Description
The bulbs of several Narcissus species contain this alkaloid which crystallizes in
the form of pale yellow needles with a pronounced yellow-green fluorescence. It
is best purified by recrystallization from either acetic acid or an aqueous mixture
of methoxyethyl alcohol. It is dextrorotatory with [α]589 + 145° or [Qh64 +
983° (c 1.5, EtOH). The ultraviolet spectrum in neutral solution (EtOH) has
absorption maxima at 252, 302 and 329 mil, while that in alkaline solution
(0.01 N/NaOH) has the maxima at 219, 249,310 and 355 mil. The O-methyl
ether forms shiny needles which also exhibit a strong blue fluorescence. The tri_x0002_acetate has been prepared as an amorphous, non-crystallizable substance. With
FeC13 the alkaloid gives a violet colour.
Chemical Properties
White crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from narcissus.
References
Ceriotti., Nature, 213,595 (1967)
Piozzi et al., Tetrahedron, 24, 1119 (1968)
Revised structure:
Mondon, Krohn., Tetrahedron Lett., 2123 (1970)
Savona, Piozzi, Marino., Chern. Cornrnun., 1006 (1970)
Absolute configuration:
Fuganti, Mazza.,J. Chern. Soc., Chern. Cornrnun., 239 (1972)
Crystal structure:
Immirzi, Fuganti., J. Chern. Soc., Chern. Cornrnun., 240 (1972)
Stereochemistry:
Mondon, Krohn., Tetrahedron Lett., 2085 (1972)
