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03179

Sigma-Aldrich

Vindoline

≥98.0% (HPLC)

Synonym(s):

Methyl (2β,3β,4β,5α,12R,19α)-4-(Acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methylaspidospermidine-3-carboxylate

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About This Item

Empirical Formula (Hill Notation):
C25H32N2O6
CAS Number:
Molecular Weight:
456.53
EC Number:
UNSPSC Code:
12352200
PubChem Substance ID:

assay

≥98.0% (HPLC)

optical activity

[α]/D -65±3°, c = 1.5 in methanol

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

CC[C@]12C=CCN3CC[C@]4([C@@H](N(C)c5cc(OC)ccc45)[C@](O)([C@@H]1OC(C)=O)C(=O)OC)[C@H]23

InChI

1S/C25H32N2O6/c1-6-23-10-7-12-27-13-11-24(19(23)27)17-9-8-16(31-4)14-18(17)26(3)20(24)25(30,22(29)32-5)21(23)33-15(2)28/h7-10,14,19-21,30H,6,11-13H2,1-5H3/t19-,20+,21+,23+,24+,25-/m0/s1

InChI key

CXBGOBGJHGGWIE-ACSXSLCXSA-N

Application

Vindoline, a monoterpenoid indole alkaloid, is used to synthesize vinblastine and vincristine via coupling catharanthine. Vindoline may be used as a reference standard during its identification and purification of from plant materials.

Biochem/physiol Actions

Vindoline is a monoterpenoid indole alkaloid exclusive to the Madagascar periwinkle plant (Catharanthus roseus). Vindoline combines catharanthine to derive the anti-cancer agents vinblastine and vincristine.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Health hazard

signalword

Warning

hcodes

pcodes

Hazard Classifications

Muta. 2

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Travis C Turner et al.
Organic letters, 15(5), 1100-1103 (2013-02-21)
The regioselective intermolecular coupling reaction of vindoline with a wide range of substrates including β-ketoesters, β-diketones, β-ketoaldehydes, β-ketonitriles, malononitriles, and β-cyanoesters provides an opportunity for the synthesis of vinblastine analogues containing deep-seated changes in the upper velbanamine subunit. The transition-metal-free
Lesley-Ann Giddings et al.
The Journal of biological chemistry, 286(19), 16751-16757 (2011-04-02)
Plant cytochrome P450s are involved in the production of over a hundred thousand metabolites such as alkaloids, terpenoids, and phenylpropanoids. Although cytochrome P450 genes constitute one of the largest superfamilies in plants, many of the catalytic functions of the enzymes
Jonathan Roepke et al.
Proceedings of the National Academy of Sciences of the United States of America, 107(34), 15287-15292 (2010-08-11)
The monoterpenoid indole alkaloids (MIAs) of Madagascar periwinkle (Catharanthus roseus) continue to be the most important source of natural drugs in chemotherapy treatments for a range of human cancers. These anticancer drugs are derived from the coupling of catharanthine and
Shouhong Gao et al.
Journal of analytical methods in chemistry, 2018, 7967694-7967694 (2018-07-27)
Therapeutic drug monitoring for anticancer drugs could timely reflect in vivo drug exposure, and it was a powerful tool for adjusting and maintaining drug concentration into a reasonable range, so that an enhanced efficacy and declined adverse reactions could be
Annie Tam et al.
Bioorganic & medicinal chemistry letters, 20(22), 6408-6410 (2010-10-12)
The examination of the catharanthine C16 substituent effects on the Fe(III)-promoted biomimetic coupling reaction with vindoline is detailed, confirming the importance of the presence of a C16 electron-withdrawing substituent, and establishing an unanticipated unique role (>10-fold) that the C16 methyl

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