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Merck

A8264

4-Aminophthalhydrazide

≥98% (HPLC), powder

Synonym(s):

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

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1 G

CZK 3,920.00

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CZK 14,900.00

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CZK 23,200.00

CZK 3,920.00

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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,

assay

≥98% (HPLC)

Quality Level

200

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
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 that comprises a phthalazine ring. It is more hydrophilic than luminol.[4] Isoluminol is commercially used in a wide variety of in vitro immunoassays and is a chemiluminescence amplifier for studying reactive oxygen species.[4] 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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
WXBF6913V
BCCH9146
BCCF4876
BCCC2589
BCBV2176

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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)
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
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
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
View All Related Papers

Global Trade Item Number

SKUGTIN
A8264-10G04061831159028
A8264-1G04061826740958
A8264-5G04061833423929

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