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

Key Documents

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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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1 of 4

This Item
A1757A0156A4685
4-Aminophthalhydrazide

Sigma-Aldrich

A8264

4-Aminophthalhydrazide

6-Azauracil ≥98%

Sigma-Aldrich

A1757

6-Azauracil

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

Sigma-Aldrich

A0156

N-(4-Aminobutyl)-N-ethylisoluminol

Luminol sodium salt

Sigma-Aldrich

A4685

Luminol sodium salt

assay

≥98% (HPLC)

assay

≥98%

assay

≥90%

assay

≥98% (titration)

solubility

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

solubility

1 M NH4OH: 50 mg/mL, clear to slightly hazy, colorless to light yellow-green

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

Quality Level

200

Quality Level

100

Quality Level

200

Quality Level

300

form

powder

form

powder

form

powder

form

powder and chunks

mp

300 °C (lit.)

mp

274-275 °C (lit.)

mp

259-260 °C (lit.)

mp

-

Application

4-Aminophthalhydrazide has been used in:
  • chemiluminescence-based reactive oxygen species (ROS) assay in bone marrow (BM) neutrophils post-Yersinia pseudotuberculosis infection[1]
  • neutrophil ROS assays post-K. pneumonia exposure[2]
  • neutrophil ROS assays in response to formylated-methionine-leucine-proline[3]

Biochem/physiol Actions

4-Aminophthalhydrazide or isoluminol is a chemiluminescent compound[4] that comprises a phthalazine ring. It is more hydrophilic than luminol.[5] Isoluminol is commercially used in a wide variety of in vitro immunoassays[4] and is a chemiluminescence amplifier for studying reactive oxygen species.[5] It is also useful as an electroluminescence (ECL) biosensor and as a probe for rapid microbial detection.[4]

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_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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Certificates of Analysis (COA)

Lot/Batch Number
WXBF6913V
BCCH9146
BCCF4876
BCCC2589
BCBV2176

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Jenna Lorenzini et al.
Cellular microbiology, 19(9) (2017-03-28)
Blastomycosis elicits a pyogranulomatous inflammatory response that involves a prominent recruitment of neutrophils to the site of infection. Although neutrophils are efficiently recruited to the site of infection, this event is paradoxically coupled with the host's inability to control infection
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
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
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
View All Related Papers

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