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382272

Sigma-Aldrich

Chelidonic acid

≥95%

Sinonimo/i:

4-Oxo-4H-pyran-2,6-dicarboxylic acid

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About This Item

Formula empirica (notazione di Hill):
C7H4O6
Numero CAS:
99-32-1
Peso molecolare:
184.10
Beilstein:
163607
Numero CE:
202-749-0
Numero MDL:
MFCD00006577
Codice UNSPSC:
12352100
ID PubChem:
24863888
NACRES:
NA.22

Saggio

≥95%

Forma fisica

powder

Punto di fusione

265 °C (dec.) (lit.)

Stringa SMILE

OC(=O)C1=CC(=O)C=C(O1)C(O)=O

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)
PBAYDYUZOSNJGU-UHFFFAOYSA-N

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Descrizione generale

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.

Applicazioni

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.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

Certificati d'analisi (COA)

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Sigma-Aldrich

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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
Hyun-Ji Shin et al.
Immunopharmacology and immunotoxicology, 33(4), 614-619 (2011-02-16)
Chelidonic acid (CA) is a γ-pyrone which is contained in the rhizome of Chelidonium majus L. It has multiple pharmacological effects including those of a mild analgesic, an antimicrobial, an oncostatic and a central nervous system sedative, but the anti-inflammatory
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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