Vindoline

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Names

[ CAS No. ]:
2182-14-1

[ Name ]:
Vindoline

[Synonym ]:
Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2β,4β,5α,12β,19α)-
methyl (2β,3β,4β,5α,12β,19α)-4-(acetyloxy)-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate
Vindoline
4-acetoxy-3-hydroxy-16-methoxy-1-methyl-6,7-didehydro-aspidospermidine-3-carboxylic acid methyl ester
(2b,3b,4b,5a,12b,19a)-4-(Acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methylaspidospermidine-3-carboxylic Acid Methyl Ester
Methyl (2β,4β,5α,12β,19α)-4-acetoxy-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate
Vindoline (8CI)
vindolin
EINECS 218-558-0
Vindoline, (-)-

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
569.8±50.0 °C at 760 mmHg

[ Melting Point ]:
163-165ºC

[ Molecular Formula ]:
C25H32N2O6

[ Molecular Weight ]:
456.531

[ Flash Point ]:
298.4±30.1 °C

[ Exact Mass ]:
456.226044

[ PSA ]:
88.54000

[ LogP ]:
2.20

[ Vapour Pressure ]:
0.0±1.6 mmHg at 25°C

[ Index of Refraction ]:
1.626

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
CJ0120000
CHEMICAL NAME :
Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1- methyl-, methyl ester, (2-beta,3-beta,4-beta,5-alpha,12-beta,19-alpha)-
CAS REGISTRY NUMBER :
2182-14-1
LAST UPDATED :
198009
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C25-H32-N2-O6
MOLECULAR WEIGHT :
456.59
WISWESSER LINE NOTATION :
T C6 B5665 2AB S BX IN QN NU JH&&TTTJ FO1 I1 KVO1 KQ LOV1 M2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
400 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - excitement
REFERENCE :
33GVAL "Catharanthus Alkaloids," Taylor, W.I., and N.R. Farnsworth, eds., New York, Marcel Dekker, 1975 Volume(issue)/page/year: -,73,1975

Safety Information

[ Symbol ]:

GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H341

[ Precautionary Statements ]:
P281

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
68

[ Safety Phrases ]:
36/37-24/25

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
CJ0120000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

  • methyl (2S,3aR,3a1R,4R,5S,5aR,10bR)-4-acetoxy-3a-ethyl-2,5-dihydroxy-8-methoxy-6-methyl-2,3,3a,3a1,4,5,5a,6,11,12-decahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate
  • Ethanoic anhydride
  • Deacetylvindoline
  • 6-METHOXY-1-METHYL-1H-INDOLE-3-CARBALDEHYDE
  • 6-methoxy-1-methylindole
  • N1-methyl-6-methoxytryptamine
  • N-(2-(6-methoxy-1-methyl-1H-indol-3-yl)ethyl)-1H-imidazole-1-carboxamide
  • N-(2-(6-methoxy-1-methyl-1H-indol-3-yl)ethyl)hydrazinecarboxamide

DownStream

  • Deacetylvindoline
  • Vincaleukoblastine, 3',4'-didehydro-4'-deoxy-
  • (S)-tert-Butyl 2-((1R,2S)-1-methoxy-2-methylbut-3-en-1-yl)pyrrolidine-1-carboxylate
  • vinleurosine

Articles

Increased availability of tryptophan in 5-methyltryptophan-tolerant shoots of Catharanthus roseus and their postharvest in vivo elicitation induces enhanced vindoline production.

Appl. Biochem. Biotechnol. 168(3) , 568-79, (2012)

Ten 5-methyltryprophan (5-MT)-resistant multiple shoot culture lines in three genotypes of Catharanthus roseus were selected in vitro. The variant shoot lines displayed a differential threshold tolera...

Simultaneous determination of vinblastine and its monomeric precursors vindoline and catharanthine in Catharanthus roseus by capillary electrophoresis-mass spectrometry.

J. Sep. Sci. 34 , 2885-2892, (2011)

Catharanthus roseus is an important dicotyledonous medicinal plant that contains various anticancer components, such as vinblastine (VLB) and its monomeric precursors (vindoline and catharanthine). A ...

Catharanthine C16 substituent effects on the biomimetic coupling with vindoline: preparation and evaluation of a key series of vinblastine analogues.

Bioorg. Med. Chem. Lett. 20(22) , 6408-10, (2010)

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 electro...


More Articles

Related Compounds

  • Dihydrovindoline
  • Deacetylvindoline
  • vindoline hydrochloride
  • 4-(aminomethyl)-N-[4-(propan-2-yl)phenyl]pyrimidin-2-amine
  • 4-(aminomethyl)-N-(2-ethoxyphenyl)pyrimidin-2-amine
  • 9-Bromo-2,8-dichloro-4-methyl-5,6-dihydro-4H-[1,4]oxazepino[5,6,7-DE]quinazoline
  • 4-(aminomethyl)-N-(3-fluorophenyl)pyrimidin-2-amine
  • 4-(aminomethyl)-N-(3-chloro-4-fluorophenyl)pyrimidin-2-amine
  • 4-(aminomethyl)-N-[4-fluoro-3-(trifluoromethyl)phenyl]pyrimidin-2-amine
  • 4-(aminomethyl)-N-[4-(trifluoromethyl)phenyl]pyrimidin-2-amine
  • 4-(aminomethyl)-N-[(4-fluorophenyl)methyl]pyrimidin-2-amine
  • 4-(aminomethyl)-N-(4-butylphenyl)pyrimidin-2-amine
  • 4-(aminomethyl)-N-(3-methylphenyl)pyrimidin-2-amine
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