5171-37-9

Basic information

• Product Name: UNCARINE E
• Synonyms: UNCARINE E;ISOPTEROPODINE;(7S,20α)-19α-Methyl-2-oxoformosanan-16-carboxylic acid methyl ester;7-Isopteropodine;(1R,4aR,10aR)-2'-keto-1-methyl-spiro[1,4a,5,5a,7,8,10,10a-octahydropyrano[3,4-f]indolizine-6,3'-indoline]-4-carboxylic acid methyl ester;methyl (1R,4aR,10aR)-1-methyl-2'-oxo-spiro[1,4a,5,5a,7,8,10,10a-octahydropyrano[3,4-f]indolizine-6,3'-1H-indole]-4-carboxylate;methyl (1R,4aR,10aR)-1-methyl-2'-oxospiro[1,4a,5,5a,7,8,10,10a-octahydropyrano[3,4-f]indolizine-6,3'-1H-indole]-4-carboxylate;Isopteropodine (20 mg)
• CAS NO: 5171-37-9
• Molecular Formula: C21H24N2O4
• Molecular Weight: 368.43
• Product Categories: standard material,plant extracts
• Mol File: 5171-37-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 209-211 °C
• Boiling Point: 555.2°C at 760 mmHg
• Flash Point: 289.6°C
• Appearance: /
• Density: 1.33
• Vapor Pressure: 2.3E-12mmHg at 25°C
• Refractive Index: 1.635
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 13.56±0.60(Predicted)
• CAS DataBase Reference: UNCARINE E(CAS DataBase Reference)
• NIST Chemistry Reference: UNCARINE E(5171-37-9)
• EPA Substance Registry System: UNCARINE E(5171-37-9)

Safety Data

• Hazardous Substances Data: 5171-37-9(Hazardous Substances Data)

Usage

Description

This alkaloid occurs in several species of Uncaria and yields colourless crystals from MeOH. It is laevorotatory with [α]D - 96° (CHCI3). The structure has been determined by spectroscopic methods.

Uses

Isopteropodine is an alkaloid extract from Uncaria Tomentosathat is believed to possess antiproliferative and pro-apoptotic effects.

References

Hart, Johns, Lamberton., Chem. Commun., 87 (1967) Hemingway, Phillipson., 1. Pharm. Pharmacol., 24, 169P (1972)

InChI:InChI=1/C21H24N2O4/c1-12-14-10-23-8-7-21(16-5-3-4-6-17(16)22-20(21)25)18(23)9-13(14)15(11-27-12)19(24)26-2/h3-6,11-14,18H,7-10H2,1-2H3,(H,22,25)/t12-,13-,14-,18?,21?/m1/s1

Upstream product

• 82564-37-2 C₂₁H₂₂N₂O₅ 
• 14019-66-0 uncarine F 
• 4697-68-1 speciophylline 
• 116005-85-7 (7aR,8S,11aS,12aS)-8-Methyl-7-oxo-5,6,7a,8,11a,12,12a,13-octahydro-7H-9-oxa-6a,13-diaza-indeno[2,1-a]anthracene-11-carboxylic acid methyl ester 
• 6474-90-4 tetrahydroalstonine 
• 5629-60-7 Pteropodine 
• 36193-47-2 2-ethoxy-19α-methyl-(7αC²,20α)-formosan-1-ene-16-carboxylic acid methyl ester 
• 2288-53-1 7-acetoxy-19α-methyl-(7ξH,20α)-7H-18-oxa-yohimb-16-ene-16-carboxylic acid methyl ester 

Downstream Products

• 14019-66-0 uncarine F 
• 4697-68-1 speciophylline 
• 5629-60-7 Pteropodine 

Relevant articles and documents

Analysis of the kinetics of isomerization of spiro oxindole alkaloids

The isomerization of the spiro oxindole alkaloids mitraphylline, isomitraphylline, pteropodine, isopteropodine, speciophylline and uncarine F in water has been studied at several temperatures and the rate coefficients have been determined. The effect of pH on the rate of reaction and the equilibrium composition has been investigated. The rate coefficients in water and in organic solvents correlate satisfactorily with the Dimroth-Reichardt solvent polarity parameter. The present results support the existence of a zwitterionic intermediate stabilized by polar solvents and show that protonation of the alkaloids inhibits the isomerization. The crystal structure of pteropodine has been determined.

Transformation of indole alkaloids. I. Conversion of oxindole alkaloids into indole alkaloids

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Yohimbane derivatives. 3. The oxidative rearrangement of indole alkaloids to their spirooxindole analogs.

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