(5S,16S,19E)-3,17-Dihydroxy-5,16-cyclo-19,20-didehydrocorynan-16-carboxylic acid methyl ester

(5S,16S,19E)-3,17-Dihydroxy-5,16-cyclo-19,20-didehydrocorynan-16-carboxylic acid methyl ester structure

CAS No.: 3650-53-1

Chemical Name:: (5S,16S,19E)-3,17-Dihydroxy-5,16-cyclo-19,20-didehydrocorynan-16-carboxylic acid methyl ester

Synonyms: Voacarpine;3,17-Dihydroxysarpagane-16-carboxylic acid methyl ester;Sarpagan-16-carboxylic acid, 3,17-dihydroxy-, methyl ester;(5S,16S,19E)-3,17-Dihydroxy-5,16-cyclo-19,20-didehydrocorynan-16-carboxylic acid methyl ester

CBNumber:: CB52137769

Molecular Formula:: C21H24N2O4

Molecular Weight:: 368.43

MDL Number:

MOL File:: 3650-53-1.mol

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(5S,16S,19E)-3,17-Dihydroxy-5,16-cyclo-19,20-didehydrocorynan-16-carboxylic acid methyl ester Properties

Melting point	227-8°C
Boiling point	548.9±50.0 °C(Predicted)
Density	1.42±0.1 g/cm3(Predicted)
pka	13.06±0.40(Predicted)

(5S,16S,19E)-3,17-Dihydroxy-5,16-cyclo-19,20-didehydrocorynan-16-carboxylic acid methyl ester Chemical Properties,Uses,Production

Description

An alkaloid isolated from Voacanga chalotiana, this base has [α]²⁰_D + 43.5° ± 4° (MeOH). It forms a methiodide, m.p. 215-6°C; [α]²⁰_D - 12° ± 4° (MeOH); the O,N-diacetyl derivative, m.p. 212-3°C and the O,N-ditosyl compound, m.p. 193-4°C. When heated with mineral acids, the alkaloid gives isovoacarpine, m.p. 227.5-228.5°C, giving an N-acetyl derivative, m.p. 256-7°C.

References

Denayer-Tournay et al., Bull. Soc. Chim. Belg., 74, 170 (1965)

(5S,16S,19E)-3,17-Dihydroxy-5,16-cyclo-19,20-didehydrocorynan-16-carboxylic acid methyl ester Preparation Products And Raw materials

Raw materials

Preparation Products

Voacarpine 3,17-Dihydroxysarpagane-16-carboxylic acid methyl ester (5S,16S,19E)-3,17-Dihydroxy-5,16-cyclo-19,20-didehydrocorynan-16-carboxylic acid methyl ester Sarpagan-16-carboxylic acid, 3,17-dihydroxy-, methyl ester 3650-53-1