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Merck

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

Key Documents

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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

100

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1 of 4

This Item
792748PHL8023922490
Chelidonic acid ≥95%

Sigma-Aldrich

382272

Chelidonic acid

Chelidamic acid

Sigma-Aldrich

792748

Chelidamic acid

Chelidonic acid phyproof® Reference Substance

PHL80239

Chelidonic acid

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

Sigma-Aldrich

22490

Chelidamic acid hydrate

assay

≥95%

assay

-

assay

≥98.0% (HPLC)

assay

≥97.0% (dried material, T)

Quality Level

100

Quality Level

100

Quality Level

-

Quality Level

200

form

powder

form

powder

form

powder

form

powder

mp

265 °C (dec.) (lit.)

mp

265-270 °C

mp

265 °C (dec.) (lit.)

mp

267 °C (dec.) (lit.)

functional group

carboxylic acid

functional group

carboxylic acid

functional group

-

functional group

carboxylic acid

Application

Chelidonic acid is suitable for use a in homogeneous preparation of native dihydrodipicolinate synthase from pea.[1] 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.[2]

General description

Chelidonic acid (CA) is a γ-pyrone.[3] It is reported as constituent of the rhizome of Chelidonium majus L. It has many pharmacological effects, such as mild analgesic and antimicrobial effects.[4] Therapeutic potential of CA for the treatment of intestinal inflammation has been investigated.[4] CA is reported as inhibitor of the rat brain glutamate decarboxylase.[5] Biosynthesis of CA in cell suspension cultures of Leucojum aestivum has been studied.[6]

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
BCBB4283
BCBB4283V
1306507
04819AE
04418PD

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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
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)
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
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
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
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