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22490

Sigma-Aldrich

Chelidamic acid hydrate

≥97.0% (dried material, T), ~1 mol/mol water

Synonym(s):

1,4-Dihydro-4-oxo-2,6-pyridinedicarboxylic acid hydrate, 4-Hydroxypyridine-2,6-dicarboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C7H5NO5 · xH2O
CAS Number:
138-60-3
Molecular Weight:
183.12 (anhydrous basis)
Beilstein:
476229
EC Number:
205-335-8
MDL number:
MFCD03818117
UNSPSC Code:
12352100
PubChem Substance ID:
57647988
NACRES:
NA.22

Assay

≥97.0% (dried material, T)

form

powder

impurities

~1 mol/mol water

mp

267 °C (dec.) (lit.)

functional group

carboxylic acid

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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Application

Chelidamic acid hydrate was used in the synthesis of 4-Chloro-N,N,N′,N′-tetraethylpyridine-2,6-dicarboxamide.

Biochem/physiol Actions

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG4193
BCCF0445
BCCD8768
BCCD2183
BCBT7880

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Anne-Sophie Chauvin et al.
Organic & biomolecular chemistry, 1(4), 737-740 (2003-08-22)
The synthesis of 4-substituted dipicolinic acid derivatives requiring palladium catalysis is described. A keto-enol equilibrium has been observed, depending on the nature of the 2,6-position substituents.
[Antiviral activity of chelidamic acid derivatives].
V E Iavorovskaia et al.
Voprosy virusologii, 29(3), 361-363 (1984-05-01)
Ahmed Moussa et al.
Chirality, 21(5), 497-506 (2008-08-14)
The perturbation of the racemic equilibrium of luminescent D3 terbium(III) complexes with chelidamic acid (CDA), a hydroxylated derivative of 2,6-pyridine-dicarboxylic acid (DPA), by added chiral biomolecules such as L-amino acids has been studied using circularly polarized luminescence and 13C NMR
Maya Tutughamiarso et al.
Acta crystallographica. Section C, Crystal structure communications, 68(Pt 9), o344-o350 (2012-09-01)
Different tautomeric and zwitterionic forms of chelidamic acid (4-hydroxypyridine-2,6-dicarboxylic acid) are present in the crystal structures of chelidamic acid methanol monosolvate, C(7)H(5)NO(5)·CH(4)O, (Ia), dimethylammonium chelidamate (dimethylammonium 6-carboxy-4-hydroxypyridine-2-carboxylate), C(2)H(8)N(+)·C(7)H(4)NO(5)(-), (Ib), and chelidamic acid dimethyl sulfoxide monosolvate, C(7)H(5)NO(5)·C(2)H(6)OS, (Ic). While the zwitterionic
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.
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