C8011

Sigma-Aldrich

Chelidamic acid hydrate

≥95%, powder

Synonym(s):
4-Hydroxypyridine-2,6-dicarboxylic acid, 1,4-Dihydro-4-oxo-2,6-pyridinedicarboxylic acid hydrate
Empirical Formula (Hill Notation):
C7H5NO5 · xH2O
CAS Number:
Molecular Weight:
183.12 (anhydrous basis)
Beilstein/REAXYS Number:
476229
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

biological source

synthetic (organic)

assay

≥95%

form

powder

color

brown

mp

267 °C (dec.) (lit.)

solubility

1 M NH4OH: 50 mg/mL, clear to slightly hazy

SMILES string

O.OC(=O)C1=CC(=O)C=C(N1)C(O)=O

InChI

1S/C7H5NO5.H2O/c9-3-1-4(6(10)11)8-5(2-3)7(12)13;/h1-2H,(H,8,9)(H,10,11)(H,12,13);1H2

InChI key

SNGPHFVJWBKEDG-UHFFFAOYSA-N

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Packaging

5, 25, 100 g in poly bottle

Biochem/physiol Actions

Among the most potent of the tested "conformationally restricted glutamate analogs" as an inhibitor of glutamate decarboxylase.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

T G Porter et al.
Biochemical pharmacology, 34(23), 4145-4150 (1985-12-01)
Twenty conformationally restricted analogues of glutamate including benzoic acids, hydroxy-benzoic acids, pyridine dicarboxylic acids, and pyran dicarboxylic acids were tested as inhibitors of glutamate decarboxylase from rat brain. Chelidonic acid, 2,6-pyridine dicarboxylic acid, chelidamic acid, gallic acid, and 3,4-dihydroxybenzoic acid...
[Use of the radial hemolysis reaction for titrating antirabies sera].
G N Zgurskaia et al.
Voprosy virusologii, 29(3), 360-361 (1984-05-01)
Elvir Ramić et al.
The journal of physical chemistry. B, 110(41), 20655-20663 (2006-10-13)
Multifrequency electron paramagnetic resonance (EPR) and electron nuclear double resonance (ENDOR) techniques were used to obtain structural information about the copper(II)-chelidamate complex. Well-resolved nitrogen ENDOR spectra could be recorded from solid solution samples by using selective excitation of spin packets....
[Antiviral activity of chelidamic acid derivatives].
V E Iavorovskaia et al.
Voprosy virusologii, 29(3), 361-363 (1984-05-01)
M Searcey et al.
Anti-cancer drug design, 13(8), 837-855 (1999-05-21)
We have explored the potential antitumour activity of DNA-intercalating free radical generators based on compounds constructed from 9-anilinoacridine and chelidamic acid as an iron (II) binding centre. Here we describe their synthesis, DNA cleaving ability and activity against a panel...

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