382272
Chelidonic acid
≥95%
Synonym(s):
4-Oxo-4H-pyran-2,6-dicarboxylic acid
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About This Item
Empirical Formula (Hill Notation):
C7H4O6
CAS Number:
Molecular Weight:
184.10
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
202-749-0
Beilstein/REAXYS Number:
163607
MDL number:
Assay:
≥95%
Form:
powder
Product Name
Chelidonic acid, ≥95%
InChI key
PBAYDYUZOSNJGU-UHFFFAOYSA-N
InChI
1S/C7H4O6/c8-3-1-4(6(9)10)13-5(2-3)7(11)12/h1-2H,(H,9,10)(H,11,12)
SMILES string
OC(=O)C1=CC(=O)C=C(O1)C(O)=O
assay
≥95%
form
powder
mp
265 °C (dec.) (lit.)
functional group
carboxylic acid
ether
ketone
Quality Level
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Application
Chelidonic acid is suitable for use a in homogeneous preparation of native dihydrodipicolinate synthase from pea. It may be used as endocyclic oxygen-containing ligand in the synthesis of aqua[bis(2-pyridylmethyl)amine][chelidonato(1.5-)]-copper(II) chelidonate(0.5-) monohydrate.
General description
Chelidonic acid (CA) is a γ-pyrone. It is reported as constituent of the rhizome of Chelidonium majus L. It has many pharmacological effects, such as mild analgesic and antimicrobial effects. Therapeutic potential of CA for the treatment of intestinal inflammation has been investigated. CA is reported as inhibitor of the rat brain glutamate decarboxylase. Biosynthesis of CA in cell suspension cultures of Leucojum aestivum has been studied.
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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Mohammad Ghadermazi et al.
Acta crystallographica. Section C, Crystal structure communications, 67(Pt 4), o134-o138 (2011-04-07)
Two related proton-transfer compounds, namely piperazine-1,4-diium 4-oxo-4H-pyran-2,6-dicarboxylate monohydrate, C(4)H(12)N(2)(2+)·C(7)H(2)O(6)(2-)·H(2)O or (pipzH(2))(cdo)·H(2)O, (I), and piperazine-1,4-diium bis(6-carboxy-4-oxo-4H-pyran-2-carboxylate), C(4)H(12)N(2)(2+)·2C(7)H(3)O(6)(-) or (pipzH(2))(cdoH)(2), (II), were obtained by the reaction of 4-oxo-4H-pyran-2,6-dicarboxylic acid (chelidonic acid, cdoH(2)) and piperazine (pipz). In (I), both carboxyl H atoms of
Aqua [bis (2-pyridylmethyl) amine][chelidonato (1.5-)] copper (II) chelidonate (0.5-) monohydrate.
Fainerman-Melnikova M, et al.
Acta Crystallographica Section E, Structure Reports Online, 62(12), m3582-m3584 (2006)
C Dereppe et al.
Plant physiology, 98(3), 813-821 (1992-03-01)
Dihydrodipicolinate synthase (EC 4.2.1.52), the first enzyme unique to lysine biosynthesis in bacteria and higher plants, has been purified to homogeneity from etiolated pea (Pisum sativum) seedlings using a combination of conventional and affinity chromatographic steps. This is the first
Shen Z-W et al.
Phytochemistry, 57(1), 33-42 (2001-05-05)
The biosynthesis of chelidonic acid was studied in cell suspension cultures of Leucojum aestivum. Cell cultures were supplied with [U-13C]glucose, [l-13C]glucose or [U-13Cs]ribose/ribulose in standard medium containing unlabeled glucose. 13C labeling patterns of amino acids obtained by hydrolysis of biomass
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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