Title: Lycorine
CAS Registry Number: 476-28-8
CAS Name: (1a,2b)-3,12-Didehydro-9,10-[methylenebis(oxy)]galanthan-1,2-diol
Additional Names: 3,3a-didehydrolycoran-1a,2b-diol; 2,4,5,7,12b,12c-hexahydro-1H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-1,2-diol; amarylline; belamarine; narcissine; galanthidine
Molecular Formula: C16H17NO4
Molecular Weight: 287.31
Percent Composition: C 66.89%, H 5.96%, N 4.88%, O 22.27%
Literature References: Alkaloid isolated from the bulbs of Lycoris radiata L., Narcissus pseudonarcissus L., N. tazetta L., from Buphane disticha Herb., in Crinum spp., Amaryllis belladonna L., Clivia miniata Regel and other Amaryllidaceae. Extraction procedure: Cook, Loudon in Manske-Holmes, Alkaloids vol. II (Academic Press, 1952) p 336. Identity of lycorine and galanthidine: Proskurnina, Dokl. Akad. Nauk SSSR 90, 565 (1953), C.A. 49, 12500c (1955). Structure: Takeda et al., J. Am. Chem. Soc. 80, 2562 (1958). Stereochemistry: Nakagawa, Uyeo, J. Chem. Soc. 1959, 3736; K. Kotera et al., Tetrahedron Lett. 1966, 2009. Crystal structure: R. Roques, Acta Crystallogr. 30B, 296 (1974). Attempted synthesis: Dyke et al., Tetrahedron 29, 213 (1973). Synthesis: Y. Tsuda et al., Chem. Commun. 1975, 933; eidem, J. Chem. Soc. Perkin Trans. 1 1979, 1358; T. Sano et al., Heterocycles 14, 1097 (1980); S. F. Martin, C. Tu, J. Org. Chem. 46, 3763 (1981). Biosynthesis: Archer et al., Proc. Chem. Soc. London 1963, 168; Fugati, Mazza, Chem. Commun. 1972, 936. Review: W. C. Wildman in The Alkaloids vol. XI, R. H. F. Manske, Ed. (Academic Press, New York, 1968) pp 307-400.
Properties: Stout prisms from alcohol, mp 275-280° (dec). [a]D16 -129° (c = 0.16 in 98% alc). Alkaline reaction to litmus; salts hydrolyze easily. Sparingly sol in alcohol, chloroform, petr ether. Sol in dilute acids. Practically insol in water, alkalies.
Melting point: mp 275-280° (dec)
Optical Rotation: [a]D16 -129° (c = 0.16 in 98% alc)
Derivative Type: Hydrochloride
Molecular Formula: C16H17NO4.HCl
Molecular Weight: 323.77
Percent Composition: C 59.35%, H 5.60%, N 4.33%, O 19.77%, Cl 10.95%
Properties: Long needles from water, mp 217° (dec with slight preliminary sintering). [a]D20 +43°.
Melting point: mp 217° (dec with slight preliminary sintering)
Optical Rotation: [a]D20 +43°
Derivative Type: Hydrochloride monohydrate
Properties: Elongated prisms from water, mp 206°. Soluble in 20 parts water.
Melting point: mp 206°
Derivative Type: Methiodide
Molecular Formula: C16H17NO4.CH3I
Molecular Weight: 429.25
Percent Composition: C 47.57%, H 4.70%, N 3.26%, O 14.91%, I 29.56%
Properties: Two forms exist which may be stereoisomeric about the nitrogen atom. a- Form: polyhedra from alc, dec 247°. [a]D20 -46° (c = 1.52). Freely sol in water; sparingly sol in hot alcohol. b-Form: prisms contg 1H2O from water, dec 198°, after recryst from alcohol, dec 281°. [a]D20 +123° (c = 2.44). Freely sol in water and hot alcohol.
Optical Rotation: [a]D20 -46° (c = 1.52); [a]D20 +123° (c = 2.44)
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