Seneciphylline
Title: Seneciphylline
CAS Registry Number: 480-81-9
CAS Name: 13,19-Didehydro-12-hydroxysenecionan-11,16-dione
Additional Names: jacodine; a-longilobine
Molecular Formula: C18H23NO5
Molecular Weight: 333.38
Percent Composition: C 64.85%, H 6.95%, N 4.20%, O 24.00%
Literature References: Hepatotoxic pyrrolizidine alkaloid, common constituent of Senecio species. Isoln from Senecio platyphllus DC. Compositae: A. Orechoff, W. Tiedebel, Ber. 68, 650 (1935); from S. jacobaea L.: G. Barger, J. J. Blackie, J. Chem. Soc. 1937, 584; from Crotalaria juncea L. Leguminosae: R. Adams, M. Gianturco, J. Am. Chem. Soc. 78, 1919 (1956). Identity with a-longilobine: R. Adams, J. H. Looker, ibid. 73, 134 (1951). Identity with jacodine: R. B. Bradbury, C. C. J. Culvenor, Chem. Ind. (London) 1954, 1021. Structural study: R. Adams et al., J. Am. Chem. Soc. 74, 700 (1952). Revised structure: S. Masume, Chem. Ind. (London) 1959, 21. Review and evaluation of toxicity and carcinogenicity studies: IARC Monographs 10, 319-325, 333-342 (1976). Comprehensive reviews of seneciphylline and other pyrrolizidine alkaloids: L. Bull et al., The Pyrrolizidine Alkaloids (North-Holland, Amsterdam, 1968) 293 pp; F. L.Warren in The Alkaloids vol. 12, R. H. F. Manske, Ed. (Academic Press, New York, 1970) pp 245-331.
Properties: Small rhombic platelets from hot alcohol or acetone, mp 217-218°. [a]D -128° (chloroform). Easily sol in chloroform, ethylene chloride; less sol in alc, acetone. Difficultly sol in ether, ligroin.
Melting point: mp 217-218°
Optical Rotation: [a]D -128° (chloroform)

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