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Merck

54274

Sigma-Aldrich

Chelidonine

≥97.0% (HPLC)

Sinónimos:

Stylophorin

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About This Item

Fórmula empírica (notación de Hill):
C20H19NO5
Número de CAS:
Peso molecular:
353.37
EC Number:
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77
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Quality Level

assay

≥97.0% (HPLC)

form

solid

impurities

~5% water

storage temp.

2-8°C

SMILES string

[H][C@]12[C@@H](O)Cc3cc4OCOc4cc3[C@@]1([H])N(C)Cc5c6OCOc6ccc25

InChI

1S/C20H19NO5/c1-21-7-13-11(2-3-15-20(13)26-9-23-15)18-14(22)4-10-5-16-17(25-8-24-16)6-12(10)19(18)21/h2-3,5-6,14,18-19,22H,4,7-9H2,1H3/t14-,18-,19+/m0/s1

InChI key

GHKISGDRQRSCII-ZOCIIQOWSA-N

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Biochem/physiol Actions

Inhibits tubulin polymerisation (IC50=24 μM), thereby disrupting microtubule structure in cells and inducing a G2/M mitotic arrest.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Skull and crossbones

signalword

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

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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Stepwise gradient in thin-layer chromatography of Chelidonium alkaloids.
G Matysik et al.
Journal of chromatography, 518(1), 273-276 (1990-09-28)
Sakineh Kazemi Noureini et al.
World journal of gastroenterology, 15(29), 3603-3610 (2009-08-05)
To investigate the potential effects of chelidonine, the main alkaloid of Chelidonium majus, on telomerase activity and its regulation in HepG2 cells. Cytotoxicity of chelidonine for HepG2 cells was determined by neutral red assay. A modified polymerase chain reaction (PCR)-based
J Wolff et al.
Biochemistry, 32(48), 13334-13339 (1993-12-07)
Chelidonine, sanguinarine, and chelerythrine are natural benzophenanthridine alkaloids that inhibit taxol-mediated polymerization of rat brain tubulin in the micromolar range. Chelidonine is a weak, competitive inhibitor of colchicine binding to tubulin but does not inhibit podophyllotoxin binding. On the other
Matthew J Fleming et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 14(7), 2112-2124 (2008-01-18)
New enantioselective syntheses of the B/C hexahydrobenzo[c]phenanthridine alkaloids (+)-homochelidonine, (+)-chelamidine, (+)-chelidonine, (+)-chelamine, and (+)-norchelidonine are described. Our rapid and convergent route to this class of natural products involved the development and application of a Pd II-catalyzed asymmetric ring-opening reaction of
Anna Petruczynik et al.
Journal of AOAC International, 100(6), 1652-1659 (2017-07-15)
An HPLC procedure on a polar reversed-phase column with mobile phases containing ionic liquid (IL) was developed for the analysis of selected alkaloids from different chemical groups. We aimed to obtain optimal conditions for the separation of alkaloids because widely

Questions

  1. Good afternoon. I ask you to send me the protocol and extraction method you have used. Kind regards

    1 answer
    1. This product is not tested for any specific application. A protocol is not available. The material is produced synthetically. The method is considered proprietary.

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