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C8011

Sigma-Aldrich

Chelidamic acid hydrate

≥95%, powder

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:
12352202
PubChem Substance ID:
24278338
NACRES:
NA.77

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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Application

Chelidamic acid hydrate has been used in eluent solution as a complexing additive in high-performance chelation ion chromatography (HPCIC) for speciation of iron. It has also been used as an organic ligand for the polyoxometalate (POM)-based lanthanoid hybrid compounds.

Biochem/physiol Actions

Chelidamic acid (CDA), a hydroxylated derivative of 2,6-pyridine-dicarboxylic acid (DPA), is a trianionic chelating agent.
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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Construction of a dinuclear cluster containing La (?) and 4-hydroxypyridine-2, 6-dicarboxylic acid to modify Keggin-type polyoxometalate
Taghipour F and Mirzaei M
Journal of Molecular Structure null
Chelidamic acid as a new eluent for the determination of Fe (II) and Fe (III) species and other metals by high performance chelation ion chromatography
Dias J, et al.
Chromatographia null
Chelidamic acid monohydrate: the proton complex of a multidentate ligand
Hall et al.
Acta crystallographica. Section C, Crystal structure communications, 56 (Pt 4), 448-450 (2000-05-18)
Maryam Samaniyan et al.
Dalton transactions (Cambridge, England : 2003), 50(5), 1895-1900 (2021-01-22)
A novel inorganic-organic hybrid, {Na[Tb(L)(H2O)4]3(SiW12O40)}·4H2O, in which L = 4-hydroxypyridine-2,6-dicarboxylic acid (chelidamic acid), was prepared and characterized by elemental analyses, Fourier transform infrared spectroscopy, and single-crystal X-ray diffraction. It consists of a trinuclear terbium cluster bonded to a Keggin-type polyoxotungstate.
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
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