4-Aminobenzohydrazid

4-Aminobenzoic acid hydrazide

HCID 21450CAS 5351-17-7

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Grundinformationen

Standard-SMILES: NNC(=O)c1ccc(N)cc1
InChIKey: WPBZMCGPFHZRHJ-UHFFFAOYSA-N
Summenformel: C7H9N3O
Durchschnittliche Molmasse: 151,17 g/mol
Monoisotopische Masse: 151,07456191

Überblick

4-aminobenzohydrazide is an aminobenzoic acid. It has a role as an EC 1.11.2.2 (myeloperoxidase) inhibitor.

Namen und Bezeichner

Bevorzugter Name: 4-Aminobenzoic acid hydrazide
IUPAC: 4-aminobenzohydrazide
Lokaler Name: 4-Aminobenzohydrazid
Englischer Name: 4-Aminobenzohydrazide
Summenformel: C7H9N3O
Molmasse: 151.17

Namen und Synonyme

5351-17-74-Aminobenzhydrazide4-Aminobenzoic acid hydrazideAminostimilp-Aminobenzoic acid hydrazidepara-AminobenzhydrazideDTXSID302017204-aminobenzoic acid-hydrazideRefChem:97833DTXCID60124211226-324-44-Aminobenzohydrazide

Weitere Namen anzeigen

4-POBN4NPhCON2WLN: ZNUYQR DZambenhydrazideTIMTEC-BB SBB007555N,4-Diaminobenzamide

Amben hydrazidep-Aminobenzhydrazide4-Aminobenzoylhydrazinep-Aminobenzoyl hydrazideBenzoic acid, 4-amino-, hydrazidep-Aminobenzoic hydrazidep-Aminobenzoylhydrazine4-Aminobenzoic hydrazide

Datenbank-Bezeichner

CAS: 5351-17-7
PubChem CID: 21450
DTXSID: DTXSID30201720
ChEMBL: CHEMBL2170241
ChEBI: CHEBI:233355
EC Number: 226-324-4
Nikkaji: J20.610E

Eigenschaften

Berechnete Struktureigenschaften

XLogP: -0,7
Polarare Oberfläche (TPSA): 81,1 Å²
H-Brücken-Donoren: 3
H-Brücken-Akzeptoren: 3
Frei drehbare Bindungen: 1
Schwere Atome: 11
Formalladung: 0
Komplexität: 141

Experimentelle und physikochemische Eigenschaften

LogP-0.75

Physikochemische Eigenschaften

Schmelzpunkt: 225 · 225-227 °C (lit.)
Siedepunkt: 273.17 °C · 273.17°C (rough estimate)
Dichte: 1.21 · 1.2100 (rough estimate)
Brechungsindex: 1.586 · 1.5860 (estimate)
storage temp.: Keep in dark place,Inert atmosphere,Room temperature
Löslichkeit: 10 mg/ml; · DMF: 10 mg/ml; DMSO: 14 mg/ml; DMSO:PBS(pH7.2) (1:1): 0.5 mg/ml
pka: 13.05 · 13.05±0.10(Predicted)
Aggregatzustand: Crystals or Powder
Farbe: White or beige
Wasserlöslichkeit: Soluble in DMSO (10 mg/ml), dilute acids, and water (partly miscible).
BRN: 639053 · 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 Datenbank: 5351 · 5351-17-7(CAS DataBase Reference)
NIST chemische Informationen: 4 · Benzoic acid, 4-amino-, hydrazide(5351-17-7)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 44 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Sicherheitsdaten

wgk: 3
hs_code: 29280000
RTECS-Nr.: DG2580000
risk_code: 36/37/38
hazard_code: Xi
safety_code: 26-36
hazard_class: IRRITANT
Speicherklasse: 11 - Combustible Solids

Chemie und Industrie

Anwendungen · 2 Einträge

Beschreibung4-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.

Verwenden4-Aminobenzhydrazide has an important role in the peroxidation activity of MPO. It is also used in enzyme preparations and in cell cultures.