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Sigma-Aldrich

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:
99-32-1
Molecular Weight:
184.10
Beilstein/REAXYS Number:
163607
EC Number:
202-749-0
MDL number:
MFCD00006577
UNSPSC Code:
12352100
PubChem Substance ID:
24863888
NACRES:
NA.22

assay

≥95%

form

powder

mp

265 °C (dec.) (lit.)

SMILES string

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)

InChI key

PBAYDYUZOSNJGU-UHFFFAOYSA-N

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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.

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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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
Dae-Seung Kim et al.
Biological & pharmaceutical bulletin, 35(5), 666-671 (2012-06-13)
Chelidonic acid (CA), a constituent of Chelidonium majus L., has many pharmacological effects, including mild analgesic and antimicrobial effects. However, the effects of CA on intestinal inflammation and the molecular mechanisms responsible are poorly understood. The aim of this study
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