UNCARINE C

UNCARINE C Structure
CAS No.
5629-60-7
Chemical Name:
UNCARINE C
Synonyms
UNCARINE C;PTEROPODINE;Isospeciophylline;(20α)-19α-Methyl-2-oxoformosanan-16-carboxylic acid methyl ester;methyl 1-methyl-2'-oxospiro[1,4a,5,5a,7,8,10,10a-octahydropyrano[3,4-f]indolizine-6,3'-1H-indole]-4-carboxylate;methyl 1-methyl-2'-oxo-spiro[1,4a,5,5a,7,8,10,10a-octahydropyrano[3,4-f]indolizine-6,3'-1H-indole]-4-carboxylate;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;Spiro[3H-indole-3,6'(4'aH)-[1H]pyrano[3,4-f]indolizine]-4'-carboxylic acid, 1,2,5',5'a,7',8',10',10'a-octahydro-1'-methyl-2-oxo-, methyl ester, (1'S,3R,4'aS,5'aS,10'aS)-
CBNumber:
CB7326387
Molecular Formula:
C21H24N2O4
Molecular Weight:
368.43
MOL File:
5629-60-7.mol
Modify Date:
2023/8/24 17:20:48

UNCARINE C Properties

Melting point 217-219℃
Density 1.33±0.1 g/cm3 (20 ºC 760 Torr)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS06
Signal word  Danger
Hazard statements  H300
Precautionary statements  P264-P270-P301+P310-P321-P330-P405-P501

UNCARINE C Chemical Properties,Uses,Production

Description

Isolated from Uncaria pteropoda, this alkaloid is probably stereoisomeric withMitraphylline (q.v.). It forms colourless plates when crystallized from MeOH and has [α]29DJ 9 - 102.5° (c 1.0, CHC13). The ultraviolet spectrum in MeOH has an absorption maximum at 246 mp. with a shoulder at 280 mp.. A crystalline picrate, m.p. 143-6°C; [α]D - 9.6° (c 0.5, EtOH) and a methiodide, m.p. 209-211°C after softening at 204°C; [α]D - 149° (c 0.53, EtOH) have been prepared. A solution of the alkaloid in pyridine forms an equilibrium mixture with 70 per cent isopteropodine when heated.

Uses

Uncarine C is a compound extracted from Uncaria tomentosa leaves. The compounds extracted from these leaves have exhibited immunomodulating, antiinflammatory and anti-cancer activity, attributed to the presence of tetra/pentacyclic oxindole alkaloids.

References

Yeoh, Chan, Morsingh., Tetrahedron Lett., 931 (1966)
Chan, Morsingh, Yeoh., 1. Chem. Soc., C, 2245 (1966)
Stereochemistry: Shamma et al., 1. Amer. Chem. Soc., 89, 1739, 2799 (1967)

UNCARINE C Preparation Products And Raw materials

Raw materials

Preparation Products

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PTEROPODINE UNCARINE C (20α)-19α-Methyl-2-oxoformosanan-16-carboxylic acid methyl ester 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 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 1-methyl-2'-oxospiro[1,4a,5,5a,7,8,10,10a-octahydropyrano[3,4-f]indolizine-6,3'-1H-indole]-4-carboxylate Isospeciophylline Spiro[3H-indole-3,6'(4'aH)-[1H]pyrano[3,4-f]indolizine]-4'-carboxylic acid, 1,2,5',5'a,7',8',10',10'a-octahydro-1'-methyl-2-oxo-, methyl ester, (1'S,3R,4'aS,5'aS,10'aS)- 5629-60-7 C21H24N2O4