4-Aminobenzohydrazide

4-Aminobenzohydrazide Property

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

pka

13.05±0.10(Predicted)

form 

Crystals or Powder

color 

White or beige

Water Solubility 

Soluble in DMSO (10 mg/ml), dilute acids, and water (partly miscible).

BRN 

639053

CAS DataBase Reference

5351-17-7(CAS DataBase Reference)

NIST Chemistry Reference

Benzoic acid, 4-amino-, hydrazide(5351-17-7)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

DG2580000

HazardClass 

IRRITANT

HS Code 

29280000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

4-Aminobenzohydrazide Chemical Properties,Usage,Production

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

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.

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