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Merck
CN

A8264

4-Aminophthalhydrazide

≥98% (HPLC), powder

Synonym(s):

6-Amino-2,3-dihydro-1,4-phthalazinedione, Isoluminol

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About This Item

Empirical Formula (Hill Notation):
C8H7N3O2
CAS Number:
3682-14-2
Molecular Weight:
177.16
NACRES:
NA.83
PubChem Substance ID:
24891326
UNSPSC Code:
12352204
MDL number:
MFCD00010560
Beilstein/REAXYS Number:
164804

Key Documents

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Product Name

4-Aminophthalhydrazide,

InChI

1S/C8H7N3O2/c9-4-1-2-5-6(3-4)8(13)11-10-7(5)12/h1-3H,9H2,(H,10,12)(H,11,13)

SMILES string

Nc1ccc2C(=O)NNC(=O)c2c1

InChI key

HUDPLKWXRLNSPC-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

mp

300 °C (lit.)

solubility

2 M NH4OH: 50 mg/mL, clear to slightly hazy

Quality Level

200

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Application

4-Aminophthalhydrazide has been used in:
  • chemiluminescence-based reactive oxygen species (ROS) assay in bone marrow (BM) neutrophils post-Yersinia pseudotuberculosis infection
  • neutrophil ROS assays post-K. pneumonia exposure
  • neutrophil ROS assays in response to formylated-methionine-leucine-proline

Biochem/physiol Actions

4-Aminophthalhydrazide or isoluminol is a chemiluminescent compound that comprises a phthalazine ring. It is more hydrophilic than luminol. Isoluminol is commercially used in a wide variety of in vitro immunoassays and is a chemiluminescence amplifier for studying reactive oxygen species. It is also useful as an electroluminescence (ECL) biosensor and as a probe for rapid microbial detection.

Features and Benefits

Produces chemiluminescence.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF6913V
BCCH9146
BCCF4876
BCCC2589
BCBV2176

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Caifeng Ding et al.
Chemical communications (Cambridge, England), 46(42), 7990-7992 (2010-09-25)
A new strategy of photoelectrochemical (PEC) analysis with chemiluminescence (CL) of the isoluminol-H(2)O(2)-Co(2+) system as a light source for the determination of physiological thiols in cancer cells was reported for the first time.
Viera Jancinová et al.
Redox report : communications in free radical research, 11(3), 110-116 (2006-06-30)
To address the question why isoluminol, but not luminol, failed to detect oxidants produced intracellularly, differences between these luminophores were investigated with respect to physicochemical parameters and the character of chemiluminescence signal. Our results showed the isoluminol molecule to be
Kazuhiko Tsukagoshi et al.
Journal of chromatography. A, 1143(1-2), 288-290 (2007-02-03)
In our previous study, we developed capillary electrophoresis with an ultraviolet absorption/chemiluminescence dual detection system. Here, to demonstrate one of the possible applications of the capable system as well as confirm the advantage, migration behavior of isoluminol isothiocyanate-labeled alpha-amino acids
B G Yushkov et al.
Bulletin of experimental biology and medicine, 150(3), 352-354 (2011-01-18)
The effects of 3-aminophthalhydrazide and carrageenan on reparative regeneration and expression of CD117 by liver cells after partial hepatectomy were studied in mice. 3-Aminophthalhydrazide stimulated regeneration of the liver and increased the count of CD117(+) hepatocytes. By contrast, carrageenan inhibited
Sundar Neelakantan et al.
Bioorganic & medicinal chemistry letters, 19(19), 5722-5726 (2009-08-25)
Rapid assays for bacteria have been developed utilizing novel LysLysLys-isoluminol (14) and GluGlu-isoluminol (16) probes that have been derived from peptides which potentially mimic bacteriophage attachment protein binding regions. Compared to two conventional methods that are widely used, namely nucleic
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