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70215

Sigma-Aldrich

2,3-Naphthalenedicarboxaldehyde

suitable for fluorescence

Synonym(s):

NDA

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About This Item

Linear Formula:
C10H6(CHO)2
CAS Number:
7149-49-7
Molecular Weight:
184.19
Beilstein:
2207267
MDL number:
MFCD00016618
UNSPSC Code:
12352108
PubChem Substance ID:
329762349
NACRES:
NA.32

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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T. Ueda et al.
Analytical Chemistry, 63, 2979-2979 (1991)
Richard C Kevin et al.
Forensic toxicology, 37(1), 17-26 (2019-02-02)
The use of novel synthetic cannabinoids as intoxicants continues in spite of associated health risks. These compounds are typically smoked or vaporized, but many synthetic cannabinoids contain thermally labile chemical moieties. This study investigated the thermal stability six carboxamide-type synthetic
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
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
P. de Montigny et al.
Analytical Chemistry, 59, 1096-1096 (1987)
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