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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:
Molecular Weight:
177.16
Beilstein:
164804
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
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

Signal Word

Warning

Hazard Statements

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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A new isoluminol reagent for chemiluminescence labeling of proteins
Palmioli A, et al.
Tetrahedron Letters, 54, 4446-4450 (2013)
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.
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
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
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

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