Napelline
Title: Napelline
CAS Registry Number: 5008-52-6
CAS Name: (1a,12a,15b)-21-Ethyl-4-methyl-16-methylene-7,20-cycloveatchane-1,12-15-triol
Additional Names: luciculine
Molecular Formula: C22H33NO3
Molecular Weight: 359.50
Percent Composition: C 73.50%, H 9.25%, N 3.90%, O 13.35%
Literature References: Isoln from Aconitum napellus L., Ranunculaceae: Freudenberg, Rogers, J. Am. Chem. Soc. 59, 2572 (1937); Jacobs, Craig, J. Biol. Chem. 143, 611 (1942). The product obtained by these isoln procedures is a mixture of at least three compounds. Structure: Wiesner, Valenta, Fortschr. Chem. Org. Naturst. 16, 53 (1958). Related stereochemical studies: Okamoto et al., Chem. Pharm. Bull. 13, 1270 (1963). Total synthesis of racemic napelline: Wiesner et al., Can. J. Chem. 52, 2353, 2355 (1974); S. P. Sethi et al., ibid. 58, 1889 (1980).
Properties: Rectangular plates from ether + petr ether.
 
Derivative Type: Hydrochloride
Molecular Formula: C22H34ClNO3
Molecular Weight: 395.96
Percent Composition: C 66.73%, H 8.65%, Cl 8.95%, N 3.54%, O 12.12%
Properties: Solvated crystals, dec 200-222°. [a]D22 -93.9° (c = 5). Sol in water.
Optical Rotation: [a]D22 -93.9° (c = 5)

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