Tazettine
Title: Tazettine
CAS Registry Number: 507-79-9
Additional Names: Sekisanine; sekisanoline; ungernine
Molecular Formula: C18H21NO5
Molecular Weight: 331.36
Percent Composition: C 65.24%, H 6.39%, N 4.23%, O 24.14%
Literature References: From Narcissus tazetta L., Lycoris radiata Herb., Ungernia sewerzowi (Rgl.) Fedtsch., and other Amaryllidaceae: Späth, Kahovec, Ber. 67, 1501 (1934). Structure and stereochemistry: Ikeda et al., J. Chem. Soc. 1956, 4749. Abs config: Highet, Highet, Tetrahedron Lett. 1966, 4099. Synthesis: Hendrickson et al., J. Am. Chem. Soc. 92, 5538 (1970); Tsuda et al., Tetrahedron Lett. 1972, 3153. Biosynthesis: Fales, Wildman, J. Am. Chem. Soc. 86, 294 (1964). Identity with sekisanine and sekisanoline: Ikeda et al., loc. cit. Stereospecific total synthesis: Hendrickson et al., J. Am. Chem. Soc. 96, 7781 (1974); S. Danishefsky et al., ibid. 102, 2838 (1980); 104, 7591 (1982).
Properties: Crystals, mp 210-211° (evac tube); racemate reported as mp 237-238° (Tsuda) and mp 175-176° (Danishefsky). [a]D25 +150.3° (82 mg in 2 ml chloroform). Sol in methanol, ethanol, choroform. Sparingly sol in ether.
Melting point: mp 210-211° (evac tube); mp 237-238° (Tsuda) and mp 175-176° (Danishefsky)
Optical Rotation: [a]D25 +150.3° (82 mg in 2 ml chloroform)
 
Derivative Type: Hydrochloride
Properties: Crystals, mp 206°, water soluble.
Melting point: mp 206°
 
Derivative Type: Methiodide
Properties: Crystals, dec 220° (evacuated tube).

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