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methyl (2beta,3beta,4beta,5alpha,12beta,19alpha)-4-(acetyloxy)-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate

Vindoline

CAS: 2182-14-1

Molecular Formula: C25H32N2O6

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  5. methyl (2beta,3beta,4beta,5alpha,12beta,19alpha)-4-(acetyloxy)-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate

methyl (2beta,3beta,4beta,5alpha,12beta,19alpha)-4-(acetyloxy)-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate - Names and Identifiers

Name Vindoline
Synonyms vindolin
Vindoline
NSC 91994
VINDOLINE
Bufexamacum
Vindoline Tartrate
Vindoline free base
thoxy-1-methyl-,methylester,(2-beta,3-beta,4-beta,5-alpha,12-beta,19-alpha)
aspidospermidine-3-carboxylicacid,4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-me
(2,3,4,5a,12,19a)-4-(Acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-aspidospermidine-3-carboxylic Acid Methyl Ester
methyl (2beta,3beta,4beta,5alpha,19alpha)-4-(acetyloxy)-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate
methyl (2beta,4beta,5alpha,12beta,19alpha)-4-(acetyloxy)-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate
methyl (2beta,3beta,4beta,5xi,12beta,19alpha)-4-(acetyloxy)-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate
methyl (2beta,3beta,4beta,5alpha,12beta,19alpha)-4-(acetyloxy)-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate
(2beta,3beta,4beta,5alpha,12beta,19alpha)-4-(Acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-aspidospermidine-3-carboxylic acid methyl ester
(2beta,3beta,4beta,5alpha,12beta,19alpha)-4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-aspidospermidine-3-carboxylic acid methyl ester
Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2beta,3beta,4beta,5alpha,12beta,19alpha)-
CAS 2182-14-1
EINECS 218-558-0
InChI InChI=1/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

methyl (2beta,3beta,4beta,5alpha,12beta,19alpha)-4-(acetyloxy)-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate - Physico-chemical Properties

Molecular FormulaC25H32N2O6
Molar Mass456.53
Density1.33±0.1 g/cm3(Predicted)
Melting Point163-1650C
Boling Point569.8±50.0 °C(Predicted)
Specific Rotation(α)D20 -18° (chloroform); D27 +42° (chloroform)
Flash Point298.421°C
Solubility Soluble in methanol, DMSO and other solvents, insoluble in petroleum ether.
Vapor Presure0mmHg at 25°C
AppearanceWhite crystal
ColorWhite to Off-White
pKa5.5 in 66% DMF (Moza, Trojánek)
Storage Condition-20°C Freezer
Refractive Index1.626
MDLMFCD27991347
Physical and Chemical PropertiesSoluble in methanol, ethanol, DMSO and other organic solvents, derived from Catharanthus roseus.

methyl (2beta,3beta,4beta,5alpha,12beta,19alpha)-4-(acetyloxy)-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate - Risk and Safety

Hazard SymbolsXn - Harmful
Harmful
Risk Codes68 - Possible risk of irreversible effects
Safety DescriptionS36/37 - Wear suitable protective clothing and gloves.
S24/25 - Avoid contact with skin and eyes.
HS Code29339900

methyl (2beta,3beta,4beta,5alpha,12beta,19alpha)-4-(acetyloxy)-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate - Reference

Reference
Show more
1. Bai Daoming, Zhou Guangtao, Dai Long. Optimization of Process for Purification of Catharanthus roseus Chinese Duoling and Vinblastine by Cation Exchange Resin [J]. Journal of Liaoning University of Traditional Chinese Medicine, 2012, 014(012):182-184.
2. [IF = 5.64] Wu Dousheng et al."Oleanolic Acid Induces the Type III Secretion System of Ralstonia solanacearum." Front Microbiol. 2015 Dec;0:1466
3. [IF = 6.268] Liu Tengfei et al."Efficient production of vindoline from tabersonine by metabolically engineered Saccharomyces cerevisiae." Commun Biol. 2021 Sep;4(1):1-9
4. [IF = 5.118] Wenzhu Tang et al."Enhancement of Vindoline and Catharanthine Accumulation, Antioxidant Enzymes Activities, and Gene Expression Levels in Catharanthus roseus Leaves by Chitooligosaccharides Elicitation." Mar Drugs. 2022 Mar;20(3):188

methyl (2beta,3beta,4beta,5alpha,12beta,19alpha)-4-(acetyloxy)-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate - Reference Information

biological activity Vindoline is a periwinkle alkaloid extracted from Catharanthus roseus leaves, which has a weak inhibitory effect on the self-assembly of tubulin (tubulin) effect.
chemical properties soluble in methanol, ethanol, DMSO and other organic solvents, derived from periwinkle.
use vendoling has antibacterial, anti-inflammatory and anti-cancer effects.
A monomer vinblastine that exhibits anti-mitotic activity by inhibiting the assembly of microtubules.
Last Update：2024-04-09 20:52:54
methyl (2beta,3beta,4beta,5alpha,12beta,19alpha)-4-(acetyloxy)-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate
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View History
methyl (2beta,3beta,4beta,5alpha,12beta,19alpha)-4-(acetyloxy)-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate
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Methanone, (2-bromophenyl)(2,3-dihydro-1,4-benzodioxin-6-yl)-
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