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S8194

Sigma-Aldrich

Salicylidene salicylhydrazide

≥98% (HPLC), solid

Synonym(s):

2-Hydroxybenzylidene 2-hydroxybenzhydrazide, NSC 87864, SCS

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About This Item

Empirical Formula (Hill Notation):
C14H12N2O3
CAS Number:
3232-36-8
Molecular Weight:
256.26
EC Number:
221-773-2
MDL number:
MFCD00043494
UNSPSC Code:
12352200
PubChem Substance ID:
24899778

assay

≥98% (HPLC)

form

solid

color

off-white

solubility

DMSO: ~20 mg/mL
H2O: insoluble

SMILES string

Oc1ccccc1\C=N\NC(=O)c2ccccc2O

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)/b15-9+

Inchi Key

OMCYEZUIYGPHDJ-OQLLNIDSSA-N

Application

Salicylidene salicylhydrazide may be used in GABAA receptor-mediated cell signaling studies.

Biochem/physiol Actions

Potent and selective inhibitor of α2β1γ1δ GABAA receptor subtype.
Potent, selective inhibitor of α2β1γ1δ GABAA receptor subtype.
Salicylidene salicylhydrazide interacts with threonine 255 located with transmembrane domain 1 and isoleucine 308 located extracellularly of the GABAA receptors with β1 subunit and allosterically inhibits them.3 It decreased the abnormal prion protein and increased the normal prion protein level in prion-infected neuroblastoma cells.4

Pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
074K4713

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E W Ainscough et al.
Journal of inorganic biochemistry, 77(3-4), 125-133 (2000-01-22)
A series of salicylaldehyde benzoylhydrazone derivatives, their copper(II) complexes and a range of transition metal complexes of the unsubstituted ligand has been synthesized and evaluated for cytotoxicity against a human adenocarcinoma cell line. A QSAR analysis revealed ligand cytotoxicity is
Tomohiro Kimura et al.
FEBS letters, 584(6), 1193-1198 (2010-02-18)
Gamma-aminobutyric acid type A (GABAA) receptor beta1 (gabrb1), a subunit of GABAA receptors involved in inhibitory effects on neurotransmission, was found to associate with the formation of protease-resistant prion protein in prion-infected neuroblastoma cells. Silencing of gabrb1 gene expression significantly
S A Thompson et al.
British journal of pharmacology, 142(1), 97-106 (2004-04-22)
1. A high-throughput assay utilizing the voltage/ion probe reader (VIPR) technology identified salicylidene salicylhydrazide (SCS) as being a potent selective inhibitor of alpha2beta1gamma1 GABA(A) receptors with a maximum inhibition of 56+/-5% and an IC(50) of 32 (23, 45) nm. 2.
Yuri A Blednov et al.
Neuropharmacology, 178, 108220-108220 (2020-08-01)
Phosphodiesterase type 4 (PDE4) inhibitors prevent hydrolysis of cyclic adenosine monophosphate and increase protein kinase A (PKA)-mediated phosphorylation. PDE4 inhibitors also regulate responses to ethanol and GABAergic drugs. We investigated mechanisms by which the PDE4 inhibitor, apremilast, regulates acute effects
Lala Rukh et al.
European journal of pharmacology, 888, 173481-173481 (2020-08-14)
Chemotherapy-induced peripheral neuropathy (CIPN) is an increasingly important problem for cancer survivors and is the foremost cause of drug-induced morbidity. In this study, the antinociceptive efficacy of salicylidene salicylhydrazide (SSH) in CIPN was investigated. SSH was evaluated for acute toxicity

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