Title: Lasiocarpine
CAS Registry Number: 303-34-4
CAS Name: (2Z)-2-Methyl-2-butenoic acid (1S,7aR)-7-[[(2R)-2,3-dihydroxy-2-[(1S)-1-methoxyethyl]-3-methyl-1-oxobutoxy]methyl]-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl ester
Molecular Formula: C21H33NO7
Molecular Weight: 411.49
Percent Composition: C 61.30%, H 8.08%, N 3.40%, O 27.22%
Literature References: Hepatotoxic pyrrolizidine alkaloid isolated from Heliotropium lasiocarpum Fish. et C. Mey. Boraginaceae: G. Menschikoff, Ber. 65, 974 (1932), C.A. 26, 48183 (1932), G. Menschikoff, J. Schdanowitsch, Ber. 69, 1110 (1936), C.A. 30, 52279 (1936). Structure: L. J. Drummond, Nature 167, 41 (1951); R. Adams, B. L. VanDuvren, J. Am. Chem. Soc. 76, 6379 (1954). Review and evaluation of studies of carcinogenicity and toxicity in laboratory animals: IARC Monographs 10, 281-290, 333-342 (1976). Comprehensive reviews: L. Bull et al., The Pyrrolizidine Alkaloids (North-Holland, Amsterdam, 1965) 293 pp; F. L. Warren in The Alkaloids vol. 12, R. H. F. Manske, Ed. (Academic Press, New York, 1970) pp 245-331; D. J. Robins, Fortschr. Chem. Org. Naturst. 41, 115-203 (1982).
Properties: Colorless leaflets from petr ether. mp 94-95.5°. [a]D -4° (10% alc). Sol on ether, alc, benzene; difficultly sol in water.
Melting point: mp 94-95.5°
Optical Rotation: [a]D -4° (10% alc) |