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22490

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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25 G

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About This Item

Empirical Formula (Hill Notation):
C7H5NO5 · xH2O
CAS Number:
138-60-3
Molecular Weight:
183.12 (anhydrous basis)
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
57647988
EC Number:
205-335-8
Beilstein/REAXYS Number:
476229
MDL number:
MFCD03818117
Assay:
≥97.0% (dried material, T)
Form:
powder

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InChI key

SNGPHFVJWBKEDG-UHFFFAOYSA-N

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

SMILES string

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

assay

≥97.0% (dried material, T)

form

powder

impurities

~1 mol/mol water

mp

267 °C (dec.) (lit.)

functional group

carboxylic acid

Quality Level

200

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1 of 4

This Item
C8011792748153281
Chelidamic acid hydrate ≥97.0% (dried material, T), ~1 mol/mol water

Sigma-Aldrich

22490

Chelidamic acid hydrate

Chelidamic acid hydrate ≥95%, powder

Sigma-Aldrich

C8011

Chelidamic acid hydrate

Chelidamic acid

Sigma-Aldrich

792748

Chelidamic acid

2,6-Dihydroxypyridine-4-carboxylic acid 97%

Sigma-Aldrich

153281

2,6-Dihydroxypyridine-4-carboxylic acid

assay

≥97.0% (dried material, T)

assay

≥95%

assay

-

assay

97%

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

100

form

powder

form

powder

form

powder

form

-

mp

267 °C (dec.) (lit.)

mp

267 °C (dec.) (lit.)

mp

265-270 °C

mp

>300 °C (lit.)

impurities

~1 mol/mol water

impurities

-

impurities

-

impurities

-

functional group

carboxylic acid

functional group

-

functional group

carboxylic acid

functional group

carboxylic acid

Application

Chelidamic acid hydrate was used in the synthesis of 4-Chloro-N,N,N′,N′-tetraethylpyridine-2,6-dicarboxamide[1].

Biochem/physiol Actions

Among the most potent of the tested "conformationally restricted glutamate analogs" as an inhibitor of glutamate decarboxylase.[2]

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

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
BCCN8455
BCCG4193
BCCF0445
BCCD8768
BCCD2183

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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.
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.
[Use of the radial hemolysis reaction for titrating antirabies sera].
G N Zgurskaia et al.
Voprosy virusologii, 29(3), 360-361 (1984-05-01)
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
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
View All Related Papers

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