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A8264

Sigma-Aldrich

4-Aminophthalhydrazide

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Synonym(s):
6-Amino-2,3-dihydro-1,4-phthalazinedione, Isoluminol
Empirical Formula (Hill Notation):
C8H7N3O2
CAS Number:
Molecular Weight:
177.16
Beilstein/REAXYS Number:
164804
MDL number:
PubChem Substance ID:
NACRES:
NA.83

assay

≥98% (HPLC)

Quality Level

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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This Item
A0156A4685C8011
4-Aminophthalhydrazide

A8264

4-Aminophthalhydrazide

N-(4-Aminobutyl)-N-ethylisoluminol ≥90%

A0156

N-(4-Aminobutyl)-N-ethylisoluminol

Luminol sodium salt

A4685

Luminol sodium salt

Chelidamic acid hydrate ≥95%, powder

C8011

Chelidamic acid hydrate

solubility

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

solubility

glacial acetic acid: 50 mg/mL, clear, colorless to yellow

solubility

water: 50 mg/mL, clear to very slightly hazy, colorless to faint red

solubility

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

form

powder

form

powder

form

powder and chunks

form

powder

mp

300 °C (lit.)

mp

259-260 °C (lit.)

mp

-

mp

267 °C (dec.) (lit.)

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Customers Also Viewed

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A new isoluminol reagent for chemiluminescence labeling of proteins
Palmioli A, et al.
Tetrahedron Letters, 54, 4446-4450 (2013)
Zian Lin et al.
Analytical chemistry, 78(15), 5322-5328 (2006-08-02)
A new method for pressurized capillary electrochromatography (pCEC) coupling with chemiluminescence (CL) detection using a modified on-column coaxial flow detection interface was developed. To evaluate the feasibility and reliability of the experimental setup, the typical CL compounds luminol and isoluminol
Chiedzo M Mpofu et al.
Gastroenterology, 133(5), 1487-1498 (2007-10-09)
Crohn's disease (CD) is mimicked by inherited phagocyte disorders and is associated with circulating antibodies against yeast mannan (anti-Saccharomyces cerevisiae antibody; ASCA). We speculated that mannans might impair phagocyte function. S cerevisiae mannan was assessed for its effects on human
Maria Dahlberg et al.
Luminescence : the journal of biological and chemical luminescence, 23(3), 139-143 (2008-05-03)
Chemiluminescence systems enhanced by either isoluminol or luminol in combination with a peroxidase are sensitive methods for the detection of reactive oxygen species (ROS) generated by phagocyte NADPH oxidase. The two amplifying substrates are structurally very similar, differing only in
Chien-Wen S Kuo et al.
Journal of immunology (Baltimore, Md. : 1950), 187(1), 361-371 (2011-06-08)
Infection of human cells by human T cell leukemia virus type 1 (HTLV-1) is mediated by the viral envelope glycoproteins. The gp46 surface glycoprotein binds to cell surface receptors, including heparan sulfate proteoglycans, neuropilin 1, and glucose transporter 1, allowing

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