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Safety Information

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:
2182-14-1
Molecular Weight:
456.53
EC Number:
218-558-0
UNSPSC Code:
12352200
PubChem Substance ID:
329747570

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
GHS08

Signal Word

Warning

Hazard Statements

H341

Precautionary Statements

P281

Hazard Classifications

Muta. 2

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBC1153
BCBC1153V

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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
Yoshikazu Sasaki et al.
Journal of the American Chemical Society, 132(38), 13533-13544 (2010-09-03)
Concise asymmetric total syntheses of vindoline (1) and vindorosine (2) are detailed based on a unique intramolecular [4 + 2]/[3 + 2] cycloaddition cascade of 1,3,4-oxadiazoles inspired by the natural product structures. A chiral substituent on the tether linking the
Péter Keglevich et al.
Molecules (Basel, Switzerland), 17(5), 5893-5914 (2012-05-23)
The synthetic investigation of biologically active natural compounds serves two main purposes: (i) the total synthesis of alkaloids and their analogues; (ii) modification of the structures for producing more selective, more effective, or less toxic derivatives. In the chemistry of
Sunil Kumar et al.
Rapid communications in mass spectrometry : RCM, 32(4), 319-332 (2017-11-28)
Catharanthus roseus is a well-known dicotyledonous medicinal plant containing diverse classes of bioactive terpene indole alkaloids (TIAs), in particular the anticancer agents vinblastine and vincristine. In view of the commercial importance of these compounds there is an urgent need to
Grégory Guirimand et al.
Journal of plant physiology, 168(6), 549-557 (2010-11-05)
Vindoline constitutes the main terpenoid indole alkaloid accumulated in leaves of Catharanthus roseus, and four genes involved in its biosynthesis have been identified. However, the spatial organization of the tabersonine-to-vindoline biosynthetic pathway is still incomplete. To pursue the characterization of
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