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A8264

Sigma-Aldrich

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
Beilstein:
164804
MDL number:
MFCD00010560
UNSPSC Code:
12352204
PubChem Substance ID:
24891326
NACRES:
NA.83

product name

4-Aminophthalhydrazide,

Assay

≥98% (HPLC)

form

powder

mp

300 °C (lit.)

solubility

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

SMILES string

Nc1ccc2C(=O)NNC(=O)c2c1

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)

InChI key

HUDPLKWXRLNSPC-UHFFFAOYSA-N

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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

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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Anna-Lena Stenfeldt et al.
Luminescence : the journal of biological and chemical luminescence, 22(5), 507-510 (2007-07-05)
A technique was designed for the determination of hydrogen peroxide release. We found, however, that the isoluminol-amplified chemiluminescence technique is a suitable tool for measuring secretion of superoxide but not hydrogen peroxide.
A new isoluminol reagent for chemiluminescence labeling of proteins
Palmioli A, et al.
Tetrahedron Letters, 54, 4446-4450 (2013)
M Rájecký et al.
International journal of laboratory hematology, 34(2), 136-142 (2011-08-13)
The differentiation between extra- and intracellular production of reactive oxygen species (ROS) in whole blood was measured by luminol- and isoluminol-enhanced chemiluminescence (CL). Azide (total CL inhibition), azide + horseradish peroxidase (HRP, restoring extracellular CL), superoxide dismutase + catalase (depleting
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
M T Abidov et al.
Bulletin of experimental biology and medicine, 153(1), 61-63 (2012-07-19)
The content of CD117(+)cells in the kidneys and CD45(low)CD117(+)cells in the bone marrow and blood of mice were studied after partial nephrectomy and under conditions of macrophage stimulation with 3-aminophthalhydrazide. The counts of tubular CD117(+)epitheliocytes sharply increased and the content
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