01-28)
A simple and automated high performance liquid chromatography (HPLC) method for the separation and quantitative determination of gamma-glutamylcysteine and reduced glutathione (GSH) in wines is reported. This technique involves the use of a pre-column derivatization with 2,3-naphthalenedialdehyde (NDA), an isocratic
Po-Ling Chang et al.
Electrophoresis, 32(9), 1080-1083 (2011-03-31)
Branched-chain amino acids (BCAAs) are one of the important biomarkers for monitoring liver disease such as hepatitis or hepatoma. In this communication, we present the determination of the concentrations of BCAA in ascites by CE light-emitted diode-induced fluorescence (LEDIF) using
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