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382272

Sigma-Aldrich

Chelidonic acid

≥95%

Synonym(s):

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

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5 G
$139.30
25 G
$441.70

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

$139.30

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Available to ship onApril 10, 2025Details

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assay

≥95%

form

powder

mp

265 °C (dec.) (lit.)

functional group

carboxylic acid
ether
ketone

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.[1] It is reported as constituent of the rhizome of Chelidonium majus L. It has many pharmacological effects, such as mild analgesic and antimicrobial effects.[2] Therapeutic potential of CA for the treatment of intestinal inflammation has been investigated.[2] CA is reported as inhibitor of the rat brain glutamate decarboxylase.[3] Biosynthesis of CA in cell suspension cultures of Leucojum aestivum has been studied.[4]

Application

Chelidonic acid is suitable for use a in homogeneous preparation of native dihydrodipicolinate synthase from pea.[5] 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.[6]

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCBB4283
BCBB4283V
1306507
04819AE
04418PD

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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
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
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