(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 Basic information
Product 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;(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
CAS:3650-53-1
MF:C21H24N2O4
MW:368.43
EINECS:
Product Categories:
Mol File:3650-53-1.mol
(5S,16S,19E)-3,17-Dihydroxy-5,16-cyclo-19,20-didehydrocorynan-16-carboxylic acid methyl ester Structure
(5S,16S,19E)-3,17-Dihydroxy-5,16-cyclo-19,20-didehydrocorynan-16-carboxylic acid methyl ester Chemical Properties
Melting point 227-8°C
Boiling point 548.9±50.0 °C(Predicted)
density 1.42±0.1 g/cm3(Predicted)
pka13.06±0.40(Predicted)
Safety Information
MSDS Information
(5S,16S,19E)-3,17-Dihydroxy-5,16-cyclo-19,20-didehydrocorynan-16-carboxylic acid methyl ester Usage And Synthesis
DescriptionAn alkaloid isolated from Voacanga chalotiana, this base has [α]20D + 43.5° ± 4° (MeOH). It forms a methiodide, m.p. 215-6°C; [α]20D - 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.
ReferencesDenayer-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
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