Lycoctonine
Title: Lycoctonine
CAS Registry Number: 26000-17-9
CAS Name: (1a,6b,14a,16b)-20-Ethyl-4-(hydroxymethyl)-1,6,14,16-tetramethoxyaconitane-7,8-diol
Additional Names: royline
Molecular Formula: C25H41NO7
Molecular Weight: 467.60
Percent Composition: C 64.21%, H 8.84%, N 3.00%, O 23.95%
Literature References: Isomeric with delsoline. Originally isolated from Aconitum lycoctonum L., Ranunculaceae: Hubschmann, Schweiz. Wochschr. Pharm. 3, 269 (1865). Widely distributed in Aconitum and Delphinium spp., Ranunculaceae. Structure: Edwards et al., Can. J. Chem. 34, 1315 (1956); Anet et al., ibid. 35, 400 (1957). Identity with royline: Edwards, Rodger, ibid. 37, 1187 (1959). Stereochemistry: Przybylska, Marion, ibid. 1843. Revised configuration: S. W. Pelletier et al., J. Am. Chem. Soc. 103, 6536 (1981).
Properties: Crystals. Bitter taste. mp 143°. [a]D20 +53° (ethanol). Slightly sol in water, ether, benzene; freely sol in alcohol, chloroform.
Melting point: mp 143°
Optical Rotation: [a]D20 +53° (ethanol)
 
Derivative Type: Ajacine
CAS Registry Number: 509-17-1
Additional Names: N-Acetylanthranilic acid ester
Molecular Formula: C34H48N2O9
Molecular Weight: 628.75
Percent Composition: C 64.95%, H 7.69%, N 4.46%, O 22.90%
Properties: Needles from 70% alcohol, mp 154°. [a]D22 +49.5° (c = 2 in abs alcohol); [a]D16 +53° (c = 0.66 in chloroform). uv max: 223, 252, 310 nm (e 28400, 16600, 5400). Slightly sol in water; sol in ether, alcohol with blue fluorescence.
Melting point: mp 154°
Optical Rotation: [a]D22 +49.5° (c = 2 in abs alcohol); [a]D16 +53° (c = 0.66 in chloroform)
Absorption maximum: uv max: 223, 252, 310 nm (e 28400, 16600, 5400)
 
Derivative Type: Lycaconitine
CAS Registry Number: 25867-19-0
Additional Names: N-Succinylanthranilic acid ester
Molecular Formula: C36H48N2O10
Molecular Weight: 668.77
Percent Composition: C 64.65%, H 7.23%, N 4.19%, O 23.92%
Literature References: Isoln: Schulze, Bierling, Arch. Pharm. 251, 8 (1913).
Properties: White, amorphous powder, mp 111-114°. [a]D +42°; also reported as +31.5°. Insol in water. Sol in alcohol, chloroform, ether.
Melting point: mp 111-114°
Optical Rotation: [a]D +42°; also reported as +31.5°

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