2-hydroxy-N'-[(1E)-(2-hydroxyphenyl)methylidene]benzohydrazide

• ChemBase ID: 154644
• Molecular Formular: C14H12N2O3
• Molecular Mass: 256.25668
• Monoisotopic Mass: 256.08479225
• SMILES: c1ccc(c(c1)/C=N/NC(=O)c1ccccc1O)O
• Canonical SMILES: Oc1ccccc1/C=N/NC(=O)c1ccccc1O
• InChI: InChI=1S/C14H12N2O3/c17-12-7-3-1-5-10(12)9-15-16-14(19)11-6-2-4-8-13(11)18/h1-9,17-18H,(H,16,19)
• InChIKey: OMCYEZUIYGPHDJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-N'-[(1E)-(2-hydroxyphenyl)methylidene]benzohydrazide; 2-hydroxy-N'-[(2-hydroxyphenyl)methylidene]benzohydrazide
• IUPAC Traditional name: 2-hydroxy-N'-[(1E)-(2-hydroxyphenyl)methylidene]benzohydrazide; 2-hydroxy-N'-[(2-hydroxyphenyl)methylidene]benzohydrazide
• Synonyms: 2-Hydroxybenzylidene 2-hydroxybenzhydrazide; NSC 87864; SCS; Salicylidene salicylhydrazide; 亚水杨基水杨基肼

Database IDs

• CAS Number: 3232-36-8
• EC Number: 221-773-2
• MDL Number: MFCD00043494
• Beilstein Number: 2944701
• PubChem SID: 162248782; 24899778
• PubChem CID: 5483116

CALCULATED PROPERTIES

• Acid pKa: 7.95573
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 3.004486
• LogD (pH = 7.4): 2.8969395
• Log P: 3.006004
• Molar Refractivity: 72.1973 cm^3
• Polarizability: 26.531672 Å^3
• Polar Surface Area: 81.92 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ~20 mg/mL; H2O: insoluble
• Apperance: off-white solid
• Melting Point: 280-284°C

Safety Information

• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H319; H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Mechanism of Action: Selective partial inhibitor of beta-1-containing GABA-A receptors

Product Information

• Purity: ≥98% (HPLC); 97%
• Application(s): Tuberculostatic
• Empirical Formula (Hill Notation): C14H12N2O3

DETAILS

Sigma Aldrich - S8194

Biochem/physiol Actions
Potent and selective inhibitor of α2β1γ1δ GABAA receptor subtype.

REFERENCES

• Thompson et al (2004) Salicylidene salicylhydrazide, a selective inhibitor of b1-containing GABAA receptors. Br.J.Pharmacol. 142 97.