Basic information Safety Supplier Related

UNCARINE C

Basic information Safety Supplier Related

UNCARINE C Basic information

Product Name:
UNCARINE C
Synonyms:
  • 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)-
CAS:
5629-60-7
MF:
C21H24N2O4
MW:
368.43
Mol File:
5629-60-7.mol
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UNCARINE C Chemical Properties

Melting point:
217-219℃
Density 
1.33±0.1 g/cm3 (20 ºC 760 Torr)
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UNCARINE C Usage And Synthesis

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.

Definition

ChEBI: Uncarine C is a member of indolizines.

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 CSupplier

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