SML0259

Sigma-Aldrich

Catharanthine

≥95% (HPLC)

Sinónimos:
(2α,5β,6α,18β)-3,4-Didehydroibogamine-18-carboxylic acid methyl ester, 7-Ethyl-9,10,12,13-tetrahydro-6,9-methano-5H-pyrido1′,2′:1,2azepino4,5-bindole-6(6aH)-carboxylic acid methyl ester, (+)-3,4-Didehydrocoronaridine
Empirical Formula (Hill Notation):
C21H24N2O2
Número de CAS:
Peso molecular:
336.43
MDL number:
PubChem Substance ID:
NACRES:
NA.77
En este momento no podemos mostrarle ni los precios ni la disponibilidad

assay

≥95% (HPLC)

form

powder

optical activity

α/D +30 to +38° (c=0.5, CDCl3)

color

white to beige

solubility

DMSO: 5 mg/mL (clear solution; warmed)

shipped in

wet ice

storage temp.

−20°C

SMILES string

CCC1=CC@@H2CN@H3CCc4c(nHc5ccccc45)C@@(C2)(C@@H13)C(=O)OC

InChI

1S/C21H24N2O2/c1-3-14-10-13-11-21(20(24)25-2)18-16(8-9-23(12-13)19(14)21)15-6-4-5-7-17(15)22-18/h4-7,10,13,19,22H,3,8-9,11-12H2,1-2H3/t13-,19+,21-/m0/s1

InChI key

CMKFQVZJOWHHDV-NQZBTDCJSA-N

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Packaging

10, 50 mg in glass bottle

Biochem/physiol Actions

Catharanthine is a precursor of the anti-tumor drugs vinblastine and vincristine, formed by dimerization of catharanthine with vindoline. Catharanthine itself is an inhibitor of tubulin self-assembly into microtubules, although not so potent as vinblastine or vincristine. Catharanthine also has anticholinergic activity. It showed muscarinic antagonism at 10 microM and fully inhibited nicotinic receptor mediated diaphragm contractions with an IC50 of 59.6 microM.

pictograms

Exclamation mark

signalword

Warning

hcodes

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Cui-Ting Wang et al.
Plant cell reports, 29(8), 887-894 (2010-06-11)
A number of genes that function in the terpenoid indole alkaloids (TIAs) biosynthesis pathway have been identified in Catharanthus roseus. Except for the geraniol 10-hydroxylase (G10H) gene, which encodes a cytochrome P450 monooxygenase, several of these genes are up-regulated by...
Mei-Liang Zhou et al.
Applied microbiology and biotechnology, 91(4), 1095-1105 (2011-05-19)
Catharanthus roseus (L.) G. Don is a plant species known for its production of a variety of terpenoid indole alkaloids, many of which have pharmacological activities. Production of catharanthine in cell cultures or in hairy roots established by transformation with...
Hugo R Arias et al.
Neurochemistry international, 57(2), 153-161 (2010-05-25)
We compared the interaction of several catharanthine alkaloids including, ibogaine, vincristine, and vinblastine, with that for the noncompetitive antagonist phencyclidine (PCP) at muscle nicotinic acetylcholine receptors (AChRs) in different conformational states. The results established that catharanthine alkaloids: (a) inhibit, in...
Hiroaki Gotoh et al.
Journal of the American Chemical Society, 134(32), 13240-13243 (2012-08-04)
A definition of the scope of aromatic substrates that participate with catharanthine in an Fe(III)-mediated coupling reaction, an examination of the key structural features of catharanthine required for participation in the reaction, and the development of a generalized indole functionalization...
Jinghua Yu et al.
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 35(23), 3093-3096 (2011-03-02)
The content of vindoline, catharanthine and vinblastine in the root, stem, leaf, flower and fruit of Catharanthus roseus at various developmental stages were determined, and the biomass allocation was also determined to find the best harvest time. The content of...

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