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54274

Sigma-Aldrich

Chelidonine

≥97.0% (HPLC)

Synonym(s):

Stylophorin

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About This Item

Empirical Formula (Hill Notation):
C20H19NO5
CAS Number:
476-32-4
Molecular Weight:
353.37
EC Number:
207-504-1
MDL number:
MFCD00069660
UNSPSC Code:
12352202
PubChem Substance ID:
329758025
NACRES:
NA.77

Quality Level

100

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
GHS06

Signal Word

Danger

Hazard Statements

H301 + H331

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCD7509
BCBZ6536
BCBF0551V
BCBV3780
BCBQ5285V

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Zhi-Xiong Ma et al.
Organic letters, 14(11), 2742-2745 (2012-05-12)
Total syntheses of chelidonine and norchelidonine featuring an enamide-benzyne-[2 + 2] cycloaddition initiated cascade is described. The cascade includes a pericyclic ring-opening and intramolecular Diels-Alder reaction.
Z Kleinrok et al.
Polish journal of pharmacology and pharmacy, 42(5), 417-424 (1990-09-01)
Chelidonine administered to rats in doses of 25, 50, 100 and 200 mg/kg ip exerted an inhibitory effect on the dopaminergic structures in the rat. It was shown that chelidonine decreased amphetamine- and apomorphine-induced hyperactivity and inhibited amphetamine and apomorphine
Stepwise gradient in thin-layer chromatography of Chelidonium alkaloids.
G Matysik et al.
Journal of chromatography, 518(1), 273-276 (1990-09-28)
Vitaliy Kaminskyy et al.
Toxicology letters, 177(3), 168-181 (2008-03-08)
Sanguinarine, chelerythrine and chelidonine possess prominent apoptotic effects towards cancer cells. In this study, we found that sanguinarine and chelerythrine induce apoptosis in human CEM T-leukemia cells, and that is accompanied by an early increase in cytosolic cytochrome c that
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
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