ChemicalBook Product Catalog Chemical Reagents Organic reagents Hydrazine 4-Aminobenzohydrazide

4-Aminobenzohydrazide

Product Name4-Aminobenzohydrazide
CAS5351-17-7
MFC7H9N3O
MW151.17
EINECS226-324-4
MOL File5351-17-7.mol

Chemical Properties

Melting point	225-227 °C (lit.)
Boiling point	273.17°C (rough estimate)
Density	1.2100 (rough estimate)
refractive index	1.5860 (estimate)
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
solubility	DMF: 10 mg/ml; DMSO: 14 mg/ml; DMSO:PBS(pH7.2) (1:1): 0.5 mg/ml
form	Crystals or Powder
pka	13.05±0.10(Predicted)
color	White or beige
Water Solubility	Soluble in DMSO (10 mg/ml), dilute acids, and water (partly miscible).
BRN	639053
InChI	1S/C7H9N3O/c8-6-3-1-5(2-4-6)7(11)10-9/h1-4H,8-9H2,(H,10,11)
InChIKey	WPBZMCGPFHZRHJ-UHFFFAOYSA-N
SMILES	NNC(=O)c1ccc(N)cc1
CAS DataBase Reference	5351-17-7(CAS DataBase Reference)
NIST Chemistry Reference	Benzoic acid, 4-amino-, hydrazide(5351-17-7)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36
WGK Germany	3
RTECS	DG2580000
HazardClass	IRRITANT
HS Code	29280000
Storage Class	11 - Combustible Solids

MSDS

Provider	Language
(4-Aminobenzoyl)hydrazide	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Description

4-Aminobenzoic acid hydrazide (4-ABAH) is an irreversible inhibitor of myeloperoxidase (MPO; IC₅₀ = 0.3 μM). It reduces the production of hypochlorous acid (HOCl) induced by opsonized zymosan or phorbol 12-myristate 13-acetate (PMA; ) in isolated human neutrophils with IC₅₀ values of 16 and 2.2 μM, respectively. 4-ABAH inhibits PMA-induced formation of neutrophil extracellular traps (NETs) in the same cells. It reduces infarct volume and the severity of neurological deficits, as well as increases survival, in a mouse model of cerebral ischemia induced by transient middle cerebral artery occlusion (MCAO) when administered at a dose of 40 mg/kg twice per day.

Chemical Properties

White or beige crystals or powder

Uses

4-Aminobenzoic hydrazide can be used as a reactant to synthesize:

Acylhydrazone Schiff base ligand by condensation reaction with 2-acetylpyridine.
Oligomeric transition metal complexes applicable in the fabrication of organic-inorganic hybrid devices with efficient electrical and photoelectrical properties.
Oxovanadium(IV)-hydrazide complex as a potential radical scavenger.

Uses

4-Aminobenzhydrazide has an important role in the peroxidation activity of MPO. It is also used in enzyme preparations and in cell cultures.

References

[1] A J KETTLE. Inhibition of myeloperoxidase by benzoic acid hydrazides.[J]. Biochemical Journal, 1995, 308 ( Pt 2): 559-563. DOI: 10.1042/bj3080559
[2] SHUICHIRO NAKABO. Activated neutrophil carbamylates albumin via the release of myeloperoxidase and reactive oxygen species regardless of NETosis.[J]. Modern Rheumatology, 2020, 30 2: 345-349. DOI: 10.1080/14397595.2019.1583819
[3] REZA FORGHANI. Myeloperoxidase propagates damage and is a potential therapeutic target for subacute stroke.[J]. Journal of cerebral blood flow and metabolism: official journal of the International Society of Cerebral Blood Flow and Metabolism, 2015: 485-493. DOI: 10.1038/jcbfm.2014.222
[4] RINA KIM. Ferroptosis of tumour neutrophils causes immune suppression in cancer[J]. Nature, 2022, 612 7939: 338-346. DOI: 10.1038/s41586-022-05443-0

4-Aminobenzohydrazide

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

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