Salutaridine
Title: Salutaridine
CAS Registry Number: 1936-18-1
CAS Name: 5,6,8,14-Tetradehydro-4-hydroxy-3,6-dimethoxy-17-methylmorphinan-7-one
Additional Names: floripavine
Molecular Formula: C19H21NO4
Molecular Weight: 327.37
Percent Composition: C 69.71%, H 6.47%, N 4.28%, O 19.55%
Literature References: Intermediate in morphine synthesis; naturally occurring in (+)-form. Isolated from various species of Croton and Papaver: Barton et al., J. Chem. Soc. 1965, 2423; Pfeifer, Kühn, Pharmazie 23, 267 (1968). Structure and identity with floripavine: Mndzhoyan et al., C.A. 68, 114787w (1968). Synthesis: T. Kametani et al., J. Chem. Soc. C 1969, 2030; G. Horvath, S. Makleit, Acta Chim. Acad. Sci. Hung. 106, 37 (1981); of racemate: T. Kametani et al., J. Chem. Soc. Perkin Trans. 1 1972, 1435; C. Szántay et al., J. Org. Chem. 47, 594 (1982); of racemate and (-)-form: W. Ludwig, H. J. Schafer, Angew. Chem. Int. Ed. 25, 1025 (1986). Review: Stuart, Chem. Rev. 1971, 47.
Properties: Rods from ethyl acetate, mp 197-198°. [a]D12 +114° (c = 0.5 in methanol). uv max (methanol): 236, 279 nm (log e 4.23, 3.76).
Melting point: mp 197-198°
Optical Rotation: [a]D12 +114° (c = 0.5 in methanol)
Absorption maximum: uv max (methanol): 236, 279 nm (log e 4.23, 3.76)
 
Derivative Type: (-)-Form
Additional Names: Sinoaculine
Properties: [a]D20 -98° (c = 0.55 g/100 ml CH3OH). uv max (methanol): 276, 240 nm (log e 3.76, 4.24).
Optical Rotation: [a]D20 -98° (c = 0.55 g/100 ml CH3OH)
Absorption maximum: uv max (methanol): 276, 240 nm (log e 3.76, 4.24)

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