(2α,17S,19E)-19,20-Didehydro-17-hydroxyajmalan-16-carboxylic acid methyl ester

CAS No.
2506-26-5
Chemical Name:
(2α,17S,19E)-19,20-Didehydro-17-hydroxyajmalan-16-carboxylic acid methyl ester
Synonyms
Vincamajine;O-Deacetylvincamedine;(2α,17S,19E)-19,20-Didehydro-17-hydroxyajmalan-16-carboxylic acid methyl ester;Ajmalan-16-carboxylic acid, 19,20-didehydro-17-hydroxy-, methyl ester, (2α,17S,19E)-
CBNumber:
CB22371281
Molecular Formula:
C22H26N2O3
Molecular Weight:
366.46
MDL Number:
MOL File:
2506-26-5.mol

(2α,17S,19E)-19,20-Didehydro-17-hydroxyajmalan-16-carboxylic acid methyl ester Properties

Melting point 226.5-227°C
Boiling point 524.1±50.0 °C(Predicted)
Density 1.36±0.1 g/cm3(Predicted)
pka 13.63±0.40(Predicted)

(2α,17S,19E)-19,20-Didehydro-17-hydroxyajmalan-16-carboxylic acid methyl ester Chemical Properties,Uses,Production

Description

A minor constituent of Vinca major, this alkaloid has been obtained by chromatography of the alkaloidal fraction followed by recrystallization from MeOH when it forms long, colourless needles. It is laevorotatory with [α]D - 55° (c 0.45, 96% EtOH). The crystalline hydrochloride has m.p. 259-261°C (dec.); [α]D -40° (c 0.38, H2O). One secondary non-phenolic hydroxyl group is present and the O-acetate is identical with Vincamedine (q.v.).

References

Janot, LeMen., Compt. rend., 241,767 (1955)

(2α,17S,19E)-19,20-Didehydro-17-hydroxyajmalan-16-carboxylic acid methyl ester Preparation Products And Raw materials

Raw materials

Preparation Products

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(2α,17S,19E)-19,20-Didehydro-17-hydroxyajmalan-16-carboxylic acid methyl ester Vincamajine Ajmalan-16-carboxylic acid, 19,20-didehydro-17-hydroxy-, methyl ester, (2α,17S,19E)- O-Deacetylvincamedine 2506-26-5